Triazole compound and preparation method therefor, and insecticidal composition and use thereof

Abstract

The present invention belongs to the technical field of pesticides, and specifically relates to a triazole compound and a preparation method therefor, and an insecticidal composition and the use thereof. The compound is as represented by general formula I, where X represents CR11 or N; X2 represents CR2 or N; W represents O or S; R1, R2, R3, R4, R5, R6, R7, R9 and R11 each independently represents hydrogen, halogen, alkyl, etc.; R8 represents hydrogen, alkyl, alkenyl, alkynyl, etc.; and R10 represents hydrogen, alkyl, alkenyl, alkynyl, etc. The compound exhibits a good control effect on Nilaparvata lugens, Rhopalosiphum padi, Laodelphax striatellus, Sogatella furcifera, Myzus persicae, Aphis craccivora, etc.

Description

Triazole compounds, their preparation methods, insecticidal compositions, and applications Technical Field

[0001] This invention belongs to the field of pesticide technology, specifically relating to a triazole 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 triazole compound, its preparation method, an insecticidal composition, and its application. The compound exhibits excellent insecticidal activity against brown planthoppers, cereal aphids, gray planthoppers, white-backed planthoppers, peach aphids, and peanut aphids.

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

[0005] A triazole compound or a salt thereof, as shown in general formula I:

[0006] Where X1 represents CR 11 Or N; X2 represents CR2 or N;

[0007] W represents O or S;

[0008] R1, R2, R3, R4, R5, R6, R7, R9, R 11 Each of the following groups independently represents hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(OR), -N(R)N(R)2, -N(R)(CO)R, -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR, or -(CO)N(R)2; wherein the alkyl, alkenyl, or alkynyl group is optionally substituted by at least one group selected from halogen, cyano, nitro, cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -O(CO)R, -O(CO)OR, -(CO)R, or -(CO)N(R)2;

[0009] R8 represents hydrogen, alkyl, alkenyl, alkynyl, -(CO)R, -N(R)2, -N(R)(CO)R, -N(R)(CO)OR, -N=C(R)2, -N=C(R)(OR), cycloalkyl, aryl, or heterocyclic; wherein the alkyl, alkenyl, or alkynyl group is optionally substituted by at least one group selected from halogen, cyano, cycloalkyl, aryl, heterocyclic, -OR, -(CO)OR, or -SR;

[0010] R 10 Represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, -OR, -N(R)2, -(CO)R, aryl, heterocyclic; wherein the alkyl, alkenyl or alkynyl is optionally substituted by at least one group selected from halogen, cyano, cycloalkyl, aryl, heterocyclic, -(CO)OR, -OR, trialkylsilyloxy or -SR;

[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;

[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, benzyl, or phenyl or benzyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

[0013] Preferably, R1, R2, R3, R4, R5, R6, R7, R9, R 11 Each of these groups independently represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(OR), -N(R)N(R)2, -N(R)(CO)R, -O(CO)R, -O(CO)OR, -(CO)R, -(C O)OR or -(CO)N(R)2; wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally substituted by at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -O(CO)R, -O(CO)OR, -(CO)R or -(CO)N(R)2;

[0014] R8 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, -(CO)R, -N(R)2, -N(R)(CO)R, -N(R)(CO)OR, -N=C(R)2, -N=C(R)(OR), C3-C8 cycloalkyl, aryl, or heterocyclic; wherein the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 ynyl is optionally substituted by at least one group selected from halogen, cyano, C3-C8 cycloalkyl, aryl, heterocyclic, -OR, -(CO)OR, or -SR;

[0015] R 10 Represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, -OR, -N(R)2, -(CO)R, aryl, heterocyclic; wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 ynyl is optionally substituted with at least one group selected from halogen, cyano, C3-C8 cycloalkyl, aryl, heterocyclic, -(CO)OR, -OR, tri(C1-C8)alkylsilyloxy or -SR;

[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 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;

[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, benzyl, or phenyl or benzyl 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] More preferably, R1, R2, R3, R4, R5, R6, R7, R9, R 11Each of these groups independently represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(OR), -N(R)N(R)2, -N(R)(CO)R, -O(CO)R, -O(CO)OR, -(CO)R, -(C O)OR or -(CO)N(R)2; wherein the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally substituted by at least one group selected from halogen, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -O(CO)R, -O(CO)OR, -(CO)R or -(CO)N(R)2;

[0019] R8 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, -(CO)R, -N(R)2, -N(R)(CO)R, -N(R)(CO)OR, -N=C(R)2, -N=C(R)(OR), C3-C6 cycloalkyl, aryl, or heterocyclic; wherein the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 ynyl is optionally substituted by at least one group selected from halogen, cyano, C3-C6 cycloalkyl, aryl, heterocyclic, -OR, -(CO)OR, or -SR;

[0020] R 10 Represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, -OR, -N(R)2, -(CO)R, aryl, heterocyclic; wherein the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 ynyl is optionally substituted with at least one group selected from halogen, cyano, C3-C6 cycloalkyl, aryl, heterocyclic, -(CO)OR, -OR, tri(C1-C6)alkylsilyloxy or -SR;

[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, benzyl, or phenyl or benzyl 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 one specific implementation, X2 represents CR 2。

[0024] 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.

[0025] 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

[0026] The terms "optional" or "optionally" mean that the event or situation described below may or may not occur, and the description includes instances where said event or situation occurs and instances where said event or situation does not occur. For example, the term "optionally...substituted" means that the specified atom or group is unsubstituted or substituted by one or more substituents. If a group is substituted by a group, this should be understood to mean that the group is substituted by one or more groups, either the same or different, selected from those groups mentioned. Furthermore, the same or different substitution characters contained in the same or different substituents are chosen independently and may be the same 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.

[0027] 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.

[0028] This invention provides a triazole compound having a chiral center as shown in Formula I':

[0029] Where the carbon atom at position * is the chiral center, and the substituents R1, R3, R4, R5, R6, R7, R8, R9, R 10 The definitions of X1, X2 and W are as described above.

[0030] In one specific embodiment, based on the content of stereoisomers having R and S configurations at position *, it has a stereochemical purity of 60-100%, preferably 70-100%, more preferably 80-100%, further preferably 90-100%, and even more preferably 95-100%.

[0031] "Stereochemical purity" refers to the percentage of the amount of the stereoisomer relative to the total amount of stereoisomers that generate chiral centers.

[0032] In this invention, the stereochemical configuration at position * in Formula I' is determined according to the Cahn-Ingold-Prelog system; however, the subject matter of this invention also relates to all stereoisomers at other positions included in Formula I, and mixtures thereof. Such Formula I compounds contain, for example, one or more additional asymmetric carbon atoms or other double bonds not specifically described in Formula I. It should be understood that this invention includes pure isomers and mixtures thereof enriched to varying degrees with pure isomers, for example, where the asymmetric carbon atom at position * has the aforementioned configuration, or in the mixture, the compound or a compound with the same chemical structure has the aforementioned configuration at position *, or is present in a proportion where the compound having the aforementioned configuration is predominantly present (at least 60% configuration), while other asymmetric carbon atoms may be present in racemic form or may be resolved to varying degrees. As long as the stereochemical configuration conditions are met, possible stereoisomers defined by specific spatial forms, such as enantiomers, diastereomers, Z- and E-isomers, are all included in Formula I and can be obtained from mixtures of stereoisomers by conventional methods, or can be prepared by stereoselective reactions in combination with stereochemically pure initial substances.

[0033] If various functional groups are present, the present invention also includes any ketone and enol tautomer forms, mixtures thereof, and salts thereof.

[0034] The method for preparing the triazole compound includes the following steps:

[0035] (1) When R8 is H, the compound of general formula I-1 is prepared from the compound of general formula II, and the reaction equation is as follows:

[0036] (2) When R8 is not H, the compound represented by general formula II reacts with the compound represented by general formula III to obtain the compound represented by general formula I. The reaction equation is as follows:

[0037] (3) When R8 is not H, the compound represented by general formula II reacts with the compound represented by general formula VI to obtain the compound represented by general formula I. The reaction equation is as follows:

[0038] (4) The compound represented by general formula IV reacts with the compound represented by general formula VII to obtain the compound represented by general formula I. The reaction equation is as follows:

[0039] (5) The compound represented by general formula VIII and the compound represented by general formula IX react to obtain the compound represented by general formula I. The reaction equation is as follows:

[0040] Where Hal represents halogen, Y represents alkali metal (such as Li, Na or K), M represents OH or halogen, and P represents N(R) 12 2. OR 12 or SR 12 Wait, R 12 Representing C1-C6 alkyl groups, R1, R3, R4, R5, R6, R7, R8, R9, R 10 The definitions of X1, X2, and W are as described above;

[0041] In one specific embodiment, the reaction (1) is carried out in the presence of a base and a solvent.

[0042] In another specific embodiment, the base is selected from at least one of inorganic or organic bases, such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KI, NaI, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, NaH, KH, DMAP, pyrazole, triethylamine, or DIEA, etc.

[0043] In another specific embodiment, the solvent is an organic acid / water; the organic acid is formic acid, acetic acid, or propionic acid, etc.

[0044] In one specific embodiment, the reaction (2) is carried out in the presence of a solvent.

[0045] In another specific embodiment, the solvent is selected from at least one of aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, THF, dioxane, dichloromethane, toluene, or ethyl acetate.

[0046] In one specific embodiment, the reaction (3) is carried out in the presence of a base and a solvent.

[0047] In another specific embodiment, the base is selected from at least one of inorganic or organic bases, such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KI, NaI, KOAc, AcONa, K3PO4, t-BuONa, t-BuOK, EtONa, NaOH, KOH, NaOMe, NaH, KH, DMAP, pyrazole, triethylamine, or DIEA, etc.

[0048] In another specific embodiment, the solvent is selected from at least one of aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, THF, dioxane, dichloromethane, diethyl ether, toluene, or ethyl acetate.

[0049] In one specific embodiment, the reaction (4) is carried out in the presence of a solvent.

[0050] In another specific embodiment, a base and / or a condensing agent are added during the reaction.

[0051] In another specific embodiment, the solvent is selected from at least one of aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, THF, dioxane, dichloromethane, toluene, or ethyl acetate.

[0052] In another specific embodiment, the base is selected from at least one of inorganic or organic bases, such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KI, NaI, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, NaH, KH, DMAP, pyrazole, triethylamine, or DIEA, etc.

[0053] In another specific embodiment, the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU, or HATU.

[0054] In one specific embodiment, the reaction (5) is carried out in the presence of a solvent.

[0055] In another specific embodiment, the solvent is an organic acid (such as formic acid, acetic acid, or propionic acid), or a combination thereof with at least one selected from aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, THF, dioxane, dichloromethane, toluene, or ethyl acetate.

[0056] In one specific embodiment, the compound represented by formula II is prepared by reacting the compound represented by formula IV and the compound represented by formula V or their salts (such as hydrochloride salts), as shown in the following reaction equation:

[0057] Where M represents OH or halogen (preferably chlorine).

[0058] In one specific embodiment, the reaction is carried out in the presence of a solvent.

[0059] In another specific embodiment, a base and / or a condensing agent are added during the reaction.

[0060] In another specific embodiment, the solvent is selected from at least one of aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, tetrahydrofuran, or ethyl acetate.

[0061] In another specific embodiment, the base is selected from at least one of inorganic or organic bases, such as K2CO3, Na2CO3, Cs2CO3, NaHCO3, KF, CsF, KI, NaI, KOAc, AcONa, K3PO4, t-BuONa, EtONa, NaOH, KOH, NaOMe, NaH, KH, DMAP, pyrazole, triethylamine, or DIEA, etc.

[0062] In another specific embodiment, the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU, or HATU.

[0063] In one embodiment, the insecticidal composition comprises at least one of the triazole compounds in a biologically effective amount, preferably further comprising a formulation adjuvant; more preferably, it further comprises other active ingredients.

[0064] The present invention also provides an intermediate, as shown in formulas II, VII, VIII or IX.

[0065] 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.

[0066] 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.

[0067] 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.

[0068] The present invention also relates to the use of compounds of Formula I as insecticides, and in particular as crop protectants.

[0069] In the context of this application, the term "insecticide" often also includes the term "crop protectant".

[0070] 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 ...

[0071] 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.

[0072] 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.

[0073] 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.

[0074] 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.

[0075] 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.

[0076] 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.

[0077] 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).

[0078] 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.

[0079] 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.

[0080] 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.

[0081] 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.

[0082] 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.

[0083] 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.

[0084] 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.

[0085] 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.

[0086] 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.

[0087] 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.

[0088] 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.

[0089] 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.

[0090] 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.

[0091] 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.

[0092] 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.

[0093] 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 use form prepared from such formulations, preferably those described below.

[0094] 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.

[0095] Insecticides / Acaricides / Nematodes

[0096] 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 can be found on the internet (e.g., http: / / www.alanwood.net / pesticides).

[0097] (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.

[0098] (2) GABA-gated chloride channel antagonists, such as cyclopentadiene organochlorines, such as chlordane and endosulfan; or phenylpyrazoles, such as ethiprole and fipronil.

[0099] (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.

[0100] (4) Nicotinic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.

[0101] (5) Allosteric activators of nicotinic acetylcholine receptors (nAChR), such as spinosides, such as spintoram and spinosad.

[0102] (6) Chloride channel activators, such as abamectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin and milbemectin.

[0103] (7) Juvenile hormone mimics, such as hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

[0104] (8) Active ingredients with unknown or non-specific mechanisms of action, such as

[0105] Alkyl halides, such as methyl bromide and other alkyl halides; or chloropicrine or thiocyanate or borax or tartar emetic.

[0106] (9) Selective antifeedants, such as pymetrozine or flonicamid.

[0107] (10) Mite growth inhibitors, such as tetradifon, thiamethoxam and diflovidazin or etoxazole.

[0108] (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.

[0109] (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.

[0110] (13) Oxidative phosphorylation decoupling agents that interrupt the H proton gradient, such as chlorfenapyr, dinitrocresol (DNOC) and sulfluramid.

[0111] (14) Nicotinic acetylcholine receptor antagonists, such as bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0112] (15) Type O chitin biosynthesis inhibitors, such as bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron, and triflumuron.

[0113] (16) Type I chitin biosynthesis inhibitors, such as buprofezin.

[0114] (17) Ecchymosis inhibitors (especially for Diptera, i.e., Diptera), such as cyromazine.

[0115] (18) Ecdysone receptor agonists, such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0116] (19) Octopus aminergic agonists, such as amitraz.

[0117] (20) Complex-III electron transport inhibitors, such as hydramethylnone, acequinocyl, or fluacrypyrim.

[0118] (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).

[0119] (22) Voltage-gated sodium channel blockers, such as indoxacarb or metaflumizone.

[0120] (23) Inhibitors of acetyl-CoA carboxylase, such as tetronic acid and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[0121] (24) Complex-IV electron transport inhibitors, such as phosphine, such as aluminum phosphide, calcium phosphide, phosphine hydrogen and zinc phosphide; or cyanide.

[0122] (25) Complex-type II electron transport inhibitors, such as cyenopyrafen and cyflumetofen.

[0123] (28) Lanni base receptor effectors, such as diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide;

[0124] 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).

[0125] fungicides

[0126] 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).

[0127] Biopesticides as a mixed component

[0128] Compounds of Formula I can be combined with biopesticides.

[0129] Biopesticides include, in particular, products produced by bacteria, fungi, yeast, plant extracts, and microorganisms, including proteins and secondary metabolites.

[0130] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria, and bacteria that can act as biological insecticides, fungicides, or nematicides.

[0131] 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.

[0132] As a safety agent for mixed components

[0133] 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).

[0134] Plants and plant parts

[0135] 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.

[0136] 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.

[0137] 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.

[0138] Transgenic plants, seed treatment, and integration events.

[0139] 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.

[0140] Crop protection – types of treatment

[0141] 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.

[0142] 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.

[0143] 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).

[0144] Seed treatment

[0145] 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.

[0146] 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.

[0147] 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.

[0148] 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.

[0149] 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.

[0150] 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.

[0151] A further advantage is that treating seeds with the compound of formula I can promote germination and emergence of the treated seeds.

[0152] Also considered advantageous is that compounds of formula I can be used, especially, for genetically modified seeds.

[0153] 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.

[0154] 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.

[0155] 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.

[0156] 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.

[0157] 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.

[0158] 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.

[0159] 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.

[0160] 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.

[0161] 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.

[0162] 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.

[0163] 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.

[0164] 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.

[0165] 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.

[0166] 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.

[0167] 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.

[0168] 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.

[0169] 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.

[0170] 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.

[0171] 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.

[0172] For animal health

[0173] 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.

[0174] 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.

[0175] 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.

[0176] 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.

[0177] In a preferred embodiment, the compound of Formula I is administered to a mammal.

[0178] In another preferred embodiment, the compound of formula I is administered to poultry, i.e., caged birds and especially poultry.

[0179] 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.

[0180] 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.

[0181] 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.

[0182] 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.

[0183] 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.

[0184] 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.

[0185] Vector control

[0186] 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).

[0187] 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.

[0188] 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.

[0189] If the compound of formula I is resistant to damage, then vector control is also possible.

[0190] 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.

[0191] Protection of industrial materials

[0192] 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.

[0193] 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.

[0194] In another embodiment, the compound of formula I is used in conjunction with at least one other insecticide and / or at least one fungicide.

[0195] 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.

[0196] 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.

[0197] Control of animal pests in the health field

[0198] 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.

[0199] 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.

[0200] 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

[0201] 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.

[0202] 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. The specific compound structures and corresponding compound information are shown in Table 1. 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.

[0203] Table 1. Compound Structures

[0204] Table 2 Compounds 1 H NMR

[0205] Table A has the same structure as Table 1 above, except that the general formula I is replaced with the general formula I' which has a chiral center. In Table A, the entries under the “Serial Number” column heading are described as 1'-108', 110'-257', and 259'-265' respectively. For example, 1' corresponds to the compound 1 in Table 1 in which the chiral carbon at the * position of the general formula is in the S configuration.

[0206] 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.

[0207] 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.

[0208] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0209] 1. Synthesis of compound 12'

[0210] (1) Compound 12-1 (7 g, 1.0 eq) was dissolved in 100 mL of DCM, and NaOH (3 eq) was dissolved in water and added to the system. 12-2 (1.1 eq) was added under ice bath conditions. The reaction was carried out overnight at room temperature. After the reaction was detected to be complete by LCMS, it was extracted with H2O and DCM (100 mL × 3). The organic phases were combined and concentrated to obtain 12-3 (8.3 g, yield 90%).

[0211] (2) Compound 12-3 (10 g, 1.0 eq) was dissolved in 50 mL of DMF, and NaH (1.5 eq) was slowly added with stirring at room temperature. The reaction was allowed to proceed for 30 min at room temperature. Then, 12-4 (1.5 eq) was added, and the mixture was heated to 100 °C and stirred overnight. After the reaction was confirmed to be complete by LCMS, the mixture was extracted with EA (200 mL), washed with H2O (200 mL × 2), and the organic phase was washed twice with saturated brine. The mixture was then dried and concentrated. The residue was purified by column chromatography to give product 12-5 (3.6 g, yield 28%).

[0212] (3) Compound 12-5 (2g, 1.0eq) and sodium acetate (1.5eq) were dissolved in 18mL of HOAc / H2O (5:1) mixed solvent and stirred overnight at 100℃. After the reaction was confirmed to be complete by LCMS, it was extracted with EA (50mL×3). The organic phases were combined and washed with H2O (10mL×2). The organic phases were dried and concentrated to obtain 12' (1.2g, yield 62%).

[0213] 2. Synthesis of compound 2'

[0214] 12' (1.2 g, 1.0 eq) and Pd / C (120 mg, 10%) were added to 100 mL of methanol. The system was then replaced with hydrogen gas and stirred overnight at room temperature. After the reaction was confirmed to be complete by LCMS, palladium on carbon was removed by diatomaceous earth filtration, and the organic phase was dried and concentrated. The residue was purified by column chromatography to give compound 2' (3.6 g, 28% yield).

[0215] 3. Synthesis of Compound 8

[0216] (1) Compound 8-1 (5 g, 1 eq) was dissolved in DCM (50 mL), and 8-2 (1.5 eq) was added. The mixture was heated under reflux for 2 h. The reaction was completed after dilution with acetonitrile. The mixture was cooled to room temperature, and the DCM and the remaining 8-2 were removed by rotation to obtain compound 8-3 (6.8 g, crude product).

[0217] (2) Dissolve product 8-3 obtained in the previous step in dioxane (50 mL) and AcOH (10 mL), add 8-4 (1 eq), and stir overnight at 50 °C. Take 0.1 mL of the reaction solution, dilute with acetonitrile, and send as a sample to show that the reaction is complete. Directly evaporate to dryness, and purify with silica gel in a normal phase to obtain compound 8-5 (4.1 g, two-step yield 43%).

[0218] (3) Compound 8-5 (0.5 g, 1.0 eq) was dissolved in 50 mL of MeCN, and potassium carbonate (0.72 g, 3.0 eq) and 8-6 (0.23 g, 1.05 eq) were added. The mixture was reacted overnight at 80 °C. The reaction was monitored by LCMS until complete, and the product was the main peak. The mixture was filtered, concentrated under reduced pressure, and purified by column chromatography to obtain a colorless liquid 8-7 (0.43 g, yield 77%).

[0219] (4) Compound 8-7 (0.4 g, 1.0 eq) was dissolved in 30 mL of acetonitrile, and triethylamine (0.17 g, 3.0 eq) and 8-8 (0.45 g, 1.2 eq) were added. The mixture was reacted overnight at 80 °C. LCMS monitoring showed that the reaction proceeded completely, and the product was the main peak. The reaction solution was evaporated to dryness, extracted three times with ethyl acetate and saturated brine, and the organic phase was concentrated. The residue was purified by column chromatography to give a pale yellow solid 8-9 (0.6 g, yield 83%).

[0220] (5) Compounds 8-9 (0.5 g, 1.0 eq) were dissolved in a solvent (15 mL acetic acid and 3 mL water), and potassium acetate (0.18 g, 2 eq) was added. The mixture was reacted overnight at 100 °C. The reaction of the starting material was monitored by LCMS until complete, and the product was the main peak. The solvent was concentrated, and the mixture was extracted with EA and water. The organic phase was washed twice with saturated brine, dried, and concentrated. The residue was purified by column chromatography to give a white solid 8 (0.35 g, yield 72.5%).

[0221] 4. Synthesis of compound 23'

[0222] (1) Compound 23-1 (30 g, 1.0 eq) was dissolved in 150 mL of DMF, and 23-2 (32.05 g, 1.0 eq), DIEA (61.1 g, 3.0 eq), and HATU (90 g, 1.5 eq) were added. The mixture was reacted overnight at room temperature. The reaction mixture was monitored by LCMS until the starting material was completely reacted, and the product was the main peak. The reaction solution was extracted with EA and water, and the organic phase was washed twice with saturated brine, dried, and concentrated. The residue was purified by column chromatography to give a pale yellow liquid 23-3 (48 g, yield 81.1%).

[0223] (2) Compound 23-3 (10 g, 1.0 eq) was dissolved in a solvent (100 mL 1,4-dioxane and 20 mL acetic acid), and 8-4 (5.78 g, 1.5 eq) was added. The mixture was reacted overnight at 50 °C. LCMS monitoring showed that the reaction of the starting material was complete, and the product was the main peak. The solvent was removed by concentration, and the mixture was extracted with EA and water. The organic phase was washed twice with saturated brine, dried, and concentrated. The residue was purified by column chromatography to give a yellow oily substance 23-4 (8.6 g, yield 71.0%).

[0224] (3) Take a 250 mL round-bottom flask and dissolve compound 23-4 (3 g, 1.0 eq) in 20 mL of hydrogen chloride / 1,4-dioxane solution. React at room temperature overnight. Monitor the reaction of the starting material by LCMS until the reaction is complete and the product is the main peak. Concentrate to remove the solvent and obtain a white solid 23-5 (to be used directly in the next step, calculated as 100% yield).

[0225] (4) The compound 23-5 obtained in the previous step was dissolved in 20 mL of acetonitrile, and triethylamine (3.34 g, 5.0 eq) was added. 8-8 (1.83 g, 1.0 eq) was added dropwise under stirring at room temperature, and the reaction was carried out at room temperature for 30 min. The reaction of the starting material was monitored by LCMS until complete, and the product was the main peak. The solvent was removed by concentration, and the product was extracted with EA and water. The organic phase was washed twice with saturated brine, dried, and concentrated. The residue was purified by column chromatography to obtain a light yellow solid 23-6 (2.4 g, two-step yield 73.5%).

[0226] (5) Compound 23-6 (180 mg, 1 eq) was dissolved in 5 mL of THF. The reaction flask was placed in an ice bath to cool, and 30% sodium methoxide solution (79 mg, 1.2 eq) was slowly added dropwise with stirring in the ice bath. The reaction was allowed to proceed overnight at room temperature. LCMS was used to monitor the reaction until the starting material was fully reacted, with the product as the main peak. The reaction solution was extracted with EA and water, and the organic phase was washed twice with saturated brine, dried, and concentrated. The residue was purified by column chromatography to give a white solid 23' (131 mg, yield 73.4%).

[0227] 5. Synthesis of Compound 11'

[0228] Compound 23' (200 mg, 1.0 eq) was dissolved in 5 mL of acetonitrile, and cuprous chloride (81 mg, 2.0 eq) and copper chloride (110 mg, 2.0 eq) were added. Tert-butyl nitrite (63.2 mg, 1.5 eq) was slowly added dropwise using a 1 mL syringe under ice bath conditions, and the mixture was allowed to rise naturally to room temperature overnight. LC-MS monitoring showed complete reaction of the starting material, with the product as the dominant peak. The mixture was filtered through diatomaceous earth, and the mother liquor was concentrated. Extraction was performed with EA and water, and the organic phase was washed twice with saturated brine, dried, and concentrated. The residue was purified by column chromatography to give a white solid 11' (185 mg, yield 89.0%).

[0229] 6. Synthesis of compound 14'

[0230] (1) Compound 23' (300 mg, 1.0 eq) was dissolved in 5 mL of acetonitrile, and cuprous bromide (176 mg, 2.0 eq) and copper bromide (274 mg, 2.0 eq) were added. Tert-butyl nitrite (95 mg, 1.5 eq) was slowly added dropwise with a 1 mL syringe under ice bath conditions, and the mixture was allowed to rise naturally to room temperature overnight. LC-MS was used to monitor the reaction until complete, with the product as the main peak. The mixture was filtered through diatomaceous earth, the mother liquor was concentrated, and extracted with EA and water. The organic phase was washed twice with saturated brine, dried, and concentrated. The residue was purified by column chromatography to give a pale yellow oil 14-1 (232 mg, yield 68.5%).

[0231] (2) Compound 14-1 (232 mg, 1.0 eq) was dissolved in a solvent (10 mL 1,4-dioxane and 1 mL H2O), and 14-2 (176 mg, 1.5 eq) and cesium carbonate (274 mg, 3.0 eq) were added. The mixture was substituted with N2 three times, and then 1,1'-bis(diphenylphosphine)ferrocene palladium(II) chloride (2.5 mol%) was added. The mixture was substituted with N2 three times, and the reaction was carried out overnight at 100 °C. The reaction of the starting material was monitored by LCMS until the reaction was complete, and the product was the main peak. The mixture was filtered through diatomaceous earth, the mother liquor was concentrated, and extracted with EA and water. The organic phase was washed twice with saturated brine, dried, and concentrated. The residue was purified by column chromatography to obtain a light yellow oily substance 14' (232 mg, yield 69.2%).

[0232] 7. Synthesis of compound 16'

[0233] (1) Compound 23' (300 mg, 1.0 eq) was dissolved in 5 mL of acetonitrile, and copper iodide (305.5 mg, 3.0 eq) and cuprous iodide (234 mg, 2.0 eq) were added. Tert-butyl nitrite (95 mg, 1.5 eq) was slowly added dropwise using a 1 mL syringe under ice bath conditions. The mixture was heated to 80 °C and reacted for one hour. LC-MS monitoring showed that the reaction of the starting material was complete, and the product was the main peak. The mixture was filtered through diatomaceous earth, the mother liquor was concentrated, and extracted with EA and water. The organic phase was washed twice with saturated brine, dried, and concentrated. The residue was purified by column chromatography to give a light yellow oil 16-1 (247 mg, yield 67.1%).

[0234] (2) Compound 16-1 (247 mg, 1.0 eq) was dissolved in 5 mL of DMF, and 16-2 (305.5 mg, 2.0 eq) and cuprous iodide (234 mg, 1.0 eq) were added. The mixture was replaced with N2 and reacted overnight at 120 °C. The reaction was monitored by LCMS until the starting material was completely reacted. The mixture was filtered through diatomaceous earth, extracted with EA and water, and the organic phase was washed twice with saturated brine, dried, and concentrated. The residue was purified by column chromatography to give a white oily substance 16' (247 mg, yield 67.1%).

[0235] 8. Synthesis of compound 22'

[0236] Compound 23' (550 mg, 1.0 eq) was dissolved in 5 mL of DCE, and 85% m-CPBA (916 mg, 4.0 eq) was added. The mixture was reacted at 80 °C for 4 h. LC-MS monitoring showed that the reaction proceeded to completion, with the product as the dominant peak. The reaction solution was extracted with water, and the organic phase was washed twice with saturated brine and twice with saturated sodium bicarbonate solution, then dried and concentrated. The residue was purified by column chromatography to give a yellow oily substance 22' (107 mg, yield 18.3%).

[0237] 9. Synthesis of compound 29'

[0238] Compound 23' (131 mg, 1.0 eq) was dissolved in 5 mL of DCM, and acetyl chloride (130 mg, 10.0 eq) was added dropwise with stirring at room temperature. The reaction was allowed to proceed overnight at room temperature. LCMS monitoring showed that the reaction proceeded to completion, with the product as the dominant peak. The reaction solution was extracted with water, and the organic phase was washed twice with saturated brine, dried, and concentrated. The residue was purified by column chromatography to give a white solid 29' (96 mg, yield 67.5%).

[0239] 10. Synthesis of compound 34'

[0240] (1) Compound 34-1 was dissolved in 1,4-dioxane (20 mL) and AcOH (20 mL), and 8-4 (6.5 g, 1 eq) was added. The mixture was stirred overnight at 50 °C. After the reaction was confirmed to be complete by LCMS, the mixture was directly evaporated to dryness and purified by normal phase chromatography with silica gel to obtain a yellow oily compound 34-2 (10 g, yield 76%).

[0241] (2) Dissolve compound 34-2 in 20 mL of EA, add 40 mL of 4 M HCl / dioxane solution, and stir at room temperature for 3-6 hours. Dilute with methanol and send the sample. After the reaction is confirmed to be complete by LCMS, evaporate directly to dryness to obtain a yellow semi-solid compound 34-3 (8 g, yield 99%).

[0242] (3) Compound 34-4 (0.23 g, 1.0 eq) was dissolved in 3 mL of DCM, two drops of DMF were added, and then oxaloyl chloride (0.277 g, 3.0 eq) was added dropwise at 0 °C. The mixture was stirred at room temperature for 1 h, and the reaction was monitored by LCMS after quenching with methanol until complete. The solvent was concentrated to obtain product 34-5 (crude product). 5 mL of DCM was added to the residue to dissolve it for later use. 34-3 (200 mg, 1.0 eq) was dissolved in 3 mL of DCM, and TEA (220 mg, 3.0 eq) was added. The DCM solution of 34-5 was added dropwise to the reaction mixture at 0 °C. The reaction was monitored by LCMS until complete, and the product was the main peak. The mixture was washed with dilute hydrochloric acid, extracted with DCM, dried, and concentrated. The residue was purified by column chromatography to obtain a white solid 34-6 (177 mg, yield 51.3%).

[0243] (2) Compound 34-6 (0.177 g, 1.0 eq) was dissolved in a solvent (2.5 mL CH3COOH and 0.5 mL H2O), and sodium acetate (44 mg, 1.5 eq) was added. The mixture was stirred overnight at 100 °C. The reaction was monitored by LCMS until complete, and the product was the main peak. The solvent was removed by concentration, and the mixture was extracted with water and EA. The organic phase was concentrated to give a colorless oil 34' (155 mg, yield 46%).

[0244] 11. Synthesis of compound 38'

[0245] (1) Dissolve 38-1 (200 mg, 1.2 eq) in DCM, add three drops of DMF, and then add oxalyl chloride (185 mg, 2.0 eq) under ice bath conditions. Monitor the reaction progress by LCMS. Concentrate the reaction solution to obtain crude 38-2. Add crude 38-2 dropwise to a DCM solution containing 34-3 (200 mg, 1.0 eq) and stir at room temperature until the reaction is complete. Wash the reaction solution with H2O (20 mL × 3), dry the organic phase with anhydrous sodium sulfate, concentrate, and purify by column chromatography to obtain 38-3 (147 mg, yield 45%).

[0246] (2) 38-3 (147 mg, 1.0 eq) and sodium acetate (40 mg, 1.5 eq) were added to 18 mL of HOAc / H2O (5:1) mixed solvent and stirred overnight at 100 °C. After the reaction was confirmed to be complete by LCMS, it was extracted with EA (30 mL × 3). The organic phases were combined and washed with H2O (10 mL × 2). The organic phases were dried and concentrated to obtain compound 38' (135 mg, yield 96%).

[0247] 12. Synthesis of compound 108'

[0248] The synthesis of compound 108-1 was performed according to 38-3. Compound 108-2 (30 mg, 0.42 mmol) was dissolved in tetrahydrofuran (5 mL) under ice bath conditions, and NaH (0.42 mmol) was added. The reaction was allowed to proceed for 1 hour, and then 108-1 (200 mg) was added. After the reaction was completed at room temperature, the mixture was quenched with water, extracted with dichloromethane, and the organic phase was evaporated to dryness. The mixture was then purified by mixing with normal phase to give compound 108' (60 mg, yield 28%).

[0249] 13. Synthesis of compound 131'

[0250] At room temperature, compound 16-1 (2.00 g, 3.33 mmol) was dissolved in dioxane (20 mL), and Pd(dppf)Cl2 (54.0 mg, 0.07 mmol), potassium carbonate (1.38 g, 9.99 mmol), and potassium vinyl fluoroborate (535 mg, 4.00 mmol) were added. After the addition was complete, N2 was used to replace the solution three times, and the temperature was raised to 100 °C. The reaction was maintained at this temperature for 16 hours. After the reaction was completed, the solution was mixed and purified in normal phase to obtain compound 131' (850 mg, yield 51%).

[0251] 14. Synthesis of compound 130'

[0252] At room temperature, compound 131' (120 mg, 0.24 mmol) was dissolved in MeOH (5 mL), and Pd / C (20.0 mg) was added. After the addition was complete, H2 was used to replace the solution three times, and the reaction was carried out at room temperature for 16 hours under H2 atmosphere. After the reaction was completed, the reaction solution was filtered, washed with MeOH, and the filtrate was mixed and passed through a column to obtain compound 130' (80.0 mg, yield 66%).

[0253] 15. Synthesis of Compound 136

[0254] Compound 12 (350 mg, 12.98 mmol) was dissolved in acetonitrile, and 6 M potassium hydroxide aqueous solution was added in an ice bath. Trifluoromethanesulfonic acid (difluoromethyl) ester (2 eq) was added dropwise, and the reaction was carried out in an ice bath for 1 h. The main peak of the product was monitored by LCMS, and EA and H2O were added for extraction. The organic phase was dried, mixed, and passed through a column. The sample was then evaporated to dryness to obtain compound 136 (250 mg, yield 63%).

[0255] 16. Synthesis of compound 137'

[0256] At room temperature, compound 131' (760 mg, 1.52 mmol) was dissolved in THF (5 mL) and water (5 mL), and NaIO4 (1.48 g, 6.84 mmol) and K2O5O4·2H2O (22.3 mg, 0.08 mmol) were added. After the addition was complete, the reaction was carried out at 65 °C for 1 hour. After the reaction was completed, EA was added and the mixture was extracted three times by separation. The organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, and the organic phase was stirred by rotary osmosis and passed through a column to obtain compound 137' (680 mg, yield 89%).

[0257] 17. Synthesis of Compound 127'

[0258] At 0 °C, compound 137' (120 mg, 0.24 mmol) was dissolved in DCM (5 mL), and diethylaminotrifluoride (116 mg, 0.72 mmol) was added. After the addition was complete, the reaction was carried out at room temperature for 2 hours. After the reaction was completed, the reaction solution was poured into ice water and extracted three times with DCM. The organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, and the organic phase was stirred by rotary evaporation and passed through a column to obtain compound 127' (100 mg, yield 80%).

[0259] 18. Synthesis of compound 133'

[0260] At room temperature, compound 137' (450 mg, 0.89 mmol) was dissolved in dichloroethane (5 mL), and NaBH(OAc)3 (226 mg, 1.07 mmol) was added. After the addition was complete, the reaction was allowed to proceed at room temperature for 2 hours. Once the reaction was complete, the reaction solution was poured into water and extracted three times with DCM. The organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, and the organic phase was evaporated to dryness to obtain compound 133' (450 mg, 99% yield).

[0261] 19. Synthesis of Compound 128'

[0262] At room temperature, compound 133' (120 mg, 0.24 mmol) was dissolved in DCM (5 mL), and diethylaminotrifluoride (116 mg, 0.72 mmol) was added. After the addition was complete, the reaction was carried out at room temperature for 2 hours. After the reaction was completed, the reaction solution was poured into ice water and extracted three times with DCM. The organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, and the organic phase was stirred by rotary evaporation and passed through a column to obtain compound 128' (80.0 mg, yield 66%).

[0263] 20. Synthesis of compound 129'

[0264] At room temperature, compound 133' (120 mg, 0.24 mmol) was dissolved in DCM (5 mL), SOCl2 (84.2 mg, 0.71 mmol) was added, and one drop of DMF was added. The reaction was carried out at 40 °C for 2 hours. After the reaction was completed, the sample was stirred and passed through a column to obtain compound 129' (60.0 mg, yield 48%).

[0265] 21. Synthesis of compound 132'

[0266] (1) At room temperature, compound 16-1 (300 mg, 0.50 mmol) was dissolved in triethylamine (5 mL), and Pd(PPh3)4 (29.0 mg, 0.03 mmol), CuI (10.0 mg, 0.05 mmol) and trimethylsilylacetylene (138 mg, 1.50 mmol) were added. The reaction was carried out at 50 °C for 4 hours. After the reaction was completed, the reaction solution was stirred and passed through a column to obtain compound 132-1 (200 mg, yield 70%).

[0267] (2) At room temperature, compound 132-1 (100 mg, 0.17 mmol) was dissolved in MeOH (5 mL), and cesium fluoride (78.0 mg, 0.51 mmol) was added. The reaction was carried out at 40 °C for 1 hour. After the reaction was completed, the reaction solution was stirred and passed through a column to obtain compound 132' (80.0 mg, yield 92%).

[0268] 22. Synthesis of compound 134'

[0269] (1) At room temperature, compound 133' (150 mg, 0.30 mmol) was dissolved in DCM (5 mL), and triethylamine (91.0 mg, 0.90 mmol) and p-toluenesulfonic anhydride (147 mg, 0.45 mmol) were added. The reaction was carried out at room temperature for 2 hours. After the reaction was completed, the reaction solution was evaporated to dryness to obtain crude compound 134-1.

[0270] (2) At room temperature, compound 134-1 (197 mg, 0.30 mmol) was dissolved in MeOH (5 mL), sodium methoxide (24.0 mg, 0.45 mmol) was added, and the reaction was maintained at room temperature for 2 hours. After the reaction was completed, the reaction solution was poured into water and extracted three times with EA. The organic phases were combined, washed once with saturated brine, dried with anhydrous sodium sulfate, and the organic phase was stirred by rotary osmosis and passed through a column to obtain compound 134' (60.0 mg, two-step yield 39%).

[0271] 23. Synthesis of compound 135'

[0272] (1) At room temperature, compound 137' (465 mg, 0.93 mmol) was dissolved in EtOH (5 mL) and water (5 mL), and hydroxylamine hydrochloride (77.0 mg, 1.11 mmol) was added. The reaction was carried out at room temperature for 2 hours. After the reaction was completed, the ethanol in the reaction solution was evaporated, EA was added, and the mixture was extracted three times. The organic phases were combined, washed once with saturated brine, dried over anhydrous sodium sulfate, and the organic phase was evaporated to dryness to obtain crude compound 135-1.

[0273] (2) At room temperature, compound 135-1 (481 mg, 0.93 mmol) was dissolved in MeOH (5 mL), Pd / C (40.0 mg) was added, H2 was replaced three times, and the reaction was carried out at room temperature for 16 hours under H2 atmosphere. After the reaction was completed, the reaction solution was filtered, washed with MeOH, and the filtrate was mixed and passed through a column to obtain compound 135' (400 mg, two-step yield 85%).

[0274] 24. Synthesis of compound 143'

[0275] At room temperature, compound 16-1 (150 mg, 0.25 mmol) was dissolved in DMF (5 mL), and Zn(CN)2 (58.5 mg, 0.50 mmol), Pd2(dba)3 (27.5 mg, 0.03 mmol), and dppf (27.7 mg, 0.05 mmol) were added. The mixture was purged with N2 for 1 minute and placed in a microwave reactor. The reaction was carried out at 120 °C for 1.5 hours. After the reaction was completed, EA and water were added for three liquid-liquid extractions. The organic phases were combined, washed three times with saturated brine, dried over anhydrous sodium sulfate, and the organic phase was stirred by rotary osmosis and passed through a column to give compound 143' (80.0 mg, yield 64%).

[0276] 25. Synthesis of compound 152'

[0277] The synthesis of compound 85' was performed according to 38-3. Cesium fluoride (570 mg, 3.79 mmol) and diethyl bromofluoromethylphosphonate (950 mg, 3.79 mmol) were added to a 5 mL solution of compound 85' (600 mg, 1.26 mmol) in DCM at room temperature. The mixture was stirred at room temperature for 12 hours. LC-MS analysis showed that the starting material was almost completely consumed. After concentrating the organic phase, the crude product was separated by column chromatography to give a white solid, compound 152' (200 mg, 30% yield).

[0278] 26. Synthesis of compound 165'

[0279] (1) Compounds 165-1 (5.0 g, 15.2 mmol) and 165-2 (1.8 g, 15.2 mmol) were dissolved in 50 ml of DCM, stirred until homogeneous, and heated to 40 °C. The reaction was allowed to proceed for 4 h, and the reaction was allowed to proceed completely under control. The solution was then directly evaporated to dryness to give a pale yellow solid compound 165-3 (5.8 g, 100% yield).

[0280] (2) Compound 165-3 (4.0 g, 10.4 mmol) and compound 165-4 (1.7 g, 10.1 mmol) were dissolved in 20 ml of dioxane and 20 ml of acetic acid. After stirring evenly, the mixture was heated to 50 °C and reacted for 4 h. The reaction was carried out under controlled monitoring until complete, and then dried and concentrated. Silica gel column chromatography was used to obtain a pale yellow solid compound 165' (653 mg, yield 13%).

[0281] 27. Synthesis of Compound 145'

[0282] The synthesis of 145-1 was based on that of 165'. 145-1 (200 mg) was dissolved in 5 mL of tetrahydrofuran, and sodium methoxide (34 mg, 1.5 eq) was added. The reaction was carried out at room temperature. After the reaction was confirmed to be complete by LCMS, the mixture was extracted with EA. The organic phases were combined, washed with H2O, dried, and concentrated to give compound 145' (88 mg, yield 44%).

[0283] 28. Synthesis of compound 167'

[0284] Compound 165' (400 mg, 0.81 mmol) and P2S5 (362 mg, 1.6 mmol) were dissolved in 20 mL of toluene, stirred until homogeneous, and then heated to 100 °C for 12 h. The reaction was carried out under controlled monitoring until complete, and the mixture was dried and concentrated. Silica gel column chromatography yielded a pale yellow solid, compound 167' (180 mg, 43% yield).

[0285] 29. Synthesis of compound 181'

[0286] The synthesis of compound 181-2 was performed according to 34-3. At room temperature, compound 181-1 (150 mg, 0.52 mmol) was dissolved in DCM (5 mL). Oxaloyl chloride (197 mg, 1.55 mmol) was added dropwise under ice bath conditions. After the addition was complete, one drop of DMF was added. The reaction was allowed to proceed at room temperature for 1 hour. A sample was taken, diluted with methanol, and the reaction was monitored for completeness by LC-MS. The reaction solution was evaporated to dryness and dissolved in ACN for later use.

[0287] Compound 181-2 (129 mg, 0.52 mmol) was dissolved in acetonitrile (5 mL), and TEA (157 mg, 1.56 mmol) was added. The prepared solution was added dropwise under ice bath conditions. After the addition was complete, the reaction was allowed to proceed at room temperature for 0.5 hours, and the reaction was monitored by LCMS to ensure complete reaction. The reaction solution was stirred and passed through a column to obtain compound 181' (70.0 mg, yield 23%).

[0288] 30. Synthesis of compound 215'

[0289] Compound 165' (300 mg, 0.61 mmol) was dissolved in 50 mL of DMF, cooled to 0 °C, and NaH (48 mg, 1.2 mmol) was added. After 30 min, acetic anhydride (122 mg, 1.2 mmol) was added, and the reaction was carried out at room temperature for 12 h, with complete reaction as monitored. The mixture was extracted three times with water and ethyl acetate. The organic phases were combined, washed three times with saturated sodium chloride solution, dried, and concentrated. Silica gel column chromatography yielded a pale yellow solid, compound 215' (210 mg, 57% yield).

[0290] 31. Synthesis of Compound 250'

[0291] Compound 250-1 (200 mg, 0.4 mmol), compound 250-2 (60 mg, 0.8 mmol), and cesium carbonate (130 mg, 0.4 mmol) were dissolved in 20 mL of acetonitrile. After stirring until homogeneous, the mixture was heated to 80 °C and reacted for 2 h. The reaction was carried out under controlled monitoring until complete, and then dried and concentrated. Silica gel column chromatography yielded a pale yellow solid, compound 250' (58 mg, yield 19%).

[0292] 32. Synthesis of compound 261'

[0293] The synthesis of compound 261-1 was performed according to 38-3. Compound 261-2 (1.08 g, 5 eq) was dissolved in diethyl ether (10 mL), and potassium tert-butoxide (0.7 g, 3 eq) was added dropwise to the reaction system under ice bath conditions. The reaction was carried out at 0 °C for half an hour. After the reaction was completed, compound 261-1 (1.0 g, 1 eq) was dissolved in diethyl ether and added dropwise to the reaction system. The reaction was carried out at room temperature for 2 hours. After the reaction was completed, the mixture was extracted with EA and water, the organic phase was concentrated and dried, and purified by column chromatography to obtain compound 261' (1.0 g, yield 87%).

[0294] 33. Synthesis of compound 263'

[0295] (1) The synthesis of compound 263-1 was performed according to 8-5. Compound 263-2 (675 mg, 3.85 mmol) and potassium carbonate (530 mg, 3.85 mmol) were added to a solution of compound 263-1 (600 mg, 1.95 mmol) in acetonitrile (10 mL) at room temperature. The reaction mixture was heated to 80 °C and stirred for 12 hours. LC-MS analysis showed that the starting material was almost completely consumed. The concentrated reaction mixture was separated by column chromatography to obtain a white solid 263-3 (800 mg, 100% yield).

[0296] (2) To a solution of compound 263-3 (800 mg, 1.97 mmol) in acetonitrile (10 mL), 8-8 (650 mg, 2.36 mmol) and triethylamine (240 mg, 2.36 mmol) were added. The mixture was stirred at room temperature for 1 hour. LCMS analysis showed that the starting material was almost completely consumed. The concentrated reaction solution was separated by column chromatography to obtain a pale yellow solid compound 263' (800 mg, yield 62%).

[0297] 34. Synthesis of compound 262'

[0298] Cesium fluoride (750 mg, 4.95 mmol) was added to a methanol (10 mL) solution of compound 263' (800 mg, 1.23 mmol) at room temperature. The mixture was stirred at room temperature for 12 hours. LCMS analysis showed that the starting material was almost completely consumed. The concentrated reaction solution was separated by column chromatography to give a pale yellow solid compound 262' (500 mg, 75% yield).

[0299] Bioactivity evaluation (insecticide activity test)

[0300] Brown planthoppers, gray planthoppers, and white-backed planthoppers: Select test insects of similar physiological condition reared indoors and place them in disposable transparent plastic cups. Introduce 40-50 test insects of uniform growth into each cup, and place rice stalks in the cups. Wrap the rice stalks with moist cotton balls to maintain humidity. Then, spray using a spray tower. After spraying, cover the cup openings. Repeat three times, using the highest dose containing acetone as a control. After application, tightly close the lid and place in a treatment room (temperature 25℃, humidity 60%). After 48 hours, investigate the number of dead insects and calculate the mortality rate.

[0301] Wheat aphids (Gnaphalium affineum): Wheat was planted in disposable small black bowls, with 3-4 grains per bowl. When the wheat seedlings reached approximately 10cm in height, the aphids were introduced. After 3-4 days, once the aphid population had reached a certain size, an experiment was conducted. A small spray bottle was used for spraying, applying the pesticide 6-9 times per bowl until both sides of the leaves were moistened but not dripping. The treatment was repeated 3 times, with the highest dose containing acetone serving as a control. After application, the bowls were placed in a treatment room (25℃, 60% humidity). The number of dead aphids was assessed after 48 hours, and the mortality rate was recorded.

[0302] Peach aphids: Radish plants were planted in disposable cups, 3-4 plants per cup. When the radish seedlings reached about 8cm in height, the aphids were inoculated. After 3-4 days, once the aphid population reached a certain size, an experiment was conducted. A small spray bottle was used for spraying, spraying each plant 10-12 times until both sides of the leaves were moist but not dripping. This was repeated 3 times, with the highest dose containing acetone serving as a control. After application, the plants were placed in a treatment room (temperature 25℃, humidity 60%). The number of dead aphids was assessed after 48 hours, and the mortality rate was recorded.

[0303] Peanut aphids: Broad bean plants were planted in disposable cups, one plant per cup. When the seedlings reached approximately 10cm in height, the aphids were introduced. After 3-4 days, once the aphid population had reached a certain size, an experiment was conducted. A small spray bottle was used for spraying, applying 6-9 sprays per cup until both sides of the leaves were moistened but not dripping. The treatment was repeated three times, with the highest dose containing acetone serving as a control. After application, the plants were placed in a treatment room (25℃, 60% humidity). The number of dead aphids was assessed after 48 hours, and the mortality rate was recorded.

[0304] Western flower thrips and bean thrips: Cut untreated flat green beans into 2-3 cm long stem segments, soak them in the drug solution for 20 seconds, remove them and dry them on absorbent paper, then put them into a small plastic box with an outer diameter of 5 cm, and introduce 30 second-instar test insects that have been starved for 2 hours. After 48 hours, investigate the number of dead insects and count the mortality rate.

[0305] Mortality rate = (Number of dead insects / Number of tested insects) × 100%

[0306] Table 3. Representative insecticidal activity test results Note: N represents no data; control compound A: Reference compound B: Reference compound C:

[0307] Furthermore, numerous tests have revealed that the compounds and their compositions described in this invention exhibit excellent control activity against many pests belonging to the orders Hemiptera, Homoptera, and Thysanoptera. For example, compounds 1', 2', 3', 4', 14', 38', 101', 165', and 183', at 60 ppm, achieved a mortality rate of over 80% against peach aphids, peanut aphids, gray planthoppers, and white-backed planthoppers. Compounds 101', 108', 138', 139', 159', 160', 162', 163', and 16... The following 4', 166'-177', 179'-182', 189'-197', 200'-206', 208'-215', 217', 224'-226', 247', 249', 257', 258, 259', 264', and 265' saturates at 100 ppm can achieve a mortality rate of over 80% against western flower thrips and bean thrips. These saturates not only possess broad-spectrum, high-efficiency, and systemic properties, but also effectively control resistant pests and have considerable commercial value.

Claims

1. A triazole compound as shown in general formula I, or a salt thereof: in, X1 represents CR 11 Or N; X2 represents CR2 or N; W represents O or S; R1, R2, R3, R4, R5, R6, R7, R9, R 11 Each of the following groups independently represents hydrogen, halogen, alkyl, alkenyl, alkynyl, cyano, nitro, cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(OR), -N(R)N(R)2, -N(R)(CO)R, -O(CO)R, -O(CO)OR, -(CO)R, -(CO)OR, or -(CO)N(R)2; wherein the alkyl, alkenyl, or alkynyl group is optionally substituted by at least one group selected from halogen, cyano, nitro, cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -O(CO)R, -O(CO)OR, -(CO)R, or -(CO)N(R)2; R8 represents hydrogen, alkyl, alkenyl, alkynyl, -(CO)R, -N(R)2, -N(R)(CO)R, -N(R)(CO)OR, -N=C(R)2, -N=C(R)(OR), cycloalkyl, aryl, or heterocyclic; wherein the alkyl, alkenyl, or alkynyl group is optionally substituted by at least one group selected from halogen, cyano, cycloalkyl, aryl, heterocyclic, -OR, -(CO)OR, or -SR; R 10 Represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, -OR, -N(R)2, -(CO)R, aryl, heterocyclic; wherein the alkyl, alkenyl or alkynyl is optionally substituted by at least one group selected from halogen, cyano, cycloalkyl, aryl, heterocyclic, -(CO)OR, -OR, trialkylsilyloxy or -SR; 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; 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, benzyl, or phenyl or benzyl substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy.

2. The triazole compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, R7, R9, R 11 Each of these groups independently represents hydrogen, halogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(OR), -N(R)N(R)2, -N(R)(CO)R, -O(CO)R, -O(CO)OR, -(CO)R, -(C O)OR or -(CO)N(R)2; wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 alkynyl is optionally substituted by at least one group selected from halogen, cyano, nitro, C3-C8 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -O(CO)R, -O(CO)OR, -(CO)R or -(CO)N(R)2; R8 represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, -(CO)R, -N(R)2, -N(R)(CO)R, -N(R)(CO)OR, -N=C(R)2, -N=C(R)(OR), C3-C8 cycloalkyl, aryl, or heterocyclic; wherein the C1-C8 alkyl, C2-C8 alkenyl, or C2-C8 ynyl is optionally substituted by at least one group selected from halogen, cyano, C3-C8 cycloalkyl, aryl, heterocyclic, -OR, -(CO)OR, or -SR; R 10 Represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, -OR, -N(R)2, -(CO)R, aryl, heterocyclic; wherein the C1-C8 alkyl, C2-C8 alkenyl or C2-C8 ynyl is optionally substituted with at least one group selected from halogen, cyano, C3-C8 cycloalkyl, aryl, heterocyclic, -(CO)OR, -OR, tri(C1-C8)alkylsilyloxy or -SR; 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, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 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-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, benzyl, or phenyl or benzyl 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. The triazole compound according to claim 1, characterized in that, R1, R2, R3, R4, R5, R6, R7, R9, R 11 Each of these groups independently represents hydrogen, halogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -N(R)(OR), -N(R)N(R)2, -N(R)(CO)R, -O(CO)R, -O(CO)OR, -(CO)R, -(C O)OR or -(CO)N(R)2; wherein the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 alkynyl is optionally substituted by at least one group selected from halogen, cyano, nitro, C3-C6 cycloalkyl, aryl, heterocyclic, -OR, -SR, -SOR, -(SO2)R, -N(R)2, -O(CO)R, -O(CO)OR, -(CO)R or -(CO)N(R)2; R8 represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, -(CO)R, -N(R)2, -N(R)(CO)R, -N(R)(CO)OR, -N=C(R)2, -N=C(R)(OR), C3-C6 cycloalkyl, aryl, or heterocyclic; wherein the C1-C6 alkyl, C2-C6 alkenyl, or C2-C6 ynyl is optionally substituted by at least one group selected from halogen, cyano, C3-C6 cycloalkyl, aryl, heterocyclic, -OR, -(CO)OR, or -SR; R 10 Represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, -OR, -N(R)2, -(CO)R, aryl, heterocyclic; wherein the C1-C6 alkyl, C2-C6 alkenyl or C2-C6 ynyl is optionally substituted with at least one group selected from halogen, cyano, C3-C6 cycloalkyl, aryl, heterocyclic, -(CO)OR, -OR, tri(C1-C6)alkylsilyloxy or -SR; 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, benzyl, or phenyl or benzyl 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 of the specification.

4. A triazole compound having a chiral center as shown in Formula I': in, The carbon atom at position * is the chiral center, and the substituents are R1, R3, R4, R5, R6, R7, R8, R9, R. 10 The definitions of X1, X2 and W are as described in any one of claims 1-3; Based on the content of stereoisomers with R and S configurations at position *, it has a stereochemical purity of 60-100%, preferably 70-100%, more preferably 80-100%, further preferably 90-100%, and even more preferably 95-100%.

5. A method for preparing a triazole compound according to any one of claims 1-4, comprising the following steps: (1) When R8 is H, the compound of general formula I-1 is prepared from the compound of general formula II, and the reaction equation is as follows: (2) When R8 is not H, the compound represented by general formula II reacts with the compound represented by general formula III to obtain the compound represented by general formula I. The reaction equation is as follows: (3) When R8 is not H, the compound represented by general formula II reacts with the compound represented by general formula VI to obtain the compound represented by general formula I. The reaction equation is as follows: (4) The compound represented by general formula IV reacts with the compound represented by general formula VII to obtain the compound represented by general formula I. The reaction equation is as follows: (5) The compound represented by general formula VIII reacts with the compound represented by general formula IX to obtain the compound represented by general formula I. The reaction equation is as follows: Where Hal represents halogen, Y represents alkali metal, M represents OH or halogen, and P represents N(R) 12 2. OR 12 or SR 12 R 12 Representing C1-C6 alkyl groups, R1, R3, R4, R5, R6, R7, R8, R9, R 10 The definitions of X1, X2 and W are as described in any one of claims 1-3; Preferably, the reaction (1) is carried out in the presence of a base and a solvent; more preferably, the base is selected from at least one of an organic base or an inorganic base; and / or the solvent is an organic acid / water, wherein the organic acid is formic acid, acetic acid or propionic acid; Preferably, the reaction (2) is carried out in the presence of a solvent; more preferably, the solvent is selected from at least one of aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, THF, dioxane, dichloromethane, toluene or ethyl acetate. Preferably, the reaction (3) is carried out in the presence of a base and a solvent; more preferably, the base is selected from at least one of organic or inorganic bases, and / or the solvent is selected from at least one of aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, THF, dioxane, dichloromethane, diethyl ether, toluene or ethyl acetate. Preferably, the reaction (4) is carried out in the presence of a solvent; more preferably, a base and / or a condensing agent are added during the reaction; even more preferably, the base is selected from at least one of organic or inorganic bases, the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU or HATU, and / or the solvent is selected from at least one of aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, THF, dioxane, dichloromethane, toluene or ethyl acetate; Preferably, the reaction (5) is carried out in the presence of a solvent; the solvent is an organic acid, or a combination thereof with at least one selected from aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, THF, dioxane, dichloromethane, toluene or ethyl acetate.

6. The preparation method according to claim 5, characterized in that, The compound represented by general formula II is prepared by reacting the compound represented by general formula IV and the compound represented by general formula V or their salts, as shown in the following reaction equation: Where M represents OH or halogen; Preferably, the reaction is carried out in the presence of a solvent; more preferably, a base and / or a condensing agent are added during the reaction; even more preferably, the solvent is selected from at least one of aromatic hydrocarbons (such as toluene, xylene), DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, dioxane, dichloromethane, tetrahydrofuran, or ethyl acetate; the base is selected from at least one of inorganic or organic bases; and / or the condensing agent is selected from at least one of Py-BOP, Py-AOP, EDCI, HOBT, DCC, HBTU, or HATU.

7. An insecticide composition, characterized in that, It includes at least one of the triazole compounds according to any one of claims 1-4 in an effective insecticidal amount; preferably, it also includes a formulation adjuvant; more preferably, it also includes other active ingredients.

8. A method for controlling pests, characterized in that, Includes a biologically effective amount of the triazole compound of any one of claims 1-4 or the composition of claim 7, which exposes the pest or its environment to the biologically effective amount.

9. Use of the triazole compound as described in any one of claims 1-4 or the composition as described in claim 7 in the control of pests.

10. An intermediate as described in formula II, VII, VIII or IX of claim 5.

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