CN111303126A - Pyrazole amide compound and application thereof as herbicide - Google Patents

Pyrazole amide compound and application thereof as herbicide Download PDF

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CN111303126A
CN111303126A CN201811516181.8A CN201811516181A CN111303126A CN 111303126 A CN111303126 A CN 111303126A CN 201811516181 A CN201811516181 A CN 201811516181A CN 111303126 A CN111303126 A CN 111303126A
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radical
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cycloalkyl
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haloalkyl
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CN111303126B (en
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杨辉斌
英君伍
马宏娟
秦博
崔东亮
程岩
王刚
孙冰
陈霖
李斌
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Shenyang Sinochem Agrochemicals R&D Co Ltd
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    • 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
    • C07D403/02—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 two hetero rings
    • C07D403/12—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 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
    • A01N43/713—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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Plant Pathology (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen Condensed Heterocyclic Rings (AREA)

Abstract

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

Description

Pyrazole amide compound and application thereof as herbicide
Technical Field
The invention belongs to the field of herbicides. In particular to a pyrazole amide compound and application thereof as a 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.
CN108290846A reports that certain benzamide compounds have herbicidal activity, such as compounds No. 1-28 (KC1) and compounds No. 1-9 (KC2) among them:
Figure BDA0001902026630000011
the pyrazole amide compounds shown in the invention are not disclosed.
Disclosure of Invention
The invention aims to provide a pyrazole amide compound which has a novel structure and is safe to crops and an application thereof as a herbicide.
In order to achieve the purpose, the technical scheme of the invention is as follows:
a pyrazole amide compound is shown as a general formula I:
Figure BDA0001902026630000012
q is the following group: q1、Q2、Q3
Figure BDA0001902026630000013
In the formula:
X1and X3Can be the same or different and is respectively selected from hydrogen, cyano, nitro, halogen and 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 or C3-C6A cycloalkyloxy group;
X2selected from hydrogen, cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Sulfoxide 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;
Y1is selected from 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;
R1is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkoxy radical C1-C3Alkyl radical, C1-C6Halogenoalkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkylthio group C1-C3Alkyl radical, C1-C6Haloalkylthio C1-C3Alkyl radical, C1-C6Alkyl sulfoxide radical C1-C3Alkyl radical, C1-C6Halogenoalkylsulfonol C1-C3Alkyl radical, C1-C6Alkyl sulfone radical C1-C3Alkyl or C1-C6Halogenoalkylsulfonyl C1-C3An alkyl group;
R2selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl or C1-C6A haloalkyl group;
R3selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, C1-C6Alkoxy radical, C2-C6Alkenyl radical, C2-C6Alkynyl or phenyl which is unsubstituted or substituted by 1 to 5 substituents selected from cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C1-C6Alkoxy radicalRadical or C1-C6A haloalkoxy group.
The preferred compounds, of formula I:
X1and X3Are the same or different and are respectively selected from cyano, nitro, halogen and C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C3Alkoxy radical, C1-C3Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl or C3-C6A cycloalkyloxy group;
X2selected from hydrogen, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Sulfoxide 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, 1 to 45-7 membered heteroatomic aliphatic heterocycle 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;
Y1is selected from 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;
R1is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkoxy radical C1-C3Alkyl radical, C1-C6Halogenoalkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkylthio group C1-C3Alkyl radical, C1-C6Haloalkylthio C1-C3Alkyl radical, C1-C6Alkyl sulfoxide radical C1-C3Alkyl radical, C1-C6Halogenoalkylsulfonol C1-C3Alkyl radical, C1-C6Alkyl sulfone radical C1-C3Alkyl or C1-C6Halogenoalkylsulfonyl C1-C3An alkyl group;
R2selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl or C1-C6A haloalkyl group;
R3selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, C1-C6Alkoxy radical, C2-C6Alkenyl radical, C2-C6Alkynyl or phenyl which is unsubstituted or substituted by 1 to 5 substituents selected from cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C1-C6Alkoxy or C1-C6A haloalkoxy group.
Said further preferred compounds, of the general formula I:
X1and X3Can be the same or different and is respectively selected from hydrogen, nitryl, halogen and C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl or C1-C6A haloalkyl group;
X2selected from hydrogen, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Sulfoxide 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;
Y1is selected from 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, 5-to 7-membered heteroaromatic ring C containing 1-4 heteroatoms1-C6Alkyl, the following is takenThe substituent is selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl or C3-C6A cycloalkoxy group;
R1is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C1-C6Alkylsulfonyl radical, C1-C6Alkylthio group C1-C3Alkyl radical, C1-C6Alkyl sulfoxide radical C1-C3Alkyl or C1-C6Alkyl sulfone radical C1-C3An alkyl group;
R2selected from hydrogen, halogen, nitro, cyano, C1-C3Alkyl or C1-C3A haloalkyl group;
R3selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl or phenyl which is unsubstituted or substituted by 1 to 5 substituents selected from cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C1-C6Alkoxy or C1-C6A haloalkoxy group.
Said further preferred compounds, formula I:
X1and X3Can be the same or different and is respectively selected from hydrogen, nitryl, halogen and C1-C3Alkylsulfonyl radical, C1-C3Alkyl or C1-C3A haloalkyl group;
X2selected from hydrogen, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkyl sulfonic acidAcyl radical, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, Y1Oxy radical, Y1Oxy radical C1-C3Alkyl radical, Y1Thio radical C1-C3Alkyl, 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 halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl or C3-C6A cycloalkoxy group;
Y1is selected from 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;
R1is selected from C1-C3Alkyl radical, C1-C3Alkylsulfonyl or C1-C3Alkyl sulfone radical C1-C3An alkyl group;
R2selected from hydrogen, halogen, C1-C3Alkyl or C1-C3A haloalkyl group;
R3selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl or C3-C6A cycloalkyl 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. Alkenyl means straight or branched chain alkenyl groups such as 1-propenyl, 2-propenyl, butenyl, pentenyl and hexenyl groups and the like. Alkynyl means straight or branched chain alkynyl groups such as 1-propynyl, 2-propynyl, butynyl, pentynyl, hexynyl 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:
the method comprises the following steps:
Figure BDA0001902026630000041
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 formula III may be prepared from the corresponding acids which are commercially available or by the procedures described in reference to WO 2009123714.
The second method comprises the following steps:
Figure BDA0001902026630000051
the compound of the general formula IV and the compound of the general formula V 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 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 formula V can be prepared from the corresponding acids (commercially available).
The preparation of the compounds of formula II is as follows:
Figure BDA0001902026630000052
reacting a compound of formula VI (commercially available) with a compound of formula VII (commercially available) in a suitable base and 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 of the compounds of the formula IV can be referred to the preparation of the formula II.
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 pyrazole amide compound disclosed by the invention has excellent herbicidal activity and 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 pyrazole amide compounds, the compound of the general formula contains a benzoyl and a pyrazole acyl substituent, 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 compound 9:
(1) synthesis of N- (1-methyl-tetrazole-5-yl) -2-methylsulfonyl-4-trifluoromethylbenzoic acid amide
Figure BDA0001902026630000061
Adding 2-methylsulfonyl-4-trifluoromethylbenzoic acid (19.1 g, 71.2 mmol), 1-methyl-5-aminotetrazole (8.5 g, 85.4 mmol), 3-methylpyridine (80 g, 855 mmol), and N-methylimidazole (11.7 g, 142 mmol) into a reaction flask, stirring at room temperature for half an hour, cooling in an ice-water bath to below 10 ℃, slowly dropping thionyl chloride (13.6 g, 114 mmol), stirring at room temperature for 2 hours, heating to 50 ℃, keeping the temperature for reaction for 2 hours, cooling in an ice-water bath to below 10 ℃, slowly dropping cold water to precipitate a solid, filtering, washing a filter cake twice with 100 ml water, and drying to obtain 17.5 g of a white solid with a yield of 70%.
(2) Synthesis of 1-ethyl-5-methyl-3-pyrazolecarbonyl chloride
Figure BDA0001902026630000071
1-Ethyl-5-methyl-3-pyrazolecarboxylic acid (20 g, 130 mmol) and toluene (100 ml) were added to a reaction flask, thionyl chloride (50 g, 42.4 mmol) was slowly added thereto, and the mixture was heated under reflux for 4 hours, and the solvent was evaporated under reduced pressure to obtain 22.3 g of a yellow oil which was used directly in the next step.
(3) Synthesis of Compound 9
Figure BDA0001902026630000072
To a reaction flask were added N- (1-methyl-tetrazol-5-yl) -2-methanesulfonyl-4-trifluoromethylbenzamide (30 g, 86 mmol), dichloromethane (100 ml), and triethylamine (13 g, 128 mmol), and a dichloromethane solution (50 ml) of the above 1-ethyl-5-methyl-3-pyrazolecarbonyl chloride was added dropwise. After stirring at room temperature for 1 hour, the solvent was evaporated under reduced pressure, ethyl acetate (500 ml) was added to the residue, followed by liquid-phase extraction with water (200 ml), the organic phase was washed successively with saturated brine (100 ml), dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was separated by column chromatography to give 22.5 g of a white solid compound 9 with a purity of 97% and a yield of 52%.
Example 2, synthesis of compound 82:
(1) synthesis of 1, 3-dimethyl-4-pyrazolecarbonyl chloride
Figure BDA0001902026630000073
1, 3-dimethyl-4-pyrazolecarboxylic acid (0.32 g, 2.3 mmol) and toluene (10 ml) were added to a reaction flask, sulfoxide chloride (0.7 g, 5.8 mmol) was slowly added to the mixture, the mixture was heated under reflux for 4 hours, and the solvent was evaporated off under reduced pressure to give 0.36 g of a yellow oil which was used directly in the next step.
(2) Synthesis of Compound 82
Figure BDA0001902026630000074
To a reaction flask, N- (1-methyl-tetrazol-5-yl) -2-methanesulfonyl-4-trifluoromethylbenzamide (0.4 g, 1.15 mmol), dichloromethane (10 ml), and triethylamine (0.35 g, 3.4 mmol) were added, and a dichloromethane solution (5 ml) of the above-obtained 1, 3-dimethyl-4-pyrazolecarbonyl chloride was added dropwise. After stirring at room temperature for 1 hour, the solvent was evaporated under reduced pressure, ethyl acetate (100 ml) was added to the residue, water (50 ml) was added for liquid-phase extraction, the organic phase was washed successively with saturated brine (20 ml), dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was separated by column chromatography to give 0.28 g of compound 82 as a white solid with a purity of 99% and a yield of 52%.
Example 3, synthesis of compound 142:
(1) synthesis of 1-ethyl-3-methyl-5-pyrazolecarbonyl chloride
Figure BDA0001902026630000081
1-Ethyl-3-methyl-5-pyrazolecarboxylic acid (0.35 g, 2.3 mmol) and toluene (10 ml) were added to a reaction flask, sulfoxide chloride (0.7 g, 5.8 mmol) was slowly added to the mixture, the mixture was heated under reflux for 4 hours, and the solvent was evaporated under reduced pressure to give 0.39 g of a yellow oil which was used directly in the next step.
(2) Synthesis of Compound 142
Figure BDA0001902026630000082
To a reaction flask were added N- (1-methyl-tetrazol-5-yl) -2-methanesulfonyl-4-trifluoromethylbenzamide (0.4 g, 1.15 mmol), dichloromethane (10 ml), and triethylamine (0.23 g, 2.3 mmol), and a dichloromethane solution (5 ml) of the above-obtained 1-ethyl-3-methyl-5-pyrazolecarbonyl chloride was added dropwise. After stirring at room temperature for 1 hour, the solvent was evaporated under reduced pressure, ethyl acetate (100 ml) was added to the residue, followed by liquid-phase extraction with water (50 ml), the organic phase was washed successively with saturated brine (20 ml), dried over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure, and the residue was subjected to column chromatography to give 0.34 g of compound 142 as a white solid with a purity of 96% and a yield of 58%.
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 BDA0001902026630000083
Q is the following group: q1、Q2、Q3：
Figure BDA0001902026630000091
Table 1 structural and physical properties of some compounds of formula I
Figure BDA0001902026630000092
Figure BDA0001902026630000101
Figure BDA0001902026630000111
Figure BDA0001902026630000121
Figure BDA0001902026630000131
Figure BDA0001902026630000141
Figure BDA0001902026630000151
Figure BDA0001902026630000161
Of partial compounds1H NMR(300MHz,CDCl3) The data are as follows：
Compounds 1:8.30(s,1H),8.01(d,1H),7.79(d,1H),6.49(s,1H),4.14(s,3H),3.74(t,2H)3.18(s,3H),2.18(s,3H),1.56-1.62(m,2H),0.76(t, 3H).
Compounds 2:8.29(s,1H),8.01(d,1H),7.79(d,1H),6.32(s,1H),4.15(s,3H),3.65(s,3H),3.18(s,3H),1.56-1.60(m,1H),0.93-0.98(m,2H),0.57-0.59(m, 2H).
Compounds 4:8.30(s,1H),8.02(d,1H),7.81(d,1H),6.52(s,1H),5.67-5.72(m,1H),5.22(d,1H),4.88(d,1H),4.41(d,2H),4.13(s,3H),3.19(s,3H),2.17(s, 3H).
Compounds 5:8.29(s,1H),8.02(d,1H),7.78(d,1H),6.74(t,1H),6.53(s,1H),5.58(d,2H),4.14(s,3H),3.17(s,3H),2.24(s, 3H).
Compounds 6:8.30(s,1H),8.01(d,1H),7.79(d,1H),6.32(s,1H),4.16(s,3H),3.98(q,2H),3.19(s,3H),1.55-1.61(m,1H),1.23(t,3H),0.95-0.97(m,2H),0.57-0.60(m, 2H).
Compounds 7:8.31(s,1H),8.02(d,1H),7.79(d,1H),6.49(s,1H),4.15(s,3H),3.96-4.02(m,1H),3.19(s,3H),2.18(s,3H),1.53-1.57(m,2H),1.18(d,3H),0.63(t, 3H).
Compounds 8:8.30(s,1H),8.02(d,1H),7.79(d,1H),6.50(s,1H),4.14(s,3H),3.57(d,2H),3.19(s,3H),2.18(s,3H),1.85-1.90(m,1H),0.77(d, 6H).
Compounds 9:8.29(s,1H),8.01(d,1H),7.79(d,1H),6.48(s,1H),4.14(s,3H),3.82(q,2H),3.18(s,3H),2.18(s,3H),1.192(t, 3H).
Compounds 10:8.29(s,1H),8.02(d,1H),7.79(d,1H),6.49(s,1H),4.15(s,3H),3.54(s,3H),3.19(s,3H),2.18(s, 3H).
Compounds 15:8.30(s,1H),8.02(d,1H),7.79(d,1H),6.48(s,1H),4.14(s,3H),3.78(t,2H),3.18(s,3H),2.18(s,3H),1.51-1.54(m,2H),1.12-1.16(m,2H),0.91(t, 3H).
Compounds 16:8.83(s,1H),8.38(d,1H),7.83(d,1H),6.45(s,1H),4.23(s,3H),3.84(q,2H),3.19(s,3H),2.19(s,3H),1.21(t, 3H).
Compounds 17:7.53(d,1H),7.39-7.42(m,2H),6.55(s,1H),4.14(s,3H),3.87(q,2H),2.21(s,3H),1.21(t, 3H).
Compounds 18:8.22(d,1H),7.68(d,1H),6.54(s,1H),5.08(s,2H),4.16(s,3H),3.58(s,3H),3.48(s,3H),3.27(s,3H),2.21(s, 3H).
Compounds 19:8.22(d,1H),7.68(d,1H),6.54(s,1H),5.08(s,2H),4.17(s,3H),3.86(q,2H),3.48(s,3H),3.27(s,3H),2.21(s,3H),1.21(t, 3H).
Compounds 20:8.22(d,1H),7.68(d,1H),6.54(s,1H),5.11(s,2H),4.17(s,3H),3.87(dd,2H),3.68(dd,2H),3.29(s,3H),2.21(s,3H),1.21-1.25(m, 6H).
Compounds 21:8.24(d,1H),7.72(d,1H),6.54(s,1H),5.34(s,2H),4.17(s,3H),4.01(q,2H),3.87(q,2H),3.24(s,3H),2.21(s,3H),1.21(t, 3H).
Compounds 22:8.04(d,1H),7.89(d,1H),6.64(s,1H),4.18(s,3H),3.93(q,2H),3.37(s,3H),2.73(s,3H),2.22(s,3H),1.09(t, 3H).
Compounds 23:8.21(d,1H),7.67(d,1H),6.54(s,1H),5.17(s,2H),4.17(s,3H),3.86(q,2H),3.74-3.77(m,2H),3.54-3.57(m,2H),3.33(s,3H),3.32(s,3H),2.21(s,3H),1.21(t, 3H).
Compounds 24:8.21(d,1H),7.67(d,1H),6.53(s,1H),5.18(s,2H),4.17(s,3H),4.05-4.08(m,1H),3.86(q,2H),3.71-3.83(m,2H),3.56-3.63(m,2H),3.32(s,3H),2.21(s,3H),1.82-1.97(m,3H),1.45-1.49(m, 1H).
Compounds 29:7.96-7.98(m,2H),7.77(d,1H),6.54(s,1H),4.16(s,3H),3.87(q,2H),3.11(s,3H),2.21(s,3H),1.19(t, 3H).
Compounds 79:8.27(s,1H),8.01-7.79(m,2H),4.11(s,3H),3.92(s,3H),3.22(s, 3H).
Compounds 80:8.32(s,1H),7.98(d,1H),7.78(d,1H),7.76(s,1H),4.03(s,3H),3.88(s,3H),3.25(s, 3H).
Compounds 82:8.36(s,1H),7.96(d,1H),7.77(d,1H),7.40(s,1H),4.02(s,3H),3.74(s,3H),3.25(s,3H),2.30(s, 3H).
Compounds 83:8.36(s,1H),7.96(d,1H),7.77(d,1H),7.45(s,1H),4.02(s,3H),3.99(q,2H),3.26(s,3H),2.31(s,3H),1.39(t, 3H).
Compounds 88:7.93(s,1H),7.88(d,1H),7.80(d,1H),7.58(dd,1H),4.09(s,3H),3.73(s,3H),2.22(s, 3H).
Compounds 96:8.17(d,1H),7.69(d,1H),5.18(d,2H),4.05-4.09(m,1H),4.00(s,3H),3.79-3.83(m,1H),3.77(s,3H),3.71-3.76(m,1H),3.63-3.65(m,1H),3.57-3.61(m,1H),3.32(s,3H),2.33(s,3H),1.92-1.98(m,1H),1.83-1.89(m,2H),1.53-1.59(m,1H), etc.
Compounds 140:8.32(s,1H),8.00(d,1H),7.93(d,1H),4.13(s,3H),3.94(s,3H),3.24(s,3H),2.49(q,2H),2.17(s,3H),1.16(t, 3H).
Compounds 142:8.35(s,1H),8.02(d,1H),7.84(d,1H),5.98(s,1H),4.28(q,2H),4.05(s,3H),3.22(s,3H),2.15(s,3H),1.34(t, 3H).
Compounds 164:8.10(d,1H),7.60(d,1H),5.93(s,1H),4.29(q,2H),4.06(s,3H),3.11(s,3H),2.74(s,3H),2.12(s,3H),1.32(t, 3H).
Compound 171:7.99(d,2H),7.84(d,1H),5.90(s,1H),4.34(q,2H),4.08(s,3H),3.11(s,3H),2.17(s,3H),1.37(t, 3H).
Examples of bioassay
Example 4 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 some of the compounds tested, compounds 9, 10, 15, 19, 20, 21, 22, 23, 24, 29, 80, 82 were administered at a dose of 600g a.i./hm2For zinnia, piemarker,The green bristlegrass and the barnyard grass have better control effect, and the control effect is more than 75 percent.
Part of the compound of formula I was tested with KC2 for zinnia control activity according to the above test methods, and the results are shown in Table 2.
Table 2: the general formula I partial compound and a control compound KC2 have the effect of preventing and killing zinnia elegans (after seedling, control effect%)
Figure BDA0001902026630000181
According to the above test method, part of the compounds of formula I and KC2 were tested for Abutilon control activity, and the results are shown in Table 3.
Table 3: the partial compound of the general formula I and a control compound KC2 have piemarker control activity (after seedling, control effect%)
Figure BDA0001902026630000182
Figure BDA0001902026630000191
According to the above test methods, part of the compounds of formula I was tested with KC1 and KC2 for their activity against barnyard grass, and the results are shown in Table 4.
Table 4: the activity of the part compound of the general formula I and control compounds KC1 and KC2 for preventing barnyard grass (after seedling, control effect%)
Figure BDA0001902026630000192
According to the test method, part of the compound shown in the general formula I is selected to be subjected to an activity test for controlling green bristlegrass with KC1 and KC2, and the results are shown in Table 5.
Table 5: the partial compound of the general formula I and control compounds KC1 and KC2 have setaria viridis activity (after seedling, control effect%)
Figure BDA0001902026630000193
Figure BDA0001902026630000201
Example 5 wheat safety test
Sowing a certain amount of wheat seeds in a paper cup with the diameter of 7cm and containing nutrient soil, covering soil of 1cm after sowing, compacting, spraying water, and culturing in a greenhouse according to a conventional method. When the wheat grows to 3 leaves, selecting a test material with uniform growth, and carrying out stem leaf spraying treatment (spraying pressure of 1.95 kg/cm) by using a crawler-type crop sprayer (designed and produced by Engineer Research Ltd. in England)2The amount of the sprayed liquid was 50mL/m2The track speed is 30cm/s, the nozzle is a fan-shaped nozzle), the test material is placed in an operation hall after being treated, and the test material is placed in a greenhouse for management according to a conventional method after the liquid medicine is naturally air-dried. After treatment, the reaction condition of wheat to the test compound is regularly observed, visual investigation is carried out 4 weeks after treatment, the inhibition rate is various damage degrees compared with a control, and is represented by 0-100%, and 0 represents no damage and 100% represents complete death.
Compound 82 of formula I was tested in parallel with KC1 for wheat safety and the results are shown in Table 6.
Table 6: part of compounds in the general formula I have safety (post-emergence damage rate%) to wheat
Figure BDA0001902026630000202
The compound with the general formula has herbicidal activity and can be used for controlling various weeds in agriculture. Meanwhile, the pyrazole amide compound disclosed by the invention has excellent herbicidal activity and is safe to crops.

Claims (7)

1. A pyrazole amide compound characterized by: the compound is shown as a general formula I:
Figure FDA0001902026620000011
q is the following group: q1、Q2、Q3
Figure FDA0001902026620000012
In the formula:
X1and X3Can be the same or different and is respectively selected from hydrogen, cyano, nitro, halogen and 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 or C3-C6A cycloalkyloxy group;
X2selected from hydrogen, cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Sulfoxide 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;
Y1is selected from 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;
R1is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl group,C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkoxy radical C1-C3Alkyl radical, C1-C6Halogenoalkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkylthio group C1-C3Alkyl radical, C1-C6Haloalkylthio C1-C3Alkyl radical, C1-C6Alkyl sulfoxide radical C1-C3Alkyl radical, C1-C6Halogenoalkylsulfonol C1-C3Alkyl radical, C1-C6Alkyl sulfone radical C1-C3Alkyl or C1-C6Halogenoalkylsulfonyl C1-C3An alkyl group;
R2selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl or C1-C6A haloalkyl group;
R3selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, C1-C6Alkoxy radical, C2-C6Alkenyl radical, C2-C6Alkynyl or phenyl which is unsubstituted or substituted by 1 to 5 substituents selected from cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C1-C6Alkoxy or C1-C6A haloalkoxy group.
2. A compound according to claim 1, wherein in formula I:
X1and X3Are the same or different and are respectively selected from cyano, nitro and halogen、C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C3Alkoxy radical, C1-C3Haloalkoxy, C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C3-C6Cycloalkyl or C3-C6A cycloalkyloxy group;
X2selected from hydrogen, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Sulfoxide 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-C6Alkyl halidesBase, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl or C3-C6A cycloalkoxy group;
Y1is selected from 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;
R1is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Haloalkenyl, C2-C6Alkynyl, C2-C6Halogenated alkynyl, C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkoxy radical C1-C3Alkyl radical, C1-C6Halogenoalkoxy radical C1-C3Alkyl radical, C1-C6Alkoxy radical C1-C3Alkoxy radical C1-C3Alkyl radical, C1-C6Alkylthio group C1-C3Alkyl radical, C1-C6Haloalkylthio C1-C3Alkyl radical, C1-C6Alkyl sulfoxide radical C1-C3Alkyl radical, C1-C6Halogenoalkylsulfonol C1-C3Alkyl radical, C1-C6Alkyl sulfone radical C1-C3Alkyl or C1-C6Halogenoalkylsulfonyl C1-C3An alkyl group;
R2selected from hydrogen, halogen, nitro, cyano, C1-C6Alkyl or C1-C6A haloalkyl group;
R3selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Halogenocycloalkyl, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C3Alkyl radical, C1-C6Alkoxy radical, C2-C6Alkenyl radical, C2-C6Alkynyl or phenyl which is unsubstituted or substituted by 1 to 5 substituents selected from cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C1-C6Alkoxy or C1-C6A haloalkoxy group.
3. A compound according to claim 2, wherein in formula I:
X1and X3Can be the same or different and is respectively selected from hydrogen, nitryl, halogen and C1-C6Alkylsulfonyl radical, C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C1-C6Alkyl or C1-C6A haloalkyl group;
X2selected from hydrogen, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkyl sulfonyl radical、C1-C6Haloalkylsulfonyl group, C1-C6Alkylsulfinyl radical, C1-C6Haloalkylsulfinyl radical, C1-C6Alkylthio radical, C1-C6Haloalkylthio, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, C3-C6Halogenocycloalkyl C1-C6Alkyl radical, Y1Oxy radical, Y1Oxy radical C1-C6Alkyl radical, Y1Thio radical C1-C6Alkyl radical, Y1Sulfoxide 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;
Y1is selected from 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, 5-to 7-membered heteroaromatic ring C containing 1-4 heteroatoms1-C6Alkyl, the following substituents are selected from nitro, halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Halogenated alkoxy、C3-C6Cycloalkyl or C3-C6A cycloalkoxy group;
R1is selected from C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical C1-C3Alkyl radical, C2-C6Alkenyl radical, C2-C6Alkynyl, C1-C6Alkylsulfonyl radical, C1-C6Alkylthio group C1-C3Alkyl radical, C1-C6Alkyl sulfoxide radical C1-C3Alkyl or C1-C6Alkyl sulfone radical C1-C3An alkyl group;
R2selected from hydrogen, halogen, nitro, cyano, C1-C3Alkyl or C1-C3A haloalkyl group;
R3selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl or phenyl which is unsubstituted or substituted by 1 to 5 substituents selected from cyano, nitro, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C3-C6Cycloalkyl radical, C1-C6Alkoxy or C1-C6A haloalkoxy group.
4. A compound according to claim 3, wherein in formula I:
X1and X3Can be the same or different and is respectively selected from hydrogen, nitryl, halogen and C1-C3Alkylsulfonyl radical, C1-C3Alkyl or C1-C3A haloalkyl group;
X2selected from hydrogen, halogen, C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkylsulfonyl radical, C3-C6Cycloalkyl radical, C3-C6Cycloalkyl radical C1-C6Alkyl radical, Y1Oxy radical, Y1Oxy radical C1-C3Alkyl radical, Y1Thio radical C1-C3Alkyl, 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 halogen and C1-C6Alkyl radical, C1-C6Haloalkyl, C1-C6Alkoxy radical, C1-C6Haloalkoxy, C3-C6Cycloalkyl or C3-C6A cycloalkoxy group;
Y1is selected from 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;
R1is selected from C1-C3Alkyl radical, C1-C3Alkylsulfonyl or C1-C3Alkyl sulfone radical C1-C3An alkyl group;
R2selected from hydrogen, halogen, C1-C3Alkyl or C1-C3A haloalkyl group;
R3selected from hydrogen, C1-C6Alkyl radical, C1-C6Haloalkyl or C3-C6A cycloalkyl 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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* Cited by examiner, † Cited by third party
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WO2014126070A1 (en) * 2013-02-15 2014-08-21 石原産業株式会社 Triazinone carboxamide compound or salt thereof
CN108290846A (en) * 2015-09-28 2018-07-17 拜耳作物科学股份公司 Acylated N- (1,2,5- oxadiazole -3- bases) -, N- (1,3,4- oxadiazole -2- bases) -, N- (tetrazolium -5- bases)-and N- (triazole -5- bases)-aryl carboxylic acid amides and its purposes as herbicide

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
WO2014126070A1 (en) * 2013-02-15 2014-08-21 石原産業株式会社 Triazinone carboxamide compound or salt thereof
CN108290846A (en) * 2015-09-28 2018-07-17 拜耳作物科学股份公司 Acylated N- (1,2,5- oxadiazole -3- bases) -, N- (1,3,4- oxadiazole -2- bases) -, N- (tetrazolium -5- bases)-and N- (triazole -5- bases)-aryl carboxylic acid amides and its purposes as herbicide

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117247363A (en) * 2023-11-17 2023-12-19 山东滨农科技有限公司 Oxadiazolone compound, weeding composition and application thereof

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