CN-121991052-A - Phenyl oxadiazole compound and application thereof

CN121991052ACN 121991052 ACN121991052 ACN 121991052ACN-121991052-A

Abstract

The invention discloses a phenyl oxadiazole compound, which has a structure shown in a general formula I: Wherein each substituent group is defined in the specification. The compound has excellent bactericidal activity and excellent control effects on powdery mildew, downy mildew, rust disease and the like.

Inventors

YANG JICHUN
GUAN AIYING
SUN QIN
LI MIAO
WANG BIN
YANG JINLONG
LI ZHINIAN
XIA XIYUAN
GUI XIAODONG

Assignees

沈阳中化农药化工研发有限公司
江苏扬农化工股份有限公司

Dates

Publication Date: 20260508
Application Date: 20241108

Claims (8)

1. A phenyl oxadiazole compound is characterized in that the phenyl oxadiazole compound is a compound shown in a general formula I; Wherein: R 1 is selected from hydrogen, halogen, cyano, nitro, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, Halogenated C 3 -C 12 cycloalkyl, C 1 -C 12 alkoxy, halogenated C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, halogenated C 1 -C 12 alkylthio, C 1 -C 12 alkylamino, C 1 -C 12 alkylsulfinyl, halogenated C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, Halogenated C 1 -C 12 alkylsulfonyl, C 2 -C 12 alkenyl, halogenated C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, halogenated C 2 -C 12 alkynyl, C 2 -C 12 alkenyloxy, halogenated C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy or halogenated C 2 -C 12 alkynyloxy; R 2 、R 3 , which may be the same or different, is selected from CR 6 or N; is positioned at the 2, 3 or 4 positions of the benzene ring; R 4 is selected from hydrogen, halogen, cyano, amino, hydroxy, mercapto, carboxyl, morpholinyl, C 1 -C 12 alkyl, halo C 1 -C 12 alkyl, cyano C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, haloC 3 -C 12 cycloalkyl, C 1 -C 12 alkoxy, haloC 1 -C 12 alkoxy, C 1 -C 12 alkylthio, Halogenated C 1 -C 12 alkylthio, C 2 -C 12 alkenyloxy, halogenated C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy, halogenated C 2 -C 12 alkynyloxy, c 1 -C 12 Alkylsulfinyl group halogenated C 1 -C 12 alkylsulfinyl radical C 1 -C 12 alkylsulfonyl, halogenated C 1 -C 12 alkylsulfonyl, c 1 -C 12 AlkoxyC 1 -C 12 alkyl, haloC 1 -C 12 AlkoxyC 1 -C 12 alkyl, C 1 -C 12 alkylamino, Halogenated C 1 -C 12 alkylamino or di (C 1 -C 12 alkylamino); R 5 is selected from hydrogen, halogen, cyano, nitro, C 1 -C 12 alkyl, halogenated C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, Halogenated C 3 -C 12 cycloalkyl, C 1 -C 12 alkoxy, halogenated C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, halogenated C 1 -C 12 alkylthio, C 1 -C 12 alkylamino, C 1 -C 12 alkylsulfinyl, halogenated C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, Halogenated C 1 -C 12 alkylsulfonyl, C 2 -C 12 alkenyl, halogenated C 2 -C 12 alkenyl, C 2 -C 12 alkynyl, halogenated C 2 -C 12 alkynyl, C 2 -C 12 alkenyloxy, halogenated C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy or halogenated C 2 -C 12 alkynyloxy; R 6 is selected from hydrogen, halogen, cyano, C 1 -C 12 alkyl, halo C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, halo C 3 -C 12 cycloalkyl, C 1 -C 12 alkoxy, halo C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, halo C 1 -C 12 alkylthio, C 1 -C 12 alkylamino, C 1 -C 12 alkylsulfinyl, halo C 1 -C 12 alkylsulfinyl, C 1 -C 12 alkylsulfonyl, halo C 1 -C 12 alkylsulfonyl, C 2 -C 12 alkenyloxy, halo C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyloxy or halo C 2 -C 12 alkynyloxy; n is selected from 0, 1, 2,3 or 4, and R 5 may be the same or different when n is greater than 1; X is selected from O or S; Y is selected from O, S or NH.
2. The compound of claim 1, wherein in the compound of formula I: R 1 is selected from hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, Halogenated C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, halogenated C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halogenated C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, C 1 -C 6 alkylsulfinyl, halogenated C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, Halogenated C 1 -C 6 alkylsulfonyl, C 2 -C 6 alkenyl, halogenated C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, halogenated C 2 -C 6 alkynyl, c 2 -C 6 alkenyloxy, halogenated C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy or halogenated C 2 -C 6 alkynyloxy; R 2 、R 3 , which may be the same or different, is selected from CR 6 or N; is positioned at the 2, 3 or 4 positions of the benzene ring; R 4 is selected from hydrogen, halogen, cyano, amino, hydroxy, mercapto, carboxyl, morpholinyl, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, cyano C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, haloC 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, haloC 1 -C 6 alkoxy, C 1 -C 6 alkylthio, Halogenated C 1 -C 6 alkylthio, C 2 -C 6 alkenyloxy, halogenated C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy, halogenated C 2 -C 6 alkynyloxy, C 1 -C 6 Alkylsulfinyl group halogenated C 1 -C 6 alkylsulfinyl radical C 1 -C 6 alkylsulfonyl, halogenated C 1 -C 6 alkylsulfonyl, C 1 -C 6 AlkoxyC 1 -C 6 alkyl, haloC 1 -C 6 AlkoxyC 1 -C 6 alkyl, C 1 -C 6 alkylamino, Halogenated C 1 -C 6 alkylamino or di (C 1 -C 6 alkylamino); R 5 is selected from hydrogen, halogen, cyano, nitro, C 1 -C 6 alkyl, halogenated C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, Halogenated C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, halogenated C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halogenated C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, C 1 -C 6 alkylsulfinyl, halogenated C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, Halogenated C 1 -C 6 alkylsulfonyl, C 2 -C 6 alkenyl, halogenated C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, halogenated C 2 -C 6 alkynyl, c 2 -C 6 alkenyloxy, halogenated C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy or halogenated C 2 -C 6 alkynyloxy; R 6 is selected from hydrogen, halogen, cyano, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, halo C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, halo C 1 -C 6 alkylthio, C 1 -C 6 alkylamino, C 1 -C 6 alkylsulfinyl, halo C 1 -C 6 alkylsulfinyl, C 1 -C 6 alkylsulfonyl, halo C 1 -C 6 alkylsulfonyl, C 2 -C 6 alkenyloxy, halo C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyloxy or halo C 2 -C 6 alkynyloxy; n is selected from 0, 1, 2,3 or 4, and R 5 may be the same or different when n is greater than 1; X is selected from O or S; Y is selected from O or S.
3. The compound according to claim 2, wherein in the compound of formula I: R 1 is selected from hydrogen, halogen, cyano, nitro, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, Halogenated C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, halogenated C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, halogenated C 1 -C 4 alkylthio, C 1 -C 4 Alkylsulfinyl group halogenated C 1 -C 4 alkylsulfinyl radical C 1 -C 4 alkylsulfonyl, halogenated C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenyl, haloC 2 -C 4 alkenyl, C 2 -C 4 alkynyl, haloC 2 -C 4 alkynyl, C 2 -C 4 alkenyloxy, Halogenated C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy or halogenated C 2 -C 4 alkynyloxy; R 2 is selected from CR 6 or N; R 3 is selected from N; is positioned at the 2, 3 or 4 positions of the benzene ring; R 4 is selected from hydrogen, halogen, cyano, amino, hydroxy, mercapto, carboxyl, morpholinyl, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, cyano C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, haloC 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, haloC 1 -C 4 alkoxy, C 1 -C 4 alkylthio, Halogenated C 1 -C 4 alkylthio, C 2 -C 4 alkenyloxy, halogenated C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, halogenated C 2 -C 4 alkynyloxy, C 1 -C 4 Alkylsulfinyl group halogenated C 1 -C 4 alkylsulfinyl radical C 1 -C 4 alkylsulfonyl, halogenated C 1 -C 4 alkylsulfonyl, C 1 -C 4 AlkoxyC 1 -C 4 alkyl, haloC 1 -C 4 AlkoxyC 1 -C 4 alkyl, C 1 -C 4 alkylamino, halogenated C 1 -C 4 alkylamino or di (C 1 -C 4 alkylamino); r 5 is selected from hydrogen, halogen, cyano, nitro, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, Halogenated C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, halogenated C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, halogenated C 1 -C 4 alkylthio, C 1 -C 4 Alkylsulfinyl group halogenated C 1 -C 4 alkylsulfinyl radical C 1 -C 4 alkylsulfonyl, halogenated C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenyl, haloC 2 -C 4 alkenyl, C 2 -C 4 alkynyl, haloC 2 -C 4 alkynyl, C 2 -C 4 alkenyloxy, Halogenated C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy or halogenated C 2 -C 4 alkynyloxy; R 6 is selected from hydrogen, halogen, cyano, C 1 -C 4 alkyl, halo C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, halo C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, halo C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, halo C 1 -C 4 alkylthio, C 1 -C 4 alkylamino, C 1 -C 4 alkylsulfinyl, halo C 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, halo C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenyloxy, halo C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy or halo C 2 -C 4 alkynyloxy; n is selected from 0,1,2 or 3, and R 5 may be the same or different when n is greater than 1; X is selected from O or S; Y is selected from O or S.
4. A compound according to claim 3, wherein in the compound of formula I: R 1 is selected from hydrogen, halogen, cyano, nitro, C 1 -C 4 alkyl, haloC 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, haloC 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, haloC 1 -C 4 alkoxy, C 1 -C 4 alkylthio, haloC 1 -C 4 alkylthio, C 1 -C 4 alkylsulfinyl, haloC 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, haloC 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenyl, C 2 -C 4 alkynyl, C 2 -C 4 alkenyloxy, haloC 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy or haloC 2 -C 4 alkynyloxy; R 2 is selected from CR 6 or N; R 3 is selected from N; is positioned at the 4-position of the benzene ring; R 4 is selected from hydrogen, halogen, cyano, amino, hydroxy, mercapto, C 1 -C 6 alkyl, haloC 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, haloC 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, haloC 1 -C 4 alkoxy, C 1 -C 4 alkylthio, haloC 1 -C 4 alkylthio, C 2 -C 4 alkenyloxy, haloC 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, haloC 2 -C 4 alkynyloxy, C 1 -C 4 alkylsulfinyl, haloC 1 -C 4 alkylsulfinyl, C 1 -C 4 alkylsulfonyl, haloC 1 -C 4 alkylsulfonyl, C 1 -C 4 alkylamino or di (C 1 -C 4 alkylamino); R 5 is selected from hydrogen, halogen, cyano, nitro, C 1 -C 4 alkyl, halo C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, halo C 1 -C 4 alkoxy, C 2 -C 4 alkenyloxy, halo C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy or halo C 2 -C 4 alkynyloxy; R 6 is selected from halogen, C 1 -C 4 alkyl, halogenated C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, halogenated C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, halogenated C 1 -C 4 alkylthio, C 1 -C 4 alkylamino, C 1 -C 4 alkylsulfonyl, halogenated C 1 -C 4 alkylsulfonyl, C 2 -C 4 alkenyloxy, halogenated C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy or halogenated C 2 -C 4 alkynyloxy; n is selected from 0,1,2 or 3, and R 5 may be the same or different when n is greater than 1; X is selected from O or S; Y is selected from O or S.
5. The compound of claim 4, wherein in the compound of formula I: R 1 is selected from hydrogen, halogen, C 1 -C 4 alkyl, C 2 -C 4 alkenyl, or C 2 -C 4 alkynyl; R 2 is selected from CR 6 or N; R 3 is selected from N; is positioned at the 4-position of the benzene ring; r 4 is selected from hydrogen, halogen, cyano, amino, hydroxy, mercapto, C 1 -C 6 alkyl, haloC 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 alkylthio, haloC 1 -C 4 alkylthio, C 2 -C 4 alkenyloxy, haloC 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, haloC 2 -C 4 alkynyloxy, C 1 -C 4 alkylsulfonyl, haloC 1 -C 4 alkylsulfonyl, or C 1 -C 4 alkylamino; R 5 is selected from hydrogen, halogen, cyano, nitro, C 1 -C 4 alkyl, halo C 1 -C 4 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 4 alkoxy, or halo C 1 -C 4 alkoxy; r 6 is selected from halogen or C 1 -C 4 alkoxy; n is selected from 0,1,2 or 3, and R 5 may be the same or different when n is greater than 1; X is selected from O or S; Y is selected from O or S.
6. The compound of claim 5, wherein the compound of formula I: r 1 is selected from hydrogen, halogen, or C 1 -C 4 alkyl; R 2 is selected from CR 6 or N; R 3 is selected from N; is positioned at the 4-position of the benzene ring; R 4 is selected from hydrogen, C 1 -C 6 alkyl, halogenated C 1 -C 5 alkyl, C 3 -C 6 cycloalkyl or C 1 -C 4 alkylamino; R 5 is selected from hydrogen, halogen, nitro, C 1 -C 4 alkyl or C 1 -C 4 alkoxy; r 6 is selected from halogen or C 1 -C 4 alkoxy; n is selected from 0,1, 2 or 3; X is selected from O or S; Y is selected from O or S.
7. The compound of claim 6, wherein the compound of formula I: R 1 is selected from hydrogen, fluorine, chlorine, bromine, iodine, methyl, ethyl, n-propyl or isopropyl; R 2 is selected from CR 6 or N; R 3 is selected from N; is positioned at the 4-position of the benzene ring; R 4 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-pentyl, 2-methylbutyl, 3-dimethylbutyl, 2-dimethylbutyl, difluoromethyl, trifluoromethyl, trifluoroethyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylamino, ethylamino, n-propylamino or isopropylamino; R 5 is selected from hydrogen, fluorine, chlorine, bromine, nitro, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, methoxy, ethoxy, n-propoxy or isopropoxy; R 6 is selected from chlorine, bromine, methoxy, ethoxy, n-propoxy or isopropoxy; n is selected from 0,1,2 or 3, and R 5 may be the same or different when n is greater than 1; X is selected from O or S; Y is selected from O or S.
8. Use of a phenyloxadiazole compound as claimed in any one of claims 1 to 7 as a fungicide in agriculture or other fields.

Description

Phenyl oxadiazole compound and application thereof Technical Field The invention belongs to the field of agricultural sterilization, and particularly relates to a novel phenyl oxadiazole compound and application thereof. Background The patents WO9636229, CN102336744 and WO2015056806 successively disclose triazolinones and tetrazolinones which have bactericidal activity. However, the phenyl oxadiazole compound with the structure shown in the general formula I is not reported. Disclosure of Invention The invention aims to provide a phenyl oxadiazole compound capable of controlling harmful germs at a very low dosage, which is used as a medicament for controlling germs in agriculture or other fields. In order to achieve the above purpose, the technical scheme of the invention is as follows: the phenyl oxadiazole compound is a compound shown in a general formula I; Wherein: R 1 is selected from hydrogen, halogen, cyano, nitro, C 1-C12 alkyl, halogenated C 1-C12 alkyl, C 3-C12 cycloalkyl, Halogenated C 3-C12 cycloalkyl, C 1-C12 alkoxy, halogenated C 1-C12 alkoxy, C 1-C12 alkylthio, halogenated C 1-C12 alkylthio, C 1-C12 alkylamino, C 1-C12 alkylsulfinyl, halogenated C 1-C12 alkylsulfinyl, C 1-C12 alkylsulfonyl, Halogenated C 1-C12 alkylsulfonyl, C 2-C12 alkenyl, halogenated C 2-C12 alkenyl, C 2-C12 alkynyl, halogenated C 2-C12 alkynyl, C 2-C12 alkenyloxy, halogenated C 2-C12 alkenyloxy, C 2-C12 alkynyloxy or halogenated C 2-C12 alkynyloxy; R 2、R3, which may be the same or different, is selected from CR 6 or N; is positioned at the 2, 3 or 4 positions of the benzene ring; R 4 is selected from hydrogen, halogen, cyano, amino, hydroxy, mercapto, carboxyl, morpholinyl, C 1-C12 alkyl, halo C 1-C12 alkyl, cyano C 1-C12 alkyl, C 3-C12 cycloalkyl, haloC 3-C12 cycloalkyl, C 1-C12 alkoxy, haloC 1-C12 alkoxy, C 1-C12 alkylthio, Halogenated C 1-C12 alkylthio, C 2-C12 alkenyloxy, halogenated C 2-C12 alkenyloxy, C 2-C12 alkynyloxy, halogenated C 2-C12 alkynyloxy, c 1-C12 Alkylsulfinyl group halogenated C 1-C12 alkylsulfinyl radical C 1-C12 alkylsulfonyl, halogenated C 1-C12 alkylsulfonyl, c 1-C12 AlkoxyC 1-C12 alkyl, haloC 1-C12 AlkoxyC 1-C12 alkyl, C 1-C12 alkylamino, Halogenated C 1-C12 alkylamino or di (C 1-C12 alkylamino); R 5 is selected from hydrogen, halogen, cyano, nitro, C 1-C12 alkyl, halogenated C 1-C12 alkyl, C 3-C12 cycloalkyl, Halogenated C 3-C12 cycloalkyl, C 1-C12 alkoxy, halogenated C 1-C12 alkoxy, C 1-C12 alkylthio, halogenated C 1-C12 alkylthio, C 1-C12 alkylamino, C 1-C12 alkylsulfinyl, halogenated C 1-C12 alkylsulfinyl, C 1-C12 alkylsulfonyl, Halogenated C 1-C12 alkylsulfonyl, C 2-C12 alkenyl, halogenated C 2-C12 alkenyl, C 2-C12 alkynyl, halogenated C 2-C12 alkynyl, C 2-C12 alkenyloxy, halogenated C 2-C12 alkenyloxy, C 2-C12 alkynyloxy or halogenated C 2-C12 alkynyloxy; R 6 is selected from hydrogen, halogen, cyano, C 1-C12 alkyl, halo C 1-C12 alkyl, C 3-C12 cycloalkyl, halo C 3-C12 cycloalkyl, C 1-C12 alkoxy, halo C 1-C12 alkoxy, C 1-C12 alkylthio, halo C 1-C12 alkylthio, C 1-C12 alkylamino, C 1-C12 alkylsulfinyl, halo C 1-C12 alkylsulfinyl, C 1-C12 alkylsulfonyl, halo C 1-C12 alkylsulfonyl, C 2-C12 alkenyloxy, halo C 2-C12 alkenyloxy, C 2-C12 alkynyloxy or halo C 2-C12 alkynyloxy; n is selected from 0, 1, 2,3 or 4, and R 5 may be the same or different when n is greater than 1; X is selected from O or S; Y is selected from O, S or NH. Further, in the compounds of formula I: R 1 is selected from hydrogen, halogen, cyano, nitro, C 1-C6 alkyl, halogenated C 1-C6 alkyl, C 3-C6 cycloalkyl, Halogenated C 3-C6 cycloalkyl, C 1-C6 alkoxy, halogenated C 1-C6 alkoxy, C 1-C6 alkylthio, halogenated C 1-C6 alkylthio, C 1-C6 alkylamino, C 1-C6 alkylsulfinyl, halogenated C 1-C6 alkylsulfinyl, C 1-C6 alkylsulfonyl, Halogenated C 1-C6 alkylsulfonyl, C 2-C6 alkenyl, halogenated C 2-C6 alkenyl, C 2-C6 alkynyl, halogenated C 2-C6 alkynyl, c 2-C6 alkenyloxy, halogenated C 2-C6 alkenyloxy, C 2-C6 alkynyloxy or halogenated C 2-C6 alkynyloxy; R 2、R3, which may be the same or different, is selected from CR 6 or N; is positioned at the 2, 3 or 4 positions of the benzene ring; R 4 is selected from hydrogen, halogen, cyano, amino, hydroxy, mercapto, carboxyl, morpholinyl, C 1-C6 alkyl, halo C 1-C6 alkyl, cyano C 1-C6 alkyl, C 3-C6 cycloalkyl, haloC 3-C6 cycloalkyl, C 1-C6 alkoxy, haloC 1-C6 alkoxy, C 1-C6 alkylthio, Halogenated C 1-C6 alkylthio, C 2-C6 alkenyloxy, halogenated C 2-C6 alkenyloxy, C 2-C6 alkynyloxy, halogenated C 2-C6 alkynyloxy, C 1-C6 Alkylsulfinyl group halogenated C 1-C6 alkylsulfinyl radical C 1-C6 alkylsulfonyl, halogenated C 1-C6 alkylsulfonyl, C 1-C6 AlkoxyC 1-C6 alkyl, haloC 1-C6 AlkoxyC 1-C6 alkyl, C 1-C6 alkylamino, Halogenated C 1-C6 alkylamino or di (C 1-C6 alkylamino); R 5 is selected from hydrogen, halogen, cyano, nitro, C 1-C6 alkyl, halogenated C 1-C6 alkyl, C 3-C6 cycloalkyl, Halogenated C 3-C6 cycloalkyl, C 1-C6 alkoxy, halogenated C 1-C6 alkoxy, C 1-C6 a