Substituted pyridine compound and preparation method therefor, insecticidal composition and use

Abstract

In the technical field of pesticides, specifically relating to a substituted pyridine compound and a preparation method therefor, an insecticidal composition, and a use. The compound is represented by the general formula (I); L represents a direct bond, -O-, -S-, -NR8-, an alkylene group, an alkenylene group, or an alkynylene group; R8 represents hydrogen or an alkyl group; Q represents a cycloalkyl group or a cycloalkenyl group; M represents an aryl group or a heterocyclic group; X represents a halogen; and Y1 and Y2 each independently represent hydrogen, a halogen, a cyano group, or the like. The compound exhibits excellent control effects against brown planthoppers, white-backed planthoppers, and the like.

Description

Substituted pyridine compound, preparation method thereof, insecticidal composition and application thereof TECHNICAL FIELD

[0001] The present application belongs to the technical field of pesticides, and particularly relates to a substituted pyridine compound, a preparation method thereof, an insecticidal composition and application thereof. BACKGROUND

[0002] In recent years, due to the long-term use of pest control agents such as insecticides or fungicides, pests have acquired resistance and become difficult to control by the existing insecticides or fungicides. In addition, some of the known pest control agents are highly toxic, or some destroy the ecological system through their long-term residual properties. In this case, although a large number of insecticides are known, there is still a need to develop new pest control agents with low toxicity and low residual properties. SUMMARY

[0003] The present application provides a substituted pyridine compound, a preparation method thereof, an insecticidal composition and application thereof, which has excellent insecticidal activity against brown planthopper, white-backed planthopper and the like.

[0004] The technical solution adopted by the present application is as follows:

[0005] A substituted pyridine compound or a salt thereof, N-oxide as shown in general formula I:

[0006] In the formula, L represents a direct bond, -O-, -S-, -NR8-, alkylene, alkenylene or alkynylene;

[0007] R8 represents hydrogen or alkyl;

[0008] Q represents cycloalkyl or cycloalkenyl;

[0009] M represents aryl or heterocyclic group;

[0010] X represents halogen;

[0011] Y1, Y2 independently represent hydrogen, halogen, cyano, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl, heterocyclic group, -OR9 or -S(O) m R9, or Y1, Y2 together with the carbon atom to which they are attached form C=N-OR9, C=C(R9)2, carbonyl or thiocarbonyl;

[0012] R9 independently represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, alkoxycarbonylalkyl, aryl, heterocyclic group, arylalkyl or heterocyclic group alkyl;

[0013] the aforementioned cycloalkyl or cycloalkenyl is optionally substituted with at least one member selected from the group consisting of hydroxy, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio or alkylsulfonyl;

[0014] the aforementioned heterocyclyl or aryl is optionally substituted with at least one member selected from the group consisting of halogen, nitro, cyano, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylalkynyl, -OR 10 , -alkylene-OR 10 , -O-alkylene-OR 10 , -alkylene-S(O) m R 10 , -S(O) m R 10 , -alkylene-COOR 10 , -COOR 10 , -COR 10 , -(CO)N(R 10 )2, trialkylsilyl or aryl or heterocyclyl which is unsubstituted or substituted with at least one member selected from the group consisting of halogen, alkyl or haloalkyl, or two adjacent carbon atoms in the ring form a cyclic structure with -(CH2) 10 -, -OCH2O-, -SCH2O-, -SCH2S- or -OCH2CH2O- which is unsubstituted or substituted with at least one member selected from the group consisting of halogen, alkyl, -COR 10 or -COOR n ;

[0015] R 10 each independently represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, or aryl, arylalkyl, heterocyclyl or heterocyclylalkyl which is unsubstituted or substituted with at least one member selected from the group consisting of alkyl, halogen, alkoxy, haloalkoxy or haloalkyl;

[0016] m represents 0, 1 or 2;

[0017] n represents 1, 2, 3 or 4.

[0018] In one specific embodiment,

[0019] L represents a direct bond, -O-, -S-, -NR8-, C1-C8 alkylene, C2-C8 alkenylene or C2-C8 alkynylene;

[0020] R8 represents hydrogen or C1-C8 alkyl;

[0021] Q represents C3-C8 cycloalkyl or C3-C8 cycloalkenyl;

[0022] M represents aryl or heterocyclic group;

[0023] X represents halogen;

[0024] Y1 and Y2 independently represent hydrogen, halogen, cyano, C1-C8 alkyl, halo-C1-C8 alkyl, C2-C8 alkenyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl, aryl, heterocyclic, -OR9 or -S(O), respectively. m R9, or Y1, Y2 together with the carbon atoms they are connected to form C=N-OR9, C=C(R9)2, carbonyl or thiocarbonyl;

[0025] R9 independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C1-C8 alkoxy-C1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, C1-C8 alkoxy-carbonyl-C1-C8 alkyl, aryl, heterocyclic, aryl-C1-C8 alkyl, or heterocyclic-C1-C8 alkyl.

[0026] The aforementioned C3-C8 cycloalkyl or C3-C8 cycloalkenyl is optionally substituted with at least one group selected from hydroxyl, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C1-C8 alkoxy, halo-C1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio or C1-C8 alkylsulfonyl;

[0027] The aforementioned heterocyclic or aryl groups are optionally selected from halogens, nitro groups, cyano groups, C1-C8 alkyl groups, halo-C1-C8 alkyl groups, C2-C8 alkenyl groups, halo-C2-C8 alkenyl groups, C2-C8 alkynyl groups, halo-C2-C8 alkynyl groups, C3-C8 cycloalkyl groups, C3-C8 cycloalkyl groups (C1-C8 alkyl), C3-C8 cycloalkyl groups (C2-C8 alkenyl), C3-C8 cycloalkyl groups (C2-C8 alkynyl), and -OR groups. 10 -(C1-C8 alkylene)-OR 10 -O-(C1-C8 alkylene)-OR 10 -(C1-C8 alkylene)-S(O) m R 10 -S(O) m R 10 -(C1-C8 alkylene)-COOR 10 -COOR 10 -COR10 -(CO)N(R) 10 2. A tri-C1-C8 alkylsilyl group or an unsubstituted or substituted aryl or heterocyclic group selected from halogen, C1-C8 alkyl, or halo-C1-C8 alkyl groups, or two adjacent carbon atoms on the ring are substituted with an unsubstituted or substituted aryl or heterocyclic group selected from halogen, C1-C8 alkyl, -COR 10 or -COOR 10 -(CH2) is substituted by at least one group. n -, -OCH2O-, -SCH2O-, -SCH2S- or -OCH2CH2O- form a ring structure;

[0028] R 10 Each of these groups independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl-C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl-C1-C8 alkyl, or an aryl, aryl-C1-C8 alkyl, heterocyclic, or heterocyclic-C1-C8 alkyl group that is unsubstituted or substituted by at least one group selected from C1-C8 alkyl, halogen, C1-C8 alkoxy, halo-C1-C8 alkoxy, or halo-C1-C8 alkyl.

[0029] m represents 0, 1, or 2;

[0030] n represents 1, 2, 3, or 4.

[0031] In another specific implementation,

[0032] L represents a direct bond, -O-, -S-, -NR8-, C1-C6 alkylene, C2-C6 alkenylene, or C2-C6 ynylene;

[0033] R8 represents hydrogen or C1-C6 alkyl;

[0034] Q represents C3-C6 cycloalkyl or C3-C6 cycloalkenyl;

[0035] M represents aryl or heterocyclic group;

[0036] X represents halogen;

[0037] Y1 and Y2 independently represent hydrogen, halogen, cyano, C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkenyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl, aryl, heterocyclic, -OR9 or -S(O), respectively. m R9, or Y1, Y2 together with the carbon atoms they are connected to form C=N-OR9, C=C(R9)2, carbonyl or thiocarbonyl;

[0038] R9represents independently for each occurrence hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, C1-C6alkoxyC1-C6alkyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C1-C6alkoxycarbonylC1-C6alkyl, aryl, heterocyclyl, arylC1-C6alkyl, or heterocyclylC1-C6alkyl;

[0039] the aforementioned C3-C6cycloalkyl or C3-C6cycloalkenyl is optionally substituted with at least one group selected from hydroxy, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, C1-C6alkoxy, haloC1-C6alkoxy, C1-C6alkoxycarbonyl, C1-C6alkylthio, or C1-C6alkylsulfonyl;

[0040] the aforementioned heterocyclyl or aryl is optionally substituted with at least one group selected from halogen, nitro, cyano, C1-C6alkyl, haloC1-C6alkyl, C2-C6alkenyl, haloC2-C6alkenyl, C2-C6alkynyl, haloC2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkenyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkylC2-C6alkenyl, C3-C6cycloalkylC2-C6alkynyl, -OR 10 , -(C1-C6alkylene)-OR 10 , -O-(C1-C6alkylene)-OR 10 , -(C1-C6alkylene)-S(O) m R 10 , -S(O) m R 10 , -(C1-C6alkylene)-COOR 10 , -COOR 10 , -COR 10 , -(CO)N(R 10 )2, triC1-C6alkylsilyl, phenyl, pyridyl, pyrimidinyl, at least one group selected from halogen, C1-C6alkyl, -COR 10 , or -COOR 10 ; or ring formed by -CH2 n -, -OCH2O-, -SCH2O-, -SCH2S-, or -OCH2CH2O- with the adjacent carbon atoms of the ring being unsubstituted or substituted with at least one group selected from halogen, C1-C6alkyl, -COR optionally substituted by at least one member selected from the group consisting of halogen, C1-C6alkyl or halogenated C1-C6alkyl;

[0041] R 10 each independently represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, halogenated C1-C6alkyl, halogenated C2-C6alkenyl, halogenated C2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkyl C1-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenyl C1-C6alkyl, or phenyl, benzyl, pyridyl, pyrimidyl, pyrazolyl, imidazolyl, thienyl, furyl, thiazolyl, oxazolyl, isoxazolyl, isothiazolyl, triazolyl, tetrazolyl, indolyl, indazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, indazolyl, indolizinyl, purinyl, indolyl, indolizinyl, benzimidazolyl, benzoxazolyl, benzothiazolyl, benzodioxolyl, naphthyl, or phenanthryl, which is unsubstituted or substituted by at least one member selected from the group consisting of halogen, C1-C6alkyl, halogenated C1-C6alkyl, C1-C6alkoxy, halogenated C1-C6alkoxy, or halogenated C1-C6alkyl;

[0042] m represents 0, 1 or 2;

[0043] n represents 1, 2, 3 or 4.

[0044] In another specific embodiment,

[0045] L represents a direct bond, -O-, C2-C6alkenylene or C2-C6alkynylene;

[0046] Q represents C3-C6cycloalkyl or C3-C6cycloalkenyl;

[0047] M represents aryl or heterocyclyl;

[0048] X represents halogen;

[0049] Y1, Y2each independently represents hydrogen, halogen, C1-C6alkyl, heterocyclyl, -OR9or -S(O) m R9, or Y1, Y2together with the carbon atom to which they are attached form C=C(R9)2or carbonyl;

[0050] R9each independently represents hydrogen, C1-C6alkyl or C3-C6cycloalkyl C1-C6alkyl;

[0051] the aforementioned C3-C6cycloalkyl or C3-C6cycloalkenyl is optionally substituted by at least one member selected from the group consisting of hydroxy or C1-C6alkyl;

[0052] the aforementioned heterocyclyl or aryl is optionally substituted by at least one member selected from the group consisting of halogen, cyano, C1-C6alkyl, halogenated C1-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkyl C2-C6alkynyl, -OR 10 , -S(O) m R 10 , -COR 10 , phenyl, pyrimidyl or substituted with at least one group selected from halogen, C1-C6alkyl, haloC1-C6alkyl, C2-C6alkenyl, haloC2-C6alkenyl, C2-C6alkynyl, haloC2-C6alkynyl, -OR substituted with at least one group selected from halogen, C1-C6alkyl, haloC1-C6alkyl, C2-C6alkenyl, haloC2-C6alkenyl, C2-C6alkynyl, haloC2-C6alkynyl, -OR

[0053] R 10 each independently represents C1-C6alkyl, haloC1-C6alkyl, or phenyl, benzyl, pyridyl, or

[0054] m represents 0, 1 or 2.

[0055] In another specific embodiment,

[0056] L represents a direct bond, -O-, -S-, -NR8-, C1-C6alkylene, C2-C6alkenylene, or C2-C6alkynylene;

[0057] R8represents hydrogen or C1-C6alkyl;

[0058] Q represents C3-C6cycloalkyl or C3-C6cycloalkenyl;

[0059] M represents aryl or heterocyclyl, said "aryl" or "heterocyclyl" being optionally substituted with at least one group selected from halogen, nitro, cyano, C1-C6alkyl, haloC1-C6alkyl, C2-C6alkenyl, haloC2-C6alkenyl, C2-C6alkynyl, haloC2-C6alkynyl, -OR 10 , -(C1-C6alkylene)-OR 10 , -(C1-C6alkylene)-S(O) m R 10 , -S(O) m R 10 , -(C1-C6alkylene)-COOR 10 , -COOR 10 , or trisC1-C6alkylsilyl, or adjacent carbon atoms on the ring form a cyclic structure with -OCH2O-, -SCH2O-, -OCH2S-, or -OCH2CH2O- being unsubstituted or substituted with at least one group selected from halogen, C1-C6alkyl; n

[0060] Y1, Y2each independently represents hydrogen, halogen, cyano, C1-C6alkyl, haloC1-C6alkyl, C2-C6alkenyl, haloC2-C6alkenyl, C2-C6alkynyl, haloC2-C6alkynyl, -OR​10 or -S(O) m R 10 , or Y1, Y2together with the common carbon atom to which they are attached form C=CH2, carbonyl or thiocarbonyl;

[0061] R 10 each independently represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, C1-C6alkoxyC1-C6alkyl, C3-C6cycloalkyl or C3-C6cycloalkylC1-C6alkyl;

[0062] m represents 0, 1 or 2;

[0063] n represents 1, 2, 3 or 4;

[0064] the aforementioned C3-C6cycloalkyl is optionally substituted with at least one group selected from hydroxy, halogen, cyano, nitro, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, C1-C6alkoxy, haloC1-C6alkoxy, C1-C6alkoxycarbonyl, C1-C6alkylthio or C1-C6alkylsulfonyl.

[0065] In another specific embodiment,

[0066] L represents a direct bond, -O-, C2-C6alkenylene or C2-C6alkynylene;

[0067] Q represents C3-C6cycloalkyl or C3-C6cycloalkenyl;

[0068] M represents aryl or heterocyclyl, said aryl or heterocyclyl being optionally substituted with at least one group selected from halogen, cyano, C1-C6alkyl, haloC1-C6alkyl, -OR 10 or -S(O) m R 10 or the two adjacent carbon atoms on the ring form a cyclic structure with -OCH2O- which is unsubstituted or substituted with at least one group selected from halogen;

[0069] Y1, Y2each independently represents hydrogen, halogen, C1-C6alkyl, -OR 10 or -S(O) m R 10 or Y1, Y2together with the common carbon atom to which they are attached form C=CH2or carbonyl;

[0070] R 10 each independently represents C1-C6alkyl or haloC1-C6alkyl;

[0071] m represents 0, 1 or 2;

[0072] The aforementioned C3-C6cycloalkyl is optionally substituted with at least one group selected from hydroxy or C1-C6alkyl.

[0073] In another specific embodiment,

[0074] L represents a direct bond, -O-, -CH=CH- or -C≡C-.

[0075] In the definition of the compounds of general formula (I) and in all the structural formulae hereinafter, the professional terms used, whether alone or in a composite, represent the following substituents: alkyl groups having more than two carbon atoms can be straight or branched. Alkyl groups are, for example, C1alkyl - methyl; C2alkyl - ethyl; C3alkyl - propyl, such as n-propyl or isopropyl; C4alkyl - butyl, such as n-butyl, isobutyl, tert-butyl or 2-butyl; C5alkyl - pentyl, such as n-pentyl; C6alkyl - hexyl, such as n-hexyl, isohexyl and 1,3-dimethylbutyl. Similarly, alkenyl is, for example, ethenyl, 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 is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Alkylene groups are, for example, -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, and the like. Multiple bonds can be in any position of each unsaturated group. Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is a monocyclic alkenyl group having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein the double bond can be in any position. Halogen is fluorine, chlorine, bromine or iodine.

[0076] Unless otherwise specifically indicated, the term "aryl" as used herein includes, but is not limited to, phenyl, naphthyl, The term "heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups The term "heterocyclyl" as used herein includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups

[0077] The term "optionally" or "optional" means that the subsequently described event or circumstance can or can not occur, and thus that the description includes instances where the event or circumstance occurs and instances where it does not. For example, the term "optionally substituted" means that the specified atom or group is either unsubstituted or substituted with one or more substituents. If a group is substituted with a group, this is to be understood as meaning that the group is substituted with one or more groups, which are the same or different, selected from those mentioned. Furthermore, the same or different substituents contained in the same or different substituents are each independently selected, which can be the same or different. This applies equally to ring systems formed from different atoms and units. At the same time, the scope of the claims is to exclude those compounds which are chemically unstable under standard conditions, as known to the person skilled in the art.

[0078] In addition, unless specifically limited otherwise, the term "substituted" as used herein means substituted with one, two, three, four, or five groups; groups not marked with a specific position of attachment (including cycloalkyl and the like) can be attached in any position, including to a C or N; and if it is substituted, the substituents can likewise be substituted in any position, as long as the rules of chemical bonding are followed.

[0079] The present application provides a substituted pyridine compound having a chiral center as shown in formula I' or a salt thereof, N-oxide:

[0080] wherein the definitions of substituents Q, L, X, Y1, Y2, M are as described above, and the carbon atom at the position C* is a chiral center (R or S configuration).

[0081] In one embodiment, it has a stereochemical purity of 60-100% (S), preferably 70-100% (S), more preferably 80-100% (S), further preferably 90-100% (S), and even further preferably 95-100% (S), based on the content of stereoisomers having R and S configurations at this position.

[0082] In another embodiment, it has a stereochemical purity of 60-100% (R), preferably 70-100% (R), more preferably 80-100% (R), further preferably 90-100% (R), and even further preferably 95-100% (R), based on the content of stereoisomers having R and S configurations at this position.

[0083] wherein the "stereochemical purity" refers to the amount of the stereoisomer described as a percentage of the total amount of stereoisomers having a chiral center that is generated.

[0084] In the present application, the stereochemical configuration at the position marked * in formula I is determined according to the Cahn-Ingold-Prelog system, however the subject matter of the present application also relates to all stereoisomers of other positions included in formula I, and mixtures thereof. Such compounds of formula I include, for example, one or more additional asymmetric carbon atoms or other double bonds not specifically indicated in formula I. It is to be understood that the present application includes pure isomers and mixtures thereof in varying degrees of enrichment of the pure isomers, provided that the stereochemical configuration is correct, and that possible stereoisomers, such as enantiomers, diastereomers, Z- and E-isomers, defined by the particular spatial order, are included in formula I and can be obtained in stereoisomerically pure form from mixtures of stereoisomers by conventional methods, or also by stereoselective reactions in combination with the use of stereochemically pure starting materials.

[0085] If various functional groups are present, the present application also includes any keto and enol tautomeric forms and mixtures and salts thereof.

[0086] The stereoisomers can be obtained from mixtures by optical resolution. Likewise, the stereoisomers can be prepared selectively by using stereoselective reactions and using optically active starting materials and / or auxiliaries. For optical resolution, it is generally possible to use conventional methods (cf. Textbooks of Stereochemistry), for example the following methods for the resolution of mixtures of diastereomers, for example physical methods such as crystallization, chromatography, in particular column chromatography and high-pressure liquid chromatography, distillation methods, if appropriate under reduced pressure, extraction and other methods, usually with chromatographic separation on chiral stationary phases, which make it possible to separate residual mixtures of enantiomers. Suitable for preparative amounts or for industrial scale are methods such as, for example, crystallization of diastereomeric salts, which can be obtained from the compounds using optically active acids and, if acidic groups are present, if appropriate using optically active bases.

[0087] The method for preparing the substituted pyridine compound or salt, N-oxide thereof, comprises the following steps:

[0088] (1) Compounds represented by general formula I are prepared by coupling reaction of compounds represented by general formula II and III, and the reaction equation is as follows:

[0089] wherein Y1, Y2, L, X, Q and M are defined as described above;

[0090] 1) when L represents a direct bond, alkylene, alkenylene or alkynylene, either of W1 and W2 is halogen, OMs or OTf, and the other is a boron reagent (such as -B(OH)2 or ), tin reagent, zinc reagent, silicon reagent or Grignard reagent, or W1 is halogen and W2 is H.

[0091] When either of W1, W2 is halogen, OMs or OTf, and the other is boron reagent, tin reagent, zinc reagent, silicon reagent or Grignard reagent:

[0092] In one embodiment, the reaction is carried out in the presence of a solvent and a catalyst.

[0093] In another embodiment, the reaction condition is further in the presence of a base.

[0094] In another embodiment, the solvent is an organic solvent / water, and the organic solvent is at least one selected from aromatic hydrocarbon (such as benzene, chlorobenzene or toluene), DMF, DMA, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

[0095] In another embodiment, the catalyst is at least one selected from Pd(PPh3)4, Pd(dppf)Cl2, Pd(OAc)2 / n-butyl bis (1-adamantyl) phosphine, Pd(OAc)2 / tricyclohexylphosphine, PdCl2(PPh3)2or 1,1'-bis(diphenylphosphino) ferrocene dichloropalladium (II) dichloromethane complex.

[0096] In another embodiment, the base is at least one selected from inorganic base (such as NaH, KH, NaOH, KOH, K2CO3, Na2CO3, Cs2CO3, potassium phosphate, sodium phosphate, cesium fluoride, potassium fluoride, etc.) or organic base (such as pyrazole, triethylamine, N, N diisopropyl ethylamine, pyridine, DIEA, potassium trimethylsilanolate, AcOK, AcONa, MeONa, EtONa, t-BuONa, t-BuOK, etc.).

[0097] When W1 is halogen and W2 is H:

[0098] In one embodiment, the reaction is carried out in the presence of a solvent and a catalyst.

[0099] In another embodiment, the solvent is at least one selected from triethylamine, pyridine, DMF, methanol or ethyl acetate.

[0100] In another embodiment, the catalyst is palladium catalyst / cuprous iodide; and the palladium catalyst is at least one selected from Pd(PPh3)4, Pd(dppf)Cl2, Pd(OAc)2, PdCl2(PPh3)2or Pd(dba)3or Pd / C.

[0101] 2) when L represents -O-, -S- or -NR1-, W1is halogen and W2is H.

[0102] In one embodiment, the reaction is carried out in the presence of a solvent and a base.

[0103] In another embodiment, the solvent is selected from at least one of aromatic hydrocarbon, DMF, DMA, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate.

[0104] In another embodiment, the base is selected from at least one of inorganic base (such as NaH, KH, NaOH, KOH, K2CO3, Na2CO3, Cs2CO3, potassium phosphate, sodium phosphate, cesium fluoride, potassium fluoride, etc.) or organic base (such as pyrazole, triethylamine, N,N diisopropylethylamine, pyridine, DIEA, potassium trimethylsilanolate, AcOK, AcONa, MeONa, EtONa, t-BuONa, t-BuOK, etc.).

[0105] or (2) when Y1is OH and Y2is H, compounds of Formula IV and V are reacted to produce compounds of Formula I’ as shown in the following reaction scheme:

[0106] wherein L, X, Q and M are as defined above.

[0107] In one embodiment, the reaction is carried out in the presence of a solvent and a base.

[0108] In another embodiment, the solvent is selected from at least one of diethyl ether, ethylene glycol dimethyl ether, carbon tetrachloride, tetrahydrofuran, pentane, hexane or cyclohexane.

[0109] In another embodiment, the base is selected from at least one of LDA, n-BuLi, methyllithium, LiHMDS, NaHMDS or KHMDS.

[0110] In addition, compounds of Formula I can be prepared according to the methods described in WO2012087630A1, WO2021155106A1, etc.

[0111] The present application also provides an intermediate, which is shown in Formula II.

[0112] Suitable salts of the compounds according to the application according to the application, such as salts with bases or acid addition salts, are in each case conventional non-toxic salts, preferably the salts which are agriculturally and / or physiologically tolerated. Preference is given to salts with inorganic bases, such as alkali metal salts (for example sodium, potassium or cesium salts), alkaline earth metal salts (for example calcium or magnesium salts), ammonium salts; or salts with organic bases, in particular with organic amines, such as triethylammonium salts, dicyclohexylammonium salts, N,N'-dibenzylethylenediammonium salts, pyridinium salts, picolinium salts or ethanolammonium salts; salts with inorganic acids (for example hydrochlorides, hydrobromides, dihydrogen sulphates, trihydrogen sulphates or phosphates); salts with organic carboxylic or sulphonic acids (for example formates, acetates, trifluoroacetates, maleates, tartrates, methanesulphonates, benzenesulphonates or 4-toluenesulphonates). It is known that tertiary amines such as some of the compounds according to the application are capable of forming N-oxides, which are likewise salts according to the application.

[0113] Depending on the nature of the substituents, the compounds of the formula I can exist in the form of geometric and / or optically active isomers or in the form of mixtures of the corresponding isomers in different compositions. These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers. The present application therefore includes pure stereoisomers as well as any mixtures of these isomers.

[0114] The present application also relates to a method for controlling animal pests, wherein a compound of the formula I can act on the animal pests and / or their habitat. The control of the animal pests is preferably carried out in agriculture and forestry, and in the protection of materials. Excluded from the method are, preferably, methods of surgical treatment and therapeutic treatment of the human or animal body and diagnostic methods which are carried out on the human or animal body.

[0115] The present application also relates to the use of a compound of the formula I as a pesticide, in particular as a crop protection agent.

[0116] In the context of the present application, the term "pesticide" also generally includes the term "crop protection agent".

[0117] Compounds of formula I having good plant tolerance, favourable homeotherm toxicity and good environmental compatibility are suitable for protecting plants and plant organs, for enhancing harvest yields, for improving the quality of the harvested material and for controlling animal pests, in particular insects, arachnids, Myriapods, Nematodes and Molluscs, that occur in agriculture, in horticulture, in livestock farming, in poultry farming, in fish farming, in forestry, in gardens and leisure facilities, in the protection of stored products and materials and in the hygiene sector. These compounds are preferably used as insecticides. They can be active against normally sensitive and resistant species and against all or some stages of development. The pests mentioned include, but are not limited to, pests from the phylum Arthropoda, in particular from the class Arachnida, from the class Chilopoda, from the class Collembola, from the class Diplopoda, from the class Insecta, from the order Coleoptera, from the order Diptera, from the order Heteroptera, from the order Homoptera, from the order Hymenoptera, from the order Isopoda, from the order Isoptera, from the order Lepidoptera, from the order Orthoptera or Saltatoria, from the order Phthiraptera, from the order Psocoptera, from the order Siphonaptera, from the order Thysanoptera, from the order Zygentoma (= Thysanura), from the class Symphyla, from the phylum Mollusca, and from the class Gastropoda.

[0118] At certain concentrations and application rates, the compounds of formula I can also optionally be used as insecticides, safeners, growth regulators or agents for improving plant properties, as fungicides and gametocides, for example as fungicides, antimycotics, bactericides, viricides (including antiviroid agents) or as agents against MLO (Mycoplasma-like organisms) and RLO (Rickettsiella-like organisms). If appropriate, they can also be used as intermediates or precursors for the synthesis of other active ingredients.

[0119] The present application also relates to formulations comprising at least one compound of the formula I and to the use thereof as a pesticidal application form, such as drenches, drip and spray liquids, prepared therefrom. In certain cases, the application forms comprise further pesticides and / or adjuvants having an improved action, such as penetrants, for example vegetable oils (such as rapeseed oil, sunflower oil), mineral oils (such as paraffin oil), alkyl esters of vegetable fatty acids (such as rapeseed oil methyl ester or soybean oil methyl ester), or alkanol alkoxylates; and / or spreaders, for example alkylsilicones and / or salts (such as organic or inorganic ammonium or phosphonium salts, for example ammonium sulfate or di-ammonium hydrogenphosphate); and / or retention promoters, for example dioctyl sulfosuccinate or hydroxypropyl guar polymer; and / or wetters, for example glycerol; and / or fertilizers, for example ammonium-, potassium- or phosphorus-containing fertilizers.

[0120] The formulations which are customary are, for example, water-soluble liquids (SL), emulsifiable concentrates (EC), aqueous emulsions (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS); these and other possible formulation types are described, for example, by Crop Life International in the following publication: Pesticide Specifications, Manual on development and use of FAO and WHO specifications for pesticides, FAO Plant Production and Protection Papers - 173, developed by the Joint FAO / WHO Committee on Pesticide Specifications, 2004, ISBN: 9251048576. The formulations optionally comprise, in addition to the compound(s) of the formula I, further agrochemically active ingredients.

[0121] These are preferably formulations or application forms which comprise auxiliaries, such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners; and or other auxiliaries, such as adjuvants. In the present context, an adjuvant is a component which enhances the biological efficacy of the formulation, whereas the component itself does not have any biological efficacy. Examples of adjuvants are agents which promote retention, spreading, adhesion to the leaf surface or penetration.

[0122] The formulations are prepared in known manner, for example by mixing the compound of the formula I with auxiliaries, such as extenders, solvents and / or solid carriers and / or further auxiliaries such as surfactants. The formulations are prepared immediately before use or during use.

[0123] The adjuvants used can be substances suitable for imparting specific properties to the formulations of the compounds of the formula I or to the use forms prepared from these formulations, such as ready-to-use insecticides, such as spray liquors or seed dressing products, for example specific physical, technical and / or biological properties.

[0124] Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, such as those selected from the group consisting of aromatic or aliphatic hydrocarbons (such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzene), alcohols and polyols (which can also be optionally substituted, etherified and / or esterified), ketones (such as acetone, cyclohexanone), esters (including fatty and oil) and (poly)ethers, unsubstituted and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethyl sulfoxide).

[0125] If the extender used is water, it is also possible to use, for example, organic solvents as cosolvents. Useful liquid solvents are mainly: aromatic compounds, such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic and aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or dichloromethane; aliphatic hydrocarbons, such as cyclohexane or paraffins, such as mineral oil fractions, mineral and vegetable oils; alcohols, such as butanol or glycol and ethers and esters thereof; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents, such as dimethylformamide, dimethylacetamide and dimethyl sulfoxide and water.

[0126] In principle, all suitable solvents can be used. Examples of suitable solvents are aromatic hydrocarbons, such as xylene, toluene or alkylnaphthalenes; chlorinated aromatic or aliphatic hydrocarbons, such as chlorobenzene, chloroethylene, dichloromethane; aliphatic hydrocarbons, such as cyclohexane, paraffins, mineral oil fractions, mineral and vegetable oils; alcohols, such as methanol, ethanol, isopropanol, butanol or glycol and ethers and esters thereof; ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strongly polar solvents, such as dimethyl sulfoxide and water.

[0127] In principle, all suitable carriers can be used. Useful carriers include, inter alia, for example, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomite; and ground synthetic materials, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used. Useful carriers for granules include, for example, crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite; and synthetic granules of inorganic and organic powders; and granules of organic materials such as sawdust, paper, coir, corn cobs and tobacco stems.

[0128] Also liquid gaseous extenders or solvents can be used. Particularly suitable extenders or carriers are those which are gaseous at ambient temperature and atmospheric pressure, for example aerosol propellant gases such as halogenated hydrocarbons, and also butane, propane, nitrogen and carbon dioxide.

[0129] Examples of emulsifiers and / or foaming, dispersing or wetting agents, or mixtures of these surfactants, having ionic or non-ionic properties are salts of polyacrylic acids; salts of lignosulphonic acids; salts of phenolsulphonic acids or naphthalenesulphonic acids; polycondensates of ethylene oxide with fatty alcohols or fatty acids or fatty amines or substituted phenols, preferably alkylphenols or arylphenols; salts of sulphosuccinic esters; taurine derivatives, preferably alkyl taurates; phosphoric esters of polyethoxylated alcohols or phenols; fatty acid esters of polyols; and derivatives of compounds containing sulphates, sulphonates and phosphates, such as alkyl aryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates, protein hydrolysates, lignosulphite waste liquors and methylcellulose. If one of the above compounds of the formula I and / or one of the above inert carriers is not water-soluble and application is to be carried out in water, the presence of a surfactant is advantageous.

[0130] Other auxiliaries which can be present in the formulations and in the use forms derived from them include colourants such as inorganic pigments, for example iron oxide, titanium oxide, Prussian Blue, and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and also nutrients and micronutrients, such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

[0131] The additional components can be stabilisers which improve chemical and / or physical stability, such as cold-stabilisers, preservatives, antioxidants, light stabilisers or other agents. Foaming and antifoaming agents can also be present.

[0132] Furthermore, the formulations and use forms derived from them can also comprise, as additional auxiliaries, sticking agents such as carboxymethylcellulose, and also natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyacrylic acid, or natural phospholipids, such as cephalins, lecithins and synthetic phospholipids. Further possible auxiliaries are mineral and vegetable oils.

[0133] Optionally, other auxiliaries can be present in the formulations and in the use forms derived from them. Examples of such additives include fragrances, protective colloids, binders, adhesives, thickeners, thixotropic agents, penetration agents, retention aids, stabilisers, sequestering and chelating agents, complexing agents, humectants and spreaders. In general, the compounds of the formula I can be combined with any solid or liquid additive which is customary for formulation purposes.

[0134] Useful retention promoters include all those substances which lower the kinetic surface tension, such as dioctyl sulfosuccinate; or all those substances which increase the viscoelasticity, such as hydroxypropyl guar polymers.

[0135] In the context of the present application, useful penetrants include all those substances which are typically used to enhance the penetration of active agrochemical ingredients into plants. In this context, penetrants are defined by their ability to penetrate the cuticle of the plant by the (usually aqueous) application liquid and / or by the spray coating, thereby increasing the mobility of the active ingredient in the cuticle. Examples include: alcohol alkoxylates, such as coconut fatty ethoxylate (10) or isotridecyl 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 phosphonium salts, such as ammonium sulfate or di-ammonium hydrogenphosphate.

[0136] The formulations preferably comprise from 0.00000001 to 98% by weight of the compound of formula I, more preferably from 0.01 to 95% by weight of the compound of formula I, most preferably from 0.5 to 90% by weight of the compound of formula I, based on the weight of the formulation.

[0137] The content of the compound of formula I in the use forms prepared from the formulations, especially the insecticides, can vary within wide ranges. The concentration of the compound of formula I in the use forms can generally be from 0.00000001 to 95% by weight of the compound of formula I, preferably from 0.00001 to 1% by weight, based on the weight of the use form. Application is carried out in the customary manner appropriate for the use form.

[0138] The compound of formula I can also be used in combination with one or more substances selected from the group consisting of suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbicides, beneficial organisms, pesticides, fertilizers, bird repellents, phytotonics, sterilants, safeners, semiochemicals and / or plant growth regulators, in order to broaden the spectrum of action, for example, to prolong the duration of action, to increase the rate of action, to prevent repellence or to prevent the development of resistance. In addition, such active ingredient combinations can improve plant growth and / or tolerance to abiotic factors, such as high or low temperatures, drought or high water content or soil salinity. It is also possible to improve flowering and fruiting performance, to optimize germination capacity and root development, to facilitate harvesting and to increase yield, to influence ripening, to improve the quality and / or nutritional value of the harvested products, to prolong the storage period and / or to improve the processing properties of the harvested products.

[0139] In addition, the compounds of the formula I can be present in mixtures with other active ingredients or semiochemicals such as attractants and / or bird repellents and / or plant activators and / or growth regulators and / or fertilizers. Likewise, the compounds of the formula I can be used in the form of mixtures with agents for improving the properties of plants such as growth, yield and quality of the harvested material.

[0140] In a particular embodiment of the present application, the compounds of the formula I are in the form of formulations or of use forms prepared from these formulations in mixture with other components, preferably those described below.

[0141] If one of the compounds mentioned below can exist in various tautomeric forms, these forms are included even if they are not explicitly mentioned in each case.

[0142] Insecticides / acaricides / nematicides

[0143] The active ingredients mentioned herein by their "common names" are known and are described, for example, in The Pesticide Manual, 16th Ed., British Crop Protection Council 2012, or can be retrieved on the internet (for example http: / / www.alanwood.net / pesticides). th

[0144] ​(1) acetylcholinesterase (AChE) inhibitors, such as carbamates, e.g. alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, triazamate, trimethacarb, XMC and xylylcarb; or organophosphates, e.g. azamethiphos, azinphos-ethyl, azinphos-methyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos / DDVP, dicrotophos, dimethoate, dimethylvinphos, disulfoton, EPN, ethion, ethoprophos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O-(methoxyaminothio-phosphoryl) salicylate, isoxathion, malathion, methacrifos, methidathion, naled, oxymetaxphos, phenthoate, phosalone, phosmet, phosphamidon, phorate, phoxim, pirimiphos- methyl, profenofos, propetamphos, prothiofos, prothoate, pyridafenthion, pyridaphore, quinalphos, sebufos, sulfotep, sulprofos, tebupirimiphos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, trichlorfon and vamidothion;malathion, mecarbam, methamidophos, methidathion, mevinphos, monocrotophos, naled, omethoate, oxydemeton-methyl, parathion, parathion-methyl, phenthoate, phorate, phosalone, phosmet, phosphamidon, phoxim, pirimiphos-methyl, profenofos, propetamphos, prothiofos, pyraclofos, pyridaphenthion, quinalphos, sulfotep, tebupirimfos, temephos, terbufos, tetrachlorvinphos, thiometon, triazophos, triclorfon and vamidothion.

[0145] (2) GABA-gated chloride ion channel antagonists, such as the cyclo- diene organochlorines, e.g. chlordane and endosulfan; or the phenylpyrazoles (fiproles), e.g. ethiprole and fipronil.

[0146] (3) Sodium channel modulators / voltage-dependent sodium channel blockers, for example pyrethroids, such as acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(1R)-trans isomers], deltamethrin, empenthrin [(EZ)-(1R) isomers], esfenvalerate, etofenprox, fenpropathrin, fenvalerate, flucythrinate, flumethrin, tau-fluvalinate, halfenprox, imiprothrin, kadethrin, permethrin, phenothrin [(1R)-trans isomers], prallethrin [(2R)-cis / trans isomers], resmethrin, imiprothrin, frethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin (dimethyl-3, 7, 11-trimethyl-2, 4, 6-decadione), ZXI 1.1 (dimethyl-3, 7, 11- trimethyl-2, 4, 6-decanedione), and ZXI 1.2 (dimethyl-3, 7, 11-trimethyl-2, 4, 6- decanedione);[isomer]), prallethrin, pyrethrine, resmethrin, silafluofen, tefluthrin, tetramethrin, tetramethrin [(1R)isomers], tralomethrin, and transfluthrin; or DDT; or methoxychloride.

[0147] (4) Nicotinic acetylcholine receptor (nAChR) agonists, such as neonicotinoids, such as acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor.

[0148] (5) Allosteric activators of nicotinic acetylcholine receptors (nAChR), such as spinosides, such as spintoram and spinosad.

[0149] (6) Chloride channel activators, such as abamectins / milbemycins, such as abamectin, emamectin benzoate, lepimectin and milbemectin.

[0150] (7) Juvenile hormone mimics, such as hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.

[0151] (8) Active ingredients with unknown or non-specific mechanisms of action, such as

[0152] Alkyl halides, such as methyl bromide and other alkyl halides; or chloropicrine or thiocyanate or borax or tartar emetic.

[0153] (9) selective feeding blockers, such as pymetrozine or fionicamid.

[0154] (10) mite growth inhibitors, such as clofentezine, hexythiazox and diflovidazin or etoxazole.

[0155] (11) microbial disruptors of insect gut 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: CrylAb, CrylAc, CrylFa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb, Cry34 / 35Ab1.

[0156] (12) oxidative phosphorylation inhibitors, ATP disruptors, such as diafenthiuron or organotin compounds, such as azocyclotin, cyhexatin and fenbutatin oxide or propargite or tetradifon.

[0157] (13) oxidative phosphorylation decouplers interrupting the H+ gradient, such as chlorfenapyr, DNOC and sulfluramid.

[0158] (14) nicotinic acetylcholine receptor agonists, such as bensultap, cartap hydrochloride, thiocyclam and thiosultap-sodium.

[0159] (15) Inhibitors of chitin biosynthesis, type 0, for example bistrifluron, chlofluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, teflubenzuron and triflumuron.

[0160] (16) Inhibitors of chitin biosynthesis, type 1, for example buprofezin.

[0161] (17) Moulting disruptor (especially for Diptera, i.e. flies), for example cyromazine.

[0162] (18) Ecdysone receptor agonists, for example chromafenozide, halofenozide, methoxyfenozide and tebufenozide.

[0163] (19) Octopaminergic agonists, for example amitraz.

[0164] (20) Complex-III electron transport inhibitors, for example hydramethylnone, or acequinocyl, or fluacrypyrim.

[0165] (21) Complex-I electron transport inhibitors, for example selected from METI acaricides, for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or rotenone (Derris spp.).

[0166] (22) Voltage-gated sodium channel blockers, for example indoxacarb or metaflumizone.

[0167] (23) Inhibitors of acetyl-CoA carboxylase, for example tetronic and tetramic acid derivatives, such as spirodiclofen, spiromesifen and spirotetramat.

[0168] (24) Complex-IV electron transport inhibitors, for example phosphines, such as aluminium phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanides.

[0169] (25) Complex-II electron transport inhibitors, for example cyenopyrafen and cyflumetofen.

[0170] (28) Ryanodine receptor effectors, for example diamides, such as chlorantraniliprole, cyantraniliprole and flubendiamide;

[0171] other active ingredients, such as afidopyropen, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, chinomethionat, cryolite, dicofol, diflovidazin, fluensulphone, flometoquin, flufenerim, flufenoxystrobin, flufiprole, fluopyram, flupyradifurone, fufenozide, heptafluthrin, imidaclothiz, iprodione, meperfluthrin, paichongding, pyflubumide, pyrifluquinazon, pyriminostrobin, tetramethylfluthrin and iodomethane, and agents based on Bacillus 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)-1 H-pyrazole-5-carboxamide (known from WO 2005 / 077934) and 1-{2-fluoro-4-methyl-5-[(2,2,2- trifluoroethyl)sulfinyl]phenyl}-3-(trifluoromethyl)-1 H-1,2,4-triazol-5-amine (known from WO 2006 / 043635), {1 '-[(2E)-3-(4-chlorophenyl)prop-2-en-1 -yl]-5-fluorospiro[indole-3,4'- piperidin]-1(2H)-yl}(2-chloropyridin-4-yl)methanone (known from WO 2003 / 106457), 2-chloro-N-[2-{1-[(2E)-3-(4-chlorophenyl)prop-2-en-1-yl]piperidin-4-yl}-4- (trifluoromethyl)phenyl]isonicotinamide (known from WO 2006 / 003494), 3-(2,5- dimethylphenyl)-4-hydroxy-8-methoxy-1,8-diazaspiro[4.5]dec-3-en-2-one (known from WO 2009 / 049851 ), 3-(2,5-dimethylphenyl)-8-methoxy-2-oxo-1,8-diazaspiro[4.5]dec-3-ene-4-yl carbonate (known from WO 2009 / 049851), 4-(but-2-yn-1-yloxy)-6-(3,5-dimethylpiperidin-1-yl)-5-fluoropyrimidine (known from WO 2004 / 099160), 4-(but-2-yn-1-yloxy)-6-(3-chlorophenyl)pyrimidine (known from WO 2003 / 076415), PF1364 (CAS Registry Number 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 WO 2005 / 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-naphthamide (known from WO 2009 / 002809), methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-chloro-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from WO 2005 / 085216), methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-ethylhydrazinecarboxylate (known from WO 2005 / 085216), methyl 2-[2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)-5-cyano-3-methylbenzoyl]-2-methylhydrazinecarboxylate (known from WO 2005 / 085216), methyl 2-[3,5-dibromo-2-({[3-bromo-1-(3-chloropyridin-2-yl)-1H-pyrazol-5-yl]carbonyl}amino)benzoyl]-2-ethylhydrazinecarboxylate (known from WO 2005 / 085216), 1-(3-chloropyridin-2-yl)-N-[4-cyano-2-methyl-6-(methylcarbamoyl)phenyl]-3-{[5-(trifluoromethyl)-2H-tetrazol-2-yl]methyl}-1H-pyrazole-5-carboxamide (known from WO 2010 / 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 CN 102057925), 3-chloro-N-(2-cyanopropan-2-yl)-N-[4-(1,1,1,2,3,3,3-Heptafluoroprop-2-yl)-2-methylphenyl] pthalic acid amide (known from WO 2012 / 034472), 8-Chloro-N-[(2-chloro-5-methoxyphenyl)sulfonyl]-6-(trifluoromethyl)imidazo[1,2-a]pyridine-2-carboxamide (known from WO 2010 / 129500), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1 -oxathian-3-yl)benzamide (known from WO 2009 / 080250), 4-[5-(3,5-dichlorophenyl)-5-(trifluoromethyl)-4,5-dihydro-1,2-oxazol-3-yl]-2-methyl-N-(1 -oxathian-3-yl)benzamide (known from WO 2012 / 029672), 1 -[(2-chloro-1,3-thiazol-5-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1 -ium-2-olate (known from WO 2009 / 099929), 1 -[(6-chloropyridin-3-yl)methyl]-4-oxo-3-phenyl-4H-pyrido[1,2-a]pyrimidin-1 -ium-2-olate (known from WO 2009 / 099929), (5S,8R)-1 -[(6-chloropyridin-3-yl)methyl]-9-nitro-2,3,5,6,7,8-hexahydro-1 H-5,8-epoxymidazo[1,2-a]azepine (known from WO 2010 / 069266), (2E)-1 -[(6-chloropyridin-3-yl)methyl]-N'-nitro-2-pentylenehydrazinecarboximidamide (known from WO 2010 / 060231 ), 4-(3-{2,6-dichloro-4-[(3,3-dichloroprop-2-en-1 -yl)oxy]phenoxy}propoxy)-2-methoxy-6-(trifluoromethyl)pyrimidine (known from CN 101337940), N-[2-(tert-butylcarbamoyl)-4-chloro-6-methylphenyl]-1 -(3-chloropyridin-2-yl)-3-(fluoromethoxy)-1 H-pyrazole-5-carboxamide (known from WO 2008 / 134969),

[0172] Fungicides

[0173] The active ingredients identified herein by their common names are known and described, for example, in the "Pesticide Manual" or on the internet (e.g. http: / / www.alanwood.net / pesticides).

[0174] Biological pesticides as mixing partners

[0175] The compounds of formula I can be combined with biological pesticides.

[0176] Biological pesticides include, inter alia, bacteria, fungi, yeasts, plant extracts and products produced by microorganisms, including proteins and secondary metabolites.

[0177] Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria which act as bioinsecticides, fungicides or nematicides.

[0178] Also included are bacteria and fungi which are added to plants or plant parts or plant organs as "inoculants" and which promote plant growth and plant health by their special properties.

[0179] Safety agents as mixing partners

[0180] The compounds of the formula I can be combined with safeners, such as, for example, benoxacor, cloquintocet (-mexyl), cyometrinil, cyprosulfamide, dichlormid, fenchlorazole (-ethyl), fenclorim, flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydride, oxabetrinil, 2-methoxy-N-{4-[(methylcarbamoyl)amino]phenyl} sulfamoyl)benzamide (CAS 129531-12-0), 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).

[0181] Plants and plant parts

[0182] All plants and plant parts can be treated in accordance with the application. Plants are to be understood as meaning all plants and plant populations such as wanted and unwanted wild plants or crop plants (including naturally occurring crop plants) such as cereals (wheat, rice, triticale, barley, rye, oats), maize, soya, potatoes, sugar beet, sugar cane, tomatoes, peas and other vegetable species, cotton, tobacco, rape and fruit plants (with the fruits mentioned: apples, pears, citrus fruits, and grapes). Crop plants can be plants which have been obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and plant cultivars which can be protected by the plant breeders' rights and which have been developed by plant breeding and selection or by biotechnological and genetic engineering methods. Plant parts are to be understood as meaning all parts and organs of the plants above and below ground such as shoot, leaf, flower and root, given as examples: leaves, needles, stems, trunks, flowers, fruit bodies, fruits and seeds, and also tubers. Plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.

[0183] The treatment of plants and plant parts with the compounds of the formula I according to the application is carried out directly or by allowing the compounds to act on the surroundings, habitat or storage space of the plants, by methods of treatment which are customary therefor, such as, for example, the dipping, spraying, vaporizing, fogging, spreading-on, painting-on, injection and, in the case of propagation material, especially seeds, the application of one or more coats.

[0184] As mentioned above, all plants and their parts can be treated in accordance with the application. In a preferred embodiment, wild plants species and plant cultivars, or those obtained by conventional biological breeding methods such as crossing or protoplast fusion, and their parts are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (genetically modified organisms), and their parts are treated. The term "parts" or "plant parts" or "parts of plants" has been explained above. It is especially preferred to treat plants and plants parts of those plants which have been so far obtained by means of conventional breeding and propagation methods or those plants which are in use in the fields or plantations. Plant cultivars are to be understood as meaning plants, which have given their properties with the aid of one or more genetic mutations or by means of a directed mutagenesis, a polyploidy, a coceptualization, a selection or a breeding, including plant cultivars which have been obtained by means of a biotechnological and genetic engineering method, such as gene technologically modified plants (genetically modified organisms). The term "plant cultivars" is to be understood to mean plants which have been modified by the interbreeding of different plant species or varieties, or by the mutations of a plant species or a plant variety. They can be obtained by conventional methods of breeding and optimization, or by biotechnological and genetic engineering methods, or by a combination of those methods. They include plants protected by plant breeders' rights and plants which are not protected by plant breeders' rights.

[0185] Transgenic plants, seed treatment and inteeration events

[0186] 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.

[0187] Crop protection – types of treatment

[0188] The treatment of plants and plant parts with the compounds of the formula I is carried out directly by the customary treatment methods, for example by immersing, spraying, atomizing, irrigating, evaporating, dusting, fogging, spreading, foaming, painting, spreading on, watering (drenching), drip irrigation, in the case of propagation material, especially in the case of seeds, also by dry seed treatment, wet seed treatment, treatment of the slurry, encrusting, coating with one or more coats, etc. It is also possible to apply the compounds of the formula I using the ultra-low-volume process or to inject them into the soil in the form of their use forms or of the compounds of the formula I themselves.

[0189] A preferred direct treatment of plants is the foliar application, which means that the compounds of the formula I are applied to the leaves, wherein the frequency of treatment and the rate of application are to be adjusted to the infestation level of the pests.

[0190] In the case of systemically active compounds, the compounds of the formula I can also enter the plant via the root system. The plant is then treated by acting on the habitat of the plant with the compounds of the formula I. This can be done, for example, by drenching; or by mixing into the soil or the nutrient solution, which means that the plant site, for example the soil or a hydroponic system, is flooded with the compounds of the formula I in liquid form; or by soil application, which means that the compounds of the formula I are introduced into the plant site in solid form, for example in the form of granules. In the case of rice crops, this can also be done by metering the compounds of the formula I in solid application form, for example as granules, into the flooded rice field.

[0191] Seed treatment

[0192] The control of animal pests by treatment of plant seeds has long been known and is the subject of constant improvements. Seed treatment, however, involves a series of problems which cannot always be solved in a satisfactory manner. There is therefore a need to develop methods for protecting seeds and germinating plants which do not require or at least significantly reduce the additional application of pesticides during storage, after sowing or after the emergence of the plants. There is also a need to optimize the amount of active ingredient used in order to provide the seeds and germinating plants with the best possible protection against attack by animal pests, without the active ingredient used impairing the plants themselves. In particular, the methods used for seed treatment should also take into account the intrinsic pesticidal and / or nematicidal properties of pest-resistant or pest-tolerant transgenic plants in order to achieve the best possible protection of the seeds and germinating plants with the least possible use of crop protection products.

[0193] Thus, more particularly, the present application also relates to a method for protecting seed and germinating plants from attack by pests by treating the seed with one of the compounds of formula I. The method of the present application for protecting seed and germinating plants from attack by pests also comprises a method wherein the seed is treated simultaneously with one of the compounds of formula I and a mixture partner in one operation or successively. It also comprises a method wherein the seed is treated with one of the compounds of formula I and a mixture partner at different times.

[0194] The present application also relates to the use of the compounds of formula I for treating seed to protect the seed and resulting plants from attack by animal pests.

[0195] The present application further relates to seed which has been treated with one of the compounds of formula I to protect it from attack by animal pests. The present application also relates to seed which has been treated simultaneously with one of the compounds of formula I and a mixture partner. The present application also relates to seed which has been treated with one of the compounds of formula I and a mixture partner at different times. In the case of seed which has been treated with one of the compounds of formula I and a mixture partner at different times, the individual components can be present in different layers of the seed. In this case, the layers comprising the compounds of formula I and the mixture partner can optionally be separated by intermediate layers. The present application also relates to seed, wherein one of the compounds of formula I and a mixture partner has been applied as part of a coating or other layer or in addition to a coating.

[0196] The present application also relates to seed which, after treatment with one of the compounds of formula I, is subjected to a film coating process to protect the seed from dust abrasion.

[0197] One of the advantages which exists when one of the compounds of formula I acts systemically is that the treatment of the seed protects not only the seed itself but also the plant which results from it (after emergence) from attack by animal pests. In this way, direct treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.

[0198] A further advantage is that treatment of the seed with one of the compounds of formula I can promote germination and emergence of the treated seed.

[0199] It is likewise considered advantageous that the compounds of formula I can also be used, inter alia, for transgenic seed.

[0200] The compounds of formula I can also be used in combination with signal technology components, as a result of which, for example, the colonization of symbionts, such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi, is improved and / or nitrogen fixation is optimized.

[0201] The compounds of the formula I are suitable for protecting the seed of any plant variety used in agriculture, in a greenhouse, in forestry or in horticulture. More particularly, the seeds include the seeds of cereals (for example wheat, barley, rye, millet and oats), maize, cotton, soybeans, rice, potatoes, sunflowers, coffee beans, tobacco, oilseed rape, oilseed rape seeds, sugar beets (for example sugar beets and fodder beets), peanuts, vegetables (for example tomatoes, cucumbers, beans, cruciferous plants, onions, lettuce), fruit plants, turf plants and ornamental plants. Of particular importance is the treatment of the seeds of cereals (wheat, barley, rye, oats), maize, soybeans, cotton, oilseed rape, oilseed rape seeds and rice.

[0202] As mentioned above, the treatment of transgenic seeds with the compounds of the formula I is also of particular importance. The seeds include the seeds of plants which usually comprise a heterologous gene which comprises the expression of at least one polypeptide which has, in particular, insecticidal and / or nematicidal properties. The heterologous gene in the transgenic seeds can be derived from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The compositions according to the application are particularly suitable for the treatment of transgenic seeds which comprise at least one heterologous gene derived from Bacillus. The heterologous gene is more preferably derived from Bacillus thuringiensis.

[0203] In the context of the present application, the compounds of the formula I are applied to the seeds. The seeds are preferably treated in a state which is sufficiently stable so that no damage occurs during the treatment. In general, the seeds can be treated at any point in time between harvesting and sowing. Seeds which have been separated from the plants and which have been freed from the husks, hulls, stems, skins, hairs or pulp are generally used. For example, seeds which have been harvested, cleaned and dried to a moisture content which allows storage can be used. Alternatively, seeds which have been dried, for example, and then treated with water and then dried again (for example, drenching) can also be used.

[0204] In general, when treating the seeds, it must be ensured that the amount of the compounds of the formula I and / or other additives which are applied to the seeds is chosen so that the germination of the seeds is not impaired and the plants which grow from the seeds are not damaged. This must be ensured in particular in the case of active ingredients which can exhibit phytotoxic effects at certain application rates.

[0205] The compounds of the formula I are generally applied to the seeds in the form of suitable formulations. Suitable formulations and seed treatment methods are known to the person skilled in the art.

[0206] The compounds of the formula I can be converted into customary seed-dressing preparations, such as solutions, emulsions, suspensions, dusts, foams, slurries or other coating compositions for seeds, and also ULV formulations.

[0207] These formulations are prepared in known manner, by mixing the compounds of the formula I with customary additives, such as customary extenders and solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, foaming agents, preservatives, secondary thickeners, stickers, gibberellins and also water.

[0208] Useful colorants which can be present in the seed-dressing preparations used according to the application are all colorants which are customary for this purpose. It is possible to use sparingly water-soluble pigments or it is possible to use water-soluble dyes. Examples include the known colorants known as Rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1.

[0209] Useful wetting agents which can be present in the seed-dressing preparations used according to the application are all substances which promote wetting and which are customary for the formulation of active agricultural-chemical ingredients. Preference is given to using alkyl naphthalene sulfonates, such as diisopropyl naphthalene sulfonate or diisobutyl naphthalene sulfonate.

[0210] Useful dispersants and / or emulsifiers which can be present in the seed-dressing preparations used according to the application are all non-ionic, anionic and cationic dispersants which are customary for the formulation of active agricultural-chemical ingredients. Preference is given to using non-ionic or anionic dispersants or mixtures of non-ionic or anionic dispersants. Suitable non-ionic dispersants include, in particular, ethylene oxide / propylene oxide block copolymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ethers, and also phosphated or sulfated derivatives thereof. Suitable anionic dispersants are, inter alia, lignosulfonates, polyacrylic acid salts and condensates of arylsulfonic acids / formaldehyde.

[0211] Antifoams which can be present in the seed-dressing preparations used according to the application are all foam inhibitors which are customary for the formulation of active agricultural-chemical ingredients. Preference is given to using silicone antifoams and magnesium stearate.

[0212] Preservatives which can be present in the seed-dressing preparations used according to the application are all substances which can be used for this purpose in agrochemical compositions. Examples include dichlorophen and benzyl alcohol hemiformal.

[0213] Secondary thickeners which can be present in the seed-dressing preparations used according to the application are all substances which can be used for this purpose in active agrochemical compositions. Preferred examples include cellulose derivatives, acrylic acid derivatives, xanthan gum, modified clays and finely divided silicas.

[0214] Useful binders which can be present in the seed dressing preparations used according to the application are all customary binders which can be used in seed dressing products. Preferred examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose.

[0215] The gibberellins which can be present in the seed dressing preparations used according to the application are preferably gibberellin A1, A3 (= gibberellic acid), A4 and A7, particularly preferred use being made of gibberellic acid.

[0216] The seed dressing preparations used according to the application can be used to treat a large number of different kinds of seed, either directly or after prior dilution with water. For example, the concentrates or the preparations obtainable therefrom by dilution with water can be used to coat the seeds of cereals (such as wheat, barley, rye, oats and triticale), and also the seeds of maize, rice, oilseed rape, peas, beans, cotton, sunflower, soybean and sugar beet, or a large number of different vegetable seeds. The seed dressing preparations used according to the application or their dilution forms used can also be used to dress the seeds of transgenic plants.

[0217] For the treatment of the seed with the seed dressing preparations used according to the application or the use forms prepared therefrom, all mixing apparatuses which are customary for seed dressing are available. More particularly, the process for seed dressing is as follows: the seeds are placed in batches or continuously in a mixer; the particular required amount of seed dressing preparation, either as such or after prior dilution with water, is added; and mixing is carried out until the preparation is uniformly distributed over the seeds. If appropriate, a drying operation can be carried out subsequently.

[0218] The application rates of the seed dressing preparations used according to the application can vary within a relatively wide range. They depend on the particular content of compounds of the formula I in the preparation and on the seeds. The application rates of the compounds of the formula I are generally from 0.001 g to 50 g per kg of seeds; preferably from 0.01 g to 15 g per kg of seeds.

[0219] For animal health

[0220] In the field of animal health, i.e. veterinary medicine, the active ingredients according to the application are used against animal parasites, especially ectoparasites or, in other embodiments, endoparasites. The term "endoparasites" includes, inter alia, helminths, such as tapeworms, roundworms or flukes; and protozoa, such as coccidia. Ectoparasites are generally and preferably arthropods, especially insects, such as biting and sucking flies, parasitic fly larvae, lice, hair lice, bird lice, fleas and the like; or mites, such as hard ticks or soft ticks; or mites, such as Demodex mites, autumn mites and bird mites and the like; and aquatic ectoparasites, such as copepods.

[0221] In the field of veterinary medicine, compounds of formula I which have a good homeotherm toxicity are suitable for controlling parasites which occur in animal breeding and animal keeping in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or specific developmental stages of the parasites.

[0222] Agricultural livestock includes, for example, mammals such as sheep, goats, horses, donkeys, camels, water buffalo, rabbits, reindeer, fallow deer, and in particular cattle and swine; poultry such as turkeys, ducks, geese, and in particular chickens; fish and crustaceans, for example in aquaculture; and insects such as bees.

[0223] Domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, in particular dogs, cats, caged birds, reptiles, amphibians and ornamental fish.

[0224] In a preferred embodiment, the compounds of formula I are administered to mammals.

[0225] In another preferred embodiment, the compounds of formula I are administered to avians, i.e. caged birds and in particular poultry.

[0226] The use of the compounds of formula I to control animal parasites is intended to reduce or prevent the cases of disease, death and performance reduction (in the case of meat, milk, wool, rawhide, eggs, honey, etc.) so that animal keeping can be more economical and simple and better keeping of the animals in good condition is achieved.

[0227] In the field of animal health, the term "control" or "controlling" means that the compounds of formula I are effective in reducing the incidence of a particular parasite to a non-damaging extent in animals infected with such parasites. More specifically, in the present context, "control" means that the compounds of formula I are able to kill, inhibit the growth of or inhibit the multiplication of the respective parasites.

[0228] In general, the active ingredients of the present application can be used as such for treating animals. It is preferred to use them in the form of pharmaceutical compositions which can contain pharmaceutically acceptable excipients and / or adjuvants known in the art (administration).

[0229] In the field of animal health and in animal husbandry, the active ingredients are used (administered) in the known manner, for example enterally, in the form of tablets, capsules, potions, drenches, granules, pastes, boluses, feed-through processes and suppositories; parenterally, for example by injection (intramuscularly, subcutaneously, intravenously, in particular intraperitoneally), by implantation; nasally; dermally, for example in the form of dips or baths, sprays, pour- ons and spot- ons, washes and dusts; and by means of mouldings comprising the active ingredients, for example collars, earmarks, tailmarks, limb bands, halters, marking devices and the like. The active ingredients can be formulated as shampoos or as suitable formulations which can be applied in the form of aerosols or non-pressurised spray agents such as pump sprays and atomised sprays.

[0230] In the case of use on livestock, poultry, domestic pets and the like, the active ingredients of the application can be used in the form of formulations (for example dusts, wettable powders ["WP"], emulsions, emulsifiable concentrates ["EC"], flowable compositions, uniform solutions and suspensions ["SC"], containing from 1% to 80% by weight of active ingredient, either directly or after dilution (for example from 100-fold to 10 000-fold), or they can be used as chemical baths.

[0231] In the case of use in the field of animal health, in order to broaden the spectrum of activity, the active ingredients of the application can be used in combination with suitable synergists, repellents or other active ingredients, for example acaricides, insecticides, anthelmintics, antiprotozoans.

[0232] Vector control

[0233] The compounds of the formula I are also useful in vector control. In the context of the present application, a vector is an arthropod, in particular an insect or an arachnid, which is capable of transmitting a pathogen, for example a virus, a helminth, a unicellular organism and a bacterium, from a reservoir (plant, animal, human being or the like) to a host. The pathogen can be transmitted to the host mechanically (for example non-stinging flies with trachoma) or can be transmitted to the host after injection (for example malaria parasites of mosquitoes).

[0234] In the context of the present application, examples of vectors are insects, for example aphids, flies, leafhoppers or thrips, which can transmit plant viruses to plants. Other carriers capable of transmitting plant viruses are spider mites, lice, beetles and nematodes.

[0235] In the context of the present application, further examples of vectors are insects and arachnids, such as mosquitoes, especially mosquitoes of the genus Aedes, Anopheles, for example A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria); and mosquitoes of the genus Culex, ticks, fleas, flies, mites and ticks, which can transmit pathogens to animals and / or humans.

[0236] If the compounds of the formula I are resistant to destruction, then vector control is also possible.

[0237] The compounds of the formula I are suitable for the prevention of diseases and / or pathogens which are transmitted by vectors. Thus, a further aspect of the present application is the use of the compounds of the formula I for vector control in, for example, agriculture, horticulture, forestry, landscaping and leisure facilities, and in the protection of materials and stored products.

[0238] Protection of industrial materials

[0239] The compounds of the formula I are suitable for protecting industrial materials against attack or damage by insects, for example insects from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.

[0240] In the present context, industrial materials are to be understood as meaning inanimate materials, for example, preferably plastics, adhesives, sizes, paper and paperboard, leather, wood and worked wood products and coating compositions. Particularly preferred is the use of the application for the protection of wood.

[0241] In a further embodiment, the compounds of the formula I are used together with at least one further insecticide and / or at least one fungicide.

[0242] In a further embodiment, the compounds of the formula I are ready-to-use insecticides, meaning that they can be applied to the materials without further modification. In particular, suitable further insecticides or fungicides are those mentioned above.

[0243] Surprisingly, it has also been found that the compounds of the formula I can be used for protecting objects which come into contact with salt water or slightly brackish water from fouling, especially ship hulls, screens, nets, buildings, mooring equipment and signalling systems. It is likewise possible for the compounds of the formula I to be used as antifouling agents, either alone or in combination with other active ingredients.

[0244] Control of animal pests in the hygiene sector

[0245] The compounds of formula I are suitable for controlling animal pests in the hygiene sector. More particularly, the present application can be used in the domestic sector, in the hygiene sector and in the protection of stored products, in particular for controlling insects, arachnids and mites in closed spaces, for example dwellings, factory premises, offices, vehicle passenger compartments. For controlling animal pests, the compounds of formula I can be used alone or in combination with other active ingredients and / or auxiliaries. They are preferably used in insecticidal products for the domestic sector. The compounds of formula I are effective against sensitive and resistant species and against all stages of development.

[0246] These pests include, for example, pests from the classes of the Arachnida, Scorpiones, Araneae and Opiliones, the classes of the Chilopoda and Diplopoda, the order of the Blattaria, the orders of the Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Thysanura, the sub-class of the Malacostraca, the order of the Isopoda.

[0247] In bait or bait stations for spreading, the following forms are applied: aerosols, pressure- free spray products such as pump sprays and atomizer sprays, automatic aerosolizing systems, fogs, foams, gels, evaporative products with evaporator tablets made of cellulose or plastic, liquid evaporators, gel and film evaporators, propeller-driven evaporators, energy-free or passive evaporating systems, moth papers, moth bags and moth gels; as granules or dusts. DETAILED DESCRIPTION

[0248] The following examples are intended to illustrate the present application and should not be construed as limiting the application in any way. The scope of the application claimed is set forth in the claims.

[0249] In view of the economy and diversity of the compounds, we have preferably synthesized some compounds, among the synthesized compounds, some are listed in the following Table 1 and Table 3. The specific compound structure and the corresponding compound information are shown in Table 1-3. The compounds in Table 1 and Table 3 are only for better illustration of the present application, but do not limit the present application, and for those skilled in the art, this should not be understood as the scope of the above-mentioned subject matter of the present application is limited to the following compounds.

[0250] Table 1 compound structure

[0251] Table 2 Compounds 1 H NMR

[0252] Table 3 Compound structures and their 1 H NMR

[0253] Note: N position indicates salt formation on the pyridine N or N-oxide, " / " stands for blank.

[0254] Table A is structured the same as Tables 1 and 3 above, except that the general formula I is replaced by the general formula I' having a chiral center wherein C* position is a chiral center. In Table A, the entries under the column heading "Seq. No." are recited in the order 2(S), 4(S)~18(S), 20(S)~30(S), 32(S)~48(S), 50(S), 52(S)~59(S), 61(S)~67(S), 69(S)~72(S), 74(S)~75(S), 77(S)~80(S), 82(S)~85(S), 87(S), 89(S)~91(S), 93(S)~95(S), 98(S)~100(S), 102(S)~107(S), 110(S)~126(S), 129(S)~131(S), 134(S), 137(S)~148(S), 151(S)~152(S), 154(S)~160(S), 162(S)~169(S), 171(S)~173(S), 175(S)~179(S), 2-1(S)~2-59(S), 2-63(S)~2-66(S), 2-68(S)~2-106(S), 2-108(S), 2-111(S), 2-113(S)~2-118(S), 2-120(S)~2-131(S), 2-139(S)~2-153(S), 2-155(S)~161(S), 163(S)~165(S), 167(S)~2-177(S), 2-179(S)~2-185(S), 2-187(S)~2-191(S), 2-193(S)~2-197(S), 2-199(S)~2-200(S), 2-203(S)~2-204(S), 2-206(S)~2-213(S), 2-215(S)~2-218(S), 2-221(S)~2-236(S), 2-238(S), 2-240(S)~248(S), 2-250(S)~2-260(S), 2-262(S)~2-265(S), 2-268(S)~2-270(S), 2-273(S)~2-274(S), 2-276(S)~2-278(S), 2-281(S)~2-287(S), 2-290(S)~2-294(S). That is, 2(S) corresponds to the compound in compound 2 in Table 1 having S configuration at C* position, 2-120(S) corresponds to the compound in compound 2-120 in Table 3 having S configuration at C* position.In Table B, the entries under the column heading "Seq. No." recited in order are 2(R), 4(R)~18(R), 20(R)~30(R), 32(R)~48(R), 50(R), 52(R)~59(R), 61(R)~67(R), 69(R)~72(R), 74(R)~75(R), 77(R)~80(R), 82(R)~85(R), 87(R), 89(R)~91(R), 93(R)~95(R), 98(R)~100(R), 102(R)~107(R), 110(R)~126(R), 129(R)~131(R), 134(R), 137(R)~148(R), 151(R)~152(R), 154(R)~160(R), 162(R)~169(R), 171(R)~173(R), 175(R)~179(R), 2-1(R)~2-59(R), 2-63(R)~2-66(R), 2-68(R)~2-106(R), 2-108(R), 2-111(R), 2-113(R)~2-118(R), 2-120(R)~2-131(R), 2-139(R)~2-153(R), 2-155(R)~161(R), 163(R)~165(R), 167(R)~2-177(R), 2-179(R)~2-185(R), 2-187(R)~2-191(R), 2-193(R)~2-197(R), 2-199(R)~2-200(R), 2-203(R)~2-204(R), 2-206(R)~2-213(R), 2-215(R)~2-218(R), 2-221(R)~2-236(R), 2-238(R), 2-240(R)~248(R), 2-250(R)~2-260(R), 2-262(R)~2-265(R), 2-268(R)~2-270(R), 2-273(R)~2-274(R), 2-276(R)~2-278(R), 2-281(R)~2-287(R), 2-290(R)~2-294(R). That is, 2(R) corresponds to the compound in Table 1, Compound 2, which is R at the C* position, 2-120(R) corresponds to the compound in Table 3, Compound 2-120, which is R at the C* position.

[0255] Several methods for preparing the compounds of the present application are illustrated in the following Schemes and Examples. Starting materials can be purchased from commercial suppliers or prepared by known literature methods or as otherwise described herein. Those skilled in the art will appreciate that other synthetic routes can be used to synthesize the compounds of the present application. Although specific starting materials and conditions are depicted in the schemes below, other starting materials and conditions can readily be substituted. The synthesis of the compounds of the present application can be further modified using conventional chemistry methods known to those skilled in the art, as described below. For example, appropriate groups can be protected during the course of a reaction or series of reactions.

[0256] The following method examples are provided to further illustrate the preparation of the compounds of the present application and are not intended to limit the scope of the application. The reagents used in the synthesis of the compounds described below are either commercially available or can be readily prepared by one of ordinary skill in the art.

[0257] Representative compounds are prepared as follows, and other compounds are prepared in a similar manner.

[0258] 1. Synthesis of Compound 2

[0259] In a 25 mL single necked flask, 2-1 (0.3 g, 1.0 eq, 0.8 mmol) was added to 5 mL of toluene and 0.5 mL of water, then cyclopropylboronic acid (0.1 g, 1.5 eq, 1.2 mmol), potassium phosphate (0.51 g, 3.0 eq, 2.4 mmol) and tricyclohexylphosphine (0.05 g, 0.2 eq, 0.16 mmol) were added, then the flask was purged with nitrogen, and then palladium acetate (0.04 g, 0.2 eq, 0.16 mmol) was added, and the reaction was carried out at 100 °C for 8 hours. After the reaction was completed, the reaction solution was poured into 20 mL of water, and 10 mL of ethyl acetate was added twice to extract, and the organic phase was collected and concentrated under reduced pressure, and silica gel was added to the sample, and the sample was separated by normal phase column chromatography. Compound 2 (0.19 g, 93% purity, 67% yield) was obtained.

[0260] 2. Synthesis of Compound 18

[0261] In a 50 mL single neck flask, compound 18-1 (0.2 g, 1.0 eq, 0.052 mmol) was dissolved in 10 mL of toluene, then cyclopropylboronic acid (0.07 g, 1.5 eq, 0.078 mmol) was added, followed by 1 mL of water, palladium acetate (0.1 eq) and n- butyldi(1-adamantyl)phosphine (0.1 eq), nitrogen was replaced three times, slowly raised to 100 °C, reacted for 12 h, the reaction was monitored until the starting material disappeared. The reaction liquid was concentrated, the residue was diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 3), the organic phase was washed with saturated brine (50 mL x 3), dried over anhydrous sodium sulfate and concentrated, then the sample was mixed and separated by column to obtain the product 18 (0.08 g, yield 44%) as colorless oil.

[0262] 3. Synthesis of compound 44

[0263] In a 50 mL single neck flask, compound 18-1 (0.2 g, 1.0 eq, 0.052 mmol) was dissolved in 10 mL of toluene, then cyclopropylboronic acid (0.07 g, 1.5 eq, 0.078 mmol) was added, followed by 1 mL of water, palladium acetate (0.1 eq) and n- butyldi(1-adamantyl)phosphine (0.1 eq), nitrogen was replaced three times, slowly raised to 100 °C, reacted for 12 h, the reaction was monitored until the starting material disappeared. The reaction liquid was concentrated, the residue was diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 3), the organic phase was washed with saturated brine (50 mL x 3), dried over anhydrous sodium sulfate and concentrated, then the sample was mixed and separated by column to obtain the product 18 (0.08 g, yield 44%) as colorless oil.

[0264] 4. Synthesis of compound 45

[0265] In a 25 mL single neck flask, 2-1 (0.3 g, 1.0 eq, 0.8 mmol) was added to 5 mL of toluene and 0.5 mL of water, followed by (E)-2-cyclopropylvinyl boronic acid pinacol ester (0.233 g, 1.5 eq, 1.2 mmol), potassium carbonate (0.334 g, 3.0 eq, 2.4 mmol) and 1,1'- bis(diphenylphosphino)ferrocene palladium dichloride (58.5 mg, 0.1 eq, 0.08 mmol), nitrogen was replaced, reacted at 100 °C for 8 h. After the reaction was completed, the reaction liquid was poured into 20 mL of water, extracted twice with 10 mL of ethyl acetate, the organic phase was collected, concentrated under reduced pressure, silica gel was added, and separated by normal phase column chromatography. The product 45 (0.13 g, purity 98%, yield 67%, white oil) was obtained.

[0266] 5. Synthesis of compound 52

[0267] In a 25 mL single neck flask, 2-1 (0.3 g, 1.0 eq, 0.8 mmol) was taken in 5 mL of triethylamine, cyclopropyl acetylene (0.1 g, 2.0 eq, 1.6 mmol) was added, purged with nitrogen, cuprous iodide (0.008 g, 0.05 eq, 0.04 mmol) and dichlorobis(triphenylphosphine)palladium (0.28 g, 0.05 eq, 0.04 mmol) were added and the reaction was carried out at 70 °C for 1 h. On completion of the reaction, the reaction was poured into 20 mL of water, extracted with ethyl acetate 10 mL x 2, the organic phase was collected and concentrated under reduced pressure, silica gel was added to the sample, and the product was separated by normal phase column chromatography. The product 52 (0.18 g, 98% purity, 62% yield) was obtained as a yellow solid.

[0268] 6. Synthesis of compound 59

[0269] (1) In a 50 mL three neck flask, compound 59-1 (5 g, 1.0 eq, 28.41 mmol) was dissolved in 20 mL of tetrahydrofuran, purged with nitrogen three times, stirred at -78 °C for 10 min, 21.3 mL of lithium diisopropylamide (4.6 g, 1.5 eq, 42.62 mmol) was added dropwise slowly, the reaction was carried out for 1 h, compound 59-2 (5.8 g, 1.1 eq, 31.25 mmol) was added dropwise at -78 °C, slowly raised to room temperature, the reaction was carried out for 2 h, the reaction was monitored until the starting material was consumed. After completion of the reaction, 20 mL of saturated aqueous ammonium chloride solution was added dropwise slowly to the reaction mixture to quench the reaction, the reaction mixture was concentrated, the residue was diluted with water and extracted with ethyl acetate three times, washed with saturated brine three times. After drying over anhydrous sodium sulfate, the sample was passed through a column to obtain the product 59-3 (9.1 g, 88% yield) as a yellow solid.

[0270] (2) In a 50 mL single neck flask, 59-3 (2 g, 1.0 eq, 5.52 mmol) was dissolved in 20 mL of dichloromethane, stirred at 0 °C for 5 min, diethylamine sulfur trifluoride (1.3 g, 1.5 eq, 8.28 mmol) was added dropwise slowly, slowly raised to room temperature, the reaction was carried out for 2 h, the reaction was monitored until the starting material was consumed. After completion of the reaction, 10 mL of saturated aqueous NaHCO3 solution was added dropwise to the reaction mixture to quench the reaction, the reaction mixture was concentrated, the residue was diluted with water (200 mL) and extracted with ethyl acetate (200 mL x 3), the organic phase was washed with saturated brine (100 mL x 3), dried over anhydrous sodium sulfate and concentrated, the sample was passed through a column to obtain the product 59-4 (1.5 g, 74% yield) as a yellow oil.

[0271] (3) In a 100 mL single neck flask, intermediate 59-4 (0.2 g, 1.0 eq, 0.055 mmol) was dissolved in 4 mL of triethylamine, and cyclopropyl acetylene (0.15 g, 4.0 eq, 2.2 mmol) was added, followed by cuprous iodide (0.05 eq) and bis(triphenylphosphine)palladium dichloride (0.05 eq), and the reaction was purged with nitrogen three times and slowly raised to 80 °C for 12 h, and the reaction was monitored until the starting material was consumed. The reaction was concentrated, and the residue was diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 3), and the organic phase was washed with saturated brine (50 mL x 3). The organic phase was dried over anhydrous sodium sulfate and concentrated, and the residue was purified by column chromatography to give the product 59 (0.07 g, 41% yield) as a yellow oil.

[0272] 7. Synthesis of compound 68

[0273] (1) In a 100 mL single neck flask, intermediate 68-1 (500 mg, 1.0 eq, 1.37 mmol) was added to a mixture of 5 mL of hydriodic acid (50% in water) and 5 mL of glacial acetic acid, and the reaction was purged with nitrogen overnight at 120 °C. Upon completion of the reaction, the reaction was concentrated and diluted with water (100 mL), and extracted with ethyl acetate (100 mL x 3). The organic phase was concentrated and dried, and purified by column chromatography to give 68-2 (200 mg, 96% purity, 42% yield).

[0274] (2) In a 100 mL single neck flask, 68-2 (200 mg, 1.0 eq, 0.57 mmol) was added to 5 mL of 1,4-dioxane and 0.5 mL of water, followed by the addition of 68-3 (95.91 mg, 1.5 eq, 0.86 mmol), cesium fluoride (173.55 mg, 2.0 eq, 1.14 mmol), and 1,1'-bis(diphenylphosphino)ferrocene palladium dichloride (20 mg, 0.1 eq, 0.57 mmol), and the reaction was purged with nitrogen at 100 °C for 8 h. Upon completion of the reaction, the reaction was cooled to room temperature and diluted with water (50 mL) and extracted with ethyl acetate (100 mL x 3). The organic phase was concentrated and dried, and purified by column chromatography to give the product 68 (52 mg, 97% purity, 27% yield) as a white oil.

[0275] 8. Synthesis of compound 87

[0276] In a 25 mL single neck flask, compound 87-1 (0.2 g, 1.0 eq, 0.48 mmol) was dissolved in 4 mL of triethylamine, 87-2 (0.076 g, 1.5 eq, 0.72 mmol) was added, cuprous iodide (0.1 eq) and bis(triphenylphosphine)palladium dichloride (0.1 eq) were added, the reaction was stirred at room temperature for 1 h after three times of nitrogen gas exchange, the reaction was monitored until the starting material disappeared. The reaction liquid was concentrated, the residue was diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 3), the organic phase was washed with saturated brine (50 mL x 3), dried over anhydrous sodium sulfate and concentrated, then the sample was mixed with silica gel and separated by column chromatography to obtain the product 87 (0.15 g, yield 79%) as brown oil.

[0277] 9. Synthesis of compound 91

[0278] In a 25 mL single neck flask, compound 87-1 (0.2 g, 1.0 eq, 0.48 mmol) was dissolved in 4 mL of triethylamine, 87-2 (0.076 g, 1.5 eq, 0.72 mmol) was added, cuprous iodide (0.1 eq) and bis(triphenylphosphine)palladium dichloride (0.1 eq) were added, the reaction was stirred at room temperature for 1 h after three times of nitrogen gas exchange, the reaction was monitored until the starting material disappeared. The reaction liquid was concentrated, the residue was diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 3), the organic phase was washed with saturated brine (50 mL x 3), dried over anhydrous sodium sulfate and concentrated, then the sample was mixed with silica gel and separated by column chromatography to obtain the product 87 (0.15 g, yield 79%) as brown oil.

[0279] 10. Synthesis of compound 2-66

[0280] In a 25 mL single neck flask, compound 87-1 (0.2 g, 1.0 eq, 0.48 mmol) was dissolved in 4 mL of triethylamine, 87-2 (0.076 g, 1.5 eq, 0.72 mmol) was added, cuprous iodide (0.1 eq) and bis(triphenylphosphine)palladium dichloride (0.1 eq) were added, the reaction was stirred at room temperature for 1 h after three times of nitrogen gas exchange, the reaction was monitored until the starting material disappeared. The reaction liquid was concentrated, the residue was diluted with water (50 mL) and extracted with ethyl acetate (50 mL x 3), the organic phase was washed with saturated brine (50 mL x 3), dried over anhydrous sodium sulfate and concentrated, then the sample was mixed with silica gel and separated by column chromatography to obtain the product 87 (0.15 g, yield 79%) as brown oil.

[0281] 11. Synthesis of compound 125

[0282] (1) In a 100 mL flask, 125-1 (0.5 g, 1.0 eq, 3.26 mmol) was added to THF (10 mL), under nitrogen atmosphere, LDA (2.45 mL, 1.5 eq, 6.52 mmol) was added dropwise at -70 °C, and the reaction was incubated for half an hour. 4-cyanobenzaldehyde (0.43 g, 1.0 eq, 3.26 mmol) was added, and the reaction was continued for half an hour. The product was monitored, and the reaction was quenched by dropwise addition of an ammonium chloride solution. EA extraction was performed twice, the organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Silica gel was added to the sample, and normal phase column chromatography was performed to isolate the product 125-2 (0.41 g, 44%).

[0283] (2) In a 50 mL flask, 125-2 (0.41 g, 1.0 eq, 1.44 mmol) was added to 10 mL of dichloromethane, and DAST (0.35 g, 1.5 eq, 2.16 mmol) was added dropwise under ice bath. After 0.5 hours, the reaction was completed, and the reaction solution was poured into 10 mL of ice water. Dichloromethane (20 mL x 2) was used for extraction, and the organic phase was collected and concentrated under reduced pressure. Silica gel was added to the sample, and normal phase column chromatography was performed to isolate the product 125 (0.36 g, 87%).

[0284] 12. Synthesis of compound 144

[0285] (1) In a 100 mL flask, 144-1 (0.5 g, 1.0 eq, 1.64 mmol) was added to 5 mL of DMF, NaH (98.3 mg, 1.5 eq, 2.46 mmol) and CH3I (348.8 mg, 1.5 eq, 2.46 mmol) were added, and the reaction was performed at room temperature for 2 hours. The reaction was monitored by LCMS, and the reaction was completed. The reaction solution was extracted with water and EA three times, the organic phase was washed with brine, silica gel was added to the sample, and normal phase column chromatography was performed to isolate the product 144-2 (0.4 g, 90% purity, 40% yield) using EA (20%).

[0286] (2) In a 100 mL flask, 144-2 (0.4 g, 1.0 eq, 1.25 mmol) was added to 5 mL of DMF, and cyclopropyl alcohol (87 mg, 1.2 eq, 1.5 mmol) and NaH (75 mg, 1.5 eq, 1.88 mmol) were added. The reaction was performed at room temperature for 3 hours, and the reaction was monitored by LCMS. The reaction was completed, and the reaction solution was extracted with water and EA three times. The organic phase was washed with brine, silica gel was added to the sample, and normal phase column chromatography was performed to isolate the product 144 (52 mg, 99% purity, 11.6% yield) using EA (20%).

[0287] 13. Synthesis of compound 163

[0288] (1) In a 50 mL single neck flask, 125 (0.30 g, 1.0 eq, 1.05 mmol) was added to 10 mL of ethanol, hydroxylamine aqueous solution (0.35 g, 5.0 eq, 5.24 mmol) was added, and the reaction was carried out at 50 °C for 5 h. After the reaction was completed, the product 163-1 crude (0.36 g) was obtained by concentration.

[0289] (2) In a 50 mL single neck flask, 163-1 (0.36 g, 1.0 eq, 1.13 mmol) was added to 10 mL of THF, TFAA (0.36 g, 1.5 eq, 1.70 mmol) was added dropwise, and the reaction was carried out at room temperature for 0.5 h. After the reaction was completed, the reaction solution was poured into 10 mL of sodium carbonate solution, extracted with EA, and the organic phase was collected and concentrated under reduced pressure. Silica gel was added to the sample, and the product 163 (0.34 g, purity 95%, yield 72%) was separated by normal phase column chromatography.

[0290] 14. Synthesis of compound 174

[0291] (1) 173 (synthesis reference 125-2, 1.0 g, 2.95 mmol, 1 eq) was dissolved in 15 mL of DCM and added to a 100 mL single neck flask, and DMP (1.50 g, 3.54 mmol, 1.5 eq) was added and the reaction was carried out at room temperature for 12 h. The reaction was monitored until the starting material disappeared, and the reaction solution was naturally cooled to room temperature and washed with saturated brine three times. After drying with anhydrous sodium sulfate, column purification was performed to obtain 174-1 (0.8 g, yield 80%).

[0292] (2) 174-1 (0.8 g, 2.37 mmol) was dissolved in 20 mL of tetrahydrofuran and added to a 100 mL three-neck flask, and nitrogen was replaced three times. The temperature was reduced to 0 °C in an ice bath, and methyl magnesium bromide (4.74 mL, 4.74 mmol, 1M in THF) was slowly added dropwise. The reaction was carried out at room temperature for 6 h, and the reaction was monitored until the starting material disappeared. The reaction solution was quenched, concentrated, and the sample was purified by normal phase to obtain 174-2 (0.56 g, yield 67%).

[0293] (3) In a 50 mL single neck flask, 174-2 (0.56 g, 1.0 eq, 1.59 mmol) was added to 10 mL of dichloromethane, triethylamine (0.48 g, 4.76 mmol, 3 eq) and trifluoromethanesulfonic anhydride (0.41 g, 2.38 mmol, 1.5 eq) were added, and the reaction was carried out at room temperature for 2 h. After the reaction was completed, the reaction solution was poured into 10 mL of ice water, extracted with dichloromethane 10 mL x 2, the organic phase was collected and concentrated under reduced pressure to obtain the product 174-3 crude 0.62 g.

[0294] (4) In a 50 mL single neck flask, 174-3 (0.62 g, 1.0 eq, 1.44 mmol) was added to 5 mL of DMA, DBU (0.21 g, 1.0 eq, 1.44 mmol) was added, and the reaction was allowed to proceed at room temperature for 1 hour. After the reaction was completed, the reaction solution was quenched with water, extracted with ethyl acetate 10 mL x 2, the organic phase was collected, and concentrated under reduced pressure. Silica gel was added to the sample, and the product 174 (0.158 g, purity 94%, yield 32%) was separated by normal phase column chromatography.

[0295] 15. Synthesis of compound 106

[0296] In a 50 mL round bottom flask, 109 (synthesis reference 174, 0.20 g, 0.59 mmol, 1 eq) was added to 10 mL of methanol, and 10% palladium-carbon catalyst (0.02 g) was added. The system was replaced with a hydrogen atmosphere, and the reaction was allowed to proceed at room temperature for 8 hours. After the reaction was completed, the system was filtered with celite to remove the palladium-carbon catalyst, and silica gel powder was added to the filtrate, which was distilled under reduced pressure. Column chromatography yielded the product 106 (0.14 g, yield 70%).

[0297] 16. Synthesis of compound 2-119

[0298] In a 50 mL round bottom flask, 2-120 (synthesis reference 125, 130 mg, 0.39 mmol, 1 eq) was added to 5 mL of methanol, and 10% palladium-carbon catalyst (0.02 g) was added. The system was replaced with a hydrogen atmosphere, and the reaction was allowed to proceed at room temperature overnight. After the reaction was completed, the system was filtered with celite to remove the palladium-carbon catalyst, and silica gel powder was added to the filtrate, which was distilled under reduced pressure. Column chromatography yielded the product 2-119 (61 mg, yield 45%).

[0299] 17. Synthesis of compound 2-122

[0300] (1) In a 50 mL round bottom flask, 2-122-1 (synthesis reference 125-2, 500 mg, 1.72 mmol, 1 eq) was added to 10 mL of DMF, and the system was cooled by stirring in an ice water bath. Then, 60% sodium hydride (137.84 mg, 3.45 mmol, 2 eq) was added, and the activation was allowed to proceed for half an hour. Then, iodomethane (733.69 mg, 5.17 mmol, 3 eq) was added. The reaction was allowed to proceed overnight. After the reaction was completed, a small amount of water was added to quench the reaction, and saturated brine 50 mL and ethyl acetate 20 mL*2 were added to extract. The organic phase was collected, silica gel powder was added, and distilled under reduced pressure. Column chromatography yielded the product 2-122-2 (100 mg, yield 18%).

[0301] (2) In a 50 mL round-bottom flask, 2-122-2 (100 mg, 0.31 mmol, 1 eq) and cyclopropanol (18.25 mg, 0.31 mmol, 1 eq) were added to 10 mL of DMF, protected by nitrogen replacement, and cooled by stirring in an ice water bath. Then, 60% sodium hydride (25.14 mg, 0.63 mmol, 2 eq) was added, and the reaction was continued overnight. After the reaction was completed, a small amount of water was added to quench the reaction, and saturated brine 50 mL and ethyl acetate 20 mL*2 were used for extraction. The organic phase was collected, silica gel powder was added, and the mixture was distilled under reduced pressure. Column chromatography yielded the product 2-122 (28 mg, yield 23%).

[0302] 18, Synthesis of compound 2-125

[0303] In a 50 mL round-bottom flask, 2-124 (synthesis reference 125-2, 250 mg, 0.76 mmol, 1 eq) was added to 5 mL of THF, protected by nitrogen replacement, and cooled by stirring in an ice water bath. Then, 60% sodium hydride (36.56 mg, 0.91 mmol, 1.2 eq) was added in batches, activated for 20 minutes, and then iodomethane (216.19 mg, 1.52 mmol, 2 eq) was slowly added dropwise. The reaction was continued for 3 hours. After the reaction was completed, a small amount of water was added to quench the reaction, and saturated brine 50 mL and ethyl acetate 20 mL*2 were used for extraction. The organic phase was collected, silica gel powder was added, and the mixture was distilled under reduced pressure. Column chromatography yielded the product 2-125 (180 mg, yield 68%).

[0304] 19, Synthesis of compound 2-136

[0305] In a 50 mL round-bottom flask, 2-132 (synthesis reference 174-1, 140 mg, 0.43 mmol, 1 eq) was added to 5 mL of pyridine, and N-methoxymethylamine hydrochloride (60.58 mg, 1.29 mmol, 3 eq) was added. The reaction was continued overnight at 80°C. After the reaction was completed, the solvent was removed by distillation under reduced pressure, and then water 50 mL and ethyl acetate 20 mL*2 were used for extraction. The organic phase was collected, silica gel powder was added, and the mixture was distilled under reduced pressure. Column chromatography yielded the product 2-136 (54 mg, yield 34%).

[0306] 20, Synthesis of compound 2-197

[0307] (1) In a 100 mL flask, 2-197-1 (0.25 g, 1.0 eq, 1.47 mmol) was added to THF (10 mL), under nitrogen atmosphere, LDA (1.11 mL, 1.5 eq, 2.21 mmol) was added dropwise at -70 °C, and the reaction was incubated for half an hour. 3-chloro-5- (cyclopropoxy) pyridine (0.23 g, 1.0 eq, 1.47 mmol) was added, and the reaction was continued for half an hour. The product was monitored, and the reaction was quenched by dropwise addition of an ammonium chloride solution. EA extraction was performed twice, the organic phase was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. Silica gel was added to the sample, and normal phase column chromatography was performed to isolate the product 2-197-2 (89 mg, 17%).

[0308] (2) In a 50 mL flask, 2-197-2 (89 mg, 1.0 eq, 0.27 mmol) was added to 10 mL of dichloromethane, and DAST (88 mg, 2.0 eq, 0.54 mmol) was added dropwise at -40 °C. After 0.5 hours, the reaction was completed, and the reaction solution was poured into 10 mL of ice water. Dichloromethane (20 mL x 2) was used for extraction, and the organic phase was collected and concentrated under reduced pressure. Silica gel was added to the sample, and normal phase column chromatography was performed to isolate the product 2-197 (66 mg, 97% purity, 72% yield).

[0309] 21. Synthesis of compound 2-280

[0310] (1) In a 100 mL flask, 2-280-1 (0.3 g, 1.0 eq, 1.45 mmol) was added to 20 mL of DMF, and pyrazole (295 mg, 1.5 eq, 2.17 mmol) and potassium carbonate (400 mg, 2.0 eq, 2.9 mmol) were added. The reaction was incubated at room temperature for 6 hours. LCMS was used to detect the completion of the reaction. The reaction solution was treated with water and EA extraction was performed three times. The organic phase was washed with brine, and silica gel was added to the sample. Normal phase column chromatography was performed to isolate the product 2-280-2 (0.15 g, 90% purity, 40% yield) using EA (30%).

[0311] (2) In a 100 mL flask, 2-280-2 (0.15 g, 1.0 eq, 0.57 mmol) was added to 20 mL of DMF, and cyclopropyl alcohol (33 mg, 1.0 eq, 0.57 mmol) and NaH (45.6 mg, 2.0 eq, 1.14 mmol) were added. The reaction was incubated at room temperature for 3 hours. LCMS was used to detect the completion of the reaction. The reaction solution was treated with water and EA extraction was performed three times. The organic phase was washed with brine, and silica gel was added to the sample. Normal phase column chromatography was performed to isolate the product 2-280 (50 mg, 99% purity, 29% yield) using EA (30%).

[0312] 22. Synthesis of compound 2-283

[0313] (1) In a 250 mL three-necked flask, 2-283-1 (1.0 g, 1.0 eq, 4.1 mmol) was added to 30 mL THF, protected by N2, and LDA (3.1 ml, 1.5 eq, 6.15 mmol) was added at -78 °C. The reaction was incubated for 1 h, and 3,5-difluoropyridine (16.5 g, 1 eq, 4.1 mmol) was continuously added. The reaction was incubated for 4 h. LCMS detection showed that the reaction was complete. The reaction solution was quenched with saturated ammonium chloride, and extracted with ethyl acetate and water. The organic phase was collected and added to silica gel, and purified by normal phase to obtain the product 2-283-2 (0.4 g, 90% purity, 28.5% yield).

[0314] (2) In a 100 mL single-necked flask, 2-283-2 (0.4 g, 1.0 eq, 1.12 mmol) was added to 20 mL DCM, and DAST (0.36 g, 2 eq, 2.24 mmol) was added. The reaction was incubated at room temperature for 4 h. LCMS detection showed that the reaction was complete. The reaction solution was quenched with ice water, and extracted with DCM and water. Silica gel was added, and purified by normal phase to obtain the product 2-283-3 (0.3 g, 90% purity, 75% yield).

[0315] (3) In a 100 mL single-necked flask, 2-283-3 (0.3 g, 1.0 eq, 0.84 mmol) was added to 20 mL DMF, and cyclopropanol (48 mg, 1.5 eq, 0.84 mmol) and NaH (67 mg, 2.0 eq, 1.68 mmol) were added. The reaction was incubated at room temperature for 3 h. LCMS detection showed that the reaction was complete. The reaction solution was quenched with water and EA was added and extracted three times. The organic phase was washed with brine, and silica gel was added. The sample was separated by normal phase column chromatography with EA (30%) to obtain the product 2-283 (0.15 g, 99% purity, 15% yield).

[0316] Biological activity evaluation (insecticidal activity test)

[0317] Brown planthopper, white-backed planthopper: select planthoppers with consistent physiological state from indoor rearing, put them into disposable transparent plastic cups, and introduce 30 test insects with consistent growth into each cup. The rice stems are wrapped with wet cotton balls to maintain humidity, and then sprayed using a spray tower. After spraying, the cup opening is covered with a cup cover. Repeat 3 times, with the highest dose containing acetone as the control. After the application is completed, place it in a treatment room (temperature 25 °C, humidity 60%). After 5 days, investigate the number of dead insects and calculate the mortality rate. Mortality rate = (number of dead insects / number of test insects) x 100%.

[0318] Table 4 representative insecticidal activity test results

[0319] Note: N represents no data; control compound A:

[0320] Table 5 comparative results of insecticidal activity test

[0321] Note: control compound B: Meanwhile, it is found through many tests that the compounds and compositions of the present application have good control activity on pests such as Homoptera (such as brown planthopper, white-backed planthopper, gray planthopper, etc.), can effectively control resistant pests, and have certain commercial value.

Claims

1. A substituted pyridine compound as shown in general formula I, or a salt or N-oxide thereof: wherein L represents a direct bond, -O-, -S-, -NR8-, alkylene, alkenylene or alkynylene; R8represents hydrogen or alkyl; Q represents cycloalkyl or cycloalkenyl; M represents aryl or heterocyclyl; X represents halogen; Y1, Y2each independently represents hydrogen, halogen, cyano, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, aryl, heterocyclyl, -OR9or -S(O)mR9; m R9, or Y1, Y2together with the carbon atom to which they are attached form C=N-OR9, C=C(R9)2, carbonyl or thiocarbonyl; R9independently represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxyalkyl, cycloalkyl, cycloalkylalkyl, alkoxycarbonylalkyl, aryl, heterocyclyl, arylalkyl or heterocyclylalkyl; the aforementioned cycloalkyl or cycloalkenyl is optionally substituted by at least one group selected from hydroxy, halogen, cyano, nitro, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio or alkylsulfonyl; The aforementioned heterocyclic or aryl group is optionally selected from halogen, nitro, cyano, alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl, cycloalkyl, cycloalkenyl, cycloalkylalkyl, cycloalkylalkenyl, cycloalkylynyl, -OR 10 ,-alkylene-OR 10 -O-alkylene-OR 10 ,-alkylene-S(O) m R 10 -S(O) m R 10 ,-alkylene-COOR 10 -COOR 10 -COR 10 -(CO)N(R) 10 2. A trialkylsilyl group or an aryl or heterocyclic group substituted with at least one group selected from halogens, alkyl groups, or haloalkyl groups, or two adjacent carbon atoms on the ring substituted with an unsubstituted or substituted group selected from halogens, alkyl groups, or -COR groups. 10 or -COOR 10 -(CH2) is substituted by at least one group. n -, -OCH2O-, -SCH2O-, -SCH2S- or -OCH2CH2O- form a ring structure; R 10 each independently represents hydrogen, alkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl, haloalkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, or aryl, arylalkyl, heterocyclyl, or heterocyclylalkyl unsubstituted or substituted with at least one group selected from alkyl, halo, alkoxy, haloalkoxy, or haloalkyl; m represents 0, 1 or 2; n represents 1, 2, 3 or 4.

2. The substituted pyridine compound or salt, N-oxide thereof according to claim 1, characterized in that, L represents a direct bond, -O-, -S-, -NR8-, C1-C8 alkylene, C2-C8 alkenylene or C2-C8 alkynylene; R8represents hydrogen or C1-C8 alkyl; Q represents C3-C8 cycloalkyl or C3-C8 cycloalkenyl; M represents aryl or heterocyclyl; X represents halogen; Y1, Y2independently represent hydrogen, halogen, cyano, Ci-C8alkyl, halo-Ci-C8alkyl, C2-C8alkenyl, halo-C2-C8alkenyl, C2-C8alkynyl, halo-C2-C8alkynyl, aryl, heterocyclyl, -OR9or -S(O)mR9; m R9, or Y1, Y2together with the carbon atom to which they are attached form C=N-OR9, C=C(R9)2, carbonyl or thiocarbonyl; R9independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, C1-C8 alkoxyC1-C8 alkyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, C1-C8 alkoxycarbonylC1-C8 alkyl, aryl, heterocyclyl, arylC1-C8 alkyl or heterocyclylC1-C8 alkyl; the aforementioned C3-C8 cycloalkyl or C3-C8 cycloalkenyl is optionally substituted by at least one group selected from hydroxy, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, haloC1-C8 alkyl, haloC2-C8 alkenyl, haloC2-C8 alkynyl, C1-C8 alkoxy, haloC1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio or C1-C8 alkylsulfonyl; The aforementioned heterocyclic or aryl groups are optionally selected from halogens, nitro groups, cyano groups, C1-C8 alkyl groups, halo-C1-C8 alkyl groups, C2-C8 alkenyl groups, halo-C2-C8 alkenyl groups, C2-C8 alkynyl groups, halo-C2-C8 alkynyl groups, C3-C8 cycloalkyl groups, C3-C8 cycloalkyl groups (C1-C8 alkyl), C3-C8 cycloalkyl groups (C2-C8 alkenyl), C3-C8 cycloalkyl groups (C2-C8 alkynyl), and -OR groups. 10 -(C1-C8 alkylene)-OR 10 -O-(C1-C8 alkylene)-OR 10 -(C1-C8 alkylene)-S(O) m R 10 -S(O) m R 10 -(C1-C8 alkylene)-COOR 10 -COOR 10 -COR 10 -(CO)N(R) 10 2. A tri-C1-C8 alkylsilyl group or an unsubstituted or substituted aryl or heterocyclic group selected from halogen, C1-C8 alkyl, or halo-C1-C8 alkyl groups, or two adjacent carbon atoms on the ring are substituted with an unsubstituted or substituted aryl or heterocyclic group selected from halogen, C1-C8 alkyl, -COR 10 or -COOR 10 -(CH2) is substituted by at least one group. n -, -OCH2O-, -SCH2O-, -SCH2S- or -OCH2CH2O- form a ring structure; R 10 each independently represents hydrogen, C1-C8alkyl, C2-C8alkenyl, C2-C8alkynyl, haloC1-C8alkyl, haloC2-C8alkenyl, haloC2-C8alkynyl, C3-C8cycloalkyl, C3-C8cycloalkylC1-C8alkyl, C3-C8cycloalkenyl, C3-C8cycloalkenylC1-C8alkyl, or aryl, arylC1-C8alkyl, heterocyclyl or heterocyclylC1-C8alkyl which is unsubstituted or substituted by at least one group selected from C1-C8alkyl, halogen, C1-C8alkoxy, haloC1-C8alkoxy or haloC1-C8alkyl; m represents 0, 1 or 2; n represents 1, 2, 3 or 4.

3. The substituted pyridine compound or salt, N-oxide thereof according to claim 1 or 2, characterized in that, L represents a direct bond, -O-, -S-, -NR8-, C1-C6 alkylene, C2-C6 alkenylene or C2-C6 alkynylene; R8represents hydrogen or C1-C6 alkyl; Q represents C3-C6 cycloalkyl or C3-C6 cycloalkenyl; M represents aryl or heterocyclyl; X represents halogen; Y1, Y2independently represent hydrogen, halogen, cyano, C1-C6alkyl, haloC1-C6alkyl, C2-C6alkenyl, haloC2-C6alkenyl, C2-C6alkynyl, haloC2-C6alkynyl, aryl, heterocyclyl, -OR9or -S(O)mR9; m R9, or Y1, Y2together with the carbon atom to which they are attached form C=N-OR9, C=C(R9)2, carbonyl or thiocarbonyl; R9each independently represents hydrogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, halo-Ci-C6-alkyl, halo-C2-C6-alkenyl, halo-C2-C6-alkynyl, Ci-C6-alkoxy-Ci-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-Ci-C6-alkyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, aryl, heterocyclyl, aryl-Ci-C6-alkyl or heterocyclyl-Ci-C6-alkyl; the aforementioned C3-C6-cycloalkyl or C3-C6-cycloalkenyl is optionally substituted by at least one radical selected from the group consisting of hydroxyl, halogen, cyano, nitro, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, halo-Ci-C6-alkyl, halo-C2-C6-alkenyl, halo-C2-C6-alkynyl, Ci-C6-alkoxy, halo-Ci-C6-alkoxy, Ci-C6-alkoxycarbonyl, Ci-C6-alkylthio or Ci-C6-alkylsulfonyl; haloC2-C6alkenyl, haloC2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkenyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkylC2-C6alkenyl, C3-C6cycloalkylC2-C6alkynyl, -OR 10 , -(C1-C6alkylene)-OR 10 , -O-(C1-C6alkylene)-OR 10 , -(C1-C6alkylene)-S(O) m R 10 , -S(O) m R 10 , -(C1-C6alkylene)-COOR 10 , -COOR 10 , -COR 10 , -(CO)N(R 10 )2, triC1-C6alkylsilyl, phenyl, pyridyl, pyrimidinyl, substituted with at least one group selected from halogen, C1-C6alkyl, -COR 10 or -COOR 10 substituted with at least one group selected from halogen, C1-C6alkyl, -COR n -CH2-, -OCH2-, -SCH2-, -SCH2S-, -OCH2O-, -SCH2O-, -SCH2S- or -OCH2CH2O- form a cyclic structure; wherein the phenyl, pyridyl, pyrimidinyl, optionally substituted by at least one radical selected from the group consisting of halogen, Ci-C6-alkyl or halo-Ci-C6-alkyl; R 10 each independently represents hydrogen, C1-C6alkyl, C2-C6alkenyl, C2-C6alkynyl, haloC1-C6alkyl, haloC2-C6alkenyl, haloC2-C6alkynyl, C3-C6cycloalkyl, C3-C6cycloalkylC1-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkenylC1-C6alkyl, or phenyl, benzyl, pyridyl, pyrimidyl, pyrazolyl, imidazolyl, thienyl, furyl, thiazolyl, oxazolyl, isoxazolyl, triazolyl, tetrazolyl, tetrahydrofuranyl, tetrahydropyranyl, tetrahydrothiopyranyl, piperidyl, piperazinyl, morpholinyl, indanyl, indenyl, indolyl, indazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzothiazolyl, benzimidazolyl, quinolinyl, isoquinolinyl, quinazolinyl, quinoxalinyl, quinuclidinyl, or indolinyl unsubstituted or substituted by at least one radical selected from C1-C6alkyl, halogen, C1-C6alkoxy, haloC1-C6alkoxy, or haloC1-C6alkyl, m represents 0, 1 or 2; n represents 1, 2, 3 or 4; Preferably, the compound is selected from any one of Table 1, Table 3, Table A or Table B.

4. A substituted pyridine compound according to any one of claims 1 to 3, or a salt, N-oxide thereof, characterized in that L represents a direct bond, -0-, C2-C6-alkenylene or C2-C6-alkynylene; Q represents C3-C6-cycloalkyl or C3-C6-cycloalkenyl; M represents aryl or heterocyclyl; X represents halogen; Y1, Y2each independently represents hydrogen, halogen, C1-C6alkyl, heterocyclyl, -OR9or -S(O)mR9; m R9, or Y1, Y2together with the carbon atom to which they are attached form C=C(R9)2or carbonyl; R9each independently represents hydrogen, Ci-C6-alkyl or C3-C6-cycloalkyl-Ci-C6-alkyl; the aforementioned C3-C6-cycloalkyl or C3-C6-cycloalkenyl is optionally substituted by at least one radical selected from the group consisting of hydroxyl or Ci-C6-alkyl; The foregoing heterocyclyl or aryl is optionally substituted with one or more substituents selected from the group consisting of halogen, cyano, C1-C6alkyl, haloC1-C6alkyl, C3-C6cycloalkenyl, C3-C6cycloalkyl, C2-C6alkynyl, -OR 10 , -S(O) m R 10 , -COR 10 , phenyl, pyrimidinyl or substituted with at least one group selected from halogen, or adjacent carbon atoms on the ring form a ring structure with -OCH2O- which is unsubstituted or substituted with at least one group selected from halogen; wherein the phenyl, pyrimidinyl or optionally substituted by at least one radical selected from the group consisting of halogen or halo-Ci-C6-alkyl; R 10 each independently represents C1-C6alkyl, haloC1-C6alkyl, or phenyl, benzyl, pyridyl, or m represents 0, 1 or 2; or L represents a direct bond, -0-, C2-C6-alkenylene or C2-C6-alkynylene; Q represents C3-C6-cycloalkyl or C3-C6-cycloalkenyl; M represents an aryl or heterocyclic group, which is optionally selected from halogens, cyano groups, C1-C6 alkyl groups, halogenated C1-C6 alkyl groups, and -OR groups. 10 or -S(O) m R 10 The ring is substituted by at least one group in the halogen, or the two adjacent carbon atoms on the ring form a ring structure with unsubstituted or substituted -OCH2O- groups selected from halogens. Y1, Y2independently represent hydrogen, halogen, C1-C6alkyl, -OR 10 or -S(O) m R 10 or Y1, Y2together with the carbon atom to which they are attached form C=CH2or a carbonyl group; R 10 each independently represents C1-C6alkyl or haloC1-C6alkyl; m represents 0, 1 or 2; the aforementioned C3-C6-cycloalkyl is optionally substituted by at least one radical selected from the group consisting of hydroxyl or Ci-C6-alkyl.

5. A substituted pyridine compound according to any one of claims 1 to 4, or a salt, N-oxide thereof, characterized in that L represents a direct bond, -0-, -CH=CH- or -C≡C-.

6. A substituted pyridine compound having a chiral center of the formula I' or a salt, N-oxide thereof: ###00019### I' wherein the definitions of the substituents Q, L, X, Y1, Y2, M and the carbon atom at the position C* being a chiral center (R or S configuration) are as described in any one of claims 1 to 5; Preferably, it has a stereochemical purity of 60-100% (R) or (S), preferably 70-100% (R) or (S), more preferably 80-100% (R) or (S), further preferably 90-100% (R) or (S), more further preferably 95-100% (R) or (S), based on the content of stereoisomers having the R and S configuration at this position.

7. A process for the preparation of a substituted pyridine compound or a salt, N-oxide thereof according to any one of claims 1 to 6, characterized in that, comprising the following steps: (1) preparing compounds represented by general formula II and III through a coupling reaction A compound as shown in general formula I, whose reaction equation is as follows: wherein Y1, Y2, L, X, Q and M are as defined in any one of claims 1-6; when L represents a direct bond, alkylene, alkenylene or alkynylene, either of W1, W2 is halogen, OMs or OTf, and the other is a boron reagent, a tin reagent, a zinc reagent, a silicon reagent or a Grignard reagent, or W1 is halogen and W2 is H; when either of W1, W2 is halogen, OMs or OTf, and the other is a boron reagent, a tin reagent, a zinc reagent, a silicon reagent or a Grignard reagent, preferably, the reaction is carried out in the presence of a solvent and a catalyst; more preferably, the reaction condition is further in the presence of a base; further preferably, the solvent is an organic solvent / water, the organic solvent is selected from at least one of aromatic hydrocarbon, DMF, DMA, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate; the catalyst is selected from at least one of Pd(PPh3)4, Pd(dppf)Cl2, Pd(OAc)2 / n-butyl bis(1-adamantyl)phosphine, Pd(OAc)2 / tricyclohexylphosphine, PdCl2(PPh3)2 or 1,1'-bis(diphenylphosphino)ferrocene dichloropalladium(II) dichloromethane complex; the base is selected from at least one of inorganic base or organic base; when W1 is halogen and W2 is H, preferably, the reaction is carried out in the presence of a solvent and a catalyst; more preferably, the solvent is selected from at least one of triethylamine, pyridine, DMF, methanol or ethyl acetate; the catalyst is a palladium catalyst / cuprous iodide; when L represents -O-, -S- or -NR1-, W1 is halogen and W2 is H; preferably, the reaction is carried out in the presence of a solvent and a base; more preferably, the solvent is selected from at least one of aromatic hydrocarbon, DMF, DMA, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane or ethyl acetate, and / or the base is selected from organic base or inorganic base; or (2) when Y1is OH and Y2is H, compounds of Formula IV and V are reacted to produce compounds of Formula I', according to the following reaction scheme: wherein L, X, Q and M are as defined in any one of claims 1-6; preferably, the reaction is carried out in the presence of a solvent and a base; more preferably, the solvent is selected from at least one of diethyl ether, ethylene glycol dimethyl ether, carbon tetrachloride, tetrahydrofuran, pentane, hexane or cyclohexane, and / or the base is selected from at least one of LDA, n-BuLi, methyllithium, LiHMDS, NaHMDS or KHMDS.

8. An insecticide composition, characterized by, comprising an insecticidally effective amount of at least one substituted pyridine compound or salt, N-oxide thereof according to any one of claims 1-6; preferably, further comprising a formulation adjuvant; more preferably, further comprising other active ingredients.

9. A method for controlling pests, characterized by, comprising contacting the pest or its environment with a biologically effective amount of a substituted pyridine compound or salt thereof, N-oxide of any one of claims 1 to 6 or a composition of claim 8.

10. Use of a substituted pyridine compound or salt thereof, N-oxide of any one of claims 1 to 6 or a composition of claim 8 for controlling pests.

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