WO2024147155A1

WO2024147155A1 - Ternary composition comprising 3-substituted phenylamidine compounds and use thereof

Info

Publication number: WO2024147155A1
Application number: PCT/IN2024/050005
Authority: WO
Inventors: Santosh Shridhar AUTKAR; Vishal A Mahajan; Siddaramaiah C R; Hagalavadi M VENKATESHA
Original assignee: PI Industries Ltd
Current assignee: PI Industries Ltd
Priority date: 2023-01-03
Filing date: 2024-01-02
Publication date: 2024-07-11
Anticipated expiration: 2025-07-03
Also published as: UY40594A; KR20250130377A; CO2025008975A2; CL2025001947A1; CN120548107A; MX2025007718A; TW202434109A; EP4646108A1; AR131546A1; AU2024206536A1; PE20252284A1

Abstract

TERNARY COMPOSITION COMPRISING 3-SUBSTITUTED PHENYLAMIDINE COMPOUNDS AND USE THEREOF The present invention discloses an agrochemical composition comprising a mixture of component (1), and at least two components selected from component (2), component (3), or a combination of component (2) 5 and component (3), wherein the component (1) is at least one compound of formula (I) Formula (I) wherein, R1, R2, R3, R4, R5, R6, R7 and n are as defined in detailed description; as component (2) at least one fungicide selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, metyltetraprole, 10 benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, inpyrfluxam, cyproconazole, mefentrifluconazole, prothioconazole, tebuconazole, chlorothalonil, mancozeb and their salts; and as component (3) at least one fungicide different from components (1) and (2) which is selected from the groups (A) inhibitors of the sterol biosynthesis, (B) inhibitors of the respiratory chain at complex I or II, (C) inhibitors of the respiratory chain at complex III, (D) compounds capable to have multisite action, or (E) inhibitors of histone 15 deacetylase.

Description

TERNARY COMPOSITION COMPRISING 3-SUBSTITUTED PHENYLAMIDINE COMPOUNDS AND USE THEREOF

FIELD OF THE INVENTION:

The present invention relates to novel agrochemical composition. More particularly, the present invention relates to a ternary composition comprising as component (1) at least one phenylamidine compound of formula (I); as component (2) at least one fungicide selected from azoxy strobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb and their salts; and as component (3) at least one additional fungicide, which is different from the compounds of components (1) and (2), selected from the groups (A) inhibitors of the sterol biosynthesis, (B) inhibitors of the respiratory chain at complex I or II, (C) inhibitors of the respiratory chain at complex III, (D) compounds capable to have a multisite action, or (E) inhibitors of histone deacetylase. Further, the agrochemical composition, according to the invention, relate to a method for controlling microorganisms such as phytopathogenic fungi and bacteria.

BACKGROUND OF THE INVENTION:

It is widely known that various fungicidal compounds out of different chemical classes are already used as fungicides for applications in various crops of cultivated plants. However, crop tolerance and spectrum of activity as well as the level of efficacy against phytopathogenic fungi on plants do not always satisfy the needs of the agricultural practice in many incidents and aspects. In order to overcome this problem, binary mixtures of arylamidine derivatives with certain fungicides have been provided in W02003024219, W02005089547, WO2018228896, W02007031507 and WO2022113033 discloses fungicide compositions comprising a N2-phenylamidine derivative together with other fungicidal compounds.

Recently, practical agricultural experience has shown that the repeated and exclusive application of an individual active compound or a binary mixture in the control of harmful fungi lead to natural or adapted resistance by fungus strains against the active compound in question. Effective control of these fungi with the active compound and/or binary mixture in question is then no longer possible.

Fungicides, that effectively control plant pathogens with a reduced quantity of the chemical agent released in the environment, are always desirable. Additionally, there is a constant need to broaden the spectrum of activity, reduce undesirable environmental effects and lower the application rates. The present invention provides agrochemical composition, which, in some of these aspects, at least achieve the stated objectives.

Surprisingly it has been found that the novel agrochemical composition, according to the invention, not only bring about the additive enhancement of the spectrum of activity with respect to the phytopathogens to be controlled, that was in principle to be expected, but also achieve a synergistic effect. The synergistic effect of the agrochemical composition of the present invention helps to reduce the application rate of component (1), component (2) and component (3) by maintaining the level of efficacy even if the three individual compounds alone have become widely ineffective at such low application rates. Over and above, it allows a substantial broadening of the spectrum of phytopathogens that can be controlled, by, at the same time, increasing the safety in use.

In addition to the fungicidal synergistic activity, the agrochemical composition, according to the invention, have further surprising properties, which, in a wider sense, may also be called synergistic, such as, for example: broadening of the activity spectrum to more phytopathogens, for example to resistant strains of plant diseases; lower application rates of the active compounds; sufficient control of plant diseases with the aid of the agrochemical composition according to the invention even at application rates where the individual compounds showed virtually no activity; advantageous behavior during formulation or during use, for example during grinding, sieving, emulsifying, dissolving or dispensing; improved storage and light stability; advantageous residue formation; improved toxicological or eco-biological behavior; improved properties of the so called effects on plant physiology, for example better growth, increased harvest yields, a better developed root system, a larger leaf area, greener leaves, stronger shoots, less seed required, mobilization of the defense system of the plant, and good plant compatibility.

Thus, the use of the novel agrochemical composition, according to the invention, contribute considerably, for example, to keep young soybean plants healthy to safeguard quality and yield.

Moreover, the novel agrochemical composition, according to the invention, may contribute to an increased systemic action. Even if the individual compounds of the composition do not have sufficient systemic properties, the novel agrochemical composition, according to the invention, may still have this property. In a similar manner, the novel agrochemical composition, according to the invention, may result in higher long lasting efficacy of the fungicidal action.

SUMMARY OF THE INVENTION:

Accordingly, the present invention provides novel agrochemical composition comprising: a mixture of component (1), and at least two components selected from component (2), component (3), or a combination of component (2) and component (3), wherein the component (1) is at least one phenylamidine compound of formula (I)

wherein,

R¹ is selected from the group consisting of methyl, ethyl, isopropyl and cyclopropyl;

R²is selected from the group consisting of ethyl, isopropyl, cyclopropyl and cyclopropylmethyl;

R³ is selected from the group consisting of halogen, cyano, methyl, ethyl, isopropyl, halomethyl and cyclopropyl;

R⁴ is selected from the group consisting of halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy and cyclopropyl;

R⁵ and R⁶ are independently selected from the group consisting of hydrogen, halogen, cyano, methyl, halomethyl, and methoxy; or

R⁵ and R⁶, together with the carbon atom to which they are bound, form a cyclopropyl;

R⁷ is selected from the group consisting of hydrogen, halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy, ethoxy, isopropoxy, halomethoxy, haloethoxy and cyclopropyl; n represent integers 0, 1, 2, 3 or 4; and salts, A-oxides, metal complexes or stereoisomers thereof; as component (2) at least one fungicide selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, metarylpicoxamid, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, difenoconazole, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts; and as component (3) at least one fungicide different from components (1) and (2) selected from the groups:

(A) inhibitors of the sterol biosynthesis,

(B) inhibitors of the respiratory chain at complex I or II,

(C) inhibitors of the respiratory chain at complex III,

(D) compounds capable to have a multisite action, or

(E) inhibitors of histone deacetylase. It has been found that the action of the composition comprising components (1), (2) and (3) as defined herein goes far beyond the fungicidal and/or plant health improving action of the individual active components (synergistic action).

Moreover, we have found that, simultaneously, that is joint or separate, the application of the components (1), (2) and (3) or a successive application in a short time interval of the components (1), (2) and (3) allows enhanced control of harmful fungi and/or plant health effects, compared to the control rates and/or plant health effects that are possible with the individual components (synergistic mixtures).

In another embodiment, the present invention provides a method for controlling unwanted microorganisms, such as unwanted fungi and bacteria, comprising the step of applying at least one novel agrochemical composition, according to the invention, to the microorganisms and/or to their habitat (to the plants, plant parts, seeds, fruits or to the soil in which the plants grow).

In yet another embodiment, the present invention provides a composition for use in seed treatment, and a method for treating the seed for protecting the plants that grow from the seed after germination.

DETAILED DESCRIPTION OF THE INVENTION:

DEFINITIONS:

In the definitions of the symbols given in the above formulae, collective terms were used which are generally representative of the following substituents:

Hydrogen: Preferably, the definition of hydrogen encompasses also isotopes of hydrogen, preferably deuterium and tritium, more preferably deuterium.

Halogen: (also in combinations such as haloalkyl, haloalkoxy etc.) fluorine, chlorine, bromine and iodine, and preferably fluorine, chlorine, bromine and more preferably fluorine and chlorine;

Alkyl: (including in combinations such as alkylthio, alkoxy etc.) saturated, straight-chained or branched hydrocarbyl radicals having 1 to 6 carbon atoms, for example, Ci-Ce-alkyl, such as methyl, ethyl, propyl,

1 -methyl ethyl, 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-l -methylpropyl, l-ethyl-2-methylpropyl, heptyl and octyl. If the alkyl is at the end of a composite substituent, for example, in alkylcycloalkyl, the part of the composite substituent at the start, for example the cycloalkyl, may be mono- or polysubstituted identically or differently and independently by alkyl. Haloalkyl: (including in combinations such as haloalkylthio, haloalkoxy etc.) straight-chained or branched alkyl groups having 1 to 6 carbon atoms (as specified above), where some or all of the hydrogen atoms in these groups may be replaced by halogen atoms as specified above, for example, C1-C3 -haloalkyl such as 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-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl and 1,1,1- tri fluoroprop-2 -yl.

Halomethyl: a methyl group, where some or all of the hydrogen atoms in these group may be replaced by halogen atoms as specified above, for example, (but not limited to) chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, and preferably difluoromethyl or trifluoromethyl.

The term "cycloalkyl" means alkyl closed to form a ring. Non-limiting examples include but are not limited to cyclopropyl, cyclopentyl and cyclohexyl. This definition also applies to cycloalkyl as a part of a composite substituent, for example, cycloalkylalkyl etc., unless specifically defined elsewhere.

The term "alkoxy" used either alone or in compound words includes Ci-Ce alkoxy. 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, l-ethyl-2-methylpropoxy and their different isomers. The term “haloalkoxy” refers to an alkoxy as defined herein wherein one or more hydrogen of the alkoxy is substituted with same or different halogen. Halomethoxy refers to methoxy group wherein one or more hydrogens is replaced with one or more same or different halogen. Examples of halomethoxy include but not limited to fluoro methoxy, difluoromethoxy, trifluoromethoxy, chloromethoxy, dichloromethoxy, trichloromethoxy, and so on. Similarly, haloethoxy refers to ethoxy group wherein one or more hydrogens is replaced with one or more same or different halogen. Examples of haloethoxy include but not limited to fluoroethoxy, difluoroethoxy, trifluoroethoxy, chloroethoxy, dichloroethoxy, trichloroethoxy, and so on.

Depending on the nature of the substituents, the compounds of formula (I) can be present as mixtures of different possible isomeric forms, in particular of stereoisomers, such as, for example, E and Z, threo and erythro, and also optical isomers, and, if appropriate, also of tautomers. If applicable, compounds of formula (I) comprise both the E and the Z isomers, and also the threo and erythro, and the optical isomers, any mixtures of these isomers, and the possible tautomeric forms.

Any of the compounds according to the invention can exist in one or more optical, geometric or chiral isomer forms depending on the number of asymmetric centres in the compound. The invention thus relates equally to all the optical isomers and to their racemic or scalemic mixtures (the term "scalemic" denotes a mixture of enantiomers in different proportions), and to the mixtures of all the possible stereoisomers, in all proportions. The diastereomers and/or the optical isomers can be separated according to the methods which are known per se by a person ordinary skilled in the art.

Any of the compounds according to the invention can also exist in one or more geometric isomer forms depending on the number of double bonds in the compound. The invention thus relates equally to all geometric isomers and to all possible mixtures, in all proportions. The geometric isomers can be separated according to general methods, which are known per se by a person ordinary skilled in the art.

Depending on the nature of the substituents, the compounds of formula (I) can also exist in one or more geometric isomer forms depending on the relative position (syn/anti or cis/trans) of the substituents. The invention thus relates equally to all syn/anti (or cis/trans) isomers and to all possible syn/anti (or cis/trans) mixtures, in all proportions. The syn/anti (or cis/trans) isomers can be separated according to general methods, which are known per se by the man ordinary skilled in the art.

The compound of formula (I) carries amidine groups which induce basic properties. Thus, these compounds can react with acids to give salts.

Examples of inorganic acids are hydrohalic acids, such as hydrogen fluoride, hydrogen chloride, hydrogen bromide and hydrogen iodide; sulfuric acid, phosphoric acid and nitric acid, and acidic salts, such as NaHSO₄ and KHSO₄.

Suitable organic acids are, for example, formic acid, carbonic acid and alkanoic acids, such as acetic acid, trifluoroacetic acid, trichloroacetic acid and propionic acid, and also glycolic acid, thiocyanic acid, lactic acid, succinic acid, citric acid, benzoic acid, cinnamic acid, oxalic acid, alkylsulfonic acids (sulfonic acids having straight-chained or branched alkyl groups having 1 to 20 carbon atoms), arylsulfonic acids or - disulfonic acids (aromatic groups, such as phenyl and naphthyl, which carry one or two sulfonic acid groups), alkylphosphonic acids (phosphonic acids having straight -chained or branched alkyl groups having 1 to 20 carbon atoms), arylphosphonic acids or aryldiphosphonic acids (aromatic radicals, such as phenyl and naphthyl, which carry one or two phosphonic acid groups), where the alkyl and aryl groups may carry further substituents, for example, p-toluenesulfonic acid, salicylic acid, p-aminosalicylic acid, 2- phenoxybenzoic acid, 2-acetoxybenzoic acid, etc. The radical definitions and explanations given above in general terms or stated within preferred ranges can, however, also be combined with one another as desired, i.e. including between the particular ranges and preferred ranges. They apply both to the end products and correspondingly to precursors and intermediates. In addition, individual definitions may not apply.

Accordingly, the present invention provides a novel agrochemical composition comprising: a mixture of component (1), and at least two components selected from component (2), component (3), or a combination of component (2) and component (3), wherein the component (1) is at least one phenylamidine compound of formula (I)

wherein,

R¹ is selected from the group consisting of methyl, ethyl, isopropyl, and cyclopropyl;

R²is selected from the group consisting of ethyl, isopropyl, cyclopropyl, and cyclopropylmethyl;

R³ is selected from the group consisting of halogen, cyano, methyl, ethyl, isopropyl, halomethyl, and cyclopropyl;

R⁴ is selected from the group consisting of halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy, and cyclopropyl;

R⁵ and R⁶ together with the carbon atom, to which they are bound, form a cyclopropyl;

R⁷ is selected from the group consisting of hydrogen, halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy, ethoxy, isopropoxy, halomethoxy, haloethoxy, and cyclopropyl; n represent integers 0, 1, 2, 3 or 4; and salts, A-oxides, metal complexes or stereoisomers thereof; as component (2) at least one fungicide selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, metarylpicoxamid, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, difenoconazole, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb and their salts; and as component (3) at least one fungicide different from components (1) and (2) which is selected from the groups: (A) inhibitors of the sterol synthesis,

(B) inhibitors of the respiratory chain at complex I or II,

(C) inhibitors of the respiratory chain at complex III,

(D) compounds capable of have a multisite action, or

(E) inhibitors of histone deacetylase; in a synergistically effective amount.

In a one more preferred embodiment, the compound of formula (I) or salts, A-oxides, metal complexes or stereoisomers thereof as component (1) is selected from:

(1-1) N'-(5-chloro-2-methyl-3-(3-methylbenzyl)phenyl)-N-ethyl-N-methylformimidamide;

(1-2) N-ethyl-N'-(5-fluoro-2-methyl-3-(3-methylbenzyl)phenyl)-N-methylformimidamide;

(1-3) N'-(5-chloro-3-(4-methoxybenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide;

(1-4) N'-(3-(2-bromobenzyl)-5-fluoro-2-methylphenyl)-N-ethyl-N-methylformimidamide;

(1-5) N-ethyl-N'-(3-(3-fluoro-2-methylbenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

(1-6) N-ethyl-N'-(3-(3-methoxybenzyl)-2,5-dimethylphenyl)-N-methylformimidamide;

(1-7) N'-(3-(4-(difluoromethoxy)benzyl)-2,5-dimethylphenyl)-N-ethyl-N-methylformimidamide;

(1-8) N-ethyl-N'-(3-(3-fluoro-5-methylbenzyl)-5-methoxy-2-methylphenyl)-N-methylformimidamide;

(1-9) N'-(5-chloro-3-(4-(difluoromethoxy)benzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide, or

(I- 10) N'-(5-chloro-3-(4-isopropoxybenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide.

In a more preferred embodiment, the compound of formula (I) or salts, A-oxides, metal complexes or stereoisomers thereof as component (1) is N'-(5-chloro-2-methyl-3-(3-methylbenzyl)phenyl)-N-ethyl-N- methylformi midamide.

The compound of formula (I) are prepared according to the analogous procedure as described in experimental examples.

In a preferred embodiment, the component (2) is at least one fungicide selected from the following groups: azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, metyltetraprole, metarylpicoxamid, benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, inpyrfluxam, difenoconazole, cyproconazole, mefentrifluconazole, prothioconazole, tebuconazole, chlorothalonil, mancozeb, and their salts.

According to a further embodiment, the component (3) in the composition, comprises at least one fungicide, which is different from components (1) and (2), selected from: (A) inhibitors of the sterol biosynthesis, for example, (A001) prothioconazole; (A002) cyproconazole; (A003) tebuconazole; (A004) mefentrifluconazole; (A005) difenoconazole; (A006) epoxiconazole; (A007) metconazole; (A008) paclobutrazol; (A009) pyrisoxazole; (A010) propiconazole; (A011) tetraconazole; (A012) triticonazole; (A013) ipfentrifluconazole; (A014) clotrimazole; (A015) econazole; (A016) isoconazole; (A017) miconazole; (A018) oxpoconazole; (A019) triflumizole; (A020) azaconazole; (A021) bromuconazole; (A022) diniconazole; (A023) diniconazole-M; (A024) etaconazole; (A025) fenbuconazole; (A026) hexaconazole; (A027) imibenconazole; (A028) penconazole; (A029) simeconazole; (A030) ipconazole; (A031) uniconazole; (A032) fenhexamid; (A033) fenpropidin; (A034) fenpropimorph; (A035) fenpyrazamine; (A036) fluquinconazole; (A037) flutriafol; (A038) imazalil; (A039) imazalil sulfate; (A040) spiroxamine; (A041) prochloraz; (A042) myclobutanil; (A043) triadimenol; (A044) tridemorph; (A045) terbinafine; (A046) buthiobate; (A047) pyrifenox; (A048) fenarimol; (A049) nuarimol; (A050) triarimol; (A051) triforine; (A052) bitertanol; (A053) pefurazoate; (A054) triadimefon; (A055) pyributicarb; (A056) dodemorph; (A057) aldimorph; (A058) trimorphamide; (A059) piperalin; (A060) naftifine;

(B) inhibitors of the respiratory chain at complex I or II, for example, (B001) benzovindiflupyr; (B002) bixafen; (B003) fluindapyr; (B004) fluxapyroxad; (B005) inpyrfluxam; (B006) boscalid; (B007) carboxin; (B008) fluopyram; (B009) flutolanil; (B010) furametpyr; (B011) isofetamid; (B012) penflufen; (BOD) penthiopyrad; (BOM) pydiflumetofen; (B015) pyraziflumid; (B016) sedaxane; (B017) isoflucypram; (B018) pyrapropoyne; (B019) fenfuram; (B020) mepronil; (B021) benodanil; (B022) oxycarboxin; (B023) diflumetorim; (B024) thifluzamide; (B025) isopyrazam;

(C) inhibitors of the respiratory chain at complex III, for example, (C001) metarylpicoxamid; (C002) azoxystrobin; (C003) metominostrobin; (C004) orysastrobin; (C005) picoxystrobin; (C006) pyraclostrobin; (C007) pyrametostrobin; (C008) pyraoxystrobin; (C009) trifloxystrobin; (C010) coumethoxystrobin; (C011) coumoxystrobin; (CO 12} dimoxystrobin; (CO 13} enoxastrobin; (COM) flufenoxystrobin; (C015) fluoxastrobin; (C016) mandestrobin; (COD) ametoctradin; (C018) amisulbrom; (C019) cyazofamid; (C020) famoxadone; (C021) fenamidone; (C022) kresoxim-methyl; (C023) metyltetraprole; (C024) florylpicoxamid; (C025) pyribencarb; (C026) fenpicoxamid;

(D) compounds capable to have a multisite action, for example, (D001) chlorothalonil; (D002) mancozeb; (D003) copper hydroxide; (D004) copper oxychloride; (D005) captafol; (D006) captan; (D007) thiram; (D008) zineb; (D009) ziram; (D010) ferbam; (D011) dichlofluanid; (D012) tolylfluanid; (DOM) guazatine; (DOM) iminoctadine; (D015) anilazine; (D016) quinomethionate; (D017) dithianon; (D018) dodine; (D019) folpet; (D020) maneb; (D021) metiram; (D022) metiram zinc; (D023) oxine-copper; (D024) propineb; (D025) copper naphthenate; (D026) copper oxide; (D027) copper sulfate; (D028) Bordeaux mixture; (D029) sulfur and sulfur preparations including calcium poly sulfide; and

(E) inhibitors of histone deacetylase, for example, (E001) flufenoxadiazam; (E002) N-methoxy-N-[[4- [5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide.

In a preferred embodiment, the compound of formula (I) or salts, A-oxides, metal complexes or stereoisomers thereof as component (1) wherein,

R¹ is methyl;

R²is selected from the group consisting of ethyl and isopropyl;

R³ is selected from the group consisting of halogen, and methyl;

R⁴ is selected from the group consisting of halogen, methyl, halomethyl and methoxy;

R⁵ and R⁶ is hydrogen;

R⁷ is selected from the group consisting of hydrogen, halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy, ethoxy, isopropoxy, halomethoxy, haloethoxy, and cyclopropyl; n represent integers 0, 1, 2, 3 or 4; as component (2) at least one fungicide selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, metarylpicoxamid, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, difenoconazole, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb and their salts; and as component (3) at least one fungicide different from components (1) and (2) which is selected from the groups:

(A) inhibitors of the sterol biosynthesis, for example, (A001) prothioconazole; (A002) cyproconazole; (A003) tebuconazole; (A004) mefentrifluconazole; (A005) difenoconazole; (A006) epoxiconazole; (A007) metconazole; (A008) paclobutrazol; (A009) pyrisoxazole; (A010) propiconazole; (A011) tetraconazole; (A012) triticonazole; (A013) ipfentrifluconazole; (A014) clotrimazole; (A015) econazole; (A016) isoconazole; (A017) miconazole; (A018) oxpoconazole; (A019) triflumizole; (A020) azaconazole; (A021) bromuconazole; (A022) diniconazole; (A023) diniconazole-M; (A024) etaconazole; (A025) fenbuconazole; (A026) hexaconazole; (A027) imibenconazole; (A028) penconazole; (A029) simeconazole; (A030) ipconazole; (A031) uniconazole; (A032) fenhexamid; (A033) fenpropidin; (A034) fenpropimorph; (A035) fenpyrazamine; (A036) fluquinconazole; (A037) flutriafol; (A038) imazalil; (A039) imazalil sulfate; (A040) spiroxamine; (A041) prochloraz; (A042) myclobutanil; (A043) triadimenol; (A044) tridemorph; (A045) terbinafine; (A046) buthiobate; (A047) pyrifenox; (A048) fenarimol; (A049) nuarimol; (A050) triarimol; (A051) triforine; (A052) bitertanol; (A053) pefurazoate; (A054) triadimefon; (A055) pyributicarb; (A056) dodemorph; (A057) aldimorph; (A058) trimorphamide; (A059) piperalin; (A060) naftifine;

(C) inhibitors of the respiratory chain at complex III, for example, (C001) metarylpicoxamid; (C002) azoxystrobin; (C003) metominostrobin; (C004) orysastrobin; (C005) picoxystrobin; (C006) pyraclostrobin; (C007) pyrametostrobin; (C008) pyraoxystrobin; (C009) trifloxystrobin; (C010) coumethoxystrobin; (C011) coumoxystrobin; (C012) dimoxystrobin; (CO 13} enoxastrobin; (COM) flufenoxystrobin; (C015) fluoxastrobin; (C016) mandestrobin; (COD) ametoctradin; (C018) amisulbrom; (C019) cyazofamid; (C020) famoxadone; (C021) fenamidone; (C022) kresoxim-methyl; (C023) metyltetraprole; (C024) florylpicoxamid; (C025) pyribencarb; (C026) fenpicoxamid;

In one embodiment component (2) at least one fungicide selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, metarylpicoxamid, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, difenoconazole, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb and their salts; In one embodiment, the present invention provide synergistic composition comprising the compound of formula (I) or salts, A-oxides, metal complexes or stereoisomers thereof as component (1); the component (2) is at least one fungicide selected from the following groups: azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, metyltetraprole, metarylpicoxamid, benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, inpyrfluxam, difenoconazole, cyproconazole, mefentrifluconazole, prothioconazole, tebuconazole, chlorothalonil, mancozeb, and their salts and the component (3) in the composition, comprises at least one fungicide, which is different from components (1) and (2), selected from: (A) inhibitors of the sterol biosynthesis, for example, (A001) prothioconazole; (A002) cyproconazole; (A003) tebuconazole; (A004) mefentrifluconazole; (A005) difenoconazole; (A006) epoxiconazole; (A007) metconazole; (A008) paclobutrazol; (A009) pyrisoxazole; (A010) propiconazole; (A011) tetraconazole; (A012) triticonazole; (A013) ipfentrifluconazole; (A014) clotrimazole; (A015) econazole; (A016) isoconazole; (A017) miconazole; (A018) oxpoconazole; (A019) triflumizole; (A020) azaconazole; (A021) bromuconazole; (A022) diniconazole; (A023) diniconazole-M; (A024) etaconazole; (A025) fenbuconazole; (A026) hexaconazole; (A027) imibenconazole; (A028) penconazole; (A029) simeconazole; (A030) ipconazole; (A031) uniconazole; (A032) fenhexamid; (A033) fenpropidin; (A034) fenpropimorph; (A035) fenpyrazamine; (A036) fluquinconazole; (A037) flutriafol; (A038) imazalil; (A039) imazalil sulfate; (A040) spiroxamine; (A041) prochloraz; (A042) myclobutanil; (A043) triadimenol; (A044) tridemorph; (A045) terbinafine; (A046) buthiobate; (A047) pyrifenox; (A048) fenarimol; (A049) nuarimol; (A050) triarimol; (A051) triforine; (A052) bitertanol; (A053) pefurazoate; (A054) triadimefon; (A055) pyributicarb; (A056) dodemorph; (A057) aldimorph; (A058) trimorphamide; (A059) piperalin; (A060) naftifine.

In one another embodiment, the present invention provide synergistic composition comprising the compound of formula (I) or salts, A-oxides, metal complexes or stereoisomers thereof as component (1); the component (2) is at least one fungicide selected from the following groups: azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, metyltetraprole, metarylpicoxamid, benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, inpyrfluxam, difenoconazole, cyproconazole, mefentrifluconazole, prothioconazole, tebuconazole, chlorothalonil, mancozeb, and their salts and the component (3) in the composition, comprises at least one fungicide, which is different from components (1) and (2), selected from: (B) inhibitors of the respiratory chain at complex I or II, for example, (B001) benzovindiflupyr; (B002) bixafen; (B003) fluindapyr; (B004) fluxapyroxad; (B005) inpyrfluxam; (B006) boscalid; (B007) carboxin; (B008) fluopyram; (B009) flutolanil; (B010) furametpyr; (B011) isofetamid; (B012) penflufen; (BOD) penthiopyrad; (BOM) pydiflumetofen; (B015) pyraziflumid; (B016) sedaxane; (B017) isoflucypram; (B018) pyrapropoyne; (BOW) fenfuram; (B020) mepronil; (B021) benodanil; (B022) oxycarboxin; (B023) diflumetorim; (B024) thifluzamide; (B025) isopyrazam;

In one another embodiment, the present invention provide synergistic composition comprising the compound of formula (I) or salts, 7V-oxides, metal complexes or stereoisomers thereof as component (1); the component (2) is at least one fungicide selected from the following groups: azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, metyltetraprole, metarylpicoxamid, benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, inpyrfluxam, difenoconazole, cyproconazole, mefentrifluconazole, prothioconazole, tebuconazole, chlorothalonil, mancozeb, and their salts and the component (3) in the composition, comprises at least one fungicide, which is different from components (1) and (2), selected from: (C) inhibitors of the respiratory chain at complex III, for example, (C001) metarylpicoxamid; (C002) azoxystrobin; (C003) metominostrobin; (C004) orysastrobin; (C005) picoxystrobin; (C006) pyraclostrobin; (C007) pyrametostrobin; (C008) pyraoxystrobin; (C009) trifloxystrobin; (C010) coumethoxystrobin; (C011) coumoxystrobin; (CO 12} dimoxystrobin; (CO 13} enoxastrobin; (COM) flufenoxystrobin; (C015) fluoxastrobin; (C016) mandestrobin; (C017) ametoctradin; (C018) amisulbrom; (C019) cyazofamid; (C020) famoxadone; (C021) fenamidone; (C022) kresoxim-methyl; (C023) metyltetraprole; (C024) florylpicoxamid; (C025) pyribencarb; (C026) fenpicoxamid.

In yet embodiment, the present invention provide synergistic composition comprising the compound of formula (I) or salts, 7V-oxides, metal complexes or stereoisomers thereof as component (1); the component (2) is at least one fungicide selected from the following groups: azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, metyltetraprole, metarylpicoxamid, benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, inpyrfluxam, difenoconazole, cyproconazole, mefentrifluconazole, prothioconazole, tebuconazole, chlorothalonil, mancozeb, and their salts. and the component (3) in the composition, comprises at least one fungicide, which is different from components (1) and (2), selected from: (D) compounds capable to have a multisite action, for example, (D001) chlorothalonil; (D002) mancozeb; (D003) copper hydroxide; (D004) copper oxychloride; (D005) captafol; (D006) captan; (D007) thiram; (D008) zineb; (D009) ziram; (D010) ferbam; (D011) dichlofluanid; (D012) tolylfluanid; (DO 13} guazatine; (DOM) iminoctadine; (D015) anilazine; (D016) quinomethionate; (DOW) dithianon; (D018) dodine; (D019) folpet; (D020) maneb; (D021) metiram; (D022) metiram zinc; (D023) oxine-copper; (D024) propineb; (D025) copper naphthenate; (D026) copper oxide; (D027) copper sulfate; (D028) bordeaux mixture; (D029) sulfur and sulfur preparations including calcium polysulfide. In yet another embodiment, the present invention provide synergistic composition comprising the compound of formula (I) or salts, A-oxides, metal complexes or stereoisomers thereof as component (1); the component (2) is at least one fungicide selected from the following groups: azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, metyltetraprole, metarylpicoxamid, benzovindiflupyr, bixafen, fluindapyr, fluxapyroxad, inpyrfluxam, difenoconazole, cyproconazole, mefentrifluconazole, prothioconazole, tebuconazole, chlorothalonil, mancozeb, and their salts. and the component (3) in the composition, comprises at least one fungicide, which is different from components (1) and (2), selected from: (E) inhibitors of histone deacetylase, for example, (E001) flufenoxadiazam; (E002) N-methoxy-N- [[4-[5-(trifluoromethyl)-l,2,4-oxadiazol-3-yl]phenyl]methyl]cyclopropanecarboxamide.

In a specific embodiment, component (3) is at least one fungicide different from components (1) and (2).

All named mixing partners of the components (2) and (3) [classes (A) to (E)] can, if their functional groups enable this, optionally form salts with suitable bases or acids. All named mixing partners of the components (2) and (3) [classes (A) to (E)] is meant herein to also include the respective salts, isomers and esters of the above mentioned compounds.

Where a component (1) or component (2) or component (3) can be present in a tautomeric form, such a compound is understood herein to include, wherever applicable, corresponding tautomeric forms, even when these are not specifically mentioned in each case.

Particularly preferred as component (3) is (A) inhibitors of the sterol biosynthesis, including (A001) prothioconazole; (A002) cyproconazole; (A003) tebuconazole; (A004) mefentrifluconazole; (A005) difenoconazole; and (A006) epoxiconazole.

Particularly preferred as component (3) is (B) inhibitors of the respiratory chain at complex I or II, including (B001) benzovindiflupyr; (B002) bixafen; (B003) fluindapyr; (B004) fluxapyroxad; and (B005) inpyrfluxam.

Particularly preferred as component (3) is (C) inhibitors of the respiratory chain at complex III, including (C001) metarylpicoxamid, (C002) azoxystrobin; (C003) metominostrobin; (C004) orysastrobin; (C005) picoxystrobin; (C006) pyraclostrobin; (C009) trifloxystrobin.

Particularly preferred as component (3) is (D) compounds capable to have a multisite action, including (D001) chlorothalonil; (D002) mancozeb; (D003) copper hydroxide; and (D004) copper oxychloride.

Particularly preferred as component (3) is (E) inhibitors of histone deacetylase, including (E001) flufenoxadiazam. In a particular preferred embodiment, the component (3) is at least one fungicide selected from the group consisting of benzovindiflupyr, bixafen, flufenoxadiazam, fluindapyr, fluxapyroxad, inpyrfluxam, epoxiconazole, prothioconazole, tebuconazole, cyproconazole, difenoconazole, mefentrifluconazole, Picoxystrobin, Metominostrobin, Metarylpicoxamid, chlorothalonil, mancozeb, copper hydroxide, copper oxy chloride, metarylpicoxamid and their salts.

In one embodiment, the ternary agrochemical composition according to the present invention, wherein the weight ratio of component (1) to component (2) is in the range from 100:1 to 1:100, preferably from 50:1 to 1:50, more preferably from 25:1 to 1:25, even more preferably from 20:1 to 1:20, including also ratios from 10:1 to 1:10, 5:1 to 1:5, 4:1 to 1:4, 3:1 to 1:3, 2:1 to 1:2, or 1:1. The weight ratio of component (1) to component (3) in ternary composition is in the range from 100:1 to 1:100, preferably from 50:1 to 1:50, more preferably from 25: 1 to 1 :25, even more preferably from 20: 1 to 1 :20, including also ratios from 10: 1 to 1:10, 5:1 to 1:5, 4:1 to 1:4, 3:1 to 1:3, 2:1 to 1:2, or 1:1. The weight ratio of component (2) to component (3) in ternary composition is in the range from 100: 1 to 1 : 100, preferably from 50: 1 to 1 :50, more preferably from 25:1 to 1:25, even more preferably from 20:1 to 1:20, including also ratios from 10:1 to 1:10, 5:1 to 1:5, 4:1 to 1:4, 3:1 to 1:3, 2:1 to 1:2, or 1:1.

The following compositions exemplify specific embodiments according to the present invention.

Examples of suitable agrochemical compositions of the invention that include components (1), (2), and (3), are listed in the following tables A to R.

Table-A: Following combinations, listed in Table-A, wherein component (1) (compound of formula (I), component (2) is azoxystrobin and another component (3), are selected from the groups (A) to (E) as defined herein (component 3, for example, (A001) or prothioconazole, in combination [(I)+ component (2) + (A001)]).

Table-A:

(1) + (component (2) + (A001), (I) + (component (2) + (A002), (I) + (component (2) + (A003), (I) + (component (2) + (A004), (I) + (component (2) + (A005), (I) + (component (2) + (A006), (I) + (component

(2) + (A007), (I) + (component (2) + (A008), (I) + (component (2) + (A009), (I) + (component (2) + (A010),

(1) + (component (2) + (A011), (I) + (component (2) + (A012), (I) + (component (2) + (A013), (I) + (component (2) + (A014), (I) + (component (2) + (A015), (I) + (component (2) + (A016), (I) + (component

(2) + (A017), (I) + (component (2) + (A018), (I) + (component (2) + (A019), (I) + (component (2) + (A020),

(1) + (component (2) + (A021), (I) + (component (2) + (A022), (I) + (component (2) + (A023), (I) + (component (2) + (A024), (I) + (component (2) + (A025), (I) + (component (2) + (A026), (I) + (component

(2) + (A027), (I) + (component (2) + (A028), (I) + (component (2) + (A029), (I) + (component (2) + (A030), (I) + (component (2) + (A031), (I) + (component (2) + (A032), (I) + (component (2) + (A033), (I) + (component (2) + (A034), (I) + (component (2) + (A035), (I) + (component (2) + (A036), (I) + (component (2) + (A037), (I) + (component (2) + (A038), (I) + (component (2) + (A039), (I) + (component (2) + (A040),

(1) + (component (2) + (A041), (I) + (component (2) + (A042), (I) + (component (2) + (A043), (I) + (component (2) + (A044), (I) + (component (2) + (A045), (I) + (component (2) + (A046), (I) + (component

(2) + (A047), (I) + (component (2) + (A048), (I) + (component (2) + (A049), (I) + (component (2) + (A050),

(1) + (component (2) + (A051), (I) + (component (2) + (A052), (I) + (component (2) + (A053), (I) + (component (2) + (A054), (I) + (component (2) + (A055), (I) + (component (2) + (A056), (I) + (component

(2) + (A057), (I) + (component (2) + (A058), (I) + (component (2) + (A059), (I) + (component (2) + (A060),

(1) + (component (2) + (B001), (I) + (component (2) + (B002), (I) + (component (2) + (B003), (I) + (component (2) + (B004), (I) + (component (2) + (B005), (I) + (component (2) + (B006), (I) + (component

(2) + (B007), (I) + (component (2) + (B008), (I) + (component (2) + (B009), (I) + (component (2) + (B010),

(1) + (component (2) + (B011), (I) + (component (2) + (B012), (I) + (component (2) + (BO ), (I) + (component (2) + (BOM), (I) + (component (2) + (B015), (I) + (component (2) + (B016), (I) + (component

(2) + (B017), (I) + (component (2) + (B018), (I) + (component (2) + (B019), (I) + (component (2) + (B020),

(1) + (component (2) + (B021), (I) + (component (2) + (B022), (I) + (component (2) + (B023), (I) + (component (2) + (B024), (I) + (component (2) + (B025), (I) + (component (2) + (C001), (I) + (component

(2) + (C002), (I) + (component (2) + (C003), (I) + (component (2) + (C004), (I) + (component (2) + (C005),

(1) + (component (2) + (C006), (I) + (component (2) + (C007), (I) + (component (2) + (C008), (I) + (component (2) + (C009), (I) + (component (2) + (CO 10), (I) + (component (2) + (C01 !), (!) + (component

(2) + (COM), (I) + (component (2) + (COM), (I) + (component (2) + (COM), (I) + (component (2) + (C015),

(1) + (component (2) + (C016), (I) + (component (2) + (C017), (I) + (component (2) + (C018), (I) + (component (2) + (CO 19), (I) + (component (2) + (C020), (I) + (component (2) + (C021), (I) + (component

(2) + (C022), (I) + (component (2) + (C023), (I) + (component (2) + (C024), (I) + (component (2) + (C025),

(1) + (component (2) + (C026), (I) + (component (2) + (D001), (I) + (component (2) + (D002), (I) + (component (2) + (D003), (I) + (component (2) + (D004), (I) + (component (2) + (D005), (I) + (component

(2) + (D006), (I) + (component (2) + (D007), (I) + (component (2) + (D008), (I) + (component (2) + (D009),

(1) + (component (2) + (DO 10), (I) + (component (2) + (D011), (I) + (component (2) + (DOM), (I) + (component (2) + (DOM), (I) + (component (2) + (DOM), (I) + (component (2) + (DOM), (I) + (component

(2) + (DO 16), (I) + (component (2) + (DO ), (I) + (component (2) + (DO 18), (I) + (component (2) + (DO 19),

(1) + (component (2) + (D020), (I) + (component (2) + (D021), (I) + (component (2) + (D022), (I) + (component (2) + (D023), (I) + (component (2) + (D024), (I) + (component (2) + (D025), (I) + (component

(2) + (D026), (I) + (component (2) + (D027), (I) + (component (2) + (D028), (I) + (component (2) + (D029), (I) + (component (2) + (E001) and (I) + (component (2) + (E002).

Table B: Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with metominostrobin.

Table C:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with picoxystrobin.

Table D:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with trifloxystrobin.

Table E:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with metyltetraprole.

Table F:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with metarylpicoxamid.

Table G:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with benzovindiflupyr.

Table H:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with bixafen.

Table I:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with fluindapyr.

Table J: Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with fluxapyroxad.

Table K:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with inpyrfluxam.

Table L:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with difenoconazole.

Table M:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with cyproconazole.

Table N:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with mefentrifluconazole.

Table O:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with prothioconazole.

Table P:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with tebuconazole.

Table Q:

Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with chlorothalonil.

Table R: Combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] are defined as combination [(I) + component (2) + (A001] to [(I) + component (2) + (E002)] of Table A, wherein component (2) in each mixture is replaced with mancozeb. In one embodiment, the composition mentioned in table-A to Table-R, wherein compound (I) is selected from compound (1-1) to compound (I- 10).

In a preferered embodiment, the composition mentioned in table-A to Table-R, wherein compound (I) is replaced with compound (1-1).

Table 1: Table 1 preferably provides agrochemical compositions of SNs. 1 to 309include, besides the listed component (2) and component (3), a compound of formula (I) as component (1).

*May be applied in the form of its enantiomer or salt, unless a specific enantiomer or salt is mentioned.

Particularly preferred agrochemical composition of components (1), (2) and (3) according to the present invention are selected from the following: Table 2:

wherein, compounds in each case may optionally be present in the form of their respective enantiomers, salts or esters, in particular their aforementioned preferred enantiomers, salts or esters, unless a specific enantiomer, salt or ester is designated.

Table 3: Compositions 1 to 278, which differ from the corresponding compositions 1 to 309 of Table 2, wherein compound (1-1) as a component (1) in each mixture is replaced with compound (1-2).

Table 4:

Compositions 1 to 278, which differ from the corresponding compositions 1 to 309 of Table 2, wherein compound (1-1) as a component (1) in each mixture is replaced with compound (1-3). Table 5: Compositions 1 to 278, which differ from the corresponding compositions 1 to 309 of Table 2, wherein compound (1-1) as a component (1) in each mixture is replaced with compound (1-4).

Table 6:

Compositions 1 to 278, which differ from the corresponding compositions 1 to 309 of Table 2, wherein compound (1-1) as a component (1) in each mixture is replaced with compound (1-5).

Table 7:

Compositions 1 to 278, which differ from the corresponding compositions 1 to 309 of Table 2, wherein compound (1-1) as a component (1) in each mixture is replaced with compound (1-6).

Table 8:

Compositions 1 to 278, which differ from the corresponding compositions 1 to 309 of Table 2, wherein compound (1-1) as a component (1) in each mixture is replaced with compound (1-7).

Table 9:

Compositions 1 to 278, which differ from the corresponding compositions 1 to 309 of Table 2, wherein compound (1-1) as a component (1) in each mixture is replaced with compound (1-8).

Table 10:

Compositions 1 to 278, which differ from the corresponding compositions 1 to 309 of Table 2, wherein compound (1-1) as a component (1) in each mixture is replaced with compound (1-9).

Table 11:

Compositions 1 to 278, which differ from the corresponding compositions 1 to 309 of Table 2, wherein compound (1-1) as a component (1) in each mixture is replaced with compound (1-10).

The novel agrochemical composition usable in accordance with the invention can be converted to the formulations such as, a suspension concentrate (SC), a water dispersible granule (WDG)/(WG), a tablet (TB), a wettable powder (WP), a water dispersible tablet (WT), an ultra-low volume (ULV), a liquid (UL), an ultra-low volume (ULV), a suspension (SU), a water soluble powder (SP), a suspo-emulsion (SE), a granule (GR), an emulsifiable granule (EG), an oil-in-water emulsion (EW), an emulsifiable granule (EG), an emulsion oil in water (EO), an emulsifiable powder (EP), an emulsion for seed treatment (ES), a solution for seed treatment (LS), a flowable concentrate for seed treatment (FS), an emulsifiable concentrate (EC), a micro-emulsion (ME), oil-in-water emulsions (EW), an oil miscible flowable concentrate (oil miscible suspension) (OF), an oil dispersible powder (OP), an oil dispersion (OD), a capsule suspension (CS), a dustable powder (DP), a soluble concentrate (SL), a water soluble granule (SG), an aerosol (AE), a mixed formulation of CS and SC (ZC), a mixed formulation of CS and SE (ZE) or a mixed formulation of CS and EW (ZW). These and further composition types are defined in the “Catalogue of pesticide formulation types and the international coding system”, Technical Monograph No. 2, 6^th Edition, May 2008, CropLife International.

The agrochemical compositions are prepared in a known manner, such as described by Mollet and Grubenmann, Formulation technology, Wiley-VCH, Weinheim, 2001; or Knowles, New developments in crop protection product formulation, Agrow Reports, DS243, T&F Informa, London, 2005. These formulations are prepared in a known manner, by mixing the active compounds with agriculturally acceptable additives, for example, customary extender(s), solvent(s) or diluent(s), dye(s), wetting agent(s), dispersant(s), emulsifier(s), antifoam(s), preservative(s), thickener(s), adhesive(s), gibberellins, solid carrier(s), liquid carrier(s), gaseous carrier(s) or filler(s), surfactant(s), binder(s), penetration enhancer(s), protective colloid(s), adhesion agent(s), disintegrating agent(s), pH adjuster(s), anti-caking agent(s), penetrant(s), anti-freezing agent(s), filler(s), stabilizer(s), coloring agent(s), humectant(s), repellent(s), attractant(s), feeding stimulant(s), compatibilizer(s), bactericide(s), and mixtures thereof and also water.

According to the invention the term "agrochemical composition" means a combination or mixture of at least three active ingredients/compounds/components with further agriculturally suitable additives, such as agriculturally suitable auxiliaries, e.g. solvents, carriers, surfactants, extenders or the like which are described above. The term "agrochemical composition" also comprises the terms "crop protection composition" and "formulation".

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

Suitable solid carrier(s) or filler(s) are mineral earths, e.g. silicates, silica gels, talc, kaolins, lime stone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharides, e.g. cellulose, starch, fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.

Suitable surfactant(s) are surface-active compounds, such as anionic, cationic, non-ionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emulsifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon’s, Vol. 1: Emulsifiers & Detergents, McCutcheon’s Directories, USA, 2020 (International Edition or North American Edition).

Suitable emulsifier(s) includes but not limited to synthetic emulsifiers such as Anionic emulsifiers, cationic emulsifiers, Non-ionic emulsifiers, and Amphoteric/Zwitterionic emulsifiers; Natural emulsifying agents such as Vegetable derivatives, Animal derivatives, Semi synthetic agents, Synthetic agents; Finely divided or finely dispersed solid particle emulsifiers; and Auxiliary agents

Suitable anionic surfactant(s) are alkali, alkaline earth or ammonium salts of sulfonates, sulfates, phosphates, carboxylates, and mixtures thereof. Examples of sulfonates are alkylarylsulfonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates. Examples of sulfates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethoxylated alcohols, or of fatty acid esters. Examples of phosphates are phosphate esters. Examples of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol ethoxylates.

Suitable nonionic surfactant(s) are alkoxylates, N-subsituted fatty acid amides, amine oxides, esters, sugar- based surfactants, polymeric surfactants, and mixtures thereof. Examples of alkoxylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents. Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide. Examples of N-substituted fatty acid amides are fatty acid glucamides or fatty acid alkanol amides. Examples of esters are fatty acid esters, glycerol esters or monoglycerides. Examples of sugar -based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolyglucosides. Examples of polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylalcohols, or vinylacetate.

Suitable cationic surfactant(s) are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines. Suitable amphoteric surfactants are alkylbetaines and imidazolines. Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide. Suitable polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of polyacrylic acid or polyacid comb -polymers. Examples of polybases are polyvinylamines or polyethyleneamines. Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the inventive mixtures on the target. Examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports, DS256, T&F Informa UK, 2006, chapter 5.

Suitable thickener(s) are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), inorganic clays (organically modified or unmodified), polycarboxylates, and silicates.

Suitable bactericide(s) are bronopol and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones .

Suitable anti-freezing agent(s) are ethylene glycol, propylene glycol, urea and glycerin.

Stabilizer(s) is selected from the group consisting of, but not limited to, drying agent such as zeolite, quick lime or magnesium oxide; antioxidant agent such as phenol type, amine type, sulfur type or phosphorus type; or ultraviolet absorber such as salicylic acid type or a benzophenone type; or methylated soybean oil; or peroxide compounds such as hydrogen peroxide and organic peroxides, alkyl nitrites such as ethyl nitrite and alkyl glyoxylates such as ethyl glyoxylate, zeolite, antioxidants such as phenol compounds, phosphoric acid compounds and the like; ultraviolet absorbers such as benzophenone compounds or derivatives thereof. However, those skilled in the art will appreciate that it is possible to utilize other conventionally known stabilizers without departing from the scope of the present invention. These stabilizers may be used alone or in combinations thereof.

Suitable anti-foaming agent(s) are silicones, long chain alcohols, and salts of fatty acids.

Suitable colorant(s) (e.g. in red, blue, or green) are pigments of low water solubility and water-soluble dyes. Examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanoferrate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).

Suitable tackifier(s) or binder(s) or solubilizer(s) are polyvinylpyrrolidones, polyvinylacetates, polyvinyl alcohols, polyacrylates, biological or synthetic waxes, polyoxyethylated castor oil, polyoxyethylated sorbitan ester and cellulose ethers.

The novel agrochemical composition generally comprises from 0.01 to 99%, from 0.05 to 98%, preferably from 0.1 to 95%, more preferably from 0.5 to 90%, most preferably from 1 to 80 % by weight of the active compounds according to the invention. The active substances are employed in a purity of 90% to 100%, preferably from 95% to 100%.

The below formulations types a) to m) further illustrate, but do not limit, the invention.

Preferred formulations of agrochemical composition and their preparations are: a) Water-soluble concentrates (SL, LS)

10-60 wt% of an inventive mixture 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) ad 100 wt%. The active substance dissolves upon dilution with water. b) Dispersible concentrates (DC)

5-25 wt% of an inventive mixture and 1-10 wt% of a dispersant (e.g. polyvinylpyrrolidone) are dissolved in an organic solvent (e.g. cyclohexanone) ad 100 wt%. The dilution with water gives a dispersion. c) Emulsifiable concentrates (EC)

15-70 wt% of an inventive mixture and 5-10 wt% of emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a water-insoluble organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. The dilution with water gives an emulsion. d) Emulsions (EW, EO, ES)

5-40 wt% of an inventive mixture and 1-10 wt% of emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in a 20-40 wt% water-insoluble organic solvent (e.g. aromatic hydrocarbon). This mixture is introduced into water ad 100 wt% by means of an emulsifying machine and made into a homogeneous emulsion. The dilution with water gives an emulsion. e) Suspensions (SC, OD, FS)

In an agitated ball mill, 20-60 wt% of an inventive mixture are comminuted with the addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0.1-2 wt% thickener (e.g. xanthan gum) and water ad 100 wt% to give a fine active substance suspension. The dilution with water gives a stable suspension of the active substance. For a FS type composition, up to 40 wt% binder (e.g. polyvinylalcohol) is added. f) Water-dispersible granules and water-soluble granules (WG, SG)

50-80 wt% of an inventive mixture are ground finely with the addition of dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) ad 100 wt% and prepared as water-dispersible or water- soluble granules by means of technical appliances (e.g. extrusion, spray tower, fluidized bed). The dilution with water gives a stable dispersion or solution of the active substance. g) Water-dispersible powders and water-soluble powders (WP, SP, WS)

50-80 wt% of an inventive mixture are ground in a rotor-stator mill with the addition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1-3 wt% wetting agents (e.g. alcohol ethoxylate) and a solid carrier (e.g. silica gel) ad 100 wt%. The dilution with water gives a stable dispersion or solution of the active substance. h) Gel (GW, GF)

In an agitated ball mill, 5-25 wt% of an inventive mixture are comminuted with the addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), of a 1-5 wt% thickener (e.g. carboxymethylcellulose) and water ad 100 wt% to give a fine suspension of the active substance. The dilution with water gives a stable suspension of the active substance. i) Microemulsion (ME)

5-20 wt% of an inventive mixture are added to 5-30 wt% of an organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), of a 10-25 wt% surfactant blend (e.g. alcohol ethoxylate and arylphenol ethoxylate), and water ad 100 %. This mixture is stirred for 1 h to produce spontaneously a thermodynamically stable microemulsion. j) Microcapsules (CS)

An oil phase comprising 5-50 wt% of an inventive mixture, 0-40 wt% of a water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% of acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization is initiated by a radical initiator and results in the formation of poly(meth)acrylate microcapsules. Alternatively, an oil phase comprising 5-50 wt% of an inventive mixture according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), and an isocyanate monomer (e.g. diphenylmethene-4,4’ -diisocyanate) are dispersed into 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 monomers amount to 1-10 wt%. The wt% relates to the total CS composition. k) Dustable powders (DP, DS)

1-10 wt% of an inventive mixture are ground finely and mixed intimately with a solid carrier (e.g. finely divided kaolin) ad 100 wt%. l) Granules (GR, FG)

0.5-30 wt% of an inventive mixture is ground finely and associated with a solid carrier (e.g. silicate) ad 100 wt%. The granulation is achieved by an extrusion, a spray-drying or a fluidized bed. m) Ultra-low volume liquids (UL)

1-50 wt% of an inventive mixture are dissolved in organic solvent (e.g. aromatic hydrocarbon) ad 100 wt%. The composition types a) to m) may optionally comprise further agriculturally acceptable additives, such as 0.1-1 wt% of bactericides, 5-15 wt% of anti-freezing agents, 0.1-1 wt% of anti-foaming agents, and 0.1- 1 wt% of colorants.

In general, the composition according to the present invention as described above preferably in a mixing ratio of from 100:1 to 1:100, preferably from 50:1 to 1:50, more preferably from 25:1 to 1:25, even more preferably from 20:1 to 1:20, including also ratios from 10:1 to 1:10, 5:1 to 1:5, 4:1 to 1:4, 3:1 to 1:3, 2:1 to 1 :2, or 1 : 1. The weight ratio of component (1) to component (3) in the ternary composition is in the range from 100:1 to 1:100, preferably from 50:1 to 1:50, more preferably from 25:1 to 1:25, even more preferably from 20:1 to 1:20, including also ratios from 10:1 to 1:10, 5:1 to 1:5, 4:1 to 1:4, 3:1 to 1:3, 2:1 to 1:2, or 1:1. The weight ratio of component (2) to component (3) in the ternary composition is in the range from 100:1 to 1:100, preferably from 50:1 to 1:50, more preferably from 25:1 to 1:25, even more preferably from 20:1 to 1:20, including also ratios from 10:1 to 1:10, 5:1 to 1:5, 4:1 to 1:4, 3:1 to 1:3, 2:1 to 1:2, or 1:1.

In another embodiment, the composition according to the invention may be admixed in a ratio of (1-80): (1-80): (1-80) of the component (1); the component (2) and the component (3), respectively.

According to the invention, the expression "composition" stands for the various mixtures or combinations of components (1), (2) and (3), for example, in a single "ready -mix" form, in a combined spray mixture composed from separate formulations of the single active compounds, such as a "tank- mix", and in a combined use of the single active ingredients when applied in a sequential manner, i.e. one after the other with a reasonably short period, such as a few hours or days. Preferably the order of applying the components (1), (2) and (3) are not essential for working the present invention.

In a certain embodiment, the agrochemical composition according to the invention further comprises an additional active ingredient as component (4), wherein the component (4) is not identical with the components (1), (2) and (3), as described herein (4-way mixture). In a specific embodiment, the agrochemical composition according to the invention comprises an active compound of formula (I) as component (1), component (2), component (3) and an additional active ingredient as component (4).

The term “component (4)” means: a compound having acaricidal, algicidal, avicidal, bactericidal, fungicidal, herbicidal, insecticidal, molluscicidal, nematicidal, rodenticidal, or virucidal properties; or (b) compound that are antifeedants, bird repellents, chemosterilants, herbicide safeners, insect attractants, insect repellents, mammal repellents, mating disrupters, plant activators, plant growth regulators, or synergists.

When applied to the useful plants component (1) is typically applied at a rate of 5 to 2000 g a.i./ha, particularly 10 to 1000 g a.i./ha, e.g. 50, 75, 100 or 200 g a.i./ha, typically in association with 1 to 5000 g a.i./ha, particularly 2 to 2000 g a.i./ha, e.g. 75, 100, 250, 500, 800, 1000, 1500 g a.i./ha of component (2). When applied to the useful plants component (1) is typically applied at a rate of 5 to 2000 g a.i./ha, particularly 10 to 1000 g a.i./ha, e.g. 50, 75, 100 or 200 g a.i./ha, typically in association with 1 to 5000 g a.i./ha, particularly 2 to 2000 g a.i./ha, e.g. 75, 100, 250, 500, 800, 1000, 1500 g a.i./ha of component (3). When applied to the useful plants component (2) is typically applied at a rate of 5 to 2000 g a.i./ha, particularly 10 to 1000 g a.i./ha, e.g. 50, 75, 100 or 200 g a.i./ha, typically in association with 1 to 5000 g a.i./ha, particularly 2 to 2000 g a.i./ha, e.g. 75, 100, 250, 500, 800, 1000, 1500 g a.i./ha of component (3).

When employed in plant protection, the amounts of active substances applied are, depending on the kind of effect desired, from 20 to 6000 g a.i./ha, preferably from 100 to 5000 g a.i./ha, more preferably from 200 to 4500 g a.i./ha, and in particular from 400 to 4000 g a.i./ha.

In agricultural practice the application rates of the composition according to the invention depend on the type of effect desired, and typically range from 20 to 4000 g of total composition/ha.

In the treatment of plant propagation materials such as seeds, e.g. by dusting, coating or drenching seed, amounts of active substance of 0.01-10 kg, preferably from 0.1-1000 g, more preferably from 1-100 g per 100 kg of plant propagation material (preferably seeds) are generally required.

When used in the protection of stored products, the amount of active substance applied depends on the kind of application area and on the desired effect. Amounts customarily applied in the protection of materials are 0.001 g to 2 kg, preferably 0.005 g to 1 kg, of active substance per cubic meter of treated material.

The rates of application vary within wide limits and depend on the nature of the soil, the method of application, the crop plant, the disease to be controlled, the prevailing climatic conditions, and other factors governed by the method of application, the time of application and the target crop. Usually the mixture of compounds may be applied at a rate of 1 to 2000 L/ha, especially from 5 to 1000 L/ha and more preferably from 10 to 500 L/ha.

The user applies the composition according to the invention usually from a pre -dosage device, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system. Usually, the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired application concentration and the ready -to- use spray liquor or the agrochemical composition according to the invention is thus obtained. Usually, 20 to 2000 L, preferably 50 to 1000 L, more preferably 30 to 400 L, of the ready-to-use spray liquor is applied per hectare of agricultural useful area. According to one embodiment, individual components of the composition according to the invention such as parts of a kit or parts of a binary mixture may be mixed by the user himself in a spray tank or any other kind of vessel used for applications (e.g. seed treater drums, seed pelleting machinery, knapsack sprayer) and further auxiliaries may be added, if appropriate. In one embodiment, the solutions for seed treatment (LS), suspoemulsions (SE), flowable concentrates (FS), powders for dry treatment (DS), water-dispersible powders for slurry treatment (WS), water-soluble powders (SS), emulsions (ES), emulsifiable concentrates (EC) and gels (GF) are usually employed for the purposes of treatment of plant propagation materials, particularly seeds, including the seed of transgenic plants. In this case, additional synergistic effects may also occur in interaction with the substances formed by expression.

The compositions in question give, after two to ten-fold dilution, active substance concentrations of 0.01 to 60% by weight, preferably from 0.1 to 40%, in the ready -to-use preparations. Application can be carried out before or during sowing. Methods for applying the inventive mixtures and compositions thereof, respectively, on to plant propagation material, especially seeds, include dressing, coating, pelleting, dusting, soaking and in-furrow application methods of the propagation material. Preferably, the inventive mixtures or the compositions thereof, respectively, are applied on to the plant propagation material by a method such that germination is not induced, e.g. by seed dressing, pelleting, coating and dusting.

In one embodiment, the invention is a kit for preparing a usable agrochemical composition, the kit comprising a) a composition comprising component (1) as defined herein and at least one auxiliary; and b) a composition comprising component (2) as defined herein and at least one auxiliary; and c) a composition comprising component (3) as defined herein and at least one auxiliary.

Application of the compound of the present disclosure or the compound of the present disclosure in a composition optionally comprising other compatible compounds to a plant or a plant material or locus thereof include application by a technique known to a person skilled in the art which includes but is not limited to spraying, coating, dipping, fumigating, impregnating, injection and dusting.

The present invention also relates to a method for controlling unwanted microorganisms, such as unwanted fungi, comprising the step of applying at least one novel agrochemical composition according to the invention to the microorganisms and/or their habitat (to the plants, plant parts, seeds, fruits or to the soil in which the plants grow).

In another embodiment, the present invention provides a method for combating phytopathogenic fungi comprising treating plants, soil, seeds or materials to be protected with the fungicidal composition as described herein.

In one embodiment, the present invention provides a method for controlling or preventing an infestation of useful plants by phytopathogenic fungi in agricultural crops and/or horticultural crops, wherein the fungicidal composition is applied to the plants, to parts thereof or to a locus thereof.

In one embodiment, the present invention provides a method for controlling or preventing infestation of useful plants by phytopathogenic fungi in agricultural crops and/or horticultural crops, comprising applying an agrochechemically effective amount of a said composition as described in the present invention to the plant or parts thereof, or to the plant seeds, or to a locus thereof.

The term “control” or “controlling” as used herein encompasses curative and protective treatment of unwanted microorganisms. The unwanted microorganisms may be pathogenic bacteria or pathogenic fungi, more specifically phytopathogenic bacteria or phytopathogenic fungi.

The term "locus thereof" includes soil, surroundings of plant or plant parts and equipment or tools used before, during or after sowing/planting a plant or a plant part.

In the context of the present invention, "control of harmful microorganisms" means a reduction in infestation by harmful microorganisms, compared with the untreated plant measured as fungicidal efficacy, preferably a reduction by 25-50 %, compared with the untreated plant (100 %), more preferably a reduction by 40-79 %, compared with the untreated plant (100 %); even more preferably, the infection by harmful microorganisms is entirely suppressed (by 70-100 %). The control may be curative, i.e. for treatment of already infected plants, or protective, for protection of plants which have not yet been infected.

An "effective but non-phytotoxic amount" or “agrochechemically effective amount” means an amount of the novel agrochemical composition which is sufficient to control the fungal disease of the plant in a satisfactory manner or to eradicate the fungal disease completely, and which, at the same time, does not cause any significant symptoms of phytotoxicity. In general, this application rate may vary within a relatively wide range. It depends on several factors, for example, on the fungus to be controlled, the plant, the climatic conditions and the ingredients of the inventive compositions.

The novel agrochemical composition according to the invention can be applied to any plants or plant parts.

Plants mean all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the genetically modified plants (GMO or transgenic plants) and the plant cultivars which are protectable and non-protectable by plant breeders' rights.

Genetically modified plants (GMO or transgenic plants) are plants of which a heterologous gene has been stably integrated into the genome. The expression "heterologous gene" essentially means a gene which is provided or assembled outside the plant and then introduced in the nuclear, chloroplastic or mitochondrial genome. This gene gives the transformed plant new or improved agronomic or other properties by expressing a protein or polypeptide of interest or by down regulating or silencing other gene(s) which are present in the plant (using for example, antisense technology, cosuppression technology, RNA interference - RNAi - technology or microRNA - miRNA - technology). A heterologous gene, located in the genome, is also called a transgene. A transgene that is defined by its particular location in the plant genome is called a transformation or transgenic event.

Plant cultivars are understood to mean plants which have new properties ("traits") and have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, varieties, bio- or genotypes.

According to the invention all plants and plant parts can be treated. By plants is meant all plants and plant populations such as desirable and undesirable wild plants, cultivars and plant varieties (whether or not protectable by plant variety or plant breeder's rights). Cultivars and plant varieties can be plants obtained by conventional propagation and breeding methods which can be assisted or supplemented by one or more biotechnological methods such as by use of double haploids, protoplast fusion, random and directed mutagenesis, molecular or genetic markers or by bioengineering and genetic engineering methods. By plant parts is meant all above ground and below ground parts and organs of plants such as shoot, leaf, blossom and root, whereby for example, leaves, needles, stems, branches, blossoms, fruiting bodies, fruits and seed as well as roots, conns and rhizomes are listed. Crops and vegetative and generative propagating material, for example, cuttings, conns, rhizomes, runners and seeds also belong to plant parts.

Plant parts are understood to mean all parts and organs of plants above and below the ground, such as shoots, leaves, needles, stalks, stems, flowers, fruit bodies, fruits, seeds, roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example, cuttings, tubers, rhizomes, slips and seeds.

Plants which can be treated in accordance with the methods of the invention include the following: cotton, flax, grapevine, fruit, vegetables, such as Rosaceae sp. (for example, pome fruits such as apples and pears, but also stone fruits such as apricots, cherries, almonds and peaches, and soft fruits such as strawberries), Ribesioidae sp., Juglandaceae sp., Betulaceae sp., Anacardiaceae sp., Fagaceae sp., Ivloraceae sp., Oleaceae sp., Actinidaceae sp., Lauraceae sp., Afusaceae sp. (for example, banana trees and plantations), Rubiaceae sp. (for example, coffee), Theaceae sp., Sterculiceae sp., Rutaceae sp. (for example, lemons, oranges and grapefruit); Solanaceae sp. (for example, tomatoes), Liliaceae sp., Asteraceae sp. (for example, lettuce), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp., Cucurbitaceae sp. (for example cucumber), Alliaceae sp. (for example, leek, onion), Papilionaceae sp. (for example, peas); major crop plants, such as Gramineae sp. (for example, maize, turf, cereals such as wheat, rye, rice, barley, oats, millet and tiiticale), Asteraceae sp. (for example, sunflower), Brassicaceae sp. (for example, white cabbage, red cabbage, broccoli, cauliflower, Brussels sprouts, pak choi, kohlrabi, radishes, and oilseed rape, mustard, horseradish and cress), Fabacae sp. (for example, bean, peanuts), Papilionaceae sp. (for example, soya bean), Solanaceae sp. (for example, potatoes), Chenopodiaceae sp. (for example, sugar beet, fodder beet, swiss chard, beetroot) ; useful plants and ornamental plants for gardens and wooded areas ; and genetically modified varieties of each of these plants.

In particular, the novel agrochemical composition according to the invention are suitable for controlling the following plant diseases:

Albugo spp. (white rust) on ornamentals, vegetables (e.g. A. Candida) and sunflowers (e.g. A. tragopogonis ); Alternaria spp. (Alternaria leaf spot) on vegetables, rape (A. brassicola or brassi cae ), sugar beets (A. tenuis), fruits, rice, soybeans, potatoes (e. g. A. solani or A. alternata), tomatoes (e. g. A. solani or A. alternata) and wheat; Aphanomyces spp. on sugar beets and vegetables; Ascochyta spp. on cereals and vegetables, e. g. A. tritici (anthracnose) on wheat and A. hordei on barley; Bipolaris and Drechslera spp. (teleomorph: Cochliobolus spp.), e.g. Southern leaf blight (D. maydis) or Northern leaf blight (B. zeicola) on corn, e. g. spot blotch ( B. sorokiniana ) on cereals and e. g. B. oryzae on rice and turfs; Blumeria (formerly Erysiphe) graminis (powdery mildew) on cereals (e.g. on wheat or barley); Botrytis cinerea (teleomorph: Botryotiniafuckeliana: grey mold) on fruits and berries (e.g. strawberries), vegetables (e.g. lettuce, carrots, celery and cabbages), rape, flowers, vines, forestry plants and wheat; Bremia lactucae (downy mildew) on lettuce; Ceratocystis (syn. Ophiostoma) spp. (rot or wilt) on broad leaved trees and evergreens, e.g. C. ulmi (Dutch elm disease) on elms; Cercospora spp. (Cercospora leaf spots) on corn (e.g. Gray leaf spot: C. zeaemaydis), rice, sugar beets(e.g. C. beticola), sugar cane, vegetables, coffee, soybeans (e.g. C. sojina or C. kikuchil) and rice; Cladosporium spp. on tomatoes (e.g. C. fulvum: leaf mold) and cereals, e.g. C. herbarum (black ear) on wheat; Claviceps purpurea (ergot) on cereals; Cochliobolus (anamorph: Helmin thosporium of Bipolaris) spp. (leaf spots) on corn (C. carbonum), cereals (e.g. C. sativus, anamorph: B. sorokiniana) and rice (e.g. C. miyabeanus, anamorph: H. oryzae); Colletotrichum (teleomorph: Glomerella) spp. (anthracnose) on cotton (e. g. C. gossypit), corn (e.g. C. gramini cola: Anthracnose stalk rot), fruits, potatoes (e.g. C. coccodes: black dot), vegetables like beans (e.g. C. lindemuthianum) and soybeans (e.g. C. truncatum or C. gloeosporioides); Corticium spp., e.g. C. sasakii (sheath blight) on rice; Corynespora cassiicola (leaf spots) on soybeans and ornamentals; Cycloconium spp., e.g. C. oleaginum on olive trees; Cylindrocarpon spp. (e.g. fruit tree canker or young vine decline, teleomorph: Nectria or Neonectria spp.) on fruit trees, vines (e. g. C. liriodendri, teleomorph: Neonectria liriodendri: Black Foot Disease) and ornamentals; Dematophora (teleomorph: Rosellinia) necatrix (root and stem rot) on soybeans; Diaporthe spp., e.g. D. phaseolorum (damping off) on soybeans; Drechslera (syn. Helminthosporium, teleomorph: Pyrenophora) spp. on corn, cereals, such as barley (e.g. D. teres, net blotch) and wheat (e.g. D. tritici-repentis: tan spot), rice and turf; Esca (dieback, apoplexy) on vines, caused by Formitiporia (syn. Phellinus) punctata, F. mediterranea, Phaeomoniella chlamydospora (earlier Phaeoacremonium chlamydosporum), Phaeoacremonium aleophilum and/or Botryosphaeria obtusa; Elsinoe spp. on pome fruits (E. pyn), soft fruits (E. veneta: anthracnose) and vines (E.ampelina: anthracnose); Entyloma oryzae (leaf smut) on rice; Epicoccum spp. (black mold) on wheat; Erysiphe spp. (powdery mildew) on sugar beets (E. betae), vegetables (e. g. E. pist), such as cucurbits (e.g. E. cichoracearum), cabbages, rape (e.g. E. crucifer arum); Eutypa lata (Eutypa canker or dieback, anamorph: Cytosporina lata, syn. Libertella blepharis) on fruit trees, vines and ornamental woods; Exserohilum (syn. Helminthosporium) spp. on corn (e.g. E. turcicumy. Fusarium (tel eo morph: Gibber ella) spp. (wilt, root or stem rot) on various plants, such as F. graminearum or F. culmorum (root rot, scab or head blight) on cereals (e.g. wheat or barley), F. oxysporum on tomatoes, F. solani (f. sp. glycines now syn. F. virguliforme ) and F. tucumaniae and F. brasiliense each causing sudden death syndrome on soybeans, and F. verticillioides on corn; Gaeumannomyces graminis (take-all) on cereals (e.g. wheat or barley) and corn; Gib berella spp. on cereals (e. g. G. zeae ) and rice (e.g. G.fujikuroi: Bakanae disease); Glomerella cingulata on vines, pome fruits and other plants and G. gossypii on cotton; Grainstaining com plex on rice; Guignardia bidwellii (black rot) on vines; Gymnosporangium spp. on rosaceous plants and junipers, e. g. G. sabinae (rust) on pears; Helminthosporium spp. (syn. Drechslera, teleomorph: Cochliobolus) on corn, cereals and rice; Hemileia spp., e.g. H. vastatrix (coffee leaf rust) on coffee; Isariopsis clavispora (syn. Cladosporium vitis) on vines; Macrophomina phaseolina (syn. phaseoft) (root and stem rot) on soybeans and cotton; Microdochium (syn. Fusarium) nivale (pink snow mold) on cereals (e. g. wheat or barley); Microsphaera diffusa (powdery mildew) on soybeans; Monilinia spp., e.g. M. laxa, M. fructicola and M. frucligena b\oom and twig blight, brown rot) on stone fruits and other rosaceous plants ; Mycosphaerella spp. on cereals, bananas, soft fruits and ground nuts, such as e. g. M. graminicola (anamorph: Septoria tritici, Septoria blotch) on wheat or M.fijiensis (black Sigatoka disease) on bananas; Peronospora spp. (downy mildew) on cabbage (e.g. P. brassicae), rape (e.g. P. parasitica), onions (e.g. P. destructor), tobacco (P. tabacina) and soybeans (e.g. P. manshurica); Phakopsora pachyrhizi and P. meibomiae (soybean rust) on soybeans; Phialophora spp. e.g. on vines (e.g. P. tracheiphila and P. tetraspora) and soybeans (e.g. P. gregata: stem rot); Phoma lingam (root and stem rot) on rape and cabbage and P. betae (root rot, leaf spot and damping-off) on sugarbeets; Phomopsis spp. on sunflowers, vines (e. g. P. viticola: can and leaf spot) and soybeans (e.g. stem rot: P. phaseoli, teleomorph: Diaporthe phaseolorum); Phy soderma maydis (brown spots) on corn; Phytophthora spp. (wilt, root, leaf, fruit and stem root) on various plants, such as paprika and cucurbits (e.g. P. capsid ), soybeans (e. g. P. megasperma, syn. P. sojae), potatoes and tomatoes (e. g. P. infestans: late blight) and broad leaved trees (e.g. P. ramorum: sudden oak death); Plasmodiophora brassicae (club root) on cabbage, rape, radish and other plants; Plasmopara spp., e.g. P. viticola (grapevine downy mildew) on vines and P. halstedii on sunflowers; Podosphaera spp. (powdery mildew) onrosa ceous plants, hop, pome and soft fruits, e.g. P. leucotricha on apples; Polymyxa spp., e.g. on cereals, such as barley and wheat P. graminis) and sugarbeets (P. betae) and thereby transmitted viral diseases; Pseudocercosporella herpotrichoides (eyespot, teleomorph: Tapesiayallundae) on cereals, e.g. wheat or barley; Pseudoperonospora (downy mildew) on various plants, e.g. P. cubensis on cucurbits or P. humili on hop; Pseudopezicula tracheiphila (red fire disease or, rotbrenner', anamorph: Phialophora) on vines; Puccinia spp. (rusts) on various plants, e.g. P. triticina (brown or leaf rust), P. striiformis (stripe or yellow rust), P. hordei (dwarf rust), P. graminis (stem or black rust) or P. recondita (brown or leaf rust) on cereals, such as e.g. wheat, barley or rye, P. kuehnii (orange rust) on sugar cane and P. asparagi on asparagus; Pyrenophora (anamorph: Drechslera) tritici- repentis (tan spot) on wheat or P. teres (net blotch) on barley; Pyricularia spp., e.g. P. oryzae (teleomorph: Magnaporthe grisea, rice blast) on rice and P. grisea on turf and cereals; Pythium spp. (damping-off) on turf, rice, corn, wheat, cotton, rape, sunflowers, soybeans, sugarbeets, vegetables and various other plants (e. g. P. ultimum or P. aphanidermatum); Ramularia spp., e. g. R. collo-cygni (Ramularia leaf spots, Physiological leaf spots) on barley and R. beticola on sugar beets; Rhizoctonia spp. on cotton, rice, potatoes, turf, corn, rape, potatoes, sugar beets, vegetables and various other plants, e. g. R. solani (root and stem rot) on soybeans, R. solani (sheath blight) on rice or R. cerealis (Rhizoctonia spring blight) on wheat or barley; Rhizopus stolonifer (black mold, soft rot) on strawberries, carrots, cabbage, vines and tomatoes; Rhynchosporium secalis (scald) on barley, rye and triticale; Sa rocladium oryzae and S. attenuatum (sheath rot) on rice; Sclerotinia spp. (stem rot or white mold) on vegetables and field crops, such as rape, sunflowers (e. g. S. sclerotiorum) and soy beans (e.g. S. rolfsii or S. sclerotiorum); Septoria spp. on various plants, e. g. S. glycines (brown spot) on soybeans, S. tritici (Septoria blotch) on wheat and S. (syn. Stagonospora) no dorum (Stagonospora blotch) on cereals; Uncinula (syn. Erysiphe) necator (powdery mildew, anamorph: Oidium tucken) on vines; Setospaeria spp. (leaf blight) on corn (e.g. S. turcicum, syn. Helminthosporium turcicum) and turf; Sphacelotheca spp. (smut) on corn, (e.g. S. reiliana: head smut), sorghum und sugar cane; Sphaerotheca fuliginea (powdery mildew) on cucurbits; Spongospora subterranea (powdery scab) on potatoes and thereby transmitted viral diseases; Stagonospora spp. on cereals, e. g. S. nodorum (Stagonospora blotch, teleomorph: Lepto sphaeria [syn. Phaeosphaeria] nodorum) on wheat; Synchytrium endobioticum on potatoes (po tato wart disease); Taphrina spp., e.g. T. deformans (leaf curl disease) on peaches and T. pruni (plum pocket) on plums; Thielaviopsis spp. (black root rot) on tobacco, pome fruits, vegetables, soybeans and cotton, e.g. T. basicola (syn. Chalara elegans); Tilletia spp. (common bunt or stinking smut) on cereals, such as e. g. 7. tritici (syn. /. caries, wheat bunt) and /. controversa (dwarf bunt) on wheat; Typhula incamata (grey snow mold) on barley or wheat; Urocystis spp., e.g. U. occulta (stem smut) on rye; Uromyces spp. (rust) on vegetables, such as beans (e.g. U. appendiculatus, syn. U. phaseoft) and sugarbeets (e.g. U. betae); Ustilago spp. (loose smut) on cereals (e. g. U. nuda and U. avaenae), corn (e. g. U. maydis: corn smut) and sugar cane; Venturia spp. (scab) on apples (e.g. V. inaequalis) and pears; and Verticillium spp. (wilt) on various plants, such as fruits and ornamentals, vines, soft fruits, vegetables and field crops, e.g. V. dahliae on strawberries, rape, potatoes and tomatoes.

The present invention is specifically directed to the use of the novel agrochemical compositions according to the invention for the treatment of soybean diseases.

Most preference is given to the following soybean diseases:

Cercospora kikuchii, Cercospora sojina; Colletotrichum gloeosporoides dematium var. truncatum; Corynespora casiicola; Diaporthe phaseolorum; Microsphaera diffusa; Peronospora manshurica; Phakopsora species, for example, Phakopsora pachyrhizi and Phakopsora meibomiae (soybean rust); Phytophthora megasperma; Phialophora gregata; Rhizoctonia solani; Sclerotinia sclerotiorum; Septoria spp. e.g. Septoria glycines, Thielaviopsis basicola.

Non-limiting examples of pathogens of fungal diseases which can be treated in accordance with the invention include:

Diseases caused by powdery mildew pathogens, for example, Blumeria species, for example, Blumeria graminis; Podosphaera species, for example, Podosphaera leucotricha; Sphaerotheca species, for example, Sphaerotheca fuliginea', Uncinula species, for example, Uncinula necator; Erysiphe species, for example, Erysiphe cichoracearu;

Diseases caused by rust disease pathogens, for example, Gymnosporangium species, for example, Gy mno sporangium sabinac, Hemileia species, for example, Hemileia vastatrix; Phakopsora species, for example, Phakopsora pachyrhizi or Phakopsora meibomiae', Puccinia species, for example, Puccinia recondita, Puccinia graminis or Puccinia striiformis and Puccinia melanocephala; Uromyces species, for example, Uromyces appendiculatus.

In particular, Cronartium ribicola (White pine blister rust); Gymnosporangium juniperi-virginianae (Cedar-apple rust); 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 Kentucky bluegrass, or black rust of cereals); Puccinia hemerocallidis (Daylily rust); Puccinia persistens subsp. triticina (wheat rust or 'brown or red rust'); Puccinia sorghi (rust in corn); Puccinia striiformis ('Yellow rust' in cereals); Puccinia melanocephala', Uromyces appendiculatus (rust of beans); Uromyces phaseoli (Bean rust); Puccinia melanocephala ('Brown rust' in sugarcane); Puccinia kuehnii ('Orange rust' in sugarcane).

Diseases caused by pathogens from the group of the Oomycetes, for example, Albugo species, for example, Albugo Candida', Bremia species, for example, Bremia lactucae; Peronospora species, for example, Peronospora pisi or P. brassicae; Phytophthora species, for example, Phytophthora infestans', Plasmopara species, for example, Plasmopara viticola; Pseudoperonospora species, for example, Pseudoperonospora humuli or Pseudoperonospora cubensis; Pythium species, for example, Pythium ultimum.

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

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

Ear and panicle diseases (including corn cobs) caused, for example, by Alternaria species, for example, Alternaria spp.; Aspergillus species, for example, Aspergillus flavus; Cladosporium species, for example, Cladosporium cladosporioides; Claviceps species, for example, Claviceps purpurea; Fusarium species, for example, Fusarium culmorum; Gibberella species, for example, Gibberella zeae; Monographella species, for example, Monographella nivalis; Stagnospora species, for example, Stagnospora nodorum; diseases caused by smut fungi, for example, Sphacelotheca species, for example, Sphacelotheca reiliana; Tilleda species, for example, Tilleda caries or Tilleda controversa; Urocyst i species, for example, Urocystis occulta; Ustilago species, for example, Ustilago nuda. Fruit rot caused, for example, by Aspergillus species, for example, Aspergillus flavus; Botrytis species, for example, Botrytis cinerea; Penicillium species, for example, Penicillium expansum or Penicillium purpurogenum; Rhizopus species, for example, Rhi opus stolonifer; Sclerotinia species, for example, Sclerotinia sclerotiorum; Verticilium species, for example, Verticilium alboatrum.

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

Cancers, galls and witches’ broom caused, for example, by Nectria species, for example, Nectria galligena; wilt diseases caused, for example, by Monilinia species, for example, Monilinia laxa.

Deformations of leaves, flowers and fruits caused, for example, by Exobasidium species, for example, Exobasidium vexans; Taphrina species, for example, Taphrina deformans.

Degenerative diseases in woody plants, caused, for example, by Esca species, for example, Phaeomoniella chlamydospora, Phaeoacremonium aleophilum or Fomitiporia mediterranea; Ganoderma species, for example, Ganoderma boninense.

Diseases of flowers and seeds caused, for example, by Botrytis species, for example Botrytis cinerea.

Diseases of plant tubers caused, for example, by Rhizoctonia species, for example, Rhizoctonia solani; Helminthosporium species, for example, Helminthosporium solani.

Diseases caused by bacterial pathogens, for example, Xanthomonas species, for example, Xanthomonas campestris pv. oryzae; Pseudomonas species, for example, Pseudomonas syringae pv. lachrymans; Erwinia species, for example, Erwinia amylovora; Ralstonia species, for example, Ralstonia solanacearum. Fungal diseases on roots and the stem base caused, for example, by black root rot (Calonectria crotalariae), charcoal rot (Macrophomina phaseolind), fusarium blight or wilt, root rot, and pod and collar rot (Fusarium oxysporum, Fusarium orthoceras, Fusarium semitectum, Fusarium equiseli). mycoleptodiscus root rot (Mycoleptodiscus lerreslris). neocosmospora (Neocosmospora vasinfectd), pod and stem blight (Diaporthe phaseolorum), stem canker (Diaporthe phaseolorum var. caulivora), phytophthora rot (Phytophthora megasperma), brown stem rot (Phialophora gregala). pythium rot (Pythium aphanidermatum, Pythium irregulare, Pythium debaryanum, Pythium myriotylum, Pythium ultimum), rhizoctonia root rot, stem decay, and damping-off (Rhizoctonia solani), sclerotinia stem decay (Sclerotinia sclerotiorum), sclerotinia southern blight (Sclerotinia rolfsii), thielaviopsis root rot (Thielaviopsis basicola).

More preference is given to controlling the following diseases of soya beans: Fungal diseases on leaves, stems, pods and seeds caused, for example, by Altemaria leaf spot (Altemaria spec, atrans lenuissima). Anthracnose (Colletotrichum gloeosporoides dematium var. truncation), brown spot (Septoria glycines ), cercospora leaf spot and blight (Cercospora kikuchii), choanephora leaf blight (Choanephora infundibulifera trispora (Syn.)), dactuliophora leaf spot (Dactuliophora glycines'), downy mildew (Peronospora manshurica), drechslera blight (Drechslera glycini), frogeye leaf spot (Cercospora sojina), leptosphaerulina leaf spot (Leptosphaerulina trifolii), phyllostica leaf spot (Phyllosticta sojaecola), pod and stem blight (Phomopsis sojae), powdery mildew (Microsphaera diffusa), pyrenochaeta leaf spot (Pyrenochaeta glycines), rhizoctonia aerial, foliage, and web blight (Rhizoctonia solani), rust (Phakopsora pachyrhizi, Phakopsora meibomiae), scab (Sphaceloma glycines), stemphylium leaf blight (Stemphylium botryosum), target spot (Corynespora cassiicola).

In one embodiment, the present invention provides the use of the fungicidal composition for controlling or preventing agricultural crops and/or horticultural crops against diseases caused by phytopathogenic fungi.

More specifically, novel agrochemical composition, according to the invention can be used as fungicides which shows excellent activity against a broad spectrum of phytopathogenic fungi. In particular, they can be useful in crop protection, for example, for the control of unwanted fungi, such as Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes. Some of them are systemically active and can be used in crop protection as foliar fungicides, as soil fungicides and as fungicides for seed dressing.

In one embodiment, the present invention provides the use of the fungicidal composition for controlling or preventing agricultural crops and/or horticultural crops against diseases caused by phytopathogenic fungi, wherein said phytopathogenic fungi are Altemaria spp., Botrytis spp., Cercospora spp., Colletotrichum spp., Corynespora spp., Erysiphe spp., Fusarium spp., Hemileia spp., Phakopsoraceae spp., Phytophthora spp, Pseudoperonospora spp, Pyricularia spp., Rhizoctonia spp., Septoria spp, Puccinia spp., and Uromyces spp.

In a preferred embodiment, the compositions disclosed in Table-1 to Table-11 and in particular when the weight ratios of component (l):component (2) component (3) are as disclosed for these mixtures as herein mentioned before, are used against crop phytopathogenic fungi like Alternaria species, for example, Alternaria solani; Botrytis species, for example, Botrytis cinerea; Corynespora spp for example Corynespora cassiicola; Fusarium spp for example Fusarium culmorum; Erysiphe spp. (e.g. Erysiphe cichor acearum); Pyricularia species, for example, Pyricularia oryzae Septoria species, for example, Septoria nodorum, Pseudoper onospor spp for example, Pseudoperonospora cubensis; Phytophthora species for example Phytophthora infestans; Puccinia spp. (rusts) on various plants, in particular P. triticina (brown or leaf rust), P. striiformis (stripe 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, P. coronata (crown rust of grasses including oats) on cereals, such as e. g. wheat, barley or rye, and Puccinia sorghi (common rust) on maize, Puccinia polysora (southern rust) on maize, and P. helianthi (sunflower rust); Puccinia melanocephala ('Brown rust' in sugarcane); Hemileia vastatrix and Hemileia cojfeicola (leaf rust and grey rust of coffee) Hemileia vastatrix (Coffee rust); Uromyces spp. on various crops; and Phakopsoraceae spp. on various plants, in particular Phakopsora pachyrhi i and P. meibomiae (soybean rust) on soybeans.

The novel agrochemical compositions according to the invention have a potent microbicidal activity. They can be used for controlling unwanted microorganisms, such as unwanted fungi and bacteria. They can be particularly useful in crop protection (by controlling microorganisms that cause plants diseases). More specifically, the agrochemical composition according to the invention can be used to protect seeds, germinating plants, emerged seedlings, plants, plant parts, fruits and the soil in which the plants grow from unwanted microorganisms.

The fact that the novel agrochemical compositions according to the invention are well tolerated by plants at the concentrations required for controlling plant diseases allows the treatment of above-ground parts of plants, of propagation stock and seeds, and of the soil.

Effective and non-phytotoxic amount means an amount that is sufficient to control or destroy the fungi present or liable to appear on the cropland and that does not entail any appreciable symptom of phytotoxicity for said crops. Such an amount can vary within a wide range depending on the fungus to be controlled, the type of crop, the climatic conditions and the respective composition of the invention used. This amount can be determined by systematic field trials that are within the capabilities of a person skilled in the art.

The agrochemical composition of the present invention can be used for curative or protective/preventive control of phytopathogenic fungi. The present invention therefore also relates to curative and protective methods for controlling phytopathogenic fungi by use of the novel agrochemical composition, which are applied to the seed, the plant or plant parts, the fruits or the soil in which the plants grow.

The novel agrochemical composition according to the invention, when they are well tolerated by plants, have favorable homeotherm toxicity and are well tolerated by the environment, are suitable for protecting plants and plant organs, for enhancing harvest yields and for improving the quality of the harvested material. They can preferably be used as crop protection compositions. They are active against normally sensitive and resistant species and against all or some stages of development.

In addition, the novel agrochemical composition of the invention can reduce the mycotoxin content in the harvested material and the foods and feeds prepared therefrom. Mycotoxins include particularly, but not exclusively, the following: deoxynivalenol (DON), nivalenol, 15 -Ac-DON, 3-Ac-DON, T2- and HT2- toxin, fumonisins, zearalenon, moniliformin, fusarin, diaceotoxyscirpenol (DAS), beauvericin, enniatin, fusaroproliferin, fusarenol, ochratoxins, patulin, ergot alkaloids and aflatoxins which can be produced, for example, by the following fungi: Fusarium spec., such as F. acuminatum, F. asiaticum, F. avenaceum, F croobvellense, F culmorum, F graminearum (Gibberella zeae), F equiseti, F fujikoroi, F musarum, F oxysporum, F proliferatum, F poae, F pseudo graminearum, F. sambucinum, F. scirpi, F semitectum, F solani, F sporotrichoides, F langsethiae, F. subglutinans, F. tricinctum, F verticillioides etc., and also by Aspergillus spec., such as A. jlavus, A. parasiticus, A. nomius, A. ochraceus, A. clavatus, A. terreus, A. versicolor, Penicillium spec., such as P. verrucosum, P. viridicatum, P. citrinum, P. expansum, P. claviforme, P. roqueforti, Claviceps spec., such as C. purpurea, C. fusiformis, C. paspali, C. africana, Stachybotlys spec, and others.

In one, the novel agrochemical composition is used for foliar application.

The novel agrochemical composition of the invention may intervene in physiological processes of plants and can therefore also be used as plant growth regulators.

Application of the inventive compositions to useful plants may also lead to an increase in the crop yield.

The novel agrochemical composition of the invention also exhibits a potent strengthening effect in plants. Accordingly, they can be used for mobilizing the defences of the plant against attack by undesirable microorganisms.

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

Abiotic stress tolerance, comprising tolerance to high or low temperatures, drought tolerance and recovery after drought stress, water use efficiency (correlating to reduced water consumption), flood tolerance, ozone stress and UV tolerance, tolerance towards chemicals like heavy metals, salts, pesticides etc.

Biotic stress tolerance comprising increased fungal resistance and increased resistance against nematodes, viruses and bacteria. In context with the present invention, biotic stress tolerance preferably comprises increased fungal resistance and increased resistance against nematodes.

In another embodiment, the present invention provides a fungicidal composition for treating seed, seed of transgenic plants and transgenic plants.

The novel agrochemical composition of the present invention is also suitable for treating seed. A large part of the damage to crop plants caused by harmful organisms is triggered by the infection of the seed during storage or after sowing as well as during and after the germination of the plant. This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive, and even minor damage may result in the death of the plant. There is therefore a great interest in protecting the seed and the germinating plant by using appropriate compositions.

The control of phytopathogenic fungi by treating the seed of plants has been known for a long time and is the subject of constant improvements. However, the treatment of seed entails a series of problems which cannot always be solved in a satisfactory manner. For instance, it is desirable to develop methods for protecting the seed and the germinating plant, which dispense with, or at least significantly reduce, the additional deployment of crop protection compositions after planting or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used to provide the best possible protection for the seed and the germinating plant from an attack by phytopathogenic fungi, but without damaging the plant itself by the active ingredient employed. In particular, methods for the treatment of seed should also take account of the intrinsic fungicidal properties of transgenic plants in order to achieve optimal protection of the seed and the germinating plant with a minimum expenditure of crop protection compositions.

For treatment of seed with the seed dressing formulations usable in accordance with the invention, or the preparations prepared therefrom by adding water, all mixing units usable customarily for the seed dressing are useful. Specifically, the procedure in the seed dressing is to place the seed into a mixer, to add the particular desired amount of seed dressing formulations, either as such or after prior dilution with water, and to mix everything until the formulation is distributed homogeneously on the seed. If appropriate, this is followed by a drying process.

The novel agrochemical compositions are suitable for protecting seeds of any plant variety which is used in agriculture, in greenhouses, in forests or in horticulture and viticulture. In particular, seeds of cereals (such as wheat, barley, rye, triticale, sorghum/millet and oats), maize, cotton, soyabean, rice, potato, sunflower, bean, coffee, beet (for example, sugar beet and fodder beet), peanut, oilseed rape, poppy, olive, coconut, cocoa, sugar cane, tobacco, vegetables (such as tomato, cucumbers, onions and lettuce), turf and ornamentals (see also below). The treatment of seeds of cereals (such as wheat, barley, rye, triticale and oats), maize, rice and soybean is of particular significance.

As also described herein, the treatment of transgenic seed with the novel agrochemical composition is of particular significance. This relates to the seed of plants containing at least one heterologous gene which enables the expression of a polypeptide or protein having insecticidal properties. The heterologous gene in transgenic seed can originate, for example, from microorganisms of the species Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. This heterologous gene preferably originates from Bacillus sp., in which case the gene product is effective against the European maize borer and/or the western maize rootworm. The heterologous gene more preferably originates from Bacillus thuringiensis.

In the context of the present invention, the novel agrochemical composition is applied to the seed alone or in a suitable formulation. Preferably, the seed is treated in a state in which it is sufficiently stable for no damage to occur in the course of treatment. In general, the seed can be treated at any time between harvest and sowing. It is customary to use seed which has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. For example, it is possible to use seed which has been harvested, cleaned and dried down to a moisture content of less than 15 % by weight. Alternatively, it is also possible to use seed which, after drying, for example, has been treated with water and then dried again.

The control of phytopathogenic fungi which damage plants post-emergence is affected primarily by treating the soil and the above-ground parts of plants with crop protection compositions. Owing to the concerns regarding a possible influence of the crop protection compositions on the environment and the health of humans and animals, there are efforts to reduce the amount of active ingredients deployed.

One of the advantages of the present invention is that, in particular, the systemic properties of the novel agrochemical composition not only protect the seed itself, but also the resulting plants after emergence, from phytopathogenic fungi.

Digital Technologies

The composition of the invention can be used in combination with models e.g. embedded in computer programs for site specific crop management, satellite farming, precision farming or precision agriculture. Such models support a site specific management of agricultural sites with data from various sources such as soils, weather, crops (e.g. type, growth stage, plant health), weeds (e.g. type, growth stage), diseases, pests, nutrients, water, moisture, biomass, satellite data, yield etc. with the purpose to optimize profitability, sustainability and protection of the environment. Particularly, such models can help to optimize agronomical decisions, control the precision of the pesticide applications and record the work performed.

As an example, the composition of the invention can be applied to a crop plant according to an appropriate dose regime if a model, models the development of a fungal disease and calculates that a threshold has been reached for which it is recommendable to apply the composition of the invention to the crop plant.

Commercially available systems which include agronomic models are e.g. FieldScriptsTM from The Climate Corporation, XarvioTM from BASF, AGLogicTM from John Deere, etc.

The composition of the invention can also be used in combination with smart spraying equipment such as e.g. spot spraying or precision spraying equipment attached to or housed within a farm vehicle such as a tractor, robot, helicopter, airplane, unmanned aerial vehicle (UAV) such as a drone, etc. Such an equipment usually includes input sensors (such as e.g. a camera) and a processing unit configured to analyze the input data and provide a decision, based on the analysis of the input data, to apply the compound of the invention to the crop plants (respectively the weeds) in a specific and precise manner. The use of such smart spraying equipment usually also requires position systems (e.g. GPS receivers) to localize recorded data and to guide or to control farm vehicles; geographic information systems (GIS) to represent the information on intelligible maps, and appropriate farm vehicles to perform the required farm action such as the spraying.

In an example, diseases can be detected from imagery acquired by a camera. The disease can be identified and/or classified based on that imagery. Such identification and / classification can make use of image processing algorithms. Such image processing algorithms can utilize machine learning algorithms, such as trained neutral networks, decision trees and utilize artificial intelligence algorithms. In this manner, the compounds described herein can be applied only where needed.

Positive crop response:

The composition of the present invention not only control plant pathogens effectively but also show positive crop response such as plant growth enhancement effects like increased root growth, enhanced tolerance to drought, high salt, high temperature, chill, frost or light radiation, improved flowering, enhanced nutrient utilization (such as improved nitrogen assimilation), enhanced quality of plant products, more number of productive tillers, enhanced resistance to insect pests and the like, which results in higher yields.

Synergystic effect:

The compositions comprising the compound of formula (I) as component (1), the component (2) and the component (3) at specific ratios are advantageously chosen so as to produce a synergistic effect.

The expected efficacies of the composition comprising the active components may be determined using Colby's formulas (Colby, S.R. "Calculating synergistic and antagonistic responses of herbicide combinations", Weeds, Volume 15, Issue 1, January 1967, pp. 20-22).

According to the present invention, the efficacy of a composition or mixture is greater than the sum of the efficacies of the individual components, hence the composition shall be considered as a synergistic combination or a synergistic mixture.

Colby's formulas:

The expected activity for a given composition of three active components (ternary composition) can be calculated as follows:

E x * y + z

X: efficacy, expressed in % of the untreated control, when using the active component (1) at the concentration a,

Y: efficacy, expressed in % of the untreated control, when using the active component (2) at the concentration b

Z: efficacy, expressed in % of the untreated control, when using the active component (3) at the concentration c.

E is the efficacy when the active compounds (1), (2) and (3) are applied at application rates of a, b and c.

However, besides the actual synergistic action with respect to fungicidal activity, the composition, according to the invention can also have further surprising advantageous properties. Examples of such advantageous properties that may be mentioned are: more advantageuos degradability, improved toxicological and/or ecotoxicological behaviour and improved plant growth and health that leads to higher yields including: better emergence, better developed root system, tillering increase, increase in plant height, bigger leaf blade, less dead basal leaves, stronger tillers, greener leaf colour, more productive tillers, earlier flowering, early grain maturity, less plant verse (lodging), increased shoot growth, improved plant vigor, and early germination. CHEMISTRY EXAMPLES:

The following representative examples set forth the manner and process of making compounds of the present invention without being a limitation thereof and include the best mode contemplated by the inventors for carrying out the invention.

Example 1: Synthesis of A'-(3-bromo-2,5-dimethylphenyl)-A-ethyl-A-methylformimidamide

Step 1: Preparation of 3-bromo-2,5-dimethylaniline

To a stirred mixture of 3-bromo-2,5-dimethylaniline hydrochloride (20.00 g, 85 mmol) in dichloromethane (250 mL) triethylamine (58.9 ml, 423 mmol) was added dropwise at 0 °C and the mixture was stirred at 25 °C for 3 h. The reaction mixture was diluted with dichloromethne (100 mL), washed twice with water (50 mL), dried over anhydrous sodium sulphate and concentrated under reduced pressure to obtain 3-bromo- 2,5 -dimethylaniline (14 g, 70.0 mmol, 83 % yield).

^TH-NMR (400 MHz, DMSO-d6) 56.57 (s, 1H), 6.41 (s, 1H), 5.07 (s, 2H), 2.09 (s, 3H), 2.08 (s, 3H); GCMS m/z 198.9 (M ⁺ ).

Step 2: Preparation of A'-(3-bromo-2,5-dimethylphenyl)-A-ethyl-A-methylformimidamide

To a stirred solution of 3-bromo-2,5-dimethylaniline (10.0 g, 50.0 mmol) in trimethyl orthoformate (120 mL), anhydrous p-toluenesulfonic acid monohydrate (0.95 g, 5.0 mmol) was added and the resulting reaction mixture was refluxed at 105 °C for 4 h. After the completion of the reaction, the solvent was evaporated under reduced pressure. The crude product was dissolved in 1,4-dioxane (120 mL) under nitrogen atmosphere, followed by the addition of A-ethylmethylamine (8.7 mL, 100 mmol). The resulting reaction mixture was heated 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 30 % ethyl acetate in hexane as an eluent to obtain -(3-bromo-2,5-dimethylphenyl)-A-ethyl-A- methylformimidamide (12 g, 50 mmol, 89 % yield).

¹H-NMR(400 MHz, DMSO-rfo) 37.62 (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/z 270.90 (M + 1).

Example 2: Synthesis of A'-(3-bromo-5-chloro-2-methylphenyl)-A-ethyl-A-methylformimidamide

Step 1: Preparation of l-bromo-5-chloro-2-methyl-3-nitrobenzene

To a stirred solution of 4-chloro-l -methyl -2 -nitrobenzene (15.00 g, 87 mmol) in trifluoroacetic acid (18.07 mL, 235 mmol), concentrated sulphuric acid (54.2 mL, 704 mmol) was added dropwise at 0 °C. Then, N- bromosuccinimide (20.2 g, 114 mmol) was added portion wise over 30 min. and the mixture was stirred at 25 °C for 16 h. The reaction mixture was carefully poured over crushed ice and extrated twice with ethyl acetate (100 mL). The combined ethyl acetate layer was washed with water (50 mL) and saturated brine solution (50 mL), dried over anhydrous sodium sulphate, filtered and evaporated. The crude product was purified by column chromatography (silica gel) using ethyl acetate in hexane as eluent to obtain 1 -bromo- 5-chloro-2-methyl-3-nitrobenzene (15 g g, 59.9 mmol, 68 % yield) as yellow solid. GCMS m/z 248.9 (M ⁺ )■

Step 2: Preparation of 3-bromo-5-chloro-2-methylaniline:

To a stirred solution of l-bromo-5-chloro-2-methyl-3-nitrobenzene (15 g, 59.9 mmol) in a mixture of ethanol and water (200 mL, 2:1), iron powder (33.4 g, 599 mmol) and ammonium chloride (32 g, 599 mmol) were added and the mixture was heated at 80 °C for 5 h. After completion of the reaction, the reaction mixture was cooled to 25 °C, filtered through celite bed and thoroughly washed with ethyl acetate. The combined filtrate was evaporated under reduced pressure. The crude product was diluted with saturated aqueous sodium bicarbonate solution and extracted three times with ethyl acetate (250 mL). The combined organic layer was washed with water and brine solution, dried over anhydrous sodium sulfate, filtered and evaporated. The curde product was purified by column chromatography using ethyl acetate in hexane as an eluent to obtain 3-bromo-5-chloro-2-methylaniline (8.5 g, 38.5 mmol, 64 % yield). GCMS m/z 218.9 (M ⁺ )■

Step 3: Preparation of 2V'-(3-bromo-5-chloro-2-methylphenyl)-iV-ethyl-iV-methylformimidamide:

To a stirred solution of 3-bromo-5-chloro-2-methylaniline (14 g, 63.5 mmol) in trimethyl orthoformate (21 mL, 190 mmol), p-toluenesulfonic acid monohydrate (1.2 g, 6.4 mmol) was added and the resulting mixture was refluxed at 100 °C for 3 h. After completion of the reaction, the reaction mixture was concentrated under reduced pressure. The residue was re-dissolved in 1,4-dioxane (100 mL) under nitrogen atmosphere, A-ethylmethylamine (16.4 mL, 190 mmol) was added and the mixture was refluxed at 80 °C for 3 h. After completion of the reaction, the reaction mixture was diluted with water (100 mL) and extracted twice with ethyl acetate (100 mL). The combined organic layer was washed with water and brine solution, dried over anhydrous sodium sulfate, filtered and evaporated. The curde product was purified by column chromatography using ethyl acetate in hexane as an eluent to obtain A'-(3-bromo-5-chloro-2- methylphenyl)-A-ethyl-A-methylformimidamide (12 g, 41.4 mmol, 65 % yield). 'H-NMR (400 MHz, DMSO-t/6) 3 7.78-7.63 (m, 1H), 7.18 (d, 1H), 6.95-6.87 (m, 1H), 3.47-3.30 (m, 2H), 3.01-2.90 (m, 3H), 2.25 (s, 3H), 1.17-1.09 (m, 3H). LCMS m/z 289.0 (M + 1 ).

Example 3: Synthesis of of 2V-ethyl-iV’-(3-(3-methoxybenzyl)-2,5-dimethylphenyl)-iV- methylformimidamide a) Preparation of 2V'-(2,5-dimethyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)-iV- ethyl-JV-methylformimidamide

A stirred mixture of M-(3-bromo-2,5-dimethylphenyl)-A-ethyl-A-methylformimidamide (5.0 g, 18.6 mmol), bis(pinacolato)diboron (7.1 g, 27.9 mmol), [l,r-Bis(diphenylphosphino)ferrocene] dichloropalladium(II) dichloromethane [PdC12(dppf)-CH2C12] (0.76 g, 0.93 mmol) and potassium acetate (3.65 g, 37.1 mmol) in 1,4-dioxane (120 mL) was degassed for 5 min with nitrogen. The reaction mixture was stirred at 95 °C for 16 h under a nitrogen atmosphere. After the reaction was completed, the mixture was diluted with dichloromethane, filtered through a celite bed and the residue was washed with dichloromethane (100 mL). The combined filtrate was washed with brine solution and dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure. The crude product was purified by column chromatography using ethyl acetate in hexane as an eluent to obtain lV-(2, 5-dimethyl-3-(4, 4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)-A-ethyl-A-methylformimidamide (3.2 g, 55 % yield). LCMS m/z 317.25 (M + 1). b) Preparation of 2V-ethyl-iV’-(3-(3-methoxybenzyl)-2,5-dimethylphenyl)-iV- methylformimidamide

A mixture of M-(2,5-dimethyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)-A-ethyl-A- methylformimidamide (1.5 g, 4.7 mmol), l-(bromomethyl)-3-methoxybenzene (1.0 g, 4.7 mmol), tetrakis(triphenylphosphine)palladium(0) [Pd(Ph3P)4] (0.3 g, 0.2 mmol) and potassium carbonate (1.6 g, 11.9 mmol) in dioxane:water (18 mL, 8:2) was degassed with nitrogen. The reaction mixture was stirred at 90 °C for 4 h under a nitrogen atmosphere. After the reaction was completed, the mixture was cooled to 25 °C and filtered through a celite bed. 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 preparative HPLC to obtain A-ethyl-A’-(3-(3-methoxybenzyl)-2,5-dimethylphenyl)-A- methylformimidamide (0.4 g, 29 % yield).

¹H-NMR (400 MHz, DMSO-^J 3 7.55 (bs, 1H), 7.16 (t, 1H), 6.74-6.70 (m, 1H), 6.67-6.63 (m, 2H), 6.57 (s, 1H), 6.45 (s, 1H), 3.83 (s, 2H), 3.68 (s, 3H), 3.40-3.27 (m, 2H), 2.89 (s, 3H), 2.17 (s, 3H), 2.03 (s, 3H), 1.09 (t, 3H); LCMS m/z 311.15(M + 1).

Example 4: Synthesis of of 2V'-(5-chloro-2-methyl-3-(3-methylbenzyl)phenyl)-iV-ethyl-iV- methylformimidamide a) Preparation of /V'-(5-chloro-2-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)phenyl)- V-ethyl- V-methylformimidamide A stirred mixture of M-(3-bromo-5-chloro-2-methylphenyl)-A-ethyl-A-methylformimidamide (10 g, 34.5 mmol), bis(pinacolato)diboron (17.5 g, 69.1 mmol), [l,l’-bis(diphenylphosphino)ferrocene] dichloropalladium(II) dichloromethane [PdC12(dppf)-CH2C12] (2.8 g, 3.5 mmol) and potassium acetate (6.8 g, 69.1 mmol) in 1,4-dioxane (100 mL) was degassed for 5 min with nitrogen. The reaction mixture was stirred at 95 °C for 16 h under nitrogen atmosphere. After the reaction was completed, the mixture was diluted with dichloromethane, filtered through a celite bed and the residue was washed with dichloromethane (100 mL). The combined filtrate was washed with brine solution and dried over anhydrous sodium sulfate. The volatiles were removed under reduced pressure. The crude product was purified by column chromatography using ethyl acetate in hexane as an eluent to obtain lV-(5-chloro-2-methyl-3- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)-A-ethyl-A-methylformimidamide (8 g, 23.7 mmol, 69 % yield). LCMS m/z 337.1 (M + 1). b) Preparation of 2V'-(5-chloro-2-methyl-3-(3-methylbenzyl)phenyl)-iV-ethyl-iV- methylformimidamide

A mixture of -(5-chloro-2-methyl-3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)phenyl)-A-ethyl-A- methylformimidamide (2.5 g, 7.4 mmol), l-(bromomethyl)-3-methylbenzene (1.4 g, 7.4 mmol), tetrakis(triphenylphosphine)palladium(0) [Pd(Ph3P)4] (0.4 g, 0.4 mmol) and potassium carbonate (2.1 g, 14.9 mmol) in dioxane:water (30 mL, 8:2) was degassed with nitrogen. The reaction mixture was stirred at 90 °C for 4 h under nitrogen atmosphere. After the reaction was completed, the mixture was cooled to 25 °C and filtered through a celite bed. The filtrate was diluted with ethyl acetate, washed with brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The crude product was purified by preparative HPLC to obtain /V-(5-chloro-2-methyl-3-(3-methylbenzyl)phenyl)-A-ethyl-A- methylformimidamide (1.6 g, 5.1 mmol, 68 % yield).

¹H-NMR (400 MHz, DMSO- _s) 37.70-7,50 (m, 1H), 7.14 (t, 1H), 6.95 (d, 1H), 6.91 (s, 1H), 6.87 (d, 1H), 6.73-6.67 (m, 2H), 3.84 (s, 2H), 3.41-3.25 (m, 2H), 2.98-2.83 (m, 3H), 2.21 (s, 3H), 2.04 (s, 3H), 1.08 (t, 3H); LCMS m/z 315.1 (M + 1).

BIOLOGY EXAMPLES:

As described herein, the compounds of formula (I) or respective composition show fungicidal activities which are exerted with respect to numerous fungi which attack on important agricultural crops. The compounds of the present invention in respective composition were assessed for their activity as described in the following tests:

The following examples are given purely by way of illustration of the invention without any limitation. Biological Test Examples

The methods followed to check the efficacy of the single compound and the respective composition on different pathogens were as following:

Example A: Pyricularia oryzae test in rice

The single compounds or respective composition were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to a calibrated spray volume of 30 mL. The test solutions were poured into spray bottles for further applications.

To test the preventive activity of compounds, healthy young rice plants, raised in the greenhouse, were sprayed with the single compound or its respective composition at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 1.4xl0⁶ Pyricularia oryzae inoculum. The inoculated plants were then kept in a greenhouse chamber at 24 °C temperature and 95 % relative humidity for disease expression.

A visual assessment of the performance of the single compounds or respective composition was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the single compound and its composition were calculated by comparing the disease rating in the treatment with the one of the untreated, inoculated control plants. The compounds and mixtures were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

The results are shown for the represent! ve compound of formula (I), particularly (1-1) in Table A

Surprisingly, the following combinations, indicated in the table below, have revealed unexpected synergistic effects:

Table-Al: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (1-1) as component (1), other components (2) is selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts, and components (3) is selected from the groups (A) to (E) against Pyricularia oryzae in rice are shown in the table below:

Table-Al:

Example B: Alternaria solani test in tomato

The single compounds or respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to a calibrated spray volume of 30 mL. The test solutions were poured into spray bottles for further applications.

To test the preventive activity of compounds, healthy young tomato plants, raised in the greenhouse, were sprayed with the single compounds or respective compositions at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 0.24xl0⁶ Alternaria solani inoculum and 2% Malt. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 90-95 % relative humidity for disease expression.

A visual assessment of the performance of the single compounds or respective composition was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the single compound and its composition was calculated by comparing the disease rating in the treatment with the one of the untreated, inoculated control plants. The compounds and respective composition were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

The results are shown for the represent! ve compound of formula (I), particularly (1-1) in Table Bl.

The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (1-1) as component (1), other components (2) is selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts, and components (3) is selected from the groups (A) to (E) against Alternaria solani on tomato plant are shown in the table below:

Table-Bl:

Example C: Erysiphe cichoracearum test in cucumber

To test the preventive activity of compounds, healthy young cucumber plants, raised in the greenhouse, were sprayed with the single compound or its composition, at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a conidial suspension containing 2xl0⁵ Erysiphe cichoracearum inoculum. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 50-60 % relative humidity for disease expression.

A visual assessment of the performance of the single compounds and the respective composition was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds and the respective composition was calculated by comparing the disease rating in the treatment with the one of the untreated, inoculated control plants. The compounds and respective composition were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis, and stunting.

The results are shown for the represent! ve compound of formula (I), particularly (1-1) in Table Cl.

Table-Cl: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (1-1) as component (1), other components (2) is selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts, and components (3) is selected from the groups (A) to (E) against Erysiphe cichoracearum in cucumber are shown in the table below:

Table-Cl:

Example D: Phakopsora pachyrhiz.i test in soybean

The single compounds or respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing an emulsifier to a calibrated spray volume of 30 ml. The test solutions were poured into spray bottles for further applications.

To test the preventive activity of compounds, healthy young soybean plants, raised in the greenhouse, were sprayed with the single compound or its composition, at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a suspension containing 2 xlO⁵ Phakopsora pachyrhizi conidia. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 80-90 % relative humidity for disease expression.

A visual assessment of the performance of the single compounds and the respective composition was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds and its composition was calculated by comparing the disease rating in the treatment with the one of the untreated, inoculated control plants. The compounds and the compositions were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

The results are shown for the represent! ve compound of formula (I), particularly (1-1) in Table DI. Surprisingly, the following combinations, indicated in the table below, have revealed unexpected synergistic effects:

Table-Dl: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (1-1) as component (1), other components (2) is selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts, and components (3) is selected from the groups (A) to (E) against Phakopsora pachyrhizi test in soybean are shown in the table below:

Table-Dl:

Example E: Parastagonospora nodorum/ Septaria nodorum/ Stagnospora nodorum test in wheat

The single compounds or respective compound combinations were dissolved in 2% DMSO/ Acetone and then mixed with water containing an emulsifier to a calibrated spray volume of 30 mL. The spray solutions were poured into spray bottles for further applications.

To test the preventive activity of the compounds and respective composition , healthy young wheat plants, raised in the greenhouse, were sprayed with the single compound or respective composition at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a suspension containing 2.8xl0⁶ Stagnospora nodorum inoculum. The inoculated plants were then kept in a greenhouse chamber at 22-25 °C temperature and 90-100 % relative humidity for disease expression.

A visual assessment of the performance of the single compounds and the respective composition was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7 and 10 days after application. Efficacy (% control) of the compounds and composition was calculated by comparing the disease rating in the treatment with the one of the untreated, inoculated control plants. The compounds and the respective compositions were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis & stunting.

The results are shown for the represent! ve compound of formula (I), particularly (1-1) in Table El.

Table-El: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (1-1) as component (1), other components (2) is selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts, and components (3) is selected from the groups (A) to (E) against Septaria nodorum in wheat are shown in the table below:

Table-El:

Example F: Botrytis cinerea test in tomato

To test the preventive activity of the compounds or respective composition , healthy young tomato plants, raised in the greenhouse, were sprayed with the single compound or respective composition, at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 1.2xl0⁶ Botrytis cinerea inoculum and 2% malt. The inoculated plants were then kept in a greenhouse chamber at 18-20 °C temperature and 90-100 % relative humidity for disease expression.

A visual assessment of the performance of the single compounds and the respective composition was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7 and 10 days after application. Efficacy (% control) of the compounds and compositions were calculated by comparing the disease rating in the treatment with the one of the untreated, inoculated control plants. The compounds and compositions were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis & stunting.

The results are shown for the represent! ve compound of formula (I), particularly (1-1) in Table Fl.

Surprisingly, the following combinations, indicated in the table below, have revealed unexpected synergistic effects: Table-Fl: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (1-1) as component (1), other components (2) is selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts, and components (3) is selected from the groups (A) to (E) against Botrytis cinerea in tomato are shown in the table below:

Table-Fl:

Example G: Phytophthora infestans test on tomato plants

The single compounds or respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to the desired test concentration in a calibrated spray volume of 50 mL. The test solutions were poured into spray bottles for further applications. To test the preventive activity of compounds, healthy young tomato plants raised in the greenhouse were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a sporangial suspension (cold sterile water containing 0.24xl0⁶ Phytophthora infestans inoculum). After inoculation, the plants were kept in darkness at 15°C during 24 h, and then moved to a greenhouse chamber with 18 °C temperature and 95- 100 % relative humidity for disease expression.

A visual assessment of the performance of the single compounds and the respective compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds and combination was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

The results are shown for the represent! ve compound of formula (I), particularly (1-1) in Table G1

Table-Gl: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (1-1) as component (1), other components (2) is selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts, and components (3) is selected from the groups (A) to (E) against Phytophthora infestans on tomato are shown in the table below:

Table-Gl:

Example H: Rhizoctonia solani test in Rice

The single compounds or compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to a calibrated spray volume of 50ml. The test solutions were poured into spray bottles for further applications. To test the preventive activity of compounds, healthy young rice seedlings/ plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles.

One day after treatment, the plants were inoculated with an equal quantity of infected Sorghum grain containing Rhizoctonia solani. The inoculated plants were then kept in a greenhouse chamber at 24-25 °C temperature and 90-95 % relative humidity for disease expression.

A visual assessment of the performance of the single compounds and respective compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

The results are shown for the represent! ve compound of formula (I), particularly (1-1) in Table Hl.

Table-Hl: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (1-1) as component (1), other components (2) is selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts, and components (3) is selected from the groups (A) to (E) against Rhizoctonia solani test in Rice are shown in the table below:

Table-Hl:

Example J: Fusarium culmorum test in Wheat

The single compounds or compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to a calibrated spray volume of 50 mL. The test solutions were poured into spray bottles for further applications.

To test the preventive activity of compounds, healthy young wheat plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 2xl0⁶ Fusarium culmorum inoculum with 2% malt. The inoculated plants were then kept in a greenhouse chamber at 24 °C temperature and 80-90 % relative humidity for disease expression.

The results are shown for the represent! ve compound of formula (I), particularly (1-1) in Table JI.

Table- JI: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (1-1) as component (1), other components (2) is selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts, and components (3) is selected from the groups (A) to (E) against Fusarium culmorum in Wheat are shown in the table below:

Table- JI:

Example K: Pseudoperonospora cubensis on cucumber plants

The single compounds or the respective compound combinations were dissolved in 2% dimethyl sulfoxide/acetone and then mixed with water containing emulsifier to the desired test concentration in a calibrated spray volume of 50ml. The test solutions were poured into the spray bottles for further applications.

To test the preventive activity of compounds, healthy young cucumber plants, raised in the greenhouse were sprayed with the active compound preparation at the stated application rates inside the spray cabinets using hallow cone nozzles. One day after treatment, the plants were inoculated with a conidial spore suspension containing 2xl0⁴ Pseudoperonospora cubensis inoculum. The inoculated plants were then kept in a greenhouse chamber at 23°C temperature & 80-90 % relative humidity for disease expression.

A visual assessment of the performance of the single compounds and the respective compound combinations was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated control. The compounds were also assessed for their plant compatibility by recording symptoms like necrosis, chlorosis and stunting.

The results are shown for the represent! ve compound of formula (I), particularly (1-1) in Table KI. Surprisingly, the following combinations, indicated in the table below, have revealed unexpected synergistic effects:

Table-Kl: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (1-1) as component (1), other components (2) is selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts, and components (3) is selected from the groups (A) to (E) against Pseudoperonospora cubensis in cucumber are shown in the table below:

Table-Kl:

Example L: Corynespora cassiicola test in Tomato plant

Compounds were dissolved in 2 % dimethyl sulfoxide/acetone and then mixed with water containing an emulsifier to the calibrated spray volume of 30 mL. Each spray solution was poured into a spray bottle for further application.

To test the preventive activity of the compound, healthy young tomato plants, raised in the greenhouse, were sprayed with the active compound preparation at the stated application rate inside the spray cabinets using hollow cone nozzles. One day after treatment, the plants were inoculated with a spore suspension containing 2.6xl0⁶ Corynespora cassiicola inoculum. The inoculated plants were then kept in a greenhouse chamber at 22-24 °C temperature and 90-95 % relative humidity for disease expression.

A visual assessment of the performance of the single compounds and the respective compound combination was carried out by rating the disease severity (0-100% scale) on treated plants 3, 7, 10 and 15 days after application. Efficacy (% control) of the compounds was calculated by comparing the disease rating in the treatment with the one of the untreated but inoculated control. The treated plants were also assessed for plant damage by recording symptoms like necrosis, chlorosis and stunting.

The results are shown for the represent! ve compound of formula (I), particularly (1-1) in Table LI.

Surprisingly, the following combinations, indicated in the table below, have revealed unexpected synergistic effects: Table-Ll: The synergistic fungicidal activity of the compositions of the present invention, wherein the representative compounds of formula (I) is particularly compound (1-1) as component (1), other components (2) is selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts, and components (3) is selected from the groups (A) to (E) against Corynespora cassiicola in tomato are shown in the table below:

Table-Ll:

Unexpected and surprisingly the composition of the present invention showed a synergistic efficacy when compared to the individual components.

Having described the invention with reference to certain preferred embodiments, other embodiments will become apparent to one skilled in the art from consideration of the specification.

Claims

WE CLAIM:

1. An agrochemical composition comprising a mixture of component (1), and at least two components selected from component (2), component (3), or a combination of component (2) and component (3), wherein the component (1) is a compound of formula (I),

wherein,

R² is selected from the group consisting of ethyl, isopropyl, cyclopropyl, and cyclopropylmethyl ;

R⁷ is selected from the group consisting of hydrogen, halogen, cyano, methyl, ethyl, isopropyl, halomethyl, methoxy, ethoxy, isopropoxy, halomethoxy, haloethoxy, and cyclopropyl; n represent integers 0, 1, 2, 3 or 4; and salts, A-oxides, metal complexes or stereoisomers thereof; as component (2) at least one fungicide selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts; and as component (3) at least one fungicide different from components (1) and (2) selected from the groups:

(A) inhibitors of the sterol biosynthesis, selected from (A001) prothioconazole; (A002) cyproconazole; (A003) tebuconazole; (A004) mefentrifluconazole; (A005) difenoconazole; (A006) epoxiconazole; (A007) metconazole; (A008) paclobutrazol; (A009) pyrisoxazole; (A010) propiconazole; (A011) tetraconazole; (A012) triticonazole; (A013) ipfentrifluconazole; (A014) clotrimazole; (A015) econazole; (A016) isoconazole; (A017) miconazole; (A018) oxpoconazole; (AO 19) triflumizole; (A020) azaconazole; (A021) bromuconazole; (A022) diniconazole; (A023) diniconazole-M; (A024) etaconazole; (A025) fenbuconazole; (A026) hexaconazole; (A027) imibenconazole; (A028) penconazole; (A029) simeconazole; (A030) ipconazole; (A031) uniconazole; (A032) fenhexamid; (A033) fenpropidin; (A034) fenpropimorph; (A035) fenpyrazamine; (A036) fluquinconazole; (A037) flutriafol; (A038) imazalil; (A039) imazalil sulfate; (A040) spiroxamine; (A041) prochloraz; (A042) myclobutanil; (A043) triadimenol; (A044) tridemorph; (A045) terbinafine; (A046) buthiobate; (A047) pyrifenox; (A048) fenarimol; (A049) nuarimol; (A050) triarimol; (A051) triforine; (A052) bitertanol; (A053) pefurazoate; (A054) triadimefon; (A055) pyributicarb; (A056) dodemorph; (A057) aldimorph; (A058) trimorphamide; (A059) piperalin; (A060) naftifine;

(B) inhibitors of the respiratory chain at complex I or II, selected from (B001) benzovindiflupyr; (B002) bixafen; (B003) fluindapyr; (B004) fluxapyroxad; (B005) inpyrfluxam; (B006) boscalid; (B007) carboxin; (B008) fluopyram; (B009) flutolanil; (B010) furametpyr; (B011) isofetamid; (B012) penflufen; (BO 13} penthiopyrad; (BOM) pydiflumetofen; (B015) pyraziflumid; (B016) sedaxane; (B017) isoflucypram; (B018) pyrapropoyne; (B019) fenfuram; (B020) mepronil; (B021) benodanil; (B022) oxycarboxin; (B023) diflumetorim; (B024) thifluzamide; (B025) isopyrazam;

(C) inhibitors of the respiratory chain at complex III, selected from (C001) metarylpicoxamid; (C002) azoxystrobin; (C003) metominostrobin; (C004) orysastrobin; (C005) picoxystrobin; (C006) pyraclostrobin; (C007) pyrametostrobin; (C008) pyraoxystrobin; (C009) trifloxystrobin; (C010) coumethoxystrobin; (C011) coumoxystrobin; (CO 12} dimoxystrobin; (COM) enoxastrobin; (COM) flufenoxystrobin; (C015) fluoxastrobin; (C016) mandestrobin; (C017) ametoctradin; (C018) amisulbrom; (C019) cyazofamid; (C020) famoxadone; (C021) fenamidone; (C022) kresoxim-methyl; (C023) metyltetraprole; (C024) florylpicoxamid; (C025) pyribencarb; (C026) fenpicoxamid;

(D) compounds capable to have a multisite action, selected from(DOOl) chlorothalonil; (D002) mancozeb; (D003) copper hydroxide; (D004) copper oxychloride; (D005) captafol; (D006) captan; (D007) thiram; (D008) zineb; (D009) ziram; (D010) ferbam; (D011) dichlofluanid; (DOM) tolylfluanid; (DOM) guazatine; (DOM) iminoctadine; (DOM) anilazine; (D016) quinomethionate; (DOM) dithianon; (DO 18) dodine; (DO 19) folpet; (D020) maneb; (D021) metiram; (D022) metiram zinc; (D023) oxine -copper; (D024) propineb; (D025) copper naphthenate; (D026) copper oxide; (D027) copper sulfate; (D028) bordeaux mixture; (D029) sulfur and sulfur preparations including calcium poly sulfide; or

(E) inhibitors of histone deacetylase selected from (E001) flufenoxadiazam; (E002) N- methoxy-N-[[4-[5-(tri fluoro methyl)-!, 2, 4-oxadiazol-3- yl]phenyl]methyl]cyclopropanecarboxamide .

2. The agrochemical composition comprising a mixture of component (1), component (2), and component (3) according to claim 1, wherein the component (1) is selected from:

(1-7) N'-(3-(4-(difluoromethoxy)benzyl)-2,5-dimethylphenyl)-N-ethyl-N- methy Iformi midamide ;

(1-8) N-ethyl-N'-(3-(3-fluoro-5-methylbenzyl)-5-methoxy-2-methylphenyl)-N- methy Iformi midamide ;

(1-9) N'-(5-chloro-3-(4-(difluoromethoxy)benzyl)-2-methylphenyl)-N-ethyl-N- methylformimidamide, or (I-10)N'-(5-chloro-3-(4-isopropoxybenzyl)-2-methylphenyl)-N-ethyl-N-methylformimidamide. and salts, A-oxides, metal complexes or stereoisomers thereof; as component (2) at least one fungicide selected from azoxystrobin, metominostrobin, picoxystrobin, trifloxystrobin, pyraclostrobin, metyltetraprole, benzovindiflupyr, bixafen, fluxapyroxad, fluindapyr, inpyrfluxam, mefentrifluconazole, cyproconazole, tebuconazole, prothioconazole, chlorothalonil, mancozeb or their salts; and as component (3) at least one fungicide different from components (1) and (2) selected from the groups:

3. The agrochemical composition according to claim 1, wherein the component (1) and the component

(2) is in a weight ratio range from 100:1 to 1:100; the weight ratio of component (1) to component

(3) in ternary composition is in the range from 100:1 to 1:100; the weight ratio of component (2) to component (3) in ternary composition is in the range from 100:1 to 1:100.

4. The agrochemical composition according to claim 1, wherein the component (1) and the component

(2) is in a weight ratio range from 50:1 to 1:50; the weight ratio of component (1) to component (3) in ternary composition is in the range from 100:1 to 1:100; the weight ratio of component (2) to component (3) in ternary composition is in the range from 100:1 to 1:100.

5. The agrochemical composition according to claim 1, wherein the component (1) and the component

(2) in a weight ratio of from 10:1 to 1:10; the weight ratio of component (1) to component (3) in ternary composition is in the range from 100:1 to 1:100; the weight ratio of component (2) to component (3) in ternary composition is in the range from 100:1 to 1:100.

6. The agrochemical composition according to claims 1, wherein said composition further comprises agriculturally acceptable additives.

7. The agrochemical composition according to claim 6, wherein agriculturally acceptable additives are selected from the group consisting of: solvent(s) or diluent(s), dye(s), wetting agent(s), dispersant(s), emulsifier(s), antifoam(s), preservative(s), thickener(s), adhesive(s), gibberellins, solid carrier(s), liquid carrier(s), gaseous carrier(s), surfactant(s), binder(s), disintegrating agent(s), pH adjuster(s), anti-caking agent(s), anti-freezing agent(s), defoaming agent(s), extender(s), filler(s), stabilizer(s), coloring agent(s) or combination thereof.

8. The agrochemical composition according to claim 6 or 7, wherein the composition is in the form of, a suspension concentrate (SC), a water dispersible granule (WDG)/(WG), a tablet (TB), a wettable powder (WP), a water dispersible tablet (WT), an ultra-low volume (ULV), a liquid (UL), an ultralow volume (ULV), a suspension (SU), a water soluble powder (SP), a suspo-emulsion (SE), a granule (GR), an emulsifiable granule (EG), an oil-in-water emulsion (EW), an emulsifiable granule (EG), an emulsion oil in water (EO), an emulsifiable powder (EP), an emulsion for seed treatment (ES), a solution for seed treatment (LS), a flowable concentrate for seed treatment (FS), an emulsifiable concentrate (EC), a micro-emulsion (ME), oil-in-water emulsions (EW), an oil miscible flowable concentrate (oil miscible suspension) (OF), an oil dispersible powder (OP), an oil dispersion (OD), a capsule suspension (CS), a dustable powder (DP), a soluble concentrate (SL), a water soluble granule (SG), an aerosol (AE), a mixed formulation of CS and SC (ZC), a mixed formulation of CS and SE (ZE) or a mixed formulation of CS and EW (ZW).

9. The agrochemical composition according to claims 1 to 8, for controlling or preventing agricultural crops and/or horticultural crops against diseases caused by phytopathogenic fungi.

10. The agrochemical composition according to claims 9, for controlling or preventing agricultural crops and/or horticultural crops against diseases caused by phytopathogenic fungi wherein said phytopathogenic fungi are Alternaria spp., Botrytis spp., Cercospora spp., Colletotrichum spp., Corynespora spp., Erysiphe spp., Fusarium spp., Hemileia spp., Phakopsoraceae spp., Phytophthora spp, Pseudoperonospora spp, Pyricularia spp., Rhizoctonia spp., Septaria spp, Puccinia spp., and Uromyces spp.

11. Use of agrochemical composition according to claims 1 to 8, for treating seed, seed of transgenic plants or transgenic plants.

12. A method for controlling or preventing infestation of useful plants by phytopathogenic fungi in agricultural crops and/or horticultural crops, comprising applying an agrochechemically effective amount of a composition according to claims 1 to 8 to the plant or parts thereof, or to the plant seeds, or to a locus thereof.