CN113024531A

CN113024531A - Isoxazoline-containing compound, preparation method thereof, herbicidal composition and application

Info

Publication number: CN113024531A
Application number: CN202011488484.0A
Authority: CN
Inventors: 连磊; 华荣保; 彭学岗; 赵德; 崔琦
Original assignee: Qingdao Kingagroot Chemical Compound Co Ltd
Current assignee: Qingdao Kingagroot Chemical Compound Co Ltd
Priority date: 2019-12-25
Filing date: 2020-12-16
Publication date: 2021-06-25
Anticipated expiration: 2040-12-16
Also published as: CN113024531B

Abstract

The invention belongs to the technical field of pesticides, and particularly relates to an isoxazoline-containing compound, a preparation method thereof, a weeding composition and application. The compound is shown as a general formula I:

wherein Q represents

Or

X represents

Or

Description

Isoxazoline-containing compound, preparation method thereof, herbicidal composition and application

Technical Field

The invention belongs to the technical field of pesticides, and particularly relates to an isoxazoline-containing compound, a preparation method thereof, a weeding composition and application.

Background

The control of weeds is a crucial step in the realization of efficient agricultural processes, and although there are various kinds of herbicides on the market, for example, WO00/50409 and the like disclose the use of 1-aryl-4-thiotriazines of the general formula as herbicides, and CN105753853A discloses an isoxazoline uracil compound and its use as herbicides. However, the herbicidal properties of these known compounds against harmful plants and the selectivity for crop plants are not entirely satisfactory. And due to the continuous expansion of the market, the resistance of weeds, the service life of drugs, the economic efficiency of drugs and the like and the increasing attention of people to the environment, scientists are required to continuously research and develop new herbicide varieties with high efficiency, safety, economy and different action modes.

Disclosure of Invention

The invention provides an isoxazoline-containing compound, a preparation method thereof, a herbicidal composition and application thereof, wherein the compound has excellent herbicidal activity at low application rate and high selectivity to crops.

The technical scheme adopted by the invention is as follows:

an isoxazoline-containing compound is shown as a general formula I:

wherein,

q represents

X represents

Y represents halogen, haloalkyl, cyano, nitro or amino;

z represents hydrogen, halogen or hydroxy;

Q₁、Q₂、Q₃、Q₄each independently represents O or S, and Q₃、Q₄At least one is S;

m represents CH or N;

R₁、R₂each independently represents hydrogen, cyano, alkyl, alkenyl, alkynyl, formylalkyl, cyanoalkyl, amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, aminosulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, R₄R₅N-(CO)-NR₃-、

R₃-S(O)_m- (alkyl)_n-、R₃-O- (alkyl)_n-、R₃- (CO) - (alkyl)_n-、R₃-O- (alkyl)_n-(CO)-、R₃- (CO) -O- (alkyl)_n-、R₃-S- (CO) - (alkyl)_n-、R₃-O- (CO) -alkyl-or R₃-O- (CO) -O-alkyl-, wherein,

each of said "alkyl", "alkenyl" or "alkynyl" is independently unsubstituted or substituted with halogen,

said "amino", "aminoalkyl", "aminocarbonyl"Each "aminocarbonylalkyl" or "aminosulfonyl" is independently unsubstituted or selected from-R₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁-alkyl- (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁-alkyl- (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, alkyl, haloalkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O-alkyl- (CO) OR₁₄Is substituted with at least one group of (a);

R₆、R₇each independently represents hydrogen, alkyl or haloalkyl;

X₁、X₂、X₃、X₄、X₅each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, carboxyl, sulfonic acid, formyl, haloformyl, azido, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, -PO (OR')₂- (CO) O-alkyl-O-N ═ C (R')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂) OR ", (CO) O-alkyl-N (R')₂- (CO) SR ", - (CS) OR", -O (CO) OR ", - (CO) O (CO) R", - (CO) O (CO) OR ", heterocyclic group, heterocyclic alkyl, aryl, arylalkyl, amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, aminocarbonyloxyalkyl, aminothiocarbonyloxyalkyl, aminosulfonyl, aminosulfonyloxyalkyl, OR any carbon atom in the ring with-CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂CH₂-、-OCH₂CH₂-、-OCH₂O-、-OCH₂CH₂O-、-CH₂CH₂The OCO-or-CH-groups are linked to form a spiro ring, wherein,

said "alkyl", "alkenyl" OR "alkynyl" are each independently unsubstituted OR selected from halogen, cyano, hydroxy, mercapto, carboxyl, -OR ", (CO) R", -SR ", (SO)₂)R”、-O(CO)R”、-O-(SO₂) R ", - (CO) OR" OR-O (CO) OR ",

said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, alkyl, haloalkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O-alkyl- (CO) OR₁₄Is substituted with at least one group selected from the group consisting of,

said "amino", "aminoalkyl", "aminocarbonyl", "aminocarbonylalkyl", "aminocarbonyloxyalkyl", "aminothiocarbonyloxyalkyl", "aminosulfonyl" or "aminosulfonyloxyalkyl" groups are each independently unsubstituted or selected from-R₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁-alkyl- (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁-alkyl- (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

said "-CH₂CH₂CH₂-”、“-CH₂CH₂CH₂CH₂-”、“-CH₂CH₂CH₂CH₂CH₂-”、“-CH₂OCH₂-”、“-CH₂CH₂OCH₂CH₂-”、“-OCH₂CH₂-”、“-OCH₂O-”、“-OCH₂CH₂O-”、“-CH₂CH₂CO-”、“-CH₂OCO-”、“-CH₂OSO₂-”、“-CH₂CH₂OCO- "," -CH ═ CHCOO- "," -CH ═ CH- "or" -CH- "or₂CH₂OCO- "are each independently unsubstituted or substituted with halogen;

r 'independently of one another represent hydrogen, halogen, cyano, alkoxy, alkoxyalkyl, alkoxycarbonyl, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl, or- (CO) O-alkyl-O-N ═ C (R')₂Group C (R')₂Together form a cyclic structure, wherein each of said "alkyl", "alkenyl", OR "alkynyl" is independently unsubstituted OR substituted with halo, and each of said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "heterocyclyl", OR "heterocyclylalkyl" is independently unsubstituted OR substituted with a group selected from oxo, halo, cyano, nitro, alkyl, haloalkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O-alkyl- (CO) OR₁₄Is substituted with at least one group of (a);

r "each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, aryl, arylalkyl, arylalkenyl, heterocyclyl, heterocyclylalkyl, OR heterocyclylalkenyl group, wherein the" alkyl "," alkenyl ", OR" alkynyl "each independently is unsubstituted OR selected from halogen, cyano, trialkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Is substituted with at least one group selected from the group consisting of "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl",arylalkenyl "," heterocyclyl "," heterocyclylalkyl "OR" heterocyclylalkenyl "are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, alkyl, haloalkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O-alkyl- (CO) OR₁₄Is substituted with at least one group of (a);

R₃、R₄、R₅each independently represents hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, heterocyclyl, heterocyclylalkyl, aryl, OR arylalkyl, wherein the "alkyl", "alkenyl", OR "alkynyl" groups are each independently unsubstituted OR substituted with halogen, and the "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "heterocyclyl", "heterocyclylalkyl", "aryl", OR "arylalkyl" groups are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, alkyl, haloalkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O-alkyl- (CO) OR₁₄Is substituted with at least one group of (a);

R₁₁each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, phenyl, benzyl group, wherein the "alkyl", "alkenyl" or "alkynyl" groups are each independently unsubstituted or substituted with halogen, and the "phenyl" or "benzyl" groups are each independently unsubstituted or substituted with at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy, or haloalkoxy;

R₁₂each independently represents hydrogen, alkyl, alkenyl, alkynyl, alkoxy, alkylsulfonyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, or- (CO) N (R)₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents a heterocyclic group having a nitrogen atom at the 1-position;

R₁₃each independently represents an alkyl, alkenyl, alkynyl, cycloalkyl, phenyl or phenyl substituted by at least one group selected from: halogen, cyano, nitro, alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxycarbonyl, alkylthio, alkylsulfonyl or phenoxy substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxy or haloalkoxy;

R₁₄each independently represents hydrogen, alkyl, haloalkyl, phenyl or phenyl substituted by at least one group selected from halogen, cyano, nitro, alkyl, haloalkyl, alkoxycarbonyl, alkylthio, alkylsulfonyl, alkoxy or haloalkoxy;

m represents 0, 1 or 2; n represents 0 or 1.

Preferably, Y represents halogen, halogeno-C1-C8 alkyl, cyano, nitro or amino;

R₁、R₂each independently represents hydrogen, cyano, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, formyl C1-C8 alkyl, cyano C1-C8 alkyl, amino C1-C8 alkyl, aminocarbonyl C1-C8 alkyl, aminosulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl C1-C8 alkyl, aryl C1-C8 alkyl, R8 alkyl₄R₅N-(CO)-NR₃-、

R₃-S(O)_m- (C1-C8 alkyl)_n-、R₃-O- (C1-C8 alkyl)_n-、R₃- (CO) - (C1-C8 alkyl)_n-、R₃-O- (C1-C8 alkyl)_n-(CO)-、R₃- (CO) -O- (C1-C8 alkyl)_n-、R₃-S- (CO) - (C1-C8 alkyl)_n-、R₃-O- (CO) - (C1-C8 alkyl) -or R₃-O- (CO) -O- (C1-C8 alkyl) -, wherein,

the "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" each independently is unsubstituted or substituted with halogen,

the "amino", "amino C1-C8 alkyl", "aminocarbonyl C1-C8 alkyl" or "aminosulfonyl" groups are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C8 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C8 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl C1-C8 alkyl", "aryl" OR "aryl C1-C8 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C8 alkyl) - (CO) OR₁₄1-4 groups of (a);

R₆、R₇each independently represents hydrogen, C1-C8 alkyl or haloC 1-C8 alkyl;

X₁、X₂、X₃、X₄、X₅each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, carboxyl, sulfonic acid, formyl, haloformyl, azido, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, -PO (OR')₂- (CO) O- (C1-C8 alkyl) -O-N-C (R')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂) OR ", (CO) O- (C1-C8 alkyl) -N (R')₂- (CO) SR ", - (CS) OR", -O (CO) OR ", - (CO) O (CO) R", - (CO) O (CO) OR ", heterocyclic C1-C8 alkyl, aryl C1-C8 alkylAmino, amino C1-C8 alkyl, aminocarbonyl C1-C8 alkyl, aminocarbonyloxy C1-C8 alkyl, aminothiocarbonyloxy C1-C8 alkyl, aminosulfonyl, aminosulfonyloxy C1-C8 alkyl, or any carbon atom in the ring with-CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂CH₂-、-OCH₂CH₂-、-OCH₂O-、-OCH₂CH₂O-、-CH₂CH₂The OCO-or-CH-groups are linked to form a spiro ring, wherein,

said "C1-C8 alkyl", "C2-C8 alkenyl" OR "C2-C8 alkynyl" are each independently unsubstituted OR substituted with a substituent selected from the group consisting of halogen, cyano, hydroxy, mercapto, carboxyl, -OR ", (CO) R", (SR) ", - (SO)₂)R”、-O(CO)R”、-O-(SO₂) 1-4 of R ", (CO) OR" OR-O (CO) OR ",

the "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "heterocyclyl C1-C8 alkyl", "aryl" OR "aryl C1-C8 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C8 alkyl) - (CO) OR₁₄Is substituted by 1 to 4 groups of (A),

the "amino", "amino C1-C8 alkyl", "aminocarbonyl C1-C8 alkyl", "aminocarbonyloxy C1-C8 alkyl", "aminothiocarbonyloxy C1-C8 alkyl", "aminosulfonyl" or "aminosulfonyloxy C1-C8 alkyl" are each independently unsubstituted or substituted by a group selected from-R₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C8 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C8 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

r 'independently of one another represents hydrogen, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl C1-C8 alkyl, heterocyclyl or heterocyclyl C1-C8 alkyl, or- (CO) O- (C1-C8 alkyl) -O-N ═ C (R')₂Group C (R')₂And taken together to form a cyclic structure, wherein "C1-C8 alkyl", "C2-C8 alkenyl", OR "C2-C8 alkynyl", each independently, is unsubstituted OR substituted with halogen, and "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "aryl C1-C8 alkyl", "heterocyclyl", OR "heterocyclyl C1-C8 alkyl", each independently, is unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C8 alkyl) - (CO) OR₁₄1-4 groups of (a);

r' represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl, C1-C8 alkylC3-C8 cycloalkenyl, C3-C8 cycloalkenyl, C1-C8 alkyl, aryl C1-C8 alkyl, aryl C2-C8 alkenyl, heterocyclyl C1-C8 alkyl, OR heterocyclyl C2-C8 alkenyl, wherein each of said "C1-C8 alkyl", "C2-C8 alkenyl", OR "C2-C8 alkynyl" is independently unsubstituted OR selected from halogen, cyano, tri-C1-C8 alkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Wherein each of said "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "aryl C1-C8 alkyl", "aryl C2-C8 alkenyl", "heterocyclyl" C1-C8 alkyl "OR" heterocyclyl C2-C8 alkenyl "is independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C8 alkyl) - (CO) OR₁₄1-4 groups of (a);

R₃、R₄、R₅each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C8-C8 cycloalkenyl, heterocyclyl C8-C8 alkyl, aryl or aryl C8-C8 alkyl, wherein said "C8-C8 alkyl", "C8-C8 alkenyl" or "C8-C8 alkynyl" are each independently unsubstituted or substituted by halogen and said "C8-C8 cycloalkyl", "C8-C8 cycloalkyl C8-C8 alkyl", "C8-C8 cycloalkenyl", "C8-C8 alkyl", "C8-C8 aryl" or "aryl is each independently unsubstituted or substituted by a halogen, Halogen, cyano, nitro, C1-C8 alkyl, halo-substituted C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C8 alkyl) - (CO) OR₁₄1-4 groups of (a);

R₁₁each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkylC3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl, benzyl, wherein said "C1-C8 alkyl", "C2-C8 alkenyl", or "C2-C8 alkynyl", respectively, are independently unsubstituted or substituted with halogen, and said "phenyl" or "benzyl" are independently unsubstituted or substituted with 1 to 4 groups selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy, or halo C1-C8 alkoxy;

R₁₂each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C1-C8 alkoxy, C1-C8 alkylsulfonyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl or C3-C8 cycloalkenyl C1-C8 alkyl, or- (CO) N (R) N₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents a heterocyclic group having a nitrogen atom at the 1-position;

R₁₃each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, phenyl or phenyl substituted by 1-4 groups selected from: halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy, halogenated C1-C8 alkoxy, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl or phenoxy substituted by 1-4 groups selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy;

R₁₄each independently represents hydrogen, C1-C8 alkyl, halogenated C1-C8 alkyl, phenyl or phenyl substituted by 1 to 4 groups selected from halogen, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.

More preferably, Y represents halogen, halogeno-C1-C6 alkyl, cyano, nitro or amino;

R₁、R₂each independently represents hydrogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, formyl C1-C6 alkyl, cyano C1-C6 alkyl,Amino, amino C1-C6 alkyl, aminocarbonyl C1-C6 alkyl, aminosulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl C1-C6 alkyl, aryl C1-C6 alkyl, R₄R₅N-(CO)-NR₃-、

R₃-S(O)_m- (C1-C6 alkyl)_n-、R₃-O- (C1-C6 alkyl)_n-、R₃- (CO) - (C1-C6 alkyl)_n-、R₃-O- (C1-C6 alkyl)_n-(CO)-、R₃- (CO) -O- (C1-C6 alkyl)_n-、R₃-S- (CO) - (C1-C6 alkyl)_n-、R₃-O- (CO) - (C1-C6 alkyl) -or R₃-O- (CO) -O- (C1-C6 alkyl) -, wherein,

the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" each independently is unsubstituted or substituted with halogen,

the "amino", "amino C1-C6 alkyl", "aminocarbonyl C1-C6 alkyl" or "aminosulfonyl" groups are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C6 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C6 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl C1-C6 alkyl", "aryl" OR "aryl C1-C6 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C6 alkyl) - (CO) OR₁₄Substituted by 1, 2 or 3 groups of；

R₆、R₇Each independently represents hydrogen, C1-C6 alkyl or haloC 1-C6 alkyl;

X₁、X₂、X₃、X₄、X₅each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, carboxyl, sulfonic acid, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, -PO (OR')₂- (CO) O- (C1-C6 alkyl) -O-N-C (R')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂) OR ", (CO) O- (C1-C6 alkyl) -N (R')₂- (CO) SR ", - (CS) OR", -O (CO) OR ", - (CO) O (CO) R", - (CO) O (CO) OR ", heterocyclic group C1-C6 alkyl, aryl C1-C6 alkyl, amino C1-C6 alkyl, aminocarbonyl C1-C6 alkyl, aminocarbonyloxy C1-C6 alkyl, aminothiocarbonyloxy C1-C6 alkyl, aminosulfonyl, aminosulfonyloxy C1-C6 alkyl, OR a combination of any one of the carbon atoms in the ring and-CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂CH₂-、-OCH₂CH₂-、-OCH₂O-、-OCH₂CH₂O-、-CH₂CH₂The OCO-or-CH-groups are linked to form a spiro ring, wherein,

said "C1-C6 alkyl", "C2-C6 alkenyl" OR "C2-C6 alkynyl" are each independently unsubstituted OR substituted with a substituent selected from the group consisting of halogen, cyano, hydroxy, mercapto, carboxyl, -OR ", (CO) R", (SR) ", - (SO)₂)R”、-O(CO)R”、-O-(SO₂) 1, 2 OR 3 of R ", - (CO) OR" OR-O (CO) OR ",

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenylC1-C6 alkyl, heterocyclyl C1-C6 alkyl, aryl OR arylC 1-C6 alkyl are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, haloC 1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C6 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 groups of (a),

the "amino", "amino C1-C6 alkyl", "aminocarbonyl C1-C6 alkyl", "aminocarbonyloxy C1-C6 alkyl", "aminothiocarbonyloxy C1-C6 alkyl", "aminosulfonyl" or "aminosulfonyloxy C1-C6 alkyl" are each independently unsubstituted or substituted by a group selected from-R₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C6 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C6 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

r' independently represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6Alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl, C1-C6 alkyl, aryl C1-C6 alkyl, heterocyclyl, or heterocyclyl C1-C6 alkyl, or- (CO) O- (C1-C6 alkyl) -O-N ═ C (R')₂Group C (R')₂And taken together to form a cyclic structure, wherein "C1-C6 alkyl", "C2-C6 alkenyl", OR "C2-C6 alkynyl", each independently, is unsubstituted OR substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "aryl C1-C6 alkyl", "heterocyclyl", OR "heterocyclyl C1-C6 alkyl", each independently, is unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C6 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 of the groups;

r' each independently represents C1-C8 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl C1-C6 alkyl, aryl C2-C6 alkenyl, heterocyclyl C1-C6 alkyl, OR heterocyclyl C2-C6 alkenyl, wherein each of said "C1-C8 alkyl", "C2-C6 alkenyl", OR "C2-C6 alkynyl" is independently unsubstituted OR selected from halogen, cyano, tri C1-C6 alkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Wherein each of said "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "aryl C1-C6 alkyl", "aryl C2-C6 alkenyl", "heterocyclyl C1-C6 alkyl" OR "heterocyclyl C2-C6 alkenyl" is independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C6 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 of the groups;

R₃、R₄、R₅each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C6-C6 cycloalkenyl, heterocyclyl C6-C6 alkyl, aryl or aryl C6-C6 alkyl, wherein said "C6-C6 alkyl", "C6-C6 alkenyl" or "C6-C6 alkynyl" are each independently unsubstituted or substituted by halogen and said "C6-C6 cycloalkyl", "C6-C6 cycloalkyl C6-C6 alkyl", "C6-C6 cycloalkenyl", "C6-C6 alkyl", "C6-C6 aryl" or "aryl is each independently unsubstituted or substituted by a halogen, Halogen, cyano, nitro, C1-C6 alkyl, halo-substituted C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C6 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 of the groups;

R₁₁each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl, benzyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl", respectively, are independently unsubstituted or substituted with halogen, said "phenyl" or "benzyl" are each independently unsubstituted or substituted with 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo C1-C6 alkoxy;

R₁₂each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C6 alkyl, or- (CO) N (R) N₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents a heterocyclic group having a nitrogen atom at the 1-position;

R₁₃each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, phenyl or phenyl substituted by 1, 2 or 3 groups selected from: halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy, halogenated C1-C6 alkoxy, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl or phenoxy substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy;

R₁₄each independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl or phenyl substituted by 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halogenated C1-C6 alkoxy.

Further preferably, X₁、X₂、X₃、X₄、X₅Each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, carboxyl, sulfonic acid, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, -PO (OR')₂- (CO) O- (C1-C3 alkyl) -O-N-C (R')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂) OR ", (CO) O- (C1-C3 alkyl) -N (R')₂- (CO) SR ", - (CS) OR", -O (CO) OR ", - (CO) O (CO) R", - (CO) O (CO) OR ", heterocyclic group C1-C3 alkyl, aryl C1-C3 alkyl, amino C1-C3 alkyl, aminocarbonyl C1-C3 alkyl, aminocarbonyloxy C1-C3 alkyl, aminothiocarbonyloxy C1-C3 alkyl, aminosulfonyl, aminosulfonyloxy C1-C3 alkyl, OR a combination of any one of the carbon atoms in the ring and-CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂CH₂-、-OCH₂CH₂-、-OCH₂O-、-OCH₂CH₂O-、-CH₂CH₂The OCO-or-CH-groups are linked to form a spiro ring, wherein,

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "heterocyclyl C1-C3 alkyl", "aryl" OR "aryl C1-C3 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C3 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 groups of (a),

the "amino", "amino C1-C3 alkyl", "aminocarbonyl C1-C3 alkyl", "aminocarbonyloxy C1-C3 alkyl", "aminothiocarbonyloxy C1-C3 alkyl", "aminosulfonyl" or "aminosulfonyloxy C1-C3 alkyl" are each independently unsubstituted or substituted by a group selected from-R₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C3 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C3 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

r 'independently of one another represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl C1-C3 alkyl, heterocyclyl or heterocyclyl C1-C3 alkyl, or- (CO) O- (C1-C3 alkyl) -O-N ═ C (R')₂Group C (R')₂Taken together to form a 5-to 6-membered saturated carbocyclic ring, wherein "C1-C6 alkyl", "C2-C6 alkenyl" OR "C2-C6 alkynyl" are each independently unsubstituted OR substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "aryl C1-C3 alkyl", "heterocyclyl" OR "heterocyclyl C1-C3 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C3 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 of the groups;

r' each independently represents C1-C8 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl C1-C3 alkyl, aryl C2-C3 alkenyl, heterocyclyl C1-C3 alkyl, OR heterocyclyl C2-C3 alkenyl, wherein each of said "C1-C8 alkyl", "C2-C6 alkenyl", OR "C2-C6 alkynyl" is independently unsubstituted OR selected from halogen, cyano, tri C1-C6 alkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃or-O (CO) OR₁₃Wherein each of said "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "aryl C1-C3 alkyl", "aryl C2-C3 alkenyl", "heterocyclyl C1-C3 alkyl" OR "heterocyclyl C2-C3 alkenyl" is independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C3 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 of the groups;

R₃、R₄、R₅each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C3 cycloalkenyl, heterocyclyl C3-C3 alkyl, aryl or aryl C3-C3 alkyl, wherein said "C3-C3 alkyl", "C3-C3 alkenyl" or "C3-C3 alkynyl" are each independently unsubstituted or substituted by halogen and said "C3-C3 cycloalkyl", "C3-C3 cycloalkyl C3-C3 alkyl", "C3-C3 cycloalkenyl", "C3-C3 alkyl", "C3-C3 aryl" or "aryl is each independently unsubstituted or substituted by a halogen, Halogen, cyano, nitro, C1-C6 alkyl, halo-substituted C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C3 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 of the groups;

R₁₁each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, phenyl, benzyl, wherein said "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" each independently is unsubstituted or substituted by halogen, said "phenyl" or "benzyl" each independently is unsubstituted or substituted by halogen, cyano, nitro, C1-C6 alkyl, halo-C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfoAcyl, C1-C6 alkoxy or halo C1-C6 alkoxy substituted by 1, 2 or 3 groups;

R₁₂each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C1-C6 alkoxy, C1-C6 alkylsulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl or C3-C6 cycloalkenyl C1-C3 alkyl, or- (CO) N (R) N₁₂)₂Or- (SO)₂)N(R₁₂)₂Group N (R) of (1)₁₂)₂Each independently represents a heterocyclic group having a nitrogen atom at the 1-position;

Even more preferably, X represents

Y represents chlorine, bromine, halogenated C1-C6 alkyl or cyano;

z represents fluorine or chlorine;

m represents CH or N;

R₁、R₂each independently represents a C1-C6 alkyl group;

R₆、R₇each independently represents C1-C6 alkyl or halogenated C1-C6 alkyl;

X₁、X₂、X₃each independently represents hydrogen or alkyl;

X₄represents- (CO) O- (C1-C3 alkyl) -O-N ═ C (R')₂- (CO) OR ', - (CO) SR', - (CS) OR ', - (CO) O (CO) OR' OR aminocarbonyl, wherein,

said "aminocarbonyl" group being unsubstituted or selected from-R₁₁、-OR₁₁Or- (SO)₂)N(R₁₂)₂Substituted with one or two groups;

r 'independently of one another represents hydrogen, C1-C6 alkoxy, C1-C6 alkoxy, C1-C3 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkyl, C3-C6 cycloalkyl or phenyl, or- (CO) O- (C1-C3 alkyl) -O-N ═ C (R')₂Group C (R')₂Together form a 5-6 membered saturated carbocyclic ring;

r' each independently represents C1-C8 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl C1-C3 alkyl, benzyl OR heterocyclyl C1-C3 alkyl, wherein each of said "C1-C8 alkyl", "C2-C6 alkenyl" OR "C2-C6 alkynyl" is independently unsubstituted OR selected from halogen, cyano, -OR₁₃、-SR₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Said "C3-C6 cycloalkyl C1-C3 alkyl", "benzyl", or "heterocyclyl C1-C3 alkyl" are each independently unsubstituted or substituted with 1, 2 or 3 groups selected from halogen or C1-C6 alkyl, and said heterocyclyl is selected from

R₁₁Each independently represents a C1-C6 alkyl group;

R₁₂each independently represents a C1-C6 alkyl group;

R₁₃each independently represents C1-C6 alkyl or C3-C6 cycloalkyl;

still further preferably, Q represents

It is to be noted that when the formula is

When the carbon atom in (A) is a chiral centre (R configuration or S configuration is present), i.e. the substituents Q, X₁、X₂、X₃、X₄Y, Z and M are as previously defined and X₃、X₄In contrast, it is preferably in the S configuration.

In the definition of the compounds of the above general formula and in all the formulae below, the terms used, whether used alone or in compound words, represent the following substituents: alkyl groups having more than two carbon atoms may be straight chain or branched. Such as the compound word "R₃-O- (alkyl)_n"the alkyl group may be-CH₂-、-CH₂CH₂-、-CH(CH₃)-、-C(CH₃)₂-and the like. Alkyl groups are, for example, C1 alkyl-methyl; c2 alkyl-ethyl; c3 alkyl-propyl such as n-propyl or isopropyl; c4 alkyl-butyl such as n-butyl, isobutyl, tert-butyl or 2-butyl; c5 alkyl-pentyl such as n-pentyl; c6 alkyl-hexyl radicals such as the n-hexyl, isohexyl and 1, 3-dimethylbutyl radical. Similarly, alkenyl is, for example, vinyl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-3-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl. Alkynyl is, for example, ethynyl, propargyl, but-2-yn-1-yl, but-3-yn-1-yl, 1-methylbut-3-yn-1-yl. Multiple bonds may be at any position per unsaturated group. Cycloalkyl is a carbocyclic saturated ring system having, for example, three to six carbon atoms, such as cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. Similarly, cycloalkenyl is monocyclic alkenyl having, for example, three to six carbocyclic members, such as cyclopropenyl, cyclobutenyl, cyclopentenyl and cyclohexenyl, wherein the double bond can be in any position. Halogen is fluorine, chlorine, bromine or iodine.

Unless otherwise specified, the term "aryl" as used herein includes, but is not limited to, phenyl, naphthyl,

The term "heterocyclyl" includes but is not limited to saturated or unsaturated non-aromatic cyclic groups

Etc., also including, but not limited to, heteroaryl, i.e., aromatic cyclic groups containing, for example, 3 to 6 ring atoms of which 1 to 4 (e.g., 1, 2, 3, or 4) heteroatoms are selected from oxygen, nitrogen, and sulfur, and optionally also benzo ring fused, for example

If a group is substituted by a group, this is understood to mean that the group is substituted by one or more identical or different radicals selected from those mentioned. The same or different substitution characters contained in the same or different substituents are independently selected and may be the same or different. The same applies to ring systems formed from different atoms and units. Also, the scope of the claims will exclude those compounds known to those skilled in the art to be chemically unstable under standard conditions.

In addition, unless otherwise specified, groups not labeled with a specific attachment position (including heterocyclic group, aryl group, etc.) in the present invention may be attached at any position, including the position to which C or N is attached; if it is substituted, the substituents can likewise be substituted in any position, provided that the bond rules are complied with. Such as by 1Heteroaryl substituted by methyl

Can represent

And the like.

Depending on the nature of the substituents and the manner in which they are attached, the compounds of formula I and their derivatives may exist as stereoisomers. For example, enantiomers and diastereomers may occur if one or more asymmetric carbon atoms are present. Stereoisomers may be obtained from the mixtures obtained in the preparation by customary separation methods, for example by chromatographic separation methods, such as chiral HPLC resolution. Stereoisomers can likewise be prepared selectively by using stereoselective reactions and using optically active starting materials and/or auxiliaries. The invention also relates to all stereoisomers contained in formula I but not specifically defined and mixtures thereof.

The compounds of formula i of the present invention can be prepared by standard methods of organic chemistry, such as the isoxazoline-containing compounds described, comprising the steps of:

a compound of the formula II

Into compounds of the general formula I, depending on the nature of the group Q. These processes are described in particular in patents US 567979791, WO2012/041789, WO2019/101551, WO00/50409, CN105753853A and the like.

For example, when Q represents

When a compound of the formula II is reacted with

Carrying out a reaction to obtain the compound shown in the general formula IIA compound represented by the formula-1 or a compound represented by the formula II with

Carrying out a reaction to obtain a compound shown as a general formula II-2, and then carrying out a cyclization reaction on the compound shown as the general formula II-1 or II-2 and a compound shown as the general formula III-1 to obtain the compound shown as the general formula I-1, wherein the chemical reaction formula is as follows:

when Q represents

When a compound of the formula II is reacted with

Reacting to obtain the compound shown as the general formula II-2 or reacting the compound shown as the general formula II with the compound shown as the general formula II

Carrying out a reaction to obtain a compound shown as a general formula II-3, and then carrying out a cyclization reaction on the compound shown as the general formula II-2 or II-3 and a compound shown as the general formula III-2 to respectively obtain a compound shown as the general formula I-2 or I-3, wherein the chemical reaction formula is as follows:

wherein L is₁、L₂、L₃And L₄Each independently represents a C1-C6 alkyl or aryl group, preferably methyl, ethyl or phenyl; hal independently represents halogen, preferably chlorine, iodine; other substituents R₁、R₂、R₆、R₇、Q₁、Q₂、Q₃、Q₄The definitions of X, Y, Z and M are as previously described.

Preferably, both steps (1), (4) are carried out in the presence of a solvent.

Preferably, said steps (2), (3), (5) and (6) are all carried out in the presence of a base and a solvent.

The base is selected from inorganic bases (e.g. K)₂CO₃、Na₂CO₃、Cs₂CO₃、NaHCO₃、KF、CsF、KOAc、AcONa、K₃PO₄t-BuONa, EtONa, NaOH, KOH, NaOMe, etc.) or an organic base (e.g., pyrazole, triethylamine, DIEA, etc.).

The solvent is at least one selected from DMF, DMA, methanol, ethanol, acetonitrile, dichloroethane, DMSO, Dioxane, dichloromethane, toluene or ethyl acetate.

Or when Q represents

(R₆' represents R₆In which the radicals are other than hydrogen), the compounds of the formula I can be prepared directly according to the process described above, or can be prepared first in the corresponding position

With R₆' -Hal is subjected to substitution reaction to prepare a target product.

In addition, the compounds of the formula I may also be represented by the corresponding Q

The compound is used as raw material in Lawson reagent

Or by conventional sulfur substitution in the presence of phosphorus pentasulfide.

A herbicidal composition comprising a herbicidally effective amount of at least one of said isoxazoline-containing compounds, preferably further comprising formulation adjuvants.

A method of controlling weeds, comprising applying a herbicidally effective amount of at least one of said isoxazoline-containing compounds or said herbicidal composition on a plant or in a weed area.

The use of at least one of the isoxazoline-containing compounds or the herbicidal composition for controlling weeds, preferably the isoxazoline-containing compound is used for controlling weeds in crops of useful plants, which are transgenic crops or crops treated by genome editing technology.

The compounds of the formula I according to the invention have outstanding herbicidal activity against a large number of economically important monocotyledonous and dicotyledonous harmful plants. The active substances according to the invention are also effective against perennial weeds which grow from rhizomes, or other perennial organs and are difficult to control. In this connection, it is generally immaterial whether the substance is used before sowing, before germination or after germination. Mention is made in particular of representative examples of the monocotyledonous and dicotyledonous weed groups which the compounds of the invention can control, without being restricted to a defined species. Examples of weed species for which the active substance acts effectively include monocotyledons: annual avena, rye, grass, alopecurus, farris, barnyard grass, digitaria, setaria and sedge, and perennial agropyron, bermudagrass, cogongrass and sorghum, and perennial sedge.

With regard to dicotyledonous weed species, the action can be extended to species such as the annual cleavers, viola, veronica, picea, chickweed, amaranthus, sinapis, ipomoea, sida, matricaria and abutilon species, and the perennial weeds cyclocarya, thistle, sorrel and artemisia. The active substances according to the invention are effective in controlling harmful plants, such as barnyard grass, sagittaria, alisma, eleocharis, saccharum and cyperus, in this particular condition of sowing of rice. If the compounds of the present invention are applied to the soil surface before germination, seedlings of weeds can be completely prevented before the weeds grow out, or the weeds stop growing when they grow out of cotyledons and finally die completely after three to four weeks. The compounds of the invention are particularly active against plants such as, for example, alpinia, sesamum indicum, polygonum convolvulus, chickweed, veronica vinifera, veronica albo, viola tricolor and amaranth, cleavers and kochia.

Although the compounds of the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, they are not at all harmful or only insignificantly harmful to the important economic crop plants, such as wheat, barley, rye, rice, maize, sugar beet, cotton and soybean. Especially good compatibility with cereal crops such as wheat, barley and maize, especially wheat. The compounds according to the invention are therefore very suitable for selectively controlling unwanted vegetation in agricultural crops or ornamental plants.

Due to their herbicidal properties, these active substances can be used for controlling harmful plants in the cultivation of genetically engineered plants which are known or are to occur. Transgenic plants often have advantageous traits, such as resistance to specific insecticides, particularly to specific herbicides, resistance to plant diseases or to microorganisms pathogenic to plant diseases, such as specific insects or microorganisms of fungi, bacteria or viruses. Other specific traits are related to the conditions of the product, such as quantity, quality, storage stability, composition and specific ingredients. Thus, it is known that the resulting transgenic plant products have an increased starch content or an improved starch quality or a different fatty acid composition.

The compounds of the formula I according to the invention or their salts are preferably used for economically important transgenic crops and ornamentals, for example cereals, such as wheat, barley, rye, oats, millet, rice, cassava and maize, or for the cultivation of sugar beet, cotton, soybean, rapeseed, potato, tomato, pea and other vegetable plants. The compounds of the formula I are preferably used as herbicides for cultivating useful plants which are resistant to the action of the herbicide or which are resistant to the toxic action of the herbicide by genetic engineering.

Conventional methods for breeding plants having improved shape over known plants include, for example, conventional mating methods and mutant breeding. In other words, new plants with improved traits may be obtained by means of methods of genetic engineering (see, for example, EP-0221044A, EP-0131624A). For example, several methods have been described:

to improve starch synthesis in plants, crop plants are altered by genetic engineering (e.g. WO 92/11376, WO 92/14827, WO 91/19806);

transgenic crop plants which are resistant to particular herbicides, to glufosinate herbicides (e.g. EP-0242236A, EP-0242246A) or to glyphosate-type herbicides (WO 92/00377), or to sulfonylurea-type herbicides (EP-0257993A, US-5013659A);

transgenic crop plants, such as cotton, which produce Bacillus thuringiensis toxins (Bt toxins) which protect against attack on plants by specific pests (EP-0142924A, EP-0193259A);

-transgenic crop plants with improved fatty acid composition (WO 91/13972).

A number of molecular biotechnologies are known which enable the production of transgenic plants with improved traits (see, for example, Sambrook et al, 1989, molecular amplification, second edition of the laboratory Manual, Cold spring harbor laboratory publications in USA, Cold spring harbor, New York; or Winnacker "Gene und Klone" [ genes and clones ], VCH Weinheim, second edition 1996 or Christou, "trends in plant science" 1(1996)423- "431)). In order to carry out the manipulation of genetic engineering, it is possible to introduce nucleic acid molecules into plasmids, which undergo mutations or sequence changes by recombination of DNA sequences. Using standard methods as described above, it is possible, for example, to exchange substrates, remove partial sequences or add natural or synthetic sequences. In order to ligate the DNA fragments to each other, it is possible to attach a binder or a linker to the fragments.

Plant cells of reduced activity gene products can be prepared, for example, by expressing at least one suitable antisense-RNA, sense-RNA to achieve a cosuppression effect, or by expressing at least one suitably configured ribozyme which specifically cleaves transcripts of the gene products.

For this purpose, it is possible to use DNA molecules which contain the entire coding sequence of the gene product, including any flanking sequences which may be present, and to use DNA molecules which contain only a part of the coding sequence which has to be long enough to achieve an antisense effect in the cell. Sequences that are highly homologous but not identical to the coding sequence of the gene product may also be used.

When expressing the nucleic acid molecule in a plant, the synthetic protein can be localized in any desired plant cell compartment. However, for localization in a specific chamber, it is possible, for example, to link the coding region to a DNA sequence in order to ensure localization in a specific location. These sequences are known to those skilled in the art (see, for example, Braun et al, EMBO J.11(1992) 3219-3227; Wolter et al, Proc. Natl. Acad. Sci. USA 85(1988), 846-850; Sonnewald et al Plant J.1(1991), 95-106).

Transgenic plant cells can be recombined into whole plants using known techniques. The transgenic plant may be of any desired plant variety, i.e., monocotyledonous and dicotyledonous plants. In this way, it is possible to obtain transgenic plants with improved traits by overexpressing, inhibiting or suppressing homologous (═ natural) genes or gene sequences, or by expressing heterologous (═ external) genes or gene sequences.

When the active substances according to the invention are used on transgenic crops, in addition to the harmful-plant-inhibiting effects observed on other crops, special effects are often observed on the corresponding transgenic crops, for example an improved or enlarged spectrum of weed control, improved application rates in the application, preferably a good combination of resistance of the transgenic crop and herbicide performance, and an influence on the growth and yield of the transgenic crop plants. The invention therefore also provides for the use of the compounds as herbicides for controlling harmful plants in transgenic crop plants.

In addition, the compound of the invention can obviously regulate the growth of crop plants. These compounds are used to target the control of plant components and to promote harvesting, such as desiccation and stunting of plants, by regulating the metabolism of plants involved. They are also suitable for regulating and inhibiting undesirable vegetation without destroying the growth of the crop plants. Inhibiting plant growth plays a very important role in many monocotyledonous and dicotyledonous crop plants, since this reduces or completely prevents lodging.

The compounds of the present invention can be applied using general formulations, and wettable powders, concentrated emulsions, sprayable solutions, powders or granules can be used. Thus the present invention also provides herbicidal compositions comprising compounds of formula I. The compounds of formula I can be formulated in a variety of ways depending on the usual biological and/or chemical physical parameters. Examples of suitable formulation choices are: wettable Powders (WP), water Soluble Powders (SP), water soluble concentrates, Emulsion Concentrates (EC), emulsions dispersed in water (EW), for example, oil-in-water and water-in-oil (EW), sprayable solutions, Suspension Concentrates (SC), dispersible oil suspensions (OD), suspensions with oil or water as diluent, solutions of miscible oils, powders (DP), Capsule Suspensions (CS), core (cutting) compositions, granules for spreading and soil application, spray granules, coated granules and absorbent granules, water dispersible granules (WG), water Soluble Granules (SG), ULV (ultra low volume) formulations, microcapsules and wax preparations. These individual formulation types are known and described in, for example, Winnacker-Kuchler, "Chemische Techologie" [ Chemicals Process ], Vol.7, C.Hauser Verlag Munich, 4 th edition 1986; wade van Valkenburg, "Pesticide Formulations," Marcel Dekker, n.y., 1973; martens, "Spray Drying" handbook, 3 rd edition 1979, g.

The necessary formulation auxiliaries, such as inerts, surfactants, solvents and other additives, are likewise known and are described in the documents mentioned below, for example in Watkins, "handbook of powdered diluents pesticides and carriers", second edition, Darland book Caldwell n.j.; h.v.01phen, "entry to clay colloid chemistry," second edition, j.wiley and Sons, n.y.; marsden, second edition "solvent guide", Interscience, n.y.1963; "annual report of detergents and emulsifiers" by McCutcheon, MC issues, Ridgewood n.j.; sisley and Wood, "surfactant encyclopedia", chemical publishing company, n.y.1964;

is/are as follows

[ ethylene oxide adduct surfactant]Uss.verlagageell.stuttgart 1976; "Chemische technology" by Winnacker-Kuchler [ chemical Process]Volume 7, c.hauser Verlag Munich, 4 th edition 1986.

Wettable powders can be uniformly dispersed in water and, in addition to the active substance, include diluents or inert substances, ionic and nonionic surfactants (wetting agents, dispersants), such as polyethoxylated alkylphenols, polyethoxylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkylsulfonates, alkylphenylsulfonates, sodium lignosulfonates, sodium 2,2 '-dinaphthylmethane-6, 6' -disulfonate, sodium dibutylnaphthalenesulfonate or sodium oleoylmethyltaurate. To prepare wettable powders, the active substances of the herbicides are finely ground, for example using customary instruments, such as hammer mills, fan mills and jet mills, with simultaneous or sequential incorporation of the adjuvants.

Emulsions are prepared by dissolving the active substance in an organic solvent, such as butanol, cyclohexanone, dimethylformamide, xylene or higher boiling aromatics or hydrocarbons or mixtures of solvents, and adding one or more ionic and/or nonionic surfactants (emulsifiers). Examples of emulsifiers which may be used are calcium alkylarylsulfonates, for example calcium dodecylbenzenesulfonate, or nonionic emulsifiers, for example polyglycol esters of fatty acids, alkylarylpolyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters, for example sorbitan fatty acid esters, or polyoxyethylene sorbitan esters, for example polyoxyethylene sorbitan fatty acid esters.

The active substance and finely divided solid substances, for example talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth, are ground to give a powder. Water or oil based suspensions may be prepared, for example, by wet milling using a commercially available bead mill, with or without the addition of a surfactant of the other formulation type described above.

For preparing emulsions, for example oil-in-water Emulsions (EW), it is possible to use aqueous organic solvents, using stirrers, colloid mills and/or static mixers, and, if desired, to add surfactants of another formulation type as described above.

Granules are prepared by spraying the active substance onto the adsorbate, granulating with inert material, or concentrating the active substance onto the surface of a carrier, for example sand, kaolinite, and granulating the inert material with a binder, for example polyvinyl alcohol, sodium polyacrylate or mineral oil. Suitable active substances can be granulated by the process for preparing fertilizer granules, if desired mixed with fertilizers. The preparation of water-suspendable granules is carried out by customary methods, for example spray-drying, fluidized-bed granulation, millstone granulation, mixing using high-speed mixers and extrusion without solid inert materials.

For the preparation of granules using a millstone, a fluidized bed, an extruder and Spray coating, see the following processes, for example "Spray Drying handbook", third edition 1979, g.goodwin ltd, london; browning, "Agglomeration", chemical and engineering 1967, page 147 ff; "Perry's handbook of Engineers of chemistry", fifth edition, McGraw-Hill, New York 1973, pages 8-57. If preparations for crop protection products are to be known, see, for example, G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, New York, pages 196181-96 and J.D. Freyer, S.A. Evans, "Weed Control Manual", fifth edition, Blackwell Scientific rules, Oxford university 1968, page 101-.

Agrochemical formulations generally comprise from 0.1 to 99%, in particular from 0.1 to 95% by weight of active substance of formula I. The concentration of active substance in wettable powders is, for example, from about 10 to 99% by weight, with usual formulation components making up the remainder to 100% by weight. The concentration of the active substance in the emulsion concentrate may be about 1 to 90%, preferably 5 to 80% by weight. Powder formulations contain from 1 to 30% by weight of active, usually preferably from 5 to 20% by weight of active, whereas sprayable solutions contain from about 0.05 to 80%, preferably from 2 to 50% by weight of active. The content of active substance in the aqueous suspension granules depends primarily on whether the active substance is liquid or solid, and the auxiliaries, fillers and the like used in granulation. The content of active substance in the water-suspendable granule formulation is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.

The active substance formulations mentioned may additionally comprise tackifiers, wetting agents, dispersants, emulsifiers, penetrants, preservatives, antifreezes, solvents, fillers, carriers, colorants, antifoams, evaporation inhibitors and generally customary pH and viscosity regulators in all cases.

On the basis of these formulations, it is also possible to mix them with other insecticide active substances, such as insecticides, acaricides, herbicides and fungicides, and also with safeners, fertilizers and/or plant growth regulators, either premixed or mixed in containers.

Suitable active substances which can be mixed with the active substances according to the invention in a compounded or tank-mixed formulation are, for example, the substances known from "the world Wide Specification of New agricultural chemical products", from the national agricultural science and technology Press, 2010.9 and the documents cited therein. For example, the herbicidal active substances mentioned below may be mixed with the mixtures of the formula I (remarks: name of the compound, either by common name according to the International organization for standardization (ISO), or by chemical name, where appropriate with a code number): acetochlor, butachlor, alachlor, propisochlor, metolachlor, s-metolachlor, pretilachlor, propyzamide, pretilachlor, napropamide, R-levulinyl-propyzamide, propanil, mefenacet, dibenzamide, diflufenican, flumetsulam, bromobutyrolac, dimethenamid, mefenacet, metazachlor, isoxaflutole, ryegrass methyl ester, loflutolane, diacrylamide, pethoxamide, butachlor, propisochlor, cyprosulfamide, flumetsulam, heptanoyl, isobutramine, propyzamide, terbutamid, dimethenamid, larvamide, trimethylcyclam, clofenamid, propyzamide, penoxulamide, carpronide, diflormid, trinitrol, butachlor, butafenacet, butachlor, benfluralin, bencarbzamide, pencyhalonil, metolachlor, bencarbzamide, pencyhalonil, buta, Grazing amine, bensulfuron, quinoxalamine, bensulfuron-methyl, naproxen, acetochlor, naphazel, thiachlor, pyraflufen, bensulfuron-methyl, prochloraz, clofenamide, butamidam, flupiram, atrazine, simazine, prometryn, cyanazine, simetryn, ametryn, prometryn, ipratron, flurazin, terbutryn, triazineone-flumetsulam, ciprofloxacin, glycazine, pradapazine, prometryn, simatong, azidezin, diuron, isopentetryn, cycloprozine, ametryn, terbuthylazine, terbuton, metocloprid, cyanazine, bentazon, clonazine, atrazine, metribuzin, cyanuric acid, indaziflazaflam, chlorsulfuron, meturon, bensulfuron, chlorimuron, tribenuron-methyl, thifensulfuron-methyl, pyrazosulfuron-methyl, sulfosulfuron-methyl, sulfometuron, Cinosulfuron, triasulfuron, sulfometuron-methyl, nicosulfuron, ethametsulfuron, amidosulfuron, ethoxysulfuron, cyclosulfamuron, rimsulfuron, azimsulfuron, primisulfuron-methyl, flusulfuron-methyl, flupyrsulfuron-methyl, epoxysulfuron, imazosulfuron, primisulfuron-methyl, prosulfuron, sulfosulfuron, trifloxysulfuron, triflusulfuron, metsulfuron-methyl sodium, flupyrazosulfuron, methisulfuron-methyl, primisulfuron, propysilfuron (Propyrisulfuron), metribusulfuron, acifluorfen-methyl, fomesafen, lactofen, fluoroglycofen-ethyl, oxyfen, prosulfuron, benfuresafen, trifloxysulfuron, metofen-ethyl, metofen, trifloxysulfuron, fluroxypyr, fluridone, benfop, benfluridone, benfurazolin, benfluridone, benfurbenflur, Dimethofen, oxyfluorfen, clofenflurate, Halosafen, chlortoluron, isoproturon, linuron, diuron, sifenuron, fluometuron, benzthiauron, methabenzuron, prosulfuron, sulfosulfuron, clomauron, clodinafuron, clofensulfuron, metoxuron, bromuron, metoxuron, meturon, fensulfuron, prosulfuron, subtilon, cuarone, metolachlor, cycloaroron, cyclouron, thifluuron, buthiuron, kuron, cumuron, metoxuron, methamidothion, metominosulfuron, trifolium, isoxafluron, isoxauron, moneuronon, aniron, methicuron, chloretron, clotururon, teuron, benuron, pennison, phenmedibensulfuron, bensulfuron, benazolin, propham, buthan, thiuron, buthan, benazolin, buthan, benazolin, buthan, benazol, Thiobencarb, merthiolane, diclofop, triallate, penoxsulam, pyributicarb, dichlorfon, edifenphos, ethiofen, prosulfocarb, clenbuterol, prosulfocarb, dichotomene, thiobencarb, promethazine, Isopolinate, Methiobencarb, 2, 4-d butyl ester, 2 methyl 4-sodium chloride, 2, 4-d isooctyl ester, 2 methyl 4-chloroisooctyl ester, 2, 4-d sodium salt, 2, 4-d dimethylamine salt, 2 methyl 4-chloroethyl thioester, 2 methyl 4 chloride, 2, 4-d propionic acid, 2, 4-d propionate, 2, 4-d butyric acid, 2 methyl 4-chloropropionic acid, 2 methyl 4-chlorobutyric acid, 2,4, 5-d nasal discharge, 2,4, 5-d propionic acid, 2,4, 5-d butyric acid, 2 methyl 4-chloropropionic acid, 2 methyl 4-d propionic acid, 2-d propionic acid, 2-cloroprionic acid, triclocarb, triclopyr, triclop, Aminodiclofenac, metocloprofenac, diclofop-methyl, fluazifop-p-butyl, haloxyfop-methyl, haloxyfop-p-butyl, quizalofop-ethyl, quizalofop-p-ethyl, fenoxaprop-p-ethyl, propaquizafop-ethyl, fenoxaprop-ethyl, clodinafop-ethyl, benazolin, clodinafop-ethyl, haloxyfop-methyl, benazolin, propalaxyl, butyfen-ethyl, chloroethafloxacin, aminofluanid, benazolin, dichlofop-ethyl, methamphetalin, propamocarb-ethyl, benfop-methyl, thiophosphine, pirimiphos-methyl, benfop-ethyl, benazolin, benfop-methyl, imax-methyl, mefenofos, mefeno, Imazamox ammonium salt, imazapic acid, imazamethabenz ester, fluroxypyr, clopyralid, picloram, triclopyr, dithiopyr, haloxydine, triclopyril, thiazopyr, fluridone, aminopyralid, diflufenzopyr, butoxyethyl triclopyr, Clodinate, sethoxydim, clethodim, cycloxydim, clethodim, topramezone, Buthidazole, metribuzin, hexazinone, metamitron, metribuzin, amitridione, Amibuzin, bromoxynil, octanoyl ioxynil, dichlobenitrile, pyraclonil, hydroxybensulam, Iodobonil, flumetsulam, penoxsulam, clofenapyr, pyraclonil, pyraflufen-ethyl, pyraoxystrobin, flumetsulam, pyraclonil, pyraoxystrobin, isoxathion, pyriftalid, pyriminobac-methyl, pyrithiobac-methyl, benzobicylon, mesotrione, sulcotrione, Tembotrione, Tefuryltrione, Bicyclopyrone, ketodradox, isoxaflutole, isoxaclomazone, fenoxasulfofone, methiozoline, isopyrafen, pyraflufen, pyrazote, difenzoquat, pyrazoxazole, pyroxaflutole, pyroxsulam, pyraclofos, pyraclonil, amicarbazone, carfentrazone, flumiclone, sulfentrazone, bencarane, bisphenomezone, butafenacil, isoxaflutole, cyclam, triclopyr, fluroxypyr, flumethazine, parnaprox, flumiclone, flumethol, carfentrazone, carzone, carfentrazone, car, Fluazifop-methyl, pyriminostrobin, bromopicrin, didaphylm, pyridaben, Pyridafol, quinclorac, chloroquine, bentazon, pyridate, oxaziclomefone, benazolin, clomazone, isoprox, isoproxypyrim, propyribac, cumylfen, clomazone, sodium chlorate, thatch, trichloroacetic acid, monochloroacetic acid, hexachloroacetone, tetrafluoropropionic acid, mequat, bromophenol oxime, triazasulam, imazazole, flurtamone, mesotrione, ethofumesate, pyrimethanil, clodinafop-methyl, clodinium, pyributaine, benfurazolin, meton, metamitron, metolachlor, dichlorvofen, triclopyr, aloac, Dietmquat, Etpronil, ipriflam, iprimazam, iprodione, Trizopyr, Thiaclonifen, chlorpyrifos, pyradifquat, chlorpyrifos, propiram, pyradifurone, pyradifon, pyradifurone, pyrazone, thion, pyrazone, clomazone, fenclorim, cloquintocet-mexyl, mefenpyr-diethyl, DOWFAUC, UBH-509, D489, LS 82-556, KPP-300, NC-324, NC-330, KH-218, DPX-N8189, SC-0744, DOWCO535, DK-8910, V-53482, PP-600, MBH-001, KIH-9201, ET-751, KIH-6127 and KIH-2023.

When used, the commercially available formulations are diluted in the usual manner, if desired, for example in wettable powders, concentrated emulsions, suspensions and granules suspended in water, using water. Powders, granules for soil application or solutions for spreading and spraying generally do not require further dilution with inert substances before use. The required amount of the compound of formula I to be used varies with the external conditions, such as temperature, humidity, the nature of the herbicide used, etc. It can vary to a large extent, for example between 0.001 and 1.0kg a.i./ha, or more active substance, but preferably between 0.005 and 750g a.i./ha, in particular between 0.005 and 250g a.i./ha.

Detailed Description

The following examples are intended to illustrate the invention and should not be construed as limiting it in any way. The scope of the invention is indicated by the appended claims.

In view of the economic and diversity of the compounds, we prefer to synthesize some of the compounds, selected ones of which are listed in tables 1-2 below. Specific compound structures and corresponding compound information are shown in tables 1-2. The compounds in tables 1-2 are only for better illustration of the present invention, but do not limit the present invention, and it should not be understood to limit the scope of the above-mentioned subject matter of the present invention to the following compounds for those skilled in the art.

Table 1 Structure of Compounds and methods of use thereof¹H NMR data

Table 2 structures of compounds and methods of making the same¹H NMR data

Several methods for preparing the compounds of the present invention are illustrated in the schemes and examples below. The starting materials are commercially available or can be prepared by methods known in the literature or as shown in detail. It will be appreciated by those skilled in the art that other synthetic routes may also be utilized to synthesize the compounds of the present invention. Although specific starting materials and conditions for the synthetic route are described below, they can be readily substituted with other similar starting materials and conditions, and variations or modifications of the preparation process of the present invention, such as various isomers of the compounds, are included in the scope of the present invention. In addition, the preparation methods described below may be further modified in accordance with the present disclosure using conventional chemical methods well known to those skilled in the art. For example, protecting the appropriate groups during the reaction, and the like.

The following process examples are provided to facilitate a further understanding of the methods of preparation of the present invention, and the particular materials, species and conditions used are intended to be further illustrative of the invention and are not intended to limit the reasonable scope thereof. The reagents used in the synthesis of the compounds indicated in the following table are either commercially available or can be readily prepared by one of ordinary skill in the art.

Examples of representative compounds are given below, and the synthesis of other compounds is similar and will not be described in detail herein.

1. Synthesis of Compound 67

1) 67-1(20g,98.3mmol,1.0eq) was added to 200 ml of EtOH, and then NH was added dropwise to the reaction at 0 deg.C₂Aqueous OH HCl (7.5g,108.1mmol,1.1eq) (30 ml). After the dropwise addition, the reaction solution was stirred at 0 ℃ for 3 hours, and LCMS detection showed that the raw material was almost completely consumed and a main new peak was generated. The reaction mixture was concentrated to remove a portion of ethanol, poured into 100ml of water, and a solid precipitated, filtered, and the filter cake was washed with water and dried to give 67-2(20g, 93% yield) (white solid).

2) 67-2(20g,91.5mmol,1.0eq) was added to 150 ml of DMF, and then NCS (13.4g,100.7mmol,1.1eq) was slowly added to the reaction mixture at 35 ℃. After the addition, the reaction was stirred at 35 ℃ for 1.5 hours and the reaction was essentially complete by LCMS. The reaction was poured into 100ml of HCl (1M) and extracted with dichloromethane, the organic phase was washed with saturated brine (100ml x 3), and the organic phase was concentrated to give crude 67-3(26g, crude) (yellow oil) which was directly put to the next step.

3) 67-3(26g), Et was added to 200 mL of DCM₃N (15.6g,154.1mmol,1.5eq), then 67-4(14.1g,123.3mmol,1.2eq) was added to the reaction at 0 ℃. The reaction was run at 0 ℃ for 1 hour before LCMS detection of product. To the reaction was added 100ml of water, extracted with dichloromethane (100ml x 3), the organic phase was dried over anhydrous sodium sulfate, concentrated and the crude product was purified by column chromatography to give 67-5(17g, 50% yield) (yellow solid).

4) To 200 ml of EtOH were added 67-5(17g,51.4mmol,1.0eq), Fe powder (8.6g,154.2mmol,3eq), and NH in that order₄Cl (5.5g,102.8mmol,2eq) and water (50 ml). Then the reaction solution reacts for 2 hours at the temperature of 80 ℃, and the LCMS detects that the raw materials disappear, and the main peak is the product peak. The reaction mixture was filtered through celite, concentrated to remove ethanol, and then water (100ml) was added, followed by extraction with ethyl acetate and concentration to obtain a black crude product. The crude product was purified by column chromatography to give 67-6(12g, 77.6% yield) (yellow solid).

5) 67-6(0.6g,2.0mmol,1.0eq), compound 67-7(0.46g,2.6mmol,1.3eq) and triethylamine (0.4g,4mmol,2eq) were added to 10ml of toluene and reacted at room temperature for 0.5 hour. LCMS detects that the raw materials are basically reacted completely, and the main peak is the product. The solvent was concentrated and the crude product was isolated by column chromatography to give 67-8(0.6g, 88% yield) (white solid).

6) A (0.48g,2.1mmol,1.5eq) and AcONa (58mg,0.7mmol,0.5eq) were added to 10ml of DMF, and then 67-8(0.48g,1.4mmol,1.0eq) was added to the reaction mixture at 60 ℃ and the mixture was reacted at 60 ℃ for 5 min. LCMS detected product. Water (10ml) was added to the reaction mixture and extracted with ethyl acetate, the organic phase was washed with saturated brine (20ml x 1), and the crude product was isolated by column chromatography after concentration of the organic phase to give 67(0.4g, 60% yield) (white solid).

2. Synthesis of Compounds 1-43 and 1-45

Raw material b (320mg, 0.67mmol, 1.0eq) was dissolved in toluene (4mL) and Lawesson's Reagent (1.35g, 3.35mmol, 5.0eq) was added and the mixture was heated to 140 ℃ in a sealed tube for 24 h. After completion of the reaction, it was cooled to room temperature and the product was checked by LCMS. EA (60mL) was added, the organic phase was washed with water (2X30mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure to remove the solvent, and the remaining portion was stirred with silica gel to give products 1-43(140mg, yellow oil, Yield: 42%) and 1-45(20mg, yellow oil, Yield: 6%).

Evaluation of biological Activity:

the activity level criteria for plant disruption (i.e. growth control rate) are as follows:

and 5, stage: the growth control rate is more than 85 percent;

4, level: the growth control rate is more than or equal to 60 percent and less than 85 percent;

and 3, level: the growth control rate is more than or equal to 40% and less than 60%;

and 2, stage: the growth control rate is more than or equal to 20% and less than 40%;

level 1: the growth control rate is more than or equal to 5% and less than 20%;

level 0: the growth control rate is less than 5%.

The growth control rate is the fresh weight control rate.

Post-emergence test experiments:

monocotyledonous and dicotyledonous weed seeds (descurainia sophia, shepherd's purse, Abutilon, Galium aparine, chickweed, Trigonella foenum-graecum, alopecurus alopecuroides, alopecurus quinata, beckmoth, devil's-claw, Conyza canadensis, Veronica officinalis, bromus, Arthron wheat, Phalaris canadensis, Amaranthus retroflexus, Chenopodium quinoa, Commelina communis, endive, Convolvulus arvensis, Epilobium spiniferum, Solanum nigrum, Acalyphaeocharum, Uncaria, Echinochloa, Japanese raisin, Raphanus sativus, Setaria viridis, Euphorbia japonica, Commelina, Iphigenia indica, Cyperus rotundus, Setaria indica, Setaria sibirica, Setaria pallidus, Pharbitidis) as well as major seeds (wheat, maize, rice, soybean, cotton, rape, millet, sorghum, potato, sesame, castor bean) are placed in a plastic pots, and then covered with 0.2, the compound of the invention to be tested is dissolved by acetone, and then tween 80 is added, and 1.5 l/ha missible oil of methyl oleate is used as a synergist, diluted into solution with certain concentration by certain water, and sprayed on plants by a spray tower. The effect of the experiment on weeds was counted after 3 weeks of cultivation in the greenhouse after application, with the compounds used in amounts of 500, 250, 125, 60, 15, 7.5g a.i./ha, repeated three times and the mean value was taken. Representative data are presented in table 3.

TABLE 3 post-emergence weed test

Note: control compound a:

pre-emergence test experiment:

placing the monocotyledon and dicotyledon weed seeds and main crop seeds (wheat, corn, rice, soybean, cotton, rape, millet and sorghum) in a plastic pot filled with soil, then covering the plastic pot with 0.5-2 cm of soil, respectively dissolving the compound of the invention to be tested by acetone, then adding Tween 80, diluting the solution into solution with a certain concentration by using a certain amount of water, and immediately spraying the solution after sowing. The results of experiments observed after 4 weeks of cultivation in a greenhouse after application show that most of the agents of the invention have superior effects under the measurement of 250g of a.i./ha, especially on weeds such as cockspur grass, crab grass, abutilon and the like, and many of the compounds have good selectivity on corn, wheat, rice and soybean.

Meanwhile, main weed tests in wheat fields and paddy fields show that the compound generally has a good weed control effect, and particularly, the compound has extremely high activity on broadleaf weeds and nutgrass flatsedge which have resistance to ALS inhibitors and are contained in wild arrowheads, Chinese iris, abnormal-shaped nutgrass flatsedge, descurainia sophia, shepherd's purse, maidenhair, cleavers, cyperus rotundus and the like.

Evaluating the safety of transplanted rice and the weed control effect of paddy field:

after the paddy field soil was filled in a tank of 1/1,000,000 hectare, seeds of barnyard grass, japanese iris, and bidens were sown, and soil was lightly covered thereon. Standing in a state of water storage depth of 0.5-1 cm in a greenhouse, and implanting tuber of Pseudobulbus Cremastrae seu pleiones in the next or 2 days. Thereafter, the water storage depth was maintained at 3 to 4 cm, and an aqueous dilution of a wettable powder or a suspension, which was prepared by a usual formulation method, was dropped uniformly by a pipette at a time point when barnyard grass, japanese iris, or burley reached 0.5 leaf and the bulb reached the primary leaf stage to obtain a predetermined amount of active ingredient.

In addition, after filling the 1/1,000,000 hectare pot with paddy field soil, leveling is carried out to ensure that the water storage depth is 3-4 cm, and the rice (japonica rice) at the 3-leaf stage is transplanted with the transplanting depth of 3 cm on the next day. The compound of the present invention was treated on the 5 th day after transplantation in the same manner as described above.

The growth state of cockspur grass, japanese iris, bidens tripartita and edible tulip on day 14 after the treatment with the chemical agent and the growth state of rice on day 21 after the treatment with the chemical agent were respectively observed by naked eyes, and the effects were evaluated on the above activity standard levels, and many compounds showed excellent activity and selectivity.

Note: the barnyard grass, the Chinese iris, the bidens tripartita seeds and the edible tulip are all collected from Heilongjiang in China, and have the drug resistance to pyrazosulfuron-ethyl with the conventional dosage through detection.

Meanwhile, a plurality of tests show that the compound and the composition thereof have good selectivity on gramineous lawns such as zoysia japonica, bermuda grass, festuca arundinacea, bluegrass, ryegrass, seashore paspalum and the like, and can prevent and kill a plurality of key gramineous weeds and broadleaf weeds. Tests on sugarcane, soybean, cotton, sunflower, potato, fruit trees, vegetables and the like under different application modes also show excellent selectivity and commercial value.

Claims

1. An isoxazoline-containing compound is shown as a general formula I:

wherein,

q represents

X represents

Y represents halogen, haloalkyl, cyano, nitro or amino;

z represents hydrogen, halogen or hydroxy;

m represents CH or N;

said "amino", "aminoalkyl", "aminocarbonyl", "aminocarbonylalkyl" or "aminosulfonyl" are each independently unsubstituted or selected from-R₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁-alkyl- (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁-alkyl- (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

R₆、R₇each independently represents hydrogen, alkyl or haloalkyl;

X₁、X₂、X₃、X₄、X₅each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, carboxyl, sulfonic acid, formyl, haloformyl, azido, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, cycloalkenyl, cycloalkenylalkyl, -PO (OR')₂- (CO) O-alkyl-O-N ═ C (R')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂) OR ", (CO) O-alkyl-N (R')₂、-(CO)SR”- (CS) OR ', -O (CO) OR', - (CO) O (CO) R ', - (CO) O (CO) OR', heterocyclyl, heterocyclylalkyl, aryl, arylalkyl, amino, aminoalkyl, aminocarbonyl, aminocarbonylalkyl, aminocarbonyloxyalkyl, aminothiocarbonyloxyalkyl, aminosulfonyl, aminosulfonyloxyalkyl, OR any carbon atom in the ring with-CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂CH₂-、-OCH₂CH₂-、-OCH₂O-、-OCH₂CH₂O-、-CH₂CH₂The OCO-or-CH-groups are linked to form a spiro ring, wherein,

r "each independently represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylalkyl group, a cycloalkenyl group, a cycloalkenylalkyl group, an aryl group, an arylalkyl group, an arylalkenyl group, a heterocyclic alkyl group, or a heterocyclic alkenyl group, wherein the" alkyl group "," alkenyl group ", or" alkynyl group "each independently represents an alkyl group, an alkenyl group, an alkynyl group, a cycloalkyl group, a cycloalkylalkyl groupIndependently unsubstituted OR selected from halogen, cyano, trialkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Each of said "cycloalkyl", "cycloalkylalkyl", "cycloalkenyl", "cycloalkenylalkyl", "aryl", "arylalkyl", "arylalkenyl", "heterocyclyl", "heterocyclylalkyl", OR "heterocyclylalkenyl", independently, is unsubstituted OR selected from oxo, halogen, cyano, nitro, alkyl, haloalkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O-alkyl- (CO) OR₁₄Is substituted with at least one group of (a);

m represents 0, 1 or 2; n represents 0 or 1.

2. The isoxazoline-containing compound according to claim 1, wherein the isoxazoline-containing compound is a compound having a structure represented by formula (I),

y represents halogen, halogeno-C1-C8 alkyl, cyano, nitro or amino;

X₁、X₂、X₃、X₄、X₅each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, sulfydryl, carboxyl, sulfonic acid group, formyl, haloformyl, azido, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, -PO (OR')₂- (CO) O- (C1-C8 alkyl) -O-N-C (R')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂) OR ", (CO) O- (C1-C8 alkyl) -N (R')₂- (CO) SR ", - (CS) OR", -O (CO) OR ", - (CO) O (CO) R", - (CO) O (CO) OR ", heterocyclic group C1-C8 alkyl, aryl C1-C8 alkyl, amino C1-C8 alkyl, aminocarbonyl C1-C8 alkyl, aminocarbonyloxy C1-C8 alkyl, aminothiocarbonyloxy C1-C8 alkyl, aminosulfonyl, aminosulfonyloxy C1-C8 alkyl, OR a combination of any one of the carbon atoms in the ring and-CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂CH₂-、-OCH₂CH₂-、-OCH₂O-、-OCH₂CH₂O-、-CH₂CH₂The OCO-or-CH-groups are linked to form a spiro ring, wherein,

the "amino group", "amino C1-C8 alkyl group" -"aminocarbonyl", "aminocarbonyl C1-C8 alkyl", "aminocarbonyloxy C1-C8 alkyl", "aminothiocarbonyloxy C1-C8 alkyl", "aminosulfonyl" or "aminosulfonyloxy C1-C8 alkyl" are each independently unsubstituted or selected from the group consisting of-R₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C8 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C8 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

r 'independently of one another represents hydrogen, halogen, cyano, C1-C8 alkoxy, C1-C8 alkoxy C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl C1-C8 alkyl, heterocyclyl or heterocyclyl C1-C8 alkyl, or- (CO) O- (C1-C8 alkyl) -O-N ═ C (R')₂Group C (R')₂Together form a cyclic structure, wherein "C1-C8 alkyl", "C2-C8 alkenyl" or "C2-C8 alkynyl" are each independently unsubstituted or substituted with halogen, and "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl"The "aryl", "aryl C1-C8 alkyl", "heterocyclyl" OR "heterocyclyl C1-C8 alkyl" are each independently unsubstituted OR substituted by a group selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C8 alkyl) - (CO) OR₁₄1-4 groups of (a);

r' each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, aryl C1-C8 alkyl, aryl C2-C8 alkenyl, heterocyclyl C1-C8 alkyl, OR heterocyclyl C2-C8 alkenyl, wherein each of said "C1-C8 alkyl", "C2-C8 alkenyl", OR "C2-C8 alkynyl" is independently unsubstituted OR selected from halogen, cyano, tri C1-C8 alkylsilyl, -OR₁₃、-SR₁₃、-O(CO)R₁₃、-(CO)R₁₃、-(CO)OR₁₃OR-O (CO) OR₁₃Wherein each of said "C3-C8 cycloalkyl", "C3-C8 cycloalkyl C1-C8 alkyl", "C3-C8 cycloalkenyl", "C3-C8 cycloalkenyl C1-C8 alkyl", "aryl C1-C8 alkyl", "aryl C2-C8 alkenyl", "heterocyclyl" C1-C8 alkyl "OR" heterocyclyl C2-C8 alkenyl "is independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C8 alkyl) - (CO) OR₁₄1-4 groups of (a);

R₃、R₄、R₅each independently represents hydrogen, C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, heterocyclyl C1-C8 alkyl, aryl, or aryl C1-C8 alkyl, wherein said "C1-C8 alkyl", "C8-C8 alkenyl" or "C8-C8 alkynyl" are each independently unsubstituted or substituted by halogen, said "C8-C8 cycloalkyl", "C8-C8 cycloalkyl C8-C8 alkyl", "C8-C8 cycloalkenyl", "C8-C8C1-C8 alkyl, heterocyclyl C1-C8 alkyl, aryl OR arylC 1-C8 alkyl are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C8 alkyl, haloC 1-C8 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C8 alkyl) - (CO) OR₁₄1-4 groups of (a);

R₁₁each independently represents C1-C8 alkyl, C2-C8 alkenyl, C2-C8 alkynyl, C3-C8 cycloalkyl, C3-C8 cycloalkyl C1-C8 alkyl, C3-C8 cycloalkenyl, C3-C8 cycloalkenyl C1-C8 alkyl, phenyl, benzyl, wherein the "C1-C8 alkyl", "C2-C8 alkenyl", or "C2-C8 alkynyl", respectively, are independently unsubstituted or substituted with halogen, each of said "phenyl" or "benzyl" is independently unsubstituted or substituted with 1 to 4 groups selected from halogen, cyano, nitro, C1-C8 alkyl, halo C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halo C1-C8 alkoxy;

R₁₄each independently represents hydrogen, C1-C8 alkyl, halogeno-C1-C8 alkyl, phenyl or a halogen selected from halogenPhenyl substituted by 1-4 groups of elements, cyano, nitro, C1-C8 alkyl, halogenated C1-C8 alkyl, C1-C8 alkoxycarbonyl, C1-C8 alkylthio, C1-C8 alkylsulfonyl, C1-C8 alkoxy or halogenated C1-C8 alkoxy.

3. The isoxazoline-containing compound according to claim 1 or 2, which is characterized in that,

y represents halogen, halogeno-C1-C6 alkyl, cyano, nitro or amino;

R₁、R₂each independently represents hydrogen, cyano, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, formyl C1-C6 alkyl, cyano C1-C6 alkyl, amino C1-C6 alkyl, aminocarbonyl C1-C6 alkyl, aminosulfonyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, heterocyclyl C1-C6 alkyl, aryl C1-C6 alkyl, R6 alkyl₄R₅N-(CO)-NR₃-、

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl C1-C6 alkyl", "aryl" OR "aryl C1-C6 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C6 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 of the groups;

the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "heterocyclyl C1-C6 alkyl", "aryl" OR "aryl C1-C6 alkyl" are each independently unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C6 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 groups of (a),

r 'independently of one another represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, aryl C1-C6 alkyl, heterocyclyl or heterocyclyl C1-C6 alkyl, or- (CO) O- (C1-C6 alkyl) -O-N ═ C (R')₂Group C (R')₂And taken together to form a cyclic structure, wherein "C1-C6 alkyl", "C2-C6 alkenyl", OR "C2-C6 alkynyl", each independently, is unsubstituted OR substituted with halogen, and "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C6 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C6 alkyl", "aryl C1-C6 alkyl", "heterocyclyl", OR "heterocyclyl C1-C6 alkyl", each independently, is unsubstituted OR selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C6 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 of the groups;

R₁₁independently represent C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C6 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C6 alkyl, phenyl, benzyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" independently represent unsubstituted or substituted by halogen, and the "phenyl" or "benzyl" independently represent unsubstituted or substituted by halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo-C1-C6 alkoxy;

4. The isoxazoline-containing compound according to any one of claims 1 to 3, wherein the isoxazoline-containing compound is a compound having a structure represented by formula (I),

X₁、X₂、X₃、X₄、X₅each independently represents hydrogen, halogen, nitro, cyano, thiocyanato, hydroxyl, mercapto, carboxyl, sulfonic acid, formyl, haloformyl, azido, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, -PO (OR')₂- (CO) O- (C1-C3 alkyl) -O-N-C (R')₂、-OR”、-(CO)R”、-SR”、-(SO)R”、-(SO₂)R”、-Si(R”)₃、-O(CO)R”、-O-(SO₂)R”、-S(CO)R”、-(SO₂) OR ", (CO) O- (C1-C3 alkyl) -N (R')₂- (CO) SR ", - (CS) OR", -O (CO) OR ", - (CO) O (CO) R", - (CO) O (CO) OR ", heterocyclic group C1-C3 alkyl, aryl C1-C3 alkyl, amino C1-C3 alkyl, aminocarbonyl C1-C3 alkyl, aminocarbonyloxy C1-C3 alkyl, aminothiocarbonyloxy C1-C3 alkyl, aminosulfonyl, aminosulfonyloxy C1-C3 alkyl, OR a combination of any one of the carbon atoms in the ring and-CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂-、-CH₂CH₂CH₂CH₂CH₂-、-OCH₂CH₂-、-OCH₂O-、-OCH₂CH₂O-、-CH₂CH₂The OCO-or-CH-groups are linked to form a spiro ring, wherein,

the "amino", "amino C1-C3 alkyl", "aminocarbonyl C1-C3 alkyl", "aminocarbonyloxy C1-C3 alkyl", "aminothiocarbonyloxy C1-C3 alkyl", "aminosulfonyl" or "ammoniaThe alkylsulfonyloxy radicals C1-C3 alkyl "are each independently unsubstituted or selected from the group consisting of₁₁、-OR₁₁、-(CO)R₁₁、-(CO)OR₁₁- (C1-C3 alkyl) - (CO) OR₁₁、-(SO₂)R₁₁、-(SO₂)OR₁₁- (C1-C3 alkyl) - (SO)₂)R₁₁、-(CO)N(R₁₂)₂Or- (SO)₂)N(R₁₂)₂Substituted with one or two of the groups in (a),

r 'independently of one another represents hydrogen, halogen, cyano, C1-C6 alkoxy, C1-C6 alkoxy C1-C3 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, aryl C1-C3 alkyl, heterocyclyl or heterocyclyl C1-C3 alkyl, or- (CO) O- (C1-C3 alkyl) -O-N ═ C (R')₂Group C (R')₂Taken together to form a 5-to 6-membered saturated carbocyclic ring, wherein "C1-C6 alkyl", "C2-C6 alkenyl" or "C2-C6 alkynyl" are each independently unsubstituted or substituted with halo, and "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "aryl C1-C3 alkyl", "heterocyclyl" or "heterocyclyl C1-C3 alkyl" are each independently unsubstituted or selected from oxo, halo, cyano, nitro,Nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C3 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 of the groups;

R₃、R₄、R₅each independently represents hydrogen, C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, heterocyclyl C1-C3 alkyl, aryl or aryl C1-C3 alkyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl", respectively, are independently unsubstituted or substituted with halogen, the "C3-C6 cycloalkyl", "C3-C6 cycloalkyl C1-C3 alkyl", "C3-C6 cycloalkenyl", "C3-C6 cycloalkenyl C1-C3 alkyl", "heterocyclyl C1-C3 alkyl", "aryl" or "aryl C1-C3 alkyl" are each independently unsubstituted or substituted.Selected from oxo, halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, -OR₁₄、-SR₁₄、-(CO)OR₁₄、-(SO₂)R₁₄OR-O- (C1-C3 alkyl) - (CO) OR₁₄Substituted with 1, 2 or 3 of the groups;

R₁₁each independently represents C1-C6 alkyl, C2-C6 alkenyl, C2-C6 alkynyl, C3-C6 cycloalkyl, C3-C6 cycloalkyl C1-C3 alkyl, C3-C6 cycloalkenyl, C3-C6 cycloalkenyl C1-C3 alkyl, phenyl, benzyl, wherein the "C1-C6 alkyl", "C2-C6 alkenyl", or "C2-C6 alkynyl", respectively, are independently unsubstituted or substituted with halogen, said "phenyl" or "benzyl" are each independently unsubstituted or substituted with 1, 2 or 3 groups selected from halogen, cyano, nitro, C1-C6 alkyl, halo C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonyl, C1-C6 alkoxy or halo C1-C6 alkoxy;

R₁₄each independently represents hydrogen, C1-C6 alkyl, halogenated C1-C6 alkyl, phenyl or a group selected from halogen, cyano, nitro, C1-C6 alkyl, halogenated C1-C6 alkyl, C1-C6 alkoxycarbonyl, C1-C6 alkylthio, C1-C6 alkylsulfonicPhenyl substituted by 1, 2 or 3 of acyl, C1-C6 alkoxy or halo C1-C6 alkoxy;

preferably, it is selected from any one of tables 1-2.

5. The isoxazoline-containing compound according to any one of claims 1 to 4, wherein the isoxazoline-containing compound is a compound having a structure represented by formula (I),

x represents

Y represents chlorine, bromine, halogenated C1-C6 alkyl or cyano;

z represents fluorine or chlorine;

m represents CH or N;

R₁、R₂each independently represents a C1-C6 alkyl group;

X₁、X₂、X₃each independently represents hydrogen or alkyl;

R₁₁Each independently represents a C1-C6 alkyl group;

R₁₂each independently represents a C1-C6 alkyl group;

R₁₃each independently represents C1-C6 alkyl or C3-C6 cycloalkyl;

preferably, Q represents

6. An S configuration compound shown as a general formula I',

wherein each substituent Q, X₁、X₂、X₃、X₄Y, Z and M are as defined in any one of claims 1 to 5 and X₃、X₄Are not identical.

7. A method for preparing the isoxazoline-containing compound according to any one of claims 1 to 6, comprising the steps of:

a compound of the formula II

The conversion to compounds of the general formula I, the substituents X, Y, Z, M and Q being as defined in claims 1 to 6.

8. A herbicidal composition comprising a herbicidally effective amount of at least one of the isoxazoline-containing compounds according to any one of claims 1 to 6, preferably further comprising formulation adjuvants.

9. A method for controlling weeds, which comprises applying a herbicidally effective amount of at least one of the isoxazoline-containing compounds according to any one of claims 1 to 6 or the herbicidal composition according to claim 8 to a plant or a weed area.

10. Use of at least one of the isoxazoline-containing compounds according to any one of claims 1 to 6 or the herbicidal composition according to claim 8 for controlling weeds, preferably in crops of useful plants, which are transgenic or treated with genome editing techniques.