Substituted isoxazole ethylamine compounds and preparation method and use thereof

Abstract

The invention discloses a substituted isoxazole ethylamine compound, the structure of which is shown in 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 activity and has excellent control effects on cucumber downy mildew, powdery mildew, corn rust, anthracnose, rice blast and the like.

Description

Technical Field

[0001] The invention belongs to the field of chemistry, and specifically relates to a substituted isoxazole ethylamine compound, a preparation method thereof and use thereof as a fungicide. Background Art

[0002] The document Bioorganic & Medicinal Chemistry (2015), 23 (6), 1260-1275 and the patent WO9219604 disclose the following substituted isoxazole ethylamine compounds, which are used in the medical field as receptor antagonists and lipoxygenase and cyclooxygenase inhibitors, respectively.

[0003]

[0004] Although the disclosed compounds in the prior art have certain similarities with the compounds of the present invention, the compounds represented by the general formula of the present invention are significantly different from the prior art and both have good fungicide activity. Summary of the invention

[0005] The object of the present invention is to provide a substituted isoxazole ethylamine compound capable of controlling a variety of pathogens, a preparation method thereof and the use of the compound in preparing medicines for controlling pathogens in agriculture or other fields.

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

[0007] A substituted isoxazole ethylamine compound, characterized in that the substituted isoxazole ethylamine compound is a compound represented by general formula I;

[0008]

[0009] Where:

[0010] R 1 Selected from hydrogen, C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkyl, C 3 -C 12 Cycloalkyl, C 1 -C 12 Alkoxy, halogenated C 1 -C 12 Alkoxy, C 2 -C 12 Alkenyl, halogenated C 2 -C 12 Alkenyl, C 2 -C 12 Alkynyl, halo C 2 -C 12 Alkynyl, C3 -C 12 Alkenyloxy, halogenated C 3 -C 12 Alkenyloxy, C 3 -C 12 Alkynyloxy, halo C 3 -C 12 Alkynyloxy, C 1 -C 12 Alkoxy C 1 -C 12 Alkyl or C 1 -C 12 Alkylthio C 1 -C 12 alkyl;

[0011] R 2 Selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkyl, C 1 -C 12 Alkoxy, halogenated C 1 -C 12 Alkoxy, C 3 -C 12 Cycloalkyl, C 1 -C 12 Alkylamino, halo C 1 -C 12 Alkylamino, di(C 1 -C 12 Alkyl)amino, di(halogenated C 1 -C 12 Alkyl)amino, C 1 -C 12 Alkylthio, halo 1 -C 12 Alkylthio, C 2 -C 12 Alkenyl, C 2 -C 12 Alkynyl, C 2 -C 12 Alkenyloxy, halogenated C 2 -C 12 Alkenyloxy, C 2 -C 12 Alkynyloxy, halo C 2 -C 12 Alkynyloxy, C 1 -C 12 Alkylsulfonyl, halo C 1 -C 12 Alkylsulfonyl, C 1 -C 12Alkylcarbonyl, haloC 1 -C 12 Alkylcarbonyl, C 1 -C 12 Alkoxycarbonyl, halocarbonyl 1 -C 12 Alkoxycarbonyl, C 1 -C 12 Alkoxy C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkoxy C 1 -C 12 Alkyl, C 1 -C 12 Alkylthio C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkylthio C 1 -C 12 Alkyl, C 1 -C 12 Alkoxycarbonyl C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkoxycarbonyl C 1 -C 12 Alkyl, C 1 -C 12 Alkylthiocarbonyl C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkylthiocarbonyl C 1 -C 12 Alkyl, C 1 -C 12 Alkylcarbonyloxy, halogenated C 1 -C 12 Alkylcarbonyloxy, C 1 -C 12 Alkoxycarbonyloxy, halo 1 -C 12 Alkoxycarbonyloxy, C 1 -C 12 Alkylsulfonyloxy, halo 1 -C 12 Alkylsulfonyloxy, C 1 -C 12 Alkoxy C 1 -C 12 Alkoxy or halogenated C 1 -C 12 Alkoxy C 1 -C 12 Alkoxy, R2 When at the 4-position of the benzene ring, it is not selected from cyano or hydroxyl;

[0012] n is an integer selected from 0 to 5. When n is 0, there is no substituent. When n is greater than 1, R 2 Same or different;

[0013] R 3 Selected from hydrogen, hydroxyl, formyl, C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkyl, C 1 -C 12 Alkoxy, halogenated C 1 -C 12 Alkoxy, C 3 -C 12 Cycloalkyl, C 2 -C 12 Alkenyl, C 2 -C 12 Alkynyl, halo C 2 -C 12 Alkenyl, halogenated C 2 -C 12 Alkynyl, C 1 -C 12 Alkoxy C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkoxy C 1 -C 12 Alkyl, C 1 -C 12 Alkylthio C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkylthio C 1 -C 12 Alkyl, C 1 -C 12 Alkylsulfinyl, halo C 1 -C 12 Alkylsulfinyl, C 1 -C 12 Alkylsulfonyl, halo C 1 -C 12 Alkylsulfonyl, C 1 -C 12 Alkylaminosulfonyl, di(C 1 -C 12 (alkyl)aminosulfonyl, C 1 -C 12 Alkylsulfonylaminocarbonyl, C 1 -C12 Alkylcarbonylaminosulfonyl, C 3 -C 12 Cycloalkyloxycarbonyl, C 1 -C 12 Alkylcarbonyl, haloC 1 -C 12 Alkylcarbonyl, C 1 -C 12 Alkoxycarbonyl, halocarbonyl 1 -C 12 Alkoxycarbonyl, C 1 -C 12 Alkylcarbonyl C 1 -C 12 Alkyl, C 1 -C 12 Alkoxycarbonyl C 1 -C 12 Alkyl, C 1 -C 12 Alkylaminocarbonyl, di(C 1 -C 12 alkyl)aminocarbonyl, C 2 -C 12 Alkenyloxycarbonyl, C 2 -C 12 Alkynyloxycarbonyl, C 1 -C 12 Alkoxy C 1 -C 12 Alkoxycarbonyl, unsubstituted or substituted by 1-5 of the following groups arylcarbonylC 1 -C 6 Alkyl, arylcarbonyl, aryloxycarbonyl, arylC 1 -C 6 Alkyloxycarbonyl, arylC 1 -C 6 Alkyl, heteroarylcarbonylC 1 -C 6 Alkyl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylC 1 -C 6 Alkyloxycarbonyl, heteroarylC 1 -C 6 Alkyl, the following groups are halogen, nitro, cyano, C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkyl, C 1 -C 6 Alkoxy or halogenated C 1 -C 6 Alkoxy;

[0014] R 4 , R5 The same or different ones are selected from hydrogen, halogen, C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkyl, C 1 -C 12 Alkoxy or halogenated C 1 -C 12 Alkoxy;

[0015] Among them, R 4 , R 5 The C connected to it can also form C 3 -C 8 Ring;

[0016] R 6 , R 7 The same or different ones are selected from hydrogen, halogen, C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkyl, C 1 -C 12 Alkoxy or halogenated C 1 -C 12 Alkoxy;

[0017] Among them, R 6 , R 7 The C connected to it can also form C 3 -C 8 Ring;

[0018] Q is unsubstituted or substituted with 1-5 R 8 Substituted aryl and heteroaryl.

[0019] R 8 Selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkyl, C 1 -C 12 Alkoxy, halogenated C 1 -C 12 Alkoxy, C 3 -C 12 Cycloalkyl, C 1 -C 12 Alkylamino, halogenated C 1 -C 12 Alkylamino, di(C 1 -C 12 alkyl)amino, halogenated di(C 1 -C 12 Alkyl)amino, C1 -C 12 Alkylthio, halo 1 -C 12 Alkylthio, C 2 -C 12 Alkenyl, C 2 -C 12 Alkynyl, C 2 -C 12 Alkenyloxy, halogenated C 2 -C 12 Alkenyloxy, C 2 -C 12 Alkynyloxy, halo C 2 -C 12 Alkynyloxy, C 1 -C 12 Alkylsulfonyl, halo C 1 -C 12 Alkylsulfonyl, C 1 -C 12 Alkylcarbonyl, haloC 1 -C 12 Alkylcarbonyl, C 1 -C 12 Alkoxycarbonyl, halocarbonyl 1 -C 12 Alkoxycarbonyl, C 1 -C 12 Alkoxy C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkoxy C 1 -C 12 Alkyl, C 1 -C 12 Alkylthio C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkylthio C 1 -C 12 Alkyl, C 1 -C 12 Alkoxycarbonyl C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkoxycarbonyl C 1 -C 12 Alkyl, C 1 -C 12 Alkylthiocarbonyl C 1 -C 12 Alkyl, halogenated C 1 -C 12 Alkylthiocarbonyl C 1 -C12 Alkyl, C 1 -C 12 Alkylcarbonyloxy, halogenated C 1 -C 12 Alkylcarbonyloxy, C 1 -C 12 Alkoxycarbonyloxy, halo 1 -C 12 Alkoxycarbonyloxy, C 1 -C 12 Alkylsulfonyloxy, halo 1 -C 12 Alkylsulfonyloxy, C 1 -C 12 Alkoxy C 1 -C 12 Alkoxy or halogenated C 1 -C 12 Alkoxy C 1 -C 12 Alkoxy.

[0020] Preferably, in the compound of general formula I:

[0021] R 1 Selected from hydrogen, C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkyl, C 3 -C 6 Cycloalkyl, C 1 -C 6 Alkoxy, halogenated C 1 -C 6 Alkoxy, C 2 -C 6 Alkenyl, halogenated C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl, halo C 2 -C 6 Alkynyl, C 3 -C 6 Alkenyloxy, halogenated C 3 -C 6 Alkenyloxy, C 3 -C 6 Alkynyloxy, halo C 3 -C 6 Alkynyloxy, C 1 -C 6 Alkoxy C 1 -C 6 Alkyl or C 1 -C 6 Alkylthio C 1-C 6 alkyl;

[0022] R 2 Selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkyl, C 1 -C 6 Alkoxy, halogenated C 1 -C 6 Alkoxy, C 3 -C 6 Cycloalkyl, C 1 -C 6 Alkylamino, halo C 1 -C 6 Alkylamino, di(C 1 -C 6 Alkyl)amino, di(halogenated C 1 -C 6 Alkyl)amino, C 1 -C 6 Alkylthio, halo 1 -C 6 Alkylthio, C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl, C 2 -C 6 Alkenyloxy, halogenated C 2 -C 6 Alkenyloxy, C 2 -C 6 Alkynyloxy, halo C 2 -C 6 Alkynyloxy, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylsulfonyl, C 1 -C 6 Alkylcarbonyl, haloC 1 -C 6 Alkylcarbonyl, C 1 -C 6 Alkoxycarbonyl, halocarbonyl 1 -C 6 Alkoxycarbonyl, C 1 -C 6 Alkoxy C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkoxy C 1 -C 6 Alkyl, C1 -C 6 Alkylthio C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkylthio C 1 -C 6 Alkyl, C 1 -C 6 Alkoxycarbonyl C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkoxycarbonyl C 1 -C 6 Alkyl, C 1 -C 6 Alkylthiocarbonyl C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkylthiocarbonyl C 1 -C 6 Alkyl, C 1 -C 6 Alkylcarbonyloxy, halogenated C 1 -C 6 Alkylcarbonyloxy, C 1 -C 6 Alkoxycarbonyloxy, halo 1 -C 6 Alkoxycarbonyloxy, C 1 -C 6 Alkylsulfonyloxy, halo 1 -C 6 Alkylsulfonyloxy, C 1 -C 6 Alkoxy C 1 -C 6 Alkoxy or halogenated C 1 -C 6 Alkoxy C 1 -C 6 Alkoxy, R 2 When at the 4-position of the benzene ring, it is not selected from cyano or hydroxyl;

[0023] n is an integer selected from 0 to 5. When n is 0, there is no substituent. When n is greater than 1, R 2 Same or different;

[0024] R 3 Selected from hydrogen, hydroxyl, formyl, C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkyl, C 1 -C6 Alkoxy, halogenated C 1 -C 6 Alkoxy, C 3 -C 6 Cycloalkyl, C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl, halo C 2 -C 6 Alkenyl, halogenated C 2 -C 6 Alkynyl, C 1 -C 6 Alkoxy C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkoxy C 1 -C 6 Alkyl, C 1 -C 6 Alkylthio C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkylthio C 1 -C 6 Alkyl, C 1 -C 6 Alkylsulfinyl, halo C 1 -C 6 Alkylsulfinyl, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylsulfonyl, C 1 -C 6 Alkylaminosulfonyl, di(C 1 -C 6 (alkyl)aminosulfonyl, C 1 -C 6 Alkylsulfonylaminocarbonyl, C 1 -C 6 Alkylcarbonylaminosulfonyl, C 3 -C 6 Cycloalkyloxycarbonyl, C 1 -C 6 Alkylcarbonyl, haloC 1 -C 6 Alkylcarbonyl, C 1 -C 6 Alkoxycarbonyl, halocarbonyl 1 -C 6 Alkoxycarbonyl, C 1 -C 6 Alkylcarbonyl C 1-C 6 Alkyl, C 1 -C 6 Alkoxycarbonyl C 1 -C 6 Alkyl, C 1 -C 6 Alkylaminocarbonyl, di(C 1 -C 6 alkyl)aminocarbonyl, C 2 -C 6 Alkenyloxycarbonyl, C 2 -C 6 Alkynyloxycarbonyl, C 1 -C 6 Alkoxy C 1 -C 6 Alkoxycarbonyl, unsubstituted or substituted by 1-5 of the following groups arylcarbonylC 1 -C 6 Alkyl, arylcarbonyl, aryloxycarbonyl, arylC 1 -C 6 Alkyloxycarbonyl, arylC 1 -C 6 Alkyl, heteroarylcarbonylC 1 -C 6 Alkyl, heteroarylcarbonyl, heteroaryloxycarbonyl, heteroarylC 1 -C 6 Alkyloxycarbonyl, heteroarylC 1 -C 6 Alkyl, the following groups are halogen, nitro, cyano, C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkyl, C 1 -C 6 Alkoxy or halogenated C 1 -C 6 Alkoxy;

[0025] R 4 , R 5 The same or different ones are selected from hydrogen, halogen, C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkyl, C 1 -C 6 Alkoxy or halogenated C 1 -C 6 Alkoxy;

[0026] Among them, R 4 , R 5 The C connected to it can also form C 3 -C6 Ring;

[0027] R 6 , R 7 The same or different ones are selected from hydrogen, halogen, C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkyl, C 1 -C 6 Alkoxy or halogenated C 1 -C 6 Alkoxy;

[0028] Among them, R 6 , R 7 The C connected to it can also form C 3 -C 6 Ring;

[0029] Q is unsubstituted or substituted with 1-5 R 8 Substituted aryl and heteroaryl.

[0030] R 8 Selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkyl, C 1 -C 6 Alkoxy, halogenated C 1 -C 6 Alkoxy, C 3 -C 6 Cycloalkyl, C 1 -C 6 Alkylamino, halogenated C 1 -C 6 Alkylamino, di(C 1 -C 6 alkyl)amino, halogenated di(C 1 -C 6 Alkyl)amino, C 1 -C 6 Alkylthio, halo 1 -C 6 Alkylthio, C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl, C 2 -C 6 Alkenyloxy, halogenated C 2 -C 6 Alkenyloxy, C 2 -C 6 Alkynyloxy, halo C 2-C 6 Alkynyloxy, C 1 -C 6 Alkylsulfonyl, halo C 1 -C 6 Alkylsulfonyl, C 1 -C 6 Alkylcarbonyl, haloC 1 -C 6 Alkylcarbonyl, C 1 -C 6 Alkoxycarbonyl, halocarbonyl 1 -C 6 Alkoxycarbonyl, C 1 -C 6 Alkoxy C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkoxy C 1 -C 6 Alkyl, C 1 -C 6 Alkylthio C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkylthio C 1 -C 6 Alkyl, C 1 -C 6 Alkoxycarbonyl C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkoxycarbonyl C 1 -C 6 Alkyl, C 1 -C 6 Alkylthiocarbonyl C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkylthiocarbonyl C 1 -C 6 Alkyl, C 1 -C 6 Alkylcarbonyloxy, halogenated C 1 -C 6 Alkylcarbonyloxy, C 1 -C 6 Alkoxycarbonyloxy, halo 1 -C 6 Alkoxycarbonyloxy, C 1 -C 6 Alkylsulfonyloxy, halo 1 -C 6 Alkylsulfonyloxy, C 1-C 6 Alkoxy C 1 -C 6 Alkoxy or halogenated C 1 -C 6 Alkoxy C 1 -C 6 Alkoxy.

[0031] Further preferably, in the compound of general formula I:

[0032] R 1 Selected from hydrogen, C 1 -C 6 Alkyl, halogenated C 1 -C 6 Alkyl, C 3 -C 6 Cycloalkyl, C 1 -C 6 Alkoxy, halogenated C 1 -C 6 Alkoxy, C 2 -C 6 Alkenyl, halogenated C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl, halo C 2 -C 6 Alkynyl;

[0033] R 2 Selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy, halogenated C 1 -C 4 Alkoxy, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylamino, halo C 1 -C 4 Alkylamino, di(C 1 -C 4 Alkyl)amino, di(halogenated C 1 -C 4 Alkyl)amino, C 1 -C 4 Alkylthio, halo 1 -C 4 Alkylthio, C 2 -C 4 Alkenyl, C 2 -C 4Alkynyl, C 2 -C 4 Alkenyloxy, halogenated C 2 -C 4 Alkenyloxy, C 2 -C 4 Alkynyloxy, halo C 2 -C 4 Alkynyloxy, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl, C 1 -C 4 Alkylcarbonyl, haloC 1 -C 4 Alkylcarbonyl, C 1 -C 4 Alkoxycarbonyl, halocarbonyl 1 -C 4 Alkoxycarbonyl, C 1 -C 4 Alkoxy C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkoxy C 1 -C 4 Alkyl, C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, C 1 -C 4 Alkoxycarbonyl C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkoxycarbonyl C 1 -C 4 Alkyl, C 1 -C 4 Alkylthiocarbonyl C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkylthiocarbonyl C 1 -C 4 Alkyl, C 1 -C 4 Alkylcarbonyloxy, halogenated C 1 -C 4 Alkylcarbonyloxy, C 1 -C 4 Alkoxycarbonyloxy, halo1 -C 4 Alkoxycarbonyloxy, C 1 -C 4 Alkylsulfonyloxy, halo 1 -C 4 Alkylsulfonyloxy, C 1 -C 4 Alkoxy C 1 -C 4 Alkoxy or halogenated C 1 -C 4 Alkoxy C 1 -C 4 Alkoxy, R 2 When at the 4-position of the benzene ring, it is not selected from cyano or hydroxyl;

[0034] n is an integer selected from 0 to 5. When n is 0, there is no substituent. When n is greater than 1, R 2 Same or different;

[0035] R 3 Selected from hydrogen, hydroxyl, formyl, C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy, halogenated C 1 -C 4 Alkoxy, C 3 -C 4 Cycloalkyl, C 2 -C 4 Alkenyl, C 2 -C 4 Alkynyl, halo C 2 -C 4 Alkenyl, halogenated C 2 -C 4 Alkynyl, C 1 -C 4 Alkoxy C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkoxy C 1 -C 4 Alkyl, C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, C 1 -C 4 Alkylsulfinyl, halo C1 -C 4 Alkylsulfinyl, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl, C 1 -C 4 Alkylaminosulfonyl, di(C 1 -C 4 (alkyl)aminosulfonyl, C 1 -C 4 Alkylsulfonylaminocarbonyl, C 1 -C 4 Alkylcarbonylaminosulfonyl, C 3 -C 4 Cycloalkyloxycarbonyl, C 1 -C 4 Alkylcarbonyl, haloC 1 -C 4 Alkylcarbonyl, C 1 -C 4 Alkoxycarbonyl, halocarbonyl 1 -C 4 Alkoxycarbonyl;

[0036] R 4 , R 5 The same or different ones are selected from hydrogen, halogen, C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy or halogenated C 1 -C 4 Alkoxy;

[0037] Among them, R 4 , R 5 The C connected to it can also form C 3 -C 4 Ring;

[0038] R 6 , R 7 The same or different are selected from hydrogen, halogen, C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy or halogenated C 1 -C 4 Alkoxy;

[0039] Among them, R 6 , R7 The C connected to it can also form C 3 -C 4 Ring;

[0040] Q is unsubstituted or substituted with 1-5 R 8 substituted phenyl, pyridyl, thienyl, furyl, pyrazolyl, thiazolyl, isothiazolyl, pyrazine, pyridazine;

[0041] R 8 Selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy, halogenated C 1 -C 4 Alkoxy, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylamino, halogenated C 1 -C 4 Alkylamino, di(C 1 -C 4 alkyl)amino, halogenated di(C 1 -C 4 Alkyl)amino, C 1 -C 4 Alkylthio, halo 1 -C 4 Alkylthio, C 2 -C 4 Alkenyl, C 2 -C 4 Alkynyl, C 2 -C 4 Alkenyloxy, halogenated C 2 -C 4 Alkenyloxy, C 2 -C 4 Alkynyloxy, halo C 2 -C 4 Alkynyloxy, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl, C 1 -C 4 Alkylcarbonyl, haloC 1 -C 4 Alkylcarbonyl, C 1 -C 4 Alkoxycarbonyl, halocarbonyl 1 -C 4 Alkoxycarbonyl, C1 -C 4 Alkoxy C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkoxy C 1 -C 4 Alkyl, C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, C 1 -C 4 Alkoxycarbonyl C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkoxycarbonyl C 1 -C 4 Alkyl, C 1 -C 4 Alkylthiocarbonyl C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkylthiocarbonyl C 1 -C 4 Alkyl, C 1 -C 4 Alkylcarbonyloxy, halogenated C 1 -C 4 Alkylcarbonyloxy, C 1 -C 4 Alkoxycarbonyloxy, halo 1 -C 4 Alkoxycarbonyloxy, C 1 -C 4 Alkylsulfonyloxy, halo 1 -C 4 Alkylsulfonyloxy, C 1 -C 4 Alkoxy C 1 -C 4 Alkoxy or halogenated C 1 -C 4 Alkoxy C 1 -C 4 Alkoxy.

[0042] Still more preferably, in the compound of general formula I:

[0043] R 1 Selected from hydrogen, C 1 -C 6Alkyl, halogenated C 1 -C 6 Alkyl, C 3 -C 6 Cycloalkyl, C 1 -C 6 Alkoxy, halogenated C 1 -C 6 Alkoxy, C 2 -C 6 Alkenyl, halogenated C 2 -C 6 Alkenyl, C 2 -C 6 Alkynyl, halo C 2 -C 6 Alkynyl;

[0044] R 2 Selected from halogen, hydroxy, amino, cyano, nitro, C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy, halogenated C 1 -C 4 Alkoxy, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylamino, halogenated C 1 -C 4 Alkylamino, di(C 1 -C 4 Alkyl)amino, di(halogenated C 1 -C 4 Alkyl)amino, C 1 -C 4 Alkylthio, halo 1 -C 4 Alkylthio, C 2 -C 4 Alkenyl, C 2 -C 4 Alkynyl, C 2 -C 4 Alkenyloxy, halogenated C 2 -C 4 Alkenyloxy, C 2 -C 4 Alkynyloxy, halo C 2 -C 4 Alkynyloxy, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl, C 1 -C4 Alkylcarbonyl, haloC 1 -C 4 Alkylcarbonyl, C 1 -C 4 Alkoxycarbonyl, halocarbonyl 1 -C 4 Alkoxycarbonyl, C 1 -C 4 Alkoxy C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkoxy C 1 -C 4 Alkyl, C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, C 1 -C 4 Alkoxycarbonyl C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkoxycarbonyl C 1 -C 4 Alkyl, C 1 -C 4 Alkylthiocarbonyl C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkylthiocarbonyl C 1 -C 4 Alkyl, C 1 -C 4 Alkylcarbonyloxy, halogenated C 1 -C 4 Alkylcarbonyloxy, C 1 -C 4 Alkoxycarbonyloxy, halo 1 -C 4 Alkoxycarbonyloxy, C 1 -C 4 Alkylsulfonyloxy, halo 1 -C 4 Alkylsulfonyloxy, C 1 -C 4 Alkoxy C 1 -C 4 Alkoxy or halogenated C 1 -C 4 Alkoxy C 1 -C4 Alkoxy, R 2 When at the 4-position of the benzene ring, it is not selected from cyano or hydroxyl;

[0045] n is an integer selected from 0 to 5. When n is 0, there is no substituent. When n is greater than 1, R 2 Same or different;

[0046] R 3 Selected from hydrogen, hydroxyl, formyl, C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy, halogenated C 1 -C 4 Alkoxy, C 3 -C 4 Cycloalkyl, C 2 -C 4 Alkenyl, C 2 -C 4 Alkynyl, halo C 2 -C 4 Alkenyl, halogenated C 2 -C 4 Alkynyl, C 1 -C 4 Alkoxy C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkoxy C 1 -C 4 Alkyl, C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkylthio C 1 -C 4 Alkyl, C 1 -C 4 Alkylsulfinyl, halo C 1 -C 4 Alkylsulfinyl, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl, C 1 -C 4 Alkylaminosulfonyl, di(C 1 -C 4 (alkyl)aminosulfonyl, C 1 -C 4 Alkylsulfonylaminocarbonyl, C1 -C 4 Alkylcarbonylaminosulfonyl, C 3 -C 4 Cycloalkyloxycarbonyl, C 1 -C 4 Alkylcarbonyl, haloC 1 -C 4 Alkylcarbonyl, C 1 -C 4 Alkoxycarbonyl, halocarbonyl 1 -C 4 Alkoxycarbonyl;

[0047] R 4 , R 5 The same or different are selected from hydrogen, halogen, C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy or halogenated C 1 -C 4 Alkoxy;

[0048] Among them, R 4 , R 5 The C connected to it can also form C 3 -C 4 Ring;

[0049] R 6 , R 7 The same or different are selected from hydrogen, halogen, C 1 -C 4 Alkyl, halogenated C 1 -C 4 Alkyl, C 1 -C 4 Alkoxy or halogenated C 1 -C 4 Alkoxy;

[0050] Among them, R 6 , R 7 The C connected to it can also form C 3 -C 4 Ring;

[0051] Q is selected from the following substituents:

[0052]

[0053] R 8 Selected from halogen, amino, cyano, nitro, C 1 -C 4 Alkyl, halogenated C 1-C 4 Alkyl, C 1 -C 4 Alkoxy, halogenated C 1 -C 4 Alkoxy, C 3 -C 4 Cycloalkyl, C 1 -C 4 Alkylamino, halogenated C 1 -C 4 Alkylamino, di(C 1 -C 4 alkyl)amino, halogenated di(C 1 -C 4 alkyl)amino, aminocarbonyl, di-C 1 -C 4 Alkylaminocarbonyl, dihalogenated C 1 -C 4 Alkylaminocarbonyl, C 1 -C 4 Alkylthio, halo 1 -C 4 Alkylthio, C 1 -C 4 Alkylsulfonyl, halo C 1 -C 4 Alkylsulfonyl.

[0054] m is an integer selected from 0 to 5. When m is 0, there is no substituent. When m is greater than 1, R 8 Same or different.

[0055] More preferably, in the compound represented by general formula I:

[0056] R 1 is selected from hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl or trifluoromethyl;

[0057] R 2 is selected from fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluoromonochloromethyl, dichloromonofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methoxycarbonyl, ethoxycarbonyl, R 2 When at the 4-position of the benzene ring, it is not selected from cyano or hydroxyl;

[0058] n is an integer selected from 0 to 5. When n is 0, there is no substituent. When n is greater than 1, R 2 Same or different;

[0059] R3 is selected from the group consisting of hydrogen, hydroxy, formyl, acetyl, propionyl, butyryl, trifluoroacetyl, benzoyl, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoroethyl, methoxy, ethoxy, trifluoroethoxy, cyclopropyloxy, allyl, propargyl, methylsulfonyl, ethylsulfonyl, trifluoroethylsulfonyl, methylaminosulfonyl, ethylaminosulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, methylsulfonylaminocarbonyl, methoxycarbonyl, ethoxycarbonyl, propoxycarbonyl, isopropoxycarbonyl, methylaminocarbonyl, dimethylaminocarbonyl, vinyloxycarbonyl, ethynyloxycarbonyl;

[0060] R 4 , R 5 are the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy;

[0061] R 6 , R 7 are the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy or tert-butoxy;

[0062] Q is selected from the following substituents:

[0063]

[0064] R 8 is selected from fluorine, chlorine, bromine, iodine, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluoromonochloromethyl, dichloromonofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methylsulfonyl, ethylsulfonyl;

[0065] m is an integer selected from 0 to 5. When m is 0, there is no substituent. When m is greater than 1, R 8 Same or different.

[0066] Still more preferably, in the compound represented by general formula I:

[0067] R 1 is selected from hydrogen or methyl;

[0068] R 3 Selected from hydrogen;

[0069] R 2 is selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, methylthio or trifluoromethoxy, R 2 When it is at the 4-position of the benzene ring, it is not selected from cyano.

[0070] R 4 , R 5 The same or different ones are selected from hydrogen, fluorine, chlorine, bromine or methyl;

[0071] R 6 , R 7 are all selected from hydrogen;

[0072] n is an integer selected from 0 to 5. When n is 0, there is no substituent on the ring; when n is greater than 1, R 2 Same or different;

[0073] Q is selected from the following substituents:

[0074]

[0075] R 8 is selected from fluorine, chlorine, bromine, iodine, cyano, amino, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy;

[0076] m is an integer selected from 0 to 4. When m is 0, there is no substituent. When m is greater than 1, R 8 Same or different.

[0077] In the definition of compounds of general formula I given above, the terms used are generally defined as follows:

[0078] 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, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, etc. Alkylsulfinyl: straight chain or branched alkyl is connected to the structure through a sulfinyl group (-SO-), such as methylsulfinyl. Haloalkylsulfinyl: straight chain or branched alkylsulfinyl, the hydrogen atoms on its alkyl can be partially or completely replaced by halogen atoms. Haloalkylsulfonyl: straight chain or branched alkylsulfonyl, the hydrogen atoms on its alkyl can be partially or completely replaced by halogen atoms. Alkylaminothio: such as CH 3 NHS-, C 2 H 5 NHS-. Dialkylaminosulfanyl: such as (CH3 ) 2 NS-, (C 2 H 5 ) 2 NS-. Alkylaminosulfonyl: alkyl-NH-SO 2 -. Dialkylaminosulfonyl: (alkyl) 2 -N-SO 2 -. Alkylsulfonylaminocarbonyl: alkyl-SO 2 -NH-CO-. Alkylcarbonylaminosulfonyl: alkyl-CO-NH-SO 2 -. Alkylcarbonylalkyl: alkyl-CO-alkyl-. Alkylsulfonyloxy: alkyl-S(O) 2 -O-. Haloalkylsulfonyloxy: The hydrogen atoms on the alkyl group of alkylsulfonyloxy can be partially or completely replaced by halogen atoms, such as CF 3 -SO 2 -O. Cycloalkyloxycarbonyl: such as cyclopropyloxycarbonyl, cyclohexyloxycarbonyl, etc. Alkoxy: straight chain or branched alkyl, connected to the structure via an oxygen atom. Haloalkoxy: straight chain or branched alkoxy, the hydrogen atoms on these alkoxy groups can be partially or completely replaced by halogen atoms. For example, chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, trifluoroethoxy, etc. Haloalkoxycarbonyl: the hydrogen atoms on the alkyl group of alkoxycarbonyl can be partially or completely replaced by halogen atoms, such as ClCH 2 CH 2 OCO-, CF 3 CH 2 OCO-, etc. Alkoxyalkyl: alkyl-O-alkyl-, such as CH 3 OCH 2 -. Haloalkoxyalkyl: The hydrogen atoms on the alkyl group of alkoxyalkyl can be partially or completely replaced by halogen atoms, such as ClCH 2 CH 2 OCH 2 -、CF 3 CH 2 OCH 2 - etc. Alkoxycarbonylalkyl: alkoxycarbonyl-alkyl-, such as CH 3 OCOCH 2 -. Haloalkoxycarbonylalkyl: The hydrogen atoms on the alkyl group of alkoxycarbonylalkyl can be partially or completely replaced by halogen atoms, such as CF 3 CH 2 OCOCH 2 -. Alkylcarbonyloxy: such as CH 3 COO-, etc. Haloalkylcarbonyloxy: The hydrogen atoms of alkylcarbonyloxy can be partially or completely replaced by halogen atoms, such as CF3 COO-, etc. Alkoxycarbonyloxy: alkoxycarbonyl-oxy-, such as CH 3 OCOO-. Haloalkoxycarbonyloxy: The hydrogen atoms on the alkyl group of alkoxycarbonyloxy may be partially or completely replaced by halogen atoms, such as CF 3 OCOO-. Alkylthiocarbonylalkyl: alkylthiocarbonyl-alkyl-, for example CH 3 SCOCH 2 -. Haloalkylthiocarbonylalkyl: The hydrogen atoms on the alkyl group of alkylthiocarbonylalkyl can be partially or completely replaced by halogen atoms, such as CF 3 CH 2 SCOCH 2 -. Alkoxyalkoxy: such as CH 3 OCH 2 O- etc. Haloalkoxyalkoxy: The hydrogen atoms on the alkoxy group can be partially or completely replaced by halogen atoms, such as CF 3 OCH 2 O-. Alkoxyalkoxycarbonyl: such as CH 3 OCH 2 CH 2 OCO-, etc. Alkylthio: a straight or branched alkyl group connected to the structure via a sulfur atom. Haloalkylthio: a straight or branched alkylthio group, in which the hydrogen atoms on the alkyl group may be partially or completely replaced by halogen atoms. For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, etc. Alkylthioalkyl: alkyl-S-alkyl-, for example CH 3 SCH 2 -. Haloalkylthioalkyl: The hydrogen atoms on the alkyl group of alkylthioalkyl can be partially or completely replaced by halogen atoms, such as ClCH 2 CH 2 SCH 2 -、CF 3 CH 2 SCH 2 - etc. Alkylamino: straight chain or branched alkyl group, connected to the structure via a nitrogen atom. Haloalkylamino: straight chain or branched alkylamino group, in which the hydrogen atoms on the alkyl group may be partially or completely replaced by halogen atoms. Dialkylamino: such as (CH 3 ) 2 N-, (CH 3 CH 2 ) 2 N-. Halodialkylamino: The hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms, such as (CF 3 ) 2 N-, (CF 3 CH 2 ) 2N-. Alkenyl: straight chain 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. Haloalkenyl: straight chain or branched alkenes, the hydrogen atoms on these alkenyls may be partially or completely replaced by halogen atoms. Alkenyloxy: straight chain or branched alkenes, connected to the structure via oxygen atoms. Haloalkenyloxy: straight chain or branched alkenyloxy, the hydrogen atoms on these alkenyloxys may be partially or completely replaced by halogen atoms. Alkenylthio: straight chain or branched alkenes, connected to the structure via sulfur atoms. Such as CH 2 =CHCH 2 S-. Alkenyloxycarbonyl: such as CH 2 =CHCH 2 OCO-, etc. Alkynyl: straight chain 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 chain or branched alkynes, the hydrogen atoms on these alkynyl groups can be partially or completely replaced by halogen atoms. Alkynyloxy: straight chain or branched alkynes, connected to the structure via an oxygen atom bond. Haloalkynyloxy: straight chain or branched alkynyloxy, the hydrogen atoms on these alkynyloxy groups can be partially or completely replaced by halogen atoms. Alkynyloxycarbonyl: such as CH≡CCH 2 OCO-, etc. Alkylsulfonyl: a straight chain or branched alkyl sulfonyl group (-SO 2 -) connected to the structure, such as methylsulfonyl. Haloalkylsulfonyl: a straight-chain or branched alkylsulfonyl group, in which the hydrogen atoms on the alkyl group may be partially or completely replaced by halogen atoms. Alkylcarbonyl: an alkyl group connected to the structure via a carbonyl group, such as CH 3 CO-, CH 3 CH 2 CO-. Haloalkylcarbonyl: The hydrogen atoms on the alkyl group of alkylcarbonyl can be partially or completely replaced by halogen atoms, such as CF 3 CO-. Alkoxycarbonyl: Alkoxy is connected to the structure via the carbonyl group. 3 OCO-, CH 3 CH 2 OCO-. Aminocarbonyl: such as NH 2 CO-. Alkylaminocarbonyl: alkyl-NH-CO-, such as CH 3 NHCO-, CH 3 CH 2 NHCO-. Dialkylaminocarbonyl: such as (CH 3 ) 2 NCO-, (CH 3 CH 2 ) 2NCO-. The aryl part in (hetero)aryl, (hetero)arylalkyl, (hetero)arylcarbonyl, (hetero)arylmethylcarbonyl, (hetero)arylcarbonylalkyl, (hetero)aryloxycarbonyl, (hetero)arylalkyloxycarbonyl includes phenyl or naphthyl, etc. Heteroaryl is a five-membered ring or six-membered ring containing one or more N, O, S heteroatoms. For example, furanyl, pyrazolyl, thiazolyl, pyridyl, pyrimidinyl, pyrazinyl, pyridazinyl, triazinyl, quinolinyl, etc. (hetero)aryl: such as phenyl, etc. (hetero)arylalkyl: such as benzyl, phenethyl, p-chlorobenzyl, 2-chloropyridin-5-yl, 2-chloro-thiazol-5-yl, etc. (hetero)arylcarbonyl: such as benzoyl, 4-chlorobenzoyl, etc. (hetero)arylmethylcarbonyl: such as PhCH 2 CO-. (Hetero)arylcarbonylalkyl: such as PhCOCH 2 -. (Hetero)aryloxycarbonyl: such as phenoxycarbonyl, 4-chlorophenoxycarbonyl, 4-nitrophenoxycarbonyl, naphthoxycarbonyl, etc. Arylalkyloxycarbonyl: such as benzyloxycarbonyl, 4-chlorobenzyloxycarbonyl, 4-trifluoromethylbenzyloxycarbonyl, etc. (Hetero)arylalkyloxycarbonyl: such as PhCH 2 OCO-, 4-Cl-PhCH 2 OCO-etc.

[0079] Table 1, Table 2, Table 3, Table 4, Table 5 respectively list the R 1 , R 3 , R 4 and R 5 , R 6 and R 7 , and some specific substituents for Q, but they are not limited to these substituents.

[0080]

[0081] Table 1 R 1 Substituents

[0082] <![CDATA[R 8 ]]> <![CDATA[R 8 ]]> <![CDATA[R 8 ]]> <![CDATA[R 8 ]]> H CN <![CDATA[CH 3 ]]> <![CDATA[C 2 H 5 ]]> <![CDATA[n-C 3 H 7 ]]> <![CDATA[i-C 3 H 7 ]]> <![CDATA[n-C 4 H 9 ]]> <![CDATA[s-C 4 H 9 ]]> <![CDATA[i-C 4 H 9 ]]> <![CDATA[t-C 4 H 9 ]]> <![CDATA[CF 3 ]]> <![CDATA[CCl 3 ]]> <![CDATA[CHF 2 ]]> <![CDATA[CH 2 F]]> <![CDATA[CH 2 Cl]]> <![CDATA[CH 2 CF 3 <!-- 8 -->]]> <![CDATA[CF 2 CF 3 ]]> <![CDATA[COOCH 3 ]]> Ph Ph-4-Cl

[0083] Table 2 R 3 Substituents

[0084]

[0085]

[0086] Table 3 R 4 (R 5 )Substituent

[0087]

[0088] Table 4 R 6 (R7 )Substituent

[0089]

[0090] Table 5 Q Substituents

[0091]

[0092]

[0093] Some of the compounds of the present invention can be illustrated by the specific compounds listed in Table 6 to Table 34, but the present invention is not limited thereto. 1 =R 3 =R 4 =R 5 =R 6 =R 7 =H.

[0094] In the general formula I, when the five-membered ring is a double bond, the general structure is as follows:

[0095]

[0096] In the general formula I-1, when Q=Q1, (R 2 ) n The substituents are shown in Table 6, and the representative compound numbers are 6-1 to 6-288.

[0097] Table 6

[0098]

[0099]

[0100]

[0101] Table 7: In the general formula I-1, when Q=Q2, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 7-1 to 7-288.

[0102] Table 8: In the general formula I-1, when Q=Q3, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 8-1 to 8-288.

[0103] Table 9: In the general formula I-1, when Q=Q4, the substituent (R 2 ) nConsistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 9-1 to 9-288.

[0104] Table 10: In the general formula I-1, when Q=Q5, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 10-1 to 10-288.

[0105] Table 11: In the general formula I-1, when Q=Q6, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 11-1 to 11-288.

[0106] Table 12: In the general formula I-1, when Q=Q7, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 12-1 to 12-288.

[0107] Table 13: In the general formula I-1, when Q=Q8, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 13-1 to 13-288.

[0108] Table 14: In the general formula I-1, when Q=Q9, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 14-1 to 14-288.

[0109] In the general formula I, when the five-membered ring is a single bond, the general structure is as follows:

[0110]

[0111] Table 15: In the general formula I-2, when Q=Q1, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 15-1 to 15-288.

[0112] Table 16: In the general formula I-2, when Q=Q2, the substituent (R 2 ) nConsistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 16-1 to 16-288.

[0113] Table 17: In the general formula I-2, when Q=Q3, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 17-1 to 17-288.

[0114] Table 18: In the general formula I-2, when Q=Q4, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 18-1 to 18-288.

[0115] Table 19: In the general formula I-2, when Q=Q5, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 19-1 to 19-288.

[0116] Table 20: In the general formula I-2, when Q=Q6, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 20-1 to 20-288.

[0117] Table 21: In the general formula I-2, when Q=Q7, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 21-1 to 21-288.

[0118] Table 22: In the general formula I-2, when Q=Q8, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 22-1 to 22-288.

[0119] Table 23: In the general formula I-2, when Q=Q9, the substituent (R 2 ) n Consistent with the substituents shown in Table 6, the substituents correspond to 6-1 to 6-288 in Table 6, and the representative compound numbers are 23-1 to 23-288.

[0120] In the general formula I-1, when Q=Q1, the substituent R3 (when not hydrogen) are different substituents as shown in Table 24, and the representative compound numbers are 24-1 to 24-140.

[0121] Table 24

[0122]

[0123]

[0124] 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:

[0125] The preparation of the compound of formula I adopts the following method:

[0126]

[0127] Intermediates II and III react under basic conditions in a suitable solvent to obtain a compound of formula I.

[0128] Suitable bases can be selected from, for example, triethylamine, potassium hydroxide, sodium hydroxide, sodium carbonate, potassium carbonate, sodium bicarbonate, pyridine, sodium methoxide, sodium ethoxide, sodium hydride, potassium tert-butoxide or sodium tert-butoxide.

[0129] The reaction is carried out in a suitable solvent, which can be selected from dichloromethane, tetrahydrofuran, 1,4-dioxane, acetonitrile, toluene, xylene, benzene, N,N-dimethylformamide, N-methylpyrrolidone, dimethyl sulfoxide, acetone or butanone.

[0130] The reaction temperature may be between room temperature and the boiling point of the solvent, usually 20-100°C.

[0131] The reaction time is from 30 minutes to 20 hours, usually from 1 to 10 hours.

[0132] The intermediate III is commercially available and can also be prepared by known methods, such as CN108947892, Journal of Medicinal Chemistry, 46 (23), 4895-4903; 2003, etc.

[0133] Intermediate II is a key intermediate for preparing the compound of formula I of the present invention, and is prepared by the following method:

[0134]

[0135] 4-Bromobutyne reacts with potassium phthalimide at a suitable temperature in a suitable solvent for 30 minutes to 20 hours, usually 1-10 hours, to obtain intermediate M1. The operation method of this step can be referred to WO2002028395 and Organic Letters, 7(4), 733-736; 2005. 4-Chlorobenzaldehyde oxime is chlorinated and reacted with M1 in a suitable solvent under alkaline conditions to obtain M2. The operation method of this step can be referred to WO2006065280 and Chemical Communications (Cambridge, United Kingdom), 47(11), 3198-3200; 2011. M2 is deaminated in a suitable solvent under alkaline conditions to obtain II. The operation method of this step can be referred to European Journal of Organic Chemistry, 2013(23), 5143-5148; 2013 and WO2016011209, etc.

[0136] Although the compounds of the general formula I of the present invention and some compounds disclosed in the prior art also belong to the substituted isoxazole ethylamine compounds, their structural features are still significantly different. And due to these structural differences, the compounds of the present invention have better fungicidal activity.

[0137] The compound of general formula I shows excellent activity against a variety of pathogens in agriculture or other fields. Therefore, the technical scheme of the present invention also includes the use of the compound of general formula I for preparing fungicides in agriculture or other fields.

[0138] The examples of diseases mentioned below are only used to illustrate the present invention, but they are by no means limiting.

[0139] 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. ;

[0140] 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.

[0141] 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.

[0142] Doses of 10 g to 5 kg of compound per hectare provide adequate control.

[0143] 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 miticide compounds 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.

[0144] 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. DETAILED DESCRIPTION

[0145] 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).

[0146] Synthesis Example

[0147] Example 1: Preparation of intermediate 2-(3-(4-p-chlorophenyl)isoxazol-5-yl)-1-ethylamine

[0148] 1) Preparation of N-(3-butyne)phthalimide

[0149]

[0150] 13.30 g (0.10 mol) of 4-bromobutyne and 18.5 g (0.1 mol) of potassium phthalimide were added to 100 ml of N,N-dimethylformamide solvent under stirring at room temperature. After stirring at 60°C for 5-7 hours, 50-100 ml of water was added to the reaction solution, filtered and washed with water to obtain 18.3 g of white solid with a yield of 92%.

[0151] 2) Preparation of 2-(3-(4-(p-chlorophenyl)isoxazol-5-yl)-1-ethylamine

[0152]

[0153] 15.5 g (0.1 mol) of 4-chlorobenzaldehyde oxime was dissolved in 50 ml of N,N-dimethylformamide solution. 14.7 g (0.11 mol) of NCS was added to the reaction flask in batches under stirring. The reaction was carried out at 50° C. for 3-4 hours. After the complete reaction of 4-chlorobenzaldehyde oxime was monitored by TLC, 19.9 g (0.1 mol) of N-(3-butyne)phthalimide and 8.4 g (0.1 mol) of sodium bicarbonate were added. The reaction was continued for 4 hours. After the reaction was completed as monitored by TLC, the reaction solution was cooled and poured into water, stirred for 30 minutes, filtered and washed with water to obtain 13.2 g of white solid with a yield of 37.4%.

[0154] The white solid obtained above was dissolved in 300 ml of THF and 60 ml of DCM, and 9.4 g of hydrazine hydrate was added. The mixture was reacted at 50° C. for 3-4 hours. After the reaction of N-(2-(3-(4-chlorophenyl)isoxazol-5-yl)ethyl)phthalimide was completely reacted as monitored by TLC, the mixture was cooled and filtered. The filtrate was concentrated under reduced pressure and DCM was added to dissolve the filtrate. The organic phase was washed with sodium hydroxide solution and dried over anhydrous magnesium sulfate to obtain 7.3 g of light yellow solid 2-(3-(4-chlorophenyl)isoxazol-5-yl)-1-ethylamine with a yield of 87.6%.

[0155] Example 2: Preparation of intermediates

[0156] 1) Preparation of N-(3-butylene)phthalimide

[0157]

[0158] 13.50 g (0.10 mol) of 4-bromobutyne and 18.5 g (0.1 mol) of potassium phthalimide were added to 100 ml of N,N-dimethylformamide solvent under stirring at room temperature. After stirring at 60°C for 5-7 hours, 50-100 ml of water was added to the reaction solution, and the solution was filtered and washed with water to obtain 17.6 g of a white solid with a yield of 87.6%.

[0159] 2) Preparation of 2-(3-(4-chlorophenyl)isoxazol-5-yl)-1-ethylamine

[0160]

[0161] 15.5 g (0.1 mol) of 4-chlorobenzaldehyde oxime was dissolved in 50 ml of N,N-dimethylformamide solution. 14.7 g (0.11 mol) of NCS was added to the reaction bottle in batches under stirring. The reaction was carried out at 50° C. for 3-4 hours. After the reaction of 4-chlorobenzaldehyde oxime was completely monitored by TLC, 20.1 g (0.1 mol) of N-(3-butyne)phthalimide and 8.4 g (0.1 mol) of sodium bicarbonate were added. The reaction was continued for 4 hours. After the reaction was completed as monitored by TLC, the reaction solution was cooled and poured into water, stirred for 30 minutes, filtered and washed with water to obtain 14.3 g of white solid with a yield of 40.3%.

[0162] The white solid obtained above was dissolved in 300 ml of THF and 60 ml of DCM, and 10 g of hydrazine hydrate was added. The mixture was reacted at 50° C. for 3-4 hours. After the reaction of N-(2-(3-(4-chlorophenyl)isoxazol-5-yl)ethyl)phthalimide was completely reacted as monitored by TLC, the mixture was cooled and filtered. The filtrate was concentrated under reduced pressure and DCM was added to dissolve the filtrate. The organic phase was washed with sodium hydroxide solution and dried over anhydrous magnesium sulfate to obtain 6.9 g of light yellow solid 2-(3-(4-chlorophenyl)isoxazol-5-yl)-1-ethylamine with a yield of 76.2%.

[0163] Example 3: Preparation of Compound 6-19

[0164]

[0165] 0.22 g (10 mmol) of 2-(3-(4-chlorophenyl)isoxazol-5-yl)-1-ethylamine was dissolved in 20 ml of acetonitrile solvent. 0.23 g (11 mol) of o-trifluoromethylbenzoyl chloride dissolved in 5 ml of acetonitrile was added dropwise into the reaction flask under stirring. The reaction was allowed to react at room temperature for 3-4 hours. After the reaction was completed as monitored by TLC, the solvent was evaporated under reduced pressure, and ethyl acetate (3×50 ml) was added for extraction. The organic phase was washed with 50 ml of saturated brine. After desolventizing, the residue was purified by column chromatography to obtain 0.24 g of a yellow oil with a yield of 60.8%.

[0166] 1H-NMR (600 MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):7.69(m,3H),7.54(m,2H),7.50(m,1H),7.42(m,2H),6.41(s,1H),6.15(s,1H),3.85(m,2H),3.17(m,2H).

[0167] Example 4: Preparation of Compounds 16-19

[0168]

[0169] 0.22 g (10 mmol) of 2-(3-(4-chlorophenyl)isoxazol-5-yl)-1-ethylamine was dissolved in 20 ml of acetonitrile solvent. 0.24 g (11 mol) of o-trifluoromethylbenzoyl chloride dissolved in 5 ml of acetonitrile was added dropwise into the reaction flask under stirring. The reaction was allowed to react at room temperature for 3-4 hours. After the reaction was completed as monitored by TLC, the solvent was evaporated under reduced pressure, and ethyl acetate (3×50 ml) was added for extraction. The organic phase was washed with 50 ml of saturated brine. After desolventizing, the residue was purified by column chromatography to obtain 0.20 g of a white solid with a yield of 49.4%.

[0170] 1 H-NMR (600 MHz, internal standard TMS, solvent CDCl 3 )δ(ppm):δ(CDCl 3 ):7.61(m,2H),7.50(s,1H),7.40(m,2H),4.92(m,1H),3.82(m,1H),3.62(m,1H),3.55(m,1H),3.05(m,1H),2.05(m,2H).

[0171] Other compounds of the present invention can be prepared by referring to the above examples.

[0172] Physical properties and NMR data of some compounds ( 1 HNMR, 600 MHz, internal standard TMS, ppm) is as follows:

[0173] Compound 6-1: oil. δ(CDCl 3 ):7.74(m,2H),7.68(m,1H),7.54(m,3H),7.43(m,3H),6.42(s,1H),6.24(s,1H),3.85(m,2H),3.17(m,2H).

[0174] Compound 6-4: oil. δ(CDCl 3):7.79(m,2H),7.68(m,1H),7.57(m,2H),7.52(m,1H),7.28(m,2H),6.42(s,1H),6.16(s,1H),3.85(m,2H),3.18(m,2H).

[0175] Compound 6-17: melting point 96.0°C. δ(CDCl 3 ):7.70(m,2H),7.58(m,1H),7.53(m,2H),7.48(m,1H),7.39(m,1H),7.34(m,1H),6.59(s,1H),6.09(s,1H),3.87(m,2H),3.21(m,2H).

[0176] Compound 6-21: oil. δ(CDCl 3 ):7.70(m,1H),7.66(m,1H),7.59(m,2H),7.54(m,2H),7.34(m,1H),6.59(s,1H),6.08(s,1H),3.87(m,2H),3.21(m,2H).

[0177] Compound 6-49: oil. δ(CDCl 3 ):7.90(m,2H),7.75(m,2H),7.70(m,1H),7.55(m,2H),7.25(m,1H),6.50(s,1H),6.07(s,1H),3.88(m,2H),3.21(m,2H).

[0178] Compound 6-57: oil. δ(CDCl 3 ):7.67(m,1H),7.62(m,2H),7.47(m,2H),7.45(m,1H),7.22(m,2H),6.38(s,1H),6.28(s,1H),3.83(m,2H),3.13(m,2H),2.38(s,3H).

[0179] Compound 6-55: melting point 90.8°C. δ(CDCl 3 ):7.69(m,1H),7.57(m,1H),7.52(m,2H),7.45(m,1H),7.33(m,1H),7.26 (m,2H),6.30(s,1H),6.16(s,1H),3.86(m,2H),3.18(m,2H),2.45(s,3H).

[0180] Compound 6-60: oil. δ(CDCl 3):7.70(m,1H),7.58(m,1H),7.53(m,2H),7.29(s,1H),7.16(m,2H),6.29 (s,1H),6.15(s,1H),3.86(m,2H),3.18(m,2H),2.40(s,3H),2.34(s,3H).

[0181] Compound 6-69: melting point 153.9°C. δ(CDCl 3 ):7.90(m,2H),7.70(m,3H),7.59(m,1H),7.52(m,2H),6.49(s,1H),6.08(s,1H),3.88(m,2H),3.21(m,2H).

[0182] Compound 6-78: oil. δ(CDCl 3 ):7.72(m,2H),7.68(m,1H),7.54(m,2H),7.48(m,1H),7.12(m,2H),6.39(s,1H),6.22(s,1H),3.84(m,2H),3.16(m,2H).

[0183] Compound 6-151: melting point 117.0°C. δ(CDCl 3 ):7.70(m,2H),7.58(m,1H),7.53(m,2H),7.24(m,1H),7.08(m,1H),6.57(s,1H),6.07(s,1H),3.87(m,2H),3.20(m,2H).

[0184] Compound 7-4: melting point 161.8°C. δ(CDCl 3 ):7.77(m,2H),7.15(m,2H),7.12(s,1H),6.40(s,1H),3.90(m,2H),3.20(m,2H).

[0185] Compound 7-19: δ(CDCl 3 ):7.72(m,2H),7.44(m,2H),7.12(s,1H),6.41(s,1H),3.90(m,2H),3.21(m,2H).

[0186] Compound 9-19: oil. δ(CDCl 3):8.61(m,1H),8.22(m,1H),7.71(m,3H),7.43(m,2H),6.48(s,1H),6.20(s,1H),3.90(m,2H),3.24(m,2H),3.11(s,3H).

[0187] Compound 10-19: δ(CDCl 3 ):7.91(s,1H),7.71(m,2H),7.43(m,2H),6.81(t,1H),6.59(s,1H),6.39(s,1H),3.91(s,3H),3.80(m,2H),3.14(m,2H).

[0188] Compound 10-21: oil. δ(CDCl 3 ):7.90(s,1H),7.58(m,1H),7.47(m,1H),7.31(m,1H),6.80(t,1H),6.58(s,1H),6.41(s,1H),3.90(s,3H),3.81(m,2H),3.15(m,2H).

[0189] Compound 11-4: melting point 103.9. δ(CDCl 3 ):7.74(m,2H),7.29(m,2H),7.24(m,1H),7.13(m,2H),6.43(s,1H),6.15(s,1H),3.90(m,2H),3.21(m,2H).

[0190] Compound 11-19: δ(CDCl 3 ):7.70(m,2H),7.43(m,2H),7.25(m,3H),6.45(s,1H),6.10(s,1H),3.90(m,2H),3.22(m,2H).

[0191] Compound 12-4: melting point 126°C. δ(CDCl 3 ):8.45(m,1H),8.08(m,1H),7.76(m,2H),7.34(m,1H),7.15(m,2H),6.76(s,1H),6.41(s,1H),3.90(m,2H),3.21(m,2H).

[0192] Compound 12-19: δ(CDCl 3):8.451(d,1H),7.72(m,2H),7.65(s,1H),7.51(m,1H),7.43(m,1H),6.55(s,1H),6.40(s,1H),3.87(m,2H),3.19(m,2H).

[0193] Compound 13-19: oil. δ(CDCl 3 ):7.71(m,2H),7.34(m,2H),6.28(s,1H),6.29(s,1H),6.24(s,1H),4.10(s,3H),3.78(m,2H),3.15(m,2H),2.23(s,3H).

[0194] Compound 14-19: δ(CDCl 3 ):7.70(m,2H),7.42(m,2H),6.40(s,1H),6.39(s,1H),3.83(m,2H),3.16(m,2H),2.72(s,3H).

[0195] Compound 15-4: oil. δ(CDCl 3 ):7.68(m,1H),7.63(m,2H),7.58(m,1H),7.53(m,2H),7.45(s,1H),7.09(m,1H),6.37(s,1H) ,4.87(m,1H),3.70(m,1H),3.61(m,1H),3.48(m,1H),3.06(m,1H),2.09(m,1H),1.98(m,1H).

[0196] Compound 15-17: oil. δ(CDCl 3 ):7.69(m,1H),7.59(m,2H),7.53(m,2H),7.43(m,1H),7.35(m,1H),7.30(m,1H),6.33 (s,1H),4.90(m,1H),3.73(m,1H),3.63(m,2H),3.25(m,1H),2.10(m,1H),2.04(m,1H).

[0197] Compound 15-19: δ(CDCl 3 ):7.70(m,1H),7.63(m,2H),7.58(m,3H),7.38(m,2H),6.31(s,1H),4.88(m,1H),3.70(m,2H),3.50(m,1H),3.05(m,1H),2.05(m,2H),.

[0198] Compound 15-21: melting point 102.2°C. δ(CDCl 3 ):7.69(m,1H),7.55(m,4H),7.45(s,1H),7.28(m,1H),6.30(s,1H),4.90(m,1H),3.71(m,1H),3.62(m,2H),3.22(m,1H),2.05(m,2H).

[0199] Compound 15-60: oil. δ(CDCl 3 ):7.70(m,1H),7.58(m,1H),7.52(m,2H),7.15(m,2H),7.11(m,1H),6.33(s,1H),4.81(m,1H),3.74 (m,1H),3.60(m,1H),3.55(m,1H),3.13(m,1H),2.48(s,3H),2.34(s,3H),2.09(m,1H),1.99(m,1H).

[0200] Compound 15-69: melting point 139°C. δ(CDCl 3 ):7.77(m,2H),7.70(m,1H),7.66(m,2H),7.60(m,1H),7.54(m,2H),6.26(s,1H),4.94 (m,1H),3.71(m,1H),3.64(m,1H),3.53(m,1H),3.10(m,1H),2.13(m,1H),2.02(m,1H).

[0201] Compound 15-78: oil. δ(CDCl 3 ):7.68(m,3H),7.58(m,1H),7.53(m,2H),7.25(m,2H),6.37(s,1H),4.89(m,1H) ,3.68(m,1H),3.61(m,1H),3.50(m,1H),3.06(m,1H),2.09(m,1H),1.99(m,1H).

[0202] Compound 15-151: melting point 60.5°C. δ(CDCl 3 ):7.69(m,1H),7.60(m,2H),7.53(m,2H),7.18(m,1H),7.03(m,1H),6.31(s,1H) ,4.90(m,1H),3.73(m,1H),3.61(m,2H),3.22(m,1H),2.10(m,1H),2.01(m,1H).

[0203] Compound 15-288: oil. δ(CDCl 3 ):7.69(m,1H),7.58(m,3H),7.52(m,2H),7.42(m,2H),6.35(s,1H),4.85(m,1H),3.73 (m,1H),3.61(m,1H),3.50(m,1H),3.06(m,1H),2.09(m,1H),1.97(m,1H),1.33(s,3H).

[0204] Compound 16-4: oil. δ(CDCl 3 ):7.65(m,2H),7.51(s,1H),7.11(m,2H),4.90(m,1H),3.83(m,1H),3.62(m,1H),3.52(m,1H),3.06(m,1H),2.12(m,1H),2.02(m,1H).

[0205] Compound 16-17: oil. δ(CDCl 3 ):7.60(m,1H),7.52(s,1H),7.43(m,1H),7.37(m,1H),7.31(m,1H),4.93(m,1H),3.85(m,1H),3.65(m,2H),3.26(m,1H),2.07(m,2H).

[0206] Compound 16-21: melting point 112.8°C. δ(CDCl 3 ):7.59(m,1H),7.48(s,1H),7.45(m,1H),7.30(m,1H),4.93(m,1H),3.84(m,1H),3.63(m,2H),3.24(m,1H),2.07(m,2H).

[0207] Compound 16-60: oil. δ(CDCl 3 ):7.58(s,1H),7.16(m,1H),7.12(m,2H),4.85(m,1H),3.85(m,1H),3.63(m,1H) ,3.57(m,1H),3.12(m,1H),2.49(s,3H),2.34(s,3H),2.09(m,1H),2.01(m,1H).

[0208] Compound 16-69: melting point 104.8°C. δ(CDCl 3):7.78(m,3H),7.67(m,2H),7.47(s,1H),4.96(m,1H),3.83(m,1H),3.62(m,1H),3.54(m,1H),3.09(m,1H),2.14(m,1H),2.04(m,1H).

[0209] Compound 16-78: oil. δ(CDCl 3 ):7.70(m,2H),7.50(s,1H),7.25(m,2H),4.93(m,1H),3.83(m,1H),3.63(m,1H),3.52(m,1H),3.07(m,1H),2.13(m,1H),2.02(m,1H).

[0210] Compound 16-151: melting point 106.1°C. δ(CDCl 3 ):7.63(m,1H),7.50(s,1H),7.19(m,1H),7.05(m,1H),4.92(m,1H),3.85(m,1H),3.63(m,2H),3.24(m,1H),2.07(m,2H).

[0211] Compound 16-288: melting point 142°C. δ(CDCl 3 ):7.60(m,2H),7.54(s,1H),7.43(m,2H),4.89(m,1H),3.84(m,1H),3.63 (m,1H),3.52(m,1H),3.07(m,1H),2.11(m,1H),2.00(m,1H),1.33(s,3H).

[0212] Compound 17-19: melting point 184.1°C. δ(CDCl 3 ):8.00(d,1H),7.88(m,1H),7.80(m,1H),7.59(m,2H),7.40(m,2H),6.69(s,1H),4.92 (m,1H),3.80(m,1H),3.64(m,1H),3.51(m,1H),3.08(m,4H),2.13(m,1H),2.03(m,1H).

[0213] Compound 18-19: melting point 189.1°C. δ(CDCl 3):8.60(d,1H),8.22(m,1H),7.78(m,1H),7.57(m,2H),7.39(m,2H),6.65(s,1H),4.92(m,1H) ,3.79(m,1H),3.63(m,1H),3.52(m,1H),3.12(s,3H),3.08(m,1H),2.14(m,1H),2.02(m,1H).

[0214] Compound 19-19:δ(CDCl 3 ):7.88(s,1H),7.59(m,2H),7.37(m,2H),6.90(t,1H),6.64(s,1H),4.87 (m,1H),3.93(s,3H),3.61(m,2H),3.46(m,1H),3.03(m,1H),2.03(m,2H).

[0215] Compound 20-19: δ(CDCl 3 ):7.57(m,2H),7.37(m,2H),7.25(m,3H),6.27(s,1H),4.93(m,1H),3.68(m,2H),3.48(m,1H),2.07(m,2H).

[0216] Compound 21-19: δ(CDCl 3 ):8.52(d,1H),7.71(m,1H),7.60(m,2H),7.54(m,1H),7.39(m,2H),6.97 (s,1H),4.92(m,1H),3.82(m,1H),3.56(m,2H),3.07(m,1H),2.05(m,2H).

[0217] Compound 22-19: oil. δ(CDCl 3 ):7.70(m,2H),7.35(m,2H),6.29(s,1H),6.27(s,1H),6.24(s,1H),4.11(s,3H),3.79(m,2H),3.16(m,2H),2.23(s,3H).

[0218] Compound 23-19: δ(CDCl 3 ):7.58(m,2H),7.38(m,2H),6.64(s,1H),4.86(m,1H),3.62(m,2H),3.48(m,1H),3.05(m,1H),2.74(s,3H),2.01(m,2H).

[0219] Meanwhile, other compounds represented by the general formula I of the present invention can be obtained by replacing the corresponding raw materials according to the contents described in the above synthesis examples.

[0220] Biological Activity Assay Example

[0221] The compound of the invention exhibits good activity against various pathogens in the agricultural field.

[0222] Example 5: Bactericidal activity assay

[0223] The samples of the compounds of the present invention were used to test the in vitro antibacterial activity or in vivo protective effect against various fungal diseases of plants. The results of the fungicidal activity test are shown in the following examples.

[0224] (1) In vitro bactericidal activity assay

[0225] The determination method is as follows: a high-throughput screening method is used, that is, the sample of the compound to be tested is dissolved in a suitable solvent (the type of solvent is acetone, methanol, DMF, etc., and is selected according to its solubility for the sample) to prepare a test solution of the required concentration. In an ultra-clean working environment, the test solution is added to the microwells of a 96-well culture plate, and then the pathogen propagule suspension is added thereto, and the treated culture plate is placed in a constant temperature incubator for culture. An investigation is conducted 24 hours later, and the germination or growth of the pathogen propagule is visually observed during the investigation, and the antibacterial activity of the compound is evaluated based on the germination or growth of the control treatment.

[0226] The test results of in vitro antibacterial activity (expressed as inhibition rate) of some compounds are as follows:

[0227] Inhibition rate of rice blast fungus:

[0228] At a dosage of 25 ppm, the compounds provided by the present invention have a good inhibition rate on rice blast. For example, compounds 12-19 etc. have an inhibition rate on rice blast of more than 80%.

[0229] (2) In vivo protective activity assay

[0230] The determination method is as follows: adopt the living potted plant determination method, that is, the sample of the compound 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 infection is completed, 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.

[0231] The in vivo protective activity test results of some compounds are as follows:

[0232] (1) Cucumber downy mildew

[0233] At a dosage of 400 ppm, the compounds provided by the present invention have a good inhibition rate on cucumber downy mildew. For example, compounds 6-1, 6-4, 6-19, 6-57, 6-78, 6-288, 7-4, 10-21, 11-4, 12-4, 12-19, 13-19, 14-19, 15-19, 15-21, 15-151, 15-69, 16-4, 16-17, 16-19, 16-21, 16-60, 16-69, 16-78, 16-151, 16-288, 19-19, 20-19, 21-19, 23-19, etc. have a prevention effect of more than 80% on cucumber downy mildew.

[0234] At a dosage of 100 ppm, compounds 6-19, 6-288, 12-19, 13-19, 16-69, and 16-151 had good inhibition rates against cucumber downy mildew, with the prevention efficacy against cucumber downy mildew being above 85%;

[0235] At a dosage of 25 ppm, compounds 6-19 and 12-19 had better inhibition rates against cucumber downy mildew, for example, etc., with a control efficiency of more than 90% against cucumber downy mildew;

[0236] (2) Wheat powdery mildew

[0237] At a dosage of 400 ppm, the compounds provided by the present invention have a good inhibition rate on wheat powdery mildew. For example, compounds 6-57, 6-288, 11-4, 12-4, 12-19, 16-4, 16-60, 23-19, etc. have a prevention effect of more than 80% on wheat powdery mildew.

[0238] At a dosage of 100 ppm, compounds 6-57, 6-288, and 16-60 had a good inhibition rate against wheat powdery mildew, with a control efficiency of more than 85% against wheat powdery mildew;

[0239] At a dosage of 25 ppm, compounds 6-57 and 6-288 had a better inhibition rate against wheat powdery mildew, with a control efficiency of more than 90% against wheat powdery mildew;

[0240] (3) Corn rust

[0241] At a dosage of 400 ppm, the compounds provided by the present invention have a good inhibition rate on corn rust. For example, compounds 6-1, 7-4, 10-21, 11-4, 12-4, 12-19, etc., have an inhibitory effect on corn rust of more than 80%.

[0242] At a dosage of 100 ppm, compounds 7-4, 10-21, 11-4, and 12-4 had a good inhibition rate against corn rust, with a control effect of more than 85% against corn rust;

[0243] (4) Cucumber Anthracnose

[0244] At a dosage of 400 ppm, the compounds provided by the present invention have a good inhibition rate on anthracnose of cucurbits. For example, compounds 6-151, 16-17, 16-19, 16-21, 16-60, 16-151, 18-19, etc. have an inhibitory effect of more than 80% on anthracnose of cucurbits.

[0245] At a dosage of 100 ppm, compounds 16-17, 16-19, 16-21, 16-69, and 16-151 had good inhibition rates against anthracnose of melons and more than 85% protection against corn rust;

[0246] At a dosage of 25 ppm, compounds 16-19, 16-21, and 16-151 had a good inhibition rate against anthracnose of melons and a control rate of more than 90% against powdery mildew of wheat;

[0247] From the above data, it can be seen that the compound represented by the novel general formula I of the present invention exhibits good activity against a variety of pathogens in the agricultural field, and the compound exhibits outstanding activity effects at some low doses, which are superior to the control compound.

[0248] Other compounds of the general formula I of the present invention may also have corresponding activities if tested in the above-mentioned biological activity assay method.

Claims

1. A substituted isoxazole ethylamine compound, characterized in that: The substituted isoxazole ethylamine compound is a compound represented by the general formula I; Where: R1 is selected from hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl; R2 is selected from halogen, hydroxyl, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C1-C4 alkoxycarbonyl, halogenated C1-C4 alkoxycarbonyl, and when R2 is at the 4th position of the benzene ring, it is not selected from cyano or hydroxyl; n is an integer selected from 0 to 5, when n is 0, there is no substituent; when n is greater than 1, R2 are the same or different; R3 is selected from hydrogen, hydroxy, C1-C4 alkyl, halogenated C1-C4 alkyl; R4 and R5 are the same or different and are selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl; R6 and R7 are the same or different and are selected from hydrogen, halogen, C1-C4 alkyl, halogenated C1-C4 alkyl; Q is selected from the following substituents: R8 is selected from halogen, amino, cyano, nitro, C1-C4 alkyl, halogenated C1-C4 alkyl, C1-C4 alkoxy, halogenated C1-C4 alkoxy, C3-C4 cycloalkyl, C1-C4 alkylthio, halogenated C1-C4 alkylthio, C1-C4 alkylsulfonyl, halogenated C1-C4 alkylsulfonyl; m is an integer selected from 0 to 5. When m is 0, there is no substituent; when m is greater than 1, R8 are the same or different.

2. The substituted isoxazole ethylamine compound according to claim 1, characterized in that: In the compound represented by general formula I: R1 is selected from hydrogen, methyl, ethyl or trifluoromethyl; R2 is selected from fluorine, chlorine, bromine, iodine, hydroxyl, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluoromonochloromethyl, dichloromonofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methoxycarbonyl, ethoxycarbonyl, and when R2 is at the 4th position of the benzene ring, it is not selected from cyano or hydroxyl; n is an integer selected from 0 to 5, when n is 0, there is no substituent; when n is greater than 1, R2 are the same or different; R3 is selected from hydrogen, hydroxy, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, trifluoroethyl; R4 and R5 are the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl; R6 and R7 are the same or different and are selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl and tert-butyl; Q is selected from the following substituents: R8 is selected from fluorine, chlorine, bromine, iodine, cyano, amino, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, trichloromethyl, difluoromonochloromethyl, dichloromonofluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec-butoxy, isobutoxy, tert-butoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy, methylsulfonyl, ethylsulfonyl; m is an integer selected from 0 to 5. When m is 0, there is no substituent; when m is greater than 1, R8 are the same or different.

3. The substituted isoxazole ethylamine compound according to claim 2, characterized in that: In the compound represented by general formula I: R1 is selected from hydrogen or methyl; R3 is selected from hydrogen; R2 is selected from fluorine, chlorine, bromine, iodine, cyano, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, methylthio or trifluoromethoxy, and when R2 is at the 4-position of the benzene ring, it is not selected from cyano; R4 and R5 are the same or different and are selected from hydrogen, fluorine, chlorine, bromine or methyl; R6 and R7 are both selected from hydrogen; n is an integer selected from 0 to 5. When n is 0, there is no substituent on the ring; when n is greater than 1, R2 are the same or different; Q is selected from the following substituents: R8 is selected from fluorine, chlorine, bromine, iodine, cyano, amino, nitro, methyl, ethyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy, methylthio, ethylthio, trifluoromethoxy, trifluoroethoxy; m is an integer selected from 0 to 4. When m is 0, there is no substituent; when m is greater than 1, R8 are the same or different.

4. A method for preparing a substituted isoxazole ethylamine compound according to claim 1, characterized in that: The preparation method of the compound shown in general formula I is:

5. Use of the substituted isoxazole ethylamine compound according to claim 1 in preparing a bactericidal pharmaceutical preparation.

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