Trifluoroolefin compounds with nematicidal activity and preparation method and use thereof

Abstract

The present invention relates to a trifluoroolefin compound having nematicidal activity, a preparation method and use thereof. Specifically, the present invention discloses a compound represented by formula (I) or its optical isomers, cis-trans isomers or pesticide-acceptable salts, and a preparation method thereof. The compound of the present invention has excellent nematicidal activity.

Description

Technical Field

[0001] The present invention belongs to the field of pesticides and specifically relates to a trifluoroolefin compound having nematicidal activity and a preparation method and use thereof. Background Art

[0002] Plant parasitic nematodes are a type of extremely harmful pathogenic microorganisms. They are widely distributed, diverse in species, and highly adaptable to the environment. They can parasitize the roots, stems, leaves, seeds, young shoots, and fruits of plants. They can cause mechanical damage to host plants through feeding activities and plunder the nutrients of host plants. In particular, their esophageal gland secretions can cause a series of lesions in host plants. They can also infect host plants with other pathogenic microorganisms, causing complex diseases and resulting in yield losses. Globally, plant parasitic nematodes cause agricultural losses of more than $100 billion each year, seriously restricting the development of the agricultural economy.

[0003] There are many means of controlling nematodes in agriculture, and chemical control is currently the main method. Widely used chemical nematicides are mainly highly toxic, high-residue organophosphorus or carbamate pesticides, such as thiosulfuron, chlorpyrifos, fenamiphos, thiathion, aldicarb, oxamyl and carbofuran, which have low safety for humans and other non-target organisms, and also cause varying degrees of pollution to soil, water sources and agricultural products. In addition, due to the single variety, such nematicides are excessively and frequently used, which has caused serious drug resistance, making the control of nematodes increasingly difficult. Therefore, it has become a technical problem in this field to urgently solve to find a novel chemical nematicide with high efficiency, low toxicity and good environmental compatibility.

[0004] In summary, there is an urgent need in the art to develop new compounds with nematicidal activity. Summary of the invention

[0005] The purpose of the present invention is to provide a novel chemical nematicide with high efficiency, low toxicity and good environmental compatibility.

[0006] Another object of the present invention is to provide a preparation method and application of the chemical nematicide.

[0007] In the first aspect, the present invention provides a compound represented by formula (I), or an optical isomer, a cis-trans isomer or a pesticide-acceptable salt thereof:

[0008]

[0009] In the formula,

[0010] A is an oxygen or sulfur atom;

[0011] G is selected from the group consisting of H, substituted or unsubstituted C 1-6 Alkyl, substituted or unsubstituted C3-6 Cycloalkyl, substituted or unsubstituted C 2-6 Alkenyl, substituted or unsubstituted C 2-6 Alkynyl, substituted or unsubstituted C 5-7 Cycloalkenyl, substituted or unsubstituted phenyl or aromatic heterocyclic group, substituted or unsubstituted naphthyl, substituted or unsubstituted 5-membered or 6-membered alicyclic group, or substituted or unsubstituted 8-membered to 12-membered heteroaromatic bicyclic group;

[0012] M is a substituted or unsubstituted 5-7 membered aromatic ring, a substituted or unsubstituted 5-7 membered carbocyclic ring, a substituted or unsubstituted 5-7 membered aromatic heterocyclic ring or a 9-12 membered condensed aromatic heterocyclic ring, or a substituted or unsubstituted 5-7 membered aliphatic heterocyclic ring, CH2SN2, substituted or unsubstituted NH, O, CO, SO, SO2, (CH2) m , wherein m is an integer of 0-5; the substituent of the ring M is selected from the following group: H, halogen, substituted or unsubstituted C 1-6 Alkyl or alkoxy, substituted or unsubstituted C 3-6 Cycloalkyl, substituted or unsubstituted C 2-6 Alkenyl, substituted or unsubstituted C 2-6 Alkynyl, substituted or unsubstituted C 5-7 Cycloalkenyl, substituted or unsubstituted phenyl or aromatic heterocyclic group, substituted or unsubstituted naphthyl, substituted or unsubstituted 5-membered or 6-membered alicyclic group, or substituted or unsubstituted 8-membered to 12-membered heteroaromatic bicyclic group;

[0013] Q is a substituted or unsubstituted 5-12 membered aromatic ring, a substituted or unsubstituted 5-12 membered carbocyclic ring, a substituted or unsubstituted 5-12 membered aromatic heterocyclic ring, a substituted or unsubstituted 5-12 membered alicyclic ring (including a fully or partially unsaturated alicyclic ring), a substituted or unsubstituted alkenyl group, or is selected from the following U-1 to U-36:

[0014]

[0015] wherein p is an integer of 0-7, preferably an integer of 0-5, most preferably an integer of 0-3;

[0016] Wherein R1 is selected from the following group: =O, substituted or unsubstituted C 1-6 Alkyl or alkoxy, halogen, substituted or unsubstituted C 3-7 Cycloalkyl, substituted or unsubstituted C 2-6 Alkenyl, substituted or unsubstituted C 2-6 Alkynyl, substituted or unsubstituted C 5-7 cycloalkenyl, substituted or unsubstituted phenyl, substituted or unsubstituted naphthyl, substituted or unsubstituted 5-membered or 6-membered aromatic heterocyclic group, substituted or unsubstituted 5-membered or 6-membered alicyclic group, or substituted or unsubstituted 8- to 12-membered heteroaromatic bicyclic group.

[0017] In a preferred embodiment, Q is a 5-12 membered aromatic ring or an aromatic heterocyclic ring.

[0018] In a further preferred embodiment, Q is a 5-12 membered benzoaromatic heterocycle or a 5-12 membered benzoaromatic heterocycle.

[0019] In a specific embodiment, the compound is as shown in Formula II, I-II, I-III, I-IV, IV or I-VI:

[0020]

[0021] Wherein, n is an integer from 0 to 2;

[0022] m, A, G and Q are as defined in claim 1;.

[0023] In a specific embodiment,

[0024] In the compound represented by formula II,

[0025] m is 0 or 1;

[0026] A is oxygen or sulfur;

[0027] G is H, substituted or unsubstituted C 1-6 Alkyl or alkoxy (preferably halogen-substituted alkyl), five-membered or six-membered aromatic heterocycle;

[0028] Q is a substituted or unsubstituted 5-12 membered aromatic ring, a substituted or unsubstituted 5-12 membered aromatic heterocyclic ring, or a substituted or unsubstituted 5-12 membered aliphatic heterocyclic ring;

[0029] In the compounds represented by formula I-III,

[0030] A is oxygen or sulfur;

[0031] G is H, substituted or unsubstituted C 1-6 Alkyl or alkoxy (preferably halogen-substituted alkyl);

[0032] M corresponding to formula I is substituted or unsubstituted NH;

[0033] Q is a substituted or unsubstituted 5-12 membered aromatic ring, or a substituted or unsubstituted 5-12 membered aromatic heterocyclic ring;

[0034] In the compounds represented by formula I-IV,

[0035] A is oxygen or sulfur;

[0036] G is H, substituted or unsubstituted C 1-6 Alkyl or alkoxy (preferably halogen-substituted alkyl);

[0037] n is 0;

[0038] Q is a substituted or unsubstituted 5-12 membered aromatic ring, or a substituted or unsubstituted 5-12 membered aromatic heterocyclic ring;

[0039] In the compound represented by formula IV,

[0040] A is oxygen or sulfur;

[0041] G is H, substituted or unsubstituted C 1-6 Alkyl or alkoxy (preferably halogen-substituted alkyl);

[0042] Q is a substituted or unsubstituted 5-12 membered aromatic heterocycle;

[0043] In the compounds represented by formula I-VI,

[0044] A is oxygen or sulfur;

[0045] G is H, substituted or unsubstituted C 1-6 Alkyl or alkoxy (preferably halogen-substituted alkyl);

[0046] L, X, Y, Z and k are as described in claim 2.

[0047] In a preferred embodiment, the aromatic ring is a substituted or unsubstituted aromatic ring-linked aromatic ring, preferably a substituted or unsubstituted phenyl-linked phenyl ring.

[0048] In a preferred embodiment, the aromatic heterocycle is a nitrogen-containing aromatic heterocycle, a five-membered or six-membered aromatic heterocycle, a benzoaromatic heterocycle, a condensed aromatic heterocycle, an aromatic heterocycle-linked aromatic heterocycle, or an aromatic heterocycle-linked aromatic heterocycle.

[0049] In a preferred embodiment, the five-membered aromatic heterocycle includes, but is not limited to: substituted or unsubstituted oxazole, substituted or unsubstituted thiadiazole, substituted or unsubstituted oxadiazole, substituted or unsubstituted isoxazole, substituted or unsubstituted isoxazoline, substituted or unsubstituted thiophenol, substituted or unsubstituted furan;

[0050] The six-membered heterocyclic ring includes, but is not limited to, substituted or unsubstituted pyridine, substituted or unsubstituted triazine ring, substituted or unsubstituted oxadiazine;

[0051] The benzoaromatic heterocycle includes but is not limited to: benzoxazole, benzotriazole, benzoquinadione ring;

[0052] The fused aromatic heterocycle includes but is not limited to: thiazolyl pyrazole, triazolothiadiazole,;

[0053] The aromatic ring-linked aromatic heterocycle includes but is not limited to a benzo-linked aromatic heterocycle, such as benzopyrazole, benzothiazole, or benzoisoxazoline;

[0054] The aromatic heterocycle-linked aromatic heterocycle includes, but is not limited to, pyrazine bipyridine and pyridine bipyrazole.

[0055] In a specific embodiment,

[0056] In the compound represented by formula II, m is 0 or 1;

[0057] A is an oxygen atom or a sulfur atom;

[0058] G is H, substituted or unsubstituted C 1-6 Alkyl or alkoxy (preferably C 1-3 alkyl or alkoxy);

[0059] Q is a substituted or unsubstituted five-membered or six-membered aromatic heterocycle, a substituted or unsubstituted five-membered or six-membered alicyclic heterocycle, a substituted or unsubstituted 5-12-membered benzoaromatic heterocycle, a substituted or unsubstituted 5-12-membered aromatic heterocycle-linked aromatic heterocycle, or a substituted or unsubstituted 5-12-membered aromatic ring-linked aromatic ring.

[0060] In a specific embodiment,

[0061] The compound shown in formula II is a compound selected from the following:

[0062]

[0063]

[0064]

[0065]

[0066]

[0067]

[0068]

[0069]

[0070]

[0071]

[0072]

[0073] The compound represented by formula I-II is selected from the following compounds:

[0074]

[0075] The compound represented by formula I-III is selected from the following compounds:

[0076]

[0077]

[0078] The compound represented by formula I-IV is selected from the following compounds:

[0079]

[0080]

[0081]

[0082] The compound shown in formula IV is a compound selected from the following:

[0083]

[0084] The compound represented by formula I-VI is selected from the following compounds:

[0085]

[0086]

[0087] In a specific embodiment,

[0088] The compound shown in formula II is a compound selected from the following:

[0089]

[0090]

[0091]

[0092] The compound represented by formula I-III is selected from the following compounds:

[0093]

[0094] The compound represented by formula I-IV is selected from the following compounds:

[0095]

[0096]

[0097] The compound shown in formula IV is a compound selected from the following:

[0098]

[0099]

[0100] The compound represented by formula I-VI is selected from the following compounds:

[0101]

[0102] In a second aspect, the present invention provides a pesticide composition comprising the compound described in the first aspect, or its optical isomers, cis-trans isomers or pesticide-acceptable salts, and optionally a pesticide-acceptable excipient.

[0103] In a preferred embodiment, the pesticide composition is used to kill nematodes.

[0104] In a third aspect, the present invention provides the use of the compound of the first aspect, or its optical isomers, cis-trans isomers or pesticide-acceptable salts, for killing nematodes or for preparing a nematicidal pesticide composition.

[0105] In a fourth aspect, the present invention provides a method for controlling or killing nematodes, characterized in that an effective amount of the compound described in the first aspect, or its optical isomers, cis-trans isomers or pesticide-acceptable salts, or the pesticide composition described in the second aspect is administered to plants or crops that need to control or kill nematodes.

[0106] In a fifth aspect, the present invention provides a method for preparing the compound of the first aspect, characterized in that the compound is prepared by the following synthetic route:

[0107] 1) When M is a substituted or unsubstituted 5-7 membered aromatic ring, a substituted or unsubstituted 5-7 membered carbocyclic ring, a substituted or unsubstituted 5-7 membered aromatic heterocyclic ring, or a substituted or unsubstituted 5-7 membered heterocyclic ring, (CH2) m Wherein m=0-5, A=0, the preparation method is as shown in the following reaction formula:

[0108]

[0109] a) chlorinating the compound of formula 1-1 to obtain the compound of formula 1-2;

[0110] b) reacting the compound represented by formula 1-2 with a corresponding amine in the presence of a base or a condensing agent to obtain a compound represented by formula 1-3;

[0111] c) reacting the compound represented by formula 1-3 with a bromide in the presence of a base to generate a compound represented by formula 1-4;

[0112] 2) When M is a substituted or unsubstituted 5-7 membered aromatic ring, a substituted or unsubstituted 5-7 membered carbocyclic ring, a substituted or unsubstituted 5-7 membered aromatic heterocyclic ring, or a substituted or unsubstituted 5-7 membered heterocyclic ring, (CH2) m Wherein m=0-5, A=S, the preparation method is as shown in the following reaction formula:

[0113]

[0114] a) chlorinating the compound of formula 2-1 to obtain the compound of formula 2-2;

[0115] b) reacting the compound represented by formula 2-2 with the corresponding amine in the presence of a base or a condensing agent to obtain the compound represented by formula 2-3;

[0116] c) reacting the compound represented by formula 2-3 with Lawesson's reagent to generate the compound represented by formula 2-4;

[0117] d) reacting the compound represented by formula 1-3 with a bromide in the presence of a base to generate a compound represented by formula 2-4;

[0118] 3) When M=O, the following reaction formula is used to prepare the compound:

[0119]

[0120] a) reacting the compound represented by formula 3-1 with the corresponding amine in the presence of a base or a condensing agent to obtain the compound represented by formula 3-2;

[0121] b) reacting the compound of formula 3-2 with a bromide in the presence of a base to generate a compound of formula 3-3;

[0122] 4) When M=N, the following reaction formula is used for preparation:

[0123]

[0124] a) reacting the compound represented by formula 4-1 with the corresponding amine in a solvent to obtain the compound represented by formula 4-2;

[0125] b) reacting the compound represented by formula 4-2 with a bromide in the presence of a base to generate a compound represented by formula 4-3;

[0126] 5) When M=S, the following reaction formula is used for preparation:

[0127]

[0128] a) reacting the compound represented by formula 5-1 with triphosgene in a solvent to obtain the compound represented by formula 5-2;

[0129] b) reacting the compound of formula 5-2 with the corresponding thiol to generate the compound of formula 5-3;

[0130] c) reacting the compound represented by formula 5-3 with a bromide in the presence of a base to generate a compound represented by formula 5-4;

[0131] 6) When M=C=O, A=O, the following reaction formula is used for preparation:

[0132]

[0133] a) reacting the compound represented by formula 6-1 with oxalyl chloride in a solvent to obtain the compound represented by formula 6-2;

[0134] b) reacting the compound of formula 6-2 with the corresponding amine to generate the compound of formula 6-3;

[0135] c) reacting the compound represented by formula 6-3 with a bromide in the presence of a base to generate a compound represented by formula 6-4.

[0136] It should be understood that within the scope of the present invention, the above-mentioned technical features of the present invention and the technical features specifically described below (such as embodiments) can be combined with each other to form a new or preferred technical solution. Due to space limitations, they will not be described one by one here. DETAILED DESCRIPTION

[0137] After long-term and in-depth research, the inventors have designed and synthesized a series of trifluoroolefin compounds with novel structures and significant insecticidal activity. The compounds have the advantages of high efficiency, low toxicity and good environmental compatibility. On this basis, the inventors have completed the present invention.

[0138] Group Definition

[0139] The term "C 1-6 The term "alkyl" refers to a straight or branched chain alkyl group having 1 to 6 carbon atoms, such as methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-butyl, or the like.

[0140] The term "C 2-6 The term "alkenyl" refers to a straight or branched alkenyl group having 2 to 6 carbon atoms, such as vinyl, allyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, or the like.

[0141] The term "C 2-6 The term "alkynyl" refers to a straight or branched chain alkynyl group having 2 to 6 carbon atoms, such as ethynyl, propynyl, or the like.

[0142] The term "C 3-7 The term "cycloalkyl" refers to a cyclic alkyl group having 3 to 7 carbon atoms, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, or the like.

[0143] The term "C 5-7The term "cycloalkenyl" refers to a cyclic alkenyl group having 5 to 7 carbon atoms and having one or more double bonds, such as cyclopentenyl, cyclohexenyl, cycloheptenyl, 1,3-cyclohexadienyl, 1,4-cyclohexadienyl, or the like.

[0144] As used herein, the term “C 1-4 The term "alkoxy" refers to a straight or branched alkoxy group having 1 to 4 carbon atoms, for example, methoxy, ethoxy, propoxy, isopropoxy, butoxy, isobutoxy, sec-butoxy, tert-butoxy, or the like.

[0145] The term "halogen" refers to fluorine, chlorine, bromine, or iodine. The term "halogenated" refers to a group substituted by the same or different one or more halogen atoms mentioned above, for example trifluoromethyl, pentafluoroethyl, heptafluoroisopropyl, or the like.

[0146] The term "ring" or "ring system" refers to a carbocyclic or heterocyclic ring.

[0147] The term "heterocycle" means that at least one of the atoms forming the heterocycle skeleton is not carbon, but a heteroatom such as nitrogen, oxygen or sulfur. It is well known to those skilled in the art that heterocycles can be divided into two categories: aliphatic heterocycles and aromatic heterocycles; heterocycles usually contain no more than 4 nitrogen atoms, no more than 2 oxygen atoms and / or no more than 2 sulfur atoms. Unless otherwise specified, heterocycles can be saturated, partially unsaturated or fully unsaturated rings.

[0148] The term "ring system" refers to two or more rings fused together.

[0149] As used herein, the term "5-membered or 6-membered heterocyclyl" refers to a 5-membered or 6-membered ring containing one or more heteroatoms selected from nitrogen, oxygen or sulfur, for example, pyridyl, thiazolyl, isothiazolyl, thienyl, furanyl, pyrrolyl, pyrazolyl, pyrimidinyl, tetrahydrofuranyl, 4,5-dihydrothiazol-2-yl, 2-cyano-4-oxo-1,3-thiazolidin-3-yl, 2-cyano-imino-4-oxo-1,3-thiazolidin-3-yl, 2-cyano-imino- -4-oxo-1,3-thiazin-3-yl, oxazolyl, isoxazolyl, 1H-tetrazolyl, 1H-1,2,3-triazolyl, 4H-1,2,4-triazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,3,4-oxadiazolyl or tetrazolyl, etc.

[0150] The term "heterocyclic ring system" refers to a ring system in which at least one ring of the ring system is a heterocyclic ring.

[0151] The term "heteroaromatic ring system" refers to a system in which at least one ring in the ring system is aromatic.

[0152] The term "alkyl" refers to a group formed by removing one hydrogen atom from an alkane molecule; the term "alkylene" refers to a group formed by removing two hydrogen atoms from an alkane molecule. Similarly, the definitions of "alkenylene", "alkynylene", "cycloalkylene", "cycloalkenylene", "phenylene", "naphthylene", "heterocyclylene" or "heteroaromatic bicyclic or tricyclic ring system" are similar.

[0153] Unless otherwise specified as "substituted or unsubstituted", the groups of the present invention may be substituted by substituents selected from the following groups: halogen, cyano, nitro, C 1-6 Alkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Halogenated alkenyl, C 2-6 Alkynyl, C 2-6 Haloalkynyl, Hydroxyl, Hydroxyl C 1-4 Alkyl, OR', Si(R')3, NR'R", C(O)R', C(O)OR', C(O)NR'R", SR', S(O) m R', S(O)2NR'R", OC(O)R', OC(O)NR'R", OS(O)2R', OS(O)2NR'R", N(R")C(O)R', NCH2R', N(R")C(O)NR'R", N(R")S(O)2R' or N(R')S(O)2NR'R", etc.;

[0154] Wherein, R' and R" are each independently H, C 1-6 Alkyl or cycloalkyl, C 1-6 Haloalkyl, C 2-6 Alkenyl, C 2-6 Halogenated alkenyl, C 2-6 Alkynyl or C 2-6 Haloalkynyl.

[0155] Inert solvents refer to various solvents that do not react with raw materials, including various linear, branched or cyclic alcohols, ethers or ketones, halogenated alkanes, 1,4-dioxane, acetonitrile, tetrahydrofuran, N,N-dimethylformamide (DMF), dimethyl sulfoxide (DMSO) and the like.

[0156] Compounds having nematicidal activity of the present invention

[0157] The term "active substance of the present invention" or "active compound of the present invention" refers to a compound having a structure represented by the general formula (I) or an agrochemically acceptable salt thereof.

[0158] In a specific embodiment, the compound of the present invention is a compound represented by the general formula I:

[0159]

[0160] A, G, M and Q in the formula are as described above.

[0161] In a further embodiment, according to the different connecting bridges M in the general formula I, the compounds of the present invention can be divided into several different types of compounds:

[0162] When M is (CH2) m , wherein m = 0-5, to obtain amide compound II;

[0163] When M is a six-membered aromatic (hetero) ring, compound I-II is obtained. Accordingly, with the specific selection of M in formula I, the compounds of the present invention are further shown in formula I-III to formula I-VI.

[0164] The active substance of the present invention can be used to control and eliminate a wide range of parasitic nematodes of agricultural and forestry plants. In this specification, "nematicide" is a general term for substances that have the effect of controlling all plant parasitic nematodes mentioned herein.

[0165] Examples of plant parasitic nematodes include, but are not limited to, root-knot nematodes, such as Meloidogynearenaria, Meloidogyne chitwoodi, Meloidogyneexigua, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, and other Meloidogyne species; cyst nematodes, such as Globodera rostochiensis, Globodera pallida, Globodera tabacum, and other Globodera species; heterodermal nematodes, such as Heterodera avenae, Heterodera spp. glycines), beet cyst nematode (Heteroderaschachtii), clover cyst nematode (Heterodera trifolii), and other Heterodera species; seed nematodes, such as Anguina funesta, Anguina tritici, and other Anguina species; stem and leaf bud nematodes, such as Aphelenchoides besseyi, Aphelenchoides fragariae, Aphelenchoides ritzemabosi, and other Aphelenchoides species; thorn nematodes, such as Belonolaimus longicaudatus and other Belonolaimus species; pine nematodes, such as Bursaphelenchus xylophilus xylophilus and other Bursaphelenchus; ring nematodes, such as Criconema, Criconemella, Criconemoides, and Mesocriconema; bulb nematodes, such as Ditylenchus destructor, Ditylenchus dipsaci, Ditylenchus myceliophagus, and other Ditylenchus;Cone nematodes, such as Dolichodorus; spiral nematodes, such as Helicotylenchus dihystera, Helicotylenchus multicintus, and other Helicotylenchus; sheath nematodes, such as Hemicycliophora and Hemicriconemoides; crown nematodes, such as Hoploaimus columbus and other Hoploaimus; pseudorhizobium nematodes, such as Nacobbus aberrans and other Nacobbus; needle nematodes, such as Longidorus elongatus and other Longidorus species; nail nematodes, such as Paratylenchus; root rot nematodes, such as Pratylenchus brachyurus, Pratylenchus coffee, Pratylenchus zeae, Pratylenchus penetrans, and other Pratylenchus species; boring nematodes, such as Radopholus similis and other Radopholus species; reniform nematodes, such as Rotylenchus robustus and other Rotylenchus species; stump nematodes, such as Trichodorus rufipogonus and other primitivus and other Trichodorus; dwarf nematodes such as Tylenchorhynchus claytoni, Tylenchorhynchus dubius, and other Tylenchorhynchus; citrus nematodes such as Tylenchulus semipipenetrans and other Tylenchulus; Xiphinema such as Xiphinema americanum, Xiphinema index, Xiphinema diversicaudatum, and other Xiphinema.

[0166] The compound of the present invention has a good control effect on the southern root-knot nematode (Meloidogyne incognita).

[0167] Nematicide composition containing the active substance of the present invention

[0168] The active substances of the present invention can be prepared into nematicide compositions by conventional methods. These active compounds can be made into conventional formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, natural and synthetic materials impregnated with active substances, microcapsules in polymers, coating compounds for seeds, and formulations for use with combustion devices, such as fumigation cartridges, fumigation pots and fumigation trays, and ULV cold mist and hot mist formulations.

[0169] These preparations can be produced in a known manner, for example by mixing the active compound with an extender, i.e. a liquid, liquefied gas or solid diluent or carrier and optionally a surfactant, i.e. an emulsifier and / or dispersant and / or foam former. For example, when water is used as the extender, an organic solvent can also be used as an auxiliary agent.

[0170] When a liquid solvent is used as a diluent or carrier, it is basically suitable, such as: aromatic hydrocarbons, for example xylene, toluene or alkylnaphthalene; chlorinated aromatic or chlorinated aliphatic hydrocarbons, for example chlorobenzene, vinyl chloride or methylene chloride; aliphatic hydrocarbons, for example cyclohexane or paraffins, for example mineral oil fractions; alcohols, for example ethanol or ethylene glycol and their ethers and lipids; ketones, for example acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; or unusual polar solvents, for example dimethylformamide and dimethyl sulfoxide, and water.

[0171] A diluent or carrier for liquefied gas refers to a liquid that will become a gas at normal temperature and pressure, such as an aerosol propellant, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.

[0172] Solid carriers can be ground natural minerals, such as kaolin, clay, talc, quartz, atavistic clay, montmorillonite, or diatomaceous earth; and ground synthetic minerals, such as highly dispersed silicic acid, alumina and silicates. Solid carriers for particles are ground and classified natural zircons, such as calcite, marble, pumice, sepiolite and dolomite, and inorganic and organic coarse powders and particles of organic materials such as sawdust, coconut shells, corn cobs and tobacco stems.

[0173] Nonionic and anionic emulsifiers can be used as emulsifiers and / or foam formers. For example, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, such as alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and albumin hydrolysates. Dispersants include lignin sulfite waste liquor and methylcellulose.

[0174] Binders such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or emulsions, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, may be used in the formulation.

[0175] Colorants such as inorganic dyes, such as iron oxide, cobalt oxide and Prussian blue; organic dyes, such as azo dyes or metal phthalocyanine dyes; and trace nutrients, such as salts of iron, manganese, boron, copper, cobalt, aluminum and zinc, etc. may be used.

[0176] The active compounds of the present invention may be mixed with other active compounds in their commercial preparations or in the use formulations prepared from these preparations, and these other active compounds are insecticides, bactericides, fungicides, herbicides, growth control agents, etc. Insecticides include, for example, phosphates, carbamates, chlorinated hydrocarbons, and substances produced by microorganisms, such as avermectin, etc., and fungicides include strobilurins, amides, triazoles, etc.

[0177] In addition, the active compounds of the present invention may also be mixed with synergists in their commercial preparations or dosage forms prepared from these preparations. These synergists are compounds that enhance the effects of the active compounds. Since the active compounds themselves are active, it is not necessary to add synergists.

[0178] These preparations usually contain 0.001-99.99% by weight, preferably 0.01-99.9% by weight, more preferably 0.05-90% by weight of the active compound of the present invention, based on the total weight of the nematicidal composition. The concentration of the active compound in the commercial preparations or use forms may vary over a wide range. The concentration of the active compound in the use form may be from 0.0000001 to 100% (g / v), preferably between 0.0001 and 1% (g / v).

[0179] Preparation method of the compound of the present invention

[0180] The compound shown in the general formula of the present invention can be prepared by the following method, but the conditions of the method, such as the amount of reactants, solvents, alkalis, compounds used, reaction temperature, reaction time required, etc. are not limited to the following explanation. The compounds of the present invention can also be prepared conveniently by combining various synthetic methods described in this specification or known in the art, and such a combination can be easily carried out by a technician in the field to which the present invention belongs. If feasible, the reagent can be purchased through commercial channels.

[0181] Typical embodiments of the compounds of the present invention can be synthesized using the following general reaction schemes. It is apparent from the description given herein that the general scheme can be changed by replacing with other materials with similar structures to obtain corresponding different products. The synthetic method can provide a large amount of production as required. The raw materials can be obtained by commercial methods or synthesized using disclosed methods. The examples given herein, through simple inspection steps, the characteristics of the final product usually make the characteristics of the necessary raw materials obvious.

[0182] Synthesis reaction parameters can use, for example, the following general methods and procedures to prepare compounds of the present invention from readily available starting materials. It will be appreciated that other process conditions may also be used where typical or optimized process conditions (i.e., reaction temperature, time, molar ratio of reactants, solvent, catalyst, pressure, etc.) are given, unless otherwise noted. Optimum reaction conditions may vary with specific reactants or solvents used, but such conditions may be determined by conventional optimization procedures by those skilled in the art.

[0183] The starting materials for the following reactions are generally known compounds or can be prepared by known procedures or obvious modifications thereof. For example, many starting materials can be obtained from commercial suppliers, and others can be prepared by procedures described in standard reference texts or obvious modifications thereof.

[0184] In the preparation method of the present invention, each reaction is usually carried out in an inert solvent at a reaction temperature of -20 to 120°C (preferably -10 to 0°C or 20 to 30°C or 80 to 100°C). The reaction time is usually 2 to 24 hours, preferably 4 to 18 hours, and the reaction time can be appropriately extended according to the reaction requirements. The specific reaction time is determined according to the degree of reaction.

[0185] The base used in the reaction includes (but is not limited to): triethylamine, pyridine, diisopropylethylamine, diethylamine, piperidine, piperazine, morpholine, N-methylmorpholine, triethylenediamine (DABCO), 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU), 1,5-diazabicyclo[4.3.0]non-5-ene (DBN), potassium carbonate, potassium bicarbonate, sodium carbonate, sodium bicarbonate, cesium carbonate, sodium hydroxide, potassium hydroxide, sodium methoxide, sodium ethoxide, or a combination thereof.

[0186] The condensing agent used in the reaction includes (but is not limited to): 4-dimethylaminopyridine (4-DMAP, PyBop), diphenylphosphoryl azide (DPPA), dicyclohexylcarbodiimide (DCC), HATU, diphenylphosphinyl chloride (DPP-Cl).

[0187] Synthesis route:

[0188] 1. When M is a substituted or unsubstituted 5-7 membered aromatic ring, a substituted or unsubstituted 5-7 membered carbocyclic ring, a substituted or unsubstituted 5-7 membered aromatic heterocyclic ring, or a substituted or unsubstituted 5-7 membered heterocyclic ring, (CH2) m When m=0-5 and A=0, the method in Scheme 1 is adopted.

[0189]

[0190] In scheme 1, 1-1 is chlorinated and then reacted with a corresponding amine in the presence of a base or a condensing agent to give 1-3.

[0191] When M is a substituted or unsubstituted 5-7 membered aromatic ring, a substituted or unsubstituted 5-7 membered carbon ring, a substituted or unsubstituted 5-7 membered aromatic heterocycle, or a substituted or unsubstituted 5-7 membered heterocycle, (CH2) m When m=0-5 and A=S, the method in Scheme 2 is adopted.

[0192] Option 2:

[0193]

[0194] a) chlorinating the compound of formula 2-1 to obtain the compound of formula 2-2;

[0195] b) reacting the compound represented by formula 2-2 with the corresponding amine in the presence of a base or a condensing agent to obtain the compound represented by formula 2-3;

[0196] c) reacting the compound represented by formula 2-3 with Lawesson's reagent to generate the compound represented by formula 2-4;

[0197] When M=O, the method in scheme 3 is adopted.

[0198] Option 3:

[0199]

[0200] a) reacting the compound represented by formula 3-1 with the corresponding amine in the presence of a base or a condensing agent to obtain the compound represented by formula 3-2;

[0201] b) reacting the compound of formula 3-2 with a bromide in the presence of a base to generate a compound of formula 3-3;

[0202] When M=N, the method in scheme 4 is adopted.

[0203] Option 4:

[0204]

[0205] a) reacting the compound represented by formula 4-1 with the corresponding amine in a solvent to obtain the compound represented by formula 4-2;

[0206] b) reacting the compound represented by formula 4-2 with a bromide in the presence of a base to generate a compound represented by formula 4-3;

[0207] When M=S, the method in scheme 5 is adopted.

[0208] Option 5:

[0209]

[0210] a) reacting the compound represented by formula 5-1 with triphosgene in a solvent to obtain the compound represented by formula 5-2;

[0211] b) reacting the compound of formula 5-2 with the corresponding thiol to generate the compound of formula 5-3;

[0212] c) reacting the compound represented by formula 5-3 with a bromide in the presence of a base to generate a compound represented by formula 5-4;

[0213] When M=C=O, A=O, adopt the method in scheme 6:

[0214] Option 6:

[0215]

[0216] a) reacting the compound represented by formula 6-1 with oxalyl chloride in a solvent to obtain the compound represented by formula 6-2;

[0217] b) reacting the compound of formula 6-2 with the corresponding amine to generate the compound of formula 6-3;

[0218] c) reacting the compound represented by formula 6-3 with a bromide in the presence of a base to generate a compound represented by formula 6-4;

[0219] Synthesis Example

[0220] 1. Preparation of Compound II

[0221] Take the preparation of II-2N-(3,4,4-trifluorobutyl-3-en-1-yl)-2-(trifluoromethyl)benzamide and II-49N-(3,4,4-trifluorobutyl-3-en-1-yl)-2-(trifluoromethyl)benzamide as examples.

[0222] (1) Preparation of intermediate II-2.

[0223] Synthesis of 2-(trifluoromethyl)benzoyl chloride.

[0224]

[0225] 2-(trifluoromethyl)benzoic acid 2mmol, dichloromethane 15mL are added to a 50mL single-mouth bottle, 2.5mmol oxalyl chloride dichloromethane solution is added dropwise in an ice bath, and 0.05mL DMF is added after the addition is complete. Stir at room temperature for 3h. After the reaction is completed, dichloromethane is distilled off to obtain crude 2-(trifluoromethyl)benzoyl chloride with a yield of 91%. It is directly used for the next step without purification.

[0226] Synthesis of 3,4,4-trifluorobutyl-3-en-1-amine

[0227]

[0228] Potassium phthalimide (30 mmol) and 4-bromo-1,1,2-trifluorobutene (20 mmol) were added to a 250 ml round-bottom flask, stirred and heated to 80°C for reaction. After the reaction was completed, the mixture was cooled to room temperature, MeCN was removed under reduced pressure, extracted with dichloromethane, the organic layers were combined, dried over anhydrous Na2SO4, and column chromatography was performed to obtain 2-(3,4,4-trifluoro-3-ene-1-yl)isoindoline-1,3-dione with a yield of 60%.

[0229] 2-(3,4,4-trifluoro-3-ene-1-yl)isoindoline-1,3-dione (6mmol), hydrazine hydrate (12mmol), and ethanol (35ml) were added to a 100ml round-bottom flask, stirred and heated to 78°C for 7h. After the reaction was completed, the reaction solution was ice-bathed to precipitate a white solid, namely 2,3-dihydrophthalazine-1,4-dione. 2,3-dihydrophthalazine-1,4-dione was removed by suction filtration. Ethanol was removed under reduced pressure to obtain a mixture of 2,3-dihydrophthalazine-1,4-dione and 3,4,4-trifluoro-3-ene-1-amine with a yield of 50%, which was directly used in the next step without purification.

[0230] (2) Preparation of II-2.

[0231]

[0232] 3,4,4-trifluoro-3-ene-1-amine 3mmol, 2-(trifluoromethyl)benzoyl chloride 3mmol, triethylamine 4.5mmol, dichloromethane 20mL, added to a single-mouth bottle, stirred at room temperature for reaction. TLC tracking, after the reaction is completed, the solvent is removed under reduced pressure, saturated ammonium chloride aqueous solution 30mL is added to the residue, dichloromethane (15mL×3) is extracted, the organic phases are combined, dried over anhydrous sodium sulfate, filtered, the filtrate is collected and concentrated, and the pure product N-(3,4,4-trifluorobutyl-3-ene-1-yl)-2-(trifluoromethyl)benzamide is obtained by petroleum ether ethyl acetate column chromatography.

[0233] (2) Preparation of II-49.

[0234]

[0235] 3mmol of N-(3,4,4-trifluorobutyl-3-en-1-yl)-2-(trifluoromethyl)benzamide, 3mmol of Lawesson's reagent, and 20mL of tetrahydrofuran were added to a single-mouth bottle and refluxed for reaction. TLC tracking, after the reaction was completed, the solvent was removed under reduced pressure, 30mL of saturated aqueous ammonium chloride solution was added to the residue, and dichloromethane (15mL×3) was used for extraction. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was collected and concentrated. The pure product N-(3,4,4-trifluorobutyl-3-en-1-yl)-2-(trifluoromethyl)benzamide was obtained by petroleum ether ethyl acetate column chromatography.

[0236] 2. Preparation of Compound I-II

[0237] Take the preparation of I-II-1 phenyl (3,4,4-trifluoro-3-en-1-yl) carbamate as an example.

[0238] (1) Preparation of intermediate I-II-1.

[0239] The synthesis of 3,4,4-trifluorobutyl-3-en-1-amine is the same as in Example 1.

[0240] (2) Preparation of I-II-1.

[0241]

[0242] 3,4,4-trifluoro-3-en-1-amine 3mmol, phenyl chloroformate 3mmol, pyridine 10mL, heated to 50℃ and stirred for reaction. TLC tracking, after the reaction is completed, the solvent is removed under reduced pressure, saturated ammonium chloride aqueous solution 30mL is added to the residue, and dichloromethane (15mL×3) is used for extraction, the organic phases are combined, dried over anhydrous sodium sulfate, filtered, the filtrate is collected and concentrated, and the pure product phenyl (3,4,4-trifluoro-3-en-1-yl) carbamate is obtained by petroleum ether ethyl acetate column chromatography.

[0243] 3. Preparation of Compounds I-III

[0244] Take the preparation of I-III-11-phenyl-3-(3,4,4-trifluoro-3-en-1-yl)urea as an example.

[0245]

[0246] 3,4,4-trifluoro-3-ene-1-amine 3mmol, isocyanate benzene 3mmol, dichloromethane 20mL, stirred at room temperature for reaction. TLC tracking, after the reaction is completed, the solvent is removed under reduced pressure, saturated ammonium chloride aqueous solution 30mL is added to the residue, dichloromethane (15mL×3) is used for extraction, the organic phases are combined, dried over anhydrous sodium sulfate, filtered, the filtrate is collected and concentrated, and the pure product 1-phenyl-3-(3,4,4-trifluoro-3-ene-1-yl)urea is obtained by petroleum ether ethyl acetate column chromatography.

[0247] 4. Preparation of Compounds I-IV

[0248] Take I-IV-1S-phenyl(3,4,4-trifluoro-3-en-1-yl)carbamate as an example.

[0249] Synthesis of 1,1,2-trifluoro-4-isocyanate butene.

[0250]

[0251] 5 mmol of 3,4,4-trifluoro-3-ene-1-amine, 10 mmol of triphosgene, and 30 mL of toluene were heated to reflux for reaction. TLC was used for tracking. After the reaction was completed, the solvent was removed under reduced pressure, 30 mL of saturated aqueous ammonium chloride solution was added to the residue, and dichloromethane (15 mL×3) was used for extraction. The organic phases were combined, dried, and the solvent was dried to obtain the crude product 1,1,2-trifluoro-4-isocyanate butene, which was directly used for the next step without purification.

[0252] (2) Preparation of I-IV-1.

[0253]

[0254] 3mmol of 1,1,2-trifluoro-4-isocyanate butene, 3mmol of thiophenol, and 20mL of dichloromethane were stirred at room temperature for reaction. TLC tracking, after the reaction was completed, the solvent was removed under reduced pressure, 30mL of saturated aqueous ammonium chloride solution was added to the residue, and dichloromethane (15mL×3) was used for extraction. The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was collected and concentrated. The pure product S-phenyl (3,4,4-trifluoro-3-en-1-yl) carbamate was obtained by petroleum ether ethyl acetate column chromatography.

[0255] 5. Preparation of IV compound

[0256] Taking IV-1 2-oxo-2-phenyl-N-(3,4,4-trifluoro-3-en-1-yl)acetamide as an example

[0257] (1) Preparation of intermediate IV-1.

[0258] Synthesis of 2-oxo-2-phenylacetyl chloride.

[0259]

[0260] 2-Oxo-2-phenylacetic acid 2mmol, dichloromethane 15mL were added to a 50mL single-mouth bottle, and a dichloromethane solution of 2.5mmol oxalyl chloride was added dropwise in an ice bath, and 0.05mL DMF was added after the addition was complete. Stir at room temperature for 3h. After the reaction was completed, dichloromethane was removed by distillation to obtain crude 2-oxo-2-phenylacetyl chloride with a yield of 91%. It was directly used for the next step without purification.

[0261] (2) Preparation of IV-1.

[0262]

[0263] 3,4,4-trifluoro-3-en-1-amine 3mmol, 2-oxo-2-phenylacetyl chloride 3mmol, triethylamine 4.5mmol, dichloromethane 20mL, added to a single-mouth bottle, stirred at room temperature for reaction. TLC tracking, after the reaction is completed, the solvent is removed under reduced pressure, saturated ammonium chloride aqueous solution 30mL is added to the residue, dichloromethane (15mL×3) is extracted, the organic phases are combined, dried over anhydrous sodium sulfate, filtered, the filtrate is collected and concentrated, and the pure product 2-oxo-2-phenyl-N-(3,4,4-trifluoro-3-en-1-yl)acetamide is obtained by petroleum ether ethyl acetate column chromatography.

[0264] 6. Preparation of I-VI compounds

[0265] Take I-VI-1 3-phenyl-N-(3,4,4-trifluoro-3-en-1-yl)-4,5-dihydroisoxazole-5-carboxamide as an example.

[0266] (1) Preparation of I-VI-2 intermediate.

[0267] Synthesis of (Z)-N-hydroxybenzimidoyl chloride.

[0268]

[0269] Add 5 mmol of (E)-benzaldehyde oxime and 2 drops of hydrochloric acid into a 100 mL single-necked bottle containing 30 mL of dichloromethane, and then add 6 mmol of NCS solution in dichloromethane. Stir the mixture at room temperature and track the reaction by TLC. After the reaction is completed, the solvent is dried to obtain the crude product of (Z)-N-hydroxybenzimidoyl chloride, which is directly used in the next step without purification.

[0270] Synthesis of 3-hydroxypropyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate.

[0271]

[0272] 5mmol of 2-hydroxyethyl acrylate was added to a dichloromethane solution containing 8mmol of (Z)-N-hydroxybenzanilide chloride, and a dichloromethane solution containing 8mmol of triethylamine was added dropwise, and the reaction was stirred at room temperature. TLC tracking, after the reaction was completed, the solvent was removed under reduced pressure, 30mL of saturated ammonium chloride aqueous solution was added to the residue, and dichloromethane (15mL×3) was used for extraction, the organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was collected and concentrated, and the pure product 3-hydroxypropyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate was obtained by petroleum ether ethyl acetate column chromatography.

[0273] Synthesis of 3-phenyl-4,5-dihydroisoxazole-5-carboxylic acid.

[0274]

[0275] 10 mmol of 3-hydroxypropyl 3-phenyl-4,5-dihydroisoxazole-5-carboxylate and 25 mL of 1 mol / L sodium hydroxide solution were added into a 100 mL single-necked bottle containing 25 mL of ethanol. The mixture was stirred at room temperature for reaction and tested by TLC. After the reaction was completed, aqueous hydrochloric acid solution was added to make the solution acidic. At this time, a white solid was precipitated and filtered to obtain pure 3-phenyl-4,5-dihydroisoxazole-5-carboxylic acid.

[0276] Synthesis of 3-phenyl-4,5-dihydroisoxazole-5-yl chloride

[0277]

[0278] 2mmol of 3-phenyl-4,5-dihydroisoxazole-5-carboxylic acid and 15mL of dichloromethane were added to a 50mL single-mouth bottle, and a dichloromethane solution of 2.5mmol of oxalyl chloride was added dropwise in an ice bath. After the addition was complete, 0.05mL of DMF was added. Stir at room temperature for 3h. After the reaction was completed, dichloromethane was removed by distillation to obtain a crude product of 3-phenyl-4,5-dihydroisoxazole-5-carboxylic acid chloride with a yield of 91%. It was directly used for the next step without purification.

[0279] (2) Preparation of I-VI-1.

[0280]

[0281] 3,4,4-trifluoro-3-ene-1-amine 3mmol, 3-phenyl-4,5-dihydroisoxazole-5-yl chloride 3mmol, triethylamine 4.5mmol, dichloromethane 20mL, added to a single-mouth bottle, stirred at room temperature for reaction. TLC tracking, after the reaction is completed, the solvent is removed under reduced pressure, saturated ammonium chloride aqueous solution 30mL is added to the residue, dichloromethane (15mL×3) is extracted, the organic phases are combined, dried over anhydrous sodium sulfate, filtered, the filtrate is collected and concentrated, and the pure product 3-phenyl-N-(3,4,4-trifluoro-3-ene-1-yl)-4,5-dihydroisoxazole-5-carboxamide is obtained by petroleum ether ethyl acetate column chromatography.

[0282] NMR data of target compound:

[0283] Table 1: NMR data of compound II

[0284]

[0285]

[0286]

[0287]

[0288]

[0289] Table 2: NMR data of compound I-II:

[0290]

[0291]

[0292] Table 3: NMR data of compounds I-III:

[0293]

[0294]

[0295] Table 4: NMR data of compounds I-IV:

[0296]

[0297]

[0298] Table 5: NMR data of compound IV:

[0299]

[0300]

[0301] Table 6: NMR data of compounds I-VI:

[0302]

[0303]

[0304] Test Example. Nematicidal activity test of the compounds of the present invention

[0305] Root-knot nematodes belong to the phylum Nematoda, order Tylenchida, suborder Tylenchida, superfamily Heteroderidea, subfamily Meloidogyninae, and genus Meloidogyne. They are a serious plant parasitic nematode.

[0306] Live activity

[0307] The southern root-knot nematode (Meloidogyne incognita) was used as the test object, cucumber seedlings were used as the test host, and the test was carried out using the test tube planting method.

[0308] Operation process: Prepare the sample to be tested into a liquid medicine according to the required concentration and prepare a sufficient amount of second-instar larvae of root-knot nematodes. After planting one-week-old cucumber seedlings in test tubes, add an appropriate amount of prepared liquid medicine to the test tubes, and inoculate about 2,000 larvae into each test tube. The test tubes are placed at 20-25°C and cultured under 10 hours of light. After 45 days, the results are investigated and the number of root knots on the roots of each plant is counted. Each sample is tested 3 times, and each sample is treated 4 times in each test.

[0309] Distilled water was used as blank control, distilled water plus root-knot nematodes was used as negative control, and avermectin solution was used as positive control.

[0310]

[0311] In vivo nematicidal activity of compounds:

[0312] Table 7: In vivo activity of compound II:

[0313]

[0314]

[0315]

[0316]

[0317]

[0318]

[0319] Table 8: In vivo activity of compounds I-II

[0320]

[0321]

[0322] Table 9: In vivo activity of compounds I-III

[0323]

[0324]

[0325]

[0326] Table 10: In vivo activity of compounds I-IV

[0327]

[0328]

[0329] Table 11: In vivo activity of compound IV

[0330]

[0331]

[0332]

[0333] Table 12: In vivo activities of compounds I-VI

[0334]

[0335]

[0336] All documents mentioned in the present invention are cited as references in this application, just as each document is cited as reference individually. In addition, it should be understood that after reading the above teachings of the present invention, those skilled in the art can make various changes or modifications to the present invention, and these equivalent forms also fall within the scope defined by the claims attached to this application.

Claims

1. The compound represented by formula II, or its optical isomers, cis-trans isomers or pesticide-acceptable salts: The compound shown in formula II is a compound selected from the following:

2. A pesticide composition comprising the compound according to claim 1, or its optical isomers, cis-trans isomers or pesticide-acceptable salts, and optionally a pesticide-acceptable excipient.

3. Use of the compound according to claim 1, or its optical isomers, cis-trans isomers or pesticide-acceptable salts thereof, for killing nematodes or for preparing a nematicidal pesticide composition.

4. A method for controlling or killing nematodes, characterized in that: An effective amount of the compound according to claim 1, or its optical isomers, cis-trans isomers or pesticide-acceptable salts, or the pesticide composition according to claim 2 is administered to plants or crops that need to control or kill nematodes.

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