TW201625555A - Aryl sulphide and aryl sulphoxide derivatives having C-C-attached (aza)uracils as pesticides - Google Patents

Abstract

The invention relates to novel compounds of the formula (I)in which R1, R2, n, V1, V2, Q, W, X and Y have the meanings given in the description, a plurality of processes and intermediates for their preparation and their use as acaricides and/or insecticides and/or nematicides for controlling animal pests, for example in crop protection or in the field of animal health.

Description

Aryl sulfide and aryl hydrazine derivative having C-C-linked (aza) uracil as a pesticide

This application relates to a novel heterocyclic compound, a process for its preparation and its use for controlling animal pests, including arthropods and especially insects.

Aryl sulfides and aryl hydrazine derivatives and their insecticidal and acaricidal effects are described in the literature, for example: WO 2013/157229, WO 2012/176856 and WO 1999/055668.

Crop protection agents (including pesticides) must meet many requirements, such as their effectiveness, duration, scope of action, and possible use. The toxicity and its compatibility with other active compounds or formulation adjuvants also play a role as well as the synthetic cost issues required for the active compounds. In addition, resistance can occur. For all of these reasons, it is believed that the search for novel crop protection agents has not yet been completed, and it is still necessary to have novel compounds that modify the good properties of the known compounds at least in each of the relevant aspects.

It is an object of the present invention to provide a compound which broadens the range of action of the pesticide in a variety of different aspects.

This object and other objects not described herein but which may be discerned or derived from the relevant discussion may be achieved by the novel compound of formula (I) Wherein (specific embodiment 1-1) V ¹ and V ² each independently represent oxygen or represent sulfur; Q represents substituted carbon or represents nitrogen; and R ¹ and R ² each independently represent hydrogen, amine or alkyl; Or represents alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cyanoalkyl, hydroxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxyalkyl, haloalkoxy An alkyl group, an alkoxy group, a haloalkoxy group, a haloalkyl group, a haloalkenyl group or a haloalkynyl group, wherein the above group may be optionally substituted; or represents an aryl group, a heteroaryl group, an arylalkyl group or a heteroaryl group. An alkyl group wherein the above group may be optionally substituted; W represents hydrogen or halogen; n represents the number 0, 1 or 2; Y represents hydrogen, halogen, cyano, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )-alkoxy or (C ₁ -C ₆ )-haloalkoxy; X represents hydrogen, Halogen, cyano, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl or (C ₁ -C ₆ )-alkoxy.

It has also been found that the novel compounds of formula (I) have good pesticide efficacy, for example against arthropods, and especially insects and mites, in addition to plants (especially crops). It has excellent compatibility and/or has advantageous toxicological and/or environmentally relevant properties.

Another specific embodiment of the compound of formula (I) (specific embodiment 1-2) is characterized in that V ¹ and V ² each independently represent oxygen or represent sulfur; Q represents a carbon substituted by the following groups: hydrogen, halogen , amine, cyano, amine, mercapto, nitro, alkyl, haloalkyl, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkyl Sulfhydryl, haloalkylsulfonyl, cycloalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxycarbonyl or alkoxy, or represents nitrogen; R ¹ and R ² each independently represent hydrogen, amine Or alkyl; or represents alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cyanoalkyl, hydroxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxyalkyl, a haloalkoxyalkyl group, an alkoxy group, a haloalkoxy group, a haloalkyl group, a haloalkenyl group or a haloalkynyl group, wherein the above group may be substituted by the following groups: halogen, alkyl, cycloalkyl, cyanogen Alkyl, nitro, alkoxy, haloalkyl or haloalkoxy, in particular fluorine, chlorine, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, cyclopropane Base, cyano group, (C ₁ -C ₄ )-alkoxy group, (C ₁ -C ₃ )-haloalkyl or (C ₁ -C ₃ )-haloalkoxy; or an aryl, heteroaryl, arylalkyl or heteroarylalkyl group, wherein the above groups may be optionally used Substituted by: halogen, alkyl, cycloalkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy, in particular fluorine, chlorine, (C ₁ -C ₃ )-alkyl (C ₃ -C ₆ )-cycloalkyl, cyclopropyl, cyano, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₃ )-haloalkyl or (C ₁ -C ₃ )-haloalkoxy; W represents hydrogen or halogen; n represents the number 0, 1 or 2; Y represents hydrogen, halogen, cyano, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )- Cycloalkyl, (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )-alkoxy or (C ₁ -C ₆ )-haloalkoxy; X represents hydrogen, halogen, cyano, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl or (C ₁ -C ₆ )-alkoxy.

A general definition of a compound of the invention is provided by formula (I). Preferred substituents or ranges for the groups shown in the above formulas and hereinafter are illustrated below (specific examples 2-1): V ¹ and V ² represent oxygen, respectively; Q represents nitrogen or CR ³ , wherein R ³ represents Hydrogen, halogen, amine, cyano, amine, mercapto, nitro, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )-alkane thio group, (C ₁ -C ₆₎ - alkylsulfinyl acyl, (C ₁ -C ₆₎ - alkylsulfonyl group, (C ₁ -C ₆₎ - haloalkyl group, (C ₁ -C ₆ )-haloalkylsulfinyl, (C ₁ -C ₆ )-haloalkylsulfonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-alkyl a carbonyl group, a (C ₁ -C ₆ )-haloalkylcarbonyl group, a (C ₁ -C ₆ )-alkoxycarbonyl group or a (C ₁ -C ₆ )-alkoxy group; R ¹ and R ² each independently represent hydrogen Or an amino group or an alkyl group; or an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylalkyl group, a cycloalkenyl group, a cyanoalkyl group, a hydroxyalkyl group, an alkylcarbonyl group, a haloalkylcarbonyl group, an alkoxy group An alkyl group, a haloalkoxyalkyl group, an alkoxy group or a haloalkoxy group, wherein the above group may be optionally substituted; or a haloalkyl group, a haloalkenyl group or a haloalkynyl group; W represents hydrogen or a halogen; The number 0 or 1; Y stands for hydrogen, Su, (C ₁ -C ₆₎ - alkyl, (C ₃ -C ₆₎ - cycloalkyl, (C ₁ -C ₆₎ - haloalkyl, (C ₁ -C ₆₎ - alkoxy or ( C ₁ -C ₆ )-haloalkoxy; X represents hydrogen, halogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl or (C ₁ -C ₆ )-alkane Oxygen.

The same preferred substituents or ranges for the groups shown in the above and below formulas are as follows (specific examples 2-2): V ¹ and V ² represent oxygen, respectively; Q represents nitrogen or CR ³ , wherein R ³ Represents hydrogen, halogen, amine, cyano, amine, mercapto, nitro, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )- alkylthio, (C ₁ -C ₆₎ - alkylsulfinyl acyl, (C ₁ -C ₆₎ - alkylsulfonyl group, (C ₁ -C ₆₎ - haloalkyl group, (C _1- C ₆ )-haloalkylsulfinyl, (C ₁ -C ₆ )-haloalkylsulfonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-alkane a carbonyl group, a (C ₁ -C ₆ )-haloalkylcarbonyl group, a (C ₁ -C ₆ )-alkoxycarbonyl group or a (C ₁ -C ₆ )-alkoxy group; R ¹ and R ² each independently represent Hydrogen, amine or alkyl; or represents alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cyanoalkyl, hydroxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxy An alkyl group, a haloalkoxyalkyl group, an alkoxy group or a haloalkoxy group, wherein the above group may be substituted by the following groups: halogen, alkyl, cycloalkyl, cyano, nitro, alkoxy , haloalkyl or haloalkoxy, Specifically, fluorine, chlorine, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, cyclopropyl, cyano, (C ₁ -C ₄ )-alkoxy, ( C ₁ -C ₃ )-haloalkyl or (C ₁ -C ₃ )-haloalkoxy; or a haloalkyl, haloalkenyl or haloalkynyl group; W represents hydrogen or halogen; n represents the number 0 or 1 Y represents hydrogen, halogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )- Alkoxy or (C ₁ -C ₆ )-haloalkoxy; X represents hydrogen, halogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl or (C ₁ - C ₆ )-alkoxy.

More preferred substituents or ranges for the groups of the formula (I) are illustrated below (specific examples 3-1). V ¹ and V ² represent oxygen, respectively; Q represents nitrogen or CR ³ , wherein R ³ represents hydrogen, amine, halogen, cyano, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-halogen Alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₄ )-alkylcarbonyl, (C ₁ -C ₄ )-haloalkylcarbonyl, (C ₁ -C ₄ )-alkoxy Alkylcarbonyl or (C ₁ -C ₄ )-alkoxy; R ¹ and R ² each independently represent hydrogen, amine, (C ₁ -C ₄ )-alkyl, cyano-(C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkoxy -(C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy or (C ₁ -C ₄ )-haloalkoxy; or represents (C ₃ -C ₆ )-cycloalkane Or (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₂ )-alkyl, wherein the above group may be substituted by the following groups: fluorine, chlorine, bromine, iodine, (C ₁ -C) ₃ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, cyano, nitro, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₃ )-haloalkyl or (C ₁ -C ₃ )-haloalkoxy; W represents hydrogen, chlorine or fluorine; n represents the number 0 or 1; Y represents halogen, (C ₁ -C ₄ )-alkyl, (C ₃ -C ₆ )-ring Alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy or (C ₁ -C ₄ )- Haloalkoxy; X represents hydrogen, halogen, (C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl or (C ₁ -C ₄ )-alkoxy.

Particularly preferred substituents or ranges for the groups of the compounds of formula (I) are illustrated below (specific examples 4-1). V ¹ and V ² represent oxygen, respectively; Q represents nitrogen or CR ³ , wherein R ³ represents hydrogen, chlorine, methyl, ethyl, methoxy, cyclopropyl, cyano or trifluoromethyl; R ¹ and R ² independently representing hydrogen, amine, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, t-butyl, CH ₂ CH(CH ₃ ) ₂ , CH ₂ CN , CH ₂ CF ₃ , CH ₂ CHF ₂ , CH ₂ CH ₂ OCH ₃ , cyclopropyl, cyclobutyl or cyclopropylmethyl; W represents fluorine; n represents the number 0 or 1; Y represents fluorine, chlorine, bromine , methyl, trifluoromethyl or methoxy; X represents hydrogen, chlorine, fluorine or methyl.

The same particularly preferred substituents or ranges for the groups of the compounds of formula (I) are illustrated below (specific examples 4-2). V ¹ and V ² represent oxygen, respectively; Q represents nitrogen or CR ³ , wherein R ³ represents hydrogen, chlorine or methyl; and R ¹ and R ² each independently represent a methyl group, a second butyl group or an amine group, preferably Respectively represent methyl; W represents fluorine; n represents the number 0 or 1; Y represents methyl; and X represents fluorine or methyl.

The same particularly preferred substituents or ranges for the groups of the compounds of formula (I) are illustrated below (specific examples 4-3). V ¹ and V ² represent oxygen, respectively; Q represents nitrogen; R ¹ and R ² each independently represent hydrogen, amine, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, Third butyl, CH ₂ CH(CH ₃ ) ₂ , CH ₂ CN, CH ₂ CF _3, CH ₂ CHF ₂ , CH ₂ CH ₂ OCH ₃ , cyclopropyl, cyclobutyl or cyclopropylmethyl; W Represents fluorine; n represents the number 0 or 1; Y represents fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy; X represents hydrogen, chlorine, fluorine or methyl.

Very particularly preferred substituents or ranges for the groups of the formula (I) are illustrated below (specific examples 5-1). V ¹ and V ² represent oxygen, respectively; Q represents nitrogen or CR ³ , wherein R ³ represents hydrogen; R ¹ and R ² represent methyl respectively; W represents fluorine; n represents the number 0 or 1; Y represents a methyl group; Fluorine or methyl.

The same very particularly preferred substituents or ranges for the groups of the compounds of formula (I) are illustrated below (specific examples 5-2). V ¹ and V ² represent oxygen, respectively; Q represents nitrogen; R ¹ represents methyl, ethyl, isopropyl or CH ₂ CF ₃ ; R ² represents methyl, ethyl or CH ₂ CF ₃ ; W represents fluorine; Represents the number 0 or 1; Y represents a methyl group; X represents a fluorine or a methyl group.

In a broad and preferred definition, unless otherwise stated, the halogen is selected from the group consisting of fluorine, chlorine, bromine and iodine, preferably selected from the group consisting of fluorine, chlorine and bromine.

In the definition of better and more visible and particularly good, unless otherwise stated Preferably, the halogen is selected from the group consisting of fluorine, chlorine, bromine and iodine, preferably selected from the group consisting of fluorine, chlorine and bromine.

Halogen-substituted groups (e.g., haloalkyl) are monohalogenated or polyhalogenated, up to the highest possible number of substituents. If polyhalogenated, the halogen atoms may be the same or different. Halogen represents fluorine, chlorine, bromine and iodine, especially fluorine, chlorine and bromine.

The saturated or unsaturated hydrocarbon group (e.g., alkyl or alkenyl group) may be a straight or branched chain, respectively, and may, if possible, be combined with a hetero atom such as, for example, an alkoxy group.

The group which may be optionally substituted may be mono- or poly-substituted, and in the case of poly-substitution, the substituents may be the same or different. Where a substituent is a substituent or optionally a substituent, unless otherwise stated, the substituents are: halo, alkyl, cycloalkyl, cyano, nitro, alkoxy, halo Or haloalkoxy, in particular fluorine, chlorine, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₆ )-cycloalkyl (especially cyclopropyl), cyano, (C ₁ - C ₄ )-alkoxy, (C ₁ -C ₃ )-haloalkyl or (C ₁ -C ₃ )-haloalkoxy.

The definitions or descriptions of the radicals within the above general terms or preferred ranges also apply correspondingly to the final product (including substructures (IA) and (IB) and (IA-1) and (IB-1) which will be described below. The compound of formula (I)), and the starting materials and intermediates. These group definitions can be combined with each other as desired, that is, including combinations of individual preferred ranges.

Preferably, a combination of the above-described preferred definitions is present in the compound of formula (I) according to the invention, and each of the above preferred embodiments constitutes a separate combination, in particular as embodiment 2-1 or a specific embodiment 2-2 Description of the combination.

More preferably, there is a combination of the above-defined definitions in the compound of the formula (I) according to the present invention, and each of the above-described preferred embodiments constitutes a separate combination, specifically a combination as described in the specific embodiment 3-1.

It is particularly preferred that the compound of formula (I) according to the invention is present as described above in particular Combinations of meanings, and each of the above-described particularly preferred embodiments constitute a separate combination, specifically as described in the specific embodiment 4-1 or the combination of the specific embodiment 4-2 or the specific embodiment 4-3.

Very particularly preferably, in accordance with the invention, a combination of the above-mentioned very particularly preferred definitions of the compounds of the formula (I), and each of the above-mentioned very particularly preferred embodiments constitute a separate combination, in particular as in the specific example 5-1 or The combination of the specific embodiments 5-2 is described.

Another embodiment, the present invention relates to a compound structure of formula (I) particularly preferred embodiment, wherein Q represents CR ^3. Resulting in a compound of formula (IA)

In the compound of the formula (I) defined by the formula (IA), the group or the structural elements R ¹ , R ² , R ³ , V ¹ , V ² , n, W, X and Y have the above definitions, specifically The description is as in the specific embodiment 1-1 (specific embodiment IA.1-1) or the specific embodiment 1-2 (specific embodiment IA.1-2).

Preferred among the compounds of the formula (I) defined by the formula (IA) are those in which a combination of the above preferred definitions is present, and each of the above preferred embodiments constitutes a separate combination, specifically as specific A combination of the description of Example 2-1 (Specific Example IA.2-1) or Specific Example 2-2 (Specific Example IA.2-2).

More preferably, among the compounds of the formula (I) defined by the formula (IA), are compounds in which a combination of the above-prepared definitions is present, and each of the above-described preferred embodiments constitutes a separate combination, specifically as specific The combination of the description of Example 3-1 (Specific Example IA.3-1).

Particularly preferred among the compounds of the formula (I) defined by the formula (I-A) are those in which a combination of the above-mentioned particularly preferred definitions is present, and each of the above-mentioned particularly preferred embodiments constitutes Independent combination, specifically as specific embodiment 4-1 (specific embodiment IA.4-1) or specific embodiment 4-2 (specific embodiment IA.4-2) or specific embodiment 4-3 (specific A combination of the descriptions of Examples IA.4-3).

Particularly preferred among the compounds of the formula (I) defined by the formula (IA) are those in which the combinations of the above-mentioned very particularly preferred combinations are present, and each of the above-mentioned very particularly preferred embodiments constitutes a separate combination, in particular The combination as described in the specific embodiment 5-1 (specific embodiment IA.5-1) or the specific embodiment 5-2 (specific embodiment IA.5-2).

More specifically, X and Y represent the following (Y, X) combinations: (Me, F), (Me, H), (Me, Cl), (Me, Me), (Cl, Cl), (Cl, F), (MeO, F), (MeO, H), (Cl, H), (Br, H), (Br, F), (F, F), (CF ₃ , H), (CF ₃ , F), particularly preferably the following (Y, X) combination: (Me, F), (Me, Me), (Cl, Cl).

Particularly preferred embodiments of the compounds of formula (IA) are those in which R ³ represents H. As a result, a compound of the formula (IA-1) is produced.

In the compound of the formula (I) defined by the formula (IA-1), the group or the structural elements R ¹ , R ² , V ¹ , V ² , n, W, X and Y have the definitions as defined above, specifically Description of Specific Embodiment 1-1 (Specific Example IA-1.1-1) or Specific Example 1-2 (Specific Example IA-1.1-2).

Preferred among the compounds of the formula (I) defined by the formula (IA-1) are those in which a combination of the above preferred definitions is present, and each of the above preferred embodiments constitutes a separate combination, in particular Specific embodiment 2-1 (specific embodiment IA-1.2-1) or specific embodiment 2-2 (Specific Example I-A-1.2-2) A combination of the descriptions.

More preferably, among the compounds of the formula (I) defined by the formula (IA-1), are compounds in which a combination of the above-defined definitions is more preferred, and each of the above-described preferred embodiments constitutes a separate combination, in particular A combination as described in the specific embodiment 3-1 (specific example IA-1.3-1).

Particularly preferred among the compounds of the formula (I) defined by the formula (IA-1) are those in which a combination of the above-mentioned particularly preferred definitions is present, and each of the above-mentioned particularly preferred embodiments constitutes a separate combination, in particular Specific embodiment 4-1 (specific embodiment IA-1.4-1) or specific embodiment 4-2 (specific embodiment IA-1.4-2) or specific embodiment 4-3 (specific embodiment IA-1.4-3 ) a combination of instructions.

Particularly preferred among the compounds of the formula (I) as defined in the formula (IA-1) are those in which a combination of the above-mentioned extremely preferred definitions is present, and each of the above-mentioned very particularly preferred embodiments constitutes a separate combination. Specifically, a combination of the specific embodiment 5-1 (specific embodiment IA-1.5-1) or the specific embodiment 5-2 (specific embodiment IA-1.5-2) is described.

More specifically, X and Y represent the following (Y, X) combinations: (Me, F), (Me, H), (Me, Cl), (Me, Me), (Cl, Cl), (Cl, F), (MeO, F), (MeO, H), (Cl, H), (Br, H), (Br, F), (F, F), (CF ₃ , H), (CF ₃ , F), particularly preferably the following (Y, X) combination: (Me, F), (Me, Me), (Cl, Cl).

In another preferred embodiment, the invention relates to a compound of formula (I) wherein Q represents N. As a result, a compound of the formula (I-B) is produced.

In the compound of the formula (I) defined by the formula (IB), the group or the structural elements R ¹ , R ² , V ¹ , V ² , n, W, X and Y have the definitions as defined above, and are specifically embodied as Description of Example 1-1 (Specific Example IB.1-1) or Specific Example 1-2 (Specific Example IB.1-2).

Preferred among the compounds of the formula (I) defined by the formula (IB) are those in which a combination of the above preferred definitions is present, and each of the above preferred embodiments constitutes a separate combination, specifically as specific A combination of the description of Example 2-1 (Specific Example IB.2-1) or Specific Example 2-2 (Specific Example IB.2-2).

More preferably, among the compounds of the formula (I) defined by the formula (IB), are compounds in which a combination of the above-defined definitions is more preferred, and each of the above-described preferred embodiments constitutes a separate combination, specifically as specific The combination of the description of Example 3-1 (Specific Example IB.3-1).

Particularly preferred among the compounds of the formula (I) defined by the formula (IB) are those in which a combination of the above-mentioned particularly preferred definitions is present, and each of the above-mentioned particularly preferred embodiments constitutes a separate combination, specifically as specific Description of Example 4-1 (Specific Example IB.4-1) or Specific Example 4-2 (Specific Example IB.4-2) or Specific Example 4-3 (Specific Example IB.4-3) The combination.

Particularly preferred among the compounds of the formula (I) defined by the formula (IB) are those in which a combination of the above-mentioned extremely preferred definitions is present, and each of the above-mentioned very particularly preferred embodiments constitutes a separate combination, in particular The combination as described in the specific embodiment 5-1 (specific embodiment IB.5-1) or the specific embodiment 5-2 (specific embodiment IB.5-2).

More specifically, X and Y represent the following (Y, X) combinations: (Me, F), (Me, H), (Me, Cl), (Me, Me), (Cl, Cl), (Cl, F), (MeO, F), (MeO, H), (Cl, H), (Br, H), (Br, F), (F, F), (CF ₃ , H), (CF ₃ , F), particularly preferably the following (Y, X) combination: (Me, F), (Me, Me), (Cl, Cl).

Particularly preferred embodiments of the compounds of formula (IB) are those wherein R ¹ and R ² represent methyl. As a result, a compound of the formula (IB-1) is produced.

In the compound of the formula (I) defined by the formula (IB-1), the group or the structural elements V ¹ , V ² , n, W, X and Y have the definitions as defined above, specifically as in the specific example 1-1 (Specific Example IB-1.1-1) or Description of Specific Example 1-2 (Specific Example IB-1.1-2).

Preferred among the compounds of the formula (I) defined by the formula (IB-1) are those in which a combination of the above preferred definitions is present, and each of the above preferred embodiments constitutes a separate combination, in particular A combination as described in the specific embodiment 2-1 (specific embodiment IB-1.2-1) or the specific embodiment 2-2 (specific embodiment IB-1.2-2).

More preferably, among the compounds of the formula (I) defined by the formula (IB-1), are compounds in which a combination of the above-defined definitions is more preferred, and each of the above-described preferred embodiments constitutes a separate combination, in particular A combination as described in the specific embodiment 3-1 (specific embodiment IB.1.3-1).

Particularly preferred among the compounds of the formula (I) defined by the formula (IB-1) are those in which a combination of the above-mentioned particularly preferred definitions is present, and each of the above-mentioned particularly preferred embodiments constitutes a separate combination, in particular Specific embodiment 4-1 (specific embodiment IB-1.4-1) or specific embodiment 4-2 (specific embodiment IB-1.4-2) or specific embodiment 4-3 (specific embodiment IB-1.4-3 ) a combination of instructions.

Particularly preferred among the compounds of the formula (I) as defined in the formula (IB-1) are those in which a combination of the above-mentioned extremely preferred definitions is present, and each of the above-mentioned very particularly preferred embodiments constitutes a separate combination. Specifically, combinations of the specific embodiments 5-1 (specific examples IB-1.5-1) or specific examples 5-2 (specific examples IB-1.5-2) are described.

More specifically, X and Y represent the following (Y, X) combinations: (Me, F), (Me, H), (Me, Cl), (Me, Me), (Cl, Cl), (Cl, F), (MeO, F), (MeO, H), (Cl, H), (Br, H), (Br, F), (F, F), (CF ₃ , H), (CF ₃ , F), particularly preferably the following (Y, X) combination: (Me, F), (Me, Me), (Cl, Cl).

The compounds of formula (I) may also be in the form of a salt, in particular an acid addition salt and a metal complex. The compounds of formula (I) and their acid addition salts and metal complexes have good potency, especially for controlling animal pests, including mitochondrial animals, and in particular insects and mites.

Suitable salts of the compounds of the general formula (I) include the conventional non-toxic salts, that is, salts formed with suitable bases and addition salts with acids. Preferred are salts formed with inorganic bases such as alkali metal salts (for example: sodium, potassium or barium salts), alkaline earth metal salts (for example: calcium or magnesium salts), ammonium salts, and organic a salt formed by a base and a salt formed with an inorganic amine (for example, triethylammonium, dicyclohexylammonium, N,N'-dibenzylmethylethylammonium, pyridinium, methylpyridinium or ethanol) a salt of ammonium), a salt formed with an inorganic acid (for example, a hydrochloride, a hydrobromide, a dihydrogen sulfate, a trihydrogen sulfate, or a phosphate), and an organic carboxylic acid or an organic sulfonic acid. a salt (for example, formate, acetate, trifluoroacetate, maleate, tartrate, methanesulfonate, besylate or p-toluenesulfonate), formed with a basic amino acid Salts (eg, arginine, aspartate or glutamate), and the like.

The compounds of formula (I) may also be in the form of stereoisomers, ie, geometric isomers and/or optical isomers or mixtures of isomers of various compositions, depending on the nature of the substituent. The present invention provides both pure stereoisomers and any desired mixtures of such isomers, but only the compounds of formula (I) are generally discussed herein.

However, it is preferred according to the invention to use optically active stereoisomers of the compounds of formula (I) and salts thereof.

The enantiomers are specifically described by the pair of compounds of formula (I) according to the invention Caused by palm sulfur atoms.

The present invention is therefore directed to both pure enantiomers and diastereomers and mixtures thereof for controlling animal pests, including arthropods and especially insects and mites. Thus, the individual configurations of the invention are related to the presence of a mixture of R enantiomers (specifically related to palm sulfur atoms) or predominantly R enantiomers, preferably wherein R to S are The ratio of the isomers is at least 60:40, and the gradual increase is better, at least 70:30, 75:25, 80:20, 85:15 and 90:10. Thus, another individual configuration of the invention relates to the presence of a mixture of the S enantiomer (specifically related to the palm sulfur atom) or predominantly the S enantiomer, preferably wherein S The ratio to the R enantiomer is at least 60:40, and is gradually improved, at least 70:30, 75:25, 80:20, 85:15 and 90:10.

The compounds of formula (I) may be in the form of different polymorphs or different polymorphs. Such pure polymorphic and polymorphic mixtures are part of the subject matter of the present invention and can be used in accordance with the present invention.

The compounds according to the invention are as generally defined by formula (I) and include all possible rotamers and mixtures thereof.

The compounds of formula (I) according to the invention may be prepared by methods well known to those skilled in the art. A variety of different preparation methods are also costly as part of the inventive subject matter, which is described below.

Preparation

The compounds of formula (I) according to the invention can be prepared by the process shown in the following reaction scheme:

Process A: The groups R ¹ , R ² , R ³ , V ¹ , V ² , W, X and Y have the above definitions. Hal represents halogen, preferably iodine or bromine.

G represents hydrogen, (C ₁ -C ₆ )-alkyl, (C ₂ -C ₆ )-alkenyl (preferably hydrogen, (C ₁ -C ₄ )-alkyl, (C ₂ -C ₄ )- Alkenyl; particularly preferably hydrogen) or B(OG) ₂ together form a 5- or 6-membered ring, preferably a 5-membered ring .

Step (a)

In a specific embodiment of the invention, the reaction of 5-halo(thio)uracil of formula (II-A) with a boronic acid compound of formula (III) or 1,3,2-dioxaborolane is produced according to A compound of the formula (I-Aa) according to the invention.

This type of reaction (the reaction of a boronic acid compound of formula (III) or a 1,3,2-dioxaborolane with a halogenated heterocyclic ring or a halogenated aromatic system) is illustrated, for example, in WO 2013/027660, JP2007/284385 or WO2007/034755.

The boronic acid compound of formula (III) or 1,3,2-dioxaborolane which is required as a starting material can be obtained from a commercial product, for example: {2-fluoro-4-methyl-5-[(2, 2,2-Trifluoroethyl)thio]phenyl}boronic acid (Aces Pharma, USA) [CAS-Accession No. 248270-00-0], or from other patent specifications, for example: from WO 2013 /157229, or it can be synthesized by methods known in the literature.

Formula (II-A) 5-halo(thio)uracil can be obtained commercially, for example, 5-iodo-1,3-dimethyluracil (Aldrich), or can be obtained by a known method, for example: similar to Synlett 2009 , (14), 2309-2311 prepared by the method described. 5-Halo-1-aminouracil is described in DE2801008 (1979).

The starting material for the preparation of (I-8) is 5-iodo-6-chloro-1,3-dimethyluracil [CAS-Accession No. 21428-30-8], which is derived from N-iodoammonium The amine is prepared by reacting with 6-chloro-1,3-dimethyluracil.

Conversion methods for the formation of the corresponding 4-sulfo- or 2,4-dithio analogs from uracil in various solvents using solvents such as: Synthesis 1987 , 256-258.

The catalyst used in the reaction of 5-halo(thio)uracil (II-A) is preferably composed of a salt or a complex of palladium, copper or nickel.

Suitable palladium catalysts are, for example, ligands (for example: 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 9,9-dimethyl-4,5-double Palladium(II) acetate, ruthenium (triphenylphosphine) palladium, bis-(three) in the presence of (diphenylphosphino)xanthene or 1,1'-bis(diphenylphosphino)ferrocene iron Phenylphosphine) palladium (II) chloride, ginseng (diphenylideneacetone) dipalladium (0).

Suitable copper salts are, for example, cuprous iodide (I), cuprous chloride (I), cuprous oxide (I), cuprous (III) triflate, copper (II) acetate, trifluoroacetate. Copper (II) methane sulfonate, often in a ligand (eg, a diamine ligand such as: N, N'-dimethylethylenediamine, N,N-dimethylethylenediamine or trans- In the presence of N,N'-dimethyl-1,2-cyclohexanediamine.

A suitable nickel catalyst is, for example, nickel(II) acetylacetonate, either alone or in combination with the above phosphorus ligand, or using nickel (II) acetylsulfonate and an imidazolium carbene ligand. .

The amount of the catalyst is usually less than the stoichiometric amount, preferably from 0.001 to 0.8 equivalents and particularly preferably from 0.01 to 0.5 equivalents based on the 5-halo(thio)uracil of the formula (II-A) used.

The reaction of the 5-halo(thio)uracil of the formula (II-A) with the boron derivative of the formula (III) is preferably carried out in a solvent selected from the conventional solvents which are inert to the main reaction conditions. Preferred are ethers such as, for example, two Alkane, tetrahydrofuran, diethyl ether or 1,2-dimethoxyethane; aromatic hydrocarbons such as, for example, benzene, toluene or xylene; aliphatic alcohols such as, for example, methanol, ethanol or isopropanol; For example: acetonitrile or propionitrile; polar aprotic solvents such as: N,N-dimethylformamide, dimethyl hydrazine, N-methylpyrrolidone and mixtures of such solvents with water.

The reaction is preferably carried out in the presence of a base. Suitable bases are inorganic bases, in particular alkali metal or alkaline earth metal acetates, phosphates, carbonates and hydrogencarbonates. Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, and potassium hydrogencarbonate. The inorganic base can also be used in an aqueous solution.

The reaction can be carried out under reduced pressure, standard pressure or under pressure, and at a temperature of from 0 to 200 ° C, preferably at a standard pressure and a temperature of from 30 to 150 ° C, optionally under an inert gas atmosphere. When the reaction is carried out, it may be carried out using any commercially available microwave device suitable for such reactions as desired (for example: Anton Paar Monowave 300, CEM Discover S, Biotage Initiator 60).

Step (b)

The compound of the formula (I-Aa) according to the invention obtained from the step (a) is reacted with an oxidizing agent to produce a hydrazine of the formula (I-Ab) according to the invention.

This reaction was carried out in a manner similar to JP2009/023910.

The oxidizing agent used is m-chloroperbenzoic acid, optionally in the presence of a buffer solution and optionally in a phase shifting catalyst (in H ₂ O ₂ , sulfuric acid containing K ₂ S ₂ O ₈ or 3-40% strength) In the presence of an onium salt in the presence of an aqueous hydrogen peroxide solution, for example, MeReO ₃ ), it may be carried out in the presence of a molecular sieve or a catalyst (for example, Na ₂ WO ₄ dihydrate or sodium periodate) as needed.

The oxidation reaction is usually carried out in a solvent selected from conventional solvents which are inert to the main reaction conditions.

Suitable solvents are halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; alcohols such as methanol or ethanol; formic acid, acetic acid or propionic acid .

The reaction can be carried out under standard pressure or pressure, and at a temperature of from -10 ° C to 80 ° C; preferably, the reaction is carried out at a standard pressure and a temperature of from 0 ° C to 40 ° C.

There are many different methods suitable for the production of enantiomerically enantiomers, as described in ARMaguire in ARKIVOC, 2011(i), 1-110: metal-catalyzed asymmetric oxidation of thioethers such as titanium and Vanadium is the most commonly used catalyst source, which is Ti(O ⁱ Pr ₄ ) and VO(acac) ₂ type, with palmitic ligands and oxidants (such as: tert-butyl hydroperoxide (TBHP), 2-Phenylpropan-2-ylhydroperoxide (CHP) or hydrogen peroxide) used together; non-metal catalyzed asymmetric oxidation, using a palmitic oxidant or a palmitic catalyst; electrochemical or biological Asymmetric oxidation reaction and kinetic analysis of hydrazine and nucleophilic migration (according to Andersen's method).

The pure enantiomer of the compound of formula (I-Ab) according to the invention can be prepared from the racemate using, for example, preparative HPLC on a palmitic stationary phase.

Process B: The groups Hal, R ¹ , R ² , R ³ , V ¹ , V ² , G, W, X and Y have the definitions as defined above.

Step (a)

In another embodiment of the invention, the halosulfide of formula (Va) is reacted with a boronic acid compound of formula (IV) or 1,3,2-dioxaborolane to yield formula (I) according to the invention. -Aa) compound. This type of reaction - the reaction of a diboronic acid compound with a halogenated heterocyclic ring or a halogenated aromatic system - has been described, for example, in WO 2012/061557.

The boronic acid compound of formula (IV) or 1,3,2-dioxaborolane which is required as a starting material can be obtained from a commercial product, for example: (1,3-dimethyl-2,4-di-oxygen) Base-1,2,3,4-tetrahydropyrimidin-5-yl)boronic acid (Combi-Blocks, USA) [CAS-Accession No. 223418-73-3], 1,3-Dimethyl-5-(4 ,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine-2,4(1H,3H)-dione (Combi-Blocks, USA) [CAS-Accession No. 269410-01-7], or (2,4-Dithio-1,2,3,4-tetrahydropyrimidin-5-yl)boronic acid (FCH-Group, Ukraine) [CAS-Login No. 125154-12-3], or known from other patent specifications, for example, from PL185090B1, or a method known in the art such as: J. Org . Chem . 1985, 50 , 841-847. synthesis.

The halogenated aromatic system of the formula (Va) which is required as a starting material can be obtained from a commodity or It is known from the multi-patent specification, for example, from WO 2013/157229, WO 2012/176856 or JP 2009/023910.

Suitable starting materials for the synthesis of the iodide of the formula (Va) are bromides of the same general formula, which can, for example, be subjected to a halogen exchange reaction, which can be converted, if desired, using a metal catalyst according to methods known in the literature, for example: analogous Chem . Lett . 1985 , 3 , 411-412.

The reaction of the boron derivative of the formula (IV) with the halosulfide of the formula (Va) is preferably carried out in the presence of a catalyst, optionally in the presence of a base, in an organic solvent or in a mixture of a solvent and water. The ambient temperature or heating is carried out to produce a compound of the formula (I-Aa) according to the invention.

The catalyst used in the reaction of the halogenated sulfide of the formula (Va) is preferably composed of a salt or a complex of palladium, copper or nickel.

Suitable palladium catalysts are, for example, ligands (for example: 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 9,9-dimethyl-4,5-double Palladium (II) acetate, ruthenium (triphenylphosphine) palladium in the presence of (diphenylphosphino)xanthene or 1,1'-bis(diphenylphosphino)ferrocene Bis(triphenylphosphine)palladium(II) chloride, ginseng (diphenylideneacetone) dipalladium (0).

Suitable copper salts are, for example, cuprous iodide (I), cuprous chloride (I), cuprous oxide (I), copper (I) triflate, copper (II) acetate, trifluoroacetate. Copper (II) methane sulfonate, often in a ligand (eg, a diamine ligand such as: N, N'-dimethylethylenediamine, N,N-dimethylethylenediamine or trans- In the presence of N,N'-dimethyl-1,2-cyclohexanediamine.

A suitable nickel catalyst is, for example, nickel(II) acetylacetonate, either alone or in combination with the above phosphorus ligand, or using nickel (II) acetylsulfonate and an imidazolium carbene ligand. .

The amount of the catalyst is usually less than the stoichiometric amount, preferably from 0.001 to 0.8 equivalents and particularly preferably from 0.01 to 0.5 equivalents based on the halogenated sulfide of the formula (Va) used.

The reaction of the halosulfide of formula (Va) with the boron derivative of formula (IV) is preferably carried out in a solvent selected from the conventional solvents which are inert to the main reaction conditions. Preferred are ethers such as, for example, two Alkane, tetrahydrofuran, diethyl ether or 1,2-dimethoxyethane; aromatic hydrocarbons such as, for example, benzene, toluene or xylene; aliphatic alcohols such as, for example, methanol, ethanol or isopropanol; For example: acetonitrile or propionitrile; polar aprotic solvents such as N,N-dimethylformamide, dimethyl hydrazine, N-methylpyrrolidone and mixtures of such solvents with water.

The reaction is preferably carried out in the presence of a base. Suitable bases are inorganic bases, in particular alkali metal or alkaline earth metal acetates, phosphates, carbonates and hydrogencarbonates. Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, and potassium hydrogencarbonate. The inorganic base can also be used in an aqueous solution.

The reaction can be carried out under reduced pressure, standard pressure or under pressure, and at a temperature of from 0 to 200 ° C, preferably at a standard pressure and a temperature of from 30 to 150 ° C, optionally under an inert gas atmosphere. When the reaction is carried out, it may be carried out using any commercially available microwave device suitable for such reactions as desired (for example: Anton Paar Monowave 300, CEM Discover S, Biotage Initiator 60).

Step (b)

The compound of the formula (I-Aa) according to the present invention, which is obtained by the process of the step B (a), is reacted with an oxidizing agent according to the description of the step A (b) of the process A to produce a hydrazine of the formula (I-Ab) according to the invention.

Process C The groups Hal, R ¹ , R ² , V ¹ , V ² , G, W, X and Y have the definitions as defined above.

Step (a)

In another embodiment of the invention, from the formula (II-B) 6-halo-1,2,4-three The reaction of -3,5(2H,4H)-dione with a boronic acid compound of formula (III) or 1,3,2-dioxaborolane gives the compound of formula (I-Ba) according to the invention.

Starting material for the preparation of (I-5), 6-bromo-2,4-dimethyl-1,2,4-tri -3,5(2H,4H)-dione [CAS-Accession No. 15870-78-7] is available from the product (Enamine, Ukraine or Ryan Scientific, USA) or as described in WO2010/006962, by 1,2 , 4-three -3,5(2H,4H)-dione is obtained by bromination followed by methylation. WO1995/001965 further describes the preparation of formula (II-B) three The method of diketone.

Boron derivative of formula (III) and 6-halo-1,2,4-tri3 of formula (II-B) -3,5(2H,4H)-dione is preferably reacted in the presence of a catalyst, optionally in the presence of a base, in an organic solvent or in a mixture of solvent and water, at ambient temperature or This is carried out under heating to give a compound of the formula (I-Ba) according to the invention.

Formula (II-B) 6-halo-1,2,4-three The catalyst used for the reaction of -3,5(2H,4H)-dione is preferably composed of a salt or a complex of palladium, copper or nickel.

Suitable palladium catalysts are, for example, ligands (for example: 2,2'-bis(diphenylphosphino)-1,1'-binaphthyl, 9,9-dimethyl-4,5-double Palladium (II) acetate, ruthenium (triphenylphosphine) palladium, bis-((diphenylphosphino)-xanthene or 1,1'-bis(diphenylphosphino) ferrocene) Triphenylphosphine) palladium (II) chloride, ginseng (diphenylideneacetone) dipalladium (0).

Suitable copper salts are, for example, cuprous iodide (I), cuprous chloride (I), cuprous oxide (I), cuprous (III) triflate, copper (II) acetate, trifluoroacetate. Copper (II) methane sulfonate, often in a ligand (eg, a diamine ligand such as: N, N'-dimethylethylenediamine, N,N-dimethylethylenediamine or trans- In the presence of N,N'-dimethyl-1,2-cyclohexanediamine.

A suitable nickel catalyst is, for example, nickel(II) acetylacetonate, either alone or in combination with the above phosphorus ligand, or using nickel (II) acetylsulfonate and an imidazolium carbene ligand. .

The amount of the catalyst is usually less than the stoichiometric amount, preferably from 0.001 to 0.8 equivalents and particularly preferably from 0.01 to 0.5 equivalents based on the azadiazepine of the formula (II-B) used.

Formula (II-B) 6-halo-1,2,4-three The reaction of the -3,5(2H,4H)-dione with the boron derivative of the formula (III) is preferably carried out in a solvent selected from the conventional solvents which are inert to the main reaction conditions. Preferred are ethers such as, for example, two Alkane, tetrahydrofuran, diethyl ether or 1,2-dimethoxyethane; aromatic hydrocarbons such as, for example, benzene, toluene or xylene; aliphatic alcohols such as, for example, methanol, ethanol or isopropanol; For example: acetonitrile or propionitrile; polar aprotic solvents such as N,N-dimethylformamide, dimethyl hydrazine, N-methylpyrrolidone and mixtures of such solvents with water.

The reaction is preferably carried out in the presence of a base. Suitable bases are inorganic bases, in particular alkali metal or alkaline earth metal acetates, phosphates, carbonates and hydrogencarbonates. Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium hydrogencarbonate, carbon Potassium hydrogenate. The inorganic base can also be used in an aqueous solution.

The reaction can be carried out under reduced pressure, standard pressure or under pressure, and at a temperature of from 0 to 200 ° C, preferably at a standard pressure and a temperature of from 30 to 150 ° C, optionally under an inert gas atmosphere. When the reaction is carried out, it may be carried out using any commercially available microwave device suitable for such reactions as desired (for example: Anton Paar Monowave 300, CEM Discover S, Biotage Initiator 60).

Step (b)

The compound of the formula (I-Ba) according to the present invention, which is obtained according to Process C, step (a), is reacted with an oxidizing agent according to the description of Process A, step (b), to produce a hydrazine of the formula (I-Bb) according to the present invention.

The groups R ¹ , R ² , G, W, X and Y have the meanings as defined above and LG represents a hydroxyl group or a leaving group such as halogen (preferably bromine, iodine), mesylate, tosylate or trifluoromethyl. Sulfonic acid.

Step (a)

Reaction of a pendant oxyphenylacetic acid derivative of the formula (VI) with a carbonic acid derivative of the formula (VII), in accordance with the process of DE 1983 0 493, FR 2 866 339 or Bioorg. Med. Chem. Lett. 2005 , 15 , 4363-4366, according to the invention A compound of formula (I-Bc).

The reaction of the pendant oxyphenylacetic acid derivative of the formula (VI) with the carbonic acid derivative of the formula (VII) may be carried out in the presence of a catalytic amount of an acid (for example, an aqueous solution of sulfuric acid or HCl), preferably at a selected one. The reaction is carried out in a solvent of a conventional solvent which is inert. Preferred are ethers such as, for example, two Alkane, tetrahydrofuran, diethyl ether or 1,2-dimethoxyethane; aromatic hydrocarbons such as, for example, benzene, toluene or xylene; aliphatic alcohols such as, for example, methanol, ethanol or isopropanol; polar aprotic Solvents such as dimethyl hydrazine or N-methylpyrrolidone or water.

The reaction can be carried out under reduced pressure, standard pressure or under pressure, and at a temperature of from 0 to 200 ° C, preferably at a standard pressure and at a temperature of from 30 to 100 ° C.

Step (b)

The compound of the formula (I-Bc) (R ² ≠H) is subsequently subjected to an alkylation reaction to give a compound of the formula (I-Bd).

The alkylation reaction is carried out according to the reaction conditions of WO2010006962, that is, from (I-Bc) and R ¹ -LG (LG = halogen, methanesulfonate, tosylate or triflate), for example: as a base In the presence of sodium hydride or potassium t-butoxide, and in DMF as a solvent, or under the conditions of Mitsunobu reaction, starting with the corresponding alcohols R ¹ —OH and triphenylphosphine, It is carried out in the presence of DEAD in THF or toluene as a solvent.

The reaction can be carried out under reduced pressure, standard pressure or under pressure, and at a temperature of from 0 to 200 ° C, preferably at a standard pressure and a temperature of from 30 to 100 ° C, optionally under an inert gas atmosphere.

Step (c)

The compound of the formula (I-Bd) according to the present invention, which is obtained according to the process of the step D (b), is reacted with an oxidizing agent according to the procedure of the step A (b) of the process A to produce a hydrazine of the formula (I-Be) according to the invention.

Process D is particularly suitable for the preparation of asymmetrically substituted three Diketone, wherein R ¹ ≠ R ² .

The groups R ¹ , R ² , G, W, X and Y have the meanings as defined above and LG represents a hydroxyl group or a leaving group such as halogen (preferably bromine, iodine), mesylate, tosylate or trifluoromethyl. Sulfonic acid.

Step (a)

Similar to the method of Bioorg. Med. Chem. Lett. 2005 , 15 , 4363-4366, by reacting a pendant oxyphenylacetic acid derivative of formula (VI) with a triazole ketone of formula (VIII) to give a formula (I according to the invention) -Bf) compound.

As described in WO8600072, the triazole ketone of formula (VIII) may be corresponding The compound R ¹ -NHNH ₂ is reacted with acetone and subsequently reacted with an alkali metal cyanate.

The reaction of the pendant oxyphenylacetic acid derivative of the formula (VI) with the triazole ketone of the formula (VIII) may be carried out in the presence of a catalytic amount of an acid (for example, sulfuric acid), preferably selected from the main reaction conditions. It is carried out in a solvent of a conventional solvent which is inert. Preferred are ethers such as, for example, two Alkane, tetrahydrofuran, diethyl ether or 1,2-dimethoxyethane; aromatic hydrocarbons such as, for example, benzene, toluene or xylene; aliphatic alcohols such as, for example, methanol, ethanol or isopropanol; For example: acetonitrile or propionitrile; a polar aprotic solvent such as dimethyl hydrazine or N-methylpyrrolidone.

The reaction can be carried out under reduced pressure, standard pressure or under pressure, and at a temperature of from 0 to 200 ° C, preferably at a standard pressure and a temperature of from 30 to 150 ° C, optionally under an inert gas atmosphere. .

Step (b)

The compound of the formula (I-Bf) according to the present invention, which is obtained according to Process E, step (a), is reacted with an oxidizing agent according to the procedure of Process A, step (b), to produce a hydrazine of the formula (I-Bg) according to the present invention.

Step (c)

The compound of the formula (I-Bf) obtained according to the process E step (a) is subjected to an alkylation reaction according to the description of the step (b) of the process D, and converted into a sulfide of the formula (I-Bh) according to the invention. .

Step (d)

The compound of the formula (I-Bh) according to the present invention, which is obtained according to Process E, step (c), is reacted with an oxidizing agent according to the procedure of Process A, step (b), to produce a hydrazine of the formula (I-Bi) according to the present invention.

Step (e)

The compound of the formula (I-Bg) according to the process of the formula E (b) is subjected to an alkylation reaction according to the description of the step (b) of the process D, and is converted into the formula (I-Bi) according to the invention. Hey.

The side oxyphenylacetic acid derivatives of formula (VI) used in Processes D and E can be prepared, for example, from aryl halide precursors by methods known in the literature, such as WO 2013/022818 Description in the middle.

Particular attention is given to the intermediates shown in the process and method of the present invention. These intermediates also form the subject of the present invention. In addition to the above intermediates, other intermediates are also described below.

The invention further provides a compound of formula (VI), Wherein G has the definitions as defined above, and W, Y and X have the same definitions as defined above, in particular as described in the specific examples 1-1 or 1-2.

Preferred compounds of formula (VI) are those in which there is a combination as defined above, and each of the above preferred embodiments constitutes a separate combination, in particular as in embodiment 2-1 or 2-2. Description.

More preferred compounds of formula (VI) are those in which there is a better definition as defined above, and each of the above preferred embodiments constitutes a separate combination, specifically as described in the specific example 3-1.

Particularly preferred compounds of the formula (VI) are those in which a combination of the above-mentioned particularly preferred definitions is present, and each of the above-mentioned particularly preferred embodiments constitutes a separate combination, specifically as in the specific example 4-1 or 4-2 or Description of 4-3.

Very particularly preferred compounds of the formula (VI) are those in which there is a very particularly preferred combination of the above, and each of the above-mentioned very particularly preferred embodiments constitutes a separate combination, in particular as in the specific examples 5-1 or 5. -2 description.

The present invention provides a compound of the formula (I-Bf), Wherein W, Y, X and R ¹ have the definitions as defined above, in particular as described in the specific examples 1-1 or 1-2.

Preferred compounds of the formula (I-Bf) are those in which there is a combination as defined above, and each of the above preferred embodiments constitutes a separate combination, in particular as in the specific example 2-1 or 2- Description of 2.

More preferred (I-Bf) compounds are those in which there is a better definition as defined above, and each of the above preferred embodiments constitutes a separate combination, specifically as described in the specific example 3-1.

Particularly preferred (I-Bf) compounds are those in which there is a combination of the above-mentioned particularly preferred definitions, and each of the above-mentioned particularly preferred embodiments constitutes a separate combination, in particular as in the specific example 4-1 or 4- Description of 2 or 4-3.

Very particularly preferred (I-Bf) compounds are combinations in which there are very particularly well defined definitions, and each of the above-mentioned very particularly preferred embodiments constitutes a separate combination, in particular as in the specific examples 5-1 Or the description of 5-2.

The invention further provides a compound of formula (I-Bg), Wherein W, Y, X and R ¹ have the definitions as defined above, in particular as described in the specific examples 1-1 or 1-2.

Preferred compounds of the formula (I-Bg) are those in which there is a combination as defined above, and each of the above preferred embodiments constitutes a separate combination, in particular as in the specific example 2-1 or 2- Description of 2.

More preferred (I-Bg) compounds are those in which there is a better definition as defined above, and each of the above preferred embodiments constitutes a separate combination, specifically as described in the specific example 3-1.

Particularly preferred (I-Bg) compounds are those in which there is a combination of the above-mentioned particularly preferred definitions, and each of the above-mentioned particularly preferred embodiments constitutes a separate combination, specifically as exemplified in Example 4-1 or 4- Description of 2 or 4-3.

Very particularly preferred (I-Bg) compounds are combinations in which there are very particularly well defined definitions, and each of the above-mentioned very particularly preferred embodiments constitutes a separate combination.

Isomer

Depending on the nature of the substituent, the compound of formula (I) may be a geometrically and/or optically active isomer or a mixture of corresponding isomers of different compositions. Such stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. Accordingly, the invention includes pure stereoisomers and any desired mixtures of such isomers.

Method and use

The invention also relates to a method of controlling an animal pest in which a compound of formula (I) acts on an animal pest and/or its habitat. The control of animal pests is preferably carried out in agriculture and forests, as well as in material protection. Preferably, the method of surgical or medical treatment of the human or animal body and the diagnostic method performed on the human or animal body are excluded.

The invention also relates to the use of a compound of formula (I) as a pesticide, especially as a crop protection agent.

In the context of the present application, the term "pesticides" in each case also always includes the term "crop protectant".

The compound of formula (I) has good plant tolerance, good toxicity to warm-blooded animals and good environmental compatibility. It is suitable for protecting plants and plant organs against biotic and abiotic stresses, increasing yield and improving harvest. Material quality, and control of animal pests, especially in the fields of agriculture, horticulture, animal husbandry, aquaculture, forests, gardens and leisure facilities, insects, spiders, worms, nematodes and mollusks, can be used to protect stock products and materials, and In the field of health. It is preferably used as a pesticide. It is effective against normal sensitive and resistant species and against all or individual stages of development. The above pests include: Arthropoda, especially arachnid (Arachnida) pests, for example: Acarus spp. ) (eg: Acarus siro), Aceria kuko, Aceria sheldoni, Aculops spp. ), Acanthope (Aculus spp. ) (for example: Aculus fockeui, Aculus schlechtendali), Amblyomma spp. ), Amphitetrany sinensis (Amphitetrany sinensis), Argas spp. ), Bovineus spp. ), Red genus (Brevipalpus spp. (eg: Brevipalpus phoenicis), Bryobia graminum, Bryobia praetiosa, Centruroides spp. ), genus (Chorioptes spp. ), Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp. ), Eotetranychus spp. ) (eg: Eotetranychus hicoriae), Epipirerus pyri, Eutetranychus spp. ) (eg Eutetranychus banksi), Eriophyes spp. ) (eg Eriophyes pyri), Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp. ) (for example: tea dust mites) (Hemitarsonemus latus) (= Polyphagotarsonemus latus), Hyologma spp. ), hard genus (Ixodes spp. ), the genus Arachnid (Latrodectus spp. ), Loxosceles spp. ), autumn scorpion (Neutrombicula autumnalis), Nuphersa genus, genus Oligonychus spp. (eg: Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp. ), the giant genus Robinia (Ornithonyssus spp. ), Red spider genus (Panonychus spp. ) (for example: Panonychus citri (= Metatetranychus citri), Panonychus ulmi (=Metatetranychus ulmi), Phyllocoptruta oleivora ), succulent leafhopper (Platytetranychus multidigituli), Polyphagotarsonemus latus, Psoroptes spp. ), Rhipicephalus spp. ), Rhizoglyphus spp. ), human genus (Sarcoptes spp. ), Scorpio maurus, Stenotarsonemus spp. ), Steneotarsonemus spinki, Tarsonemus spp. ) (for example: Tarsonemus confusus, Tarsonemus pallidus), Tetranychus spp. (eg: Tetranychus canadensis, Tetranychus cinnabarinus, Tetranychus turkestani, Tetranychus urticae), Trimculcula alfreddugesi, Vaejovis Spp. ), Vasates lycopersici; Chilopoda, for example: Geophilus spp. ), genus (Scutigera spp. ); Collembola or Collembola, for example: Onychiurus armatus; Sminthurus viridis; Diplopoda, for example: Blanciulus guttulatus; Insecta, for example: Blattodea, for example: Blatta orientalis, Blattella asahinai, Germany Blattella germanica, Leucophaea maderae, Panchlora spp. ), Pacoblatta spp. ), family genus (Periplaneta spp. (for example: Periplaneta americana, Periplaneta australasiae), Supella longipalpa, Coleoptera, for example: Acalymma vittatum, Acanthoscelides Obtectus), Adoretus spp. ), Agelastica alni, Agitoes spp. (eg: Agriotes linneatus, Agriotes mancus), Alphitobius diaperinus, Amphimallon solstitialis, Anobium punctatum, and beetle Genus (Anoplophora spp. ), cotton boll weevil (Anthonomus spp. ) (for example: Anthonomus grandis), Anthrenus spp. ), pear genus (Apion spp. ), Sugarcane genus (Apogonia spp. ), Atomaria spp. ) (eg, Atomaria linearis), Attagenus spp. ), Baris caerulescens, Bruchidius obtectus, Bruuchus spp. ) (for example: Bruchus pisorum, Bruchus rufimanus), Cassida spp. ), soybean leaf (Cerotoma trifurcate), genus (Ceuthorrhynchus spp. (eg: Ceutorrhynchus assimilis, Ceutorrhynchus quadridens, Ceutorrhynchus rapae), Chaetocnema spp. (eg: Chaetocnema confinis, Chaetocnema denticulata, Chaetocnema ectypa), Cleonus mendicus, Conoderus spp. ), bulbous genus (Cosmopolites spp. ) (eg: Cosmopolites sordidus), Costelytra zealandica, Ctenicera Spp. ), genus Curculio spp. ) (eg: Curculio caryae, Curculio caryatrypes, Curculio obtusus, Curculio sayi), Cryptolestes ferrugineus, horn chest Cryptolestes pusillus, Cryptorhynchus lapathi, Cryptorhynchus mangiferae, Cylindrocopturus spp. ), Cylindrocopturus adspersus, Cylindrocopturus furnissi, Dermestes spp. ), A. genus (Diabrotica spp. (eg: Diabrotica balteata, Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera Virgifera), Diabrotica virgifera zeae, Dichocrocis spp. ), rice iron beetle (Dicladispa armigera), Argentine genus (Diloboderus spp. ), Ladybug (Epilachna spp. ) (eg, Epilachna borealis, Epilachna varivestis), Epitrix spp. (eg: Epitrix cucumeris, Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis), Botrytis ( Faustinus spp. ), Gibbium psylloides, Gnathocerus cornutus, Hellula undalis, Heteronychus arator, Heteronyx spp. ), Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp. (eg: Hypothenemus hampei, Hypothenemus obscurus, Hypothenemus pubescens), Lachnosterna consanguinea, Lasioderma serricorne, Long Shougu (Latheticus oryzae), Lathridius spp. ), negative genus (Lema spp. ), potato beetle (Leptinotarsa decemlineata), leaf Moth (Leucoptera spp. ) (eg: Leucoptera coffeella), Lisorhoptrus oryzophilus, Lixus spp. ), Luperomorpha xanthodera, Luperodes spp. ), Lycium spp. ), American genus (Megascelis spp. ), the genus of the genus Melanotus spp. (eg: Melanotus longulus oregonensis), Meligethes aeneus, Melonontha spp. ) (eg: Melonontha melolontha), M. genus (Migdolus spp. ), the genus of the genus Monochamus spp. ), Napactus xanthographus, Necrobia spp. ), Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus spp. (eg: Otiorhynchus cribricollis, Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus), Silver-pointed tortoise (Oxycetonia jucunda), Phaedon cochleariae, Phyllophaga spp. ), Phyllophaga helleri, Phyllotreta spp. ) (eg: Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata), Popillia japonica, small Genus (Premnotrypes spp. ), Prostephanus truncatus, Psylliodes spp. ) (eg Psylliodes affinis, Psylliodes chrysocephala, Psylliodes punctulata), Ptinus spp. ), Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp. (eg: Sitophilus granarius, Sitophilus linearis, Sitophilus oryzae, Sitophilus zeamais), Sphenophorus spp. ), Stembium paniceum, Stemichus spp. ) (eg: bean stem image (Sternechus Paludatus)), scapula (Symphyletes spp. ), the genus of the genus (Tanymecus spp. (eg: Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliates), Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp . (eg: Tribolium audax, Tribolium castaneum, Tribolium confusum), Trojanderma spp. ), the genus of the genus (Tychius spp. ), Xylotrechus spp. ), the genus of the genus (Zabrus spp. ) (for example: Zabrus tenebrioides); Diptera, for example: Aedes spp. (eg: Aedes aegypti, Aedes albopictus, Aedes sticticus, Aedes vexans), Agromyza spp. ) (eg Agromyza frontella, Agromyza parvicornis), Anastrepha spp. ), Anopheles spp. (eg: Anopheles quadrimaculatus, Anopheles gambiae), Asphondylia spp. ), the fruit fly (Bactrocera spp. (eg: Bactrocera cucurbitae, Bactrocera dorsalis, Bactrocera oleae), Bibio hortulanus, Calliphora erythrocephala, Calliphora vicina , Mediterranean fruit fly (Ceratitis capitata), Chironomus spp. ) Chrysomyia spp. ), genus Chrysops spp. ), Chrysozona pluvialis, Cochliomyia spp. ), Contarinia spp. (eg: Contarinia johnsoni, Contarinia nasturtii, Contarinia pyrivora, Contarinia schulzi, Contarinia sorghicola, Contarinia) Tritici)), Cordylobia anthropophaga, Cricotopus sylvestris, Culex spp. ) (eg Culex pipiens, Culex quinquefasciatus), Culicoides spp. ), Culexeta spp. Fly Genus (Cuterebra spp. ), Drosophila (Dacus oleae), Aedes (Dasyneura spp. (eg: Dasineura brassicae), Delia spp. (eg, Delia antiqua, Delia coarctata, Delia florilega, Delia platura, Delia radicum), Dermatobia hominis, Drosophila spp. ) (eg Drosphila melanogaster, Drosphila suzukii), Echinocnemus spp. ), genus Flyfly (Fannia spp. ), the genus of the genus Gastrophilus spp. ), Glossina spp. ), genus Haematopota spp. ), genus Hydrellia spp. ), Rice leaf fly (Hydrellia griseola), Hydrangea (Hylemyia spp. ), the genus Hypobesca spp. ), the genus Hypoderma spp. ), Liriomyza spp. (eg: Liriomyza brassicae, Liriomyza huidobrensis, Liriomyza sativae), Lucilia spp. ) (eg Lucilia cuprina), Lutzomyia spp. ), the genus Mosquito (Mansonia spp. ), Musca spp. ) (eg Musca domestica, Musca domestica vicina), Oestro spp. ), Swedish fly (Oscinella frit), Chironus (Paratanytarsus spp. ), Chiarozoa (Paralauterborniella subcincta), Lepidoptera (Pegomya spp. (eg Pegomya betae, Pegomya hyoscyami, Pegomya rubivora), Phlebotomus spp. ), the genus Hypora (Phorbia spp. ), the genus Phormia spp. ), Piophila casei, Prodiplosis spp. ), Psila rosae, Rhagoletis spp. (eg, Rhagoletis cingulata, Rhagoletis completa, Rhagoletis fausta, Rhagoletis indifferens, Rhodoletis indifferens, Rhagoletis mendax ), Rhagoletis pomonella, Sarcophaga spp. ), genus (Simulium spp. ) (for example: Simulium meridionale), Stomoxys spp. ), genus (Tabanus spp. Straight (Tetanops spp. ), the genus of the genus (Tipula spp. (eg: Tipula paludosa, Tipula simplex); Hemiptera, such as: Acizzia acaciaebaileyanae, Acizzia dodonaeae, hibiscus ( Acizzia uncatoides), Acrida turrita, Acyrthosipon spp. ) (eg: Acyrthosiphon pisum), Acrogonia spp. ), Aeneolamia genus, Aragonoscena spp. ), Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus floccosus, Durian durian (Allocaridara malayensis), and genus Amrasca spp. (eg: Amrasca bigutulla, Amrasca devastans), Anuraphis cardui, Aonidiella spp. (eg: Aonidiella aurantii, Aonidiella citrina, Aonidiella inornata), Aphanostigma piri, Aphis (Aphis) Spp. (eg: Aphis citricola, Aphis craccivora, Aphis fabae, Aphis forbesi, Aphis glycines, Aphis gossypii, often Aphis hederae, Aphis illinoisensis, Aphis middletoni, Aphis nasturtii, Aphis nerii, Aphis pomi, Spiraea (Aphis) Spiraecola), Aphis viburniphila, Arboridia apicalis, Arytainilla spp. ), Aspidiella spp. ), the round shield genus (Aspidiotus spp. (eg: Aspidiotus nerii), Atanus genus, Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, light tube Brachycaudus helichrysi, Brachycolus spp. ), Brasserie (Brevicoryne brassicae), Liriodendron (Cacopsylla spp. ) (eg: pear yellow hibiscus) (Cacopsylla pyricola)), Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp. ), Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chondracris rosea, Chromaphis juglandicola, Chrysomphalus Ficus), Cicadulina mbila, Coccomytilus halli, Coccus spp. (eg: Coccus hesperidum, Coccus longulus, Coccus pseudomagnoliarum, Coccus viridis), Cryptomyzus ribis, Cryptoneossa Genus, Compressed genus (Ctenarytaina spp. ), Dalbulus spp. ), Dialeurodes citri, Diaphorina citri, Diaspis spp. ), Drosicha spp. ), Stem Aphid (Dysaphis spp. ) (for example: Dysaphis apiifolia, Dysaphis plantaginea, Dysaphis tulipae), Dysmicoccus spp. ), small green leaf genus (Empoasca spp. (eg: Empoasca abrupta, Emppoasca fabae, Emppoasca maligna, Emppoasca solana, Emppoasca stevensi) Genus (Eriosoma spp. (eg: Eriosoma americanum, Eriosoma lanigerum, Eriosoma pyricola), Erythroneura spp. ), Lemon Eucalyptus (Eucalyptolyma spp. ), brown wood (Euphyllura spp. ), Euscelis bilobatus, Ferrisia spp. ), coffee powder (Geococcus coffeae), hibiscus (Glycaspis spp. ), Heteropsylla cubana, Heteropsylla spinulosa, Homalodisca coagulata, Hyalopterus arundinis, Hyalopterus pruni, blown cotton Genus (Icerya spp. ) (eg, Icerya purchasi), Idiocerus spp. ), green leaves Genus (Idioscopus spp. ), Laodelphax striatellus, Lecanium spp. ) (eg Lecanium corni (Parthenolecanium corni), Lepidosaphes spp. ) (eg: Lepidosaphes ulmi), Lipaphis erysimi, Lycorma delicatula, Macrosiphum spp. (eg: Macrosiphum euphorbiae, Macrosiphum lilii, Macrosiphum rosae), Macrosteles facifrons, Mahanarva spp. ), Melanaphis sacchari, Metcalfiella, Metcalfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, peach aphid Genus (Myzus spp. (eg: Myzus ascalonicus, Myzus cerasi, Myzus ligustri, Myzus ornatus, Myzus persicae, Tobacco) Zu (Myzus nicotianae)), lettuce 蚜 (Nasonovia ribisnigri), genus Nephotettix spp. (eg: Nephotettix cincticeps, Nephotettix nigropictus), Nilaparvata lugens, Oncometopia, Orthezia praelonga, Oxya chinensis ), Pachypsylla spp. ), Parabemisia myricae, Paratrioza spp. ) (eg: Paratrioza cockerelli), Parlatoria spp. ), 瘿 蚜 (Pemphigus spp. (eg: Pemphigus bursarius, Pemphigus populivenae), Peregrinus maidis, Phenacoccus spp. (eg: Phenacoccus madeirensis), Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp. (eg: Phylloxera devastatrix, Phylloxera notabilis), Pinnaspis aspidistrae, Planococcus spp. ) (for example: Planococcus citri), Prosopidopsylla flava, pear-shaped cotton aphid (Protopulvinaria pyriformis), Pseudaulacaspis pentagona, Pseudococcus spp. (eg, Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni), Psyllopsis , hibiscus (Psylla spp. ) (for example: Psylla buxi, Psylla mali, Psylla pyri), Pteromalus spp. ), spider genus (Pyrilla spp. ), Round genus (Quadraspidiotus spp. (for example: Quadraspidiotus juglansregiae, Quadraspidiotus ostreaeformis, Quadraspidiotus perniciosus), Quesada gigas, Rastrococcus spp. ), Rhopalosiphum spp. (eg: Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominale), Saissetia spp. (eg: Saissetia coffeae, Saissetia miranda, Saissetia neglecta, Saissetia oleae), Scaphoides titanus, Schizaphis graminum, Shield 蚧Selenaspidus articulatus), Sitobion avenae, and Sagata spp. ), Sogatella furcifera, Sogatodes spp. ), Stictocephala festina, Siphoninus phillyreae, Tenalaphara malayensis, Tetragonocephela, Tinocallis caryaefoliae, Tomaspis spp. ), the genus of the genus (Toxoptera spp. ) (eg: Toxoptera aurantii, Toxoptera citricidus), greenhouse whitefly (Trialeurodes vaporariorm), hibiscus (Trioza spp. ) (eg Trioza diospyri), Typhlocyba spp. ), Shield genus (Unaspis spp. ), Vineus vitifolii, Zygina spp. ); Heteroptera, for example: Anasa tristis, Mantis genus Antestiopsis Spp. ), Red genus (Boisea spp. ), genus Blissus spp. ), genus Clolocoris spp. ), Campylomma livida, two-tailed genus (Cavelerius spp. ), bedbug (Cimex spp. (eg: Cimex adjunctus, Cimex hemipterus, Cimex lectularius, Cimex pilosellus), Collaria spp. ), Creontiades dilutus, Dasynus piperis, Dielops furcatus, Diconocoris hewetti, Dysdercus spp. ), skunk genus (Euschistus spp. (eg: Euschistus heros, Euschistus servus, Euschistus tristigmus, Euschistus variolarius), Eurygaster spp. ), Halyomorpha halys, Heliopeltis spp. ), Horbians nobilellus, Leptocorisa spp. ), Leptocorisa varicornis, Leptoglossus occidentalis, Leptoglossus phyllopus, Lygocoris spp. ) (for example: Lygocoris pabulinus), Lygus spp. (eg: Lygus elisus, Lygus hesperus, Lygus lineolaris), Macropes excavatus, Monalonion atratum, Green genus (Nezara spp. ) (eg: Nezara viridula), Oebalus spp. ), the proposed pest (Piesma quadrata), the genus (Pezodorus spp. ) (for example: Piezodorus guildinii), Psallus spp. ), Pearudacysta persea, Rhodonius spp. ), Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp. ), Stephanitis nashi, and Tibraca spp. ), Tricusoma spp. ); Hymenoptera, for example: Acromyrmex spp. ), Athalia spp. ) (for example: Athalia rosae), Atta spp. ), Dipterus spp. ) (eg: Diprion similis), Hormone (Hoplocampa) Spp. ) (eg: Hoplocampa cookei, Hoplocampa testudinea), genus (Lasius spp. ), Argentine ants (Linepithema humile), kitchen ants (Monomorium pharaonis), tree genus (Sirex spp. ), invasive red fire ant (Solenopsis invicta), acid odorant genus ((Tapinoma spp. ), tree bee (Urocerus spp. ), Vespa (Vespa spp. ) (for example: Vespa crabro), Xeris spp. Isopoda, for example: Armadillidium vulgare, Oniscus asellus, Porcellio scaber; Isoptera, for example: Coptotermes spp. ) (for example: Coptotermes formosanus), termites (Cornitermes cumulans), and genus Quyptotermes spp. ), Termite genus (Incisitermes spp. ), sugar termites (Microtermes obesi), termite genus (Odontotermes spp. ), termite genus (Reticulitermes spp. (for example: Reticulitermes flavipes, Reticulitermes hesperus); Lepidoptera, for example: Achroia grisella, Acronicta major, leaf curl Moth (Adoxophyes spp. ) (eg: Adoxophyes orana), Aedia leucomelas, Agrotis spp. ) (eg Agrotis segetum, Agrotis ipsilon), Alabama spp. (eg: Alabama argillacea), Amyelois transitella, Anarsia spp. ), the genus Noctuidae (Anticarsia spp. ) (eg: Anticarsia gemmatalis), Astragalus spp. ), Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp. ), Cacoecia spp. ), Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Genus (Chilo spp. ) (eg Chilo plejadellus, Chilo suppressalis), Choristoneura spp. ), Clysia ambiguella, Cnaphalocerus spp. ), Cnaphalocrocis medinalis, Cnephasia spp. ), Conopomorpha spp. ), Black genus (Conotrachelus spp. ), Noctuidae (Copitarsia spp. ), Cydia spp. (eg: Cydia nigricana, Cydia pomonella), Dalaca noctuides, Diaphania spp. ), the small cane toad (Diatraea saccharalis), the Egyptian diamond genus (Earias spp. ), Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia spp. (eg: Ephestia elutella, Ephestia kuehniella), Epinotia spp. ), Apple moth (Epiphyas postvittana), Ethella spp. ), Elia spp. ), Eupoecilia ambiguella, Euproctis spp. ) (for example: Euproctis chrysorrhoea), cut genus (Euxoa spp. ), Heliothis sp. (Feltia spp. ), Galleria mellonella, Gracilla aria spp. ), the small heartworm (Grapholitha spp. ) (eg, Grapholita molesta, Grapholita prunivora), Hedylepta spp. ), Noctuidae (Helicoverpa spp. ) (eg: Helicoverpa armigera, Helicoverpa zea), Heliothis spp. ) (eg: Heliothis virescens), Hofmannophila pseudospretella, Homoeosoma spp. ), Homona spp. ), Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp. ), Leucinodes orbonalis, Leucoptera spp. ) (eg: Leucoptera coffeella), Lithocolletis spp. ) (for example: Lithocolletis blancardella, Lithophena antennata), Moth (Lobesia spp. ) (for example: Lobesia botrana), Loxaltis albicosta, Lymantria spp. ) (eg Lymantria dispar), Lyonetia spp. (eg, Lyonetia clerkella), Malacosoma neustria, Maruca testulalis, Mamstra brassicae, Melanitis leda, Mocis spp . ), Monopis obviella, Mythimna separate, Nemapogon cloacellus, Nymphula spp. ), genus Oiketicus spp. ), Noctuidae (Oria spp. ), Orthaga spp. ), corn genus (Ostrinia spp. (eg: Ostrinia nubilalis), Oulema melanopus, Oulema oryzae, Panolis flammea, Parnara spp. ), red bollworm (Pectinophora spp. ) (eg, Pectinophora gossypiella), Perileucoptera spp. ), genus Phthorimaea spp. ) (eg: Phthorimaea operculella), Phylcrostis citrella, Phyllonycter spp. (eg: Phyllonycter blancardella, Phyllonycter crataegella), Pieris spp. ) (eg, Pieris rapae), Platynota stultana, Plodia interpunctella, Plusia spp. ), Plutella xylostella (=Plutella maculipennis), P. rapae (Prays spp. ), the genus Mycobacterium (Prodenia spp. ), the genus Moth (Protoparce spp. ), genus Pseudaletia spp. (eg Pseudaletia unipuncta), Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp. ) (for example: Schoenobius bipunctifer), Scirpophaga spp. ) (eg: Scirpophaga innotata), Scotia segetum, Sesamia spp. ) (eg: Sesamia inferens), Sparganothis spp. ), Spodoptera spp. (eg, Spodoptera eradiana, Spodoptera exigua, Spodoptera frugiperda, Spodoptera praefica), Stathmopoda spp. ), Stomopteryx subsecivella, Synanthedon spp. ), Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Liriodendron (Tortrix spp. ), Trichophaga tapetzella, Trichoplusia spp. ) (eg Trichoplusia ni), Tryporyza incertulas, Tuta absoluta, Virachola spp. ); Orthoptera or Saltatoria, for example: Acheta domesticus, Dichroplus spp. ), genus (Gryllotalpa spp. ) (eg: Gryllotalpa gryllotalpa), cane genus (Hieroglyphus spp. ), genus Locusta spp. ) (eg: Locusta migratoria), Melanoplus spp. (eg, Melanoplus devastator), Paratlanticus ussuriensis, Schistocerca gregaria, Phthiraptera, for example, Damalinia spp. ), genus Haematopinus spp. ), canine genus (Linognathus spp. ), human genus (Pediculus spp. ), Phylloera vastatrix, Pthirus pubis, Trichodectes spp. ); Psocoptera, for example: Lepinatus spp. ), the book genus (Liposcelis spp. ); Siphonaptera, for example: Ceratophyllus spp. ), Ctenocephalides spp. (eg: Ctenocephalides canis, Ctenocephalides felis), Pulex irritans, Tunga penetrans, Xenopsylla cheopis; Thysanoptera, for example: Anaphothrips obscurus, Baliothrips biformis, Drepanothris reuteri, Enneothrips fIavens, Frankliniella Spp. (eg: Frankliniella fusca, Frankliniella occidentalis, Frankliniella schultzei, Frankliniella tritici, Frankliniella vaccinii ), Frankliniella williamsi, and Heliothrips spp. ), Green Chestnut Horse (Hercinothrips femoralis), Rhipiphorothrips cruentatus, Hard Horse (Scirtothrips spp. ), eni马 (Taeniothrips cardamoni), 蓟 genus (Thrips spp. (eg: Thrips palmi, Thrips tabaci); Zygentoma (=Thysanura), for example: Ctenolepisma spp. ), Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; Symphyla, for example: Scutigerella spp. ), for example: Scutigerella immaculata; Mollusca, a pest of the specific bivalve (Bivalva), for example: Dreissena spp. And Gastropoda, for example: Arion spp. ) (for example: Arion ater rufus), Biomphalaria spp. ), genus Bulinus spp. ), genus genus (Deroceras spp. ) (eg: Deroceras leave), Galba spp. ), Lymnaea spp. ), Oncomelania spp. ), Pomacea spp. ), Amber snail (Succinea spp. ); animal and human parasites from the genus Platyhelminthes and Nematoda, for example: Aelurostrongylus spp. ), Nematodes (Amidostomum) Spp. ), Hookworm (Ancylostoma spp. ), live the nematode (Angiostrongylus spp. ), Sea genus Nematode (Anisakis spp. ), Anopheles genus (Anoplocephala spp. ), Ascaris spp. ), Avian genus (Ascaridia spp. ), Bailey's genus (Baylisascaris spp. ), Brugia spp. ), Anthurium genus (Bunostomum spp. ), Capillaria spp. ), Nematode (Chabertia spp. ), Clostridium spp. ), Cooperaria spp. ), C. elegans (Crenosoma spp. ), the genus Arthropod (Cyathostoma spp. ), Dicrocoelium spp. ), Dictyocaulus spp. ), Diphyllobothrium spp. ), genus Aphid (Dipylidium spp. ), Dirofilaria spp. ), Dracunculus spp. ), Echinococcus spp. ), Echinostoma spp. ), Aphid (Enterobius spp. ), Eucalyptus nematode (Eucoleus spp. ), genus genus (Faciola spp. ), Fascioloides spp. ), Ginger (Fasciolopsis spp. ), genus Nematode (Filaroides spp. ), genus Nematode (Gongylonema spp. ), the third generation of genus (Gyrodactylus spp. ), the genus Nematode (Habronema spp. ), Haemonchus spp. ), Heliconia genus (Heligmosomoides spp. ), Heterarias spp. ), membrane shell aphid (Hymenolepis spp. ), H. elegans (Hyostrongylus spp. ), Litoosoides spp. ), Loa spp. ), the genus Metastrongylus spp. ), the genus Paragonimus (Metorchis spp. ), the genus of the genus Aphis (Mesocestoides spp. ), Monizia spp. ), Muellerius spp. ), hookworm (Necator spp. ), Nematodirus spp. ), N. elegans (Nippostrongylus spp. ), Nematodes (Oesophagostomum spp. ), Anelidae (Ollulanus spp. ), Onchocerca spp. ), genus genus Opis genus (Opisthorchis spp. ), Oslerus spp. ), stomach genus (Ostertagia spp. ), Oxynris spp. ), Capreolus spp. ), Parafilaria spp. ), Paragonimus spp. Bismuth (Paramphistomum spp. ), Paranoplocephala spp. ), Parascaris spp. ), genus Nematode (Passalurus spp. ), Protostrongylus spp. ), Schistosoma spp. ), Filamentous genus (Setaria spp. ), Trichomonas (Spirocerca spp. ), Crown genus (Stephanofilaria spp. ), Coronaria genus (Stephanurus spp. ), the genus Strionics (Strongyloides spp. ), Round genus (Strongylus spp. ), genus Heteropharus (Syngamus spp. ), with aphids (Taenia spp. ), the genus Boletus (Teladorsagia spp. ), sucking nematode (Thelazia spp. ), Toxascaris spp. ), Toxoca serrata (Toxocara spp. ), Trichinella spp. ), Trichobilharzia spp. ), Trichostrongylus spp. ), whipworm (Trichuris spp. ), Uncinaria spp. ), Wucer nematode (Wuchereria spp. ); a plant pest from the Nematoda, also known as a plant-parasitic nematode, in particular: Agenchus spp. ) (eg: Aglenchus agricola), Anguina spp. ) (eg: Anguina tritici), Aphelenchoides spp. (eg: Aphelenchoides arachidis, Aphelenchoides fragariae), Nematodes (Belonolaimus spp. (eg: Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni), Bursaphelenchus spp. (eg: Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus), Cacopaurus spp. ) (eg: Cacopaurus pestis), Criconemella spp. ) (eg: Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax (= ring rot) Nematode (Mesocriconema xenoplax), Nematode (Criconemoides spp. ) (eg, Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum), Ditylenchus spp. ) (eg Ditylenchus dipsaci), Conlichworm (Dolichodorus spp. ), cystic nematode (Globodera spp. (eg, Globodera pallida, Globodera rostochiensis), Helicopterus spp. ) (eg: Heliconicones dihystera), Hemicriconemoides spp. ), Nematode (Hemicycliophora spp. ), Heterodera spp. (eg: Heterodera avenae, Heterodera glycines, Heterodera schachtii), Hoplolaimus spp. ), Longidarus spp. ) (eg: Longidorus africanus), Meloidogyne spp. (eg: Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita), Melolinema spp. ), pseudo-root nodule nematode (Nacobbus spp. ), Nematolinus spp. ), Paraphelenchus spp. ), Trichoderma genus (Paratrichodorus spp. ) (eg, Paratrichodorus minor), Pratylenchus spp. (eg puncdy nematode (Pratylenchus penetrans)), Pseudohalenchus spp. ), smoothing edge nematode (Psilenchus spp. ), cystic genus (Punctodera spp. ), Groats (Quinisulcius spp. ), perforated nematode (Radopholus spp. ) (eg Radopholus citrophilus, Radopholus similis), Rotylenchulus spp. ), the genus Nematode (Rotylenchus spp. ), Spirulina spp. ), the genus Trianguina spp. ), Trichoderma genus (Trichodorus spp. ) (eg Trichodorus obtusus, primitive burr nematode (Trichodorus) Primitivus)), dwarf nematode (Tylenchorhynchus spp. ) (for example: Tylenchorhynchus annulatus), Tylenchulus spp. ) (eg, Tylenchulus semipenetrans), Xiphinema spp. (for example: the standard Xiphinema index); in addition, it can also control the Protozoa, Coccidia, for example: Eimeria spp. ).

Nematode

As used herein, the term "nematode" includes all species of Nematoda and, in particular, plants or fungi (eg, from Aphelenchida, Meloidogyne, Tylenchida). And other species) or humans and animals (eg, species from Trichinellida, Tylenchida, Rhabditina, and Spirurida) or Parasitic species that cause damage in or on organisms, and other parasitic worms.

The nematicides used to protect crops described herein can control nematodes.

The term "controlling nematodes" refers to killing or preventing or hindering the development or growth of nematodes, or preventing or hindering their penetration into plant tissue or the consumption of plant tissues.

In this case, the potency of the compound is determined between the plants treated with the compound of formula (I), the part of the plant or the treated soil and the untreated plant or part of the plant or the untreated soil (100%). Compare the mortality of nematodes, the formation of worms, the formation of cysts, the nematode density per unit volume of soil, the nematode density per root, the number of nematode eggs per unit volume of soil, and the nematode infection rate. At this time, compared with the untreated plants, part of the plants or the untreated soil, it is better to achieve a reduction of 25-50%, more preferably a reduction of 51-79% and the best system completely kills or completely prevents the development of nematodes. And growth, up to 80 to 100%. The nematode control described herein also includes control of nematode reproduction (eg, development of cysts and/or eggs). The compound of formula (I) can also be used To maintain the health of plants or animals, and it can be used for curative, prophylactic or systemic control of nematodes.

Those skilled in the art are familiar with determining nematode mortality, worm formation, cyst formation, nematode density per unit volume of soil, nematode density per root, number of nematode eggs per unit volume of soil, nematode activity. method.

The use of the compound of formula (I) maintains plant health and also reduces plant damage caused by nematodes and increases yield.

As used herein, the term "plant nematode" refers to a plant nematode that includes all nematodes that can harm plants. Plant nematodes include plant-parasitic nematodes and soil-derived nematodes. Plant-parasitic nematodes include, but are not limited to, ectoparasites such as: Xiphinema spp., Longidorus spp., and Trichodorus spp.; semi-parasitic, such as : Tylenchulus spp.; migratory endoparasites, such as: Pratylinchus spp., Radoclus spp., and Scutellonerna spp.; non-walking Parasites such as Heterodera spp., Globoderal spp. and Meloidogyne spp., and endoparasites of stems and leaves, such as Ditylenchus Spp.), Aphelenchoides spp. and Hirshmaniella spp. Parasitic soil nematodes that particularly damage the roots are, for example, the cystic forming nematodes of Heterodera or Globodera, and/or the nodule nematodes of the genus Meloidogyne. Nociceptive species of these genus are, for example, Meloidogyne incognita, Heterodera glycines (soybean cyst nematode), Globodera pallida, and Globodera rostochiensis (Globodera rostochiensis) Yellow potato cyst nematode), the compounds described herein are effective in controlling these species. However, the use of the compounds described herein is by no means limited to such genus or species, but may be applied to other nematodes in the same manner.

Plant nematodes include (but are not limited to): for example: C. elegans (Aglenchus agricola), Anguina tritici, Aphelenchoides arachidis, Aphelenchoides fragaria, and stem and leaf internal parasites of the genus Aphelenchoides spp. Belonolaimus gracilis, Belonolaimus longicaudatus, Belonolaimus nortoni, Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus ) and Bursaphelenchus spp.; Cacopaurus pestis, Criconemella curvata, Criconemella onoensis, Criconemella ornata, ring Nematodes (Criconemella rusium), Criconemella xenoplax (=Mesocriconema xenoplax) and Criconemella spp., Criconemoides ferniae, Cryptocaryon elegans Criconemoides onoense), Criconemoides ornatum and C. elegans (Cri Conemoides spp.); Stem and leaf endoparasites of Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus, and Ditylenchus spp.; Dolichodorus heterocephalus), Globodera pallida (=Heterodera pallida), Globodera rostochiensis (yellow potato cyst nematode), Globodera solanacearum, tobacco golden nematode ( Globodera tabacum), non-walking cystic parasite of the genus Globodera virginia and Globodera spp.; Helicopterus digonicus, Helicotylenchis dihystera ), Helicotylchus erythrine, Helicoterlenchus multicinctus, Helicotyllenchus nannus, Helicotylenchus pseudorobustus, and Helicoverpa armigera (Helicotylenchus spp.); Hemicriconemoides, Hemicycliophora arenaria, Hemicycliophora nudata, Hemicycliophora parvana, Heterodera avenae, cross Heterodera cruciferae, Heterodera glycines (soybean cyst nematode), Heterodera oryzae, Heterodera schachtii, Heterodera zeae And non-walking cystic parasites of the genus Heterodera spp.; Hirschmaniella gracilis, Hirschmaniella oryzae, Hirschmaniella spinicaudata and Stem and leaf endoparasites of the genus Hirschmaniella spp.; Hoplolaimus aegyptii, Hoplolaimus californicus, Hoplolaimus columbus, Hoplolaimus galeatus , Hoplolaimus indicus, large needle nematode (Hoplolaimus magnistylu) s), Hoplolaimus pararobustus, Longidorus africanus, Longidorus breviannulatus, Longidorus elongatus, Longidorus laevicapitatus, long An ectoparasite of Longidorus vineacola and Longidorus spp.; Meloidogyne acronea, Meloidogyne africana, Meloidogyne arenaria, Peanut nodule nematode soup Meloidogyne arenaria thamesi, Meloidogyne artiella, Meloidogyne chitwoodi, Meloidogyne coffeicola, Meloidogyne ethiopica, Meloidogyne exigua ), Meloidogyne fallax, Meloidogyne graminicola, Meloidogyne graminis, Meloidogyne hapla, Meloidogyne incognita, South Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne kikuyensis, Meloidogyne minor, Meloidogyne naasi, coffee root nodule Non-walking parasites of the genus Meloidogyne paranaensis, Meloidogyne thamesi and Meloidogyne spp.; Meloinema spp., Nacobbus aberrans, Stem nematode ( Neotylenchus vigissi), Paraphelenchus pseudoparietinus, Paratrichodorus allius, Paratrichodorus lobatus, Paratrichodorus minor, Paratrichodorus nanus, perforated Paratrichodorus porosus, Paratrichodorus teres and Paratrichodorus spp.; Paratylenchus hamatus, Paratylenchus minutus, Paratylenchus projectus ) and the genus Nematode ( Paratylenchus spp.); short-winged nematodes (Pratylenchus agilis), A. striata (Pratylenchus alleni), Andean short-lived nematodes (Pratylenchus and inus), short-tailed short-stem nematodes (Pratylenchus brachyurus), wheat short-stem nematodes ( Pratylenchus cerealis), Platylenchus coffeae, Pratylenchus crenatus, Pratylenchus delattrei, Pratylenchus giibbicaudatus, and C. elegans Pratylenchus goodeyi), Pratylenchus hamatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus penetrans ), Platyllenchus pratensis, Pratylenchus scribneri, Pratylenchus teres, Pratylenchus thornei, Tradylenchus vulnus ), short-tailed nematode (Pratylenchus zeae) and short-body nematode (Pratylenchus spp.) migratory internal parasite; Pseudohalenchus minutus, Psilenchus magnidens, Psilenchus tumidus, Punctodera chalcoensis , the genus Quinisulcius acutus, Radopholus citrophilus, Radopholus similis, the vaginal parasite of the genus Radopholus spp., Rotylenchulus borealis, Rotylenchulus parvus, Rotylenchulus reniformis, and Rotylenchulus spp.; Rotylenchus laurentinus, Rotylenchus macrodoratus, T. elegans (Rotylenchus robustus), Rotylenchus uniformis and Rotylenchus spp.; Scutellonema brachyurum, Scutellonema bradys, Scutellonema clathricaudatum and spiral Nematode (Scutellonema spp.) Migratory parasites; Subanguina radiciola, Tetylenchus nicotianae, Trichodorus cylindricus, Trichodorus minor, Trichodorus primitivus, C. serrata (Trichodorus proximus), similar ectoparasites of Trichodorus similis, Trichodorus sparsus and Trichodorus spp.; Tylenchorhynchus agri, Tylenchorhynchus brassicae ), Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, and the largest dwarf nematode (Tylenchorhynchus maximus) ), Tylenchorhynchus nudus, Tylenchorhynchus vulgaris, and Tylenchorhynchus spp.; Tylenchulus semipenetrans and half A semi-parasitic genus of the genus Tylenchulus spp.; Xiphinema americanum, Xiphinema brevicolle, Xiphinema dimorphicaudatum, Xiphinema index, and An ectoparasite of the genus Xiphinema spp.

Nematodes that can be controlled using compounds of formula (I) include: Meloidogyne elegans such as Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla, and Peanut root nematode ( Meloidogyne arenaria); Ditylenchus nematodes, such as: Ditylenchus destructor and stem and bulb nematodes (Ditylenchus dipsaci); genus of the genus Pratylenchus, such as: cob root rot Nematodes (Pratylenchus penetrans), Chrysanthemum root rot (Pratylenchus fallax), Coffee root nematode (Pratylenchus coffeae), Tea tree root nematode (Luss nematode) (Pratylenchus loosi)) and Walnut root rot nematode (Pratylenchus vulnus); gold cystic nematode (Globodera) nematodes, such as: yellow potato cyst nematode (Globodera rostochiensis) and white Potato cyst nematode (Globodera pallida); Nematodes of Heterodera, such as: large Nematodes (Heterodera glycines) and beet cyst nematodes (Heterodera schachtii); Aphelenchoides nematodes, such as the rice white-spotted nematode (Aphelenchoides besseyi)), Chrysanthemum nematode (Aphelenchoides ritzemabosi) and strawberry nematode (Aphelenchoides fragariae); Aphelenchus nematodes, such as: fungal nematodes (oats) Aphelenchus avenae; a nematode of the genus Radopholus, such as a perforated nematode (Radopholus similis); a nematode of the genus Tylenchulus, such as a citrus root nematode (citrus half puncture) Nematode (Tylenchulus Semipenetrans)); Rotylenchulus elegans, such as: nematode (Rotylenchulus reniformis); wood nematode, such as: Bursaphelenchus xylophilus and coconut red ring rot nematode ( Bursaphelenchus cocophilus), etc.

Plants which can be protected with a compound of formula (I) include plants such as cereals (eg, rice, barley, wheat, rye, oats, corn, etc.), beans (soybeans, red beans, beans, broad beans, peas, peanuts). , etc.), fruit trees/fruits (apples, citrus varieties, pears, grapes, peaches, Japanese apricots, cherries, walnuts, almonds, bananas, strawberries, etc.), vegetable varieties (cabbage, tomato, spinach, broccoli) , lettuce, onions, shallots, green peppers, etc.), root crops (carrots, potatoes, sweet potatoes, radishes, lotus roots, kohlrabi, etc.), industrial raw materials (cotton, hemp, mulberry, tri-tree, rapeseed, Beets, hops, sugar cane, sugar beets, olives, rubber, palm trees, coffee, tobacco, tea, etc.), melons (pumpkins, cucumbers, watermelons, melons, etc.), grassland plants (Dactyls, sorghum, Timothy, clover, valerian, etc.), turf (Taipei grass, Kangsui grass, etc.), spice plants, etc. (lavender, rosemary, thyme, balinese, pepper, ginger, etc.) And flowers (chrysanthemums, roses, Orchid, etc.).

The compounds of formula (I) are particularly suitable for controlling coffee worms, in particular: Pratylenchus brachyurus, Pratylenchus coffeae, Meloidogyne exigua, Meloidogyne incognita, Meloidogyne coffeicola, Helicotylenchus spp. and Meloidogyne paranaensis, Rotylenchus spp., Xiphinema spp., Dylenchorhynchus Spp.) and Scutellonema spp.

The compounds of formula (I) are particularly suitable for controlling potato nematodes, in particular: Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus scribneri, short-stem nematodes (Pratylenchus Penetrans), coffee larvae (Pratylenchus coffeae), stem worm (Ditylenchus dipsaci) and A. striata (Pratylenchus alleni), Andean short-stem nematode (Pratylenchus and inus), wheat short-stem nematode (Pratylenchus cerealis), nick Platylenchus crenatus, Pratylenchus hexincisus, Pratylenchus loosi, Pratylenchus neglectus, Pratylenchus teres, Soxhlet short body Nematodes (Pratylenchus thornei), Tratylenchus vulnus, Belonolaimus longicaudatus, Trichodorus cylindricus, Trichodorus primitivus, Trichodorus proximus, Similar to Trichodorus similis, Trichodorus sparsus, Paratrichodorus minor, Paratrichodorus allius, Paratrichodorus nanus, Barley smoothing burr (Paratrichodorus) Teres), peanut root nodule nematode (Meloi Dogyne arenaria), Meloidogyne fallax, Meloidogyne hapla, Meloidogyne thamesi, Meloidogyne incognita, Meloidogyne chitwoodi, Nematode nocturnal nematode (Meloidogyne javanica), Nacobbus aberrans, Globodera rostochiensis, Globodera pallida, Ditylenchus destructor, Radopholus similis, Renal nematode (Rotylenchulus reniformis), Neotylenchus vigissi, Paraphelenchus pseudoparietinus, Aphelenchoides fragariae and Melolinema spp.

The compounds of formula (I) are particularly suitable for controlling tomato nematodes, in particular: Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, puncture Pratylenchus penetrans and Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus vulnus, tiny Paratrichodorus minor, Meloidogyne exigua, Nacobbus aberrans, Globodera solanacearum, Dolichodorus heterocephalus, and Rotylenchulus reniformis .

The compounds of formula (I) are particularly suitable for controlling myriad plant nematodes, in particular: Meloidogyne arenaria, Meloidogyne hapla, Meloidogyne javanica, Meloidogyne incognita, kidney Rotylenchulus reniformis and Pratylenchus thornei.

The compounds of formula (I) are particularly suitable for controlling cotton nematodes, in particular: Belonolaimus longicaudatus, Meloidogyne incognita, Hoplolaimus columbus, Hoplolaimus galeatus and kidney Nematode (Rotylenchulus reniformis).

The compounds of formula (I) are particularly suitable for controlling corn worms, in particular: Belonolaimus longicaudatus, Paratrichodorus minor and Pratylenchus brachyurus, Pratylenchus delattrei , Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus zeae, Belonolaimus gracilis, Belonolaimus nortoni, short loop length Longidorus breviannulatus, Meloidogyne arenaria, Meloidogyne arenaria thamesi, Graminea nematode (Meloidogyne) Graminis), Meloidogyne incognita, Meloidogyne incognita acrita, Meloidogyne javanica, Meloidogyne naasi, Heterodera avenae Heterodera oryzae, Heterodera zeae, Punctodera chalcoensis, Ditylenchus dipsaci, Hoplolaimus aegyptii, and the big needle nematode (Hoplolaimus) Magnistylus), Hoplolaimus galeatus, Hoplolaimus indicus, Helicotylenchus digonicus, Helicotylenchus dihystera, Helicotylenchus pseudorobustus, American sword Nematodes (Xiphinema americanum), Dolichodorus heterocephalus, Criconemella ornata, Criconemella onoensis, Radopholus similis, Rotylenchulus borealis, Tiny kidney Nematode (Rotylenchulus parvus), Tylenchorhynchus agri, Tylenchorhynchus clarus, Tylenchorhynchus claytoni, Tylenchorhynchus maximus, Tylenchorhynchus Nudus), Tylenchorhynchus vulgaris, Quinisulcius acutus, Paratylenchus minutus, Hemicycliophora parvana, Aglenchus agricola, wheat granules Anguina tritici, Aphelenchoides arachidis, Scutellonema brachyurum and Subanguina radiciola.

The compounds of formula (I) are particularly suitable for controlling soybean nematodes, in particular: Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus penetrans, Scribner short-body nematodes (Pratylenchus Scribneri), Belonolaimus longicaudatus, Heterodera glycines, Hoplolaimus columbus, and Pratylinchus coffeae, Pratylenchus hexincisus, unsuccessful Nematode (Pratylenchus neglectus), Platyllenchus crenatus, Pratylenchus alleni, Pratylenchus agilis, Pratylenchus zeae, disability short body Nematode (Pratylenchus vulnus), (Belonolaimus gracilis), Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Meloidogyne hapla, Columbus nucleus Nematode (Hoplolaimus columbus), Hoplolaimus galeatus and Rotylenchulus reniformis.

The compounds of formula (I) are particularly suitable for controlling tobacco nematodes, in particular: Meloidogyne incognita, Meloidogyne javanica and Pratylenchus brachyurus, Pratylenchus pratensis, Pratylenchus hexincisus, Pratylenchus penetrans, Pratylenchus neglectus, Pratylenchus crenatus, Pratylenchus thornei, disability Pratylenchus vulnus, Pratylenchus zeae, Longidorus elongatu, Paratrichodorus lobatus, Trichodorus spp., Meloidogyne arenaria ), Meloidogyne hapla, Globodera tabacum, Globodera solanacearum, Globodera virginiae, Ditylenchus dipsaci, Rotylenchus spp .), Heliconia (Helicotylenchus spp.), Americas Nematode (Xiphinema americanum), the ring Strongyloides (Criconemella spp.), Rotylenchulus reniformis, Tylenchorhynchus claytoni, Paratylenchus spp. and Tetylenchus nicotianae.

The compounds of formula (I) are particularly suitable for controlling citrus nematodes, in particular: Pratylenchus coffeae and Pratylenchus brachyurus, Pratylenchus vulnus, Belonolaimus longicaudatus ), Paratrichodorus minor, Paratrichodorus porosus, Trichodorus, Meloidogyne incognita, Meloidogyne incognita acrita, Java Meloidogyne javanica, Rotylenchus macrodoratus, Xiphinema americanum, Xiphinema brevicolle, Xiphinema index, Criconemella spp .), Hemicriconemoides, Radopholus similis and Radopholus citrophilus, Hemicycliophora arenaria, Hemicycliophora nudata and Tylenchulus semipenetrans ).

The compounds of formula (I) are particularly suitable for controlling banana nematodes, in particular: Pratylinchus coffeae, Radopholus similis and Pratylenchus giibbicaudatus, Prasylenchus Loosi), Meloidogyne spp., Helicotyllenchus multicinctus, Helicotyllenchus dihystera, and Rotylenchulus Spp.

The compound of formula (I) is particularly suitable for controlling pineapple nematodes, in particular: Pratylenchus zeae, Pratylenchus pratensis, short-tailed short body Nematodes (Pratylenchus brachyurus), Pratylenchus goodeyi, Meloidogyne spp., Rotylenchulus reniformis, Longidorus elongatus, and long-stem nematode ( Longidorus laevicapitatus), Trichodorus primitivus, Trichodorus minor, Heterodera spp., Ditylenchus myceliophagus, Hoplolaimus californicus, and T. elegans (Hoplolaimus pararobustus), Hoplolaimus indicus, Helicotylenchus dihystera, Helicotylenchus nannus, Helicopterchus multicinctus, Helicotylenchus erythrine, Double Xiphinema dimorphicaudatum, Radopholus similis, Tylenchorhynchus digitatus, Tylenchorhynchus ebriensis, Paratylenchus minutus, Cavanes Helix (Scutellonema clathricaudatum), Scutellonema bradys, Psilenchus tumidus, Psilenchus magnidens, Pseudohalenchus minutus, Criconemoides Ferniae), Criconemoides onoense and Criconemoides ornatum.

The compounds of formula (I) are particularly suitable for controlling grapevine nematodes, in particular: Pratylenchus vulnus, Meloidogyne arenaria, Meloidogyne incognita, Meloidogyne javanica, Xiphinema americanum, Xiphinema index, Pratylenchus pratensis, Pratylenchus scribneri, Pratylenchus neglectus, short-tailed short Nematodes (Pratylenchus brachyurus), P. striata (Pratylenchus thornei) and citrus semi-puncture nematodes (Tylenchulus semipenetrans).

The compounds of formula (I) are particularly suitable for controlling tree-crop-C. elegans, in particular Pratylenchus penetrans and Pratylenchus vulnus, Longidorus elongatus, Southern Meloidogyne incognita and Meloidogyne hapla.

The compounds of formula (I) are particularly suitable for controlling tree-crop nematodes, in particular: Pratylenchus penetrans, Pratylenchus vulnus, Meloidogyne arenaria, Northern nodule nematodes (Meloidogyne hapla), Meloidogyne javanica, Meloidogyne incognita, Criconemella xenoplax and Pratylenchus brachyurus, Pratylenchus coffeae, Pratylenchus scribneri, Pratylenchus zeae, Belonolaimus longicaudatus, Helicotylenchus dihystera, Xiphinema americanum, curved ringworm Criconemella curvata), Tylenchorhynchus claytoni, Paratylenchus hamatus, Paratylenchus projectus, Scutellonema brachyurum and Hoplolaimus galeatus.

The compounds of formula (I) are particularly suitable for controlling tree crops, sugar cane and rice worms, in particular: Trichodorus spp., Criconemella spp. and Pratylenchus spp. , Paratrichodorus spp., Meloidogyne spp., Helicopterus spp., Tylenchorhynchus spp., Aphelenchoides spp., different Heterodera spp., Xiphinema spp. and Cacopaurus pestis.

As used herein, the term "nematode" also refers to nematodes that can harm humans or animals.

The clear nematode species that can harm humans or animals are: Trichinellida, for example: Trichuris spp., Capillaria spp., Paracapillaria spp. Necoleus spp., Trichomosoides spp., Trichinella spp., Tylenchida, for example: Micronema spp., Fecal nematode ( Strongyloides spp.) Rhabditina, for example: Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp. ), Gyalocephalus spp., Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp. Oesophagostomum spp., Chabertia spp., Stephanurus spp., Ancylostoma spp., Uncinaria spp., Hookworm (Necator spp.), Echinochloa (Bunostom) Um spp.), Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp .), Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp .), Spicocaulus spp., Elaphostrongylus spp., Parelaphostrongylus spp., Crenosoma spp., Parasitic nematode ( Paracrenosoma spp.), Oslerus spp., Angiostrongylus spp., L. (Aelurostrongylus spp.), Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Oster nematode Genus (Ostertagia spp.), genus Teladorsagia spp., Marshallagia spp., Cooperia spp., Nippostrongylus spp., Helicover Heligmosomoides spp.), Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus Spr.) Spirurida, for example: Oxyuris spp., Enterobius spp., Passalus spp., Syphacia spp., none Aspiculuris spp., Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp., Bailey aphid Genus (Baylisascaris spp.), Parascaris spp., Anisakis spp. ), Ascaridia spp.; Gnathostoma spp., Physaloptera spp., Thelazia spp., Gongylonema spp., horse Habronema spp., Parabronema spp.; Draschia spp., Dracunculus spp.; Stephanofilaria spp. Parafilaria spp., Setaria spp., Loa spp., Dirofilaria spp., Litomosoides spp. ), Brugia spp., Wuchereria spp., Onchocerca spp., Spirocerca spp.

Many known nematicides are also active against other parasitic helminths and can therefore be used to control parasites of humans and animals that are not necessarily nematodes. The invention also relates to the use of a compound of formula (I) as an anthelmintic. Pathogenic parasitic worms including flat animal gates (Platyhelmintha) (eg, monochomonas, aphids, and flukes), spines, and lingual animals. Preferably, the following helminths are mentioned: Monoogenea: for example: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.; Aphids: Pseudophyllidea, for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp. ), Bothridium spp., Diphlogonoporus spp.; Cyclophyllida, for example: Mesocestoides spp., Aphis genus Anoplocephala spp.), Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia spp., yolk-free gland Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Bertiella spp., belt Taenia spp., Echinococcus spp., Hydatigera spp .), Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle Spp.), Diochis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp.; trematode: complex Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., hairy Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp. ) (Echinostoma spp.), Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp. ), Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Fischoederius spp., Schistosoma (Gastrothylacus spp.), Notocotylus spp., Catatropis spp., Plagiorchis spp., Prosthogonimus spp. Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus spp., Collyriclum Spp.), Nanophyetus spp., Opisthorchis spp., Clonorchis spp., Metalschis spp., Alien Heterophyes spp., Metagonimus spp.; Acanthocephala: Oligacanthorhynchida, for example: Macracanthorhynchus spp. Prosthenorchis spp.; Polymorphida, for example: Filiocollis spp.; Moniliformida, for example: Moniliformis spp .); Echinorhynchida, for example: Acanthocephalus spp., Echinorhynchus spp., Leptorhynchoides spp.; (Pentastoma): Porocephalida, for example: Linguatula spp.

In the field of veterinary and animal husbandry, the compound of formula (I) is in a suitable application form, administered by methods known in the art, directly administered or by enteral, parenteral, transdermal Skin or nasal administration. The administration method can be prophylactic or medical.

The compounds of formula (I) may also be used as herbicides, safeners, growth regulators or formulations for improving the properties of plants, or as microbicides or gametocides, such as fungicides, at certain concentrations or application rates. , anti-fungal agents, bactericides, virucides (including anti-viral preparations) or as preparations against MLO (mycoplasma-like organisms) and RLO (like rickettsia organisms). If appropriate, it can also be used as an intermediate or precursor for the synthesis of other active compounds.

Formulation

The invention further relates to a formulation comprising at least one compound of the formula (I) and an application form from which the pesticide is made, for example, an infusion, a drip and a spray. In some instances, such application forms may further comprise other pesticides and/or improved utility adjuvants such as penetrants such as vegetable oils (eg, rapeseed oil, sunflower oil), mineral oils (eg, paraffin oil) An alkyl ester of a vegetable fatty acid (for example: rapeseed oil methyl ester or soybean oil methyl ester), or an alkanol alkoxide, and/or a distribution agent, such as an alkyl oxane, and / or salts, such as: organic or inorganic ammonium or phosphonium salts, such as: ammonium sulfate or diammonium hydrogen phosphate, and / or promote retention agents, such as: dioctyl sulfosuccinate or hydroxypropyl Guanhua gum A polymer, and/or a humectant, such as glycerin, and/or a fertilizer, such as a fertilizer containing ammonium, potassium or phosphorus.

Commonly used formulations are, for example, water-soluble liquid (SL), emulsified concentrate (EC), aqueous emulsion (EW), suspension concentrate (SC, SE, FS, OD), water-dispersible granules (WG), granules. Agent (GR) and capsule concentrate (CS); these and other possible formulation types are described, for example, in the FAO/WHO Joint Meeting on Pesticide Specifications (2004, ISBN: 9251048576) International Crop and Pesticides Description, FAO and WHO Pesticide Development and Usage Manual, FAO Plant Life and Development Report -173 (Crop Life International and in Pesticide Specifications, Manual on development and use Of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers- 173)". In addition to one or more compounds of formula (I), other agrochemically active compounds may optionally be included in the formulation.

These preferably comprise adjuvants (for example: supplements, solvents, spontaneous accelerators, carriers, emulsifiers, dispersants, frost protectants, biocides, thickeners and/or other adjuvants such as: The formulation or application pattern of the adjuvant). As used herein, an adjuvant refers to a component that can emphasize the biological effects of the ligand but does not have any biological effects per se. Examples of adjuvants are formulations that promote retention, distribution, attachment to leaf surfaces or penetration.

These formulations are prepared in a known manner, for example by mixing a compound of formula (I) with an adjuvant, for example a supplement, a solvent and/or a solid carrier and/or other adjuvants, for example a surfactant. Formulations are made in a suitable device or prior to or during administration.

The adjuvants used may be specially formulated for the formulation of the compound of formula (I) or the application form made of such formulations (for example: ready-to-use pesticides such as sprays or seed dressings) A property, such as a substance of some physical, technical, and/or biological nature.

Suitable extenders are, for example, water, polar and non-polar organic chemical liquids such as aromatic and non-aromatic hydrocarbons (eg, paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes), alcohols and polyols. (Alternatively, substituted, etherified and/or esterified), ketones (eg acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted And substituted amines, guanamines, indoleamines (such as N-alkylpyrrolidone) and lactones, terpenoids and amidoxines (such as: dimethyl hydrazine).

When water is used as a supplement, for example, an organic solvent can also be used as an auxiliary solvent. Substantially applicable liquid solvents are: aromatic hydrocarbons (eg xylene, toluene, or alkylnaphthalenes), chlorinated aromatic hydrocarbons or chlorinated aliphatic hydrocarbons (eg chlorobenzene, vinyl chloride or dichloromethane) , aliphatic hydrocarbons (such as: cyclohexane or paraffin, such as: petroleum fractions, mineral oils and vegetable oils), alcohols (such as: Butanol or glycols, and their ethers and esters), ketones (such as: acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strong polar solvents (such as: dimethyl Formamide and dimethyl hydrazine), and water.

It is possible in principle to use all suitable solvents. Examples of suitable solvents are: aromatic hydrocarbons (eg xylene, toluene or alkylnaphthalenes), chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons (eg chlorobenzene, vinyl chloride or dichloromethane), aliphatic Hydrocarbons (eg cyclohexane, paraffin, petroleum fractions, mineral oils and vegetable oils), alcohols (eg methanol, ethanol, isopropanol, butanol or glycols and their ethers and esters), ketones Classes (eg acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone), strong polar solvents (eg dimethyl hydrazine), and water.

It is possible in principle to use all suitable carriers. Suitable carriers include, for example, ammonium salts and natural mineral mills such as kaolin, clay, talc, chalk, quartz, strontium, montmorillonite or diatomaceous earth, and synthetic mineral powders such as high dispersion. Vermiculite, alumina and natural or synthetic silicates, resins, waxes and/or solid fertilizers. Mixtures of such carriers can also be used. Carriers suitable for granules include, for example, pulverized and divided natural ores such as calcite, marble, pumice, sepiolite, dolomite, and synthetic particles of inorganic and organic powders, and particles of organic materials such as sawdust, Paper, coconut shells, corn cobs and tobacco stalks.

Liquefied gas supplements or solvents can also be used. Particularly suitable are those supplements or carriers which are gaseous at standard temperature and standard pressure, such as: aerosol propellant gases such as halocarbons and butane, propane, nitrogen and carbon dioxide.

Examples of ionic or nonionic emulsifiers and/or foam formers, dispersants or humidifiers, or mixtures of such surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, phenolsulfonic acid Or a salt of naphthalenesulfonic acid, a polycondensate of ethylene oxide with a fatty alcohol or with a fatty acid or with an aliphatic amine, with a substituted phenol (preferably an alkylphenol or an arylphenol), sulfosuccinic acid a salt of an ester, a taurine derivative (preferably an alkyl taurate), a phosphate of a polyethoxylated alcohol or phenol, a fatty acid ester of a polyhydric alcohol, and a sulfate, a sulfonate and a phosphoric acid. Root Derivatives of the compounds, for example: alkyl aryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolysates, lignin sulfite waste liquids and Methylcellulose. If one of the compounds of formula (I) and/or one of the inert carriers is insoluble in water and when applied using water, it is preferred to include a surfactant.

Other adjuvants that may be present in the formulation and the application form from which it is derived include dyes such as inorganic pigments (eg, iron oxide, titanium oxide and Prussian blue) and organic dyes (eg, alizarin dyes, even Nitrogen dyes and metal phthalocyanine dyes, and nutrients and micronutrients such as iron, manganese, boron, copper, cobalt, molybdenum and zinc.

Other components may be stabilizers such as low temperature stabilizers, preservatives, antioxidants, light stabilizers or other agents that improve chemical/physical stability. A foam former or an antifoaming agent may also be included.

In addition, the formulation and its derived application form may also contain other adjuvants, such as carboxymethyl cellulose, and natural and synthetic powder, granule or latex polymers, such as: gum arabic, Polyvinyl alcohol, polyvinyl acetate, or natural phospholipids such as cephalin and lecithin, and synthetic phospholipids. Other possible adjuvants are mineral oils and vegetable oils.

Other adjuvants may also be included in the formulation and the forms of application from which it is derived. Examples of such additives include perfumes, protective colloids, binders, adhesives, thickeners, shakers, penetrants, retention retention agents, stabilizers, chelating agents, error agents, humectants, and distribution agents. In general, the compound of formula (I) can be used in combination with any conventional solid or liquid additive for the purpose of formulation.

Suitable promoting retention agents include all materials which reduce the dynamic surface tension, such as dioctyl sulfosuccinate, or substances which increase viscoelastic properties, such as hydroxypropyl croton gum polymers.

Suitable penetrants herein include all of them commonly used to improve agrochemical activation The compound penetrates into all the substances in the plant. As used herein, a penetrant is defined as the ability to apply a liquid from (usually aqueous) and/or from the spray layer into the plant skin layer and thereby increase the mobility of the active compound in the epidermis. This property can be determined by the method described in the literature (Baur et al. 1997, Pesticide Science 51, 131-152). Examples thereof include alcohol alkoxides (e.g., coconut fatty ethoxylate (10) or isotridecyl ethoxylate (12)), fatty acid esters (e.g., rapeseed oil methyl ester or soybean oil methyl ester) a fatty amine alkoxide (for example: tallow amine ethoxylate (15)), or an ammonium and/or phosphonium salt, for example ammonium sulphate or diammonium hydrogen phosphate.

Preferably, the formulation comprises a compound of formula (I) in an amount of from 0.00000001% to 98% by weight, based on the weight of the formulation, or particularly preferably from 0.01% to 95% by weight, based on the compound of formula (I), more preferably from 0.5% to 90% by weight of the compound of formula (I).

The content of the compound of the formula (I) in the application form (specifically, the pesticide) made from the formulation can vary over a wide range. The concentration of the compound of the formula (I) in the application form is usually from 0.00000001% to 95% by weight, preferably from 0.00001% to 1% by weight, based on the weight of the application form. This application is achieved in the usual manner suitable for such application patterns.

mixture

The compound of formula (I) may also be combined with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbicides, beneficial substances, herbicides, fertilizers Use of a mixture of bird repellents, fortified botanicals, infertility agents, safeners, chemical information substances and/or plant growth regulators, for example, to broaden the scope of action, extend the duration of action, increase the rate of action, prevent rejection or prevent Develop resistance. In addition, this combination of active compounds can improve plant growth and/or tolerance to abiotic factors, for example, to high or low temperatures, to drought or to increased moisture or salt content. It can also improve flowering and performance, optimize germination and root development, promote harvest and improve yield, affect maturity, improve the quality and/or nutritional value of harvested products, extend shelf life for harvested products and/or change Good workability.

Furthermore, the compounds of the formula (I) may be admixed with other active compounds or chemical information substances, such as attractants and/or bird repellents and/or plant activators and/or growth regulators and/or fertilizers. Likewise, the compounds of formula (I) can be used in admixture with formulations which improve the properties of the plant, such as, for example, growth, yield, and quality of the material being harvested.

According to a particular embodiment of the invention, the compound of formula (I) is formed into a mixture with other compounds, preferably a compound described below, in the form of a formulation or an application form made from the formulation.

If one of the compounds described below may exhibit different tautomeric forms, these forms are included even if not individually presented.

Insecticide / acaricide / nematicide

Active compounds are referred to herein by their common names and are described, for example, in the Pesticides Manual ("Pesticide Manual", 16th Edition, British Crop Protection Council 2012) or can be found in the Internet (Example: http://www.alanwood.net/pesticides).

(1) Acetylcholinesterase (AChE) inhibitors, such as, for example, urethanes, for example: alanycarb, aldicarb, bendiocarb, Benfka (benfuracarb), butocarboxim, buthoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fen Fenobucarb, formetanate, furathiocarb, isoprocarb, metiocarb, methomyl, metolcarb, killing (oxamyl), pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and sputum (xylylcarb); or organic phosphorus Acid esters, for example: acephate, azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorzene ( Chlorethoxyfos), chlorfenfos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton -S-methyl, diazinon, dichlorvos/DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN , ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, fly Heptonenophos, imicyafos, isofenphos, O-(methoxyaminothiophosphonium) isopropyl salicylate, isoxathion, marathon (malathion), mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, narcissus (naled), omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate ), phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, and pudansong Propetamphos), prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos , terbufos, tetrachlorvinphos, thiometon, triazophos, triclofen and vamidothion.

(2) GABA-Gate-controlled chloride channel antagonists, for example: cyclodiene organochlorines, such as: chlordane and endosulfan; or phenylpyrazoles (feipulo ( Fiprole)), example Such as: ethiprole and fipronil.

(3) Sodium channel modulators/voltage-dependent sodium channel blockers, such as, for example, pyrethroids, for example: acrinathrin, allethrin, d-cis-trans Allethrin, allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, biscitron Bioresmethrin), cycloprothrin, cyfluthrin, cyfluthrin, cyhalothrin, cy- cyhalothrin, γ-cylonin ), cypermethrin, cypermethrin, cypermethrin, cypermethrin, cypermethrin, cyphenothrin ) [(1R)-trans isomer], deltamethrin, emtemphrin [(EZ)-(1R) isomer], esfenvalerate, efenine ( Etofenprox), fenpropathrin, fenvalerate, flucythrinate, flumethrin, τ-fuvalinate, halfenprox, Yipu (imiprothrin), kadethrin, permethrin, phenothrin [(1R)-trans isomer], prallethrin, pyrethrins (pyrethrins) Pyrethrum)), resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R) isomer), typhine (tralomethrin) and transfluthrin; or DDT; or methoxychlor.

(4) Nicotine-induced acetylcholine receptor (nAChR) agonists, such as neonicotinoids, for example: acetamiprid, clothianidin, dinotefuran ), imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or nicotine or sulfoxaflor.

(5) Atopic activators of nicotine-induced acetylcholine receptor (nAChR), for example: (Spinosyns), for example: spinetoram and spinosad.

(6) Chloride channel activators, for example: avermectins/milbemycin, for example: abamectin, emamectin benzoate, benefit Lepimectin and milbemectin.

(7) a juvenile hormone mimetic, such as a juvenile hormone analog, such as: hydroprene, kinoprene and metoprene; or fenoxycarb; Pypriroxyfen.

(8) active compounds which are undesired or non-specific, such as alkyl halides such as methyl bromide and other alkyl halides; or chloropicrin; or thiopurine; or borax ( Borax); or tartar emetic.

(9) Selective antifeeding agents, for example, pymetrozine or flonicamid.

(10) Indole growth inhibitors, for example: clofentezine, hexythiazox and diflovidazin or etoxazole.

(11) Microbial resolving agents for insect intestinal membranes, for example, Bacillus thuringiensis subspecies israelensis , Bacillus sphaericus , Bacillus thuringiensis subspecies aizawai , Bacillus thuringiensis Bacillus thuringiensis subspecies kurstaki , Bacillus thuringiensis subspecies tenebrionis and BT plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34/35Ab1.

(12) oxidative phosphorylation inhibitor, ATP disintegrator, for example: diafenthiuron; or organotin compounds such as azocyclotin, cyhexatin and fenbutatin Oxide; or propargite or tetradifon.

(13) Oxidative phosphorylation reaction decoupling agent that interferes with the H-proton gradient, for example: kefenpyr (chlorfenapyr), DNOC and sulfluramid.

(14) Nicotine-induced acetylcholine receptor antagonists, for example, bensultap, cartap hydrochloride, thiocylam, and thiosultap- sodium.

(15) Chitin biosynthesis inhibitors, type 0, for example: bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, Hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

(16) Chitin biosynthesis inhibitor, type 1, for example, buprofezin.

(17) A mutated inhibitor (specifically, a Diptera, that is, a Diptera insect), such as, for example, cyromazine.

(18) Opioid receptor agonists, for example, chromafenozide, hafenfenzide, methoxyfenozide, and tebufenozide.

(19) Octopamine-induced agonist, for example: amitraz.

(20) Complex-III electron transport inhibitors, for example, hydramethylnone or acequinocyl or fluacrypyrim.

(21) Complex-I electron transport inhibitors, for example: METI acaricides, for example: fenazaquin, fenpyroximate, pyrimidifen, pyridaben, up to Tebufenpyrad and tolfenpyrad; or rotenone (Derris).

(22) Voltage-gated sodium channel blockers, such as indoxacarb or metaflumizone.

(23) Inhibitors of acetyl-Co-A carboxylases, for example, quaternary keto acids and pyrrolidone derivatives, such as: spirodiclofen, spiromesifen, and spirotetramat ).

(24) Complex-IV electron transport inhibitors, for example: phosphines such as: aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanide.

(25) Complex-II electron transport inhibitors, for example, cyenopyrafen and cyflumetofen.

(28) Ryanodine receptor effector, for example, diamines, for example, chlorantraniliprole, cyantraniliprole and flubendiamide, other active ingredients, For example: afidopyropen, azadirachtin, benclothiaz, benzoximate, bifenazate, bromomethylate, chinomethionat , cryolite, dicofol, diflovidazin, fluensulfone, flometoquin, flufenerim, flufenoxystrobin , flufiprole, fluopyram, flupyradifurone, fufenozide, heptafluthrin, imidaclothiz, Iprodione, meperfluthrin, paichongding, pyflubumide, pyrifluquinazon, pyriminostrobin, tetrafluthrin Tetramethylfluthrin) with methyl iodide; and based on Bacillus firm Us) formulation (I-1582, BioNeem, Votivo), with the following compound: 3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)aminecarbamyl] Phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known in WO2005/077934) and 1-{2-fluoro-4-methyl-5 -[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazole-5-amine (from WO2006/ Known in 043635), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]-5-fluorospiro[吲哚-3,4'-piperidine -1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO2003/106457), 2-chloro-N-[2-{1-[(2E)-3- (4-Chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4-(trifluoromethyl)phenyl]isonicotinamide (known from WO2006/003494) , 3-(2,5-Dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazospiro[4.5]indole-3-en-2-one (from WO 2009/049851) 3-(2,5-Dimethylphenyl)-8-methoxy-2-oxo-1,8-diazospiro[4.5]indol-3-yl-4-yl carbonate -ethyl ester (known from WO 2009/049851), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoro Pyrimidine (known from WO2004/099160), 4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known from WO2003/076415), PF 1364 (CAS Accession No. 1204776-60-2), 4-[5-(3,5-Dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2- Zyrid-3-yl]-2-methyl-N-{2-p-oxy-2-[(2,2,2-trifluoroethyl)amino]ethyl}benzamide (from WO2005/ Known in 085216), 4-{5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2- Zyrid-3-yl}-N-{2-p-oxy-2-[(2,2,2-trifluoroethyl)amino]ethyl}-1-naphthylguanamine (from WO 2009/002809) Known), 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3- Methyl benzhydryl]-2-methylindolecarboxylate (known in WO2005/085216), 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl) -1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzylidene]-2-ethylindolecarboxylic acid methyl ester (known from WO2005/085216) 2-[2-({[3-Bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methyl Methyl benzhydryl]-2-methylindolecarboxylate (known in WO2005/085216), 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloro) Methyl pyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzimidyl]-2-ethylindolecarboxylate (known from WO2005/085216), 1-(3) -chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylamine-mercapto)phenyl]-3-{[5-(trifluoromethyl)-2H -tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide (known from WO2010/069502), N-[2-(5-amino-1,3,4-thia Diazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (from CN102057925 in Know), 3-chloro-N-(2-cyanopropan-2-yl)-N-[4-(1,1,1,2,3,3,3-heptafluoropropan-2-yl)-2- Methylphenyl]decylamine (known from WO2012/034472), 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl) Imidazo[1,2-a]pyridine-2-carboxamide (known from WO2010/129500), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl) )-4,5-dihydro-1,2- Zyrid-3-yl]-2-methyl-N-(1-oxo-oxathiolan-3-yl)benzamide (known in WO2009/080250), 4-[5-( 3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2- Zyrid-3-yl]-2-methyl-N-(1-oxo-oxathiolan-3-yl)benzamide (known from WO2012/029672), 1-[(2- Chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-indole-2-alkanoate ( Known from WO2009/099929), 1-[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidine- 1-non-2-alkanoate (known from WO2009/099929), (5S,8R)-1-[(6-chloropyridin-3-yl)methyl]-9-nitro-2,3 ,5,6,7,8-hexahydro-1H-5,8-epoxyimidazo[1,2-a]azepane (known from WO2010/069266), (2E)-1- [(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentanylguanidinium (known from WO2010/060231), 4-(3-{2,6-di Chloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine Known in CN101337940), N-[2-(t-butylaminomethylmercapto)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-( Fluoromethoxy)-1H-pyrazole-5-carboxamide (known in WO 2008/134969).

Fungicide

Active compounds which are referred to herein by their common names are known and are described, for example, in "The Pesticide Manual" or the Internet (for example: http://www.alanwood.net/pesticides).

(1) ergosterol biosynthesis inhibitors, for example: (1.1) aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) butoconazole (bromuconazole), (1.5) cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8) diconazole, (1.9) Diconicon-M, (1.10) dodemorph, (1.11) dodemorph acetate, (1.12) epoxiconazole, (1.13) statazole ( Etaconzole), (1.14) fenarimol, (1.15) fenbuconazole, (1.16) fenhexamide, (1.17) fenpropidin, (1.18) fenfluz ( Fenpropimorph), (1.19) fluquinconazole, (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafol, (1.23) fluconazole (furconazole), (1.24) fluconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) ima sulphate (imazalil sulphate) ), (1.28) imibenconazole, (1.29) fepconazole (ipcon) Azole, (1.30) metconazole, (1.31) myclobutanil, (1.32) naftifin, (1.33) nuarimol, (1.34) Oxpoconazole, (1.35) paclobutrazole, (1.36) pefurazoate, (1.37) penconazole, (1.38) piperalin, (1.39) poker (prochloraz), (1.40) propiconazole, (1.41) prothioconazole, (1.42) pyributicarb, (1.43) pyrifenox, (1.44) claconazole ( Quinconazole), (1.45) simeconazole, (1.46) spiroxamine, (1.47) tebuconazole, (1.48) terbinafin, (1.49) terconazole ), (1.50) triadimefon, (1.51) triadimenol, (1.52) tridemorph, (1.53) triflumizol, (1.54) triforine, (1.55) triticonazole, (1.56) uniconazole, (1.57) euconazole-P (uniconazol-P), (1.58) viniconazole, (1.59) Fukang Voriconazole, (1.60) 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61) 1-(2,2- Methyl dimethyl-2,3-dihydro-1H-indol-1-yl)-1H-imidazole-5-carboxylate, (1.62) N'-{5-(difluoromethyl)-2-methyl Base-4-[3-(three矽alkyl)propoxy]phenyl}-N-ethyl-N-methylformamidine, (1.63) N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoro Methyl)-4-[3-(trimethyldecyl)propoxy]phenyl}formamidine with (1.64)O-[1-(4-methoxyphenoxy)-3,3-di Methylbutan-2-yl]-1H-imidazole-1-thioformate, (1.65) pyrisoxazole.

(2) Respiratory inhibitors (respiratory chain inhibitors), for example: (2.1) bixafen, (2.2) boscalid, (2.3) carboxin, (2.4) Diflumetorim, (2.5) fenfuram, (2.6) fluopyram, (2.7) flutolanil, (2.8) fluxapyroxad, (2.9) Furametpyr, (2.10) furmecyclox, (2.11) isoprozol cis-epimer racemate 1RS, 4SR, 9RS and anti-epimer elimination Spin 1RS, 4SR, 9SR mixture, (2.12) isopyrazam (trans-epimer racemate), (2.13) isopyrazam (anti-epimer alignment) Isomers 1R, 4S, 9S), (2.14) Isoprozam (anti-epimer enantiomers 1S, 4R, 9R), (2.15) Isoproza (isopyrazam) - Epimer racemate 1RS, 4SR, 9RS), (2.16) Isoprozam (cis-epimomer enantiomers 1R, 4S, 9R), (2.17) Isopyrazam (cis-epimomer enantiomers 1S, 4R, 9S), (2.18) mepronil, (2.19) oxycarboxin, (2.20) Benfu (penflufen), (2.21) this game (penthio Pyrad), (2.22) sedaxane, (2.23) flufluzamid, (2.24) 1-methyl-N-[2-(1,1,2,2-tetrafluoroethoxy) Phenyl]-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, (2.25) 3-(difluoromethyl)-1-methyl-N-[2-(1, 1,2,2-tetrafluoroethoxy)phenyl]-1H-pyrazole-4-carboxamide, (2.26) 3-(difluoromethyl)-N-[4-fluoro-2-(1) ,1,2,3,3,3-hexafluoropropoxy)phenyl]-1-methyl-1H-pyrazole-4-carboxamide, (2.27) N-[1-(2,4- Dichlorophenyl)-1-methoxypropan-2-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.28) 5,8- Difluoro-N-[2-(2-fluoro-4-{[4-(trifluoromethyl)pyridin-2-yl]oxy}phenyl)ethyl]quinazolin-4-amine, (2.29) Benzovindiflupyr, (2.30) N-[(1S,4R)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methylenenaphthalene- 5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide and (2.31) N-[(1R,4S)-9-(dichloromethylene )-1,2,3,4-tetrahydro-1,4-methylenenaphthalen-5-yl]-3-(difluoro Methyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.32) 3-(difluoromethyl)-1-methyl-N-(1,1,3-trimethyl- 2,3-Dihydro-1H-indol-4-yl)-1H-pyrazole-4-carboxamide, (2.33) 1,3,5-trimethyl-N-(1,1,3-three Methyl-2,3-dihydro-1H-indol-4-yl)-1H-pyrazole-4-carboxamide, (2.34) 1-methyl-3-(trifluoromethyl)-N-( 1,1,3-trimethyl-2,3-dihydro-1H-indol-4-yl)-1H-pyrazole-4-carboxamide, (2.35) 1-methyl-3-(trifluoro) Methyl)-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-indol-4-yl]-1H-pyrazole-4-carboxamide, (2.36 1-methyl-3-(trifluoromethyl)-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-indol-4-yl]-1H- Pyrazole-4-carboxyguanamine, (2.37) 3-(difluoromethyl)-1-methyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro- 1H-indol-4-yl]-1H-pyrazole-4-carboxamide, (2.38) 3-(difluoromethyl)-1-methyl-N-[(3R)-1,1,3- Trimethyl-2,3-dihydro-1H-indol-4-yl]-1H-pyrazole-4-carboxamide, (2.39) 1,3,5-trimethyl-N-[(3R) -1,1,3-trimethyl-2,3-dihydro-1H-indol-4-yl]-1H-pyrazole-4-carboxamide, (2.40) 1,3,5-trimethyl -N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-indol-4-yl]-1H-pyrazole-4-carboxamide, (2.41) wheat rust Spirit (benodanil), (2.42) 2-chloro-N-(1,1,3-trimethyl -2,3-Dihydro-1H-indol-4-yl)pyridine-3-carboxamide, (2.43) isofetamid.

(3) Respiratory inhibitors (breathing chain inhibitors) acting on the respiratory chain complex III, for example: (3.1) ametoctradin, (3.2) amisulbrom, (3.3) atoramine (azoxystrobin), (3.4) cyazofamid, (3.5) coumethoxystrobin, (3.6) coumoxystrobin, (3.7) dimoxystrobin, (3.8) olefin Essence (enestroburin), (3.9) famoxadone, (3.10) fenamidone, (3.11) flufenoxystrobin, (3.12) fluoxastrobin, (3.13) Kresoxim-methyl, (3.14) methotrexate, (3.15) orysastrobin, (3.16) picoxystrobin, (3.17) pyraclostrobin Ester (pyraclostrobin), (3.18) pyramitostrobin, (3.19) pyraoxystrobin, (3.20) pyridencarb, (3.21) triclopyricarb, (3.22) Trifloxystrobin, (3.23) (2E)-2-(2-{[6-(3-Chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxy Iminoamino)-N-methylacetamide, (3.24) (2E)-2-(methoxyimino)-N-methyl-2-(2-{[({(1E)-) 1-[3-(Trifluoromethyl)phenyl]ethylidene]amino)oxy]methyl}phenyl)acetamide, (3.25)(2E)-2-(methoxyimino) -N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imido)methyl]phenyl}acetamide, (3.26) (2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy)phenyl)ethylidene) ]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide, (3.27)(2E)-2-{2-[({[(2E) ,3E)-4-(2,6-dichlorophenyl)butylene-3-en-2-yl]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N -methylacetamide, (3.28) 2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-indol-4-yl)pyridine-3-carboxamide, (3.29) 5-Methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylidene))oxy)] Methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, (3.30)(2E)-2-{2-[({cyclopropyl[(4) -Methoxyphenyl)imido]methyl}thio)methyl]phenyl}-3-methoxyprop-2-enoate, (3.31 N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(carbamimidino)-2-hydroxybenzamide, (3.32) 2-{2-[( 2,5-Dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide.

(4) Inhibitors of mitosis and cell differentiation, for example: (4.1) benomyl, (4.2) carbendazim, (4.3) chlorfenazole, (4.4) Diethofencarb), (4.5) ethaboxam, (4.6) fluopicolide, (4.7) fuberidazole, (4.8) pencycuron, (4.9) thiabendazole ), (4.10) thiophanate-methyl, (4.11) thiophanate, (4.12) zoxamide, (4.13) 5-chloro-7-(4-methyl Piperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine with (4.14)3-chloro-5- (6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)anthracene .

(5) Compounds having multiple site activities, for example: (5.1) Bordeaux mixture, (5.2) captafol, (5.3) captan, (5.4) tetrachloroisophthalonitrile (chlorothalonil), (5.5) Copper preparations such as: copper hydroxide, (5.6) copper naphthoate, (5.7) copper oxide, (5.8) basic copper oxychloride, (5.9) copper sulfate, (5.10) dichlofluanid, (5.11) nitrile Dithianon, (5.12) dodine, (5.13) tannin free base, (5.14) ferbam, (5.15) fluorfolpet, (5.16) fore (folpet), (5.17) guazatine, (5.18) guazatine acetate, (5.19) iminoctadine, (5.20) succinyl sulfonate (iminoctadine) Albesilate), (5.21) iminoctadine triacetate, (5.22) manganese (mancopper), (5.23) manganese powder (mancozeb), (5.24) manganese iripy (maneb), (5.25) Met (metiram), (5.26) 得 锌 zinc salt, (5.27) copper-oxine, (5.28) propamidine, (5.29) methyl zinc propimb (propineb), ( 5.30) Sulfur and sulfur preparations such as, for example, calcium polysulfide, (5.31) thiram, (5.32) tolylfluanid, (5.33) zinc napu (zineb), (5.34) Ziram) and (5.35) anilazine.

(6) Resistance-inducing agents, for example: (6.1) acibenzolar-S-methyl, (6.2) isotianil, (6.3) probenazole, (6.4) Tiadinil and (6.5) laminarin.

(7) Amino acids and protein biosynthesis inhibitors, for example, (7.1), (7.2) blasticidin-S, (7.3) cyprodinil, (7.4) Kasugamycin, (7.5) kasugamycin hydrochloride hydrate, (7.6) mepanipyrim, (7.7) pyrimethanil, (7.8) 3-(5-fluoro -3,3,4,4-tetramethyl-3,4-dihydroisoquinolin-1-yl)quinoline, and (7.9) oxytetracycline and (7.10) streptomycin .

(8) ATP production inhibitors such as, for example, (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide and (8.4) Silthiofam.

(9) Cell wall synthesis inhibitors, for example: (9.1) benthiavalicarb, (9.2) (dimethomorph), (9.3) flumorph, (9.4) iprovalicarb, (9.5) mandipropamid, (9.6) polyoxins, (9.7) Baolingling (polyoxorim), (9.8) validamycin A, (9.9) valifenalate and (9.10) polyoxin B.

(10) Lipid and membrane synthesis inhibitors, for example: (10.1) biphenyl, (10.2) chloroneb, (10.3) dicloran, (10.4) edifenphos, (10.5) ) etridiazole, (10.6) iodocarb, (10.7) iprobenfos, (10.8) isoprothiolane, (10.9) propamocarb, (10.10) propamocarb hydrochloride, (10.11) prothiocarb, (10.12) pyrazophos, (10.13) quintozene, (10.14) tetrachloronitrate Benzene (tecnazene) and (10.15) tolclofos-methyl.

(11) melanin synthesis inhibitors, for example: (11.1) capellamid (), (11.2) diccoymet, (11.3) fenoxanil, (11.4) fthalide ), (11.5) pyroquilon, (11.6) tricyclazole and (11.7) {3-methyl-1-[(4-methylbenzhydryl)amino]butane- 2-Base} 2,2,2-trifluoroethyl carbamate.

(12) Inhibitors of nucleic acid synthesis, for example: (12.1) benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate (12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furaxax, (12.8) hymexazol, (12.9) metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11) ofofce, (12.12) oxadixyl ), (12.13) oxolinic acid and (12.14) octhilinone.

(13) Signal transduction inhibitors, for example: (13.1) chlozolinate, (13.2) fenpiclonil, (13.3) fludioxonil, (13.4) iprodione (13.5) Procymidone, (13.6) quinoxyfen, (13.7) vinclozolin and (13.8) proquinazid.

(14) Decoupling agents, for example: (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam and (14.5) Meptyldinocap.

(15) Other compounds, for example: (15.1) benzizole, (15.2) benzene (bethoxazine), (15.3) cappmycin (capsimycin), (15.4) carvone, (15.5) quinoline thioacetate (quinethionat), (15.6) pyrofenone (pyriofenone) (chlazafenon), (15.7) cufraneb, (15.8) cyflufenamid, (15.9) cymoxanil, (15.10) cyprosulfamide, ( 15.11) dazomet, (15.12) debacarb, (15.13) dichlorophen, (15.14) dimlomezine, (15.15) difenzoquat, ( 15.16) morphazole methyl sulfate, (15.17) diphenylamine, (15.18) espressan (EcoMate), (15.19) fenpyrazamine, (15.20) flumetover, (15.21) ) fluoromid, (15.22) flusulphamide, (15.23) flutianil, (15.24) fosetyl-aluminium, (15.25) forsythia calcium ( Fosetyl-calcium), (15.26) fosetyl-sodium, (15.27) hexachlorobenzene, (15.28) irumamycin, (15.29) methasulfocarb, (15.30) Methyl thiocyanate, (15.31) metrafenone, (15.32) medemycin (m Ildiomycin), (15.33) natamycin, (15.34) nickel dimethyldithiocarbamate, (15.35) nitrothal-isopropyl, (15.36) octhilinone (15.37) oxamocarb, (15.38) oxyfenthiin, (15.39) pentachlorophenol and its salts, (15.40) phenothrin, (15.41) phosphate and its salts, (15.42) propamocarb-fosetylate, (15.43) propanosine-sodium, (15.44) pyrymorph, (15.45)(2E)-3-(4- Tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (15.46)(2Z)-3- (4-tert-butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (15.47) pyrroline ( Pyrrolnitrin), (15.48) tebufloquin, (15.49) tecloftalam, (15.50) tolnifanid, (15.51) triazoxide, (15.52) trichloropurine Tricholide, (15.53) zarilamid, (15.54) 2-methylpropionic acid (3S,6S,7R,8R)-8-benzyl-3-[({3-[( Isobutyryloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-di-oxy-1 ,5-dioxan-7-yl ester, (15.55) 1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydrol -1,2- Zyrid-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl Ethyl ketone, (15.56) 1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2- Zyrid-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl Ethylketone, (15.57) 1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2- Zyrid-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl Ethyl ketone, (15.58) 1H-imidazol-1-carboxylic acid 1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl ester, (15.59) 2,3, 5,6-tetrachloro-4-(methylsulfonyl)pyridine, (15.60) 2,3-dibutyl-6-chlorothieno[2,3-d]pyrimidin-4(3H)-one, (15.61) 2,6-Dimethyl-1H,5H-[1,4]disulfide And [2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone, (15.62)2-[5-methyl-3-(trifluoro Methyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2- Zyrid-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, (15.63) 2-[5-methyl-3-(trifluoromethyl)-1H-pyridyl Zin-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2- Zyrid-3-yl]-1,3-thiazol-2-yl}piperidin-1-yl)ethanone, (15.64) 2-[5-methyl-3-(trifluoromethyl)-1H-pyridyl Zin-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2- Zyridin-3-yl)-1,3-thiazol-2-yl]piperidin-1-yl}ethanone, (15.65) 2-butoxy-6-iodo-3-propyl-4H-chromene- 4-ketone, (15.66) 2-chloro-5-[2-chloro-1-(2,6-difluoro-4-methoxyphenyl)-4-methyl-1H-imidazol-5-yl] Pyridine, (15.67) 2-phenylphenol and salts, (15.68) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl Quinoline, (15.69) 3,4,5-trichloropyridine-2,6-dicarbonitrile, (15.70) 3-chloro-5-(4-chlorophenyl)-4-(2,6-di Fluorophenyl)-6-methyloxime , (15.71) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylhydrazine , (15.72) 5-amino-1,3,4-thiadiazole-2-thiol, (15.73) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl Thiophene-2-sulfinyl hydrazine, (15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (15.75) 5-fluoro-2-[(4- Methylbenzyloxy)pyrimidine-4-amine, (15.76) 5-methyl-6-octyl[1,2,4]triazolo[1,5-a]pyrimidin-7-amine, ( 15.77) (2Z)-3-Amino-2-cyano-3-phenylethyl acrylate, (15.78) N'-(4-{[3-(4-chlorobenzyl)-1,2, 4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methylformamidine, (15.79)N-(4-chlorobenzyl)- 3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamine, (15.80) N-[(4-chlorophenyl)(cyano)methyl] -3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propanamine, (15.81) N-[(5-bromo-3-chloropyridin-2-yl) )methyl]-2,4-dichloroshitamine, (15.82) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloroshitamine , (15.83) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodoguanidine, (15.84) N-{(E)-[( Cyclopropylmethoxy)imido][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, (15.85) N-{( Z)-[(cyclopropylmethoxy)imido][6-(difluoromethoxy) )-2,3-difluorophenyl]methyl}-2-phenylacetamidine, (15.86) N'-{4-[(3-tert-butyl-4-cyano-1,2- Thiazol-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methylformamidine, (15.87) N-methyl-2-(1-{[5- Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethenyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthalene-1- -1,3-1,3-thiazol-4-carboxamide, (15.88) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazole-1 -yl]ethinyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxyguanamine , (15.89) N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]ethenyl}piperidin-4-yl) -N-[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]-1,3-thiazole-4-carboxyguanamine, (15.90){6-[({[(1- Methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}ammonium formate, (15.91) phene 1-carboxylic acid, (15.92) quinoline-8-ol, (15.93) quinoline-8-ol sulfate (2:1), (15.94) {6-[({[(1-methyl-1H) -tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamic acid tert-butyl ester, (15.95) 1-methyl-3-(three Fluoromethyl)-N-[2'-(trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (15.96) N-(4'-chlorobiphenyl-2 -yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (15.97) N-(2',4'-dichlorobiphenyl-2-yl) -3-(Difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (15.98) 3-(difluoromethyl)-1-methyl-N-[4'-( Trifluoromethyl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (15.99) N-(2',5'-difluorobiphenyl-2-yl)-1-methyl -3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, (15.100) 3-(difluoromethyl)-1-methyl-N-[4'-(prop-1-yne) -1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxyguanamine, (15.101) 5-fluoro-1,3-dimethyl-N-[4'-(prop-1- Alkyn-1-yl)biphenyl-2-yl]-1H-pyrazole-4-carboxamide, (15.102) 2-chloro-N-[4'-(prop-1-yn-1-yl) Benz-2-yl]nicotinamine, (15.103) 3-(difluoromethyl)-N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2 -yl]-1-methyl-1H-pyrazole-4-carboxyguanamine, (15.104) N-[4'-(3,3-di Butyl-1-yn-1-yl)biphenyl-2-yl]-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (15.105) 3-(difluoro Methyl)-N-(4'-ethynylbiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide, (15.106) N-(4'-ethynylbiphenyl- 2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (15.107) 2-chloro-N-(4'-ethynylbiphenyl-2-yl) Nicotinamide, (15.108) 2-chloro-N-[4'-(3,3-dimethylbut-1-yn-1-yl)biphenyl-2-yl]nicotamine, (15.109)4 -(Difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)biphenyl-2-yl]-1,3-thiazole-5-carboxamide, (15.110) 5- Fluorine-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4- Carboxylamidine, (15.111) 2-chloro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]nicotamine, (15.112) 3-(Difluoromethyl)-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl]-1-methyl-1H -pyrazole-4-carboxyguanamine, (15.113) 5-fluoro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)biphenyl-2-yl ]-1,3-Dimethyl-1H-pyrazole-4-carboxamide, (15.114) 2-chloro-N-[4'-(3-methoxy-3-methylbut-1-yne) -1-yl)biphenyl-2-yl]nicotamine, (15.115) (5-bromo-2-methoxy-4-methylpyridinium -3-yl)(2,3,4-trimethoxy-6-methylphenyl)methanone, (15.116) N-[2-(4-{[3-(4-chlorophenyl)propene- 2-alkyn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methylsulfonyl)decylamine, (15.117) 4-sided oxy-4-[(2 -Phenylethyl)amino]butyric acid, (15.118){6-[({[(Z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amine) (yloxy)methyl]pyridin-2-yl}carbamic acid but-3-yn-1-yl ester, (15.119) 4-amino-5-fluoropyrimidin-2-ol (tautomeric form: 4- Amino-5-fluoropyrimidine-2(1H)-one), (15.120) propyl 3,4,5-trihydroxybenzoate, (15.121)1,3-dimethyl-N-(1,1, 3-trimethyl-2,3-dihydro-1H-indol-4-yl)-1H-pyrazole-4-carboxamide, (15.122)1,3-dimethyl-N-[(3R) -1,1,3-trimethyl-2,3-dihydro-1H-indol-4-yl]-1H-pyrazole-4-carboxamide, (15.123)1,3-dimethyl-N -[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-indol-4-yl]-1H-pyrazole-4-carboxamide, (15.124) [3-( 4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2- Zin-4-yl](pyridin-3-yl)methanol, (15.125)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)- 1,2- Zin-4-yl](pyridin-3-yl)methanol, (15.126)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)- 1,2- Zin-4-yl](pyridin-3-yl)methanol, (15.127) 2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxirane-2 -yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.128) 1-{[3-(2-chlorophenyl)thiocyanate -2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl ester, (15.129) 5-(allyl Thiothio)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2, 4-triazole, (15.130) 2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-di Hydrogen-3H-1,2,4-triazole-3-thione, (15.131)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-di Fluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.132)2-{[rel(2R) , 3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-2,4-dihydro-3H-1, 2,4-triazole-3-thione, (15.133) thiocyanate 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorobenzene) Ethylene oxide-2-yl]methyl}-1H-1,2,4-triazol-5-yl ester, (15.134) thiocyanate 1-{[rel(2R,3R)-3 -(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazol-5-yl ester, (15.135) 5-(allyl -1{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)oxiran-2-yl]methyl}-1H -1,2,4-triazole, (15.136) 5-(allylthio)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4 -difluorophenyl)oxiran-2-yl]methyl}-1H-1,2,4-triazole, (15.137)2-[(2S,4S,5S)-1-(2,4 -dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione , (15.138) 2-[(2R,4S,5S)-1-(2,4-Dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2 ,4-dihydro-3H-1,2,4-triazole-3-thione, (15.139) 2-[(2R,4R,5R)-1-(2,4-dichlorophenyl)-5 -hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.140) 2-[( 2S,4R,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H- 1,2,4-triazole-3-thione, (15.141) 2-[(2S,4S,5R)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6 -trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.142)2-[(2R,4S,5R)-1 -(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole -3-thione, (15.143) 2-[(2R,4R,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6- Trimethylheptane-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.144)2-[(2S,4R,5S)-1- (2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylheptan-4-yl]-2,4-dihydro-3H-1,2,4-triazole- 3-thione, (15.145) 2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-indol-4-yl)benzene Formamide, (15.146) 2-(6-benzylpyridin-2-yl)quinazoline, (15.147) 2-[6-(3-fluoro-4-methoxyphenyl)-5- Pyridin-2-yl]quinazoline, (15.148) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinolin-1-yl)quinoline, 15.149) Abscisic acid, (15.150) 3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propane -2-yl]-1H-pyrazole-4-carboxamide, (15.151) N'-[5-bromo-6-(2,3-dihydro-1H-indol-2-yloxy)-2- Methylpyridin-3-yl]-N-ethyl-N-methylformamidine, (15.152) N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy ]-2-methylpyridin-3-yl}-N-ethyl-N-methylformamidine, (15.153) N'-{5-bromo-6-[(1R)-1-(3,5- Difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methylformamidine, (15.154) N'-{5-bromo-6-[(1S) 1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-A Formazan, (15.155) N'-{5-bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N- Methylformamidine, (15.156) N'-{5-bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl- N-methylformamidine, (15.157) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyridyl Azole-4-carboxamide, (15.158) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H- Pyrazole-4-carboxyguanamine, (15.159) N-(2-t-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl- 1H-pyrazole-4-carboxyguanamine, (15.160) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1 -methyl-1H-pyrazole-4-carboxyguanamine, (15.161) N-(5-chloro-2-isopropylbenzyl)-N-cyclopropyl-3-(difluoromethyl)- 5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.162) N-cyclopropyl-3-(difluoromethyl)-N-(2-ethyl-5-fluorobenzene Methyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.163) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(5 -fluoro-2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (15.164) N-cyclopropyl-N-(2-cyclopropyl-5-fluoro Benzyl)-3-( Fluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.165) N-(2-cyclopentyl-5-fluorobenzyl)-N-cyclopropyl -3-(Difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.166) N-cyclopropyl-3-(difluoromethyl)-5- Fluorine-N-(2-fluoro-6-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (15.167) N-cyclopropyl-3-(difluoromethyl) -N-(2-ethyl-5-methylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.168) N-cyclopropyl-3 -(Difluoromethyl)-5-fluoro-N-(2-isopropyl-5-methylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, (15.169)N -cyclopropyl-N-(2-cyclopropyl-5-methylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxyindole Amine, (15.170) N-(2-tert-butyl-5-methylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H- Pyrazole-4-carboxamide, (15.171) N-[5-chloro-2-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-5-fluoro -1-methyl-1H-pyrazole-4-carboxamide, (15.172) N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-N-[5-A Benzyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (15.173) N-[2-chloro-6-(trifluoromethyl)benzyl]-N -cyclopropyl-3-(difluoro 5-)fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.174) N-[3-chloro-2-fluoro-6-(trifluoromethyl)benzyl]- N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.175) N-cyclopropyl-3-(difluoromethyl) -N-(2-ethyl-4,5-dimethylbenzyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.176) N-cyclopropane 3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxythioguanamine, (15.177)3- (difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-indol-4-yl)-1-methyl-1H-pyrazole- 4-carboxyguanamine, (15.178) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-indole- 4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (15.179) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3- Trimethyl-2,3-dihydro-1H-indol-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (15.180) N'-(2,5-dimethyl -4-phenoxyphenyl)-N-ethyl-N-methylformamidine, (15.181) N'-{4-[(4,5-dichloro-1,3-thiazol-2-yl) Oxy]-2,5-dimethylphenyl}-N-ethyl-N-methylformamidine, (15.182) N-(4-chloro-2,6-difluorophenyl)-4-(2 -Chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine. All of the mixed components described in the above categories (1) to (15) are depending on their functional groups, and may form a salt with a suitable acid or base as needed.

Biological pesticide as a mixed component

The compound of formula (I) can be combined with a biological pesticide.

Biological pesticides include, in particular, bacteria, fungi, yeast, plant extracts and products formed by microorganisms, including proteins and secondary metabolites.

Biological pesticides include bacteria such as bacteria that form spores, bacteria that colonize the roots, and bacteria that have biological insecticides, fungicides, or nematicides.

These bacteria can be used as biological pesticides of example are: liquefaction of starch Bacillus (Bacillus amyloliquefaciens) strain FZB42 (DSM 231179), or Bacillus cereus (Bacillus cereus), specific words cereus (B. cereus) strain CNCM I -1562 or Bacillus firmus strain I-1582 (accession number CNCM I-1582) or Bacillus pumilus , specifically strain GB34 (accession number ATCC 700814) and strain QST2808 (accession number NRRL B) -30087), or Bacillus subtilis , specific strain GB03 (accession number ATCC SD-1397), or Bacillus subtilis strain QST713 (accession number NRRL B-21661) or Bacillus subtilis Strain OST 30002 (accession number NRRL B-50421), Bacillus thuringiensis , specifically B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (login number ATCC 1276), or Bacillus thuringiensis aizawai (B.thuringiensis subsp.aizaaai), specific words strain ABTS-1857 (SD-1372) , or Bacillus thuringiensis Costa Nokia species (B.thuringiensis subsp.kurstaki) strain HD-1, or Bacillus thuringiensis subsp Insecticidal (B.thuringiensis subsp. Tenebrionis) strain NB 176 (SD-5428), Pasteurella puncture (of Pasteuria Penetrans ), Pasteuria spp . ( Rotylenchulus reniformis ) -PR3 (accession number ATCC SD-5834), Streptomyces microflavus strain AQ6121 (=QRD 31.013, NRRL B-50550), Streptomyces galbus strain AQ 6047 (accession number NRRL 30232).

Examples of such fungi and yeasts that have been or can be used as biological insecticides are: Beauveria bassiana , specifically strain ATCC 74040; Coniothyrium minitans , specific words The strain CON/M/91-8 (accession number DSM-9660); Verticillium spp ., specifically the strain HRO LEC 12; Lecanicillium lecanii (formerly known as Verticillium lecanii) ), specifically strain KV01; Metarhizium anisopliae , specifically strain F52 (DSM3884/ATCC 90448); Metschnikowia fructicola , specific strain NRRL Y-30752; Paecilomyces fumosoroseus (now known as: Isaria fumosorosea ), specifically strain IFPC 200613, or strain Apopka 97 (accession number ATCC 20874); Paecilomyces lilacinus , specifically, P. lilacinus strain 251 (AGAL 89/030550); Talaromyces flavus , specifically strain V117b; Trichoderma atroviride , specific words Bacteria Strain SC1 (accession number CBS 122089); Trichoderma harzianum , specifically T. harzianum rifai T39 (accession number CNCM I-952).

Examples of such viruses that have been or can be used as biological insecticides are: Adoxophyes orana granulosis virus (GV), Cydia pomonella granulosis virus (GV), tomato night Helicoverpa armigera (cotton mites) nuclear polyhedrosis virus (NPV), Spodoptera exigua mNPV, Spodoptera frugiperda mNPV, Spodoptera littoralis NPV.

It also includes the addition of bacteria and fungi as 'bacteria' to plants or plant parts or plant organs, and uses its special properties to promote plant growth and plant health. Examples include: Agrobacterium spp ., Azorhizobium caulinodans , Azospirillum spp ., Azotobacter spp ., Bradyrhizobium spp . ), Burkholderia spp . (especially Burkholderia cepacia (formerly known as Pseudomonas cepacia )), Gigaspora spp . Or Gigaspora monosporum , Glomus spp ., Laccaria spp ., Lactobacillus buchneri , Paraglomus Spp .), Pisolithus tinctorus , Pseudomonas spp ., Rhizobium spp . (especially Rhizobium trifolii ), Rhizopogon spp . Scleroderma spp ., Suillus spp ., Streptomyces spp .

Examples of plant extracts that have been or can be used as biological pesticides and products formed by microorganisms, including proteins and secondary metabolites, are: Allium sativum, Artemisia absinthium, Neem Azadirachtin, Biokeeper WP, Cassia nigricans, Celastrus angulatus, Chenopodium anthelminticum, chitin, Armour-Zen, Dryopteris filix-mas, phoenix Equisetum arvense, Fortune Aza, Fungastop, Heads Up (Chenopodium quinoa saponin extract), pyrethrum/pyremethrin, Quasisia amara, Quercus, soap tree Quillaja), Regalia, "Requiem ^TM Insecticide", rotenone, ryania / ryanodine, Symphytum officinale, Tanacetum vulgare, thymol, Triact 70, TriCon, Tropaeulum majus, Urtica dioica, Veratrin, Viscum album, Cruciferous extract, specifically rapeseed meal or mustard powder.

As a safe component for mixed components

The compound of formula (I) may be combined with a safener, for example: benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichloropropene Dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, turfgrass Furilazole, diphenyl Isozoic acid (isethyldifen (-ethyl)), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-({4-[(methyl) Aminomethyl)amino]phenyl}sulfonyl)benzamide (CAS 129531-12-0), 4-(dichloroethenyl)-1-oxa-4-azaspiro[4.5 ] decane (CAS 71526-07-3), 2,2,5-trimethyl-3-(dichloroethenyl)-1,3- Azole (CAS 52836-31-4).

Plant and plant parts

All plant and plant parts can be treated in accordance with the present invention. At this time, the salty plant refers to all plants and plant groups, such as wild plants or crops (including natural crops) that are needed and not needed, for example: cereals (wheat, rice, durum wheat, barley, rye, oats) ,jade Rice, soybeans, potatoes, beets, sugar cane, tomatoes, beans and other vegetables, cotton, tobacco, canola, and fruit plants (apples, pears, citrus fruits and grapes). Crops may be obtained from traditional breeding methods and optimization methods or using biotechnology and genetic engineering methods or combinations of such methods, including genetically modified plants, and including protected or unprotected by plant breeders' rights. Plant cultivars. It is understood that plant parts mean all above-ground and underground parts and organs of plants, such as buds, leaves, flowers and roots. Examples can be described as: broadleaf, needles, stems, trunks, flowers, fruit bodies, Fruits and seeds, and roots, bulbs, and rhizomes. The plant parts also include harvested plants, as well as vegetative and sexually propagated materials such as cuttings, bulbs, rhizomes, cuttings and seeds.

The method of treating plants and plant parts using the compounds of formula (I) according to the invention is carried out according to conventional treatments or by acting on the surrounding, environmental or stock space, for example: soaking, spraying, evaporating, atomizing, spreading , brushing, injecting, and when processing the propagation material, one or more layers of coating may also be applied when the seed is treated specifically.

As mentioned above, all plants and parts thereof can also be treated according to the invention. In a preferred embodiment, wild plant varieties and plant cultivars or those obtained by conventional biological breeding methods (e.g., mating method or protoplast fusion method) are treated with some of the plants. In another preferred embodiment, the transgenic plants and plant cultivars (genetically modified organisms) obtained by genetic engineering methods (and, if appropriate, conventional methods), and parts thereof are treated. The terms "part" or "plant part" or "partial plant" have been described above. Particularly preferred, the present invention is a plant that processes plant cultivars obtained or used in the art. It is understood that plant cultivars mean plants having novel properties ("traits") obtained by conventional breeding methods, mutagenesis methods or recombinant DNA techniques. It can be a cultivar, a variant, a biotype or a genotype.

Transgenic plants, seed treatment and integrated items

Preferred transgenic plants or plant cultivars (which are acquired by genetic engineering) treated in accordance with the present invention, including all through genetic modification processes, receive special endowment A plant of genetic material ("trait"). Examples of such properties are to improve plant growth, increase tolerance to high or low temperatures, increase tolerance to drought or water content or soil salt content, increase flowering rate, simplify harvest, accelerate ripening, increase harvest, and increase The quality of the harvested product and/or improved nutritional value, better shelf life of the harvested product and/or improved processability. Other and particularly emphasized examples of such properties are the enhancement of the defensiveness of plants against animal pests and harmful microorganisms, such as, for example, toxins formed in plants, in particular by genetic material from Bacillus thuringiensis ( For example: the genes CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and combinations thereof to produce toxins in plants against insects, spiders, nematodes, mites , cockroaches and snails, further utilizing, for example, acquired whole plant resistance (SAR), systemin, phytoalexins, elicitors and resistance genes, and corresponding proteins and toxins, Increasing the resistance of plants to phytopathogenic fungi, bacteria and/or viruses, and also increasing the herbicidal activity of certain compounds, such as imidazolinones, sulfonylureas, glyphosata or glufosinate ( Tolerance of phosphonotricin) (eg "PAT" gene). These genes, which confer the desired trait, can also be combined into a transgenic plant. Examples of genetically modified plants include important crops such as: cereals (wheat, rice, durum wheat, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, tomatoes, peas and other vegetable varieties, cotton, tobacco , rapeseed and fruit plants (production of apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugar cane, tomatoes and canola. A special emphasis on the nature ("traits") is to increase the resistance of plants to insects, spiders, nematodes, mites and snails.

Crop Protection Law - Treatment Type

The method of treating plants and plant parts using a compound of formula (I) is carried out by conventional treatment or by applying the compound to its surroundings, habitat or stock space, for example: soaking, spraying, spraying, pouring, evaporating, dusting , atomization, spreading, foaming, painting, spreading, Injection, watering (pouring), drip irrigation, when the propagation material is treated, in particular, when the seed is treated, the powder for dry treatment, the solution of the wet treated seed, the water-soluble powder of the pulp treated seed, Encapsulating, coating one or more layers of coating, and the like. The compound of formula (I) may also be further applied by ultra low volume method or by injection of the compound of formula or formula (I) into the soil.

A preferred direct treatment of plants is the foliar application method, i.e., the compound of formula (I) is applied to the leaves, wherein the frequency of treatment and the rate of application are adjusted to match the degree of infection of the pest in question.

In the case of a whole plant active compound, the compound of formula (I) can also reach the plant via the root system. The plant can thus be treated by the action of the compound of formula (I) on the locus of the plant. The method can be, for example, immersion or mixing into soil or nutrient solution, that is, immersing in the liquid form of the compound of formula (I) at the plant site (for example, soil or hydroponic system), or by soil application method, (I) The compound is added to the locus of the plant in a solid form (for example, in the form of a granule). In the case of a rice crop, the method is to measure the solid application form of the compound of formula (I) (for example, granules) and add it to the paddy field.

Seed treatment

It has long been known to control animal pests by treating plant seeds and still in the process of improvement. However, when dealing with seeds, there are often problems that cannot be solved in a satisfactory manner. There is therefore a need to develop a method of protecting seeds and germinating plants which can dispense with, or at least significantly reduce, the additional application of pesticides during storage, after sowing or after germination of the plants. It is also desirable to provide the active compound with optimum protection of the seed and the germinating plant in an optimum amount to avoid infestation by the animal pest and not to damage the plant itself by the active compound used. In particular, the method of seed treatment should also consider the insecticidal or nematicidal properties inherent in plants that are resistant or resistant to pests, so as to provide optimal protection of seeds and germinating plants at the lowest pesticide dosage. degree.

In particular, the invention therefore also relates to the use of a compound of formula (I) for treating species A method to protect seeds and germinating plants from pests. The method for protecting a seed from a germinating plant against pests according to the present invention also comprises a method of simultaneously treating or sequentially treating the compound of the formula (I) with the mixed component in one operation. Also included are methods of treating seeds with the compound of formula (I) and the mixed components at different times.

The invention is also related to the use of a compound of formula (I) for treating seed to protect the seed from the grown plant from animal pests.

Furthermore, the invention relates to a seed which has been treated with a compound of formula (I) to protect against animal pests. The invention also relates to a seed which is treated simultaneously with a compound of formula (I) and a mixed component. The invention also relates to a seed treated at a different point in time via a compound of formula (I) and a mixed component. If the seed of the compound of formula (I) and the mixed component are treated at different time points, the individual substances may be present in different coatings of the seed. In this case, the coating comprising the compound of formula (I) and the coating comprising the mixed component may optionally be separated by an intermediate layer. The invention is also directed to a seed which has been subjected to the compound of formula (I) and the mixed component as part of the coating or as another layer or layers coated other than the coating.

Furthermore, the present invention relates to a seed which, after being treated with a compound of formula (I), is subjected to a coating process to prevent the seed from being worn by the dust.

One of the advantages of the whole plant-active compound of the compound of the formula (I) is that the seed treated by such treatment not only protects the seed itself, but also protects the seed from growing into a plant after the seed is unearthed, against the pest of the animal. In this way, it is not necessary to treat the crop immediately during sowing or shortly after sowing.

Another advantage is that the treatment of the seed through the compound of formula (I) promotes germination and emergence of the treated seed.

It can also be considered to be advantageous in that the compounds of the formula (I) can also be used in particular for the transfer of genetic seeds.

In addition, the compounds of formula (I) can also be used in combination with signal transduction technology compositions to improve colonization with commensal bacteria such as, for example, rhizobium, mycorrhizal and/or endophytic bacteria or fungi, and / or up to the best nitrogen fixation.

The compounds of formula (I) are suitable for protecting any seed of plant cultivars used in agriculture, greenhouses, forests or horticulture. More specifically, it includes cereals (eg, wheat, barley, rye, oats and millet), corn, cotton, soybeans, rice, potatoes, sunflowers, coffee, tobacco, canola, canola, and beets (eg, for sugar production) Beets and fodder beets), peanuts, vegetables (eg tomatoes, courgettes, beans, cruciferous vegetables, onions and lettuce), fruit plants, turf and ornamental plants. Of particular importance is the treatment of cereals (eg wheat, barley, rye and oats), corn, soybeans, cotton, canola, canola and rice seeds.

As also mentioned above, the compounds of formula (I) are also of particular importance for the treatment of genetically engineered seeds. At this point the plant seed typically comprises at least one heterologous gene that can control the expression of a polypeptide having insecticidal properties and/or nematicidal properties in particular. The transfected gene seed colonization of these heterologous genes may be derived from the following species of microorganisms, such as: Bacillus (Bacillus), Rhizobium (with Rhizobium), Pseudomonas (of Pseudomonas), Serratia (SERRATIA), Trichoderma (Trichoderma), rod-shaped bacilli (Clavibacter), mycorrhizal fungi (Glomus) or sticky broom mildew (Gliocladium). The invention is particularly suitable for treating seed of a transgenic gene comprising at least one heterologous gene from Bacillus sp . More preferably, the heterologous gene line is derived from Bacillus thuringiensis .

In the context of the present invention, the compound of formula (I) is applied to the seed. The seed to be treated is preferably in a sufficiently stable state to avoid damage during processing. Typically, the seed can be treated at any point during harvesting to sowing. The seeds used have generally been separated from the plant and have been removed from the shaft, shell, stalk, coating, ear or pulp. Thus, for example, seeds that have been harvested, cleaned and dried to a moisture content that can be stored can be used. Alternatively, it may be used after drying, for example, a seed which has been dried after being treated with water, for example, a bottom treatment. When dealing with rice seeds, you can also use, for example: Seeds that have been absorbed to a specific stage (chicken-chest stage) to improve germination and more consistent emergence.

When treating seeds, it is usually necessary to carefully select the amount of the compound of formula (I) and/or other additives applied to the seed so as not to damage the seed germination or to damage the grown plant. This must be ensured especially when the active compound may be phytotoxic at a particular application rate.

Typically, the compound of formula (I) is applied to the seed in a suitable formulation. Suitable formulations and methods for treating seeds are well known to those skilled in the art.

The compound of formula (I) can be converted to conventional seed dressing formulations such as solutions, emulsions, suspensions, powders, foaming agents, other coating compositions of seeds or seeds, and ULV formulations.

These formulations may be prepared in a known manner by admixing the compound of formula (I) with conventional additives, such as: conventionally used supplements, and solvents or diluents, dyes, wetting agents, dispersing agents, emulsifiers, defoaming agents. Agents, preservatives, secondary thickeners, adhesives, gibberellins, and water.

Suitable dyes which may be included in the seed dressing formulations which may be used in accordance with the invention are generally used for such purposes. At this time, a pigment which is hardly soluble in water may be used, or a water-soluble dye may be used. Examples which may be mentioned include those known by the names Rhodamin B, C.I. Red (Pigment Red) No. 112 and C.I. Solvent Red No. 1.

Suitable moisturizing agents which may be included in the seed dressing formulations which can be used in accordance with the invention are all materials which are customary for promoting wetting and agrochemically active compounds. It is preferred to use alkyl naphthalenesulfonates such as diisopropyl naphthalenesulfonate or di-isobutyl ester.

Suitable dispersing agents and/or emulsifiers which may be included in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersing agents which are customary in the formulation of agrochemically active compounds. It is preferred to use a mixture of a nonionic or anionic dispersant or a nonionic or anionic dispersant. Suitable nonionic dispersants include, in particular, ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and their phosphoric acid Chemical or sulfated derivatives. Suitable anionic dispersants are especially referred to as lignosulfonates, polyacrylates and arylsulfonate/formaldehyde condensates.

Defoamers which may be included in the seed dressing formulations which can be used in accordance with the invention are all foam inhibiting substances which are conventionally used in the formulation of agrochemically active compounds. Preferably, a polyfluorene defoamer and magnesium stearate are used.

Preservatives which may be included in the seed dressing formulations which may be employed in accordance with the invention are all materials commonly used in agrochemical compositions for such purposes. Examples thereof include dichlorophen and benzyl alcohol hemiformal.

Secondary thickeners which may be included in the seed dressing formulations which may be employed in accordance with the invention are all materials commonly used in agrochemical compositions for such purposes. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clay and highly dispersible vermiculite.

Suitable adhesives which may be included in the seed dressing formulations which can be used in accordance with the invention are all commonly used binders in the seed dressing product. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and tylose.

The gibberellins which may be included in the seed dressing formulations which can be used according to the invention are preferably gibberellins A1, A3 (=gibberellic acid), A4 and A7; particularly preferred for the use of gibberellic acid. This gibberellin is known (see R. Wegler "Chemie der Pflanzenschutz-und Schädlings bekämpfungsmittel", Vol. 2, Springer Verlag, 1970, pp. 401-412).

The seed dressing formulations which can be used in accordance with the invention can be used directly or after dilution with water for the treatment of various seeds. For example, the concentrate or its diluted water-added preparation can be used to coat seeds of cereals (eg, wheat, barley, rye, oats, and durum wheat), and corn, rice, canola, peas, beans, cotton, Sunflower, soybean and beet seeds, or each Seeds of different vegetables. Seed dressing formulations which may be used in accordance with the invention or their diluted application forms may also be used to coat seeds of transgenic plants.

When the seed dressing formulations which can be used according to the invention or the application forms thereof are used for the treatment of the seed, all suitable mixing devices which are customary for seed dressing can be used. Specifically, when the seed dressing process is carried out, the seed is placed in a mixer, and the specific amount of the desired seed dressing is added according to batch or continuous operation, and can be directly added or diluted with water and added, mixed until blending The matter is evenly distributed on the seed. The drying process can then be carried out if appropriate.

The application rate of the seed dressing formulations which can be used in accordance with the invention can vary over a considerable range. It varies depending on the particular amount of the compound of formula (I) in the formulation and on the basis of the seed. The application rate of the compound of the formula (I) is usually between 0.001 and 50 g per kg of seed, preferably between 0.01 and 15 g per kg of seed.

Animal health

In the field of animal health (ie, the field of veterinary medicine), the compounds of formula (I) are active against animal parasites, in particular ectoparasites or endoparasites. The term "endoparasite" includes, inter alia, helminths and protozoa, such as Coccidia. Extracorporeal parasites are usually and preferably arthropods, especially insects and mites.

In the field of veterinary medicine, the compound of formula (I) which is advantageously toxic to warm-blooded animals is suitable for controlling parasites present in animal husbandry and animal husbandry in livestock, farm animals, zoo animals, laboratory animals, laboratory animals and livestock animals. . It can be active against all or specific stages of development of the parasite.

Agricultural livestock include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffalos, rabbits, reindeer, elk and especially cattle and pigs; poultry such as turkeys, ducks, geese, and especially chickens Fish and crustaceans, such as: aquaculture, and insects such as bees.

Livestock animals include, for example, mammals such as hamsters, guinea pigs, rats, Mice, chinchillas, ferrets, and specific dogs, cats, birds in cages, reptiles, amphibians, or fish in aquaria.

In a preferred embodiment, the compound of formula (I) is administered to a mammal.

In another preferred embodiment, the compound of formula (I) is administered to birds, i.e., birds in a cage, and especially to birds.

The use of a compound of formula (I) to control animal parasites is intended to reduce or prevent the onset of illness, death and decline (referred to as meat, dairy, wool, hide, egg, honey, etc.), thereby achieving a more economical Simpler animal management and better animal benefits.

In the field of animal health, the term "control" or "control" means that the compound of formula (I) is effective in reducing the incidence of specific parasites in animals infected with such parasites, rendering such parasites harmless. degree. More specifically, "control" as used herein refers to a compound of formula (I) that is effective in killing, inhibiting, or inhibiting the growth of various parasites.

Arthropods include: Anoplurida, for example: Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., tube Solenopotes spp.; Mallophagida and Amblycerina and Ischnocerina, for example: Trimenopon spp., Menopon spp. , Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., ostrich Genus (Trichodectes spp.), Felicola spp.; Diptera and Nematocerina and Brachycerina, for example: Aedes spp. , Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Sand fly genus Lutzomyia spp.), Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia spp., tumor Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia, Braula spp., Musca domestica (Musca spp.), Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp. ), Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., genus Sarcophaga spp.), Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippotosca spp., Lipoptena spp. Melophagus spp., Rhinoestrus spp., Tipula spp.; Siphonapterida, for example: Pulex spp., genus Ctenocephalides spp.), Tunga spp., Xenopsylla spp., Ceratophyllus spp.; Heteropterida, for example, Cimex spp. Triatoma spp., Rhododendron genus (R Hodnius spp.), Panstrongylus spp.; and Blattaria are disturbing and sanitary pests.

Arthropods further include: Acari subfamily (Acarina) and Metastigmata, for example: Argasidae, such as Argas spp. ), Ornithodorus spp., Otobius spp.; Ixodidae, such as: Ixodes spp., Amblyomma spp., fan Rhipicephalus (Boophilus) genus, Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp. (the original genus of the genus genus); Mesostigmata, such as: Dermanyssus spp., Ornithonyssus spp., Pneumonyssus spp. Railietia spp., lung locust (Pneumonyssus spp.), Sternostoma spp., Varroa spp., Acarapis spp.; Actinedida (Prostigmata) For example, Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp. , Demodex spp., Trombula spp., Neotrombicula spp., Listrophorus spp.; and Acaridida (no gas (Astigmata), for example: Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., pterygium Genus (Pterolichus spp.), Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp. ), genus Knemidocoptes spp., Cytodites spp., Laminosioptes spp.

Examples of parasitic protozoa include: Mastigophora (Flagellata), for example: Trypanosomatidae, for example: Trypanosoma b. brucei, Trypanosoma brucei (Tbgambiense), Tbrhodesiense, T. congolense, T. cruzi, T. evansi, and trypanosomes (T. convanolense) T. equinum), T. lewisi, T. percae, T. simiae, T. vivax, Leishmania Brasiliensis), L. donovani, L. tropica, for example: Trichomonadidae, for example: Giardia lamblia, G. canis Sarcomastigophora (Rhizopoda), such as Entamoebidae, for example: Entamoeba histolytica , Hartmanellidae, for example: Acanthamoeba sp., Harman prototheca (Harmanella sp.) Apicomplexa (Sporozoa), such as: Eimeridae, such as: Eimeria acervulina, Adenoid Eimeria (E .adenoides), E. alabamensis, E. anatis, E. anseris, E. arloingi ), E. ashata, E. auburnensis, E. bovis, E. brunetti , E. canis, E. chinchillae, E. clupearum, E. columbae, reversal of Eimeria (E. contorta), E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales ), E. falciformis, E. faurei, E. flavescens, E. gallopavonis ), E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, giant Emerald E. maxima, E. media, E. meleagridis, turkey and E. meleagrimitis, and Eimeria (E. coli) .mitis), E. necatrix, E. ninakohlyakimovae, E. ovis, E. parva, Peacock E. pavonis, E. perforans, E. phasani, E. piriformis, early maturing Eimeria (E. praecox), E. residua, E. scabra, E. spec., E. stiedai , E. suis, E. tenella, E. truncata, E. truttae, Zhu Ai E.zuernii, Globidium spec., Isospora belli, canine I. canis, I. felis, genus I. ohioensis, I. rivolta, etc., Isospora (I. Spec.), I. suis, genus Cystisospora spec., Cryptosporidium spec., specifically C. parvum; For example: Toxoplasmadidae, for example: Toxoplasma gondii, Hammondia heydornii, Neospora caninum, Besnoitia besnoitii; : Sarcocystidae, for example: Sarcocystis bovicanis, S. bovihominis, S. ovicanis, and sheep sarcocystis (S. Ovifelis), S.neurona, S. spec., S. suihominis; for example: Leucozoidae, for example, S. cerevisiae (Leucozytozoon simondi); for example: Plasmodiidae, for example: Plasmodium berghei, P. falciparum, three days Plasmodium (P. malariae), Plasmodium falciparum (P.ovale), Plasmodium vivax (P. vivax), Plasmodium (P. spec.); eg, Piroplasmea, For example: Babesia argentina, B. bovis, B. canis, B. spec., Theileria parva, Theileria spec.; for example: Adeleina, for example: Hepatozoon canis, H. spec.

Pathogenic endoparasites are helminths, including: flat phylum (Platyhelmintha) (eg, monogonim, aphid, and trematode), nematodes, echinoderms, and lingual animals, including: Monogenea): for example: Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.; Aphid: Pseudophyllidea, for example: Aphididae Genus (Diphyllobothrium spp.), Spirometra spp., Schistocephalus spp., tongue Ligula spp., Bothridium spp., Diphlogonoporus spp.; Cyclophyllida, for example, Mesocestoides spp. ), Anoplocephala spp., Paranoplocephala spp., Moniezia spp., Thysanosoma spp., Thysaniezia Spp.), Avitellina spp., Stilesia spp., Cittotaenia spp., Andyra spp., Burt's genus (Bertiella spp.), Taenia spp., Echinococcus spp., Hydatigera spp., Davainea spp., Aphis genus Raillietina spp.), Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diochis spp., Aphis genus (Dipylidium spp.), Joyeuxiella spp., Diplopylidium spp.; fluke: Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., hair Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp .), Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., liver fluke Genus (Fasciola spp.), Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., double Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocotyle spp., Phytophthora (Fischoederius spp.), Gastrothylacus spp., Notocotylus spp., Catatropis spp., Plagiorchis spp. Prosthogonimus spp., Dicrocoelium spp., Eurytrema spp., Troglotrema spp., Paragonimus Spp.), Collyriclum spp., Nanophyetus spp., Opisthorchis spp., Clonorchis spp., subtestis Metorchis spp., Heterophyes spp., Metagonimus spp.; Nematode: Trichinellida, for example: Trichuris spp. ), Capillaria spp., Paracapillaria spp., Eucoleus spp., Trichomosa spp., Trichinella spp.; (Tylenchida), for example: Micronema spp., Strongyloides spp.; Rhabditina, for example: round wire Strongylus spp., Triodontophorus spp., Oesophagodontus spp., Trichonema spp., Gyalocephalus spp., Nematode Cylindropharynx spp., Poteriostomum spp., Cyclococercus spp., Cylicostephanus spp., Oesophagostomum spp., Summer locust genus Chabertia spp.), Stephanurus spp., Ancylostoma spp., Uncinaria spp., Necator spp., Bunostomum spp. , Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., 缪Muellerius spp., Protostrongylus spp., New round nematode Genus (Neostrongylus spp.), Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp. Nematode (Parelaphostrongylus spp.), Crenosoma spp., Paracrenosoma spp., Oslerus spp., Angiostrongylus spp. , Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp. Ostertagia spp., Teladorsagia spp., Marshallagia spp., Cooperia spp., Nippostrongylus spp. Heliconia (Heligmosomoides spp.), Nematodirus spp., Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., anal sphincter Ollulanus spp.; Spirurida, example Such as: Oxyuris spp., Enterobius spp., Passalus spp., Syphacia spp., Aspiculuris spp. Heterakis spp.; Ascaris spp., Toxascaris spp., Toxocara spp., Baylisascaris spp., deputy Genus (Parascaris spp.), Anisakis spp., Ascaridia spp.; Gnathostoma spp., Physaloptera spp., Nematode Thelazia spp.), Gongylonema spp., Habronema spp., Parabronema spp., Draschia spp., and genus Dracunculus spp.); Stephanofilaria spp., Parafilaria spp., Setaria spp., Loa spp., Drosophila Genus (Dirofilaria spp.), Litomosoides spp., Brucella (Brugia spp.), Wuchereria spp., Onchocerca spp., Spirocerca spp.; Acantocephala: Oligacanthorhynchida For example: Macracanthorhynchus spp., Prosthenorchis spp.; Polymorphida, for example: Filiocollis spp.; Rosary (Moniliformida), for example: Moniliformis spp.; Echinorhynchida, for example: Acanthocephalus spp., Echinorhynchus spp., like Leptorhynchoides spp.; Pentastoma: Porocephalida, for example, Linguatula spp.

In the field of veterinary and animal feeding, the compound of formula (I) is in a suitable formulation and is administered by methods known in the art, such as enteral, parenteral, transdermal or nasal routes. The administration method can be prophylactic or medical.

Thus, a specific embodiment of the invention refers to the use of a compound of formula (I) as a medicament.

Another aspect refers to the use of a compound of formula (I) as an endoparasite, in particular an anthelmintic or antiprotozoal agent. The compounds of the formula (I) are suitable for use as an endoparasite, in particular an anthelmintic or antiprotozoal agent, in the field of animal husbandry, animal husbandry, animal husbandry and hygiene.

Another aspect relates to the use of a compound of formula (I) as an antibody ectoparasite, in particular an arthropodicide, such as an insecticide or an acaricide. Another aspect refers to a compound of formula (I) as an antibody ectoparasite in animal breeding, animal husbandry, animal husbandry and health, for example, arthropodicides such as insecticides or killing agents. The use of tincture.

Vector control

The compounds of formula (I) can also be used to control vectors. In the context of the present invention, a disease vector system transmits pathogenic bacteria (eg, viruses, worms, single-celled organisms, and bacteria) from the original (plants, animals, humans, etc.) to the host arthropods, especially insects or spiders. class. The pathogen can be transmitted mechanically to the host (eg, trachoma via non-bite flies) or via injection to a host (eg, malaria parasite transmitted by mosquitoes).

Examples of vectors and diseases or pathogens transmitted by them are: 1) mosquitoes - Anopheles: malaria, filariasis; - Culex: Japanese encephalitis, filariasis, other viral diseases, creeps Propagation of insects; - Aedes: yellow fever, dengue fever, filariasis, other viral diseases; - Simuliidae: spread worms, specifically, Onchocerca volvulus; 2) : skin infections, epidemic typhus; 3) fleas: blight, mouse-type typhus; 4) flies: sleeping sickness (trypanosis); cholera, other bacterial diseases; 5) cockroaches: livestock rickets , epidemic typhus, rickettsialpox, tularamia, Saint-Louis encephalitis, tick-borne encephalitis (TBE), Crimean-Congo blood Krim-Kongo haematologic fever, Borrelia; 6) 蜱: Borelliosis, such as: Borrelia duttoni, sputum-transmitted encephalitis, Q-heat (C. faecalis) (Coxiella burnetii)), coccidiosis (Babesia canis canis).

An example of a vector in the context of the present invention is an insect, for example, a plant virus is transmitted. Aphids, flies, leafhoppers or thrips that give plants. Other vectors that transmit plant viruses are spider mites, mites, beetles and nematodes.

Examples of other vectors in the context of the present invention are insects and arachnids, such as: mosquitoes, especially Aedes, Anopheles, Anopheles, etc., which transmit pathogens to animals and/or humans, for example: Anopheles gambiae (A.gambiae), A. arabiensis, A. funestus, A. dirus (malaria) and Culex, cockroaches, fleas, flies, cockroaches And 蜱.

It is also possible to use a compound of formula (I) that breaks through resistance to control the vector.

The compounds of formula (I) are useful for the prevention of diseases and/or pathogenic bacteria transmitted by vectors. Thus, another aspect of the invention is the use of a compound of formula (I) for controlling a vector, for example, for use in agricultural, horticultural, garden and recreational activities, and also for protecting materials and stock products.

Protection of industrial materials

The compounds of formula (I) are suitable for the protection of industrial materials against insect damage or destruction, for example: Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Diptera (Lepidoptera) Psocoptera) and total tail (Zygentoma).

It is understood that the industrial materials referred to herein are inanimate materials, such as: plastics, adhesives, glues, paper and cardboard, leather, wood, processed wood products and coatings. The use of the invention is particularly suitable for protecting wood.

In another embodiment, the compound of formula (I) is used in combination with at least one other insecticide and/or at least one fungicide.

In another embodiment, the compound of formula (I) is a ready-to-use pesticide, i.e., it can be applied to the desired material without further modification. Suitable other insecticides or fungicides are specifically described above.

It has also surprisingly been found that the compounds of formula (I) can be used to protect from salt water or salt water. Touch items, specific hulls, partitions, nets, buildings, mooring equipment and signal systems to prevent contamination. Likewise, the compounds of formula (I) can be used alone or in combination with other active compounds as anti-sick plugs.

Control animal pests in the health sector

The compounds of formula (I) are suitable for controlling animal pests in the hygiene sector. More specifically, the present invention can be applied to home, health, and inventory protection products, especially insects, spiders, and mites that appear in closed spaces such as homes, factories, offices, and cars. The compounds of formula (I) may be used alone or in combination with other active compounds and/or adjuvants for controlling animal pests. These are preferably household insecticide products. The compounds of formula (I) are effective against sensitive and resistant varieties and are resistant to all stages of development.

Such pests include, for example, Arachnida, Scorpiones, Araneae and Opiliones; Chilopoda and Diplopoda; Insecta, 蜚蠊(Blattodea), Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera ), Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma, and Malacostraca Isopoda.

It may be, for example, an aerosol, a pressureless spray product such as: a pump and atomizer sprayer, an automatic spray system, an atomizer, a foam, a gel, using a vaporized sheet made of cellulose or plastic. Evaporator products, liquid evaporators, gel and membrane evaporators, screw-driven evaporators, energy-free or passive evaporation systems, insect-proof paper, insect-proof bags and insect-repellent glue, in the form of granules or dust particles. Used in the form of a spread bait or in a bait table.

Example:

The following preparations and application examples illustrate the invention, but are not limited. The product characteristics were discriminated by 1H-NMR or 13C-NMR spectrometer and/or LC-MS (gas chromatography-mass spectrometer).

The logP value method is based on EEC Directive 79/831 Annex V.A8, using HPLC (High Performance Liquid Chromatography), using reverse phase column (C18), according to the following method:

[a] The LC-MS assay was carried out in a pH range of 2.7 using a 0.1% aqueous formic acid solution and acetonitrile (containing 0.1% formic acid) as the dissolving agent, with a linear gradient from 10% acetonitrile to 95% acetonitrile. The table is represented by logP (HCOOH).

[b] The LC-MS assay was carried out in a neutral range of pH 7.8 using a linear gradient of 10% acetonitrile to 95% acetonitrile using a 0.001 molar aqueous solution of ammonium bicarbonate and acetonitrile as the dissolving agent. The table is represented by logP (neutral).

Calibration was performed using unbranched alkan-2-ones (having 3 to 16 carbon atoms) with known logP-values (logP values were determined using linear interpolation of residence time between two consecutive alkanones).

The λ-maximum is the maximum value of the chromatographic signal measured by UV spectroscopy from 200 nm to 400 nm.

The NMR data for the selected examples are listed by convention (δ value, number of hydrogen atoms, split peak multiplicity) or NMR peaks.

The solvents in the NMR spectrum are presented separately in each case.

Preparation example:

Preparation Example 1: 5-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-1,3-dimethylpyrimidine-2 ,4(1H,3H)-dione (I-1)

At 0 ° C, first add 150 mg (0.414 mmol) of 5-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)thio]phenyl}-1,3- Dimethylpyrimidine-2,4(1H,3H)-dione (I-2) to 5 ml of acetic acid. After adding a catalytic amount of sodium tungstate at 0 to 4 ° C, 510 mg (0.45 mmol) of a 3% aqueous hydrogen peroxide solution was added in portions, and the reaction mixture was stirred at room temperature for 24 h. After adding a 33% strength aqueous solution of sodium hydrogen sulfite, the mixture was extracted twice with dichloromethane. The combined organic phases were washed with water, dried over sodium sulfate and filtered. After the solvent was removed under reduced pressure, the residue was purified mjjjjjjjjjjj A white solid of 100 mg of product was obtained (63.9% of theory, 100% purity according to LC/MS).

1H-NMR (D6-DMSO) δ ppm: 8.02 (s, 1H), 7.88-7.86 (m, 1H), 7.35-7.32 (m, 1H), 4.24 - 4.13 (m, 1H), 4.02-3.90 (m) , 1H), 3.39 (s, 3H), 3.24 (s, 3H), 2.41 (s, 3H)

logP(HCOOH): 1.81 logP (neutral): 1.77

Preparation Example 2: 5-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)thio]phenyl}-1,3-dimethylpyrimidine-2,4 (1H,3H)-dione (I-2)

440 mg (1.65 mmol) of 5-iodo-1,3-dimethylpyrimidine-2,4(1H,3H)-dione and 160 mg (0.228 mmol) of bis(triphenylphosphine)palladium (at room temperature) II) Dichloride in 20ml II Stir in the alkane for 2 h. Then add 480 mg (1.79 mmol) of {2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)thio]phenyl}boronic acid and 9 ml of 2 molar sodium carbonate solution, mixture Heated under reflux for 18 h. After cooling, water was added and the reaction mixture was extracted with dichloromethane. After filtration through a silica gel layer, the combined organic phases were dried over MgSO ₄ and evaporated. After the solvent was removed under reduced pressure, the residue was purified eluted eluted eluted eluted eluted eluted elution A light yellow viscous oil of 209 g of product (33.6% of theory, 96.4% purity according to LC/MS).

1H-NMR (D ₆ -DMSO) δ ppm: 7.94 (s, 1H), 7.60-7.58 (m, 1H), 7.25-7.22 (m, 1H), 3.91-3.83 (q, 2H), 3.38 (s, 3H), 3.23 (s, 3H), 2.43 (s, 3H)

logP(HCOOH): 2.81 logP (neutral): 2.72

Preparation Example 3: 6-chloro-5-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-1,3-dimethyl Pyrimidine-2,4(1H,3H)-dione (I-3)

40 mg (0.101 mmol) of 6-chloro-5-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)thio]phenyl was added at 0-4 °C. }-1,3-Dimethylpyrimidine-2,4(1H,3H)-dione to 10 ml of chloroform. After adding 45 mg of buffer pH 7 (KH ₂ PO ₄ /Na ₂ HPO ₄ ) and 6 mg of benzyltriethylammonium chloride, 30 mg (77%, 0.134 mmol) of m-chloroperbenzene was taken at 0-4 ° C. Formic acid was added in small portions each time and the reaction mixture was stirred at room temperature for 24 h. After adding 33% strength aqueous sodium hydrogen sulfite solution, the mixture was extracted twice with dichloromethane. The combined organic phases were washed with water, dried over sodium sulfate and filtered. After the solvent was removed under reduced pressure, the residue was purified eluting eluting eluting eluting eluting eluting eluting A white solid of 18 mg of product was obtained (43.3% theory, 100% purity according to LC/MS).

1H-NMR (D6-DMSO) δ ppm: 7.80-7.78 (m, 1H), 7.40-7.37 (m, 1H), 4.32-4.20 (m, 1H), 3.97-3.84 (m, 1H), 3.56/3.55 (s, 3H), 3.24/3.23 (s, 3H), 2.42 (s, 3H) (diastereomers due to atropisomerism)

logP(HCOOH): 2.21 logP (neutral): 2.18

Preparation Example 4: 5-{2,4-Dimethyl-5-[(2,2,2-trifluoroethyl)thio]phenyl}-1,3-dimethylpyrimidine-2,4 ( 1H,3H)-dione (I-4)

120 mg (0.401 mmol) of 5-bromo-2,4-dimethylphenyl-2,2,2-trifluoroethyl sulfide and 40 mg (0.057 mmol) of bis(triphenylphosphine) were taken at room temperature. Palladium (II) dichloride in 10ml two Stir in the alkane for 2 h. Then add 100 mg (0.544 mmol) of (1,3-dimethyl-2,4-di-oxy-1,2,3,4-tetrahydropyrimidin-5-yl)boronic acid and 3 ml of 2 molar concentration of carbonic acid The sodium solution was stirred and the mixture was heated under reflux for 18 h. After cooling, water was added and the reaction mixture was extracted with dichloromethane. After filtration through the mash layer, the combined organic phases were dried over MgSO ₄ The residue was subjected to column chromatography on a 10 g SNAP column (Biotage) and purified using mobile phase ethyl acetate / cyclohexane ( gradient 10-80% ethyl acetate). A pale yellow viscous resin of 41 mg of product was obtained which crystallised upon grinding to yield a white solid (27.5% theory, purity 93.7% according to LC/MS).

1H-NMR (D ₆ -DMSO) δ ppm: 7.74 (s, 1H), 7.31 (s, 1H), 7.15 (s, 1H), 3.89-3.81 (q, 2H), 3.36 (s, 3H), 3.23 (s, 3H), 2.37 (s, 3H), 2.11 (s, 3H)

logP(HCOOH): 2.97 logP (neutral): 2.88

Preparation Example 5: 6-{2,4-Dimethyl-5-[(2,2,2-trifluoroethyl)thio]phenyl}-2,4-dimethyl-1,2,4 -three -3,5(2H,4H)-dione (I-5)

Take 100 mg (0.454 mmol) of 6-bromo-2,4-dimethyl-1,2,4-tri -3,5(2H,4H)-dione and 50 mg (0.043 mmol) of ruthenium (triphenylphosphine) palladium in 10 ml two In the alkane, with 160 mg (0.462 mmol) of 2-{2,4-dimethyl-5-[(2,2,2-trifluoroethyl)thio]phenyl}-4,4,5,5- Tetramethyl-1,3,2-dioxaborolane and 3 ml of a 2 molar aqueous sodium carbonate solution were heated under reflux for 18 h. After cooling, water was added and the reaction mixture was extracted with dichloromethane. The organic layer was combined with MgSO _{4 and} evaporated to dryness. The residue was subjected to column chromatography on a 25 g SNAP column (Biotage) and purified using mobile phase ethyl acetate / cyclohexane ( gradient 5-60% ethyl acetate). A yellow oil of 77 g of product was obtained (44.8% of theory, 95.1% purity according to LC/MS).

1H-NMR (D ₆ -DMSO) δ ppm: 7.49 (s, 1H), 7.21 (s, 1H), 3.85-3.78 (q, 2H), 3.57 (s, 3H), 3.23 (s, 3H), 2.40 (s, 3H), 2.19 (s, 3H)

logP(HCOOH): 3.38 logP (neutral): 3.29

Preparation Example 6: 6-{2-Fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-2,4-dimethyl-1, 2,4-three -3,5(2H,4H)-dione (I-6)

At 0 ° C, first add 304 mg (0.837 mmol) of 6-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)thio]phenyl}-2,4- Dimethyl-1,2,4-three -3,5(2H,4H)-dione to 8 ml of acetic acid. After adding a catalytic amount of sodium tungstate at 0 to 4 ° C, 1010 mg (0.891 mmol) of a 3% aqueous hydrogen peroxide solution was added in portions, and the reaction mixture was stirred at room temperature for 24 h. After adding 33% strength aqueous sodium hydrogen sulfite solution, the mixture was extracted twice with dichloromethane. The combined organic phases were washed with water, dried over sodium sulfate and filtered. The solvent was removed under reduced pressure to give a white solid (yield: <RTIgt;>

1H-NMR (D6-DMSO) δ ppm: 7.98-7.97 (m, 1H), 7.43-7.40 (m, 1H), 4.27-4.18 (m, 1H), 3.99-3.93 (m, 1H), 3.60 (s) , 3H), 3.24 (s, 3H), 2.43 (s, 3H)

logP(HCOOH): 2.06 logP (neutral): 2.04

Preparation Example 7: 4-ethyl-6-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-methyl-1,2, 4-three -3,5-dione (I-15)

First add 200 mg (0.57 mmol) of 6-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-methyl-1,2,4- three -3,5-dione (I-Bf-1) to 3 ml of N,N -dimethylformamide. 279 mg (0.86 mmol) of cesium carbonate and 0.07 ml (0.86 mmol) of ethyl iodide were added. The suspension was stirred at room temperature for 3 h then diluted with ethyl acetate. The organic phase was washed with cold water and a saturated sodium chloride solution, separated, dried over anhydrous sodium sulfate and filtered. After the solvent was removed under reduced pressure, the residue was purified and purified using EtOAc (EtOAc) 150 mg of the title compound were obtained (55% theory, purity 93.7% according to LC/MS).

1H-NMR (CDCl ₃ , 400MHz) δ ppm: 7.68 (d, 1H), 7.07 (d, 1H), 4.07 (q, 2H), 3.72 (s, 3H), 3.35 (q, 2H), 2.53 (s) , 3H), 1.30(t, 3H)

logP(HCOOH): 3.52

Preparation Example 8: 4-ethyl-6-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-2-methyl-1, 2,4-three -3,5-dione (I-18)

120 mg (0.32 mmol) of 4-ethyl-6-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl]-2 was added at room temperature. -methyl-1,2,4-three -3,5-dione (I-15) to 8 ml of acetone/water mixture (1:1). 195 mg (0.32 mmol) of Oxone ^{(R) was added} and the mixture was stirred at room temperature for 3 h. The organic solvent was then removed under reduced pressure, and the residue was diluted with water and evaporated. The combined organic phases were washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel using mobile phase 20% ethyl acetate / petroleum ether. 65 mg of the title compound were obtained (52% theory, purity 97.3% according to LC/MS).

1H-NMR (CDCl ₃ , 400MHz) δ ppm: 8.12 (d, 1H), 7.10 (d, 1H), 4.07 (q, 2H), 3.72 (s, 3H), 3.53-3.40 (m, 2H), 2.45 (s, 3H), 1.30 (t, 3H)

logP(HCOOH): 2.38

Similar to these examples and according to the above process, the following compounds of formula (IA) can be obtained: Where V ¹ =V ² =O and W=F

The specific optical rotation of one enantiomer of Compound I-11 was determined. Therefore, it is the R enantiomer (I-12) shown below.

Similar to these examples and according to the above process, the following compounds of formula (IB) can be obtained: Where V ¹ =V ² =O and W=F

NMR peak list method

The 1H NMR data for the selected examples are presented as a 1H NMR-peak list. Each signal peak is first expressed in δ-values (ppm), and then the signal strength is listed in parentheses. A semicolon is used as a separator between each pair of δ-value-signal strengths of the different signal peaks listed.

Therefore, the peak list type of an example is: δ ₁ (intensity ₁ ); δ ₂ (intensity ₂ ); ...; δ _i (intensity _i ); ...; δ _n (intensity _n )

The steep signal intensity is correlated with the height of the signal (in cm) in the printed NMR spectrum example and shows the true proportional relationship of the signal strength. In the wide-peak signal, a plurality of peaks or intermediate signals and their relative intensities relative to the highest intensity signal in the spectrum can be produced.

The chemical shift of the 1H NMR spectrum was calibrated using chemical shifts of tetramethylnonane and/or solvent, especially when the spectrum was measured in DMSO. Therefore, the tetramethylnonane peak is possible but not necessarily present in the NMR peak list.

The 1H NMR peak list is similar to the typical 1H NMR map printed, and therefore typically contains all of the peaks listed in a typical NMR interpretation.

In addition, as with the typical 1H NMR image printed, it also shows the solvent signal, the stereoisomer of the target compound (which is also part of the subject matter of the invention), and the peak of the signal and/or impurity.

When the compound signal is displayed in the δ-range of solvent and/or water, our 1H NMR peak list will show the general solvent peak (eg DMSO peak in DMSO-D ₆ ) and the water peak, which is usually high intensity. The average value is expressed.

The average intensity of the stereoisomer peaks and/or impurity peaks of the target compound is generally lower than the peak intensity of the target compound (eg, purity >90%).

Such stereoisomers and/or impurities are typically found in a particular process. Therefore, its peak helps to identify the reproducibility of our system by "byproduct fingerprinting."

Experts who can use known methods (MestreC, ACD-simulation, but also use the expected values of experimental analysis) to calculate the peak of the target compound can additionally use other intensity filters to separate the peaks of the target compound. This singularity method is similar to the relevant peak selection method in a typical 1H NMR interpretation.

Further details regarding the 1H NMR peak list can be found in Research Disclosure Database Number 564025.

NMR data and logP values: logP(HCOOH)=logP[a]logP(neutral)=logP[b]

Synthetic intermediate method

6-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)phenyl]-2-methyl-1,2,4-tri -3,5-dione (I-Bf-1)

Step 1: 1-(1-ethoxyvinyl)-2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)benzene

First, 15.0 g (49.5 mmol) of 1-bromo-2-fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)benzene and 21.4 g (59.4 mmol) of 1-ethoxy Vinyl vinyl) tributylstannane to 150 ml of toluene. The flask was degassed for 20 min and filled with argon. After the addition of 1.73 g (2.47 mmol) of dichlorobis(triphenylphosphine)palladium(II), the reaction mixture was heated at 110 ° C for 16 h. After cooling, water was added and the reaction mixture was extracted repeatedly with ethyl acetate. The combined organic phases were washed with water and a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate, filtered and evaporated. Residue 18 g, 60% of the desired mass according to LC/MS, was continued without further purification.

Step 2: 2-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylthio)epi]-2-oxoacetic acid (VI-1)

The obtained 18.0 g (60% purity according to LC/MS, 36.7 mmol) 1-(1-ethoxyvinyl)-2-fluoro-4-methyl-5-(2,2,2- Trifluoroethylthio)benzene was added to 90 ml of pyridine, and 16.3 g (146.9 mmol) of selenium dioxide was added. The reaction mixture was heated at 100 ° C for 16 h. After cooling, the reaction mixture was evaporated under reduced pressure. The aqueous phase was acidified using a 2N aqueous solution of hydrochloric acid and extracted with ethyl acetate. The combined organic phases were washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and evaporated. The residue was purified by silica gel using mobile phase 10% methanol / dichloromethane. 8 g of the title compound were obtained (55% of theory after 2 steps and >98% purity according to 1H NMR).

1H-NMR (D ₆ -DMSO, 400MHz) δ ppm: 7.94 (d, 1H), 7.31 (d, 1H), 3.89 (q, 2H), 2.47 (s, 3H)

Step 3: 6-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-methyl-1,2,4-tri -3,5-dione (I-Bf-1)

First, add 5.00g (16.7mmol) of 2-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-oxoacetic acid (VI-1) And 11.0 g (28% purity according to GC-MS, 25.3 mmol) 2,5,5-trimethyl-1,2,4-triazolidine-3-one to 50 ml 1,4-two To the alkane, 3.2 g (16.9 mmol) of p-toluenesulfonic acid was added, and the reaction mixture was stirred at 100 ° C for 16 h. After cooling, the reaction mixture was evaporated under reduced pressure. The combined organic phases were washed with a saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and evaporated. The residue was purified by silica gel using mobile phase 15% ethyl acetate / petroleum ether. 850 mg of the title compound was obtained (14% theory, purity 98.8% according to LC/MS).

1H-NMR (CDCl ₃ , 400MHz) δ ppm: 8.83 (b, 1H), 7.79 (d, 1H), 7.07 (d, 1H), 3.71 (s, 3H), 3.35 (q, 2H), 2.53 (s) , 3H)

logP(HCOOH): 2.62

6-[2-Fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfinyl)phenyl]-2-methyl-1,2,4-tri -3,5-dione (I-Bg-1)

Add 100 mg (0.29 mmol) of 6-[2-fluoro-4-methyl-5-(2,2,2-trifluoroethylsulfanyl)phenyl]-2-methyl-1 at room temperature , 2, 4-three -3,5-dione (I-Bf-1) to 1 ml of acetone and 1.6 ml of water. After adding 175 mg (0.29 mmol) of Oxone ^(R) , the reaction mixture was stirred at room temperature for 3 h. The organic solvent was removed under reduced pressure, the residue was diluted with water and ethyl acetate. The combined organic phases were washed with a saturated sodium chloride solution, dried over sodium sulfate, filtered and concentrated. The residue was purified by silica gel using mobile phase 20% ethyl acetate / petroleum ether. 47 mg of the title compound were obtained (45% theory, purity 97.9% according to LC/MS).

1H-NMR (CDCl ₃ , 400MHz) δ ppm: 9.00 (b, 1H), 8.14 (d, 1H), 7.10 (d, 1H), 3.71 (s, 3H), 3.56-3.41 (m, 2H), 2.45 (s, 3H)

logP(HCOOH): 1.72

Similar to these examples and according to the above preparation, the following compounds of the formula (I-Bf) or (I-Bg) can be obtained: (n=0: I-Bf; n=1: I-Bg), where V ¹ =V ² =O and W=F

NMR data logP values: logP (HCOOH) = logP [ a] logP ( neutral) = logP [b]

Applications:

Boophilus microplus - injection test

Solvent: dimethyl hydrazine

When a suitable active compound preparation is made, 10 mg of the active compound is mixed with 0.5 ml of the solvent, and the concentrate is diluted with a solvent to the desired concentration.

1 μl of the active compound solution was injected into the abdomen of 5 adult females of Boophilus microplus. The animals were transferred to a Petri dish and kept in an artificial climate chamber.

After 7 days, the potency was analyzed from the eggs that were hatched. Eggs that are not visually observable for hatching are stored in an artificial climate chamber until they hatch after about 42 days. 100% effectiveness means that no burdock produces any hatching eggs, 0% means that all eggs have hatching power.

In this test, for example, the compounds of the following preparation examples showed 100% potency at an application rate of 20 μg/animal: I-1, I-2, I-6, I-7, I-9, I-10

Meloidogyne incognita test

Solvent: 125.0 parts by weight acetone

In the preparation of a suitable active compound preparation, one part by weight of the active compound is mixed with the above amount of solvent and the concentrate is diluted with water to the desired concentration.

The container is filled with sand, active compound solution, egg/larva suspension of Meloidogyne incognita and lettuce seeds. Let the lettuce seeds germinate and grow into plants. Forming insects at the roots.

After 14 days, the potency of nematicidal was determined based on the formed insects. 100% means that no insects appeared; 0% means that the number of insects in the treated group was equivalent to the untreated control.

In this test, for example, the following preparation examples show a 100% potency at an application rate of 20 ppm: I-22

In this test, for example, the compounds of the following preparation examples showed 90% efficacy at an application rate of 20 ppm: I-1, I-21

Myzus persicae - spray test

Solvent: 78.0 parts by weight acetone

1.5 parts by weight of dimethylformamide

Emulsifier: alkyl aryl polyglycol ether

When preparing a suitable active compound preparation, the active compound is dissolved in a proportion by weight of the solvent in a specified portion by weight, and water containing 1000 ppm emulsifier concentration is added until the desired concentration is reached. It was further diluted with water containing an emulsifier to further prepare other test concentrations.

The active compound preparation of the desired concentration is sprayed onto the leaf disc of Brassica pekinensis of Myzus persicae at all stages of infection.

After 6 days, the potency was determined. 100% means that all mites have died; 0% means that no mites have died.

In this test, for example, the following preparation examples show a 100% potency at an application rate of 500 g/ha: I-7

Phaedon cochleariae - spray test

Solvent: 78.0 parts by weight acetone

1.5 parts by weight of dimethylformamide

Emulsifier: alkyl aryl polyglycol ether

When preparing a suitable active compound preparation, the active compound is dissolved in a specified proportion by weight of the solvent and the water containing 1000 ppm emulsifier concentration is added until the desired concentration is reached. The preparation was further diluted with water containing an emulsifier and further prepared to other test concentrations.

Cabbage leaves of Brassica pekinensis are sprayed with the active compound preparation at the desired concentration, dried and inoculated with larvae of Phaedon cochleariae .

After 7 days, the potency % was determined. 100% means that all locust larvae die; 0% means that no locust larvae die.

In this test, for example, the compounds of the following preparation examples showed 100% potency at an application rate of 500 g/ha: I-2, I-9, I-16, I-21

In this test, for example, the following preparation examples show an efficacy of 83% at an application rate of 500 g/ha: I-6

Tetranychus urticae - spray test, OP-resistant

Solvent: 78.0 parts by weight acetone

1.5 parts by weight of dimethylformamide

Emulsifier: alkyl aryl polyglycol ether

When preparing a suitable active compound preparation, the active compound is dissolved in a specified proportion by weight of the solvent and the water containing 1000 ppm emulsifier concentration is added until the desired concentration is reached. The preparation was diluted with water containing an emulsifier and further prepared to other test concentrations.

In preparation of the desired concentration of active compound is sprayed infection at all stages of the greenhouse spider mite (Tetranychus urticae) of kidney bean (Phaseolus vulgaris) leaf discs.

After 6 days, the potency was determined. 100% means that all spider mites die; 0% means that no spider mites die.

In this test, for example, the compounds of the following preparation examples showed 100% potency at an application rate of 500 g/ha: I-1, I-2, I-6, I-7, I-8, I-9, I -10, I-11, I-13, I-14, I-15, I-16, I-17, I-18

In this test, for example, the compounds of the following preparation examples showed 90% potency at an application rate of 500 g/ha: I-5, I-12, I-19, I-20, I-21, I-22

Tetranychus urticae - spray test, OP-resistant

Solvent: 7 parts by weight of dimethylformamide

Emulsifier: alkyl aryl polyglycol ether

When preparing a suitable active compound preparation, the active compound is dissolved in a specified proportion by weight of the solvent and the water containing 1000 ppm emulsifier concentration is added until the desired concentration is reached. The preparation was diluted with water containing an emulsifier and further prepared to other test concentrations. If it is desired to add an ammonium salt and/or a penetrant, it is separately added to the formulation solution at a concentration of 1000 ppm.

The active compound preparation of the desired concentration is sprayed on the leguminous plant ( Phenolus vulgaris ) which is severely infected by the greenhouse, Tetranychus urticae .

After 7 days, the potency % was determined. 100% means that all red leafhoppers die; 0% means that there is no death of any red leafhopper.

In this test, for example, the compounds of the following preparation examples show 100% efficacy at an application rate of 20 ppm: I-4

Claims (22)

a compound of formula (I), Wherein V ¹ and V ² each independently represent oxygen or represent sulfur; and Q represents a carbon substituted with the following groups: hydrogen, halogen, amine, cyano, aminecaraki, nitro, alkyl, haloalkyl, Alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, cycloalkyl, alkylcarbonyl, haloalkyl a carbonyl group, an alkoxycarbonyl group or an alkoxy group, or represents a nitrogen; R ¹ and R ² each independently represent a hydrogen, an amine group or an alkyl group; or an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylalkyl group, Cycloalkenyl, cyanoalkyl, hydroxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxyalkyl, haloalkoxyalkyl, alkoxy, haloalkoxy, haloalkyl, haloalkyl Or haloalkynyl, wherein the above group may be substituted by the following groups: halogen, alkyl, cycloalkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy, in particular fluorine , chlorine, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, cyclopropyl, cyano, (C ₁ -C ₄ )-alkoxy, (C ₁ -C ₃₎ - haloalkyl or (C ₁ -C ₃₎ - haloalkoxy; or represents aryl, heteroaryl, a aryl, arylalkyl or heteroarylalkyl group, wherein the above group may be substituted by the following groups: halogen, alkyl, cycloalkyl, cyano, nitro, alkoxy, haloalkyl or haloalkyl Alkoxy, in particular fluorine, chlorine, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, cyclopropyl, cyano, (C ₁ -C ₄ )-alkoxy a group, (C ₁ -C ₃ )-haloalkyl or (C ₁ -C ₃ )-haloalkoxy; W represents hydrogen or halogen; n represents the number 0, 1 or 2; Y represents hydrogen, halogen, cyano , (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )-alkoxy or (C ₁ -C ₆ )-haloalkoxy; X represents hydrogen, halogen, cyano, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl or (C ₁ -C ₆ ) - alkoxy. A compound according to claim 1, wherein V ¹ and V ² represent oxygen, respectively; Q represents nitrogen or CR ³ , wherein R ³ represents hydrogen, halogen, amine, cyano, aminecaraki, nitro, ( C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )-alkylthio, (C ₁ -C ₆ )-alkylsulfinyl, (C ₁ -C ₆ )-alkylsulfonyl, (C ₁ -C ₆ )-haloalkylthio, (C ₁ -C ₆ )-haloalkylsulfinyl, (C ₁ -C ₆ )-haloalkylsulfonyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₆ )-alkylcarbonyl, (C ₁ -C ₆ )-haloalkylcarbonyl, (C ₁ - C ₆ )-alkoxycarbonyl or (C ₁ -C ₆ )-alkoxy; R ¹ and R ² each independently represent hydrogen, amine or alkyl; or represent alkenyl, alkynyl, cycloalkyl, Cycloalkylalkyl, cycloalkenyl, cyanoalkyl, hydroxyalkyl, alkylcarbonyl, haloalkylcarbonyl, alkoxyalkyl, haloalkoxyalkyl, alkoxy or haloalkoxy, Wherein the above group may be substituted by the following groups: halogen, alkyl, cycloalkyl, cyano, nitro, alkoxy, haloalkyl or haloalkoxy, in particular fluorine, chlorine, (C ₁ -C ₃₎ - alkyl, (C ₃ -C ₆₎ - ring , Cyclopropyl, cyano, (C ₁ -C ₄₎ - alkoxy, (C ₁ -C ₃₎ - alkyl or halo (C ₁ -C ₃₎ - haloalkoxy; represents a halogen or an alkoxy Alkyl, haloalkenyl or haloalkynyl; W represents hydrogen or halogen; n represents the number 0 or 1; Y represents hydrogen, halogen, (C ₁ -C ₆ )-alkyl, (C ₃ -C ₆ )-cycloalkane , (C ₁ -C ₆ )-haloalkyl, (C ₁ -C ₆ )-alkoxy or (C ₁ -C ₆ )-haloalkoxy; X represents hydrogen, halogen, (C ₁ -C ₆ )-alkyl, (C ₁ -C ₆ )-haloalkyl or (C ₁ -C ₆ )-alkoxy. A compound according to claim 1 or 2 wherein V ¹ and V ² represent oxygen, respectively; Q represents nitrogen or CR ³ , wherein R ³ represents hydrogen, amine, halogen, cyano, (C ₁ -C ₄ ) -alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₄ )-alkylcarbonyl, (C ₁ -C ₄ )-halane a carbonyl group, a (C ₁ -C ₄ )-alkoxycarbonyl group or a (C ₁ -C ₄ )-alkoxy group; R ¹ and R ² each independently represent hydrogen, an amine group, (C ₁ -C ₄ )- Alkyl, cyano-(C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy-(C ₁ -C ₄ )-alkane , (C ₁ -C ₄ )-haloalkoxy-(C ₁ -C ₄ )-alkyl, (C ₁ -C ₄ )-alkoxy or (C ₁ -C ₄ )-haloalkoxy Or represents (C ₃ -C ₆ )-cycloalkyl or (C ₃ -C ₆ )-cycloalkyl-(C ₁ -C ₂ )-alkyl, wherein the above groups may be substituted by the following groups as needed: Fluorine, chlorine, bromine, iodine, (C ₁ -C ₃ )-alkyl, (C ₃ -C ₆ )-cycloalkyl, cyano, nitro, (C ₁ -C ₄ )-alkoxy, ( C ₁ -C ₃ )-haloalkyl or (C ₁ -C ₃ )-haloalkoxy; W represents hydrogen, chlorine or fluorine; n represents the number 0 or 1; Y represents halogen, (C ₁ -C ₄ ) -alkyl, (C ₃ -C ₆ )-cycloalkyl, (C ₁ -C ₄ )-haloalkyl, (C ₁ -C ₄ )-alkoxy or (C ₁ -C ₄ )-haloalkoxy; X represents hydrogen, halogen, (C ₁ -C ₄ )-alkane group, (C ₁ -C ₄₎ - haloalkyl or (C ₁ -C ₄₎ - alkoxy. The compound according to any one of claims 1 to 3, wherein V ¹ and V ² represent oxygen, respectively; Q represents nitrogen or CR ³ , wherein R ³ represents hydrogen, chlorine, methyl, ethyl, methoxy , cyclopropyl, cyano or trifluoromethyl; R ¹ and R ² each independently represent hydrogen, amine, methyl, ethyl, n-propyl, isopropyl, n-butyl, t-butyl, Third butyl, CH ₂ CH(CH ₃ ) ₂ , CH ₂ CN, CH ₂ CF ₃ , CH ₂ CHF ₂ , CH ₂ CH ₂ OCH ₃ , cyclopropyl, cyclobutyl or cyclopropylmethyl; W Represents fluorine; n represents the number 0 or 1; Y represents fluorine, chlorine, bromine, methyl, trifluoromethyl or methoxy; X represents hydrogen, chlorine, fluorine or methyl. The compound according to any one of claims 1 to 4, wherein V ¹ and V ² represent oxygen, respectively; Q represents nitrogen or CR ³ , wherein R ³ represents hydrogen, chlorine or methyl; R ¹ and R ² are each other Respectively represent methyl, dibutyl or amine groups, preferably each represents methyl; W represents fluorine; n represents the number 0 or 1; Y represents methyl; and X represents fluorine or methyl. Patent scope of the compounds of any one of 1 to 4, wherein V ¹ and V ² represent oxygen; Q represents N; R & lt ¹ represents methyl, ethyl, isopropyl or CH ^₂ CF _3; R ₂ Represents methyl, ethyl or CH ₂ CF ₃ ; W represents fluorine; n represents the number 0 or 1; Y represents a methyl group; and X represents a fluorine or a methyl group. The compound according to any one of claims 1 to 6, wherein Q represents CR ³ , and R ¹ , R ² , R ³ , V ¹ , V ² , n, W, X and Y have the scope of the patent application The definition of item 1 is either as defined in claim 2 or as defined in claim 3 or as defined in claim 4 or as defined in claim 5 or as claimed Definition of item 6. The compound according to any one of claims 1 to 6, wherein Q represents N, and R ¹ , R ² , V ¹ , V ² , n, W, X and Y have the same as in claim 1 Definition or as defined in the second paragraph of the patent application or as defined in claim 3 or as defined in claim 4 or as defined in claim 5 or as in claim 6 definition. a compound of formula (VI), Wherein W, Y and X have the definitions as defined in item 1 of the scope of application or as defined in item 2 of the scope of application or as defined in item 3 of the scope of application or as defined in item 4 of the scope of application or as patent application The definition of the fifth item or the definition of the sixth item of the patent application, and G represents hydrogen, (C ₁ -C ₆ )-alkyl or (C ₂ -C ₆ )-alkenyl, specifically hydrogen, C ₁ -C ₄ )-alkyl or (C ₂ -C ₄ )-alkenyl, and very particularly preferably represents hydrogen. a compound of the formula (I-Bf), Wherein W, Y, X and R ¹ have the definitions as defined in claim 1 or as defined in claim 2 or as defined in claim 3 or as defined in claim 4 or For example, the definition of the fifth paragraph of the patent application or the definition of the sixth item of the patent application. a compound of the formula (I-Bg), Wherein W, Y, X and R ¹ have the definitions as defined in claim 1 or as defined in claim 2 or as defined in claim 3 or as defined in claim 4 or For example, the definition of the fifth paragraph of the patent application or the definition of the sixth item of the patent application. A formulation, especially an agrochemical formulation, comprising at least one compound of formula (I) according to any one of claims 1 to 8. The formulation according to claim 12, further comprising at least one extender and/or at least one surface active substance. The formulation of claim 12 or 13, wherein the compound of formula (I) forms a mixture with at least one other active compound. A method for controlling a pest, in particular an animal pest, characterized by a compound of the formula (I) according to any one of claims 1 to 8 of the patent application or according to any one of claims 12 to 14 of the patent application. The formulation acts on the pest and/or its habitat. The method of claim 15, wherein the pest is an animal pest and comprises an insect, a dragonfly or a nematode, or wherein the pest is an insect, a dragonfly or a nematode. A use of a compound of the formula (I) according to any one of claims 1 to 8 or a formulation according to any one of claims 12 to 14 for controlling animal pests. The use according to claim 17, wherein the animal pest comprises an insect, a cockroach or a nematode, or wherein the animal pest is an insect, a cockroach or a nematode. It is used to protect crops according to the use of paragraph 17 or 18 of the patent application. It is used in the field of animal health according to the use of item 17 or 18 of the patent application. A method for protecting a seed or a germinating plant from pests (especially animal pests), the method comprising the step of or treating the seed with a compound of the formula (I) according to any one of claims 1 to 8 The formulation of any one of claims 12 to 14 is contacted. A seed obtained according to the method of claim 21 of the patent application.