RU2828212C2 - 3-substituted phenylamidine compounds, production and use thereof - Google Patents

Abstract

FIELD: chemistry.

SUBSTANCE: invention relates to 3-substituted phenylamidine compound of general formula (I) or an agriculturally acceptable salt or stereoisomer, where R¹ is C₁-C₆alkyl; R² is C₁-C₆alkyl; R³ is selected from the group consisting of X, C₁-C₆alkyl, C₁-C₆haloalkyl and S(O)nR′′′; R⁴ is selected from the group consisting of X, cyano, C₁-C₆alkyl, C₁-C₆haloalkyl and OR′′; R^4a and R^4b are hydrogen; A is -{[C(R⁶R⁷)]_0-2-(B)_0-1}-, where B is NR⁵ or CR⁶R⁷; or A is -O-CR⁶R⁷-C(O)-; R⁵ is selected from the group consisting of hydrogen and C₁-C₆alkyl; R⁶ and R⁷ are hydrogen; ring E is selected from the group consisting of phenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl and benzothiazolyl, which are optionally substituted with one to three R⁸ groups; R⁸ is selected from a group consisting of hydrogen, X, cyano, nitro, C₁-C₆alkyl, C₁-C₆haloalkyl, OR′′ and S(O)nR′′′; two R⁸ together with the atoms to which they are attached, or together with additional atoms selected from the group consisting of N, O, can form a five-six-membered ring; X is a halogen; R" is selected from the group consisting of C₁-C₆alkyl and C₁-C₆haloalkyl; R" is selected from R"; n is integer 0. Invention also relates to a method of producing a compound of formula (I), a composition for controlling and/or preventing the appearance of phytopathogenic fungi, comprising a compound of formula (I), method of controlling or preventing occurrence of phytopathogenic fungi, comprising using a compound of formula (I) or a composition, method of controlling rust diseases, comprising using a compound of formula (I) or a composition, treating a seed with a compound of formula (I) for protection against phytopathogenic fungi, method of controlling and preventing infection of useful plants with phytopathogenic fungi, comprising using a compound of formula (I) or a composition, a compound of formula (A), where Z is X; R¹ is C_1-6alkyl; R² is C_1-6alkyl; R³ is selected from the group consisting of X, C_1-6alkyl, C_1-6haloalkyl and S(O)_nR′′′; R⁴ is selected from the group consisting of X, cyano, C_1-6alkyl, C_1-6haloalkyl and OR′′, where R and R '' 'are defined in cl. 1, and an intermediate compound selected from the group for obtaining a compound of formula (I).

EFFECT: control or prevention of phytopathogenic microorganisms appearance.

27 cl, 1 tbl, 17 ex

Description

REGION TECHNIQUES, TO WHICH RELATED INVENTION

The present invention relates to 3-substituted phenylamidine compounds. More particularly, the present invention relates to 3-substituted phenylamidine compounds of general formula (I), to a method for producing and to the use of the compounds as a crop protection agent.

PREREQUISITES INVENTIONS

Pathogenic fungi continue to pose a serious threat to public health and agriculture. Therefore, control of plant diseases caused by plant pathogenic fungi is of utmost importance to achieve high crop productivity. Plant diseases affecting ornamentals, vegetables, field crops, cereals, and fruit crops can significantly reduce yields and thereby increase costs to the consumer. In addition to often being extremely harmful, plant diseases can be difficult to control and resistance to commercial fungicides can develop. A large number of products are available on the market for these purposes, but there remains a need for new fungicidal compounds that are more effective, less expensive, less toxic, more environmentally friendly, or have different sites of action.

For example, WO2000046184, WO2003024219, WO2005089547, WO2003093224, WO2007031507 disclose phenylamidine derivatives and their use as fungicides either alone or as part of compositions.

The effectiveness of the phenylamidine derivatives described in the prior art is good, but in various cases leaves much to be desired. Therefore, in agriculture, there is always great interest in the use of new pesticide compounds to eliminate and/or control the development of microorganisms, such as fungal or bacterial pathogens, or pests resistant to known active ingredients. Therefore, there is great interest in the use of new compounds that are more active than those already known, in order to reduce the amount of active compound used while maintaining an effectiveness at least equivalent to that of the already known compounds.

Nowadays, the ecological and economic demands on fungicides are constantly increasing, for example with regard to the spectrum of activity, toxicity, selectivity, application rate, residue formation and favorable production processes, and the occurrence of, for example, resistance problems is also increasing, therefore, there is a constant need for new fungicidal compounds that will overcome these ecological and economic demands and/or reduce the problems associated with resistance to pathogens. Accordingly, the present invention provides a new family of compounds that have the above-mentioned effects or advantages, thereby providing an unexpected and significantly higher activity against undesirable microorganisms, such as fungal or bacterial pathogens.

ESSENCE PRESENT INVENTIONS

Accordingly, the present invention provides a 3-substituted phenylamidine compound of general formula (I) or agriculturally acceptable salts, structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs or N-oxides thereof.

where R ¹ , R ² , R ³ , R ⁴ , R ^4a , R ^4b , A and E are defined in the detailed description.

In one embodiment, the present invention provides a process for producing a compound of general formula (I) or an agriculturally acceptable salt thereof.

In another embodiment, the present invention provides a composition comprising at least one compound of general formula (I) and optionally at least one other active compound selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and/or mixtures thereof.

In another embodiment, the present invention provides the use of compounds of formula (I) and compositions based thereon for controlling and/or preventing the occurrence of phytopathogenic microorganisms in agricultural crops and/or horticultural crops.

In another embodiment, the present invention provides the use of at least one compound of the present invention in combinations or compositions and methods of using it, in particular in the field of agriculture, especially for plant protection.

The compounds of the present invention have increased activity against microorganisms, in particular against phytopathogenic fungi. The compounds of the present invention can be used in the field of agriculture or can be used as intermediates for the synthesis of compounds having wider application options.

DETAILED DESCRIPTION INVENTIONS

DEFINITIONS

The following definitions provided for the terminology used in the present invention are intended for illustrative purposes only and are not intended to limit the scope of the present invention disclosed herein in any way.

The transitional phrase "comprises," "comprising," "includes," "including," "has," "having," "contains," "containing," "characterized by," or any other variations thereof, are intended to cover non-exclusive inclusion, subject to any limitations being expressly stated. For example, a composition, mixture, process, or method that includes a list of elements is not necessarily limited to only those elements, but may include other elements not expressly listed or not inherent in such composition, mixture, process, or method.

The transitional phrase "consisting of" excludes any unspecified element, step, or ingredient. When this phrase appears in a claim, it limits the inclusion in the claim of materials other than those recited, excluding impurities normally associated therewith. When the phrase "consisting of" appears in a sentence of the characterizing part of a claim, rather than immediately following the preamble, it limits only the element recited in that sentence; other elements are not excluded from the claim as a whole.

The transitional phrase "consisting essentially of" is used to define a composition or method that includes materials, steps, features, components, or elements in addition to those literally disclosed, provided that these additional materials, steps, features, components, or elements do not materially affect the basic and novel characteristics of the claimed invention. The term "consisting essentially of" occupies a middle ground between "comprising" and "consisting of."

Also, unless explicitly stated otherwise, "or" refers to an inclusive "or" rather than an exclusive "or." For example, the condition "A" or "B" is satisfied by any of the following: A is true (or present) and B is false (or absent), A is false (or absent) and B is true (or present), and A and B are both true (or present).

In addition, an element or component in the singular form of the present invention is intended for an unlimited number of occurrences (i.e., occurrences) of the element or component. Therefore, singular forms should be read as including one or at least one, and the singular form of an element or component also includes a plural, unless the number clearly means singular.

As referred to in the present invention, the term "pesticide" in each instance also always includes the term "crop protection agent".

The term "undesirable microorganisms" or "phytopathogenic microorganisms" such as fungal or bacterial pathogens includes more specifically Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes and Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae , respectively.

The term "agronomic" refers to the production of field crops such as those for food, fuels, biofuels, any biomaterials and fibres, and includes, but is not limited to, the cultivation of corn, soybeans and other legumes, rice, cereals (e.g. wheat, oats, barley, rye, rice, maize), leafy vegetables (e.g. lettuce, cabbage and other brassicas), fruit-bearing vegetables (e.g. tomatoes, peppers, eggplants, brassicas and cucurbits), potatoes, sweet potatoes, grapes, cotton, tree fruits (e.g. pome fruits, stone fruits and citrus fruits), soft fruit crops (berries, cherries), biofuel crops such as corn, sugar/starch crops, sugar beets and sweet sorghum, pulp crops such as switchgrass, miscanthus, corn straw, poplar, rapeseed (canola) crops for diesel biofuel, soybeans, palm oil, mustard, camelina, safflower, sunflower and jatropha and other specialty crops (e.g. canola, sunflower, olives).

The term "non-agronomic" refers to crops other than field crops, such as horticultural crops (e.g., greenhouse plants, nursery plants, or ornamentals not grown in the field), residential, agricultural, commercial, and industrial applications, turf (e.g., sod farm, pasture, golf course, lawn, sports field, etc.), wood products, stored products, agroforestry and vegetation management, public health (i.e., human health), and animal health (e.g., domesticated animals such as pets, livestock, and poultry, non-domesticated animals such as wildlife).

The terms alkyl, alkenyl, alkynyl, carbocyclyl, heterocyclyl, aryl and heteroaryl groups as defined herein are optionally substituted (e.g., a "substituted" or "unsubstituted" alkyl, a "substituted" or "unsubstituted" alkenyl, a "substituted" or "unsubstituted" alkynyl, a "substituted" or "unsubstituted" carbocyclyl, a "substituted" or "unsubstituted" heterocyclyl, a "substituted" or "unsubstituted" aryl or a "substituted" or "unsubstituted" heteroaryl group). In general, the term "substituted", whether or not preceded by the term "optionally", means that at least one hydrogen atom present in the group (e.g., a carbon or nitrogen atom, etc.) is replaced by a permissible substituent, e.g., a substituent which, when substituted, results in a stable compound, e.g., a compound which does not undergo spontaneous transformation such as rearrangement, cyclization, elimination, or other reactions under normal conditions (temperature, pressure, air, etc.). Unless otherwise specified, a "substituted" group has a substituent at one or more substitutable positions of the group, and when more than one position in any given structure is substituted, the substituent is either the same or different at each position.

The term "alkyl" whether used alone or in compound words such as "alkylthio" or "haloalkyl" includes straight or branched _C1 - _C24 alkyl, preferably _C1 - _C15 alkyl, more preferably _C1 - _C10 alkyl, most preferably _C1 - _C6 alkyl. Non-limiting examples of alkyl include methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl and 1-ethyl-2-methylpropyl or various isomers. If the alkyl is at the end of a complex substituent, as in alkylcycloalkyl, then the part of the complex substituent at the beginning, for example, cycloalkyl, can be mono- or polysubstituted equally or differently, and independently, by alkyl. The same applies to complex substituents that have other radicals at the end, for example, alkenyl, alkynyl, hydroxyl, halogen, carbonyl, carbonyloxy, etc.

The term "alkenyl", whether used alone or in compound words, includes branched or ramified _C2 - _C24 alkenes, preferably _C2 - _C15 alkenes, more preferably _C2 - _C10 alkenes, most preferably _C2 - _C6 alkenes. Non-limiting examples of alkenes include ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-l-propenyl, l-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, l-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, l-methyl-3-butenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, l-ethyl-2-propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl-1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, l-methyl-3-pentenyl, 2-methyl-3-pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-l-butenyl, 3,3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl- 1-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl and 1-ethyl-2-methyl-2-propenyl and various isomers. "Alkenyl" also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl. This definition also applies to alkenyl as part of a complex substituent, such as haloalkenyl and the like, unless otherwise specifically indicated elsewhere.

The term "alkynyl", whether used alone or in compound words, includes branched or ramified _C2 - _C24 alkynes, preferably _C2 - _C15 alkynes, more preferably _C2 - _C10 alkynes, most preferably _C2 - _C6 alkynes. Non-limiting examples of alkynes include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1,1-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl and various isomers. This definition also applies to alkynyl as part of a complex substituent, e.g., haloalkynyl, etc., unless otherwise specifically stated elsewhere. "Alkynyl" may also include moieties consisting of multiple triple bonds, such as 2,5-hexadiynyl.

The term "cycloalkyl" means an alkyl group closed to form a ring. Non-limiting examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, and cyclohexyl. This definition also applies to cycloalkyl as part of a complex substituent, such as cycloalkylalkyl, etc., unless otherwise specifically stated elsewhere.

The term "cycloalkenyl" means alkenyl closed to form a ring comprising a monocyclic, partially unsaturated hydrocarbon group. Non-limiting examples include, but are not limited to, cyclopentenyl and cyclohexenyl. This definition also applies to cycloalkenyl as part of a complex substituent, such as cycloalkenylalkyl, etc., unless otherwise specifically stated elsewhere.

The term "cycloalkynyl" means an alkynyl group closed to form a ring incorporating a monocyclic, partially unsaturated group. This definition also applies to cycloalkynyl as part of a complex substituent, e.g., cycloalkynylalkyl, etc., unless otherwise specifically stated elsewhere.

The terms "cycloalkoxy", "cycloalkenyloxy", etc. are defined similarly. Non-limiting examples of cycloalkoxy include cyclopropyloxy, cyclopentyloxy and cyclohexyloxy. This definition also applies to cycloalkoxy as part of a complex substituent, such as cycloalkoxyalkyl, etc., unless otherwise specifically stated elsewhere.

The term "alkoxy" whether used alone or in compound words includes _C1 - _C24 alkoxy, preferably _C1 - _C15 alkoxy, more preferably _C1 - _C10 alkoxy, most preferably _C1 - _C6 alkoxy. Non-limiting examples of alkoxy include methoxy, ethoxy, propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy and various isomers. This definition also applies to alkoxy as part of a complex substituent, e.g., haloalkoxy, alkynylalkoxy, etc., unless otherwise specifically stated elsewhere.

The term "alkylthio" includes branched or unbranched alkylthio moieties such as methylthio, ethylthio, propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio, 1,1-dimethylethylthio, pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, 1,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio and various isomers.

Non-limiting examples of "alkylsulfinyl" include, but are not limited to, methylsulfinyl, ethylsulfinyl, propylsulfinyl, 1-methylethylsulfinyl, butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1,1-dimethylethylsulfinyl, pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, hexylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl and 1-ethyl-2-methylpropylsulfinyl and various isomers. The term "arylsulfinyl" includes Ar-S(O), where Ar may be any carbocycle or heterocycle. This definition also applies to alkylsulfinyl as part of a complex substituent, e.g., haloalkylsulfinyl, etc., unless otherwise specifically indicated elsewhere.

Non-limiting examples of "alkylsulfonyl" include, but are not limited to, methylsulfonyl, ethylsulfonyl, propylsulfonyl, 1-methylethylsulfonyl, butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1,1-dimethylethylsulfonyl, pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, hexylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, 1-ethyl-1-methylpropylsulfonyl and 1-ethyl-2-methylpropylsulfonyl and various isomers. The term "arylsulfonyl" includes Ar-S(O) ₂ , where Ar may be any carbocycle or heterocycle. This definition also applies to alkylsulfonyl as part of a complex substituent, e.g., alkylsulfonylalkyl, etc., unless otherwise specified elsewhere.

The term "hydroxy" means -OH, "amino" means -NRR, where R may be H or any possible substituent such as alkyl; "carbonyl" means -C(O)-, "carbonyloxy" means -OC(O)-, "sulfinyl" means SO, "sulfonyl" means S(O) ₂ .

The term "halogen", either alone or in compound words such as "haloalkyl", includes fluorine, chlorine, bromine or iodine. Furthermore, when used in compound words such as "haloalkyl", said alkyl may be partially or completely replaced by halogen atoms, which may be the same or different.

Non-limiting examples of "haloalkyl" include chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 1,1-dichloro-2,2,2-trifluoroethyl and 1,1,1-trifluoroprop-2-yl. This definition also applies to haloalkyl as part of a complex substituent, such as haloalkylaminoalkyl, etc., unless otherwise specifically stated elsewhere.

The terms "haloalkenyl" and "haloalkynyl" are defined similarly, except that instead of an alkyl group, alkenyl and alkynyl groups are present as part of the substituent.

The term "haloalkoxy" means a straight or branched alkoxy group, some or all of the hydrogen atoms in such groups may be replaced by halogen atoms as defined above. Non-limiting examples of haloalkoxy include chloromethoxy, bromomethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1-bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy and 1,1,1-trifluoroprop-2-oxy. This definition also applies to haloalkoxy as part of a complex substituent, such as haloalkoxyalkyl, etc., unless otherwise specifically stated elsewhere.

The term "haloalkylthio" or "haloalkylsulfanyl" means a straight or branched alkylthio group wherein some or all of the hydrogen atoms in such groups may be replaced by halogen atoms as defined above. Non-limiting examples of haloalkylthio include chloromethylthio, bromomethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-chloroethylthio, 1-bromoethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio, pentafluoroethylthio and 1,1,1-trifluoroprop-2-ylthio. This definition also applies to haloalkylthio as part of a complex substituent, e.g. haloalkylthioalkyl, etc., unless otherwise specifically stated elsewhere.

Examples of "haloalkylsulfinyl" include CF ₃ S(O), CCl ₃ S(O), CF ₃ CH ₂ S(O) and CF ₃ CF ₂ S(O). Examples of "haloalkylsulfonyl" include CF ₃ S(O) ₂ , CCl ₃ S(O) ₂ , CF ₃ CH ₂ S(O) ₂ and CF ₃ CF ₂ S(O) ₂ .

The term "bicyclic ring or ring system" refers to a ring system consisting of two or more common atoms.

The term "aromatic" indicates that Huckel's rule is satisfied, and the term "non-aromatic" indicates that Huckel's rule is not satisfied.

The terms "carbocycle" or "carbocyclic" or "carbocyclyl" include "aromatic carbocyclic ring system" and "non-aromatic carbocyclic ring system" or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds in which the ring may be aromatic or non-aromatic (where "aromatic" indicates that the Huckel rule is satisfied and non-aromatic indicates that the Huckel rule is not satisfied).

Non-limiting examples of non-aromatic carbocyclic ring system are cyclopropyl, cyclobutyl, cyclopentyl, norbornyl, etc.

Non-limiting examples of aromatic carbocyclic ring system are phenyl, naphthyl, etc.

The term "aryl" as used herein is a group that contains any carbon-based aromatic group, including but not limited to phenyl, naphthalene, biphenyl, anthracene, and the like. The aryl group may be substituted or unsubstituted. In addition, the aryl group may be a single ring structure or contain multiple ring structures that are either fused ring structures or attached via one or more bridging groups, such as a carbon-carbon bond.

The term "aralkyl" refers to aryl hydrocarbon radicals comprising an alkyl moiety as defined above. Non-limiting examples include benzyl, phenylethyl, and 6-naphthylhexyl. As used herein, the term "aralkenyl" refers to aryl hydrocarbon radicals comprising an alkenyl moiety as defined above and an aryl moiety as defined above. Non-limiting examples include styryl, 3-(benzyl)-prop-2-enyl, and 6-naphthylhex-2-enyl.

The term "hetero" together with rings refers to a ring in which at least one atom in the ring is not a carbon atom and which may contain 1-4 heteroatoms independently selected from the group consisting of nitrogen, oxygen and sulfur, provided that each ring contains no more than 4 nitrogen atoms, no more than 2 oxygen atoms and no more than 2 sulfur atoms.

The term "heterocycle" or "heterocyclic" includes "aromatic heterocycle" or "heteroaryl ring systems" and "non-aromatic heterocyclyl ring systems", or polycyclic or bicyclic (spiro, fused, bridged, non-fused) ring compounds, in which the ring may be aromatic or non-aromatic, wherein the heterocyclyl ring contains at least one heteroatom selected from N, O, S(O) _0-2 , and/or C as a member of the heterocycle ring may be replaced by C(=O), C(=S), C(=CR*R*) and C=NR*, wherein * indicates integers.

The term "non-aromatic heterocycle" or "non-aromatic heterocyclic compound" means a three- to fifteen-membered, preferably three- to twelve-membered, saturated or partially unsaturated heterocycle containing from one to four heteroatoms from the group of oxygen, nitrogen and sulfur: mono-, bi- or tricyclic heterocycles which contain, in addition to the members in the carbon ring, from one to three nitrogen atoms and/or one oxygen or sulfur atom, or one or two oxygen and/or sulfur atoms; if the ring contains more than one oxygen atom, they are not directly adjacent; for example, (without limitation) oxiranyl, aziridinyl, oxetanyl, azetidinyl, thietanyl, 2-tetrahydrofuranyl, 3-tetrahydrofuranyl, 2-tetrahydrothienyl, 3-tetrahydrothienyl, 1-pyrrolidinyl, 2-pyrrolidinyl, 3-pyrrolidinyl, 3-isoxazolidinyl, yl, 5-isoxazolidinyl, 3-isothiazolidinyl, 4-isothiazolidinyl, 5-isothiazolidinyl, 1-pyrazolidinyl, 3-pyrazolidinyl, 4-pyrazolidinyl, 5-pyrazolidinyl, 2-oxazolidinyl, 4-oxazolidinyl, 5-oxazolidinyl, 2-thiazolidinyl, 5-thiazolidinyl, 1-imidazolidinyl, 2-imidazolidinyl, 4-imidazolidinyl, 1,2,4-oxadiazolidin-3-yl, 1,2,4-oxadiazolidin-5-yl, 1,2,4-thiadiazolidin-3-yl, 1,2,4-thiadiazolidin-5-yl, 1-yl, 1,2,4-triazolidin-3-yl, 1,3,4-oxadiazolidin-2-yl, 1,3,4-thiadiazolidin-2-yl, 1,3,4-triazolidin-1-yl, 1,3,4-triazolidin-2-yl, 2,3-dihydrofur-2-yl, 2,3-dihydrofur-3-yl, 2,4-dihydrofur-2-yl, 2,4-dihydrofur-3-yl, 2,3-dihydrothien-2-yl, 2,3-dihydrothien-3-yl, 2,4-dihydrothien-2-yl, 2,4-dihydrothien-3-yl, pyrrolinyl, 2-pyrrolin-2-yl, 2-pyrrolin-3-yl, 3-pyrrolin-2-yl, 3-pyrrolin-3-yl, 2-isoxazolin-3-yl, 3-isoxazolin-3-yl, 4-isoxazolin-3-yl, 2-isoxazolin-4-yl, 3-isoxazolin-4-yl, 4-isoxazolin-4-yl, 2-isoxazolin-5-yl, 3-isoxazolin-5-yl, 4-isoxazolin-5-yl, 2-isothiazolin-3-yl, 3-isothiazolin-3-yl, 4-isothiazolin-3-yl, 2-isothiazolin-4-yl, 3-isothiazolin-4-yl, 4-isothiazolin-4-yl, 2-isothiazolin-5-yl, 3-isothiazolin-5-yl, 4-isothiazolin-5-yl, 2,3-di hydropyrazol-1-yl, 2,3-dihydropyrazol-2-yl, 2,3-dihydropyrazol-3-yl, 2,3-dihydropyrazol-4-yl, 2,3-dihydropyrazol-5-yl, 3,4-dihydropyrazol-1-yl, 3,4-dihydropyrazol-3-yl, 3,4-dihydropyrazol-4-yl, -5-il, 4,5-dihydropyrazol-1-yl, 4,5-dihydropyrazol-3-yl, 4,5-dihydropyrazol-4-yl, 4,5-dihydropyrazol-5-yl, 2,3-dihydrooxazol-2-yl, 2,3-dihydrooxazol-3-yl, 2,3-dihydrooxazol-4-yl, , 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, 3,4-dihydrooxazol-5-yl, 3,4-dihydrooxazol-2-yl, 3,4-dihydrooxazol-3-yl, 3,4-dihydrooxazol-4-yl, piperidinyl, idinyl, 3-piperidinyl, 4-piperidinyl, pyrazinyl, morpholinyl, thiomorpholinyl, 1,3-dioxan-5-yl, 2-tetrahydropyranyl, 4-tetrahydropyranyl, 2-tetrahydrothienyl, 3-hexahydropyridazinyl, 4-hexahydropyridazinyl, 2-hexahydropyrimidinyl, 4-hexahydropyrimidinyl, 5-hexahydropyrimidinyl, 2-piperazinyl, cycloserines. This definition also applies to heterocyclyl as part of a complex substituent, e.g., heterocyclylalkyl, etc., unless otherwise specifically stated elsewhere.

The term "heteroaryl" means a 5- or 6-membered, completely unsaturated, monocyclic ring system containing from one to four heteroatoms from the oxygen, nitrogen and sulfur groups; wherein if the ring contains more than one oxygen atom, the oxygen atoms are not immediately adjacent; 5-membered heteroaryl containing one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom: 5-membered heteroaryl groups which in addition to carbon atoms may contain one to four nitrogen atoms or one to three nitrogen atoms and one sulfur or oxygen atom as ring members, such as (but not limited to) furyl, thienyl, pyrrolyl, isoxazolyl, isothiazolyl, pyrazolyl, oxazolyl, thiazolyl, imidazolyl, 1,2,4-oxadiazolyl, 1,2,4-thiadiazolyl, 1,2,4-triazolyl, 1,3,4-oxadiazolyl, 1,3,4-thiadiazolyl, 1,3,4-triazolyl, tetrazolyl; a nitrogen-linked 5-membered heteroaryl containing one to four nitrogen atoms or a benzo-fused nitrogen-linked 5-membered heteroaryl containing one to three nitrogen atoms: 5-membered heteroaryl groups which in addition to carbon atoms may contain from one to four nitrogen atoms or from one to three nitrogen atoms as ring members, and in which two adjacent carbon atoms as ring members or one nitrogen atom and one adjacent carbon atom as a ring member may be bridged by a buta-1,3-diene-1,4-diyl group in which one or two carbon atoms may be replaced by nitrogen atoms, wherein these rings are attached to the skeleton through one of the nitrogen atoms as ring members, for example (without limitation), 1-pyrrolyl, 1-pyrazolyl, 1,2,4-triazolyl, 1-imidazolyl, 1,2,3-triazolyl and 1,3,4-triazolyl;

6-membered heteroaryl which contains from one to four nitrogen atoms: 6-membered heteroaryl groups which in addition to the carbon atoms may contain, respectively, from one to three and from one to four nitrogen atoms as ring members, such as (but not limited to) 2-pyridinyl, 3-pyridinyl, 4-pyridinyl, 3-pyridazinyl, 4-pyridazinyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, 2-pyrazinyl, 1,3,5-triazin-2-yl, 1,2,4-triazin-3-yl and 1,2,4,5-tetrazin-3-yl; benzofused 5-membered heteroaryl containing one to three nitrogen atoms or one nitrogen atom and one oxygen or sulfur atom: for example (without limitation), indol-1-yl, indol-2-yl, indol-3-yl, indol-4-yl, indol-5-yl, indol-6-yl, indol-7-yl, benzimidazol-1-yl, benzimidazol-2-yl, benzimidazol-4-yl, benzimidazol-5-yl, indazol-1-yl, indazol-3-yl, indazol-4-yl, indazol-5-yl, indazol-6-yl, indazol-7-yl, indazol-2-yl, 1-benzofuran-2-yl, 1-benzofuran-3-yl, 1-benzofuran-4-yl, 1-benzofuran-5-yl, 1-benzofuran-6-yl, 1-benzofuran-7-yl, 1-benzothiophen-2-yl, 1-benzothiophen-3-yl, 1-benzothiophen-4-yl, 1-benzothiophen-5-yl, 1-benzothiophen-6-yl, 1-benzothiophen-7-yl, 1,3-benzothiazol-2-yl, 1,3-ben Zothiazol-4-yl, 1,3-benzothiazol-5-yl, 1,3-benzothiazol-6-yl, 1,3-benzothiazol-7-yl, 1,3-benzoxazol-2-yl, 1,3-benzoxazol-4-yl, 1,3-benzoxazol-5-yl, 1,3-benzoxazol-6-yl and 1,3-benzoxazol-7-yl; a benzo-fused 6-membered heteroaryl which contains from one to three nitrogen atoms: for example (without limitation), quinolin-2-yl, quinolin-3-yl, quinolin-4-yl, quinolin-5-yl, quinolin-6-yl, quinolin-7-yl, quinolin-8-yl, isoquinolin-1-yl, isoquinolin-3-yl, isoquinolin-4-yl, isoquinolin-5-yl, isoquinolin-6-yl, isoquinolin-7-yl and isoquinolin-8-yl.

Non-limiting examples of fused 6- to 5-membered heteroaryl include indolizinyl; pyrazolo[1,5-a]pyridinyl; imidazo[1,2-a]pyridinyl; pyrrolo[1,2-a]pyrimidinyl; pyrazolo[1,5-a]pyrimidinyl; imidazo[1,2-a]pyrimidinyl; pyrrolo[1,2-a]pyrazinyl; pyrazolo[1,5-a]pyrazinyl; imidazo[1,2-a]pyrazinyl and the like.

This definition also applies to heteroaryl as part of a complex substituent, such as heteroarylalkyl, etc., unless otherwise specifically stated elsewhere.

The term "amide" means A-R'C=ONR''-B, where R' and R'' are substituents and A and B are any group.

The term "thioamide" means A-R'C=SNR''-B, where R' and R'' are substituents and A and B are any group.

The term "leaving group" means all substituents that have sufficient nucleophilicity under the prevailing reaction conditions, or a nucleophilically exchangeable group; examples of suitable leaving groups include halogens, triflate, mesylate, tosylate, or _SO2 -Me.

The total number of carbon atoms in a substituent group is indicated by the prefix "C _i -C _j ", where i and j are numbers from 1 to 21. For example, C ₁ -C ₃ alkylsulfonyl denotes methylsulfonyl through propylsulfonyl; C ₂ alkoxyalkyl denotes CH ₃ OCH ₂ ; C ₃ alkoxyalkyl denotes, for example, CH ₃ CH(OCH ₃ ), CH ₃ OCH ₂ CH ₂ or CH ₃ CH ₂ OCH ₂ ; and C ₄ alkoxyalkyl denotes various isomers of an alkyl group substituted by an alkoxy group containing a total of four carbon atoms, examples include CH ₃ CH ₂ CH ₂ OCH ₂ and CH ₃ CH ₂ OCH ₂ CH ₂ . In the above listings, if a compound of formula I consists of one or more heterocyclic rings, then all substituents are attached to these rings through any available carbon or nitrogen atom by replacing a hydrogen atom at the specified carbon or nitrogen atom.

If the compound is substituted with a substituent with a specified subscript, which means that the number of said substituents may exceed 1, then said substituents (if they exceed 1) are independently selected from the group of specified substituents. In addition, if the subscript m in (R) _m means an integer in the range, for example, from 0 to 4, then the number of substituents may be selected from integers from 0 to 4 inclusive.

If a group contains a substituent which may be hydrogen, the group is considered to be unsubstituted if the substituent is taken to be hydrogen.

The embodiments provided herein and their various features and advantageous details are explained with reference to non-limiting embodiments in the description. Descriptions of well-known components and processing methods are omitted so as not to unnecessarily obscure the understanding of the embodiments provided herein. The examples used herein are intended only to provide a simplified understanding of the ways in which the embodiments herein may be practiced and to further enable those skilled in the art to practice the embodiments provided herein. Accordingly, the examples should not be understood as limiting the scope of the embodiments provided herein.

The foregoing description of specific embodiments will so fully disclose the general character of the embodiments herein that others may, by application of current knowledge, readily modify and/or adapt such specific embodiments to various applications without departing from the general concept, and therefore such adaptations and modifications should be understood and are intended to be understood within the meaning and range of equivalents of the disclosed embodiments. It should be understood that the language or terminology used herein is intended to be descriptive and not limiting. Accordingly, although the embodiments provided herein have been described in the context of preferred embodiments, those skilled in the art will recognize that the embodiments provided herein may be practiced with modification within the spirit and scope of the embodiments as described herein.

Any reference to documents, acts, materials, devices, articles, etc. included in this description is made solely for the purpose of providing context for the present invention. It is not intended that all or any of these materials form part of the prior art or were generally known in the art to which the present invention pertains because they were otherwise known prior to the priority date of this application.

The numerical values given in the description and the claims mentioned above, although they may form an important part of the present invention according to the present disclosure, any deviation from such numerical values will still be within the scope of the present invention if this deviation follows the same scientific principle as in the present invention disclosed in the present disclosure.

The term "pest" for the purposes of the present invention includes, without limitation, fungi, stramenopiles (oomycetes), bacteria, nematodes, mites, ticks, insects and rodents.

The term "plant" in this document refers to all plants and plant populations, such as desirable and undesirable wild plants or cultivated plants (including naturally occurring crop plants). Crops may be plants that may be obtained by conventional breeding and optimization techniques or by biotechnology and genetic engineering techniques or combinations of these techniques, including transgenic plants and including plant cultivars that are and are not protected by plant breeders' rights.

For the purposes of the present invention, the term "plant" includes a living organism, exemplified by trees, shrubs, herbs, grasses, ferns and mosses, commonly growing in a site, absorbing water and essential substances through its roots and synthesizing nutrients in its leaves by photosynthesis.

Examples of "plants" for the purpose of the present invention include, but are not limited to, agricultural crops such as wheat, rye, barley, triticale, oats or rice; beets, such as sugar beets or fodder beets; fruits and fruit trees, such as pome fruits, stone fruits or berries, such as apples, pears, plums, peaches, almonds, cherries, strawberries, raspberries, blackberries or gooseberries; leguminous plants, such as lentils, peas, alfalfa or soybeans; oilseed crops, such as rapeseed, mustard, olives, sunflowers, coconut, cocoa beans, castor oil plants, oil palms, groundnuts or soybeans; cucurbits, such as squash, cucumbers or melons; plant fibers, such as cotton, flax, hemp or jute; Citrus fruits and citrus trees, such as oranges, lemons, grapefruits or tangerines; any garden plants, vegetables such as spinach, lettuce, asparagus, cabbage varieties, carrot varieties, onion varieties, tomato varieties, potato varieties, pumpkin varieties or paprika; laurel plants such as avocado, cinnamon or camphor; cucurbits; oil plants; energy and raw material plants such as cereals, corn, soybeans, other leguminous plants, canola, sugarcane or oil palm; tobacco; nuts; coffee plant; tea plant; cocoa tree; banana trees; pepper varieties; climbing plants (table grapes and grape vines for grape juice); hops; turf; sweet leaf (also called stevia); natural rubber plants or ornamental and forestry plants such as flowers, shrubs, broad-leaved trees or evergreens such as conifers; and plant propagation material such as seeds and grown material of these plants.

Preferred plants for the purposes of the present invention include, but are not limited to, cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, grapes, nuts and nut trees, citrus and citrus trees, any garden plants, cucurbits, oil plants, tobacco, coffee plant, tea plant, cocoa tree, sugar beet, sugar cane, cotton, potato, tomato, onion species, pepper species and vegetables, ornamental plants, any floricultural plants and other plants for human and animal use.

The term "plant parts" means all parts and organs of plants above and below ground. For the purposes of the present invention, the term "plant parts" includes, but is not limited to, cuttings, leaves, branches, tubers, flowers, seeds, twigs, roots including taproots, lateral roots, root hairs, root tip, root cap, rhizomes, stems, shoots, fruits, fruiting bodies, bark, stalk, buds, accessory buds, meristems, nodes and internodes.

The term "growing place" includes the soil, the surrounding area of the plant or its parts, and the equipment or tools used before, during or after sowing/planting the plant or plant part.

The use of the compounds of the present invention or a compound of the present invention in a composition optionally containing other compatible compounds, in relation to a plant or plant material or its locus includes application by a method known to a person skilled in the art, which includes, but is not limited to, spraying, coating, dipping, fumigation, impregnation, injection and dusting.

The term "applied" means adhesion to a plant or plant part, either physically or chemically, including by impregnation.

In view of the above, the present invention provides a compound of general formula (I),

Where

R ¹ is selected from the group consisting of hydrogen, cyano, C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ alkynyl, C ₁ -C ₁₂ haloalkyl, C ₁ -C ₁₂ alkoxy, C ₃ -C ₈ cycloalkyl and C ₄ -C ₈ cycloalkylalkyl; wherein one or more carbon atoms in the cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S);

R ² is selected from the group consisting of C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ alkynyl, C ₁ -C ₁₂ haloalkyl, (C=O)-R″ and C ₃ -C ₈ cycloalkyl; wherein one or more carbon atoms in the cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S); or

R ¹ and R ² together with the atoms to which they are attached or together with additional atoms selected from the group consisting of C, N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S), may form a three- to seven-membered non-aromatic ring which, in turn, may be substituted with one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′) ₂ , COOR′ and CON(R′) ₂ ;

each R ¹ and R ² group may optionally be substituted with one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′) ₂ , COOR′ and CON(R′) ₂ ;

R ³ is selected from the group consisting of X, cyano, C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ alkynyl, C ₁ -C ₁₂ haloalkyl, N(R′R′′′), OR′′, S(O) _n R′′′, (C=O)-R″ and C ₃ -C ₈ cycloalkyl; wherein one or more carbon atoms in the cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S);

R ⁴ is selected from the group consisting of X, cyano, C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ alkynyl, C ₁ -C ₁₂ haloalkyl, N(R′R′′′), OR″, S(O) _n R′′′, (C=O)-R″, C ₃ -C ₈ cycloalkyl and C ₇ -C ₁₂ aralkyl; wherein one or more carbon atoms in the cyclic ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S).

R ^4a and R ^4b are independently selected from the group consisting of hydrogen, X, cyano, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ haloalkyl, OR″, S(O) _n R′ and C ₃ -C ₅ cycloalkyl;

each R ³ and R ⁴ group may optionally be substituted with one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′) ₂ , COOR′ and CON(R′) ₂ ;

A is - { [C(R ⁶ R ⁷ )] _0-2 -(B) _0-1 }-, - { [BC(R ⁶ R ⁷ )] _0-1 -C(=Y)}-; where B is O, S, NR ⁵ or CR ⁶ R ⁷ ; and Y is O or S;

R ⁵ is selected from the group consisting of hydrogen, C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, C ₁ -C ₈ haloalkyl, S(O) _n R′′′, OR′′, NR′R″, (C=O)-R″ and C ₃ -C ₈ cycloalkyl; wherein one or more carbon atoms in the cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O), C(=S);

R ⁶ and R ⁷ are independently selected from the group consisting of hydrogen, X, cyano, C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, C ₁ -C ₈ haloalkyl, N(R″) ₂ , OR′′, (C=O)-R″ and C ₃ -C ₈ cycloalkyl; wherein one or more carbon atoms in the cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S); or

R ⁶ and R ⁷ together with the atom to which they are attached or together with additional atoms selected from the group consisting of C, N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S), may form a three- to six-membered ring which, in turn, may be substituted with one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′) ₂ , COOR′ and CON(R′) ₂ ;

each R ⁵ , R ⁶ and R ⁷ group may optionally be substituted with one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′) ₂ , COOR′ and CON(R′) ₂ ;

ring E is selected from the group consisting of fused or unfused _C3 - _C18 carbocyclyl and _C3 - _C18 heterocyclyl, which may optionally be substituted with one or more ^R8 groups;

R ⁸ is selected from the group consisting of hydrogen, X, cyano, nitro, C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ alkynyl, C ₁ -C ₁₂ haloalkyl, C ₂ -C ₁₂ haloalkenyl, C ₂ -C ₁₂ haloalkynyl, C ₃ -C ₈ cycloalkyl, C ₄ -C ₈ cycloalkenyl, C ₄ -C ₈ cycloalkynyl, C ₇ -C ₁₉ aralkyl, C ₅ -C ₁₂ bicycloalkyl, C ₆ -C ₁₀ aryl, C ₃ -C ₆ heterocyclyl, SCN, SF ₅ , N(R′R′′′), OR′′, S(O) _n R′′′, (C=O)-R′′′, C1 _{- C8} alkyl-S(O) _nR ″, _C1 - _C8 alkyl-(C=O)-R″, CR′=NR″, -S( ^R9 )=N( ^R10 ), -S( ^R9 )(O)=N( ^R10 ), S( ^R9 ) ₂ =N-, S( ^R9 ) ₂ (O)=N- and S( ^R9 ) ₂ (O)=NC( ^R6aR7a )-; wherein one or more carbon atoms in the cyclic ring may be replaced by heteroatoms selected from ^the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S);

R ^6a and R ^7a are independently selected from the group consisting of hydrogen, X, cyano, C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, C ₁ -C ₈ haloalkyl, C ₂ -C ₈ haloalkenyl, (NR″) ₂ , OR″, S(O) _n R′′′, (C=O)-R″ and C ₃ -C ₈ cycloalkyl; or

R ^6a and R ^7a together with the atom to which they are attached or together with additional atoms selected from the group consisting of C, N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S), may form a three- to six-membered ring which, in turn, may be substituted with one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′) ₂ , COOR′ and CON(R′) ₂ ; or

R ^6a and R ^7a together with the atom to which they are attached can form a =O or =S group;

R ⁹ is independently selected from the group consisting of C ₁ -C ₈ alkyl and C ₃ -C ₈ cycloalkyl;

R ¹⁰ is selected from the group consisting of hydrogen, cyano, C ₁ -C ₈ alkyl, C ₂ -C ₈ alkenyl, C ₂ -C ₈ alkynyl, (C=O)-R′′, S(O) _n R′″ and C ₃ -C ₈ cycloalkyl; or

R ⁹ and R ¹⁰ together with the atom to which they are attached or together with additional atoms selected from the group consisting of C, N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S), may form a three- to seven-membered ring which, in turn, may be substituted with one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′) ₂ , COOR′ and CON(R′) ₂ ; or

R ⁸ and R ⁹ or R ¹⁰ together with the atom to which they are attached or together with additional atoms selected from the group consisting of C, N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S), may form a three- to seven-membered ring which, in turn, may be substituted with one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′) ₂ , COOR′ and CON(R′) ₂ ;

R ⁵ , or R ⁶ , or R ⁷ and R ⁸ , or two R ⁸ together with the atom to which they are attached or together with additional atoms selected from the group consisting of C, N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S), can form a three- to ten-membered ring which, in turn, can be substituted with one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′) ₂ , COOR′ and CON(R′) ₂ ;

each R ⁸ , R ⁹ or R ¹⁰ group may optionally be substituted with one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′R″), COOR′ and CON(R′R″);

X represents halogen;

R′ is selected from the group consisting of hydrogen, _C1 - _C8 alkyl and _C3 - _C8 cycloalkyl; wherein the alkyl and cycloalkyl groups may optionally be substituted with one or more X;

R″ is selected from the group consisting of hydrogen, _C1 - _C8 alkyl, _C1 - _C8 haloalkyl, _C3 - _C8 cycloalkyl, N(R′) ₂ , OR′ and _C6 - _C18 aryl; wherein one or more carbon atoms in the cyclic ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S);

R′′′ is selected from the group consisting of cyano, R″, _C2 - _C8 alkenyl, _C2 - _C8 alkynyl, _C3 - _C8 cycloalkyl, _C4 - _C8 cycloalkenyl, _C4 - _C8 cycloalkynyl, OR′, (C=O)-R′, COOR′, CON(R′) ₂ , _C6 - _C18 aryl and _C7 - _C19 aralkyl; wherein one or more carbon atoms in the cyclic ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S);

each R″ and R′″ group may be substituted by one or more groups selected from the group consisting of X, CN, R′, OR′, SR′, N(R′) ₂ , COOR′ and CON(R′) ₂ ;

n is an integer 0, 1, or 2;

m is an integer 0, 1, or 2;

or its agriculturally acceptable salts, isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, polymorphs, metal complexes or N-oxides;

provided that the following compounds are excluded from the definition of a compound of formula (I); N'-(2-cyano-3-((3,3-difluoro-1-methylpiperidin-4-yl)oxy)-5-methoxyphenyl)-N,N-dimethylformimidamide and N'-(5-bromo-2-cyano-3-((2,4-dimethoxybenzyl)oxy)phenyl)-N,N-dimethylformimidamide.

In another embodiment, the present invention provides a compound of formula (Ia),

where R ¹ , R ² , R ³ , R ⁴ , R ^4a , R ^4b , R ⁶ , R ⁷ , R ⁷ and E are defined above.

In another embodiment, the present invention provides a compound of formula (Ib and Ic),

where R ¹ , R ² , R ³ , R ⁴ , R ^4a , R ^4b , R ⁵ , R ⁶ , R ⁷ and E are defined above.

In another embodiment, the present invention provides a compound of formula (Id and Ie),

where R ¹ , R ² , R ³ , R ⁴ , R ^4a , R ^4b , A and E are defined above.

In another embodiment, the present invention provides a compound of formula (If and Ig),

where R ¹ , R ² , R ³ , R ⁴ , R ^4a , R ^4b , R ⁶ , R ⁷ , B and E are defined above.

In a preferred embodiment of the present invention, the present invention provides a compound of formula (I), wherein

R ¹ is selected from the group consisting of C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₁ -C ₆ alkoxy, C ₃ -C ₅ cycloalkyl and C ₄ -C ₈ cycloalkylalkyl;

R ² is selected from the group consisting of C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₃ -C ₈ cycloalkyl and C ₁ -C ₆ haloalkyl;

R ³ and R ⁴ are independently selected from the group consisting of X, cyano, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, N(R′R′′′), OR′′, S(O) _n R′′′, (C=O)-R″ and C ₃ -C ₈ cycloalkyl;

R ⁵ is selected from the group consisting of hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₈ cycloalkyl and OR′;

R ⁶ and R ⁷ are independently selected from the group consisting of hydrogen, X, cyano, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ haloalkyl and C ₃ -C ₄ cycloalkyl; wherein one or more carbon atoms in the cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) or C(=S);

ring E is selected from the group consisting of fused or non-fused _C3 - _C10 carbocyclyl and _C5 - _C10 heterocyclyl, which may optionally be substituted with one or more ^R8 groups;

or its agriculturally acceptable salts, isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs or N-oxides.

In a more preferred embodiment of the present invention, the present invention provides a compound of formula (I), wherein

R ¹ and R ² are independently selected from the group consisting of C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₃ -C ₅ cycloalkyl and C ₄ -C ₈ cycloalkylalkyl;

R ³ and R ⁴ are independently selected from the group consisting of X, cyano, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₅ cycloalkyl and OR′′;

R ⁵ is selected from the group consisting of hydrogen, C ₁ -C ₆ alkyl, C ₂ -C ₆ alkenyl, C ₂ -C ₆ alkynyl, C ₁ -C ₆ haloalkyl, C ₃ -C ₅ cycloalkyl and OR′;

R ⁶ and R ⁷ are independently selected from the group consisting of hydrogen, X, cyano, C ₁ -C ₄ alkyl, C ₂ -C ₄ alkenyl, C ₂ -C ₄ alkynyl, C ₁ -C ₄ haloalkyl, OR′′ and C ₃ -C ₅ cycloalkyl;

ring E is selected from cyclopropyl, cyclobutyl, phenyl, naphthalenyl, furyl, thienyl, pyrrolyl, isoxazolyl, thiazolyl, isothiazolyl, thiadiazolyl, pyrazolyl, oxazolyl, imidazolyl, oxadiazolyl, triazolyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl, triazinyl, indolyl, benzimidazolyl, indazolyl, benzofuranyl, benzothiophenyl, benzothiazolyl, benzoxazolyl, quinolinyl, isoquinolinyl, quinazolinyl, cinnonyl, indolizinyl, pyrazolo[1,5-a]pyridinyl, imidazo[1,2-a]pyridinyl, pyrrolo[1,2-a]pyrimidinyl, pyrazolo[1,5-a]pyrimidinyl, imidazo[1,2-a]pyrimidinyl, pyrrolo[1,2-a]pyrazinyl, pyrazolo[1,5-a]pyrazinyl, imidazo[1,2-a]pyrazinyl, wherein each substituent E is optionally substituted with one or more R ⁸ ;

or its agriculturally acceptable salts, isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs or N-oxides.

In a preferred embodiment, the compound of formula (I) is selected from the group consisting of N'-(2-chloro-5-methyl-3-(p-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2,5-dimethyl-3-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(2,5-dimethyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(3-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-((2-fluorophenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-((2-fluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(phenylamino)phenyl)-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(phenylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(phenyl)amino)phenyl)-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(2-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(o-tolylamino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((4-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluorophenyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(3-((4-(tert-butyl)phenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(o-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((4-(tert-butyl)phenyl)amino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((4-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluorophenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-methoxyphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(m-tolylamino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluorophenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(3-((3-chlorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(m-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3-chlorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(m-tolyl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((3-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chlorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(m-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(2-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(4-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-chloro-4-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3,5-dimethylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-chloro-2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(5-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-isopropylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-chlorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-chlorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-isopropylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(pyridin-3-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3,4-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluoro-3-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3,5-difluoro-4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3,4-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3,4-difluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3,5-difluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2,4-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((2,4-difluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3,5-difluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3,5-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-benzyl-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((2,4-difluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3,4-difluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2,4-difluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3,4-difluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3,5-difluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(pyridin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((3-methylpyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-fluoro-3,5-dimethylbenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(2-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(2,6-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(2-chloro-6-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(pyridin-2-ylamino)phenyl)-N-methylformimidamide, N'-(3-((3-chloro-5-fluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chloro-5-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((5-chloro-2-methylphenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chloro-5-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((5-chloro-2-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(2-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(2-cyanobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3-chloro-5-fluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(3-methylpyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(2-chloro-3-((5-chloro-2-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-fluoro-5-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((5-chloro-3-methylpyridin-2-yl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((2-chloro-5-methylphenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluoro-5-methylphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-chloro-5-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((5-chloro-2-methylphenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((2-chloro-5-methylphenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((5-chloro-3-methylpyridin-2-yl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluoro-5-methylphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-chloro-5-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluoro-6-methylphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluoro-3-methylphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-fluoro-3-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromobenzyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-fluoro-3-methylbenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3,4-difluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3-chloro-4-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-chloro-3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((3-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-fluoro-6-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-chloro-2-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((3-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((4-chloro-2-fluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2-fluoro-6-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2-fluoro-3-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((4-chloro-2-fluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(2-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(2-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(2-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(3-(3-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluoro-6-methylphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3-methylbenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(3-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(2-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-benzyl-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluoro-3-methylphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(3-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(m-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(phenylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-chloro-2-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(3-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chloro-5-(trifluoromethyl)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(m-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((4-methoxyphenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-chlorophenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3-bromophenyl)amino)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((2-fluorophenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-fluorophenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((4-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-cyanobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-(4-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N'-(3-(3-cyanobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-(difluoromethoxy)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((2-fluorophenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-fluorophenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-chlorophenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((2-(trifluoromethyl)benzyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((4-fluoro-3-methylbenzyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(5-chloro-3-((3-chlorobenzyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(o-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(pyrimidin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(pyrimidin-2-ylamino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(2-bromo-3-(3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(3-fluorobenzyl)-5-methyl-2-(methylthio)phenyl)-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(o-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(pyrimidin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(pyrazin-2-ylamino)phenyl)-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(pyrazin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((1-(pyrazin-2-yl)propan-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(((5-methylpyrazin-2-yl)methyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((1-(pyrazin-2-yl)propan-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(((5-methylpyrazin-2-yl)methyl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(pyrazin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(pyrimidin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(3-(4-cyanobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(4-fluoro-3-methylbenzyl)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(4-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(3-bromobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-chloro-3-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-benzyl-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(2,5-dimethyl-3-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-bromo-5-methyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(pyrazin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(pyrazin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(pyrimidin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(pyrazin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(pyrimidin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromo-4-fluorobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromo-3-methylbenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromo-2-fluorobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide, N'-(3-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(4-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide, N'-(3-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(benzo[d]thiazol-6-ylamino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((6-ethylpyridin-2-yl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-((6-ethylpyridin-2-yl)amino)-5-fluoro-2-methylphenyl)-N-methylformimidamide, N'-(3-(benzo[d]thiazol-6-ylamino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-chloro-5-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromo-4-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(5-fluoro-2-methylbenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(4-bromo-3-methylbenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromo-5-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(3-fluoro-5-methylbenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(4-bromo-2-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(3-fluoro-5-methoxybenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(benzo[d]thiazol-6-yl(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-((6-ethylpyridin-2-yl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-methylformimidamide, N'-(3-(benzo[d]thiazol-6-yl(methyl)amino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4-(methylthio)benzyl)phenyl)-N-methylformimidamide, N'-(3-(benzo[d]thiazol-6-ylamino)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((6-ethylpyridin-2-yl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-(3-bromobenzyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-cyanobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(pyridin-3-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3-cyanobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((6-ethylpyridin-2-yl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluoro-4-methoxyphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((3-fluoro-4-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-fluoro-4-methoxyphenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluoro-4-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((3-fluoro-4-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3-nitrobenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(pyridin-3-ylmethyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(3-(4-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(2-methylbenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(4-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-(3-chlorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-chlorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(2-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N'-(5-chloro-3-((3-fluoro-4-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-3-((2-methoxyphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-((3-fluoro-4-methoxyphenyl)amino)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-3-((2-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-((3-fluoro-4-methoxyphenyl)(methyl)amino)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(5-chloro-2-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-fluoro-3-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-((4-fluoro-3-methoxyphenyl)amino)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-(3-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(3-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-(4-chlorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(3-nitrobenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(3-(5-fluoro-2-methylbenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N'-(3-(3-chloro-4-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-((4-fluoro-3-methoxyphenyl)(methyl)amino)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(3-(3,4-difluorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-fluoro-3-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(3-(3-fluoro-5-methylbenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N'-(3-(2-chloro-5-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(4-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(5-cyano-3-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-benzyl-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-methylformimidamide, N'-(5-chloro-2-methyl-3-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-methylformimidamide, N'-(3-(2-(2-chloro-4-methoxyphenoxy)acetyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N'-(3-(3-cyanobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(2-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(3-benzyl-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-cyano-3-(3-cyanobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-cyano-3-(4-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-chlorobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-cyano-2-methyl-3-(3-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-(3-bromobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide and N'-(5-cyano-2-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide.

Any of the compounds according to the present invention may exist in one or more optical, geometrical or chiral isomeric forms depending on the number of asymmetric centers in the compound. The present invention therefore relates equally to all optical isomers and to their racemic or scalemic mixtures (the term "scalemic" means a mixture of enantiomers in different ratios), and to mixtures of all possible stereoisomers in all ratios. Diastereomers and/or optical isomers can be separated according to methods that are known per se to a person of ordinary skill in the art.

Any of the compounds according to the present invention may also exist in one or more geometric isomeric forms depending on the number of double bonds in the compound. The present invention therefore applies equally to all geometric isomers and to all possible mixtures in all proportions. Geometric isomers can be separated according to general methods that are known per se to a person of ordinary skill in the art.

Any of the compounds according to the present invention may also exist in one or more amorphous or isomorphous or polymorphous forms, depending on their preparation, purification, storage and various other influencing factors. The present invention thus relates to all possible amorphous, isomorphous and polymorphous forms in all ratios. The amorphous, isomorphous and polymorphous forms can be prepared and/or separated and/or purified according to general methods that are known per se to a person of ordinary skill in the art.

In one embodiment, the present invention provides a compound of formula (A);

Where

Z represents OH, _NH2 , SH, X, or a leaving group;

R ¹ is selected from the group consisting of C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ alkynyl, C ₁ -C ₁₂ haloalkyl and C ₃ -C ₈ cycloalkyl;

R ² is selected from the group consisting of cyano, C ₂ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ alkynyl, C ₁ -C ₁₂ haloalkyl, (C=O)-R″, C ₃ -C ₈ cycloalkyl and C ₃ -C ₈ cycloalkyl-C ₁ -C ₃ alkyl;

R ³ is selected from the group consisting of X, cyano, C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ alkynyl, C ₁ -C ₁₂ haloalkyl, N(R′R′′′), OR′′, S(O) _n R′′′, (C=O)-R″ and C ₃ -C ₈ cycloalkyl; wherein one or more carbon atoms in the cycloalkyl ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) and C(=S);

R ⁴ is selected from the group consisting of X, cyano, C ₁ -C ₁₂ alkyl, C ₂ -C ₁₂ alkenyl, C ₂ -C ₁₂ alkynyl, C ₁ -C ₁₂ haloalkyl, N(R′R′′′), OR″, S(O) _n R′′′, (C=O)-R″, C ₃ -C ₈ cycloalkyl and C ₇ -C ₁₂ aralkyl; wherein one or more carbon atoms in the cyclic ring may be replaced by heteroatoms selected from the group consisting of N, O, S(O) _m , and optionally including 1-3 ring members selected from the group consisting of C(=O) and C(=S).

In one embodiment, the present invention provides a compound of formula (B);

where R ³ , R ⁴ , R ^4a , R ^4b , A and E are defined above.

In a preferred embodiment, the compound of formula (B) is selected from 2-chloro-5-methyl-N ¹ -(p-tolyl)benzene-1,3-diamine, 2,5-dimethyl-3-(4-methylbenzyl)aniline, 3-(3-chlorobenzyl)-2,5-dimethylaniline, 2,5-dimethyl-3-(2-methylbenzyl)aniline, 3-(3-fluorobenzyl)-2,5-dimethylaniline, N ¹ -(2-fluorophenyl)-2,5-dimethylbenzene-1,3-diamine, N ¹ -(2-fluorophenyl)-N ¹ ,2,5-trimethylbenzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -phenylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -phenylbenzene-1,3-diamine, 2-chloro-N ¹ ,5-dimethyl-N ¹ -phenylbenzene-1,3-diamine, 5-fluoro-N ¹ ,2-dimethyl-N ¹ -phenylbenzene-1,3-diamine, 2-chloro-5-methyl-3-(2-methylbenzyl)aniline, 2-chloro-3-(2-chlorobenzyl)-5-methylaniline, 2-chloro-3-(2-fluorobenzyl)-5-methylaniline, 5-fluoro-2-methyl-N ¹ -(o-tolyl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(4-((trifluoromethyl)thio)phenyl)benzene-1,3-diamine, 2-chloro-5-methyl-3-(3-methylbenzyl)aniline, 2-chloro-5-methyl-3-(4-methylbenzyl)aniline, 5-fluoro-N ¹ -(2-fluorophenyl)-2-methylbenzene-1,3-diamine, N ¹ -(4-(tert-butyl)phenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-5-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 2-chloro-3-(3-fluorobenzyl)-5-methylaniline, chloro-N ¹ -(2-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(o-tolyl)benzene-1,3-diamine, N ¹ -(4-(tert-butyl)phenyl)-2-chloro-5-methylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(4-((trifluoromethyl)thio)phenyl)benzene-1,3-diamine, 2-chloro-3-(3-chlorobenzyl)-5-methylaniline, 2-chloro-3-(3-methoxybenzyl)-5-methylaniline, 5-fluoro-N ¹ -(3-fluorophenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-N ¹ -(3-methoxyphenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(m-tolyl)benzene-1,3-diamine, 5-fluoro-N ¹ -(3-fluorophenyl)-N ¹ ,2-dimethylbenzene-1,3-diamine, N ¹ -(3-chlorophenyl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-chlorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(m-tolyl)benzene-1,3-diamine, N ¹ -(3-chlorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 5-fluoro-N ¹ ,2-dimethyl-N ¹ -(m-tolyl)benzene-1,3-diamine, 5-fluoro-N ¹ -(3-methoxyphenyl)-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-fluorophenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-chlorophenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-methoxyphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ ,5-dimethyl-N ¹ -(m-tolyl)benzene-1,3-diamine, 2-chloro-3-(4-fluorobenzyl)-5-methylaniline, 3-(2-bromobenzyl)-2 -chloro-5-methylaniline, 4-(3-amino-2-chloro-5-methylbenzyl)benzonitrile, 2-(3-amino-2-chloro-5-methylbenzyl)benzonitrile, 3-(3-amino-2-chloro-5-methylbenzyl)benzonitrile, 2-chloro-N ¹ -(3-methoxyphenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 2-chloro-5-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 2-chloro-5-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 2-chloro-5-methyl-3-(4-(trifluoromethoxy)benzyl)aniline, 2-chloro-5-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 2-chloro-3-(3-chloro-4-fluorobenzyl)-5-methylaniline, 2-chloro-3-(3,5-dimethylbenzyl)-5-methylaniline, 2-chloro-3-(3-chloro-2-fluorobenzyl)-5-methylaniline, 2-chloro-3-(5-fluoro-2-methylbenzyl)-5-methylaniline, 2-chloro-N ¹ -(3-isopropylphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(4-chlorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(4-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(4-methoxyphenyl) ^-5 -methylbenzene- ^1,3 -diamine , 2-chloro-N ¹ -(4-chlorophenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 2-chloro-N ^{1 -(3-isopropylphenyl)-N 1,5-dimethylbenzene-1,3-diamine, 2-chloro-N 1} -(4-methoxyphenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 2-chloro-3-(4-fluoro-2-methylbenzyl)-5-methylaniline, 2-chloro-5-methyl-3-(pyridin-3-ylmethyl)aniline, 2-chloro-3-(3,4-difluorobenzyl)-5-methylaniline, 2-chloro-3-(4-fluoro-3-methylbenzyl)-5-methylaniline, 2-chloro-N ¹ -(4-fluorophenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 3-benzyl-2-chloro-5-methylaniline, 2-chloro-3-(3,5-difluoro-4-methoxybenzyl)-5-methylaniline, 2-chloro-N ¹ -(3,4-difluorophenyl)-5-methylbenzene-1,3-diamine, N ¹ -(3,4-difluorophenyl) ^-5 -fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(3,5-difluorophenyl)-N 1,5-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(2,4-difluorophenyl)-5-methylbenzene-1,3-diamine, N ¹ -(2,4-difluorophen yl)-5-fluoro-2-methylbenzene-1,3-diamine, N ¹ -(3,5-difluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(3,5-difluorophenyl)-5-methylbenzene-1,3-diamine, 3-benzyl-5-chloro-2-methylaniline, N ¹ -(2,4-difluorophenyl )-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3,4-difluorophenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(2,4-difluorophenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, N ¹ -(3,4-difluorophenyl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, N ¹ -(3,5-difluorophenyl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(pyridin-2-yl)benzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(3-methylpyridin-2-yl)benzene-1,3-diamine, 5-chloro-3-(4-fluoro-3,5-dimethylbenzyl)-2-methylaniline, 5-chloro-2-methyl-3-(2-methylbenzyl)aniline, 5-chloro-3-(2-chlorobenzyl)-2-methylaniline, 3-(2-bromobenzyl)-5-chloro-2-methylaniline, 2-chloro-3-(2,6-difluorobenzyl)-5-methylaniline, 2-chloro-3-(2-chloro-6-fluorobenzyl)-5-methylaniline, 3-(4-bromobenzyl)-2-chloro-5-methylaniline, 5-chloro-2-methyl-3-(3-methylbenzyl)aniline, 5-fluoro-2-methyl-N ¹ -(pyridin-2-yl)benzene-1,3-diamine, N ¹ -(3-chloro-5-fluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-chloro-5-fluorophenyl)-5-methylbenzene-1,3-diamine, N ¹ -( ⁵ -chloro-2-methylphenyl)-5-fluoro-N 1,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-chloro-5-fluorophenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(5-chloro-2-methylphenyl)-5-methylbenzene-1,3-diamine, 5-chloro-3-(3-chlorobenzyl)-2-methylaniline, 5-chloro-3-(3-fluorobenzyl)-2-methylaniline, 5-chloro-3-(2-fluorobenzyl)-2-methylaniline, 2-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(4-methylbenzyl)aniline, N ¹ -(3-chloro-5-fluorophenyl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ ,5-dimethyl-N ¹ -(pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ¹ ,5-dimethyl-N ¹ -(3-methylpyridin-2-yl)benzene-1,3-diamine, 5-fluoro-N ¹ ,2-dimethyl-N ¹ -(pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ¹ -(5-chloro-2-methylphenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-fluoro-5-methylphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(5-chloro-3-methylpyridin-2-yl)-5-methylbenzene-1,3-diamine, N ¹ -(2-chloro- 5-methylphenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 5-fluoro-N ¹ -(3-fluoro-5-methylphenyl)-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(2-chloro-5-methylphenyl)-5-methylbenzene-1,3-diamine, N ¹ -(5-chloro-2-methylphenyl)-5-fluoro-2-methylbenzene-1,3-diamine, N ¹ -(2-chloro-5-methylphenyl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(5-chloro-3-methylpyridin-2-yl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 5-fluoro-N ¹ -(3-fluoro-5-methylphenyl)-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(2-chloro-5-methylphenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 5-fluoro-N ¹ -(2-fluoro-6-methylphenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-N ¹ -(2-fluoro-3-methylphenyl)-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(2-fluoro-3-methylphenyl)-5-methylbenzene-1,3-diamine, 5-chloro-3-(4-fluorobenzyl)-2-methylaniline, 3-(4-bromobenzyl)-5-chloro-2-methylaniline, 5-chloro-3-(4-chlorobenzyl)-2-methylaniline, 5-chloro-2-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 5-chloro-3-(4-fluoro-3-methylbenzyl)-2-methylaniline, 5-chloro-3-(3,4-difluorobenzyl)-2-methylaniline, 5-chloro-3-(3-chloro-4-fluorobenzyl)-2-methylaniline, 5-chloro-3-(4-chloro-3-fluorobenzyl)-2-methylaniline, 5-fluoro-2-methyl-N ¹ -(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ¹ -(2-fluoro-6-methylphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(4-chloro-2-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, N ¹ -(4-chloro-2-fluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-chloro-5-(trifluoromethyl)phenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(2-fluoro-6-methylphenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(2-fluoro-3-methylphenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, N ¹ - (4-chloro-2-fluorophenyl)-5-fluoro-N ^1,2 -dimethylbenzene-1,3-diamine, 5-fluoro-3-(2-fluorobenzyl)-2-methylaniline, 3-(2-chlorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 3-(3-chlorobenzyl)- 5-fluoro-2-methylaniline, 5-fluoro-N ¹ -(2-fluoro-6-methylphenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, 5-fluoro-2-methyl-3-(3-methylbenzyl)aniline, 5-fluoro-3-(3-fluorobenzyl)-2-methylaniline, 5-fluoro-2-methyl-3-(2-methylbenzyl)aniline, 3-benzyl-5-fluoro-2- methylaniline, 2-chloro-3-(4-methoxybenzyl)-5-methylaniline, 3-(2-bromobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-N ¹ -(2-fluoro-3-methylphenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, 5-fluoro-N ^1,2 -dimethyl-N ¹ -(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N ¹ -(m-tolyl)benzene-1,3-diamine, 5-chloro-2-methyl-N ¹ -phenylbenzene-1,3-diamine, 2-chloro-N ¹ -(4-chloro-2-fluorophenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ ,5-dimethyl-N ¹ -(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ¹ -(3-chloro-5-(trifluoromethyl)phenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 5-chloro-N ¹ ,2-dimethyl-N ¹ -phenylbenzene-1,3-diamine, 5-chloro-N ¹ ,2-dimethyl-N ¹ -(m-tolyl)benzene-1,3-diamine, N ¹ -(3-chloro-5-(trifluoromethyl)phenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(4-methoxyphenyl)-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(3-chlorophenyl)-2-methylbenzene-1,3-diamine, N ¹ -(3-bromophenyl)-5-chloro-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(2-fluorophenyl)-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(3-fluorophenyl)-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(4-methoxyphenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, 2-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 2-chloro-N ¹ -(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-methylbenzene-1,3-diamine, 5-fluoro-2 -methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 5-fluoro-2-methyl-3-(4-methylbenzyl)aniline, 3-(4-chlorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(3-(trifluoromethoxy)benzyl)aniline, 3-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 3-(4-bromobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(4-(trifluoromethoxy)benzyl)aniline, 2-chloro-N ¹ -(2-(difluoromethoxy)phenyl)-5-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(2-fluorophenyl)-N ^1,2 -dimethylbenzene-1,3 -diamine, 5-chloro-N ¹ -(3-fluorophenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, 5-chloro-N ¹ -(3-chlorophenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(2-(trifluoromethyl)benzyl)benzene-1,3-diamine, 5-ph torus-N ¹ -(4-fluoro-3-methylbenzyl)-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(3-chlorobenzyl)-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N ^1,5 -dimethylbenzene-1,3-diamine, 5-chloro -2-methyl-N ¹ -(o-tolyl)benzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 2-bromo-3-(3-fluorobenzyl)-5-methylaniline, 3-(3-fluorobenzyl)-5-methyl-2-(methylthio)aniline, 5-chloro-N ¹ ,2-dimethyl-N ¹ -(o-tolyl)benzene-1,3-diamine, 2-chloro-N ¹ ,5-dimethyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl- ^{N 1 -} (pyrazin-2-yl)benzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(1-(pyrazin-2-yl)propan-2-yl)benzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -((5-methylpyrazin-2-yl)methyl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(1-(pyrazin-2-yl)propan-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -((5-methylpyrazin-2-yl)methyl)benzene-1,3-diamine, 5-fluoro-N ¹ ,2-dimethyl -N ¹ -(pyrazin-2-yl)benzene-1,3-diamine, 5-fluoro-N ^1,2 -dimethyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 4-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 5-fluoro-3-(4-fluoro-3-methylbenzyl)-2-methylaniline, 5-fluoro-3-(4-fluorobenzyl)-2-methylaniline, 3-(3-bromobenzyl)-5-fluoro-2-methylaniline, 3-(4-chloro-3-fluorobenzyl)-5-fluoro-2-methylaniline, 3-benzyl-2,5-dimethylaniline, 2,5-dimethyl -3-(3-methylbenzyl)aniline, 2-bromo-5-methyl-3-(2-methylbenzyl)aniline, 2-chloro-N ¹ ,5-dimethyl-N ¹ -(pyrazin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N ¹ -(pyrazin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 5-chloro-N ¹ ,2-dimethyl-N ¹ -(pyrazin-2-yl)benzene-1,3-diamine, 5-chloro-N ¹ ,2-dimethyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 3-(2-bromo-4-fluorobenzyl)-2-chloro-5-methylaniline, 3-(4-bromo-3-methylbenzyl)-2-chloro-5-methylaniline, 3-(4-bromo-2-fluorobenzyl)-2-chloro-5-methylaniline, 2-chloro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-5-methylaniline, 3-(2-fluorobenzyl)-2,5-dimethylaniline, 3-(2-chlorobenzyl)-2,5-dimethylaniline, 3-(2-bromobenzyl)-2,5-dimethylaniline, 3-(4-fluorobenzyl)-2,5-dimethylaniline, 3-(4-bromobenzyl)-2,5-dimethylaniline, 3-(4-chlorobenzyl)-2,5-dimethylaniline, N ¹ -(benzo[d]thiazol-6-yl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(6-ethylpyridin-2-yl)-5-methylbenzene-1,3-diamine, N ¹ -(6-ethylpyridin-2-yl)-5-fluoro-2-methylbenzene-1,3-diamine, N ¹ -(benzo[d]thiazol-6-yl)-2-chloro-5-methylbenzene-1,3-diamine, 3-(2-chloro-5-fluorobenzyl)-5-fluoro-2-methylaniline, 3-(2-bromo-4-fluorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-3-(5-fluoro-2-methylbenzyl)-2-methylaniline, -bromo-3-methylbenzyl)-5-fluoro-2-methylaniline, 3-(2-bromo-5-fluorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-2-methylaniline, 5-fluoro-3-(3-fluoro-5-methylbenzyl)-2-methylaniline, 3-(4-bromo-2-fluorobenzyl) )-5-fluoro-2-methylaniline, 5-fluoro-3-(3-fluoro-5-methoxybenzyl)-2-methylaniline, N ¹ -(benzo[d]thiazol-6-yl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, N ¹ -(6-ethylpyridin-2-yl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, N ¹ -(benzo[d]thiazol-6-yl)-2-chloro-N ¹ ,5-dimethylbenzene-1,3-diamine, 5-fluoro-2-methyl-3-(4-(methylthio)benzyl)aniline, N ¹ -(benzo[d]thiazol-6-yl)-5-chloro-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(6-ethylpyridin-2-yl)-2-methylbenzene-1,3-diamine, 5-chloro-2-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 3-(3-bromobenzyl)-5-chloro-2-methylaniline, 4-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 5-chloro-2-methyl-3-(pyridin-3-ylmethyl)aniline, 5-chloro-2-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 3-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(3-(trifluoromethoxy)benzyl)aniline, 5-chloro-2-methyl-3-(4-(methylthio)benzyl)aniline, 5-chloro-N ¹ -(6-ethylpyridin-2-yl)-N ¹ ,2-dimethylbenzene-1,3-diamine, 5-fluoro-N ¹ -(3-fluoro-4-methoxyphenyl)-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-fluoro-4-methoxyphenyl)-5-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(3-fluoro-4-methoxyphenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-N ¹ -(3-fluoro-4-methoxyphenyl)-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-fluoro-4-methoxyphenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 5-fluoro-2-methyl-3-(3-nitrobenzyl)aniline, 5-fluoro-2-methyl-3-(pyridin-3-ylmethyl)aniline, 3-(4-fluorobenzyl)-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(2-methylbenzyl)aniline, 5-methoxy-2-methyl-3-( 4-methylbenzyl)aniline, 3-(3-chlorobenzyl)-5-methoxy-2-methylaniline, 3-(2-chlorobenzyl)-5-methoxy-2-methylaniline, 3-(2-fluorobenzyl)-5-methoxy-2-methylaniline, 5-chloro-N ¹ -(3-fluoro-4-methoxyphenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, 5 -methoxy-N ¹ -(2-methoxyphenyl)-2-methylbenzene-1,3-diamine, N ¹ -(3-fluoro-4-methoxyphenyl)-5-methoxy-2-methylbenzene-1,3-diamine, 5-methoxy-N ¹ -(2-methoxyphenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, N ¹ -(3-fluoro-4-methoxyphenyl)-5-meth oxy-N ^1,2 -dimethylbenzene-1,3-diamine, 5-methoxy-2-methyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ¹ -(4-fluoro-3-methoxyphenyl)-5-methylbenzene-1,3-diamine, N ¹ -(4-fluoro-3-methoxyphenyl)-5-methoxy-2-methylbenzene-1,3-diamine, 3-(3-fluorobenzyl)-5-methoxy-2- methylaniline, 5-methoxy-2-methyl-3-(3-methylbenzyl)aniline, 3-(4-chlorobenzyl)-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(3-nitrobenzyl)aniline, 3-(5-fluoro-2-methylbenzyl)-5-methoxy-2-methylaniline, 3-(3-chloro-4-fluorobenzyl)-5-methoxy-2-methyl aniline, 2-chloro-5-methyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, N ¹ -(4-fluoro-3-methoxyphenyl)-5-methoxy-N ^1,2 -dimethylbenzene-1,3- ^diamine , 5-methoxy-N 1,2-dimethyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)ben zol-1,3-diamine, 3-(3,4-difluorobenzyl)-5-methoxy-2-methylaniline, 3-(4-bromobenzyl)-5-methoxy-2-methylaniline, 2-chloro-N ¹ -(4-fluoro-3-methoxyphenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 5-chloro-N ^1,2 -dimethyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ^1,5 -dimethyl-N ¹ -(6-(trifluoromethyl) ^{pyridin-2-yl)benzene-1,3-diamine, 5-fluoro-N 1,2-dimethyl-N 1 -} (6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine on, 3-(3-fluoro-5-methylbenzyl)-5-methoxy-2-methylaniline, 3-(2-chloro-5-fluorobenzyl)-5-methoxy-2-methylaniline, 3-(2-bromobenzyl)-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 5-methoxy-2-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 3-amino-5-(3-fluorobenzyl)-4-methylbenzonitrile, 3-benzyl-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 5-methoxy-2-methyl-N ¹ -(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 5-chloro-2-methyl-N ¹ -(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 1-(3-amino-5-fluoro-2-methylphenyl)-2-(2-chloro-4-methoxyphenoxy)ethan-1-one, 5-methoxy-2-methyl-3-(3-(trifluoromethoxy)benzyl)aniline, 3-(3-amino-5-methoxy-2-methylbenzyl)benzonitrile, 5-methoxy-2-methyl-3-(2-(trifluoromethyl)benzyl)aniline , 3-amino-5-benzyl-4-methylbenzonitrile, 3-amino-5-(3-cyanobenzyl)-4-methylbenzonitrile, 3-amino-5-(4-fluorobenzyl)-4-methylbenzonitrile, 3-amino-5-(4-chlorobenzyl)-4-methylbenzonitrile, 3-amino-4-methyl-5-(3-nitrobenzyl)benzonitrile , 3-amino-5-(3-bromobenzyl)-4-methylbenzonitrile and 3-amino-4-methyl-5-(2-(trifluoromethoxy)benzyl)benzonitrile.

There are a large number of suitable known standard methods, such as alkylation, halogenation, acylation, amidation, oximation, oxidation and reduction. The selection of the preparation methods that are suitable depends on the properties (reactivity) of the substituents in the intermediates. Such reactions may conveniently be carried out in a solvent. Such reactions may conveniently be carried out at different temperatures. Such reactions may conveniently be carried out under an inert atmosphere. The reactants may react in the presence of a base.

The reactants can react with each other as such, i.e. without adding a solvent or diluent. In most cases, however, it is advantageous to add an inert solvent or diluent or a mixture thereof. If the reaction is carried out in the presence of a base, bases that are used in excess, such as triethylamine, pyridine, N-methylmorpholine or N,N-diethylaniline, can also act as solvents or diluents. The reaction is advantageously carried out at a temperature in the range from about -80°C to about +140°C, preferably from about -30°C to about +100°C, in many cases in the range from ambient temperature to about +80°C.

A compound of formula (I) can be converted in a manner known per se into another compound of formula (I) by replacing in a standard manner one or more substituents of the starting compound of formula (I) with other substituents according to the present invention. Depending on the choice of reaction conditions and starting materials, which are suitable in each case, it is possible, for example, in one reaction step to replace only one substituent with another substituent according to the present invention, or a plurality of substituents can be replaced with other substituents according to the present invention in the same reaction step. Salts of compounds of formula (I) can be prepared in a manner known per se. Thus, for example, acid addition salts of compounds of formula (I) are prepared by treatment with a suitable acid or a suitable ion exchange reagent, and salts with bases are prepared by treatment with a suitable base or a suitable ion exchange reagent. The salt is selected depending on its stability with respect to the use of the compound, such as stability in agricultural applications or physiological stability. The salts of the compounds of formula (I) can be converted in a standard manner into the free compounds (I), acid addition salts, for example by treatment with a suitable basic compound or a suitable ion exchange reagent, and into salts with bases, for example by treatment with a suitable acid or a suitable ion exchange reagent. The salts of the compounds of formula (I) can be converted in a manner known per se into other salts of the compounds of formula (I), acid addition salts, for example into other acid addition salts, for example by treating a salt of an inorganic acid, such as a hydrochloride, with a suitable metal salt, such as a sodium, barium or silver salt, of an acid, for example silver acetate, in a suitable solvent in which the inorganic salt, which forms, for example, silver chloride, is insoluble and thus precipitates from the reaction mixture.

In one embodiment, the present invention provides a process for preparing compounds of formula (I).

In another embodiment, the present invention provides a process for preparing a 3-substituted phenylamidine compound of formula (I), wherein the process comprises at least one of the following steps (a) to (h):

a) converting a compound of formula (XXVI) or (XXIV) into a compound of formula (XXIII) according to the reaction scheme as shown below:

,

b) reacting the compound of formula (XXIII) with a suitable secondary amine (HNR ¹ R ² ) to obtain the compound of formula (III) according to the reaction scheme as depicted below:

,

c) reacting a compound of formula (III) with a compound of formula (XII), (XVI), (XVII) or (XXXI) to obtain a compound of formula (I) according to the reaction scheme as shown below:

,

d) converting the compound of formula (III) into the compound of formula (II) according to the reaction scheme as shown below:

,

e) reacting the compound of formula (II) with the compound of formula (XXX) to obtain the compound of formula (I) according to the reaction scheme as shown below:

,

f) reacting a compound of formula (XV) with a compound of formula (XII), (XVI), (XVII) or (XXXI) to obtain a compound of formula (XIV) according to the reaction scheme as shown below:

,

g) converting the compound of formula (XIV) into the compound of formula (XIII) according to the reaction scheme as shown below:

,

h) reacting the compound of formula (XIII) with a suitable secondary amine (HNR ¹ R ² ) to obtain the compound of formula (I) according to the reaction scheme as depicted below:

,

where in the above schemes ^R1 , ^R2 , ^R3 , ^R4 , ^R4a , ^R4b , A, X and E have the same meanings as defined above, and M is selected from the group consisting of a lithium derivative, a boronic acid ester, a boronic acid, MgX and ZnX.

The compounds of the present invention, as defined by general formula (I) and/or in Table I, can be prepared in a known manner in various ways, as described in Schemes 1-21.

A. Synthesis derivative C-bridge amidine

In one embodiment according to the present invention, an arylamidine of formula (Ia), wherein R ¹ -R ⁷ are as defined herein, can be prepared using the process described in the following Schemes 1-8.

Scheme 1

The C-bridged amidine of formula (Ia) can be prepared by palladium-catalyzed cross-coupling of the corresponding boronate ester derivatives of formula (II) with suitable aryl halides in the presence of a base such as potassium carbonate or sodium bicarbonate, according to a similar procedure disclosed in prior art WO2018069841, as shown in Scheme 1.

Scheme 2

The boronate ester of the amidine derivative of formula (II) is an important intermediate and can be prepared (Scheme 2) from the corresponding halogenated amidine derivatives of formula (III) using bispinacolatodiborane in the presence of a palladium catalyst followed by the Miyaura borylation method as disclosed in J. Org. Chem. , 1995, 60 , 7508-7510.

The arylamidine of formula (Ia), wherein R ¹ -R ⁷ are defined herein above, can also be prepared stepwise using the method described in the following schemes 3-8.

Scheme 3

The C-bridged amidine of formula (Ia) can be prepared by treating the corresponding aniline derivatives of formula (IV) with N-(dimethoxymethyl)-N-methylethanamine in 1,4-dioxane using a catalytic amount of anhydrous p- toluenesulfonic acid according to a similar procedure as disclosed in US20110130282.

Scheme 4

The aniline derivative of formula (IV) can be obtained by reducing the corresponding intermediate nitro compound of formula (V) using various reduction methods disclosed in the literature, for example, using iron powder in the presence of aqueous ammonium chloride or hydrogenation in the presence of Pd/C, according to a similar procedure disclosed in US2006194801A1.

Scheme 5

A compound of formula (V), wherein R ³ preferably represents an alkyl group; can be prepared by palladium-catalyzed cross-coupling of a corresponding alkyl boronic acid of formula (VI) with a bromine derivative of formula (VII) in the presence of a base, for example potassium carbonate or potassium phosphate, according to a similar procedure as disclosed in US2017355679A1.

Scheme 6

The corresponding halogen derivatives of formula (VII) can be prepared by the Sandmeyer reaction of the corresponding aniline derivatives of formula (VIII) according to a similar procedure disclosed in J. Org. Chem. , 1980, 45, 2570-2575. This approach provides various functionalization possibilities at this position by converting the corresponding amino group to various halogen atoms, nitrile, hydroxy, trifluoromethyl, etc., as disclosed in J. Fluorine Chem., 2001, 107 , 31-34 and Synthesis , 2007, 81-84.

Scheme 7

The C-bridged derivative of formula (VIII) can be prepared from the intermediate boronate ester of formula (IX) followed by a Suzuki coupling reaction with various benzyl bromides, heteroaryl bromides or alkyl bromides in the presence of a palladium catalyst according to a similar procedure disclosed in WO2018069841.

Scheme 8

The boronate ester derivative of formula (IX) can be prepared from the corresponding commercially available bromine derivative of formula (X) using bispinacolatodiborane in the presence of a palladium catalyst according to the Miyaura borylation reaction using a suitable base, as disclosed in WO 2016210234.

B. Synthesis N-bridged derivative amidine formulas (Ib And Ic)

In one embodiment according to the present invention, an arylamidine of formula (Ib), wherein R ¹ -R ⁷ are defined herein above, can be prepared using the process described in the following Schemes 9-10.

Scheme 9

An N-bridged amidine of formula (Ib) can be prepared by N-alkylation of an amidine derivative of formula (XI) in the presence of a suitable base and a suitable alkyl halide, wherein R ⁵ is defined herein above, according to a similar procedure as disclosed in WO2018069842.

Scheme 10

The amidine derivative of formula (XI) is prepared by palladium-catalyzed cross-coupling of the corresponding amine derivatives of formula (XII) in the presence of a suitable base according to the Buchwald-Hartwig coupling reaction as disclosed in J. Med. Chem. , 2012, 55 , 19, 8538-48 and J. Org. Chem. , 2010, 75 , 19, 6477-88.

C. Synthesis O- And S-bridge derivative amidine formulas (Id And Ie)

In one embodiment according to the present invention, an arylamidine of formula (Id and Ie), wherein R ¹ -R ⁷ are defined herein above, can be prepared using the process described in the following Schemes 11-13.

Scheme 11

In one embodiment, the compound of formula (Id and Ie) can be prepared by treating the corresponding aniline derivatives of formula (XIII) with an excess of trimethyl orthoformate using a catalytic amount of p -toluenesulfonic acid (Scheme 11). The resulting intermediate was heated with a secondary amine (HNR ¹ R ² ) in dioxane to obtain the desired amidine derivatives, followed by a similar procedure as disclosed in US20110130282.

Scheme 12

The amine derivative of formula (XIII) is a key intermediate obtained by reducing the intermediate nitro compound of formula (XIV) using iron and an aqueous solution of ammonium chloride or tin(II) chloride in hydrochloric acid in a suitable solvent and at a suitable temperature according to a similar procedure as disclosed in US2006194801A1.

Scheme 13

The nitro compound derivative of formula (XIV) is an important intermediate and can be prepared by coupling a halogen derivative of formula (XV) and the corresponding substituted phenols or thiophenols using a suitable copper(I) reagent and a solvent according to a similar procedure disclosed in WO2018069842.

D. Synthesis united bridge connection With carbonyl derivative amidine type (If)

In one embodiment according to the present invention, a formamidine derivative of formula (If) can be prepared using the process described in the following scheme 14 .

Scheme 14

The amidine derivative of formula (If) is prepared by performing an acylation reaction using metal-halogen exchange of compounds of formula (III) in the presence of suitable lithiated reagents/Grignard reagents followed by treatment with the appropriate ester or Weinreb amide derivatives of formula (XVI) and according to a similar method as disclosed in Angew. Chem. Int. Ed. , 56(43), 13319-13323 and J. Org. Chem. , 67(11), 3585-3594; 2002.

E. Synthesis united bridge connection With carbonylmethyl derivative amidine formulas (Ig)

In one embodiment according to the present invention, an amidine derivative of formula (Ig), wherein R ¹ -R ⁷ are defined herein above, wherein B is O, S, N, can be prepared by the process described in the following scheme 15.

Scheme 15

The amidine derivative of formula (If) is prepared using metal-halogen exchange of compounds of formula (III) in the presence of suitable lithiated reagents/Grignard reagents followed by treatment with the appropriate ester or Weinreb amide derivatives of formula (XVII) according to a similar method as disclosed in Chem. Pharma. Bull. , 2001, 49(2), 173-182, WO 2012029942 and Eur. J. Med. Chem. , 2013, 69, 244-261.

Scheme 16

The key intermediate of formula (XVI) is obtained by alkylation reaction using ethyl bromoacetate with the corresponding phenols, thiophenols and anilines in the presence of a suitable base according to a similar procedure as disclosed in Tet. Lett. , 2012, 53, 15, 2001-2004 and J. Med. Chem. , 2012, 55, 1, 515-527.

In one embodiment according to the present invention, arylamidines of formula (Ig), wherein R ¹ -R ⁷ are defined herein above and B is CR ⁶ R ⁷ , can be prepared by the process described in the following Schemes 17-20.

Scheme 17

The compound of formula (Ig) can be prepared by treating the corresponding aniline derivatives of formula (XIX) with an excess of trimethyl orthoformate using a catalytic amount of p -toluenesulfonic acid (Scheme 17). The resulting intermediate was heated with a secondary amine (HNR ¹ R ² ) in dioxane to obtain the compound of formula (Ig) according to a similar procedure as disclosed in US20110130282.

Scheme 18

The amine derivative of formula (XIX) is a key intermediate obtained by reducing the intermediate nitro compound of formula (XX) using iron and an aqueous solution of ammonium chloride or tin(II) chloride in hydrochloric acid in a suitable solvent and at a suitable temperature according to a similar procedure as disclosed in US2006194801A1.

Scheme 19

The intermediate nitro compound of formula ( XX ) can be prepared by aldol condensation of the intermediate ketone compound of formula ( XXI ) with the corresponding aldehyde/ketone derivatives in the presence of a suitable base, for example, aqueous sodium or potassium hydroxide solution, according to a similar procedure as disclosed in Synthesis , 1980, 8, 647-650.

Scheme 20

The intermediate nitro compound of formula (XXI) can be prepared by nitration of the corresponding commercially available acetophenone according to a similar procedure disclosed in J. Org. Chem. , 1986, 51, 3439-3446.

F. Synthesis derivative 3-bromoamidine formulas (III)

In one embodiment according to the present invention, an important key intermediate of the arylamidine of formula (III), wherein R ¹ -R ⁴ are defined herein above, can be prepared using the process described in the following scheme 21.

Scheme 21

The compound of formula (III) can be prepared by treating the corresponding aniline derivatives of formula (XXIII) with an excess of trimethyl orthoformate using a catalytic amount of p -toluenesulfonic acid (Scheme 21, step e). The resulting intermediate was heated with a secondary amine (HNR ¹ R ² ) in dioxane to obtain the compound of formula (III) according to a similar procedure as disclosed in US20110130282.

The intermediate aniline compound of formula (XXIII) can be prepared by one of the methods as described in Scheme 21.

In one embodiment, the aniline intermediate of formula (XXIII) is prepared from the corresponding substituted 3-bromobenzoic acid of formula (XXIV) by a Curtius rearrangement (Scheme 21, step d) in the presence of diphenylphosphoryl azide followed by treatment with acid according to a similar procedure disclosed in J. Am. Chem. Soc., 2005, 127, 16408 and Org. Lett., 2012, 14, 608-611. The 3-bromobenzoic acid intermediate of formula (XXIV) can be prepared by bromination (Scheme 21, step b'') of a commercially available 2,5-disubstituted benzoic acid (XXV) followed by the literature method disclosed in J. Org. Chem. , 2013, 78, 2589-2599.

The aniline intermediates of formula (XXIII) are alternatively (Scheme 21, step c) prepared from the intermediate nitro compound of formula (XXVI) by reducing the corresponding nitro function of formula (XXVI) in the presence of a suitable reducing agent, for example iron and aqueous ammonium chloride or tin(II) chloride in hydrochloric acid in a suitable solvent, according to a similar procedure as disclosed in US2006194801 A1 and J. Am. Chem. Soc. , 2003, 125, 40, 12074-12075.

The nitro intermediate of formula (XXVI) can alternatively be prepared from a commercially available nitroaniline intermediate of formula (XXIX) by a Sandmeyer reaction (Scheme 21, step a) followed by radical nucleophilic substitution as disclosed in the literature JOC , 1980, 45, 2570-2575; Synlett , 2012, 23, 13, 1893-1896 and Org Pro Res and Dev , 2003, 7, 5, pp. 762-768.

The intermediate nitro compound of formula (XXVI), wherein the ^R3 / ^R4 group is preferably OH, SH can be alkylated with a suitable alkylating agent (Scheme 21, step b') to give intermediate nitro compounds of formula (XXVII) with a suitable R" group.

The nitro intermediate of formula (XXVI) can alternatively be prepared from a commercially available nitrobenzene intermediate of formula (XXVIII) by a bromination reaction (Scheme 21, step b'') to give a 3-bromo 2,5-disubstituted nitrobenzene derivative, as disclosed in the literature method Chem Comm. 2012, 48, 3442-3444; Bio. Org. Med. Chem 2014, 22, 1156-1162.

In one embodiment, the present invention provides the use of compounds of formula (I) and compositions based thereon for the control and/or prevention of the occurrence of phytopathogenic fungi in agricultural crops and/or horticultural crops.

In another embodiment of the present invention, there is provided the use of compounds of formula (I) and compositions based thereon for the control of rust diseases of agricultural crops and/or horticultural crops.

In a preferred embodiment, the present invention provides the use of a compound of formula (I) and compositions based thereon, which are particularly suitable for controlling and/or preventing diseases of agricultural crops such as cereals, corn, soybeans and other leguminous plants; fruits and fruit trees; nuts and nut trees; citrus and citrus trees; any garden plants; oil plants; coffee plant, tea plant and other vegetables and ornamental plants.

In a more preferred embodiment, the compounds of formula (I) can be used to treat multiple fungal pathogens. Non-limiting examples of fungal pathogens that can be treated according to the present invention include:

diseases caused by powdery mildew pathogens, such as Blumeria species, such as Blumeria graminis ; Podosphaera species, such as Podosphaera leucotricha ; Sphaerotheca species, such as Sphaerotheca fuliginea ; Uncinula species, such as Uncinula necator ; Erysiphe species, such as Erysiphe cichoracearu ;

diseases caused by rust pathogens, such as Gymnosporangium species, such as Gymnosporangium sabinae ; Hemileia species, such as Hemileia vastatrix ; Phakopsora species, such as Phakopsora pachyrhizi or Phakopsora meibomiae ; Puccinia species, such as Puccinia recondita , Puccinia graminis or Puccinia striiformis and Puccinia melanocephala ; Uromyces species, such as Uromyces appendiculatus ;

in particular, Cronartium ribicola (blister rust of white pine); Gymnosporangium juniperi-virginianae (rust of apple and pear); Hemileia vastatrix (coffee rust); Phakopsora meibomiae and P. pachyrhizi (soybean rust); Puccinia coronata (crown rust of oats and ryegrass); Puccinia graminis (stem rust of wheat and bluegrass, or black rust of cereals); Puccinia hemerocallidis (daylily rust); Puccinia persistens subsp. triticina (wheat rust, or "brown or red rust"); Puccinia sorghi (corn rust); Puccinia striiformis ("yellow rust" of cereals); Puccinia melanocephala ; Uromyces appendiculatus (bean rust); Uromyces phaseoli (bean rust); Puccinia melanocephala (sugarcane "brown rust"); Puccinia kuehnii (sugarcane "orange rust").

diseases caused by pathogens from the Oomycetes group, such as speciesAlbugo, For example Albugo candida; typesBremia, For example Bremia lactucae; typesPeronospora, For example Peronospora pisi or P. brassicae; typesPhytophthora, For example Phytophthora infestans; typesPlasmopara, For example Plasmopara viticola; typesPseudoperonospora, For example Pseudoperonospora humuli or Pseudoperonospora cubensis; typesPythium, For example Pythium ultimum;

leaf spot diseases and leaf wilt diseases caused by, for example, Alternaria species, such as Alternaria solani ; Cercospora species, such as Cercospora beticola ; Cladiosporium species, such as Cladiosporium cucumerinum ; Cochliobolus species, such as Cochliobolus sativus (conidial form: Drechslera, syn.: Helminthosporium) or Cochliobolus miyabeanus ; Colletotrichum species, such as Colletotrichum lindemuthanium, Colletotrichum capsici ; Cycloconium species, such as Cycloconium oleaginum ; Diaporthe species, such as Diaporthe citri ; Elsinoe species, such as Elsinoe fawcettii ; Gloeosporium species, such as Gloeosporium laeticolor ; Glomerella spp., such as Glomerella cingulata ; Guignardia spp., such as Guignardia bidwelli ; Leptosphaeria spp., such as Leptosphaeria maculans ; Magnaporthe spp., such as Magnaporthe grisea ; Microdochium spp., such as Microdochium nivale ; Mycosphaerella spp., such as Mycosphaerella graminicola , Mycosphaerella arachidicola or Mycosphaerella fijiensis ; Phaeosphaeria spp., such as Phaeosphaeria nodorum; Pyrenophora spp., such as Pyrenophora teres or Pyrenophora tritici repentis ; Ramularia spp., such as Ramularia collo-cygni or Ramularia areola ; Rhynchosporium spp., such as Rhynchosporium secalis ; Septoria species, such as Septoria apii , Septoria tritici or Septoria lycopersici ; Stagonospora species, such as Stagonospora nodorum ; Typhula species, such as Typhula incarnata ; Venturia species, such as Venturia inaequalis ;

root and stem diseases caused by, for example, Corticium species, such as Corticium graminearum ; Fusarium species, such as Fusarium oxysporum ; Gaeumannomyces species, such as Gaeumannomyces graminis ; Plasmodiophora species, such as Plasmodiophora brassicae ; Rhizoctonia species, such as Rhizoctonia solani ; Sarocladium species, such as Sarocladium oryzae ; Sclerotium species, such as Sclerotium oryzae ; Tapesia species, such as Tapesia acuformis ; Thielaviopsis species, such as Thielaviopsis basicola ; Ganoderma species, such as Ganoderma lucidum ;

ear and panicle diseases (including ears of maize) caused by, for example, Alternaria species, such as Alternaria spp .; Aspergillus species, such as Aspergillus flavus ; Cladosporium species, such as Cladosporium cladosporioides ; Claviceps species, such as Claviceps purpurea ; Fusarium species, such as Fusarium culmorum ; Gibberella species, such as Gibberella zeae ; Monographella species, such as Monographella nivalis ; Stagnospora species, such as Stagnospora nodorum ;

diseases caused by smut fungi, such as Sphacelotheca species, such as Sphacelotheca reiliana ; Tilletia species, such as Tilletia caries or Tilletia controversa ; Urocystis species, such as Urocystis occulta ; Ustilago species, such as Ustilago nuda ;

fruit rot caused by, for example, Aspergillus species, such as Aspergillus flavus ; Botrytis species, such as Botrytis cinerea ; Penicillium species, such as Penicillium expansum or Penicillium purpurogenum ; Rhizopus species, such as Rhizopus stolonifer ; Sclerotinia species, such as Sclerotinia sclerotiorum ; Verticilium species, such as Verticilium alboatrum ;

Seed- and soil-borne rot and wilt diseases and seedling diseases caused by, for example, Alternaria species, such as Alternaria brassicicola ; Aphanomyces species, such as Aphanomyces euteiches ; Ascochyta species, such as Ascochyta lentis ; Aspergillus species, such as Aspergillus flavus ; Cladosporium species, such as Cladosporium herbarum ; Cochliobolus species , such as Cochliobolus sativus (conidial form: Drechslera, syn. Bipolaris: Helminthosporium); Colletotrichum species, such as Colletotrichum coccodes ; Fusarium species, such as Fusarium culmorum ; Gibberella species, such as Gibberella zeae ; Macrophomina species, such as Macrophomina phaseolina ; Microdochium species, such as Microdochium nivale ; Monographella species, such as Monographella nivalis ; Penicillium species, such as Penicillium expansum ; Phoma species, such as Phoma lingam ; Phomopsis species, such as Phomopsis sojae ; Phytophthora species, such as Phytophthora cactorum ; Pyrenophora species, such as Pyrenophora graminea ; Pyricularia species, such as Pyricularia oryzae ; Pythium species, such as Pythium ultimum ; Rhizoctonia species, such as Rhizoctonia solani ; Rhizopus species, such as Rhizopus oryzae ; Sclerotium species, such as Sclerotium rolfsii ; Septoria species, such as Septoria nodorum ; Typhula species, such as Typhula incarnata ; Verticillium species, such as Verticillium dahliae ;

cancers, galls and witches' brooms caused by, for example, Nectria species, such as Nectria galligena ;

wilt diseases caused, for example, by Monilinia species, such as Monilinia laxa ;

deformations of leaves, flowers and fruits caused by, for example, Exobasidium species, such as Exobasidium vexans ; Taphrina species, such as Taphrina deformans ;

degenerative diseases of woody plants caused, for example, by Esca species, such as Phaeomoniella chlamydospora , Phaeoacremonium aleophilum or Fomitiporia mediterranea ; Ganoderma species, such as Ganoderma boninense ;

diseases of flowers and seeds caused, for example, by Botrytis species, such as Botrytis cinerea ;

diseases of plant tubers caused by, for example, Rhizoctonia species, such as Rhizoctonia solani ; Helminthosporium species, such as Helminthosporium solani ;

diseases caused by bacterial pathogens, such as Xanthomonas species, such as Xanthomonas campestris pv. oryzae ; Pseudomonas species, such as Pseudomonas syringae pv. lachrymans ; Erwinia species, such as Erwinia amylovora ; Ralstonia species, such as Ralstonia solanacearum .

Fungal diseases of the roots and base of the stem, caused, for example, by black root rot (Calonectricia crotalariae), coal rot (Macrophomincauseda phaseolina), fusarium rot or wilt, root rot and pod and branch rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseti), root rot caused by Mycoleptodiscus (Mycoleptodiscus terrestris), Neocosmospora (Neocosmospora vasinfecta), rot of beans and stems (Diaporthe phaseolorum), stem cancer (Diaporthe phaseolorum var. caulivora), late blight rot (Phytophthora megasperma), brown stem rot (Phialophora gregata), mushroom rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), root rot caused by Rhizoctonia, stem rot and black leg (Rhizoctonia solani), stem rot caused by Sclerotinia (Sclerotinia sclerotiorum), sclerotial southern rot (Sclerotinia rolfsii), root rot caused by Thielaviopsis (Thielaviopsis basicola).

Plants that can be treated according to the present invention include the following: Rosaceae sp. (e.g. pome crops such as apples, pears, apricots, cherries, almonds and peaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Musaceae sp. (e.g. banana trees and green spaces), Rubiaceae sp. (e.g. coffee tree), Theaceae sp., Sterculiceae sp., Rutaceae sp. (e.g. lemons, oranges and grapefruits); Vitaceae sp. (e.g. grapes); Solanaceae sp. (e.g. tomatoes, peppers), Liliaceae sp., Asteraceae sp. (e.g. lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (e.g. cucumber), Alliaceae sp. (e.g. leek, onion), Papilionaceae sp. (e.g. pea); major agricultural crops, e.g. Poaceae/Gramineae sp. (e.g. maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and triticale), Asteraceae sp. (e.g. sunflower), Brassicaceae sp. (e.g. white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, Chinese cabbage, kohlrabi, radish and oilseed rape, mustard, horseradish and watercress), Fabacae sp. (e.g. beans, peanuts), Papilionaceae sp. (e.g. soybeans), Solanaceae sp. (e.g. potato species), Chenopodiaceae sp. (e.g. sugar beet, fodder beet, Swiss chard, red beet); Malvaceae (e.g. cotton); useful plants and ornamental plants for gardens and forests; and genetically modified species of each of such plants.

More priority is given to control the following diseases of soybeans. Fungal diseases on leaves, stems, pods and seeds are caused by, for example, Altemaria leaf spot ( Altemaria spec. atrans tenuissima), anthracnose (Colletotrichum gloeosporoides dematium var. truncatum ), brown spot ( Septoria glycines ), Cercospora leaf spot and wilt ( Cercospora kikuchii ), Choanephora leaf wilt ( Choanephora infundibulifera trispora (Syn.) ), Dactuliophora leaf spot ( Dactuliophora glycines ), downy mildew ( Peronospora manshurica ), Drechslera wilt ( Drechslera glycini ), selenophorous leaf spot ( Cercospora sojina ), Leptosphaerulina leaf spot ( Leptosphaerulina trifolii ), Phyllostica leaf spot ( Phyllosticta sojaecola ), bean and stalk blight ( Phomopsis sojae ), powdery mildew ( Microsphaera diffusa ), Pyrenochaeta leaf spot ( Pyrenochaeta glycines ), Rhizoctonia aerial part rot, leaf rot and web rot ( Rhizoctonia solani ), rust ( Phakopsora pachyrhizi, Phakopsora meibomiae ), scab ( Sphaceloma glycines ), Stemphylium leaf rot ( Stemphylium botryosum ), target spot ( Corynespora cassiicola ).

The present invention also relates to the use of compounds of formula I, combinations thereof or compositions thereof for the control or prevention of the following plant diseases: Puccinia spp. (rust) on various plants, such as, but not limited to, P. triticina (brown or leaf rust), P. striiformis (strip or yellow rust ), Puccinia melanocephala (sugarcane rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as wheat, barley or rye, and Phakopsoraceae spp . on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans, Hemileia vastatrix (coffee rust), Uromyces appendiculatus, Uromyces fabae and Uromyces phaseoli (legume rust).

In one embodiment, the present invention provides the use of compounds of formula (I) and compositions thereof for the control and/or prevention of plant diseases caused by pathogens such as : Pyricularia oryzae, Rhizoctonia solani, Botrytis cinerea, Alternaria solani, Colletotrichum capsici, Septoria lycopersici, Fusarium culmorum, Phakopsora pachyrhizi, Sphaerotheca fuliginea, Pseudoperonospora cubensis, Puccinia triticina, Septoria tritici, Phytopthora infestans, Plasmopara viticola or Uncinula necator.

In a preferred embodiment, the present invention provides the use of compounds of formula (I) and compositions thereof for the control and/or prevention of plant diseases such as Puccinia spp. (rust species) on various plants, selected from, but not limited to, P. triticina (brown or leaf rust), P. striiformis (strip or yellow rust ), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals selected from wheat, barley or rye, and Phakopsoraceae spp . on various plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans.

In a more preferred embodiment, the present invention provides the use of compounds of formula (I) and compositions based thereon for controlling and/or preventing the occurrence of phytopathogenic fungi, such as Phakopsora pachyrhizi, Phakopsora meibomiae, on agricultural crops and/or horticultural crops.

The present invention provides a method for controlling unwanted microorganisms, wherein the compounds of formula (I) are applied to the microorganisms and/or their environment.

The present invention further provides a method for protecting seed from unwanted microorganisms using treatment of the seed with at least one compound of formula (I).

The compounds of formula (I) may have strong bactericidal activity and may be used to control unwanted microorganisms such as fungi and bacteria in crop protection and in the protection of such materials.

The compounds of formula (I) have fungicidal properties and can be used in crop protection, for example for the control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes .

The compounds of formula (I) can be used as bactericidal agents in crop protection, for example for the control of Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.

The compounds of formula (I) can be used for the curative or protective control of phytopathogenic fungi. Thus, the present invention also relates to curative and protective methods for controlling phytopathogenic fungi using active ingredients or compositions that are applied to seeds, plants or parts of plants, fruits or to the soil in which the plants grow.

In one embodiment, the present invention provides a composition for controlling and/or preventing the occurrence of phytopathogenic microorganisms, comprising a compound of formula (I), its isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts and one or more inert carriers.

The present invention provides a composition wherein the concentration of the compound of formula (I) is in the range of 10 to 90% by weight relative to the total weight of the composition, preferably 30 to 70% by weight relative to the total weight of the composition.

The composition may further comprise one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers.

In one embodiment, the present invention provides a combination comprising a compound of formula (I), its isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts and one or more active compatible compounds selected from fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, nutrients or fertilizers.

According to the present invention, as defined above, the carrier is a natural or synthetic, organic or inorganic substance with which the active ingredients are mixed or combined for better application, in particular for application to plants or parts of plants or seeds. The carrier, which can be solid or liquid, is generally inert and will be suitable for use in agriculture.

Suitable solid carriers include, for example, ammonium salts and powders of natural rocks such as kaolin types, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and powders of synthetic rocks such as finely divided silica, alumina and silicates; useful solid carriers for granules include, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic flour and granules of organic material such as paper, sawdust, coconut shells, corn cobs and tobacco stalks; useful emulsifiers and/or foaming agents include, for example, nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, arylsulfonates, and protein hydrolysates; Suitable dispersing agents are nonionic and/or ionic substances, for example from the classes of alcohol-POE and/or -POP ethers, acid and/or POP esters of POE, alkylaryl and/or POP ethers of POE, fatty acid and/or POP POE adducts, POE and/or POP polyol derivatives, POE and/or POP sorbitan or -sugar adducts, alkyl or aryl sulfates, alkyl or aryl sulfonates and alkyl or aryl phosphates or the corresponding PO ether adducts. Also suitable are oligo- or polymers, for example those obtained from vinyl monomers, from acrylic acid, from EO and/or PO alone or in combination, for example with (poly)alcohols or (poly)amines. It is also possible to use lignin and its sulfonic acid derivatives, unmodified and modified types of cellulose, aromatic and/or aliphatic sulfonic acids, as well as their adducts with formaldehyde.

The active ingredients can be used as such, or can be converted into conventional formulations, or can be in the form of their formulations, or can be in forms for use obtained from them, such as ready-to-use solutions, emulsions, aqueous or oil-based suspensions, powders, wettable powders, pastes, soluble powders, soluble tablets, powder, soluble granules, granules for distribution, suspoemulsion concentrates, natural products impregnated with the active ingredient, synthetic substances impregnated with the active ingredient, fertilizers, as well as microcapsules in polymeric substances. The application is carried out in the usual way, for example by watering, spraying, atomizing, using boxes for finishing, sprinkling, dusting, foaming, spreading, etc. It is also possible to introduce the active ingredients using the ultra-low volume method or to introduce a preparation of the active ingredient or the active ingredient itself into the soil. It is also possible to treat plant seeds.

Active ingredients can be further formulated into nanoformulation to further improve aqueous solubility, thermal stability, bioavailability, sensory properties and physiological characteristics.

In addition, the choice of composition type will depend on the specific application.

The said compositions can be prepared in a manner known per se, for example by mixing the active ingredients with at least one conventional filler, solvent or diluent, emulsifier, dispersant and/or binder or fixing agent, wetting agent, water-repellent, optionally drying agents and UV stabilizers and, optionally, dyes and pigments, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins, as well as other processing aids.

The present invention includes not only compositions that are ready for use and can be applied by means of a suitable device to a plant or seed, but also commercial concentrates that must be diluted with water before use.

The auxiliary substances used may be substances that are suitable for imparting specific properties to the composition itself and/or preparations obtained from it (e.g. spray solutions, seed dressings), such as certain technical properties and/or also certain biological properties. Typical auxiliary substances include fillers, solvents and carriers.

Suitable excipients are, for example, water, polar and non-polar organic chemical liquids, for example from the classes of aromatic and non-aromatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols (which may optionally be substituted, etherified and/or esterified), ketones (such as acetone, cyclohexanone), esters (including fats and oils) and (poly)esters, unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).

Liquefied gaseous fillers or carriers are liquids which are gaseous at normal temperature and pressure, such as aerosol propellants such as halogenated hydrocarbons, or butane, propane, nitrogen and carbon dioxide.

The formulations may use tackifiers such as carboxymethyl cellulose, natural and synthetic polymers in powder, granule or latex form such as acacia, polyvinyl alcohol and polyvinyl acetate, or natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Additional additives may be mineral, vegetable and methylated seed oils.

If water is used as a filler, it is also possible to use, for example, organic solvents as auxiliary solvents. Suitable liquid solvents are mainly aromatic substances such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic substances or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example petroleum fractions, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, or else water.

Compositions containing compounds of formula (I) may additionally contain additional components, such as surfactants. Suitable surfactants are emulsifiers and/or foaming agents, dispersants or wetting agents having ionic or non-ionic properties, or mixtures of these surfactants. Examples thereof are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, substituted phenols (preferably alkylphenols or arylphenols), salts of esters of sulfosuccinic acid, taurine derivatives (preferably alkyl taurates), esters of phosphoric acid with polyethoxylated alcohols or phenols, esters of fatty acids with polyols and derivatives of compounds containing sulfates, sulfonates and phosphates, for example alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin sulfite waste liquors and methyl cellulose. The presence of a surfactant is necessary if one of the active ingredients and/or one of the inert carriers is insoluble in water and if the application takes place in water. The proportion of surfactants is from 5 to 40 percent by weight of the composition according to the present invention.

The present invention also relates to agrochemical compositions containing an excipient and at least one compound of formula (I) according to the present invention.

The agrochemical composition comprises a fungicidally effective amount of a compound of formula (I). The term "effective amount" means an amount of the composition or compounds of formula (I) that is sufficient to control harmful fungi on cultivated plants or to protect materials and that does not cause significant damage to the treated plants. Such an amount may vary over a wide range and depends on various factors such as the fungal species to be controlled, the cultivated plant or material being treated, climatic conditions and the specific compound of formula (I) used.

The compounds of formula (I), their oxides and salts can be converted into agrochemical compositions of conventional types, such as solutions, emulsions, suspensions, powders, powders, pastes, granules, pressed articles, capsules and mixtures thereof. Examples of composition types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g. CS, ZC), pastes, lozenges, wettable powders or powders (e.g. WP, SP, WS, DP, DS), pressed forms (e.g. BR, TB, DT), granules (e.g. WG, SG, GR, FG, GG, MG), insecticidal articles (e.g. LN) and also gel formulations for treating plant propagation materials such as seeds (e.g. GF). These and additional formulation types are defined in "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 61h Ed. May 2008, Croplife International.

The compositions are obtained in a known manner, for example, as described in Mollet and Grubemann, Formulation technology, Wiley VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, TandF lnforma, London, 2005.

Suitable auxiliary substances are solvents, liquid carriers, solid carriers or fillers, surface-active substances, dispersants, emulsifiers, wetting agents, auxiliaries, solubilizers, penetration enhancers, protective colloids, adhesion additives, thickeners, humectants, water repellents, attractants, feeding stimulants, compatibilizers, bactericides, antifreezes, defoamers, colorants, tackifiers and binders.

Suitable solvents and liquid carriers are water and organic solvents such as medium to high boiling point mineral oil fractions, such as kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, such as toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, such as ethanol, propanol, butanol, benzyl alcohol, cyclohexanol; glycols; DMSO; ketones, such as cyclohexanone; esters, such as lactates, carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, such as N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.

Suitable solid carriers or fillers are mineral substances, such as silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, such as cellulose, starch; fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea; products of plant origin, such as cereal flour, tree bark flour, wood flour, nutshell flour, and mixtures thereof.

Suitable surfactants are surface-active compounds such as anionic, cationic, nonionic and amphoteric surfactants, block copolymers, polyelectrolytes and mixtures thereof. Such surfactants can be used as an emulsifier, dispersant, solubilizer, wetting agent, penetration enhancer, protective colloid or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1: Emulsifiers and Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).

Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates and mixtures thereof. Examples of sulfonates are alkyl aryl sulfonates, diphenyl sulfonates, alpha-olefin sulfonates, lignin sulfonates, fatty acid and oil sulfonates, ethoxylated alkyl phenol sulfonates, alkoxylated aryl phenol sulfonates, condensed naphthalene sulfonates, dodecyl and tridecyl benzene sulfonates, naphthalene and alkyl naphthalene sulfonates, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, ethoxylated alkyl phenols, alcohols, ethoxylated alcohols or fatty acid esters. Examples of phosphates are phosphoric acid esters. Examples of carboxylates are alkyl carboxylates and carboxylated alcohol or alkyl phenol ethoxylates.

Suitable nonionic surfactants are alkoxylates, N-substituted fatty acid amides, amine oxides, esters, sugar surfactants, polymeric surfactants and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters that have been alkoxylated using 1 to 50 equivalents. Ethylene oxide and/or propylene oxide, preferably ethylene oxide, can be used for the alkoxylation. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanolamides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose-glucose esters or alkyl polyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinyl alcohols or vinyl acetate.

Suitable cationic surfactants are quaternary surfactants, such as quaternary ammonium compounds with one or two hydrophobic groups or salts of long-chain primary amines. Suitable amphoteric surfactants are alkyl betaines and imidazolines. Suitable block copolymers are block copolymers of the A-B or A-B-A type, containing blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type, containing an alkanol, polyethylene oxide and polypropylene oxide.

Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or grafted comb copolymers of the polyacid. Examples of polybases are polyvinylamines or polyethyleneamines.

Suitable adjuvants are compounds which have little or no pesticidal activity in themselves and which improve the biological effectiveness of the compound of formula (I) on the target. Examples are surfactants, mineral or vegetable oils and other adjuvants. Further examples are listed in Knowles, Adjuvants and additives, Agrow Reports DS256, TandF lnforma UK, 2006, chapter 5.

Suitable thickeners include polysaccharides (e.g. xanthan gum, carboxymethyl cellulose), inorganic clays (organically modified or unmodified), polycarboxylates and silicates.

Suitable bactericidal agents are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones.

Suitable antifreeze agents are ethylene glycol, propylene glycol, urea and glycerol. Suitable antifoams are silicones, long-chain alcohols and fatty acid salts. Suitable colouring agents (e.g. red, blue or green) are pigments with low water solubility and water-soluble dyes. Examples are inorganic colouring agents (e.g. iron oxide, titanium oxide, iron hexacyanoferrate) and organic colouring agents (e.g. alizarin, azo and phthalocyanine colouring agents).

Suitable tackifiers or binders include polyvinylpyrrolidones, polyvinyl acetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes and cellulose ethers.

Examples of composition types and their production are as follows.

Water-soluble concentrates (SL, LS)

10-60 wt. % of the compound of formula (I) and 5-15 wt. % of a wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) to 100 wt. %. The active substance dissolves upon dilution with water.

Dispersible concentrates (DC)

5-25 wt. % of the compound of formula (I) and 1-10 wt. % of a dispersing agent (e.g. polyvinylpyrrolidone) are dissolved in an organic solvent (e.g. cyclohexanone) to 100 wt. %. Dilution with water provides dispersion.

Emulsifiable concentrates (EC)

15-70 wt. % of the compound of formula (I) and 5-10 wt. % of emulsifiers (for example, calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (for example, an aromatic hydrocarbon) to 100 wt. %. Dilution with water provides an emulsion.

Emulsions (EW, EO, ES)

5-40 wt. % of the compound of formula (I) and 1-10 wt. % of emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in 20-40 wt. % of a water-insoluble organic solvent (e.g. an aromatic hydrocarbon). This mixture is introduced into water to 100 wt. % using an emulsifier and converted into a homogeneous emulsion. Dilution with water provides an emulsion.

Suspensions (SC, OD, FS)

In a stirred ball mill, 20-60 wt. % of the compound of formula (I) is finely ground with the addition of 2-10 wt. % of dispersing agents and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt. % of a thickener (e.g. xanthan gum) and water up to 100 wt. % to obtain a finely ground suspension of the active substance. Dilution with water ensures the production of a stable suspension of the active substance. For the FS composition type, no more than 40 wt. % of a binder (e.g. polyvinyl alcohol) is added.

Water dispersible granules and water soluble granules (WG, SG)

50-80% by weight of the compound of formula (I) are finely ground with the addition of dispersing agents and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) to 100% by weight and obtained in the form of water-dispersible or water-soluble granules using technical means (e.g. extrusion, spray tower, fluidized bed). Dilution with water provides a stable dispersion or solution of the active substance.

Water-dispersible powders and water-soluble powders (WP, SP, WS)

50-80 wt. % of the compound of formula (I) are ground in a rotor-stator mill with the addition of 1-5 wt. % of dispersing agents (e.g. sodium lignosulfonate), 1-3 wt. % of wetting agents (e.g. alcohol ethoxylate) and a solid carrier (e.g. silica gel) up to 100 wt. %. Dilution with water ensures the production of a stable dispersion or solution of the active substance.

Gel (GW, GF)

In a stirred ball mill, 5-25 wt. % of the compound of formula (I) is ground with the addition of 3-10 wt. % of dispersing agents (e.g. sodium lignosulfonate), 1-5 wt. % of a thickener (e.g. carboxymethylcellulose) and water up to 100 wt. % to obtain a finely ground suspension of the active substance. Dilution with water ensures the formation of a stable suspension of the active substance.

Microemulsion (ME)

5-20 wt. % of the compound of formula (I) are added to 5-30 wt. % of a mixture of organic solvents (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt. % of a mixture of surfactants (e.g. alcohol ethoxylate and arylphenol ethoxylate) and water to 100%. This mixture is stirred for 1 hour with spontaneous formation of a thermodynamically stable microemulsion.

Microcapsules (CS)

An oil phase comprising 5-50% by weight of a compound of formula (I), 0-40% by weight of a water-insoluble organic solvent (e.g. an aromatic hydrocarbon), 2-15% by weight of acrylic monomers (e.g. methyl methacrylate, methacrylic acid and di- or triacrylate) is dispersed in an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The radical polymerization results in the formation of microcapsules of poly(meth)acrylate. Alternatively, an oil phase comprising 5-50% by weight of a compound of formula (I) according to the present invention, 0-40% by weight of a water-insoluble organic solvent (e.g. an aromatic hydrocarbon) and an isocyanate monomer (e.g. diphenylmethene-4,4'-diisocyanate) is dispersed in an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). The addition of a polyamine (e.g. hexamethylenediamine) results in the formation of polyurea microcapsules. The amount of monomers is up to 1-10 wt.%. The wt.% refers to the entire CS composition.

Dust-like powders (DP, DS)

1-10% by weight of the compound of formula (I) is finely ground and thoroughly mixed with a solid carrier (for example, finely ground kaolin) to 100% by weight.

Granules (GR, FG)

0.5-30% by weight of the compound of formula (I) is finely ground and combined with a solid carrier (e.g. silicate) to 100% by weight. Granulation is achieved by extrusion, spray drying or fluidized bed.

Ultra Low Volume (UL) Liquids

1-50 wt.% of the compound of formula (I) was dissolved in an organic solvent (e.g., an aromatic hydrocarbon) to 100 wt.%.

Compositions of types i) to xiii) may optionally contain additional auxiliary substances, for example 0.1-1 wt.% bactericidal substances, 5-15 wt.% antifreeze substances, 0.1-1 wt.% antifoams and 0.1-1 wt.% colorants.

Agrochemical compositions generally contain from 0.01 to 95%, preferably from 0.1 to 90% and in particular from 0.5 to 75% by weight of the active substance.

Active substances are used with a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

For treating plant propagation materials, in particular seeds, seed treatment solutions (LS), suspoemulsions (SE), liquid concentrates (FS), powders for dry treatment (DS), water-dispersible powders for treating suspensions (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are commonly used. The compositions in question, after dilution by two to ten times, provide active substance concentrations of 0.01 to 60% by weight, preferably 0.1 to 40%, in ready-to-use preparations. The application can be carried out before or during sowing. Methods for applying the compound of formula (I) and compositions based on it, respectively, to plant propagation material, in particular seeds, include dressing, coating, granulation, dusting and soaking, as well as in-furrow application methods. Preferably, the compound of formula (I) or compositions thereof, respectively, are applied to the plant propagation material in a manner that does not cause germination, for example by seed dressing, granulation, coating and dusting.

When used for plant protection, the amount of active substances applied, depending on the desired effect, is from 0.001 to 2 kg per ha, preferably from 0.005 to 2 kg per ha, more preferably from 0.05 to 0.9 kg per ha and, in particular, from 0.1 to 0.75 kg per ha.

When treating plant propagation materials such as seeds, for example by dusting, coating or impregnating the seeds, the active substance is generally required in an amount of from 0.1 to 1000 g, preferably from 1 to 1000 g, more preferably from 1 to 100 g and most preferably from 5 to 100 g per 100 kg of plant propagation material (preferably seeds).

When used to protect materials or stored products, the amount of active substance applied depends on the type of area to be applied and the desired effect. The amount typically used to protect materials is 0.001 g to 2 kg, preferably 0.005 g to 1 kg of active substance per cubic meter of material to be treated.

Various types of oils, wetting agents, adjuvants, fertilizers or micronutrients, as well as additional pesticides (e.g. herbicides, insecticides, fungicides, growth regulators, safeners, biopesticides) can be added to the active substances or compositions containing them as an additive or, if necessary, only immediately before use (tank mix). These agents can be mixed with the compositions according to the present invention in a weight ratio of 1:100 to 100:1, preferably 1:10 to 10:1.

A pesticide is generally a chemical or biological agent (such as a pesticidal active ingredient, compound, composition, virus, bacterium, antimicrobial, or disinfectant) that acts to repel, inactivate, kill, or otherwise inhibit pests. Target pests may include insects, plant pathogens, weeds, shellfish, birds, mammals, fish, nematodes (roundworms), and microbes that destroy property, cause a nuisance, spread disease, or transmit disease. The term pesticides also includes plant growth regulators, which alter the expected rate of growth, flowering, or reproduction of plants; defoliants, which cause leaves or other foliage to fall from a plant, usually to facilitate harvesting; desiccants, which promote drying of living tissue such as unwanted plant tips; plant activators, which activate plant physiology to provide defense against specific pests; Safeners, which reduce the undesirable herbicidal action of pesticides on agricultural plants; and plant growth promoters, which affect plant physiology to increase plant growth, biomass, yield or any other quality parameter of the crop of agricultural plants.

Biopesticides have been defined as a form of pesticide based on microorganisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds such as metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http://www.epa.gov/pesticides/biopesticides/). Biopesticides are typically created by cultivating and concentrating naturally occurring organisms and/or their metabolites, including bacteria and other microbes, fungi, viruses, nematodes, proteins, etc. They are often considered important components of integrated pest management (IPM) programs.

Biopesticides are divided into two main classes: microbial and biochemical pesticides.

1. Microbial pesticides are composed of bacteria, fungi or viruses (and often include metabolites produced by bacteria and fungi), entomopathogenic nematodes are also microbial pesticides, even though they are multicellular.

2. Biochemical pesticides are naturally occurring substances that control pests or provide other plant protection uses as defined below, but are relatively non-toxic to mammals.

The user typically applies the composition according to the present invention from a pre-dosing device, a knapsack sprayer, a spray tank, a spray aircraft or an irrigation system. Typically, the agrochemical composition is formulated with water, a buffer and/or other auxiliary substances to the desired concentration for application, and thus a ready-to-use spray solution or agrochemical composition according to the present invention is obtained. Typically, from 20 to 2000 liters, preferably from 50 to 500 liters of ready-to-use spray liquid are applied per hectare of agricultural useful area.

The present invention further relates to a composition for controlling undesirable microorganisms, comprising at least one of the compounds of formula (I) and/or one or more active compatible compounds selected from fungicides, bactericides, acaricides, insecticides, nematicides, herbicides, biopesticides, plant growth regulators, antibiotics, fertilizers and/or mixtures thereof.

Typically, the compound of the present invention is administered in the form of a composition (e.g., formulation) containing a carrier. The compound of the present invention and the compositions thereof can be used in various forms such as an aerosol spray, a capsule suspension, a cold fog concentrate, a dusty powder, an emulsifiable concentrate, an oil-in-water emulsion, a water-in-oil emulsion, an encapsulated granule, a fine granule, a flowable concentrate for seed treatment, a gas (under pressure), a gas-generating product, a granule, a hot fog concentrate, a macro granule, a micro granule, an oil dispersible powder, an oil miscible flowable concentrate, an oil miscible liquid, a paste, a plant rod, a powder for dry seed treatment, a seed coating with a pesticide, a soluble concentrate, a soluble powder, a seed treatment solution, a suspension concentrate (flowable concentrate), an ultra-low volume (ULV) liquid, an ultra-low volume (ULV) suspension, water-dispersible granules or tablets, a water-dispersible powder for semi-dry dressing, a water-soluble granule or tablets, water-soluble powder for seed treatment and wettable powder.

The composition typically comprises a liquid or solid carrier and optionally one or more conventional auxiliary substances, which may be solid or liquid auxiliary substances, such as non-epoxidized or epoxidized vegetable oils (e.g. epoxidized coconut oil, rapeseed oil or soybean oil), antifoaming agents, such as silicone oil, preservatives, clays, inorganic compounds, viscosity regulators, surfactants, binders and/or tackifiers. The composition may also additionally comprise a fertilizer, a microelement donor or other preparations that affect plant growth, and may also comprise a combination comprising a compound of the present invention with one or more other biologically active substances, such as bactericides, fungicides, nematicides, plant activators, acaricides and insecticides.

Accordingly, the present invention also provides the possibility of preparing a composition comprising a compound of the present invention and a carrier for agricultural use and optionally one or more conventional formulation excipients.

The compositions are prepared in a manner known per se, in the absence of auxiliary substances, for example by grinding, sifting and/or pressing the solid compound of the present invention, and in the presence of at least one auxiliary substance, for example by thoroughly mixing and/or grinding the compound of the present invention with the auxiliary substance(s). In the case of solid compounds according to the present invention, grinding/milling of the compounds is necessary to ensure a specific particle size. These methods for preparing the compositions and the use of the compounds according to the present invention for preparing these compositions are also an object of the invention.

The compositions contain from 0.1 to 99%, in particular from 0.1 to 95% of the compound according to the invention and from 1 to 99.9%, in particular from 5 to 99.9%, of at least one solid or liquid carrier, as a rule, this is possible in the case of a content of from 0 to 25%, in particular from 0.1 to 20% of surfactants in the composition (% in each case means percentage by weight). While concentrated compositions are usually preferred for commercial products, the end user usually uses diluted compositions, which have significantly lower concentrations of the active ingredient.

Examples of foliar application types for premix compositions are as follows.

Examples of types of seed treatment compositions for pre-mixture compositions are as follows.

Examples of formulation types suitable for tank mix compositions include solutions, dilute emulsions, suspensions or mixtures thereof, and powders.

As with the nature of the formulations, the methods of application, such as foliar application, drenching, spraying, atomizing, dusting, scattering, coating or pouring, are selected according to the intended purposes and the prevailing circumstances.

Tank-mix compositions are typically prepared by dilution with a solvent (e.g. water), wherein one or more pre-mix compositions contain various pesticides and optionally additional auxiliaries. Suitable carriers and auxiliaries may be solid or liquid and are substances commonly used in formulation technology, such as natural or regenerated mineral substances, solvents, dispersants, wetting agents, tackifiers, thickeners, binders or fertilizers.

Typically, the tank mix composition for foliar or soil application comprises from 0.1 to 20%, in particular from 0.1 to 15% of the required ingredients and from 99.9 to 80%, in particular from 99.9 to 85% of solid or liquid adjuvants (including, for example, a solvent such as water), where the adjuvants may be a surfactant in an amount of from 0 to 20%, in particular from 0.1 to 15%, based on the tank mix composition. Typically, the foliar premix formulation comprises from 0.1 to 99.9%, in particular from 1 to 95% of the required ingredients and from 99.9 to 0.1%, in particular from 99 to 5% of solid or liquid adjuvants (including, for example, a solvent such as water), where the adjuvants may be a surfactant in an amount of from 0 to 50%, in particular from 0.5 to 40%, based on the premix formulation.

Typically, the tank mix composition for seed treatment comprises from 0.25 to 80%, in particular from 1 to 75% of the required ingredients and from 99.75 to 20%, in particular from 99 to 25% of solid or liquid adjuvants (including, for example, a solvent such as water), where the adjuvants may be a surfactant in an amount of from 0 to 40%, in particular from 0.5 to 30%, based on the tank mix composition.

Typically, the premix formulation for seed treatment comprises from 0.5 to 99.9%, in particular from 1 to 95% of the required ingredients and from 99.5 to 0.1%, in particular from 99 to 5% of a solid or liquid adjuvant (including, for example, a solvent such as water), where the adjuvants may be a surfactant in an amount of from 0 to 50%, in particular from 0.5 to 40%, based on the premix formulation, with commercial products preferably being formulated as concentrates (e.g. a premix composition) and the end user typically using diluted formulations (e.g. a tank mix formulation).

Preferred seed treatment premix formulations are aqueous suspension concentrates. The formulation can be applied to the seed using conventional processing techniques and devices, such as fluidized bed methods, roller mill methods, rotostatic seed treaters, and drum coaters. Other methods, such as spouted beds, can also be used. The seed size can be pre-determined before coating. After coating, the seed is typically dried and then transferred to a sizing machine for sizing. Such procedures are known in the art. The compounds of the present invention are particularly suitable for use in soil and seed treatment.

Typically, the premix compositions of the present invention comprise from 0.5 to 99.9%, in particular from 1 to 95%, preferably from 1 to 50% by weight of the required ingredients and from 99.5 to 0.1%, in particular from 99 to 5% by weight of a solid or liquid auxiliary (including, for example, a solvent such as water), where the auxiliary substances (or auxiliary) may be a surfactant in an amount of from 0 to 50%, in particular from 0.5 to 40% by weight, based on the composition of the premix.

The compound of formula (I) in a preferred embodiment, independently of any other embodiments, is in the form of a composition for treating (or protecting) plant propagation material, wherein said composition for protecting plant propagation material may further comprise a dye. The composition or mixture for protecting plant propagation material may also comprise at least one polymer of water-soluble and water-dispersible film-forming polymers that improve the adhesion of the active ingredients to the treated plant propagation material, wherein the polymer typically has an average molecular weight of at least 10,000 to about 100,000.

In one embodiment, the present invention provides a method for controlling or preventing infection of useful plants by phytopathogenic microorganisms of agricultural crops and/or horticultural crops, wherein said compound of general formula (I), isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts, composition or combination thereof is applied to plants, plant seeds, parts thereof or their growing site.

In another embodiment, the present invention provides a method for controlling or preventing the occurrence of phytopathogenic microorganisms on agricultural and/or horticultural crops using a compound of formula (I), its isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts, a composition or a combination thereof, which comprises the step of applying an effective dose of the compound or the composition or combination in amounts ranging from 1 g to 2 kg per hectare of agricultural and/or horticultural crops.

In another embodiment, the present invention provides a method for controlling phytopathogenic fungi, comprising treating plants, soil, seeds or materials to be protected with a compound of formula (I), its isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts, a composition or a combination thereof.

Examples of methods for applying the compounds of the present invention and compositions based thereon, i.e. methods for controlling pests in agriculture, are spraying, dusting, brushing, dressing, scattering or pouring, which should be selected in accordance with the intended purposes of the prevailing circumstances.

One method of application in agriculture is application to the foliage of plants (foliar application), wherein the frequency and rate of application can be selected according to the risk of infestation by the pests or fungi in question. Alternatively, the active ingredient can reach the plants via the root system (systemic action), by applying the compound to the locations of the plants, for example by applying a liquid composition of the compound to the soil (by irrigation) or by applying a solid form of the compound in the form of granules to the soil (soil application). In the case of paddy rice plants, such granules can be dosed into a flooded rice field. Soil application of the compounds of the present invention is a preferred method of application.

Typical application rates per hectare are generally between 1 and 2000 g active ingredient per hectare, in particular between 10 and 1000 g/ha, preferably between 10 and 600 g/ha, such as between 50 and 300 g/ha.

Dyes such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, as well as labeled nutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts can be used.

Additional additives may include fragrances, mineral or vegetable, optionally modified oils, waxes and nutrients (including labelled nutrients) such as iron, manganese, boron, copper, cobalt, molybdenum and zinc salts.

Additional components may be stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other substances that improve chemical and/or physical stability.

Other additional components may also be present if necessary, such as protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrating agents, stabilizers, metal ion chelating agents, complexing agents. As a rule, the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.

The compositions typically contain from 0.05 to 99% by weight, from 0.01 to 98% by weight, preferably from 0.1 to 95% by weight, more preferably from 0.5 to 90% by weight of the active ingredient, most preferably from 10 to 70% by weight.

The above-described compositions can be used to control unwanted microorganisms, wherein compositions containing compounds of formula (I) are applied to the microorganisms and/or their habitat.

The compounds of formula (I) according to the present invention, as well as their salts, N-oxides, metal complexes, stereoisomers or polymorphs can be used as such or in compositions based on them and can be mixed with known mixing partners to expand, for example, the spectrum of activity or to prevent the development of resistance. Suitable mixing components include, for example, known fungicides, insecticides, acaricides, nematicides, biopesticides and bactericides. A mixture with other known active ingredients, such as herbicides, or with fertilizers and growth regulators, safeners and/or chemical signal substances is also possible.

According to one embodiment, the individual components of the composition according to the present invention, such as parts of a kit or parts of a two-component or three-component mixture, can be mixed by the user himself in a spray tank or in any other type of tank used for application (e.g. seed dressing drums, seed pelleting equipment, knapsack sprayer), and other auxiliaries can be added if necessary.

Therefore, in one embodiment of the present invention there is provided a kit for preparing a suitable pesticidal composition, the kit comprising a) a composition comprising component 1) as defined herein and at least one excipient; and b) a composition comprising component 2) as defined herein and at least one excipient; and optionally c) a composition comprising at least one excipient and optionally a further active component 3) as defined herein.

Compounds of formula I, their combinations and compositions containing them, when used as fungicides with other fungicides, can lead to an expansion of the resulting fungicidal spectrum of activity or to the prevention of the development of resistance to fungicides. In addition, in many cases, unusual effects are achieved.

This can be achieved by simultaneously applying the compound(s) of formula I and at least one further pesticidally active substance either together (e.g. as a tank mix) or separately or sequentially, wherein the time interval between the individual applications is selected to ensure that the active substance applied first is still present at the site of action in sufficient quantity when the next pesticidally active substance(s) is applied. The order of application is not important for the practice of the present invention.

Known and registered active compounds such as fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients can be combined with at least one compound of formula I according to the present invention. For example, fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, safeners, plant growth regulators, antibiotics, fertilizers and nutrients disclosed and indicated in WO2017076739 (A to O) can be combined with a compound of formula I according to the present invention. The present invention also relates to such combinations comprising a compound of the present invention and the active compatible compounds described in WO2017076739.

Fungicides, insecticides, nematicides, acaricides, biopesticides, herbicides, plant growth regulators, antibiotics, fertilizers and nutrients described in WO2017076739 are not reproduced herein for brevity and are incorporated herein by reference as non-limiting examples in combination with at least one compound of formula I of the present invention.

According to the present invention, all plants and parts of plants can be treated. Plants in this document are understood to mean all plants and plant populations, such as desirable and undesirable wild plants or cultivated plants (including naturally occurring cultivated plants). Agricultural crops can be plants that can be obtained by traditional breeding and optimization methods or biotechnology and genetic engineering methods or combinations of these methods, including transgenic plants and including plant cultivars that are protected and not protected by plant breeders' rights. Parts of plants are understood to mean all parts and organs of plants above and below ground, such as shoots, leaves, flowers and roots, examples of which include leaves, needles, legs, stems, flowers, fruiting bodies, fruits and seeds, as well as roots, tubers and rhizomes. Parts of plants also include plant material, vegetative and generative propagation material, such as cuttings, tubers, rhizomes, shoots and seeds.

In one embodiment, the present invention provides a seed comprising a compound of formula (I), its agriculturally acceptable salts, isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides or S-oxides, wherein the amount of the compound of formula (I), its isomers/structural isomers, stereoisomers, diastereomers, enantiomers, tautomers, metal complexes, polymorphs, N-oxides, S-oxides or agriculturally acceptable salts is from 0.1 g to 10 kg per 100 kg of seed.

Furthermore, the present invention includes a method for treating seeds, in particular seeds (in the dormant stage, primed, pre-germinated or even with roots and leaves emerging), treated with at least one of the compounds of formula (I) and compositions based on them. The seeds according to the present invention are used in methods for protecting seeds and germinated plants from seeds from phytopathogenic harmful fungi. These methods use seeds treated with at least one active ingredient according to the present invention.

It is also desirable to optimize the amount of active ingredient used to ensure the best possible protection of seeds, germinating plants and germinated seedlings against infection by phytopathogenic fungi, but without damaging the plants themselves with the active ingredient used. In particular, seed treatment methods should also take into account the inherent phenotypes of transgenic plants in order to achieve optimal protection of seeds and germinating plants using a minimum amount of plant protection compositions.

Thus, the present invention also relates to a method for protecting seeds, germinating plants and sprouted seedlings from attack by animal pests and/or phytopathogenic harmful microorganisms by treating the seeds with a composition according to the present invention. The invention also relates to the use of compositions according to the present invention for treating seeds in order to protect seeds, germinating plants and sprouted seedlings from animal pests and/or phytopathogenic microorganisms. The present invention also relates to seeds that have been treated with a composition according to the present invention for protection against animal pests and/or phytopathogenic microorganisms.

One of the advantages of the present invention is that the treatment of seeds with these compositions protects not only the seeds themselves, but also the resulting plants after germination from animal pests and/or harmful phytopathogenic microorganisms. Thus, immediate treatment of the agricultural crop during sowing or shortly thereafter protects the plants, as does the treatment of the seeds before sowing. It is also considered advantageous that the active ingredients or compositions according to the present invention can be used in particular also for transgenic seeds, in which case the plant that grows from these seeds is capable of expressing a protein that acts against pests, herbicide damage or abiotic stress. The treatment of such seeds with the active ingredients or compositions according to the present invention, for example an insecticidal protein, can lead to the control of certain pests. Surprisingly, in this case an additional synergistic effect can be observed, which further increases the effectiveness of the protection against attack by pests, microorganisms, weeds or abiotic stress.

The compounds of formula (I) are suitable for protecting the seeds of any plant variety used in agriculture, greenhouse, forestry or horticulture. In particular, the seeds are the seeds of cereals (such as wheat, barley, rye, millet and oats), oilseed rape, corn, cotton, soybeans, rice, potatoes, sunflowers, beans, coffee trees, beets (such as sugar beets and fodder beets), peanuts, vegetables (such as tomatoes, cucumbers, onions and lettuce), lawns and ornamental plants. Of particular importance is the treatment of wheat, soybeans, oilseed rape, corn and rice seeds.

As described below, the treatment of transgenic seeds with the active ingredients or compositions according to the invention is of particular importance. This applies to plant seeds containing at least one heterologous gene which provides for the expression of a polypeptide or protein, for example having insecticidal properties. Such heterologous genes in transgenic seeds can originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. Such heterologous genes preferably originate from Bacillus sp ., in which case the gene product is effective against the European corn borer and/or the western corn rootworm. In particular, it is preferred that the heterologous genes originate from Bacillus thuringiensis .

In the context of the present invention, the composition of the present invention is applied to the seeds either separately or in a suitable formulation. Preferably, the seeds are treated in a state in which they are sufficiently stable so that they are not damaged during the treatment. As a rule, the seeds can be treated at any time between harvesting and some time after sowing. Typically, seeds are used that have been separated from the plant and freed from cobs, shells, stems, shells, hairs or fruit pulp. For example, it is possible to use seeds that have been collected, cleaned and dried to a moisture content of less than 15% by weight. Alternatively, it is also possible to use seeds that, after drying, have been, for example, treated with water and then dried again, or seeds immediately after priming, or seeds stored under priming conditions, or pre-germinated seeds, or seeds sown in brooder trays, tapes or paper.

Usually, when treating seeds, the selection of the amount of the composition according to the invention applied to the seeds and/or the amount of additional additives must be ensured in such a way that the germination of the seeds is not disturbed or that the resulting plant is not damaged. This must be ensured in particular in the case of using active ingredients that can exhibit phytotoxic effects at certain application rates.

The compounds of formula (I) can be applied directly, i.e. without any other components and without dilution. In general, it is preferable to apply the compositions to the seeds in the form of a suitable formulation. Suitable formulations and methods for treating seeds are known to those skilled in the art. The compounds of formula (I) can be converted into conventional formulations suitable for application to seeds, such as solutions, emulsions, suspensions, powders, foams, slurries, or used in combination with other seed coating compositions, such as film-forming materials, granulation materials, finely dispersed iron or other metal powder, granules, inactivated seed coating material, and ULV formulations.

When treating seeds to facilitate planting, the seeds can be coated with a polymer. The polymer coating consists of a binder, wax and pigment, as well as one or more stabilizers in an amount effective to stabilize the suspension. The binder can be a polymer selected from the group consisting of a copolymer of vinyl acetate and ethylene, a homopolymer of vinyl acetate, a copolymer of vinyl acetate and acrylic, vinyl acrylic, acrylic polymer, ethylene vinyl chloride, maleic anhydride of vinyl ether or butadiene styrene. Other similar polymers can be used.

These compositions are prepared in a known manner by mixing the active ingredients or combinations of active ingredients with conventional additives, such as conventional fillers and solvents or diluents, colorants, wetting agents, dispersing agents, emulsifiers, antifoaming agents, preservatives, secondary thickeners, adhesives, gibberellins, and water.

All suitable dyes that may be present in the seed dressing compositions used in accordance with the present invention are dyes conventional for such purposes. Either pigments that are minimally soluble in water or dyes that are soluble in water may be used. Examples include the dyes known under the names rhodamine B, pigment C.I. red 112 and solvent C.I. red 1.

Suitable wetting agents that may be present in the seed dressing compositions useful in accordance with the present invention are all substances that promote wetting and that are conventionally used to formulate active agrochemical ingredients. Preferably, alkyl naphthalene sulfonates such as diisopropyl or diisobutyl naphthalene sulfonates are used.

Suitable dispersants and/or emulsifiers which may be present in the seed dressing compositions useful according to the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of active agrochemical ingredients. Preferably, nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants are used. Suitable nonionic dispersants include, in particular, ethylene oxide/propylene oxide block copolymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, as well as phosphated or sulfated derivatives thereof. Suitable anionic dispersants are, in particular, lignosulfonates, polyacrylic acid salts and arylsulfonate/formaldehyde condensates.

The antifoaming agents that may be present in the seed dressing compositions useful in accordance with the present invention are all antifoaming agents conventionally used to formulate active agrochemical ingredients. Silicone antifoaming agents and magnesium stearate are preferably used.

Preservatives that may be present in seed dressing compositions useful in accordance with the present invention are all substances used for such purposes in agrochemical compositions. Examples include dichlorophen and benzyl alcohol hemiformal.

Secondary thickeners that may be present in the seed dressing compositions used in accordance with the present invention are all substances used for such purposes in agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.

All adhesives that may be present in the seed dressing compositions used in accordance with the present invention are conventional binders used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

The seed application compositions that can be used according to the present invention can be used to treat a large number of different types of seeds, either directly or after preliminary dilution with water. For example, concentrates or preparations obtained from them by dilution with water can be used to treat the seeds of cereals, such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, soybeans, rice, oilseed rape, peas, beans, cotton, sunflower and beets, as well as a variety of different vegetable seeds. The compositions used according to the present invention, or diluted preparations thereof, can also be used for the seeds of transgenic plants. In this case, additional synergistic effects can also occur when interacting with substances formed during expression.

For treating seeds with the compositions applicable according to the present invention or with preparations obtained from them by adding water, all mixing devices commonly used for application to seeds are suitable. In particular, the procedure for application to seeds consists of placing the seeds in a mixer, adding the specific desired amount of compositions, as such or after preliminary dilution with water, and mixing everything until all the applied compositions are uniformly distributed on the seeds. If necessary, this is followed by a drying step.

The compounds of the present invention and the compositions based on them are also suitable for protecting plant propagation material, for example seeds, such as fruits, tubers or kernels, or seedlings, from pests of the above-mentioned type. The propagation material can be treated with the compound before planting, for example the seeds can be treated before sowing. Alternatively, the compound can be applied to the seed kernels (coating) either by soaking the kernels in a liquid composition or by applying a layer of a solid composition. It is also possible to use the compositions when the propagation material is planted in the place of application, for example in a seed furrow during sowing. These methods for treating the plant propagation material and the plant propagation material treated in this way are further objects of the invention. Typical application rates will depend on the plant and the pest/fungus to be controlled and will typically be from 1 to 200 grams per 100 kg of seed, preferably from 5 to 150 grams per 100 kg of seed, such as from 10 to 100 grams per 100 kg of seed. Application of the compounds of the present invention to seed is the preferred method of application.

The application rate of the compositions used in accordance with the present invention may vary over a relatively wide range. It is determined by the specific content of the active ingredients in the compositions and the seeds. The application rates of each individual active ingredient are usually from 0.001 to 15 g per kilogram of seeds, preferably from 0.01 to 5 g per kilogram of seeds.

When using the compounds of formula (I) as fungicides, the application rates may vary over a relatively wide range depending on the type of application. The application rate of the active ingredients according to the present invention is:

in the case of treatment of plant parts, such as leaves: from 0.1 to 10,000 g/ha, preferably from 10 to 1,000 g/ha, more preferably from 30 to 300 g/ha (in the case of application by pouring or dripping, the application rate can even be reduced, especially when using inert substrates such as mineral wool or perlite);

in the case of seed treatment: from 0.1 to 200 g per 100 kg of seed, preferably from 1 to 150 g per 100 kg of seed, more preferably from 2.5 to 25 g per 100 kg of seed, even more preferably from 2.5 to 12.5 g per 100 kg of seed;

in case of soil cultivation: from 0.1 to 10,000 g/ha, preferably from 1 to 5,000 g/ha.

These application rates are given only as an example and do not limit the objectives of the invention.

In some cases, the compounds of formula (I) can also be used, at certain concentrations or application rates, as herbicides, safeners, growth regulators or plant property improvers or as microbicides, such as fungicides, antifungals, bactericides, viricides (including compositions against viroids) or as compositions against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms).

The compounds of formula (I) interfere with the physiological processes of plants and can therefore also be used as plant growth regulators. Plant growth regulators can have different effects on plants. The effect of the substances depends mainly on the time of application relative to the development stage of the plant, the plant variety, as well as on the amount of active ingredient applied to the plants or their environment and on the type of application. In each case, the growth regulators must have the desired effect on the crop plants.

Growth regulating effects include earlier germination, better emergence, more developed root systems and/or improved root growth, increased tillering ability, more productive tillers, earlier flowering, increased plant height and/or biomass, shorter stems, improved tiller growth, number of grains per spike, number of ears per ^m2 , number of stolons and/or number of flowers, improved percentage of yield to total plant weight, larger leaves, fewer dead basal leaves, improved leaf arrangement, earlier maturity/earlier ripening of fruits, uniform ripening, increased duration of grain filling, better fruit aftertaste, larger fruit/vegetable size, resistance to sprouting and less lodging.

Increased or improved yield refers to total biomass per hectare, yield per hectare, kernel/fruit weight, seed size and/or hectolitre weight, and improved product quality including:

improved processing suitability related to size distribution (kernel, fruit, etc.), uniform ripening, grain moisture content, better milling, better vinification, better brewing, increased juice yield, yield, digestibility, sedimentation number, falling number, pod stability, storage stability, improved fibre length/strength/uniformity, improved milk and/or meat quality from silaged animals, adaptation to cooking and roasting;

additionally including improved marketability related to improved fruit/grain quality, size distribution (kernel, fruit, etc.), increased shelf life/expiration date, firmness/softness, flavour (aroma, texture, etc.), variety (size, shape, number of berries, etc.), number of berries/fruits in a bunch, crispness, freshness, wax coating, reduced incidence of physiological disorders, colour, etc.;

additionally including an increased amount of necessary ingredients, such as, for example, protein content, fatty acid content, oil content, oil quality, amino acid composition, sugar content, acid content (pH), sugar/acid ratio (Brix), polyphenol content, starch content, nutritional value, gluten content/index, caloric content, taste, etc.;

and additionally including reduced amounts of undesirable ingredients such as, for example, lower amounts of mycotoxins, lower amounts of aflatoxins, geosmin levels, phenolic aromas, lactase, polyphenol oxidase and peroxidase, nitrate content, etc.

Plant growth regulating compounds can be used, for example, to slow down the vegetative growth of plants. Such growth slowing is of economic interest, for example, in the case of grasses, since it is possible to reduce the frequency of grass cutting in ornamental gardens, parks and sports facilities, on roadsides, at airports or in fruit crops. Also of importance is the suppression of the growth of herbaceous and woody plants on roadsides and near pipelines or overhead cables, or in general in areas where intensive plant growth is undesirable.

It is also important to use growth regulators to suppress the longitudinal growth of grain crops. This reduces or completely eliminates the risk of lodging of plants before harvest. In addition, grain growth regulators can strengthen the stem, which also prevents lodging. Using growth regulators to shorten and strengthen the stems allows for the application of large volumes of fertilizers to increase yields without any risk of lodging of grain crops.

In many crops, inhibition of vegetative growth allows denser plantings, and thus higher yields can be obtained depending on the soil surface. Another advantage of the smaller plants obtained in this way is that the crop is easier to grow and harvest.

Reducing vegetative plant growth can also result in increased or improved yields, since nutrients and assimilants are more beneficial to flower and fruit production than to vegetative plant parts.

Alternatively, growth regulators can also be used to stimulate vegetative growth. This is very useful when harvesting vegetative parts of plants. However, stimulating vegetative growth can also promote generative growth, as more assimilants are formed, which leads to more or larger fruits.

In addition, positive effects on growth or yield can be achieved through improved nutrient use efficiency, especially nitrogen (N) use efficiency, phosphorus (P) use efficiency, water use efficiency, improved transpiration rate, respiration and/or _CO2 assimilation, improved nodulation, improved calcium metabolism, etc.

Similarly, growth regulators can be used to change the composition of plants, which in turn can lead to an improvement in the quality of the harvested products. Under the influence of growth regulators, parthenocarpic fruits can be formed. In addition, it is possible to influence the sex of flowers. It is also possible to obtain sterile pollen, which is of great importance in breeding and obtaining hybrid seeds.

The use of growth regulators allows the control of plant branching. On the one hand, the disruption of apical dominance can promote the development of lateral shoots, which can be very desirable, especially when growing ornamental plants, also in combination with growth suppression. On the other hand, however, the growth of lateral shoots can also be suppressed. This effect is of particular interest, for example, when growing tobacco or when growing tomatoes.

Under the influence of growth regulators, the number of leaves on plants can be controlled so that defoliation of plants is achieved at the desired time. Such defoliation plays an important role in mechanical harvesting of cotton, but is also of interest to facilitate harvesting of other crops, such as viticulture. Plant defoliation can also be carried out to reduce transpiration of plants before they are transplanted.

In addition, growth regulators can modulate plant senescence, which can lead to an increase in the duration of green leaf area, a longer grain filling phase, improved crop quality, etc.

Growth regulators can also be used to regulate fruit cracking. On the one hand, it is possible to prevent premature fruit cracking. On the other hand, it is also possible to promote fruit cracking or even to stop the development of flowers to achieve the desired weight ("thinning"). It is also possible to use growth regulators during harvesting to reduce the effort required to separate the fruit, to enable mechanical harvesting or to facilitate manual harvesting.

Growth regulators can also be used to accelerate or slow down the ripening of the harvested material before or after harvesting. This is particularly advantageous, as it allows optimal adaptation to market requirements. Moreover, growth regulators can in some cases improve the colour of the fruit. In addition, growth regulators can also be used to synchronize ripening over a certain period of time. This creates the necessary conditions for complete mechanical or manual harvesting in one step, for example in the case of tobacco, tomatoes or coffee.

By using growth regulators, it is possible to additionally influence the dormancy of seeds or buds of plants, so that plants such as pineapple or ornamental plants in nursery departments, for example, germinate, emerge or flower at a time when they would not normally be inclined to do so. In areas where there is a risk of frost, it may be desirable to delay budding or seed germination with growth regulators to avoid damage due to late frosts.

Finally, growth regulators can make plants resistant to frost, drought, or high soil salinity. This allows plants to be grown in regions that are not usually suitable for this purpose.

The compounds of formula (I) also have a strong strengthening effect on plants. Accordingly, they can be used to mobilize the plant's defenses against infection by unwanted microorganisms.

Plant strengthening substances (resistance-inducing substances) in the context of the present invention are substances capable of stimulating the plant defense system in such a way that the treated plants, when subsequently inoculated with undesirable microorganisms, develop a high degree of resistance to these microorganisms.

Furthermore, in the context of the present invention, the physiological effects of plants include the following.

Tolerance to abiotic stress, including tolerance to high or low temperatures, tolerance to drought and recovery from drought stress, water use efficiency (correlated with reduced water consumption), tolerance to flooding, tolerance to ozone stress and ultraviolet radiation, tolerance to chemicals such as heavy metals, salts, pesticides, etc.

Resistance to biotic stress, including increased resistance to fungi and increased resistance to nematodes, viruses and bacteria. In the context of the present invention, resistance to biotic stress preferably includes increased resistance to fungi and increased resistance to nematodes.

Improved plant vigor including plant vigor/plant quality and seed vigor, reduced stand damage, improved appearance, accelerated recovery from periods of stress, improved pigmentation (e.g. chlorophyll content, green retention effects, etc.) and increased photosynthetic efficiency.

In addition, the compounds of formula (I) can reduce the content of mycotoxins in the collected material, as well as in food products and feed prepared from them. Mycotoxins include, in particular, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15-Ac-DON, 3-Ac-DON, T2 and HT2 toxins, fumonisins, zearalenone, moniliformin, fusarin, diacetoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins, which can be produced, for example, by the following fungi: Fusarium species, such as F. acuminatum, F. asiaticum, F. avenaceum, F. crookwellense, F. culmorum, F. graminearum (Gibberella zeae), F. equiseti, F. fujikoroi, F. musarum, F. oxysporum, F. proliferatum, F. poae, F. pseudograminearum, F. sambucinum, F. scirpi, F. semitectum, F. solani, F. sporotrichoides, F. langsethiae, F. subglutinans, F. tricinctum, F. verticillioides, etc., as well as Aspergillus species, for example A. flavus, A. parasiticus, nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spp ., e.g. P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spp ., e.g. C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotrys spp . and other.

Compounds of formula (I) can also be used for the protection of materials, for the protection of industrial materials from contamination and destruction by phytopathogenic fungi.

In addition, the compounds of formula (I) can be used as antifouling compositions alone or in combination with other active ingredients.

Industrial materials in this context are understood to mean inanimate materials that have been prepared for use in industry. For example, industrial materials that are to be protected by the compositions of the present invention against microbial alteration or destruction may be adhesives, glues, paper, wallpaper and thick paper/cardboard, textiles, carpets, leather, wood, fibers and fabrics, paints and plastic products, cooling lubricants and other materials that may be contaminated or destroyed by microorganisms. Parts of industrial plants and buildings, such as cooling water circuits, cooling and heating systems, as well as ventilation and air conditioning devices, which may be damaged by the proliferation of microorganisms, may also be mentioned within the scope of the materials to be protected. Industrial materials within the scope of the present invention preferably include adhesives, powdered glue, paper and cardboard, leather, wood, paints, cutting fluids and heat exchange fluids, more preferably wood.

Compounds of formula (I) can prevent adverse effects such as rotting, decay, fading, discolouration or mold formation.

In the case of wood treatment, the compounds of formula (I) can also be used against diseases caused by fungi that can grow on or in wood. The term "wood" means all types of wood and all types of treatment of this wood intended for construction, for example solid wood, high-density wood, laminated wood and plywood. The method for treating wood according to the present invention essentially consists in bringing into contact with the composition according to the present invention; this includes, for example, direct application, spraying, dipping, injection or any other suitable methods.

In addition, the compounds of formula (I) can be used to protect objects that come into contact with salt or brackish water, especially hulls, screens, nets, buildings, piers and alarm systems, from fouling.

The compounds of formula (I) can also be used to protect stored goods. Stored goods are understood to be natural substances of plant or animal origin or products of their processing, which are of natural origin and for which long-term protection is desirable.

Stored goods of plant origin, such as plants or parts of plants, such as stems, leaves, tubers, seeds, fruits, grains, can be protected immediately after harvesting or after processing by (pre-) drying, moistening, crushing, grinding, pressing or roasting. Stored goods also include wood, both untreated, such as construction timber, electric poles and barriers, and in the form of finished products, such as furniture. Stored goods of animal origin include, for example, skins, leather, fur and wool. The compositions according to the invention can prevent adverse effects such as rotting, decay, fading, discolouration or mold formation.

Microorganisms capable of breaking down or changing industrial materials include, for example, bacteria, fungi, yeasts, algae and slime organisms. The compounds of formula (I) are preferably active against fungi, especially moulds, wood-bleaching and wood-destroying fungi ( Ascomycetes, Basidiomycetes, Deuteromycetes and Zygomycetes ), and against slime organisms and algae. Examples include microorganisms of the following genera: Alternaria , such as Alternaria tenuis; Aspergillus, such as Aspergillus niger; Chaetomium, such as Chaetomium globosum; Coniophora, such as Coniophora puetana; Lentinus, such as Lentinus tigrinus; Penicillium, such as Penicillium glaucum; Polyporus , such as Polyporus versicolor; Aureobasidium , such as Aureobasidium pullulans; Sclerophoma , for example Sclerophoma pityophila; Trichoderma, for example Trichoderma viride; Ophiostoma spp., Ceratocystis spp., Humicola spp., Petriella spp., Trichurus spp., Coriolus spp., Gloeophyllum spp., Pleurotus spp., Poria spp., Serpula spp. and Tyromyces spp., Cladosporium spp., Paecilomyces spp. Mucor spp., Escherichia, eg Escherichia coli; Pseudomonas, for example Pseudomonas aeruginosa; Staphylococcus, for example Staphylococcus aureus, Candida spp. and Saccharomyces spp., for example Saccharomyces cerevisae.

In addition, the compounds of formula (I) also have a good antifungal effect. They have a very broad spectrum of antifungal activity, especially against dermatophytes and yeasts, molds and biphasic fungi (e.g. Candida species, e.g. Candida albicans, Candida glabrata ), as well as Epidermophyton floccosum, Aspergillus species, e.g. Aspergillus niger and Aspergillus fumigatus, Trichophyton species, e.g. Trichophyton mentagrophytes, Microsporon species , e.g. Microsporon canis and audouinii . The listing of these fungi is in no way a limitation of the spectrum of fungi covered, but is purely illustrative.

The compounds can also be used to control important fungal pathogens in fish and crustacean farming, such as saprolegnia diclina in trout, saprolegnia parasitica in crayfish.

Therefore, the compounds of formula (I) can be used in both medicinal and non-medicinal applications.

The compounds of formula (I) can be used as such in the form of their formulations or forms of use obtained from them, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, powders and granules. The application is carried out in the usual way, for example by pouring, spraying, atomizing, sprinkling, dusting, foaming, spreading, etc. It is also possible to introduce the active ingredients using the ultra-low volume method or to introduce a preparation of the active ingredient/the active ingredient itself into the soil. It is also possible to treat plant seeds.

It is possible to treat all plants and parts thereof according to the present invention, preferably wild plant species and plant cultivars or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, as well as parts thereof. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods in combination, if appropriate, with conventional methods (genetically modified organisms) and parts thereof are treated. The terms "parts" or "plant parts" have been explained above. More preferably, plant cultivars that are commercially available or used are treated according to the present invention. Plant cultivars are understood to mean plants that have new properties ("traits") and have been obtained by conventional breeding, mutagenesis or by means of recombinant DNA methods. These can be varieties, varieties, bio- or genotypes.

The method of treatment according to the present invention can be used in the treatment of genetically modified organisms (GMOs), such as plants or seeds. Genetically modified plants (or transgenic plants) are plants whose heterologous gene is stably integrated into the genome. The expression "heterologous gene" essentially means a gene that is provided or assembled outside the plant and, when introduced into the nuclear, chloroplast or mitochondrial genome, confers new or improved agronomic or other properties to the transformed plant by expressing a protein or polypeptide of interest or by downregulating or suppressing the expression of other genes present in the plant (using, for example, antisense technology, cosuppression technology, RNA interference (RNAi) technology or microRNA (miRNA) technology). A heterologous gene located in a genome is also called a transgene. A transgene defined by its specific position in the plant genome is called a transformation or a transgenic event.

Plants and plant cultivars that are preferably to be treated according to the present invention include all plants that have genetic material that imparts to these plants particularly advantageous, useful characteristics (regardless of whether they are obtained by breeding and/or biotechnology methods).

Plants and plant cultivars which are also preferably treated according to the present invention are resistant to one or more biotic stresses, i.e. said plants exhibit better protection against animal and microbial pests such as nematodes, insects, mites, phytopathogenic fungi, bacteria, viruses and/or viroids.

Plants and plant cultivars that can also be treated according to the present invention are plants that are resistant to one or more abiotic stresses. Abiotic stress conditions can include, for example, drought, exposure to low temperatures, heat exposure, osmotic stress, flooding, increased soil salinity, increased exposure to minerals, exposure to ozone, exposure to strong light, limited availability of nitrogen nutrients, limited availability of phosphorus nutrients, shade avoidance.

Plants and plant cultivars that can also be processed according to the present invention are plants characterized by improved yield characteristics. The increased yield of said plants can be the result of, for example, improved physiology, growth and development of plants, such as water use efficiency, water retention efficiency, improved nitrogen use, increased carbon assimilation, improved photosynthesis, increased germination efficiency and accelerated maturation. In addition, the yield can be affected by improved plant structure (under stress and non-stress conditions), including but not limited to early flowering, control of flowering to obtain hybrid seeds, seedling viability, plant size, number and spacing of nodes, root growth, seed size, fruit size, pod size, number of pods or spikelets, number of seeds per pod or spikelet, seed weight, improved seed filling, reduced seed scattering, reduced pod cracking and lodging resistance. Additional crop traits include seed composition such as carbohydrate content and composition such as cottonseed or starch, protein content, oil content and composition, nutritional value, reduction of anti-nutritional compounds, improved processability and better storage stability.

Plants that can be treated according to the present invention are hybrid plants that already exhibit characteristics of heterosis or hybrid vigor, which generally results in higher yield, vigor, vigor and resistance to biotic and abiotic stresses.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can be treated according to the present invention are herbicide-resistant plants, i.e. plants that have acquired resistance to one or more of the said herbicides. Such plants can be obtained either by genetic transformation or by selection of plants containing a mutation that confers such resistance to herbicides.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be processed according to the present invention are insect-resistant transgenic plants, i.e. plants that have obtained resistance to attack by certain target insects. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such resistance to insects.

Plants or plant cultivars (obtained by plant biotechnology methods, such as genetic engineering), which can also be processed according to the present invention, are resistant to abiotic stresses. Such plants can be obtained by genetic transformation or by selection of plants containing a mutation that confers such resistance to stress.

Plants or plant cultivars (obtained by plant biotechnology methods such as genetic engineering) that can also be processed according to the present invention exhibit altered quantity, quality and/or storage stability of the harvested product and/or altered properties of certain ingredients of the harvested product.

Plants or plant cultivars (which may be obtained by plant biotechnology methods such as genetic engineering) which may also be processed according to the present invention are plants, such as cotton plants, with altered fibre characteristics. Such plants may be obtained by genetic transformation or by selection of plants containing a mutation which imparts such altered fibre characteristics.

Plants or plant cultivars (which may be obtained by plant biotechnology methods such as genetic engineering) which may also be processed according to the present invention are plants such as oilseed rape or Brassica related plants with altered oil profile characteristics. Such plants may be obtained by genetic transformation or by selection of plants containing a mutation which imparts such altered oil profile characteristics.

Plants or plant cultivars (which may be obtained by plant biotechnology methods such as genetic engineering) which may also be processed according to the present invention are plants, such as oilseed rape or Brassica related plants, with altered seed cracking characteristics. Such plants may be obtained by genetic transformation or by selection of plants containing a mutation conferring such altered seed cracking characteristics, and include plants, such as oilseed rape plants, with delayed or reduced seed cracking.

Plants or plant cultivars (which may be obtained using plant biotechnology techniques such as genetic engineering) that may also be processed according to the present invention are plants, such as tobacco plants, with altered patterns of post-translational protein modification.

The compounds of the present invention not only effectively control unwanted phytopathogenic microorganisms, but also exhibit positive responses in crops, such as plant growth enhancement effects, such as enhanced crop vigor, enhanced root growth, increased resistance to drought, high salt, high temperature, cold, frost or light, improved flowering, efficient use of water and nutrients (e.g. improved nitrogen uptake), improved plant product quality, more productive shoots, increased resistance to fungi, insects, pests, etc., which results in higher yields.

In one embodiment, the compounds of general formula (I) as disclosed in the present invention are used for non-agronomic use.

CHEMICAL EXAMPLES

The following examples set forth the procedure and method for preparing the compounds of the present invention without limiting them and include the best mode contemplated by the present inventors for carrying out the present invention.

Example 1. Synthesis intermediate connections 3-bromoamidine (III)

a) N'-(3-Bromo-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (III)

Stage 1. Receiving 3-bromo-2,5-dimethylbenzoic acids (XXIV)

A mixture of 2,5-dimethylbenzoic acid (2 g, 13.3 mmol) and sulfuric acid (20 mL) was cooled to 0 °C, N-bromosuccinimide (2.4 g, 13.3 mmol) was added to the reaction mixture and stirred at 0 °C for 1.5 h. After completion of the reaction, the reaction mixture was poured onto crushed ice and extracted with ethyl acetate (50 mL). The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography using 50% ethyl acetate in hexane as eluent to give 3-bromo-2,5-dimethylbenzoic acid (1.6 g, yield 52%), LCMS (M-1): 229.00.

Stage 2. Receiving rubs -butyl-(3-bromo-2,5-dimethylphenyl)carbamate

A reaction mixture of 3-bromo-2,5-dimethylbenzoic acid (1 g, 4.3 mmol), triethylamine (1.5 ml, 10.9 mmol) and diphenylphosphoryl azide (1.8 g, 6.5 mmol) in anhydrous tert -butanol was heated at 80 °C for 6 h. After completion of the reaction, the reaction mixture was poured onto crushed ice and extracted with ethyl acetate (50 ml). The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography using 50% ethyl acetate in hexane as eluent to give tert -butyl (3-bromo-2,5-dimethylphenyl)carbamate (0.9 g, 69% yield).

Stage 3. Receiving 3-bromo-2,5-dimethylaniline (XXIII)

Trifluoroacetic acid (10 ml, 130 mmol) was added dropwise to a solution of tert -butyl (3-bromo-2,5-dimethylphenyl)carbamate (1 g, 3.3 mmol) in dichloromethane (20 ml) at 0 °C. The reaction mixture was stirred at 25 °C for 6 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude residue was dissolved in dichloromethane (30 ml) and washed twice with saturated sodium bicarbonate solution (10 ml). The organic layer was separated, washed with brine, then dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography using 50% ethyl acetate as eluent to give 3-bromo-2,5-dimethylaniline (0.45 g, 2.2 mmol, 67% yield). ¹ H-NMR (400 MHz, DMSO -d ₆ ) δ 6.59 (s, 1H), 6.42 (s, 1H), 5.10 (s, 2H), 2.11 (s, 3H), 2.09 (s, 3H).

Stage 4. Receiving N'-(3-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (III)

To a stirred solution of 3-bromo-2,5-dimethylaniline (1.00 g, 5.0 mmol) in trimethyl orthoformate (15 mL) was added anhydrous p -toluenesulfonic acid monohydrate (0.05 g, 0.2 mmol), and the resulting reaction mixture was heated under reflux at 105 °C for 4 h. The crude product was dissolved in 1,4-dioxane (50 mL) under nitrogen atmosphere, followed by the addition of N-ethylmethylamine (0.9 mL, 10 mmol). The resulting reaction mixture was heated under reflux at 80 °C for 3 h. After the completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by column chromatography using 7% ethyl acetate in hexane as eluent to give N'-(3-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (1 g, 3.5 mmol, 71% yield). ¹ H NMR (400 MHz, DMSO -d ₆ ) δ 7.62 (brs, 1H), 6.96 (s, 1H), 6.59 (s, 1H), 3.40-3.31 (m, 2H), 2.91 (s, 3H), 2.22 (s, 3H), 2.18 (s, 3H), 1.11 (t, 3H); LCMS (M+1): 270.90.

b) N'-(3-Bromo-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide

Stage 1. Receiving 1-bromo-5-fluoro-2-methyl-3-nitrobenzene

To a solution of 4-fluoro-1-methyl-2-nitrobenzene (2.00 g, 12.9 mmol) in trifluoroacetic acid (10 mL) was added sulfuric acid (3 mL) at 0 °C, followed by the addition of N-bromosuccinimide (2.4 g, 13.3 mmol) to the reaction mixture, and the reaction mixture was stirred at 0 °C for 1.5 h. After completion of the reaction, the reaction mixture was poured onto crushed ice and extracted with ethyl acetate (50 mL). The ethyl acetate layer was washed with brine, dried over anhydrous sodium sulfate, and evaporated under reduced pressure. The crude product was purified by column chromatography using 10% ethyl acetate in hexane as eluent to give 1-bromo-5-fluoro-2-methyl-3-nitrobenzene (2.2 g, 9.4 mmol, 73% yield) as a yellow liquid. ¹ H-NMR (400 MHz, CDCl ₃ ) δ 7.57 (dd, 1H), 7.50 (dd, 1H), 2.52 (s, 3H); GCMS: 234.9.

Stage 2. Receiving 3-bromo-5-fluoro-2-methylaniline

To a stirred solution of 1-bromo-5-fluoro-2-methyl-3-nitrobenzene (1.0 g, 4.3 mmol) in aqueous ethanol (15 mL, 2:1) were added iron powder (1.7 g, 29.9 mmol) and ammonium chloride (1.1 g, 21.3 mmol). The reaction mixture was heated at 80 °C for 2 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, filtered through a pad of celite and washed thoroughly with ethyl acetate. The combined filtrate was evaporated under reduced pressure. The crude product was neutralized with saturated aqueous sodium bicarbonate (25 mL) and extracted three times with ethyl acetate (50 mL). The combined ethyl acetate layers were washed with water, brine and dried over anhydrous sodium sulfate, evaporated under reduced pressure to give the crude product, which was purified by column chromatography using 10% ethyl acetate in hexane as eluent to give 3-bromo-5-fluoro-2-methylaniline (0.8 g, 3.8 mmol, 89% yield); GCMS: 202.9.

Stage 3. Receiving N'-(3-bromo-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide

To a stirred solution of 3-bromo-5-fluoro-2-methylaniline (1.0 g, 4.9 mmol) in 1,4-dioxane (10 mL) were added p- toluenesulfonic acid monohydrate (0.05 g, 0.2 mmol) and N-(dimethoxymethyl)-N-methylethanamine (1.6 g, 12.3 mmol), and the resulting reaction mixture was heated under reflux at 105 °C for 4 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by column chromatography using 7% ethyl acetate in hexane as the eluent to give N'-(3-bromo-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide (1 g, 3.5 mmol, 72% yield) as a brown liquid. ¹ H-NMR (400 MHz, DMSO -d ₆ ) δ 7.75 (s, 1H), 7.01 (dd, 1H), 6.74-6.71 (m, 1H), 3.44-3.31 (m, 2H), 2.92 (s, 3H), 2.24 (s, 3H), 1.14-1.09 (m, 3H); LCMS (M+1): 274.80.

c) N'-(3-Bromo-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide

Stage 1. Receiving 1-bromo-2-chloro-5-methyl-3-nitrobenzene

To a stirred mixture of 2-bromo-4-methyl-6-nitroaniline (2.0 g, 8.7 mmol), copper(I) chloride (1.7 g, 17.3 mmol) in acetonitrile (20 mL) was added dropwise at 0 °C. After complete addition, the reaction mixture was stirred at 25 °C for 1 h. After completion of the reaction, the reaction mixture was filtered through a pad of celite, washed with acetonitrile. The filtrate was concentrated under reduced pressure. The crude product was dissolved in ethyl acetate (50 mL), washed with aqueous ammonium chloride solution, brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to give a crude product which was purified by column chromatography using 10% ethyl acetate as eluent to give 1-bromo-2-chloro-5-methyl-3-nitrobenzene (1.6 g, 6.6 mmol, 76% yield). ¹ H-NMR (400 MHz, DMSO -d ₆ ) δ 8.02-7.97 (1H), 7.94-7.90 (1H), 2.40-2.37 (3H); GCMS: 252.80.

Stage 2. Receiving 3-bromo-2-chloro-5-methylaniline

To a stirred solution of 1-bromo-2-chloro-5-methyl-3-nitrobenzene (1.00 g, 4 mmol) in aqueous ethanol (15 mL, 2:1) were added iron powder (1.6 g, 27.9 mmol) and ammonium chloride (1.1 g, 20 mmol). The reaction mixture was heated at 80 °C for 2 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, filtered through a pad of celite and washed thoroughly with ethyl acetate. The combined filtrate was evaporated under reduced pressure. The crude product was neutralized with saturated aqueous sodium bicarbonate and extracted three times with ethyl acetate (50 mL). The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the crude product, which was purified by column chromatography using 10% ethyl acetate as eluent to give 3-bromo-2-chloro-5-methylaniline (0.8 g, 3.5 mmol, 89% yield) as a brown liquid. ¹ H-NMR (400 MHz, DMSO -d ₆ ) δ 6.73-6.71 (m, 1H), 6.59-6.57 (m, 1H), 5.57 (s, 2H), 2.15 (s, 3H); LCMS (M+1): 222.00.

Stage 3. Receiving N'-(3-bromo-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide

To a stirred solution of 3-bromo-2-chloro-5-methylaniline (1.0 g, 4.5 mmol) in 1,4-dioxane (10 mL) were added anhydrous p- toluenesulfonic acid monohydrate (0.04 g, 0.2 mmol) and N-(dimethoxymethyl)-N-methylethanamine (1.5 g, 11.3 mmol), and the resulting mixture was heated under reflux at 105 °C for 4 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by column chromatography using 7% ethyl acetate in hexane as the eluent to give N'-(3-bromo-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide (0.9 g, 3.3 mmol, 73% yield) as a brown liquid. ¹ H-NMR (400 MHz, DMSO -d ₆ ) δ 7.74 (s, 1H), 7.13-7.11 (m, 1H), 6.84-6.78 (m, 1H), 3.47-3.31 (m, 2H), 2.94 (s, 3H), 2.23 (s, 3H), 1.16-1.1 2 (m, 3H); LCMS (M+1): 290.80.

Example 2. Receiving N'-(3-benzyl-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide

a) Receipt N'-(2,5-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide

A stirred mixture of N'-(3-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (1.0 g, 3.7 mmol), bis(pinacol)diboron (1.9 g, 7.4 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane [PdCl ₂ (dppf)-CH ₂ Cl ₂ ] (0.2 g, 0.2 mmol), and potassium acetate (0.7 g, 7.4 mmol) in 1,4-dioxane (30 mL) was degassed with nitrogen for 5 min. The reaction mixture was stirred at 95 °C for 16 h under nitrogen. After completion of the reaction, the reaction mixture was diluted with dichloromethane, filtered through a pad of celite, and the residue was washed with dichloromethane (100 mL). The combined filtrate was washed with brine and dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure. The crude product was purified by column chromatography using 10% ethyl acetate in hexane as eluent to give N'-(2,5-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide (0.8 g, 70% yield).

b) Receipt N'-(3-benzyl-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide

A mixture of N'-(2,5-dimethyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)-N-ethyl-N-methylformimidamide (0.5 g, 1.6 mmol), (bromomethyl)benzene (0.3 g, 1.6 mmol), Pd(Ph ₃ p) ₄ [tetrakis(triphenylphosphine)palladium(0)] (0.09 g, 0.08 mmol) and potassium carbonate (0.5 g, 3.9 mmol) in dioxane:water (12 mL, 8:2) was degassed with nitrogen. The reaction mixture was stirred at 100 °C for 4 h under nitrogen atmosphere. After completion of the reaction, the reaction mixture was cooled to 25 °C, filtered through a pad of celite. The filtrate was diluted with ethyl acetate and washed with brine, dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using 7% ethyl acetate in hexane as eluent to give N'-(3-benzyl-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide (0.4 g, 63% yield).

Example 3. Receiving N-ethyl-N'-(3-(3-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide

a) Receipt 4-methyl-2-nitro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline

A stirred mixture of 2-bromo-4-methyl-6-nitroaniline (2.00 g, 8.7 mmol), bis(pinacol)diboron (4.4 g, 17.3 mmol), [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II)dichloromethane [ _PdCl2 (dppf) _{-CH2Cl2 ]} (0.35 g, 0.4 mmol), and potassium acetate (2.1 g, 21.6 mmol) in 1,4-dioxane (30 mL) was degassed with nitrogen. The reaction mixture was stirred at 95 °C for 16 h under nitrogen. After completion of the reaction, the reaction mixture was diluted with dichloromethane, filtered through a pad of celite, and the residue was washed with dichloromethane (100 mL). The combined filtrate was washed with brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by column chromatography with 10% ethyl acetate in hexane to give 4-methyl-2-nitro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2 g, 7.3 mmol, 85% yield) as a yellow solid. ¹ H NMR (400 MHz, DMSO -d ₆ ) δ 7.97 (d, 1H), 7.65 (d, 1H), 7.30 (s, 2H), 2.21 (s, 3H), 1.33 (s, 12H); GCMS: 278.2.

b) Receipt 2-(3-fluorobenzyl)-4-methyl-6-nitroaniline

A mixture of 4-methyl-2-nitro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (2.0 g, 7.2 mmol), 1-(bromomethyl)-3-fluorobenzene (1.4 g, 7.2 mmol), tetrakis(triphenylphosphine)palladium(0) [Pd(Ph ₃ P) ₄ ] (0.42 g, 0.4 mmol) and potassium carbonate (2.5 g, 17.9 mmol) in dioxane:water (35 mL, 8:2) was degassed with nitrogen. The reaction mixture was stirred at 100 °C for 4 h under nitrogen atmosphere. After completion of the reaction, the reaction mixture was cooled to 25 °C, filtered through a pad of celite. The filtrate was diluted with ethyl acetate (200 mL) and washed with brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using 10% ethyl acetate in hexane as eluent to give 2-(3-fluorobenzyl)-4-methyl-6-nitroaniline (1.4 g, 5.2 mmol, 73% yield) as a yellow solid. ¹ H NMR (400 MHz, DMSO -d ₆ ) δ 7.74 (d, 1H), 7.35-7.29 (m, 1H), 7.14 (d, 1H), 7.09-7.00 (m, 3H), 3.98 (s, 2H), 2.16 (s, 3H); GCMS: 260.1.

c) Receipt 2-bromo-1-(3-fluorobenzyl)-5-methyl-3-nitrobenzene

To a stirred mixture of 2-(3-fluorobenzyl)-4-methyl-6-nitroaniline (2.0 g, 8.3 mmol), copper(I) bromide (2.2 g, 15.4 mmol) in acetonitrile (20 mL) was added dropwise at 0 °C. After complete addition, the reaction mixture was stirred at 25 °C for 1 h. After completion of the reaction, the reaction mixture was filtered through a pad of celite, washed with acetonitrile. The filtrate was concentrated under reduced pressure. The crude product was dissolved in ethyl acetate (50 mL), washed with aqueous ammonium chloride solution, brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure to give the crude product, which was purified by column chromatography using 10% ethyl acetate in hexane as eluent to give 2-bromo-1-(3-fluorobenzyl)-5-methyl-3-nitrobenzene (1.8 g, 5.5 mmol, 71% yield) as a yellow solid. ¹ H NMR (400 MHz, DMSO -d ₆ ) δ 7.68 (d, 1H), 7.49 (d, 1H), 7.37-7.31 (m, 1H), 7.07-7.01 (m, 3H), 4.17 (s, 2H), 2.32 (s, 3H); GCMS: 324.9.

d) Receiving 3-(3-fluorobenzyl)-2,5-dimethylaniline

A mixture of 2-bromo-1-(3-fluorobenzyl)-5-methyl-3-nitrobenzene (2.0 g, 6.2 mmol), methyl boronic acid (0.7 g, 12.3 mmol), _PdCl2 (dppf) _-CH2Cl2 adduct (0.5 g, 0.6 _mmol ) and tribasic potassium phosphate (3.3 g, 15.4 mmol) in dioxane:water (35 mL, 8:2) was degassed with nitrogen. The reaction mixture was stirred at 100 °C for 4 h under nitrogen atmosphere. After completion of the reaction, the reaction mixture was cooled to 25 °C, filtered through a pad of celite. The filtrate was diluted with ethyl acetate (200 mL) and washed with brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by column chromatography using 10% ethyl acetate in hexane as eluent to give 1-(3-fluorobenzyl)-2,5-dimethyl-3-nitrobenzene (1.4 g, 5.5 mmol, 89% yield) as a yellow solid. ¹ H NMR (400 MHz, DMSO -d ₆ ) δ 7.55 (s, 1H), 7.36-7.30 (m, 2H), 7.05-7.00 (m, 1H), 6.96 (d, 2H), 4.08 (s, 2H), 2.32 (s, 3H), 2.18 (s, 3H); GCMS: 259.1.

e) Receipt 3-(3-fluorobenzyl)-2,5-dimethylaniline

To a stirred solution of 1-(3-fluorobenzyl)-2,5-dimethyl-3-nitrobenzene (1 g, 3.8 mmol) in aqueous ethanol (15 mL, 2:1) were added iron powder (1.0 g, 19.2 mmol) and ammonium chloride (1.4 g, 27.0 mmol). The reaction mixture was heated at 80 °C for 2 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, filtered through a pad of celite and washed thoroughly with ethyl acetate. The combined filtrate was evaporated under reduced pressure. The crude product was diluted with saturated aqueous sodium bicarbonate and extracted three times with ethyl acetate (50 mL). The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the crude product, which was purified by column chromatography using 10% ethyl acetate in hexane as eluent to give 3-(3-fluorobenzyl)-2,5-dimethylaniline (0.8 g, 3.4 mmol, 89% yield) as a brown liquid. ¹ H-NMR (400 MHz, DMSO -d ₆ ) δ 7.32-7.27 (m, 1H), 7.00-6.95 (m, 2H), 6.88 (d, 1H), 6.38 (s, 1H), 6.26 (s, 1H), 4.69 (s, 2H), 3.86 (s, 2H), 2 .12 (s, 3H), 1.85 (s, 3H); GCMS: 229.1.

f) Receipt N-ethyl-N'-(3-(3-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide

To a stirred solution of 3-(3-fluorobenzyl)-2,5-dimethylaniline (1.0 g, 4.3 mmol) in 1,4-dioxane (10 mL) were added anhydrous p- toluenesulfonic acid monohydrate (0.04 g, 0.2 mmol) and N-(dimethoxymethyl)-N-methylethanamine (0.6 g, 4.3 mmol), and the resulting mixture was heated under reflux at 105°C for 4 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The crude product was purified by column chromatography using 7% ethyl acetate in hexane as eluent to give N-ethyl-N'-(3-(3-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide (0.9 g, 3.1 mmol, 70% yield) as a brown liquid. ¹ H-NMR (400 MHz, DMSO - _d6 ) δ 7.57 (brs, 1H), 7.33-7.27 (m, 1H), 7.01-6.95 (m, 2H), 6.91-6.87 (m, 1H), 6.61 (s, 1H), 6.50 (s, 1H), 3.91 (s, 2H), 3.41-3.33 (m, 2H), 2.92 (s, 3H), 2.20 (s 3H), 2.04 (s, 3H), 1.12 (t, 3H); LCMS (M+1): 299.15.

Example 4. Receiving N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(pyridin-2-yl)amino)phenyl)-N-methylformimidamide

a) Receipt 3-bromo-5-fluoro-2-methylaniline

To a stirred solution of 1-bromo-5-fluoro-2-methyl-3-nitrobenzene (10 g, 42.7 mmol) in aqueous ethanol (130 mL, 2:1) were added iron powder (23.9 g, 427 mmol) and ammonium chloride (22.9 g, 427 mmol). The reaction mixture was heated at 80 °C for 2 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, filtered through a pad of celite and washed thoroughly with ethyl acetate (250 mL). The combined filtrate was evaporated under reduced pressure. The crude product was diluted with saturated aqueous sodium bicarbonate and extracted three times with ethyl acetate (150 mL). The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the crude product, which was purified by column chromatography using 5% ethyl acetate in hexane as eluent to give the desired 3-bromo-5-fluoro-2-methylaniline (8 g, 39.0 mmol, 91% yield); GCMS: 202.9.

b) Receipt N'-(3-bromo-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide

To a stirred solution of 3-bromo-5-fluoro-2-methylaniline (8 g, 39.2 mmol) in trimethyl orthoformate (50 mL) was added anhydrous p -toluenesulfonic acid monohydrate (0.75 g, 3.9 mmol), and the resulting mixture was heated under reflux at 105 °C for 4 h. The crude product was dissolved in 1,4-dioxane (50 mL) under nitrogen atmosphere, followed by the addition of N-ethylmethylamine (10.1 mL, 12 mmol). The resulting reaction mixture was heated under reflux at 80 °C for 3 h. The crude product was purified by column chromatography using 7% ethyl acetate in hexane as eluent to give N'-(3-bromo-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide (8 g, 29.3 mmol, 75% yield). ¹ H NMR (400 MHz, DMSO -d ₆ ) δ 7.75-7.64 (m, 1H), 7.00 (dd, 1H), 6.77-6.71 (m, 1H), 3.46-3.33 (m, 2H), 3.01-2.92 (m, 3H), 2.25 (d, 3H), 1.13 (t, 3H); LCMS (M+1) 272.7,

c) Receipt N-ethyl-N'-(5-fluoro-2-methyl-3-(pyridin-2-ylamino)phenyl)-N-methylformimidamide

A stirred suspension of N'-(3-bromo-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide (0.7 g, 2.5 mmol), pyridin-2-amine (0.3 g, 3.1 mmol), cesium carbonate (2.1 g, 6.4 mmol) in anhydrous toluene (10 mL) was degassed with nitrogen for 15 min. Palladium acetate (0.03 g, 0.1 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) (BINAP) (0.16 g, 0.3 mmol) were added and the reaction mixture was heated at 100 °C for 16 h under nitrogen. After completion of the reaction, the reaction mixture was passed through celite, washed thoroughly with ethyl acetate (25 mL). The combined organic layers were washed twice with water (50 mL), once with brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude product was purified by column chromatography using 40% ethyl acetate in hexane as eluent to give N-ethyl-N'-(5-fluoro-2-methyl-3-(pyridin-2-ylamino)phenyl)-N-methylformimidamide (0.3 g, 1 mmol, 38% yield); LCMS: 286.95.

d) Receiving N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(pyridin-2-yl)amino)phenyl)-N-methylformimidamide

A solution of N-ethyl-N'-(5-fluoro-2-methyl-3-(pyridin-2-ylamino)phenyl)-N-methylformimidamide (0.2 g, 0.7 mmol) in N,N'- dimethylformamide (3 mL) was added dropwise at 0-5 °C to a suspension of sodium hydride (0.06 g, 1.4 mmol) and the reaction mixture was stirred for 15 min. Then methyl iodide (0.12 g, 1.4 mmol) was added dropwise and stirring was continued for 45 min. After completion of the reaction, the mixture was quenched in ice water and extracted twice with ethyl acetate (50 mL). The organic layer was washed twice with water (50 mL) and then with brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated. The resulting crude product was purified by column chromatography using 10% ethyl acetate in hexane as eluent to give N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(pyridin-2-yl)amino)phenyl)-N-methylformimidamide (0.16 g, 0.5 mmol, 74% yield); LCMS: 301.4.

Example 5. Synthesis N'-(2-chloro-5-methyl-3-(methyl(pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide

a) Receipt 1-bromo-2-chloro-5-methyl-3-nitrobenzene

To a solution of 2-bromo-4-methyl-6-nitroaniline (15 g, 64.9 mmol) in acetonitrile (150 mL) was added copper(I) chloride (9.6 g, 97 mmol), and the reaction mixture was stirred at 25 °C for 30 min. Then tert -butyl nitrite (38.5 mL, 325 mmol) was added dropwise at 0 °C, and the reaction mixture was slowly brought to 25 °C with continued stirring for 2 h. After completion of the reaction, the reaction mixture was quenched with aqueous ammonium chloride solution and extracted three times with ethyl acetate (200 mL). The combined organic layers were washed with brine (200 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The resulting crude product was purified by column chromatography using 10% ethyl acetate in hexane as eluent to give 1-bromo-2-chloro-5-methyl-3-nitrobenzene (12 g, 48 mmol, 74% yield); GCMS: 251.0.

b) Receipt 3-bromo-2-chloro-5-methylaniline

To a stirred solution of 1-bromo-2-chloro-5-methyl-3-nitrobenzene (13 g, 51.9 mmol) in aqueous ethanol (130 mL, 2:1) were added iron powder (29 g, 519 mmol) and ammonium chloride (27.8 g, 519 mmol). The reaction mixture was heated at 80 °C for 2 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, filtered through a pad of celite and washed thoroughly with ethyl acetate. The combined filtrate was evaporated under reduced pressure. The crude product was diluted with saturated aqueous sodium bicarbonate and extracted three times with ethyl acetate (250 mL). The combined organic layers were washed with water, brine, dried over anhydrous sodium sulfate, filtered and evaporated under reduced pressure to give the crude product, which was purified by column chromatography using 10% ethyl acetate in hexane as eluent to give 3-bromo-2-chloro-5-methylaniline (9.1 g, 41 mmol, 79% yield); GCMS: 220.9.

c) Receipt N'-(3-bromo-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide

To a stirred solution of 3-bromo-2-chloro-5-methylaniline (8.5 g, 38.5 mmol) in trimethyl orthoformate (50 mL) was added anhydrous p -toluenesulfonic acid monohydrate (0.7 g, 3.8 mmol), and the resulting mixture was heated under reflux at 105 °C for 4 h. The crude product was dissolved in 1,4-dioxane (50 mL) under nitrogen atmosphere, followed by the addition of N-ethylmethylamine (10.1 mL, 118 mmol). The resulting reaction mixture was heated under reflux at 80 °C for 3 h. The crude product was purified by column chromatography using 7% ethyl acetate in hexane as eluent to give N'-(3-bromo-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide (8.9 g, 31.4 mmol, 82% yield). ¹ H NMR (400 MHz, DMSO -d ₆ ) δ 7.74-7.63 (m, 1H), 7.12 (q, 1H), 6.80 (d, 1H), 3.47-3.30 (m, 4H), 3.03-2.94 (m, 3H), 2.22 (d, 3H), 1.15 (t, 3H); LCMS (M+1) 291.0.

d) Receiving N'-(2-chloro-5-methyl-3-(pyridin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide

A mixture of N'-(3-bromo-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide (0.7 g, 2.41 mmol), pyridin-2-amine (0.3 g, 3.1 mmol), cesium carbonate (2 g, 6.0 mmol) in anhydrous toluene (10 mL) was degassed with nitrogen. Palladium acetate (0.03 g, 0.1 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) (BINAP) (0.15 g, 0.2 mmol) were added and the reaction mixture was heated at 100 °C for 16 h under nitrogen. After completion of the reaction, the reaction mixture was passed through celite and washed with ethyl acetate (50 mL). The combined organic layers were washed twice with water (50 mL), brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude product was purified by column chromatography using 40% ethyl acetate in hexane as eluent to give N'-(2-chloro-5-methyl-3-(pyridin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide (0.5 g, 40.8 mmol, 72% yield); LCMS: 303.4.

e) Receipt N'-(2-chloro-5-methyl-3-(methyl(pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide

To a suspension of sodium hydride (0.1 g, 1.7 mmol) in N,N -dimethylformamide (5 mL) was added dropwise at 0-5 °C a solution of N'-(2-chloro-5-methyl-3-(pyridin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide (0.3 g, 1.1 mmol) in N,N -dimethylformamide (3 mL). After stirring for 15 min, methyl iodide (0.2 g, 1.4 mmol) was added to the reaction mixture and stirring was continued for another 1 h. After completion of the reaction, the reaction mixture was quenched in ice water, extracted twice with ethyl acetate (50 mL). The organic layer was washed twice with water (25 mL), brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude product was purified by column chromatography using 10% ethyl acetate in hexane as eluent to give N'-(2-chloro-5-methyl-3-(methyl(pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide (0.22 g, 0.7 mmol, 62% yield); LCMS: 317.40.

Example 6. Receiving N'-(3-(2-(2-chloro-4-methoxyphenoxy)acetyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide

a) Receipt 2-chloro-N-methoxy-N-methylacetamide

To a stirred solution of N,O-dimethylhydroxylamine hydrochloride (25 g, 256 mmol) in diethyl ether (50 mL) and water (50 mL) was added potassium carbonate (78 g, 564 mmol) followed by 2-chloroacetyl chloride (24.50 mL, 308 mmol). The reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was quenched by addition of water and the mixture was extracted twice with 1,2-dichloromethane (250 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over sodium sulfate and evaporated under reduced pressure to give 2-chloro-N-methoxy-N-methylacetamide (25 g, 182 mmol, 71% yield).

b) Receipt 2-(2-chloro-4-methoxyphenoxy)-N-methoxy-N-methylacetamide

To a stirred solution of 2-chloro-4-methoxyphenol (2.77 g, 17.45 mmol) in N,N -dimethylformamide (15 mL) was added potassium carbonate (4.02 g, 29.1 mmol) followed by 2-chloro-N-methoxy-N-methylacetamide (2 g, 14.54 mmol) and the reaction mixture was stirred at 25 °C for 16 h. After completion of the reaction, the reaction mixture was quenched with ice water and extracted three times with ethyl acetate (150 mL). The combined organic layers were washed with water, brine, dried over sodium sulfate and the solvent was evaporated under reduced pressure to give 2-(2-chloro-4-methoxyphenoxy)-N-methoxy-N-methylacetamide (2.9 g, 11.17 mmol, 77% yield).

c) Receipt N'-(3-(2-(2-chloro-4-methoxyphenoxy)acetyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide

To a stirred solution of N'-(3-bromo-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide (0.7 g, 2.56 mmol) in tetrahydrofuran (10 mL) was added n-butyllithium (2.56 mL, 5.13 mmol) at -78 °C. The reaction mixture was stirred at -78 °C for 1 h and then 2-(2-chloro-4-methoxyphenoxy)-N-methoxy-N-methylacetamide (0.799 g, 3.08 mmol) was added and the reaction mixture was allowed to stir for 1 h at -78 °C. After completion of the reaction, the reaction mixture was quenched with aqueous ammonium chloride solution and extracted three times with ethyl acetate (75 mL). The combined organic layers were washed with water (50 mL), brine and dried over anhydrous sodium sulfate; the solvent was evaporated under reduced pressure. The crude product was further purified by preparative high-performance liquid chromatography to give N'-(3-(2-(2-chloro-4-methoxyphenoxy)acetyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide (0.116 g, 0.295 mmol, 11% yield).

Example 7. Receiving N'-(2-chloro-5-methyl-3-((2-(trifluoromethyl)benzyl)amino)phenyl)-N-ethyl-N-methylformimidamide

A stirred suspension of N'-(3-bromo-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide (0.7 g, 2.417 mmol), (2-(trifluoromethyl)phenyl)methanamine (0.441 mL, 3.14 mmol), and cesium carbonate (1.969 g, 6.04 mmol) in anhydrous toluene (10 mL) was degassed with nitrogen for 15 min. Palladium acetate (0.027 g, 0.121 mmol) and 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl) (BINAP) (0.151 g, 0.242 mmol) were added to the reaction mixture, and the reaction mixture was heated at 100 °C for 16 h under nitrogen. After completion of the reaction, the reaction mixture was passed through celite, washed thoroughly with ethyl acetate (25 mL). The combined organic layers were washed twice with water (50 mL), once with brine (50 mL), dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The resulting crude product was purified by column chromatography using 40% ethyl acetate in hexane as eluent to give N'-(2-chloro-5-methyl-3-((2-(trifluoromethyl)benzyl)amino)phenyl)-N-ethyl-N-methylformimidamide (0.16 g, 0.417 mmol, 17% yield).

The following compounds in Table I were prepared using similar procedures as described in Schemes 1–21 or in the Examples.

Table I

* Names of compounds obtained using Chemdraw Professional 17.1

As described herein, the compounds of general formula (I) exhibit fungicidal activity against numerous phytopathogenic fungi that attack important agricultural crops. The compounds of the present invention were evaluated for their activity as described in the following tests.

Examples biological tests, trial in vitro

Example 1. Pyricularia oryzae (blast disease) rice)

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium immediately before dispensing into Petri dishes. Five milliliters of medium containing the desired concentration of compound were dispensed into 60-mm sterile Petri dishes. After the medium had solidified, each plate was seeded with a 5-mm mycelial disk taken from the peripheral zone of a plate containing an actively growing virulent culture. The plates were incubated in growth chambers at 25°C and 60% relative humidity for seven days, and then radial growth was measured and compared with that of an untreated control. Connections 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 44, 45, 46, 47, 48, 49, 50, 51, 52, 54, 55, 56, 57, 58, 59, 60, 61, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 75, 76, 77, 78, 79, 80, 82, 83, 86, 87, 88, 89, 90, 91, 92, 93, 94, 96, 97, 98, 100, 101, 102, 103, 104, 05, 107, 108, 111, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 129, 130, 133, 134, 135, 136, 137, 138, 139, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 154, 155, 157, 159, 160, 1, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 179, 181, 182, 183, 185, 188, 190, 191, 201, 202, 203, 204, 205, 206, 207, 208, 213, 214, 216, 217, 218, 219, 220, 221, 222, 223, 224, 225, 228, 23 0, 231, 232, 233, 234, 235, 236, 237, 238, 240, 241, 242, 243, 244, 245, 246, 247, 248, 249, 250, 251, 252, 253, 254, 259, 261, 262, 263, 264, 265, 266, 267, 271, 272, 273, 274, 275, 276, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 308, 309, 310, 311, 313 at 300 ppm provided at least 70% control in such tests compared to untreated controls, which demonstrated extensive disease development.

Example 2. Rhizoctonia solani (disease epidermis rice/black scab potatoes)

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium immediately before dispensing into Petri dishes. Five milliliters of medium containing the desired concentration of compound were dispensed into 60-mm sterile Petri dishes. After the medium had solidified, each plate was seeded with a 5-mm mycelial disk taken from the peripheral zone of a plate containing an actively growing virulent culture. The plates were incubated in growth chambers at 25°C and 60% relative humidity for seven days, and then radial growth was measured and compared with that of an untreated control. Connections 1, , 2, 3, 4, 5, 6, 7, 9, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 34, 35, 37, 38, 42, 44, 45, 46, 48, 50, 51, 52, 54, 55, 56, 58, 59, 60, 61, 64, 65, 67, 68, 69, 70, 71, 72, 73, 75, 76, 77, 79, 80, 82, 83, 84, 87, 88, 89, 90, 91, 92, 93, 94, 96, 98, 100, 102, 103, 104, 105, 113, 124, 125, 126, 127, 128, 129, 130, 31, 133, 134, 135, 136, 138, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 154, 161, 162, 163, 164, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 181, 182, 183, 185, 188, 189, 190, 191, 201, 202, 203, 204, 5, 206, 207, 208, 209, 213, 214, 216, 217, 218, 219, 220, 221, 222, 223, 224, 229, 230, 231, 232, 233, 234, 235, 236, 239, 241, 242, 243, 244, 245, 246, 247, 253, 254, 255, 259, 260, 261, 262, 263, 264, 265, 266, 273, 274, 275, 276, 286, 287, 292, 293, 294, 295, 296, 298, 299, 300, 301, 302, 303, 305, 306, 307, 308, 311 at 300 ppm provided at least 70% control in such tests compared to untreated controls, which demonstrated extensive disease development.

Example 3. Botrytis cinerea (gray mold)

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium immediately before dispensing into Petri dishes. Five milliliters of medium containing the desired concentration of compound was dispensed into 60-mm sterile Petri dishes. After the medium had solidified, each plate was seeded with a 5-mm mycelial disk taken from the peripheral zone of a plate containing an actively growing virulent culture. The plates were incubated in growth chambers at 22°C and 90% relative humidity for seven days, and then radial growth was measured and compared with that of an untreated control. Connections 2, , 3, 4, 5, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 24, 25, 26, 27, 29, 31, 32, 33, 34, 35, 37, 38, 40, 41, 42, 43, 44, 45, 46, 50, 51, 52, 54, 55, 56, 57, 58, 59, 60, 62, 63, 65, 67, 68, 70, 71, 72, 73, 76, 77, 79, 80, 81, 83, 84, 87, 88, 89, 90, 91, 92, 93, 94, 96, 98, 100, 102, 103, 105, 106, 110, 117, 118, 119, 122, 123, 124, 125, 126, 128, 129, 133, 134, 136, 140, 141, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 159, 160, 161, 163, 164, 166, 170, 171, 172, 173, 174, 175, 176, 178, 179, 181, 182, 183, 185, 188, 191, 201, 202, 203, 204, 205, 206, 207, 208, 213, 6, 217, 220, 221, 222, 223, 224, 229, 230, 231, 232, 233, 235, 236, 237, 244, 245, 246, 247, 259, 261, 262, 263, 264, 273, 274, 286, 287, 288, 292, 293, 294, 295, 296, 297, 299, 301, 302, 303, 305, 307, 308, 310, 311 at 300 ppm provided at least 70% control in such tests compared to untreated controls which showed extensive disease development.

Example 4. Alternaria solani (Alternaria blight tomatoes/potatoes)

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium immediately before dispensing into Petri dishes. Five milliliters of medium containing the desired concentration of compound were dispensed into 60-mm sterile Petri dishes. After the medium had solidified, each plate was seeded with a 5-mm mycelial disk taken from the peripheral zone of a plate containing an actively growing virulent culture. The plates were incubated in growth chambers at 25°C and 60% relative humidity for seven days, and then radial growth was measured and compared with that of an untreated control. Connections, , 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 22, 23, 24, 25, 26, 27, 28, 29, 30, 31, 32, 33, 34, 35, 36, 37, 38, 39, 40, 41, 42, 43, 44, 45, 46, 47, 48, 49, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 61, 62, 63, 64, 65, 66, 67, 68, 69, 70, 71, 72, 73, 74, 75, 76, 77, 78, 79, 80, 81, 82, 83, 84, 85, 86, 87, 88, 89, 90, 91, , 93, 94, 96, 98, 100, 101, 102, 103, 104, 105, 106, 108, 110, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 123, 125, 126, 127, 128, 129, 130, 131, 133, 136, 137, 138, 140, 142, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 4, 155, 156, 157, 159, 160, 161, 162, 163, 164, 165, 166, 167, 168, 169, 170, 171, 172, 173, 174, 175, 176, 177, 178, 180, 181, 182, 183, 185, 188, 189, 190, 191, 201, 202, 203, 204, 205, 206, 207, 208, 209, 213, 214, 216, 217, 218, 219, 0, 221, 222, 223, 224, 225, 226, 227, 228, 229, 230, 231, 232, 233, 234, 235, 236, 237, 238, 239, 240, 241, 242, 243, 245, 246, 247, 253, 254, 255, 259, 260, 261, 262, 263, 264, 265, 266, 268, 269, 271, 272, 273, 274, 275, 276, 286, 287, 288, 289, 290, 291, 292, 293, 294, 295, 296, 297, 298, 299, 300, 301, 302, 303, 304, 305, 306, 307, 308, 310 at 300 ppm provided a minimum of 70% control in such trials compared to untreated controls, which demonstrated extensive disease progression.

Example 5. Colletotrichum capsicum (anthracnose)

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium immediately before dispensing into Petri dishes. Five milliliters of medium containing the desired concentration of compound were dispensed into 60-mm sterile Petri dishes. After the medium had solidified, each plate was seeded with a 5-mm mycelial disk taken from the peripheral zone of a plate containing an actively growing virulent culture. The plates were incubated in growth chambers at 25°C and 60% relative humidity for seven days, and then radial growth was measured and compared with that of an untreated control. Connections, , 1, 2, 3, 4, 5, 7, 9, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 21, 23, 24, 25, 26, 27, 31, 34, 35, 36, 37, 38, 39, 40, 41, 44, 45, 46, 48, 50, 51, 56, 58, 59, 60, 61, 62, 65, 67, 68, 71, 73, 75, 77, 79, 88, 89, 90, 91, 92, 93, 94, 96, 98, 100, 101, 102, 103, 105, 112, 113, 114, 115, 116, 118, 120, 123, 124, 125, 126, 128, 129, 131, 133, 139, 143, 144, 150, 2, 156, 161, 162, 163, 171, 172, 181, 183, 189, 190, 201, 203, 204, 207, 208, 209, 213, 216, 217, 219, 220, 221, 222, 224, 225, 226, 233, 235, 236, 244, 245, 246, 254, 255, 263, 275, 287 at 300 ppm provided at least 70% control in such tests compared to untreated controls which showed extensive disease development.

Example 6. Septoria lycopersic / Corynespora cassicola (CORYCA) (spotting leaves tomatoes)

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium immediately before dispensing into Petri dishes. Five milliliters of medium containing the desired concentration of compound were dispensed into 60-mm sterile Petri dishes. After the medium had solidified, each plate was seeded with a 5-mm mycelial disk taken from the peripheral zone of a plate containing an actively growing virulent culture. The plates were incubated in growth chambers at 25°C and 70% relative humidity for seven days, and then radial growth was measured and compared with that of an untreated control. Connections 2, , 3, 4, 5, 6, 9, 10, 11, 12, 13, 14, 15, 16, 17, 18, 19, 20, 22, 23, 24, 25, 29, 30, 31, 35, 36, 37, 38, 43, 44, 50, 51, 52, 54, 55, 56, 58, 59, 60, 67, 70, 72, 73, 76, 77, 79, 84, 89, 91, 92, 94, 96, 100, 101, 103, 112, 113, 114, 115, 116, 117, 118, 119, 120, 121, 123, 124, 125, 126, 128, 129, 130, 131, 133, 136, 138, 140, 141, 142, 143, 144, 145, 146, 7, 148, 149, 151, 159, 161, 162, 163, 164, 165, 166, 188, 189, 191, 201, 203, 204, 205, 206, 207, 208, 209, 213, 214, 217, 219, 220, 221, 222, 223, 224, 226, 235, 236, 237, 243, 259, 261, 262, 263, 264, 265, 266, 271, 272, 273, 274, 275, 276, 286, 287, 291, 292, 293, 294, 295, 296, 297, 299, 300, 301, 302, 303, 305, 307, 308 at 300 ppm provided at least 70% control in such tests compared to untreated controls, which demonstrated extensive disease development.

Example 7. Fusarium culmorum (root rot cereals)

Compounds were dissolved in 0.3% dimethyl sulfoxide and then added to potato dextrose agar medium immediately before dispensing into Petri dishes. Five milliliters of medium containing the desired concentration of compound were dispensed into 60-mm sterile Petri dishes. After the medium had solidified, each plate was seeded with a 5-mm mycelial disk taken from the peripheral zone of a plate containing an actively growing virulent culture. The plates were incubated in growth chambers at 25°C and 60% relative humidity for seven days, and then radial growth was measured and compared with that of an untreated control. Connections 1, , 2, 3, 4, 5, 12, 13, 17, 18, 20, 25, 26, 35, 44, 46, 51, 52, 54, 55, 56, 59, 73, 77, 87, 88, 105, 112, 116, 120, 124, 125, 126, 129, 142, 162, 163, 164, 188, 190, 204, 207, 208, 214, 220, 221, 222, 223, 224, 236, 246, 261, 262, 263, 264, 265, 266, 271, 275, 286, 287, 292, 293, 294, 295, 299, 305, 307 at 300 ppm provided at least 70% control in such tests compared to untreated controls which showed extensive disease development.

Examples biological tests on plants in vivo

Example A. Trial rice V relation Pyricularia oryzae

The compounds were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to an exact spray volume of 50 ml. 50 ml of this spray solution was poured into spray bottles for additional applications.

To test the preventive activity of the compounds, healthy young rice seedlings/plants grown in a greenhouse were sprayed with a formulation of the active compound at the specified application rates inside spray chambers using hollow cone nozzles. One day after the treatment, the plants were inoculated with a spore suspension (sterile water) containing 1.4 x 10 ⁶ Pyricularia oryzae inoculum. The inoculated plants were then maintained in a greenhouse chamber at 24°C and 95% relative humidity for disease development.

Visual assessment of the efficacy of the compounds was performed by rating the disease severity (0-100% scale) on the treated plants at 3, 7, 10 and 15 days after application. The efficacy (% control) of the compounds was calculated by comparing the disease severity of the treated plants with that of the untreated control. The treated plants were also assessed for plant compatibility by recording symptoms such as necrosis, chlorosis and stunting. Compounds 50, 51, 52, 54, 55, 94, 178, 180, 181, 277 at 500 ppm provided at least 70% control in these tests compared to the untreated control which showed extensive disease development.

Example B. Trial tomatoes V relation Botrytis cinera

The compounds were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to an exact spray volume of 50 ml. 50 ml of this spray solution was poured into spray bottles for additional applications.

To test the preventive activity of the compounds, healthy young bean/capsicum plants grown in a greenhouse were sprayed with a formulation of the active compound at the specified application rates inside spray chambers using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension (2% malt) containing 1.2 x 10 ⁶ Botrytis cinerea inoculum. The inoculated plants were then maintained in a greenhouse chamber at 18-20°C and 90-100% relative humidity for disease development.

Visual assessment of the efficacy of the compounds was performed by rating the disease severity (0-100% scale) on the treated plants at 3, 7, 10 and 15 days after application. The efficacy (% control) of the compounds was calculated by comparing the disease severity of the treated plant with that of the untreated control. The treated plants were also assessed for plant compatibility by recording symptoms such as necrosis, chlorosis and stunting. Compounds 27, 36, 39, 45, 49, 192, 258, 263, 264, 269, 282 at 500 ppm provided at least 70% control in these tests compared to the untreated control which showed extensive disease development.

Example C. Trial soybeans V relation Phakopsora pachyrrhizi

The compounds were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to an exact spray volume of 50 ml. 50 ml of this spray solution was poured into spray bottles for additional applications.

To test the preventive activity of the compounds, healthy young soybean plants grown in a greenhouse were sprayed with a formulation of the active compound at the specified application rates inside spray chambers using hollow cone nozzles. One day after treatment, the plants were inoculated with a suspension containing 2 x 10 ⁵ Phakopsora pachyrhizi conidia . The inoculated plants were then maintained in a greenhouse chamber at 22-24°C and 80-90% relative humidity for disease development.

Visual assessment of the efficacy of the compounds was performed by assessing the severity of the disease (scale 0-100%) on the treated plants at 3, 7, 10 and 15 days after application. The efficacy (% control) of the compounds was calculated by comparing the severity of the disease in the treated plant with that in the untreated control. The sprayed plants were also assessed for plant compatibility by recording symptoms such as necrosis, chlorosis and stunting. Connections 14, 16, 17, 18, 20, 21, 22, 23, 26, 28, 29, 30, 31, 32, 33, 34, 36, 38, 39, 40, 41, 42, 43, 44, 45, 50, 51, 52, 53, 54, 55, 56, 57, 58, 59, 60, 65, 66, 67, 68, 69, 70, 71, 77, 79, 80, 81, 84, 85, 86, 87, 88, 89, 90, 91, 92, 93, 94, 95, 98, 100, 101, 102, 103, 104, 105, 109, 111, 113, 114, 115, 116, 117, 119, 120, 121, 122, 123, 124, 125, 126, 127, 128, 13 0, 131, 133, 134, 143, 144, 145, 146, 147, 148, 149, 150, 151, 152, 153, 155, 156, 157, 159, 160, 161, 178, 179, 181, 183, 184, 185, 187, 188, 189, 190, 191, 192, 193, 194, 195, 196, 201, 202, 203, 204, 205, 206, 207, 208, 209, 210, 211, 4, 215, 216, 217, 218, 219, 220, 221, 222, 223, 224, 229, 230, 231, 232, 233, 234, 235, 236, 237, 239, 242, 253, 255, 261, 262, 263, 264, 266, 270, 273, 274, 275, 276, 277, 278, 279, 281, 282, 284, 286, 287, 294, 295, 296, 297, 298, 299, 300, 301, at 500 ppm provided at least 70% control in such tests compared to untreated controls, which demonstrated extensive disease development.

Having described the present invention with reference to certain preferred aspects, other aspects will become apparent to those skilled in the art in view of the specification. It will be apparent to those skilled in the art that many modifications of both materials and methods can be practiced without departing from the scope of the present invention.

Claims (59)

1. Compound of formula (I) where R ¹ is C ₁ -C ₆ alkyl; R ² is C ₂ -C ₆ alkyl; R ³ is selected from the group consisting of X, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl and S(O) _n R'''; R ⁴ is selected from the group consisting of X, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl and OR''; R ^4a and R ^4b represent hydrogen; A is -{[C(R ⁶ R ⁷ )] _0-2 -(B) _0-1 }-, where B is NR ⁵ or CR ⁶ R ⁷ ; or A is -O-CR ⁶ R ⁷ -C(O)-; R ⁵ is selected from the group consisting of hydrogen and C ₁ -C ₆ alkyl; R ⁶ and R ⁷ represent hydrogen; ring E is selected from the group consisting of phenyl, pyridinyl, pyridazinyl, pyrimidinyl, pyrazinyl and benzothiazolyl, which are optionally substituted with one to three R ⁸ groups; R ⁸ is selected from the group consisting of hydrogen, X, cyano, nitro, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl, OR'' and S(O) _n R'''; two R ⁸ together with the atoms to which they are attached or together with additional atoms selected from the group consisting of N, O, may form a five- or six-membered ring; X represents halogen; R'' is selected from the group consisting of C ₁ -C ₆ alkyl and C ₁ -C ₆ haloalkyl; R''' is selected from R''; n represents the integer 0; or its agriculturally acceptable salts or stereoisomers. 2. A compound of formula (I) according to claim 1, wherein ring E is selected from the group consisting of phenyl, pyridinyl, pyrimidinyl, pyrazinyl and benzothiazolyl, which are optionally substituted with one to three R ⁸ groups; or its agriculturally acceptable salts or stereoisomers. 3. A compound of formula (I) according to claim 1, wherein said compound of formula (I) is selected from the group consisting of N'-(2-chloro-5-methyl-3-(p-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2,5-dimethyl-3-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-(3-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N-(2,5-dimethyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(3-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-((2-fluorophenyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-((2-fluorophenyl)(methyl)amino)-2,5-dimethylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(phenylamino)phenyl)-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(phenylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(phenyl)amino)phenyl)-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(2-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(o-tolylamino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((4-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N-(5-fluoro-3-((2-fluorophenyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(3-((4-(tert-butyl)phenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(o-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((4-(tert-butyl)phenyl)amino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-(2-chloro-5-methyl-3-((4-((trifluoromethyl)thio)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-chlorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluorophenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N-(5-fluoro-3-((3-methoxyphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(m-tolylamino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluorophenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(3-((3-chlorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(m-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3-chlorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(m-tolyl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((3-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chlorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(m-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(2-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-cyanobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(4-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-chloro-4-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3,5-dimethylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3-chloro-2-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(5-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-isopropylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-chlorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-chlorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-isopropylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluoro-2-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(pyridin-3-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3,4-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluoro-3-methylbenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-benzyl-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(3,5-difluoro-4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3,4-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3,4-difluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3,5-difluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2,4-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((2,4-difluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3,5-difluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3,5-difluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-benzyl-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((2,4-difluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3,4-difluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2,4-difluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3,4-difluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3,5-difluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(pyridin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((3-methylpyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-fluoro-3,5-dimethylbenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(2-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(2,6-difluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(2-chloro-6-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N-(5-fluoro-2-methyl-3-(pyridin-2-ylamino)phenyl)-N-methylformimidamide, N'-(3-((3-chloro-5-fluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chloro-5-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((5-chloro-2-methylphenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chloro-5-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((5-chloro-2-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(2-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(2-cyanobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(4-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3-chloro-5-fluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(3-methylpyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(2-chloro-3-((5-chloro-2-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-fluoro-5-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((5-chloro-3-methylpyridin-2-yl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((2-chloro-5-methylphenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluoro-5-methylphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-chloro-5-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((5-chloro-2-methylphenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((2-chloro-5-methylphenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((5-chloro-3-methylpyridin-2-yl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluoro-5-methylphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-chloro-5-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluoro-6-methylphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluoro-3-methylphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-fluoro-3-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromobenzyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-chlorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-fluoro-3-methylbenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3,4-difluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3-chloro-4-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(4-chloro-3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((3-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-fluoro-6-methylphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-chloro-2-fluorophenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((3-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((4-chloro-2-fluorophenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2-fluoro-6-methylphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2-fluoro-3-methylphenyl)(methyl)amino)-5-methyl phenyl)-N-ethyl-N-methylformimidamide, N'-(3-((4-chloro-2-fluorophenyl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(2-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(2-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(2-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N-(3-(3-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((2-fluoro-6-methylphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3-methylbenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(3-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(2-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-benzyl-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-methoxybenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N-(5-fluoro-3-((2-fluoro-3-methylphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(3-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(m-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(phenylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-chloro-2-fluorophenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(3-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((3-chloro-5-(trifluoromethyl)phenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(m-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-(3-((3-chloro-5-(trifluoromethyl)phenyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((4-methoxyphenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-chlorophenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-((3-bromophenyl)amino)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((2-fluorophenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-fluorophenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((4-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-cyanobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N-(5-fluoro-2-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-(4-chlorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N'-(3-(3-cyanobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N'-(2-chloro-3-((2-(difluoromethoxy)phenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((2-fluorophenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-fluorophenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-chlorophenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((2-(trifluoromethyl)benzyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((4-fluoro-3-methylbenzyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(5-chloro-3-((3-chlorobenzyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((2,3-dihydrobenzo[b][1,4]dioxin-6-yl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(o-tolylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(pyrimidin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(pyrimidin-2-ylamino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(2-bromo-3-(3-fluorobenzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(3-fluorobenzyl)-5-methyl-2-(methylthio)phenyl)-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(o-tolyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(pyrimidin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(pyrazin-2-ylamino)phenyl)-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(pyrazin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((1-(pyrazin-2-yl)propan-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(((5-methylpyrazin-2-yl)methyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N-'(5-fluoro-2-methyl-3-((1-(pyrazin-2-yl)propan-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(((5-methylpyrazin-2-yl)methyl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(pyrazin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(pyrimidin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(3-(4-cyanobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(4-fluoro-3-methylbenzyl)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(4-fluorobenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(3-bromobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-chloro-3-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-benzyl-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(2,5-dimethyl-3-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-bromo-5-methyl-3-(2-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(pyrazin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(pyrazin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(pyrimidin-2-ylamino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(pyrazin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(pyrimidin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromo-4-fluorobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromo-3-methylbenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-bromo-2-fluorobenzyl)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(2-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide, N'-(3-(2-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(4-fluorobenzyl)-2,5-dimethylphenyl)-N-methylformimidamide, N'-(3-(4-bromobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(4-chlorobenzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(benzo[(1]thiazol-6-ylamino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((6-ethylpyridin-2-yl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-((6-ethylpyridin-2-yl)amino)-5-fluoro-2-methylphenyl)-N-methylformimidamide, N'-(3-(benzo[(1]thiazol-6-ylamino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-chloro-5-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromo-4-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N-(5-fluoro-3-(5-fluoro-2-methylbenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(4-bromo-3-methylbenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromo-5-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(3-fluoro-5-methylbenzyl)-2-methylphenyl)-N-methylformimidamide, N-(3-(4-bromo-2-fluorobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-(3-fluoro-5-methoxybenzyl)-2-methylphenyl)-N-methylformimidamide, N'-(3-(benzo[d]thiazol-6-yl(methyl)amino)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-((6-ethylpyridin-2-yl)(methyl)amino)-5-fluoro-2-methylphenyl)-N-methylformimidamide, N-(3-(benzo[d]thiazol-6-yl(methyl)amino)-2-chloro-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(4-(methylthio)benzyl)phenyl)-N-methylformimidamide, N'-(3-(benzo[d]thiazol-6-ylamino)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((6-ethylpyridin-2-yl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(2-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-(3-bromobenzyl)-5-chloro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-(5-chloro-3-(4-cyanobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(pyridin-3-ylmethyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(4-(trifluoromethyl)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-(3-cyanobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(3-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(4-(methylthio)benzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((6-ethylpyridin-2-yl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-3-((3-fluoro-4-methoxyphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((3-fluoro-4-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-3-((3-fluoro-4-methoxyphenyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N-(5-fluoro-3-((3-fluoro-4-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N'-(2-chloro-3-((3-fluoro-4-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(3-nitrobenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(pyridin-3-ylmethyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(3-(4-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(2-methylbenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(4-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-(3-chlorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-chlorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-(2-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N'-(5-chloro-3-((3-fluoro-4-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-3-((2-methoxyphenyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-((3-fluoro-4-methoxyphenyl)amino)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-3-((2-methoxyphenyl)(methyl)amino)-2-methylphenyl)-N-methylformimidamide, N-ethyl-N-(3-((3-fluoro-4-methoxyphenyl)(methyl)amino)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(5-chloro-2-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-fluoro-3-methoxyphenyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(3-((4-fluoro-3-methoxyphenyl)amino)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(3-(3-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(3-methylbenzyl)phenyl)-N-methylformimidamide, N'-(3-(4-chlorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(3-nitrobenzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(3-(5-fluoro-2-methylbenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N'-(3-(3-chloro-4-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N-(3-((4-fluoro-3-methoxyphenyl)(methyl)amino)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N'-(3-(3,4-difluorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-(3-(4-bromobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-3-((4-fluoro-3-methoxyphenyl)(methyl)amino)-5-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-chloro-2-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-(methyl(6-(trifluoromethyl)pyridin-2-yl)amino)phenyl)-N-methylformimidamide, N-ethyl-N'-(3-(3-fluoro-5-methylbenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide, N'-(3-(2-chloro-5-fluorobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-(2-bromobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(4-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(3-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(5-cyano-3-(3-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(3-benzyl-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-methylformimidamide, N'-(5-chloro-2-methyl-3-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N'-(2-chloro-5-methyl-3-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-fluoro-2-methyl-3-((2-(trifluoromethoxy)phenyl)amino)phenyl)-N-methylformimidamide, N'-(3-(2-(2-chloro-4-methoxyphenoxy)acetyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N-(5-methoxy-2-methyl-3-(3-(trifluoromethoxy)benzyl)phenyl)-N-methylformimidamide, N'-(3-(3-cyanobenzyl)-5-methoxy-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-ethyl-N'-(5-methoxy-2-methyl-3-(2-(trifluoromethyl)benzyl)phenyl)-N-methylformimidamide, N'-(3-benzyl-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-cyano-3-(3-cyanobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-cyano-3-(4-fluorobenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, N-(3-(4-chlorobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide, N'-(5-cyano-2-methyl-3-(3-nitrobenzyl)phenyl)-N-ethyl-N-methylformimidamide, N'-(3-(3-bromobenzyl)-5-cyano-2-methylphenyl)-N-ethyl-N-methylformimidamide and N'-(5-cyano-2-methyl-3-(2-(trifluoromethoxy)benzyl)phenyl)-N-ethyl-N-methylformimide amide. 4. A method for producing a compound of formula (I) according to claim 1, wherein said method comprises steps (a)-(c): a) converting a compound of formula (XXVI) or (XXIV) into a compound of formula (XXIII) according to the reaction scheme as shown below: b) reacting the compound of formula (XXIII) with a suitable secondary amine (HNR ¹ R ² ) to obtain the compound of formula (III) according to the reaction scheme as depicted below: c) reacting a compound of formula (III) with a compound of formula (XII), (XVII) or (XXXI) to obtain a compound of formula (I) according to the reaction scheme as shown below: where in the above reaction schemes M is selected from the group consisting of a lithium derivative, a boronic acid ester, and a boronic acid. 5. A composition for controlling and/or preventing the occurrence of phytopathogenic fungi, comprising a compound of formula (I), its stereoisomers or agriculturally acceptable salts according to claim 1 and one or more inert carriers. 6. The composition according to claim 5, wherein the concentration of the compound of formula (I) is in the range from 10 to 90% by weight relative to the total weight of the composition, preferably from 30 to 70% by weight relative to the total weight of the composition. 7. A method for controlling or preventing the occurrence of phytopathogenic fungi on agricultural crops and/or horticultural crops, comprising the use of an effective amount of a compound of formula (I), its stereoisomers or agriculturally acceptable salts according to claim 1. 8. The method according to claim 7, wherein the phytopathogenic fungi are selected from Phakopsora pachyrhizi, Phakopsora meibomiae of agricultural and/or horticultural crops. 9. The method according to claim 7 or 8, wherein said agricultural crops are cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, nuts and nut trees, citrus and citrus trees, any garden plants, pumpkin plants, oil plants, tobacco, coffee plant, tea plant, cocoa tree, sugar beet, sugar cane, cotton, potato, tomato, onion species, pepper species and other vegetables and ornamental plants. 10. A method for controlling or preventing the appearance of phytopathogenic fungi on agricultural crops and/or horticultural crops, comprising using an effective amount of the composition according to paragraph 5. 11. The method according to claim 10, wherein the phytopathogenic fungi are selected from Phakopsora pachyrhizi, Phakopsora meibomiae of agricultural and/or horticultural crops. 12. The method according to claim 10 or 11, wherein said agricultural crops are cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, nuts and nut trees, citrus fruits and citrus trees, any garden plants, pumpkin plants, oil plants, tobacco, coffee plant, tea plant, cocoa tree, sugar beet, sugar cane, cotton, potato, tomato, onion species, pepper species and other vegetables and ornamental plants. 13. A method for controlling rust diseases of agricultural crops and/or horticultural crops caused by phytopathogenic fungi, comprising using an effective amount of a compound of formula (I) according to claim 1. 14. The method of claim 13, wherein said rust diseases of crops are Hemileia vastatrix (coffee rust), Uromyces appendiculatus/fabae/phaseoli (bean rust), Puccinia spp . (rust species) on different plants selected from P. triticina (brown or leaf rust), P. striiformis (linear or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. reconduct (brown or leaf rust) on cereals selected from wheat, barley or rye, and Phakopsora spp . on different plants, in particular Phakopsora pachyr hizi and P. meibomiae (soybean rust) on soybeans. 15. The method according to claim 13, wherein the phytopathogenic fungi are selected from Phakopsora pachyrhizi, Phakopsora meibomiae of agricultural and/or horticultural crops. 16. The method according to claim 13 or 15, wherein said agricultural crops are cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, nuts and nut trees, citrus fruits and citrus trees, any garden plants, pumpkin plants, oil plants, tobacco, coffee plant, tea plant, cocoa tree, sugar beet, sugar cane, cotton, potato, tomato, onion species, pepper species and other vegetables and ornamental plants. 17. A method for controlling rust diseases of agricultural crops and/or horticultural crops caused by phytopathogenic fungi, comprising using an effective amount of the composition according to paragraph 5. 18. The method of claim 17, wherein said rust diseases of crops are Hemileia vastatrix (coffee rust), Uromyces appendiculatus/fabae/phaseoli (bean rust), Puccinia spp . (rust species) on different plants selected from P. triticina (brown or leaf rust), P. striiformis (linear or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals selected from wheat, barley or rye, and Phakopsora spp . on different plants, in particular Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans. 19. The method according to claim 17, wherein the phytopathogenic fungi are selected from Phakopsora pachyrhizi, Phakopsora meibomiae of agricultural and/or horticultural crops. 20. The method according to claim 17 or 19, wherein said agricultural crops are cereals, corn, rice, soybeans and other legumes, fruits and fruit trees, nuts and nut trees, citrus fruits and citrus trees, any garden plants, pumpkin plants, oil plants, tobacco, coffee plant, tea plant, cocoa tree, sugar beet, sugar cane, cotton, potato, tomato, onion species, pepper species and other vegetables and ornamental plants. 21. Seed treated with a compound of formula (I), its agriculturally acceptable salts or stereoisomers according to claim 1 for protection against phytopathogenic fungi, wherein the amount of the compound of formula (I), its stereoisomers or agriculturally acceptable salts is from 0.1 g to 1 kg per 100 kg of seed. 22. A method for controlling or preventing infection of useful plants by phytopathogenic fungi on agricultural crops and/or horticultural crops, wherein the compound of formula (I), its stereoisomers or agriculturally acceptable salts according to claim 1 or the composition according to claim 5 are applied to plants, their parts or their growing site. 23. A method for controlling or preventing infection of useful plants by phytopathogenic fungi on agricultural crops and/or horticultural crops, wherein the compound of formula (I), its stereoisomers or agriculturally acceptable salts according to claim 1 or the composition according to claim 5 are used in relation to plant seeds. 24. A method for controlling or preventing the occurrence of phytopathogenic fungi on agricultural crops and/or horticultural crops using a compound of formula (I), its stereoisomers or agriculturally acceptable salts according to claim 1 or a composition according to claim 5, which comprises the step of applying an effective dose of the compound or composition in amounts ranging from 1 g to 2 kg per hectare of agricultural and/or horticultural crops. 25. A method for combating phytopathogenic fungi, comprising treating plants, soil, seeds or materials to be protected with a compound of formula (I), its stereoisomers or agriculturally acceptable salts according to claim 1 or a composition according to claim 5. 26. Compound of formula (A) where Z is X; R ¹ is C ₁ -C ₆ alkyl; R ² is C ₂ -C ₆ alkyl; R ³ is selected from the group consisting of X, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl and S(O) _n R'''; R ⁴ is selected from the group consisting of X, cyano, C ₁ -C ₆ alkyl, C ₁ -C ₆ haloalkyl and OR'', where R'', R''' are defined in paragraph 1. 27. An intermediate compound for preparing a compound of formula (I) according to claim 1, selected from 2-chloro-5-methyl-N ¹ -(p-tolyl)benzene-1,3-diamine, 2,5-dimethyl-3-(4-methylbenzyl)aniline, 3-(3-chlorobenzyl)-2,5-dimethylaniline, 2,5-dimethyl-3-(2-methylbenzyl)aniline, 3-(3-fluorobenzyl)-2,5-dimethylaniline, N-(2-fluorophenyl)-2,5-dimethylbenzene-1,3-diamine, N ¹ -(2-fluorophenyl)-N ¹ ,2,5-trimethylbenzene-1,3-diamine, 6-fluoro-N-methyl-N ¹ -phenylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -phenylbenzene-1,3-diamine, 2-chloro-N ¹ ,5-dimethyl-N ¹ -phenylbenzene-1,3-diamine, 5-fluoro-N ¹ ,2-dimethyl-N ¹ -phenylbenzene-1,3-diamine, 2-chloro-5-methyl-3-(2-methylbenzyl)aniline, 2-chloro-3-(2-chlorobenzyl)-5-methylaniline, 2-chloro-3-(2-fluorobenzyl)-5-methylaniline, 5-fluoro-2-methyl-N ¹ -(o-tolyl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(4-((trifluoromethyl)thio)phenyl)benzene-1,3-diamine, 2-chloro-5-methyl-3-(3-methylbenzyl)aniline, 2-chloro-5-methyl-3-(4-methylbenzyl)aniline, 5-fluoro-N ¹ -(2-fluorophenyl)-2-methylbenzene-1,3-diamine, N-(4-(tert-butyl)phenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-5-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 3-(3-fluorobenzyl)-5-methylaniline, 2-chloro-N ¹ -(2-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(o-tolyl)benzene-1,3-diamine, N ¹ -(4-(tert-butyl)phenyl)-2-chloro-5-methylbenzene-1,3-diamine, 5-methyl-N ¹ -(4-((trifluoromethyl)thio)phenyl)benzene-1,3-diamine, 2-chloro-3-(3-chlorobenzyl)-5-methylaniline, 2-chloro-3-(3-methoxybenzyl)-5-methylaniline, 5-fluoro-N ¹ -(3-fluorophenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-N ¹ -(3-methoxyphenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(m-tolyl)benzene-1,3-diamine, 5-fluoro-N ¹ -(3-fluorophenyl)-N ¹ ,2-dimethylbenzene-1,3-diamine, N ¹ -(3-chlorophenyl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-chlorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(m-tolyl)benzene-1,3-diamine, N ¹ -(3-chlorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 5-fluoro-N ¹ ,2-dimethyl-N ¹ -(m-tolyl)benzene-1,3-diamine, 5-fluoro-N ¹ -(3-methoxyphenyl)-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-fluorophenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 2-chloro-N' ¹ -(3-chlorophenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-methoxyphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ^1,5 -dimethyl-N-(m-tolyl)benzene-1,3-diamine, 2-chloro-3-(4-fluorobenzyl)-5-methylaniline, 3-(2-bromobenzyl)-2 -chloro-5-methylaniline, 4-(3-amino-2-chloro-5-methylbenzyl)benzonitrile, 2-(3-amino-2-chloro-5-methylbenzyl)benzonitrile, 3-(3-amino-2-chloro-5-methylbenzyl)benzonitrile, 2-chloro-N ¹ -(3-methoxyphenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 2-chloro-5-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 2-chloro-5-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 2-chloro-5-methyl-3-(4-(trifluoromethoxy)benzyl)aniline, 2-chloro-5-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 2-chloro-3-(3-chloro-4-fluorobenzyl)-5-methylaniline, 2-chloro-3-(3,5-dimethylbenzyl)-5-methylaniline, 2-chloro-3-(3-chloro-2-fluorobenzyl)-5-methylaniline, 2-chloro-3-(5-fluoro-2-methylbenzyl)-5-methylaniline, 2-chloro-N ¹ -(3-isopropylphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(4-chlorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(4-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(4-methoxyphenyl) ^-5 -methylbenzene- ^1,3 -diamine , 2-chloro-N ¹ -(4-chlorophenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 2-chloro-N ^{1 -(3-isopropylphenyl)-N 1,5-dimethylbenzene-1,3-diamine, 2-chloro-N 1} -(4-methoxyphenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 2-chloro-3-(4-fluoro-2-methylbenzyl)-5-methylaniline, 2-chloro-5-methyl-3-(pyridin-3-ylmethyl)aniline, 2-chloro-3-(3,4-difluorobenzyl)-5-methylaniline, 2-chloro-3-(4-fluoro-3-methylbenzyl)-5-methylaniline, 2-chloro-N-(4-fluorophenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 3-benzyl-2-chloro-5-methylaniline, 2-chloro-3-(3,5-difluoro-4-methoxybenzyl)-5-methylaniline, 2-chloro-N ¹ -(3,4-difluorophenyl)-5-methylbenzene-1,3-diamine, N ¹ -(3,4-difluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(3,5-difluorophenyl)-5-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(2,4-difluorophenyl)-5-methylbenzene-1,3-diamine, N ¹ -(2,4-difluorophenyl)-5- fluoro-2-methylbenzene-1,3-diamine, N ¹ -(3,5-difluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N' ¹ -(3,5-difluorophenyl)-5-methylbenzene-1,3-diamine, 3-benzyl-5-chloro-2-methylaniline, N ¹ -(2,4-difluorophenyl)-5- fluorine-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3,4-difluorophenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(2,4-difluorophenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, N ¹ -(3,4-difluorophenyl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, N ¹ -(3,5-difluorophenyl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(pyridin-2-yl)benzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(3-methylpyridin-2-yl)benzene-1,3-diamine, 5-chloro-3-(4-fluoro-3,5-dimethylbenzyl)-2-methylaniline, 5-chloro-2-methyl-3-(2-methylbenzyl)aniline, 5-chloro-3-(2-chlorobenzyl)-2-methylaniline, 3-(2-bromobenzyl)-5-chloro-2-methylaniline, 2-chloro-3-(2,6-difluorobenzyl)-5-methylaniline, 2-chloro-3-(2-chloro-6-fluorobenzyl)-5-methylaniline, 3-(4-bromobenzyl)-2-chloro-5-methylaniline, 5-chloro-2-methyl-3-(3-methylbenzyl)aniline, 5-fluoro-2-methyl-N ¹ -(pyridin-2-yl)benzene-1,3-diamine, N ¹ -(3-chloro-5-fluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-chloro-5-fluorophenyl)-5-methylbenzene-1,3-diamine, N ¹ -(3-chloro-methylphenyl-N-fluoro-N ¹ N-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3 lor-5-fluorophenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(5-chloro-2-methylphenyl)-5-methylbenzene-1,3-diamine, 5-chloro-3-(3-chlorobenzyl)-2-methylaniline, 5-chloro-3-(3-fluorobenzyl)-2-methylaniline, 5-chloro-3-(2-fluorobenzyl)-2-methylaniline, 2-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(4-methylbenzyl)aniline, N ¹ -(3-chloro-5-fluorophenyl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ ,5-dimethyl-N ¹ -(pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ¹ ,5-dimethyl-N ¹ -(3-methylpyridin-2-yl)benzene-1,3-diamine, 5-fluoro-N ¹ ,2-dimethyl-N ¹ -(pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ¹ -(5-chloro-2-methylphenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-fluoro-5-methylphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(5-chloro-3-methylpyridin-2-yl)-5-methylbenzene-1,3-diamine, N ¹ -(2-chloro- 5-methylphenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 5-fluoro-N ¹ -(3-fluoro-5-methylphenyl)-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(2-chloro-5-methylphenyl)-5-methylbenzene-1,3-diamine, N ¹ -(5-chloro-2-methylphenyl)-5-fluoro-2-methylbenzene-1,3-diamine, N ¹ -(2-chloro-5-methylphenyl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(5-chloro-3-methylpyridin-2-yl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 5-fluoro-N ¹ -(3-fluoro-5-methylphenyl)-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(2-chloro-5-methylphenyl-N ¹ ,5-dimethylbenzene-1,3-diamine, 5-fluoro-N ¹ -(2-fluoro-6-methylphenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-N ¹ -(2-fluoro-3-methylphenyl)-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(2-fluoro-3-methylphenyl)-5-methylbenzene-1,3-diamine, 5-chloro-3-(4-fluorobenzyl)-2-methylaniline, 3-(4-bromobenzyl)-5-chloro-2-methylaniline, 5-chloro-3-(4-chlorobenzyl)-2-methylaniline, 5-chloro-2-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 5-chloro-3-(4-fluoro-3-methylbenzyl)-2-methylaniline, 5-chloro-3-(3,4-difluorobenzyl)-2-methylaniline, 5-chloro-3-(3-chloro-4-fluorobenzyl)-2-methylaniline, 5-chloro-3-(4-chloro-3-fluorobenzyl)-2-methylaniline, 5-fluoro-2-methyl-N ¹ -(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ¹ -(2-fluoro-6-methylphenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(4-chloro-2-fluorophenyl)-5-methylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, N ¹ -(4-chloro-2-fluorophenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-chloro-5-(trifluoromethyl)phenyl)-5-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(2-fluoro-6-methylphenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(2-fluoro-3-methylphenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, N ¹ - (4-chloro-2-fluorophenyl)-5-fluoro-N ^1,2 -dimethylbenzene-1,3-diamine, 5-fluoro-3-(2-fluorobenzyl)-2-methylaniline, 3-(2-chlorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 3-(3-chlorobenzyl)- 5-fluoro-2-methylaniline, 5-fluoro-N ¹ -(2-fluoro-6-methylphenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, 5-fluoro-2-methyl-3-(3-methylbenzyl)aniline, 5-fluoro-3-(3-fluorobenzyl)-2-methylaniline, 5-fluoro-2-methyl-3-(2-methylbenzyl)aniline, 3-benzyl-5-fluoro-2- methylaniline, 2-chloro-3-(4-methoxybenzyl)-5-methylaniline, 3-(2-bromobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-N ¹ -(2-fluoro-3-methylphenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, 5-fluoro-N ^1,2 -dimethyl-N ¹ -(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N ¹ -(m-tolyl)benzene-1,3-diamine, 3-chloro-N-methyl-N ¹ -phenylbenzene-1,3-diamine, 2-chloro-N ¹ -(4-chloro-2-fluorophenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ ,5-dimethyl-N ¹ -(3-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ¹ -(3-chloro-5-(trifluoromethyl)phenyl)-N ¹ ,5-dimethylbenzene-1,3-diamine, 5-chloro-N ¹ -dimethyl-N ¹ -phenylbenzene-1,3-diamine, 3-chloro-N ¹ ,2-dimethyl-N ¹ -(m-tolyl)benzene-1,3-diamine,N ¹ -(3-chloro-5-(trifluoromethyl)phenyl)-5-fluoro-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(4-methoxyphenyl)-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(3-chlorophenyl)-2-methylbenzene-1,3-diamine, N ¹ -(3-bromophenyl)-5-chloro-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(2-fluorophenyl)-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(3-fluorophenyl)-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(4-methoxyphenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, 2-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 2-chloro-N ¹ -(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-5-methylbenzene-1,3-diamine, 5-fluoro-2 -methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 5-fluoro-2-methyl-3-(4-methylbenzyl)aniline, 3-(4-chlorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(3-(trifluoromethoxy)benzyl)aniline, 3-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 3-(4-bromobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-2-methyl-3-(4-(trifluoromethoxy)benzyl)aniline, 2-chloro-N ¹ -(2-(difluoromethoxy)phenyl)-5-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(2-fluorophenyl)-N ^1,2 -dimethylbenzene-1,3 -diamine, 5-chloro-N ¹ -(3-fluorophenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, 5-chloro-N ¹ -(3-chlorophenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(2-(trifluoromethyl)benzyl)benzene-1,3-diamine, 5-ph torus-N ¹ -(4-fluoro-3-methylbenzyl)-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(3-chlorobenzyl)-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-N ^1,5 -dimethylbenzene-1,3-diamine, 5-chloro -2-methyl-N ¹ -(o-tolyl)benzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 2-bromo-3-(3-fluorobenzyl)-5-methylaniline, 3-(3-fluorobenzyl)-5-methyl-2-(methylthio)aniline, 5-chloro-N ¹ ,2-dimethyl-N ¹ -(o-tolyl)benzene-1,3-diamine, 2-chloro-N ¹ ,5-dimethyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(pyrazin-2-yl)benzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(pyrazin-2-yl)benzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(1-(pyrazin-2-yl)propan-2-yl)benzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -((5-methylpyrazin-2-yl)methyl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(1-(pyrazin-2-yl)propan-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -((5-methylpyrazin-2-yl)methyl)benzene-1,3-diamine, 5-fluoro-N ¹ ,2-dimethyl -N ¹ -(pyrazin-2-yl)benzene-1,3-diamine, 5-fluoro-N ^1,2 -dimethyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 4-(3-amino-5-fluoro-2-methylbenzyl)benzonitrile, 5-fluoro-3-(4-fluoro-3-methylbenzyl)-2-methylaniline, 5-fluoro-3-(4-fluorobenzyl)-2-methylaniline, 3-(3-bromobenzyl)-5-fluoro-2-methylaniline, 3-(4-chloro-3-fluorobenzyl)-5-fluoro-2-methylaniline, 3-benzyl-2,5-dimethylaniline, 2,5-dimethyl -3-(3-methylbenzyl)aniline, 2-bromo-5-methyl-3-(2-methylbenzyl)aniline, 2-chloro-N ¹ ,5-dimethyl-N ¹ -(pyrazin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N ¹ -(pyrazin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 5-chloro-N ¹ ,2-dimethyl-N ¹ -(pyrazin-2-yl)benzene-1,3-diamine, 5-chloro-N ¹ ,2-dimethyl-N ¹ -(pyrimidin-2-yl)benzene-1,3-diamine, 3-(2-bromo-4-fluorobenzyl)-2-chloro-5-methylaniline, 3-(4-bromo-3-methylbenzyl)-2-chloro-5-methylaniline, 3-(4-bromo-2-fluorobenzyl)-2-chloro-5-methylaniline, 2-chloro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-5-methylaniline, 3-(2-fluorobenzyl)-2,5-dimethylaniline, 3-(2-chlorobenzyl)-2,5-dimethylaniline, 3-(2-bromobenzyl)-2,5-dimethylaniline, 3-(4-fluorobenzyl)-2,5-dimethylaniline, 3-(4-bromobenzyl)-2,5-dimethylaniline, 3-(4-chlorobenzyl)-2,5-dimethylaniline, N ¹ -(benzo[(1]thiazol-6-yl)-5-fluoro-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(6-ethylpyridin-2-yl)-5-methylbenzene-1,3-diamine, N ¹ -(6-ethylpyridin-N-yl-1,3-fluoro-2-methylbenzene-1,3-diamine, N ¹ -(benzo[d]thiazol-6-yl)-2-chloro-5-methylbenzene-1,3-diamine, 3-(2-chloro-5-fluorobenzyl)-5-fluoro-2-methylaniline, 3-(2-bromo-4-fluorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-3-(5-fluoro-2-methylbenzyl)-2-methylaniline, -bromo-3-methylbenzyl)-5-fluoro-2-methylaniline, 3-(2-bromo-5-fluorobenzyl)-5-fluoro-2-methylaniline, 5-fluoro-3-(4-fluoro-3-(trifluoromethyl)benzyl)-2-methylaniline, 5-fluoro-3-(3-fluoro-5-methylbenzyl)-2-methylaniline, 3-(4-bromo-2-fluorobenzyl) )-5-fluoro-2-methylaniline, 5-fluoro-3-(3-fluoro-5-methoxybenzyl)-2-methylaniline, N ¹ -(benzo[d]thiazol-6-yl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, N ¹ -(6-ethylpyridin-2-yl)-5-fluoro-N ¹ ,2-dimethylbenzene-1,3-diamine, N ¹ -(benzo[d]thiazol-6-yl-N-chloro-N ¹ ,3-dimethylbenzene-1,3-diamine, 5-fluoro-2-methyl-3-(4-(methylthio)benzyl)aniline, N ¹ -(benzo[d]thiazol-6-yl)-5-chloro-2-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(6-ethylpyridin-2-yl)-2-methylbenzene- 1,3-diamine, 5-chloro-2-methyl-3-(2-(trifluoromethyl)benzyl)aniline, 3-(3-bromobenzyl)-5-chloro-2-methylaniline, 4-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 3-(pyridin-3-ylmethyl)aniline, 5-chloro-2-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 3-(3-amino-5-chloro-2-methylbenzyl)benzonitrile, 5-chloro-2-methyl-3-(3-(trifluoromethoxy)benzyl)aniline, 5-chloro-2-methyl-3-(4-(methylthio)benzyl)aniline, 5-chloro-N ¹ -(6-ethylpyridin-2-yl)-N ¹ ,2-dimethylbenzene-1,3-diamine, 5-fluoro-N ¹ -(3-fluoro-4-methoxyphenyl)-2-methylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-fluoro-4-methoxyphenyl)-5-methylbenzene-1,3-diamine, 5-chloro-N ¹ -(3-fluoro-4-methoxyphenyl)-2-methylbenzene-1,3-diamine, 5-fluoro-N ¹ -(3-fluoro-4-methoxyphenyl)-N ¹ ,2-dimethylbenzene-1,3-diamine, 2-chloro-N ¹ -(3-fluoro-N-methoxyphenyl-N ¹ ,2-dimethylbenzene-1,3-diamine, 5-fluoro-2-methyl-3-(3-nitrobenzyl)aniline, 5-fluoro-2-methyl-3-(pyridin-3-ylmethyl)aniline, 3-(4-fluorobenzyl)-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(2-methylbenzyl)aniline, 5-methoxy-2-methyl-3-(4-methylbenzyl)aniline, benzyl)-5-methoxy-2-methylaniline, 3-(2-chlorobenzyl)-5-methoxy-2-methylaniline, 3-(2-fluorobenzyl)-5-methoxy-2-methylaniline, 5-chloro-N ¹ -(3-fluoro-4-methoxyphenyl)-N,2-dimethylbenzene-1,3-diamine, 5-methoxy-N ¹ -(2-methoxyphenyl)-2-methylbenzene-1,3-diamine, N ¹ -(3-fluoro-N-methoxyphenyl-N3-methoxy-2-methylbenzene-1,3-diamine, 5-methoxy-N ¹ -(2-methoxyphenyl)-N ^1,2 -dimethylbenzene-1,3-diamine, N ¹ -(3-fluoro-N-methoxyphen-N-3-methoxy- ^N 1,2-dimethylbenzene-1,3-diamine, 5-methoxy-2-methyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 5-chloro-2-methyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ¹ -(4-fluoro-3-methoxyphenyl)-5-methylbenzene-1,3-diamine, 5-N-fluoro-3-methoxyphenyl-N ¹ -methoxy-N-methylbenzene-1,3-diamine, 3-(3-fluorobenzyl)-5-methoxy-2-methyl aniline, 5-methoxy-2-methyl-3-(3-methylbenzyl)aniline, 3-(4-chlorobenzyl)-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(3-nitrobenzyl)aniline, 3-(5-fluoro-2-methylbenzyl)-5-methoxy-2-methylaniline, 3-(3-chloro-4-fluorobenzyl)-5-methoxy-2-methylaniline Lina, 2-chloro-5-methyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, N ¹ -(4- ^fluoro -3-methoxyphenyl)-5-methoxyN ^1,2 -dimethylbenzene-1,3-diamine, 5-methoxy-N 1,2-dimethyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)benzene -1,3-diamine, 3-(3,4-difluorobenzyl)-5-methoxy-2-methylaniline, 3-(4-bromobenzyl)-5-methoxy-2-methylaniline, 2-chloro-N ¹ -(4-fluoro-3-methoxyphenyl)-N ^1,5 -dimethylbenzene-1,3-diamine, 5-chloro-N ^1,2 -dimethyl-N ¹ -(6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine, 2-chloro-N ^1,5 -dimethyl-N ¹ -(6-(trifluoromethyl) ^{pyridin-2-yl)benzene-1,3-diamine, 5-fluoro-N 1,2-dimethyl-N 1 -} (6-(trifluoromethyl)pyridin-2-yl)benzene-1,3-diamine on, 3-(3-fluoro-5-methylbenzyl)-5-methoxy-2-methylaniline, 3-(2-chloro-5-fluorobenzyl)-5-methoxy-2-methylaniline, 3-(2-bromobenzyl)-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(4-(trifluoromethyl)benzyl)aniline, 5-methoxy-2-methyl-3-(3-(trifluoromethyl)benzyl)aniline, 3-amino-5-(3-fluorobenzyl)-4-methylbenzonitrile, 3-benzyl-5-methoxy-2-methylaniline, 5-methoxy-2-methyl-3-(2-(trifluoromethoxy)benzyl)aniline, 5-methoxy-2-methyl-N ¹ -(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 5-chloro-2-methyl-N ¹ -(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 2-chloro-5-methyl-N ¹ -(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 5-fluoro-2-methyl-N ¹ -(2-(trifluoromethoxy)phenyl)benzene-1,3-diamine, 1-(3-amino-5-fluoro-2-methylphenyl)-2-(2-chloro-4-methoxyphenoxy)ethan-1-one, 5-methoxy-2-methyl-3-(3-(trifluoromethoxy)benzyl)aniline, 3-(3-amino-5-methoxy-2-methylbenzyl)benzonitrile, 5-methoxy-2-methyl-3-(2-(trifluoromethyl)benzyl)aniline , 3-amino-5-benzyl-4-methylbenzonitrile, 3-amino-5-(3-cyanobenzyl)-4-methylbenzonitrile, 3-amino-5-(4-fluorobenzyl)-4-methylbenzonitrile, 3-amino-5-(4-chlorobenzyl)-4-methylbenzonitrile, 3-amino-4-methyl-5-(3-nitrobenzyl)benzonitrile , 3-amino-5-(3-bromobenzyl)-4-methylbenzonitrile and 3-amino-4-methyl-5-(2-(trifluoromethoxy)benzyl)benzonitrile.