A pyridazinone compound containing aromatic ring substitution and its preparation method and use

Abstract

The invention discloses a pyridazinone compound containing an aromatic ring substitution, the structure of which is shown in the general formula I: the definition of each substituent in the formula is shown in the specification. The compound of the invention has a broad-spectrum fungicidal, insecticidal and acaricidal activity, and has excellent control effects on cucumber downy mildew, wheat powdery mildew, corn rust, cucumber anthracnose, armyworm, diamondback moth, peach aphid, cinnabarinus spider mite and the like.

Description

Technical Field

[0001] The invention belongs to the field of agricultural sterilization, insecticide and acaricide, and specifically relates to a novel pyridazinone compound containing aromatic ring substitution, a preparation method and application thereof. Background Art

[0002] Patent EP0665223A1 discloses a pyridazinone compound CK1 (patent number 107) as shown in the following general formula. The patent introduces its preparation and activity as an anti-tumor drug, but does not mention its use as a pesticide.

[0003]

[0004] However, there is no report on the use of pyridazinone compounds with the structure shown in the general formula I of the present invention as agricultural fungicides, insecticides and acaricides. Summary of the invention

[0005] The object of the present invention is to provide a pyridazinone compound containing aromatic ring substitution which can control a variety of pathogens, pests and mites, and the compound can be used for preparing drugs for preventing and controlling pathogens and / or pests and mites in agriculture or other fields.

[0006] To achieve the above object, the technical solution of the present invention is as follows:

[0007] A pyridazinone compound containing an aromatic ring substitution, characterized in that: the pyridazinone compound containing an aromatic ring substitution is a compound represented by general formula I;

[0008]

[0009] R1 is selected from hydrogen, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, C1-C 12 Alkoxy C1-C 12 Alkyl, C2-C 12 Alkenyl, C2-C 12 Alkynyl, C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, dimethylamino C1-C 12 alkyl, aryl, benzyl, heteroarylmethyl, unsubstituted or substituted by 1 to 5 of the following groups, the following groups are halogen, hydroxy, amino, cyano, nitro, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy, C3-C 12 Cycloalkyl, C1-C 12 Alkylamino, halogenated C1-C 12Alkylamino, di(C1-C 12 alkyl)amino, halogenated di(C1-C 12 Alkyl)amino, di(C1-C 12 Alkyl)aminocarbonyl, C1-C 12 Alkylthio, halogenated C1-C 12 Alkylthio, C2-C 12 Alkenyl, C2-C 12 Alkynyl, C2-C 12 Alkenyloxy, halogenated C2-C 12 Alkenyloxy, C2-C 12 Alkynyloxy, halogenated C2-C 12 Alkynyloxy, C1-C 12 Alkylsulfonyl, halogenated C1-C 12 Alkylsulfonyl, C1-C 12 Alkylcarbonyl, halogenated C1-C 12 Alkylcarbonyl, C1-C 12 Alkoxycarbonyl, halogenated C1-C 12 Alkoxycarbonyl, C1-C 12 Alkoxy C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy C1-C 12 Alkyl, C1-C 12 Alkylthio C1-C 12 Alkyl, halogenated C1-C 12 Alkylthio C1-C 12 Alkyl, C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, C1-C 12 Alkylthiocarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkylthiocarbonyl C1-C 12 Alkyl, C1-C 12 Alkylcarbonyloxy, halogenated C1-C 12 Alkylcarbonyloxy, C1-C 12 Alkoxycarbonyloxy, halogenated C1-C 12 Alkoxycarbonyloxy, C1-C 12 Alkylsulfonyloxy, halogenated C1-C 12 Alkylsulfonyloxy, C1-C 12 Alkoxy C1-C 12 Alkoxy or halogenated C1-C 12 Alkoxy C1-C 12 Alkoxy;

[0010] R2 and R3 may be the same or different and independently selected from hydrogen, halogen, cyano, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, C3-C 12 Cycloalkyl, C2-C 12 Alkenyl, C2-C 12 Alkynyl, C1-C 12 Alkoxy C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy C1-C 12 Alkyl, C1-C 12 Alkylthio C1-C 12 Alkyl, halogenated C1-C 12 Alkylthio C1-C 12 Alkyl, C4-C 12 Cycloalkylalkyl or halogenated C4-C 12 Cycloalkylalkyl;

[0011] R4, R5, R6, and R7 may be the same or different and independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, carboxyl, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy, C3-C 12 Cycloalkyl, C1-C 12 Alkylamino, halogenated C1-C 12 Alkylamino, di(C1-C 12 alkyl)amino, halogenated di(C1-C 12 Alkyl)amino, C1-C 12 Alkylthio, halogenated C1-C 12 Alkylthio, C2-C 12 Alkenyl, C2-C 12 Alkynyl, C2-C 12 Alkenyloxy, halogenated C2-C 12 Alkenyloxy, C2-C 12 Alkynyloxy, halogenated C2-C 12 Alkynyloxy, C1-C 12 Alkylsulfonyl, halogenated C1-C 12 Alkylsulfonyl, C1-C 12 Alkylcarbonyl, halogenated C1-C 12 Alkylcarbonyl, C1-C 12 Alkoxycarbonyl, halogenated C1-C 12 Alkoxycarbonyl, C1-C 12 Alkoxy C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy C1-C12 Alkyl, C1-C 12 Alkylthio C1-C 12 Alkyl, halogenated C1-C 12 Alkylthio C1-C 12 Alkyl, C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, C1-C 12 Alkylthiocarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkylthiocarbonyl C1-C 12 Alkyl, C1-C 12 Alkylcarbonyloxy, halogenated C1-C 12 Alkylcarbonyloxy, C1-C 12 Alkoxycarbonyloxy, halogenated C1-C 12 Alkoxycarbonyloxy, C1-C 12 Alkylsulfonyloxy, halogenated C1-C 12 Alkylsulfonyloxy, C1-C 12 Alkoxy C1-C 12 Alkoxy or halogenated C1-C 12 Alkoxy C1-C 12 Alkoxy;

[0012] X is selected from halogen;

[0013] A is selected from O, S, S=O, O=S=O;

[0014] Het is selected from oxadiazole substituted with one of the following groups, wherein the following groups are hydrogen, halogen, cyano, hydroxyl, amino, carboxyl, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy, C3-C 12 Cycloalkyl, halogenated C3-C 12 Cycloalkyl, C1-C 12 Alkylamino, halogenated C1-C 12 Alkylamino, di(C1-C 12 alkyl)amino, halogenated di(C1-C 12 Alkyl)amino, C1-C 12 Alkylthio, halogenated C1-C 12 Alkylthio, C2-C 12 Alkenyl, C2-C 12 Alkynyl, C2-C 12 Alkenyloxy, halogenated C2-C 12Alkenyloxy, C2-C 12 Alkynyloxy, halogenated C2-C 12 Alkynyloxy, C1-C 12 Alkylsulfonyl, halogenated C1-C 12 Alkylsulfonyl, C1-C 12 Alkylsulfinyl, halogenated C1-C 12 Alkylsulfinyl, C1-C 12 Alkylcarbonyl, halogenated C1-C 12 Alkylcarbonyl, C1-C 12 Alkoxycarbonyl, halogenated C1-C 12 Alkoxycarbonyl, C1-C 12 Alkoxy C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy C1-C 12 Alkyl, C1-C 12 Alkylthio C1-C 12 Alkyl, halogenated C1-C 12 Alkylthio C1-C 12 Alkyl, C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, C1-C 12 Alkylthiocarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkylthiocarbonyl C1-C 12 Alkyl, C1-C 12 Alkylcarbonyloxy, halogenated C1-C 12 Alkylcarbonyloxy, C1-C 12 Alkoxycarbonyloxy, halogenated C1-C 12 Alkoxycarbonyloxy, C1-C 12 Alkylcarbonylthio, halogenated C1-C 12 Alkylcarbonylthio, C1-C 12 Alkoxycarbonylthio, halogenated C1-C 12 Alkoxycarbonylthio, C1-C 12 Alkylsulfonyloxy, C1-C 12 Alkylsulfonylthio, halogenated C1-C 12 Alkylsulfonylthio, halogenated C1-C 12 Alkylsulfonyloxy, C1-C 12 Alkoxy C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy C1-C 12 Alkoxy, C1-C 12 Alkoxy C1-C12 Alkylthio, halogenated C1-C 12 Alkoxy C1-C 12 Alkylthio, C1-C 12 Alkylthio C1-C 12 Alkylthio or halogenated C1-C 12 Alkylthio C1-C 12 Alkylthio, substituted phenyl, substituted naphthyl, substituted heteroaryl;

[0015] The substituted phenyl and substituted naphthyl groups refer to phenyl or naphthyl groups substituted by 1 to 5 or 1 to 7 of the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, amino, carboxyl, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy, C1-C 12 Alkylamino, halogenated C1-C 12 Alkylamino, di(C1-C 12 alkyl)amino, halogenated di(C1-C 12 Alkyl)amino, C1-C 12 Alkylthio, halogenated C1-C 12 Alkylthio, C2-C 12 Alkenyl, C2-C 12 Alkynyl, C2-C 12 Alkenyloxy, halogenated C2-C 12 Alkenyloxy, C2-C 12 Alkynyloxy, halogenated C2-C 12 Alkynyloxy, C1-C 12 Alkylsulfonyl, halogenated C1-C 12 Alkylsulfonyl, C1-C 12 Alkylcarbonyl, halogenated C1-C 12 Alkylcarbonyl, C1-C 12 Alkoxycarbonyl, halogenated C1-C 12 Alkoxycarbonyl, C1-C 12 Alkoxy C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy C1-C 12 Alkyl, C1-C 12 Alkylthio C1-C 12 Alkyl, halogenated C1-C 12 Alkylthio C1-C 12 Alkyl, C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, C1-C12 Alkylthiocarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkylthiocarbonyl C1-C 12 Alkyl, C1-C 12 Alkylcarbonyloxy, halogenated C1-C 12 Alkylcarbonyloxy, C1-C 12 Alkoxycarbonyloxy, halogenated C1-C 12 Alkoxycarbonyloxy, C1-C 12 Alkylsulfonyloxy, halogenated C1-C 12 Alkylsulfonyloxy, C1-C 12 Alkoxy C1-C 12 Alkoxy or halogenated C1-C 12 Alkoxy C1-C 12 Alkoxy;

[0016] The heteroaryl group refers to a five-membered, six-membered heterocyclic ring or a ten- to twelve-membered heterocyclic ring group. The aforementioned heteroaryl group may be substituted by 1 to 7 of the following groups: hydrogen, halogen, cyano, nitro, hydroxyl, amino, carboxyl, C1-C 12 Alkyl, halogenated C1-C 12 Alkyl, C1-C 12 Alkoxy, halogenated C1-C 12 Alkoxy, C1-C 12 Alkylamino, halogenated C1-C 12 Alkylamino, di(C1-C 12 alkyl)amino, halogenated di(C1-C 12 Alkyl)amino, C1-C 12 Alkylthio, halogenated C1-C 12 Alkylthio, C2-C 12 Alkenyl, C2-C 12 Alkynyl, C2-C 12 Alkenyloxy, halogenated C2-C 12 Alkenyloxy, C2-C 12 Alkynyloxy, halogenated C2-C 12 Alkynyloxy, C1-C 12 Alkylsulfonyl, halogenated C1-C 12 Alkylsulfonyl, C1-C 12 Alkylcarbonyl, halogenated C1-C 12 Alkylcarbonyl, C1-C 12 Alkoxycarbonyl, halogenated C1-C 12 Alkoxycarbonyl, C1-C 12 Alkoxy C1-C 12 Alkyl, halogenated C1-C 12 Alkoxy C1-C 12 Alkyl, C1-C12 Alkylthio C1-C 12 Alkyl, halogenated C1-C 12 Alkylthio C1-C 12 Alkyl, C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkoxycarbonyl C1-C 12 Alkyl, C1-C 12 Alkylthiocarbonyl C1-C 12 Alkyl, halogenated C1-C 12 Alkylthiocarbonyl C1-C 12 Alkyl, C1-C 12 Alkylcarbonyloxy, halogenated C1-C 12 Alkylcarbonyloxy, C1-C 12 Alkoxycarbonyloxy, halogenated C1-C 12 Alkoxycarbonyloxy, C1-C 12 Alkylsulfonyloxy, halogenated C1-C 12 Alkylsulfonyloxy, C1-C 12 Alkoxy C1-C 12 Alkoxy or halogenated C1-C 12 Alkoxy C1-C 12 Alkoxy.

[0017] Preferably, in the compound of formula I

[0018] R1 is selected from hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxycarbonyl C1-C8 alkyl, dimethylamino C1-C8 alkyl, phenyl, benzyl, heteroarylmethyl which are unsubstituted or substituted by 1 to 5 of the following groups, wherein the following groups are halogen, hydroxy, amino, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C3-C8 cycloalkyl, C1-C8 alkylamino, halogenated C1-C8 alkylamino, di(C1-C8 alkyl)amino, halogenated di(C1-C8 alkyl)amino, di(C1-C8 alkyl)aminocarbonyl, C1-C8 alkylthio, halogenated C1-C8 alkylthio, C2-C8 alkenyl, C2-C8 alkynyl, C2-C8 alkenyloxy, halogenated C2-C8 alkenyloxy, C2-C8 alkynyloxy, halogenated C2-C8 alkynyloxy, C1-C8 Alkylsulfonyl, halogenated C1-C8 alkylsulfonyl, C1-C8 alkylcarbonyl, halogenated C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, halogenated C1-C8 alkoxycarbonyl, C1-C8 alkoxy C1-C8 alkyl, halogenated C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylthio C1-C8 alkyl, halogenated C1-C8 alkylthio C1-C8 alkyl, C1-C8 alkoxycarbonyl C1-C8 alkyl, halogenated C1-C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylthiocarbonyl C1-C8 alkyl, halogenated C1-C8 alkylthiocarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyloxy, halogenated C1-C8 alkylcarbonyloxy, C1-C8 alkoxycarbonyloxy, halogenated C1-C8 alkoxycarbonyloxy, C1-C8 alkylsulfonyloxy, halogenated C1-C8 alkylsulfonyloxy, C1-C8 alkoxy C1-C8 alkoxy or halogenated C1-C8 alkoxy C1-C8 alkoxy;

[0019] R2 and R3 may be the same or different and are independently selected from hydrogen, halogen, cyano, C1-C8 alkyl, halogenated C1-C8 alkyl;

[0020] R4, R5, R6, and R7 may be the same or different and are independently selected from hydrogen, halogen, cyano, nitro, hydroxyl, amino, carboxyl, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C3-C8 cycloalkyl, C1-C8 alkylamino, halogenated C1-C8 alkylamino, di(C1-C8 alkyl)amino, halogenated di(C1-C8 alkyl)amino, C1-C8 alkylthio, halogenated C1-C8 alkylthio, C2-C8 alkenyl, C2-C8 alkynyl, C2-C8 alkenyloxy, halogenated C2-C8 alkenyloxy, C2-C8 alkynyloxy, halogenated C2-C8 alkynyloxy, C1-C8 alkylsulfonyl, halogenated C1-C8 alkylsulfonyl, C1-C8 alkylcarbonyl, halogenated C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, Halogenated C1-C8 alkoxycarbonyl, C1-C8 alkoxy C1-C8 alkyl, halogenated C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylthio C1-C8 alkyl, halogenated C1-C8 alkylthio C1-C8 alkyl, C1-C8 alkoxycarbonyl C1-C8 alkyl, halogenated C1-C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylthiocarbonyl C1-C8 alkyl, Halogenated C1-C8 alkylthiocarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyloxy, halogenated C1-C8 alkylcarbonyloxy, C1-C8 alkoxycarbonyloxy, halogenated C1-C8 alkoxycarbonyloxy, C1-C8 alkylsulfonyloxy, halogenated C1-C8 alkylsulfonyloxy, C1-C8 alkoxy C1-C8 alkoxy or halogenated C1-C8 alkoxy C1-C8 alkoxy;

[0021] X is selected from halogen;

[0022] A is selected from O, S, S=O, O=S=O;

[0023] Het is selected from 1,3,4-oxadiazole-2-yl substituted at the 5-position, 1,2,4-oxadiazole-3-yl substituted at the 5-position, and 1,2,4-oxadiazole-5-yl substituted at the 3-position, and the substituent group is hydrogen, halogen, cyano, hydroxyl, amino, carboxyl, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C3-C8 cycloalkyl, halogenated C3-C8 cycloalkyl, C1-C8 alkylamino, halogenated C1-C8 alkylamino, di(C1-C8 alkyl)amino, halogenated di(C1-C8 alkyl)amino, C1-C8 8 alkylthio, halogenated C1-C8 alkylthio, C2-C8 alkenyl, C2-C8 alkynyl, C2-C8 alkenyloxy, halogenated C2-C8 alkenyloxy, C2-C8 alkynyloxy, halogenated C2-C8 alkynyloxy, C1-C8 alkylsulfonyl, halogenated C1-C8 alkylsulfonyl, C1-C8 alkylsulfinyl, halogenated C1-C8 alkylsulfinyl, C1-C8 alkylcarbonyl, halogenated C1-C8 alkylcarbonyl, C1-C8 alkoxycarbonyl, halogenated C1-C8 alkoxycarbonyl, C1-C8 alkoxy C1-C8 alkyl, halogenated C1-C8 alkoxy C1-C8 alkyl C1-C8 alkylthio C1-C8 alkyl, halogenated C1-C8 alkylthio C1-C8 alkyl, C1-C8 alkoxycarbonyl C1-C8 alkyl, halogenated C1-C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylthiocarbonyl C1-C8 alkyl, halogenated C1-C8 alkylthiocarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyloxy, halogenated C1-C8 alkylcarbonyloxy, C1-C8 alkoxycarbonyloxy, halogenated C1-C8 alkoxycarbonyloxy, C1-C8 alkylcarbonylthio, halogenated C1-C8 alkylcarbonylthio, C1-C8 alkoxy Carbonylthio, halogenated C1-C8 alkoxycarbonylthio, C1-C8 alkylsulfonyloxy, C1-C8 alkylsulfonylthio, halogenated C1-C8 alkylsulfonylthio, halogenated C1-C8 alkylsulfonyloxy, C1-C8 alkoxy C1-C8 alkoxy, halogenated C1-C8 alkoxy C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkylthio, halogenated C1-C8 alkoxy C1-C8 alkylthio, C1-C8 alkylthio C1-C8 alkylthio or halogenated C1-C8 alkylthio C1-C8 alkylthio, substituted phenyl, substituted naphthyl, substituted heteroaryl;

[0024] The substituted phenyl and substituted naphthyl refer to phenyl or naphthyl substituted by 1 to 5 or 1-7 of the following groups, wherein the following groups are hydrogen, halogen, cyano, nitro, hydroxyl, amino, carboxyl, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkylamino, halogenated C1-C8 alkylamino, di(C1-C8 alkyl)amino, halogenated di(C1-C8 alkyl)amino, C1-C8 alkylthio, halogenated C1-C8 alkylthio, C2-C8 alkenyl, C2-C8 alkynyl, C2-C8 alkenyloxy, halogenated C2-C8 alkenyloxy, C2-C8 alkynyloxy, halogenated C2-C8 alkynyloxy, C1-C8 alkylsulfonyl, halogenated C1-C8 alkylsulfonyl, C1-C8 alkylcarbonyl, halogenated C1-C8 alkylcarbonyl, C1-C8 alkoxy C1-C8 alkylthiocarbonyl, halogenated C1-C8 alkoxycarbonyl, C1-C8 alkoxy C1-C8 alkyl, halogenated C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylthio C1-C8 alkyl, halogenated C1-C8 alkylthio C1-C8 alkyl, C1-C8 alkoxycarbonyl C1-C8 alkyl, halogenated C1-C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylthiocarbonyl C1-C8 alkyl alkyl, halogenated C1-C8 alkylthiocarbonyl C1-C8 alkyl, C1-C8 alkylcarbonyloxy, halogenated C1-C8 alkylcarbonyloxy, C1-C8 alkoxycarbonyloxy, halogenated C1-C8 alkoxycarbonyloxy, C1-C8 alkylsulfonyloxy, halogenated C1-C8 alkylsulfonyloxy, C1-C8 alkoxy C1-C8 alkoxy or halogenated C1-C8 alkoxy C1-C8 alkoxy;

[0025] The heteroaryl refers to a five-membered, six-membered heterocyclic or ten- to twelve-membered heterocyclic group, and the aforementioned heteroaryl may be substituted by 1 to 7 of the following groups, the following groups being hydrogen, halogen, cyano, nitro, hydroxyl, amino, carboxyl, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkylamino, halogenated C1-C8 alkylamino, di(C1-C8 alkyl)amino , halogenated di(C1-C8 alkyl)amino, C1-C8 alkylthio, halogenated C1-C8 alkylthio, C2-C8 alkenyl, C2-C8 alkynyl, C2-C8 alkenyloxy, halogenated C2-C8 alkenyloxy, C2-C8 alkynyloxy, halogenated C2-C8 alkynyloxy, C1-C8 alkylsulfonyl, halogenated C1-C8 alkylsulfonyl, C1-C8 alkylcarbonyl, halogenated C1-C8 alkylcarbonyl, C1-C8 C8 alkoxycarbonyl, halogenated C1-C8 alkoxycarbonyl, C1-C8 alkoxy C1-C8 alkyl, halogenated C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkylthio C1-C8 alkyl, halogenated C1-C8 alkylthio C1-C8 alkyl, C1-C8 alkoxycarbonyl C1-C8 alkyl, halogenated C1-C8 alkoxycarbonyl C1-C8 alkyl, C1-C8 alkylthiocarbonyl C1-C8 C1-C8 alkyl, halogenated C1-C8 alkylthiocarbonyl, C1-C8 alkylcarbonyloxy, halogenated C1-C8 alkylcarbonyloxy, C1-C8 alkoxycarbonyloxy, halogenated C1-C8 alkoxycarbonyloxy, C1-C8 alkylsulfonyloxy, halogenated C1-C8 alkylsulfonyloxy, C1-C8 alkoxy C1-C8 alkoxy or halogenated C1-C8 alkoxy C1-C8 alkoxy.

[0026] Further preferably, in the general formula I

[0027] R1 is selected from hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, dimethylamino C1-C6 alkyl, phenyl which is unsubstituted or substituted by 1 to 5 of the following groups, benzyl, the following groups are halogen, hydroxyl, amino, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 Alkoxy, C3-C6 cycloalkyl, C1-C6 alkylamino, halogenated C1-C6 alkylamino, di(C1-C6 alkyl)amino, halogenated di(C1-C6 alkyl)amino, di(C1-C6 alkyl)aminocarbonyl, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 alkenyloxy, halogenated C2-C6 alkenyloxy, C2-C6 alkynyloxy, halogenated C2-C6 alkynyloxy, C1-C6 alkylsulfonyl Acyl, halogenated C1-C6 alkylsulfonyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxycarbonyl, C1-C6 alkoxy C1-C6 alkyl, halogenated C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, halogenated C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, halogenated C1-C6 alkoxycarbonyl C1-C6 alkyl -C6 alkyl, C1-C6 alkylthiocarbonylC1-C6 alkyl, halogenated C1-C6 alkylthiocarbonylC1-C6 alkyl, C1-C6 alkylcarbonyloxy, halogenated C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyloxy, halogenated C1-C6 alkoxycarbonyloxy, C1-C6 alkylsulfonyloxy, halogenated C1-C6 alkylsulfonyloxy, C1-C6 alkoxyC1-C6 alkoxy or halogenated C1-C6 alkoxyC1-C6 alkoxy;

[0028] R2 and R3 may be the same or different and are independently selected from hydrogen, halogen, cyano, C1-C6 alkyl, halogenated C1-C6 alkyl;

[0029] R4, R5, R6, and R7 may be the same or different and are independently selected from hydrogen, halogen, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, C1-C6 alkoxy C1-C6 alkyl, halogenated C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, halogenated C1-C6 alkylthio C1-C6 alkyl;

[0030] X is selected from halogen;

[0031] A is selected from O, S, S=O, O=S=O;

[0032] Het is selected from 1,3,4-oxadiazole-2-yl substituted at the 5-position, 1,2,4-oxadiazole-3-yl substituted at the 5-position, and 1,2,4-oxadiazole-5-yl substituted at the 3-position, and the substituent group is hydrogen, halogen, cyano, hydroxyl, amino, carboxyl, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C6 alkylamino, halogenated C1-C6 alkylamino, di(C1-C6 alkyl)amino, halogenated di(C1-C6 alkyl)amino, C1-C alkylthio, halogenated C1-C6 alkylthio, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 alkenyloxy, halogenated C2-C6 alkenyloxy, C2-C6 alkynyloxy, halogenated C2-C6 alkynyloxy, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, C1-C6 alkylsulfinyl, halogenated C1-C6 alkylsulfinyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxycarbonyl, C1-C6 alkoxyC1-C6 alkyl, halogenated C1-C6 alkoxyC1-C6 alkyl C1-C6 alkylthio C1-C6 alkyl, halogenated C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, halogenated C1-C6 alkoxycarbonyl C1-C6 alkyl, C1-C6 alkylthiocarbonyl C1-C6 alkyl, halogenated C1-C6 alkylthiocarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyloxy, halogenated C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyloxy, halogenated C1-C6 alkoxycarbonyloxy, C1-C6 alkylcarbonylthio, halogenated C1-C6 alkylcarbonylthio, C1-C6 alkoxy Carbonylthio, halogenated C1-C6 alkoxycarbonylthio, C1-C6 alkylsulfonyloxy, C1-C6 alkylsulfonylthio, halogenated C1-C6 alkylsulfonylthio, halogenated C1-C6 alkylsulfonyloxy, C1-C6 alkoxy C1-C6 alkoxy, halogenated C1-C6 alkoxy C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkylthio, halogenated C1-C6 alkoxy C1-C6 alkylthio, C1-C6 alkylthio C1-C6 alkylthio or halogenated C1-C6 alkylthio C1-C6 alkylthio, substituted phenyl, substituted naphthyl, substituted heteroaryl;

[0033] The substituted phenyl and substituted naphthyl refer to phenyl or naphthyl substituted by 1 to 5 or 1-7 of the following groups, wherein the following groups are hydrogen, halogen, cyano, nitro, hydroxyl, amino, carboxyl, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylamino, halogenated C1-C6 alkylamino, di(C1-C6 alkyl)amino, halogenated di(C1-C6 alkyl)amino, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 alkenyloxy, halogenated C2-C6 alkenyloxy, C2-C6 alkynyloxy, halogenated C2-C6 alkynyloxy, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1-C6 alkoxy C1-C6 alkoxycarbonyl, halogenated C1-C6 alkoxycarbonyl, C1-C6 alkoxy C1-C6 alkyl, halogenated C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, halogenated C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, halogenated C1-C6 alkoxycarbonyl C1-C6 alkyl, C1-C6 alkylthiocarbonyl C1-C6 alkyl alkyl, halogenated C1-C6 alkylthiocarbonyl C1-C6 alkyl, C1-C6 alkylcarbonyloxy, halogenated C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyloxy, halogenated C1-C6 alkoxycarbonyloxy, C1-C6 alkylsulfonyloxy, halogenated C1-C6 alkylsulfonyloxy, C1-C6 alkoxyC1-C6 alkoxy or halogenated C1-C6 alkoxyC1-C6 alkoxy;

[0034] The heteroaryl refers to a five-membered, six-membered heterocyclic or ten- to twelve-membered heterocyclic group, and the aforementioned heteroaryl may be substituted by 1 to 7 of the following groups, the following groups being hydrogen, halogen, cyano, nitro, hydroxyl, amino, carboxyl, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkylamino, halogenated C1-C6 alkylamino, di(C1-C6 alkyl)amino , halogenated di(C1-C6 alkyl)amino, C1-C6 alkylthio, halogenated C1-C6 alkylthio, C2-C6 alkenyl, C2-C6 alkynyl, C2-C6 alkenyloxy, halogenated C2-C6 alkenyloxy, C2-C6 alkynyloxy, halogenated C2-C6 alkynyloxy, C1-C6 alkylsulfonyl, halogenated C1-C6 alkylsulfonyl, C1-C6 alkylcarbonyl, halogenated C1-C6 alkylcarbonyl, C1- C6 alkoxycarbonyl, halogenated C1-C6 alkoxycarbonyl, C1-C6 alkoxy C1-C6 alkyl, halogenated C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkylthio C1-C6 alkyl, halogenated C1-C6 alkylthio C1-C6 alkyl, C1-C6 alkoxycarbonyl C1-C6 alkyl, halogenated C1-C6 alkoxycarbonyl C1-C6 alkyl, C1-C6 alkylthiocarbonyl C1-C6 alkyl C1-C6 alkyl, halogenated C1-C6 alkylthiocarbonyl, C1-C6 alkyl, C1-C6 alkylcarbonyloxy, halogenated C1-C6 alkylcarbonyloxy, C1-C6 alkoxycarbonyloxy, halogenated C1-C6 alkoxycarbonyloxy, C1-C6 alkylsulfonyloxy, halogenated C1-C6 alkylsulfonyloxy, C1-C6 alkoxy C1-C6 alkoxy or halogenated C1-C6 alkoxy C1-C6 alkoxy.

[0035] In further preferred embodiments, in the general formula I

[0036] R1 is selected from hydrogen, C1-C4 alkyl, halo-substituted C1-C4 alkyl, C1-C4 alkoxy C1-C4 alkyl, C2-C4 alkenyl, C2-C4 alkynyl, C1-C4 alkoxycarbonyl C1-C4 alkyl, phenyl which is unsubstituted or substituted by 1 to 5 of the following groups, wherein the following groups are halogen, cyano, nitro, C1-C4 alkyl, halo-substituted C1-C4 alkyl, C1-C4 alkoxy, halo-substituted C1-C4 alkoxy;

[0037] R2 and R3 are selected from hydrogen;

[0038] R4, R5, R6, and R7 may be the same or different and are independently selected from hydrogen, halogen, C1-C4 alkoxy, C1-C4 alkyl, and halogenated C1-C4 alkyl;

[0039] X is selected from halogen;

[0040] A is selected from O, S, S=O, O=S=O;

[0041] Het is selected from 1,3,4-oxadiazole-2-yl substituted at the 5-position, 1,2,4-oxadiazole-3-yl substituted at the 5-position, and 1,2,4-oxadiazole-5-yl substituted at the 3-position, and the substituent group is hydrogen, halogen, cyano, hydroxyl, amino, carboxyl, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C6 cycloalkyl, halogenated C3-C6 cycloalkyl, C1-C4 alkylamino, halogenated C1-C4 alkylamino, di(C1-C4 alkyl)amino, halogenated di(C1-C4 alkyl)amino, C1-C C2-C4 alkylthio, halogenated C1-C4 alkylthio, C2-C4 alkenyl, C2-C4 alkynyl, C2-C4 alkenyloxy, halogenated C2-C4 alkenyloxy, C2-C4 alkynyloxy, halogenated C2-C4 alkynyloxy, C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl, C1-C4 alkylsulfinyl, halogenated C1-C4 alkylsulfinyl, C1-C4 alkylcarbonyl, halogenated C1-C4 alkylcarbonyl, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, C1-C4 alkoxyC1-C4 alkyl, halogenated C1-C4 alkoxyC1-C4 alkyl C1-C4 alkylthio C1-C4 alkyl, halogenated C1-C4 alkylthio C1-C4 alkyl, C1-C4 alkoxycarbonyl C1-C4 alkyl, halogenated C1-C4 alkoxycarbonyl C1-C4 alkyl, C1-C4 alkylthiocarbonyl C1-C4 alkyl, halogenated C1-C4 alkylthiocarbonyl C1-C4 alkyl, C1-C4 alkylcarbonyloxy, halogenated C1-C4 alkylcarbonyloxy, C1-C4 alkoxycarbonyloxy, halogenated C1-C4 alkoxycarbonyloxy, C1-C4 alkylcarbonylthio, halogenated C1-C4 alkylcarbonylthio, C1-C4 alkoxy Carbonylthio, halogenated C1-C4 alkoxycarbonylthio, C1-C4 alkylsulfonyloxy, C1-C4 alkylsulfonylthio, halogenated C1-C4 alkylsulfonylthio, halogenated C1-C4 alkylsulfonyloxy, C1-C4 alkoxy C1-C4 alkoxy, halogenated C1-C4 alkoxy C1-C4 alkoxy, C1-C4 alkoxy C1-C4 alkylthio, halogenated C1-C4 alkoxy C1-C4 alkylthio, C1-C4 alkylthio C1-C4 alkylthio or halogenated C1-C4 alkylthio C1-C4 alkylthio, substituted phenyl, substituted naphthyl, substituted heteroaryl;

[0042] The substituted phenyl and substituted naphthyl refer to phenyl or naphthyl substituted by 1 to 5 or 1-7 of the following groups, wherein the following groups are hydrogen, halogen, cyano, nitro, hydroxyl, amino, carboxyl, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C1-C4 alkylamino, halogenated C1-C4 alkylamino, di(C1-C4 alkyl)amino, halogenated di(C1-C4 alkyl)amino, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C2-C4 alkenyl, C2-C4 alkynyl, C2-C4 alkenyloxy, halogenated C2-C4 alkenyloxy, C2-C4 alkynyloxy, halogenated C2-C4 alkynyloxy, C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl, C1-C4 alkylcarbonyl, halogenated C1-C4 alkylcarbonyl, C1-C4 alkoxy C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, C1-C4 alkoxy C1-C4 alkyl, halogenated C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkylthio C1-C4 alkyl, halogenated C1-C4 alkylthio C1-C4 alkyl, C1-C4 alkoxycarbonyl C1-C4 alkyl, halogenated C1-C4 alkoxycarbonyl C1-C4 alkyl, C1-C4 alkylthiocarbonyl C1-C4 alkyl alkyl, halogenated C1-C4 alkylthiocarbonyl C1-C4 alkyl, C1-C4 alkylcarbonyloxy, halogenated C1-C4 alkylcarbonyloxy, C1-C4 alkoxycarbonyloxy, halogenated C1-C4 alkoxycarbonyloxy, C1-C4 alkylsulfonyloxy, halogenated C1-C4 alkylsulfonyloxy, C1-C4 alkoxyC1-C4 alkoxy or halogenated C1-C4 alkoxyC1-C4 alkoxy;

[0043] The heteroaryl group refers to a five-membered, six-membered heterocyclic ring or a ten- to twelve-membered heterocyclic ring group. The aforementioned heteroaryl group may be substituted by 1 to 7 of the following groups, the following groups being hydrogen, halogen, cyano, nitro, hydroxyl, amino, carboxyl, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C1-C4 alkylamino, halogenated C1-C4 alkylamino, di(C1-C4 alkyl)amino , halogenated di(C1-C4 alkyl)amino, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C2-C4 alkenyl, C2-C4 alkynyl, C2-C4 alkenyloxy, halogenated C2-C4 alkenyloxy, C2-C4 alkynyloxy, halogenated C2-C4 alkynyloxy, C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl, C1-C4 alkylcarbonyl, halogenated C1-C4 alkylcarbonyl, C1-C4 C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, C1-C4 alkoxy C1-C4 alkyl, halogenated C1-C4 alkoxy C1-C4 alkyl, C1-C4 alkylthio C1-C4 alkyl, halogenated C1-C4 alkylthio C1-C4 alkyl, C1-C4 alkoxycarbonyl C1-C4 alkyl, halogenated C1-C4 alkoxycarbonyl C1-C4 alkyl, C1-C4 alkylthiocarbonyl C1-C4 alkyl C1-C4 alkyl, halogenated C1-C4 alkylthiocarbonyl, C1-C4 alkylcarbonyloxy, halogenated C1-C4 alkylcarbonyloxy, C1-C4 alkoxycarbonyloxy, halogenated C1-C4 alkoxycarbonyloxy, C1-C4 alkylsulfonyloxy, halogenated C1-C4 alkylsulfonyloxy, C1-C4 alkoxyC1-C4 alkoxy or halogenated C1-C4 alkoxyC1-C4 alkoxy.

[0044] More preferably, in the general formula I

[0045] R1 is selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, tert-butyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl, ethoxymethyl, methoxyethyl, allyl, propargyl, phenyl, 3,4-dichlorophenyl;

[0046] R2 and R3 are selected from hydrogen;

[0047] R4, R5, R6, and R7 may be the same or different and independently selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, and trifluoromethyl;

[0048] X is selected from fluorine, chlorine, bromine and iodine;

[0049] A is selected from O, S, S=O, O=S=O;

[0050] Het is selected from 1,3,4-oxadiazol-2-yl substituted at the 5-position, 1,2,4-oxadiazol-3-yl substituted at the 5-position, 1,2,4-oxadiazol-5-yl substituted at the 3-position, and the substituent group is hydrogen, amino, methoxy, ethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, tert-butyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl;

[0051] More preferably, in the general formula I

[0052] R1 is selected from hydrogen, tert-butyl, phenyl, 3,4-dichlorophenyl;

[0053] R2 and R3 are selected from hydrogen;

[0054] R4, R5, R6, and R7 may be the same or different and independently selected from hydrogen, fluorine, chlorine, and trifluoromethyl;

[0055] X is selected from chlorine;

[0056] A is selected from O, S, S=O, O=S=O;

[0057] Het is selected from 1,3,4-oxadiazol-2-yl substituted at the 5-position, 1,2,4-oxadiazol-3-yl substituted at the 5-position, 1,2,4-oxadiazol-5-yl substituted at the 3-position, and the substituent group is hydrogen, amino, methoxy, ethoxy, trifluoromethoxy, 2,2,2-trifluoroethoxy, methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, tert-butyl, trifluoromethyl, 2,2,2-trifluoroethyl;

[0058] In the definition of compounds of general formula I given above, the terms used are generally defined as follows:

[0059] Halogen: refers to fluorine, chlorine, bromine or iodine. Alkyl: straight chain or branched alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl. Cycloalkyl: substituted or unsubstituted cyclic alkyl, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen, etc. Haloalkyl: straight chain or branched alkyl, the hydrogen atoms on these alkyl can be partially or completely replaced by halogen atoms, such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc. Haloalkoxy: straight chain or branched alkoxy, the hydrogen atoms on these alkoxy can be partially or completely replaced by halogen atoms. For example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc. Alkoxyalkyl: alkyl-O-alkyl-, such as CH3OCH2-. Halogenated alkoxyalkyl: The hydrogen atoms on the alkyl group of alkoxyalkyl can be partially or completely replaced by halogen atoms, such as ClCH2CH2OCH2-, CF3CH2OCH2-, etc. 12Alkyl: (CH3)2N-alkyl-, for example (CH3)2N-CH2-. Alkylamino: straight chain or branched alkyl, connected to the structure via a nitrogen atom. Haloalkylamino: straight chain or branched alkylamino, the hydrogen atoms on these alkyl groups may be partially or completely replaced by halogen atoms. Dialkylamino: such as (CH3)2N-, (CH3CH2)2N-. Halodialkylamino: the hydrogen atoms on the alkyl group may be partially or completely replaced by halogen atoms, such as (CF3)2N-, (CF3CH2)2N-. Alkoxycarbonylalkyl: alkoxycarbonyl-alkyl-, for example CH3OCOCH2-. Alkoxyalkoxy: such as CH3OCH2O-, etc. Haloalkoxyalkoxy: the hydrogen atoms on the alkoxy group may be partially or completely replaced by halogen atoms, for example CF3OCH2O-. Alkylthio: straight chain or branched alkyl, connected to the structure via a sulfur atom. Halogenated alkylthio: straight or branched alkylthio, the hydrogen atoms on these alkyl groups may be partially or completely replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, etc. Alkylthioalkyl: alkyl-S-alkyl-, such as CH3SCH2-. Halogenated alkylthioalkyl: the hydrogen atoms on the alkyl group of alkylthioalkyl may be partially or completely replaced by halogen atoms, such as ClCH2CH2SCH2-, CF3CH2SCH2-, etc. Alkenyl: straight or branched alkenes, such as vinyl, 1-propenyl, 2-propenyl and different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes, such as 1,2-propadienyl and 2,4-hexadienyl. Halogenated alkenyl: straight or branched alkenes, the hydrogen atoms on these alkenyl groups may be partially or completely replaced by halogen atoms. Alkenyloxy: straight or branched alkenes, connected to the structure via an oxygen atom. Haloalkenyloxy: straight or branched alkenyloxy, the hydrogen atoms on these alkenyloxy groups may be partially or completely replaced by halogen atoms. Alkenylthio: straight or branched alkenes, connected to the structure via a sulfur atom. Such as CH2=CHCH2S-. Alkenyloxycarbonyl: such as CH2=CHCH2OCO-, etc. Alkynyl: straight or branched alkynes, such as ethynyl, 1-propynyl, 2-propynyl and different butynyl, pentynyl and hexynyl isomers. Alkynyl also includes groups composed of multiple triple bonds, such as 2,5-hexadiynyl. Haloalkynyl: straight or branched alkynes, the hydrogen atoms on these alkynyl groups may be partially or completely replaced by halogen atoms. Alkynyloxy: straight or branched alkynes, connected to the structure via an oxygen atom. Haloalkynyloxy: straight or branched alkynyloxy, the hydrogen atoms on these alkynyloxy groups may be partially or completely replaced by halogen atoms. Cycloalkylalkyl: an alkyl chain with a substituted or unsubstituted cyclic alkyl group, such as cyclopropylmethyl, cyclohexylmethyl, etc. Alkylsulfonyl: a straight or branched chain alkyl group connected to the structure via a sulfone group, such as CH3SO2-. Haloalkylsulfonyl: a straight or branched chain alkylsulfonyl group, in which the hydrogen atoms may be partially or completely replaced by halogen atoms.Alkylcarbonyl: for example, CH3CO. Haloalkylcarbonyl: a straight or branched chain alkylcarbonyl, in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkoxycarbonyl: for example, CH3OCO. Haloalkoxycarbonyl: a straight or branched chain alkoxycarbonyl, in which the hydrogen atoms may be partially or completely replaced by halogen atoms. Alkylsulfonyloxy: for example, CH3SO2O-. Haloalkylsulfonyloxy: the hydrogen atoms on the alkylsulfonyloxy may be partially or completely replaced by halogen atoms. For example, CF3SO2O-. Haloalkoxycarbonylalkyl: the hydrogen atoms on the alkoxycarbonyl-alkyl- may be partially or completely replaced by halogen atoms. Alkylthiocarbonylalkyl: alkylthiocarbonyl-alkyl-, for example, CH3SCOCH2-. Haloalkylthiocarbonylalkyl: the hydrogen atoms on the alkylthiocarbonyl-alkyl- may be partially or completely replaced by halogen atoms. Alkylcarbonyloxy: for example, CH3CO2-. Haloalkylcarbonyloxy: The hydrogen atoms on the alkylcarbonyloxy group may be partially or completely replaced by halogen atoms. For example, CF3CO2-. Alkoxycarbonyloxy: such as CH3OCO2-, etc. Haloalkoxycarbonyloxy: The hydrogen atoms on the alkoxycarbonyloxy group may be partially or completely replaced by halogen atoms. For example, CF3OCO2-, etc. Heteroaryl is a five-membered ring or a six-membered ring containing one or more heteroatoms. For example, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, thienyl, thiazolyl, etc. Heteroarylmethyl is heteroaryl-CH2-.

[0060] The general or preferred radical definitions or descriptions listed above can also be combined with each other as needed, i.e. including combinations within the respective ranges and preferred ranges. The definitions apply to both the final product and, accordingly, to the precursors and intermediates. In addition, some definitions may not apply.

[0061] The compounds of the present invention are prepared according to the following method, and the reaction formula is as follows, wherein the groups have the same definitions as above unless otherwise specified:

[0062] According to the different connected heterocyclic rings, the general formula compound I can be represented as I-1, I-2, and I-3 respectively. The preparation of the general formula compound I can be carried out by the following method:

[0063]

[0064] Note: “L” represents a leaving group, such as hydroxyl, chlorine, etc.

[0065] Intermediate II-1 or II-2 is reacted with the corresponding carboxylic acid or acid chloride or acid anhydride or orthoester in a suitable solvent to obtain a compound of formula I. If necessary, an acid or base and / or a catalyst are required to participate in the reaction. It can be prepared by the following methods: II-1 or II-2 reacts with the corresponding acid chloride, anhydride or orthoester and a catalyst [such as Synthetic Communications, 2014, 44 (13), 1978-1986; Advanced Synthesis & Catalysis, 2017, 359 (5), 772-778; Synthesis, 2016, 48 (20), 3597-3602]; II-1 or II-2 reacts with the corresponding carboxylic acid and a condensation agent or acylating agent [such as Tetrahedron Letters, 2016, 57 (26), 2898-2900; ARKIVOC (Gainesville, FL, United States), 2018, (7), 458-470], etc.; II-1 reacts with the corresponding aldehyde and an oxidant (such as iodine) [such as Green Chemistry Letters and Reviews, 4 (1), 87-89; 2011], etc. Suitable acids can be selected from sulfuric acid, trifluoroacetic acid, trifluoromethanesulfonic acid, etc. Suitable bases can be selected from triethylamine, pyridine, etc. II-3 can be prepared by reacting the corresponding carboxylic acid (or acid chloride, acid anhydride) with N-hydroxyamidine according to the method of I-2.

[0066] Intermediate II-1 is a key intermediate for preparing the compound of formula I-2 of the present invention, and can be prepared according to known methods, for example, refer to the literature Journal of Medicinal Chemistry, 59(6), 2362-2380; 2016.

[0067] Intermediate II-2 is a key intermediate for preparing the compound of general formula I-2 of the present invention, and is prepared by the following method:

[0068]

[0069] Part of the intermediate III is commercially available, or can be prepared by a known method, for example, by the method described in Jiangsu Chemical Industry 1999V27No3P21-22.

[0070] Part of intermediate V is commercially available or can be prepared by a known method, for example, by reacting it with a halogenating agent (such as dichlorohydantoin, dibromohydantoin, chlorine, bromine, N-chlorosuccinimide, N-bromosuccinimide, etc.) in a suitable solvent (such as chloroform, dichloroethane, carbon tetrachloride, etc.) in the presence of a free radical initiator (such as diazoisobutyronitrile, benzoyl peroxide).

[0071] Intermediates III and V react under alkaline conditions in a suitable solvent to obtain intermediate VI.

[0072] Suitable bases can be selected from potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide, etc.

[0073] The reaction is carried out in a suitable solvent, which can be selected from dichloromethane, chloroform, tetrahydrofuran, 1,4-dioxane, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, acetone or butanone.

[0074] The reaction temperature may be between low temperature and the boiling point of the solvent, usually -10°C to 100°C.

[0075] The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.

[0076] Intermediate VI can be reacted with hydroxylamine (or a hydroxylamine salt and a suitable base) in a suitable solvent to give intermediate II-2.

[0077] The hydroxylamine salt may be selected from hydroxylamine hydrochloride, hydroxylamine sulfate and the like.

[0078] Suitable bases can be selected from potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide, etc.

[0079] The reaction is carried out in a suitable solvent, which can be selected from one or a mixture of two or more solvents such as dichloromethane, chloroform, tetrahydrofuran, 1,4-dioxane, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, acetone or butanone, water, ethanol, etc.

[0080] The reaction temperature may be between low temperature and the boiling point of the solvent, usually -10°C to 100°C.

[0081] The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.

[0082] Intermediate II-3 is a key intermediate for preparing the compound of general formula I-3 of the present invention, and is prepared by the following method:

[0083]

[0084] Part of the intermediate X is commercially available, or can be prepared by a known method, for example, by reacting with a halogenating agent (such as dichlorohydantoin, dibromohydantoin, chlorine, bromine, N-chlorosuccinimide, N-bromosuccinimide, etc.) in a suitable solvent (such as chloroform, dichloroethane, carbon tetrachloride, etc.) in the presence of a free radical initiator (such as diazoisobutyronitrile, benzoyl peroxide).

[0085] Intermediate III and X are reacted in a suitable solvent under basic conditions to obtain intermediate XI.

[0086] Suitable bases can be selected from potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide, etc.

[0087] The reaction is carried out in a suitable solvent, which can be selected from dichloromethane, chloroform, tetrahydrofuran, 1,4-dioxane, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, acetone or butanone.

[0088] The reaction temperature may be between low temperature and the boiling point of the solvent, usually -10°C to 100°C.

[0089] The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.

[0090] Intermediate XI can be reacted with sodium hydroxide in a suitable solvent to give intermediate II-3.

[0091] The reaction is carried out in a suitable solvent, which can be selected from one or a mixture of two or more solvents such as tetrahydrofuran, 1,4-dioxane, water, methanol, ethanol, etc.

[0092] The reaction temperature may be between low temperature and the boiling point of the solvent, usually -10°C to 100°C.

[0093] The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.

[0094] Or reference EP0665223A1 etc. are prepared according to the following method:

[0095]

[0096] Intermediates III and IV react under basic conditions in a suitable solvent to obtain compounds of formula I.

[0097] Suitable bases can be selected from potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, triethylamine, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide, etc.

[0098] The reaction is carried out in a suitable solvent, which can be selected from dichloromethane, chloroform, tetrahydrofuran, 1,4-dioxane, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, acetone or butanone.

[0099] The reaction temperature may be between low temperature and the boiling point of the solvent, usually -10°C to 100°C.

[0100] The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.

[0101] Intermediate IV is a key intermediate for preparing the compound of formula I of the present invention. Depending on the different heterocyclic rings connected, intermediate IV can be represented as IV-1 and IV-2, respectively, and can be prepared by the following methods:

[0102]

[0103] Intermediate VII-1 is reacted with hydrazine hydrate solution at a suitable temperature and in a suitable solvent for 30 minutes to 20 hours, usually 6-14 hours, to obtain intermediate VIII-1. The operation method of this step is referred to: Journal of Medicinal Chemistry, 59(6), 2362-2380; 2016.

[0104] Intermediate IX-1 can be prepared by the following method: VIII-1 reacts with the corresponding acid chloride, anhydride or orthoester and a catalyst [such as Synthetic Communications, 2014, 44 (13), 1978-1986; Advanced Synthesis & Catalysis, 2017, 359 (5), 772-778; Synthesis, 2016, 48 (20), 3597-3602; WO2017018803A1]; VIII-1 reacts with the corresponding carboxylic acid and a condensation agent [such as Tetrahedron Letters, 2016, 57 (26), 2898-2900; ARKIVOC (Gainesville, FL, United States), 2018, (7), 458-470], etc.; VIII-1 reacts with the corresponding aldehyde and iodine catalysis.

[0105]

[0106] Intermediate Ⅶ-2 is reacted with hydroxylamine (or hydroxylamine salt and base) at a suitable temperature and in a suitable solvent for 30 minutes to 20 hours, usually 6-14 hours, to obtain intermediate Ⅷ-2. The operation method of this step is referred to: WO2017178549A1.

[0107] Intermediate IX-2 can be prepared by the following method: VIII-2 is reacted with the corresponding acid chloride, anhydride or orthoester and a catalyst [such as Synthetic Communications, 2014, 44 (13), 1978-1986; Advanced Synthesis & Catalysis, 20 [such as Tetrahedron Letters, 2016, 57 (26), 2898-2900; ARKIVOC (Gainesville, FL, United States), 2018, (7), 458-470], etc.

[0108] R8, R9 and R recorded in the above preparation process 10 The selection of is the same as the substituents on Het described in the claims.

[0109] A use of the compound of general formula I in agriculture or other fields for preparing bactericidal and insecticidal drugs.

[0110] A bactericidal and insecticidal composition comprises the compound of general formula I as an active component and a carrier acceptable for agriculture, forestry or hygiene, wherein the weight content of the compound of general formula I as an active component in the composition is 1-99%.

[0111] A method for controlling diseases, wherein the composition is applied to the diseases to be controlled or the medium where they grow at an effective dosage of 10 to 1000 grams per hectare.

[0112] Although the compounds of general formula I of the present invention and some compounds disclosed in the prior art also belong to the pyridazinone class of compounds, there are still differences in their structural features. And due to these structural differences, the compounds of the present invention have better fungicidal and insecticidal activities.

[0113] The compounds of general formula I show excellent activity against a variety of pathogens and pests in agriculture or other fields. Therefore, the technical scheme of the present invention also includes the use of the compounds of general formula I in agriculture or other fields for preparing fungicides and insecticides.

[0114] The examples of diseases mentioned below are only used to illustrate the present invention, but they are by no means limiting.

[0115] The compounds of general formula I can be used to control the following diseases: Oomycete diseases, such as downy mildew (cucumber downy mildew, rape downy mildew, soybean downy mildew, beet downy mildew, sugarcane downy mildew, tobacco downy mildew, pea downy mildew, loofah downy mildew, wax gourd downy mildew, melon downy mildew, cabbage downy mildew, spinach downy mildew, radish downy mildew, grape downy mildew, onion downy mildew), white rust (rape white rust, cabbage white rust), damping-off disease (rapeseed damping-off, tobacco damping-off, tomato damping-off, pepper damping-off, eggplant damping-off, cucumber damping-off, cotton seedling damping-off), cotton rot (pepper cotton rot, loofah cotton rot, wax gourd cotton rot), blight (broad bean blight, cucumber blight, pumpkin blight, wax gourd blight, watermelon blight, melon blight, pepper blight, leek blight, garlic blight, cotton blight), late blight (potato late blight, tomato late blight), etc.;Deuteromycin diseases, such as wilt (sweet potato wilt, cotton wilt, sesame wilt, castor wilt, tomato wilt, kidney bean wilt, cucumber wilt, loofah wilt, pumpkin wilt, wax gourd wilt, watermelon wilt, melon wilt, pepper wilt, broad bean wilt, rapeseed wilt, soybean wilt), root rot (pepper root rot, eggplant root rot, kidney bean root rot, cucumber root rot, bitter melon root rot, cotton black root rot, broad bean root rot), damping-off (cotton seedling damping-off, sesame damping-off, pepper damping-off, cucumber damping-off, cabbage damping-off), anthracnose (sorghum anthracnose, cotton anthracnose, hemp anthracnose, jute anthracnose, flax anthracnose, tobacco anthracnose, mulberry anthracnose Disease, pepper anthracnose, eggplant anthracnose, bean anthracnose, cucumber anthracnose, bitter gourd anthracnose, zucchini anthracnose, wax gourd anthracnose, watermelon anthracnose, melon anthracnose, litchi anthracnose), Verticillium wilt (cotton wilt, sunflower wilt, tomato wilt, pepper wilt, eggplant wilt), black spot (zucchini black spot, wax gourd black spot, melon black spot), gray mold (cotton boll gray mold, hemp gray mold, tomato gray mold, pepper gray mold, kidney bean gray mold, celery gray mold, spinach gray mold, kiwifruit gray mold), brown spot (cotton brown spot, jute brown spot, beet brown spot, peanut brown spot, pepper brown spot, wax gourd brown spot, soybean brown spot, sunflower brown spot, pea brown spot Black spot (false black spot of flax, black spot of rape, black spot of sesame, black spot of sunflower, black spot of castor, black spot of tomato, black spot of pepper, black spot of eggplant, black spot of kidney bean, black spot of cucumber, black spot of celery, black rot of carrot, black spot of carrot, black spot of apple, black spot of peanut), spot blight (spot blight of tomato, spot blight of pepper, spot blight of celery), early blight (early blight of tomato, early blight of pepper, early blight of eggplant, early blight of potato, early blight of celery), ring rot (soybean ring rot, sesame ring rot, kidney bean ring rot), leaf blight (sesame leaf blight, sunflower leaf blight, watermelon leaf blight, melon leaf blight), stem base rot (stem base rot of tomato, vegetable Bean stem base rot), and others (corn round spot, jute waist break disease, rice blast, chestnut black sheath disease, sugarcane eye spot disease, cotton boll Aspergillus disease, peanut crown rot, soybean stem blight, soybean black spot disease, melon large spot disease, peanut web spot disease, tea red leaf spot disease, pepper white star disease, wax gourd leaf spot disease, celery black rot, spinach heart rot, jute leaf mold, jute spot disease, jute stem spot disease, soybean purple spot disease, sesame leaf spot disease, castor gray spot disease, tea brown leaf spot disease, eggplant brown round star disease, kidney bean red spot disease, bitter melon white spot disease, watermelon spot disease, jute blight rot, sunflower root and stem rot disease, kidney bean charcoal rot, soybean target spot disease, eggplant coryneform leaf spot disease, cucumber target spot disease, tomato leaf mold disease, eggplant leaf mold disease, broad bean red spot disease, etc.);Basidiomycete diseases, such as rust (wheat stripe rust, wheat stem rust, wheat leaf rust, flower rust, sunflower rust, sugarcane rust, leek rust, onion rust, chestnut rust, soybean rust), smut (corn silk smut, corn powdery mildew, sorghum silk smut, sorghum loose smut, sorghum hard smut, sorghum column powdery mildew, chestnut kernel smut, sugarcane smut, bean rust) and others (such as wheat sheath blight, rice sheath blight, etc.); Ascomycete diseases, such as powdery mildew (wheat powdery mildew, rape powdery mildew, sesame powdery mildew, Powdery mildew of sunflower, beet, eggplant, pea, loofah, pumpkin, zucchini, wax gourd, melon, grape, broad bean), sclerotinia (flax, rape, soybean, peanut, tobacco, pepper, eggplant, bean, pea, cucumber, bitter melon, wax gourd, watermelon, celery), scab (apple scab, pear scab), etc. ;

[0116] The compounds shown in general formula I can be used to control the following pests:

[0117] Coleoptera (Beetles): Acanthoscelides spp. (Weevils), Acanthoscelides obtectus (Common Pea Weevils), Agrilus planipennis (Willow Ash Borer), Agriotes spp. (Wireworms), Anoplophora glabripennis (Asian Longhorn Beetle), Anthonomus spp. (Curculidae), Anthonomus grandis (Cotton Bollworm), Aphidius spp., Apion spp. (Weevils), Apogonia spp. (Grubs), Atacnius sprctulus (Black Velvet Beetle), Atomaria linearis (Pygmy Beetle), mangold beetle, Aulacophore spp., Bothynoderes punctiventris (beetroot weevil), Bruchus spp. (weevil), Bruchus pisorum (pea weevil), Cacoesia spp., Callosobruchus maculatus (southern cowpea weevil), Carpophilus hemipteras (dried fruit beetle), Cassida vittata, Ccrostcrna spp., Ccrotoma spp. (chrysomcides), Cerotoma trifur cata (bean leaf beetle), Ceutorhynchus spp.) (weevils), Ceutorhynchus assimilis (cabbage seedpod weevil), Ceutorhynchus napi (cabbage curculio), Chaetocnema spp. (trichomoniasis), Colaspis spp.) (earth beetle), Conoderus scalaris, Conoderus stigmosus, Conotrachelus nenuphar (Plum cone weevil), Cotinus nitidis (Green June beetle), Crioceris asparagi (Asparagi beetle), Cryptolestes ferrugincus (rusty grain beetle), Cryptolestes pusillus (grain beetle), Cryptolestes turcicus (Turkish grain beetle), Ctenicera spp. (nematodes), Curculio spp. (weevils), Cyclocephala spp. (grubs), Cylindrocpturus adspersus (sunflower stem weevil), Deporaus marginatus (mango leaf-cutting weevil), Dermestes lardarius (ham stem weevil), Dermestes maculates (white-bellied weevil), Diabrotica spp. (leaf beetles), Epilactina varivcstis (Mexican bean beetle), Raustinus cubae, Hylobius pales (pales weevil), Hypera spp. (weevils), Hypera postica (alfalfa weevil), Hyperdoes spp. (Hyperodes weevil), Hypothenemus hampei) (coffee berry beetle), Ips spp.) (engravers), Lasioderma serricorne (tobacco beetle), Leptinotarsa ​​decemlineata (Colorado potato beetle), Liogenys fuscus, Liogenys suturalis, Lissorhoptrus oryzophilus (rice water weevil), Lyctus spp. (powder post beetles), Maecolaspis joliveti, Megascelis spp., Melanotus communis, Meligethes spp., Meligethes aeneus (blossom beetle), Melolontha melolontha (common European beetle), Oberea brevis, Oberea linearis, Oryctes rhinoceros (date palm beetle), Oryzaephilus mercator (merchant grain beetle), Oryzaephilus surinamensis (sawtooth grain beetle), Otiorhynchus spp. (weevils), Oulema melanopus (cerealleaf beetle), Oulema oryzae, Pantomorus spp. (weevils), Phyllophaga spp. (May / June beetles), Phvllophaga cuyabana, Phyllotreta spp.) (Trichomonas), Phynchites spp.), Popillia japonica (Japanese beetle), Prostephanus truncates (larger grain borer), Rhizopertha dominica (lesser grain borer), Rhizotrogus spp. (Eurpoean chafer), Rhynchophorus spp. (weevils), Scolytus spp. (wood moths), Shenophorus spp. (grain weevils), Sitona lincatus (pea leaf weevil), Sitophilus spp. (grain weevils), Sitophilus granaries (granary weevil), Sitophilus oryzae (rice weevil), weevil), Stegobium paniceum (drugstore beetle), Tribolium spp. (flour weevil), Tribolium castaneum (red flour beetle), Tribolium confusum (confused flour beetle), Trogoderma variabile (warehouse beetle), and Zabrus tenebioides.

[0118] Dermaptcra (earwigs).

[0119] Dictyoptera (cockroaches): Blattella germanica (German cockroach), Blatta orientalis (Oriental cockroach), Parcoblatta pennylvanica, Periplaneta americana (American cockroach), Periplaneta australoasiae (Australian cockroach), Periplaneta brunnca (brown cockroach), Periplaneta fuliginosa (smoky brown cockroach), Pyncoselus suninamensis (Surinam cockroach), and Supella longipalpa) (brownbanded cockroach).

[0120] Diptera (flies): Aedes spp. (mosquitoes), Agromyzafrontella (alfalfa blotch leafminer), Agromyza spp. (leafminers), Anastrepha spp. (fruit flies), Anastrepha suspensa (Caribbean fruit fly), Anopheles spp. (mosquitoes), Batrocera spp. (fruit flies), Bactrocera cucurbitae (melon fly), Bactrocera dorsalis (orange fruit fly), Ceratitis spp. (fruit flies), Ceratitis capitata (Mediterranean fruit fly), Chrysops spp.) (deer flies), Cochliomyia spp. (bloom fly larvae), Contarinia spp. (mosquitoes), Culex spp. (mosquitoes), Dasineura spp. (mosquitoes), Dasineura brassicae (cabbage midges), Delia spp., Delia platura (seed corn maggots), Drosophila spp. (vinegar flies), Fannia spp. (house flies), Fannia canicularis (little house fly), Fannia scalaris (gray-bellied toilet fly), Gasterophilus intestinalis (horse stomach fly), Gracillia perseae, Haematobia irritans (horn fly), Hylemyia spp. (root maggot), Hypoderma lineatum (common cattle grub), Liriomyza spp.) (leaf miner), Liriomyza brassica (serpentine leaf miner), Melophagus ovinus (sheep tick), Musca spp. (muscid fly), Musca autumnalis (face fly), Vusca domestica (house fly), Oestrus ovis (sheep bot fly), Oscinella frit (Swedish straw fly), Pegomyia betae (beet leaf miner), Phorbia spp., Psila rosae (carrotrust fly), Rhagoletis cerasi (cherry fruit fly), Rhagoletis pomonella (apple maggot), Sitodiplosismosellana (orange wheat blossom midge), stomoxyscalcitruns (stable fly), Tahanus spp. (horse flies), and Tipula spp. (crane flies).

[0121] Hemiptera (Stinkbugs): Acrosternum hilare (green stinkbug), Blissus leucopterus (chinch bug), Calocoris norvegicus (potato mirid), Cimex hemipterus (tropical bed bug), Cimex lectularius (bed hug), Daghertus fasciatus, Dichelops furcatus, Dysdercus suturellus (cotton stainer), Edessa meditabunda, Eurygaster maura (cereal bug), Euschistus heros, Euschistus servus) (brown stink bug), Helopeltis antonii, Helopeltis theivora (tea blight plant bug), Lagynotomus spp. (stink bugs), Leptocorisa oratorius, Leptocorisa varicornis, Lygus spp. (plant bugs), Lygushesperus (western tarnished plant bug), Maconellicoccus hirsutus, Neurocolpus longirostris, Nezara viridula (southern green stink bug), PhyLocoris spp.)(blind bug), Phytocoris californicus, Phytocoris relativus, Piezodorus guildingi, Poecilocapsus lineatus (fourlined plant bug), Psallus vaccinicola, Pseudacysta perseae, Scaptocoris castanea, and Triatoma spp. (bloodsucking conenoses / kissing bugs).

[0122] Homoptera (aphids, scales, whiteflies, leafhoppers): Acrythosiphonpisum (pea aphid), Adelges spp. (adelgids), Aleurodes proletella (cabbage whitefly), Aleurodicus disperses, Aleurothrixus flccosus (woolly whitefly), Aluacaspis spp., Amrasca bigutella bigutella, Aphrophora spp. (leafhopper), Aonidiella aurantii (California redscale), Aphis spp. (aphids), Aphis gossypii (cotton aphid), Aphis apple aphid (apple aphid), Aphis spp. (cotton aphid), Aphis spp. (cotton whitefly ... pomi (apple aphid), Aulacorthitm solani (foxglove aphid), Bemisia spp. (whitefly), Bemisia argentifolii, Bemisia tabaci (sweetpotato whitefly), Brachycolus noxius (Russian aphid), Brachycorynclia asparagi (asparagus aphid), Brevennia rehi, Brevicoryne brassicae (cabbage aphid), Ceroplastes spp. (scale), Ceroplastes rubens (red wax scale), Chionaspis spp.) (scale), Chrysomphalus spp. (scale), Coccus spp. (scale), Dysaphis plantaginea (rosy apple aphid), Empoasca spp.) (leafhopper), Eriosoma lanigerum (woolly apple aphid), Icerya purchasi (cottony cushion scale), Idioscopus nitidulus (mango leafhopper), Laodelphax striatellus (smaller brown planthopper), Lepidosaphes spp., Macrosiphum spp., Macrosiphum euphorbiae (potato aphid), Macrosiphum granarium (English grain aphid), Macrosiphum rosae (rose aphid), Macrosteles quadrilineatus (asterleafhopper), Mahanarva frimbiolata, Metopolophium dirhodum (rose grain aphid), Midis longicornis, Myzus persicae (green peach aphid), Nephotettix spp. (leafhopper), Nephotettix cinctipes (green leafhopper), Nilaparvata lugens (brown planthopper), Parlatoria pergandii (chaff scale), Parlatoriaziziphi (ebony scale), Peregrinus maidis (corn delphacid), Philaenus spp. (foam bug), Phylloxera vitifoliae (grapephylloxera), Physokermes piceae (spruce bud scale), Planococcus spp.) (mealybugs), Pseudococcus spp.)(mealybug), Pscudococcus brcvipcs(pinc apple mcalybug), Quadraspidiotus perniciosus(San Jose scale), Rhapalosiphum spp.(aphids), Rhapalosiphum maida(corn leaf aphid), Rhapalosiphumpadi(oatbird-cherry aphid), Saissetia spp.(scale), Saissetiaoleae(black scale), Schizaphis graminum(g eenbug), Sitobion avenge(British wheat aphid), Sogatella furcifera(white-backed planthopper), furcifera)(white-backed planthopper), Therioaphis spp.(aphids), Toumeyella spp.(scale), Toxoptera spp.(aphids), Trialeurodes spp.(whiteflies), Trialeurodes vaporariorum(greenhouse whitefly), Trialeurodes abutiloneus(bandedwing whitefly), Unaspis spp.(scale), Unaspis yanonensis(arrowhead scale), and Zulia entreriana.

[0123] Hymenoptera (Ants, Wasps and Bees): Acromyrrmex spp., Athalia rosae, Atta spp. (Ieafcutting ants), Camponotus spp. (carpenter ants), Diprion spp. (sawflies), Formica spp. (ants), Iridomyrmex humilis (Argentine ants), Monomorium ssp., Monomorium minumum (little black ant), Monomorium pharaonis (Pharaoh ant), Neodiprion spp. (sawflies), Pogonomyrmex humilis (Argentine ants), spp. (harvester ants), Polistes spp. (paper wasps), Solenopsis spp. (fire ants), Tapoinoma sessile (odorous house ants), Tetranomorium spp. (pavement ants), Vespula spp. (yellow jackets), and Xylocopa spp. (carpenter bees).

[0124] Isoptera (Termites): Coptotermes spp., Coptotermes curvignathus, Coptotermes frenchii, Coptotermesformosanus (Formosan subterranean termite), Cornitermes spp. (nasute termite), Cryptotermes spp. (drywood termite), Heterotermes spp. (desert subterranean termite), Iletotermes aureus, Kalotermes spp. (drywood termite), Incistitermes spp. (drywood termite), Macrotermes spp. spp.) (fungusgrowing termite), Marginitermes spp. (drywood termites), Microcerotermes spp. (harvester termites), Microtermesobesi, Procornitermes spp., Reticulitermes spp. (soil-dwelling termites), Reticulitermes banyulensis, Reticulitermes grassei, Reticulitermes flavipes (Eastern soil-dwelling termites), Reticulitermes shageni, Reticulitermes hesperus (Western soil-dwelling termites), Reticulitermes santonensis, Reticulitermes speratus, Reticulitermes tibialis), Reticulitermes virginicus, Schedorhinotermes spp., and Zootermopsis spp. (wood-destroying termites).

[0125] Lepidoptera (moths and butterflies): Achoea janata, Adoxophyes spp., Adoxophyes orana, Agrotis spp. (cutworms), Agrotis ipsilon (black cutworm), Alabama argillacea (cotton leafworm), Amorbia cuneana, Amyelosis transitella (navel orangeworm), Anacamptodes defectaria, Anarsia lineatella (peach twig borer), Anomis sabulijera (jute looper), Anticarsia gemmatalis (velvet bean caterpillar), Archips argyrospila (fruit tree leaf roller), Archips rosana (rose leaf roller), roller), Argyrotaenia spp. (tortricid moths), Argyrotaenia citrana (orange tortrix), Autographa gamma, Bonagota cranaodcs, Borbocinnara (rice leaf folder), Bucculatrix thurberiella (cottonleaf perforator), Caloptilia spp. (leaf miners), Capua reticulana, Carposina niponensis (peach fruit moth), Chilo spp., Chlumetia transversa (mango shoot borer), Choristoneura rosaceana (oblique banded leaf roller), Chrysodeixis spp.), Cnaphalocerus medinalis (grass leafroller), Coli spp., Conpomorpha cramerella, Cossus cossus (wood moth), Crambus spp. (Sod webworms), Cydia funebrana (plum fruit moth), Cydia molesta (oriental fruit moth), Cydia nignicana (pea moth), Cydia pomonella (codling moth), Darna diducta, Diaphania spp. (stem borer), Diatraceae spp.) (stalk borer), Diatraea saccharalis (sugarcane borer), Diatraea graniosella (southwester cornborer), Earias spp. (cotton bollworm), Earias insulata (Egyptian bollworm), Earias vit.ella (rough northern bollworm), Ecdytopophaaurantianum, Elasmopalpus lignosellus (lesser cornstalk borer), Epiphysias postruttana (light brown apple moth), Ephestia spp. (powdery moth), Ephestia cautella (almond moth), Ephestia elutella) (tobbaco moth), Ephestia kuehniella (Mediterranean flour moth), Epimeces spp.), Epinotiaaporema, Erionota thrax (banana skipper), Eupoeciliaambiguella (grape berry moth), Euxoa auxiliaris (army cutworm), Feltia spp. (cutworms), Gortyna spp. (stem borers), Grapholita molesta (oriental fruit moth), Hedylepta indicata (bean leaf webber), Helicoverpa spp. (snoctuid armyworms), Helicoverpa armigera (cotton bollworm), Helicoverpazea (corn borer / bollworm), Heliothis spp. (noctuid), Heliothis virescens (tobacco budworm), Hellula undalis (cabbage webworm), Indarbela spp. (root borer), Keiferia lycopersicella (tomato pinworm), Leucinodes orbonalis (eggplant fruit borer), Leucoptera malifoliella, Lithocollectis spp., Lobesia botrana (grape fruit moth), Loxagrotis spp. (noctuid), Loxagrotis albicosta (western bean cutworm), Lymantria dispar (gypsy moth), Lyonetia clerkella (apple leaf miner), Mahasena corbetti (oil palm bagworm), Malacosoma spp.)(tent caterpillars), Mamestra brassicae(cabbage armyworm), Maruca testulalis(bean borer), Metisa plana(knotworm), Mythimna unipuncta(true armyworm), Neoleucinodes elegantalis(small tomato borer), Nymphula depunctalis(rice caseworm), Operophthera brumata(winter moth), Ostrinianubilalis(European corn borer), Oxydia vesulia, Pandemiscerasana(common currant tortrix), Pandemis heparana(brown apple tortrix), Papilio demodocus, Pectinophoragossypiella (pink bollworm), Peridroma spp. (cutworm), Peridroma saucia (variegated cutworm), Perileucopteracoffeella (white coffee leafminer), Phthorimaea operculella (potato tuber moth), Phyllocnisitis citrella, Phyllonorycter spp.) (leaf miner), Pieris rapae (imported cabbageworm), Plathypena scabra, Plodia interpunctella (Indian meal moth), Plutella xylostella (diamondback moth), Polychrosis viteana (grape berry moth), Prays endocarps, Prsys oleae (olive moth), Pseudaletia spp. (snow moth), Pseudaletia unipunctata (army bug), Pseudoplusia includens (soybean looper), Rachiplusia nu, Scirpophaga incertulas, Sesamia spp. (stem borers), Sesamia inferens (pink rice stemborer), Sesamianonagrioides, Setora nitens, Sitotroga cerealella (Angoumoisgrain moth), Sparganothis pilleriana, Spodoptera spp. (armyworms), Spodoptera exigua (beet armyworm), Spodoptera fugipcrda (fall armyworm), Spodoptera oridania (southern armyworm), Synanthedon spp. (root borers), Thecla basilides, Thermisia gemmatalis, Tineola bisselliella (webbingclothes moth), Trichoplusia ni (cabbage armyworm), looper), Tutsabsoluta, Yponomeuta spp.), Zeuzera coffeae (red branchborer), and Zeuzera pyrina (pear leopard moth).

[0126]

[0043] Mallophaga (Mallophaga chewing lice): Bovicola ovis (sheep biting louse), Menacanthus stramineus (chicken body louse), and Menopon gallinea (common hen house).

[0127]

[0043] From the Order of Orthoptera (grasshoppers, locusts and crickets): Anabrus simplex (Mormon cricket), Gryllotalpidae (mole cricket), Locusta migratoria, Melanoplus spp. (grasshoppers), Microcentrum retinerve (angular winged katydid), Pterophylla spp. (katydids), chistocerca gregaria, Scudderia furcata (fork tailed bush katydid) and Valanga nigricorni.

[0128]

[0043] From the order of Phthiraptera (sucking louse): Haematopinus spp. (cattle and pig lice), Linognathus ovillus (sheep louse), Pediculus humanus capitis (body louse), Pediculus humanus humanus (body louse), and Pthirus pubis (crab louse).

[0129] Siphonaptera (Fleas): Ctenocephalides canis (dog flea), Ctenocephalides felis (cat flea), and Pulex irritans (human flea).

[0130] Thysanoptera (Thrips): Frankliniella fusca (tobacco thrip), Frankliniella occidentalis (western flower thrips), Frankliniella shultzei, Frankliniella williamsi (corn thrip), Ileiothrips haemorrhaidalis (greenhouse thrip), Riphiphorothrips cruentatus, Scirtothrips spp., Scirtothrips cirri (citrus thrip), Scirtothrips dorsalis (yellow tea thrips), Taeniothrips rhopalantennalis, and Thrips spp.

[0131] From the order of the Thysanura (bristletails): Lepisma spp. (silverfish) and Thermobia spp. (silverfish).

[0132] Order Acarina (mites and ticks): Acarapsis woodi (tracheal mite of honeybee), Acarus spp. (food mite), Acarus siro (grain mite), Aceria mangiferae (mango bud mite), Aculops spp., Aculops lycopersici (tomato russetmite), Aculops pelekasi, Aculus pelekassi, Aculusschlechtendali (apple rust mite), Amblyomma amcricanum (lone star tick), Boophilus spp.) (ticks), Brevipalpus obovatus (privet mite), Brevipalpus phoenicis (red and black flat mite), Demodex spp. (mange mites), Dermacentor spp. (hard ticks), Dermacentor variabilis (American dog tick), Dermatophagoides pteronyssinus (house dust mite), Eotetranycus spp., Eotetranychus carpini (yellow spider mite), Epitimerus spp., Eriophyes spp., Ixodes spp. (ticks), Metatetranycus spp. spp.), Notoedres cati, Oligonychus spp., Oligonychus coffee, Oligonychus ilicus (southernred mite), Panonychus spp.), Panonychus cirri (citrus red mite), Panonychus ulmi (European red mite), Phyllocoptruta oleivora (citrus rust mite), Polyphagotarsonemun latus (broad mite), Rhipicephalus sanguineus (brown dog tick), Rhizoglyphus spp. (bulb mite), Sarcoptes scabiei (itch mite), Tegolophus perseaflorae, Tetranychus spp., Tetranychus urticae (twospotted spider mite), mite) and Varroa destructor (honey bee mite).

[0133] Nematodes: Aphelenchoides spp. (bud and leaf & pine wood nematodes), Belonolaimus spp. (sting nematodes), Criconemella spp. (ring nematodes), Dirofilaria immitis (dog heartworm), Ditylenchus spp. (stem and bulb nematodes), Heterodera spp. (cyst nematode), Heterodera zeae (corn cyst nematode), Hirschmanniella spp. (root nematodes), Hoplolaimus spp. (lance nematodes), Meloidogyne spp.) (root-knot nematode), Meloidogyne incognita (root-knot nematode), Onchocerca volvulus (hook-tail worm), PraLylenchus spp. (lesion nematode), Radopholus spp. (burrowing nematode), and Rotylenchus reniformis (kidney-shaped nematode).

[0134] Synthesize (integrated insect class): White pine borer (Scutigerella immaculata).

[0135] Due to their positive properties, the above-mentioned compounds can be advantageously used for protecting important agricultural and horticultural crops, livestock and breeding stock, as well as the environment frequented by humans from pathogens, insect pests and acarids.

[0136] To obtain the desired effect, the amount of compound used will vary depending on factors such as the compound used, the crop to be protected, the type of pest, the degree of infestation, climatic conditions, the method of application, and the formulation employed.

[0137] Doses of 10 g to 5 kg of compound per hectare provide adequate control.

[0138] The present invention also includes a bactericidal, insecticidal and acaricidal composition with the compound of general formula I as an active component. The weight percentage of the active component in the bactericidal, insecticidal and acaricidal composition is between 0.5-99%. The bactericidal, insecticidal and acaricidal composition also includes a carrier acceptable for agriculture, forestry and hygiene.

[0139] The composition of the present invention can be applied in the form of a preparation. The compound shown in general formula I is dissolved or dispersed in a carrier as an active ingredient or formulated into a preparation so that it is easier to disperse when used as a bactericidal or insecticidal agent. For example, these chemical preparations can be made into wettable powders, oil suspensions, water suspensions, aqueous emulsions, aqueous solutions or emulsifiable concentrates. In these compositions, at least one liquid or solid carrier is added, and when necessary, a suitable surfactant can be added.

[0140] The technical scheme of the present invention also includes a method for preventing and controlling pathogens, insect pests and mites: applying the bactericidal, insecticidal and acaricidal composition of the present invention to the pathogens or their growth medium. The generally selected effective amount is 10 to 1000 grams per hectare, and the preferred effective amount is 20 to 500 grams per hectare.

[0141] For certain applications, such as in agriculture, one or more other fungicides, insecticides, acaricides, herbicides, plant growth regulators or fertilizers may be added to the fungicidal, insecticide and acaricide composition of the present invention, thereby producing additional advantages and effects.

[0142] It should be understood that various changes and modifications can be made within the scope of the present invention as defined by the claims. DETAILED DESCRIPTION

[0143] The following specific examples are used to further illustrate the present invention, but the present invention is by no means limited to these examples (unless otherwise noted, all raw materials used are commercially available).

[0144] Synthesis Example

[0145] Example 1: Preparation of intermediate p-methylbenzoyl hydrazide

[0146]

[0147] 16.42g (0.1mol) of ethyl p-methylbenzoate and 10mL of hydrazine hydrate (85%) were placed in a single-mouth bottle containing 50mL of ethanol and refluxed for 12 to 18 hours. After the reaction was completed, colorless needle-shaped crystals were precipitated by natural cooling, filtered and washed with a cold 10% ethanol aqueous solution, and dried to obtain 8.90g of colorless crystals with a yield of 59.26%.

[0148] Example 2: Preparation of intermediate 2-p-tolyl-5-trifluoromethyl-1,3,4-oxadiazole

[0149]

[0150] 7.51g (0.05mol) of p-methylbenzoyl hydrazide and 6.84g (0.06mol) of trifluoroacetic acid were placed in a single-mouth bottle, 10mL of phosphorus oxychloride was added dropwise, and the mixture was refluxed for 12 to 18 hours. After the reaction was completed, volatiles were removed, water was added after cooling, and the mixture was stirred for 30 minutes to precipitate a white solid, which was filtered and washed with water. After drying, 9.20g of a white solid was obtained, with a yield of 80.64%.

[0151] Example 3: Preparation of the intermediate 2-(4-bromomethylphenyl)-5-trifluoromethyl-1,3,4-oxadiazole

[0152]

[0153] Take 6.85g (0.03mol) 2-p-tolyl-5-trifluoromethyl-1,3,4-oxadiazole and 50mL carbon tetrachloride and put them into a three-necked flask. After heating to reflux, add catalytic amount of AIBN, and then add 5.87g (0.033mol) NBS in batches, and reflux for 4 to 10 hours. After the reaction is completed, remove the volatile matter, dissolve it in ethyl acetate and wash it with 5% sodium carbonate solution, concentrate the organic layer, and perform column chromatography to obtain a colorless oil, which becomes a colorless solid of 6.17g after long-term storage, with a yield of 66.98%.

[0154] Example 4: Preparation of Compound I-1-20 5-((4-(5-trifluoromethyl-1,3,4-oxadiazol-2-yl)benzylthio)-2-tert-butyl-4-chloropyridazin-3(2H)-one

[0155]

[0156] 0.307g (1mmol) 2-(4-bromomethylphenyl)-5-trifluoromethyl-1,3,4-oxadiazole and 2.19g (1mmol) 2-tert-butyl-4-chloro-5-mercaptopyridazine-3(2H)-one were placed in a single-mouth bottle containing 5mL DMF, and 1.38g (1mmol) potassium carbonate was added at room temperature, and the reaction was continued for 2 to 18 hours. After the reaction was completed, the reaction solution was poured into water, filtered, and the filter cake was washed with water, dried, dissolved in ethyl acetate, and mixed, and 0.338g of white solid was obtained by silica gel column chromatography, with a yield of 75.98%.

[0157] Example 5: Preparation of Intermediate 4-(((1-tert-butyl-5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)thiomethyl)benzonitrile

[0158]

[0159] 15.16g (0.1mol) of p-cyanobenzyl chloride and 21.87g (0.1mol) of 2-tert-butyl-4-chloro-5-mercaptopyridazine-3(2H)-one were placed in a three-necked flask containing 250mL of DMF, and 13.82g (0.1mol) of potassium carbonate was added in batches at room temperature, and the reaction was continued for 2 to 18 hours. After the reaction was completed, the reaction solution was poured into water, filtered, and the filter cake was washed with water, dried, dissolved in ethyl acetate, and mixed, and 17.05g of white solid was obtained by silica gel column chromatography, with a yield of 51.07%.

[0160] 1 H NMR (600MHz, Chloroform-d) δ7.66 (d, J = 8.2Hz, 2H), 7.53 (d, J = 8.1Hz, 2H), 7.50 (s, 1H), 4.29 (s, 2H), 1.61 (s, 9H).

[0161] Example 6: Preparation of intermediates 4-((1-tert-butyl-5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)thiomethyl)benzamide and N-hydroxy-4-((1-tert-butyl-5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)thiomethyl)benzamide

[0162]

[0163] 3.34g (0.01mol) of 4-((1-tert-butyl-5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)thiomethyl)benzonitrile, 1.38g (0.02mol) of hydroxylamine hydrochloride and 2.76g (0.02mol) of potassium carbonate were placed in a three-necked flask containing 20mL of ethanol and refluxed for 10 to 18 hours. After the reaction was completed, the reaction solution was poured into water, filtered and the filter cake was washed with water, dried, dissolved in ethyl acetate and mixed, and separated by silica gel column chromatography.

[0164] White solid, 0.9 g of 4-((1-tert-butyl-5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)thiomethyl)benzamide, yield: 25.58%. 1 HNMR(600MHz,Chloroform-d)δ7.66(d,J=8.2Hz,2H),7.53(d,J=8.1Hz,2H),7.50(s,1H),4.29(s,2H),1.61(s,9H).

[0165] White solid, 2.1 g of N-hydroxy-4-((1-tert-butyl-5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)thiomethyl)benzamidine, yield 57.24%. 1H NMR (600MHz, Chloroform-d) δ7.62(d,J=8.3Hz,2H),7.56(s,1H),7.44(d,J=8.4Hz,2H),4.87(s,2H),4.27(s,2H),1.61(s,9H).

[0166] Example 7: Preparation of Compound I-2-11 5-((4-(1,2,4-oxadiazol-3-yl)benzylthio)-2-tert-butyl-4-chloropyridazin-3(2H)-one

[0167]

[0168] 0.366g (1mmol) of N-hydroxy-4-((1-tert-butyl-5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)thiomethyl)benzamide, 3mL of trimethyl orthoformate and 1mL of trifluoroacetic acid were placed in a single-mouth bottle and refluxed for 10 to 18 hours. After the reaction was completed, the sample was directly mixed and silica gel column chromatography was performed to obtain 0.271g of white solid compound I-2-11 5-((4-(1,2,4-oxadiazol-3-yl)benzylthio)-2-tert-butyl-4-chloropyridazin-3(2H)-one, with a yield of 71.91%.

[0169] Embodiment 8:

[0170] Preparation of the intermediate 4-((1-tert-butyl-5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)thiomethyl)-N-(dimethylaminomethylene)benzamide of reference compound CK1

[0171]

[0172] 0.704g (2mmol) of 4-((1-tert-butyl-5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)thiomethyl)benzamide and 3mL of N,N-dimethylformamide dimethyl acetal were placed in a single-mouth bottle and refluxed for 10 to 18 hours. After the reaction was completed, the sample was directly stirred and subjected to silica gel column chromatography to obtain 0.750g of a yellow solid with a yield of 92.15%.

[0173] 1 H NMR (600MHz, Chloroform-d) δ8.63(s,1H),8.25(d,J=8.3Hz,2H),7.54(s,1H),7.45(d,J=8.2Hz,2H),4.29(s,2H),3.21(s,3H),3.19(s,3H),1.59(s,9H).

[0174] Preparation of reference compound CK15-(4-(1H-1,2,4-triazol-5-yl)benzylthio)-2-tert-butyl-4-chloropyridazin-3(2H)-one

[0175]

[0176] 0.406g (1mmol) of 4-((1-tert-butyl-5-chloro-6-oxo-1,6-dihydropyridazin-4-yl)thiomethyl)-N-(dimethylaminomethylene)benzamide and 0.060g (1.2mmol) of hydrazine hydrate (85%) were placed in a single-mouth bottle, and 5mL of ethanol was added. The mixture was refluxed for 10 to 18 hours. After the reaction was completed, the sample was directly stirred and 0.210g of a white solid was obtained by silica gel column chromatography, with a yield of 55.87%.

[0177] White solid, mp 148.5℃. 1 H NMR δ8.24(s,1H),8.10–8.05(m,2H),7.61(s,1H),7.52–7.47(m,2H),4.30(s,2H),1.60(s,9H).

[0178] According to the preparation method of the compound of general formula I described above, and the specific process given in the synthesis example, other compounds represented by general formula I can be obtained by simply replacing the raw materials (see Tables 1 and 2).

[0179]

[0180] Note: R2, R3 = H;

[0181] Table 1 Structures and physical properties of some compounds of general formula I-1

[0182]

[0183]

[0184]

[0185]

[0186]

[0187]

[0188]

[0189]

[0190]

[0191]

[0192]

[0193]

[0194]

[0195]

[0196]

[0197]

[0198] Note: R2, R3 = H;

[0199] Table 2 Structures and physical properties of some compounds of general formula I-2

[0200]

[0201]

[0202]

[0203]

[0204]

[0205]

[0206]

[0207]

[0208]

[0209]

[0210]

[0211]

[0212]

[0213]

[0214]

[0215]

[0216] Note: R2, R3 = H;

[0217] Table 3 Structures and physical properties of some compounds of general formula I-3

[0218]

[0219]

[0220]

[0221]

[0222]

[0223]

[0224]

[0225]

[0226]

[0227]

[0228]

[0229]

[0230]

[0231]

[0232]

[0233] Other compounds of the present invention can be prepared by referring to the above examples.

[0234] Physical properties and NMR data of some compounds ( 1 HNMR, 600 MHz, internal standard TMS, ppm) is as follows:

[0235] Compound I-1-2: 1 H NMR (600MHz, Chloroform-d) δ8.08(d,J=8.4Hz,2H),7.71(s,1H),7.55(d,J=8.7Hz,2H),5.37(s,2H),2.62(s,3H),1.62(s,9H).

[0236] Compound I-1-9: 1H NMR (600MHz, Chloroform-d) δ8.17(d,J=8.3Hz,2H),7.71(s,1H),7.61(d,J=8.4Hz,2H),6.92(t,J=51.7Hz,1H),5.39(s,2H),1.63(s,9H).

[0237] Compound I-1-10: 1 H NMR (600MHz, Chloroform-d) δ8.17(d,J=8.3Hz,2H),7.71(s,1H),7.63(d,J=8.3Hz,2H),5.39(s,2H),1.63(s,9H).

[0238] Compound I-1-12: 1 H NMR (600MHz, Chloroform-d) δ8.02(d,J=8.4Hz,2H),7.55(s,1H),7.54(d,J=8.3Hz,2H),4.31(s,2H),2.61(s,3H),1.60(s,9H).

[0239] Compound I-1-19: 1 H NMR (600MHz, Chloroform-d) δ8.12(d,J=8.4Hz,2H),7.62–7.57(m,2H),7.54(s,1H),6.91(t,J=51.7Hz,1H),4.33(s,2H),1.60(s,9H).

[0240] Compound I-1-20: 1 H NMR (600MHz, Chloroform-d) δ8.12(d,J=8.3Hz,1H),7.61(d,J=8.4Hz,1H),7.54(s,1H),4.33(s,1H),1.61(s,6H).

[0241] Compound I-1-32: 1 H NMR(600MHz,Chloroform-d)δ7.82(dd,J=8.0,1.6Hz,1H),7.76(dd,J=10.1,1.6H z,1H),7.59(s,1H),7.57(t,J=7.7Hz,1H),4.32(s,2H),2.62(s,3H),1.61(s,9H).

[0242] Compound I-1-39: 1H NMR(600MHz,Chloroform-d)δ7.92(dd,J=8.0,1.7Hz,1H),7.86(dd,J=9.8,1.7Hz,1H) ,7.64(t,J=7.7Hz,1H),7.58(s,1H),6.91(t,J=51.6Hz,1H),4.34(s,2H),1.61(s,9H).

[0243] Compound I-1-40: 1 H NMR (600MHz, Chloroform-d) δ7.92(dd,J=8.0,1.7Hz,1H),7.87(dd,J=9.7,1.7Hz,1H),7.65(t,J=7.7Hz,1H),7.58(s,1H),4.35(s,2H),1.61(s,9H).

[0244] Compound I-1-159: 1 H NMR(600MHz,Chloroform-d)δ7.99(dd,J=8.0,1.6Hz,1H),7.89(dd,J=9.9,1.6Hz,1H ),7.77(s,1H),7.76–7.73(m,1H),6.92(t,J=51.7Hz,1H),5.43(s,2H),1.64(s,9H).

[0245] Compound I-1-160: 1 H NMR (600MHz, Chloroform-d) δ7.99(dd,J=8.0,1.6Hz,1H),7.89(dd,J=9.8,1.6Hz,1H),7.82–7.73(m,1H),7.77(s,1H),5.43(s,2H),1.64(s,9H).

[0246] Compound I-2-10: 1 H NMR (600MHz, Chloroform-d) δ8.18(d,J=8.4Hz,2H),7.72(s,1H),7.59(d,J=8.4Hz,2H),5.39(s,2H),1.64(s,9H).

[0247] Compound I-2-11: 1 H NMR (600MHz, Chloroform-d) δ8.76(s,1H),8.12(d,J=8.2Hz,2H),7.57(s,1H),7.55(d,J=8.2Hz,2H),4.32(s,2H),1.60(s,9H).

[0248] Compound I-2-12: 1H NMR (600 MHz, Chloroform-d) δ 8.06 (d, J = 8.4 Hz, 2H), 7.57 (s, 1H), 7.52 (d, J = 8.2 Hz, 2H), 4.30 (s, 2H), 2.65 (s, 3H), 1.61 (s, 9H).

[0249] Compound I-2-13: 1 H NMR(600MHz,Chloroform-d)δ8.07(d,J=8.3Hz,1H),7.56(s,1H),7.52(d,J=8.3 Hz,1H),4.30(s,1H),2.97(q,J=7.6Hz,1H),1.60(s,9H),1.44(t,J=7.6Hz,3H).

[0250] Compound I-2-15: 1 H NMR(600MHz,Chloroform-d)δ8.07(d,J=8.3Hz,1H),7.56(s,1H),7.52(d,J=8.3 Hz, 1H), 4.30 (s, 2H), 3.28 (p, J = 7.0Hz, 1H), 1.60 (s, 9H), 1.45 (d, J = 7.0Hz, 6H).

[0251] Compound I-2-16: 1H NMR (600 MHz, Chloroform-d) δ 8.06 (d, J = 8.3 Hz, 1H), 7.56 (s, 1H), 7.52 (d, J = 8.3 Hz, 1H), 4.30 (s, 1H), 2.96–2.92 (m, 2H), 1.89–1.80 (m, 2H), 1.60 (s, 9H), 1.48–1.41 (m, 2H), 0.96 (t, J = 7.4 Hz, 3H).

[0252] Compound I-2-18: 1 H NMR (600MHz, Chloroform-d) δ8.11–8.03(m,2H),7.55(s,1H),7.53–7.50(m,2H),4.30(s,2H),1.60(s,9H),1.48(s,9H).

[0253] Compound I-2-20: 1H NMR (600MHz, Chloroform-d) δ8.13(d,J=8.5Hz,2H),7.59(d,J=8.2Hz,2H),7.57(s,1H),4.33(s,2H),1.62(s,9H).

[0254] Compound I-2-50: 1 H NMR (600MHz, Chloroform-d) δ8.21(d,J=2.0Hz,1H),8.12(dd,J=8.3,2.0Hz,1H),7.78(d,J=8.3Hz,1H),7.77(s,1H),5.46(s,2H),1.65(s,9H).

[0255] Compound I-2-60: 1 H NMR (600MHz, Chloroform-d) δ8.20(d,J=1.5Hz,1H),8.03(dd,J=7.7,2.0Hz,1H),7.66(d,J=8.2Hz,1H),7.57(s,1H),4.43(s,2H),1.63(s,9H).

[0256] Compound I-2-110: 1 H NMR (600MHz, Chloroform-d) δ8.47(s,1H),8.39(dd,J=8.3,1.9Hz,1H),7.98(d,J=8.2Hz,1H),7.72(s,1H),5.55(s,2H),1.64(s,9H).

[0257] Compound I-2-120: 1 H NMR (600MHz, Chloroform-d) δ8.45(d,J=1.9Hz,1H),8.31(dd,J=8.3,1.9Hz,1H),7.88(d,J=8.2Hz,1H),7.49(s,1H),4.50(s,2H),1.61(s,9H).

[0258] Compound I-2-143: 1H NMR (600 MHz, Chloroform-d) δ 8.09–8.00 (m, 1H), 7.51 (s, 1H), 7.34–7.29 (m, 2H), 4.29 (s, 2H), 2.99 (q, J = 7.6 Hz, 2H), 1.60 (s, 9H), 1.44 (t, J = 7.6 Hz, 3H).

[0259] Compound I-2-145: 1H NMR (600 MHz, Chloroform-d) δ 8.05 (dd, J = 8.0, 7.1 Hz, 1H), 7.51 (s, 1H), 7.35–7.28 (m, 2H), 4.29 (s, 2H), 3.30 (hept, J = 7.0 Hz, 1H), 1.61 (s, 9H), 1.45 (d, J = 7.0 Hz, 6H).

[0260] Compound I-2-150: 1 H NMR (600MHz, Chloroform-d) δ8.16(t,J=7.6Hz,1H),7.71(s,1H),7.40(s,1H),7.39(s,1H),5.38(s,2H),1.65(s,9H).

[0261] Compound I-2-151: 1 H NMR (600MHz, Chloroform-d) δ8.81(s,1H),8.10(t,J=7.6Hz,1H),7.52(s,1H),7.35(t,J=10.0Hz,1H),4.30(s,2H),1.61(s,9H).

[0262] Compound I-2-152: 1 H NMR (600MHz, Chloroform-d) δ8.03(t,J=7.9Hz,1H),7.52(s,1H),7.32(t,J=9.0Hz,2H),4.29(s,2H),2.67(s,3H),1.61(s,9H).

[0263] Compound I-2-158: 1 H NMR (600MHz, Chloroform-d) δ8.06(t,J=7.6Hz,1H),7.50(s,1H),7.34–7.28(m,2H),4.29(s,2H),1.61(s,9H),1.48(s,9H).

[0264] Compound I-2-160: 1 H NMR (600MHz, Chloroform-d) δ8.10(t,J=7.2Hz,1H),7.53(s,1H),7.38(t,J=9.3Hz,2H),4.32(s,2H),1.62(s,9H).

[0265] Compound I-2-172: 1H NMR (600MHz, Chloroform-d) δ7.90(d,J=8.0Hz,1H),7.59(d,J=1.8Hz,1H),7.51(s,1H),7.43(dd,J=8.1,1.8Hz,1H),4.27(s,2H),2.68(s,3H),1.61(s,9H).

[0266] Compound I-2-178: 1 H NMR (600MHz, Chloroform-d) δ7.94(d,J=8.0Hz,1H),7.58(d,J=1.8Hz,1H),7.50(s,1H),7.43(dd,J=8.0,1.8Hz,1H),4.27(s,2H),1.61(s,9H),1.49(s,9H).

[0267] Compound I-2-180: 1 H NMR (600MHz, Chloroform-d) δ8.00(d,J=8.1Hz,1H),7.64(d,J=1.8Hz,1H),7.52(s,1H),7.48(dd,J=8.1,1.8Hz,1H),4.29(s,2H),1.61(s,9H).

[0268] Compound I-2-420: 1 H NMR (600MHz, DMSO-d6) δ8.23(s,1H),8.05(d,J=8.3Hz,2H),7.71(d,J=8.3Hz,2H),7.51–7.44(m,4H),7.42–7.38(m,1H),4.72(s,2H).

[0269] Compound I-2-462: 1 H NMR (600MHz, Chloroform-d) δ8.03(d,J=8.3Hz,2H),7.54(d,J=8.2Hz,2H),7.53(s,1H),4.56(s,2H),4.31(s,2H),1.60(s,9H).

[0270] Compound I-2-514: 1 H NMR (600MHz, Chloroform-d) δ8.04(t,J=7.5Hz,1H),7.55(s,1H),7.15–7.06(m,2H),4.37(d,J=13.3Hz,1H),4.21(d,J=13.3Hz,1H),1.62(s,9H).

[0271] Compound I-2-524: 1 H NMR (600MHz, Chloroform-d) δ8.09 (dd, J = 8.2, 7.1Hz, 1H), 7.90 (s, 1H), 7.31–7.27 (m, 2H), 4.69 (s, 2H), 1.63 (s, 9H).

[0272] Biological Activity Assay Example

[0273] The compound of the invention exhibits good activity against various pathogens in the agricultural field.

[0274] Example 10: Bactericidal activity assay

[0275] The samples of the compounds of the present invention were used to test the protective effect of the compounds on various fungal diseases of plants. The results of the fungicidal activity test are shown in the following examples.

[0276] (1) In vivo protective activity assay

[0277] The determination method is as follows: adopt the living potted plant determination method, that is, the sample of the compound of the general formula I obtained above to be tested is dissolved with a small amount of solvent (the type of solvent is such as acetone, methanol, DMF, etc., and is selected according to its solubility for the sample, and the volume ratio of the amount of solvent to the amount of spraying liquid is equal to or less than 0.05), and diluted with water containing 0.1% Tween 80 to prepare the required concentration of the test solution. On the crop sprayer, the test solution is sprayed on the disease host plant (the host plant is a standard potted seedling cultivated in a greenhouse), and the disease is inoculated 24 hours later. According to the characteristics of the disease, the diseased plants that need to be cultivated with temperature control and moisture retention are inoculated and placed in an artificial climate chamber for cultivation. After the disease is completely infected, they are moved to the greenhouse for cultivation. The diseased plants that do not need moisture retention cultivation are directly inoculated and cultivated in the greenhouse. After the control is fully diseased (usually one week), the disease prevention effect of the compound is evaluated.

[0278] The in vivo protective activity test results of some compounds are as follows:

[0279] In vivo protective activity against cucumber downy mildew:

[0280] At a dose of 400 ppm, compounds I-1-2, I-1-9, I-1-10, I-1-12, I-1-19, I-1-20, I-1-32 , I-1-39, I-1-40, I-1-159, I-1-160, I-2-10, I-2-12, I-2-13, I-2-15, I- 2-18, I-2-20, I-2-60, I-2-143, I-2-145, I-2-151, I-2-152, I-2-158, I- 2-172, I-2-178, I-2-180, I-2-420, I-2-514, I-2-524, etc. have a control effect of more than 80% on cucumber downy mildew;

[0281] In vivo protective activity against wheat powdery mildew:

[0282] At a dosage of 400 ppm, compounds I-2-13, I-2-15, I-2-16, I-2-20, I-2-50, I-2-120, I-2-145, I-2-160, I-2-172, I-2-180, etc. had a control effect of more than 80% on wheat powdery mildew, while compound CK1 had a control effect of 0 on wheat powdery mildew at a dosage of 400 ppm;

[0283] In vivo protective activity against corn rust:

[0284] At a dosage of 400 ppm, compounds I-2-10, I-2-11, I-2-12, I-2-13, I-2-15, I-2-16, I-2-20, I-2-50, I-2-60, I-2-180, I-2-420, I-2-524, etc., have a protective effect of more than 85% against corn rust;

[0285] At a dosage of 100 ppm, compounds I-2-10, I-2-12, I-2-20, I-2-50, etc., have a protective effect of more than 85% against corn rust;

[0286] In vivo protective activity against cucumber anthracnose:

[0287] At a dosage of 400 ppm, compounds I-1-20, I-2-18, I-2-145, I-2-180, I-2-514, and I-2-524 had a protective effect of more than 80% against cucumber anthracnose, while compound CK1 had a protective effect of 0 against cucumber anthracnose;

[0288] According to the above method, some compounds of the present invention and the known compound CK1 (self-made, numbered 107 in patent EP0665223A1) were selected for parallel determination of the activity of preventing and controlling cucumber downy mildew. The test results are shown in Table 3.

[0289] Table 4: Comparison of the protective effects of some compounds of the present invention and known compounds on cucumber downy mildew (fonthiapyr resistant bacteria)

[0290]

[0291] According to the above method, some compounds of the present invention and known compounds were selected for parallel determination of their activity against wheat powdery mildew. The test results are shown in Table 5.

[0292] Table 5: Comparison of the control effects of some compounds of the present invention and known compounds on wheat powdery mildew

[0293]

[0294] According to the above method, some compounds of the present invention and known compounds were selected for parallel determination of their activity against corn rust. The test results are shown in Table 6.

[0295] Table 6: Comparison of the efficacy of some compounds of the present invention and known compounds against corn rust

[0296]

[0297] According to the above method, some compounds of the present invention and known compounds were selected for parallel determination of their activity against cucumber anthracnose. The test results are shown in Table 7.

[0298] Table 7: Comparison of the protective effects of some compounds of the present invention and known compounds on cucumber anthracnose

[0299]

[0300] Example 11: Insecticidal and acaricidal activity assay

[0301] The compounds of the present invention were used to carry out insecticidal activity tests on several insects. The test method is as follows:

[0302] The test compound was dissolved in a mixed solvent of acetone / methanol (1:1 (v / v)) and then diluted with water containing 0.1% (wt) Tween 80 to the desired concentration.

[0303] The insecticidal activity was determined by airbrush spraying with Plutella xylostella, armyworm, aphid and spider mite as targets.

[0304] (1) Determination of activity against Plutella xylostella

[0305] Test method: Use a punch to punch cabbage leaves into leaf discs with a diameter of 3 cm and use an airbrush to spray them at a pressure of 10 psi (about 0.7 kg / cm 2), spray each leaf disc on both sides, with a spray volume of 0.5 ml. After drying in the shade, 10 3rd-instar test insects were inoculated in each treatment, and each treatment was repeated 3 times. After treatment, they were placed in an observation room at 25°C and a relative humidity of 40-60%. After 72 hours, the number of surviving insects was investigated and the mortality rate was calculated.

[0306] Some test results on Plutella xylostella are as follows: At a dosage of 100 ppm, the mortality rates of compounds: I-2-12, I-2-15, I-2-20, I-2-60, I-2-151, I-2-152, I-2-160, etc. to Plutella xylostella are over 90%, while the mortality rate of compound CK1 to Plutella xylostella is 0.

[0307] (2) Determination of activity against armyworms;

[0308] Test method: Cut corn leaves into 4-5 cm long segments and spray with airbrush at a pressure of 10 psi (about 0.7 kg / cm 2 ), spray each leaf segment on both sides, with a spray volume of 0.5 ml. After drying in the shade, 10 3rd-instar test insects were inoculated in each treatment, and each treatment was repeated 3 times. After treatment, they were placed in an observation room at 25°C and a relative humidity of 40-60%. After 72 hours, the number of surviving insects was investigated and the mortality rate was calculated.

[0309] Some of the test results on armyworms are as follows:

[0310] At a dosage of 100 ppm, the mortality rates of compounds I-2-11, I-2-12, I-2-16, I-2-20, I-2-151, I-2-152, I-2-160, etc. to armyworms were over 90%, while the mortality rate of compound CK1 to armyworms was 0.

[0311] (3) Determination of activity against green peach aphids

[0312] Determination method: Select cabbage leaves infected with a certain number of aphids, and use an airbrush sprayer to evenly spray the front and back of the leaves at a pressure of 10 psi (about 0.7 kg / cm 2 ), the spray volume was 0.5 ml. Each treatment was repeated 3 times, and the plants were placed in a standard observation room after treatment. The number of surviving peach aphids was investigated 48 hours later, and the mortality rate was calculated.

[0313] Some of the test results on green peach aphid are as follows:

[0314] At a dosage of 100 ppm, the mortality rates of compounds I-2-12, I-2-13, I-2-15, I-2-16, I-2-20, I-2-143, I-2-145, I-2-152, I-2-160, and I-2-172 to peach aphids were over 80%, while the mortality rate of compound CK1 to aphids was 0.

[0315] (4) Determination of activity against Tetranychus cinnabarinus

[0316] Determination method: Take two true leaf bean seedlings, inoculate them with adult spider mites and investigate the base number, then use an airbrush sprayer to treat the whole plant at a pressure of 10 psi (about 0.7 kg / cm 2 ), the spray volume was 0.5 mL. Each treatment was repeated 3 times, and the mites were placed in a standard observation room after treatment. The number of surviving mites was investigated after 72 hours, and the mortality rate was calculated.

[0317] Some of the test results on Tetranychus cinnabarinus are as follows:

[0318] At a dosage of 100 ppm, the mortality rates of compounds I-2-12, I-2-15, I-2-16, I-2-18, I-2-20, I-2-145, I-2-158, I-2-178, I-2-180, etc. to Tetranychus cinnabarinus were over 80%, while the mortality rate of compound CK1 to Tetranychus cinnabarinus was 0.

Claims

1. A pyridazinone compound containing an aromatic ring substitution, characterized in that: The pyridazinone compounds containing aromatic ring substitution are compounds represented by the general formula I-1 and I-2; R1 is selected from hydrogen, C1-C 12 Alkyl, halogenated C1-C 12 alkyl; R2 and R3 are selected from hydrogen; R4, R5, R6, and R7 may be the same or different and independently selected from hydrogen, halogen, C1-C 12 Alkyl, halogenated C1-C 12 alkyl; X is selected from halogen; A is selected from O, S, S=O, O=S=O; R8, R9 are selected from hydrogen, halogen, amino, C1-C 12 Alkyl, halogenated C1-C 12 alkyl.

2. The pyridazinone compound containing aromatic ring substitution according to claim 1, characterized in that: In the compounds of general formula I-1 and I-2 R1 is selected from hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl; R2 and R3 are selected from hydrogen; R4, R5, R6, and R7 may be the same or different and are independently selected from hydrogen, halogen, C1-C8 alkyl, and halogenated C1-C8 alkyl; X is selected from halogen; A is selected from O, S, S=O, O=S=O; R8 and R9 are selected from hydrogen, halogen, amino, C1-C8 alkyl, and halogenated C1-C8 alkyl.

3. The pyridazinone compound containing aromatic ring substitution according to claim 2, characterized in that: In the compounds of general formula I-1 and I-2 R1 is selected from hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl; R2 and R3 are selected from hydrogen; R4, R5, R6, and R7 may be the same or different and are independently selected from hydrogen, halogen, C1-C6 alkyl, and halogenated C1-C6 alkyl; X is selected from halogen; A is selected from O, S, S=O, O=S=O; R8 and R9 are selected from hydrogen, halogen, amino, C1-C6 alkyl, and halogenated C1-C6 alkyl.

4. The pyridazinone compound containing aromatic ring substitution according to claim 3, characterized in that: In the compounds of general formula I-1 and I-2 R1 is selected from hydrogen, C1-C4 alkyl, halogenated C1-C4 alkyl; R2 and R3 are selected from hydrogen; R4, R5, R6, and R7 may be the same or different and are independently selected from hydrogen, halogen, C1-C4 alkyl, and halogenated C1-C4 alkyl; X is selected from halogen; A is selected from O, S, S=O, O=S=O; R8 and R9 are selected from hydrogen, halogen, amino, C1-C4 alkyl, and halogenated C1-C4 alkyl.

5. The pyridazinone compound containing aromatic ring substitution according to claim 4, characterized in that: In the compounds of general formula I-1 and I-2 R1 is selected from hydrogen, methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, tert-butyl, monofluoromethyl, difluoromethyl, trifluoromethyl, 2,2,2-trifluoroethyl; R2 and R3 are selected from hydrogen; R4, R5, R6, and R7 may be the same or different and independently selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, and trifluoromethyl; X is selected from fluorine, chlorine, bromine and iodine; A is selected from O, S, S=O, O=S=O; R8 and R9 are selected from hydrogen, amino, methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, tert-butyl, monofluoromethyl, difluoromethyl, trifluoromethyl, and 2,2,2-trifluoroethyl.

6. The pyridazinone compound containing aromatic ring substitution according to claim 5, characterized in that: In the compounds of general formula I-1 and I-2 R1 is selected from hydrogen, tert-butyl; R2 and R3 are selected from hydrogen; R4, R5, R6, and R7 may be the same or different and independently selected from hydrogen, fluorine, chlorine, and trifluoromethyl; X is selected from chlorine; A is selected from O, S, S=O, O=S=O; R8 and R9 are selected from hydrogen, amino, methyl, ethyl, propyl, isopropyl, butyl, 2-butyl, isobutyl, tert-butyl, trifluoromethyl, and 2,2,2-trifluoroethyl.

7. Use of the compound according to claim 1 for preparing bactericidal and insecticidal drugs in agriculture or other fields.

8. A fungicide and insecticide composition comprising the compound as claimed in claim 1 as an active ingredient and an agricultural, forestry or hygienic acceptable carrier, wherein the weight content of the compound as an active ingredient in the composition is 1-99%.

9. A method for controlling diseases, characterized in that: The composition of claim 8 is applied to the disease to be controlled or the medium where it grows at an effective dosage of 10 to 1000 grams per hectare.

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