A condensed heterocyclic compound, a preparation method thereof, an insecticidal composition and application thereof

Abstract

The application belongs to the technical field of pesticides, and particularly relates to a fused heterocyclic compound, a preparation method, an insecticidal composition and application thereof. The compound is shown in the general formula I: wherein Q represents N or CR6; X represents a cycloalkyl group, an aryl group or a heterocyclic group; R1, R2, R3, R4, R5 and R6 independently represent hydrogen, halogen, an alkyl group, an alkenyl group and the like; and the compound has excellent control effects on Spodoptera exigua, Mythimna separata, Spodoptera litura and the like.

Description

Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a fused heterocyclic compound, its preparation method, insecticidal composition, and application. Background Technology

[0002] In recent years, due to the long-term use of pest control agents, such as insecticides or fungicides, pests have acquired resistance, becoming difficult to control with existing pesticides or fungicides. Furthermore, some known pest control agents are highly toxic, or some damage ecosystems through their long-term persistence. Therefore, despite the large number of known pesticides, there is a need to develop new pest control agents with low toxicity and low residue. Summary of the Invention

[0003] This invention provides a fused heterocyclic compound, its preparation method, an insecticidal composition, and its application. The compound exhibits excellent insecticidal activity against fall armyworm, armyworm, and beet armyworm.

[0004] The technical solution adopted in this invention is as follows:

[0005] A fused heterocyclic compound, as shown in general formula I:

[0006]

[0007] Where Q represents N or CR6;

[0008] X represents a cycloalkyl, aryl, or heterocyclic group;

[0009] R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclic, and -OR, respectively. 21 -SR 21 -SOR 21 -(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR 21 -(CO)R 21 -(CO)OR 21 or -(CO)N(R) 21 )2; The alkyl, alkenyl, or alkynyl group is optionally selected from halogen, cyano, nitro, cycloalkyl, aryl, heterocyclic, -OR 21 -SR 21 -SOR 21 -(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR21 -(CO)R 21 or -(CO)N(R) 21 At least one group in )2 is replaced;

[0010] R 21 Each of these can be hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, arylalkyl, or heterocyclic alkyl, and each can be independently hydrogen, alkyl, alkenyl, or heterocyclic alkyl.

[0011] The aforementioned "cycloalkyl", "heterocyclic" or "aryl" may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R; or two adjacent carbon atoms on the ring may be connected to -(CH2)3- or -(CH2)4- to form a fused ring;

[0012] R independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl substituted with at least one group selected from halogen, hydroxyl, alkoxy, cyano or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

[0013] In one specific embodiment, X represents a C3-C8 cycloalkyl, aryl, or heterocyclic group;

[0014] R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, and -OR, respectively. 21 -SR 21 -SOR 21 -(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR 21 -(CO)R 21 -(CO)OR 21 or -(CO)N(R) 21 )2; The C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl group is optionally selected from halogen, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, -OR 21 -SR 21 -SOR 21-(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR 21 -(CO)R 21 or -(CO)N(R) 21 At least one group in )2 is replaced;

[0015] R 21 Each of these can be independently hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, aryl, heterocyclic, aryl-C1-C8 alkyl, or heterocyclic-C1-C8 alkyl;

[0016] The aforementioned “C3-C8 cycloalkyl”, “heterocyclic” or “aryl” may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halogenated C1-C8 alkyl, halogenated C2-C8 alkenyl, halogenated C2-C8 ynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R; or two adjacent carbon atoms on the ring may be connected to -(CH2)3- or -(CH2)4- to form a fused ring;

[0017] R independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted with at least one group selected from halogen, hydroxyl, C1-C8 alkoxy, cyano or C1-C8 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo-C1-C8 alkoxy.

[0018] In another specific embodiment, X represents a C3-C6 cycloalkyl, aryl, or heterocyclic group;

[0019] R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, and -OR, respectively. 21 -SR 21-SOR 21 -(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR 21 -(CO)R 21 -(CO)OR 21 or -(CO)N(R) 21 )2; The C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl group is optionally selected from halogen, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, -OR 21 -SR 21 -SOR 21 -(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR 21 -(CO)R 21 or -(CO)N(R) 21 At least one group in )2 is replaced;

[0020] R 21 Each of these can be independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, aryl, heterocyclic, aryl-C1-C6 alkyl, or heterocyclic-C1-C6 alkyl;

[0021] The aforementioned “C3-C6 cycloalkyl”, “heterocyclic” or “aryl” may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halogenated C1-C6 alkyl, halogenated C2-C6 alkenyl, halogenated C2-C6 ynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R;

[0022] R independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl substituted with at least one group selected from halogen, hydroxyl, C1-C6 alkoxy, cyano or C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenylC1-C6 alkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy.

[0023] In the definitions of compounds shown in the above general formulas and in all the following structural formulas, the technical terms used, whether alone or in compound terms, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chain or branched. For example, in the compound term "cycloalkylalkyl," the alkyl group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group is, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, alkenyl groups are, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl groups are, for example, ethynyl, propynyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds can be in any position in each unsaturated group. Cycloalkyl groups are carbocyclic saturated ring systems having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl groups are monocyclic alkenyl groups having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bonds can be in any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0024] Unless otherwise specified, the term "aryl" in this invention includes, but is not limited to, phenyl, naphthyl, and... The "heterocyclic group" includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups. And, including but not limited to, heteroaryl groups, i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms and optionally fused with benzo[a] rings, wherein 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms are selected from oxygen, nitrogen, and sulfur, for example

[0025] If a group is substituted by another group, this should be understood to mean that the group is substituted by one or more identical or different groups selected from those groups mentioned. Furthermore, the identical or different substitution characters contained in the identical or different substituents are chosen independently and may be identical or different. This also applies to ring systems formed from different atoms and units. Meanwhile, the scope of the claims excludes compounds that are chemically unstable under standard conditions, as known to those skilled in the art.

[0026] Furthermore, unless otherwise specified, the phrase "replaced by at least one group" in this invention refers to being replaced by, for example, 1, 2, 3, 4, or 5 groups; groups without specific attachment positions (including heterocyclic groups, aryl groups, etc.) can be attached at any position, including positions attached to C or N; if it is substituted, the substituent can also be substituted at any position, as long as it conforms to the rules of chemical bond attachment. For example, a heteroaryl group substituted by one methyl group. Can represent wait.

[0027] If various functional groups are present, the present invention also includes any ketone and enol tautomer forms, mixtures thereof, and salts thereof.

[0028] The method for preparing the fused heterocyclic compound includes the following steps:

[0029] The compound of general formula II is reacted with the compound of general formula III to prepare the compound of general formula I. The reaction equation is as follows:

[0030]

[0031] In this case, either Q1 or Q2 is a halogen, and the other is a... The definitions of R1, R2, R3, R4, R5, Q, and X are as described above.

[0032] In one specific embodiment, the reaction is carried out in the presence of a solvent.

[0033] In another specific embodiment, the solvent is an organic solvent / water.

[0034] In another specific embodiment, the organic solvent is selected from at least one of aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, THF, acetonitrile, methanol, ethanol, isopropanol, dichloroethane, DMSO, dioxane, dichloromethane, or ethyl acetate.

[0035] In another specific embodiment, a base and a catalyst are added during the reaction.

[0036] In another specific embodiment, the base is selected from at least one of inorganic or organic bases, such as at least one of K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KI, NaI, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, NaH, KH, DMAP, pyrazole, triethylamine, or DIEA.

[0037] In another specific embodiment, the catalyst is selected from Pd(dppf)Cl2, Pd(dppf)Cl2 . At least one of CH2Cl2, Pd(OAc)2, PdCl2, Pd(PPh3)4, or PdCl2(PPh3)2.

[0038] The present invention also provides an intermediate, as shown in general formula II.

[0039] Salts of the compounds suitable for use according to the present invention, such as salts of bases or salts of acid addition, are conventional, non-toxic salts, preferably agriculturally and / or physiologically acceptable salts. Salts with inorganic bases are preferred, such as alkali metal salts (e.g., sodium, potassium, or cesium salts), alkaline earth metal salts (e.g., calcium or magnesium salts), ammonium salts; or salts with organic bases, particularly organic amines, such as triethylammonium salts, dicyclohexylammonium salts, N,N'-dibenzylethylidene diammonium salts, pyridinium salts, methylpyridinium salts, or ammonium ethanolate salts; salts with inorganic acids (e.g., hydrochlorides, hydrobromates, dihydrogen sulfates, trihydrogen sulfates, or phosphates); and salts with organic carboxylic acids or organic sulfonic acids (e.g., formates, acetates, trifluoroacetates, maleates, tartrates, methanesulfonates, benzenesulfonates, or 4-toluenesulfonates). Tertiary amines, such as some compounds of the present invention, are known to form N-oxides, which are also salts of the present invention.

[0040] Depending on the nature of the substituents, compounds of Formula I can exist as geometrically and / or optically active isomers or mixtures of corresponding isomers with different compositions. These stereoisomers are, for example, enantiomers, diastereomers, transisomers, or geometric isomers. Therefore, the present invention includes pure stereoisomers and any mixtures of these isomers.

[0041] The present invention also relates to a method for controlling animal pests, wherein the compound of formula I can act on the animal pests and / or their habitats. The control of said animal pests is preferably carried out in agriculture and forestry, as well as in the protection of materials. Methods preferably excluded from this method include surgical and therapeutic treatments for humans or animals, and diagnostic methods performed on humans or animals.

[0042] The present invention also relates to the use of compounds of Formula I as insecticides, and in particular as crop protectants.

[0043] In the context of this application, the term "insecticide" often also includes the term "crop protectant".

[0044] Compounds of Formula I, exhibiting good plant tolerance, favorable homeothermic animal toxicity, and good environmental compatibility, are suitable for the following uses: protecting plants and plant organs from biotic and abiotic stresses; increasing harvest yield; improving the quality of harvested material; and controlling animal pests, especially insects, arachnids, worms, nematodes, and mollusks, encountered in agriculture, horticulture, livestock farming, aquaculture, forestry, landscaping and recreational facilities, protection of stored products and materials, and in the sanitation sector. These compounds are preferably used as insecticides. They are effective against commonly susceptible and resistant species and are resistant to all or part of the developmental stages. The aforementioned pests include, but are not limited to: pests from the phylum Arthropoda, especially from the class Arachnida; pests from the class Chilopoda; pests from the orders Collembola; pests from the class Diplopoda; pests from the class Insecta; pests from the order Coleoptera; pests from the order Diptera; pests from the order Heteroptera; pests from the order Homoptera; pests from the order Hymenoptera; and pests from the order Isopoda. a) Pests, including those from the order Isoptera, Lepidoptera, Orthoptera or Saltatoria, Phthiraptera, Psocoptera, Siphonaptera, Thysanoptera, Zygentoma (=Thysanura) (a) (a) (a) (b) (c) (c) (d ...

[0045] At certain concentrations and application rates, compounds of Formula I may also optionally be used as insecticides, safeners, growth regulators, or agents for improving plant performance; as fungicides and gametoxins, for example as fungicides, antifungals, bactericides, antivirals (including antiviral agents), or as agents against MLO (mycoplasma-like organisms) and RLO (rickettsia-like organisms). Where appropriate, they may also be used as intermediates or precursors for the synthesis of other active ingredients.

[0046] The present invention also relates to formulations comprising at least one compound of formula I and forms of use prepared therefrom as insecticides, such as impregnation, dripping, and spraying liquids. In some cases, the forms of use include other insecticides and / or adjuvants with enhancing effects, such as penetrants, for example, vegetable oils (e.g., rapeseed oil, sunflower oil), mineral oils (e.g., paraffin oil), alkyl esters of vegetable fatty acids (e.g., rapeseed oil methyl ester or soybean oil methyl ester), or alkanol alkoxylates; and / or spreaders, such as alkylsiloxanes and / or salts (e.g., organic or inorganic ammonium or phosphate salts, such as ammonium sulfate or diammonium hydrogen phosphate); and / or retention promoters, such as dioctyl sulfosuccinic acid or hydroxypropyl guar gum polymers; and / or wetting agents, such as glycerin; and / or fertilizers, such as ammonium-, potassium-, or phosphorus-containing fertilizers.

[0047] Commonly used formulations include, for example, water-soluble liquids (SL), emulsifiable concentrates (EC), emulsions (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR), and capsule concentrates (CS); these formulations and other possible formulation types are described, for example, by Crop Life International in the following literature: Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, and FAO Plant Production and Protection Papers-173 – developed by the FAO / WHO Joint Committee on Pesticide Standards, 2004, ISBN: 9251048576. In addition to one or more compounds of Formula I, the formulations may optionally contain other agrochemically active ingredients.

[0048] These are preferably formulations or forms of use comprising: adjuvants, such as fillers, solvents, spontaneous accelerators, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners; and other adjuvants, such as adjuvants. In this context, an adjuvant is a component that enhances the biological efficacy of the formulation, while the component itself does not have any biological efficacy. Examples of adjuvants are agents that promote retention, spreading, adhesion to leaf surfaces, or penetration.

[0049] These formulations are prepared in a known manner, for example by mixing a compound of formula I with an adjuvant, such as a filler, solvent, and / or solid carrier, and / or other adjuvants such as surfactants. The formulation is prepared in a suitable device or before or during application.

[0050] The adjuvant used may be a formulation suitable for imparting the compound of Formula I or a substance prepared from such formulations that has specific properties for use in a form of application (such as ready-to-use insecticides, such as spray liquids or seed dressing products), said specific properties being, for example, specific physical properties, technical properties and / or biological properties.

[0051] Suitable fillers are, for example, water, polar and nonpolar organic chemical liquids, such as those selected from: aromatic or non-aromatic hydrocarbons (e.g., paraffin, alkylbenzene, alkylnaphthalene, chlorobenzene), alcohols and polyols (which may optionally be substituted, etherified and / or esterified), ketones (e.g., acetone, cyclohexanone), esters (including fats and oils) and (poly)ethers, unsubstituted and substituted amines, amides, lactams (e.g., N-alkylpyrrolidone) and lactones, sulfones and sulfoxides (e.g., dimethyl sulfoxide).

[0052] If the filler used is water, organic solvents may also be used as co-solvents. Useful liquid solvents include: aromatic compounds such as xylene, toluene, or alkylnaphthalene; chlorinated aromatic and aliphatic hydrocarbons such as chlorobenzene, vinyl chloride, or dichloromethane; aliphatic hydrocarbons such as cyclohexane or paraffins such as mineral oil fractions, mineral oils, and vegetable oils; alcohols such as butanol or ethylene glycol and their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; highly polar solvents such as dimethylformamide, dimethylacetamide, and dimethyl sulfoxide, as well as water.

[0053] In principle, all suitable solvents may be used. Examples of suitable solvents include aromatic hydrocarbons such as xylene, toluene, or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzene, vinyl chloride, and dichloromethane; aliphatic hydrocarbons such as cyclohexane, paraffin, mineral oil fractions, mineral oil, and vegetable oil; alcohols such as methanol, ethanol, isopropanol, butanol, or ethylene glycol and their ethers and esters; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, or cyclohexanone; strongly polar solvents such as dimethyl sulfoxide; and water.

[0054] In principle, all suitable carriers may be used. Useful carriers include, in particular, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, magnesia, montmorillonite, or diatomaceous earth; and ground synthetic materials such as finely ground silica, alumina, and natural or synthetic silicates, resins, waxes, and / or solid fertilizers. Mixtures of these carriers may also be used. Useful carriers for granules include, for example, crushed and graded natural rocks such as calcite, marble, pumice, sepiolite, and dolomite; and synthetic granules of inorganic and organic powders; and granules of organic materials such as sawdust, paper, coconut husks, corn cobs, and tobacco stems.

[0055] Liquefied gaseous fillers or solvents can also be used. Particularly suitable fillers or carriers are those that are gaseous at ambient temperature and atmospheric pressure, such as aerosol propellant gases, including halogenated hydrocarbons, as well as butane, propane, nitrogen, and carbon dioxide.

[0056] Examples of emulsifiers and / or foaming agents, dispersants, or wetting agents, or mixtures of these surfactants, having ionic or nonionic properties, include: salts of polyacrylic acid; salts of lignin sulfonic acid; salts of phenol sulfonic acid or naphthalene sulfonate; condensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines or substituted phenols (preferably alkylphenols or arylphenols); salts of sulfosuccinates; taurine derivatives (preferably alkyl taurine esters); phosphate esters of polyethoxylated alcohols or phenols; fatty acid esters of polyols; and derivatives of compounds containing sulfates, sulfonates, and phosphates, such as alkylaryl polyethylene glycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates, protein hydrolysis products, lignin sulfite waste, and methylcellulose. The presence of a surfactant is advantageous when one of the compounds of Formula I above and / or one of the inert carriers above is insoluble in water and is applied in water.

[0057] Other adjuvants that may be present in formulations and derived forms of use include colorants, such as inorganic pigments like iron oxide, titanium dioxide, and Prussian blue; and organic dyes, such as alizarin dyes, azo dyes, and metal phthalocyanine dyes; as well as nutrients and micronutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum, and zinc.

[0058] Additional components may be stabilizers that improve chemical and / or physical stability, such as low-temperature stabilizers, preservatives, antioxidants, light stabilizers, or other reagents. Foaming agents and defoamers may also be present.

[0059] In addition, formulations and derived forms of use may contain the following substances as additional adjuvants: adhesives, such as carboxymethyl cellulose; and natural and synthetic polymers in powder, granule, or latex form, such as gum arabic, polyvinyl alcohol, and polyvinyl acetate; or natural phospholipids, such as cephalin, lecithin, and synthetic phospholipids. Other possible adjuvants include mineral oils and vegetable oils.

[0060] Optionally, other adjuvants may be present in the formulation and in forms of use derived therefrom. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetrants, retention enhancers, stabilizers, chelating agents, complexing agents, wetting agents, and spreading agents. Generally, compounds of Formula I can be combined with any solid or liquid additive commonly used for formulation purposes.

[0061] Useful retention promoters include all those substances that reduce kinetic surface tension, such as dioctyl sulfosuccinate; or all those substances that increase viscoelasticity, such as hydroxypropyl guar polymer.

[0062] In the context of this invention, useful penetrants include all those substances commonly used to enhance the penetration of active agricultural chemicals into plants. Hereinafter, penetrants are defined as those that penetrate the plant epidermis by (typically aqueous) application liquids and / or by spray coatings, thereby increasing the fluidity of the active ingredient within the epidermis. Examples include: alcohol alkoxylates, such as coconut fat ethoxylate (10) or isotrigine ethoxylate (12); fatty acid esters, such as rapeseed oil methyl ester or soybean oil methyl ester; fatty amine alkoxylates, such as tallow amine ethoxylate (15); or ammonium and / or phosphate salts, such as ammonium sulfate or diammonium hydrogen phosphate.

[0063] The formulation preferably comprises 0.00000001% by weight to 98% by weight of a compound of formula I, more preferably 0.01% by weight to 95% by weight of a compound of formula I, and most preferably 0.5% by weight to 90% by weight of a compound of formula I, based on the weight of the formulation.

[0064] The content of the compound of Formula I in the application form prepared from the formulation (especially insecticide) can vary over a wide range. The concentration of the compound of Formula I in the application form is typically from 0.00000001% by weight to 95% by weight, preferably from 0.00001% by weight to 1% by weight, based on the weight of the application form. Application is carried out in a conventional manner suitable for the application form.

[0065] Compounds of Formula I can also be used in mixtures with one or more of the following substances: suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbial agents, beneficial organisms, pesticides, fertilizers, bird repellents, phytotonics, sterilizing agents, safeners, chemical pheromones, and / or plant growth regulators, thereby, for example, broadening the spectrum of action, prolonging the duration of action, increasing the rate of action, preventing rejection, or preventing the development of resistance. In addition, such active ingredient compositions can improve plant growth and / or tolerance to abiotic factors (such as high or low temperatures), drought, or tolerance to high water content or soil salinity. They may also improve flowering and fruiting performance, optimize germination capacity and root development, promote harvesting and increase yield, influence ripening, improve the quality and / or nutritional value of harvested products, prolong storage life, and / or improve the processing properties of harvested products.

[0066] Additionally, compounds of Formula I can be present in mixtures with other active ingredients or chemical pheromones such as attractants and / or bird repellents and / or plant activators and / or growth regulators and / or fertilizers. Similarly, compounds of Formula I can be used in mixtures with reagents used to improve plant performance such as growth, yield, and the quality of harvested material.

[0067] In a particular embodiment of the invention, the compound of formula I is a formulation in the form of a mixture with other components or in a form of use prepared from such formulations, preferably those described below.

[0068] If one of the compounds mentioned below can exist in multiple tautomeric forms, these forms are included even if they are not explicitly mentioned in various cases.

[0069] Insecticides / Acaricides / Nematodes

[0070] The active ingredients mentioned in this article by their "generic names" are known and described, for example, in The Pesticide Manual, 16 th Ed., British Crop Protection Council 2012, or available on the Internet (e.g., http: / / / / www.alanwood.net / pesticides Found on ).

[0071] (1) Acetylcholinesterase (AChE) inhibitors, such as carbamates, including alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, and furathioc. (ARB), isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC, and xylylcarb; or organophosphates, such as azamethiphos and azinphos-ethyl. Azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chloropyrifos, chloropyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, didrotophos, and others. Dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl o-(methoxyaminothiophosphoryl)salicylic acid, isoxathionMalathion, mecarbam, methamidophos, methidathion, mevinphos, monocotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, and other similar pesticides. Piririmiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclofon, and vamidothion.

[0072] (2) GABA-gated chloride channel antagonists, such as cyclopentadiene organochlorines, such as chlordane and endosulfan; or phenylpyrazoles, such as ethiprole and fipronil.

[0073] (3) Sodium channel modulators / voltage-dependent sodium channel blockers, such as pyrethroids, including acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, and bioallethrin S-cyclopentenyl isomer. isomer), pyrethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomer] isomers]), deltamethrin, empenthrin[(EZ)-(1R)isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin[(1R)-trans isomers], phenothrin[(1R)-trans isomers][isomer]), prallethrin, pyrethrine, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)isomers], tralomethrin, and transfluthrin; or DDT; or methoxychloride.

[0074] (4) Nicotinic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.

[0075] (5) Allosteric activators of nicotinic acetylcholine receptors (nAChR), such as spinosides, such as spintoram and spinosad.

[0076] (6) Chloride channel activators, such as abamectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin and milbemectin.

[0077] (7) Juvenile hormone mimics, such as hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

[0078] (8) Active ingredients with unknown or non-specific mechanisms of action, such as

[0079] Alkyl halides, such as methyl bromide and other alkyl halides; or chloropicrine or thiocyanate or borax or tartar emetic.

[0080] (9) Selective antifeedants, such as pymetrozine or flonicamid.

[0081] (10) Mite growth inhibitors, such as tetradifon, thiamethoxam and diflovidazin or etoxazole.

[0082] (11) Microbial disruptors of insect intestinal membranes, such as Bacillus thuringiensis subspecies israelensis, Bacillus sphaericus, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis, and BT plant proteins: Cry1Ab, Cry1Ac, Cry1Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.

[0083] (12) Inhibitors of oxidative phosphorylation, ATP interfering agents, such as butyl ether urea or organotin compounds, such as triazole tin, tricyclic tin and fenbutatin oxide or propargite or tetradifon.

[0084] (13) Oxidative phosphorylation decoupling agents that interrupt the H proton gradient, such as chlorfenapyr, dinitrocresol (DNOC) and sulfluramid.

[0085] (14) Nicotinic acetylcholine receptor antagonists, such as bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0086] (15) Type O chitin biosynthesis inhibitors, such as bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[0087] (16) Type I chitin biosynthesis inhibitors, such as buprofezin.

[0088] (17) Ecchymosis inhibitors (especially for Diptera, i.e., Diptera), such as cyromazine.

[0089] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0090] (19) Octopus aminergic agonists, such as amitraz.

[0091] (20) Complex-III electron transport inhibitors, such as hydramethylnone, acequinocyl, or fluacrypyrim.

[0092] (21) Complex-type I electron transport inhibitors, such as those selected from METI acaricides, such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or rotenone (Rotenone).

[0093] (22) Voltage-gated sodium channel blockers, such as indoxacarb or metaflumizone.

[0094] (23) Inhibitors of acetyl-CoA carboxylase, such as tetronic acid and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[0095] (24) Complex-IV electron transport inhibitors, such as phosphine, such as aluminum phosphide, calcium phosphide, phosphine hydrogen and zinc phosphide; or cyanide.

[0096] (25) Complex-type II electron transport inhibitors, such as cyenopyrafen and cyflumetofen.

[0097] (28) Lanni base receptor effectors, such as diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide;

[0098] Other active ingredients include afidopyropen, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, dicofol, diflovidazin, fluensulphone, fometoquin, flufenerim, flufenoxystrobin, and flufeniprin. role), fluopyram, flupyradifurone, fufenozide, heptafluthrin, imidaclothiz, iprodione, meperfluthrin, paichongding, pyflubumide, pyrifluquinazon, pyriminostrobin, tetramethylfluthrin, and iodomethane; and based on Bacillus thuringiensis. The reagents of firmus, I-1582, BioNeem, Votivo, and the following compounds: 3-bromo-N-{2-bromo-4-chloro-6-[(1-cyclopropylethyl)carbamoyl]phenyl}-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known from WO2005 / 077934) and 1-{2-fluoro-4-methyl-5-[(2,2,2-trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1H-1,2,4-triazol-5-amine (known from WO2006 / 043635), {1'-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl] -5-Fluorospiro[indol-3,4'-piperidin]-1(2H)-yl}(2-chloropyridin-4-yl) methyl ketone (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-diazaspiro[4,5]dec-3-en-2-one (known from WO2009 / 049851), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-Dazaspiro[4.5]dec-3-en-4-yl ethyl carbonate (known from WO2009 / 049851), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO2004 / 099160), 4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known from WO2003 / 076415), PF1364 (CAS Registry No. 1204776-60-2), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-{2-oxo-2-[ (2,2,2-trifluoroethyl)amino]ethyl}benzamide (known from WO2005 / 085216), 4-{5-[3-chloro-5-(trifluoromethyl)phenyl]-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl}-N-{2-oxo-2-[(2,2,2-trifluoroethyl)amino]ethyl}-1-naphthylcarboxamide (known from WO2009 / 002809), 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazine carboxylate methyl ester (known from WO2005 / 085216), 2-[2 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazine carboxylate (known from WO2005 / 085216), 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazine carboxylate (known from WO2005 / 085216), 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazine carboxylate (known from W Known from O2005 / 085216), 1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazole-2-yl]methyl}-1H-pyrazole-5-carboxamide (known from WO2010 / 069502), N-[2-(5-amino-1,3,4-thiadiazol-2-yl)-4-chloro-6-methylphenyl]-3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazole-5-carboxamide (known from CN102057925), 3-chloro-N-(2-cyanopropyl-2-yl)-N-[4-(1,1,1,2,3,3,[3-Hepheptafluoroprop-2-yl]-2-methylphenyl]phthalamide (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-oxazol-3-yl]-2-methyl-N-(1-oxothionylbutane-3-yl)benzamide (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), 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (known from WO2010 / 129500), 8-chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (known from WO2012 / 034472 ... Known from WO2009 / 080250), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1-oxothiacyclobutane-3-yl)benzamide (known from WO2012 / 029672), 1-[(2-chloro-1,3-thiazo-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidine-1-onthium-2-phenol salt (known from WO2009 / 099929), 1-[(6 [-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1-onthium-2-phenol salt (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]aza (known from WO2010 / 069266), (2E)-1-[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-imide Pentylhydrazine benzamide (known from WO2010 / 060231), 4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1-yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN101337940), and N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1-(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1H-pyrazole-5-carboxamide (known from WO2008 / 134969).

[0099] fungicides

[0100] The active ingredients identified in this article by their common names are known and documented, for example, in “Pesticide Manual” or on the Internet (e.g., http: / / www.alanwood.net / pesticides).

[0101] (1) Ergosterol biosynthesis inhibitors, such as (1.1) aldimorph, (1.2) azaconazole, (1.3) bitertanol, (1.4) bromuconazole, (1.5) cyproconazole, (1.6) diclobutrazole, (1.7) difenoconazole, (1.8) diniconazole, (1.9) diniconazole-M, (1.10) dodemorph, and (1.11) dodemorph acetate. (1.12) Acetate, (1.13) Etaconazole, (1.14) Fenarimol, (1.15) Fenbuconazole, (1.16) Fenhexamid, (1.17) Fenpropidin, (1.18) Fenpropimorph, (1.19) Fluquinazole (1.20) flurprimidol, (1.21) flusilazole, (1.22) flutriafole, (1.23) furconazole, (1.24) furconazole-cis, (1.25) hexaconazole, (1.26) imazalil, (1.27) imazalil sulfate sulfate), (1.28) imibenconazole, (1.29) ipconazole, (1.30) metconazole, (1.31) myclobutanil, (1.32) naftifine, (1.33) nuarimol, (1.34) oxpoconazole, (1.35) paclobutrazol, (1.36) pefurazoate, (1.37) penconazole, (1.38) piperalin, (1.39) prochloraz, (1.40) propiconazole, (1.41) Prothioconazole, (1.42) Pyributicarb, (1.43) Pyrifenox, (1.44) Quinconazole, (1.45) Simeconazole, (1.46) Spiroxamine, (1.47) Tebuconazole, (1.48) Terbinafine, (1.49) Tetraconazole, (1.50) Triadimefon, (1.51) Triadimenol, (1.52) Trididemorph, (1.53) Triflumizole, (1.54) Triforine, (1.55) Triticonazole, (1.56) Unicazole (1.57) uniconazole, (1.58) viniconazole, (1.59) voriconazole, (1.60) 1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol, (1.61) methyl 1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazol-5-carboxylic acid, (1.62) N'-{5-( (1.63)N-ethyl-N-methyl-N'-{2-methyl-5-(trifluoromethyl)-4-[3-(trimethylsilyl)propoxy]phenyl}iminoformamide, (1.64)o-[1-(4-methoxyphenoxy)-3,3-dimethylbutan-2-yl]1H-imidazolium-1-thiocarbamate, (1.65)pyrisoxazole.

[0102] (2) Respiratory inhibitors (respiratory chain inhibitors), such as (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) furamepyr, (2.10) furmecyclox, (2.11) (2.12) Pyrazothiamethoxam (trans-episode racemates), (2.13) Pyrazothiamethoxam (trans-episode racemates 1R, 4S, 9S), (2.14) Pyrazothiamethoxam (trans-episode racemates 1S, 4R, 9R), (2.15) Pyrazothiamethoxam (cis-episode racemates 1RS, 4SR, 9RS), (2.16) Pyrazothiamethoxam (cis-episode racemates 1R, 4S, 9R), (2.17) Pyrazothiamethoxam (cis-episode racemates 1R, 4S, 9R) (S, 4R, 9S), (2.18) mepronil, (2.19) oxycarboxin, (2.20) penflufen, (2.21) penthiopyrad, (2.22) sedaxane, (2.23) thifluzamide, (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- (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-methoxypropyl-2-yl]-3-(difluoromethyl)-1-methyll-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-methanolnaphthyl-5-yl]-3-(difluoromethyl)-1-methyll-1H-pyrazole-4-carboxamide, and (2.31) N-[(1R,4S)-9-(dichloromethylene)-1,2,3,4-tetrahydro-1,4-methanolnaphthyl-5-yl]-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (2.32) 3-(difluoromethyl)-1-methyllN-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)- 1H-pyrazole-4-carboxamide, (2.33)1,3,5-trimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl)-1H-pyrazole-4-carboxamide, (2.34)1-methyl-3-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl)-1H-pyrazole-4-carboxamide, (2.35)1-methyl-3-(trifluoromethyl)-N-[(1R)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, (2.36) 1-Methyl-3-(trifluoromethyl)-N-[(1S)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, (2.37) 3-(difluoromethyl)-1-methyllN-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, (2.38) 3-(difluoromethyl)-1-methyllN-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, (2.39) 1, 3,5-Trimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, (2.40)1,3,5-trimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, (2.41) benodanil, (2.42)2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl)pyridine-3-carboxamide, (2.43) isofetamid.

[0103] (3) Respiratory inhibitors acting on complex III of the respiratory chain (respiratory chain inhibitors), such as (3.1) ametoctradin, (3.2) amisulbrom, (3.3) azoxystrobin, (3.4) cyazofamid, (3.5) coumethoxystrobin, (3.6) coumoxystrobin, (3.7) dimoxystrobin, (3.8) enestroburin, and (3.9) famoxad. (3.10) Fenamidone, (3.11) Flufenoxystrobin, (3.12) Fluoxastrobin, (3.13) Kresoxim-methyl, (3.14) Metominostrobin, (3.15) Orysastrobin, (3.16) Picoxystrobin, (3.17) Pyraclostrobin, (3.18) Pyrametostrobin, ( 3.19) Pyraoxystrobin, (3.20) Pyribencarb, (3.21) Trilopyricarb, (3.22) Trifloxystrobin, (3.23) (2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-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-(methoxyimine)-N-methyl-2-{2-[(E)-({1-[3-(trifluoromethyl)phenyl]ethoxy}imino)methyl]phenyl}acetamide、(3.26)(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-styryl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimine)-N-methylacetamide、(3.27)(2E)-2-{2-[({[(2E,3E)-4-(2,6-dichlorophenyl)but-3-yn-2-ylene]amino}oxy)methyl]phenyl}-2-(methoxyimine)-N-methylacetamide、(3.28) 2-Chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)pyridine-3-carboxamide, (3.29) 5-methoxy-2-methyl-4-(2-{[({(1E)-1-[3-(trifluoromethyl)phenyl]ethylene}amino)oxy]methyl}phenyl)-2,4-dihydro-3H-1,2,4-triazol-3-one, (3.30) methyl(2E)-2 -{2-[({cyclopropyl[(4-methoxyphenyl)imine]methyl}thio)methyl]phenyl}-3-methoxypropyl-2-enoic acid methyl ester, (3.31)N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(carbamoyl)-2-hydroxybenzamide, (3.32)2-{2-[(2,5-dimethylphenoxy)methyl]phenyl}-2-methoxy-N-methylacetamide.

[0104] (4) Inhibitors of mitosis and cell division, such as (4.1) benomyl, (4.2) carbendazim, (4.3) chlorfenazole, (4.4) diethofencarb, (4.5) ethaboxam, (4.6) fluopicolid, (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-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazole[1,5-a]pyrimidine, (4.14) 3-chloro-5-(6-chloropyridin-3-yl)-6-methyl-4-(2,4,6-trifluorophenyl)pyridazine.

[0105] (5) Compounds with multi-site activity, such as (5.1) Bordeaux mixture, (5.2) captafol, (5.3) captan, (5.4) chlorothalonil, (5.5) copper hydroxide, and (5.6) copper naphthenate. (5.7) naphthenate, (5.8) copper oxychloride, (5.9) copper sulfate, (5.10) dichlofluanid, (5.11) dithianon, (5.12) dodine, (5.13) dodine free base, (5.14) ferbam, (5.15) fluorofolpet, (5.16) folpet, (5.17) guazatine, (5.18) guazatine octanoate. (5.19) iminoctadine, (5.20) iminoctadine albesilate, (5.21) iminoctadine triacetate, (5.22) mancopper, (5.23) mancozeb, (5.24) mancozeb, (5.25) metiram, (5.26) zinc metiram (5.27) metiram, (5.28) copper-oxine, (5.29) propamidine, (5.30) methyl zinc mancozeb, (5.31) sulfur and sulfur preparations such as calcium polysulfide, (5.32) thiram, (5.33) tolylfluanid, (5.34) zinc mancozeb, (5.35) ziram and (5.36) anilazine.

[0106] (6) Resistance inducers, such as (6.1) acibenzolar-S-methyl, (6.2) isothiazine, (6.3) probenazole, (6.4) tiadinil and (6.5) laminarin.

[0107] (7) Inhibitors of amino acid and protein biosynthesis, such as (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-dihydroisoquinoline-1-yl)quinoline, (7.9) oxytetracycline, and (7.10) streptomycin.

[0108] (8) ATP production inhibitors, such as (8.1) fentin acetate, (8.2) fentin chloride, (8.3) fentin hydroxide, and (8.4) silthiofam.

[0109] (9) Cell wall synthesis inhibitors, such as (9.1) benthiavalicarb, (9.2) dimethomorph, (9.3) flumorph, (9.4) iprovalicarb, (9.5) mandipropamid, (9.6) polyoxins, (9.7) polyoxorim, (9.8) validamycin A, (9.9) valifenalate and (9.10) polyoxin B.

[0110] (10) Lipid and membrane synthesis inhibitors, such as (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) Tetraoxanezene, and (10.15) Tolclofos-methyl.

[0111] (11) Inhibitors of melanin biosynthesis, such as (11.1) carpropamid, (11.2) diclocymet, (11.3) fenoxanil, (11.4) fthalide, (11.5) pyroquilon, (11.6) tricyclazole, and (11.7) 2,2,2-trifluoroethyl{3-methyl-1-[(4-methylbenzoyl)amino]butane-2-yl}carbamate;

[0112] (12) Nucleic acid synthesis inhibitors, such as (12.1) benalaxyl, (12.2) benalaxyl-M (kiralaxyl), (12.3) bupirimate, (12.4) clozylacon, (12.5) dimethirimol, (12.6) ethirimol, (12.7) furaxyl, (12.8) hymexazol, (12.9) metalaxyl, (12.10) metalaxyl-M (mefenoxam), (12.11) offurace, (12.12) oxadixyl, (12.13) oxolinic acid, and (12.14) octhilinone.

[0113] (13) Signal transduction inhibitors, such as (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;

[0114] (14) Uncoupling agents, such as (14.1) binapacryl, (14.2) dinocap, (14.3) ferimzone, (14.4) fluazinam and (14.5) meptyldinocap.

[0115] (15) Other compounds, such as (15.1) bethoxazine, (15.2) capsimycin, (15.4) carvone, (15.5) chinomethionat, (15.6) pyriofenone (chlazafenone), (15.7) cufraneb, (15.8) cyfluthrin namid), (15.9) cymoxanil, (15.10) cyprosulfamide, (15.11) dazomet, (15.12) debacarb, (15.13) dichlorophen, (15.14) diclomezine, (15.15) difenzoquat, (15.16) difenzoquat methyl sulfate methylsulphate), (15.17) diphenylamine, (15.18) EcoMate, (15.19) fenpyrazamine, (15.20) flumetover, (15.21) fluorimid, (15.22) flusulfamide, (15.23) flutianil, (15.24) fosetyl-aluminium, (15.25) fosetyl-calcium, (15.26) fosetyl-sodium, (15.27) hexachlorobenzene, (15.2) 8) Irumamycin, (15.29) Methasulfocarb, (15.30) Methylisothiocyanate, (15.31) Metrafenone, (15.32) Mildiomycin, (15.33) Natamycin, (15.34) Nickel dimethyl dithiocarbamate, (15.35) Nitrothal-isopropyl, (15.36) Octhilinone, (15.37) Oxamocarb, (15.38) Oxyfenthiin, (15.39) Pentachlorophenol and its salts, (15.40) Phenothrin, (15.41) Phosphoric acid and its salts, (15.42) Propamocarb-fosetylate, (15.43) Propanosine-sodium, (15.44) Pyrimorph, (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) Butylphenyl)-3-(2-chloropyridin-4-yl)-1-(morpholin-4-yl)prop-2-en-1-one, (15.48) pyrrolnitrin, (15.49) tebufloquin, (15.50) tolnifanide, (15.51) triazoxide, (15.52) trichloroamide, (15.53) zarilamid, (15.54) (3S,6S,7R,8R)-8-benzyl-3-[({3-[(isobutyl) [Acyloxy)methoxy]-4-methoxypyridin-2-yl}carbonyl)amino]-6-methyl-4,9-dioxo-1,5-dioxane-7-yl 2-methylpropionate, (15.55)1-(4-{4-[(5R)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazo-2-yl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetone, (15.56)1-(4-{4-[(5S)-5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazo-2-yl}piperidin-1-yl)-2-[5 -Methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetone, (15.57)1-(4-{4-[5-(2,6-difluorophenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazolyl}piperidin-1-yl)-2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetone, (15.58)1-(4-methoxyphenoxy)-3,3-dimethylbutane-2-yl 1H-imidazol-1-carboxylic acid 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]dithia[2,3-c:5,6-c']dipyrrole-1,3,5,7(2H,6H)-tetraone, (15.62) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5R)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazolyl}piperidin-1-yl)acetone, (15.63) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-(4-{4-[(5S)-5-phenyl-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazolyl}piperidin-1-yl)acetone (15.64) 2-[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]-1-{4-[4-(5-phenyl-4,5-dihydro-1,2-oxazol-3-yl)-1,3-thiazolyl]piperidin-1-yl} ethyl ketone, (15.65) 2-butoxy-6-iodo-3-propyl-4H-benzopyran-4-one, (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 its salts, (15.68) 3-(4,4,5-trifluoro-3,3-dimethyl-3,4-dihydroisoquinoline-1-yl)quinoline (15.69) 3,4,5-trichloropyridine-2,6-dicarboxynitrile, (15.70) 3-chloro-5-(4-chlorophenyl)-4-(2,6-difluorophenyl)-6-methylpyridazine, (15.71) 4-(4-chlorophenyl)-5-(2,6-difluorophenyl)-3,6-dimethylpyridazine, (15.72) 5-amino-1,3,4-thiadiazol-2-thiol, (15.73) 5-chloro-N'-phenyl-N'-(prop-2-yn-1-yl)thiophene-2-sulfonylhydrazine, (15.74) 5-fluoro-2-[(4-fluorobenzyl)oxy]pyrimidine-4-amine, (15.75) 5-fluoro-2-[(4-methylbenzyl)oxy]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-phenyl acrylate, (15.78)N'-(4-{[3-(4-chlorobenzyl)-1,2,4-thiadiazol-5-yl]oxy}-2,5-dimethylphenyl)-N-ethyl-N-methyliminocarbamate, (15.79)N-(4-chlorobenzyl)-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propionamide, (15.80)N-[(4-chlorophenyl)(cyano)methyl]-3-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]propionamide, (15.81) N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide, (15.82) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide, (15.83) N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide, (15.84) N-{(E)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, (15.85) N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methyl}-2-phenylacetamide, (15.86) )N'-{4-[(3-tert-butyl-4-cyano-1,2-thiazolyl-5-yl)oxy]-2-chloro-5-methylphenyl}-N-ethyl-N-methyliminocarboxamide, (15.87)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-(1,2,3,4-tetrahydronaphthyl-1-yl)-1,3-thiazolyl-4-carboxamide, (15.88)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1R)-1,2,3,4-tetrahydronaphthyl-1-yl]-1,3-thiazolyl-4-yl) Formamide, (15.89)N-methyl-2-(1-{[5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl]acetyl}piperidin-4-yl)-N-[(1S)-1,2,3,4-tetrahydronaphthyl-1-yl]-1,3-thiazolyl-4-carboxamide, (15.90){6-[({[(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}phenyl carbamate, (15.91)phenazine-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}phenyl carbamate (15.95) 1-Methyl-3-(trifluoromethyl)-N-[2'-(trifluoromethyl)diphenyl-2-yl]-1H-pyrazole-4-carboxamide, (15.96) N-(4'-chlorodiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (15.97) N-(2',4'-dichlorodiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide, (15.98) 3-(difluoromethyl)-1-methyl-N-[4'-(trifluoromethyl)diphenyl-2-yl]-1H-pyrazole-4-carboxamide, (15.99)99) N-(2,5'-difluorodiphenyl-2-yl)-1-methyl-3-(trifluoromethyl)-1H-pyrazole-4-carboxamide, (15.100) 3-(difluoromethyl)-1-methyl-N-[4'-(prop-1-yn-1-yl)diphenyl-2-yl]-1H-pyrazole-4-carboxamide, (15.101) 5-fluoro-1,3-dimethyl-N-[4'-(prop-1-yn-1-yl)diphenyl-2-yl]-1H-pyrazole-4-carboxamide, (15.102) 2-chloro-N-[4'-(prop-1-yn-1-yl)diphenyl-2-yl]nicotinamide, (15.103) 3-(difluoromethyl)-N-[4'-(3,3'-yl)-[4'-[4'-[4'-[4'-[4'-[4'-[4'-[3,3'-yl]-[4'-[4'-[4'-[4'-[4'-[3 ... (15.104)N-[4'-(3,3-dimethylbut-1-yn-1-yl)diphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide, (15.105)3-(difluoromethyl)-N-(4'-ethynyldiphenyl-2-yl)-1-methyl-1H-pyrazole-4-carboxamide, (15.106)N-(4'-ethynyldiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (15.107)2-chloro-N-(4'-ethynyldiphenyl-2-yl)-5-fluoro-1,3-dimethyl-1H-pyrazole-4-carboxamide, (15.108) 2-chloro-N-[4'-(3,3-dimethylbut-1-yn-1-yl)diphenyl-2-yl]nicotinamide, (15.109) 4-(difluoromethyl)-2-methyl-N-[4'-(trifluoromethyl)diphenyl-2-yl]-1,3-thiazolyl-5-carboxamide, (15.110) 5-fluoro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)diphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, (15.111) 2-chloro-N-[4'-(3-hydroxy-3-methylbut-1-yn-1-yl)diphenyl-2-yl]nicotinamide, (15.112) 3 -(difluoromethyl)-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)diphenyl-2-yl]-1-methyl-1H-pyrazole-4-carboxamide, (15.113)5-fluoro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)diphenyl-2-yl]-1,3-dimethyl-1H-pyrazole-4-carboxamide, (15.114)2-chloro-N-[4'-(3-methoxy-3-methylbut-1-yn-1-yl)diphenyl-2-yl]nicotinamide, (15.115)(5-bromo-2-methoxy-4-methylpyridin-3-yl)(2,3,4-trimethoxy-6-methylphenyl) methyl ketone, (15.116) N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N2-(methanesulfonyl)valine, (15.117) 4-oxo-4-[(2-phenylethyl)amino]butyric acid, (15.118) {6-[({[(z)-(1-methyl-1H-tetrazol-5-yl)(phenyl)methylene]amino}oxy)methyl]pyridin-2-yl}carbamate butyl-3-yn-1-yl ester, (15.119) 4-amino-5-fluoropyrimidin-2-ol (tautomer form: 4-amino-5-fluoropyrimidin-2(1H)-one), (15.120) propyl 3,4,5-trihydroxybenzoate, (1 5.121) 1,3-Dimethyl-N-(1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl)-1H-pyrazole-4-carboxamide, (15.122) 1,3-Dimethyl-N-[(3R)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, (15.123) 1,3-Dimethyl-N-[(3S)-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1H-pyrazole-4-carboxamide, (15.124) [3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15. 125)(S)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.126)(R)-[3-(4-chloro-2-fluorophenyl)-5-(2,4-difluorophenyl)-1,2-oxazol-4-yl](pyridin-3-yl)methanol, (15.127)2-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)ethylene oxide-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.128)1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)ethylene oxide-2-yl]methyl}-1 H-1,2,4-triazole-5-yl ester, (15.129)5-(allylthio)-1-{[3-(2-chlorophenyl)-2-(2,4-difluorophenyl)ethylene oxide-2-yl]methyl}-1H-1,2,4-triazole, (15.130)2-[1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.131)2-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)ethylene oxide-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)ethylene oxide-2-yl]methyl}-2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.133) 1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)ethylene oxide-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (15.134) 1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)ethylene oxide-2-yl]methyl}-1H-1,2,4-triazol-5-yl thiocyanate, (15.1 35) 5-(allylthio)-1-{[rel(2R,3S)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)ethylene oxide-2-yl]methyl}-1H-1,2,4-triazole, (15.136) 5-(allylthio)-1-{[rel(2R,3R)-3-(2-chlorophenyl)-2-(2,4-difluorophenyl)ethylene oxide-2-yl]methyl}-1H-1,2,4-triazole, (15.137) 2-[(2S,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazole-3-thione, (15.1 38) 2-[(2R,4S,5S)-1-(2,4-dichlorophenyl)-5-hydroxy-2,6,6-trimethylhept-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-trimethylhept-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-trimethylhept-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-trimethylhept-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-trimethylhept-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-trimethylhept-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-trimethylhept-4-yl]-2,4-dihydro-3H-1,2,4-triazol-3-thione, (15.145)2-fluoro-6-(trifluoromethyl)-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)benzamide (15.146) 2-(6-benzylpyridin-2-yl)quinazoline, (15.147) 2-[6-(3-fluoro-4-methoxyphenyl)-5-methylpyridin-2-yl]quinazoline, (15.148) 3-(4,4-difluoro-3,3-dimethyl-3,4-dihydroisoquinoline-1-yl)quinoline, (15.149) abscisic acid (15.150)3-(difluoromethyl)-N-methoxy-1-methyl-N-[1-(2,4,6-trichlorophenyl)propyl-2-yl]-1H-pyrazole-4-carboxamide, (15.151)N'-[5-bromo-6-(2,3-dihydro-1H-indene-2-yloxy)-2-methylpyridin-3-yl]-N-ethyl-N-methyliminocarboxamide, (15.152)N'-{5-bromo-6-[1-(3,5-difluorophenyl)ethoxy]-2- (15.153)N'-{5-bromo-6-[(1R)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (15.154)N'-{5-bromo-6-[(1S)-1-(3,5-difluorophenyl)ethoxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (15.155)N'- {5-Bromo-6-[(cis-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (15.156)N'-{5-Bromo-6-[(trans-4-isopropylcyclohexyl)oxy]-2-methylpyridin-3-yl}-N-ethyl-N-methyliminocarboxamide, (15.157)N-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-carboxamide, ( 15.158) N-cyclopropyl-N-(2-cyclopropylbenzyl)-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.159) N-(2-tert-butylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (15.160) N-(5-chloro-2-ethylbenzyl)-N-cyclopropyl-3-(difluoromethyl)-5-fluoro-1-methyl-1H-pyrazole-4-carboxamide, (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-fluorobenzyl)-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-fluorobenzyl)-3-(difluoromethyl)-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-fluoro-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-carboxamide, (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-methyl-2-(trifluoromethyl)benzyl]-1H-pyrazole-4-carboxamide, (15.173)N -[2-chloro-6-(trifluoromethyl)benzyl]-N-cyclopropyl-3-(difluoromethyl)-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-cyclopropyl-3-(difluoromethyl)-5-fluoro-N-(2-isopropylbenzyl)-1-methyl-1H-pyrazole-4-thiocarboxamide, (15.177) 3-(difluoromethyl)-N-(7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl)-1-methyl-1H-pyrazole-4-carboxamide, (15.178) 3-(difluoromethyl)-N-[(3R)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-indene-4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (15.179) 3-(difluoromethyl)-N-[(3S)-7-fluoro-1,1,3-trimethyl-2,3-dihydro-1H-indene- [4-yl]-1-methyl-1H-pyrazole-4-carboxamide, (15.180)N'-(2,5-dimethyl-4-phenoxyphenyl)-N-ethyl-N-methyliminocarboxamide, (15.181)N'-{4-[(4,5-dichloro-1,3-thiazolyl-2-yl)oxy]-2,5-dimethylphenyl}-N-ethyl-N-methyliminocarboxamide, (15.182)N-(4-chloro-2,6-difluorophenyl)-4-(2-chloro-4-fluorophenyl)-1,3-dimethyl-1H-pyrazole-5-amine. Depending on the circumstances, all mixtures mentioned in classes (1) to (15) may form salts with a suitable base or acid, if they are capable of doing so on the basis of their functional groups.

[0116] Biopesticides as a mixed component

[0117] Compounds of Formula I can be combined with biopesticides.

[0118] Biopesticides include, in particular, products produced by bacteria, fungi, yeast, plant extracts, and microorganisms, including proteins and secondary metabolites.

[0119] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria, and bacteria that can act as biological insecticides, fungicides, or nematicides.

[0120] It also includes bacteria and fungi added as "inoculants" to plants or plant parts or organs, which promote plant growth and plant health through their special properties.

[0121] As a safety agent for mixed components

[0122] Compounds of Formula I may be combined with a safener, such as benoxacor, cloquintocet(-mexyl)), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole(-ethyl)), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen(-ethyl)), mefenpyr(-diethyl), oxabetrinil, 2-methoxy-N-{4-[(methylcarbamoyl)amino]phenyl}sulfonyl)benzamide (CAS129531-12-0), 4-(dichloroacetyl)-1-oxa-4-azaspiro[4.5]decane (CAS... 71526-07-3), 2,2,5-trimethyl-3-(dichloroacetyl)-1,3-oxazolidine (CAS 52836-31-4).

[0123] Plants and plant parts

[0124] All plants and plant parts can be processed according to the present invention. In this document, "plant" is understood to mean all plants and plant populations, such as desired and undesirable wild plants or crop plants (including naturally occurring crop plants), such as cereals (wheat, rice, rye, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peas and other vegetable species, cotton, tobacco, rapeseed, and fruit plants (having fruits such as apples, peas, citrus fruits, and grapes). Crop plants can be plants obtained through conventional breeding and optimization methods or through biotechnological methods or genetic engineering methods or combinations thereof, including transgenic plants and cultivars, including those protected and unprotected by plant breeders' rights. Plant parts should be understood to mean all above-ground and below-ground parts and organs of a plant, such as buds, leaves, flowers, and roots, with examples given including leaves, needles, stems, trunks, flowers, fruiting bodies, fruits and seeds, as well as tubers, roots, and rhizomes. Plant parts also include harvested materials as well as materials for asexual and sexual reproduction, such as cuttings, tubers, rhizomes, slips, and seeds.

[0125] The treatment of plants and plant parts by the present invention using compounds of Formula I is carried out directly by conventional treatment methods or by applying the compounds to their environment, habitat or storage space, such conventional treatment methods as impregnation, spraying, evaporation, atomization, dispersing, spraying, injection, and, in the case of propagation materials, especially seeds, one or more layers of coating may also be applied.

[0126] As described above, all plants and their parts can be treated according to the present invention. In one preferred embodiment, wild plant species and cultivars, or those obtained through conventional biological breeding such as crossbreeding or protoplast fusion, and their parts are treated. In another preferred embodiment, transgenic plants and cultivars (genetically modified organisms) obtained through genetic engineering—which can be combined with conventional methods if appropriate—and their parts are treated. The terms "part" or "plant part" have been explained above. Particularly preferred are those commercially available conventional cultivars or those currently in use, treated according to the present invention. Cultivars are understood to mean plants with new performance "characteristics" that have been obtained through conventional breeding, through mutation, or through recombinant DNA technology. They can be cultivars, varieties, biotypes, or genotypes.

[0127] Transgenic plants, seed treatment, and integration events.

[0128] Preferred transgenic plants or plant cultivars (obtained through genetic engineering) treated according to the present invention include all plants that have undergone genetic modification and received genetic material that endows these plants with particularly advantageous and useful properties. Examples of such properties include: better plant growth, enhanced tolerance to high or low temperatures, enhanced tolerance to drought or to water levels or soil salinity, improved flowering performance, easier harvesting, accelerated maturation, higher yield, higher quality and / or higher nutritional value of the harvested product, longer shelf life and / or processability of the harvested product. Other, and particularly emphasized, examples of this property include enhanced plant resistance to animal and microbial pests, such as insects, arachnids, nematodes, mites, slugs, and snails, for example, due to toxins formed in the plant, particularly those formed in the plant through genetic material from Bacillus thuringiensis (e.g., through genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb, and CryIF and combinations thereof); enhanced plant resistance to plant pathogenic fungi, bacteria, and / or viruses, induced, for example, by systemically acquired resistance (SAR), systemins, phytoalexins, inducers, and resistance genes, as well as corresponding expressed proteins and toxins; and increased plant tolerance to specific active insecticidal ingredients, such as imidazolinones, sulfonylureas, glyphosate, or glufosinate (e.g., the "PAT" gene). Genes conferring the desired traits can exist in transgenic plants in a combined form. Examples of transgenic plants include important crop plants such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes, peas and other types of vegetables, cotton, tobacco, rapeseed, and fruit plants (with fruits such as apples, pears, citrus fruits and grapes), with particular emphasis on corn, soybeans, wheat, rice, potatoes, cotton, sugarcane, tobacco, and rapeseed. A particularly emphasized trait is enhanced plant resistance to insects, arachnids, nematodes, slugs, and snails.

[0129] Crop protection – types of treatment

[0130] Treatment of plants and plant parts with compounds of Formula I can be carried out directly by conventional treatment methods or by applying the compounds to their environment, habitat, or storage space. These conventional treatment methods include, for example, soaking, spraying, misting, irrigation, evaporation, dusting, atomization, broadcasting, foaming, coating, spreading, injection, watering (soaking), and drip irrigation. In the case of propagation materials, especially seeds, methods such as dry seed treatment, wet seed treatment, suspension treatment, crusting, and coating with one or more layers can also be used. Compounds of Formula I can also be applied using ultra-low-dose methods or injected into the soil in their intended form or the compound itself.

[0131] A preferred direct treatment for plants is foliar application, which means applying the compound of Formula I to the leaves, wherein the treatment frequency and application rate should be adjusted according to the level of infection of the pest.

[0132] In the case of systemically active compounds, compounds of Formula I can also enter the plant via the root system. The plant then treats the plant's habitat by acting on the compound of Formula I. This can be accomplished, for example, by infiltration; or by mixing into the soil or nutrient solution, meaning that the plant site (e.g., soil or hydroponic system) is filled with the liquid form of the compound of Formula I; or by soil application, meaning that the compound of Formula I is introduced into the plant site in solid form (e.g., in granular form). In the case of rice crops, this can also be accomplished by metering the compound of Formula I into the flooded paddy field in solid application form (e.g., as granules).

[0133] Seed treatment

[0134] The control of animal pests through seed treatment is a well-established and continuously evolving topic. However, seed treatment involves a number of problems that are not always satisfactorily resolved. Therefore, there is a need to develop methods for protecting seeds and germinating crops that do not require, or at least significantly reduce, the additional application of pesticides during storage, after sowing, or after emergence. It is also necessary to optimize the amount of active ingredient used to provide optimal protection for seeds and germinating plants against animal pests without harming the plant itself. In particular, methods for seed treatment should also take into account the inherent insecticidal and / or nematicidal properties of pest-resistant or pest-tolerant transgenic plants to achieve optimal protection for seeds and germinating plants with minimal use of crop protection products.

[0135] Therefore, more particularly, the present invention also relates to a method for protecting seeds and germinating plants from pests by treating seeds with one of the compounds of Formula I. The method of the present invention for protecting seeds and germinating plants from pests also includes a method in which seeds are treated simultaneously with a compound of Formula I and a mixture thereof in one operation or continuously. It also includes a method of treating seeds with a compound of Formula I and a mixture thereof at different times.

[0136] The present invention also relates to the use of compounds of formula I for treating seeds to protect the seeds and the resulting plants from animal pests.

[0137] The present invention further relates to seeds treated with a compound of Formula I to protect them from animal pests. The present invention also relates to seeds treated simultaneously with a compound of Formula I and a mixed component. The present invention further relates to seeds treated with a compound of Formula I and a mixed component at different times. In the case of seeds treated with a compound of Formula I and a mixed component at different times, the components may be present in different layers of the seed. In this case, the layers containing the compound of Formula I and the mixed component may optionally be separated by an intermediate layer. The present invention also relates to seeds in which a compound of Formula I and a mixed component have been applied as part of a coating or other layer, or in addition to a coating.

[0138] The present invention also relates to seeds that, after being treated with a compound of formula I, undergo a film coating process to prevent the seeds from being abraded by dust.

[0139] One advantage of using one of the compounds of Formula I systematically is that the seed treatment protects not only the seed itself but also the plant derived from it (after emergence) from animal pests. In this way, direct treatment of the crop at sowing or shortly thereafter can be eliminated.

[0140] A further advantage is that treating seeds with the compound of formula I can promote germination and emergence of the treated seeds.

[0141] Also considered advantageous is that compounds of formula I can be used, especially, for genetically modified seeds.

[0142] Compounds of Formula I can also be used in combination with signaling technology components, resulting in, for example, better colonization of symbionts, such as rhizobia, mycorrhizae and / or endophytic bacteria or fungi, and / or optimized nitrogen fixation.

[0143] Compounds of Formula I are suitable for protecting the seeds of any plant variety used in agriculture, greenhouses, forestry, or horticulture. More particularly, said seeds include the seeds of cereals (e.g., wheat, barley, rye, millet, and oats), corn, cotton, soybeans, rice, potatoes, sunflowers, coffee beans, tobacco, rapeseed, canola, sugar beets (e.g., sugar beets and forage beets), peanuts, vegetables (e.g., tomatoes, cucumbers, beans, cruciferous plants, onions, lettuce), fruit plants, turfgrasses, and ornamental plants. Of particular importance are the seeds of cereals (wheat, barley, rye, oats), corn, soybeans, cotton, rapeseed, canola, and rice.

[0144] As mentioned above, treatment of transgenic seeds with compounds of Formula I is also particularly important. These seeds typically comprise seeds of plants containing a heterologous gene expressing at least one polypeptide with insecticidal and / or nematicidal properties. The heterologous gene in the transgenic seed may originate from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus, or Gliocladium. The compositions of the present invention are particularly suitable for treating transgenic seeds containing at least one heterologous gene derived from Bacillus. More preferably, the heterologous gene is derived from Bacillus thuringiensis.

[0145] In the context of this invention, the compound of formula I is applied to seeds. It is preferable to treat the seeds in a state that is sufficiently stable so that no damage occurs during treatment. Generally, seeds can be treated at any point between harvesting and sowing. Seeds that have been isolated from the plant and from which the rachis, outer shell, stem, epidermis, hairs, or pulp have been removed are typically used. For example, seeds that have been harvested, cleaned, and dried to a moisture content suitable for storage can be used. Alternatively, seeds that have been dried, for example, treated with water again, and then dried again (e.g., irrigation) can also be used.

[0146] Generally, when treating seeds, it is essential to ensure that the amount of Formula I compound and / or other additives applied to the seeds is chosen such that seed germination and the resulting plant are not impaired. This must be especially ensured in cases where active ingredients may exhibit toxic effects on plants at certain application rates.

[0147] Compounds of Formula I are typically applied to seeds in suitable formulations. Suitable formulations and seed treatment methods are known to those skilled in the art.

[0148] Compounds of Formula I can be converted into conventional seed coating formulations, such as solutions, emulsions, suspensions, powders, foams, slurries, or other seed coating compositions, as well as ULV formulations.

[0149] These formulations are prepared in a known manner by mixing a compound of Formula I with conventional additives, such as conventional fillers and solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins, and water.

[0150] Useful colorants that may be present in the seed dressing formulations used according to the invention are all colorants commonly used for the purposes described herein. Pigments that are slightly soluble in water can be used, or water-soluble dyes can be used. Examples include known colorants named Rhodamine B, CI Pigment Red 112, and CI Solvent Red 1.

[0151] Useful wetting agents that may be present in the seed dressing formulations used according to the invention are all substances that promote wetting and are generally used in formulations of active agricultural chemicals. Alkyl naphthalene sulfonates, such as diisopropyl naphthalene sulfonate or diisobutyl naphthalene sulfonate, are preferred.

[0152] Useful dispersants and / or emulsifiers that may be present in seed dressing formulations used according to the invention are all nonionic, anionic, and cationic dispersants commonly used in formulations of active agrochemical ingredients. Nonionic or anionic dispersants, or mixtures of nonionic or anionic dispersants, are preferred. Suitable nonionic dispersants particularly include ethylene oxide / propylene oxide block copolymers, alkylphenol polyethylene glycol ethers, and tristyrylphenol polyethylene glycol ethers, as well as their phosphorylated or sulfated derivatives. Suitable anionic dispersants are especially lignin sulfonates, polyacrylates, and aryl sulfonate / formaldehyde condensates.

[0153] The defoamer that may be present in the seed dressing formulation used according to the present invention is any foam inhibitor commonly used in formulations of active agrochemical ingredients. Silicone defoamers and magnesium stearate are preferred.

[0154] Preservatives that may be present in the seed dressing formulations used according to the present invention are all substances that can be used for this purpose in agricultural chemical compositions. Examples include dichlorophenol and benzyl alcohol hemiacetal.

[0155] The secondary thickener that may be present in the seed dressing formulation used according to the present invention is any substance that can be used for this purpose in an active agrochemical composition. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clay, and finely dispersed silica.

[0156] Useful adhesives that can be present in the seed dressing formulations used according to the present invention are all conventional adhesives that can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and tylose.

[0157] The gibberellins that can be present in the seed dressing formulation used according to the present invention are preferably gibberellins A1, A3 (=gibberellic acid), A4 and A7, with gibberellic acid being particularly preferred.

[0158] The seed dressing formulations used according to the present invention can be used directly or after pre-diluting with water to treat a variety of different types of seeds. For example, concentrates or formulations obtained therefrom by dilution with water can be used to coat the following seeds: seeds of cereals (such as wheat, barley, rye, oats, and triticale), and seeds of corn, rice, rapeseed, peas, beans, cotton, sunflower, soybeans, and sugar beets, or a variety of different vegetable seeds. The seed dressing formulations used according to the present invention, or their diluted forms, can also be used to treat the seeds of genetically modified plants.

[0159] For treating seeds with the seed dressing formulation used according to the present invention or in a form prepared therefrom, all conventional mixing equipment used for seed dressing is available. More specifically, the seed dressing process involves placing seeds in batches or continuously in a mixer; adding the desired amount of the seed dressing formulation, either on its own or pre-diluted with water; and mixing until the formulation is evenly distributed on the seeds. If appropriate, a drying operation may then be performed.

[0160] The application rate of the seed dressing formulation used according to the present invention can vary within a relatively wide range. It depends on the specific content of the compound of Formula I in the formulation and the seeds. The application rate of the compound of Formula I is typically from 0.001 g to 50 g per kilogram of seeds; preferably from 0.01 g to 15 g per kilogram of seeds.

[0161] For animal health

[0162] In the field of animal health, i.e., veterinary medicine, the active ingredient of this invention is used to combat animal parasites, particularly ectoparasites or, in other embodiments, endoparasites. The term "endoparasites" particularly includes worms such as tapeworms, nematodes, or flukes; and protozoa such as coccidia. Ectoparasites are generally and preferably arthropods, especially insects such as flies (biting flies and sucking flies), parasitic fly larvae, lice, hair lice, bird lice, fleas, etc.; or scabies mites such as ticks, such as hard ticks or soft ticks; or mites such as scabies mites, fall mites, and bird mites; and aquatic ectoparasites such as copepods.

[0163] In the field of veterinary medicine, compounds of formula I with good homeothermic toxicity are suitable for the prevention and treatment of parasites and are found in animal breeding and animal husbandry of livestock, breeding animals, zoo animals, laboratory animals, experimental animals, and domestic animals. They are effective against parasites at all or specific developmental stages.

[0164] Agricultural livestock include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffalo, rabbits, reindeer, fallow deer, and especially cattle and pigs; poultry such as turkeys, ducks, geese, and especially chickens; aquaculture such as fish and crustaceans; and insects such as bees.

[0165] Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, especially dogs, cats, caged birds, reptiles, amphibians, and ornamental fish.

[0166] In a preferred embodiment, the compound of Formula I is administered to a mammal.

[0167] In another preferred embodiment, the compound of formula I is administered to poultry, i.e., caged birds and especially poultry.

[0168] The use of compounds of Formula I to control animal parasites aims to reduce or prevent disease, mortality, and performance loss (in the case of meat, milk, wool, raw hides, eggs, honey, etc.), so as to make animal husbandry more economical and simpler, and to achieve better maintenance of animal health.

[0169] In the field of animal health, the term "control" or "controlling" refers to compounds of Formula I that are effective in reducing the incidence of specific parasites in animals infected with such parasites to a harmless level. More specifically, in this context, "control" refers to compounds of Formula I that can kill the parasites, inhibit their growth, or suppress their proliferation.

[0170] Typically, the active ingredients of this invention can be used directly when treating animals. They are preferably used (administered) in the form of pharmaceutical compositions that may contain pharmaceutically acceptable excipients and / or adjuvants known in the art.

[0171] In animal health and animal husbandry, the active ingredient is used (administered) in the following known ways: enteral administration, in the form of tablets, capsules, potions, drench, granules, pastes, bolus, feed-through process, and suppositories; parenteral administration, such as by injection (intramuscular, subcutaneous, intravenous, especially intraperitoneal), implantation; nasal administration; skin administration, in the form of, for example, immersion or bathing, spraying, infusion and dripping, detergents and powders; and by means of molded articles containing the active ingredient, such as collars, ear tags, tail tags, limb bands, halters, marking devices, etc. The active ingredient can be formulated into shampoos or suitable formulations that can be applied in the form of aerosols or non-pressurized sprays such as pump sprays and nebulizers.

[0172] When used for livestock, poultry, pets, etc., the active ingredients of the present invention may be used directly or after dilution (e.g., 100 to 10,000 times dilution) in formulations containing 1% to 80% by weight of the active ingredients, or they may be used as a chemical bath.

[0173] In applications in animal health, to broaden the activity spectrum, the active ingredients of the present invention can be used in combination with suitable synergists, anthelmintics, or other active ingredients, such as acaricides, insecticides, anthelmintics, and antiprotozoa agents.

[0174] Vector control

[0175] Compounds of Formula I can also be used for vector control. In the context of this invention, vectors are arthropods, particularly insects or arachnids, capable of transmitting pathogens such as viruses, worms, single-celled organisms, and bacteria from a host (plant, animal, human, etc.) to a host. Pathogens can be transmitted to a host mechanically (e.g., trachoma in non-stinging flies) or after injection (e.g., malaria parasites in mosquitoes).

[0176] In the context of this invention, examples of disease vectors are insects, such as aphids, flies, leafhoppers, or thrips, which can transmit plant viruses to plants. Other vectors capable of transmitting plant viruses include spider mites, lice, beetles, and nematodes.

[0177] In the context of this invention, other examples of disease vectors are insects and arachnids, such as mosquitoes, especially mosquitoes of the genera Aedes and Anopheles, such as Anopheles gambiae, Anopheles arbiensis, Anopheles funestus, and Anopheles dirus (malaria); as well as mosquitoes of the genus Culex, lice, fleas, flies, mites, and ticks, which can transmit pathogens to animals and / or humans.

[0178] If the compound of formula I is resistant to damage, then vector control is also possible.

[0179] Compounds of Formula I are suitable for use in the prevention of vector-borne diseases and / or pathogens. Therefore, another aspect of the invention is the use of compounds of Formula I in, for example, agriculture, horticulture, forestry, landscaping, and recreational facilities, as well as in the protection of materials and stored products for vector control.

[0180] Protection of industrial materials

[0181] Compounds of Formula I are suitable for protecting industrial materials from insect attack or damage, such as from insects of the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psciformes, and Zygentoma.

[0182] In this context, industrial materials should be understood to mean inanimate materials, such as, preferably, plastics, adhesives, glues, paper and paper sheets, leather, wood and processed wood products, and coating compositions. The use of this invention for the protection of wood is particularly preferred.

[0183] In another embodiment, the compound of formula I is used in conjunction with at least one other insecticide and / or at least one fungicide.

[0184] In another embodiment, the compounds of Formula I are ready-to-use insecticides, meaning they can be applied to the material without further modification. In particular, suitable other insecticides or fungicides are those mentioned above.

[0185] Surprisingly, compounds of Formula I have also been found to protect objects in contact with saltwater or brackish water from contamination, particularly ship hulls, screens, nets, structures, mooring equipment, and signaling systems. It is also possible that compounds of Formula I can be used alone or in combination with other active ingredients as antifouling agents.

[0186] Control of animal pests in the health field

[0187] Compounds of Formula I are suitable for the control of animal pests in the sanitation field. More specifically, the present invention can be used in the household, sanitation, and storage product protection fields, particularly for the control of insects, arachnids, and mites in enclosed spaces such as residences, factory workshops, offices, and vehicle cabins. For the control of animal pests, compounds of Formula I can be used alone or in combination with other active ingredients and / or adjuvants. They are preferably used in household insecticide products. Compounds of Formula I are effective against both susceptible and resistant species and at all developmental stages.

[0188] These pests include, for example, those from the following classes: Arachnida; Scorpiones, Araneae, and Opiliones; Chilopoda and Diplopoda; Blattodea; Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psciformes, Saltatoria, Orthoptera, Siphonaptera, and Silverfish; and Malacostraca, Isopoda.

[0189] In baits or bait stations used for deployment, application is carried out in the following forms: aerosols, unpressurized spray products such as pump-action and atomizing sprays, automatic fogging systems, smoke agents, foaming agents, gels, evaporating products with evaporator tablets made of cellulose or plastic, liquid evaporators, gel and film evaporators, propeller-driven evaporators, energy-free or passive evaporation systems, moth traps, moth traps, and moth trap glue; as granules or powders. Detailed Implementation

[0190] The following examples are for illustrative purposes only and should not be construed as limiting the invention in any way. The scope of protection of this invention is defined by the claims.

[0191] Given the economic efficiency and diversity of the compounds, we preferentially synthesized a number of compounds, some of which are listed in Table 1 below. Specific compound structures and corresponding compound information are shown in Tables 1 and 2. The compounds in Table 1 are only for better illustration of the present invention and do not limit the invention. Those skilled in the art should not interpret this as limiting the scope of the above-mentioned subject matter of the invention to the following compounds.

[0192] Table 1. Compound Structures

[0193]

[0194]

[0195]

[0196]

[0197]

[0198]

[0199]

[0200]

[0201]

[0202]

[0203]

[0204] Table 2 Compounds 1 H NMR

[0205]

[0206]

[0207]

[0208]

[0209]

[0210] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The raw materials can be commercially available or prepared by methods known in the literature or as detailed in the description. Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention. Although specific raw materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar raw materials and conditions. Such variations or modifications to the preparation methods of the present invention, such as various isomers of the compounds, are all included within the scope of the present invention. Furthermore, the preparation methods described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protecting appropriate groups during the reaction process, etc.

[0211] The following method examples are provided to further illustrate the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further explain the invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds shown below are either commercially available or can be easily prepared by those skilled in the art.

[0212] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0213] 1. Synthesis of Compound 1

[0214] (1) In a 100 mL single-necked flask, add 1-1 (232 mg, 533.06 μmol), 1-2 (203.05 mg, 799.60 μmol), and potassium acetate (104.63 mg, 1.07 mmol). Add 20 mL of 1,4-dioxane, purge with nitrogen once, add PdCl2 (dppf) (43 mg, 53.31 μmol), purge with nitrogen three times, heat directly to 100 °C, and stir overnight. LC-MS detected the main peak of the product. Add silica gel powder and mix to purify the sample, obtaining product 1-3 (175 mg, yield 67.6%).

[0215]

[0216] (2) In a 100 mL single-necked flask, add 1-3 (175 mg, 362.86 μmol), 2-bromopyrimidine (86.53 mg, 544.28 μmol), cesium fluoride (110.24 mg, 725.71 μmol), 20 mL of 1,4-dioxane, and 2 mL of water. Purge with nitrogen once, then add PdCl2 (dppf) (29 mg, 36.3 μmol), purge with nitrogen three times, and directly heat to 100 °C and stir overnight. The main peak of the product was detected by LC-MS. Silica gel powder was added and the sample was purified to obtain a white solid compound 1 (78 mg, yield 33.4%).

[0217]

[0218] 2. Synthesis of Compound 13

[0219] (1) In a 50 mL single-necked flask, 13-1 (800 mg, 2.15 mmol) was dissolved in 5 mL of anhydrous ethanol, and 13-2 (455 mg, 2.80 mmol) was added. The mixture was stirred at 90 °C for 2 h. The reaction was monitored by LCMS until complete. The solvent in the reaction solution was evaporated and slurryed with methanol to obtain 13-3 (680 mg, yield 72%, white solid).

[0220]

[0221] (2) In a 50 mL single-necked flask, 13-3 (230 mg, 0.53 mmol) was dissolved in 5 mL of 1,4-dioxane, potassium acetate (104 mg, 1.06 mmol) and 1-2 (202 mg, 0.79 mmol) were added, and the mixture was purged with nitrogen once. Then, Pd(dppf)Cl2 (9 mg, 0.01 mmol) was added, and the mixture was purged with nitrogen three times. The mixture was stirred at 100 °C for 4 h. The reaction was monitored by LCMS until complete. The crude product of the reaction solution was used directly in the next step.

[0222]

[0223] (3) To the crude product from the previous step, add 5 ml of 1,4-dioxane and 1 ml of water, then add cesium fluoride (241 mg, 1.59 mmol) and 13-5 (157 mg, 0.79 mmol), purge once with nitrogen, then add Pd(dppf)Cl2 (9 mg, 0.0 mmol), purge three times with nitrogen, and stir at 100 °C for 12 h. Monitor the reaction for completeness using LCMS. Quench the reaction solution with water, extract with ethyl acetate, wash the organic phase with water and saturated brine, dry and concentrate, and purify the residue by column chromatography (EA / PE = 2 / 3) to give compound 13 (50 mg, yield 18%, white solid).

[0224]

[0225] 3. Synthesis of Compound 25

[0226] In a 50 mL single-necked flask, 13-4 (270 mg, 0.57 mmol) was dissolved in 10 mL of 1,4-dioxane, 1 mL of water was added, followed by cesium fluoride (263 mg, 1.72 mmol) and 25-1 (154 mg, 0.86 mmol). The mixture was purged with nitrogen once, and then Pd(dppf)Cl2 (23 mg, 0.03 mmol) was added. The mixture was purged with nitrogen three times, and the mixture was stirred at 100 °C for 12 h. The reaction was monitored by LC-MS until complete. The reaction solution was quenched with water, extracted with ethyl acetate, and the organic phase was washed with water and saturated brine. The solution was dried and concentrated, and the residue was purified by column chromatography (EA / PE = 2 / 3) to give compound 25 (110 mg, 39% yield, yellow solid).

[0227]

[0228] 4. Synthesis of Compound 42

[0229] (1) Compound 13-3 (2 g, 4.61 mmol), (Tributylstannyl)methanol (2.22 g, 6.91 mmol), XPhos Pd G2 (377.13 mg, 460.58 μmol), and 30 mL of 1,4-dioxane were added to a 100 mL single-necked flask and stirred overnight at 100 °C. The main peak of the product was detected by LCMS. Silica gel powder was added and the sample was mixed. The product was separated and purified (DCM / MeOH = 15%) to obtain product 42-1 (1.4 g, yield 79%).

[0230]

[0231] (2) Compound 42-1 (1.4 g, 3.62 mmol), Dess-Martin periodinane (2.31 g, 5.44 mmol), and 30 mL of DCM were added to a 100 mL single-necked flask and stirred overnight at room temperature. The main peak of the product was detected by LC-MS. Saturated ammonium chloride aqueous solution was added, followed by DCM and water extraction. The organic phase was separated, silica gel powder was added and mixed, and the product was purified (PE / EA = 30%) to obtain 42-2 (500 mg, yield 36%).

[0232]

[0233] (3) Compound 42-2 (500.00 mg, 1.30 mmol), hydroxylamine hydrochloride (181.27 mg, 2.61 mmol), sodium acetate (213.99 mg, 2.61 mmol), 20 mL of ethanol, and 4 mL of water were added to a 100 mL single-necked flask and stirred at room temperature for 3 h. The main peak of the product was detected by LC-MS. The solvent was evaporated, and EA and water were added for extraction. The organic phase was evaporated to dryness to obtain crude product 42-3 (514 mg, yield 98.9%).

[0234]

[0235] (4) Compound 42-3 (200.00 mg, 502.06 μmol) and 20 mL of DMF were added to a 100 mL single-necked flask, followed by the slow addition of NCS (134.08 mg, 1.00 mmol). The mixture was heated to 50 °C and stirred for 3 h. The main peak of the product was detected by LC-MS. EA and water were added for extraction. The organic phase was washed three times with saturated sodium chloride aqueous solution. The organic phase was then evaporated to dryness to obtain crude product 42-4 (154 mg, yield 65.7%).

[0236]

[0237] (5) Compound 42-4 (154.00 mg, 329.59 μmol), isobutylene (369.86 mg, 6.59 mmol), sodium bicarbonate (138.44 mg, 1.65 mmol), and 15 mL of isopropanol were added to a 100 mL single-necked flask. The mixture was slowly heated to 50 °C and stirred for 4 h. The main peak of the product was detected by LC-MS. Silica gel powder was added and the mixture was directly stirred. The product was then separated and purified (PE / EA = 25%) to obtain compound 42 (50 mg, yield 31%).

[0238]

[0239] 5. Synthesis of Compound 49

[0240] (1) Under a nitrogen atmosphere, substrate 13-4 (400 mg, 0.832 mmol) was dissolved in 10 mL of dioxane:H2O = 10:1 in a single-necked flask. 49-1 (181 mg, 0.998 mmol), cesium fluoride (317 mg, 1.664 mmol), and [1,1'-bis(diphenylphosphine)ferrocene]palladium dichloromethane dichloride complex (33 mg, 0.04 mmol) were added, and the reaction was carried out at 100 °C for 4 h. The reaction was monitored by LCMS until completion. The reaction solution was filtered through diatomaceous earth, and the filtrate was concentrated and purified by column chromatography (EA / PE = 1 / 1) to obtain a light yellow solid 49-2 (200 mg, yield 48.1%).

[0241]

[0242] (2) At 0°C, substrate 49-2 (140 mg, 0.279 mmol) was dissolved in 5 mL of DMF in a single-necked flask, and NCS (37 mg, 0.279 mmol) was added. The reaction was carried out at 90°C for 4 h. The reaction was monitored by LCMS until completion. The reaction solution was quenched with water, extracted with EA, and the organic phase was concentrated and recrystallized from methanol to give a light yellow solid product 49 (80 mg, yield 53.7%).

[0243]

[0244] 6. Synthesis of Compound 50

[0245] (1) Prepare a 250 ml carbonyl flask. Dissolve compound 13-3 (1.50 g, 3.45 mmol) in 70 ml of methanol. Add triethylamine (1.04 g, 10.35 mmol) and 0.5 g of 1,1'-bis(diphenylphosphine)ferrocene palladium(II) dichloromethane complex as a catalyst. Evacuate the system and then introduce CO. The purging pressure is greater than or equal to 0.2 MPa. React at 70 °C for 10 h. Monitor the reaction until the starting material disappears. Concentrate the reaction solution, stir and pass it through a normal phase column (PE:EA = 4:1) to obtain 50-1 (1.3 g, yield 90.6%).

[0246]

[0247] (2) In a 100 mL single-necked flask, compound 50-1 (1.30 g, 3.14 mmol) was dissolved in 30 mL of THF, and an aqueous solution of lithium hydroxide (150.62 mg, 6.29 mmol) dissolved in 10 mL of water was added. The mixture was stirred at room temperature for 4 h. The main peak of the product was detected by LC-MS. The pH of the solution was adjusted to 3-5 by adding hydrochloric acid, and EA and water were added for extraction. The organic phase was separated and evaporated to dryness to obtain 50-2 (1.22 g, yield 97.1%).

[0248]

[0249] (3) Compound 50-2 (700.00 mg, 1.75 mmol), 30 mL of DCM, and 2 mL of oxalyl chloride were added to a 100 mL single-necked flask and stirred at room temperature for 2 h. The main peak of the product was detected by LC-MS. The reaction solution was evaporated to dryness to obtain crude product 50-3 for later use. In another 100 mL single-necked flask, hydroxylamine hydrochloride (139.05 mg, 2.00 mmol), potassium carbonate (276.55 mg, 2.00 mmol), and EA (20 mL) were added and stirred in an ice bath for 10 min. Crude product 50-3 was slowly added, followed by 2 mL of water. The reaction was carried out for 4 h. The main peak of the product was detected by LC-MS. EA and water were added for extraction. The mixture was separated and the organic phase was evaporated to dryness to obtain product 50-4 (684 mg, yield 94.1%).

[0250]

[0251] (4) Compound 50-4 (300 mg, 724.01 μmol), potassium carbonate (200.12 mg, 1.45 mmol), 1,2-dibromoethane (272.03 mg, 1.45 mmol) and 20 mL of DMF were added to a 100 mL single-necked flask. The mixture was slowly heated to 80 °C and reacted for 4 h. The product was detected by LCMS. EA and water were added for extraction. The mixture was washed three times with saturated saline solution. The mixture was separated and purified by adding silica gel powder (PE / EA = 21%) to obtain compound 50 (108 mg, yield 33.8%).

[0252]

[0253] 7. Synthesis of Compound 51

[0254] (1) Compounds 13-3 (1.00 g, 2.30 mmol), 51-1 (404.67 mg, 3.45 mmol), XPhos (219.57 mg, 460.58 μmol), cesium carbonate (1.50 g, 4.61 mmol), and 1,4-dioxane (30 mL) were added to a 100 mL single-necked flask. The mixture was purged with nitrogen once, and then tris(dibenzylacetone)palladium (210.89 mg, 230.29 μmol) was added. The mixture was purged with nitrogen three times, and stirred overnight at 100 °C. The main peak of the product was detected by LCMS. Silica gel powder was added and the mixture was stirred. The product was then separated and purified (PE / EA = 65%) to obtain 51-2 (571 mg, yield 52.6%).

[0255]

[0256] (2) Compound 51-2 (571.00 mg, 1.21 mmol) and 20 mL of DCM were added to a 100 mL single-necked flask, followed by the addition of trifluoroacetic acid (1.38 g, 12.14 mmol). The mixture was stirred overnight at room temperature. The main peak of the product was detected by LCMS. Saturated sodium bicarbonate aqueous solution was added, followed by the addition of DCM and water for extraction. The organic phase was separated, and the solvent was evaporated to obtain crude product 51-3.

[0257]

[0258] (3) Crude products 51-3 (449.00 mg, 1.21 mmol), 51-4 (276.26 mg, 1.33 mmol), and 20 mL of acetic acid were added to a 100 mL single-necked flask. The mixture was heated to 100 °C and stirred overnight. The main peak of the product was detected by LCMS. The solvent was evaporated, and the product was dissolved in dichloromethane. The mixture was then mixed with silica gel powder and purified (PE / EA = 55%) to obtain compound 51-5 (258 mg, yield 39.3%).

[0259]

[0260] (4) Compound 51-5 (128.00 mg, 239.97 μmol), methyl iodoform (21.65 mg, 719.90 μmol), potassium carbonate (66.33 mg, 479.94 μmol), and 20 mL of DMF were added to a 100 mL single-necked flask and stirred at room temperature for 3 h. The main peak of the product was detected by LCMS. EA and water were added for extraction, and the sample was washed three times with saturated saline. The sample was mixed with silica gel powder and purified (PE / EA = 30%) to obtain compound 51 (50 mg, yield 38%).

[0261]

[0262] 8. Synthesis of Compound 5

[0263] Compound 1-3 (250 mg, 0.52 mmol) and 25-1 (180 mg, 0.57 mmol) were dissolved in 20 mL of dioxane and 2 mL of water, followed by the addition of cesium fluoride (236 mg, 1.56 mmol). The system was protected under nitrogen, and a catalytic amount of Pd(dppf)Cl2 catalyst was added, followed by nitrogen protection. The reaction was carried out overnight at 100 °C. The reaction was monitored until the starting material disappeared, at which point the reaction was terminated. The reaction solution was concentrated and purified in a normal phase to give compound 5 (0.05 g, 19.3% yield, white solid).

[0264]

[0265] 9. Synthesis of Compound 15

[0266] Compound 13-4 (500 mg crude) was dissolved in 5 mL of 1,4-Dioxane:H₂O = 10:1. Cesium fluoride (474.0 mg, 3.11 mmol), 15-1 (241.3 mg, 1.24 mmol), and PdCl₂ (dppf)·CH₂Cl₂ (84.6 mg, 0.10 mmol) were added sequentially under a nitrogen atmosphere. The reaction was carried out at 100 °C for 4 h. LC-MS showed that the reaction was complete. The reaction solution was concentrated, and the crude product was diluted with water and ethyl acetate. The organic phase was washed with saturated brine, dried, filtered, and concentrated. The residue was purified by column chromatography to give compound 15 (230.0 mg, 47.3% yield, white solid).

[0267]

[0268] 10. Synthesis of Compound 126

[0269] The preparation of compound 126-1 was performed following that of compound 50-4. 126-1 (400 mg, 0.96 mmol) was dissolved in N,N-dimethylformamide, followed by the sequential addition of 1,2-dibromoethane (271 mg, 1.44 mmol) and potassium carbonate (399 mg, 2.89 mmol). The mixture was then heated to 80 °C and stirred for 5 h. The reaction was stopped when the starting material disappeared and no change was observed in the system. The system was cooled, quenched with water, washed three times with ethyl acetate, and the organic phase was purified by rotary evaporation to give compound 126 (50 mg, 11.8% yield, white solid).

[0270]

[0271] 11. Synthesis of Compound 143

[0272] Compound 15 (230 mg, 0.49 mmol) was dissolved in 5 mL of N,N-dimethylformamide, and NBS (91.6 mg, 0.51 mmol) was added at 0 °C. The reaction was carried out at 90 °C for 2 h. The reaction was monitored by LC-MS until complete. The reaction solution was diluted with water and ethyl acetate, the organic phase was washed with semi-saturated brine, dried, filtered, and concentrated. The residue was purified by column chromatography to give compound 143 (200.0 mg, yield 74.6%, white solid).

[0273]

[0274] 12. Synthesis of Compound 144

[0275] Compound 143 (200.0 mg, 0.36 mmol) was dissolved in 4 mL of 1,4-dioxane. Trimethylcyclotriboroxane (135.5 mg, 1.08 mmol), potassium carbonate (149.2 mg, 1.08 mmol), and PdCl2(dppf)CH2Cl2 (29.3 mg, 0.03 mmol) were added sequentially under a nitrogen atmosphere. The reaction was carried out at 100 °C for 12 h. The reaction was monitored by LC-MS until complete. The reaction solution was concentrated, and the crude product was diluted with water and ethyl acetate. The organic phase was washed with saturated brine, dried, filtered, and concentrated. The residue was purified by column chromatography to give compound 144 (98 mg, 0.20 mmol, white solid).

[0276]

[0277] Bioactivity evaluation (insecticide activity test)

[0278] Fall armyworm, armyworm, and beet armyworm: The technical grade pesticide was diluted with acetone to prepare gradient concentrations. Leaves (young corn leaves) of 3-4 leaves from untreated host plants (not containing insect-resistant genes) were collected, cut into 3-4 cm lengths, and placed in a 9 cm diameter plastic box. Ten test insects that had been starved for 2 hours were introduced into the box, and the pesticide was applied using a spray tower. The treatment was repeated three times, with the highest dose containing acetone serving as a control. After application, the box was tightly sealed and placed in a treatment room (temperature 25℃, humidity 60%). The number of dead insects was investigated after 48 hours, and the mortality rate was calculated. Representative data are shown in Table 3. Mortality rate = (number of dead insects / number of test insects) × 100%

[0279] Table 3 Insecticidal activity test results (2DAA)

[0280]

[0281]

[0282] Note: N indicates no data.

[0283] Furthermore, numerous tests have revealed that the compounds and their compositions described in this invention exhibit excellent control activity against many agricultural pests, including Lepidoptera (such as corn borers, rice stem borers, diamondback moths, beet armyworms, cotton bollworms, fall armyworms, and armyworms), Homoptera (such as cotton aphids, turnip aphids, pea aphids, peanut aphids, and green mirid bugs), Acari (such as two-spotted spider mites, truncated spider mites, and Turkestan spider mites), Diptera (such as leek leeks), Coleoptera (such as yellow flea beetles and small ape leaf beetles), and thrips (such as palm thrips, onion thrips, and tobacco thrips), as well as sanitary pests such as cockroaches (such as termites and cockroaches) and flies (such as flies and mosquitoes). These compounds not only possess broad-spectrum, high-efficiency, and systemic characteristics, but also effectively control resistant pests and have considerable commercial value.

Claims

1. A fused heterocyclic compound, as shown in general formula I: in, Q represents N or CR6; X represents a cycloalkyl, aryl, or heterocyclic group; R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclic, and -OR, respectively. 21 -SR 21 -SOR 21 -(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR 21 -(CO)R 21 -(CO)OR 21 or -(CO)N(R) 21 )2; The alkyl, alkenyl, or alkynyl group is optionally selected from halogen, cyano, nitro, cycloalkyl, aryl, heterocyclic, -OR 21 -SR 21 -SOR 21 -(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR 21 -(CO)R 21 or -(CO)N(R) 21 At least one group in )2 is replaced; R 21 Each of these can be hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, aryl, heterocyclic, arylalkyl, or heterocyclic alkyl, and each can be independently hydrogen, alkyl, alkenyl, or heterocyclic alkyl. The aforementioned "cycloalkyl", "heterocyclic" or "aryl" may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R; or two adjacent carbon atoms on the ring may be connected to -(CH2)3- or -(CH2)4- to form a fused ring; R independently represents hydrogen, alkyl, alkenyl, alkynyl, alkyl, alkenyl or alkynyl substituted with at least one group selected from halogen, hydroxyl, alkoxy, cyano or alkoxycarbonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

2. The fused heterocyclic compound according to claim 1, characterized in that, X represents a C3-C8 cycloalkyl, aryl, or heterocyclic group; R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, and -OR, respectively. 21 -SR 21 -SOR 21 -(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR 21 -(CO)R 21 -(CO)OR 21 or -(CO)N(R) 21 )2; The C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl group is optionally selected from halogen, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, -OR 21 -SR 21 -SOR 21 -(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR 21 -(CO)R 21 or -(CO)N(R) 21 At least one group in )2 is replaced; R 21 Each of these can be independently hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, aryl, heterocyclic, aryl-C1-C8 alkyl, or heterocyclic-C1-C8 alkyl; The aforementioned "C3-C8 cycloalkyl", "heterocyclic" or "aryl" may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R; or two adjacent carbon atoms on the ring may be connected to -(CH2)3- or -(CH2)4- to form a fused ring; R independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl substituted with at least one group selected from halogen, hydroxyl, C1-C8 alkoxy, cyano or C1-C8 alkoxycarbonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C8 alkyl, halo-C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo-C1-C8 alkoxy.

3. A fused heterocyclic compound according to claim 1 or 2, characterized in that, X represents a C3-C6 cycloalkyl, aryl, or heterocyclic group; R1, R2, R3, R4, R5, and R6 independently represent hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, and -OR, respectively. 21 -SR 21 -SOR 21 -(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR 21 -(CO)R 21 -(CO)OR 21 or -(CO)N(R) 21 )2; The C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 alkynyl group is optionally selected from halogen, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, -OR 21 -SR 21 -SOR 21 -(SO2)R 21 -N(R) 21 )2、-O(CO)R 21 -O(CO)OR 21 -(CO)R 21 or -(CO)N(R) 21 At least one group in )2 is replaced; R 21 Each of these can be independently hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl-C1-C6 alkyl, aryl, heterocyclic, aryl-C1-C6 alkyl, or heterocyclic-C1-C6 alkyl; The aforementioned "C3-C6 cycloalkyl", "heterocyclic" or "aryl" may optionally be replaced by at least one group selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, -OR, -SR, -(CO)R, -(CO)OR, -(CO)N(R)2, -(CS)N(R)2, -(SO)R or -(SO2)R; R independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl substituted with at least one group selected from halogen, hydroxyl, C1-C6 alkoxy, cyano or C1-C6 alkoxycarbonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl or phenyl substituted with at least one group selected from halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy; Preferably, the compound is selected from any one of the compounds in Table 1.

4. A method for preparing a fused heterocyclic compound as described in any one of claims 1-3, characterized in that, Includes the following steps: The compound of general formula II reacts with the compound of general formula III to produce the compound of general formula I, and the reaction equation is as follows: In this case, either Q1 or Q2 is a halogen, and the other is a... The definitions of R1, R2, R3, R4, R5, Q, and X are as described in any one of claims 1-3; Preferably, the reaction is carried out in the presence of a solvent; more preferably, a base and a catalyst are added during the reaction; even more preferably, the base is selected from at least one of inorganic or organic bases; the catalyst is selected from Pd(dppf)Cl2, Pd(dppf)Cl 2. At least one of CH2Cl2, Pd(OAc)2, PdCl2, Pd(PPh3)4, or PdCl2(PPh3)2; and / or the solvent is an organic solvent / water, wherein the organic solvent is preferably at least one of aromatic hydrocarbons, DMF, DMA, THF, acetonitrile, methanol, ethanol, isopropanol, dichloroethane, DMSO, dioxane, dichloromethane, or ethyl acetate.

5. An insecticide composition, characterized in that, It includes at least one of the fused heterocyclic compounds according to any one of claims 1-3 in an insecticidal effective amount; preferably, it also includes a formulation adjuvant; more preferably, it also includes other active ingredients.

6. A method for controlling pests, characterized in that, The composition includes a biologically effective amount of the fused heterocyclic compound of any one of claims 1-3 or the composition of claim 5, which exposes the pest or its environment to the biologically effective amount.

7. Use of the fused heterocyclic compound as described in any one of claims 1-3 or the composition as described in claim 5 in the control of pests.

8. An intermediate as described in Formula II of claim 4.

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