CN112624989A - Amide compound and application thereof - Google Patents

Amide compound and application thereof Download PDF

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CN112624989A
CN112624989A CN201910950931.0A CN201910950931A CN112624989A CN 112624989 A CN112624989 A CN 112624989A CN 201910950931 A CN201910950931 A CN 201910950931A CN 112624989 A CN112624989 A CN 112624989A
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radical
alkyl
alkoxy
cycloalkyl
haloalkyl
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CN112624989B (en
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杨辉斌
英君伍
马宏娟
秦博
商璐
孙冰
王刚
陈霖
王明欣
梁爽
张帆
李斌
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Jiangsu Yangnong Chemical Co Ltd
Shenyang Sinochem Agrochemicals R&D Co Ltd
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D257/00—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms
    • C07D257/02—Heterocyclic compounds containing rings having four nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D257/04—Five-membered rings
    • C07D257/06—Five-membered rings with nitrogen atoms directly attached to the ring carbon atom
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D249/14—Nitrogen atoms
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    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/08—1,2,5-Oxadiazoles; Hydrogenated 1,2,5-oxadiazoles
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    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
    • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
    • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
    • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D285/00—Heterocyclic compounds containing rings having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by groups C07D275/00 - C07D283/00
    • C07D285/01—Five-membered rings
    • C07D285/02—Thiadiazoles; Hydrogenated thiadiazoles
    • C07D285/04—Thiadiazoles; Hydrogenated thiadiazoles not condensed with other rings
    • C07D285/12—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles
    • C07D285/125—1,3,4-Thiadiazoles; Hydrogenated 1,3,4-thiadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
    • C07D285/135—Nitrogen atoms
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    • C07—ORGANIC CHEMISTRY
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    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Abstract

The invention discloses an amide compound and application thereof, wherein the compound is shown as a general formula (I):

Description

Amide compound and application thereof
Technical Field
The invention belongs to the field of herbicides. In particular to an amide compound and application thereof.
Background
Due to succession and transition of weed populations and generation and rapid development of chemical pesticide resistance, people continuously strengthen the awareness of ecological environment protection, and continuously increase the attention to chemical pesticide pollution, understanding of the influence of pesticides on non-target organisms and problems of lodging in the pesticide ecological environment. With the diminishing area of cultivated land in the world, the increasing population and the increasing demand for food, people are forced to rapidly develop agricultural production techniques, improve the complete cultivation system, and need to continuously invent novel and improved herbicidal compounds and compositions.
CN108290846A reports that some diamide compounds have herbicidal activity.
The tetra-amide compounds according to the invention are not disclosed.
Disclosure of Invention
The invention aims to provide a tetra-amide compound which is novel in structure and safe to crops and an application thereof.
In order to achieve the purpose, the technical scheme of the invention is as follows:
an amide compound is shown as a general formula I:
Figure BDA0002225631000000011
in the formula:
X1、X2、X3、X4each independently selected from cyano, nitro, halogen, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyl oxy, C2-C6Alkenyl radical, C2-C6Alkynyl, or phenyl unsubstituted or substituted with 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 heteroatoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl or halophenyl;
W1selected from N or CX5；
W2Selected from N or CX6；
X5、X6Each independently selected from hydrogen, cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Thio radical, Y1Y2Amino group, Y1Sulfoxide group, Y1Sulfone group, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Y2Amino group C1-C6Alkyl radical, Y1Sulfoxide group C1-C6Alkyl radical, Y1Sulfone group C1-C6Alkyl, COY1、COOY1、OCOOY1、NY1COOY2、C(O)NY1Y2、NY1C(O)NY1Y2、OC(O)N Y1Y2、C(O)N(Y1)OY2、NY1SO2Y2、NY1COY2、OSO2Y1、CH＝NOY1、C1-C6alkyl-CH-NOY1、C1-C6alkyl-O-N-C Y1Y2Or phenyl which is unsubstituted or substituted by 1 to 5 substituents, a 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms, a 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 heteroatoms, a 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Y1、Y2each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C1-C6Alkoxy radical C1-C6Alkyl, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Q1、Q2each independently selected from the following:
Figure BDA0002225631000000021
R1、R2、R3each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl or halophenyl;
R4、R5、R6each independently selected from hydrogen, halogen, cyano, nitro, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyloxy, phenyl or halophenyl;
l is selected from the following:
Figure BDA0002225631000000022
R7、R9each independently selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl or C2-C6Alkynyl C1-C6An alkyl group;
R8is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl radical, C2-C6Alkynyl C1-C6Alkyl or, optionally phenyl which is unsubstituted or substituted by 1 to 5 substituents selected from the group consisting of halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C2-C6Alkenyl or C2-C6An alkynyl group;
m1、m2n is independently selected from 0-10;
Z1、Z2each independently selected from the group consisting of a bond, CH2O, S or NH;
agriculturally acceptable salts of the compounds of formula I.
The preferred compounds, of formula I:
X1、X2、X3、X4each independently selected from cyano, nitro, halogen, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radicalRadical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyl oxy, C2-C6Alkenyl radical, C2-C6Alkynyl, or phenyl unsubstituted or substituted with 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 heteroatoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl or halophenyl;
W1selected from N or CX5；
W2Selected from N or CX6；
X5、X6Each independently selected from hydrogen, cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Thio radical, Y1Y2Amino group, Y1Sulfoxide group, Y1Sulfone group, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Y2Amino group C1-C6Alkyl radical, Y1Sulfoxide group C1-C6Alkyl radical, Y1Sulfone group C1-C6Alkyl, COY1、COOY1、OCOOY1、CH＝NOY1、C1-C6alkyl-CH-NOY1、C1-C6alkyl-O-N-C Y1Y2Or phenyl which is unsubstituted or substituted by 1 to 5 substituents, a 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms, a 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 heteroatoms, a 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Y1、Y2each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C1-C6Alkoxy radical C1-C6Alkyl, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Q1、Q2each independently selected from the following:
Figure BDA0002225631000000031
R1、R2、R3each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C2-C6Alkenyl or C2-C6An alkynyl group;
R4、R5、R6each independently selected from hydrogen, halogen, cyano, nitro, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyloxy, phenyl or halophenyl;
l is selected from the following:
Figure BDA0002225631000000032
R7、R9each independently selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl or C2-C6Alkynyl C1-C6An alkyl group;
R8is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl radical, C2-C6Alkynyl C1-C6Alkyl or phenyl, or phenyl unsubstituted or substituted by 1 to 5 substituents selected from halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C2-C6Alkenyl or C2-C6An alkynyl group;
m1、m2n is independently selected from 0-10;
Z1、Z2each independently selected from the group consisting of a bond, CH2O, S or NH;
hydrochloride, sulfate, acetate or phosphate of the compound shown in the general formula I.
The further preferred compounds, of formula I:
X1、X2、X3、X4each independently selected from cyano, halogen, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyloxy, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl or halophenyl;
W1selected from N or CX5；
W2Selected from N or CX6；
X5、X6Each independently selected from hydrogen, cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Thio radical, Y1Y2Amino group, Y1Sulfone group, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Y2Amino group C1-C6Alkyl radical, Y1Sulfone group C1-C6Alkyl, COY1、COOY1Unsubstituted or substituted by 1 to 5Phenyl substituted by the substituent, 5-7 membered aliphatic heterocyclic ring containing 1-4 hetero atoms, 5-7 membered aromatic heterocyclic ring containing 1-4 hetero atoms, 5-7 membered aliphatic heterocyclic ring containing 1-4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Y1、Y2each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C1-C6Alkoxy radical C1-C6Alkyl, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl or C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Q1、Q2each independently selected from the following:
Figure BDA0002225631000000041
R1、R3each independently selected from C1-C6Alkyl radical, C1-C3Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C2-C6Alkenyl or C2-C6An alkynyl group;
R4、R5each independently selected from hydrogen, halogen, cyano, nitro, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyloxy, phenyl or halophenyl;
l is selected from the following:
Figure BDA0002225631000000051
R7、R9each independently selected from C1-C6Alkyl radical, C1-C6Haloalkyl or C1-C6Alkoxy radical C1-C6An alkane;
R8is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl radical, C2-C6Alkynyl C1-C6Alkyl or phenyl, or phenyl unsubstituted or substituted by 1 to 5 substituents selected from halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C2-C6Alkenyl or C2-C6An alkynyl group;
m1、m2n is independently selected from 0-10;
Z1、Z2each independently selected from the group consisting of a bond, CH2O, S or NH.
In a further preferred compound, formula I:
X1、X2、X3、X4each independently selected from halogen, C1-C3Alkylsulfonyl radical, C1-C3Haloalkylsulfonyl group, C1-C3Alkyl radical, C1-C3Haloalkyl, C1-C3Alkoxy radical, C1-C3Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C3Alkoxy radical C1-C3Alkoxy radical, C1-C3Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyloxy, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C3Alkyl radical, C1-C3Haloalkyl, C1-C3Alkoxy radical, C1-C3Haloalkoxy, C3-C6Cycloalkyl or C3-C6A cycloalkoxy group;
W1selected from N or CX5；
W2Selected from N or CX6；
X5、X6Each independently selected from hydrogen, halogen, C1-C3Alkyl radical, C1-C3Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, Y1Oxy radical, Y1Sulfone group, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Y2Amino group C1-C6Alkyl radical, Y1Sulfone group C1-C6Alkyl, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl or C3-C6A cycloalkoxy group;
Y1、Y2each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C1-C6Alkoxy radical C1-C6Alkyl, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl or C3-C6A cycloalkoxy group;
Q1、Q2each independently selected from the following:
Figure BDA0002225631000000061
R1、R3each independently selected from C1-C6Alkyl radical, C1-C3Haloalkyl or C3-C6A cycloalkyl group;
R4、R5each independently selected from halogen, C1-C6Alkyl radical, C1-C3Haloalkyl or C3-C6A cycloalkyl group;
l is selected from the following:
Figure BDA0002225631000000062
R7、R9each independently selected from C1-C6Alkyl radical, C1-C6Haloalkyl or C1-C6Alkoxy radical C1-C6An alkane;
R8is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl radical, C2-C6Alkynyl C1-C6Alkyl or phenyl; the hydrogen on the phenyl ring may be substituted by one or more substituents selected from halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C2-C6Alkenyl or C2-C6An alkynyl group;
m1、m2n is independently selected from 0-8;
Z1、Z2each independently selected from the group consisting of a bond, CH2O, S or NH.
In the definitions of the compounds of the general formula I given above, the terms used are collectively defined as follows:
alkyl means straight or branched chain forms, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, isopentyl, n-hexyl and the like. Cycloalkyl is meant to include cyclic chain forms such as cyclopropyl, methylcyclopropyl, cyclopropylcyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and the like. Alkoxy means a group having an oxygen atom attached to the terminal of an alkyl group, such as methoxy, ethoxy, n-propoxy, isopropoxy, t-butoxy, and the like. The 5-7 membered aliphatic heterocyclic ring containing 1-4 hetero atoms means a 5-7 membered heterocyclic compound containing 1-4 hetero atoms and having no aromatic character, such as ethylene oxide, tetrahydrofuran, imidazolidinone, caprolactam, etc. The 5-7 membered aromatic heterocyclic ring containing 1-4 hetero atoms refers to a 5-7 membered heterocyclic compound containing 1-4 hetero atoms and having aromatic characteristics, such as furan, thiophene, pyrazole, pyridine and the like.
The compound I with the general formula can be prepared by the following method:
Figure BDA0002225631000000063
the compound of the general formula II and the compound of the general formula III react in a proper solvent at the temperature of-10 ℃ to the boiling point of the proper solvent for 0.5 to 48 hours to prepare the target compound I.
Suitable solvents are selected from dichloromethane, 1, 2-dichloroethane, chloroform, carbon tetrachloride, hexane, benzene, toluene, ethyl acetate, acetonitrile, acetic acid, tetrahydrofuran, dioxane, N-dimethylformamide or dimethyl sulfoxide, and the like.
The addition of suitable alkali substances in the reaction system can be beneficial to the reaction. Suitable bases are selected from organic bases such as triethylamine, N-dimethylaniline or pyridine, etc., or inorganic bases such as sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, sodium methoxide, sodium tert-butoxide or potassium tert-butoxide, etc.
The compounds of the formula IV are commercially available or can be prepared from the corresponding acids.
The preparation of the compounds of formula II is as follows:
Figure BDA0002225631000000071
reacting a compound of formula V (commercially available) with a compound of formula VI (commercially available) in a suitable base and a suitable solvent with a suitable activating agent at a temperature of-10 ℃ to the boiling point of the suitable solvent for 0.5 to 48 hours to produce a compound of formula II; suitable solvents are selected from petroleum ether, hexane, benzene, toluene, chlorobenzene, ethyl acetate, acetonitrile, tetrahydrofuran, N-dimethylformamide, dimethyl sulfoxide, pyridine, 2-methylpyridine, 3-methylpyridine or 4-methylpyridine, and the like. Suitable activators are selected from phosgene, triphosgene, CDI, DCC, thionyl chloride, oxalyl chloride, phosphorus oxychloride or phosphorus pentachloride, among others. Suitable bases are selected from N-methylimidazole, DMAP, or the like.
The preparation method of the compound in the general formula III is the same as that of the compound in the general formula II.
The compound of the general formula I and the salt thereof have herbicidal activity and can be used for preventing and controlling various weeds in agriculture. Compared with the compounds disclosed in the prior art, the benzamide compound disclosed by the invention not only has excellent herbicidal activity, but also is safe to crops.
The invention also comprises a weeding composition taking the compound shown in the general formula I and the salt thereof as active components. The weight percentage of the active components in the weeding composition is 1-99%. The herbicidal composition also includes an agriculturally acceptable carrier.
The herbicidal compositions of the present invention can be applied in the form of various formulations. The compounds of the present invention are typically formulated to be more easily dispersed for use as herbicides by dissolving or dispersing the compounds in a carrier. For example: the chemical preparation can be prepared into wettable powder or missible oil and the like. Thus, in these compositions, at least one liquid or solid carrier is added, and it is generally necessary to add a suitable surfactant.
The present invention also provides an implementation method for controlling weeds, which comprises applying a herbicidally effective amount of the herbicidal composition of the present invention to the weeds or to the locus where the weeds grow or to the surface of a growth medium thereof. Preferably, the effective dose is from 1 to 1000 grams per hectare, preferably from 10 to 500 grams per hectare. For certain applications, one or more additional herbicides may be added to the herbicidal compositions of the present invention, thereby providing additional advantages and benefits.
The compounds of the present invention can be used alone or in combination with other known insecticides, fungicides, plant growth regulators or fertilizers.
It should be understood that various changes and modifications may be made within the scope of the present invention as defined by the claims.
The invention has the advantages that:
compared with the known benzamide compounds, the compound of the general formula contains two different benzoyl substitutions, has a novel structure, has unexpected high herbicidal activity, has high herbicidal activity under a lower dosage, is high in efficiency, reduces the using amount of pesticides, reduces the cost and reduces the pollution to the environment.
Detailed Description
The following examples and biological test results are provided to further illustrate the invention and are not meant to limit the invention.
Synthesis examples
Example 1, synthesis of compounds 1-21:
(1) synthesis of N- (1-methyl-tetrazole-5-yl) -2-chloro-3-methoxymethyl-4-methylsulfonyl benzamide
Figure BDA0002225631000000081
To a reaction flask were added 2-chloro-3-methoxymethyl-4-methylsulfonylbenzoic acid (4 g, 14.3 mmol), 1-methyl-5-amino-tetrazole (1.7 g, 17.24 mmol), and N-methylimidazole (2.4 g, 28.7 mmol), and 20ml of 3-methylpyridine was added and stirred at room temperature for 30 minutes. After gradually cooling to 0 ℃, thionyl chloride (2.73 g, 23 mmol) was slowly added dropwise and stirred at room temperature for 24 hours. The reaction mixture was acidified by adding concentrated hydrochloric acid, extracted 2 times with ethyl acetate (100 ml. times.2), the combined organic phases were washed with saturated brine (50 ml), dried over anhydrous magnesium sulfate, the solvent was evaporated off under reduced pressure, and the residue was separated by column chromatography to give 1.2 g of a white solid with a yield of 23%.
(2) Synthesis of Compounds 1 to 21
Figure BDA0002225631000000082
N- (1-methyl-tetrazol-5-yl) -2-chloro-3-methoxymethyl-4-methylsulfonylbenzamide (0.6 g, 1.7 mmol), dichloromethane (10 ml), and triethylamine (0.34 g, 3.3 mmol) were added to a reaction flask, and then cooled to 10 ℃ in an ice bath, adipoyl chloride (0.76 g, 4.2 mmol) was added dropwise to the reaction flask, and reacted at room temperature for 30 minutes. The reaction mixture was subjected to column chromatography directly to give 0.27 g of a white solid with a purity of 83% and a yield of 16%.
Example 2, synthesis of compounds 1-70:
Figure BDA0002225631000000083
n- (1-methyl-tetrazol-5-yl) -2-chloro-3-methoxymethyl-4-methylsulfonylbenzamide (0.6 g, 1.7 mmol), dichloromethane (10 ml), and triethylamine (0.34 g, 3.3 mmol) were added to a reaction flask, and cooled to 10 ℃ in an ice bath, and azelaic acid chloride (0.94 g, 4.2 mmol) was dropwise added to the reaction flask and reacted at room temperature for 30 minutes. The reaction mixture was subjected to column chromatography directly to give 0.45 g of a white solid with a purity of 87% and a yield of 31%.
According to the description of the preparation method, the compound shown in the general formula I can be obtained after raw materials are replaced in the reaction process,the compounds are shown in table 1, table 2 and table 3; wherein, in the compounds of the general formula I shown in Table 1, W1Is CX5、W2Is CX6(ii) a In the compounds of the general formula I, W is shown in Table 21、W2Is N; in Table 3, W is shown as1Is CX5、W2Is N. A compound of the general formula I, wherein W1Is CX5、W2Is CX6。
Figure BDA0002225631000000091
Table 1 structural and physical properties of some compounds of formula I
Figure BDA0002225631000000092
Figure BDA0002225631000000101
Figure BDA0002225631000000111
Figure BDA0002225631000000121
Figure BDA0002225631000000131
Figure BDA0002225631000000141
Figure BDA0002225631000000151
Figure BDA0002225631000000161
Figure BDA0002225631000000171
Figure BDA0002225631000000181
Figure BDA0002225631000000191
Figure BDA0002225631000000201
Figure BDA0002225631000000211
Figure BDA0002225631000000221
Figure BDA0002225631000000231
A compound of the general formula I, wherein W1、W2Is N.
Figure BDA0002225631000000241
Table 2 structural and physical properties of part of compounds of formula I
Figure BDA0002225631000000242
Figure BDA0002225631000000251
Figure BDA0002225631000000261
Figure BDA0002225631000000271
Figure BDA0002225631000000281
Figure BDA0002225631000000291
Figure BDA0002225631000000301
Figure BDA0002225631000000311
Figure BDA0002225631000000321
A compound of the general formula I, wherein W1Is CX5、W2Is N.
Figure BDA0002225631000000322
Table 3 structural and physical properties of part of compounds of formula I
Figure BDA0002225631000000323
Figure BDA0002225631000000331
Figure BDA0002225631000000341
Figure BDA0002225631000000351
Figure BDA0002225631000000361
Figure BDA0002225631000000371
Figure BDA0002225631000000381
Figure BDA0002225631000000391
Figure BDA0002225631000000401
Figure BDA0002225631000000411
Figure BDA0002225631000000421
Figure BDA0002225631000000431
Figure BDA0002225631000000441
Figure BDA0002225631000000451
Figure BDA0002225631000000461
Figure BDA0002225631000000471
Of partial compounds1H NMR(600MHz,DMSO-d6) The data are as follows:
compounds 1-21: 8.05(d,2H),7.89(d,2H),4.92(s,4H),4.09(s,6H),3.37(s,6H),3.34(s,6H),2.65(s,4H),1.49(s, 4H).
Compounds 1-70: 10(d,2H),7.56(d,2H),5.02(s,4H),4.00(s,6H),3.45(s,6H),3.22(s,6H),2.2.55(t,4H),1.57(m,4H),1.24(m, 6H).
Examples of bioassay
Example 3 determination of herbicidal Activity
Sowing seeds of broad-leaved weeds (zinnia elegans and abutilon) or grassy weeds (green bristlegrass and barnyard grass) in a paper cup with the diameter of 7cm and containing nutrient soil, covering soil for 1cm after sowing, compacting, spraying water, culturing in a greenhouse according to a conventional method, and spraying stems and leaves after 2-3 leaf periods of the weeds.
After the original drug is dissolved by acetone, the solution to be tested with the required concentration is prepared by using 1 per mill of Tween 80 to stand tap water according to the test requirements. The dosage is designed according to the experiment inSpraying treatment (spraying pressure 1.95 kg/cm) was carried out on a crawler-type crop sprayer (Engineer Research Ltd. design, UK)2The amount of the liquid spray is 500L/hm2And the track speed is 1.48 km/h). The experiment was repeated 3 times. After being treated, the test material is placed in an operation hall, after the liquid medicine is naturally dried in the shade, the test material is placed in a greenhouse for management according to a conventional method, the reaction condition of weeds to the agent is observed and recorded, the weed control effect of the test agent to weeds is regularly observed and visually observed after the treatment, the weed control effect is expressed by 0-100%, and the weed control effect is expressed by 0% to 100%, and the weed control effect is expressed by 100%.
Test results show that the compound of the general formula I has higher control effect on broad leaf weeds and grassy weeds generally. Some of the compounds tested, e.g., compounds 1-21, 1-70, were administered at a dose of 600g a.i./hm2The composition has better prevention effect on zinnia elegans, piemarker, green bristlegrass herb and cockspur grass, and the prevention effect is more than 90 percent.
The compound with the general formula has herbicidal activity and can be used for controlling various weeds in agriculture. Meanwhile, the amide compound disclosed by the invention has excellent herbicidal activity and is safe to crops.

Claims (7)

1. An amide compound characterized in that: the compound is shown as a general formula I:
Figure FDA0002225630990000011
in the formula:
X1、X2、X3、X4each independently selected from cyano, nitro, halogen, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyl oxy, C2-C6Alkenyl radical, C2-C6Alkynyl, or phenyl unsubstituted or substituted with 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 heteroatoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl or halophenyl;
W1selected from N or CX5；
W2Selected from N or CX6；
X5、X6Each independently selected from hydrogen, cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Thio radical, Y1Y2Amino group, Y1Sulfoxide group, Y1Sulfone group, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Y2Amino group C1-C6Alkyl radical, Y1Sulfoxide group C1-C6Alkyl radical, Y1Sulfone group C1-C6Alkyl, COY1、COOY1、OCOOY1、NY1COOY2、C(O)NY1Y2、NY1C(O)NY1Y2、OC(O)N Y1Y2、C(O)N(Y1)OY2、NY1SO2Y2、NY1COY2、OSO2Y1、CH＝NOY1、C1-C6alkyl-CH-NOY1、C1-C6alkyl-O-N-C Y1Y2Or phenyl which is unsubstituted or substituted by 1 to 5 substituents, a 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms, a 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 heteroatoms, a 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Y1、Y2each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C1-C6Alkoxy radical C1-C6Alkyl, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6HalogenatedAlkyl radical, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Q1、Q2each independently selected from the following:
Figure FDA0002225630990000021
R1、R2、R3each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl or halophenyl;
R4、R5、R6each independently selected from hydrogen, halogen, cyano, nitro, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radicalBase, C3-C6Cycloalkyloxy, phenyl or halophenyl;
l is selected from the following:
Figure FDA0002225630990000022
R7、R9each independently selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl or C2-C6Alkynyl C1-C6An alkyl group;
R8is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl radical, C2-C6Alkynyl C1-C6Alkyl or, optionally phenyl which is unsubstituted or substituted by 1 to 5 substituents selected from the group consisting of halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C2-C6Alkenyl or C2-C6An alkynyl group;
m1、m2n is independently selected from 0-10;
Z1、Z2each independently selected from the group consisting of a bond, CH2O, S or NH;
agriculturally acceptable salts of the compounds of formula I.
2. A compound according to claim 1, wherein in formula I:
X1、X2、X3、X4each independently selected from cyanogenRadical, nitro radical, halogen, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyl oxy, C2-C6Alkenyl radical, C2-C6Alkynyl, or phenyl unsubstituted or substituted with 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 heteroatoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl or halophenyl;
W1selected from N or CX5；
W2Selected from N or CX6；
X5、X6Each independently selected from hydrogen, cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Thio radical, Y1Y2Amino group, Y1Sulfoxide group, Y1Sulfone group, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Y2Amino group C1-C6Alkyl radical, Y1Sulfoxide group C1-C6Alkyl radical, Y1Sulfone group C1-C6Alkyl, COY1、COOY1、OCOOY1、CH＝NOY1、C1-C6alkyl-CH-NOY1、C1-C6alkyl-O-N-C Y1Y2Or phenyl which is unsubstituted or substituted by 1 to 5 substituents, a 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms, a 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 heteroatoms, a 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 heteroatoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Y1、Y2each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C1-C6Alkoxy radical C1-C6Alkyl, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl radicals or containing 15-7 membered heteroaromatic ring C of 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Q1、Q2each independently selected from the following:
Figure FDA0002225630990000031
R1、R2、R3each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C2-C6Alkenyl or C2-C6An alkynyl group;
R4、R5、R6each independently selected from hydrogen, halogen, cyano, nitro, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyloxy, phenyl or halophenyl;
l is selected from the following:
Figure FDA0002225630990000032
R7、R9each independently selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl or C2-C6Alkynyl C1-C6An alkyl group;
R8is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl radical, C2-C6Alkynyl C1-C6Alkyl or phenyl, or phenyl unsubstituted or substituted by 1 to 5 substituents selected from halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C2-C6Alkenyl or C2-C6An alkynyl group;
m1、m2n is independently selected from 0-10;
Z1、Z2each independently selected from the group consisting of a bond, CH2O, S or NH;
hydrochloride, sulfate, acetate or phosphate of the compound shown in the general formula I.
3. A compound according to claim 2, wherein in formula I:
X1、X2、X3、X4each independently selected from cyano, halogen, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyloxy, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl or halophenyl;
W1selected from N or CX5；
W2Selected from N or CX6；
X5、X6Each independently selected from hydrogen, cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Thio radical, Y1Y2Amino group, Y1Sulfone group, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Y2Amino group C1-C6Alkyl radical, Y1Sulfone group C1-C6Alkyl, COY1、COOY1Phenyl unsubstituted or substituted by 1 to 5 substituents, a 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, a 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, a 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl radical, C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Y1、Y2each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C1-C6Alkoxy radical C1-C6Alkyl, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6HalogenatedAlkoxy radical, C3-C6Cycloalkyl or C3-C6Cycloalkoxy, C2-C6Alkenyl radical, C2-C6Alkynyl, phenyl and halophenyl;
Q1、Q2each independently selected from the following:
Figure FDA0002225630990000041
R1、R3each independently selected from C1-C6Alkyl radical, C1-C3Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C2-C6Alkenyl or C2-C6An alkynyl group;
R4、R5each independently selected from hydrogen, halogen, cyano, nitro, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyloxy, phenyl or halophenyl;
l is selected from the following:
Figure FDA0002225630990000051
R7、R9each independently selected from C1-C6Alkyl radical, C1-C6Haloalkyl or C1-C6Alkoxy radical C1-C6An alkane;
R8is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl radical, C2-C6Alkynyl C1-C6Alkyl or phenyl, or phenyl unsubstituted or substituted by 1 to 5 substituents selected from halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C2-C6Alkenyl or C2-C6An alkynyl group;
m1、m2n is independently selected from 0-10;
Z1、Z2each independently selected from the group consisting of a bond, CH2O, S or NH.
4. A compound according to claim 3, wherein in formula I:
X1、X2、X3、X4each independently selected from halogen, C1-C3Alkylsulfonyl radical, C1-C3Haloalkylsulfonyl group, C1-C3Alkyl radical, C1-C3Haloalkyl, C1-C3Alkoxy radical, C1-C3Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C3Alkoxy radical C1-C3Alkoxy radical, C1-C3Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Cycloalkyl radical C1-C3Alkoxy radical, C3-C6Cycloalkyloxy, or unsubstituted or substituted by 1 to 5Phenyl, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C3Alkyl radical, C1-C3Haloalkyl, C1-C3Alkoxy radical, C1-C3Haloalkoxy, C3-C6Cycloalkyl or C3-C6A cycloalkoxy group;
W1selected from N or CX5；
W2Selected from N or CX6；
X5、X6Each independently selected from hydrogen, halogen, C1-C3Alkyl radical, C1-C3Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, Y1Oxy radical, Y1Sulfone group, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Y2Amino group C1-C6Alkyl radical, Y1Sulfone group C1-C6Alkyl, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl or C3-C6A cycloalkoxy group;
Y1、Y2each independently selected from hydrogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C1-C6Alkoxy radical C1-C6Alkyl, or phenyl unsubstituted or substituted by 1 to 5 substituents, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aromatic heterocyclic ring containing 1 to 4 hetero atoms, 5-to 7-membered aliphatic heterocyclic ring containing 1 to 4 hetero atoms C1-C6Alkyl or 5-to 7-membered heteroaromatic ring C containing 1 to 4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl or C3-C6A cycloalkoxy group;
Q1、Q2each independently selected from the following:
Figure FDA0002225630990000052
R1、R3each independently selected from C1-C6Alkyl radical, C1-C3Haloalkyl or C3-C6A cycloalkyl group;
R4、R5each independently selected from halogen, C1-C6Alkyl radical, C1-C3Haloalkyl or C3-C6A cycloalkyl group;
l is selected from the following:
Figure FDA0002225630990000061
R7、R9each independently selected from C1-C6Alkyl radical, C1-C6Haloalkyl or C1-C6Alkoxy radical C1-C6An alkane;
R8is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C2-C6Alkenyl radical C1-C6Alkyl radical, C2-C6Alkynyl C1-C6Alkyl or phenyl; the hydrogen on the phenyl ring may be substituted by one or more substituents selected from halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C2-C6Alkenyl or C2-C6An alkynyl group;
m1、m2n is independently selected from 0-8;
Z1、Z2each independently selected from the group consisting of a bond, CH2O, S or NH.
5. The use of compounds of the general formula I according to claim 1 and their salts for controlling weeds.
6. A herbicidal composition characterized by: the herbicidal composition is an active substance and an agriculturally acceptable carrier, the active ingredient is the compound of the general formula I and the salt thereof as claimed in claim 1, and the weight percentage of the active ingredient in the composition is 1-99%.
7. A method of controlling weeds with a herbicidal composition according to claim 6, characterized in that: applying a herbicidally effective dose of the herbicidal composition of claim 6 to the weeds or to a growth medium or locus of the weeds.
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