Amide compound with sterilization and nematicidal effects and application thereof

Abstract

The present invention provides a compound of formula I, and salts and stereoisomers thereof, x1, X2, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R10 are defined in the specification. The compound disclosed by the invention has relatively good bactericidal and nematicidal activity.

Description

Technical Field

[0001] The present invention belongs to the field of pesticide chemistry, and specifically relates to an amide compound having dual bactericidal and nematode-killing effects. The present invention also relates to compositions containing the compounds of the present invention and to their use in preventing plant diseases and pests in agriculture. Background Art

[0002] Plant parasitic nematodes are important plant pathogens, characterized by their cryptic nature, multi-host nature, persistence, and ease of transmission. Their rapid population growth and difficulty in control have severely impacted the yield and economic benefits of my country's grains, vegetables, and cash crops. Their primary host crops include soybeans, potatoes, cotton, corn, tomatoes, carrots, and sugar beets. Nematode damage is becoming increasingly severe, posing a serious threat to crop production. Globally, nematode damage can cause up to 14% annual crop yield losses, resulting in economic losses of US$80 billion to US$100 billion. In my country, nematode damage causes up to 12% annual crop yield losses, with annual soybean yield losses due to nematodes alone ranging from 5% to 80%. Parasitic nematodes damage plant roots, which can easily trigger pathogenic fungal infections, exacerbating bacterial, fungal, and viral attacks, disrupting plant growth and reducing crop yield and quality.

[0003] Amide compounds are used for bactericidal purposes primarily by inhibiting mitochondrial respiration by hindering electron transfer in succinate dehydrogenase in the respiratory chain. They have the characteristics of broad-spectrum bactericidal activity and good bactericidal efficacy. The applicant previously reported a class of novel amide compounds in patent CN116947749A. The general structure is as follows:

[0004]

[0005] , this type of compound has a good insecticidal effect.

[0006] CN106242998A reports a class of bisamide compounds with insecticidal activity, which have the following structure:

[0007]

[0008] CN104024225A discloses a class of compounds for killing insects, which have the following structure:

[0009]

[0010] Although the patent claims that it can be used to control agricultural pests and damage to plants caused by fungal diseases, it only measures its activity against nematodes and does not contain any data indicating that it can prevent and control plant diseases.

[0011] The amide compounds reported in the prior art do not show good nematicidal and plant disease control effects at low application rates. Developing amide compounds with high efficiency, excellent fungicidal effects and good nematicidal effects is an important research and development direction in the pesticide field. Summary of the Invention

[0012] The present invention provides an amide compound having excellent fungicidal and nematicidal activities at a low application amount.

[0013] Specifically, the present invention provides a compound of formula I and its salts and stereoisomers,

[0014]

[0015] in;

[0016] X1 and X2 are each independently N or C;

[0017] R1, R2, R3 and R4 are independently selected from H, halogen, CN, NO2, optionally substituted C1-C 10 Alkyl acyl, optionally substituted C1-C 10 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C1-C 10 Alkylsulfinyl, optionally substituted C1-C 10 alkylsulfonyl;

[0018] R5 and R6 are independently selected from H, halogen, nitro, cyano, optionally substituted C1-C6 alkyl;

[0019] R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, optionally substituted C1-C 10 Alkyl acyl, optionally substituted C1-C 10 alkyl, optionally substituted C2-C6 alkenyl, optionally substituted C2-C6 alkynyl, optionally substituted C2-C6 alkenyloxy, optionally substituted C2-C6 alkynyloxy, optionally substituted C3-C8 cycloalkyl, optionally substituted C1-C 10 Alkylsulfinyl, optionally substituted C1-C 10 Alkylsulfonyl, optionally substituted C1-C 10 Alkoxy, optionally substituted C1-C 10 Alkylthio.

[0020] The present invention also provides a composition comprising the compound of formula I of the present invention, its salt and stereoisomer thereof and at least one auxiliary agent selected from the group consisting of surfactants, solid diluents and liquid diluents.

[0021] The present invention also provides use of compound I, its salts, stereoisomers and the composition of the present invention in preventing and controlling plant diseases and insect pests.

[0022] Beneficial effects

[0023] The compound of the present invention has excellent nematode and fungicide effects and has broad application prospects in preventing and controlling plant diseases and insect pests. DETAILED DESCRIPTION

[0024] In order to make the purpose, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions in the embodiments of the present invention will be clearly and completely described below. Obviously, the described embodiments are part of the embodiments of the present invention, not all of the embodiments. Based on the embodiments of the present invention, all other embodiments obtained by ordinary technicians in this field without making creative work are within the scope of protection of the present invention. Unless otherwise expressly stated, throughout the specification and claims, the term "including" or its variations such as "comprising" or "including" will be understood to include the stated components or steps, without excluding other material components or steps.

[0025] Furthermore, in order to better illustrate the present invention, numerous specific details are given in the following detailed description.

[0026] Those skilled in the art will appreciate that the present invention can be practiced without certain specific details. In some embodiments, raw materials, methods, means, etc. well known to those skilled in the art are not described in detail in order to highlight the main purpose of the present invention.

[0027] When the compounds of the present invention are capable of existing in tautomeric forms, the above and below references to

[0028] The compounds described are to be understood as also comprising the corresponding tautomeric forms, even if these are not explicitly mentioned in each case.

[0029] If the compounds of the formula I according to the invention have functional groups which can be ionized, they can also be used in the form of their agriculturally acceptable salts or mixtures thereof.

[0030] The term "C1-C 10 The term "alkyl" refers to, for example, a straight or branched chain alkyl group containing 1 to 10 carbon atoms, preferably a C1-C6 alkyl group, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, neopentyl or n-hexyl, but is not limited thereto.

[0031] In the present invention, "C1-C 10The term "alkoxy" refers to, for example, a straight or branched alkoxy group containing 1 to 10 carbon atoms, preferably a C1-C6 alkoxy group, such as methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, n-pentoxy, isopentoxy, neopentoxy, or n-hexyloxy, but is not limited thereto.

[0032] In the present invention, "C 1- C 10 The term "alkylthio" refers to, for example, a straight or branched chain alkylthio group containing 1 to 10 carbon atoms, preferably a C1-C6 alkylthio group, such as methylthio, ethylthio, n-propylthio, isopropylthio, n-butylthio, sec-butylthio, tert-butylthio, n-pentylthio, isopentylthio, or n-hexyl, but is not limited thereto.

[0033] In the present invention, "C3-C8 cycloalkyl" refers to a cycloalkyl group containing 3-8 carbon atoms, which is a monocyclic group, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, etc., but not limited thereto.

[0034] In the present invention, "C1-C 10 "Alkylsulfinyl" refers to a straight or branched chain alkylsulfinyl group containing 1 to 10 carbon atoms, preferably a C1-C6 alkylsulfinyl group, for example, methylsulfinyl Examples of haloalkylsulfinyl groups include, but are not limited to, ethylsulfinyl, propylsulfinyl, propylsulfinyl, isopropylsulfinyl, n-butylsulfinyl, isobutylsulfinyl, secondary butylsulfinyl, and tertiary butylsulfinyl. Examples of haloalkylsulfinyl groups include, but are not limited to, chloro- and / or fluoro-halogenated substituents thereof, such as difluoromethylsulfinyl, trifluoromethylsulfinyl, and chlorodifluoromethylsulfinyl.

[0035] In the present invention, "C1-C 10 "Alkylsulfonyl" refers to a straight or branched chain alkylsulfonyl group containing 1 to 10 carbon atoms, preferably a C1-C6 alkylsulfonyl group, for example, methylsulfonyl Examples of the alkylsulfonyl group include, but are not limited to, ethylsulfonyl, propylsulfonyl, isopropylsulfonyl, n-butylsulfonyl, isobutylsulfonyl, secondary butylsulfonyl, and tertiary butylsulfonyl. Examples of the alkylsulfonyl group include, but are not limited to, alkylsulfonyl groups substituted with alkylsulfonyl groups having alkylsulfonyl groups and ...

[0036] In the present invention, "C2-C6 alkenyl" refers to a straight chain or branched alkenyl group containing 2-6 carbon atoms, which contains one or more double bonds, for example, vinyl, 1-propenyl, 1,3-butadienyl, etc., but is not limited thereto.

[0037] In the present invention, "C2-C6 alkynyl" refers to a straight chain or branched chain containing 2 to 6 carbon atoms and may have a triple bond at any position.

[0038] The present invention's "C3-C 10 Cycloalkyl C2-C6 alkynyl" refers to C3-C 10 The cycloalkyl group is linked to a C2-C6 alkynyl group, for example, cyclopropylethynyl, but not limited thereto.

[0039] The "C2-C6 alkenyloxy group" of the present invention refers to an alkenyloxy group containing 2 to 6 carbon atoms, for example, vinyloxy group, but is not limited thereto.

[0040] The "C2-C6 alkynyloxy group" of the present invention refers to an alkynyloxy group containing 2 to 6 carbon atoms, for example, ethynyloxy and 1-propynyloxy, but is not limited thereto.

[0041] The present invention "C1-C 10 The term "alkyl acyl" refers to a straight chain or branched chain alkyl acyl group containing 1 to 10 carbon atoms, preferably a C1-C6 alkyl acyl group, for example, formyl, acetyl, etc., but is not limited thereto.

[0042] The term "optionally substituted" means that the relevant group may be substituted by a substituent or may not be substituted.

[0043] When the group is substituted, the substituent may be C1-C 10 Alkyl, cyano, nitro, C3-C6 cycloalkyl, C1-C 10 Alkyl amido, C1-C 10 Alkoxy and halogen, etc., but not limited thereto, for example, when an alkyl group is substituted by a halogen, a haloalkyl group is formed, and the haloalkyl group preferably has a chain length of 1 to 6 carbon atoms, more preferably a chain length of 1 to 4 carbon atoms. Examples of haloalkyl groups include fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, 2,2,2-trifluoroethyl, 2-fluoroethyl, 2-chloroethyl, pentafluoroethyl, 1,1-difluoro-2,2,2-trichloroethyl, 2,2,3,3-tetrafluoroethyl and 2,2,2-trichloroethyl; preferably fluoromethyl, difluoromethyl, trifluoromethyl, trichloromethyl, difluorochloromethyl and dichlorofluoromethyl. Halogenated C1-C 10 Examples of the alkylsulfonyl group include, but are not limited to, a fluoromethylsulfonyl group and a trifluoromethylsulfonyl group.

[0044] In the present invention, halogen is usually fluorine, chlorine, bromine or iodine, preferably fluorine, bromine or chlorine.

[0045] The compounds of formula I in each case in free form or in salt form, and where appropriate their tautomers, may be present in the form of one of the possible isomers or as a mixture of these, for example in the form of pure isomers, such as enantiomers and / or diastereomers, or as isomer mixtures, such as enantiomeric mixtures, for example racemates, diastereomeric mixtures or racemic mixtures, depending on the number, absolute and relative configuration of the asymmetric carbon atoms present in the molecule, 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 isomer mixtures and the present invention should be understood in this sense in each case above and below (even if no specific stereochemical details are mentioned in each case). Therefore, the present invention covers all such isomers and tautomers and their mixtures in all proportions, as well as isotopic forms, such as deuterated compounds.

[0046] The present invention also encompasses salts or N-oxides of each compound of Formula I.

[0047] One of ordinary skill in the art will also appreciate that because salts of chemical compounds exist in equilibrium with their corresponding non-salt forms in the environment and under physiological conditions, the salts also possess the biological utility of the non-salt forms.

[0048] Therefore, the various salts of the compound of the present invention (and the active ingredient used in combination with the active ingredient of the present invention) can be used for preventing and treating plant diseases and insect pests. The salt among the salts allowed in agriculture and / or physiology includes the acid addition salts formed with the following inorganic acid or organic acid, 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. The salt among the salts allowed in agriculture and / or physiology can also be those whose cations do not adversely affect the plant disease prevention and treatment effect of the compound of Formula I. Therefore, especially suitable cations are ions of alkali metals (including sodium, potassium and lithium), ions of alkaline earth metals (including calcium and magnesium), and ions of transition metals (including manganese, copper, iron, zinc, cobalt, lead, silver, nickel).

[0049] Specifically, the present invention provides a compound of formula I and its salts and stereoisomers,

[0050]

[0051] in;

[0052] X1 and X2 are each independently N or C;

[0053] R1, R2, R3 and R4 are independently selected from H, halogen, CN, NO2, optionally substituted C1-C10 Alkyl acyl, optionally substituted C1-C 10 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C1-C 10 Alkylsulfinyl, optionally substituted C1-C 10 alkylsulfonyl;

[0054] R5 and R6 are independently selected from H, halogen, nitro, cyano, optionally substituted C1-C6 alkyl;

[0055] R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, optionally substituted C1-C 10 Alkyl acyl, optionally substituted C1-C 10 alkyl, optionally substituted C2-C6 alkenyl, optionally substituted C2-C6 alkynyl, optionally substituted C2-C6 alkenyloxy, optionally substituted C2-C6 alkynyloxy, optionally substituted C3-C8 cycloalkyl, optionally substituted C1-C 10 Alkylsulfinyl, optionally substituted C1-C 10 Alkylsulfonyl, optionally substituted C1-C 10 Alkoxy, optionally substituted C1-C 10 Alkylthio.

[0056] In Formula I of the present invention, X1, X2, R1, R2, R3 and R4 can be any of the following preferred combinations:

[0057] Preferably, X1 and X2 are each independently N or C.

[0058] Preferably, R1, R2, R3 and R4 are independently selected from H, halogen, CN, NO2, C1-C 10 Alkyl acyl, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, halogenated C1-C 10 Alkylsulfinyl and halogenated C1-C 10 An alkylsulfonyl group.

[0059] Preferably, R5 and R6 are independently selected from one of hydrogen, C1-C6 alkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogen, nitro and cyano.

[0060] Preferably, R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, C1-C 10Alkyl acyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C 10 Cycloalkyl C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, halogenated C1-C 10 Alkylsulfinyl, halogenated C1-C 10 Alkylsulfonyl, C1-C 10 Alkoxy and C1-C 10 One of the alkylthio groups.

[0061] In some embodiments, X1 and X2 are not N or C at the same time.

[0062] In some embodiments, X1 and X2 are both N or C.

[0063] In some embodiments, R1, R2, R3 and R4 are independently selected from H, halogen, CN, NO2, C1-C6 alkylacyl, C1-C6 alkyl, halo-substituted C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halo-substituted C1-C6 alkylsulfinyl and halo-substituted C1-C6 alkylsulfonyl.

[0064] In some embodiments, R1, R2, R3 and R4 are each independently selected from H, halogen, CN, NO2, halo-substituted C1-C6 alkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halo-substituted C1-C6 alkylsulfinyl and halo-substituted C1-C6 alkylsulfonyl.

[0065] In some embodiments, R1, R2, R3 and R4 are each independently selected from one of H, halogen, halogenated C1-C6 alkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfinyl and halogenated C1-C6 alkylsulfonyl.

[0066] In some embodiments, R1 and R4 are each independently selected from one of halogen, halogenated C1-C6 alkyl, C1-C6 alkylsulfonyl, and halogenated C1-C6 alkylsulfonyl.

[0067] In some embodiments, R1 and R4 are each independently selected from halogen, trifluoromethyl, trifluoromethylsulfonyl, or ethylsulfonyl.

[0068] In some embodiments, R5 and R6 are each independently selected from H, C1-C6 alkyl, halogen, nitro, or cyano.

[0069] In some embodiments, R5 is selected from C1-C6 alkyl, halogen, nitro, or cyano, and R6 is H.

[0070] In some embodiments, R5 is selected from ethyl and R6 is H.

[0071] In some embodiments, R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, C2-C6 alkynyl, C3-C 10 Cycloalkyl C2-C6 alkynyl, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, halogenated C1-C 10 Alkylsulfinyl, halogenated C1-C 10 Alkylsulfonyl, C1-C 10 Alkoxy and C1-C 10 One of the alkylthio groups.

[0072] In some embodiments, R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, C2-C6 alkynyl, C3-C 10 Cycloalkyl C2-C6 alkynyl, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, C1-C 10 Alkoxy and C1-C 10 One of the alkylthio groups.

[0073] In some embodiments, R7 and R9 are independently selected from halogen, nitro, cyano, C3-C 10 Cycloalkyl C2-C6 alkynyl, halogenated C1-C 10 Alkyl, C1-C 10 Alkylsulfonyl; preferably halogen, nitro, cyano, C3-C 10 Cycloalkyl C2-C6 alkynyl, halogenated C1-C6 alkyl, C1-C6 alkylsulfonyl.

[0074] In some embodiments, R7 and R9 are each independently selected from halogen, cyclopropylethynyl, trifluoromethyl, and ethylsulfonyl.

[0075] In some preferred embodiments, X1 is N, X2 is C, R1 is selected from chloro, trifluoromethyl or ethylsulfonyl, R2, R3 and R4 are H at the same time; R5 is selected from ethyl, R6 is H; R7 and R9 are independently selected from halogen, cyclopropylethynyl, trifluoromethyl and ethylsulfonyl; R8 and R 10 For H.

[0076] In some preferred embodiments, X1 is C, X2 is N, R1 is selected from chloro, trifluoromethyl or ethylsulfonyl, R2, R3 and R4 are H at the same time; R5 is selected from ethyl, R6 is H; R7 and R9 are independently selected from halogen, cyclopropylethynyl, trifluoromethyl and ethylsulfonyl; R8 and R 10 For H.

[0077] In some preferred embodiments, X1 is N, X2 is N, R1 is selected from chloro, trifluoromethyl or ethylsulfonyl, R2, R3 and R4 are H at the same time; R5 is selected from ethyl, R6 is H; R7 and R9 are independently selected from halogen, cyclopropylethynyl, trifluoromethyl and ethylsulfonyl; R8 and R 10 For H.

[0078] Particularly preferably, the compound of formula I of the present invention is selected from the following compounds:

[0079]

[0080] General synthesis process

[0081] In this specification, if there is any difference between the chemical name and the chemical structure, the structure is the preferred one. Generally, the compounds of the present invention can be prepared by the methods described herein, unless otherwise specified. The following synthetic schemes and examples are provided to further illustrate the present invention.

[0082] Those skilled in the art will recognize that the chemical reactions described herein can be used to appropriately prepare many other compounds of the present invention, and other methods for preparing the compounds of the present invention are considered to be within the scope of the present invention. For example, the synthesis of non-exemplified compounds according to the present invention can be successfully accomplished by those skilled in the art through modification methods, such as appropriate protection of interfering groups, by utilizing other known reagents (in addition to those described herein), or by making some conventional modifications to the reaction conditions. In addition, the reactions disclosed herein or known reaction conditions are also generally applicable to the preparation of other compounds of the present invention.

[0083] The compounds of the present invention can be synthesized by the following routes:

[0084]

[0085] Among them, X1, X2, R1, R2, R3, R4, R5, R6, R7, R8, R9 and R 10 The definition of is as defined above.

[0086] A specific synthesis process is to directly contact and react the compound III with the compound II under alkaline conditions in the presence of a condensing agent to synthesize compound I. Preferably, the condensing agent is HATU, HOBT, PyBOP, EDCI, etc., the base is triethylamine, pyridine, potassium carbonate, sodium carbonate, etc., and the reaction temperature is 20-30 degrees Celsius.

[0087] Preferably, the above synthesis process is to react the compound of formula I with an acylating agent to form an acyl chloride, and then the acylated product is contacted with the compound of formula II under alkaline conditions to synthesize compound III. Preferably, the acylating agent is thionyl chloride or oxalyl chloride, the reaction solvent is dichloroethane, dichloromethane, toluene, chloroform, chlorobenzene, etc., the base is triethylamine, pyridine, potassium carbonate, sodium carbonate, etc., and the reaction temperature is 20-80 degrees Celsius.

[0088] The present invention also discloses a compound of formula II as an intermediate for preparing a compound of formula I, having the following structure:

[0089]

[0090] wherein X2 are each independently N or C;

[0091] R1, R2, R3 and R4 are independently selected from H, halogen, CN, NO2, optionally substituted C1-C 10 Alkyl acyl, optionally substituted C1-C 10 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C1-C 10 Alkylsulfinyl, optionally substituted C1-C 10 Alkylsulfonyl.

[0092] Preferably, X2 is independently N or C.

[0093] Preferably, R1, R2, R3 and R4 are independently selected from H, halogen, CN, NO2, C1-C 10 Alkyl acyl, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, halogenated C1-C 10 Alkylsulfinyl and halogenated C1-C 10 Alkylsulfonyl.

[0094] In some embodiments, R1, R2, R3 and R4 are independently selected from one of H, halogen, CN, NO2, C1-C6 alkylacyl, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfinyl and halogenated C1-C6 alkylsulfonyl.

[0095] In some embodiments, R1, R2, R3 and R4 are each independently selected from one of H, halogen, CN, NO2, halogenated C1-C6 alkyl, C1-C6 alkylsulfonyl and halogenated C1-C6 alkylsulfonyl.

[0096] In some embodiments, R1, R2, R3 and R4 are each independently selected from one of H, halogen, halogenated C1-C6 alkyl, C1-C6 alkylsulfonyl and halogenated C1-C6 alkylsulfonyl.

[0097] In some embodiments, R1 and R4 are independently selected from one of halogen, halogenated C1-C6 alkyl or C1-C6 alkylsulfonyl, C1-C6 alkylsulfonyl and halogenated C1-C6 alkylsulfonyl.

[0098] In some embodiments, R1 and R4 are each independently selected from one of halogen, trifluoromethyl, ethylsulfonyl, and trifluoromethylsulfonyl.

[0099] In some preferred embodiments, X2 is C, and R1 is selected from one of chloro, trifluoromethyl, ethylsulfonyl and trifluoromethylsulfonyl.

[0100] In some preferred embodiments, X2 is N, and R1 is selected from one of chloro, trifluoromethyl, ethylsulfonyl and trifluoromethylsulfonyl.

[0101] The present invention also provides a compound of formula III for preparing a compound of formula I,

[0102]

[0103] in;

[0104] X1 is selected from N or C;

[0105] R5 and R6 are independently selected from H, halogen, nitro, cyano, optionally substituted C1-C6 alkyl;

[0106] R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, optionally substituted C1-C 10 Alkyl acyl, optionally substituted C1-C 10alkyl, optionally substituted C2-C6 alkenyl, optionally substituted C2-C6 alkynyl, optionally substituted C2-C6 alkenyloxy, optionally substituted C2-C6 alkynyloxy, optionally substituted C3-C8 cycloalkyl, optionally substituted C1-C 10 Alkylsulfinyl, optionally substituted C1-C 10 Alkylsulfonyl, optionally substituted C1-C 10 Alkoxy, optionally substituted C1-C 10 Alkylthio.

[0107] Preferably, X1 is selected from N or C.

[0108] Preferably, R5 and R6 are independently selected from R5 and R6 are independently selected from H, halogen, nitro, cyano, C1-C6 alkyl.

[0109] Preferably, R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, C1-C 10 Alkyl acyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C 10 Cycloalkyl C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, halogenated C1-C 10 Alkylsulfinyl, halogenated C1-C 10 Alkylsulfonyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio.

[0110] In some embodiments, R5 and R6 are each independently selected from H, C1-C6 alkyl, halogen, nitro, or cyano.

[0111] In some embodiments, R5 is selected from C1-C6 alkyl, halogen, nitro, or cyano.

[0112] In some embodiments, R5 is selected from ethyl and R6 is H.

[0113] In some embodiments, R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, C2-C6 alkynyl, C3-C 10 Cycloalkyl C2-C6 alkynyl, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C1-C 10 Alkylsulfinyl, C1-C10 Alkylsulfonyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio.

[0114] In some embodiments, R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, C2-C6 alkynyl, C3-C 10 Cycloalkyl C2-C6 alkynyl, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, halogenated C1-C 10 Alkylsulfinyl, halogenated C1-C 10 Alkylsulfonyl, C1-C 10 Alkoxy, C1-C 10 Alkylthio.

[0115] In some embodiments, R7 and R9 are independently selected from halogen, nitro, cyano, C3-C 10 Cycloalkyl C2-C6 alkynyl, halogenated C1-C 10 Alkyl, C1-C 10 Alkylsulfonyl, halogenated C1-C 10 Alkylsulfinyl, halogenated C1-C 10 alkylsulfonyl;

[0116] In some embodiments, R7 and R9 are independently selected from halogen, cyclopropylethynyl, trifluoromethyl, and ethylsulfonyl;

[0117] In some preferred embodiments, X1 is N, R1 is selected from chloro, trifluoromethyl or ethylsulfonyl; R5 is selected from ethyl, R6 is H; R7 and R9 are independently selected from halogen, cyclopropylethynyl, trifluoromethyl and ethylsulfonyl; R8 and R 10 is H;

[0118] In some preferred embodiments, X1 is C, R1 is selected from chloro, trifluoromethyl or ethylsulfonyl; R5 is selected from ethyl, R6 is H; R7 and R9 are independently selected from halogen, cyclopropylethynyl, trifluoromethyl and ethylsulfonyl; R8 and R 10 For H.

[0119] The present invention also provides a composition comprising the compound of formula II of the present invention and at least one adjuvant selected from the group consisting of surfactants, solid diluents and liquid diluents.

[0120] The present invention relates to use of the compound or a composition containing the compound as a fungicide and insecticide in agriculture or gardening, for controlling or preventing useful plants from being attacked by diseases and pests.

[0121] The diseases described in the present invention include, but are not limited to, the following:

[0122] Oomycete diseases, such as downy mildew, white rust, damping-off, cotton rot, blight, late blight, etc.;

[0123] Deuteromycin diseases, such as wilt, root rot, damping-off, anthracnose, verticillium wilt, black spot, gray mold, brown spot, black spot, leaf spot, early blight, ring rot, leaf blight, and stem base rot;

[0124] Basidiomycete diseases, such as rust and smut;

[0125] Ascomycete diseases, such as powdery mildew, sclerotinia disease (flax sclerotinia disease, rapeseed sclerotinia disease, soybean sclerotinia disease, peanut sclerotinia disease, tobacco sclerotinia disease, pepper sclerotinia disease, eggplant sclerotinia disease, bean sclerotinia disease, pea sclerotinia disease, cucumber sclerotinia disease, bitter melon sclerotinia disease, wax gourd sclerotinia disease, watermelon sclerotinia disease, celery sclerotinia disease), black spot disease, etc.

[0126] The compound represented by formula I or its salt as an active ingredient can be used as a nematocide, which is suitable for controlling nematodes in the soil of fruit trees, vegetables, other crops and ornamental plants.

[0127] Examples of nematodes to which the nematicides of the present invention can be applied include, but are not limited to, root-knot nematodes such as southern root-knot nematodes (Meloidogyne incognita), Javan root-knot nematodes (Meloidogyne javanica), northern root-knot nematodes (Meloidogyne hapla), and peanut root-knot nematodes (Meloidogyne arenaria); Ditylenchus nematodes such as potato rot nematodes (Ditylelenchus destructor) and bulb-rot nematodes (Ditylelenchus dipsaci); Pratylenchus nematodes such as northern root-rot nematodes (Pratylenchus penetrans), chrysanthemum root-rot nematodes (Pratylenchus pseudobrylenchus); and fallax), coffee root rot nematodes (Pratylenchus coffeae), tea root rot nematodes (Pratylenchus loosi), and walnut root rot nematodes (Pratylenchus vulnus); nematodes of the genus Heterodera, such as the golden wireworm (Globodera rostochiensis) and the potato cyst nematode (Globodera pallida); nematodes of the genus Heterodera, such as the soybean cyst nematode (Heterodera glycines) and the beet cyst nematode (Heterodera shachtoii); nematodes of the genus Aphelenchoides, such as the rice stem cyst nematode (Aphelenchoides spp.); besseyi), chrysanthemum leaf bud sliding nematode (chrysanthemum sliding nematode (Aphelenchoidesritzemabosi)) and strawberry sliding nematode (strawberry sliding nematode (Aphelenchoidesfragarieae)); true sliding nematodes such as the fungus-feeding nematode (oat true sliding nematode (Aphelenchus avenae)); Radopholus nematode such as the radial nematode (banana radial nematode (Radopholus similis)); Pad nematode nematode such as the citrus nematode (Tylenchulus semipenetrans); Rotylenchulus nematode such as the kidney-shaped spiral nematode (Rotylenchulus reniformis); nematodes occurring on trees such as the pine wood nematode (Bursaphelenchus xylophilus), etc.Furthermore, the nematode-killing composition of the present invention is also effective against animal parasitic nematodes such as Ascaris, Pinworm, Anisakis, Filarial worms, Wuchereria bancrofti, Onchocerca volvulus and Gnathostoma.

[0128] The plant objects to which the compounds of the present invention can be applied are not particularly limited; for example, cereals (e.g., rice, barley, wheat, rye, oats, corn, sorghum, etc.), legumes (soybeans, adzuki beans, broad beans, peas, peanuts, etc.), fruit trees / fruits (apples, citrus, pears, grapes, peaches, Japanese apricots, cherries, walnuts, apricots, bananas, strawberries, etc.), vegetables (cabbage, tomatoes, spinach, broccoli, lettuce, onions, green onions, green peppers, etc.), root vegetables (carrots, potatoes, sweet potatoes, radishes, etc.), The main crops include: radish, lotus root, turnip, etc.), industrial crops (cotton, hemp, paper mulberry, jasmine, rapeseed, sugar beet, hops, sugarcane, sugar beet, olives, rubber, coffee, tobacco, tea, etc.), berries (pumpkin, cucumber, watermelon, melon, etc.), forage grasses (orchard grass, milo, timothy, alfalfa, lucerne, etc.), lawn grasses (Korean zoysia, bentgrass, etc.), spices and other crops (lavender, rosemary, thyme, parsley, pepper, ginger, etc.), and flowers (chrysanthemum, rose, orchid, etc.).

[0129] The compounds of the present invention can generally be used as active ingredients of pesticides in compositions or formulations, which usually also include pesticide-acceptable surfactants and carriers. The carriers can be solid carriers or liquid carriers.

[0130] Suitable solid carriers include natural or synthetic clays and silicates, such as natural silica and diatomaceous earth; magnesium silicates, such as talc; magnesium aluminum silicates, such as kaolinite, kaolin, montmorillonite and mica; white carbon black, calcium carbonate, light calcium carbonate; calcium sulfate; limestone; sodium sulfate; ammonium salts, such as ammonium sulfate, hexamethylenediamine and urea, etc.

[0131] Liquid carriers include water and organic solvents. When water is used as the solvent or diluent, organic solvents can also be used as adjuvants or antifreeze additives. Useful liquefied gaseous fillers or carriers are those liquids that are gaseous at standard temperature and standard pressure, such as aerosol propellants, such as halogenated hydrocarbons, butane, propane, nitrogen and carbon dioxide, etc.

[0132] Suitable organic solvents include aromatic hydrocarbons, such as benzene, xylene, toluene, etc.; chlorinated hydrocarbons, such as chlorobenzene, vinyl chloride, chloroform, dichloromethane, etc.; aliphatic hydrocarbons, such as petroleum fractions, cyclohexane, light mineral oil; alcohols, such as isopropyl alcohol, butanol, ethylene glycol, glycerol and cyclohexanol, etc.; and their ethers and esters; ketones, such as acetone, cyclohexanone, dimethylformamide and N-methyl-pyrrolidone, vegetable oils, such as soybean oil, rapeseed oil and cottonseed oil, etc.

[0133] Suitable surfactants (adjuvants, emulsifiers, dispersants, protective colloids, wetting agents and binders) include all common ionic and nonionic substances, for example ethoxylated nonylphenols, polyalkylene glycol ethers of linear or branched alcohols, reaction products of alkylphenols with ethylene oxide and / or propylene oxide, reaction products of fatty acid amines with ethylene oxide and / or propylene oxide, and also fatty acid esters, alkylsulfonates, alkyl sulfates, alkyl ether sulfates, alkyl ether phosphates, aryl sulfates, ethoxylated arylalkylphenols (such as tristyrylphenol ethoxylate), and ethoxylated and propoxylated arylalkylphenols, such as sulfated and phosphated arylalkylphenol ethoxylates and -ethoxylates and -propoxylates. Other examples are natural and synthetic water-soluble polymers, such as ligninsulfonates, gelatin, gum arabic, phospholipids, starch, hydrophobically modified starch and cellulose derivatives, in particular cellulose esters and cellulose ethers, as well as polyvinyl alcohol, polyvinyl acetate, polyvinyl pyrrolidone, polyacrylic acid, polymethacrylic acid and copolymers of (meth)acrylic acid and (meth)acrylic esters, as well as copolymers of methacrylic acid and methacrylic esters neutralized with alkali metal hydroxides, and condensates of optionally substituted naphthalenesulfonates with formaldehyde. If one of the active ingredients and / or one of the inert carriers is insoluble in water and application is carried out in water, the presence of a surfactant is essential.

[0134] The pesticide / insecticide of the present invention can be prepared by a conventional method. For example, the active substance is mixed with a liquid solvent and / or a solid carrier, and a surfactant such as an emulsifier, dispersant, stabilizer, or wetting agent is added. Other adjuvants such as adhesives, defoamers, foaming agents, antioxidants, crystallization inhibitors, viscosity modifiers, suspending agents, spray droplet regulators, pigments, neutralizers and buffers, corrosion inhibitors, dyes, flavoring agents, spreading agents, penetration aids, micronutrients, dispersants, thickeners, freezing point depressants, and antimicrobial agents may also be added.

[0135] The fungicide / insecticide of the present invention can be applied in the form of its formulation or in a use form prepared therefrom, such as, but not limited to, capsule suspensions, fine granules, foams, pastes, suspension concentrates, suspoemulsion concentrates, soluble concentrates, suspensions, wettable powders, soluble powders, dusts and granules, water-soluble and water-dispersible granules or tablets, and the like.

[0136] The formulation of the present invention may also contain other components, such as other fungicides, insecticides, herbicides, plant growth regulators, attractants, acaricides, nematicides, fertilizers, safeners, etc., which can be formulated with liquid fertilizers or solid, granular fertilizer carriers such as ammonium nitrate, urea, etc., or mixed with fine sand or soil.

[0137] When a pesticide composition containing a compound of Formula I of the present invention is used to control plant pests and diseases in the form of an emulsifiable concentrate, wettable powder, or microemulsion, these formulations are typically diluted with water to a concentration of the active ingredient [i.e., the compound of Formula I] within a range of 0.01 to 5000 ppm for application. Granules or powders have been studied for application without dilution. Research results have shown that the compound of Formula I of the present invention has an inhibition rate or lethality of at least 90% against certain diseases and pests at a concentration of 0.01 to 100 ppm (0.01 mg / L to 100 mg / L), preferably at a concentration of 0.01 ppm to 10 ppm. Particularly preferred compounds have an inhibition rate or lethality of at least 80% against certain diseases and pests at a concentration of 0.1 ppm to 1.5 ppm.

[0138] Preparation Example

[0139] In this specification, if there is any difference between the chemical name and the chemical structure, the structure is preferred. Generally, the compounds of the present invention can be prepared by the methods described herein, unless otherwise specified. The raw materials, reagents, etc. used to prepare the compounds of the present invention are all commercially available or can be prepared by methods conventional in the art.

[0140] Example 1 Preparation of N-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-ethylcyclopropyl)methyl)-2-(trifluoromethyl)nicotinamide (PPN-01)

[0141]

[0142] The specific preparation process is as follows:

[0143] (1) In a 250 mL reaction flask equipped with a stirrer, reflux condenser, and thermometer, add the compound 2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl}-acetonitrile (11 g, 0.05 mol), 60 ml of methanol, and pyridine (15.9 g, 0.2 mol), then heat to 50°C, and add n-propanal (17.4 g, 0.3 mol) dropwise over 2 h. After reacting for 4 h, the resulting reaction solution was desolvated to obtain 15.6 g of compound (E)-2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)pent-2-enenitrile.

[0144] (2) In a 250 mL reaction flask equipped with a stirrer, reflux condenser and thermometer, 60 mL of DMSO, trimethylsulfoxide iodide (13.2, 0.06 mol) and sodium hydroxide (2.4 g, 0.06 mol) were added and stirred at room temperature for 20 minutes. Then, (E)-2-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)pent-2-enenitrile was added and stirred at room temperature for 2 hours. The reaction was stopped and extracted with water and ethyl acetate. The organic phase was washed twice with water and then washed with saturated brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The obtained product was separated and purified by column chromatography to obtain 7 g of compound 1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-ethylcyclopropane-1-carbonyl.

[0145] (3) Add 7 g of 1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-ethylcyclopropane-

[0146] 1-carbonyl, 40 g of methanol, 0.7 g of Raney nickel, 3 eq of ammonia water, and 30 kg of hydrogen were added. The mixture was reacted at 90° for 6 h, filtered, and the filter cake was rinsed with methanol. The filtrate was dried to obtain 7.7 g of (1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-ethylcyclopropyl)methanamine.

[0147] (4) In a 250 mL reaction flask equipped with a stirrer, reflux condenser, and thermometer, 5.56 g of (1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-ethylcyclopropyl)methylamine, 40 ml of tetrahydrofuran, EDCI (5.7 g, 0.03 mol), and 2-trifluoromethylnicotinic acid (3.8 g, 0.02 mol) were added dropwise at room temperature. After the addition was complete, the reaction was allowed to proceed for 0.5 h. The reaction was stopped and most of the tetrahydrofuran was removed. The mixture was extracted with water and ethyl acetate. The organic phase was desolvated to obtain 10 g. Column chromatography gave 3 g of N-(1-(3-chloro-5-(trifluoromethyl)pyridin-2-yl)-2-ethylcyclopropyl)methyl)-2-(trifluoromethyl)nicotinamide, with a yield of 33.3%. 1 HNMR(500MHz,DMSO)δ8.95(t,J=6.3Hz,1H),8.82(d,J=4.8Hz,1H),8.43(s,1H),8.16(s,1H),7.94(d,J=7.9Hz,1H),7.09(dd,J=7.9,4.8Hz,1H) ,3.91(d,J=6.3Hz,2H),,1.49(q,J=6.9Hz,2H),1.39(m,4H),1.27(dd,J=11.0,8.1Hz,1H), 0.97(dd,J=11.0,7.5Hz,1H), 0.86(t,J=7.4Hz,3H).

[0148] Example 2 Preparation of N-(1-(4-(cyclopropylethynyl)-2-(ethylsulfonyl)phenyl)cyclopropyl)methyl)-2-(trifluoromethyl)nicotinamide (PPN-03)

[0149]

[0150] The specific preparation process is as follows:

[0151] (1) In a 250 mL reaction flask equipped with a stirrer, reflux condenser and thermometer, 2-(4-bromo-2-chlorophenyl)acetonitrile (23 g, 0.1 mol) and 60 ml of THF were added, and the temperature was lowered to about 0 degrees. Sodium ethanethiolate (8.4 g, 0.1 mol) was added slowly at 0 degrees. After the addition was completed, the mixture was stirred at 0 degrees for 1 hour and then at room temperature for 3 hours. The mixture was quenched with sodium hypochlorite aqueous solution, and then extracted with water and ethyl acetate. The organic phase was washed twice with water, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The obtained product was separated and purified by column chromatography to obtain 11.5 g of compound 2-(4-bromo-2-(ethylsulfonyl)phenyl)acetonitrile.

[0152] (2) In a 250 mL reaction flask equipped with a stirrer, reflux condenser and thermometer, add the compound 2-(4-bromo-2-(ethylsulfonyl)phenyl)acetonitrile (11.5 g, 0.05 mol) and 60 ml of DMF, then cool to about 0 degrees Celsius. Add NaH (60%, 6 g, 0.15 mol) in batches while controlling the temperature at about 0 degrees Celsius. After the addition is complete, stir for 0.5 hours, then add 1,3-dibromoethane (28, 0.15 mol) dropwise for 1 hour. After reacting at room temperature for 3 hours, add water, and extract with ethyl acetate. Wash the organic phase twice with water, wash the organic phase with saturated brine, dry over anhydrous sodium sulfate, filter, and concentrate the filtrate under reduced pressure. The obtained product is separated and purified by column chromatography to obtain 7 g of the compound 1-(4-bromo-2-(ethylsulfonyl)phenyl)cyclopropane-1-carbonitrile.

[0153] (3) To a 250 ml hydrogenation reactor were added 7 g of 1-(4-bromo-2-(ethylsulfonyl)phenyl)cyclopropane-1-carbonitrile, 40 g of methanol, 0.7 g of Raney nickel, and 3 g of aqueous ammonia. 20 kg of hydrogen was introduced and the reaction was carried out at room temperature for 6 h. The mixture was filtered and the filter cake was rinsed with methanol. The filtrate was dried to obtain 7.7 g of the crude compound (1-(4-bromo-2-(ethylsulfonyl)phenyl)cyclopropyl)methanamine.

[0154] (4) In a 250 mL reaction flask equipped with a stirrer, reflux condenser, and thermometer, 4.6 g of the crude intermediate (1-(4-bromo-2-(ethylsulfonyl)phenyl)cyclopropyl)methylamine, 40 ml of tetrahydrofuran, EDCI (5.7 g, 0.03 mol), and 2-trifluoromethylnicotinic acid (3.8 g, 0.02 mol) were added dropwise at room temperature. After the addition was complete, the reaction was allowed to proceed for 0.5 h. The reaction was stopped and most of the tetrahydrofuran was removed. After addition of water, ethyl acetate was added for extraction. The organic phase was desolvated to obtain 8 g of the compound N-(1-(4-bromo-2-(ethylsulfonyl)phenyl)cyclopropyl)methyl)-2-(trifluoromethyl)nicotinamide.

[0155] (5) A 250 mL reaction flask equipped with a stirrer, reflux condenser, and thermometer was charged with 4.5 g of N-(1-(4-bromo-2-(ethylsulfonyl)phenyl)cyclopropyl)methyl)-2-(trifluoromethyl)nicotinamide and 40 mL of DMF. Triphenylphosphine (2 mmol), palladium chloride (2 mmol), triethylamine (0.015 mol), and cyclopropylacetylene (0.02 mol) were added under nitrogen protection and reacted at 90°C for 3 h. The mixture was cooled to room temperature, extracted with water and ethyl acetate, and the organic phase was washed with saturated brine, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting product was separated and purified by column chromatography to obtain 1.8 g of N-(1-(4-(cyclopropylethynyl)-2-(ethylsulfonyl)phenyl)cyclopropyl)methyl)-2-(trifluoromethyl)nicotinamide in a yield of 43%. 1 H NMR (500MHz, DMSO) δ8.95(t,J=6.3Hz,1H),8.82(d,J=4.8Hz,1H),8.43(s,1H),8.16(s,1H),7.94(d,J=7.9Hz,1H),7.09(dd,J=7.9,4 .8Hz,1H),3.91(d,J=6.3Hz,2H),3.54(q,J=7.2Hz,2H),1.79(tt,J=8.1,7.5Hz,1H),1.41(q,J=7.2Hz,3H),1.21(m,4H),0.81(m,4H).

[0156] Table 1 Example compounds and compounds synthesized by similar methods according to the above examples

[0157]

[0158]

[0159] Biological activity assay

[0160] 1. Determination of nematicidal activity of southern root-knot nematodes

[0161] 1. Test reagents

[0162] Compounds PPN-01, PPN-02 and PPN-03 were prepared by the applicant's laboratory.

[0163] 2. Preparation of medicine

[0164] Preparation of pharmaceutical preparation: Dissolve the compound of the present invention and the control drug in acetone respectively, then add Tween 80 to dilute and prepare single-dose stock solutions. Set up multiple groups of ratios, and the amount of drug solution for each mass concentration should be no less than 10 ml for standby use.

[0165] 3. Preparation of nematode solution:

[0166] (1) Picking up root-knot nematode eggs: Use pointed tweezers to peel off the root-knot nematode eggs on the surface of the root system of the plant (cucumber), then put them into a beaker filled with pure water, pierce the hole with filter paper, and incubate them at 25℃ for 48 hours.

[0167] (2) Preparation of nematode liquid: After culturing the eggs for 48 h, filter through filter cloth to remove the egg masses and obtain the second-instar larvae of the same age.

[0168] (3) Population Base Survey: Take 1 ml of the mixed liquid containing root-knot nematodes and place it in a counting dish. Count the nematodes under a dissecting microscope to ensure that the nematode suspension contains ≥100 nematodes per ml. If the number of nymphs is small, centrifuge the suspension at 1000 rpm for 2 minutes, discard the supernatant, and centrifuge again. Finally, dilute the nematode suspension with pure water to ≥100 nematodes per ml and set aside.

[0169] 4. Nematicidal test on southern root-knot nematode

[0170] Pipette 100 μL of the hatched nematode fluid into a well of a culture plate. Dilute the aforementioned preparation to active ingredient concentrations of 10 ppm, 5 ppm, and 2.5 ppm. Add 100 μL of each concentration to the culture dish. Maintain the room temperature at 25°C during the experiment. Perform three replicates for each concentration and observe after 24 hours. A blank control containing no chemical was also used: water.

[0171] 5. Investigation

[0172] 24 hours after drug administration, the nematode death was observed under a dissecting microscope.

[0173] 6. Data calculation method

[0174] Based on the survey data, the mortality rate and the adjusted mortality rate of each treatment were calculated in percentage (%). The calculation results were rounded to four decimal places according to companies (1) and (2).

[0175]

[0176] Where:

[0177] P1 represents mortality rate;

[0178] K represents the number of dead nematodes;

[0179] N represents the total number of insects surveyed.

[0180]

[0181] Where:

[0182] P2 represents the adjusted mortality rate;

[0183] P t represents the mortality of treated nematodes;

[0184] P0 represents the mortality rate of control nematodes.

[0185] Table 2 Nematicidal test data on southern root-knot nematodes

[0186]

[0187]

[0188] 2. Determination of the activity of mango anthracnose

[0189] 1. Test pathogens

[0190] Pathogen: Mango Anthrax. The pathogen is cultured and expanded under aseptic operation in the laboratory for future use.

[0191] 2. Preparation of medicine is the same as

[0192] Preparation of pharmaceutical preparation: The compound PPN-01 of the present invention and the control drug were dissolved in acetone, and then diluted with Tween 80 to prepare single-dose stock solutions. Multiple groups of preparation ratios were set up, and the amount of drug solution for each mass concentration was not less than 10 ml.

[0193] 3. Preparation of drug-containing tablets

[0194] First, melt the PDA culture medium (potato dextrose agar) and cool it to 45-50℃, add the drug according to the experimental design concentration, mix well and pour it into the culture dish to make a drug-containing plate, and cool it naturally for use.

[0195] 4. Inoculation

[0196] A 6 mm diameter punch was used to punch bacterial cakes along the edge of the colony. These cakes were then placed on culture media containing a series of pre-concentrations (5 ppm, 2.5 ppm, 1.25 ppm, 0.625 ppm, and 0.3125 ppm) of the compound PPN-01 of this invention. Untreated culture media served as a control. One bacterial cake was placed on each plate, and this process was repeated three times. After incubation at 25°C for 8 days, the colonies were assessed for growth.

[0197] 5. Survey Methods

[0198] After culturing anthrax for 8 days, the colony diameter or extended growth was measured with a caliper and the average value was obtained by the cross-hatch method.

[0199] 6. Calculation method

[0200] According to the survey results, the mycelial growth inhibition rate of each concentration on the target bacteria was calculated according to formula (1) (2), and the unit was percentage (%). The calculation results were rounded to two decimal places.

[0201] D=D1-D2…………(1)

[0202]

[0203] Where: D—colony growth diameter; D1—colony diameter; D2—bacteria cake diameter; I—mycelial growth inhibition rate; D0—blank control colony growth diameter; D t —The growth diameter of the colony after drug treatment.

[0204] The mycelium growth inhibition rate was converted into the inhibition probability value (Y), and the drug concentration was converted into the concentration logarithm (X). The toxicity formula of different fungicides on pathogens was obtained by the concentration logarithm and probability value regression method, and the inhibition median concentration (EC) of each agent on the pathogen was calculated from the toxicity formula. 50 )value.

[0205] Table 3 Inhibitory effect of the compounds of the present invention on mango anthracnose

[0206]

[0207] The preferred embodiments of the present invention have been described in detail above, but the present invention is not limited thereto. Within the technical concept of the present invention, various simple variations of the technical solution of the present invention may be made, including combining the various technical features in any other appropriate manner. These simple variations and combinations should also be regarded as disclosed in the present invention and fall within the scope of protection of the present invention.

Claims

1. A compound of formula I and its salts and stereoisomers, in; X1 and X2 are each independently N or C; R1, R2, R3 and R4 are independently selected from H, halogen, CN, NO2, optionally substituted C1-C 10 Alkyl acyl, optionally substituted C1-C 10 alkyl, optionally substituted C3-C8 cycloalkyl, optionally substituted C1-C 10 Alkylsulfinyl, optionally substituted C1-C 10 alkylsulfonyl; R5 and R6 are independently selected from H, halogen, nitro, cyano, optionally substituted C1-C6 alkyl; R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, optionally substituted C1-C 10 Alkyl acyl, optionally substituted C1-C 10 alkyl, optionally substituted C2-C6 alkenyl, optionally substituted C2-C6 alkynyl, optionally substituted C2-C6 alkenyloxy, optionally substituted C2-C6 alkynyloxy, optionally substituted C3-C8 cycloalkyl, optionally substituted C1-C 10 Alkylsulfinyl, optionally substituted C1-C 10 Alkylsulfonyl, optionally substituted C1-C 10 Alkoxy, optionally substituted C1-C 10 Alkylthio.

2. The compound of formula I and its salt and stereoisomers according to claim 1, characterized in that: R1, R2, R3 and R4 are independently selected from H, halogen, CN, NO2, C1-C 10 Alkyl acyl, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, halogenated C1-C 10 Alkylsulfinyl and halogenated C1-C 10 One of alkylsulfonyl groups; preferably one of H, halogen, CN, NO2, C1-C6 alkylacyl, C1-C6 alkyl, halogenated C1-C6 alkyl, C3-C6 cycloalkyl, C1-C6 alkylsulfinyl, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfinyl and halogenated C1-C6 alkylsulfonyl.

3. The compound of formula I and its salt and stereoisomer thereof according to claim 1, characterized in that: R1 and R4 are independently selected from one of halogen, halogenated C1-C6 alkyl, C1-C6 alkylsulfonyl and halogenated C1-C6 alkylsulfonyl; preferably one of halogen, trifluoromethyl, trifluoromethylsulfonyl and ethylsulfonyl.

4. The compound of formula I and its salt and stereoisomer thereof according to claim 1, characterized in that: R5 and R6 are each independently selected from H or C1-C6 alkyl.

5. The compound of formula I and its salt and stereoisomers according to claim 1, characterized in that: R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, C1-C 10 Alkyl acyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C 10 Cycloalkyl C2-C6 alkynyl, C2-C6 alkenyloxy, C2-C6 alkynyloxy, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C3-C 10 Cycloalkyl, C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, halogenated C1-C 10 Alkylsulfinyl, halogenated C1-C 10 A C1-C 10 Alkoxy and C1-C 10 One of the alkylthio groups; preferably, R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, nitro, cyano, C2-C6 alkynyl, C3-C 10 Cycloalkyl C2-C6 alkynyl, C1-C 10 Alkyl, halogenated C1-C 10 Alkyl, C1-C 10 Alkylsulfinyl, C1-C 10 Alkylsulfonyl, C1-C 10 Alkoxy and C1-C 10 One of the alkylthio groups.

6. The compound of formula I and its salt and stereoisomers according to claim 1, characterized in that: R7, R8, R9 and R 10 are independently selected from hydrogen, halogen, C3-C 10 One of cycloalkyl C2-C6 alkynyl, halogenated C1-C6 alkyl and C1-C6 alkylsulfonyl.

7. The compound of formula I and its salt and stereoisomer thereof according to claim 1, characterized in that , the compound of formula I is selected from the following compounds:

8. A composition, characterized in that The invention comprises the compound of formula I and its salt and stereoisomer thereof according to any one of claims 1 to 7 and at least one auxiliary agent selected from the group consisting of a surfactant, a solid diluent and a liquid diluent.

9. Use of the compound I according to any one of claims 1 to 7, its salts and stereoisomers thereof, and the composition according to claim 8 in preventing and controlling plant diseases and insect pests.

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