CN1090624C - 具有卤代烷氧基取代基的磺酰氨基羰基三唑啉酮类 - Google Patents
具有卤代烷氧基取代基的磺酰氨基羰基三唑啉酮类 Download PDFInfo
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- CN1090624C CN1090624C CN96193575A CN96193575A CN1090624C CN 1090624 C CN1090624 C CN 1090624C CN 96193575 A CN96193575 A CN 96193575A CN 96193575 A CN96193575 A CN 96193575A CN 1090624 C CN1090624 C CN 1090624C
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- alkyl
- chlorine
- fluorine
- bromine
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- 239000002798 polar solvent Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 239000002243 precursor Substances 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
- ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 238000007363 ring formation reaction Methods 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- ZVCDLGYNFYZZOK-UHFFFAOYSA-M sodium cyanate Chemical compound [Na]OC#N ZVCDLGYNFYZZOK-UHFFFAOYSA-M 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
- 229910001948 sodium oxide Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 235000014347 soups Nutrition 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
- DZLFLBLQUQXARW-UHFFFAOYSA-N tetrabutylammonium Chemical compound CCCC[N+](CCCC)(CCCC)CCCC DZLFLBLQUQXARW-UHFFFAOYSA-N 0.000 description 1
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C07D249/12—Oxygen or sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Abstract
本发明涉及式(1)的具有卤代烷氧基取代基的新的磺酰氨基羰基二唑啉酮及式(1)化合物的盐,用于制备化合物(1)的方法和新中间体,以及它们作为除草剂和/或杀真菌剂的应用。其中R1代表氢、羟基、氨基、亚烷基氨基,或是均可被任选取代的以下基团:烷基、链烯基、炔基、烷氧基、烯氧基、烷氨基、二烷氨基、烷酰氨基、环烷基、环烷基烷基、环烷基氨基、芳基和芳烷基,R2代表卤素取代的烷基或链烯基,R3代表均可被任选取代的烷基、芳烷基、芳基或杂芳基。
Description
本发明涉及具有卤代烷氧基取代基新的磺酰氨基羰基三唑啉酮类,用于制备它们的多种方法和新中间体,以及它们作为除草剂和杀真菌剂的应用。
已知某些磺酰氨基羰基三唑啉酮类具有除草性能(见EP-A34148、EP-A 422469、EP-A 425948、EP-A 431291、EP-A 507171)。但是,这些化合物的活性不是在所有方面都令人满意。
R1代表氢、羟基、氨基、亚烷基氨基或者均可被任选取代的以下基团:烷基、链烯基、炔基、烷氧基、烯氧基、烷氨基、二烷氨基、烷酰氨基、环烷基、环烷基烷基、环烷基氨基、芳基、芳烷基,
R2代表卤素取代的烷基或链烯基,
R3代表均可被任选取代的以下基团:烷基、芳烷基、芳基或杂芳基。
通式(1)的具有卤代烷氧基取代基的新的磺酰氨基羰基三唑啉酮用以下方法得到:
(a)通式(II)的三唑啉酮与通式(III)的磺酰基异氰酸酯反应,如果合适在反应助剂和稀释剂存在下进行其中R1和R2均定义如上,
R3-SO2-N=C=O (III)其中R3的定义如上,或
(b)通式(IV)的三唑啉酮衍生物与通式(V)的磺酰胺反应,如果合适在酸受体和稀释剂存在下进行其中R1和R2均定义如上,Z代表卤素、烷氧基、芳基烷氧基或芳氧基,
R3-SO2-NH2 (V)其中R3的定义如上,或
R3-SO2-NH-CO-Z (VI)其中R3的定义同上,Z代表卤素、烷氧基、芳基烷氧基或芳氧基,或
R3-SO2-X (VII)其中R3的定义同上,X代表卤素,
MOCN (VIII)其中M代表碱金属或碱土金属等价物,
如果合适,用常用方法将方法(a)、(b)、(c)或(d)得到的式(1)化合物转化成盐。
通式(1)的有卤代烷氧基取代基的新的磺酰氨基羰基三唑啉酮具有强的除草和/或杀真菌活性。
本发明优选提供式(1)化合物,其中
R1代表氢、羟基、氨基、C1-C6亚烷基氨基,任选被氟、氯、溴、氰基、C1-C4烷氧基、C1-C4烷羰基或C1-C4烷氧羰基取代的C1-C6烷基,均可被氟、氯和/或溴任选取代的C2-C6链烯基或C2-C6炔基,均可被氟和/或氯任选取代的C1-C6烷氧基或C2-C6烯氧基,均可被氟和/或氯任选取代的C1-C6烷氨基、二(C1-C4烷基)氨基或C1-C4烷酰氨基,均可被氟、氯、溴和/或C1-C4烷基任选取代的C3-C6环烷基或C3-C6环烷基-C1-C4烷基,或者均可被氟、氯、溴、氰基、硝基、C1-C4烷基、三氟甲基、C1-C4烷氧基和/或C1-C4烷氧羰基任选取代的苯基或苯基C1-C4烷基,
R2代表被氟、氯和/或溴取代的C1-C6烷基或C2-C6链烯基,
R3代表以下基团其中
R4和R5相同或不同,各自代表氢、氟、氯、溴、碘、硝基、C1-C6烷基(它可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷氨基羰基、二(C1-C4烷基)氨基羰基、羟基、C1-C4烷氧基、甲酰氧基、C1-C4烷基羰氧基、C1-C4烷氧羰氧基、C1-C4烷氨基羰氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、二(C1-C4烷基)氨基磺酰基、C3-C6环烷基或苯基取代),或C2-C6链烯基(它可任选地被氟、氯、溴、氰基、C1-C4烷氧羰基、羧基或苯基取代),或C2-C6炔基(它可任选地被氟、氯、溴、氰基、C1-C4烷氧羰基、羧基或苯基取代),或C1-C4烷氧基(它可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代),或C1-C4烷硫基(它可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代),或C2-C6烯氧基(它可任选地被氟、氯、溴、氰基或C1-C4烷氧羰基取代),或C2-C6烯硫基(它可任选地被氟、氯、溴、氰基、硝基、C1-C3烷硫基或C1-C4烷氧羰基取代),C3-C6炔氧基,C3-C6炔硫基或基团-S(O)P-R6,其中
P代表数字1或2,和
R6代表C1-C4烷基(它可任选地被氟、氯、溴、氰基或C1-C4烷氧羰基取代),C3-C6链烯基,C3-C6炔基,C1-C4烷氧基,C1-C4烷氧基C1-C4烷氨基,C1-C4烷氨基,二(C1-C4烷基)氨基,苯基或者基团-NHOR7,其中
R7代表C1-C12烷基(它可任选地被氟、氯、氰基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、C1-C4烷基羰基、C1-C4烷氧羰基、C1-C4烷氨基羰基或二(C1-C4烷基)氨基羰基取代),或C3-C6链烯基(它可任选地被氟、氯或溴取代),C3-C6炔基,C3-C6环烷基,C3-C6环烷基C1-C2烷基,苯基C1-C2烷基(它可任选地被氟、氯、硝基、氰基、C1-C4烷基、C1-C4烷氧基或C1-C4烷氧羰基取代),或是二苯甲基或苯基(它可任选地被氟、氯、硝基、氰基、C1-C4烷基、三氟甲基、C1-C4烷氧基、C1-C2氟代烷氧基、C1-C4烷硫基、三氟甲硫基或C1-C4烷氧羰基取代),
R4和/或R5还各自代表苯基或苯氧基,或C1-C4烷基羰基氨基,C1-C4烷氧羰基氨基,C1-C4烷氨基羰基氨基,二(C1-C4烷基)氨基羰基氨基,或基团-COR8,其中
R8代表氢、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C3-C6环烷氧基、C3-C6链烯氧基、C3-C6炔氧基、C1-C4烷硫基、C1-C4烷氨基、C1-C4烷氧氨基、C1-C4烷氧基C1-C4烷氨基或二(C1-C4烷基)氨基(它们均可任选地被氟和/或氯取代),
R4和/或R5还各自代表三甲基甲硅烷基、噻唑啉基、C1-C4烷磺酰氧基、二(C1-C4烷基)氨基磺酰氨基或基团-CH=N-R9,其中
R9代表任选被氟、氯、氰基、羧基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代的C1-C6烷基,或是任选被氟或氯取代的苄基,或是任选被氟或氯取代的C3-C6链烯基或C3-C6炔基,或是任选被氟、氯、溴、C1-C4烷基、C1-C4烷氧基、三氟甲基、三氟甲氧基或三氟甲硫基取代的苯基,或是任选被氟和/或氯取代的C1-C6烷氧基、C3-C6烯氧基、C3-C6炔氧基或苄氧基,或是氨基、C1-C4烷氨基、二(C1-C4烷基)氨基、苯氨基、C1-C4烷基羰基氨基、C1-C4烷氧羰基氨基、C1-C4烷基磺酰氨基,或可任选被氟、氯、溴或甲基取代的苯磺酰氨基,
或者是,
R10代表氢或C1-C4烷基,
R11和R12相同或不同,各自代表氢、氟、氯、溴、硝基、氰基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、羧基、C1-C4烷氧羰基、二甲氨基羰基、C1-C4烷磺酰基或二(C1-C4烷基)氨基磺酰基;
或者是,
R3代表以下基团其中R13和R14相同或不同,各自代表氢、氟、氯、溴、硝基、氰基、C1-C4烷基(它可任选地被氟和/或氯取代)或C1-C4烷氧基(它可任选地被氟和/或氯取代);
或者是,
R3代表以下基团其中R15和R16相同或不同,各自代表氢、氟、氯、溴、硝基、氰基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代),或是C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它们各可任选地被氟和/或氯取代),或是氨基磺酰基、一(C1-C4烷基)氨基磺酰基,或二(C1-C4烷基)氨基磺酰基或C1-C4烷氧羰基或二甲氨基羰基;
或者是,
R3代表以下基团其中R17和R18相同或不同,各自代表氢、氟、氯、溴、C1-C4烷基(它可任选地被氟和/或溴取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代),或是C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它们均可任选地被氟和/或氯取代),或二(C1-C4烷基)氨基磺酰基;
或者是,
R3代表以下基团其中
R19和R20相同或不同,各自代表氢、氟、氯、溴、氰基、硝基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基(它可任选地被氟和/或氯取代),二(C1-C4烷基)氨基磺酰基、C1-C4烷氧羰基或二甲氨基羰基,和
A代表氧、硫或基团N-Z1,其中
Z1代表氢、C1-C4烷基(它可任选地被氟、氯、溴或氰基取代)、C3-C6环烷基、苄基、苯基(它可任选地被氟、氯、溴或硝基取代)、C1-C4烷基羰基、C1-C4烷氧羰基或二(C1-C4烷基)氨基羰基;
或者,
R3代表以下基团
其中
R21和R22相同或不同,各自代表氢、C1-C4烷基、卤素、C1-C4烷基羰基、C1-C4烷氧基或C1-C4卤代烷氧基,
Y1代表硫或基团N-R23,其中
R23代表氢或C1-C4烷基;
或者,
R24代表氢、C1-C4烷基、苄基、吡啶基、喹啉基或苯基,
R25代表氢、卤素、氰基、硝基、C1-C4烷基(它可任选地被氟和/或氯取代)、C1-C4烷氧基(它可任选地被氟和/或氯取代)、二氧戊环基或C1-C4烷氧羰基,和
R26代表氢、卤素或C1-C4烷基。
另外,本发明优选提供其中的n、R1、R2和R3均具有上述优选含义的式(1)化合物的钠盐、钾盐、镁盐、钙盐、铵盐、C1-C4烷基铵盐、二(C1-C4烷基)铵盐、三(C1-C4烷基)铵盐、四(C1-C4烷基)铵盐、三(C1-C4烷基)锍盐、C5或C6环烷基铵盐和二(C1-C2烷基)苄铵盐。
本发明特别提供了下述式(1)化合物,其中
R1代表均可任选地被氟、氯、氰基、甲氧基或乙氧基取代的甲基、乙基、正或异丙基、正、异、仲或叔丁基,或者代表均可任选被氟、氯或溴取代的丙烯基、丁烯基、丙炔基或丁炔基,或者代表均可被氟和/或氯取代的甲氧基、乙氧基、正或异丙氧基、正、异、仲或叔丁氧基、丙烯氧基或丁烯氧基,或者代表甲氨基、乙氨基、正或异丙氨基、正、异、仲或叔丁氨基、二甲氨基或二乙氨基,或者代表均可任选地被氟、氯、溴、甲基或乙基取代的环丙基、环丁基、环戊基、环己基、环丙基甲基、环丁基甲基、环戊基甲基或环己基甲基,或者代表均可任选地被氟、氯、溴、氰基、甲基、三氟甲基或甲氧基取代的苄基或苯基,
R2代表被氟和/或氯取代的甲基、乙基、正或异丙基、正、异、仲或叔丁基,和
R4代表氟、氯、溴、甲基、乙基、正或异丙基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基、三氟甲氧基、2-氯乙氧基、2-甲氧乙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基、乙磺酰基、二甲氨基磺酰基、二乙氨基磺酰基、N-甲氧基-N-甲氨基磺酰基、苯基、苯氧基、甲氧羰基、乙氧羰基、正或异丙氧羰基,和
R5代表氢、甲基、乙基、氟、氯或溴;
或者,
R10代表氢,
R11代表氟、氯、溴、甲基、甲氧基、二氟甲氧基、三氟甲氧基、乙氧基、甲氧羰基、乙氧羰基、甲磺酰基或二甲氨基磺酰基,和
R12代表氢;
或者,
R3代表以下基团其中
R代表甲基、乙基、正或异丙基,或者
R24代表甲基、乙基、正或异丙基、苯基或吡啶基,
R25代表氢、氟、氯或溴,和
R26代表氟、氯、溴、甲氧羰基或乙氧羰基。
上述的一般的或优选的基团定义适用于式(1)的最终产物,也相应地适用于各情形的制备中所需的前体或中间体。这些基团的定义可以根据需要彼此组合,从而包括了在所示优选范围之间的组合。
在这些基团的定义中,诸如烷基、链烯基或炔基等烃基,即使是在与杂原子的组合(如烷氧基、烷硫基或烷氨基)中,也可以是直链或支链的,虽然这一点未明确说明。
卤素一般代表氟、氯、溴或碘,优选氟、氯或溴,特别是氟或氯。
使用例如2-三氟甲氧基苯磺酰基异氰酸酯和4-乙基-5-二氟甲氧基-2,4-二氢-3H-1,2,4-三唑-3-酮作为起始物,本发明方法(a)中的反应过程可以用以下反应式示例说明:
使用例如2-乙硫基苯磺酰胺和2-氯羰基-4-苄基-5-(2,2-二氟乙氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮作为起始物,本发明方法(b)中的反应过程可以用以下反应式示例说明:
在本发明制备式(1)化合物的方法(a)、(c)和(d)中作为起始物使用的三唑啉酮的一般定义由式(II)给出。
在式(II)中,R1和R2各自优选或者特别优选具有上面关于本发明式(1)化合物的说明中作为优选或特别优选的R1和R2已经指出的那些含义。
通式(II)的三唑啉酮尚未在文献中公开;作为新物质,它们也构成本申请主题的一部分。
如果合适,反应在稀释剂(如甲醇)存在下于0-100℃的温度下进行,将这样形成的式(XI)化合物进行环化缩合,如果合适,在中间体分离后于稀释剂(如甲苯)存在下在20-150℃的温度下进行(参见制备实施例)其中R、R1和R2定义同上。
其中的R2代表二氟甲基(R1定义如上)的式(II)三唑啉酮的制备方法最好是,使通式(XII)的尿唑与氯二氟甲烷在酸受体(如氢氧化钠)和稀释剂(如异丙醇和/或水)存在下在0-100℃的温度下反应(参见制备实施例)。其中R1定义同上。
在本发明制备式(1)化合物的方法(a)中也作为起始物使用的磺酰基异氰酸酯的一般定义由式(III)给出。
在式(III)中,R3优选或特别优选具有上面关于本发明式(1)化合物的说明中作为优选或特别优选的R3已经指出的那些含义。
式(III)起始物是已知的,和/或可以用本身已知的方法制备(参见 US-P 4127405,US-P 4169719,US-P 4371391,EP-A 7687,EP-A 13480,EP-A 21641,EP-A 23141,EP-A 23422,EP-A 30139,EP-A 35893;EP-A 44808;EP-A 44809,EP-A 48143,EP-A 51466,EP-A64322,EP-A 70041,EP-A 173312)。
在本发明制备通式(1)化合物的方法(b)中作为起始物使用的三唑啉酮衍生物的一般定义由式(IV)给出。在式(IV)中,R1和R2各自优选或特别优选具有上面关于式(I)化合物的说明中作为优选或特别优选的R1和R2已经指出的那些含义;Z优选代表氟、氯、溴、甲氧基、乙氧基、苄氧基、苯氧基、卤代或硝基苯氧基,特别是代表甲氧基、苯氧基或4-硝基苯氧基。
式(IV)起始物文献中尚未公开;作为新物质,它们也构成本申请主题的一部分。
Z-CO-Z1 (XIII)其中Z的定义同上,Z1代表卤素、烷氧基、芳基烷氧基或芳氧基,如果合适,反应在酸受体(例如叔丁醇钾)和稀释剂(如四氢呋喃或二甲氧基乙烷)存在下于0-100℃的温度下进行。
在本发明制备通式(1)化合物的方法(b)中也作为起始物使用的磺酰胺的一般定义由式(V)给出。在式(V)中,R3优选或特别优选具有上面关于式(1)化合物的说明中作为优选或特别优选的R3已经指出的那些含义。
式(V)起始化合物是已知的和/或可以用本身已知的方法制备(参见 US-P 4127405,US-P 4169719,US-P 4371391,EP-A 7687,EP-A 13480,EP-A 21641,EP-A 23141,EP-A 23422,EP-A 30139,EP-A 35893,EP-A 44808,EP-A 44809,EP-A 48143,EP-A 51466,EP-A64322,EP-A 70041,EP-A 173312)。
在本发明制备式(1)化合物的方法(c)中作为起始物使用的磺酰胺衍生物的一般定义由式(VI)给出。在式(VI)中,R3优选或特别优选具有上面关于式(1)化合物的说明中作为优选或特别优选的R3已经指出的那些含义;Z优选代表氟、氯、溴、甲氧基、乙氧基、苄氧基或苯氧基,特别是代表甲氧基或苯氧基。
式(VI)起始物是已知的和/或可以按照本身已知的方法制备。
在本发明制备式(1)化合物的方法(d)中作为起始物使用的磺酰卤化物的一般定义由式(VII)给出。在式(VII)中,R3优选或特别优选具有上面关于式(1)化合物的说明中作为优选或特别优选的R3已经指出的那些含义;X优选代表氟、氯或溴,特别是代表氯。
式(VII)的起始物是已知的和/或可以按照本身已知的方法制备。
用于制备式(1)新化合物的本发明方法(a)、(b)、(c)和(d)优选使用稀释剂进行。这方面合适的稀释剂实际上是所有的惰性有机溶剂。这些溶剂优选包括可任选卤化的脂族和芳族烃类,例如戊烷、己烷、庚烷、环己烷、石油醚、汽油、粗汽油、苯、甲苯、二甲苯、二氯甲烷、氯化乙烯、氯仿、四氯甲烷、氯苯和邻二氯苯;醚类,例如乙醚和二丁醚、乙二醇二甲醚和二乙二醇二甲醚、四氢呋喃及二噁烷;酮类,例如丙酮、甲乙酮、甲基异丙基酮和甲基异丁基酮;酯类,例如乙酸甲酯和乙酸乙酯;腈类,例如乙腈和丙腈;酰胺类,例如二甲基甲酰胺、二甲基乙酰胺和N-甲基吡咯烷酮,以及二甲基亚砜、四氢噻吩砜和六甲基磷酸三酰胺。
作为本发明方法(a)、(b)、(c)和(d)中的反应助剂和/或酸受体,可以使用通常用于此类反应的所有酸结合剂。优选碱金属氢氧化物(例如氢氧化钾和钠),碱土金属氢氧化物(例如氢氧化钙),碱金属碳酸盐和醇盐(例如碳酸钠和碳酸钾、叔丁醇钠和叔丁醇钾),以及碱性氮化合物,例如三甲胺,三乙胺,三丙胺,三丁胺,三异丁胺,二环己胺,乙基二异丙胺,乙基二环己胺,N,N-二甲基苄胺,N,N-二甲基苯胺,吡啶,2-甲基-、3-甲基-、4-甲基-、2,4-二甲基-、2,6-二甲基-、2-乙基-、4-乙基-和5-乙基-2-甲基吡啶,1,5-二氮杂双环〔4,3,0〕-壬-5-烯(DBN),1,8-二氮杂双环〔5,4,0〕-十一碳-7-烯(DBU)和1,4-二氮杂双环〔2,2,2〕-辛烷(DABCO)。
本发明方法(a)、(b)、(c)和(d)中的反应温度可以在相当宽的范围内变化。反应一般在-20℃至+100℃的温度下进行,优选在0℃至+80℃的温度下进行。
本发明方法(a)、(b)、(c)和(d)一般在大气压下进行。但是也可以在增压或减压下进行。
为进行本发明方法(a)、(b)、(c)和(d),各种情形中所需要的起始物通常以近似等摩尔量使用。但是在每种情形也可以使用有较大过剩量的某一组分。反应一般在合适的稀释剂中于酸受体存在下进行,在所要求的特定温度下将反应混合物搅拌几小时。在本发明方法(a)、(b)、(c)和(d)中,后处理均用常用方法进行(参见制备实施例)。
如果需要,可以制备本发明通式(1)化合物的盐。这些盐可以按照简单的方式用常用的成盐方法得到,例如将式(1)化合物溶解或分散在合适的溶剂中,如二氯甲烷、丙酮、叔丁基甲基醚或甲苯中,并加入合适的碱。如果需要,在长时间搅拌后可以用浓缩或抽气过滤的方法将盐分离。
本发明化合物可以作为落叶剂、干燥剂、杀茎杆剂,尤其是作为除草剂使用。所谓杂草,在最广泛的含义上,应理解为生长在不应生长地方的所有植物。本发明物质是作为灭生性除草剂还是作为选择性除草剂起作用,主要取决于用量。
本发明活性化合物可用于例如以下植物:
以下各属双子叶杂草:欧白芥属,独行菜属,猪殃殃属,繁缕属,母菊属,春黄菊属,牛膝菊属,藜属,荨麻属,千里光属,苋属,马齿苋属,苍耳属,旋花属,番薯属,蓼属,田菁属,豚草属,蓟属,飞廉属,苦苣菜属,茄属,蔊菜属,节节菜属,母草属,野芝麻属,婆婆纳属,苘麻属,刺酸模属,曼陀罗属,堇菜属,鼬瓣花属,罂粟属,矢车菊属,三叶草属,毛茛属和蒲公英属。
以下各属双子叶栽培作物:棉属,大豆属,甜菜属,胡萝卜属,菜豆属,豌豆属,茄属,亚麻属,番薯属,野豌豆属,烟草属,番茄属,花生属,芸苔属,莴苣属,黄瓜属和南瓜属。
以下各属单子叶杂草:稗属,狗尾草属,黍属,马唐属,梯牧草属,早熟禾属,羊茅属,蟋蟀草属,臂形草属,黑麦草属,雀麦属,燕麦属,莎草属,高粱属,冰草属,狗牙根属,雨久花属,飘拂草属,慈姑属,荸荠属,藨草属,雀稗属,鸭嘴草属,尖瓣花属,龙爪茅属,剪股颍属,看麦娘属和风草属。
以下各属单子叶栽培作物:稻属,玉蜀泰属,小麦属,大麦属,燕麦属,黑麦属,高粱属,黍属,甘蔗属,凤梨属,天门冬属和葱属。
然而,本发明活性化合物的用途绝不仅限于以上各属,而是以同样的方式扩展到其它植物。
因浓度而异,这类化合物适用于诸如工业场地和铁路线上以及有或无树林的道路和广场上作灭生性除草。同样,这类化合物也可用于防治多年生栽培作物中的杂草,多年生栽培作物如造林带、装饰性林木、果园、葡萄园、桔园、坚果园、香蕉园、咖啡园、茶场、橡胶园、油棕园、可可园、浆果园和啤酒花田除草,草坪、草地和牧场。另外,本发明化合物可用于选择性地防治一年生栽培作物中的杂草。
本发明式(1)化合物优选适合于单子叶和双子叶栽培作物中选择性地防治单子叶和双子叶杂草,可以是出苗前或出苗后。
另外,本发明活性化合物具有有效的杀微生物作用,可以实际应用于防治不良的微生物。这类活性化合物适合作为作物保护剂,特别是作为杀真菌剂使用。
植物保护中的杀真菌剂是用来防治根肿菌纲、卵菌纲、壶菌纲、接合菌纲、子囊菌纲、担子菌纲和半知菌类的真菌。
植物保护中的杀细菌剂是用来防治假单胞菌科、根瘤菌科、肠杆菌科、棒状杆菌科和链霉菌科的细菌。
归入上述各属名称内的某些真菌性及细菌性病害的病原体可以叙述如下,但只是作为例子,而不是对它的限制:
黄单孢菌属,如田野黄单孢菌稻变种;
假单胞菌属,如丁香假单胞菌瓜变种;
欧文氏杆菌属,如解淀欧文氏杆菌;
腐霉属,如终极腐霉;
疫霉属,如蔓延疫霉;
假霜霉属,如葎草假霜霉或古巴假霜霉;
单轴霉属,如葡萄生单轴霉;
盘梗霉属,如莴苣盘梗霉;
霜霉属,如豌豆霜霉或芸苔霜霉;
白粉菌属,如禾白粉菌;
单丝壳菌属,如苍耳单丝壳菌;
柄球菌属,如苹果白粉病柄球菌;
黑星菌属,如苹果黑星菌;
核腔菌属,如园核腔菌或麦类核腔菌
(分生孢子形式:Drechslera,同物异名:Helminthosporium);
旋孢霉属,如禾旋孢霉
(分生孢子形式:Drechslera,同物异名:Helminthosporium);
单胞锈菌属,如菜豆单胞锈菌;
柄锈菌属,如隐匿柄锈菌;
核盘菌属,如油菜核盘菌;
腥黑粉菌属,如小麦网腥黑粉菌;
黑粉菌属,如裸黑粉菌或燕麦黑粉菌;
薄膜革菌属,如佐佐木氏薄膜革菌;
梨孢属,如稻梨孢;
镰孢属,如大刀镰孢;
葡萄孢属,如灰色葡萄孢;
壳针孢属,如颍枯壳针孢;
小球腔菌属,如颍枯小球腔菌;
尾孢属,如赤豆尾孢;
链格孢属,如甘蓝黑斑病链格孢;
小假尾孢属,如蔓毛小假尾孢。
栽培作物对于为防治作物病害所需浓度的活性化合物的良好耐受性,使得有可能对植物的地上部分、无性繁殖的块茎和种子以及天壤进行处理。
式(1)化合物特别适合对苹果样的水果(如苹果)进行保护性处理,杀灭苹果白粉病的病原体(苹果白粉病柄球菌),在一定程度上还可用于杀灭稻中的稻梨孢。
这类活性化合物可以转化成常用的制剂,例如溶液、乳剂、可湿性粉剂、悬浮液、粉剂、喷粉剂、糊剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然与合成物质、以及在聚合物中的很细小的胶囊。
这些制剂用已知方法制成,例如任选地使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)将活性化合物与填充剂(即液体溶剂和/或固体载体)混合。
如果采用水作为填充剂,则也可以用例如有机溶剂作助溶剂。适用的液体溶剂主要有:芳族化合物(如二甲苯、甲苯或烷基萘),氯化芳族化合物和氯化脂族烃类(如氯苯、氯乙烯或二氯甲烷),脂族烃类(如环己烷或链烷烃,例如石油馏分),矿物和植物油,醇类(如丁醇或乙二醇及它们的醚和酯),酮类(如丙酮、甲乙酮、甲基异丁基酮或环己酮),强极性溶剂(如二甲基甲酰胺和二甲基亚砜,以及水)。
合适的固体载体有:如铵盐和磨碎的天然矿物(例如高岭土、粘土、滑石粉、白垩、石英、硅镁土、蒙脱土或硅藻土)以及磨碎的合成矿物(如高度分散的二氧化硅、氧化铝和硅酸盐);适合颗粒剂的固体载体有:如粉碎并分级的天然岩石(例如方解石、大理石、浮石、海泡石和白云石)及无机或有机粗粉的合成颗粒,以及有机材料(如锯末、椰壳、玉米芯和烟草杆)的颗粒;适用的乳化剂和/或起泡剂有:如非离子和阴离子乳化剂,例如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚(如烷基芳基聚乙二醇醚)、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐以及蛋白质水解产物;合适的分散剂有:木质素亚硫酸盐废液和甲基纤维素。
在制剂中可以使用粘合剂,例如羧甲基纤维素和粉末、颗粒或胶乳形式的天然及合成聚合物,如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯,以及天然磷脂(如脑磷脂和卵磷脂)和合成磷脂。其它添加剂可以是矿物和植物油。
可以使用着色剂,例如无机颜料(如氧化铁、二氧化钛和普鲁士兰)和有机染料(如茜素染料、偶氮染料和金属酞菁染料),以及微量的营养素(如铁、锰、硼、铜、钴、钼和锌的盐)。
制剂中一般含有0.1-95%重量的活性化合物,最好是0.5-90%。
为防治杂草,本发明的活性化合物本身或其制剂形式,也可以以与已知的除草剂一起的混合物、配好备用的制剂或可能的桶混物的形式使用。
可用于混合物中的组分是已知的除草剂,例如N-酰苯胺类,如吡氟草胺和敌稗;芳基羧酸类,如二氯吡啶甲酸、麦草畏和毒莠定;芳氧基链烷酸,如2,4-滴、2,4-滴丁酸、2,4-滴丙酸、氟草烟、2甲4氯、2甲4氯丙酸和定草酯;芳氧苯氧基链烷酸酯,如禾草灵、噁唑禾草灵、吡氟禾草灵、吡氟氯禾灵和喹禾灵;连氮酮类,如杀草敏和达草灭;氨基甲酸酯类,如氯苯胺灵、甜菜安、甜菜宁和苯胺灵;氯乙酰苯胺类,如甲草胺、乙草胺、丁草胺、吡草胺、异丙甲草胺、丙草胺和毒草胺;二硝基苯胺类,如安磺灵、二甲戊乐灵和氟乐灵;二苯醚类,如三氟羧草醚、甲羧除草醚、乙羧除草醚、氟黄胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚;脲类,如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和甲基苯噻隆;羟胺类,如禾草灭、烯草酮、噻草酮、稀禾定和肟草酮;咪唑啉酮类,如咪草烟、咪草酯、灭草烟和灭草喹;腈类,如溴苯腈、敌草腈和碘草腈;氧乙酰胺类,如苯噻草胺;磺酰脲类,如amidosulfuron、苄嘧黄隆、氯嘧黄隆、绿黄隆、醚黄隆、甲黄隆、烟嘧黄隆、氟嘧黄隆、吡嘧黄隆、噻黄隆、醚苯黄隆和苯黄隆;硫代氨基甲酸酯类,如丁草特、灭草特、燕麦敌、茵达灭、禾草畏、草达灭、苄草丹、杀草丹和野麦畏;三嗪类,如阿特拉津、草净津、西玛津、西草净、去草净和特丁津;三嗪酮类,如环嗪酮、苯嗪草酮和嗪草酮;其它,例如杀草强、呋草黄、灭草松、环庚草醚、异噁单酮、二氯吡啶酸、双苯唑快、氟硫草定、乙呋草黄、氟咯草酮、草铵磷、草甘膦、isoxaben、哒草灭、二氯喹啉酸、喹草酸、草硫膦和灭草环。
也可以与已知的其它活性化合物混合,例如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱乌剂、植物营养剂和改进土壤结构的试剂。
活性化合物可以照原样、以制剂形式或者通过进一步稀释配制的使用形式(例如配好备用的溶液、悬浮液、乳液、粉末、糊和颗粒)使用。它们可以按常用方式使用,例如浇灌、喷雾、弥雾或撒施。
本发明化合物可以在植物出苗之前或之后施用。它们也可以在播种前掺加到土壤中。
活性化合物的用量可以在相当大的范围内变化。这主要取决于所要求的效果。一般来说,用量为每公顷地表面用1g-10kg活性化合物,优选每公顷5g-2kg。
由以下实施例可以看到本发明活性化合物的制备及用途。制备实施例:
实施例1(用万法(a))
将1.9g(9.5mmol)4-甲基-5-(2,2,2-三氟乙氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮在50ml乙腈中的溶液与2.4g(10mmol)2-甲氧羰基苯磺酰基异氰酸酯混合,混合物在20℃下搅拌12小时,然后减压浓缩,残余物自乙醚中结晶。
得到3.7g(理论值的89%)2-(2-甲氧羰基苯磺酰氨基羰基)-4-甲基-5-(2,2,2-三氟乙氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点153℃。
将3.8g(12mmol)4-甲基-2-苯氧羰基-5-(2,2,2-三氟乙氧基)-2,4-二氢-3H-1,2,4-三唑-酮溶于20ml乙腈中,并与3.4g(12mmol)2-(N-甲氧基-N-甲基氨磺酰)苯磺酰胺和1.9g(12.5mmol)二氮杂双环十一烯(DBU)混合。在20℃下将混合物搅拌1小时后,倒入二氯甲烷/5%盐酸的混合物中,分离出有机相,用硫酸钠干燥,减压浓缩。残余物用乙醚结晶。
得到3.3g(理论值的55%)2-〔2-(N-甲氧基-N-甲基氨基磺酰)苯磺酰氨基羰基〕4-甲基-5-(2,2,2-三氟乙氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点183℃。
利用实施例1和2的方法并根据本发明制备方法的一般说明,还可以制备例如下面表1中列出的式(1)化合物。表1:式(1)化合物实例实施例 R1 R2 R3编号 熔点(℃)实施例R1 R2 R3编号 熔点(℃)实施例R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3编号 熔点(℃)实施例 R1 R2 R3 熔点编号 (℃)式(II)起始物
将723g(2.45mol)二甲氧基二丁锡与777g(5.89mol)2,2,3,3-四氟丙醇在氮气下加热至120℃。通过柱子蒸走此过程中放出的大部分甲醇,然后在水泵抽气下(约15毫巴)基本上除掉剩下的甲醇和多余的2,2,3,3-四氟丙醇,余下的残余物为二(2,2,3,3-四氟丙氧基)二丁锡。步骤2:二(2,2,3,3-四氟丙基)甲基亚氨基碳酸酯
在40℃下将175g(2.39mol)异硫氰酸甲酯逐滴加到上面得到的二(2,2,3,3-四氟丙氧基)二丁锡中,随后在氮气下将混合物在120℃下加热36小时。接着将混合物粗馏,先在水泵真空下,然后用油泵(底部最终温度:170℃,1毫巴)。在油泵真空下精馏,得到555g(理论值的77%)二(2,2,3,3-四氟丙基)甲基亚氨基碳酸酯。沸点:73℃(15毫巴),纯度:98.3%。步骤3:4-甲基-5-(2,2,3,3-四氟丙氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮
将555g(1.83mol)二(2,2,3,3-四氟丙基)甲基亚氨基碳酸酯溶于500ml四氢呋喃中,在冰冷却下(0-5℃)与18.7g(183mmol)新戊酸(催化剂)和278g(1.83mol)肼基甲酸苯酯混合。将混合物在20℃下搅拌2小时,然后温热至50℃,结果形成搅拌费力的晶体浆状物。将其加热至80℃时,溶液再次变均匀。先在约200毫巴下馏出大部分四氢呋喃,然后在约15毫巴下馏出大部分2,2,3,3-四氟丙醇和苯酚。在塔头温度130℃和约0.5毫巴的压力下除掉残余物中剩余的挥发物组分,随后溶在400ml热甲苯中。冷却到0℃后,抽气过滤分离出晶态产物。
得到280g(理论值的67%)4-甲基-5-(2,2,3,3-四氟丙氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点101℃。
将11.85g(0.10mol)4-甲基脲唑溶在100ml异丙醇、25ml水和12g 45%浓度氢氧化钠水溶液(0.30mol NaOH)的混合物中。在40℃和搅拌下缓慢地通入二氟氯甲烷(氟里昂22)。通入27.7g(0.41mol)后,中止反应并将反应混合物冷却。分离出异丙醇相,减压浓缩。残余物与乙醚一起搅拌,滤掉不溶的组分。将醚相减压浓缩,残余物用制层色谱法纯化(洗脱剂二氯甲烷/甲醇=20/3)。
得到0.9g(理论值的5.5%)5-二氟甲氧基-4-甲基-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点111℃。
利用实施例(II-1)和(II-2)的方法,还可以制备例如下面表2中列出的式(II)化合物表2:式(II)化合物实例实施例 R1 R2编号 熔点(℃)实施例 R1 R2编号 熔点(℃)实施例 R1 R2编号 熔点(℃)式(IV)起始物:
实施例(IV-1)
在20℃和有效的搅拌下将51.7g(0.33mol)氯甲酸苯酯逐滴加到59.1g(0.30mol)4-甲基-5-(2,2,2-三氟乙氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮、100ml水、400ml二氯甲烷、13.2g(0.33mol)氢氧化钠和1.0g溴化四丁铵的混合物中。加完后继续搅拌16小时,分离出有机相用水洗,干燥,浓缩。残余物自异丙醚中结晶。
得到87.6g(理论值的92%)4-甲基-2-苯氧羰基-5-(2,2,2-三氟乙氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点105℃。
实施例A苗前试验溶剂:5重量份丙酮乳化剂:1重量份烷基芳基聚乙二醇醚
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述数量的溶剂混合,加入所述数量的乳化剂,用水将该浓缩物稀释至所要求的浓度。
将试验植物播种在普通土壤中。24小时后用活性化合物制剂浇灌土壤。最好是保持每单位面积的水量恒定。制剂中活性化合物的浓度并不重要,只有每单位面积上施加的活性化合物数量才是决定性的。三周后与未处理的对照样的生长情况比较,将植物的损伤程度按损伤%分级。数字表示:
0%=无作用(与未处理的对照样相同)
100%=完全摧毁
在此试验中,例如制备实施例1、2、3、4、5、6、9、11、12、15、16、17、25、50、54、66、83、84、85、86、87、88、89、91、93、94、95、96、97、98、99、100和101显示出强的杀灭杂草作用。
表A:苗前试验/温室
化合物的制备实施例编号 | 施用率(克/公顷) | 雀麦属 | 黑麦草属 | 早熟禾属 | 苋属 | 牛膝菊属 | 母菊属 | 欧白芥属 | 茄属 |
83 | 125 | 95 | 95 | 95 | 90 | 95 | 90 | 90 | 95 |
84 | 125 | 90 | 90 | 90 | 90 | 95 | 90 | 90 | 95 |
85 | 125 | 90 | 95 | 90 | 90 | 95 | 95 | 90 | 95 |
86 | 125 | 95 | 80 | 90 | 90 | 95 | 95 | 95 | 95 |
1 | 125 | 95 | 95 | 95 | 90 | 90 | 90 | 80 | 95 |
3 | 125 | 95 | 90 | 80 | 80 | 70 | 95 | 80 | 90 |
4 | 125 | 95 | 95 | 95 | 95 | 95 | 90 | 95 | 95 |
5 | 125 | 95 | - | 80 | 95 | 95 | 95 | 95 | 95 |
6 | 125 | 95 | 50 | 95 | 95 | 70 | 60 | 90 | 95 |
50 | 125 | 95 | 90 | 90 | 90 | 80 | 90 | 90 | 90 |
54 | 125 | 95 | 90 | 90 | 90 | 95 | 90 | 70 | 90 |
87 | 125 | 90 | 90 | 90 | 90 | 70 | 50 | 80 | 90 |
88 | 125 | 90 | 90 | 90 | 80 | 95 | 95 | 80 | 90 |
89 | 125 | 90 | 80 | 80 | 90 | 95 | 95 | 80 | 90 |
91 | 125 | 90 | 70 | 80 | 80 | 80 | 70 | 80 | 90 |
表A(续)
化合物的制备实施例编号 | 施用率(克/公顷) | 雀麦属 | 黑麦草属 | 早熟禾属 | 苋属 | 牛膝菊属 | 母菊属 | 欧白芥属 | 茄属 |
9 | 125 | 95 | 95 | 95 | 95 | 95 | 100 | 80 | 95 |
11 | 125 | - | 60 | 50 | 90 | 100 | 100 | 80 | 70 |
12 | 125 | 80 | 80 | 80 | 95 | 100 | 80 | 80 | 80 |
15 | 125 | 95 | - | 60 | 95 | 70 | 95 | 90 | 90 |
16 | 125 | 80 | 90 | 95 | 95 | 60 | 80 | 90 | 90 |
93 | 125 | 95 | 95 | 95 | 95 | 95 | 95 | 95 | 95 |
94 | 125 | 90 | 90 | 90 | 80 | 95 | 90 | 80 | 90 |
95 | 125 | 80 | 90 | - | 90 | 95 | 90 | 90 | 90 |
96 | 125 | 95 | 95 | 90 | 90 | 90 | 90 | 90 | 80 |
97 | 250 | 95 | 95 | 90 | 95 | 95 | 95 | 90 | 95 |
2 | 250 | 95 | 95 | 95 | 95 | 95 | 80 | 80 | 95 |
17 | 125 | 95 | 70 | 80 | 90 | 90 | 90 | 80 | 90 |
98 | 125 | 90 | 70 | 80 | 90 | 90 | 80 | 80 | 90 |
25 | 125 | - | - | 90 | 60 | 100 | 95 | 90 | 70 |
66 | 125 | 90 | 95 | 90 | 70 | 95 | 95 | 70 | 95 |
表A(续)
实施例B苗后试验溶剂:5重量份丙酮乳化剂:1重量份烷基芳基聚乙二醇醚
化合物的制备实施例编号 | 施用率(克/公顷) | 雀麦属 | 黑麦草属 | 早熟禾属 | 苋属 | 牛膝菊属 | 母菊属 | 欧白芥属 | 茄属 |
99 | 125 | 90 | 90 | 95 | 100 | 70 | 50 | 90 | 90 |
100 | 125 | - | 95 | 95 | 50 | - | 70 | 80 | 95 |
101 | 125 | 70 | 95 | 90 | 90 | 80 | 50 | 80 | 90 |
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述数量的溶剂混合,加入所述数量的乳化剂,用水将该浓缩物稀释至所要求的浓度。
用活性化合物制剂向高度5-15cm的试验植物喷雾,在每单位面积上施加特定数量所要的活性化合物。选择喷雾液体的浓度,使得特定数量所要的活性化合物是以每公顷2000升水的方式施用。三周后与未处理的对照样的生长情况比较,将植物受损伤的程度按损伤%分级。
数字表示:
0%=无作用(与未处理的对照样相同)
100%=完全摧毁
在此试验中,制备实施例1、2、4、5、9、16、17、25、50、66、83、84、85、86、87、88、89、93、94、95、96、98、99和100的化合物显示出强的杀灭杂草作用。
表B:苗后试验/温室
实施例C苹果白粉病保护性防治试验溶剂:4.7重量份丙酮乳化剂:0.3重量份烷基芳基聚乙二醇醚
化合物的制备实施例编号 | 施用率(克/公顷) | 看麦)娘属 | 燕麦属 | 黑麦草属 | 苋属 | 曼陀罗属 | 拉拉藤属 | 向日葵属 | 茄属 | 婆婆纳属 |
83 | 250 | 90 | 90 | 95 | 90 | 90 | 90 | 90 | 90 | 90 |
84 | 250 | - | 95 | 70 | 70 | 90 | 80 | 90 | 90 | 95 |
85 | 250 | - | - | 95 | 70 | 90 | 90 | 90 | 80 | 95 |
86 | 500 | - | 80 | 90 | 100 | 90 | 90 | 100 | 95 | 100 |
1 | 250 | 90 | 90 | 100 | 80 | 80 | 70 | 90 | 90 | 95 |
4 | 250 | 90 | 70 | 90 | 80 | 90 | 70 | 90 | 90 | 90 |
5 | 250 | 80 | 50 | - | 95 | 90 | 70 | 95 | 90 | 100 |
87 | 125 | 70 | 80 | 50 | 80 | 95 | 70 | 80 | 90 | 90 |
50 | 60 | 80 | 50 | 80 | 95 | 50 | 85 | - | 90 | 70 |
88 | 250 | 80 | - | 70 | 95 | 95 | 90 | 100 | 90 | 90 |
89 | 125 | 50 | - | 80 | 95 | 95 | 90 | 95 | 95 | 95 |
9 | 60 | 100 | 95 | 80 | 95 | 90 | 90 | 80 | 95 | 90 |
16 | 125 | - | 50 | 70 | 95 | 80 | 50 | 100 | 95 | 70 |
93 | 125 | 95 | 90 | 80 | 95 | 95 | 90 | 100 | 95 | 70 |
94 | 125 | 80 | 90 | 80 | 70 | 90 | 70 | 80 | 90 | - |
95 | 60 | 70 | 70 | - | 90 | - | 95 | 70 | 70 | 80 |
17 | 125 | 50 | - | - | 90 | 80 | 50 | 100 | 95 | 90 |
98 | 125 | - | - | - | 95 | 50 | - | 100 | 80 | 90 |
96 | 60 | 95 | 70 | 90 | 95 | 70 | 90 | 80 | - | 50 |
2 | 125 | 60 | 60 | 50 | 80 | 80 | - | 95 | 80 | 80 |
25 | 60 | 60 | 50 | - | 80 | 80 | 50 | 100 | 90 | - |
66 | 60 | 50 | - | - | 80 | 80 | 50 | 100 | 90 | - |
99 | 60 | 60 | 50 | 50 | 90 | 95 | 95 | 60 | 90 | 70 |
100 | 125 | - | 90 | 80 | 90 | 90 | 90 | - | 95 | 90 |
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述数量的溶剂和乳化剂混合,用水将该浓缩物稀释至所要求的浓度。
为试验保护性活性,幼小的植株用活性化合物制剂喷雾。在喷雾液层干燥后,通过喷粉,在植株上接种苹果白粉病病原体(苹果白粉病柄球菌)的分生孢子。
然后将植株放在相对湿度约70%的23℃温室中。
接种10天后进行评价。
在此试验中,例如,制备实施例1、3、83和85的化合物在活性化合物浓度为25ppm时,效力为87-100%。
表C` 苹果白粉病保护性防治试验
实施例D黄瓜白粉病保护性防治试验溶剂:4.7重量份丙酮乳化剂:0.3重量份烷基芳基聚乙二醇醚
活性化合物(化合物的制备实施例号) | 活性化合物浓度为25ppm时与未处理对照相比的效力% |
138385 | 898710099 |
为制备合适的活性化合物制剂,将1重量份的活性化合物与所述数量的溶剂和乳化剂混合,用水将该浓缩物稀释至所要求的浓度。
为试验保护作用,幼小的植株用活性化合物喷雾。在喷雾液层干燥后,将植株用苍耳单丝壳菌的分生孢子喷粉。
然后将植株放在温度为23-24℃、相对大气湿度约75%的温室中。
接种10天后进行评价。
在此试验中,例如制备实施例50的化合物,在活性化合物浓度为100ppm时,效力为92%。
表D
黄瓜白粉病保护性防治试验
活性化合物(化合物的制备实施例编号) | 活性化合物浓度为100ppm时与未处理对照相比的效力% |
50 | 92 |
Claims (6)
1.通式(1)的具有卤代烷氧基取代基的磺酰氨基羰基三唑啉酮类或其盐,其中,
R1代表任选被氟、氯、溴、氰基、C1-C4烷氧基、C1-C4烷羰基或C1-C4烷氧羰基取代的C1-C6烷基,均可被氟、氯和/或溴任选取代的C2-C6链烯基或C2-C6炔基,均可被氟、氯、溴和/或C1-C4烷基任选取代的C3-C6环烷基,
R2代表被氟、氯和/或溴取代的C1-C6烷基或C2-C6链烯基,
R3代表以下基团其中
R4和R5相同或不同,各自代表氢、氟、氯、溴、碘、C1-C6烷基,该基团可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷氨基羰基、二(C1-C4烷基)氨基羰基、羟基、C1-C4烷氧基、甲酰氧基、C1-C4烷基羰氧基、C1-C4烷氧羰氧基、C1-C4烷氨基羰氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基、C1-C4烷基磺酰基、二(C1-C4烷基)氨基磺酰基、C3-C6环烷基或苯基取代,或C1-C4烷氧基,该基团可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷氧基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代,或C1-C4烷硫基,该基团可任选地被氟、氯、溴、氰基、羧基、C1-C4烷氧羰基、C1-C4烷硫基、C1-C4烷基亚磺酰基或C1-C4烷基磺酰基取代,或C2-C6烯氧基,该基团可任选地被氟、氯、溴、氰基或C1-C4烷氧羰基取代,或C2-C6烯硫基,该基团可任选地被氟、氯、溴、氰基、硝基、C1-C3烷硫基或C1-C4烷氧羰基取代,C3-C6炔氧基,C3-C6炔硫基或基团-S(O)P-R6,其中
P代表数字1或2,和
R6代表C1-C4烷基,C1-C4烷氧基C1-C4烷氨基,C1-C4烷氨基,二(C1-C4烷基)氨基,
R4和/或R5还代表基团-COR8,其中
R8代表氢、C1-C6烷基、C3-C6环烷基、C1-C6烷氧基、C3-C6环烷氧基、C3-C6链烯氧基、C3-C6炔氧基、C1-C4烷硫基、C1-C4烷氨基、C1-C4烷氧氨基、C1-C4烷氧基C1-C4烷氨基或二(C1-C4烷基)氨基,它们均可任选地被氟和/或氯取代,
R10代表氢,
R11和R12相同或不同,各自代表氢、氟、氯、溴、C1-C4烷基,该基团可任选地被氟和/或氯取代,C1-C4烷氧基,该基团可任选地被氟和/或氯取代。
2.根据权利要求1的式(1)化合物或其盐,其特征在于
R1代表均可任选地被氟、氯、氰基、甲氧基或乙氧基取代的甲基、乙基、正或异丙基、正、异、仲或叔丁基,或者代表均可任选地被氟、氯或溴取代的丙烯基、丁烯基、丙炔基或丁炔基,或者代表均可任选地被氟、氯、溴、甲基或乙基取代的环丙基、环丁基、环戊基、环己基,
R2代表被氟和/或氯取代的甲基、乙基、正或异丙基、正、异、仲或叔丁基,和
R4代表氟、氯、溴、甲基、乙基、正或异丙基、三氟甲基、甲氧基、乙氧基、正或异丙氧基、二氟甲氧基、三氟甲氧基、2-氯乙氧基、2-甲氧乙氧基、甲硫基、乙硫基、正或异丙硫基、甲基亚磺酰基、乙基亚磺酰基、甲磺酰基、乙磺酰基、二甲氨基磺酰基、二乙氨基磺酰基、N-甲氧基-N-甲氨基磺酰基、甲氧羰基、乙氧羰基、正或异丙氧羰基,
R5代表氢、甲基、乙基、氟、氯或溴;
或者,
R10代表氢,
R11代表氟、氯、溴、甲基、甲氧基、二氟甲氧基、三氟甲氧基、乙氧基,和
R12代表氢。
3.制备权利要求1的式(1)化合物及其盐的方法,其特征在于
R3-SO2-N=C=O (III)其中R3如权利要求1中所定义,或
(b)通式(IV)的三唑啉酮衍生物与通式(V)的磺酰胺反应,如果合适在酸受体和稀释剂存在下进行其中R1和R2均定义如上,Z代表卤素、烷氧基、芳基烷氧基或芳氧基,
R3-SO2-NH2 (V)其中R3的定义如上,或
R3-SO2-NH-CO-Z (VI)其中R3的定义同上,Z代表卤素、烷氧基、芳基烷氧基或芳氧基,或
R3-SO2-X (VII)其中R3的定义同上,X代表卤素,
MOCN (VIII)其中M代表碱金属或碱土金属等价物,
如果需要,用常用方法将方法(a)、(b)、(c)或(d)得到的式(1)化合物转化成盐。
4.除草剂和杀真菌剂,其特征在于,其中含有至少一种权利要求1的式(1)化合物。
5.权利要求1的通式(1)化合物在防治不良植物和/或植物病原真菌方面的应用。
6.防治杂草和/或植物病原真菌的方法,其特征在于,使 1的通式(1)化合物作用于杂草或真菌或其栖息地上。
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DE19508118.8 | 1995-03-08 | ||
DE19508118A DE19508118A1 (de) | 1995-03-08 | 1995-03-08 | Sulfonylaminocarbonyltriazoline mit Halogenalkoxy-Substituenten |
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CN1090624C true CN1090624C (zh) | 2002-09-11 |
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US (1) | US6121204A (zh) |
EP (1) | EP0813528B1 (zh) |
JP (1) | JP4084413B2 (zh) |
CN (1) | CN1090624C (zh) |
AU (1) | AU703474B2 (zh) |
BR (1) | BR9607239A (zh) |
DE (2) | DE19508118A1 (zh) |
DK (1) | DK0813528T3 (zh) |
ES (1) | ES2177764T3 (zh) |
HU (1) | HU224046B1 (zh) |
MX (1) | MX9706770A (zh) |
WO (1) | WO1996027590A1 (zh) |
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DE19525162A1 (de) | 1995-07-11 | 1997-01-16 | Bayer Ag | Sulfonylamino(thio)carbonylverbindungen |
USRE39607E1 (en) | 1995-07-11 | 2007-05-01 | Bayer Aktiengesellschaft | Herbicidal sulphonylamino(thio) carbonyl compounds |
DE19802697A1 (de) | 1998-01-24 | 1999-07-29 | Bayer Ag | Selektive Herbizide auf Basis von N-Aryl-triazolin(thi)onen und N-Arylsulfonylamino(thio)carbonyltriazolin(thi)onen |
DE10031825A1 (de) | 2000-06-30 | 2002-01-10 | Bayer Ag | Selektive Herbizide auf Basis von Arylsulfonylaminocarbonyltriazolinonen |
DE10143083A1 (de) * | 2001-09-03 | 2003-03-20 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten Arylsulfonylaminocarbonyltriazolinonen und Safenern |
DE10146590A1 (de) | 2001-09-21 | 2003-04-10 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen und Safenern |
DE10146591A1 (de) | 2001-09-21 | 2003-04-10 | Bayer Cropscience Ag | Herbizide auf Basis von substituierten Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)onen |
DE10201391A1 (de) | 2002-01-16 | 2003-07-31 | Bayer Cropscience Ag | Verwendung von Alkoholethoxylaten als Penetrationsförderer |
CN1548425A (zh) * | 2003-05-13 | 2004-11-24 | 拜尔农作物科学股份公司 | 取代的三唑甲酰胺 |
EP2371823A1 (de) | 2010-04-01 | 2011-10-05 | Bayer CropScience AG | Cyclopropyl-substituierte Phenylsulfonylamino(thio)carbonyltriazolinone, ihre Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
US9981940B2 (en) | 2013-06-20 | 2018-05-29 | Bayer Cropscience Aktiengesellschaft | Aryl sulfide derivatives and aryl sulfoxide derivatives as acaricides and insecticides |
CN110734433B (zh) * | 2018-07-19 | 2020-09-11 | 东莞市东阳光农药研发有限公司 | 三氮唑化合物及其在农业中的应用 |
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EP0507171A1 (de) * | 1991-04-04 | 1992-10-07 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit über Sauerstoff gebundenen Substituenten |
US5356865A (en) * | 1990-09-22 | 1994-10-18 | Bayer Aktiengesellschaft | Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones |
US5488028A (en) * | 1989-04-13 | 1996-01-30 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having two substituents bonded via oxygen |
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DE3815765A1 (de) * | 1988-05-09 | 1989-11-23 | Bayer Ag | 2-sulfonylaminocarbonyl-2,4-dihydro-3h-1,2,4- triazol-3-one einschliesslich 4,5-kondensierter, bicyclischer derivate, verfahren und neue zwischenprodukte zu ihrer herstellung und ihre verwendung als pflanzenbehandlungsmittel |
DE4030063A1 (de) * | 1990-09-22 | 1992-03-26 | Bayer Ag | Substituierte 5-alkoxy-1,2,4,-triazol-3-(thi)one |
DE4131842A1 (de) * | 1991-09-25 | 1993-04-01 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit zwei ueber sauerstoff gebundenen substituenten |
US5057144A (en) * | 1988-05-09 | 1991-10-15 | Bayer Aktiengesellschaft | Sulphonylaminocarbonyltriazolinones |
US5534486A (en) * | 1991-04-04 | 1996-07-09 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen |
-
1995
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- 1996-03-01 JP JP52658696A patent/JP4084413B2/ja not_active Expired - Fee Related
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- 1996-03-01 DE DE59609369T patent/DE59609369D1/de not_active Expired - Lifetime
- 1996-03-01 US US08/894,931 patent/US6121204A/en not_active Expired - Fee Related
- 1996-03-01 CN CN96193575A patent/CN1090624C/zh not_active Expired - Fee Related
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- 1996-03-01 DK DK96905829T patent/DK0813528T3/da active
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US5488028A (en) * | 1989-04-13 | 1996-01-30 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having two substituents bonded via oxygen |
US5356865A (en) * | 1990-09-22 | 1994-10-18 | Bayer Aktiengesellschaft | Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones |
EP0507171A1 (de) * | 1991-04-04 | 1992-10-07 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit über Sauerstoff gebundenen Substituenten |
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MX9706770A (es) | 1997-11-29 |
WO1996027590A1 (de) | 1996-09-12 |
ES2177764T3 (es) | 2002-12-16 |
EP0813528A1 (de) | 1997-12-29 |
AU703474B2 (en) | 1999-03-25 |
BR9607239A (pt) | 1997-11-11 |
DE19508118A1 (de) | 1996-09-12 |
HU224046B1 (hu) | 2005-05-30 |
DK0813528T3 (da) | 2002-10-14 |
CN1183094A (zh) | 1998-05-27 |
EP0813528B1 (de) | 2002-06-19 |
JPH11501307A (ja) | 1999-02-02 |
US6121204A (en) | 2000-09-19 |
DE59609369D1 (de) | 2002-07-25 |
HUP9800817A3 (en) | 1999-04-28 |
HUP9800817A2 (hu) | 1998-07-28 |
JP4084413B2 (ja) | 2008-04-30 |
AU4943596A (en) | 1996-09-23 |
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