WO2021073487A1 - 一种具有旋光活性的异恶唑啉类化合物及用途 - Google Patents
一种具有旋光活性的异恶唑啉类化合物及用途 Download PDFInfo
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- WO2021073487A1 WO2021073487A1 PCT/CN2020/120547 CN2020120547W WO2021073487A1 WO 2021073487 A1 WO2021073487 A1 WO 2021073487A1 CN 2020120547 W CN2020120547 W CN 2020120547W WO 2021073487 A1 WO2021073487 A1 WO 2021073487A1
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- PSRVQQFHOLSZLL-UHFFFAOYSA-N CCOC(C(C)(C1)ON=C1c(c(Cl)c1)cc(N)c1F)=O Chemical compound CCOC(C(C)(C1)ON=C1c(c(Cl)c1)cc(N)c1F)=O PSRVQQFHOLSZLL-UHFFFAOYSA-N 0.000 description 1
- PSRVQQFHOLSZLL-ZDUSSCGKSA-N CCOC([C@](C)(C1)ON=C1c(c(Cl)c1)cc(N)c1F)=O Chemical compound CCOC([C@](C)(C1)ON=C1c(c(Cl)c1)cc(N)c1F)=O PSRVQQFHOLSZLL-ZDUSSCGKSA-N 0.000 description 1
- ZFQQLFKHTMIGJX-SFHVURJKSA-N CCOC([C@](C)(C1)ON=C1c(cc(c(F)c1)N(C(C=C(C(F)(F)F)N2C)=O)C2=O)c1Cl)=O Chemical compound CCOC([C@](C)(C1)ON=C1c(cc(c(F)c1)N(C(C=C(C(F)(F)F)N2C)=O)C2=O)c1Cl)=O ZFQQLFKHTMIGJX-SFHVURJKSA-N 0.000 description 1
Classifications
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- 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
- C07D413/10—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 carbon chain containing aromatic rings
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- 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
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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
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- 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
Definitions
- the invention belongs to the field of agricultural herbicides, and specifically relates to an isoxazoline compound with optical activity and uses thereof.
- CN105753853 discloses isoxazoline compounds with the following general structural formula and herbicidal activity. However, there is no report concerning the optical isomers of these compounds, nor does it involve the same or different herbicidal activity among the optical isomers, nor does it involve which optical isomer is more effective as the active ingredient of the herbicide. Differences are difficult to predict without specific experimental research.
- the purpose of the present invention is to provide an isoxazoline compound with optical activity and its use.
- the technology adopted by the present invention is:
- optically active isoxazoline compound with excellent herbicidal activity of the present invention is represented by general formula (I):
- R 1 is selected from CH 3 or NH 2 ;
- R 2 is selected from C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
- R 3 and R 4 are respectively selected from hydrogen, halogen, C 1 -C 6 alkyl or C 1 -C 6 alkoxy;
- R 5 is selected from hydrogen, cyano, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, phenyl or further substituted by 1-4 independently selected from the following groups The phenyl group: halogen, CN, NO 2 , C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 1 -C 6 alkoxy, C 1 -C 6 haloalkoxy, C 1 -C 6 Alkylthio or C 1 -C 6 alkylsulfonyl;
- R 6 is selected from C 1 -C 6 alkyl CO 2 R 7 , CO 2 R 7 or CONR 8 R 9 ;
- R 7 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 6 alkoxy C 1 -C 6 alkyl, C 1 -C 6 alkoxycarbonyl C 1 -C 4 alkyl, C 1 -C 6 alkylcarbonyloxy C 2 -C 4 alkyl, unsubstituted or Benzyl, furylidene, thiazolemethylene, tetrahydrofurylidene or pyridinemethylene further substituted by 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 8 alkane Group, C 1 -C 8 haloalkyl, C 1 -C 8 alkoxy, C 1 -C 8 haloalkoxy, C 1 -C 8 alkoxycarbonyl,
- R 8 and R 9 are respectively selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, or C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkyl.
- the configuration at the central asymmetric carbon atom represented by * is the S configuration.
- R 1 is selected from CH 3 or NH 2 ;
- R 2 is selected from methyl, isopropyl, tert-butyl, trifluoromethyl, trichloromethyl, difluoromethyl or heptafluoroisopropyl;
- R 3 and R 4 are respectively selected from hydrogen, fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy or isopropoxy;
- R 5 is selected from hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, phenyl or further substituted by 1-4 independently selected from the following groups The phenyl group: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, C 1 -C 4 Alkylthio or C 1 -C 4 alkylsulfonyl;
- R 6 is selected from C 1 -C 4 alkyl CO 2 R 7 , CO 2 R 7 or CONR 8 R 9 ;
- R 7 is selected from hydrogen, C 1 -C 6 alkyl, C 1 -C 6 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 4 alkoxy C 1 -C 4 alkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkyl, C 1 -C 4 alkylcarbonyloxy C 2 -C 4 alkyl, unsubstituted or Benzyl, furylidene or tetrahydrofurylidene further substituted by 1-4 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 6 alkyl or C 1 -C 6 haloalkyl;
- R 8 and R 9 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or C 1 -C 4 alkoxycarbonyl C 1 -C 4 alkyl.
- a further preferred compound of the present invention is: in the general formula (I)
- R 1 is selected from CH 3 or NH 2 ;
- R 2 is selected from methyl, trifluoromethyl, trichloromethyl or difluoromethyl
- R 3 and R 4 are respectively selected from hydrogen, fluorine, chlorine, bromine, methyl, methoxy, ethoxy or isopropoxy;
- R 5 is selected from hydrogen, cyano, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, phenyl or further substituted by 1-4 independently selected from the following groups The phenyl group: halogen, CN, NO 2 , C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 1 -C 4 alkoxy or C 1 -C 4 haloalkoxy;
- R 6 is selected from C 1 -C 4 alkyl CO 2 R 7 , CO 2 R 7 or CONR 8 R 9 ;
- R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, C 3 -C 6 cycloalkyl, C 3 -C 6 alkenyl, C 3 -C 6 alkynyl, C 1- C 4 alkoxy C 1 -C 2 alkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 2 alkyl, C 1 -C 4 alkylcarbonyloxy C 2 -C 4 alkyl, unsubstituted or Benzyl, furimethylene or tetrahydrofurimethylene further substituted by 1-3 independently selected from the following groups: halogen, CN, NO 2 , C 1 -C 4 alkyl or C 1 -C 4 haloalkyl;
- R 8 and R 9 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or C 1 -C 4 alkoxycarbonyl C 1 -C 2 alkyl.
- the more preferred compound of the present invention is: in general formula (I)
- R 1 is selected from CH 3 or NH 2 ;
- R 2 is selected from trifluoromethyl, trichloromethyl or difluoromethyl
- R 3 and R 4 are respectively selected from hydrogen, fluorine, chlorine, bromine or isopropoxy
- R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, phenyl or 1 -4 independently substituted phenyl groups selected from the following groups: halogen, CN, NO 2 , methyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy , Isopropoxy, trifluoromethoxy, difluoromethoxy or trifluoroethoxy;
- R 6 is selected from C 1 -C 4 alkyl CO 2 R 7 , CO 2 R 7 or CONR 8 R 9 ;
- R 7 is selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, allyl, 2-methylallyl, 1,1-dimethylallyl, allyl, alkyne Propyl, alkynyl, cyclopropyl, cyclohexyl, C 1 -C 3 alkoxy C 1 -C 2 alkyl, C 1 -C 4 alkoxycarbonyl C 1 -C 2 alkyl, C 1- C 4 alkylcarbonyloxy C 2 -C 3 alkyl, unsubstituted or further substituted by 1-3 independently selected from the following groups benzyl, furylidene or tetrahydrofurylidene: halogen, CN, NO 2 Or C 1 -C 4 alkyl;
- R 8 and R 9 are respectively selected from hydrogen, C 1 -C 4 alkyl, C 1 -C 4 haloalkyl, or C 1 -C 4 alkoxycarbonyl C 1 -C 2 alkyl.
- a further preferred compound of the present invention is: in the general formula (I)
- R 1 is selected from CH 3 or NH 2 ;
- R 2 is selected from trifluoromethyl, trichloromethyl or difluoromethyl
- R 3 and R 4 are respectively selected from hydrogen, fluorine, chlorine, bromine or isopropoxy
- R 5 is selected from hydrogen, cyano, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, tert-butyl, trifluoromethyl, difluoromethyl, phenyl or 1 -2 further substituted phenyl groups independently selected from the following groups: halogen, CN, NO 2 , methyl, isopropyl, tert-butyl, trifluoromethyl, difluoromethyl, methoxy, ethoxy , Isopropoxy, trifluoromethoxy, difluoromethoxy or trifluoroethoxy;
- R 6 is selected from CH 2 CO 2 R 7 , CH 2 CH 2 CO 2 R 7 , CO 2 R 7 or CONR 8 R 9 ;
- R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, trifluoromethyl, difluoroethyl, heptafluoroiso Propyl, allyl, propargyl, 2-methylallyl, 1,1-dimethylallyl, allyl, propargyl, propargyl, cyclopropyl, cyclohexyl, methyl Oxyethyl, ethoxyethyl, isopropoxyethyl, CH 3 OCOCH 2 , CH 3 CH 2 OCOCH 2 , (CH 3 ) 2 CHOCOCH 2 , CH 3 OCOCH 2 CH 2 , CH 3 CH 2 OCOCH 2 CH 2 , (CH 3 ) 2 CHOCOCH 2 CH 2 , CH 3 OCOCH (CH 3 ), CH 3 CH 2 OCOCH (CH 3
- R 8 is selected from hydrogen, C 1 -C 4 alkyl or C 1 -C 4 haloalkyl
- R 9 is selected from hydrogen, C 1 -C 4 alkyl or C 1 -C 4 alkoxycarbonyl C 1 -C 2 alkyl.
- the further preferred compound of the present invention is: in the general formula (I)
- R 1 is selected from CH 3 or NH 2 ;
- R 2 is selected from trifluoromethyl or difluoromethyl
- R 3 and R 4 are respectively selected from hydrogen, fluorine, chlorine, bromine or isopropoxy
- R 5 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl;
- R 6 is selected from CH 2 CO 2 R 7 , CH 2 CH 2 CO 2 R 7 , CO 2 R 7 or CONR 8 R 9 ;
- R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, trifluoromethyl, difluoroethyl, heptafluoroiso Propyl, allyl, propargyl, 2-methylallyl, 1,1-dimethylallyl, allyl, propargyl, propargyl, cyclopropyl, cyclohexyl, methyl Oxyethyl, ethoxyethyl, isopropoxyethyl, CH 3 OCOCH 2 , CH 3 CH 2 OCOCH 2 , (CH 3 ) 2 CHOCOCH 2 , CH 3 OCOCH 2 CH 2 , CH 3 CH 2 OCOCH 2 CH 2 , (CH 3 ) 2 CHOCOCH 2 CH 2 , CH 3 OCOCH (CH 3 ), CH 3 CH 2 OCOCH (CH 3
- R 8 is selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, trifluoroethyl, difluoroethyl, 1-chloroethyl, 1-chloropropyl or 2-chloropropyl;
- R 9 is selected from hydrogen, methyl, ethyl, isopropyl, n-propyl, n-butyl, tert-butyl, CH 3 OCOCH 2 , CH 3 CH 2 OCOCH 2 , (CH 3 ) 2 CHOCOCH 2 , CH 3 OCOCH 2 CH 2 , CH 3 CH 2 OCOCH 2 CH 2 , (CH 3 ) 2 CHOCOCH 2 CH 2 , CH 3 OCOCH (CH 3 ), or CH 3 CH 2 OCOCH (CH 3 ).
- R 1 is selected from CH 3 or NH 2 ;
- R 2 is selected from trifluoromethyl or difluoromethyl
- R 3 and R 4 are each selected from hydrogen, fluorine, chlorine or isopropoxy
- R 5 is selected from hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl or tert-butyl;
- R 6 is selected from CH 2 CO 2 R 7 , CH 2 CH 2 CO 2 R 7 or CO 2 R 7 ;
- R 7 is selected from hydrogen, methyl, ethyl, n-propyl, n-butyl, isopropyl, isobutyl, tert-butyl, trifluoroethyl, trifluoromethyl, difluoroethyl, heptafluoroiso Propyl, allyl, propargyl, 2-methylallyl, 1,1-dimethylallyl, allyl, propargyl, propargyl, cyclopropyl, cyclohexyl, methyl Oxyethyl, ethoxyethyl, isopropoxyethyl, CH 3 OCOCH 2 , CH 3 CH 2 OCOCH 2 , (CH 3 ) 2 CHOCOCH 2 , CH 3 OCOCH 2 CH 2 , CH 3 CH 2 OCOCH 2 CH 2 , (CH 3 ) 2 CHOCOCH 2 CH 2 , CH 3 OCOCH (CH 3 ), CH 3 CH 2 OCOCH (CH 3
- Halogen refers to fluorine, chlorine, bromine or iodine.
- Alkyl straight or branched chain alkyl, such as methyl, ethyl, propyl, isopropyl, n-butyl or tert-butyl.
- Cycloalkyl A substituted or unsubstituted cyclic alkyl group, such as cyclopropyl, cyclopentyl or cyclohexyl. Substituents such as methyl, halogen and the like.
- Halogenated alkyl groups straight or branched chain alkyl groups.
- the hydrogen atoms on these alkyl groups can be partially or fully replaced by halogen atoms, for example, chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, dichloromethane, Fluoromethyl, trifluoromethyl, etc.
- Alkoxy a straight or branched chain alkyl group, which is connected to the structure via an oxygen atom bond.
- Halogenated alkoxy groups straight-chain or branched-chain alkoxy groups. The hydrogen atoms on these alkoxy groups may be partially or completely replaced by halogen atoms.
- alkylthio straight or branched chain alkyl, connected to the structure via a sulfur atom bond.
- Halogenated alkylthio linear or branched alkylthio. The hydrogen atoms on these alkyl groups can be partially or completely replaced by halogen atoms.
- Alkenyl straight or branched chain alkenes, such as vinyl, 1-propenyl, 2-propenyl and the different butenyl, pentenyl and hexenyl isomers. Alkenyl also includes polyenes such as 1,2-propadienyl and 2,4-hexadienyl.
- Alkylsulfonyl A straight or branched chain alkyl group is connected to the structure via a sulfonyl group (-SO 2 -), such as a methylsulfonyl group.
- Halogenated alkylsulfonyl linear or branched alkylsulfonyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms.
- Alkylsulfinyl A straight or branched chain alkyl group is connected to the structure via a sulfonyl group (-SO-), such as a methylsulfinyl group.
- Halogenated alkylsulfonyl linear or branched alkylsulfinyl, the hydrogen atoms on the alkyl group can be partially or completely replaced by halogen atoms.
- Alkoxycarbonyl The alkoxy is connected to the structure via a carbonyl group, such as CH 3 OCO- or CH 3 CH 2 OCO-.
- Alkoxyalkyl alkyl-O-alkyl-, such as CH 3 OCH 2 -.
- Alkylcarbonyloxyalkoxycarbonyl alkyl-CO-O-alkyl- OCO-, such as CH 3 COOCH 2 OCO-, CH 3 COOCH 2 CH 2 OCO- or C 2 H 5 COOCH 2 CH 2 OCO- etc. .
- Alkylcarbonyl The alkyl group is connected to the structure via the carbonyl group, such as CH 3 CO- or CH 3 CH 2 CO-.
- Haloalkylcarbonyl The haloalkyl is connected to the structure via a carbonyl group, such as CF 3 CO- or CF 2 HCO-.
- Cycloalkylcarbonyl Cycloalkyl is connected to the structure via carbonyl, such as cyclopropanoyl or cyclohexylformyl.
- Halogenated cycloalkylcarbonyl group The halogenated cycloalkyl group is connected to the structure via a carbonyl group, such as 1-chlorocyclopropanoyl and the like.
- Alkylaminosulfonyl alkyl -NH-SO 2 -, such as CH 3 NHSO 2 -or C 2 H 5 NHSO 2 -and so on.
- Dialkylaminosulfonyl dialkyl-N-SO 2 -, such as (CH 3 ) 2 NSO 2 -or (C 2 H 5 ) 2 NSO 2 -, etc.
- Alkylaminocarbonyl alkyl-NH-CO-, such as CH 3 NHCO- or C 2 H 5 NHCO- etc.
- Dialkylaminocarbonyl dialkyl-N-CO-, such as (CH 3 ) 2 NCO- or (C 2 H 5 ) 2 NCO-, etc.
- Dialkylaminothiocarbonyl dialkyl-N-CS-, such as (CH 3 ) 2 NCS- or (C 2 H 5 ) 2 NCS-, etc.
- Alkylthioalkylcarbonyl alkyl-S-alkyl-CO, such as CH 3 SCH 2 CO or CH 3 SCH 2 CH 2 CO.
- Aryl polyvalent aromatic groups, such as phenyl and naphthyl. Heteroaryl is a five-membered ring or six-membered ring containing one or more N, O, S heteroatoms.
- optically active compound of formula I of the present invention can be prepared from the optically active amino compound II by methods reported in known literature, such as CN105753853, CN108570041 or WO2016095768.
- the optically active amino compound II can be obtained by using a chiral column to resolve the racemic amino compound III.
- the racemic amino compound III can be prepared by referring to the method in CN105753853.
- the compound of general formula (I) can control various weeds and can also be used for the control of resistant weeds.
- the compound of the general formula (I) can effectively control various broad-leaved weeds, gramineous weeds and Cyperaceae weeds, such as barnyardgrass, setaria, alien sedge, water sedge, oil sedge, horse Tang, Myrtle, Abutilon, Zinnia, Amaranthus, Purslane, Cocklebur, Solanum, Cassia, Wild Watermelon Seedlings, Wild Soybeans, Amaranthus, Nodular Amaranth, Bidens, Kochia scoparia , Morning Glory, Gooseweed, Orangutan, Wild Buckwheat, Green Setaria, Pseudosorghum, Little Scabies, Seed Maiden, Big Ear Seed Maiden, Wild Oats, Bluegrass, Fructus Brome, Quinoa, Small Seed Phalaenopsis, wild radish, chickweed, cornflower, pig stalk, purple wild sesame, small white chrysanthemum, corn poppy, polygonum
- It has certain safety to wheat, corn, rice, soybean, sugar beet and other crops. It can be used as a selective herbicide in crop fields in agriculture, and it can also be used as a biocidal herbicide in non-arable land, fallow land, woodland, orchard. , Ridge and so on.
- the compound of the present invention can be used to control weeds before and after emergence, and can also be used for soil treatment. Therefore, the present invention also includes the use of compounds of general formula (I) for controlling weeds.
- the compounds of the general formula (I) of the present invention are also suitable for drying and/or defoliating plants.
- a herbicidal composition uses the compound of the general formula (I) as an active component, and the weight percentage of the active component in the composition is 0.1-99%.
- the herbicidal activity test method of the compound of the present invention is as follows:
- test design dose spray treatment (spray pressure 1.95kg/cm 2 , spray volume 500L/hm 2 , crawler speed 1.48km/h) on a crawler crop sprayer (designed and produced by British Engineer Research Ltd.).
- the test is set to be repeated 3 times. After the test materials are processed, they are placed in the operation hall. After the liquid is naturally dried in the shade, it is placed in the greenhouse for management according to conventional methods. Observation and recording of the weeds' response to the medicament is carried out. After treatment, the test medicament's control effect on weeds is regularly visually inspected.
- control effect classification standard 0 means invalid, 100% means complete kill or severe suppression of weeds.
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Abstract
Description
Claims (10)
- 一种具有旋光活性的异恶唑啉类化合物,其特征在于:化合物结构如通式(I)所示:式中:*代表构型为S的不对称碳原子;R 1选自CH 3或NH 2;R 2选自C 1-C 4烷基或C 1-C 4卤代烷基;R 3、R 4分别选自氢、卤素、C 1-C 6烷基或C 1-C 6烷氧基;R 5选自氢、氰基、C 1-C 6烷基、C 1-C 6卤代烷基、C 3-C 6环烷基、苯基或被1-4个独立选自以下基团进一步取代的苯基:卤素、CN、NO 2、C 1-C 6烷基、C 1-C 6卤代烷基、C 1-C 6烷氧基、C 1-C 6卤代烷氧基、C 1-C 6烷硫基或C 1-C 6烷基磺酰基;R 6选自C 1-C 6烷基CO 2R 7、CO 2R 7或CONR 8R 9;R 7选自氢、C 1-C 6烷基、C 1-C 6卤代烷基、C 3-C 6环烷基、C 3-C 6烯基、C 3-C 6炔基、C 1-C 6烷氧基C 1-C 6烷基、C 1-C 6烷氧基羰基C 1-C 4烷基、C 1-C 6烷羰基氧基C 2-C 4烷基,未取代或者被1-4个独立选自以下基团进一步取代的苄基、呋喃亚甲基、噻唑亚甲基、四氢呋喃亚甲基或吡啶亚甲基:卤素、CN、NO 2、C 1-C 8烷基、C 1-C 8卤代烷基、C 1-C 8烷氧基、C 1-C 8卤代烷氧基、C 1-C 8烷氧基羰基、C 1-C 8烷硫基或C 1-C 8烷基磺酰基;R 8、R 9分别选自氢、C 1-C 6烷基、C 1-C 6卤代烷基或C 1-C 4烷氧基羰基C 1-C 4烷基。
- 按照权利要求1所述的化合物,其特征在于:通式(I)中*代表构型为S的不对称碳原子;R 1选自CH 3或NH 2;R 2选自甲基、异丙基、叔丁基、三氟甲基、三氯甲基、二氟甲基或七氟异丙基;R 3、R 4分别选自氢、氟、氯、溴、甲基、乙基、异丙基、叔丁基、甲氧基、乙氧基或异丙氧基;R 5选自氢、氰基、C 1-C 4烷基、C 1-C 4卤代烷基、C 3-C 6环烷基、苯基或被1-4个独立选自以下基团进一步取代的苯基:卤素、CN、NO 2、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基、C 1-C 4卤代烷氧基、C 1-C 4烷硫基或C 1-C 4烷基磺酰基;R 6选自C 1-C 4烷基CO 2R 7、CO 2R 7或CONR 8R 9;R 7选自氢、C 1-C 6烷基、C 1-C 6卤代烷基、C 3-C 6环烷基、C 3-C 6烯基、C 3-C 6炔基、C 1-C 4烷氧基C 1-C 4烷基、C 1-C 4烷氧基羰基C 1-C 4烷基、C 1-C 4烷羰基氧基C 2-C 4烷基,未取代或者被1-4个独立选自以下基团进一步取代的苄基、呋喃亚甲基或四氢呋喃亚甲基:卤素、CN、NO 2、C 1-C 6烷基或C 1-C 6卤代烷基;R 8、R 9分别选自氢、C 1-C 4烷基、C 1-C 4卤代烷基或C 1-C 4烷氧基羰基C 1-C 4烷基。
- 按照权利要求2所述的化合物,其特征在于:通式(I)中*代表构型为S的不对称碳原子;R 1选自CH 3或NH 2;R 2选自甲基、三氟甲基、三氯甲基或二氟甲基;R 3、R 4分别选自氢、氟、氯、溴、甲基、甲氧基、乙氧基或异丙氧基;R 5选自氢、氰基、C 1-C 4烷基、C 1-C 4卤代烷基、C 3-C 6环烷基、苯基或被1-4个独立选自以下基团进一步取代的苯基:卤素、CN、NO 2、C 1-C 4烷基、C 1-C 4卤代烷基、C 1-C 4烷氧基或C 1-C 4卤代烷氧基;R 6选自C 1-C 4烷基CO 2R 7、CO 2R 7或CONR 8R 9;R 7选自氢、C 1-C 4烷基、C 1-C 4卤代烷基、C 3-C 6环烷基、C 3-C 6烯基、C 3-C 6炔基、C 1-C 4烷氧基C 1-C 2烷基、C 1-C 4烷氧基羰基C 1-C 2烷基、C 1-C 4烷羰基氧基C 2-C 4烷基,未取代或者被1-3个独立选自以下基团进一步取代的苄基、呋喃亚甲基或四氢呋喃亚甲基:卤素、CN、NO 2、C 1-C 4烷基或C 1-C 4卤代烷基;R 8、R 9分别选自氢、C 1-C 4烷基、C 1-C 4卤代烷基或C 1-C 4烷氧基羰基C 1-C 2烷基。
- 按照权利要求3所述的化合物,其特征在于:通式(I)中*代表构型为S的不对称碳原子;R 1选自CH 3或NH 2;R 2选自三氟甲基、三氯甲基或二氟甲基;R 3、R 4分别选自氢、氟、氯、溴或异丙氧基;R 5选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、三氟甲基、二氟甲基、苯基或被1-4个独立选自以下基团进一步取代的苯基:卤素、CN、NO 2、甲基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、异丙氧基、三氟甲氧基、二氟甲氧基或三氟乙氧基;R 6选自C 1-C 4烷基CO 2R 7、CO 2R 7或CONR 8R 9;R 7选自氢、C 1-C 4烷基、C 1-C 4卤代烷基、烯丙基、2-甲基烯丙基、1,1-二甲基烯丙基、烯丁基、炔丙基、炔丁基、环丙基、环己基、C 1-C 3烷氧基C 1-C 2烷基、C 1-C 4烷氧基羰基C 1-C 2烷基、C 1-C 4烷羰基氧基C 2-C 3烷基,未取代或者被1-3个独立选自以下基团进一步取代的苄基、呋喃亚甲基或四氢呋喃亚甲基:卤素、CN、NO 2或C 1-C 4烷基;R 8、R 9分别选自氢、C 1-C 4烷基、C 1-C 4卤代烷基或C 1-C 4烷氧基羰基C 1-C 2烷基。
- 按照权利要求4所述的化合物,其特征在于:通式(I)中*代表构型为S的不对称碳原子;R 1选自CH 3或NH 2;R 2选自三氟甲基、三氯甲基或二氟甲基;R 3、R 4分别选自氢、氟、氯、溴或异丙氧基;R 5选自氢、氰基、甲基、乙基、正丙基、异丙基、正丁基、异丁基、叔丁基、三氟甲基、二氟甲基、苯基或被1-2个独立选自以下基团进一步取代的苯基:卤素、CN、NO 2、甲基、异丙基、叔丁基、三氟甲基、二氟甲基、甲氧基、乙氧基、异丙氧基、三氟甲氧基、二氟甲氧基或三氟乙氧基;R 6选自CH 2CO 2R 7、CH 2CH 2CO 2R 7、CO 2R 7或CONR 8R 9;R 7选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、三氟甲基、二氟乙基、七氟异丙基、烯丙基、炔丙基、2-甲基烯丙基、1,1-二甲基烯丙基、烯丁基、炔丙基、炔丁基、环丙基、环己基、甲氧基乙基、乙氧基乙基、异丙氧基乙基、CH 3OCOCH 2、CH 3CH 2OCOCH 2、(CH 3) 2CHOCOCH 2、CH 3OCOCH 2CH 2、CH 3CH 2OCOCH 2CH 2、(CH 3) 2CHOCOCH 2CH 2、CH 3OCOCH(CH 3)、CH 3CH 2OCOCH(CH 3)、未取代或者被1-2个独立选自以下基团进一步取代的苄基、呋喃亚甲基或四氢呋喃亚甲基:氟、氯、溴、CN、NO 2、甲基、异丙基或叔丁基;R 8选自氢、C 1-C 4烷基或C 1-C 4卤代烷基;R 9选自氢、C 1-C 4烷基或C 1-C 4烷氧基羰基C 1-C 2烷基。
- 按照权利要求5所述的化合物,其特征在于:通式(I)中*代表构型为S的不对称碳原子;R 1选自CH 3或NH 2;R 2选自三氟甲基或二氟甲基;R 3、R 4分别选自氢、氟、氯、溴或异丙氧基;R 5选自氢、甲基、乙基、正丙基、异丙基、正丁基、异丁基或叔丁基;R 6选自CH 2CO 2R 7、CH 2CH 2CO 2R 7、CO 2R 7或CONR 8R 9;R 7选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、三氟甲基、二氟乙基、七氟异丙基、烯丙基、炔丙基、2-甲基烯丙基、1,1-二甲基烯丙基、烯丁基、炔丙基、炔丁基、环丙基、环己基、甲氧基乙基、乙氧基乙基、异丙氧基乙基、CH 3OCOCH 2、CH 3CH 2OCOCH 2、(CH 3) 2CHOCOCH 2、CH 3OCOCH 2CH 2、CH 3CH 2OCOCH 2CH 2、(CH 3) 2CHOCOCH 2CH 2、CH 3OCOCH(CH 3)、CH 3CH 2OCOCH(CH 3)、呋喃亚甲基或四氢呋喃亚甲基、未取代或者被1-2个独立选自以下基团进一步取代的苄基:氟、氯、溴、CN、NO 2、甲基、异丙基或叔丁基;R 8选自氢、甲基、乙基、异丙基、正丙基、正丁基、叔丁基、三氟乙基、二氟乙基、1-氯乙基、1-氯丙基或2-氯丙基;R 9选自氢、甲基、乙基、异丙基、正丙基、正丁基、叔丁基、CH 3OCOCH 2、CH 3CH 2OCOCH 2、(CH 3) 2CHOCOCH 2、CH 3OCOCH 2CH 2、CH 3CH 2OCOCH 2CH 2、(CH 3) 2CHOCOCH 2CH 2、CH 3OCOCH(CH 3)或CH 3CH 2OCOCH(CH 3)。
- 按照权利要求6所述的化合物,其特征在于:通式(I)中*代表构型为S的不对称碳原子;R 1选自CH 3或NH 2;R 2选自三氟甲基或二氟甲基;R 3、R 4分别选自氢、氟、氯或异丙氧基;R 5选自氢、甲基、乙基、正丙基、异丙基、正丁基、异丁基或叔丁基;R 6选自CH 2CO 2R 7、CH 2CH 2CO 2R 7或CO 2R 7;R 7选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、三氟甲基、二氟乙基、七氟异丙基、烯丙基、炔丙基、2-甲基烯丙基、1,1-二甲基烯丙基、烯丁基、炔丙基、炔丁基、环丙基、环己基、甲氧基乙基、乙氧基乙基、异丙氧基乙基、CH 3OCOCH 2、CH 3CH 2OCOCH 2、(CH 3) 2CHOCOCH 2、CH 3OCOCH 2CH 2、CH 3CH 2OCOCH 2CH 2、(CH 3) 2CHOCOCH 2CH 2、CH 3OCOCH(CH 3)、CH 3CH 2OCOCH(CH 3)、呋喃亚甲基或四氢呋喃亚甲基、未取代或者被1-2个独立选自以下基团进一步取代的苄基:氟、氯、溴、CN、NO 2、甲基、异丙基或叔丁基。
- 一种根据权利要求1所述的通式(I)化合物用于防治杂草中的应用。
- 一种除草组合物,其特征在于:以权利要求1所述的通式(I)化合物作为活性组分,组合物中的活性组分的重量百分含量为0.1-99%。
- 一种根据权利要求9所述的除草组合物用于防治杂草中的应用。
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