CN112939958A - Condensed ring acyl compound and application thereof - Google Patents

Condensed ring acyl compound and application thereof Download PDF

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Publication number
CN112939958A
CN112939958A CN201911260893.2A CN201911260893A CN112939958A CN 112939958 A CN112939958 A CN 112939958A CN 201911260893 A CN201911260893 A CN 201911260893A CN 112939958 A CN112939958 A CN 112939958A
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radical
alkyl
alkoxy
cycloalkyl
halogenocycloalkyl
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程岩
杨辉斌
马宏娟
王明欣
崔东亮
英君伍
秦博
王刚
陈霖
孙冰
梁爽
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
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • 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
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
    • A01N43/14—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings
    • A01N43/18—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom six-membered rings with sulfur as the ring hetero 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
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/06—Benzothiopyrans; Hydrogenated benzothiopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Abstract

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

Description

Condensed ring acyl compound and application thereof
Technical Field
The invention belongs to the field of herbicides. In particular to a condensed ring acyl compound and application thereof as herbicide.
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.
CN103282354B reports that certain benzamide compounds have herbicidal activity, for example, among them compound KC 1:
Figure BDA0002311554680000011
the condensed ring acyl compounds shown in the invention are not disclosed.
Disclosure of Invention
The invention aims to provide a condensed ring acyl compound which has a novel structure and is safe to crops and application thereof as a herbicide.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a condensed ring acyl compound, which is characterized in that: the compound is shown as a general formula I:
Figure BDA0002311554680000012
in the formula:
x is selected from hydrogen, halogen, cyano, nitro, thiocyanato, 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, C3-C6Halogenocycloalkyl, C3-C6halogenocycloalkyl-C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl or C2-C6A haloalkynyl group;
n represents 0, 1, 2;
q is selected from Q1, Q2, Q3, Q4, Q5, Q6 or Q7 groups;
Figure BDA0002311554680000013
Figure BDA0002311554680000021
R1selected from hydrogen, Y, YCO, YOCO or Ysulfonyl;
y is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, phenyl C1-C6Alkyl, heteroaryl C1-C6Alkyl, heterocyclic radical C1-C6Alkyl, phenyl, heteroaryl or heterocyclic radical, the hydrogen on the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C3Alkoxy 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-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C1-C6Halogenoalkoxy radical C1-C6Alkyl, heterocyclic radical C1-C6Alkoxy, heterocyclic radical C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, C2-C6Alkenyloxy radical C1-C6Alkyl radical, C2-C6Alkynyloxy C1-C6Alkyl, phenyl, heteroaryl, heterocyclyl, heteroaryl C1-C6Alkyl or heterocyclyl radicals C1-C6The hydrogen of the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro and C1-C6Alkyl or C1-C6A haloalkyl group;
R2selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Haloalkynyl, heterocyclyl which is unsubstituted or substituted by at least one substituent selected from the group consisting of: halogen, nitro, cyano, thiocyanato, C1-C6Alkyl or C1-C6A haloalkyl group;
R3selected from hydrogen, halogen, cyano, nitro, C1-C6Alkyl, aryl, heteroaryl, and heteroaryl,C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, 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, C3-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl or C3-C6A haloalkynyl group.
The preferred compounds, of formula I:
x is selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl or C1-C6A haloalkyl group;
n represents 0, 1, 2;
q is selected from Q1, Q2, Q3, Q4, Q5, Q6 or Q7 groups;
Figure BDA0002311554680000022
Figure BDA0002311554680000031
R1selected from hydrogen, Y, YCO, YOCO or Ysulfonyl;
y is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, phenyl C1-C6Alkyl, heteroaryl C1-C6Alkyl, heterocyclic radical C1-C6Alkyl, phenyl, heteroaryl or heterocyclic radical, the hydrogen on the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C3Alkoxy 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-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C1-C6Halogenoalkoxy radical C1-C6Alkyl, heterocyclic radical C1-C6Alkoxy, heterocyclic radical C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, C2-C6Alkenyloxy radical C1-C6Alkyl radical, C2-C6Alkynyloxy C1-C6Alkyl, phenyl, heteroaryl, heterocyclyl, heteroaryl C1-C6Alkyl or heterocyclyl radicals C1-C6The hydrogen of the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro and C1-C6Alkyl or C1-C6A haloalkyl group;
R2selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl or C2-C6A haloalkynyl group;
R3selected from hydrogen, halogen, cyano, nitro, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, 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, C3-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl or C3-C6A haloalkynyl group.
Further preferred are compounds of formula I:
x is selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl or C1-C6A haloalkyl group;
n represents 0, 1, 2;
q is selected from the group Q1, Q3, Q6 or Q7;
Figure BDA0002311554680000032
R1selected from hydrogen, Y, YCO, YOCO or Ysulfonyl;
y is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, phenyl C1-C6Alkyl, heteroaryl C1-C6Alkyl, heterocyclic radical C1-C6Alkyl, phenyl, heteroaryl or heterocyclic radical, the hydrogen on the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C3Alkoxy 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-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C1-C6Halogenoalkoxy radical C1-C6Alkyl, heterocyclic radical C1-C6Alkoxy, heterocyclic radical C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, C2-C6Alkenyloxy radical C1-C6Alkyl radical, C2-C6Alkynyloxy C1-C6Alkyl, phenyl, heteroaryl, heterocyclyl, heteroaryl C1-C6Alkyl or heterocyclyl radicals C1-C6Alkyl radicals, the above-mentioned benzenesThe hydrogen on the group, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro and C1-C6Alkyl or C1-C6A haloalkyl group;
R2selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl or C2-C6A haloalkynyl group;
R3selected from hydrogen, halogen, cyano, nitro, 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 or C3-C6A cycloalkyloxy group.
Even more preferred are compounds of formula I wherein:
x is selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl or C1-C6A haloalkyl group;
n represents 0, 1, 2;
q is selected from the group Q1, Q3, Q6 or Q7;
Figure BDA0002311554680000041
R1selected from YCO;
y is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl, phenyl C1-C6Alkyl, heteroaryl C1-C6Alkyl, heterocyclic radical C1-C6Alkyl, phenyl, heteroaryl or heterocyclic radical, the hydrogen on the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C3Alkoxy 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-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C1-C6Halogenoalkoxy radical C1-C6Alkyl, heterocyclic radical C1-C6Alkoxy, heterocyclic radical C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, C2-C6Alkenyloxy radical C1-C6Alkyl radical, C2-C6Alkynyloxy C1-C6Alkyl, phenyl, heteroaryl, heterocyclyl, heteroaryl C1-C6Alkyl or heterocyclyl radicals C1-C6The hydrogen of the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro and C1-C6Alkyl or C1-C6A haloalkyl group;
R2is selected from C1-C6An alkyl group;
R3is selected from C1-C6An alkyl group.
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. Heterocyclyl means 3-7 membered heterocyclic compounds containing 1-4 heteroatoms without aromatic character, such as ethylene oxide, tetrahydrofuran, imidazolidinone, caprolactam, and the like. Heteroaryl refers to 5-7 membered aromatic heterocyclic compounds containing 1-4 heteroatoms, such as furan, thiophene, pyrazole, pyridine, and the like.
The compound I with the general formula can be prepared by the following method:
the method comprises the following steps:
Figure BDA0002311554680000051
the compound of the general formula Ia reacts in a proper solvent and in the presence of an oxidant 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.
Suitable oxidants are selected from hydrogen peroxide, m-chloroperoxybenzoic acid, nitric acid or magnesium monoperoxy-o-dibenzoate and the like.
The second method comprises the following steps:
when Q is Q1, the composition,
Figure BDA0002311554680000052
the compound shown in the general formula II and the compound shown in the general formula III react in a proper solvent at the temperature of-10 ℃ to the boiling point of the proper solvent for 0.5-48 hours to prepare the target compound Ib.
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 compound of formula III is commercially available or is prepared by reference to CN 103282354B.
The compounds of the general formula II are prepared by the process described in WO2018052967A 1.
When Q is Q2, Q3, Q4 and Q5, the preparation method thereof refers to the synthesis method when Q is Q1.
When Q is Q6, the composition,
Figure BDA0002311554680000061
l is selected from a leaving group.
The compound Id and the compound IV react in a proper solvent at a temperature of-10 ℃ to the boiling point of the proper solvent for 0.5 to 48 hours to prepare the target compound Ic. 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 is 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 formula IV can be prepared from the corresponding acids which are commercially available.
The compounds of formula Id are prepared as follows:
Figure BDA0002311554680000062
the compound of the general formula V reacts in a proper solvent under the action of alkali and a catalyst at the temperature of-10 ℃ to the boiling point of the proper solvent for 0.5 to 48 hours to prepare the compound of the general formula Id. 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. Suitable bases are selected from sodium carbonate, potassium carbonate or triethylamine and the like. Suitable catalysts are selected from sodium carbonate, potassium carbonate, acetone cyanohydrin, azide, quaternary ammonium azide, metal cyanide or DMAP, and the like.
The preparation of the compounds of formula V is as follows:
Figure BDA0002311554680000063
the compound of formula VI is reacted with a compound of formula VII (prepared as described in commercially available or reference EP 0240001) in a suitable solvent at a temperature of from-10 ℃ to the boiling point of the suitable solvent for a period of from 0.5 to 24 hours to produce a compound of formula V. 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 is 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 starting carboxylic acid (commercially available) corresponding to the compound of formula VI is reacted with an acid halogenating agent in a suitable solvent at a temperature of from-10 deg.C to the boiling point of the suitable solvent for a period of from 0.5 to 48 hours to produce the compound of formula V. The acyl halide reagent is selected from oxalyl chloride, thionyl chloride, phosphorus oxychloride, phosphorus trichloride, phosphorus pentachloride and the like. Suitable solvents are selected from dichloromethane, 1, 2-dichloroethane, hexane, benzene, toluene, acetonitrile, acetic acid or dioxane, and the like.
When Q is Q7, the compound can be prepared by a synthetic method when Q is Q6.
The compound of the general formula I has herbicidal activity and can be used for preventing and controlling various weeds in agriculture. Compared with the compounds disclosed in the prior art, the condensed ring acyl 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 in the general formula I as an active component. 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 condensed ring acyl compounds, the compounds in the general formula contain two different benzoyl substitutions, the structure is novel, the condensed ring acyl compounds have unexpected high herbicidal activity, and also have high herbicidal activity under a lower dosage, so that the efficiency is high, the use amount of pesticides is reduced, the cost is reduced, and the pollution to the environment is reduced.
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 compound 1:
(1) synthesis of 3-trifluoromethyl-6- (2-formylethylthio) benzoic acid
Figure BDA0002311554680000081
Reaction system A: to a 100 ml single-neck flask was added 2-amino-4-trifluoromethylbenzoic acid (10 g, 48.7 mmol), 20 ml of water was added, and the mixture was stirred at room temperature. Sodium hydroxide (1.92 g, 48.0 mmol) was weighed into a small beaker and dissolved in 30 ml of water. The sodium hydroxide solution was added to reaction system a, stirred at room temperature until the reaction product was completely dissolved, and sodium nitrite (4.03 g, 58.4 mmol) was added and stirred at room temperature for further use.
Reaction system B: to a 1000 ml four-necked flask was added concentrated hydrochloric acid (17.5 g, 175.5 mmol), ice-cooled (0 ℃ C.), added 17.5 g water, and mechanically stirred in ice-cooled (0 ℃ C.). Reaction A was added dropwise to reaction B, and stirred in an ice bath (0 ℃ C.) for about 3 hours. And (3) taking a drop of reaction liquid to starch potassium iodide test paper, wherein the starch potassium iodide test paper turns blue and does not fade for 5 minutes, and the reaction is finished. Potassium acetate was added, and water was added to adjust the reaction solution to pH 6 to 7. The four-necked bottle was placed in an ice bath for further use.
Reaction system C: to a three-necked flask was added potassium ethylxanthate (16.8 g, 107.2 mmol), 8.6 g of water was added, and the mixture was stirred at 85 ℃. Slowly dropwise adding the reaction system B into the reaction system C, stirring at 85 ℃ for about 2.5h after the dropwise adding is finished, and cooling to room temperature. Adding concentrated hydrochloric acid to adjust pH to 3, stirring, and precipitating viscous oily solid. The supernatant was poured off, a small amount of water was added, the solid was washed twice, and the supernatant was poured off. Adding 80 g of 10% sodium hydroxide solution, stirring at 80 ℃ for 2h, adding 6-8 g of sodium hydrosulfite, stirring for 10min, and cooling to room temperature. 3-Bromopropionic acid (8.2 g, 53.6 mmol) was added and stirred at room temperature.
Concentrated hydrochloric acid is added into a reaction bottle to adjust the pH value to be 1-2, a large amount of yellow solid is separated out, and a target product 11.81 g of yellow solid with the content of 95.5 percent and the yield of 78.7 percent is obtained by filtration.
(2) Synthesis of 5-trifluoromethyl-4-thiochromanone-8-formic acid
Figure BDA0002311554680000082
To a 100 ml three-necked flask were added 3-trifluoromethyl-6- (2-formylethylthio) benzoic acid (10 g, 34.0 mmol), polyphosphoric acid (100 g), and the solution was mechanically stirred at 120 ℃ for 4h to turn yellow to red. Adding water into a three-necked bottle in ice bath, releasing heat, separating out a solid, filtering, washing a filter cake twice, dissolving the filter cake with ethyl acetate, extracting an aqueous phase with ethyl acetate, combining an organic phase with the solid obtained by filtering, carrying out rotary evaporation/adding ethyl acetate for extraction, drying the organic phase, carrying out rotary evaporation, and carrying out column chromatography to obtain 3.6 g of a mixture.
(3) Synthesis of Compound 1
Figure BDA0002311554680000083
5-trifluoromethyl-4-thiochromanone-8-carboxylic acid (1.2 g, 4.2 mmol), 1-methyl-5-aminotetrazole (0.6 g, 6.4 mmol), 3-methylpyridine (0.4 g, 4.2 mmol), N-methylimidazole (0.7 g, 8.5 mmol) were added to a reaction flask, stirred at room temperature for half an hour, cooled in an ice water bath to below 10 ℃, thionyl chloride (1.0 g, 8.5 mmol) was slowly added dropwise, stirred at room temperature, and the reaction was monitored by TLC. Extracting with ethyl acetate and water, and drying, rotary evaporating and desolventizing the organic phase. The compound 1 is separated by column chromatography to obtain 0.2 g of orange solid with the purity of 94 percent and the yield of 12.42 percent.
Example 2, synthesis of compound 3:
(1) synthesis of Compound 3
Figure BDA0002311554680000091
Compound 1(0.1 g, 0.3 mmol, see example 1, step 3 for preparation), 5 ml of acetic acid as solvent, sodium tungstate (0.008 g, 0.03 mmol), stirring at 60 ℃, dropwise addition of hydrogen peroxide (0.03 g, 0.8 mmol), stirring at 60 ℃ for about 4 hours, and monitoring the reaction by TLC. Cooling to room temperature, adding a large amount of water, precipitating a solid, and filtering to obtain 0.04 g of compound 3 yellow solid with the purity of 90 percent and the yield of 33 percent.
Example 3, synthesis of compound 266:
(1) synthesis of 5-trifluoromethyl-4-thiochromanone-8-formyl chloride
Figure BDA0002311554680000092
5-trifluoromethyl-4-thiochromanone-8-carboxylic acid (1.5 g, 5.43 mmol, see example 1, step 2 for its preparation), toluene (10 ml), thionyl chloride (2.6 g, 21.7 mmol) were added to a reaction flask, refluxed for 4 hours, and desolventized under reduced pressure to give 5-trifluoromethyl-4-thiochromanone-8-carbonyl chloride, which was used directly in the next step.
(2) Synthesis of 5-trifluoromethyl-4-thiochromanone-8-methanesulfonyl (1, 3-dimethylpyrazol-5-yl) ester
Figure BDA0002311554680000093
To a reaction flask, 1, 3-dimethyl-5-hydroxypyrazole (0.7 g, 6.5 mmol) and dichloromethane (5 ml) were added, triethylamine (0.9 g, 7.8 mmol) was added, and 5-trifluoromethyl-4-thiochromanone-8-carbonyl chloride was dissolved in dichloromethane (5 ml) and added dropwise to the reaction flask, followed by stirring at room temperature. Adding water and ethyl acetate for extraction, drying and desolventizing the organic phase, and performing column chromatography to obtain 0.5 g of 5-trifluoromethyl-4-thiochromanone-8-methylsulfonyl (1, 3-dimethylpyrazol-5-yl) ester with the yield of 57 percent.
(3) Synthesis of Compound 266
Figure BDA0002311554680000101
To a reaction flask was added 5-trifluoromethyl-4-thiochromanone-8-methanesulfonyl (1, 3-dimethylpyrazol-5-yl) ester (0.5 g, 1.4 mmol), dichloromethane (5 ml), triethylamine (0.27 g, 2.7 mmol) and acetone cyanohydrin (0.5 g, 5.4 mmol), and reacted for 4 hours. Water and ethyl acetate are added for extraction, and organic phase is dried and desolventized to obtain 0.4 g of 1, 3-dimethyl-4- (5-trifluoromethyl-4-thiochromanone-8-methylsulfonyl) -5-hydroxypyrazole with the yield of 80 percent.
Example 4, synthesis of compound 301:
(1) synthesis of 1-ethyl-5-methyl-1H-pyrazole-3-carbonyl chloride
Figure BDA0002311554680000102
1-ethyl-5-methyl-1H-pyrazole-3-carboxylic acid (0.25 g, 1.6 mmol) and toluene (5 ml) are added into a reaction flask, thionyl chloride (0.8 g, 6.5 mmol) is added, reflux reaction is carried out for 4 hours, and decompression and desolventization are carried out to obtain 1-ethyl-5-methyl-1H-pyrazole-3-formyl chloride which is directly used in the next step.
(2) Synthesis of Compound 301
Figure BDA0002311554680000103
To a reaction flask was added 1, 3-dimethyl-4- (5-trifluoromethyl-4-thiochromanone-8-methanesulfonyl) -5-hydroxypyrazole (0.4 g, 1.1 mmol, see example 3, step 3 for its preparation), dichloromethane (10 ml), triethylamine (0.13 g, 1.3 mmol) was added, and 1-ethyl-5-methyl-1H-pyrazole-3-carbonyl chloride was dissolved in dichloromethane (10 ml) and added dropwise to the reaction flask, and stirred at room temperature. Adding water and ethyl acetate for extraction, drying and desolventizing the organic phase, and separating by column chromatography to obtain 0.32 g of a target product with the yield of 33%.
Example 5, synthesis of compound 303:
Figure BDA0002311554680000111
compound 301(0.2 g, 0.395 mmol, see example 4, step 2 for its preparation), acetic acid (5 ml), hydrogen peroxide (0.04 g, 1.2 mmol), sodium tungstate (0.02 g, 0.07 mmol) were added to the reaction flask. The oil bath was warmed to 60 ℃ and stirred for 4 hours. Adding water and ethyl acetate to extract, washing for three times, and separating by column chromatography to obtain 0.05 g of compound with purity of 97% and yield of 23%.
Example 6, synthesis of compound 324:
(1) synthesis of 5-trifluoromethyl-4-thiochromanone-8-formyl chloride
Figure BDA0002311554680000112
To a reaction flask was added 5-trifluoromethyl-4-thiochromanone-8-carboxylic acid (0.2 g, 0.7 mmol, see example 1, step 2 for its preparation), toluene (10 ml), thionyl chloride (0.09 g, 0.7 mmol), refluxed for 4 hours, and desolventized under reduced pressure to give 5-trifluoromethyl-4-thiochromanone-8-carbonyl chloride, which was used directly in the next step.
(2) Synthesis of 3- (5-trifluoromethyl-4-thiochromanone-8-acyl) oxy-2-cyclohexene-1-one
Figure BDA0002311554680000113
To a reaction flask were added 1, 3-cyclohexanedione (0.09 g, 0.8 mmol) and triethylamine (0.09 g, 0.9 mmol), and dichloromethane (5 ml), and a solution of 5-trifluoromethyl-4-thiochromanone-8-carbonyl chloride in dichloromethane was added dropwise and reacted at room temperature for 1 hour. Washing with water, desolventizing the organic phase, and separating by column chromatography to obtain 0.13 g of the product with the purity of 61% and the yield of 30%.
(3) Synthesis of Compound 324
Figure BDA0002311554680000114
To a reaction flask were added 3- (5-trifluoromethyl-4-thiochromanone-8-acyl) oxy-2-cyclohexen-1-one (0.4 g, 1.1 mmol), dichloromethane (10 ml), triethylamine (0.1 g, 1.1 mmol) and acetone cyanohydrin (0.1 g, 1.1 mmol), and the mixture was refluxed for 3 hours. Adding water and ethyl acetate for extraction, drying and desolventizing the organic phase, and separating by column chromatography to obtain 0.15 g of brown solid with the purity of 70 percent and the yield of 26 percent.
The compounds represented by general formula I can be obtained by substituting the raw materials during the reaction according to the above-mentioned preparation method, and the compounds are shown in table 1.
Figure BDA0002311554680000121
Table 1: the structure and physical properties of part of the compounds of the general formula I
Figure BDA0002311554680000122
Figure BDA0002311554680000131
Figure BDA0002311554680000141
Figure BDA0002311554680000151
Figure BDA0002311554680000161
Figure BDA0002311554680000171
Figure BDA0002311554680000181
Figure BDA0002311554680000191
Figure BDA0002311554680000201
Figure BDA0002311554680000211
Figure BDA0002311554680000221
Figure BDA0002311554680000231
Figure BDA0002311554680000241
Figure BDA0002311554680000251
Figure BDA0002311554680000261
Figure BDA0002311554680000271
Of partial compounds1H NMR(600MHz,CDCl3) The data are as follows:
compounds 1:8.13-8.15(d,1H),8.76-8.77(d,1H),4.13(s,3H),3.18-3.20(m,2H),3.14-3.16(m, 2H).
Compounds 266:8.26-8.27(d,1H),7.67-7.69(d,1H),3.73(s,3H),3.20-3.23(m,2H),3.14-3.17(m,2H),2.27(s, 3H).
Compounds 301:7.33-7.34(d,1H),7.35-7.36(d,1H),6.21(s,1H),4.10-4.14(m,2H),3.63(s,3H),3.17-3.20(t,2H),3.01-3.03(t,2H),2.56(s,3H),3.28(s,3H),1.23-1.25(t, 3H).
Compounds 303:7.77-7.79(d,1H),7.56-7.57(d,1H),6.24(s,1H),4.09-4.13(m,2H),3.72-3.74(t,2H),3.60(s,3H),3.30-3.32(t,2H),2.60(s,3H),2.31(s,3H),1.40-1.42(t, 3H).
Compounds 324:8.19-8.20(d,1H),7.60-7.62(m,1H),3.16-3.18(m,2H),3.09-3.13(m,2H),2.60-2.62(t,2H),2.06-2.10(m,2H),1.98-2.04(m, 2H).
Examples of bioassay
Example 7 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 spray treatment (spray pressure 1.95 kg/cm) was carried out on a crawler-type crop sprayer (Engineer Research Ltd. in England) at the experimental design dose2The 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. Of the compounds tested, compounds 1,3, 266, 303, 324 exhibited better control of zinnia, piemarker, green bristlegrass or cockspur grass at a dose of 600g a.i./hm2, with greater than 80% control.
Compound 3 was selected for parallel comparison with KC1 for control of abutilon according to the test methods above and the results are shown in Table 2.
Table 2: abutilon-controlling activity of compound 3 and control compound KC1
(post-emergence, control effect%)
Figure BDA0002311554680000281
"/" denotes: not tested, the same shall apply
The compound with the general formula has herbicidal activity and can be used for controlling various weeds in agriculture. Meanwhile, the condensed ring acyl compound has excellent herbicidal activity and is safe to crops.

Claims (7)

1. A condensed ring acyl compound, which is characterized in that: the compound is shown as a general formula I:
Figure FDA0002311554670000011
in the formula:
x is selected from hydrogen, halogen, cyano, nitro, thiocyanato, 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, C3-C6Halogenocycloalkyl, C3-C6halogenocycloalkyl-C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl or C2-C6A haloalkynyl group;
n represents 0, 1, 2;
q is selected from Q1, Q2, Q3, Q4, Q5, Q6 or Q7 groups;
Figure FDA0002311554670000012
R1selected from hydrogen, Y, YCO, YOCO or Ysulfonyl;
y is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, phenyl C1-C6Alkyl, heteroaryl C1-C6Alkyl, heterocyclic radical C1-C6Alkyl, phenyl, heteroaryl or heterocyclic radical, the hydrogen on the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C3Alkoxy 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-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C1-C6Halogenoalkoxy radical C1-C6Alkyl, heterocyclic radical C1-C6Alkoxy, heterocyclic radical C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, C2-C6Alkenyloxy radical C1-C6Alkyl radical, C2-C6Alkynyloxy C1-C6Alkyl, phenyl, heteroaryl, heterocyclyl, heteroaryl C1-C6Alkyl or heterocyclyl radicals C1-C6The hydrogen of the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro and C1-C6Alkyl or C1-C6A haloalkyl group;
R2selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Haloalkynyl, heterocyclyl which is unsubstituted or substituted by at least one of the following substituents: the substituent group is selected from: halogen, nitro, cyano, thiocyanato, C1-C6Alkyl or C1-C6A haloalkyl group;
R3selected from hydrogen, halogen, cyano, nitro, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, 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, C3-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl or C3-C6A haloalkynyl group.
2. A compound according to claim 1, wherein in formula I:
x is selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl or C1-C6A haloalkyl group;
n represents 0, 1, 2;
q is selected from Q1, Q2, Q3, Q4, Q5, Q6 or Q7 groups;
Figure FDA0002311554670000021
R1selected from hydrogen, Y, YCO, YOCO or Ysulfonyl;
y is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, phenyl C1-C6Alkyl, heteroaryl C1-C6Alkyl, heterocyclic radical C1-C6Alkyl, phenyl, heteroaryl or heterocyclic radical, the hydrogen on the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C6Alkoxy radical C1-C6Alkyl radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C3Alkoxy 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-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C1-C6Halogenoalkoxy radical C1-C6Alkyl, heterocyclic radical C1-C6Alkoxy, heterocyclic radical C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, C2-C6Alkenyloxy radical C1-C6Alkyl radical, C2-C6Alkynyloxy C1-C6Alkyl, phenyl, heteroaryl, heterocyclyl, heteroaryl C1-C6Alkyl or heterocyclyl radicals C1-C6The hydrogen of the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro and C1-C6Alkyl or C1-C6A haloalkyl group;
R2selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl or C2-C6A haloalkynyl group;
R3selected from hydrogen, halogen, cyano, nitro, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, 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, C3-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl or C3-C6A haloalkynyl group.
3. A compound according to claim 2, wherein in formula I:
x is selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl or C1-C6A haloalkyl group;
n represents 0, 1, 2;
q is selected from the group Q1, Q3, Q6 or Q7;
Figure FDA0002311554670000031
R1selected from hydrogen, Y, YCO, YOCO or Ysulfonyl;
y is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, phenyl C1-C6Alkyl, heteroaryl C1-C6Alkyl, heterocyclic radical C1-C6Alkyl, phenyl, heteroaryl or heterocyclic radical, the hydrogen on the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C3Alkoxy 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-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C1-C6Halogenoalkoxy radical C1-C6Alkyl, heterocyclic radical C1-C6Alkoxy, heterocyclic radical C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, C2-C6Alkenyloxy radical C1-C6Alkyl radical, C2-C6Alkynyloxy C1-C6Alkyl, phenyl, heteroaryl, heterocyclyl, heteroaryl C1-C6Alkyl or heterocyclyl radicals C1-C6The hydrogen of the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro and C1-C6Alkyl or C1-C6A haloalkyl group;
R2selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl or C2-C6A haloalkynyl group;
R3selected from hydrogen, halogen, cyano, nitro, 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 or C3-C6A cycloalkyloxy group.
4. A compound according to claim 3, wherein in formula I:
x is selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl or C1-C6A haloalkyl group;
n represents 0, 1, 2;
q is selected from the group Q1, Q3, Q6 or Q7;
Figure FDA0002311554670000041
R1selected from YCO;
y is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl, phenyl C1-C6Alkyl, heteroaryl C1-C6Alkyl, heterocyclic radical C1-C6Alkyl, phenyl, heteroaryl or heterocyclic radical, the hydrogen on the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro, thiocyanato, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C3Alkoxy 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-C6Halogenocycloalkyl, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, C1-C6Halogenoalkoxy radical C1-C6Alkyl, heterocyclic radical C1-C6Alkoxy, heterocyclic radical C1-C6Alkoxy radical C1-C6Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl radical、C2-C6Halogenated alkynyl, C2-C6Alkenyloxy radical C1-C6Alkyl radical, C2-C6Alkynyloxy C1-C6Alkyl, phenyl, heteroaryl, heterocyclyl, heteroaryl C1-C6Alkyl or heterocyclyl radicals C1-C6The hydrogen of the phenyl, heteroaryl and heterocyclic radical can be substituted by one or more substituent groups selected from halogen, cyano, nitro and C1-C6Alkyl or C1-C6A haloalkyl group;
R2is selected from C1-C6An alkyl group;
R3is selected from C1-C6An alkyl group.
5. Use of a compound of formula I according to claim 1 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 a compound of the general formula I 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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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07291970A (en) * 1994-04-22 1995-11-07 Idemitsu Kosan Co Ltd Pyrazole derivative and herbicide using the same
CN103282354A (en) * 2010-09-01 2013-09-04 拜耳知识产权有限责任公司 N-(tetrazol-5-l)- and n-(triazol-5-yl)arylcarboxamides and use thereof as herbicides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH07291970A (en) * 1994-04-22 1995-11-07 Idemitsu Kosan Co Ltd Pyrazole derivative and herbicide using the same
CN103282354A (en) * 2010-09-01 2013-09-04 拜耳知识产权有限责任公司 N-(tetrazol-5-l)- and n-(triazol-5-yl)arylcarboxamides and use thereof as herbicides

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