WO2020168997A1 - Dérivés d'isoxazoline et leurs utilisations en agriculture - Google Patents

Dérivés d'isoxazoline et leurs utilisations en agriculture Download PDF

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Publication number
WO2020168997A1
WO2020168997A1 PCT/CN2020/075509 CN2020075509W WO2020168997A1 WO 2020168997 A1 WO2020168997 A1 WO 2020168997A1 CN 2020075509 W CN2020075509 W CN 2020075509W WO 2020168997 A1 WO2020168997 A1 WO 2020168997A1
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Prior art keywords
alkyl
haloc
compound
cycloalkyl
och
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PCT/CN2020/075509
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English (en)
Inventor
Yitao LI
Jian Lin
Weilin CHI
Shuiming ZENG
Shuangzhi WU
Xinshuo LIU
Bingbing ZHANG
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Dongguan Hec Tech R&D Co., Ltd.
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Publication of WO2020168997A1 publication Critical patent/WO2020168997A1/fr

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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
    • A01P13/00—Herbicides; Algicides
    • A01P13/02—Herbicides; Algicides selective
    • 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
    • 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
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention provides a novel isoxazoline derivative and preparation method thereof; composition containing the compound and uses thereof in agriculture.
  • Isoxazoline compounds are a class of compounds with excellent biological activities, and their herbicidal activities have been described in literatures such as WO 2002062770, WO 2003000686 and WO 2003010165.
  • isoxazoline compounds used as active ingredients known from the above cited documents have disadvantages in use, for example, (a) no or only insufficient herbicidal effect on ruderal plants, (b) too narrow spectrum of ruderal plant to be controlled, or (c) too low selectivity for useful crops.
  • the present invention provides a novel isoxazoline compound having excellent herbicidal activity and excellent selectivity between crops and weeds.
  • Y is alkoxy, alkoxyalkoxy, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy or haloalkynyloxy;
  • each of R 1 and R 2 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, alkyl, haloalkyl, cycloalkyl or cycloalkylalkyl; or, R 1 and R 2 together with the carbon atom to which they are attached, form a 3-to 12-membered ring;
  • each of R 3 and R 4 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, alkyl, haloalkyl, cycloalkyl or cycloalkylalkyl; or, R 3 and R 4 together with the carbon atom to which they are attached, form a 3-to 12-membered ring;
  • each of R 5 and R 6 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, alkyl, alkenyl or alkynyl; or, R 5 and R 6 together with the carbon atom to which they are attached, form a 3-to 12-membered ring;
  • n 0, 1 or 2;
  • each m is independently 0, 1 or 2;
  • R 7 when Y is methoxy or difluoromethoxy, R 7 is ethyl or isopropyl, R 5 and R 6 are both hydrogen, n is 0 or 2, R 3 and R 4 are both hydrogen, and R 1 is methyl, R 2 is not chloromethyl; or, when Y is methoxy or difluoromethoxy, R 7 is ethyl or isopropyl, R 5 and R 6 are both hydrogen, n is 0 or 2, R 3 and R 4 are both hydrogen, and R 2 is methyl, R 1 is not chloromethyl.
  • Y is C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkoxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, haloC 1-6 alkoxy, haloC 2-6 alkenyloxy or haloC 2-6 alkynyloxy;
  • each of R 1 and R 2 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-6 alkyl, haloC 1-6 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl-C 1-6 alkyl; or, R 1 and R 2 together with the carbon atom to which they are attached, form a 3-to 8-membered ring;
  • each of R 3 and R 4 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-6 alkyl, haloC 1-6 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl-C 1-6 alkyl; or, R 3 and R 4 together with the carbon atom to which they are attached, form a 3-to 8-membered ring;
  • each of R 5 and R 6 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-6 alkyl, C 2-6 alkenyl or C 2-6 alkynyl; or, R 5 and R 6 together with the carbon atom to which they are attached, form a 3-to 8-membered ring;
  • each of R 1 and R 2 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-4 alkyl, haloC 1-4 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl-C 1-3 alkyl; or, R 1 and R 2 together with the carbon atom to which they are attached, form a 3-to 6-membered ring;
  • each of R 3 and R 4 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-3 alkyl, haloC 1-3 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl-C 1-3 alkyl; or, R 3 and R 4 together with the carbon atom to which they are attached, form a 3-to 6-membered ring;
  • each of R 5 and R 6 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-4 alkyl, C 2-4 alkenyl, or C 2-4 alkynyl; or, R 5 and R 6 together with the carbon atom to which they are attached, form a 3-to 6-membered ring.
  • provided herein is a compound having Formula (Ia) or a stereoisomer, an N-oxide or a salt thereof,
  • Y and R 7 are as defined herein.
  • Y is C 1-4 alkoxy, C 1-4 alkoxy-C 1-4 alkoxy, C 2-4 alkenyloxy, C 2-4 alkynyloxy, haloC 1-4 alkoxy, haloC 2-4 alkenyloxy or haloC 2-4 alkynyloxy.
  • R 7 is -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CH (CH 3 ) 2 , -CH 2 CH (CH 3 ) 2 , -CH 2 F, -CHF 2 , -CH 2 Cl, -CH 2 Br, -CF 3 , -CH 2 CF 3 , -CH 2 CH 2 F, -CH 2 CH 2 Cl, -CH 2 CH 2 Br, -CH 2 CHF 2 , -CH 2 CH 2 CF 3 , -CH 2 CH 2 CH 2 F, -CH 2 CH 2 CH 2 Cl, -CH 2 CH 2 CH 2 Br, -CHFCH 2 CH 3 , -CHClCH 2 CH 3 , cyclopropylmethyl, phenyl, 3-fluorophenyl, 2, 4-difluorophenyl or phenylsulfonyl.
  • the invention provides a composition comprising a compound disclosed herein, and further comprising at least one additional component required for the formulation.
  • the composition disclosed herein is a composition for weed control.
  • the invention provides the use of the compound or the composition comprising the compound described herein in agriculture.
  • the invention provides the use of the compound or the composition comprising the compound described herein for plant disease control.
  • the invention provides the use of the compound or the composition comprising the compound described herein in agriculture for weed control.
  • provided herein is the use of the compound or the composition comprising the compound described herein as an herbicide.
  • provided herein is the use of the compound or the composition comprising the compound described herein as a pre-emergent herbicide.
  • provided herein is the use of the compound or the composition comprising the compound described herein as a post-emergent herbicide.
  • the invention provides the use of the compound or the composition comprising the compound described herein for controlling unwanted plants.
  • the invention provides a method for controlling unwanted plants comprising applying an effective amount of the compound or the composition comprising the compound described herein to a plant, a plant seed, soil in which or on which the plant grows, or a cultivation area.
  • the invention provides a method for controlling growth of weed in a growing field of useful plant comprising applying an effective amount of the compound or the composition comprising the compound described herein to a plant, a plant seed, soil in which or on which the plant grows, or a cultivation area.
  • the weed comprises broadleaf weed and grass weed.
  • the broadleaf weed is abutilon theophrastis, amaranthus retroflexus or eclipta prostrata; and the grass weed is digitaria sanguinalis, echinochloa crusgalli or setaria viridis.
  • the useful plant is cotton, oilseed rape, soybean or peanut.
  • the compounds having Formula (I) or Formula (Ia) may exist in different stereoisomers or optical isomers or tautomers.
  • the present invention encompasses all such isomers and tautomers, as well as mixtures thereof in various ratios.
  • Any asymmetric atom (e.g., carbon or the like) of the compound (s) disclosed herein can be present in racemic or enantiomerically enriched, for example the (R) -, (S) -or (R, S) -configuration.
  • grammatical articles “a” , “an” and “the” are intended to include “at least one” or “one or more” unless otherwise indicated herein or clearly contradicted by the context.
  • the articles are used herein to refer to one or more than one (i.e. at least one) of the grammatical objects of the article.
  • a component means one or more components, and thus, possibly, more than one component is contemplated and may be employed or used in an implementation of the described embodiments.
  • Stereoisomers refers to compounds which have identical chemical constitution, but differ with regard to the arrangement of the atoms or groups in space. Stereoisomers include enantiomer, diastereomers, conformer (rotamer) , geometric (cis/trans) isomer, atropisomer, etc.
  • Enantiomers refer to two stereoisomers of a compound which are non-superimposable mirror images of one another.
  • Diastereomer refers to a stereoisomer with two or more centers of chirality and whose molecules are not mirror images of one another. Diastereomers have different physical properties e.g., melting point, boiling point, spectral properties and reactivity. Mixture of diastereomers may separate under high resolution analytical procedures such as electrophoresis and chromatography such as HPLC.
  • optically active compounds i.e., they have the ability to rotate the plane of plane-polarized light.
  • prefixes D and L, or R and S are used to denote the absolute configuration of the molecule about its chiral center (s) .
  • the prefixes d and l or (+) and (-) are employed to designate the sign of rotation of plane-polarized light by the compound, wherein the compound with the prefix (-) or l means levorotatory.
  • the compound with the prefix (+) or d means dextrorotatory.
  • a specific stereoisomer may be referred to as an enantiomer, and a mixture of such stereoisomers is called an enantiomeric mixture.
  • a 50: 50 mixture of enantiomers is referred to as a racemic mixture or a racemate, which may occur where there has been no stereoselection or stereospecificity in a chemical reaction or process.
  • compounds disclosed herein may optionally be substituted with one or more substituents, such as are illustrated generally below, or as exemplified by particular classes, subclasses, and species of the invention.
  • substituents such as are illustrated generally below, or as exemplified by particular classes, subclasses, and species of the invention.
  • the phrase “optionally substituted” is used interchangeably with the phrase “substituted or unsubstituted” .
  • substituted refers to the replacement of one or more hydrogen radicals in a given structure with the radical of a specified substituent.
  • an optionally substituted group may have a substituent at each substitutable position of the group.
  • substituents described herein include, but are not limited to, deuterium, fluorine, chlorine, bromine, iodine, cyano, hydroxy, nitro, amino, carboxy, alkyl, alkoxy, alkoxyalkyl, alkoxyalkoxy, alkoxyalkylamino, aryloxy, heteroaryloxy, heterocyclyloxy, arylalkoxy, heteroarylalkoxy, heterocyclylalkoxy, cycloalkylalkoxy, alkylamino, alkylaminoalkyl, alkylaminoalkylamino, cycloalkylamino, cycloalkylalkylamino, alkylthio, haloalkyl, haloalkoxy, hydroxy-substituted alkyl, hydroxy-substituted alkyl, hydroxy-substi
  • substituents of compounds disclosed herein are disclosed in groups or in ranges. It is specifically intended that the invention include each and every individual subcombination of the members of such groups and ranges.
  • the term “C 1 -C 6 alkyl” or “C 1-6 alkyl” is specifically intended to individually disclose methyl, ethyl, C 3 alkyl, C 4 alkyl, C 5 alkyl, and C 6 alkyl.
  • alkyl refers to a saturated linear or branched-chain monovalent hydrocarbon radical of 1 to 20 carbon atoms, wherein the alkyl radical may be optionally substituted with one or more substituents described herein. Unless otherwise specified, the alkyl group contains 1-20 carbon atoms. In some embodiments, the alkyl group contains 1-12 carbon atoms. In other embodiments, the alkyl group contains 1-10 carbon atoms. In some embodiments, the alkyl group contains 1-8 carbon atoms. In other embodiments, the alkyl group contains 1-6 carbon atoms. In other embodiments, the alkyl group contains 1-4 carbon atoms. In still other embodiments, the alkyl group contains 1-3 carbon atoms.
  • alkyl group examples include, methyl (Me, -CH 3 ) , ethyl (Et, -CH 2 CH 3 ) , n-propyl (n-Pr, -CH 2 CH 2 CH 3 ) , isopropyl (i-Pr, -CH (CH 3 ) 2 ) , n-butyl (n-Bu, -CH 2 CH 2 CH 2 CH 3 ) , isobutyl (i-Bu, -CH 2 CH (CH 3 ) 2 ) , sec-butyl (s-Bu, -CH (CH 3 ) CH 2 CH 3 ) , tert-butyl (t-Bu, -C (CH 3 ) 3 ) , n-pentyl (-CH 2 CH 2 CH 2 CH 3 ) , 2-pentyl (-CH (CH 3 ) CH 2 CH 2 CH 3 ) , 3-pentyl (-CH (CH 2 CH 3 )
  • alkenyl refers to a linear or branched-chain monovalent hydrocarbon radical of 2 to 12 carbon atoms with at least one site of unsaturation, i.e., a carbon-carbon, sp 2 double bond, wherein the alkenyl radical may be optionally substituted with one or more substituents described herein, and includes radicals having “cis” and “trans” orientations, or alternatively, “E” and “Z” orientations.
  • the alkenyl group contains 2-10 carbon atoms.
  • the alkenyl group contains 2-8 carbon atoms.
  • the alkenyl group contains 2-6 carbon atoms.
  • the alkenyl group contains 2-4 carbon atoms.
  • alkynyl refers to a linear or branched monovalent hydrocarbon radical of 2 to 12 carbon atoms with at least one site of unsaturation, i.e., a carbon-carbon, sp triple bond, wherein the alkynyl radical may be optionally substituted with one or more substituents described herein.
  • the alkynyl group contains 2-10 carbon atoms; in some embodiments, the alkynyl group contains 2-8 carbon atoms; in other embodiments, the alkynyl group contains 2-6 carbon atoms; and in still other embodiments, the alkynyl group contains 2-4 carbon atoms.
  • alkynyl groups include, but are not limited to, -C ⁇ CH, -C ⁇ CCH 3 , -CH 2 -C ⁇ CH, -CH 2 -C ⁇ CCH 3 , -CH 2 CH 2 -C ⁇ CH, -CH 2 -C ⁇ CCH 2 CH 3 , -CH 2 CH 2 -C ⁇ CCH 2 CH 3 , and the like.
  • alkenyloxy refers to an alkenyl group attached to the parent molecular moiety via an oxygen atom, wherein the alkenyl group is as defined herein.
  • alkynyloxy refers to an alkynyl group attached to the parent molecular moiety via an oxygen atom, wherein the alkynyl group is as defined herein. Examples of such groups include, but are not limited to, -O-C ⁇ CH, -O-C ⁇ CCH 3 , -O-CH 2 -C ⁇ CH, and the like.
  • alkoxy refers to an alkyl group attached to the parent molecular moiety via an oxygen atom, wherein the alkyl group is as defined herein. Unless otherwise specified, the alkoxy group contains 1-12 carbon atoms. In some embodiments, the alkoxy group contains 1-10 carbon atoms. In other embodiments, the alkoxy group contains 1-8 carbon atoms. In some embodiments, the alkoxy group contains 1-6 carbon atoms. In other embodiments, the alkoxy group contains 1-4 carbon atoms. In still other embodiments, the alkoxy group contains 1-3 carbon atoms. The alkoxy group may be optionally substituted with one or more substituents disclosed herein.
  • alkoxy group examples include methoxy (MeO, -OCH 3 ) , ethoxy (EtO, -OCH 2 CH 3 ) , 1-propoxy (n-PrO, n-propoxy, -OCH 2 CH 2 CH 3 ) , 2-propoxy (i-PrO, i-propoxy, -OCH (CH 3 ) 2 ) , 1-butoxy (n-BuO, n-butoxy, -OCH 2 CH 2 CH 2 CH 3 ) , 2-methyl-l-propoxy (i-BuO, i-butoxy, -OCH 2 CH (CH 3 ) 2 ) , 2-butoxy (s-BuO, s-butoxy, -OCH (CH 3 ) CH 2 CH 3 ) , 2-methyl-2-propoxy (t-BuO, t-butoxy, -OC (CH 3 ) 3 ) , 1-pentoxy (n-pentoxy, -OCH 2 CH 2 CH 3 ) ,
  • alkylamino refers to “N-alkylamino” and “N, N-dialkylamino” wherein amino groups are independently substituted with one alkyl radical or two alkyl radicals, respectively.
  • the alkylamino group is a lower alkylamino group that contains one or two C 1-6 alkyl attached to the nitrogen atom.
  • the alkylamino group is a lower alkylamino group that contains one C 1-3 alkyl group.
  • alkylamino group examples include monoalkylamino or dialkylamino such as N-methylamino, N-ethylamino, N, N-dimethylamino, N, N-diethylamino, and the like.
  • alkylthio refers to a linear or branched-alkyl radical attached to the rest of the molecular via a divalent sulfur atom, and wherein the alkyl group is as defined herein.
  • alkylthio include -SCH 3 , -SCH 2 CH 3 , -SCH 2 CH 2 CH 3 , and the like.
  • halogen refers to fluorine (F) , chlorine (Cl) , bromine (Br) , or iodine (I) .
  • haloalkyl refers to alkyl substituted with one or more halogen atoms.
  • haloalkyl group include, but are not limited to, -CH 2 F, -CHF 2 , -CH 2 Cl, -CH 2 Br, -CF 3 , -CH 2 CF 3 , -CH 2 CH 2 F, -CH 2 CH 2 Cl, -CH 2 CH 2 Br, -CH 2 CHF 2 , -CH 2 CH 2 CF 3 , -CH 2 CH 2 CH 2 F, -CH 2 CH 2 CH 2 Cl, -CH 2 CH 2 CH 2 Br, -CHFCH 2 CH 3 , -CHClCH 2 CH 3 , and the like.
  • haloalkoxy refers to an alkoxy, as the case may be, substituted with one or more halogen atoms.
  • haloalkoxy group include, but are not limited to, -OCH 2 F, -OCHF 2 , -OCH 2 Cl, -OCH 2 Br, -OCF 3 , -OCH 2 CF 3 , -OCH 2 CH 2 F, -OCH 2 CH 2 Cl, -OCH 2 CH 2 Br, -OCH 2 CHF 2 , -OCH 2 CH 2 CF 3 , -OCH 2 CH 2 CH 2 F, -OCH 2 CH 2 CH 2 Cl, -OCH 2 CH 2 CH 2 Br, -OCHFCH 2 CH 3 , -OCHClCH 2 CH 3 , and the like.
  • haloalkylamino refers to an alkylamino, as the case may be, substituted with one or more halogen atoms.
  • haloalkylthio refers to an alkylthio, as the case may be, substituted with one or more halogen atoms.
  • haloalkenyl refers to an alkenyl, as the case may be, substituted with one or more halogen atoms.
  • haloalkynyl refers to an alkynyl, as the case may be, substituted with one or more halogen atoms.
  • haloalkenyloxy refers to an alkenyloxy, as the case may be, substituted with one or more halogen atoms.
  • haloalkynyloxy refers to an alkynyloxy, as the case may be, substituted with one or more halogen atoms.
  • x-membered where x is an integer typically describes the number of ring-forming atoms in a moiety and the number of ring-forming atoms is x.
  • piperidyl is an example of a 6 membered heterocyclyl group.
  • 3-to 12-membered ring refers to the carbocyclic ring, heterocyclic ring or aromatic ring system having 3 to 12 ring members, i.e., the saturated, partial unsaturated or completely unsaturated ring system optionally containing one or more heteroatoms.
  • 3-to 10-membered ring refers to the carbocyclic ring, heterocyclic ring or aromatic ring system having 3 to 10 ring members, i.e., the saturated, partial unsaturated or completely unsaturated ring system optionally containing one or more heteroatoms.
  • 3-to 8-membered ring refers to the carbocyclic ring, heterocyclic ring or aromatic ring system having 3 to 8 ring members, i.e., the saturated, partial unsaturated or completely unsaturated ring system optionally containing one or more heteroatoms.
  • 3-to 6-membered ring refers to the carbocyclic ring, heterocyclic ring or aromatic ring system having 3 to 6 ring members, i.e., the saturated, partial unsaturated or completely unsaturated ring system optionally containing one or more heteroatoms.
  • carbocyclyl refers to a monovalent or multivalent, nonaromatic, saturated or partially unsaturated ring having 3 to 12 carbon atoms as a monocyclic, bicyclic or tricyclic ring system.
  • a carbobicyclyl group includes a spiro carbobicyclyl group or a fused carbobicyclyl group. Suitable carbocyclyl groups include, but are not limited to, cycloalkyl, cycloalkenyl and cycloalkynyl.
  • carbocyclyl groups include cyclopropyl, cyclobutyl, cyclopentyl, 1-cyclopent-l-enyl, l-cyclopent-2-enyl, l-cyclopent-3-enyl, cyclohexyl, 1-cyclohex-l-enyl, l-cyclohex-2-enyl, l-cyclohex-3-enyl, cyclohexadienyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, and the like.
  • cycloalkyl refers to a monovalent or multivalent saturated monocyclic, bicyclic or tricyclic system containing 3-12 carbon atoms. In some embodiments, the cycloalkyl group contains 3-12 carbon atoms; in some embodiments, the cycloalkyl group contains 3-10 carbon atoms; in other embodiments, the cycloalkyl group contains 3-8 carbon atoms; and in still other embodiments, the cycloalkyl group contains 3-6 carbon atoms.
  • the cycloalkyl group is optionally substituted with one or more substituents disclosed herein.
  • Such examples include, but are not limited to, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, adamantyl, and the like.
  • cycloalkylalkyl refers to an alkyl group substituted with cycloalkyl group, wherein the alkyl and cycloalkyl groups are as defined herein.
  • cycloalkenyl refers to a 3-to 12-membered monovalent or multivalent monocyclic, bicyclic, or tricyclic ring system containing at least one carbon-carbon double bond, wherein the ring system is non-aromatic.
  • the cycloalkenyl contains 3 to 10 carbon atoms.
  • the cycloalkenyl contains 3 to 8 carbon atoms.
  • the cycloalkenyl contains 3 to 6 carbon atoms.
  • the cycloalkenyl group is optionally substituted with one or more substituents disclosed herein. Some non-limiting examples include cyclobutenyl, cyclopentenyl, cyclohexenyl, cyclohexadienyl, and the like.
  • unsaturated refers to a moiety having one or more units of unsaturation.
  • heteroatom refers to oxygen (O) , sulfur (S) , nitrogen (N) , phosphorus (P) and silicon (Si) , including any oxidized form of nitrogen (N) , sulfur (S) , or phosphorus (P) ; primary amine, secondary amine, tertiary amine and quaternary ammonium forms; or a substitutable nitrogen of a heterocyclic ring, for example, N (as in 3, 4-dihydro-2H-pyrrolyl) , NH (as in pyrrolidyl) or NR (as in N-substituted pyrrolidyl) .
  • heterocycle refers to a saturated or partially unsaturated monocyclic, bicyclic or tricyclic ring containing 3-15 ring atoms of which at least one ring atom is selected from nitrogen, sulfur and oxygen, and no aromatic ring exists in the monocyclic, bicyclic or tricyclic ring.
  • the sulfur can be optionally oxygenized to S-oxide.
  • the nitrogen atom can be optionally oxygenized to N-oxide.
  • the heterocyclyl group include oxiranyl, azetidinyl, oxetanyl, thietanyl, pyrrolidyl (i.e., 2-pyrrolidyl) , 2-pyrrolinyl, 3-pyrrolinyl, pyrazolidinyl, imidazolinyl, imidazolidinyl, tetrahydrofuranyl, dihydrofuranyl, tetrahydrothienyl, dihydrothienyl, 1,3-dioxolanyl, dithiolanyl, tetrahydropyranyl, dihydropyranyl, 2H-pyranyl, 4H-pyranyl, tetrahydrothiopyranyl, piperidyl (2-piperidyl, 3-piperidyl, 4-piperidyl) , morpholinyl, thiomorpholinyl,
  • heterocyclyl with oxidized ring sulfur atom include sulfolanyl and 1, 1-dioxo-thiomorpholinyl.
  • the hetercyclyl group is optionally substituted with one or more substituents disclosed herein.
  • heterocyclylalkyl refers to an alkyl substituted with heterocyclyl, wherein the heterocyclyl and alkyl are as defined herein.
  • heterocyclyloxy refers to an optionally subsituted heterocyclyl group attached to the parent molecular moiety via an oxygen atom, wherein the heterocyclyl group is as defined herein.
  • aryl refers to monocyclic, bicyclic and tricyclic carbocyclic ring systems having a total of 6 to 14 ring members, or 6 to12 ring members, or 6 to 10 ring members, wherein at least one ring in the system is aromatic, wherein each ring in the system contains 3 to 7 ring members and that has a single point or multipoint of attachment to the rest of the molecule.
  • aryl may be used interchangeably with the term “aromatic ring” . Examples of aryl ring may include phenyl, indenyl, naphthyl and anthryl. The aryl group is optionally substituted with one or more substituents disclosed herein.
  • arylalkyl refers to an alkyl group substituted with one or more aryl groups, and the arylalkyl group attaches to the rest of the molecular via the alkyl group, wherein the alkyl and aryl groups are as defined herein.
  • aryloxy refers to an optionally substituted aryl group attached to the rest of the molecule via an oxygen atom, wherein the aryl group is as defined herein.
  • heteroaryl refers to a monocyclic, bicyclic, or tricyclic ring system having a total of 5 to 12 ring members, preferably, 5 to 10 ring members, and more preferably 5 to 6 ring members, wherein at least one ring in the system is aromatic and at least one ring in the system contains one or more heteroatoms, and wherein each ring in the system contains 5 to 7 ring members and the heteroaryl group has one or more points of attachment to the rest of the molecule.
  • heteroaryl may be used interchangeably with the term “heteroaryl ring” , “aromatic heterocyclic” , “heteroaromatic compound” or the term “heteroaromatic” .
  • the heteroaryl group is optionally substituted with one or more substituents disclosed herein.
  • the heteroaryl group is a 5-to 10-membered heteroaryl comprising 1, 2, 3 or 4 heteroatoms independently selected from O, S and N.
  • the ring atom of the heteroaryl group comprises 1-9 carbon atoms and 1-4 heteroatoms selected from N, O or S; in another embodiment, the ring atom of the heteroaryl group comprises 1-5 carbon atoms and 1-4 heteroatoms selected from N, O or S.
  • the heteroaryl group refers to a 5-membered or 6-membered heteroaryl containg 1-4 N atoms; in other embodiments, the heteroaryl group refers to a 5-membered heteroaryl containg 1-3 heteroatoms selected from N, O or S; in other embodiments, the heteroaryl group refers to a 5-membered heteroaryl containg 1-3 heteroatoms selected from N or O; in other embodiments, the heteroaryl group refers to a 5-membered heteroaryl containg 1-3 heteroatoms selected from N or S.
  • heteroaryl group examples include 2-furyl, 3-furyl, N-imidazolyl, 2-imidazolyl, 4-imidazolyl, 5-imidazolyl, 3-isoxazolyl, 4-isoxazolyl, 5-isoxazolyl, 2-oxazolyl, 4-oxazolyl, 5-oxazolyl, N-pyrrolyl, 2-pyrrolyl, 3-pyrrolyl, 2-pyridyl, 3-pyridyl, 4-pyridyl, 2-pyrimidinyl, 4-pyrimidinyl, 5-pyrimidinyl, pyridazinyl (e.g., 3-pyridazinyl) , 2-thiazolyl, 4-thiazolyl, 5-thiazolyl, tetrazolyl (e.g., 5-tetrazolyl) , triazolyl (e.g., 2-triazolyl and 5-triazolyl) , 2-thienyl, 3-thien
  • heteroarylalkyl refers to an alkyl group substituted with one or more heteroaryl groups, and the heteroarylalkyl group attaches to the rest of the molecular via the alkyl group, wherein the alkyl and heteroaryl group are as defined herein.
  • alkoxyalkoxy refers to an alkoxy group substituted with one or more alkoxy groups, wherein the alkoxy group is as defined herein.
  • salts of the compounds of the invention include those derived from alkali or alkaline earth metals and those derived from ammonia or amines.
  • Preferred cations include sodium, potassium, magnesium, and ammonium cations having the formula N + (R 19 R 20 R 21 R 22 ) , wherein each R 19 , R 20 , R 21 and R 22 is independently selected from hydrogen, C 1 -C 6 alkyl and C 1 -C 6 hydroxyalkyl.
  • the salt of the compound of Formula (I) or Formula (Ia) can be obtained by using a metal hydroxide such as sodium hydroxide or an amine such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine or benzylamine) to treat a compound of Formula (I) or Formula (Ia) .
  • a metal hydroxide such as sodium hydroxide or an amine such as ammonia, trimethylamine, diethanolamine, 2-methylthiopropylamine, bisallylamine, 2-butoxyethylamine, morpholine, cyclododecylamine or benzylamine
  • an acceptable salt may be formed from organic acid and inorganic acid, such as acetic acid, propionic acid, lactic acid, citric acid, tartaric acid, succinic acid, fumaric acid, maleic acid, malonic acid, mandelic acid, malic acid, phthalic acid, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, methanesulfonic acid, naphthalenesulfonic acid, benzenesulfonic acid, toluenesulfonic acid, camphorsulfonic acid, and the known acceptable acid.
  • organic acid and inorganic acid such as acetic acid, propionic acid, lactic acid, citric acid, tartaric acid, succinic acid, fumaric acid, maleic acid, malonic acid, mandelic acid, malic acid, phthalic acid, hydrochloric acid, hydrobromic acid, phosphoric acid, nitric acid, sulfuric acid, methanesulfonic acid
  • the present invention is aimed to provide a novel isoxazoline compound, an herbicidal composition and formulation containing the compound, and uses thereof.
  • a compound having Formula (I) or a stereoisomer, an N-oxide or a salt thereof is provided herein.
  • Y is alkoxy, alkoxyalkoxy, alkenyloxy, alkynyloxy, haloalkoxy, haloalkenyloxy or haloalkynyloxy;
  • each of R 1 and R 2 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, alkyl, haloalkyl, cycloalkyl or cycloalkylalkyl; or, R 1 and R 2 together with the carbon atom to which they are attached, form a 3-to 12-membered ring;
  • each of R 3 and R 4 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, alkyl, haloalkyl, cycloalkyl or cycloalkylalkyl; or, R 3 and R 4 together with the carbon atom to which they are attached, form a 3-to 12-membered ring;
  • each of R 5 and R 6 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, alkyl, alkenyl or alkynyl; or, R 5 and R 6 together with the carbon atom to which they are attached, form a 3-to 12-membered ring;
  • n 0, 1 or 2;
  • each m is independently 0, 1 or 2;
  • R 7 when Y is methoxy or difluoromethoxy, R 7 is ethyl or isopropyl, R 5 and R 6 are both hydrogen, n is 0 or 2, R 3 and R 4 are both hydrogen, and R 1 is methyl, R 2 is not chloromethyl; or, when Y is methoxy or difluoromethoxy, R 7 is ethyl or isopropyl, R 5 and R 6 are both hydrogen, n is 0 or 2, R 3 and R 4 are both hydrogen, and R 2 is methyl, R 1 is not chloromethyl.
  • the inventor of the present application found by activity test that the compound having Formula (I) has superior effect for weed control when Y, R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , and R 7 are confirmed, and n is 2 in Formula (I) .
  • Y is C 1-6 alkoxy, C 1-6 alkoxy-C 1-6 alkoxy, C 2-6 alkenyloxy, C 2-6 alkynyloxy, haloC 1-6 alkoxy, haloC 2-6 alkenyloxy or haloC 2-6 alkynyloxy.
  • each of R 1 and R 2 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-6 alkyl, haloC 1-6 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl-C 1-6 alkyl; or, R 1 and R 2 together with the carbon atom to which they are attached, form a 3-to 8-membered ring.
  • each of R 3 and R 4 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-6 alkyl, haloC 1-6 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl-C 1-6 alkyl; or, R 3 and R 4 together with the carbon atom to which they are attached, form a 3-to 8-membered ring.
  • each of R 5 and R 6 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-6 alkyl, C 2-6 alkenyl , or C 2-6 alkynyl; or, R 5 and R 6 together with the carbon atom to which they are attached, form a 3-to 8-membered ring.
  • provided herein is a compound having Formula (Ia) or a stereoisomer, an N-oxide or a salt thereof,
  • Y and R 7 are as defined herein.
  • each of R 1 and R 2 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-4 alkyl, haloC 1-4 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl-C 1-3 alkyl; or, R 1 and R 2 together with the carbon atom to which they are attached, form a 3-to 6-membered ring.
  • each of R 3 and R 4 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-3 alkyl, haloC 1-3 alkyl, C 3-6 cycloalkyl or C 3-6 cycloalkyl-C 1-3 alkyl; or, R 3 and R 4 together with the carbon atom to which they are attached, form a 3-to 6-membered ring.
  • each of R 5 and R 6 is independently hydrogen, fluorine, chlorine, bromine, iodine, amino, nitro, cyano, hydroxy, carboxy, C 1-4 alkyl, C 2-4 alkenyl, or C 2-4 alkynyl; or, R 5 and R 6 together with the carbon atom to which they are attached, form a 3-to 6-membered ring.
  • Y is C 1-4 alkoxy, C 1-4 alkoxy-C 1-4 alkoxy, C 2-4 alkenyloxy, C 2-4 alkynyloxy, haloC 1-4 alkoxy, haloC 2-4 alkenyloxy or haloC 2-4 alkynyloxy.
  • R 7 is -CH 3 , -CH 2 CH 3 , -CH 2 CH 2 CH 3 , -CH (CH 3 ) 2 , -CH 2 F, -CHF 2 , -CH 2 Cl, -CH 2 Br, -CF 3 , -CH 2 CF 3 , -CH 2 CH 2 F, -CH 2 CH 2 Cl, -CH 2 CH 2 Br, -CH 2 CHF 2 , -CH 2 CH 2 CF 3 , -CH 2 CH 2 CH 2 F, -CH 2 CH 2 CH 2 Cl, -CH 2 CH 2 CH 2 Br, -CHFCH 2 CH 3 , -CHClCH 2 CH 3 , phenyl, 3-fluorophenyl, 2, 4-difluorophenyl or phenylsulfonyl.
  • provided herein is a compound having Formula (Ia) or a stereoisomer, an N-oxide or a salt thereof,
  • Y is haloC 1-4 alkoxy
  • R 7 is C 1-4 alkyl or halo C 1-4 alkyl.
  • Y is haloC 1-2 alkoxy
  • R 7 is C 1-2 alkyl or halo C 1-2 alkyl.
  • Y is -OCH 2 F, -OCHF 2 , -OCF 3 , -OCH 2 CHF 2 or -OCH 2 CF 3 ;
  • R 7 is -CH 3 , -CH 2 CH 3 , -CF 3 , -CH 2 CH 2 F, -CH 2 CHF 2 or -CH 2 CF 3 .
  • Y is -OCHF 2 , -OCH 2 CHF 2 or -OCH 2 CF 3 ;
  • R 7 is -CH 3 , -CH 2 CH 3 or -CH 2 CF 3 .
  • the invention provides a composition comprising the compound described herein.
  • the composition further comprises at least one additional component required for the formulation.
  • the composition disclosed herein is a composition for weed control.
  • the invention provides the use of the compound or the composition comprising the compound described herein in agriculture.
  • provided herein is the use of the compound or the composition comprising the compound described herein as an herbicide.
  • provided herein is the use of the compound or the composition comprising the compound described herein as a pre-emergent herbicide.
  • provided herein is the use of the compound or the composition comprising the compound described herein as a post-emergent herbicide.
  • the invention provides the use of the compound or the composition comprising the compound described herein for plant disease control.
  • the invention provides the use of the compound or the composition comprising the compound described herein for controlling unwanted plants.
  • the invention provides a method for controlling unwanted plants comprising applying an effective amount of the compound or the composition comprising the compound described herein to a plant, a plant seed, soil in which or on which the plant grows, or a cultivation area.
  • provided herein is a method for controlling the growth of weed in a growing field of useful plant comprising applying an effective amount of the compound or the composition comprising the compound described herein to the field before seedling.
  • the weed comprises broadleaf weed and grass weed.
  • the broadleaf weed is abutilon theophrastis, amaranthus retroflexus or eclipta prostrata.
  • the grass weed is digitaria sanguinalis, echinochloa crusgalli or setaria viridis.
  • the useful plant is cotton, oilseed rape, soybean or peanut.
  • the compound provided herein is a novel compound which is more effective for weeds, lower in cost, less toxic, and safe to crops.
  • the compound of the present invention is generally useful as herbicidal active ingredient in compositions or formulation, wherein the composition or formulation has at least one additional component selected from surfactant, solid diluent, liquid diluent, wetting agent, dispersant, emulsifier, thickener, disintegrating agent, antifreeze agent, defoaming agent, preservative and stabilizer, etc., which meet the requirements of pesticides are all within the scope of the present invention.
  • the formulation or composition ingredients are selected to be consistent with the physical properties of the active ingredients, mode of application and environmental factors such as soil type, moisture and temperature.
  • Liquid compositions include solutions (including emulsifiable concentrates) , suspensions, emulsions (including microemulsions and/or suspoemulsions) and the like, which optionally can be thickened into gels.
  • aqueous liquid compositions are soluble concentrate, suspension concentrate, capsule suspension, concentrated emulsion, microemulsion and suspo-emulsion.
  • nonaqueous liquid compositions are emulsifiable concentrate, microemulsifiable concentrate, dispersible concentrate and oil dispersion.
  • compositions are dusts, powders, granules, pellets, prills, pastilles, tablets, filled films (including seed coatings) and the like, which can be water-dispersible ( “wettable” ) or water-soluble. Films and coatings formed from film-forming solutions or flowable suspensions are particularly useful for seed treatment.
  • Active ingredient can be (micro) encapsulated and further formed into a suspension or solid formulation; alternatively the entire formulation of active ingredient can be encapsulated (or “overcoated” ) . Encapsulation can control or delay the release of the active ingredient.
  • An emulsifiable granule combines the advantages of both an emulsifiable concentrate formulation and a dry granular formulation. High-strength compositions are primarily used as intermediates for other formulation.
  • Sprayable formulations are typically extended in a suitable medium before spraying. Such liquid and solid formulations are formulated to be readily diluted in the spray medium, usually water. Spray volumes can range from about one to several thousand liters per hectare, but more typically are in the range from about ten to several hundred liters per hectare. Sprayable formulations can be in tank mixed with water or another suitable medium for foliar treatment by aerial or ground application, or for application to the growing medium of the plant. Liquid and dry formulations can be metered directly into drip irrigation systems or metered into the furrow during planting.
  • the formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up to 100 percent by weight.
  • Solid diluents include, for example, clays such as bentonite, montmorillonite, attapulgite and kaolin, gypsum, cellulose, titanium dioxide, zinc oxide, starch, dextrin, sugars (e.g., lactose, sucrose) , silica, talc, mica, diatomaceous earth, urea, calcium carbonate, sodium carbonate and sodium bicarbonate, and sodium sulfate.
  • Typical solid diluents are described in Watkins et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey.
  • Liquid diluents include, for example, water, N, N-dimethylalkanamides (e.g., N, N-dimethylformamide) , limonene, dimethyl sulfoxide, N-alkylpyrrolidones (e.g., N-methylpyrrolidinone) , ethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, polypropylene glycol, propylene carbonate, butylene carbonate, paraffins (e.g., white mineral oils, normal paraffins, isoparaffins) , alkylbenzenes, alkylnaphthalenes, glycerine, glycerol triacetate, sorbitol, aromatic hydrocarbons, dearomatized aliphatics, alkylbenzenes, alkylnaphthalenes, ketones such as cyclohexanone, 2-heptanone, isophorone and 4-hydroxy-4-
  • Liquid diluents also include glycerol esters of saturated and unsaturated fatty acids (typically C 6 -C 22 ) such as plant seed and fruit oils (e.g, oils of olive, castor, linseed, sesame, corn (maize) , peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel) , animal-sourced fats (e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil) , and mixtures thereof.
  • plant seed and fruit oils e.g, oils of olive, castor, linseed, sesame, corn (maize) , peanut, sunflower, grapeseed, safflower, cottonseed, soybean, rapeseed, coconut and palm kernel
  • animal-sourced fats e.g., beef tallow, pork tallow, lard, cod liver oil, fish oil
  • Liquid diluents also include alkylated fatty acids (e.g., methylated, ethylated, butylated) wherein the fatty acids may be obtained by hydrolysis of glycerol esters from plant and animal sources, and can be purified by distillation.
  • alkylated fatty acids e.g., methylated, ethylated, butylated
  • Typical liquid diluents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950.
  • the solid and liquid compositions of the present invention often include one or more surfactants.
  • surfactants also known as “surface-active agents”
  • surface-active agents generally modify, most often reduce the surface tension of the liquid.
  • surfactants can be useful as wetting agents, dispersants, emulsifiers or defoaming agents.
  • Nonionic surfactants useful for the present compositions include, but are not limited to: alcohol alkoxylates such as alcohol alkoxylates based on natural and synthetic alcohols (which may be branched or linear) and prepared from the alcohols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof; amine ethoxylates, alkanolamides and ethoxylated alkanolamides; alkoxylated triglycerides such as ethoxylated soybean, castor and rapeseed oils; alkylphenol alkoxylates such as octylphenol ethoxylates, nonylphenol ethoxylates, dinonyl phenol ethoxylates and dodecyl phenol ethoxylates (prepared from the phenols and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof) ; block polymers prepared from ethylene oxide or propylene oxide or propylene oxide or mixtures thereof) ; block poly
  • Useful anionic surfactants include, but are not limited to: alkylaryl sulfonic acids and their salts; carboxylated alcohol or alkylphenol ethoxylates; diphenyl sulfonate derivatives; lignin and lignin derivatives such as lignosulfonates; maleic or succinic acids or their anhydrides; olefin sulfonates; phosphate esters such as phosphate esters of alcohol alkoxylates, phosphate esters of alkylphenol alkoxylates and phosphate esters of styryl phenol ethoxylates; protein-based surfactants; sarcosine derivatives; styryl phenol ether sulfate; sulfates and sulfonates of oils and fatty acids; sulfates and sulfonates of ethoxylated alkylphenols; sulfates of alcohols; sulfates of e
  • Useful cationic surfactants include, but are not limited to: amides and ethoxylated amides; amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxylated amines, ethoxylated diamines and propoxylated amines (prepared from the amines and ethylene oxide, propylene oxide, butylene oxide or mixtures thereof) ; amine salts such as amine acetates and diamine salts; quaternary ammonium salts such as quaternary salts, ethoxylated quaternary salts and diquaternary salts; and amine oxides such as alkyldimethylamine oxides and bis- (2-hydroxyethyl) -alkylamine oxides.
  • amines such as N-alkyl propanediamines, tripropylenetriamines and dipropylenetetramines, and ethoxyl
  • compositions i.e. final mixtures
  • nonionic and anionic surfactants or mixtures of nonionic and cationic surfactants.
  • Nonionic, anionic and cationic surfactants and their recommended uses are disclosed in a variety of published references including McCutcheon's Emulsi ⁇ ers and Detergents, annual American and International Editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964; and A. S. Davidson and B. Milwidsky, Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987.
  • compositions of this invention may also contain formulation auxiliaries and additives, known to those skilled in the art as formulation aids (some of which may be considered to also function as solid diluents, liquid diluents or surfactants) .
  • formulation auxiliaries and additives may control: pH (buffers) , foaming during processing (antifoams such polyorganosiloxanes) , sedimentation of active ingredients (suspending agents) , viscosity (thixotropic thickeners) , in-container microbial growth (antimicrobials) , product freezing (antifreezes) , color (dyes/pigment dispersions) , wash-off (film formers or stickers) , evaporation (evaporation retardants) , and other formulation attributes.
  • Film formers include, for example, polyvinyl acetates, polyvinyl acetate copolymers, polyvinylpyrrolidone-vinyl acetate copolymer, polyvinyl alcohols, polyvinyl alcohol copolymers and waxes.
  • formulation auxiliaries and additives include those listed in McCutcheon's Volume 2: Functional Materials, annual International and North American editions published by McCutcheon's Division, The Manufacturing Confectioner Publishing Co.; and PCT Publication WO 03/024222.
  • the compounds of the invention and any other active ingredients are typically incorporated into the present compositions by dissolving the active ingredient in a solvent or by grinding in a liquid or dry diluent.
  • Solutions, including emulsifiable concentrates can be prepared by simply mixing the ingredients. If the solvent of a liquid composition intended for use as an emulsifiable concentrate is water-immiscible, an emulsifier is typically added to emulsify the active-containing solvent upon dilution with water.
  • Active ingredient slurries, with particle diameters of up to 2,000 ⁇ m can be wet milled using media mills to obtain particles with average diameters below 3 ⁇ m.
  • Aqueous slurries can be made into finished suspension concentrates (see, for example, U.S. 3,060,084) or further processed by spray drying to form water-dispersible granules. Dry formulations usually require dry milling processes, which produce average particle diameters in the 2 to 10 ⁇ m range. Dusts and powders can be prepared by blending and usually grinding (such as with a hammer mill or fluid-energy mill) . Granules and pellets can be prepared by spraying the active material upon preformed granular carriers or by agglomeration techniques.
  • Pellets can be prepared as described in U.S. 4,172,714.
  • Water-dispersible and water-soluble granules can be prepared as proposed in U.S. 4,144,050, U.S. 3,920,442 and DE 3,246,493.
  • Tablets can be prepared as proposed in U.S. 5,180,587, U.S. 5,232,701 and U.S. 5,208,030.
  • Films can be prepared as proposed in GB 2,095,558 and U.S. 3,299,566.
  • the herbicide of the present invention can be used by spraying to a plant, applying it to the soil, or applying it to the surface of water.
  • the amount of the active component is appropriately determined to meet the application purpose.
  • the content of the active component is appropriately determined according to the purpose.
  • the amount of the compound of the invention depends on the kind of the compound to be used, the target weed, the tendency of the weed to appear, the environmental conditions, the type of the herbicide, and the like.
  • the form of the herbicide itself of the present invention is used, for example, in the form of a powder or granules, it is suitably used in an amount of from 1 g to 50 kg, preferably from 10 g to 10 kg per hectare, of the active ingredient.
  • the herbicide of the present invention is used in the form of a liquid, for example, in the form of an emulsifiable concentrate, a wettable powder or a flowable preparation, it is suitably used in an amount of from 0.1 to 50,000 ppm, preferably from 10 to 10,000 ppm.
  • the invention provides a method of controlling weeds in crops of useful plants, comprising applying to said weeds, the locus of said weeds, said useful crop plants or the locus of said useful crop plants a compound or a composition of the invention.
  • the invention also provides a method of selectively controlling grasses and/or weeds in crops of useful plants which comprises applying to the useful plants, locus thereof or the area of cultivation a herbicidally effective amount of a compound of Formula (I) or Formula (Ia) .
  • herbicide denotes a compound which controls or modifies the growth of plants.
  • herbicidally effective amount indicates the quantity of such a compound or combination of such compounds which is capable of producing a controlling or modifying effect on the growth of plants. Controlling or modifying effects include all deviation from natural development, for example: killing, retardation, leaf burn, albinism, dwarfing and the like.
  • plants refers to all physical parts of a plant, including seeds, seedlings, saplings, roots, tubers, stems, stalks, foliage and fruits.
  • locus is intended to include soil, seeds, and seedlings, as well as established vegetation and includes not only areas where weeds may already be growing, but also areas where weeds have yet to emerge, and also to areas under cultivation with respect to crops of useful plants.
  • “Areas under cultivation” include land on which the crop plants are already growing and land intended for cultivation with such crop plants.
  • weeds as used herein means any undesired plant, and thus includes not only agronomically important weeds as described below, but also volunteer crop plants.
  • Crops of useful plants in which the composition according to the invention can be used include, but are not limited to, perennial crops, such as citrus fruit, grapevines, nuts, oil palms, olives, pome fruit, stone fruit and rubber, and annual arable crops, such as cereals, for example barley and wheat, cotton, oilseed rape, maize, rice, soy beans, sugar beet, sugar cane, sunflowers, ornamentals, switchgrass, turf and vegetables, especially cereals, maize and soy beans.
  • perennial crops such as citrus fruit, grapevines, nuts, oil palms, olives, pome fruit, stone fruit and rubber
  • annual arable crops such as cereals, for example barley and wheat, cotton, oilseed rape, maize, rice, soy beans, sugar beet, sugar cane, sunflowers, ornamentals, switchgrass, turf and vegetables, especially cereals, maize and soy beans.
  • the grasses and weeds to be controlled may be both monocotyledonous species, for example Agrostis, Alopecurus, Avena, Brachiaria, Bromus, Cenchrus, Cyperus, Digitaria, Echinochloa, Eriochloa, Lolium, Monochoria, Panicum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sida and Sorghum, and dicotyledonous species, for example Abutilon, Amaranthus, Chenopodium, Chrysanthemum, Euphorbia, Galium, Ipomoea, Kochia, Nasturtium, Polygonum, Sida, Sinapis, Solanum, Stellaria, Veronica, Viola and Xanthium.
  • Agrostis Alopecurus
  • Avena Brachiaria
  • Bromus Cenchrus
  • Cyperus Digitaria
  • Echinochloa Eriochloa
  • Lolium Monochori
  • Compounds of this invention may show tolerance to important agronomic crops including, but are not limited to, alfalfa, barley, cotton, wheat, rape, sugar beets, corn (maize) , sorghum, soybeans, rice, oats, peanuts, vegetables, tomato, potato, perennial plantation crops including coffee, cocoa, oil palm, rubber, sugarcane, citrus, grapes, fruit trees, nut trees, banana, plantain, pineapple, hops, tea and forests such as eucalyptus and conifers (e.g., loblolly pine) , and turf species (e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass) .
  • turf species e.g., Kentucky bluegrass, St. Augustine grass, Kentucky fescue and Bermuda grass
  • the compounds of Formula (I) or Formula (Ia) in the invention may also be combined with other active ingredients, such as other herbicides and/or insecticides and/or acaricides and/or nematicides and/or molluscicides and/or fungicides and/or plant growth regulators.
  • active ingredients such as other herbicides and/or insecticides and/or acaricides and/or nematicides and/or molluscicides and/or fungicides and/or plant growth regulators.
  • the mixtures of the invention also include mixtures of two or more different compounds having Formula (I) or Formula (Ia) .
  • the invention also relates to a composition of the invention comprising at least one additional herbicide in addition to a compound having Formula (I) or Formula (Ia) .
  • the compound is characterized by the corresponding structure.
  • the compounds disclosed herein may be prepared by methods described herein, except where further noted. The following synthetic schemes and examples are provided to further illustrate the contents of the present invention.
  • Compound having Formula (5a) can be prepared according to the procedure described in Scheme 1, wherein R 2a is alkyl, alkoxyalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl or haloalkynyl; R 7 is as defined herein.
  • Compound having Formula (a’) can react with thiourea in HBr to give compound having Formula (b’) ; ethyl difluoroacetoacetate can react with R 1 NHNH 2 to give a compound having Formula (1a) and compound having Formula (1b) ; the compound having Formula (1a) can react with R 2a -Cl to give a compound having Formula (2a) ; the compound having Formula (2a) can react with paraformaldehyde and hydrochloric acid to give a compound having Formula (3a) ; the compound having Formula (3a) with a compound having Formula (b’) in an alkaline condition (such as K 2 CO 3 ) can undergo condensation reaction to give a compound having Formula (4a) ; the compound having Formula (4a) can further be oxidized to give a compound having Formula (5a) .
  • alkaline condition such as K 2 CO 3
  • Compound having Formula (5b) can be prepared according to the procedure described in Scheme 2, wherein R 2a is alkyl, alkoxyalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl or haloalkynyl; R 7 is as defined herein.
  • Compound having Formula (1b) can react with R 2a -Cl to give a compound having Formula (2b) ; the compound having Formula (2b) can react with paraformaldehyde and hydrochloric acid to give a compound having Formula (3b) ; the compound having Formula (3b) with a compound having Formula (b’) in an alkaline condition (such as K 2 CO 3 ) can undergo condensation reaction to give a compound having Formula (4b) ; the compound having Formula (4b) can further be oxidized to give a compound having Formula (5b) .
  • an alkaline condition such as K 2 CO 3
  • Compound having Formula (5a) can be prepared according to the procedure described in Scheme 3, wherein R 2a is alkyl, alkoxyalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl or haloalkynyl; R 7 is as defined herein.
  • Ethyl difluoroacetoacetate can first react with hydrazine hydrate to give a product, which then can react with phosphorus oxychloride to give an intermidate, and the intermidate can react with R 7 -I to give a compound having Formula (1c) and compound having Formula (1d) ;
  • the compound having Formula (1c) can react with R 2a -OH, potassium tert-butoxide to give a compound having Formula (2c) ;
  • the compound having Formula (2c) can undergo reduction reaction to give a compound having Formula (3c) ;
  • the compound having Formula (3c) can react with bromohydrocarbon (such as carbon tetrabromide) to give a compound having Formula (4c) ;
  • the compound having Formula (4c) with a compound having Formula (b’) in an alkaline condition such as K 2 CO 3 ) can undergo condensation reaction to give a compound having Formula (5c) ;
  • the compound having Formula (5c) can further be oxidized to give
  • Compound having Formula (5b) can be prepared according to the procedure described in Scheme 4, wherein R 2a is alkyl, alkoxyalkyl, alkenyl, alkynyl, haloalkyl, haloalkenyl or haloalkynyl; R 7 is as defined herein.
  • Compound having Formula (1d) can react with R 2a -OH, potassium tert-butoxide to give a compound having Formula (2d) ; the compound having Formula (2d) can undergo reduction reaction to give a compound having Formula (3d) ; the compound having Formula (3d) can react with bromohydrocarbon (such as carbon tetrabromide) to give a compound having Formula (4d) ; the compound having Formula (4d) with a compound having Formula (b’) in an alkaline condition (such as K 2 CO 3 ) can undergo condensation reaction to give a compound having Formula (5d) ; the compound having Formula (5d) can further be oxidized to give a compound having Formula (5b) .
  • Example 1 3- ( ( (5- (difluoromethoxy) -3- (difluoromethyl) -1- (2, 2, 2-trifluoroethyl) -1H-pyrazol -4-yl) methyl) sulfonyl) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • Step 1 synthesis of 5, 5-dimethyl-4, 5-dihydroisoxazole-3-ylisothiourea hydrobromide
  • Step 2 synthesis of 3- (difluoromethyl) -1- (2, 2, 2-trifluoroethyl) -1H-pyrazol-5-ol
  • Step 3 synthesis of 5- (difluoromethoxy) -3- (difluoromethyl) -1- (2, 2, 2-trifluoroethyl) -1H-pyrazole
  • Step 4 synthesis of 4- (chloromethyl) -5- (difluoromethoxy) -3- (difluoromethyl) -1-(2, 2, 2-trifluoroethyl) -1H-pyrazole
  • Step 5 3- ( ( (5- (difluoromethoxy) -3- (difluoromethyl) -1- (2, 2, 2-trifluoroethyl) -1H-pyrazol -4-yl) methyl) thio) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • Step 6 3- ( ( (5- (difluoromethoxy) -3- (difluoromethyl) -1- (2, 2, 2-trifluoroethyl) -1H-pyrazol -4-yl) methyl) sulfonyl) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • reaction mixture was washed with saturated aqueous sodium hydrogen sulfite (100 mL) and saturated aqueous sodium bicarbonate (100 mL) in turn, then extracted with dichloromethane (50 mL) .
  • the combined organic layers were dried over anhydrous sodium sufate, and then concentrated in vacuo to remove the solvent.
  • Example 2 3- ( ( (3- (difluoromethyl) -1-ethyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazol-4-yl) methyl) sulfonyl) -5, 5-dimethyl-4, 5-dihydroisoxazole (compound (24) ) and 3- ( ( (3- (difluoromethyl) -1-ethyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazol-4-yl) methyl) sulfinyl) -5, 5-dim ethyl-4, 5-dihydroisoxazole (compound (25) )
  • Step 1 synthesis of 5-chloro-3- (difluoromethyl) -1-ethyl-1H-pyrazol-4-formaldehyde
  • Step 2 synthesis of 3- (difluoromethyl) -1-ethyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazol -4-formaldehyde
  • Step 3 synthesis of (3- (difluoromethyl) -1-ethyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazol-4-yl) methanol
  • Step 4 synthesis of 4- (bromomethyl) -3- (difluoromethyl) -1-ethyl-5- (2, 2, 2 -trifluoroethoxy) -1H-pyrazole
  • Step 5 synthesis of 3- ( ( (3- (difluoromethyl) -1-ethyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazol -4-yl) methyl) thio) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • Step 6 synthesis of 3- ( ( (3- (difluoromethyl) -1-ethyl-5- (2, 2, 2-trifluoroethoxy -1H-pyrazol-4-yl) methyl) sulfonyl) -5, 5-dimethyl-4, 5-dihydroisoxazole (compound (24) ) and 3- ( ( (3- (difluoromethyl) -1-ethyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazol-4-yl) methyl) sulfinyl) -5, 5-dimethyl-4, 5-dihydroisoxazole (compound (25) )
  • Example 3 3- ( ( (5- (difluoromethoxy) -3- (difluoromethyl) -1-methyl-1H-pyrazol-4-yl) methyl) sulfonyl) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • Step 1 synthesis of 3- (difluoromethyl) -1-methyl-1H-pyrazol-5-ol
  • Step 2 synthesis of 5- (difluoromethoxy) -3- (difluoromethyl) -1-methyl-1H-pyrazole
  • Step 3 synthesis of 4- (chloromethyl) -5- (difluoromethoxy) -3- (difluoromethyl) -1-methyl-1H-pyrazole
  • Step 4 3- ( ( (5- (difluoromethoxy) -3- (difluoromethyl) -1-methyl -1H-pyrazol-4-yl) methyl) thio) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • Step 5 3- ( ( (5- (difluoromethoxy) -3- (difluoromethyl) -1-methyl-1H-pyrazol-4-yl) methyl) sulfonyl) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • reaction mixture was washed with saturated aqueous sodium hydrogen sulfite (200 mL) and saturated aqueous sodium bicarbonate (200 mL) in turn, then extracted with dichloromethane (100 mL) .
  • the combined organic layers were dried over anhydrous sodium sulfate, and then concentrated in vacuo to remove the solvent.
  • Example 4 3- ( ( (3- (difluoromethyl) -1-methyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazol-4-yl) methyl) sulfonyl) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • Step 1 synthesis of 5-chloro-3- (difluoromethyl) -1-methyl-1H-pyrazol-4-carbaldehyde
  • Step 2 synthesis of 3- (difluoromethyl) -1-methyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazol -4-formaldehyde
  • Step 3 synthesis of (3- (difluoromethyl) -1-methyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazol-4-yl) methanol
  • Step 4 synthesis of 4- (bromomethyl) -3- (difluoromethyl) -1-methyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazole
  • Step 5 synthesis of 3- ( ( (3- (difluoromethyl) -1-methyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazol-4-yl) methyl) thio) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • Step 6 synthesis of 3- ( ( (3- (difluoromethyl) -1-methyl-5- (2, 2, 2-trifluoroethoxy) -1H-pyrazol-4-yl) methyl) sulfonyl) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • Example 5 3- ( ( (5- (2, 2-difluoroethoxy) -3- (difluoromethyl) -1-methyl-1H-pyrazol-4-yl) methyl) sulfonyl) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • Step 1 synthesis of 5- (2, 2-difluoroethoxy) -3- (difluoromethyl) -1-methyl-1H-pyrazol -4-formaldehyde
  • Step 2 synthesis of (5- (2, 2-difluoroethoxy) -3- (difluoromethyl) -1-methyl -1H-pyrazol-4-yl) methanol
  • Step 3 synthesis of 4- (bromomethyl) -5- (2, 2-difluoroethoxy) -3- (difluoromethyl) -1-methyl-1H-pyrazole
  • Step 4 synthesis of 3- ( ( (5- (2, 2-difluoroethoxy) -3- (difluoromethyl) -1-methyl-1H-pyrazol -4-yl) methyl) thio) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • Step 5 synthesis of 3- ( ( (5- (2, 2-difluoroethoxy) -3- (difluoromethyl) -1-methyl -1H-pyrazol-4-yl) methyl) sulfonyl) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • reaction mixture was washed with saturated aqueous sodium hydrogen sulfite (30 mL) and saturated aqueous sodium bicarbonate (30 mL) , then extracted with dichloromethane (30 mL) .
  • the combined organic layers dried over anhydrous sodium sulfate, and then concentrated in vacuo to remove the solvent.
  • Step 1 synthesis of 5- (2, 2-difluoroethoxy-3- (difluoromethyl) -1-ethyl-1H-pyrazol -4-formaldehyde
  • Step 2 synthesis of (5- (2, 2-difluoroethoxy-3- (difluoromethyl) -1-ethyl-1H -pyrazol-4-yl) methanol
  • Step 3 synthesis of 4- (bromomethyl) -5- (2, 2-difluoroethoxy) -3- (difluoromethyl) -1-ethyl-1H-pyrazole
  • Step 4 synthesis of 3- ( ( (5- (2, 2-difluoroethoxy) -3- (difluoromethyl) -1-ethyl-1H-pyrazol -4-yl) methyl) thio) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • Step 5 3- ( ( (5- (2, 2-difluoroethoxy-3- (difluoromethyl) -1-ethyl-1H-pyrazol-4-yl) methyl) sulfonyl) -5, 5-dimethyl-4, 5-dihydroisoxazole
  • reaction mixture was washed with 30 mL of saturated aqueous sodium hydrogen sulfite and saturated aqueous sodium bicarbonate, then extracted with dichloromethane (50 mL) .
  • dichloromethane 50 mL
  • the combined organic layers dried over anhydrous sodium sulfate, and then concentrated in vacuo to remove the solvent.
  • Preparation of compound A certain amount of the compound of the invention was weighed on an analytical balance (0.0001 g) , dissolved in DMF containing 1%Tween-80 emulsifier to prepare a 1.0 wt%mother liquor, and then the mother liquid was diluted with distilled water for use.
  • Test method potted plant method, the target of the test was abutilon theophrastis, amaranthus retroflexus, eclipta prostrata, digitaria sanguinalis, echinochloa crusgalli and setaria viridis.
  • a flower pot with an inner diameter of 7.5 cm was taken, and compound soil (garden soil: seedling substrate, 1: 2, v/v) was filled to 3/4 of the flower pot, then the above six weed targets (bud rate ⁇ 85%) were sown directly with covering soil 0.2 cm. Water was added to keep the soil moist for 24 hours for use.
  • Each compound placed in an automatic spray tower (model: 3WPSH-700E) was applied to the weed targets at a dose of 150 g a.i. /ha.
  • the herbicidal activity of compound (21) was superior to that of compound (20)
  • the herbicidal activity of compound (21) , compound (24) and compound (28) on abutilon theophrastis was 95%, 100%, and 90%, while the herbicidal activity of compound (20) , compound (25) , and compound (27) on abutilon theophrastis was 50%, 20%, 30%.
  • Table 2 The pre-emergence herbicidal activity of compound of the invention at a dose of 150 g a.i. /ha
  • Table 2 show that the herbicidal activities of the compound of the present invention against abutilon theophrastis, amaranthus retroflexus, eclipta prostrata, digitaria sanguinalis, echinochloa crusgalli and setaria viridis at 150 g a.i. /ha are superior to those of Pyroxasulfone.
  • Preparation of compound A certain amount of the compound of the invention was weighed on an analytical balance (0.0001 g) , dissolved in DMF containing 1 %Tween-80 emulsifier to prepare a 1.0 wt%mother liquor, and then the mother liquid was diluted with distilled water for use.
  • Test method potted plant method, the test targets were soybean, peanut, cotton, oilseed rape.
  • a flower pot with an inner diameter of 7.5 cm was taken, and compound soil (garden soil: seedling substrate, 1: 2, v/v) was filled to 3/4 of the flower pot, then the above four weed targets (bud rate ⁇ 85%) were sown directly with covering soil 0.2 cm. Water was added to keep the soil moist for 24 hours for use.
  • Each compound placed in an automatic spray tower (model: 3WPSH-700E) was applied to the weed targets at a specified dose. After the liquid on the soil surface was dried, the weed targets in the flower pot were transferred to a greenhouse for culture, and 25 days later, the phytotoxicity of each compound to crops was investigated (%) . wherein “0”denotes crop had no injury or was in normal growth process, “100” denotes crop had no emergence or at least part of the crop on the above ground was completely dead.
  • the compounds of the invention have good control effects on broadleaf weeds (such as abutilon theophrastis, amaranthus retroflexus, eclipta prostrata, ) and grass weeds (such as digitaria sanguinalis, echinochloa crusgalli, setaria viridis) ;
  • broadleaf weeds such as abutilon theophrastis, amaranthus retroflexus, eclipta prostrata,
  • grass weeds such as digitaria sanguinalis, echinochloa crusgalli, setaria viridis

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Abstract

L'invention concerne un composé de formule (I), qui peut être utilisé en agriculture, en particulier utilisé en tant qu'herbicide pour lutter contre des plantes indésirables.
PCT/CN2020/075509 2019-02-18 2020-02-17 Dérivés d'isoxazoline et leurs utilisations en agriculture WO2020168997A1 (fr)

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US20040110749A1 (en) * 2001-02-08 2004-06-10 Masao Nakatani Isoxazoline derivative and herbicide comprising the same as active ingredient
WO2004014138A1 (fr) * 2002-08-07 2004-02-19 Kumiai Chemical Industry Co., Ltd. Compositions herbicides
US20100255988A1 (en) * 2007-11-30 2010-10-07 Bayer Cropscience Ag Chiral 3-(benzylsulfinyl)-5,5-dimethyl-4,5-dihydroisoxazole derivatives and 5,5-dimethyl-3-[(1H-pyrazol-4-ylmethyl)sulfinyl]-4,5-dihydroisoxazole derivatives, method for the production thereof, and use of same as herbicides and plant growth regulations

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WO2021002484A3 (fr) * 2019-10-31 2021-03-11 クミアイ化学工業株式会社 Herbicide et procédé de production d'un intermédiaire de celui-ci
JPWO2021002484A1 (ja) * 2019-10-31 2021-09-13 クミアイ化学工業株式会社 除草剤及びその中間体の製造方法
KR20220097436A (ko) * 2019-10-31 2022-07-07 구미아이 가가쿠 고교 가부시키가이샤 제초제 및 그 중간체의 제조방법
KR102523028B1 (ko) 2019-10-31 2023-04-17 구미아이 가가쿠 고교 가부시키가이샤 제초제 및 그 중간체의 제조방법
EP4053125A4 (fr) * 2019-10-31 2023-07-05 Kumiai Chemical Industry Co., Ltd. Herbicide et procédé de production d'un intermédiaire de celui-ci

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