WO2020057391A1 - 哒嗪胺类化合物的制备及其应用 - Google Patents
哒嗪胺类化合物的制备及其应用 Download PDFInfo
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- WO2020057391A1 WO2020057391A1 PCT/CN2019/104960 CN2019104960W WO2020057391A1 WO 2020057391 A1 WO2020057391 A1 WO 2020057391A1 CN 2019104960 W CN2019104960 W CN 2019104960W WO 2020057391 A1 WO2020057391 A1 WO 2020057391A1
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- 0 C*(C)c1nnc(*I)c(N(C)C(N=IC*2(C)C(C)C2)=CN=I)c1 Chemical compound C*(C)c1nnc(*I)c(N(C)C(N=IC*2(C)C(C)C2)=CN=I)c1 0.000 description 2
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
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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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/58—1,2-Diazines; Hydrogenated 1,2-diazines
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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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
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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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- A01N43/70—Diamino—1,3,5—triazines with only one oxygen, sulfur or halogen atom or only one cyano, thiocyano (—SCN), cyanato (—OCN) or azido (—N3) group directly attached to a ring carbon atom
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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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/707—1,2,3- or 1,2,4-triazines; Hydrogenated 1,2,3- or 1,2,4-triazines
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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
- A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
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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
- A01N43/84—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 six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
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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
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/20—Nitrogen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/22—Nitrogen and oxygen atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/10—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D237/24—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
- C07D413/04—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 directly linked by a ring-member-to-ring-member bond
Definitions
- This application belongs to the field of agricultural herbicides.
- the invention relates to a new type of pyridazamine compounds and compositions, their uses and methods of use.
- Farmland weeds are an important factor affecting crop production.
- the area of farmland affected by weeds in China is 43 million hectares, which reduces 17.5 million tons of grain output each year.
- Weed chemical control is the most important method for weed control in farmland. It has the advantages of labor-saving, time-saving, high-efficiency and quickness.
- Pyridazine compounds are generally used in medicine for anti-cancer and anti-inflammatory applications.
- the pyridazamine compounds of the present application have excellent herbicidal activity, and such structures have not been reported in the literature as herbicides. These compounds are agriculturally useful as herbicides.
- the present application provides a novel pyridazine amine compound, a method for controlling weeds, and an agricultural application of components containing these compounds.
- R 1 is selected from hydrogen, halogen, cyano, unsubstituted or substituted by 1-4 phenoxy or heteroaryloxy groups independently selected from halogen, nitro, cyano, C 1 -C 12 Alkyl, halo C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halo C 1 -C 12 alkoxy, C 3 -C 12 cycloalkyl, C 1 -C 12 alkylcarbonyl Or C 1 -C 12 alkoxycarbonyl;
- R 2 is selected from hydrogen, C 1 -C 12 alkyl, halo C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halo C 1 -C 12 alkoxy, C 3 -C 6 ring Alkyl, cyano C 1 -C 12 alkyl, C 1 -C 12 alkylamino, halo C 1 -C 12 alkylamino, C 2 -C 6 dialkylamino, C 2 -C 12 alkenyl , Halogenated C 2 -C 12 alkynyl, C 2 -C 12 alkenyloxy, halogenated C 2 -C 12 alkenyloxy, C 2 -C 12 alkenyl, halogenated C 2 -C 12 alkenyl, C 2- C 12 alkynyloxy, halo C 2 -C 12 alkynyloxy, C 1 -C 12 alkylsulfonyl, C 1 -C 12 alkylcarbonyl,
- R 3 is selected from unsubstituted or substituted by 1-4 phenyl, benzyl or heteroaryl groups independently selected from the group consisting of halogen, hydroxy, nitro, cyano, CHO, COOH, COONa, C 1- C 12 alkyl, halo C 1 -C 12 alkyl, C 1 -C 12 alkoxy, halo C 1 -C 12 alkoxy, C 3 -C 6 cycloalkyl, cyano C 1 -C 12 alkyl, C 1 -C 12 alkylamino, halogenated C 1 -C 12 alkylamino, C 2 -C 6 dialkylamino, C 2 -C 12 alkenyl, halogenated C 2 -C 12 alkyne , C 2 -C 12 alkenyloxy, halo C 2 -C 12 alkenyloxy, C 2 -C 12 alkynyl, halo C 2 -C 12 alkynyl,
- R 2 NR 3 may also constitute a five- or six-membered ring substituted or unsubstituted by one to four groups independently selected from the group consisting of halogen, hydroxyl, nitro, cyano CHO, COOH, COONa, C 1 -C 12 alkyl, halo C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 12 alkoxy, halo C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, C 1 -C 12 alkylcarbonyl, or C 1 -C 12 alkoxycarbonyl;
- R 4 is selected from halogen, cyano, CHO, COOH, COONa, C 1 -C 12 alkylsulfonyl, halo C 1 -C 12 alkylsulfonyl or substituted by 1-4 groups independently selected from Unsubstituted arylsulfonyl, the independently substituted group is selected from the group consisting of halogen, hydroxy, nitro, cyano, CHO, COOH, COONa, C 1 -C 12 alkyl, halo C 1 -C 12 alkyl, C 3 -C 12 cycloalkyl, C 1 -C 12 alkoxy, halo C 1 -C 12 alkoxy, C 1 -C 12 alkylthio, C 1 -C 12 alkylcarbonyl Or C 1 -C 12 alkoxycarbonyl;
- R 1 is selected from hydrogen, Cl, Br, F, I, cyano, unsubstituted or substituted by 1-4 phenoxy or heteroaryloxy groups independently selected from halogen, nitro, cyano , C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, C 1 -C 6 alkylcarbonyl or C 1 -C 6 alkoxycarbonyl;
- R 2 is selected from hydrogen, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 3 -C 6 ring Alkyl, cyano C 1 -C 6 alkyl, C 1 -C 6 alkylamino, halogenated C 1 -C 6 alkylamino, C 2 -C 6 dialkylamino, C 2 -C 6 alkenyl , Halogenated C 2 -C 6 alkenyl, C 2 -C 6 alkenyloxy, halogenated C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyl, halogenated C 2 -C 6 alkenyl, C 2- C 6 alkynyloxy, halo C 2 -C 6 alkynyloxy, C 1 -C 6 alkylsulfonyl, C 1 -C 6 alkylcarbonyl
- R 3 is selected from unsubstituted or substituted by 1-4 phenyl, benzyl or heteroaryl groups independently selected from Cl, Br, F, I, hydroxyl, nitro, cyano, CHO, COOH , COONa, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 1 -C 6 alkoxy, halo C 1 -C 6 alkoxy, C 3 -C 6 cycloalkyl, Cyano C 1 -C 6 alkyl, C 1 -C 6 alkylamino, halo C 1 -C 6 alkylamino, C 2 -C 6 dialkylamino, C 2 -C 6 alkenyl, halo C 2 -C 6 alkynyl, C 2 -C 6 alkenyloxy, halo C 2 -C 6 alkenyloxy, C 2 -C 6 alkynyl, halo C 2 -C 6 alkynyl
- R 2 NR 3 may also constitute a five- or six-membered ring substituted or unsubstituted by one to four groups independently selected from the group consisting of Cl, Br, F, I, Hydroxyl, nitro, cyano, CHO, COOH, COONa, C 1 -C 6 alkyl, halo C 1 -C 6 alkyl, C 3 -C 6 cycloalkyl, C 1 -C 6 alkoxy, Halo C 1 -C 6 alkoxy, C 1 -C 6 alkylthio, C 1 -C 6 alkylcarbonyl or C 1 -C 6 alkoxycarbonyl;
- R 4 is selected from Cl, Br, F, I, cyano, CHO, COOH, COONa, C 1 -C 6 alkylsulfonyl or halo C 1 -C 6 alkylsulfonyl;
- a further preferred compound of the present application is: in the general formula (I)
- R 1 is selected from H, Cl, Br, F, I, CN, CH 3 , CH 2 CH 3 , tert-butyl, cyclopropyl, CF 3 , CH 2 CF 3 , OCH 3 , OCF 3 , OCH 2 CF 3 , SO 2 CH 3 , CO 2 CH 3 , unsubstituted or substituted phenoxy, the substituent is selected from 1-3 groups: Cl, Br, F, I, CN, NO 2 , CHO, COOH, COONa, CH 3 , CH 2 CH 3 , tert-butyl, cyclopropyl, CHF 2 , CF (CF 3 ) 2 , CF 3 , CH 2 CF 3 , OCH 3 , OCHF 2 , OCF 3 , OCH 2 CF 3 or SO 2 CH 3 ;
- R 2 is selected from H, methyl, ethyl, propyl, isopropyl, t-butyl, n-butyl or methoxy, cyclopropyl, cyanoethyl, methylamino, methanesulfonyl, allyl , Propargyl, methanesulfonyl, p-toluenesulfonyl, ethylcarbonyl or formyl;
- R 3 is selected from unsubstituted or substituted by 1-3, phenyl, benzyl or heteroaryl groups independently selected from the group consisting of OH, Cl, Br, F, I, CN, NO 2 , CHO, COOH, COONa, CH 3 , CH 2 CH 3 , tert-butyl, cyclopropyl, CHF 2 , CF 3 , CF (CF 3 ) 2 , CH 2 CF 3 , OCH 3 , OCHF 2 , OCF 3 , OCH 2 CF 3 or SO 2 CH 3 ;
- R 2 NR 3 may also constitute a five- or six-membered ring substituted or unsubstituted by one to three groups independently selected from the group consisting of OH, Cl, Br, F, I, CN, NO 2 , CH 3 , CH 2 CH 3 , tert-butyl, cyclopropyl, CHF 2 , CF (CF 3 ) 2 , CF 3 , CH 2 CF 3 , OCH 3 , OCHF 2 , OCF 3 , OCH 2 CF 3 or SO 2 CH 3 ;
- R 4 is selected from Cl, Br, F, I, CN, SO 2 CH 3 or SO 2 CH 2 CH 3 ;
- a further preferred compound of the present application is: in the general formula (I)
- R 1 is selected from Cl, Br, F, I, 2-methylphenol, 2-isopropylphenol, 2-cyclopropylphenol, 2-methyl-6-cyclopropylphenol, or 2-iodophenol;
- R 2 is selected from H, CH 3 , CH 2 CH 3 , cyclopropyl, methoxy or methylamino;
- R 3 is selected from unsubstituted or substituted by 1-3, independently selected from phenyl, pyrimidinyl, pyrazolyl, pyridyl, or pyridazinyl: OH, Cl, Br, F, I, CN, NO 2 , CHO, COOH, COONa, CH 3 , CH 2 CH 3 , tert-butyl, cyclopropyl, CHF 2 , CF 3 , CH 2 CF 3 , OCH 3 , OCHF 2 , OCF 3 , CF (CF 3 ) 2. OCH 2 CF 3 or SO 2 CH 3 ;
- R 2 NR 3 may also form morpholine, piperazine, piperidine, pyrrole ring, pyrazole ring, triazole ring, pyrimidine ring or Wait;
- R 4 is selected from Cl, Br, F, I or CN;
- a further preferred compound of the present application is: in the general formula (I)
- R 1 is selected from Cl, Br, F or I;
- R 2 is selected from H, CH 3 or CH 2 CH 3 ;
- R 3 is selected from unsubstituted or substituted by 1-3, phenyl, pyridyl, or pyridazinyl independently selected from the group: OH, Cl, Br, F, I, CN, NO 2 , CHO, COOH, COONa, CH 3 , CH 2 CH 3 , tert-butyl, CHF 2 , CF 3 , CH 2 CF 3 , CF (CF 3 ) 2 , OCH 3 , OCHF 2 , OCF 3 , OCH 2 CF 3 or SO 2 CH 3 ;
- R 2 NR 3 can also be composed Ring etc
- R 4 is selected from Cl, Br, F, I or CN;
- stereoisomers can be formed because different groups or substituents are attached to a chiral carbon or nitrogen (respectively different configurations are represented by R and S).
- This application includes the R-isomer and S-isomer and mixtures thereof in any proportion.
- Halogen refers to fluorine, chlorine, bromine or iodine.
- Alkyl linear, branched or cyclic alkyl, such as methyl, ethyl, propyl, isopropyl, tert-butyl or cyclopropyl.
- Haloalkyl A straight or branched chain haloalkyl group.
- the hydrogen atoms on these alkyl groups may be partially or completely replaced by halogen atoms.
- haloalkyl groups such as chloromethyl, dichloromethyl, trichloromethyl, and fluoromethyl. Radical, difluoromethyl or trifluoromethyl.
- Alkoxy linear, branched or cyclic alkoxy, such as methoxy, ethoxy, propoxy, isopropoxy, tert-butoxy or cyclopropoxy.
- Haloalkoxy linear or branched haloalkoxy.
- the hydrogen atoms on these alkoxy groups may be partially or completely replaced by halogen atoms.
- haloalkyl such as chloromethoxy, dichloromethoxy, trichloro Methoxy, fluoromethoxy, difluoromethoxy or trifluoromethoxy.
- Alkylthio A linear or branched alkyl group attached to the structure via a sulfur atom bond.
- Haloalkylthio A straight or branched chain alkylthio group.
- the hydrogen atoms on these alkylthio groups may be partially or completely replaced by halogen atoms.
- halogen atoms For example, chloromethylthio, dichloromethylthio, trichloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, or chlorofluoromethylthio, and the like.
- Alkenyl straight or branched and may have a double bond at any position, such as vinyl or allyl.
- Alkynyl straight or branched and may have a triple bond at any position, such as ethynyl or propargyl.
- the aryl group in the aryl group and the aralkyl group includes a phenyl group or a naphthyl group.
- the heteroaryl group referred to in this application is a five-membered ring, six-membered ring or fused heterocyclic compound containing one or more N, O, and S heteroatoms.
- R 1 , R 2 , R 3 and R 4 have the same meanings as defined in the general formula (I).
- Acids that can be salted with pyridazinamine represented by the general formula (II) in the present application include: carboxylic acids such as acetic acid, propionic acid, butyric acid, oxalic acid, or trifluoroacetic acid; sulfonic acids such as methanesulfonic acid, p-toluene Sulfonic acid or dodecylbenzenesulfonic acid; and inorganic acids such as hydrochloric acid, sulfuric acid, nitric acid or carbonic acid.
- the bases and metals that can be salted with the pyridazinamine represented by the general formula (II) in the present application include: metals such as sodium, alkali, calcium, or magnesium; organic bases such as sodium methoxide, sodium ethoxide, and sodium tert-butoxide , Potassium methoxide, potassium ethoxide, sodium formate, butyllithium or sodium acetate, etc .; inorganic bases, such as sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, sodium hydride or sodium amide;
- Tables 1 and 2 respectively list specific substituents of the R 1 and R 4 moieties in the general formula I, but they are not limited to these substituents.
- R 1 represents some specific substituents
- R 4 represents some specific substituents
- the compound of general formula (I) of the present application can be obtained from pyridazine compound II by the method described in the literature, such as
- R 2 NR 3 indicates Groups can be prepared from compound A with reference to the literature, such as: CN105753853A and CN103058933.
- the reaction is performed in a suitable solvent.
- the suitable solvent may be selected from benzene, toluene, xylene, acetone, tetrahydrofuran, acetonitrile, N, N-dimethylformamide, N-methylpyrrolidone, dichloromethane, chloroform, Ethyl chloride or ethyl acetate.
- the reaction can be carried out in the presence or absence of a base. When the reaction is carried out in the presence of a base, the reaction can be accelerated.
- the base may be selected from: alkali metal hydrides, such as sodium hydride, lithium hydride, or sodium amide; etc .; alkali metal hydroxides, such as sodium hydroxide or potassium hydroxide; alkali metal carbonates, such as sodium carbonate or carbonate Potassium; organic bases, such as pyridine, 4-dimethylaminopyridine, triethylamine, N-methylpyrrole or diisopropylethylamine.
- the reaction temperature may be between -10 ° C and a suitable solvent boiling temperature selected for the reaction, and is usually 0-100 ° C.
- the reaction time is 30 minutes to 20 hours, and usually 1 to 10 hours.
- X and Z are both leaving groups, and X and Z are selected from fluorine, chlorine, bromine, iodine, mesylate or p-toluenesulfonate.
- Compound I and its agriculturally acceptable salts are suitable for use as herbicides in the form of mixtures of isomers and in the form of pure isomers. They are suitable for direct use or for use in suitably formulated compositions.
- the herbicidal composition comprising Compound I is very effective in controlling plant growth in non-crop areas, especially at high application rates. They act in crops such as wheat, rice, corn, soybeans and cotton on broadleaf and grass weeds without causing any significant damage to the crop. This effect is mainly observed at low application rates.
- compounds I or compositions comprising them can be additionally used in many other crops to eliminate unwanted plants.
- suitable crops are:
- Compound I or a herbicidal composition comprising compound I may be, for example, ready-to-spray aqueous solutions, powders, suspensions and highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, powders, materials for broadcasting or
- the granular form is used by spraying, atomizing, dusting, sowing, watering or treating the seeds or mixing with the seeds.
- the use form depends on the intended purpose; in each case, the best possible distribution of the active ingredients of the application should be ensured.
- the herbicidal composition comprises a herbicidally effective amount of at least one compound of formula I or an agriculturally acceptable salt of I and an adjuvant commonly used in formulating crop protection agents.
- auxiliaries commonly used in the formulation of crop protection agents are: inert auxiliaries, solid carriers, surfactants (such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers), organic and inorganic thickeners, Fungicides, antifreezes, and defoamers, if appropriate, colorants and binders for seed formulations.
- surfactants such as dispersants, protective colloids, emulsifiers, wetting agents and tackifiers
- organic and inorganic thickeners such as Fungicides, antifreezes, and defoamers, if appropriate, colorants and binders for seed formulations.
- thickeners i.e. compounds which impart modified flow properties to the formulation, i.e. high viscosity at rest and low viscosity at movement
- polysaccharides such as xanthan gum
- organic and inorganic flake minerals are examples of thickeners.
- defoamers are: polysiloxane emulsions, long-chain alcohols, fatty acids, fatty acid salts, organic fluorine compounds, and mixtures thereof.
- antifreeze examples include: ethylene glycol, propylene glycol, urea or glycerol.
- binder examples include polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol, and sodium cellulose acetate.
- Suitable inert auxiliaries are, for example, the following: medium- to high-boiling mineral oil fractions such as kerosene and diesel, but also coal tar and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons such as paraffin, four Hydrogenated naphthalenes, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone or strong polar solvents such as Amines such as N-methylpyrrolidone, and water.
- medium- to high-boiling mineral oil fractions such as kerosene and diesel, but also coal tar and oils of vegetable or animal origin
- aliphatic, cyclic and aromatic hydrocarbons such as paraffin
- four Hydrogenated naphthalenes alkylated naphthal
- the solid carriers are: mineral earth such as silica, silica gel, silicate, talc, kaolin, limestone, lime, chalk, red basalt, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide. Crushed synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and urea, and products of plant origin such as cereal flour, bark flour, wood flour and nut shell flour, cellulose flour or other solid carriers.
- mineral earth such as silica, silica gel, silicate, talc, kaolin, limestone, lime, chalk, red basalt, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate and magnesium oxide. Crushed synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate and urea, and products of plant origin such
- Suitable surfactants are aromatic sulfonic acids such as lignosulfonic acid (e.g. Borrespers type, Borregaard), phenolsulfonic acid, naphthalenesulfonic acid (Morwet Type, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal type, BASF SE) and alkali metal salts, alkaline earth metal salts and ammonium salts of fatty acids, alkyl- and alkylaryl sulfonates, alkyl sulfates, Lauryl ether sulfates and fatty alcohol sulfates, as well as sulfated cetyl-, hepta- and octadecyl alcohol, and fatty alcohol glycol ether salts, sulfonated naphthalene and its derivatives with formaldehyde.
- aromatic sulfonic acids such as lignosulfonic acid (e.g. Borre
- Condensates condensation products of naphthalene or naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octyl phenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylbenzene
- Polyglycol ether alkylaryl polyether alcohol, isotridecanol, fatty alcohol / ethylene oxide condensate, ethoxylated castor oil, polyoxyethylene alkyl ether or polyoxypropylene alkyl ether, Lauryl alcohol polyethylene glycol ether acetate, sorbitol ester, lignin sulfite waste liquid and protein, denatured protein, polysaccharide (such as methyl cellulose) Hydrophobic modified starch, polyvinyl alcohol (Mowiol type, Clariant), polycarboxylates (BASF SE, Sokalan type), polyal
- Powders, spreading materials and dusts can be prepared by mixing or grinding the active ingredients with a solid carrier.
- Particles such as coated particles, impregnated particles and homogeneous particles can be prepared by adhering the active ingredient to a solid carrier.
- Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water.
- the compounds of the formula I or Ia can be homogenized directly or dissolved in oil or solvents with the aid of a wetting agent, tackifier, dispersant or emulsifier.
- concentrates containing active substances, wetting agents, tackifiers, dispersants or emulsifiers and, if necessary, solvents or oils such concentrates being suitable for dilution with water.
- the concentration of the compound of formula I in the ready-to-use preparations can be varied within wide limits.
- the formulations usually contain at least one active compound in an amount of 0.001 to 98% by weight, preferably 0.01 to 95% by weight.
- the active compound is used in a purity of 90-100%, preferably 95-100% (according to the NMR spectrum).
- Formulations or ready-to-use preparations may also contain acid, base or buffer systems, suitable examples are: phosphoric acid or sulfuric acid, or urea or ammonia.
- Compound I of the present application can be formulated, for example, as follows:
- the active compound 20 parts by weight of the active compound is dissolved in 70 parts by weight of cyclohexanone and 10 parts by weight of a dispersant such as polyvinylpyrrolidone is added. Dilute with water to obtain a dispersion.
- the active compound content is 20% by weight.
- the active compound 15 parts by weight of the active compound are dissolved in 75 parts by weight of an organic solvent such as an alkylarene and calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight) are added. Dilute with water to obtain an emulsion.
- the formulation has an active compound content of 15% by weight.
- the active compound 25 parts by weight of the active compound are dissolved in 35 parts by weight of an organic solvent such as an alkylarene and calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight) are added.
- an organic solvent such as an alkylarene and calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight) are added.
- This mixture was introduced into 30 parts by weight of water by means of an emulsifier (Ultraturrax) and made into a homogeneous emulsion. Dilute with water to obtain an emulsion.
- the formulation has an active compound content of 25% by weight.
- the active compound is finely ground and added with 50 parts by weight of a dispersant and a wetting agent, and it is made into water-dispersible or water-soluble particles by means of an industrial device (such as an extruder, a spray tower, a fluidized bed). Dilution with water gives a stable dispersion or solution of the active compound.
- the formulation has an active compound content of 50% by weight.
- the active compound 75 parts by weight of the active compound are ground in a rotor-stator mill and 25 parts by weight of a dispersant, a humectant and silica gel are added. Dilution with water gives a stable dispersion or solution of the active compound.
- the formulation has an active compound content of 75% by weight.
- 0.5 parts by weight of the active compound are finely ground and combined with 99.5 parts by weight of the carrier.
- Current methods are extrusion, spray drying or fluidized bed methods. This gives granules with an active compound content of 0.5% by weight applied without dilution.
- Compounds I or herbicidal compositions comprising them can be applied before or after emergence, or together with the seeds of crops.
- the herbicidal composition or active compound can also be applied by applying the seeds of a crop plant pretreated with the herbicidal composition or active compound. If the active compounds are not well tolerated by certain crops, it can be used in which the herbicidal composition is sprayed by means of a spraying device so that they do not touch the leaves of sensitive crops as much as possible, while the active ingredients reach the leaves of the unwanted plants growing Or application techniques on bare soil surfaces.
- the compound of formula I or a herbicidal composition thereof can be applied by treating the seeds.
- Seed treatment basically includes all procedures well-known to those skilled in the art based on the compound of Formula I or the composition prepared therefrom (seed dressing, seed coating, seed dusting, seed soaking, seed coating, seed multilayer Coating, seed coating, seed dripping and seed granulation).
- the herbicidal composition can be applied here with or without dilution.
- seed includes all types of seeds, such as grains, seeds, fruits, tubers, cuttings and similar forms.
- seed describes grains and seeds.
- the seeds used may be seeds of the useful plants described above, but may also be seeds of transgenic plants or plants obtained by conventional breeding methods.
- the application rate of the active compound is 0.001-3.0 kg / ha, preferably 0.01-1.0 kg / ha of active substance (a.s.), depending on the control target, season, target plant and growth stage.
- Compound I is usually used in an amount of 0.001-10 kg / 100 kg of seeds.
- Safeners are compounds that prevent or reduce damage to useful plants without significantly affecting the herbicidal effect of compounds of formula I on unwanted plants. They can be used before sowing (for example in seed treatment or on cuttings or seedlings) and before or after emergence of useful plants. The safener and the compound of formula I can be used simultaneously or sequentially.
- Suitable safeners are, for example, (quinoline-8-oxy) acetic acid, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acid, 1-phenyl-4, 5-dihydro-5-alkyl-1H-pyrazole-3,5-dicarboxylic acid, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acid, dichloroacetamide Type, ⁇ -oxime phenylacetonitrile, acetophenone oxime, 4,6-dihalo-2-phenylpyrimidine, N-[[4- (aminocarbonyl) phenyl] sulfonyl] -2- Benzamide, 1,8-naphthalenedicarboxylic anhydride, 2-halo-4-haloalkyl-5-thiazolecarboxylic acids, phosphorothioates and O-phenyl N-alkyl carbamates and their applications
- the compounds of formula I can be mixed with a number of other representative or safeners of herbicidal or growth-regulating active compounds and applied in combination.
- Suitable mixed pairs are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acids and their derivatives, aminotriazoles, amidoanilines, aryloxy / Heteroaryloxyalkanoic acid and its derivatives, benzoic acid and its derivatives, benzothiadiazinone, 2-heteroaroyl / aroyl-1,3-cyclohexanedione, hetero Aryl aryl ketones, benzyl isoxazolidinones, m-CF3-phenyl derivatives, carbamates, quinoline carboxylic acids and their derivatives, chloroacetanilides, cyclohexanone oxime ethers Derivatives, diazines, dichloropropi
- Compound I alone or in combination with other herbicides, or it may also be applied in combination with other crop protection agents, such as in combination with a composition for controlling pests or plant pathogenic fungi or bacteria Compound I.
- crop protection agents such as in combination with a composition for controlling pests or plant pathogenic fungi or bacteria Compound I.
- miscibility with inorganic salt solutions used to alleviate nutritional and trace element deficiencies is also of interest.
- Other additives such as non-phytotoxic oils and oil concentrates can also be added.
- herbicides that can be used in combination with the pyridine compound of formula I of the present application are:
- lipid biosynthesis inhibitor selected from the group consisting of clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop , Cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop-ethyl, fluazifop, fluflufop Fluazifop-butyl, fluazifop-P, fluazifop-P-butyl, haloxyfop, haloxyfop -methyl), haloxyfop-P, haloxyfop-P-methyl, metafop, pinoxaden, cyproben Ketone (profoxydim), propaquizafop, quizalofop, quizalofop-ethyl, quizalofop-tefuryl, quizalofop -P), quizalofop-
- an ALS inhibitor selected from the group consisting of bensulfuron, bensulfuron-methyl, bispyribac, cinosulfuron, cloransulam , Cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuron-methyl, ethoxysulfuron-methyl ethoxysulfuron, flazasulfuron, florasulam, flucarbazone, flucetosulfuron, flumetsulam, flupyrsulfuron ), Flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazosulfuron, iodosulfuron (Iodosulfuron), iodosulfuron-methyl-sodium, mesosulfuron, metosulam, metsulfuron, mets, met
- a photosynthesis inhibitor selected from the group consisting of: ametryn, amidcarbazone, atrazine, bentazone, bentazone-sodium, and bromacil ), Bromofenoxim, bromoxynil and its salts and esters, chlorobromuron, chloridazone, cyanazine, desmedipham, Desmetryn, diquat-dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isopropyl Isoproturon, isouron, karbutilate, lenacil, linuron, metamitron, methabenzthiazuron, carbazoxan (paraquat-dimetilsulfate), pentanochlor, phenmedipham, phenmedipham-ethyl, prometon, prometryn, propanil, extinguish Propazine, pyridafol, pyridate, sidur
- protoporphyrinogen-IX oxidase inhibitors acifluorfen, aciflorfen-sodium, azafenidin, bencarbazone, diflufenazone (benzfendizone), bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, indoxazone (cinidon-ethyl), iprazol (fuazolate), fufenpyr (flufenpyr), flufenpyr-ethyl (flufenpyr-ethyl), flumiclorac, imidophenoxy Flumiclorac-pentyl, flumioxazin, fluoroglycofen, fluoroglycofen-ethyl, fluthiacet, fluthiacet- methyl), fomesafen, halosafen, lactofen, oxadiargyl,
- a bleaching herbicide selected from the group consisting of aclofen, amitrol, beflubutamid, benzobicyclon, benzofenap, isopropyl Clomazone, diflufenican, fluridone, flurochloridone, flurtamone, isoxaflutole, mesotrione (mesotrione), norflurazon, picolinafen, pyrasulfutole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, topramezone, bixlozone , Trisulcotrione, Ciclotrione, Diflufenazone, 4-Hydroxy-3-[[2-[(2-methoxyethoxy) methyl] -6- (trifluoromethyl ) -3-pyridyl] carbonyl] bicyclo [3.2.1] oct-3-en-2-one (H-7;
- an EPSP synthetase inhibitor selected from the group consisting of glyphosate, glyphosate-isopropylammonium, and glyphosate-trimesium (sulfosate);
- a glutamine synthetase inhibitor selected from the group consisting of bilanaphos (bialaphos), bilanaphos-sodium and glufosinate-ammonium;
- b9) is selected from the following mitotic inhibitors: amiprophos, amiprophos-methyl, benfluralin, butamiphos, butralin, longan Carbamide, chlorpropham, chlorthal, chlorthal-dimethyl, dinitramine, dithiopyr, ethalfluralin ), Fluchloralin, oryzalin, pendimethalin, prodiamine, propham, propyzamide, tebutam ), Thiazopyr and trifluralin;
- VLCFA inhibitor selected from the group consisting of acetochlor, alachlor, anilofos, butachlor, cafenstrole, and dimethachlor ), Dimethanamid, dimethenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet , Metazachlor, metolachlor, S-metolachlor-S, naproanilide, napropamide, pethoxamid, Piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KIH-485), and thenylchlor );
- a cellulose biosynthesis inhibitor selected from the group consisting of chlorthiamid, dichlobenil, flupoxam, and isoxaben;
- a separating agent herbicide selected from the group consisting of dinoseb, dinoterb, and DNOC and salts thereof;
- auxin herbicide selected from the group consisting of 2,4-D and salts and esters thereof, 2,4-DB and salts and esters thereof, aminopyralid and salts thereof such as ammonium salt ( aminopyralid-tris (2-hydroxypropyl) ammonium) and its esters, benazolin, benazolin-ethyl, chloramben and its salts and esters, clomeprop, diammonium Clopyralid and its salts and esters, dicamba and its salts and esters, 2,4-dichlorprop and its salts and esters, and high 2,4-dipropionic acid ( dichlorprop-P) and its salts and esters, fluroxypyr, fluroxypyr-butometyl, fluroxypyr-meptyl, MCPA and its salts and esters, 2 methyl 4-chloroethyl thiosulfate (MCPA-thioethyl), MCPB and its salts and esters, 2
- auxin transport inhibitor selected from the group consisting of diflufenzopyr and naptalam;
- herbicides selected from the group consisting of bromobutide, chlorflurenol, chlorflurenol-methyl, cinmethylin, cumyluron, Thatch, dazomet, difenzoquat, difenzoquat-metilsulfate, dimethipin, sodium formazan (DSMA), dymron, endothal ) And its salts, flamprop, flamprop-M-isopropyl, flamprop-M-methyl, flurenol, flurenol-butyl, Flurprimidol, fosamine, fosamine-ammonium, indanofan, maleic hydrazide, mefluidide, methamphetamine (methyl- dymron), oxaziclomefone, pelargonic acid, piributicarb, and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4- Pyridazinol (H-10;
- Examples of the preferred safener C are: benoxacor, cloquintocet, cymetrinil, cyprosulfamide, dichlormid, dicyclonone, dietholate, fenchlorazole, Fenclorim, flurazole, fluxofenim, furilazole, isoxadifen, mefenpyr, mephenate, naphthalenedicarboxylic anhydride ( naphthalic anhydride), oxabetrinil, 4- (dichloroacetyl) -1-oxa-4-azaspiro [4.5] decane (H-11; MON4660, CAS 71526-07-3), and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (H-12; R-29148, CAS 52836-31-4).
- the b1) -b15) groups of active compounds and safeners are known herbicides and safeners, see, for example, The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, RR Schmidt, Herbizide [herbicide], Georg Thieme Verlag, Stuttgart, 1995.
- Other herbicidally active compounds are described in WO 96/26202, WO 97/41116, WO 97/41117, WO 97/41118, WO 01/83459, and WO 2008/074991, W. (Edit) "Modern Crop Protection Compounds", Vol. 1, Wiley VCH, 2007 and the literature cited therein are known.
- the application also relates to a composition in the form of a crop protection composition formulated as a one-component composition comprising at least one pyridazine compound of formula I and at least one preferably selected from the group b1-b15 Active compounds Other active compounds Active compound combinations and at least one solid or liquid carrier and / or one or more surfactants and, if necessary, one or more other adjuvants commonly used in crop protection compositions.
- the application also relates to a composition in the form of a crop protection composition formulated as a two-component composition comprising at least one pyridazine compound of formula I, a solid or liquid carrier and / or one or A first component of a plurality of surfactants and a second component containing at least one other active compound selected from the group b1 to b15, a solid or liquid carrier, and / or one or more surfactants, wherein These two components may additionally contain other adjuvants commonly used in crop protection compositions.
- the compound I and the composition of the present application may also have a plant enhancing effect. They are therefore suitable for mobilizing the plant's defense system against attack by unwanted microorganisms such as harmful fungi as well as viruses and bacteria.
- Plant enhancement (induced resistance) substances are understood in the context of the present application to mean those capable of stimulating the defense system of the treated plants such that the treated plants show significant resistance to these microorganisms when subsequently inoculated with unwanted microorganisms substance.
- Compound I can be used to protect plants from unwanted microorganisms for a certain period of time after treatment.
- the period of time for protection is usually 1-28 days, preferably 1-14 days, after treatment of the plant or the seeds with compound I, up to 9 months after sowing.
- the compounds I and compositions of the present application are also suitable for increasing harvest yield.
- Compound I-B-1 melting point 140-142 ° C. ⁇ ppm 7.95-8.05 (1H, s), 8.30-8.40 (1H, s), 8.60-8.70 (1H, s), 9.00-9.10 (1H, s).
- the culture vessel used was a plastic flowerpot containing loamy sand containing about 3.0% humus soil as a substrate. Seeds of the test plants were sown individually for each variety.
- the active ingredients suspended or emulsified in water are applied directly after sowing by means of fine distribution nozzles.
- the container is gently irrigated to promote germination and growth, and then covered with a transparent plastic cover until the plant takes root. This coverage results in uniform germination of the test plants unless damaged by the active compound.
- test plants For post-emergence treatment, the test plants are first grown to a height of 3-15 cm, depending on plant habits, and only treated with active ingredients suspended or emulsified in water at this time. To this end, the test plants are sown directly and grown in the same container, or they are first grown individually as seedlings and transplanted into the test container a few days before treatment.
- the plants are kept at 10-25 ° C or 20-35 ° C.
- the test period is 2-4 weeks. Plants were cared for during this period and their response to each treatment was evaluated.
- Evaluation is performed using a scale of 0-100. 100 means no plant emerges, or at least part of the ground is completely damaged, while 0 means no damage or normal growth. A good herbicidal activity is given a score of at least 70 and a very good herbicidal activity is given a score of at least 85.
- the plants used in the greenhouse tests belong to the following varieties:
- the compounds I-A-8, I-I-1, and I-A-19 applied by the post-emergence method showed very good herbicidal activity against Goosegrass.
- the compound I-I-1 applied by the post-emergence method showed very good herbicidal activity against Yarrow.
- the compound I-I-1 applied by the post-emergence method showed very good herbicidal activity against Mai Niang.
- the compound I-I-1 applied by the post-emergence method showed very good herbicidal activity against bluegrass.
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Abstract
Description
R 4 | R 4 | R 4 | R 4 | R 4 |
H | F | Cl | Br | I |
CHO | CN | COOH | SO 2CH 3 | SO 2CH 2CH 3 |
(R 6) n | (R 6) n | (R 6) n |
2-F | 2-Br | 2-CH 3-4-Cl-6-CON(CH 3) 2 |
2,4-2F | 2,6-2Br-4-NO 2 | 2-CH 3-4-Cl-6-CONHCH(CH 3) 2 |
2,6-2F | 2,6-2Br-4-OCF 3 | 2-CH 3-4-Cl-6-CONHC(CH 3) 3 |
2-F-5-CH 3 | 3-Br-4-CN | 2-CH 3-4-Br-6-CO 2CH 3 |
2-F-5-NO 2 | 4-Br | 2-CH 3-4-Br-6-CONH 2 |
2-F-4-CN | 2-I | 2-CH 3-4-Br-6-CON(CH 3) 2 |
2,3,4-3F | 4-I | 2-CH 3-4-NO 2-6-F |
2-F-4-NO 2 | 2-NO 2 | 2-CH 3-4-NO 2-6-Cl |
2,6-2F-4-CF 3 | 2-NO 2-4-Cl | 2-CH 3-4-NO 2-6-Br |
2,5-2F-4-CO 2C 2CH 5 | 2-NO 2-4-CN | 2-CH 3-4-NO 2-6-CN |
2,6-2F-4-NO 2 | 2-NO 2-5-Cl | 2-CH 3-4-NO 2-6-CF 3 |
2,6-2F-4-OCF 3 | 2,6-2NO 2-4-Cl | 2-CH 3-4-NO 2-6-OCH 3 |
2-F-4-NO 2-6-Cl | 2,6-2NO 2-4-SOCH 3 | 2-CH 3-4-NO 2-6-SO 2CH 3 |
2-F-4-CN-5-CO 2CH 3 | 2,6-2NO 2-4-SO 2CH 5 | 2-CH 3-4-NO 2-6-CO 2H |
2-F-4-CN-5-NO 2 | 2-NO 2-4,6-2Cl | 2-CH 3-4-NO 2-6-CO 2CH 3 |
2-F-4-CN-6-OCH 3 | 2-NO 2-4-Cl-6-F | 2-CH 3-4,6-2CN |
2-F-4-NO 2-6-Cl | 2-NO 2-4-CN-6-Cl | 2-CH 3-4-CN-6-NO 2 |
2-F-4-NO 2-6-Br | 2-NO 2-3-C 2H 5-6-CO 2H 3 | 2-CH 3-4-CN-6-CF 3 |
2-F-4-CN-6-Cl | 2-NO 2-4-CO 2H 3-6-SCH 3 | 4-CH 3 |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
3-I | 5-CHO | 4-I-5-CH 3 | 3,5-2F-4-CF 3 |
4-Cl | 3-NH 2 | 4-I-5-CF 3 | 3,6-2F-4-CF 3 |
4-Br | 4-NH 2 | 5-I-6-C 2H 5 | 3-F-5-CN-6-Cl |
4-I | 5-NH 2 | 3-NO 2-4-Cl | 3-F-5-CO 2CH 3-6-Cl |
5-Cl | 6-NH 2 | 3-NO 2-4-CH 3 | 3-F-5-CONH 2-6-Cl |
5-Br | 3-CONH 2 | 3-NO 2-5-Cl | 3-F-5-CONHCH(CH 3) 2-6-Cl |
5-I | 4-CONH 2 | 3-NO 2-5-Br | 3,5-2Cl-4-CH 3 |
6-Cl | 5-CONH 2 | 3-NO 2-5-I | 3,5-2Cl-6-CH 3 |
6-Br | 3-F-5-Cl | 3-NO 2-6-Cl | 3,5-2Cl-4,6-2CH 3 |
3-NO 2 | 3-F-5-CN | 3-NO 2-6-CH 3 | 3,5-2Cl-6-OCH 2CO 2CH 3 |
4-NO 2 | 3-F-4-CF 3 | 3-NO 2-6-OCH 3 | 3,6-2Cl-5-CF 3 |
5-NO 2 | 3-F-5-CF 3 | 4-NO 2-6-CH 3 | 3,5,6-3Cl |
6-NO 2 | 3-F-4-CHO | 5-NO 2-6-Cl | 3-Br-5-CF 3-6-Cl |
3-CN | 4,6-2F | 5-NO 2-6-CH 3 | 3,5-2Br-4-CH 3 |
4-CN | 5-F-6-CH 3 | 5-NO 2-6-NHCOCH 3 | 3,5-2Br-6-CH 3 |
5-CN | 3,5-2Cl | 3-CN-6-CH 3 | 3-Br-5,6-2CH 3 |
6-CN | 4,6-2Cl | 3-CN-4-OCH 3 | 3-NO 2-4-CH 3-5-Br |
3-CH 3 | 3,5-2Br | 3-CH 3-5-CN | 3,5-2CN-6-Cl |
4-CH 3 | 3-Cl-5-Br | 4-CH 3-5-Br | 3-CN-5-F-6-Cl |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
H | 2-CH 3 | 2-Cl-5-CH 3 | 5-CO 2H-6-Cl |
2-F | 4-CH 3 | 2-Cl-5-CF 3 | 5-CO 2CH 3-6-Cl |
2-Br | 4-CF 3 | 2-Cl-4-CHO | 5-CONH 2-6-Cl |
2-Cl | 5-CF 3 | 2-Cl-5-SO 2NH 2 | 2,5,6-3F |
2-I | 6-CF 3 | 5-Cl-6-CN | 2,6-2F-5-Cl |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
H | 2-CF 3 | 3,5-2Cl | 2,6-2NO 2 |
2-F | 3-CF 3 | 3,5-2Br | 3,5-2CH 3 |
3-F | 5-CF 3 | 3,5-2I | 2,6-2CH 3 |
2-Cl | 2-OCH 3 | 2-F-5-CH 3 | 3-CH 3-2-Cl |
2-Br | 3-OCH 3 | 2-F-3-CHO | 3,6-2Cl-5-CF 3 |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
H | 5-CO 2C 2H 5 | 4-Cl-5-NO 2 | 4-CF 3-5-CO 2C 2H 5 |
4-F | 5-CO 2C(CH 3) 3 | 4-Cl-5-CN | 4-CF 3-5-CONH 2 |
4-Cl | 5-CHO | 4-Cl-5-CH 3 | 4-OCH 3-5-Br |
4-CN | 5-NH 2 | 4-Cl-6-CH 3 | 4,6-2OCH 3 |
4-NO 2 | 5-CONH 2 | 4-Cl-6-CH(CH 3) 2 | 4-CO 2CH 3-6-Cl |
4-CH 3 | 5-CONHCH 3 | 4-Cl-5-CF 3 | 4-CO 2C 2H 5-6-Cl |
4-CF 3 | 5-CONHC 2H 5 | 4-Cl-5-OCH 3 | 4-CO 2CH 3-6-CH 3 |
4-OCH 3 | 5-CONHCH(CH 3) 2 | 4-Cl-6-OCH 3 | 4-CO 2C 2H 5-6-CH 3 |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
H | 2,5-2Cl | 2-CH 3-6-Cl | 2-SCH 3-5-CONH 2 |
2-F | 2,6-2Cl | 5-CH 3-6-Cl | 2-SO 2CH 3-6-Cl |
2-Cl | 2-Cl-5-Br | 2-CH 3-5-CN | 2-SO 2CH 3-5-Br |
2-OC 2H 5 | 2-Cl-5-I | 2-CH 3-5-C(CH 3) 3 | 2-SO 2CH 3-6-OCH 3 |
2-SCH 3 | 2-Cl-5-NO 2 | 2-CF 3-5-CO 2C 2H 5 | 5-CHO-6-Cl |
2-SOCH 3 | 2-Cl-5-CN | 2-OCH 3-6-Cl | 5-CHO-6-NH 2 |
2-SO 2CH 3 | 2-Cl-5-CH 3 | 2-SCH 3-6-Cl | 5-CO 2H-6-Cl |
2-NHCH 3 | 2-Cl-6-CH 3 | 2-SCH 3-5-Br | 2-NH 2-6-CH(CH 3) 2 |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
H | 4-Cl | 2,4-2Br | 2-SCH 3-4-CO 2CH 3 |
2-F | 4-Br | 4,6-2Br | 2-SCH 3-4-CO 2H |
2-Cl | 2,4-2F | 2-OCH 3-4-Cl | 2-SCH 3-4-CONH 2 |
2-Br | 4,6-2F | 2-OCH 3-4-Br | 2-SCH 3-4-CSNH 2 |
2-I | 2,4,6-3F | 2,4-2OCH 3 | 2-SO 2CH 3-4-Cl |
2-CN | 2,4-2Cl | 4,6-2OCH 3 | 2-CH 3-4,6-2Cl |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
6-Cl | 6-CO 2CH 3 | 6-CON(CH 3) 2 | 4-Cl-6-CO 2CH 3 |
6-Br | 6-CO 2C 2H 5 | 6-CON(C 2H 5) 2 | 4-Cl-6-CONHCH 3 |
H | 6-CO 2C(CH 3) 3 | 6-CSNH 2 | 5,6-2Cl |
6-CN | 6-CO 2H | 6-CSNHCH 3 | 4-Br-6-CN |
6-CH 3 | 6-NH 2 | 4-F-6-CN | 4-Br-6-CO 2CH 3 |
6-OCH 3 | 6-N(CH 3) 2 | 4-F-6-CO 2CH 3 | 4-Br-6-CONHCH 3 |
6-SCH 3 | 6-CONH 2 | 4-F-6-CONHCH 3 | 4-CH 3-6-CN |
6-SOCH 3 | 6-CONHCH 3 | 3-Cl-5-NHCOCH 3 | 4-CH 3-6-CO 2CH 3 |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
H | 5,6-2Cl | 5-Cl-6-OCH 3 | 3-Cl-5-NHCOCH 3 |
3-Cl | 3-Cl-6-OCH 3 | 5-Cl-6-SCH 3 | 3-Cl-5-NHCO 2CH 3 |
6-Cl | 3-Cl-6-SCH 3 | 5-Cl-6-SOCH 3 | 5,6-2OCH 3 |
3,6-2Cl | 5-Cl-6-N(CH 3) 2 | 5-Cl-6-SO 2CH 3 | 5,6-2SCH 3 |
3,6-2F | 3,6-2Br | 3,6-2I | 3-F-6-Cl |
3-F-6-Br | 3-F-6-I | 3-Cl-6-F | 3-Cl-6-Br |
3-Cl-6-I | 3-Br-6-F | 3-Br-6-Cl | 3-Br-6-I |
3-I-6-F | 3-I-6-Cl | 3-I-6-Br | 3-SO 2CH 3-6-Cl |
3-SO 2C 2H 5-6-Cl | 3-CN-6-Cl | 3-Cl-6-CF 3 | 3-CN-6-CF 3 |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
H | 6-CO 2CH 3 | 6-CONHCH 3 | 4-CH 3-6-CN |
6-Cl | 6-CO 2C 2H 5 | 6-CONHC 2H 5 | 4-F-6-CO 2CH 3 |
6-Br | 6-CO 2C(CH 3) 3 | 6-CON(CH 3) 2 | 4-Cl-6-CO 2CH 3 |
6-CN | 6-CO 2H | 6-CSNH 2 | 4-Br-6-CO 2CH 3 |
6-CH 3 | 6-CO 2Na | 6-CSNHCH 3 | 4-CH 3-6-CO 2CH 3 |
6-OCH 3 | 6-CO 2NH 4 | 5,6-2Cl | 4-F-6-CONHCH 3 |
6-SCH 3 | 6-NH 2 | 4-F-6-CN | 4-Cl-6-CONHCH 3 |
6-SOCH 3 | 6-N(CH 3) 2 | 4-Cl-6-CN | 4-Br-6-CONHCH 3 |
6-SO 2CH 3 | 6-CONH 2 | 4-Br-6-CN | 4-CH 3-6-CONHCH 3 |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
4-Cl | 4-OCH 3-6-NHCH 3 | 4-N(CH 3) 2 | 4-NH-i-Pr-6-NHCOCH 3 |
4-CN | 4,6-2SCH 3 | 4-NH 2-6-Cl | 4-NH-i-Pr-6-NH 2 |
4-SCH 3 | 4-SCH 3-6-Cl | 4-NH 2-6-OCH 3 | 4-NH-i-Pr-6-NHCH 3 |
4-SOCH 3 | 4-SCH 3-6-NHCH 3 | 4-NH 2-6-SCH 3 | 4-NH-t-Bu-6-Cl |
4-SO 2CH 3 | 4-SOCH 3-6-Cl | 4-NH 2-6-SOCH 3 | 4-NH-t-Bu-6-CN |
4,6-2Cl | 4-SO 2CH 3-6-Cl | 4-NH 2-6-SO 2CH 3 | 4-NH-t-Bu-6-OCH 3 |
4-CN-6-Cl | 4-NHCOH 3-6-Cl | 4-NH-i-Pr-6-Cl | 4-NH-t-Bu-6-SCH 3 |
4,6-2CH 3 | 4-NHCOH 3-6-OCH 3 | 4-NH-i-Pr-6-CN | 4-NH-t-Bu-6-NH 2 |
4,6-2OCH 3 | 4-NHCOH 3-6-SCH 3 | 4-NH-i-Pr-6-OCH 3 | 4-NH-t-Bu-6-NHCH 3 |
4-OCH 3-6-Cl | 4-NHCOH 3-6-SO 2CH 3 | 4-NH-i-Pr-6-SCH 3 | 4-NH-t-Bu-6-NHCOH 3 |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
5-F-6-CN | 5-Br-6-CO 2CH 3 | 6-CO 2CH 3 | 6-CONH(C 2H 5) 2 |
5-Cl-6-CN | 5-F-6-CONCH 3 | 6-CO 2H | 6-CSNH 2 |
5-Br-6-CN | 5-Cl-6-CONCH 3 | 6-CONH 2 | 6-CSNHCH 3 |
5-CH 3-6-CN | 5-F-Br-CONCH 3 | 6-CONHCH 3 | 6-CSNHC 2H 5 |
5-F-6-CO 2CH 3 | 5-CH 3-6-CO 2CH 3 | 6-CONHC 2H 5 | 6-CSN(CH 3) 2 |
5-Cl-6-CO 2CH 3 | 6-CN | 6-CONH(CH 3) 2 | 6-CSN(C 2H 5) 2 |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
3-CN | 3-CONHCH 3 | 3-CSN(CH 3) 2 | 3-CO 2CH 3-6-Cl |
3-CO 2CH 3 | 3-CONHC 2H 5 | 3-CSN(C 2H 5) 2 | 3-CO 2CH 3-6-Br |
3-CO 2C 2H 5 | 3-CON(CH 3) 2 | 3-CN-6-F | 3-CO 2CH 3-6-CH 3 |
3-CO 2H | 3-CON(C 2H 5) 2 | 3-CN-6-Cl | 3-CONHCH 3-6-F |
3-CO 2Na | 3-CSNH 2 | 3-CN-6-Br | 3-CONHCH 3-6-Cl |
3-CO 2NH 4 | 3-CSNHCH 3 | 3-CN-6-CH 3 | 3-CONHCH 3-6-Br |
3-CONH | 3-CSNHC 2H 5 | 3-CO 2CH 3-6-F | 3-CONHCH 3-6-CH 3 |
(R 6)n | (R 6)n | (R 6)n | (R 6)n |
3-CN | 3-CONH 2 | 3-CSNHC 2H 5 | 3-CO 2CH 3-5-Cl |
3-CO 2CH 3 | 3-CONHCH 3 | 3-CSN(CH 3) 2 | 3-CO 2CH 3-5-Br |
3-CO 2C 2H 5 | 3-CONHC 2H 5 | 3-CN-5-F | 3-CO 2CH 3-5-CH 3 |
3-CO 2C(CH 3) 3 | 3-CON(CH 3) 2 | 3-CN-5-Cl | 3-CONHCH 3-5-F |
3-CO 2H | 3-CON(C 2H 5) 2 | 3-CN-5-Br | 3-CONHCH 3-5-Cl |
3-CO 2Na | 3-CSNH 2 | 3-CN-5-CH 3 | 3-CONHCH 3-5-Br |
3-CO 2NH 4 | 3-CSNHCH 3 | 3-CO 2CH 3-5-F | 3-CONHCH 3-5-CH 3 |
Claims (10)
- 一种通式I所表示的取代哒嗪胺或其N-氧化物或可农用盐:式中:R 1选自氢、卤素、氰基、未取代的或被1-4个独立选自以下基团取代的苯氧基或杂芳氧基:卤素、硝基、氰基、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 3-C 12环烷基、C 1-C 12烷基羰基或C 1-C 12烷氧基羰基;R 2选自氢、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 3-C 6环烷基、氰基C 1-C 12烷基、C 1-C 12烷基氨基、卤代C 1-C 12烷基氨基、C 2-C 6二烷基氨基、C 2-C 12烯基、卤代C 2-C 12炔基、C 2-C 12烯氧基、卤代C 2-C 12烯氧基、C 2-C 12炔基、卤代C 2-C 12烯基、C 2-C 12炔氧基、卤代C 2-C 12炔氧基、C 1-C 12烷基磺酰基、C 1-C 12烷基羰基、卤代C 1-C 12烷基羰基或卤代C 1-C 12烷磺酰基;R 3选自未取代的或被1-4个独立选自以下基团取代的苯基、苄基或杂芳基:卤素、羟基、硝基、氰基、CHO、COOH、COONa、C 1-C 12烷基、卤代C 1-C 12烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 3-C 6环烷基、氰基C 1-C 12烷基、C 1-C 12烷基氨基、卤代C 1-C 12烷基氨基、C 2-C 6二烷基氨基、C 2-C 12烯基、卤代C 2-C 12炔基、C 2-C 12烯氧基、卤代C 2-C 12烯氧基、C 2-C 12炔基、卤代C 2-C 12炔基、C 2-C 12炔氧基、卤代C 2-C 12炔氧基、C 1-C 12烷硫基、卤代C 1-C 12烷硫基、C 1-C 12烷基磺酰基、C 1-C 12烷基羰基、卤代C 1-C 12烷基羰基或卤代C 1-C 12烷磺酰基;R 2NR 3也可以组成被1-4个独立选自以下基团取代或未取代的五元或六元环,所述独立取代基团选自以下基团:卤素、羟基、硝基、氰基、CHO、COOH、COONa、C 1-C 12烷基、卤代C 1-C 12烷基、C 3-C 12环烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 1-C 12烷硫基、C 1-C 12烷基羰基或C 1-C 12烷氧基羰基;R 4选自卤素、氰基、CHO、COOH、COONa、C 1-C 12烷基磺酰基、卤代C 1-C 12烷基磺酰基或被1-4个独立选自以下基团取代或未取代的芳基磺酰基,所述独立取代基团选自以下基团:卤素、羟基、硝基、氰基、CHO、COOH、COONa、C 1-C 12烷基、卤代C 1-C 12烷基、C 3-C 12环烷基、C 1-C 12烷氧基、卤代C 1-C 12烷氧基、C 1-C 12烷硫基、C 1-C 12烷基羰基或C 1-C 12烷氧基羰基;或通式(I)化合物的N-氧化物或可农用盐。
- 根据权利要求1所述的哒嗪胺类化合物,其特征在于:通式(I)中式中:R 1选自氢、Cl、Br、F、I、氰基、未取代的或被1-4个独立选自以下基团取代的苯氧基或杂芳氧基:卤素、硝基、氰基、C 1-C 6烷基、卤代C 1-C 6烷基、C 1-C 6烷氧基、卤代C 1-C 6烷氧基、C 3-C 6环烷基、C 1-C 6烷基羰基或C 1-C 6烷氧基羰基;R 2选自氢、C 1-C 6烷基、卤代C 1-C 6烷基、C 1-C 6烷氧基、卤代C 1-C 6烷氧基、C 3-C 6环烷基、氰基C 1-C 6烷基、C 1-C 6烷基氨基、卤代C 1-C 6烷基氨基、C 2-C 6二烷基氨基、C 2-C 6烯基、卤代C 2-C 6烯基、C 2-C 6烯氧基、卤代C 2-C 6烯氧基、C 2-C 6炔基、卤代C 2-C 6炔基、C 2-C 6炔氧基、卤代C 2-C 6炔氧基、C 1-C 6烷基磺酰基、C 1-C 6烷基羰基、卤代C 1-C 6烷基羰基或卤代C 1-C 6烷磺酰基;R 3选自未取代的或被1-4个独立选自以下基团取代的苯基、苄基或杂芳基:Cl、Br、F、I、羟基、硝基、氰基、CHO、COOH、COONa、C 1-C 6烷基、卤代C 1-C 6烷基、C 1-C 6烷氧基、卤代C 1-C 6烷氧基、C 3-C 6环烷基、氰基C 1-C 6烷基、C 1-C 6烷基氨基、卤代C 1-C 6烷基氨基、C 2-C 6二烷基氨 基、C 2-C 6烯基、卤代C 2-C 6炔基、C 2-C 6烯氧基、卤代C 2-C 6烯氧基、C 2-C 6炔基、卤代C 2-C 6炔基、C 2-C 6炔氧基、卤代C 2-C 6炔氧基、C 1-C 6烷硫基、卤代C 1-C 6烷硫基、C 1-C 6烷基磺酰基、C 1-C 6烷基羰基、卤代C 1-C 6烷基羰基或卤代C 1-C 6烷磺酰基;R 2NR 3也可以组成被1-4个独立选自以下基团取代或未取代的五元或六元环,所述独立取代基团选自以下基团:Cl、Br、F、I、羟基、硝基、氰基、CHO、COOH、COONa、C 1-C 6烷基、卤代C 1-C 6烷基、C 3-C 6环烷基、C 1-C 6烷氧基、卤代C 1-C 6烷氧基、C 1-C 6烷硫基、C 1-C 6烷基羰基或C 1-C 6烷氧基羰基;R 4选自Cl、Br、F、I、氰基、CHO、COOH、COONa、C 1-C 6烷基磺酰基或卤代C 1-C 6烷基磺酰基;或通式(I)化合物的N-氧化物或可农用盐。
- 根据权利要求2所述的化合物,其特征在于:通式(I)中R 1选自H、Cl、Br、F、I、CN、CH 3、CH 2CH 3、叔丁基、环丙基、CF 3、CH 2CF 3、OCH 3、OCF 3、OCH 2CF 3、SO 2CH 3、CO 2CH 3、未取代或取代的苯氧基,所述的取代基选自1-3个如下基团:Cl、Br、F、I、CN、NO 2、CHO、COOH、COONa、CH 3、CH 2CH 3、叔丁基、环丙基、CHF 2、CF(CF 3) 2、CF 3、CH 2CF 3、OCH 3、OCHF 2、OCF 3、OCH 2CF 3或SO 2CH 3;R 2选自H、甲基、乙基、丙基、异丙基、叔丁基、正丁基、甲氧基、环丙基、氰基乙基、甲氨基、甲磺酰基、烯丙基、炔丙基、甲磺酰基、对甲苯磺酰基、乙基羰基或甲酰基;R 3选自未取代的或被1-3个独立选自以下基团取代的苯基、苄基或杂芳基:OH、Cl、Br、F、I、CN、NO 2、CHO、COOH、COONa、CH 3、CH 2CH 3、叔丁基、环丙基、CHF 2、CF 3、CF(CF 3) 2、CH 2CF 3、OCH 3、OCHF 2、OCF 3、OCH 2CF 3或SO 2CH 3;R 2NR 3也可以组成被1-3个独立选自以下基团取代或未取代的五元或六元环,所述独立取代基团选自以下基团:OH、Cl、Br、F、I、CN、NO 2、CH 3、CH 2CH 3、叔丁基、环丙基、CHF 2、CF(CF 3) 2、CF 3、CH 2CF 3、OCH 3、OCHF 2、OCF 3、OCH 2CF 3或SO 2CH 3;R 4选自Cl、Br、F、I、CN、SO 2CH 3或SO 2CH 2CH 3;或通式(I)化合物N-氧化物以及与盐酸、硫酸、磷酸、甲酸、乙酸、草酸、三氟乙酸、甲磺酸、对甲苯磺酸、苹果酸、柠檬酸、锂、钙、钠或者钾形成的盐。
- 根据权利要求3所述的化合物,其特征在于:通式(I)中R 1选自Cl、Br、F、I、2-甲基苯酚、2-异丙基苯酚、2-环丙基苯酚、2-甲基-6-环丙基苯酚或2-碘苯酚;R 2选自H、CH 3、CH 2CH 3、环丙基、甲氧基或甲氨基;R 3选自未取代的或被1-3个独立选自以下基团取代的苯基、嘧啶基、吡唑基、吡啶基或哒嗪基:OH、Cl、Br、F、I、CN、NO 2、CHO、COOH、COONa、CH 3、CH 2CH 3、叔丁基、环丙基、CHF 2、CF 3、CH 2CF 3、OCH 3、OCHF 2、OCF 3、CF(CF 3) 2、OCH 2CF 3或SO 2CH 3;R 4选自Cl、Br、F、I或CN;或通式(I)化合物与盐酸、硫酸、磷酸、锂、钙、钠或者钾形成的盐。
- 一种根据权利要求I所述的通式(I)化合物用于苗前或苗后茎叶处理防治杂草的应用。
- 根据权利要求I所述的通式I哒嗪胺类化合物用于植物干燥/脱叶的用途。
- 一种除草组合物,其特征在于:以权利要求I所述的化合物(I)化合物作为活性组分,组合物中的活性组分的重量百分比含量为0.1-99%。
- 根据权利要求8所述的除草组合物用于杂草防治的应用。
- 一种如权利要求8所述的除草剂组合物也可以和其他已知的杀虫剂、杀菌剂、植物生长调节剂或肥料(包括除草剂安全剂)等一起混合使用。
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Also Published As
Publication number | Publication date |
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EP3854791A4 (en) | 2021-10-27 |
EP3854791A1 (en) | 2021-07-28 |
CN109053693B (zh) | 2021-02-05 |
BR112021005242A2 (pt) | 2021-06-15 |
CN109053693A (zh) | 2018-12-21 |
US20210337797A1 (en) | 2021-11-04 |
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