Piperidine compound, and preparation method therefor, composition thereof and use thereof

Abstract

The present invention belongs to the technical field of pesticides, and specifically relates to a piperidine compound, and a preparation method therefor, a composition thereof and the use thereof. The compound is represented by general formula I, wherein M1, M2, M3, M4 and M5 each independently represent CR or N; X represents O or NR8; Y1, Y2, Y3 and Y4 each independently represent hydrogen, halogen, alkyl or haloalkyl; R1 represents hydrogen, halogen, etc.; each R2 independently represents hydrogen, halogen, nitro, cyano, etc.; each R independently represents hydrogen, halogen, nitro, etc.; and R8 represents hydrogen, alkyl or haloalkyl. The compound exhibits an excellent control effect on various species of nematodes, such as Bursaphelenchus xylophilus and second-stage juveniles of root-knot nematodes.

Description

A piperidine compound, its preparation method, composition and application Technical Field

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

[0002] Nematodes are tiny, worm-like, multicellular animals adapted to aquatic life. The number of nematode species is estimated to be half a million. As an important part of the soil fauna, nematodes live in labyrinths formed by interconnected pathways called pores, which are created by soil processes. Direct feeding by nematodes can severely reduce the nutrient and water uptake of plants. Current nematode control primarily focuses on preventing nematode attacks on plants. Once a plant is parasitized, killing the nematodes without damaging the plant is practically impossible. Therefore, providing nematode control compounds and methods for treating plants to prevent or reduce nematode damage is beneficial. Summary of the Invention

[0003] To address the aforementioned problems in the prior art, this invention provides a piperidine compound, its preparation method, composition, and application, wherein the compound exhibits excellent control effects against different types of nematodes.

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

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

[0006] Among them, M1, M2, M3, M4, and M5 independently represent CR or N;

[0007] X represents O or NR8;

[0008] Y1, Y2, Y3, and Y4 each independently represent hydrogen, halogen, alkyl, or haloalkyl;

[0009] R1 represents hydrogen, halogen, -N(R) 21 2. Alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl or -OR 21 ;

[0010] R2 represents hydrogen, halogen, nitro, cyano, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-OR 21 ,-alkylene-OR 21 -(CO)R 21 or-(CO)OR 21 ;

[0011] R can independently represent hydrogen, halogen, nitro, cyano, thiocyano, alkyl, alkenyl, ynyl, cycloalkyl, cycloalkenyl, heterocyclic, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-(SO2)N(R 21 )2、-OR 21 -(CO)R 21 -(CO)SR 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -O(CO)OR 21 -CR 21 =N-OR 21 -C(N(R) 21 )2)=N-OR 21 or-(CO)OR 21 The "alkyl", "alkenyl" or "alkynyl" is optionally selected from halogen, nitro, cyano, cycloalkyl, cycloalkenyl, heterocyclic, aryl or -OR 21 At least one group in it is replaced;

[0012] R8 represents hydrogen, alkyl, or haloalkyl;

[0013] R 21 Each of these groups independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclic or heterocyclic alkyl, wherein the "alkyl", "alkenyl" or "alkynyl" group is optionally substituted by at least one group selected from halogen, cyano, alkoxy or haloalkoxy.

[0014] The aforementioned "cycloalkyl", "cycloalkenyl", "heterocyclic" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 At least one group in )2 is replaced;

[0015] R 10 Each can be independently represented by hydrogen, alkyl, or haloalkyl.

[0016] In one specific embodiment, Y1, Y2, Y3, and Y4 independently represent hydrogen, halogen, C1-C8 alkyl, or halo-C1-C8 alkyl, respectively.

[0017] R1 represents hydrogen, halogen, -N(R) 21 2. C1-C8 alkyl, halo-C1-C8 alkyl, C2-C8 alkyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl or -OR 21 ;

[0018] R2 represents hydrogen, halogen, nitro, cyano, C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 ynyl, halogenated C2-C8 ynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-OR 21 -(C1-C8 alkylene)-OR 21 -(CO)R 21 or-(CO)OR 21 ;

[0019] R can independently represent hydrogen, halogen, nitro, cyano, thiocyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-(SO2)N(R 21 )2、-OR 21 -(CO)SR 21 -(CO)R 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -O(CO)OR 21 -CR 21 =N-OR 21 -C(N(R) 21 )2)=N-OR 21 or-(CO)OR 21 The "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally selected from halogen, nitro, cyano, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic, aryl or -OR 21 At least one group in it is replaced;

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

[0021] R 21 Each of these groups independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, aryl, aryl C1-C8 alkyl, heterocyclic or heterocyclic C1-C8 alkyl, wherein the “C1-C8 alkyl”, “C2-C8 alkenyl” or “C2-C8 alkynyl” is optionally substituted by at least one group selected from halogen, cyano, C1-C8 alkoxy or haloC1-C8 alkoxy;

[0022] The aforementioned “C3-C8 cycloalkyl,” “C3-C8 cycloalkenyl,” “heterocyclic,” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 ynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 At least one group in )2 is replaced;

[0023] R 10 Each of these can be independently represented as hydrogen, C1-C8 alkyl, or halo-C1-C8 alkyl.

[0024] In one specific embodiment, Y1, Y2, Y3, and Y4 independently represent hydrogen, halogen, C1-C6 alkyl, or halogenated C1-C6 alkyl, respectively.

[0025] R1 represents hydrogen, halogen, -N(R) 21 2. C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl or -OR 21 ;

[0026] R2 represents hydrogen, halogen, nitro, cyano, C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 ynyl, halogenated C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-OR 21 -(C1-C6 alkylene)-OR 21 -(CO)R 21or-(CO)OR 21 ;

[0027] R can independently represent hydrogen, halogen, nitro, cyano, thiocyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-(SO2)N(R 21 )2、-OR 21 -(CO)SR 21 -(CO)R 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -O(CO)OR 21 -CR 21 =N-OR 21 -C(N(R) 21 )2)=N-OR 21 or-(CO)OR 21 The "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally selected from halogen, nitro, cyano, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl or -OR 21 At least one group in it is replaced;

[0028] R8 represents hydrogen, C1-C6 alkyl, or halo-C1-C6 alkyl;

[0029] R 21 Each of these groups independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, aryl, aryl C1-C6 alkyl, heterocyclic or heterocyclic C1-C6 alkyl, wherein the “C1-C6 alkyl”, “C2-C6 alkenyl” or “C2-C6 alkynyl” is optionally substituted by at least one group selected from halogen, cyano, C1-C6 alkoxy or haloC1-C6 alkoxy;

[0030] The aforementioned “C3-C6 cycloalkyl,” “C3-C6 cycloalkenyl,” “heterocyclic,” or “aryl” is optionally selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 At least one group in )2 is replaced;

[0031] R 10 Each of these can be independently represented as hydrogen, C1-C6 alkyl, or halo-C1-C6 alkyl.

[0032] In the definitions of compounds shown in the above general formulas and in all the following structural formulas, the technical terms used, whether alone or in compound terms, represent the following substituents: alkyl groups having more than two carbon atoms can be straight-chain or branched. For example, in the compound term "cycloalkylalkyl," the alkyl group can be -CH2-, -CH2CH2-, -CH(CH3)-, -C(CH3)2-, etc. The alkyl group is, for example, C1 alkyl-methyl; C2 alkyl-ethyl; C3 alkyl-propyl such as n-propyl or isopropyl; C4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl, or 2-butyl; C5 alkyl-pentyl such as n-pentyl; C6 alkyl-hexyl such as n-hexyl, isohexyl, and 1,3-dimethylbutyl. Similarly, alkenyl groups are, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl, and 1-methylbut-2-en-1-yl. Alkynyl groups are, for example, ethynyl, propynyl, but-2-yn-1-yl, but-3-yn-1-yl, and 1-methylbut-3-yn-1-yl. Multiple bonds can be in any position in each unsaturated group. Cycloalkyl groups are carbocyclic saturated ring systems having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl, or cyclohexyl. Similarly, cycloalkenyl groups are monocyclic alkenyl groups having, for example, three to six carbon ring members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl, and cyclohexenyl, wherein double bonds can be in any position. Halogens are fluorine, chlorine, bromine, or iodine.

[0033] Unless otherwise specified, the term "aryl" in this invention includes, but is not limited to, phenyl, naphthyl, and... The "heterocyclic group" includes, but is not limited to, saturated or unsaturated non-aromatic cyclic groups. And, including but not limited to, heteroaryl groups, i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms and optionally fused with benzo[a] rings, wherein 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms are selected from oxygen, nitrogen, and sulfur, for example

[0034] The terms "optional" or "optionally" mean that the event or situation described below may or may not occur, and the description includes instances where said event or situation occurs and instances where said event or situation does not occur. For example, the term "optionally...substituted" means that the specified atom or group is unsubstituted or substituted by one or more substituents. If a group is substituted by a group, this should be understood to mean that the group is substituted by one or more groups, either the same or different, selected from those groups mentioned. Furthermore, the same or different substitution characters contained in the same or different substituents are chosen independently and may be the same or different. This also applies to ring systems formed from different atoms and units. Meanwhile, the scope of the claims excludes compounds that are chemically unstable under standard conditions, as known to those skilled in the art.

[0035] Furthermore, unless otherwise specified, the phrase "replaced by at least one group" in this invention refers to being replaced by, for example, 1, 2, 3, 4, or 5 groups; groups without specific attachment positions (including heterocyclic groups, aryl groups, etc.) can be attached at any position, including positions attached to C or N; if it is substituted, the substituent can also be substituted at any position, as long as it conforms to the rules of chemical bond attachment. For example, a heteroaryl group substituted by one methyl group. Can represent wait.

[0036] Compounds of Formula I, in their respective free or salt forms, and where appropriate, their tautomers, may exist as one of the possible isomers or as mixtures thereof, for example, as pure isomers, such as enantiomers and / or diastereomers, or as mixtures of isomers, such as mixtures of enantiomers, such as racemic mixtures, diastereomer mixtures, or racemic mixtures, depending on the number of asymmetric carbon atoms present in the molecule, their absolute and relative configurations, and / or on the configuration of the non-aromatic double bonds present in the molecule; the present invention relates to these pure isomers and also to all possible mixtures of isomers and should be understood in this sense in each of the above and below, even if stereochemical details are not specifically mentioned in each case. The present invention therefore covers all such isomers and tautomers and mixtures thereof in all proportions, together with isotopic forms, such as deuterated compounds.

[0037] The present invention also covers salts or N-oxides of each compound having chemical formula I.

[0038] Those skilled in the art also understand that salts possess biological benefits in their non-salt forms because the salts of compounds are in equilibrium with their corresponding non-salt forms in the environment and under physiological conditions. Salts permissible in agriculture and / or physiology include acid addition salts formed with inorganic or organic acids such as hydrobromic acid, hydrochloric acid, nitric acid, phosphoric acid, sulfuric acid, acetic acid, butyric acid, fumaric acid, lactic acid, maleic acid, malonic acid, oxalic acid, propionic acid, salicylic acid, tartaric acid, 4-toluenesulfonic acid, or valeric acid. Suitable salts for agricultural and / or physiological purposes may also be cationic salts, particularly suitable cations are alkali metal ions including sodium, potassium and lithium, alkaline earth metal ions including calcium and magnesium, and transition metal ions including manganese, copper, iron, zinc, cobalt, lead, silver and nickel; as well as ammonium or organic ammonium including monoalkylammonium, dialkylammonium, trialkylammonium, tetraalkylammonium, monoalkenylammonium, dienylammonium, trialkenylammonium, monoynylammonium, diynylammonium, monoalkanolammonium, dialkanolammonium, C5-C6-cycloalkylammonium, piperidinium, morpholinium, pyrrolidineammonium, or benzylammonium, in addition to phosphonium ions and sulfonium ions.

[0039] Those skilled in the art will also understand that, unless otherwise stated, additional substitutions are permitted, provided that the rules of chemical bonding and strain energy are satisfied and the product still exhibits nematicidal activity.

[0040] This invention also provides a method for preparing piperidine compounds, comprising the following steps:

[0041] (1) The compound of general formula II or its salt (such as hydrochloride) is reacted with the compound of general formula III to prepare the compound of general formula I. The reaction equation is as follows:

[0042] Alternatively, (2) reacting the compound of general formula IV or its salt (such as hydrochloride) with the compound of general formula V yields the compound of general formula I, with the following reaction equation:

[0043] Alternatively, (3) react compound VII with compound VI to obtain compound I, and the reaction equation is as follows:

[0044] Where L1 represents halogen, and L2 represents halogen, -B(OH)2, or... L3 represents -B(OH)2 or Hal represents halogen, and the substituents M1, M2, M3, M4, M5, R1, R2, Y1, Y2, Y3, Y4 and X are defined as described above.

[0045] In one specific embodiment, the reactions in steps (1), (2) and (3) are all carried out in the presence of a solvent and a base.

[0046] In another specific embodiment, a catalyst is added to the reactions in steps (2) and (3).

[0047] In another specific embodiment, the solvent in steps (1) and (2) is selected from at least one of dimethyl sulfoxide, N,N-dimethylformamide, dimethylacetamide, acetonitrile, dichloroethane, dioxane, dichloromethane, tetrahydrofuran, ethyl acetate, or toluene.

[0048] In another specific embodiment, the solvent in step (3) is a mixture of organic solvent (such as ethanol, dioxane, tetrahydrofuran, etc.) and water.

[0049] In another specific embodiment, the base in steps (1), (2) and (3) is selected from at least one of inorganic or organic bases, such as K2CO3, Na2CO3, Cs2CO3, KF, NaF, CsF, LiOH, NaOH, KOH, NaH, KH, N,N-diisopropylethylamine, 4-dimethylaminopyridine, triethylamine, etc.

[0050] In another specific embodiment, the catalyst is selected from at least one of palladium catalysts (such as tridibenzylacetone dipalladium [Pd2(dba)3] / 2-biscyclohexylphosphine-2',4',6'-triisopropylbiphenyl [X-Phos], tridibenzylacetone dipalladium [Pd2(dba)3] / 1,1′-binaphthyl-2,2'-bisdiphenylphosphine [Binap], 1,1′-bisdiphenylphosphine ferrocene palladium dichloride [Pd(dppf)Cl2], palladium(II) acetate [Pd(OAc)2] / triphenylphosphine [Ph3P], etc.) or copper catalysts (such as copper acetate, copper chloride, copper(II) trifluoromethanesulfonate [Cu(OTf)2], etc.).

[0051] In addition, compounds represented by general formula I can also be prepared by referring to the methods shown in DE4208254A1, CN112745297A, etc.

[0052] The present invention also provides an intermediate, as shown in formula II, IV or VII.

[0053] The present invention also provides a nematicide composition comprising a biologically effective amount of at least one of the piperidine compounds described above.

[0054] In one embodiment, the composition further includes a formulation adjuvant.

[0055] In another embodiment, the composition further includes other active ingredients.

[0056] The present invention also provides a method for controlling nematodes, comprising exposing the nematodes or their environment to a biologically effective amount of the piperidine compound or the composition thereof.

[0057] The present invention also provides the use of the piperidine compounds or the compositions thereof in the control of nematodes.

[0058] Compounds with chemical formula I have been found to be used to control damage caused by pests and / or fungi.

[0059] In one embodiment, a compound having chemical formula I can be used in agriculture.

[0060] Therefore, the present invention further relates to a method for controlling damage and / or yield loss caused by pests and / or fungi, the method comprising applying an effective amount of a compound having chemical formula I to the pest, the site of the pest, or to plants susceptible to pest and / or fungal attack, or to plant propagation material.

[0061] These compounds according to the invention can be used to control, i.e., limit or destroy, harmful organisms and / or fungi that appear, particularly on plants, especially useful and ornamental plants in agriculture, horticulture and forestry, or on the organs of such plants, such as fruits, flowers, leaves, stems, rhizomes, seeds or roots, and in some cases, even on plant organs formed at later times, providing protection against these harmful organisms.

[0062] The compounds of Formula I according to the present invention are active ingredients with preventive and / or therapeutic value in the field of pest control. Even when applied in low doses, they can be used to combat pests and / or fungi resistant to biocides. These compounds of Formula I have a very favorable biocidal spectrum and are well tolerated by warm-blooded species, fish and plants.

[0063] The compounds according to the invention can act on all or individual developmental stages of normally sensitive and resistant animal pests (such as insects or representatives of mites). The insecticidal or acaricidal activity of the compounds according to the invention can be directly manifested, i.e., destruction of pests during molting, which occurs immediately or after a period of time; or indirectly manifested, e.g., reduced oviposition and / or hatching rates, with good activity corresponding to a destruction rate (mortality rate) of at least 50%-60%.

[0064] It has now been discovered that compounds having chemical formula I according to the present invention possess (for practical purposes) a highly advantageous activity spectrum for protecting animals and useful plants against nematode attacks and damage. Therefore, the present invention also includes nematicidal compositions having chemical formula I.

[0065] These compounds with chemical formula I are particularly useful for controlling nematodes. Therefore, in another aspect, the present invention also relates to a method for controlling damage to plants or parts thereof caused by plant-parasitic nematodes (endoparasitic, semi-endoparasitic, and ectoparasitic nematodes), particularly the following plant-parasitic nematodes: root knot nematodes, northern root knot nematode (Meloidogyne hapla), southern root knot nematode (Meloidogyne incognita), Javan root knot nematode (Meloidogyne javanica), peanut root knot nematode (Meloidogyne arenaria), and other Meloidogyne species; cyst-forming nematodes, potato golden nematode (Globodera rostochiensis), and other Globodera species; cereal cyst nematode (Heterodera avenae), soybean cyst nematode (Heterodera glycines), and beet cyst nematode (Heterodera... schachtii), Heterodera trifolii, and other Heterodera species; Seed gall nematodes, Anguina species; Stem and foliar nematodes, Aphelenchoides species; Sting nematodes, Eelonolaimus longicaudatus, and other Belonolaimus species; Pine nematodes, Bursaphelenchus xylophilus, and other Bursaphelenchus species; Ring nematodes, Criconema species, Criconemella species, Criconemoides species, and Mesocriconema species.Stem and bulb nematodes, *Ditylenchus destructor*, *Ditylenchus dipsaci*, and other *Ditylenchus* species; *Awl nematodes*, *Dolichodorus* species; *Spiral nematodes*, *Heliocotylenchus multicinctus*, and other *Helicotylenchus* species; *Sheath and sheathoid nematodes*, *Hemicycliophora* species, and *Hemicriconemoides* species; *Hirshmanniella* species; *Lance nematodes*, *Hoploaimus* species; false rootknot nematodes. *Needle nematodes*, *Nacobbus* species; *Needle nematodes*, *Longidorus elongatus* and other *Longidorus* species; *Pin nematodes*, *Pratylenchus* species; *Lesion nematodes*, *Pratylenchus neglectus*, *Pratylenchus penetrans*, *Pratylenchus curvitatus*, *Pratylenchus goodeyi* and other *Pratylenchus* species; *Burrowing nematodes*, *Radipholus similis* and other *Radipholus* species;*Reniform nematodes*, *Rotylenchus robustus*, *Rotylenchus reniformis*, and other species of the genus *Rotylenchus*; *Scutellonema* species; *Stubby root nematodes*, *Trichodorus primitivus*, and other species of the genus *Trichodorus*, *Paratrichodorus* species; *Stunt nematodes*, *Tylenchorhynchus claytoni*, *Tylenchorhynchus dubius*, and other species of the genus *Tylenchorhynchus*; *Citrus nematodes*, and species of the genus *Tylenchulus*; *Dagger nematode*. This includes species of *Nematodes* and *Xiphinema*, as well as other plant-parasitic nematodes such as *Subanguina* spp., *Hypsoperine* spp., *Macroposthonia* spp., *Melinius* spp., *Punctodera* spp., and *Quinisulcius* spp.

[0066] In particular, the compounds of the present invention can control these nematode species: *Root-knot Nematodes*, *Heterodera*, *Cyclophora*, and *Brief-bodied Nematodes*.

[0067] In another aspect, the invention also relates to a method for controlling or preventing pathogenic microbial infection of useful plants, wherein a compound having Formula I is applied as an active ingredient to the plant, its parts, or the site thereof. The compounds having Formula I according to the invention are distinguished by their activity, good plant tolerance, and environmental safety. They possess highly useful therapeutic, preventative, and systemic properties and are used to protect a wide variety of useful plants. Compounds having Formula I can be used to inhibit or destroy diseases occurring on a variety of different useful plants or plant parts (fruits, flowers, leaves, stems, tubers, roots), while also protecting, for example, later-grown plant parts from pathogenic microbial invasion. It is also possible to use compounds having Formula I as dressing agents for treating plant propagation material, particularly seeds (fruits, tubers, grains) and plant cuttings (e.g., rice), to protect against fungal infection as well as against pathogenic fungi present in the soil.

[0068] Examples of fungi include: Deuteromycetes (e.g., *Botrytis*, *Pyrrosia*, *Helicobacter*, *Fusarium*, *Syneosporium*, *Cercospora*, and *Cladosporium*); Basidiomycetes (e.g., *Rhizoctonia*, *Pythium*, and *Phyllostachys*); Ascomycetes (e.g., *Acer niger*, *Pythium*, *Candida*, and *Uncaria*); Oomycetes (e.g., *Phytophthora*, *Pythium*, and *Monocotyle*); Zygomycetes (e.g., *Rhizopus*); Sterilophyceae, especially those of the genus *Sterilophys*, such as *Synostachys beanus*, also known as Asian soybean rust; and those of the family Sterilophyceae, especially those of the genus *Sterilophys*, such as *Sterilophys gracilis*, also known as stem rust or black rust, a problematic disease in cereals; and *Sterilophys cryptica*, also known as brown rust.

[0069] These plants, and the possible diseases of these plants protected by the method according to the invention, include:

[0070] - Wheat, for the control of the following seed diseases: Fusarium (Fusarium solani and Fusarium pink), blackhead (Wheat net smut, Wheat dwarf smut or Wheat Indian smut), spore diseases (Synthia spp.) and smut.

[0071] - Wheat, for controlling the following diseases of the aboveground parts of the plant: cereal eye spot (Tapesia yallundae, Tapesia acuiformis), take-all (oat take-all fungus), root blight (Fusarium culmorum, Fusarium graminearum), black spot (Rhizoctonia graminearum), powdery mildew (Erysiphe graminis forma specie tritici), rust (Rhizoctonia gracilis and Rhizoctonia cryptica), and diseases of the genus *Syngonium* (Syngonium leuciscus and Syngonium glomeratum);

[0072] - Wheat and barley are effective in controlling bacterial and viral diseases, such as barley yellow mosaic virus; - Barley is effective in controlling the following seed diseases: net blotch (Cytosporum oryzae, Cytosporum rotundum, and Cytosporum gracilis), loose smut (loose smut), and Fusarium (Fusarium solani and Fusarium oxysporum).

[0073] - Barley is effective in controlling the following diseases of the above-ground parts of the plant: cereal eye spot (Tapesia yallundae), net spot (Erysiphe graminis formas pecie hordei), powdery mildew (Erysiphe graminis formas pecie hordei), dwarf leaf rust (barley stalk rust) and leaf spot (barley cloud spot fungus);

[0074] - Potatoes are effective in controlling tuber diseases (especially potato psoriasis fungus, Phoma tuberosa, Rhizoctonia solani, Fusarium solani), mold (pathogenic Phytophthora), and certain viruses (virus Y).

[0075] - For potatoes, control the following foliar diseases: early blight (Alternaria alternata), mildew (Phytophthora infestans);

[0076] - Cotton, for controlling the following diseases in young plants that grow from seeds: damping-off and blight (Rhizoctonia solani, Fusarium oxysporum) and black root rot (Rhizoctonia solani);

[0077] - Protein-producing plants, such as peas, are beneficial for controlling the following seed diseases: anthracnose (pea brown spot fungus, pea coccidioidomycetes), Fusarium (Fusarium oxysporum), gray mold (Botrytis cinerea), and mildew (pea downy mildew);

[0078] - Oil-bearing plants, such as rapeseed, are used to control the following seed diseases: Brassica stem bud mold, Alternaria brassicae, and Sclerotinia sclerotiorum;

[0079] - Corn, for controlling a variety of seed diseases: (Rhizopus, Penicillium, Trichoderma, Aspergillus and Fusarium graminearum);

[0080] - Flax, for controlling this seed disease: Alternaria linicola;

[0081] - Forest trees are helpful in controlling damping-off disease (Fusarium oxysporum, Rhizoctonia solani);

[0082] - Rice, used to control the following diseases of the above-ground parts: blast (rice blast) and bordered sheath spot (Rhizoctonia solani);

[0083] - Leguminosae plants, for controlling the following diseases of seeds or young plants growing from seeds: damping-off and blight (Fusarium oxysporum, Fusarium oxysporum, Rhizoctonia solani, Pythium spp.);

[0084] - Leguminosae plants, for controlling the following diseases of the above-ground parts: gray mold (Botrytis cinerea), powdery mildew (especially Asteraceae powdery mildew, Cucurbita powdery mildew, and Pepper powdery mildew), Fusarium (Fusarium oxysporum, Fusarium oxysporum), leaf spot (Cladosporium), Cladosporium leaf spot (Cladosporium), anthracnose (Anthracnose), Phytophthora leaf spot (Phytophthora), black spot (Rhizoctonia solani), and mildew (e.g., lettuce downy mildew, Downy mildew, Pseudomonas, Phytophthora);

[0085] - For fruit trees, it helps control various diseases of the above-ground parts: Candida diseases (Monilia fructigenae, M. laxa), scab (Apple black spot fungus), and powdery mildew (Monilia leucocephala); - For vines, it helps control the following leaf diseases: especially gray mold (Botrytis cinerea), powdery mildew (Botrytis cinephala), black rot (Guignardia bidwellii), and mildew (Botrytis cinephala).

[0086] - Beetroot is susceptible to the following diseases of the above-ground parts: Cercospora blight (beet brown spot fungus), powdery mildew (beet powdery mildew fungus), and leaf spot (beet leaf spot fungus).

[0087] The fungicidal compositions according to the invention can also be used to combat fungal diseases that readily grow on or inside wood. The term "wood" refers to all types of wood species, and all types of wood intended for construction work, such as solid wood, high-density wood, laminated wood, and plywood. Methods for treating wood according to the invention primarily involve contacting one or more of the compounds of the invention or the compositions according to the invention; this includes, for example, direct application, spraying, soaking, injection, or any other suitable means.

[0088] When used alone, the compounds of the present invention are effective in controlling nematodes, insects, ticks, mites, and / or fungal pathogens in growing or harvested agronomical plants. They can also be used in combination with other bioactive agents used in agriculture, such as one or more nematicides, insecticides, acaricides, fungicides, bactericides, plant activators, molluscicides, and pheromones (chemical or biological). Combining the compounds of the present invention, or combinations thereof, in their pest-killing form with other pest-killing agents often results in a broader spectrum of pest-killing activity. For example, these compounds of the present invention having Formula I can be effectively combined or used in combination with compounds such as pyrethroids, neonicotinoids, macrolides, diamides, phosphates, carbamates, cyclodienes, formamidin, phenoltin compounds, chlorinated hydrocarbons, benzoylphenylurea, pyrroles, and the like.

[0089] By adding, for example, one or more insecticidal, acaricidal, nematicidal, and / or fungicidal active agents, the activity of these compositions according to the invention can be significantly broadened and adapted to the dominant environment. Combinations of compounds having Formula I with other insecticidal, acaricidal, nematicidal, and / or fungicidal active agents can also have further, unexpected advantages, which can be described more broadly as synergistic activity. For example, better plant tolerance, reduced phytotoxicity, control of pests or fungi at different developmental stages, or better behavior during their production (e.g., during grinding or mixing, during storage, or during use).

[0090] When used alone, the compounds of the present invention are effective in controlling nematodes, insects, ticks, mites, and / or fungal pathogens in growing or harvested agronomical plants. They can also be used in combination with other bioactive agents used in agriculture, such as one or more nematicides, insecticides, acaricides, fungicides, bactericides, plant activators, molluscicides, and pheromones (chemical or biological). Mixing the compounds of the present invention or combinations thereof in pesticide form with other pesticides generally produces a broader spectrum of insecticidal action. For example, these compounds of the present invention having Formula I can be effectively combined or used in combination with compounds such as pyrethroids, neonicotinoids, macrolides, diamides, phosphates, carbamates, cyclodienes, formamidin, phenoltin compounds, chlorinated hydrocarbons, benzoylphenylurea, pyrroles, and the like.

[0091] By adding, for example, one or more insecticidal, acaricidal, nematicidal, and / or fungicidal active agents, the activity of these compositions according to the invention can be significantly broadened and adapted to current conditions. Combinations of compounds having Formula I with other insecticidal, acaricidal, nematicidal, and / or fungicidal active agents can also have further, unexpected advantages. For example, better plant tolerance, reduced phytotoxicity, control of pests or fungi at different developmental stages, or better behavior during their production (e.g., during grinding or mixing, during storage, or during use).

[0092] Other fungicides may include: 2-(thiocyanatomethylthio)-benzothiazole, 2-phenylphenol, 8-hydroxyquinoline sulfate, ametoctradin, amisulbrom, antimycin, Ampelomyces quisqualis, azaconazole, azoxystrobin, Bacillus subtilis, and Bacillus subtilis strain QST713. QST713), benalaxyl, benomyl, benthiavalicarb-isopropyl, benzylaminobenzene-sulfonate (BABS) salt, bicarbonates, biphenyl compounds, bismerthiazol, bittertanol, bixafen, blasticidin-S, borax, Bordeaux mixture, boscalid, bromuconazole, bupirimate, lime sulfur. Polysulfide, captafol, captan, carbendazim, carboxin, carpropamid, carvone, chlazafenone, chloroneb, chlorothalonil, chlozolinate, Coniothyrium minitans, copper hydroxide, copper octanoate, copper oxychloride, copper sulfate, copper sulfate (tribasic), cuprous oxide, cyazofamid.Cyflufenamid, cymoxanil, cyproconazole, cyprodinil, dazomet, debacarb, diammonium ethylenebis(dithiocarbamate), dichlofluanid, dichlorophen, diclocymet, diclomezine, dichloran, diethofencarb, difenoconazole, difenzoquat ion), diflumetorim, dimethomorph, dimoxystrobin, diniconazole, diniconazole-M, dinobuton, dinocap, diphenylamine, dithianon, dodemorph, dodemorph acetate, dodine, dodine free base Freebase), edifenphos, enestrobin, enestroburin, epoxiconazole, ethaboxam, ethoxyquin, etridiazole, famoxadone, fenamidone, fenarimol, fenbuconazole, fenfuram, fenhexamid, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph, fenpyrazamine, fentin, fentin acetate, fentin hydroxide Hydroxide, ferbam, ferimzone, fluazinam, fludioxonil, flumorphFluopicolide, fluopyram, fluoroimide, fluoxastrobin, fluquinconazole, flusilazole, flusulfamide, flutianil, flutolanil, flutriafol, fluxapyroxad, folpet, formaldehyde, triethylamine Fosetyl, Fosetyl-aluminium, Fuberidazole, Furalaxyl, Furametpyr, Guazatine, Guazatine acetates, Sodium tetrasulfide (GY-81), Hexachlorobenzene, Hexaconazole, Hymexazol, Imazalil, Imazalil sulfate sulfate), imibenconazole, iminoctadine, iminoctadine triacetate, iminoctadine tris (albesilate), iodocarb, ipconazole, ipfenpyrazolone, iprobenfos, iprodione, iprovalicarb, isoprothiolane, isopyrazam, isothiazine, kasugamycin, kasugamycin hydrochloride hydrate), kresoxim-methyl, laminarin, mancopper, mancozeb, mandipropamid, maneb, mefenoxam, mepanipyrim, mepronil, meptyl-dinocap, mercuric chloride, mercuric oxideMercurous chloride, metalaxyl, metalaxyl-M, metam, metam-ammonium, metam-potassium, metam-sodium, metconazole, methasulfocarb, methyl iodide, methyl isothiocyanate, metiram, metominostrobin, metrafenone, mildiomycin, myclobutanil, nabam, nitrothal-isopropyl, nuarimol, octhilinone, ofuronamide, oleic acid (fatty acid) Acid), Oxysastrobin, Oxadixyl, Oxine-copper, Oxpoconazole fumarate, Oxycarboxin, Pefurazoate, Penconazole, Pencycuron, Penflufen, Pentachlorophenol, Pentachlorophenyl laurate, Penthiopyrad, Phenylmercuryacetate, Phosphonic acid, Phthalide, Picoxystrobin, Polyoxin B, Polyoxins, Polyoxorim, Potassium bicarbonate, Potassium hydroquinoline sulfate), allylbenzazole, prochloraz, procymidone, propamocarb, propamocarb hydrochloride, propiconazole, propineb,Proquinazid, prothioconazole, piraclostrobin, pirametostrobin, piraoxystrobin, pyrazophos, pyribencarb, pyributicarb, pyrifenox, pyrimethanil, pyriofenone, pyroquilon, quinoclamine, quinoxyfen, quintozene, Reynoutriasachalinensis extract, sedaxane, silthiofam, simeconazole, sodium 2-phenylphenoxide, sodium bicarbonate Bicarbonate, sodium pentachlorophenoxide, spiroxamine, sulfur, SYP-Z048, wood tar, tebuconazole, tebufloquin, tetraconazole, thiabendazole, thifluzamide, thiophanate-methyl, thiram, tiadinil, tolclofos-methyl, tolylfluanid, triadimefon, triad... imenol), triazoloxide, tricyclazole, tridemorph, trifloxystrobin, triflumizole, triforine, triticonazole, validamycin, valifenalate, valiphenal, vinclozolin, zineb, ziram, zoxamide, Candida oleophila.The fungus causing wilt (Fusarium oxysporum), *Gliocladium* spp., *Phlebiopsis gigantea*, *Streptomyces griseoviridis*, *Trichoderma* spp., (RS)-N-(3,5-dichlorophenyl)-2-(methoxymethyl)-succinimide, 1,2-dichloropropane, 1,3-dichloro-1,1,3,3-tetrafluoroacetone hydrate hydrate), 1-chloro-2,4-dinitronaphthalene, 1-chloro-2-nitropropane, 2-(2-heptadecyl-2-imidazolin-1-yl)ethanol, 2,3-dihydro-5-phenyl-1,4-dithi-ine 1,1,4,4-tetraoxide, 2-methoxyethylmercury acetate, 2-methoxyethylmercury chloride, 2-methoxyethylmercury silicate Silicate, 3-(4-chlorophenyl)-5-methylrhodanine, 4-(2-nitroprop-1-enyl)phenylthiocyanate, ampropylfos, anilazine, azithiram, barium polysulfide, Bayer 32394, benodanil, benquinox, bentaluron, benzalkonium chloride; benzamacril-isobutyl benzamacrilBenzamorf, binapacryl, bis(methylmercury)sulfate, bis(tributyltin)oxide, buthiobate, cadmium calcium copper zinc chromate sulfate, carbamorph, CECA, chlobenthiazone, chloraniformethan, chlorfenazole, chlorquinox, climbazole, copper bis(3-phenylsalicylate), copper zinc chromate, cufraneb, copper hydrazine sulfate Sulfate), Copper chloride (cuprobam), Cycloafuramid, Cypendazole, Cyprofuram, Decafentin, Dichloronaphthoquinone, Dichlozoline, Diclobutrazol, Dimethirimol, Diocton, Dinosulfon, Dinoterbon, Dipyrithione, Ditalimfos, Dodicin, Drazoxolon, E. coli BP), ESBP, eticonazole, etem, ethirim, fenaminosulf, fenapanil, finitropan, fluotrimazole, furcarbanil, furconazole, furconazole-cis, furmecyclox, furophanate, glyodine, griseofulvin, halacrinate, Hercules 3944, hexylthiofos, propiconazole (ICIA0858),Isopamphos, isovaledione, mebenil, mecarbinzid, metazoxolon, methfuroxam, methylmercury dicyandiamide, metsulfovax, milneb, mucochloric anhydride, myclozolin, N-3,5-dichlorophenylsuccinimide, N-3-nitrophenylitaconimide, natamycin, N-ethylmercurio-4-toluenesulfonanilide, nickel di(dimethyldithiocarbamate) Bis(dimethyldithiocarbamate), octachlorophenone (OCH), phenylmercurydimethyldithiocarbamate, phenylmercury nitrate, phosdiphen, prothiocarb; prothiocarb hydrochloride, piracarbolid, pyridinitril, pyroxychlor, pyroxyfur, quinacetol; quinacetol sulfate, quinazamid, quinconazole, rabenzazole, salicylamide e), azoxystrobin (SSF-109), sulfadiazine (sultropen), tecoram, thiadifluor, thicyofen, thiochlorfenphim, thiophanate, thioquinox, tioxymid, triamiphos, triarimol, triazbutil, trihlamide,Urbacid, Zarilamid, and any combination thereof.

[0093] Other nematicides may include: AKD-3088, 1,2-dibromo-3-chloropropane, 1,2-dichloropropane, 1,2-dichloropropane and 1,3-dichloropropene, 1,3-dichloropropene, 3,4-dichlorotetrahydrothiophene 1,1-dioxide, 3-(4-chlorophenyl)-5-methylrhodanine, 5-methyl-6-thio-1,3,5-thiadiazin-3-ylacetic acid, 6-isopentenylaminopurine, avermectin, acetamiprid, malathion, and aldicarb. icarb), aldoxycarb, AZ60541, benclothiaz, benclothiazide, butylpyridaben, cadusafos, carbofuran, carbon disulfide, thiocarbofuran, chloropicrin, chlorpyrifos, cloethocarb, cytokinins, dazomet, DBCP, DCIP Diamidafos, dichlofenthion, didiciphos, dimethoate, imadin, imadin benzoate, eprimectin, ethoprophos, ethane dibromo, fenamiphos, fenpyrad, fensulfothion, fosthiazate, fosthietan, furfural, GY-81, heterophos, methyl iodide, isamidophos, isazofos, chlorpyrifos, kinetin, mecarphon, mecarphon, methyl methamidophos, potassium methamidophos, sodium methamidophos, methyl bromomethane, methyl isothiocyanate, milbemycin oxime), moxifloxacin, Myrothecium verrucaria components, NC-184, chlorpyrifos, phorate, phosphocarb, sebufos, selamectin, spinosad, terbam, terbufos, tetrachlorothiophene, thiafenox, thionazin, triazophos, triazuron, xylenol, YI-5302 and zeatin, fluensulfone [318290-98-1], and any combination thereof.

[0094] References in square brackets following the active ingredient, such as [3878-19-1], refer to Chemical Abstracts Registry numbers. Generally, in any combination of the two components in this invention, the mass ratio between them is independently from 100:1 to 1:100, preferably from 75:1 to 1:75, more preferably from 50:1 to 1.50, especially from 25:1 to 1:25, advantageously 10:1 means 1:10, such as from 5:1 to 1:5, for example from 1:3 to 3:1. These mixing ratios are understood to include, on the one hand, by mass, and on the other hand, a molar ratio.

[0095] Examples of methods of application of the compounds and compositions thereof used in this invention, namely methods for controlling harmful organisms / fungi in agriculture, such as spraying, atomizing, dusting, brushing, seed dressing, broadcasting, or irrigating - are selected to suit the intended purpose of the environment at the time.

[0096] In agriculture, a preferred method of application is to the leaves of these plants (foliar application), with the frequency and rate of application chosen to match the risk of infection by the pests / fungi discussed. Alternatively, the active ingredient can reach the plant via the root system (systemic absorption), achieved by applying the compound to the site of the plant, for example, by applying a liquid composition of the compound to the soil (through saturation) or by applying the compound in solid form as granules to the soil (soil application). In the case of rice plants, such granules can be metered and added to flooded paddy fields.

[0097] The application rate per hectare is generally 1g to 2000g of active ingredient per hectare, especially 10g / ha to 1000g / ha, preferably 10g / ha to 600g / ha, such as 50g / ha to 300g / ha.

[0098] These compounds and compositions of the present invention are also suitable for the protection of plant propagation material (e.g., seeds, fruits, tubers, or grains, or nursery plants) against the aforementioned types of pests. The propagation material can be treated with the compound before planting; for example, seeds can be treated before sowing. Alternatively, the compound can be applied to the seed grains (coating), which is achieved by immersing the grains in a liquid composition or by applying a layer of solid composition. When the propagation material is planted at the application site, these compositions may also be applied, for example, during row sowing. These methods of treating plant propagation material and the plant propagation material thus treated are further subjects of the present invention. Typically, the treatment rate will depend on the plant to be controlled and the pest / fungus, generally between 1 gram and 200 grams per 100 kg of seeds, preferably between 5 grams and 150 grams per 100 kg of seeds, such as between 10 grams and 100 grams per 100 kg of seeds.

[0099] The term seed includes all kinds of seeds and plant propagules, including but not limited to true seeds, seed tubers, suckers, grains, bulbs, fruits, tubers, cereals, rhizomes, cuttings, cut branches and the like, and in a preferred embodiment refers to true seeds.

[0100] The present invention also includes seeds coated or treated with or containing a compound having Formula I. The term "coated with or treated with and / or containing" generally indicates that, in most cases, the active ingredient is on the surface of the seed when applied, although a portion of the ingredient may penetrate into the seed material, depending on the method of application. When the seed product is (re)planted, it can absorb the active ingredient. In one embodiment, the present invention makes it possible to obtain a plant propagation material having a compound having Formula I adhered thereto. Furthermore, a composition comprising plant propagation material treated with a compound having Formula I is thus obtained.

[0101] Seed treatment includes all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, and seed granulation. The application of a compound having chemical formula I can be achieved by any known method, such as spraying or dusting before or during sowing / planting of these seeds.

[0102] Suitable target plants include cereals such as wheat, barley, rye, oats, rice, corn, or sorghum; beets such as sugar beets or fodder beets; fruits such as pome fruits, drupes, or seedless fruits such as apples, pears, plums, peaches, almonds, cherries, or berries such as strawberries, raspberries, or blackberries; legumes such as beans, lentils, peas, or soybeans; oilseed crops such as rapeseed, mustard, chestnuts, olives, sunflowers, coconuts, castor beans, cocoa, or peanuts; and cucurbit crops such as pumpkins, cucumbers, or melons. Fiber plants, such as cotton, flax, hemp, or jute; citrus fruits, such as oranges, lemons, grapes, or tangerines; vegetables, such as spinach, lettuce, asparagus, cabbage, carrots, onions, tomatoes, potatoes, or bell peppers; Lauraceae plants, such as avocados, camphor (Cinnamonium), or camphor; and also tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper, grapevines, hops, plantains, rubber plants, and ornamental plants (such as flowers and lawn plants or turf).

[0103] In one embodiment, the plant is selected from cereals, corn, soybeans, rice, sugarcane, vegetables, and oilseed plants.

[0104] The term "plant" should be understood to also include plants transformed using recombinant DNA technology that are capable of synthesizing one or more selectively acting toxins, such as those known from toxin-producing bacteria, particularly those of the genus Bacillus.

[0105] Transgenic plants containing one or more genes encoding pesticide resistance and expressing one or more toxins are known, and some of them are commercially available.

[0106] The compounds of the present invention are typically used in the form of a composition comprising a carrier (e.g., a formulation). The compounds and compositions thereof of the present invention can be used in various forms, such as aerosol sprayers, capsule suspensions, cold atomized concentrates, pulverizable powders, emulsifiable concentrates, oil-in-water emulsions, water-in-oil emulsions, capsule granules, fine granules, flowable concentrates for seed treatment, gases (under pressure), gas-producing products, granules, thermal atomized concentrates, large granules, microgranules, oil-dispersible powders, oil-miscible flowable concentrates, oil-miscible liquids, pastes, plant sticks, powders for dry seed treatment, seeds coated with pesticides, soluble concentrates, soluble powders, solutions for seed treatment, suspension concentrates (flowable concentrates), ultra-low volume (ULV) liquids, ultra-low volume (ULV) suspensions, water-dispersible granules or tablets, water-dispersible powders for slurry treatment, water-soluble granules or tablets, water-soluble powders for seed treatment, and wettable powders.

[0107] A formulation typically includes a liquid or solid carrier and optionally one or more commonly used formulation aids, which may be solid or liquid, such as non-epoxidized or epoxidized vegetable oils (e.g., epoxidized coconut oil, rapeseed oil, or soybean oil), defoamers, such as silicone oils, preservatives, clays, inorganic compounds, viscosity modifiers, surfactants, adhesives, and / or thickeners. The composition may further include a fertilizer, micronutrient donor, or other product affecting plant growth, and may include a combination comprising the compounds of the present invention and one or more other bioactive agents, such as bactericides, fungicides, nematicides, plant activators, acaricides, and insecticides.

[0108] Therefore, the present invention also makes it possible to obtain a composition comprising a compound of the present invention, an agriculturally economical carrier, and optionally one or more commonly used formulation aids.

[0109] These compositions are prepared by methods known per se, in the absence of additives, for example by grinding, sieving, and / or pressing the solid compounds of the present invention, and in the presence of at least one additive, for example by tightly mixing and / or grinding the compound of the present invention with one or more additives. In the case of the solid compounds of the present invention, the grinding / crushing of the compound is to ensure a specific particle size. These methods for preparing these compositions, and the use of these compounds of the present invention for preparing these compositions, are also a subject of the present invention.

[0110] Examples of compositions used in agriculture include emulsifiable concentrates, suspension concentrates, microemulsions, oil dispersibles, direct sprayable or dilutable solutions, coatable pastes, diluted emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules, or capsules in polymeric substances. These compositions comprise at least one compound according to the invention, and the type of composition is selected to suit the intended purpose and the prevailing environment.

[0111] Examples of suitable liquid carriers are: unhydrogenated or partially hydrogenated aromatic hydrocarbons, preferably C8 to C9. 12 Alkylbenzene moieties, such as xylene mixtures, alkylated naphthalene or tetrahydronaphthalene, aliphatic or alicyclic hydrocarbons, such as paraffin or cyclohexane, alcohols such as ethanol, propanol or butanol, ethylene glycol and their ethers and esters such as propylene glycol, dipropylene glycol ether, ethylene glycol or ethylene glycol monomethyl ether or hexanediol monoethyl ether, ketones such as cyclohexanone, isophorone or diacetone alcohol, strongly polar solvents such as N-methylpyrrolidone-2-one, dimethyl sulfoxide or N,N-dimethylformamide, water, unepoxidized or epoxidized vegetable oils such as unepoxidized or epoxidized rapeseed oil, castor oil, coconut oil or soybean oil, and silicone oil.

[0112] Examples of solid carriers used for products such as dusts and dispersible powders are typically ground natural minerals such as calcite, talc, kaolin, montmorillonite, or attapulgite. To improve physical properties, it is also possible to add highly dispersed silica or highly dispersed absorbent polymers. Suitable particulate absorbent carriers for granules are porous, such as pumice, gravel, sepiolite, or bentonite, while suitable non-absorbent carrier materials are calcite or sand. Furthermore, a wide variety of granulated inorganic or organic natural materials can be used, particularly dolomite or pulverized plant residues.

[0113] Depending on the type of active ingredient to be formulated, suitable surfactants are nonionic, cationic, and / or anionic surfactants or mixtures of surfactants that possess good emulsifying, dispersing, and wetting properties. The surfactants mentioned below are merely examples; a large number of other surfactants commonly used in formulations and suitable for use according to the present invention are described in the relevant literature.

[0114] Suitable nonionic surfactants are, in particular, polyethylene glycol ether derivatives of aliphatic or alicyclic alcohols, polyethylene glycol ether derivatives of saturated or unsaturated fatty acids, or polyethylene glycol ether derivatives of alkylphenols, which may contain about 3 to about 30 glycol ether groups and about 8 to about 20 carbon atoms in the (cyclic)aliphatic hydrocarbon residues, or about 6 to about 18 carbon atoms in the alkyl moiety of the alkylphenol. Also suitable are water-soluble polyethylene oxide adducts with polypropylene glycol, ethylenediaminopolypropylene glycol, or alkylpolypropylene glycol (having about 1 to about 10 carbon atoms in the alkyl chain and about 20 to about 250 glycol ether groups and about 10 to about 100 propylene glycol ether groups). Typically, each propylene glycol unit of the above compounds contains about 1 to about 5 glycol units. Examples that may be mentioned are nonylbenzene alcohol ether, castor oil polyethylene glycol ether, polypropylene glycol / polyethylene oxide adduct, tributylphenoxy polyethylene glycol, polyethylene glycol, or octylphenoxy polyethylene glycol. Also suitable are fatty acid esters of polyoxyethylene sorbitan, such as polyoxyethylene sorbitan trioleate.

[0115] These cationic surfactants are, in particular, quaternary ammonium salts that typically have at least one alkyl residue (about 8 to about 22 C atoms) as a substituent and (unhalogenated or halogenated) lower alkyl or hydroxyalkyl or benzyl residues as other substituents. These salts are preferably in the form of halides, methyl sulfates, or ethyl sulfates. Examples are stearyltrimethylammonium chloride and benzylbis(2-chloroethyl)ethylammonium bromide.

[0116] Examples of suitable anionic surfactants are water-soluble soaps or water-soluble synthetic surfactant compounds. Examples of suitable soaps are alkali metal salts, alkaline earth metal salts, or (unsubstituted or substituted) ammonium salts of fatty acids having about 10 to about 22 carbon atoms, such as sodium or potassium salts of oleic acid or stearic acid or mixtures of natural fatty acids (obtainable from, for example, coconut oil or tall oil); fatty acid methyl taurine must also be mentioned. However, synthetic surfactants are more commonly used, particularly fatty sulfonates, fatty sulfates, sulfonated benzimidazole derivatives, or alkyl aryl sulfonates. Typically, these fatty sulfonates and fatty sulfates are alkali metal salts, alkaline earth metal salts, or (substituted or unsubstituted) ammonium salts and they generally have alkyl residues having about 8 to about 22 carbon atoms, alkyl also understood to include an alkyl moiety comprising an acyl residue; examples that may be mentioned are sodium or calcium salts of lignin sulfonate, sodium or calcium salts of dodecyl sulfate, or sodium or calcium salts of mixtures of fatty alcohol sulfates prepared from natural fatty acids. This group also includes sulfate and sulfonate salts of fatty alcohol / ethylene oxide adducts. These sulfonated benzimidazole derivatives preferably contain two sulfonyl groups and fatty acid residues of about 8 to about 22 carbon atoms. Examples of alkylaryl sulfonates are sodium, calcium, or triethanolamine salts of decylbenzenesulfonic acid, dibutylnaphthalenesulfonic acid, or naphthalenesulfonic acid / formaldehyde condensates. Additionally, suitable phosphates (esters), such as phosphate salts of p-nonylphenol / (4-14)ethylene oxide adducts, or phospholipids, are also possible.

[0117] Typically, these compositions contain 0.1% to 99% (particularly 0.1% to 95%) of the compound according to the invention and 1% to 99.9% (particularly 5% to 99.9%) of at least one solid or liquid carrier. It is also possible, in principle, that 0% to 25% (particularly 0.1% to 20%) of the composition is a surfactant (in each case, % represents a weight percentage). However, for commercial purposes, concentrated compositions are generally preferred, and end users, in principle, use diluted compositions with significantly lower concentrations of the active ingredient.

[0118] Examples of formulation types suitable for barrel mixing compositions include solutions, diluted emulsions, suspensions or mixtures thereof, and dust.

[0119] Regarding the properties of these preparations, the methods of the present invention, such as leafing, wetting, spraying, atomizing, dusting, spreading, coating, or dumping, can be selected according to the intended purpose and the dominant environment.

[0120] This tank-mix formulation composition is generally prepared by diluting one or more premixed compositions containing different biocides and optionally additional adjuvants with a solvent (e.g., water).

[0121] Suitable carriers and adjuvants can be solid or liquid and are substances commonly used in formulation technology, such as natural or recycled minerals, solvents, dispersants, wetting agents, thickeners, fillers, adhesives or fertilizers.

[0122] In general, tank-mixed formulations for foliar or soil application comprise 0.1% to 20%, particularly 0.1% to 15%, of the desired ingredient, and 99.9% to 80%, particularly 99.9% to 85%, of solid or liquid adjuvants (including, for example, a solvent such as water), which may be a surfactant, in an amount based on the tank-mixed formulation being 0% to 20%, particularly 0.1% to 15%.

[0123] Typically, premixed formulations for foliar application comprise 0.1% to 99.9%, particularly 1% to 95%, of the desired ingredient, and 99.9% to 0.1%, particularly 99% to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein such adjuvants may be a surfactant, and the amount of which is 0% to 50%, particularly 0.5% to 40%, based on the premixed formulation.

[0124] Typically, tank-mixed formulations for seed treatment application comprise 0.25% to 80%, particularly 1% to 75%, of the desired ingredient, and 99.75% to 20%, particularly 99% to 25%, of solid or liquid adjuvants (including, for example, a solvent such as water), wherein these adjuvants may be a surfactant, and the amount based on the tank-mixed formulation is 0% to 40%, particularly 0.5% to 30%.

[0125] Typically, premixed formulations for seed treatment application comprise 0.5% to 99.9%, particularly 1% to 95%, of the desired ingredient, and 99.5% to 0.1%, particularly 99% to 5%, of a solid or liquid adjuvant (including, for example, a solvent such as water), wherein such adjuvants may be a surfactant, and the amount of which is 0% to 50%, particularly 0.5% to 40%, based on the tank mixture formulation.

[0126] Commercial products are preferably formulated as concentrates (e.g., premixed compositions (formulations)), while end users typically use diluted formulations (e.g., tank-mixed compositions).

[0127] Preferred seed treatment premixes are aqueous suspension concentrates. These premixes can be applied to seeds using conventional processing techniques and machinery, such as fluidized bed technology, drum milling methods, rotostatic seed processors, and rotary drum applicators. Other methods, such as spray beds, can also be useful. The seeds can be pre-coated before coating. After coating, the seeds are typically dried and then transferred to a coating machine for further coating. Such methods are well known in the art.

[0128] In general, the premixed compositions of the present invention comprise 0.5% to 99.9%, particularly 1% to 95%, advantageously 1% to 50% by weight of the desired ingredient, and 99.5% to 0.1%, particularly 99% to 5% by weight of a solid or liquid adjuvant (including, for example, a solvent, such as water), wherein these adjuvants (or adjuvants) may be a surfactant, the amount of which is 0% to 50%, particularly 0.5% to 40% by weight based on the premixed formulation.

[0129] In a preferred embodiment, independent of any other embodiment, a compound having chemical formula I is in the form of a composition for treating (or protecting) plant propagation material, wherein the composition for protecting plant propagation material further comprises a colorant. Such a composition or mixture for protecting plant propagation material may also comprise at least one copolymer of a water-soluble and water-dispersible film-forming polymer that improves the adhesion of the active ingredient to the treated plant propagation material, the polymer having an average molecular weight of at least 10,000 to about 100,000.

[0130] The combination of the present invention (i.e., those including the compounds of the present invention and one or more other bioactive agents) can be administered simultaneously or sequentially.

[0131] In this case, a combination of components is applied sequentially (i.e., one by one), within a mutually reasonable period, to achieve biological performance, such as within hours or days. The order of application of these components in the combination, i.e., whether the compound having chemical formula I should be applied first, is not critical to the implementation of this invention.

[0132] In this case, the components of these combinations are applied simultaneously in the present invention, and they can be applied as a composition containing the combination, wherein (A) the compound having chemical formula I and one or more components of the combination can be obtained from a separate formulation source and mixed together (referred to as a barrel mix, ready-to-use, spray broth, or slurry), or (B) the compound having chemical formula I and one or more components of the combination can be obtained as a separate formulation mixture source (referred to as a premix, i.e., mixture, concentrate, or formulation product).

[0133] In one embodiment, independent of other embodiments, a compound according to the invention is applied as a combination. Therefore, the invention also provides a composition comprising a compound according to the invention as described herein, one or more other bioactive agents, and optionally one or more conventional formulation adjuvants; the composition may be in the form of a barrel-mixed or premixed composition.

[0134] These combinations of the present invention can have advantageous properties, examples of which may be mentioned are: advantageous behavior during formulation and / or application (e.g., when grinding, screening, emulsifying, dissolving, or dispersing); increased storage stability; improved photostability; more advantageous degradability; improved toxicological and / or ecotoxicological behavior; or other advantages familiar to those skilled in the art. Detailed Implementation

[0135] The following examples are for illustrative purposes only and should not be construed as limiting the invention in any way. The scope of protection of this invention is defined by the claims.

[0136] Given the economic efficiency and diversity of the compounds, we preferentially synthesized a number of compounds, some of which are listed in Table 1 below. Specific compound structures and corresponding compound information are shown in Tables 1-2. The compounds in Table 1 are only for better illustration of the present invention and do not limit the invention. Those skilled in the art should not interpret this as limiting the scope of the above-mentioned subject matter of the invention to the following compounds.

[0137] Table 1. Compound Structures

[0138] Table 2 Compounds 1 H NMR values

[0139] Several methods for preparing the compounds of the present invention are described in detail in the following schemes and examples. The raw materials can be commercially available or prepared by methods known in the literature or as detailed in the description. Those skilled in the art will understand that other synthetic routes can also be used to synthesize the compounds of the present invention. Although specific raw materials and conditions in the synthetic routes have been described below, they can be easily replaced with other similar raw materials and conditions. Such variations or modifications to the preparation methods of the present invention, such as various isomers of the compounds, are all included within the scope of the present invention. Furthermore, the preparation methods described below can be further modified according to the disclosure of the present invention using conventional chemical methods well known to those skilled in the art. For example, protecting appropriate groups during the reaction process, etc.

[0140] The following method examples are provided to further illustrate the preparation methods of the present invention. The specific substances, types, and conditions used are intended to further explain the invention and are not intended to limit its reasonable scope. The reagents used in the synthetic compounds shown below are either commercially available or can be easily prepared by those skilled in the art.

[0141] Examples of representative compounds are given below. The synthesis methods of other compounds are similar and will not be described in detail here.

[0142] 1. Synthesis of Compound 151

[0143] (1) Compound 151-1 (10.5 g, 1.0 eq, 32.21 mmol) and cesium carbonate (31.40 g, 3.0 eq, 96.63 mmol) were added to a single-necked flask and dissolved in a mixture of dioxane and water. Then, pinacol isopropenylborate (8.12 g, 1.5 eq, 48.31 mmol) was added, and the mixture was purged with nitrogen three times. Pd(dppf)Cl2·DCM catalyst (2.63 g, 0.1 eq, 3.22 mmol) was added, and the mixture was purged with nitrogen three more times. The mixture was heated to 110 °C and stirred overnight. The sample was directly passed through a column to obtain product 151-2 (7.8 g, yield 72.97%).

[0144] (2) Compound 151-2 (7.8 g, 1.0 eq, 23.49 mmol) was added to a single-necked flask, dissolved in HCl / Dioxane solution, heated to 40 °C, and stirred for 2 hours. The reaction solution was directly evaporated to dryness to obtain 6 g of white solid 151-3.

[0145] (3) Compound 151-3 (0.2 g, 1.0 eq, 0.75 mmol) and cesium carbonate (1.21 g, 5.0 eq, 3.73 mmol) were added to a single-necked flask, dissolved in DMA, and then 151-4 (0.18 g, 1.2 eq, 0.90 mmol) was added. The mixture was heated to 150 °C and stirred for 1 day. The mixture was extracted with EA / water, and the organic phase was passed through a column with dry stirring to obtain product 151 (64 mg, yield 18.88%).

[0146] 2. Synthesis of Compound 160

[0147] In a 100 mL round-bottom flask, 151-3 (0.6 g, 1.0 eq, 2.58 mmol) was added to 20 mL of toluene, followed by 160-1 (0.9 g, 1.5 eq, 3.88 mmol), cesium carbonate (2.5 g, 3.0 eq, 7.76 mmol), and X-phos (0.247 g, 0.2 eq, 0.52 mmol). The mixture was purged with nitrogen three times. Then, Pd2(dba)3 (0.237 g, 0.1 eq, 0.25 mmol) was added, and the mixture was purged with nitrogen three more times. The mixture was heated to 110 °C and stirred overnight. The reaction was monitored by LCMS until complete. The mixture was extracted with water and EA, the organic phase was evaporated to dryness, and purified by column chromatography. Compound 160 was given, weighing 37 mg (90% purity, 3.7% yield).

[0148] 3. Synthesis of Compound 180

[0149] (1) In a 50 mL single-necked flask, 180-1 (0.8 g, 1.0 eq, 4.47 mmol) was added to 10 mL of N,N-dimethylformamide, followed by 180-2 (1.5 g, 1.2 eq, 5.36 mmol) and N,N-diisopropylethylamine (1.16 g, 2 eq, 8.94 mmol). The mixture was reacted overnight at 80 °C. After the reaction was complete, the reaction solution was poured into 20 mL of water, and ethyl acetate was added (10 mL x 2) for extraction. The organic phase was collected, concentrated under reduced pressure, stirred with silica gel, and separated by normal-phase column chromatography to obtain product 180-3, weighing 1.3 g (purity 95%, yield 75%).

[0150] (2) Dissolve 180-3 (0.2 g, 1 eq, 0.52 mmol) in 8 ml of Dioxane and 1 ml of H2O, add pinacol isopropenylborate (0.1 g, 1.2 eq, 0.62 mmol) and cesium fluoride (0.16 g, 2 eq, 1.03 mmol), purge with nitrogen once, add Pd(dppf)Cl2 (0.02 g, 0.05 eq, 0.02 mmol), purge with nitrogen three more times, react at 100 °C for 12 h, monitor the reaction until the starting material disappears, dry the reaction solution by rotary evaporation, and purify the organic phase by column chromatography to obtain 180 (43 mg, purity 98%, yield 21%), a light yellow oil.

[0151] 4. Synthesis of Compound 185

[0152] (1) Dissolve 185-1 (12g, 1eq, 35.00mmol) in 135ml Dioxane and 15ml H2O, add pinacol isopropenylborate (7.06g, 1.2eq, 42.00mmol) and cesium fluoride (10.63g, 2eq, 70.01mmol), purge once with nitrogen, add Pd(dppf)Cl2 (1.28g, 0.05eq, 1.75mmol), purge three more times with nitrogen, react at 100℃ for 12h, monitor the reaction until the starting material disappears, dry the reaction solution by rotary evaporation, and purify the organic phase by column chromatography to obtain 185-2 (6g, purity 92%, yield 49%), a white solid.

[0153] (2) Dissolve 185-2 (6g, 1eq, 17.22mmol) in 60ml of 1,4-dioxane hydrochloric acid solution and react at room temperature for 5h. Monitor the reaction until the starting material disappears. The reaction solution is evaporated to dryness to obtain compound 185-3 (4.6g, light yellow solid).

[0154] (3) Compound 185-3 (0.2 g, 1 eq, 0.81 mmol) was dissolved in 5 ml of toluene, and 1-bromo-4-(trifluoromethylthio)benzene 185-4 (0.25 g, 1.2 eq, 0.97 mmol) and cesium carbonate (0.52 g, 2 eq, 1.61 mmol) were added. The mixture was purged with nitrogen once, and X-Phos (0.07 g, 0.2 eq, 0.16 mmol) and Pd2(dba)3 (0.14 g, 0.2 eq, 0.16 mmol) were added. The mixture was purged with nitrogen three more times. The reaction was carried out at 120 °C for 12 h. The reaction was monitored until the starting material disappeared. The reaction solution was dried by rotary evaporation and purified by column chromatography to obtain compound 185 (93 mg, purity 99%, yield 27%), a white solid.

[0155] 5. Synthesis of Compound 189

[0156] In a 20 mL single-necked flask, 189-1 (0.3 g, 2.1 eq, 1.1 mmol), 185-3 (150 mg, 1 eq, 0.53 mmol), cesium carbonate (517 mg, 3.0 eq, 1.59 mmol), and Xphos (24 mg, 0.1 eq, 0.05 mmol) were added to 6 mL of toluene. The mixture was purged with nitrogen for 30 s. Then, Pd2(dba)3 (46 mg, 0.1 eq, 0.05 mmol) was added, and the mixture was purged with nitrogen for 30 s. The flask was sealed, and the mixture was stirred overnight at 110 °C. The reaction was monitored to confirm completion. The reaction solution was concentrated under reduced pressure and purified under normal phase to obtain product 189, weighing 89 mg (purity 94%, yield 33%).

[0157] 6. Synthesis of Compound 194

[0158] In a 50 mL single-necked flask, 185-3 (2 g, 1.0 eq, 8.05 mmol) was added to 20 mL of N,N-dimethylformamide, followed by 2-chloro-4-fluorobenzonitrile (1.5 g, 1.2 eq, 9.66 mmol) and N,N-diisopropylethylamine (2.08 g, 2 eq, 16.11 mmol). The reaction mixture was reacted overnight at 80 °C. After the reaction was complete, the reaction solution was poured into 20 mL of water, and extracted with ethyl acetate (10 mL x 2). The organic phase was collected, concentrated under reduced pressure, stirred with silica gel, and separated by normal-phase column chromatography. Product 194 was obtained, weighing 1 g (purity 99%, yield 32%).

[0159] 7. Synthesis of Compound 195

[0160] (1) In a 50 mL single-necked flask, 194 (0.5 g, 1.0 eq, 1.30 mmol) was added to 5 mL of anhydrous ethanol, followed by an aqueous solution of hydroxylamine (0.25 g, 3 eq, 3.91 mmol, 50%). The mixture was reacted at 80 °C for 2 h. After the reaction was complete, the mixture was concentrated under reduced pressure to obtain crude product 195-1, 0.54 g.

[0161] (2) In a 50 mL single-necked flask, 195-1 (0.12 g, 1.0 eq, 0.29 mmol) was added to 2 mL of anhydrous tetrahydrofuran, followed by difluoroacetic anhydride (0.07 g, 1.5 eq, 0.43 mmol). The mixture was reacted at room temperature for 2 h. After the reaction was complete, the mixture was concentrated under reduced pressure and separated by normal-phase column chromatography. Product 195 (61 mg, purity 95%, yield 44%) was obtained as a pale yellow oil.

[0162] Bioactivity evaluation (nematode 96-well plate bioassay):

[0163] (1) Preparation of test reagents

[0164] Accurately weigh the test reagent, dissolve it in DMSO to prepare a stock solution, and dilute it into solutions of different concentration gradients.

[0165] (2) Isolation of target nematodes

[0166] Mixed nematode stage of pine wood nematode: Under a stereomicroscope, select a plate with a large number of nematodes on the lid of a culture dish, wash off the nematodes on the lid with sterile water, transfer them to a 10ml centrifuge tube, and dilute the nematode solution to about 1000 nematodes per milliliter for later use.

[0167] Second-instar root-knot nematodes: When egg masses emerge from the root nodes, use forceps under a dissecting microscope to remove the egg masses and place them in clean water. Soak them in a 0.25% sodium hypochlorite solution for about 1 minute, then wash and sieve them through a 500-mesh sieve. Place them in a 90mm petri dish containing an appropriate amount of tap water and put them in a sieving device. Incubate at 28℃ for 3 days. The egg masses will then hatch into second-instar larvae. Observe the concentration of the nematode suspension under a microscope and dilute it to a nematode suspension of about 1000 nematodes / mL for later use.

[0168] (3) Chemical treatment

[0169] Add 100 μL each of the prepared test reagent and nematode suspension to a 96-well culture plate, cover to prevent evaporation, and incubate at 28°C. Include a water control and a reagent control; if a solvent is used, include a solvent control as well.

[0170] (4) Cultivation and Observation

[0171] The nematodes treated with the agent were cultured under normal conditions for 72 hours, and the mortality rate was measured: Mortality rate (%) = (Number of dead nematodes / Number of test nematodes) * 100. Representative experimental results are shown in Table 3.

[0172] Table 3 Results of the nematicide test

[0173] Note: N represents no data; control compound A:

[0174] Furthermore, numerous tests have revealed that the compounds and their compositions described in this invention possess broad-spectrum, high-efficiency, and strong systemic properties, effectively controlling various types of nematodes and demonstrating certain commercial value.

Claims

1. A piperidine compound, as shown in general formula I: in, M1, M2, M3, M4, and M5 each independently represent CR or N; X represents O or NR8; Y1, Y2, Y3, and Y4 each independently represent hydrogen, halogen, alkyl, or haloalkyl; R1 represents hydrogen, halogen, -N(R) 21 2. Alkyl, haloalkyl, alkenyl, haloalkenyl, ynyl, haloynyl or -OR 21 ; R2 represents hydrogen, halogen, nitro, cyano, alkyl, haloalkyl, alkenyl, haloalkenyl, alkynyl, haloalkynyl, cycloalkyl, cycloalkenyl, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-OR 21 ,-alkylene-OR 21 -(CO)R 21 or-(CO)OR 21 ; R can independently represent hydrogen, halogen, nitro, cyano, thiocyano, alkyl, alkenyl, ynyl, cycloalkyl, cycloalkenyl, heterocyclic, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-(SO2)N(R 21 )2、-OR 21 -(CO)SR 21 -(CO)R 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -O(CO)OR 21 -CR 21 =N-OR 21 -C(N(R) 21 )2)=N-OR 21 or-(CO)OR 21 The "alkyl", "alkenyl" or "alkynyl" is optionally selected from halogen, nitro, cyano, cycloalkyl, cycloalkenyl, heterocyclic, aryl or -OR 21 At least one group in it is replaced; R8 represents hydrogen, alkyl, or haloalkyl; R 21 Each of these groups independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclic or heterocyclic alkyl, wherein the "alkyl", "alkenyl" or "alkynyl" is optionally substituted by at least one group selected from halogen, cyano, alkoxy or haloalkoxy. The aforementioned "cycloalkyl", "cycloalkenyl", "heterocyclic" or "aryl" is optionally selected from oxo, halogen, cyano, nitro, alkyl, alkenyl, ynyl, cycloalkyl, haloalkyl, haloalkenyl, haloynyl, halocycloalkyl, alkyl-substituted cycloalkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 At least one group in )2 is replaced; R 10 Each can be independently represented by hydrogen, alkyl, or haloalkyl.

2. The piperidine compound according to claim 1, characterized in that, Y1, Y2, Y3, and Y4 independently represent hydrogen, halogen, C1-C8 alkyl, or halo-C1-C8 alkyl, respectively; R1 represents hydrogen, halogen, -N(R) 21 2. C1-C8 alkyl, halo-C1-C8 alkyl, C2-C8 alkyl, halo-C2-C8 alkenyl, C2-C8 ynyl, halo-C2-C8 ynyl or -OR 21 ; R2 represents hydrogen, halogen, nitro, cyano, C1-C8 alkyl, halogenated C1-C8 alkyl, C2-C8 alkenyl, halogenated C2-C8 alkenyl, C2-C8 ynyl, halogenated C2-C8 ynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-OR 21 -(C1-C8 alkylene)-OR 21 -(CO)R 21 or-(CO)OR 21 ; R can independently represent hydrogen, halogen, nitro, cyano, thiocyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-(SO2)N(R 21 )2、-OR 21 -(CO)SR 21 -(CO)R 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -O(CO)OR 21 -CR 21 =N-OR 21 -C(N(R) 21 )2)=N-OR 21 or-(CO)OR 21 The "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally selected from halogen, nitro, cyano, C3-C8 cycloalkyl, C3-C8 cycloalkenyl, heterocyclic, aryl or -OR 21 At least one group in it is replaced; R8 represents hydrogen, C1-C8 alkyl, or halo-C1-C8 alkyl; R 21 Each of these groups independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkylC1-C8 alkyl, aryl, arylC1-C8 alkyl, heterocyclic or heterocyclicC1-C8 alkyl, wherein the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" is optionally substituted by at least one group selected from halogen, cyano, C1-C8 alkoxy or haloC1-C8 alkoxy; The aforementioned "C3-C8 cycloalkyl", "C3-C8 cycloalkenyl", "heterocyclic" or "aryl" may optionally be selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 ynyl, C3-C8 cycloalkyl, halo-C1-C8 alkyl, halo-C2-C8 alkenyl, halo-C2-C8 ynyl, halo-C3-C8 cycloalkyl, C3-C8 cycloalkyl substituted with C1-C8 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 At least one group in )2 is replaced; R 10 Each of these can be independently represented as hydrogen, C1-C8 alkyl, or halo-C1-C8 alkyl.

3. The piperidine compound according to claim 1 or 2, characterized in that, Y1, Y2, Y3, and Y4 independently represent hydrogen, halogen, C1-C6 alkyl, or halogenated C1-C6 alkyl, respectively; R1 represents hydrogen, halogen, -N(R) 21 2. C1-C6 alkyl, halo-C1-C6 alkyl, C2-C6 alkyl, halo-C2-C6 alkenyl, C2-C6 ynyl, halo-C2-C6 ynyl or -OR 21 ; R2 represents hydrogen, halogen, nitro, cyano, C1-C6 alkyl, halogenated C1-C6 alkyl, C2-C6 alkenyl, halogenated C2-C6 alkenyl, C2-C6 ynyl, halogenated C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-OR 21 -(C1-C6 alkylene)-OR 21 -(CO)R 21 or-(CO)OR 21 ; R can independently represent hydrogen, halogen, nitro, cyano, thiocyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl, -N(R) 21 )2、-(CO)N(R 21 )2、-O(CO)N(R 21 )2、-(SO2)N(R 21 )2、-OR 21 -(CO)SR 21 -(CO)R 21 -SR 21 -(SO)R 21 -(SO2)R 21 -O(CO)R 21 -O(CO)OR 21 -CR 21 =N-OR 21 -C(N(R) 21 )2)=N-OR 21 or-(CO)OR 21 The "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" is optionally selected from halogen, nitro, cyano, C3-C6 cycloalkyl, C3-C6 cycloalkenyl, heterocyclic, aryl or -OR 21 At least one group in it is replaced; R8 represents hydrogen, C1-C6 alkyl, or halo-C1-C6 alkyl; R 21 Each of these groups independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, C3-C6 cycloalkylC1-C6 alkyl, aryl, arylC1-C6 alkyl, heterocyclic or heterocyclicC1-C6 alkyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 ynyl" is optionally substituted by at least one group selected from halogen, cyano, C1-C6 alkoxy or haloC1-C6 alkoxy; The aforementioned "C3-C6 cycloalkyl", "C3-C6 cycloalkenyl", "heterocyclic" or "aryl" may optionally be selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 ynyl, C3-C6 cycloalkyl, halo-C1-C6 alkyl, halo-C2-C6 alkenyl, halo-C2-C6 ynyl, halo-C3-C6 cycloalkyl, C3-C6 cycloalkyl substituted with C1-C6 alkyl, -OR 10 -SR 10 -(CO)OR 10 -(SO2)R 10 or -N(R) 10 At least one group in )2 is replaced; R 10 Each of these can be independently represented as hydrogen, C1-C6 alkyl, or halo-C1-C6 alkyl.

4. The piperidine compound according to any one of claims 1-3, characterized in that, The compound is selected from any one of the compounds in Table 1.

5. A method for preparing a piperidine compound as described in any one of claims 1-4, comprising the following steps: (1) Prepared by reacting the compound of general formula II or its salt with the compound of general formula III. The reaction equation for compounds represented by general formula I is as follows: Alternatively, (2) react the compound of general formula IV or its salt with the compound of general formula V to prepare the compound of general formula I, and the reaction equation is as follows: Alternatively, (3) react compound VII with compound VI to obtain compound I, and the reaction equation is as follows: Where L1 represents halogen, and L2 represents halogen, -B(OH)2, or... L3 represents -B(OH)2 or Hal represents a halogen, and the substituents M1, M2, M3, M4, M5, R1, R2, Y1, Y2, Y3, Y4 and X are defined as described in any one of claims 1-4; Preferably, the reactions in steps (1), (2), and (3) are all carried out in the presence of a solvent and a base; More preferably, a catalyst is added to the reactions in steps (2) and (3); More preferably, the solvent in steps (1) and (2) is selected from at least one of dimethyl sulfoxide, N,N-dimethylformamide, dimethylacetamide, acetonitrile, dichloroethane, dioxane, dichloromethane, tetrahydrofuran, ethyl acetate, or toluene; the solvent in step (3) is a mixture of an organic solvent and water; the base in steps (1), (2), and (3) is selected from at least one of an inorganic base or an organic base; and / or the catalyst is selected from at least one of a palladium catalyst or a copper catalyst.

6. A nematicide composition, characterized in that, The compound comprises a biologically effective amount of any one of claims 1-4 of a piperidine compound; preferably, it further comprises a formulation adjuvant; more preferably, it further comprises other active ingredients.

7. A method for controlling nematodes, characterized in that, Includes a biologically effective amount of the piperidine compound of any one of claims 1-4 or the composition of claim 6, which exposes the nematode or its environment to biologically effective amounts.

8. Use of the piperidine compound as described in any one of claims 1-4 or the composition as described in claim 6 in the control of nematodes.

9. An intermediate as described in formula II, IV or VII of claim 5.

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