CN1315952A - 取代的噻唑(啉)亚基氨基磺酰基氨基(硫代)羰基－三唑啉酮类 - Google Patents
取代的噻唑(啉)亚基氨基磺酰基氨基(硫代)羰基－三唑啉酮类 Download PDFInfo
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- CN1315952A CN1315952A CN99810288A CN99810288A CN1315952A CN 1315952 A CN1315952 A CN 1315952A CN 99810288 A CN99810288 A CN 99810288A CN 99810288 A CN99810288 A CN 99810288A CN 1315952 A CN1315952 A CN 1315952A
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- Prior art keywords
- alkyl
- chlorine
- fluorine
- cyano
- optionally substituted
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- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical class C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 title abstract 2
- HYTBRWPZCWWCOW-UHFFFAOYSA-N s-(sulfonylamino) 5-oxo-4h-triazole-1-carbothioate Chemical class O=S(=O)=NSC(=O)N1N=NCC1=O HYTBRWPZCWWCOW-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 69
- 238000000034 method Methods 0.000 claims abstract description 23
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 11
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 11
- 239000001301 oxygen Substances 0.000 claims abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 11
- -1 (thio) carbonyl-triazolinone compounds Chemical class 0.000 claims description 281
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 52
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 43
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 37
- 125000004432 carbon atom Chemical group C* 0.000 claims description 24
- 241000196324 Embryophyta Species 0.000 claims description 23
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 23
- 239000000460 chlorine Chemical group 0.000 claims description 23
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 238000002360 preparation method Methods 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 15
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- 125000003545 alkoxy group Chemical group 0.000 claims description 11
- 125000000304 alkynyl group Chemical group 0.000 claims description 11
- CPPKAGUPTKIMNP-UHFFFAOYSA-N cyanogen fluoride Chemical compound FC#N CPPKAGUPTKIMNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 11
- 239000011737 fluorine Substances 0.000 claims description 11
- 229910052731 fluorine Inorganic materials 0.000 claims description 11
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 10
- 239000005864 Sulphur Chemical group 0.000 claims description 10
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 10
- 125000003342 alkenyl group Chemical group 0.000 claims description 9
- 229910052736 halogen Inorganic materials 0.000 claims description 9
- 150000002367 halogens Chemical class 0.000 claims description 9
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 8
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 claims description 8
- 150000003254 radicals Chemical class 0.000 claims description 8
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000003282 alkyl amino group Chemical group 0.000 claims description 7
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 7
- 125000001997 phenyl group Chemical class [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 6
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 6
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 6
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 5
- MYMALJRSNVUBAI-UHFFFAOYSA-N 1,3-thiazol-4-imine Chemical class N=C1CSC=N1 MYMALJRSNVUBAI-UHFFFAOYSA-N 0.000 claims description 5
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000001153 fluoro group Chemical group F* 0.000 claims description 5
- 230000002363 herbicidal effect Effects 0.000 claims description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 5
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 4
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 4
- 125000005108 alkenylthio group Chemical group 0.000 claims description 4
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000004104 aryloxy group Chemical group 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000000440 benzylamino group Chemical group [H]N(*)C([H])([H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000005366 cycloalkylthio group Chemical group 0.000 claims description 4
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 4
- 125000003506 n-propoxy group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])O* 0.000 claims description 4
- DWWCTYAZNNHYJA-UHFFFAOYSA-N s-(chlorosulfonylamino) 5-oxo-4h-triazole-1-carbothioate Chemical compound ClS(=O)(=O)NSC(=O)N1N=NCC1=O DWWCTYAZNNHYJA-UHFFFAOYSA-N 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 3
- 238000007796 conventional method Methods 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical class 0.000 claims description 2
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- 125000005236 alkanoylamino group Chemical group 0.000 claims description 2
- 125000005237 alkyleneamino group Chemical group 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 125000005110 aryl thio group Chemical group 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 10
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 125000002252 acyl group Chemical class 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 7
- 229910052717 sulfur Chemical group 0.000 abstract 1
- 239000011593 sulfur Chemical group 0.000 abstract 1
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 15
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 11
- 239000007858 starting material Substances 0.000 description 10
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 238000009472 formulation Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000003995 emulsifying agent Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
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- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- 239000000370 acceptor Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- DBGIVFWFUFKIQN-UHFFFAOYSA-N (+-)-Fenfluramine Chemical compound CCNC(C)CC1=CC=CC(C(F)(F)F)=C1 DBGIVFWFUFKIQN-UHFFFAOYSA-N 0.000 description 3
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 3
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00
- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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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
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
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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
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
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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
- 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
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Abstract
本发明涉及新的式(Ⅰ)的取代的噻唑(啉)亚基氨基磺酰基氨基(硫代)羰基－三唑啉酮,其中Q代表氧或硫,且R1、R2、R3、R4和R5具有不同的含义。本发明还涉及式(Ⅰ)化合物的盐、涉及新化合物的制备方法以及其作为除草剂的应用。
Description
本发明涉及新颖的取代的噻唑(啉)亚基氨基磺酰基氨基(硫代)羰基-三唑啉酮类化合物，其多种制备方法及其作为除草剂的应用。
业已知道某些取代的噻唑(啉)亚基氨基磺酰基氨基(硫代)羰基-三唑啉酮类具有除草性能(参见，例如，EP 341489、EP 422469、EP 425948、EP 431291、EP 507171、WO 93/24482、WO 94/08979、WO 95/27703、WO 96/22982)。然而，这些化合物的性能不总是完全令人满意。
因此，本发明提供新颖的通式(Ⅰ)的噻唑(啉)亚基氨基磺酰基氨基(硫代)羰基-三唑啉酮类化合物及其盐
其中
Q代表氧或硫，
R1代表氢、氨基、亚烷基氨基，或代表各任选被取代的烷基、烷氧基、烷基氨基、二烷基氨基、链烷酰基氨基、链烯基、炔基、链烯氧基、环烷基、环烷基烷基、环烷基氨基、芳基和芳烷基，
R2代表氢、氰基、卤素，或代表各任选被取代的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、二烷基氨基、链烯基、炔基、链烯氧基、链烯硫基、链烯基氨基、环烷基、环烷基烷基、环烷基氧基、环烷基硫基、环烷基氨基、芳基、芳氧基、芳硫基、芳氨基、芳烷基、芳烷氧基、芳烷硫基和芳烷基氨基，
R3代表各任选被取代的烷基、烷氧基、链烯基、炔基、环烷基、环烷基烷基、芳基和芳烷基，
R4代表氢、氰基、卤素或任选被取代的烷基，
R5代表氢、氰基、卤素或任选被取代的烷基。
通式(Ⅰ)是由下文通式(ⅠA)和(ⅠB)定义的化合物的总和。
在通式(ⅠA)和(ⅠB)中，Q、R1、R2、R3、R4和R5各具有上文通式(Ⅰ)化合物的定义中给出的含义。如果式(ⅠB)化合物中R4和R5均不为氢，则可能产生顺/反式异构体；本发明包含这二种异构体以及任何异构体比率的顺/反式混合物。
新颖的本发明通式(Ⅰ)化合物如下获得：
(a)如果适宜在反应辅助剂存在下和如果适宜在稀释剂存在下，
使通式(Ⅱ)的氯代磺酰基氨基(硫代)羰基三唑啉酮类
其中
Q、R1和R2各如上定义，
与通式(Ⅲ)的亚氨基噻唑啉(烷)类反应
其中
R3、R4和R5各如上所定义，
-或与通式(Ⅲ)化合物的酸加合物反应，
且，如果适宜，将所得的式(Ⅰ)化合物用常规的方法转化成盐，
或
(b)如果适宜在反应辅助剂存在下和如果适宜在稀释剂存在下，
使通式(Ⅳ)的三唑啉酮类
其中
R1和R2各如上定义，
与通式(Ⅴ)的异(硫代)氰酸氯磺酰基酯反应 (Ⅴ)其中
Q如上定义，
且，如果适宜在反应辅助剂存在下和如果适宜在稀释剂存在下，将所得的通式(Ⅱ)的氯代磺酰基氨基(硫代)羰基三唑啉酮类，其中
Q、R1和R2各如上所定义，
与通式(Ⅲ)的亚氨基噻唑啉(烷)类反应
其中
R3、R4和R5各如上所定义，
且如果适宜，将所得的式(Ⅰ)化合物用常规方法转化成盐。
其它可能的制备本发明通式(Ⅰ)化合物的方法列于下文，其中，Q、R1、R2、R3、R4和R5各如上所定义。
(c)如果适宜在酸受体存在下和如果适宜在稀释剂存在下，
使通式(Ⅵ)的三唑啉酮衍生物
其中
Q、R1和R2各如上所定义，和
Z代表卤素、烷氧基、芳烷氧基或芳氧基，与通式(Ⅶ)的氨基磺酰基亚氨基噻唑啉(烷)反应其中
R3、R4和R5各如上所定义，
(d)如果适宜在酸受体存在下和如果适宜在稀释剂存在下，
使通式(Ⅳ)的噻唑啉酮类其中
R1和R2各如上所定义，
与通式(Ⅸ)的磺酰胺衍生物反应其中
Q、R3、R4和R5各如上所定义，和
Z代表卤素、烷氧基、芳烷氧基或芳氧基。
新的通式(Ⅰ)化合物具有强的除草活性。
此外，下列适合于通式(Ⅰ)的定义：
Q优选代表氧或硫。
R1优选代表氢、氨基、C1-C6-亚烷基氨基，代表任选由氟-、氯-、溴-、氰基-、C1-C4-烷氧基-、C1-C4-烷基-羰基-或C1-C4-烷氧基-羰基-取代的C1-C6-烷基，代表各任选由氟-、氯-和/或溴-取代的C2-C6-链烯基或C2-C6-炔基，代表C1-C6-烷氧基或C2-C6-链烯氧基，代表各任选由氟-和/或氯-取代的C1-C6-烷基氨基、二-(C1-C4-烷基)-氨基或C1-C4-链烷酰基氨基，代表各任选由氟-、氯-、溴-和/或C1-C4-烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基，或代表各任选由氟-、氯-、溴-、氰基-、硝基-、C1-C4-烷基-、三氟甲基-、C1-C4-烷氧基-和/或C1-C4-烷氧基-羰基-取代的苯基或苯基-C1-C4-烷基。
R2优选代表氢、氰基、氟、氯、溴、碘，代表各任选由氟、氯-、溴-、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-烷氧基-羰基-或C3-C6-环烷基-取代的各在烷基中具有1至6个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基或二烷基氨基，代表各任选由氟-、氯-和/或溴-取代的各在链烯基中具有2至6个碳原子的链烯基、链烯氧基、链烯硫基或链烯氨基，代表具有2至6个碳原子的炔基、代表各任选由氟-、氯-、溴-、氰基-和/或C1-C4-烷基-取代的各在环烷基中具有3至6个碳原子和任选在烷基部分具有1至3个碳原子的环烷基、环烷基烷基、环烷基氧基、环烷基硫基或环烷基氨基，代表各任选由氟-、氯-、溴-、氰基-、硝基-、C1-C4-烷基-、三氟甲基-、C1-C4-烷氧基-、二氟甲氧基-或三氟甲氧基-取代的苯基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄氨基。
R3优选代表任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、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-烷氧基-羰基-、C1-C4-烷基氨基-羰基-或二-C1-C4-烷基-氨基-羰基-取代的具有1至6个碳原子的烷基，代表任选由氰基-、氟-、氯-或C1-C4-烷氧基-取代的具有1-6个碳原子的烷氧基，代表各任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、溴-、C1-C4-烷基-羰基-、C1-C4-烷氧基-羰基-、C1-C4-烷基氨基羰基-或二-C1-C4-烷基-氨基-羰基-取代的各具有2至6个碳原子的链烯基或炔基，代表各任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷基羰基-、C1-C4-烷氧基-羰基-、C1-C4-烷基氨基-羰基-或二-C1-C4-烷基-氨基-羰基-取代的各在环烷基中具有3至6个碳原子和任选在烷基部分具有1至3个碳原子的环烷基或环烷基烷基，或代表苯基或苄基，它们各任选由硝基、氰基、羧基、氨基甲酰基、氟、氯、溴或由(各任选由氟-和/或氯-取代的)C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基取代。
R4优选代表氢、氰基、氟、氯、溴或任选由氟-和/或氯-取代的具有1至4个碳原子的烷基。
R5优选代表氢、氰基、氟、氯、溴或任选由氟-和/或氯-取代的具有1至4个碳原子的烷基。
本发明优选提供其中Q、R1、R2、R3、R4和R5各如上作为优选定义的式(Ⅰ)化合物的钠、钾、镁、钙、铵、C1-C4-烷基铵、二-(C1-C4-烷基)-铵、三-(C1-C4-烷基)-铵、四-(C1-C4-烷基)-铵、三-(C1-C4-烷基)-锍、C5或C6-环烷基铵和二-(C1-C2-烷基)-苄基铵的盐。
优选这样一组通式(ⅠA)化合物，其中Q、R1、R2、R3、R4和R5各具有上文给出的优选的含义。
优选这样一组通式(ⅠB)化合物，其中Q、R1、R2、R3、R4和R5各具有上文给出的优选的含义。
Q特别优选代表氧或硫。
R1特别优选代表各任选由氟-、氯-、氰基-、甲氧基-或乙氧基-取代的甲基、乙基、正或异丙基，代表各任选由氟-、氯-或溴-取代的乙烯基、丙烯基、丁烯基、丙炔基或丁炔基，代表甲氧基、乙氧基、正或异丙氧基，或代表烯丙氧基，代表甲基氨基、乙基氨基、正或异丙基氨基、二甲基氨基或二乙基氨基，或代表任选由氟-、氯-、溴-、甲基-或乙基-取代的环丙基。
R2特别优选代表氯或溴，代表各任选由氟-、氯-、溴-、氰基-、甲氧基-、乙氧基-、甲硫基-、乙硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-或乙基磺酰基-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正或异丙氧基、正-、异-、仲-或叔丁氧基、甲硫基、乙硫基、正或异丙硫基、正-、异-、仲-或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正或异丙基亚磺酰基、正-、异-、仲-或叔丁基亚磺酰基、正-、异-、仲-或叔丁基磺酰基、甲基氨基、乙基氨基、正或异丙基氨基、正-、异-、仲-或叔丁基氨基、二甲氨基或二乙氨基，代表各任选由氟-、氯-和/或溴-取代的乙烯基、丙烯基、丁烯基、乙烯氧基、丙烯氧基、丁烯氧基、丙烯硫基、丁烯硫基、丙烯氨基或丁烯氨基，代表丙炔基、丁炔基、丙炔氧基、丁炔氧基、丙炔硫基或丁炔硫基，代表各任选由氟-、氯-、溴-、氰基-和/或甲基-取代的环丙基、环丁基、环戊基、环己基、环己烯基、环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环丙基硫基、环丁基硫基、环戊基硫基或环己基硫基，代表各任选由氟-、氯-、溴-、氰基-、甲基-、三氟甲基-、甲氧基-、二氟甲氧基-或三氟甲氧基-取代的苯基、苯氧基、苯硫基、苯氨基、苄基、苄氧基、苄硫基或苄氨基。
R3特别优选代表各任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、甲氧基-、乙氧基-、正或异丙氧基-、甲硫基-、乙硫基-、正或异丙硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-、甲基氨基羰基-、乙基氨基羰基-、正或异丙基氨基羰基-、二甲基氨基羰基-或二乙基氨基羰基-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基，代表各任选由氰基-、氟-、氯-、甲氧基-或乙氧基-取代的甲氧基、乙氧基、正或异丙氧基，代表各任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、溴-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-、甲基氨基羰基-、乙基氨基羰基-、正或异丙基氨基羰基-、二甲基氨基羰基-或二乙基氨基羰基-取代的乙烯基、丙烯基、丁烯基、乙炔基、丙炔基或丁炔基，代表各任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、溴-、甲基-、乙基-、正或异丙基-、正-、异-、仲-或叔丁基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-、甲基氨基羰基-、乙基氨基羰基-、正或异丙基氨基羰基、二甲基氨基羰基-或二乙基氨基羰基-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，或代表苯基或苄基，它们各任选由硝基-、氰基-、羧基-、氨基甲酰基-、氟-、氯-、溴-或由(各优选由氟和/或氯取代的)甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基取代。
R4特别优选代表氢、氰基、氟、氯、溴或任选由氟-和/或氯-取代的甲基、乙基、正或异丙基。
R5特别优选代表氢、氰基、氟、氯、溴或任选由氟-和/或氯-取代的甲基、乙基、正或异丙基。
列于上文中的一般或优选的基团定义适合于式(Ⅰ)的终产物，且相应地，适合于在每一种制备情况下所需的起始原料和中间体。这些基团定义可以相互间按需要组合，即，包括优选化合物的给定范围间的组合。
即使未明确地提到，在基团定义中提以的烃基如烷基、链烯基或炔基，可以是直链或支链的，包括与杂原子的组合如在烷氧基、烷硫基或烷基氨基中的情况。
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-氯磺酰基氨基羰基-5-乙氧基-4-甲基-2,4-二氢-3H-1,2,4-三唑-3-酮和3-乙氧基-3H-2-亚基胺作为起始原料，本发明方法(a)中的反应过程可以用下列反应式来说明：
使用例如4-乙基-5-甲硫基-2,4-二氢-3H-1,2,4-三唑-3-酮和氯代磺酰基异氰酸酯和之后3-(2-氯-乙基)-噻唑啉-2-亚基胺作为起始原料，本发明方法(b)之反应过程可以用下列反应式来说明：
式(Ⅱ)提供在制备式(Ⅰ)化合物的本发明方法(a)中用作起始原料的氯磺酰基氨基(硫代)羰基噻唑啉酮的一般定义。在式(Ⅱ)中，Q、R1和R2各优选或特别优选具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的Q、R1和R2的优选或特别优选的含义。
通式(Ⅱ)的起始原料是已知的和/或可以通过本身已知的方法制备(参见，WO 94/08979、WO 95/27703)。
式(Ⅲ)提供在制备式(Ⅰ)化合物的本发明方法(a)和(b)中用作起始原料的亚氨基噻唑啉(烷)的一般定义；式(Ⅲ)化合物还优选是指噻唑(啉)亚基胺。在式(Ⅲ)中，R3、R4和R5各优选或特别优选具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的R3、R4和R5的优选或特别优选的含义。
通式(Ⅲ)的起始原料是已知的和/或可以通过本身已知的方法制备(参见，WO 93/00336/EP 592676)。
式(Ⅳ)提供在制备式(Ⅰ)化合物的本发明方法(b)中用作起始原料的噻唑啉酮的一般定义；在式(Ⅳ)中，R1和R2各优选或特别优选具有在上文有关本发明式(Ⅰ)化合物的描述中业已提到的R1和R2的优选或特别优选的含义。
通式(Ⅳ)的起始原料是已知的和/或可以通过本身已知的方法制备(参见，EP 283876、EP 294666、EP 301946、EP 298371、EP 341489、EP 399294、EP 398096、EP 422469、EP 425948、EP 431291、EP 477646)。
制备新的式(Ⅰ)化合物的本发明方法(a)和(b)优选是在稀释剂中进行的。适合的稀释剂实际上是所有的惰性有机溶剂。这些溶剂优选包括脂肪族或芳族的任选卤代的烃，诸如，例如戊烷、己烷、庚烷、环己烷、石油醚、汽油、轻石油、苯、甲苯、二甲苯、二氯甲烷、二氯乙烷、氯仿、四氯化碳、氯苯和邻二氯苯，醚类，如乙醚和丁醚、乙二醇二甲醚和二甘醇二甲醚、四氢呋喃和二噁烷；酮类，如丙酮、甲基乙基酮、甲基异丙基酮和甲基异丁基酮；酯类，如乙酸甲酯或乙酸乙酯；腈类，如乙腈和丙腈；酰胺类，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，四亚甲基砜和六甲基磷酰三胺。
适合于用在本发明方法(a)和(b)的酸受体是所有的常规用于此类反应的酸结合剂。优选的是碱金属氢氧化物、如氢氧化钠和氢氧化钾，碱土金属氢氧化物如氢氧化钙，碱金属碳酸盐和醇化物，如碳酸钠和碳酸钾、叔丁醇钠和叔丁醇钾，以及碱性有机氮化合物如三甲胺、三乙胺、三丙胺、三丁胺、二异丁基胺、二环己基胺、乙基二异丙基胺、乙基二环己基胺、N,N-二甲基-苄基胺、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，1,5-二氮杂二环[4,3,0]-壬-5-烯(DBN)、1,8-二氮杂二环[5,4,0]-十一-7-烯(DBU)和1,4-二氮杂二环[2,2,2]-辛烷(DABCO)。
进行本发明方法(a)和(b)时，反应温度可以在较宽的范围内进行的。通常，反应是在-20℃至+80℃，优选在0℃至+50℃间的温度下进行。
本发明的方法(a)和(b)通常是在常压下进行的。然而，本发明方法也可以在加压或减压下进行。
进行本发明方法(a)和(b)时，通常采用大致等摩尔量的起始原料。然而，也可以相对大地过量采用反应组分之一。反应通常是在适合的稀释剂中、在酸受体存在下进行的，且反应混合物通常在所需的温度下搅拌数小时。本发明方法(a)和(b)的后处理各是用常规方法进行(参见，制备实施例)。
如果适宜，盐可以由本发明通式(Ⅰ)化合物制备。这些盐是用简单的常规用于成盐的方法获得，例如，通过将式(Ⅰ)化合物溶解或分散适合的溶剂如二氯甲烷、丙酮、叔丁基甲基醚或甲苯中，并加入适合的碱。这些盐之后可以-如果适宜在长时间搅拌之后-通过浓缩或抽吸过滤而分离。
本发明活性化合物可以用作脱叶剂、干燥剂、杀茎杆剂，和特别是用作除草剂。所谓的杂草，就其最广义而言，应理解为生长在不该生长的地方的所有植物。本发明的物质是作为灭生性除草剂或是选择性除草剂基本上取决于所用的量。
本发明化合物可以与例如下列植物相关使用：
下列属的双子叶杂草：芥属、独行草属、猪殃殃属、繁缕属、母菊属、春黄菊属、牛膝属、藜属、荨麻属、千里光属、苋属、马齿苋属、苍耳属、旋花属、甘薯属、蓼属、田菁属、豚草属、蓟属、飞廉属、苦苣菜属、茄属、蔊菜属、节节草属、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、蒲公英属，
下列属的双子叶作物：棉属、大豆属、甜菜属、胡萝卜属、菜豆属、豌豆属、茄属、亚麻属、甘薯属、巢菜属、烟草属、蕃茄属、花生属、芸苔属、莴苣属、黄瓜属、南瓜属，
下列属的单子叶杂草：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、高梁属、冰草属、狗牙根属、雨久花属、飘拂草属、慈菇属、荸荠属、藨草属、雀稗属、鸭嘴草属、尖瓣花属、龙爪茅属、剪股颖属、看麦娘属、风草属、山羊草属、虉草属，
下列属的单子叶作物：稻属、玉米属、小麦属、大麦属、燕麦属、黑麦属、高梁属、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应用决不限于这些属，且也可以相同的方式延伸至其它植物。
取决于化合物的浓度，化合物适合于灭生性防治杂草，例如工业地域和铁道线，以及有或无种植树林的道路和广场。同样，化合物可以用于防治多年生作物中的杂草，例如森林、装饰树林、果园、葡萄园、柑桔林、坚果园、蕉种植园、咖啡种植园、茶园、橡胶种植园、油棕榈种植园、可可种植园、软果林和啤酒花田、草场、体育场和牧场中的杂草。且本发明化合物还可以用于选择性地防治一年生作物中的杂草。
本发明式(Ⅰ)化合物当用于植物地上部分时，具有强的除草活性和宽阔的活性谱；它们中的一些同样适合于以芽前和芽后二种方式选择性地防治单子叶和双子叶作物中的单子叶和双子叶杂草。
在某种程度上，本发明式(Ⅰ)化合物还具有杀真菌活性，例如防治卵菌纲(Oomyceten)和镰孢菌(Fusarien)。
活性化合物可以转化成常规的制剂，如溶液、乳剂、可湿性粉剂、悬浮剂、粉剂、粉尘剂、膏剂、可溶性粉剂、颗粒剂、悬乳剂、用活性化合物浸渍的天然或合成材料，以及包在聚合物中的微细胶囊。
这些制剂可以用已知的方式生产，例如，将活性化合物与扩充剂，即液体溶剂和/或与固体载体混合，并任选使用表面活性剂，即乳化剂和/或分散剂和/或起泡剂。
如果用水作扩充剂，也可以用有机溶剂作助溶剂。适合的液体溶剂主要有：芳族化合物，如二甲苯，甲苯或烷基萘，氯代芳族化合物或氯代脂肪烃，如氯代苯类、氯乙烯类或二氯甲烷，脂族烃，如环己烷或石蜡，例如石油馏份、矿物和植物油，醇类，如丁醇或乙二醇以及其醚和酯，酮类，如丙酮、甲乙酮、甲基异丁基酮或环己酮，强极性溶剂，如二甲基甲酰胺或二甲基亚砜，以及水。
适合的固体载体是：例如铵盐和磨碎的天然矿物质，如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土，和磨碎的合成矿物质，如高分散二氧化硅、矾土和硅酸盐，适合用于颗粒剂的固体载体有：例如压碎并分级的天然矿物质如方解石、大理石、浮石、海泡石和白云石，以及有机和无机粉的合成颗粒，和如下有机物的颗粒：锯木屑、椰壳、玉米穗轴和烟茎；适合的乳化剂和/或起泡剂是：例如非离子和阴离子乳化剂，如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪醇醚，例如，烷芳基聚乙二醇醚，烷基磺酸盐，烷基硫酸盐，芳基磺酸盐以及白蛋白水解产物；适合的分散剂是：例如，木素亚硫酸废液和甲基纤维素。
制剂中可以使用粘合剂如羧甲基纤维素和粉状、颗粒或乳胶形式的天然和合成聚合物，如阿拉伯胶、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。其它可能的添加剂是矿物油和植物油。
也可以使用着色剂，如无机颜料，例如氧化铁、氧化钛和普鲁士蓝，和有机染料，如茜素染料、偶氮染料和金属酞菁染料，和微量营养元素如铁、锰、硼、铜、钴、钼和锌的盐。
制剂中通常含有按重量计0.1至95％的活性化合物，优选0.5至90％。
为防治杂草，本发明活性化合物，其原样或以其制剂形式，也可以作为与已知除草剂一起的混合物使用，可以是终制剂或桶混物。
混合物的可能的共组分是已知除草剂，例如，乙草胺、三氟羧草醚(钠盐)、苯草醚、甲草胺、禾草灭(钠盐)、莠灭净、amidochlor、酰嘧黄隆、莎稗磷、磺草灵、莠去津、azafenidin、四唑嘧黄隆、草除灵、呋草黄、苄嘧黄隆(甲酯)、灭草松、吡草酮、新燕灵(乙酯)、双丙氨酰磷、甲羧除草醚、双草醚、溴丁酰草胺、溴酚肟、溴苯腈、丁草胺、butroxydim、丁草敌、cafenstrole、caloxydim、双酰草胺、carfentrazone(-ethyl)、甲氧除草醚、草灭畏、杀草敏、氯嘧黄隆(乙酯)、草枯醚、绿黄隆、绿麦隆、cinidon(-ethyl)、环庚草醚、醚黄隆、烯草酮、炔草酸、异噁草酮、氯甲酰草胺、二氯吡啶酸、clopyrasulfuron(-methyl)、cloransulam(-methyl)、cumyluron、氰草津、cybutryne、灭草特、环丙嘧磺隆、噻草酮、氰氟草酯、2,4-滴、2,4-滴丁酸、2,4-滴丙酸、甜菜安、燕麦敌、麦草畏、禾草灵(甲酯)、diclosulam、乙酰甲草胺、野燕枯、吡氟草胺、diflufenzopyr、唑隆、哌草丹、二甲草胺、二甲丙乙净、二甲吩草胺、dimexyflam、氨氟灵、双苯酰草胺、敌草快、氟硫草定、敌草隆、杀草隆、epoprodan、茵达灭、戊草丹、乙丁烯氟灵、胺苯黄隆(甲酯)、乙呋草黄、ethoxyfen、ethoxysulfuron、etobenzanid、噁唑禾草灵乙酯、麦草伏(异丙酯)、麦草伏(异丙酯-L)、麦草伏(甲酯)、啶嘧黄隆、吡氟禾草灵(丁酯)、fluazolate、flucarbazone、flufenacet、唑嘧磺草胺、氟烯草酸、丙炔氟草胺、flumipropyn、氟草隆、氟咯草隆、乙羧氟草醚(乙酯)、胺草唑、flupropacil、flurpyrsulfuron(-methyl、sodium)、芴丁酸、氟啶草酮、氯氟吡氧乙酸、氟嘧醇、flurtamone、fluthiacet(-methyl)、fluthiamide、氟黄胺草醚、草铵磷(铵盐)、草甘磷(异丙铵盐)、halosafen、吡氟氯禾灵(乙氧基乙酯)、精吡氟氯禾灵(甲酯)、环嗪酮、咪草酯(甲酯)、imazamethapyr、imazamox、imazapic、灭草烟、灭草喹、咪草烟、咪唑黄隆、碘磺隆、碘苯腈、异丙乐灵、异丙隆、异噁隆、异噁酰草胺、isoxachlortole、isoxaflutole、噁草醚、乳氟禾草灵、环草定、利谷隆、2甲4氯、2甲4氯丙酸、苯噻酰草胺、mesotrione、苯嗪草酮、吡唑草胺、甲基苯噻隆、吡喃隆、秀谷隆、(α-)异丙甲草胺、磺草唑胺、甲氧隆、嗪草酮、甲黄隆(甲酯)、草达灭、绿谷隆、萘丙胺、萘氧丙草胺、草不隆、烟嘧黄隆、哒草伏、坪草丹、安磺乐灵、oxadiargyl、噁草酮、oxasulfuron、oxaziclomefone、乙氧氟草醚、百草枯、壬酸、二甲戊乐灵、pentoxazone、甜菜宁、哌草磷、丙草胺、氟嘧黄隆(甲酯)、扑草净、毒草胺、敌稗、喔草酯、异丙草胺、戊炔草胺、苄草丹、氟磺隆、pyraflufen(-ethyl)、吡唑特、吡嘧黄隆(乙酯)、苄草唑、pyribenzoxim、稗草丹、哒草特、pyriminobac(-methyl)、嘧草硫醚、二氯喹啉酸、喹草酸、灭藻醌、喹禾灵(乙酯)、喹禾灵(四氢糠酯)、砜嘧黄隆、稀禾定、西玛津、西草净、sulcotrione、甲磺草胺、嘧黄隆(甲酯)、草锍磷、甲嘧磺隆、牧草胺、特丁噻草隆、tepraloxydim、特丁津、特丁净、噻吩草胺、噻呋酰胺、噻唑烟酸、thidiazimin、噻黄隆(甲酯)、杀草丹、仲草丹、肟草酮、野燕畏、醚苯黄隆、苯黄隆(甲酯)、绿草定、灭草环、氟乐灵和氟胺黄隆。
也可以是与其它已知活性化合物如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物养料和土壤结构改良剂一起的混合物。
活性化合物可以以其本身、以其制剂或由之经进一步稀释而制备的使用形式使用，如直接可用溶液、悬浮液、乳液、粉剂、膏剂和颗粒剂。它们以常规方法使用，例如浇泼、喷雾、弥雾或撒施等等。
本发明活性化合物可以在植物萌发前或后施用。它们也可以在播种前掺入土壤中。
所用的活性化合物的量可以在相当宽的范围内变化。用量基本上取决于所需的效果。通常，使用量在每公顷土表面积用1克至10千克之间，优选每公顷5克至5千克。
本发明活性化合物的制备和使用可以参见下列实施例。
制备实施例：
实施例1
在室温(大约20℃)下，将1.7g(10mmol)3-(3-氟丙基)-3H-噻唑-2-亚基胺和1.2g(12mmol)三乙胺在5ml二氯甲烷中的溶液搅拌下滴加入到1.5g(10mmol)5-乙氧基-4-甲基-2,4-二氢-3H-1,2,4-三唑-3-酮、1.5g(10mmol)异氰酸氯磺酰基酯和50ml二氯甲烷的混合物中。反应混合物在室温下搅拌大约30分钟，之后用水洗涤，用硫酸钠干燥并过滤。滤液在水泵真空下浓缩，残余物用异丙醇消化，所得的晶状产物通过抽吸过滤分离。
由此给出2.2g(理论值的54％)2-[(3-氟-丙基)-3H-噻唑-2-亚基氨基磺酰基氨基羰基]-5-乙氧基-4-甲基-2,4-二氢-3H-1,2,4-三唑-3-酮，熔点178℃。
类似于制备实施例1，并根据本发明制备方法的一般描述，也可以制备出例如列于下文表1中的式(Ⅰ)化合物-或式(ⅠA)和(ⅠB)化合物。表1：式1-式(ⅠA)和(ⅠB)化合物的实施例
表1(续)
表1(续)表1(续)表1(续)
表1(续)
表1(续)
表1(续)
表1(续)表1(续)说明：实施例139中的基团R1(其大小已大大地缩小)具有下列含义
应用实施例
实施例A
芽前试验
溶剂： 5份重量丙酮
乳化剂： 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时，将1份重量的活性化合物与所述量的溶剂混合，将所述量的乳化剂加入，并用水将此乳油稀释至所需浓度。
将试验植物的种子播入通常的土壤中，约24小时后，土壤用活性化合物制剂浇水，在每单位面积上施用特定量的活性成分。选择喷雾液的浓度，使所需的活性化合物的特定量以1000升水/公顷的喷雾量施用。
三周后，将植物的损害程度与未处理对照的发育相比较，目测定出损害％。
数值的含义如下：
0％=无作用(与未处理相同)
100％=完全破坏
在此试验中，例如，制备实施例1、29、30、33、51、56、124、125、130和131化合物对杂草显示出非常强的活性，它们中的一些能被作物如玉米和甜菜很好地耐受。表A：芽前试验/温室表A：(续)
表A：(续)
表A：(续)表A：(续)
表A：(续)
表A：(续)表A：(续)
实施例B
芽后试验
溶剂： 5份重量丙酮
乳化剂： 1份重量的烷芳基聚乙二醇醚
制备适合的活性化合物制剂时，将1份重量的活性化合物与所述量的溶剂混合，将所述量的乳化剂加入，并用水将此乳油稀释至所需浓度。
向株高5-15厘米的试验植物按单位面积喷雾施用一定量的所需活性化合物制剂。选择喷雾液的浓度，使所需化合物的特定量以1,000升水/公顷的量施用。
三周后，将植物的损害程度与未处理对照相比较，定出损害％。
数值的含义如下：
0％=无作用(与未处理相同)
100％=完全破坏
在此试验中，制备实施例1、2、9、33、34、41、48、49、55、125、130和131化合物对杂草显示出非常强的活性。表B：芽前试验/温室表B：(续)
表B：(续)
表B：(续)
表B：(续)
表B：(续)
表B：(续)
Claims (8)
1．通式(Ⅰ)的噻唑(啉)亚基氨基磺酰基氨基(硫代)羰基-三唑啉酮化合物及其盐，
其中
Q代表氧或硫，
R1代表氢、氨基、亚烷基氨基，或代表各任选被取代的烷基、烷氧基、烷基氨基、二烷基氨基、链烷酰基氨基、链烯基、炔基、链烯氧基、环烷基、环烷基烷基、环烷基氨基、芳基和芳烷基，
R2代表氢、氰基、卤素，或代表各任选被取代的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基、二烷基氨基、链烯基、炔基、链烯氧基、链烯硫基、链烯基氨基、环烷基、环烷基烷基、环烷基氧基、环烷基硫基、环烷基氨基、芳基、芳氧基、芳硫基、芳氨基、芳烷基、芳烷氧基、芳烷硫基和芳烷基氨基，
R3代表各任选被取代的烷基、烷氧基、链烯基、炔基、环烷基、环烷基烷基、芳基和芳烷基，
R4代表氢、氰基、卤素或任选被取代的烷基，
R5代表氢、氰基、卤素或任选被取代的烷基。
2．根据权利要求1的式(Ⅰ)化合物，其特征在于，
Q代表氧或硫，
R1代表氢、氨基、C1-C6-亚烷基氨基，代表任选由氟-、氯-、溴-、氰基-、C1-C4-烷氧基-、C1-C4-烷基-羰基-或C1-C4-烷氧基-羰基-取代的C1-C6-烷基，代表各任选由氟-、氯-和/或溴-取代的C2-C6-链烯基或C2-C6-炔基，代表C1-C6-烷氧基或C2-C6-链烯氧基，代表各任选由氟-和/或氯-取代的C1-C6-烷基氨基、二-(C1-C4-烷基)-氨基或C1-C4-链烷酰基氨基，代表各任选由氟-、氯-、溴-和/或C1-C4-烷基-取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基，或代表各任选由氟-、氯-、溴-、氰基-、硝基-、C1-C4-烷基-、三氟甲基-、C1-C4-烷氧基-和/或C1-C4-烷氧基-羰基-取代的苯基或苯基-C1-C4-烷基，
R2代表氢、氰基、氟、氯、溴、碘，代表各任选由氟、氯-、溴-、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-烷氧基-羰基-或C3-C6-环烷基-取代的各在烷基中具有1至6个碳原子的烷基、烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烷基氨基或二烷基氨基，代表各任选由氟-、氯-和/或溴-取代的各在链烯基中具有2至6个碳原子的链烯基、链烯氧基、链烯硫基或链烯氨基，代表具有2至6个碳原子的炔基、代表各任选由氟-、氯-、溴-、氰基-和/或C1-C4-烷基-取代的各在环烷基中具有3至6个碳原子和任选在烷基部分具有1至3个碳原子的环烷基、环烷基烷基、环烷基氧基、环烷基硫基或环烷基氨基，代表各任选由氟-、氯-、溴-、氰基-、硝基-、C1-C4-烷基-、三氟甲基-、C1-C4-烷氧基-、二氟甲氧基-或三氟甲氧基-取代的苯基、苯氧基、苯硫基、苯基氨基、苄基、苄氧基、苄硫基或苄氨基，
R3代表任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、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-烷氧基-羰基-、C1-C4-烷基氨基-羰基-或二-C1-C4-烷基-氨基-羰基-取代的具有1至6个碳原子的烷基，代表任选由氰基-、氟-、氯-或C1-C4-烷氧基-取代的具有1-6个碳原子的烷氧基，代表各任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、溴-、C1-C4-烷基-羰基-、C1-C4-烷氧基-羰基-、C1-C4-烷基氨基羰基-或二-C1-C4-烷基-氨基-羰基-取代的各具有2至6个碳原子的链烯基或炔基，代表各任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、溴-、C1-C4-烷基-、C1-C4-烷基羰基-、C1-C4-烷氧基-羰基-、C1-C4-烷基氨基-羰基-或二-C1-C4-烷基-氨基-羰基-取代的各在环烷基中具有3至6个碳原子和任选在烷基部分具有1至3个碳原子的环烷基或环烷基烷基，或代表苯基或苄基，它们各任选由硝基、氰基、羧基、氨基甲酰基、氟、氯、溴或由(各任选由氟-和/或氯-取代的)C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基取代，
R4代表氢、氰基、氟、氯、溴或任选由氟-和/或氯-取代的具有1至4个碳原子的烷基，
R5代表氢、氰基、氟、氯、溴或任选由氟-和/或氯-取代的具有1至4个碳原子的烷基，
和式(Ⅰ)化合物的钠、钾、镁、钙、铵、C1-C4-烷基铵、二-(C1-C4-烷基)-铵、三-(C1-C4-烷基)-铵、四-(C1-C4-烷基)-铵、三-(C1-C4-烷基)-锍、C5或C6-环烷基铵和二-(C1-C2-烷基)-苄基铵的盐。
3．根据权利要求1的式(Ⅰ)化合物，其特征在于，
Q代表氧或硫，
R1代表各任选由氟-、氯-、氰基-、甲氧基-或乙氧基-取代的甲基、乙基、正或异丙基，代表各任选由氟-、氯-或溴-取代的乙烯基、丙烯基、丁烯基、丙炔基或丁炔基，代表甲氧基、乙氧基、正或异丙氧基，或代表烯丙氧基，代表甲基氨基、乙基氨基、正或异丙基氨基、二甲基氨基或二乙基氨基，或代表任选由氟-、氯-、溴-、甲基-或乙基-取代的环丙基，
R2代表氯或溴，代表各任选由氟-、氯-、溴-、氰基-、甲氧基-、乙氧基-、甲硫基-、乙硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-或乙基磺酰基-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正或异丙氧基、正-、异-、仲-或叔丁氧基、甲硫基、乙硫基、正或异丙硫基、正-、异-、仲-或叔丁硫基、甲基亚磺酰基、乙基亚磺酰基、正或异丙基亚磺酰基、正-、异-、仲-或叔丁基亚磺酰基、正-、异-、仲-或叔丁基磺酰基、甲基氨基、乙基氨基、正或异丙基氨基、正-、异-、仲-或叔丁基氨基、二甲氨基或二乙氨基，代表各任选由氟-、氯-和/或溴-取代的乙烯基、丙烯基、丁烯基、乙烯氧基、丙烯氧基、丁烯氧基、丙烯硫基、丁烯硫基、丙烯氨基或丁烯氨基，代表丙炔基、丁炔基、丙炔氧基、丁炔氧基、丙炔硫基或丁炔硫基，代表各任选由氟-、氯-、溴-、氰基-和/或甲基-取代的环丙基、环丁基、环戊基、环己基、环己烯基、环丙基氧基、环丁基氧基、环戊基氧基、环己基氧基、环丙基硫基、环丁基硫基、环戊基硫基或环己基硫基，代表各任选由氟-、氯-、溴-、氰基-、甲基-、三氟甲基-、甲氧基-、二氟甲氧基-或三氟甲氧基-取代的苯基、苯氧基、苯硫基、苯氨基、苄基、苄氧基、苄硫基或苄氨基，
R3代表各任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、甲氧基-、乙氧基-、正或异丙氧基-、甲硫基-、乙硫基-、正或异丙硫基-、甲基亚磺酰基-、乙基亚磺酰基-、甲基磺酰基-、乙基磺酰基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-、甲基氨基羰基-、乙基氨基羰基-、正或异丙基氨基羰基-、二甲基氨基羰基-或二乙基氨基羰基-取代的甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基，代表各任选由氰基-、氟-、氯-、甲氧基-或乙氧基-取代的甲氧基、乙氧基、正或异丙氧基，代表各任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、溴-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-、甲基氨基羰基-、乙基氨基羰基-、正或异丙基氨基羰基-、二甲基氨基羰基-或二乙基氨基羰基-取代的乙烯基、丙烯基、丁烯基、乙炔基、丙炔基或丁炔基，代表各任选由氰基-、羧基-、氨基甲酰基-、氟-、氯-、溴-、甲基-、乙基-、正或异丙基-、正-、异-、仲-或叔丁基-、乙酰基-、丙酰基-、甲氧基羰基-、乙氧基羰基-、正或异丙氧基羰基-、甲基氨基羰基-、乙基氨基羰基-、正或异丙基氨基羰基-、二甲基氨基羰基-或二乙基氨基羰基-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，或代表苯基或苄基，它们各任选由硝基-、氰基-、羧基-、氨基甲酰基-、氟-、氯-、溴-、或由(各任选被氟和/或氯取代的)甲基、乙基、正或异丙基、正-、异-、仲-或叔丁基、甲氧基、乙氧基、正或异丙氧基、甲硫基、乙硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基取代，
R4代表氢、氰基、氟、氯、溴或任选由氟-和/或氯-取代的甲基、乙基、正或异丙基，
R5代表氢、氰基、氟、氯、溴或任选由氟-和/或氯-取代的甲基、乙基、正或异丙基。
4．制备权利要求1的式(Ⅰ)化合物的方法，其特征在于，
(a)如果适宜在反应辅助剂存在下和如果适宜在稀释剂存在下，使通式(Ⅱ)的氯代磺酰基氨基(硫代)羰基三唑啉酮类
其中
Q、R1和R2各如权利要求1中定义，
与通式(Ⅲ)的亚氨基噻唑啉(烷)类反应其中
R3、R4和R5各权利要求1中定义，
-或与通式(Ⅲ)化合物的酸加合物反应，
且，如果适宜，将所得的式(Ⅰ)化合物用常规的方法转化成盐，
或
(b)如果适宜在反应辅助剂存在下和如果适宜在稀释剂存在下，
使通式(Ⅳ)的三唑啉酮类
其中
R1和R2各如上定义，
与通式(Ⅴ)的异(硫代)氰酸氯磺酰基酯反应
Q如上定义，
且，如果适宜在反应辅助剂存在下和如果适宜在稀释剂存在下，将所得的通式(Ⅱ)的氯代磺酰基氨基(硫代)羰基三唑啉酮类，
其中
Q、R1和R2各如上所定义，
与通式(Ⅲ)的亚氨基噻唑啉(烷)类反应其中
R3、R4和R5各如上所定义，
且如果适宜，将所得的式(Ⅰ)化合物用常规方法转化成盐。
5．除草组合物，其特征在于，它们包含至少一种权利要求1的式(Ⅰ)化合物。
6．权利要求1的式(Ⅰ)化合物防治不希望的植物的应用。
7．防治杂草的方法，其特征在于，使权利要求1的式(Ⅰ)化合物作用于杂草或其栖生地。
8．制备除草组合物的方法，其特征在于，将权利要求1的式(Ⅰ)化合物与扩充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19843766.8 | 1998-09-24 | ||
| DE19843766A DE19843766A1 (de) | 1998-09-24 | 1998-09-24 | Substituierte Thiazol(in)ylidenaminosulfonylamino(thio)carbonyl-triazolinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1315952A true CN1315952A (zh) | 2001-10-03 |
Family
ID=7882060
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN99810288A Pending CN1315952A (zh) | 1998-09-24 | 1999-09-13 | 取代的噻唑(啉)亚基氨基磺酰基氨基(硫代)羰基－三唑啉酮类 |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US6403535B1 (zh) |
| EP (1) | EP1115722A1 (zh) |
| JP (1) | JP2002526496A (zh) |
| KR (1) | KR20010074840A (zh) |
| CN (1) | CN1315952A (zh) |
| AU (1) | AU745986B2 (zh) |
| BR (1) | BR9913918A (zh) |
| CA (1) | CA2345031A1 (zh) |
| DE (1) | DE19843766A1 (zh) |
| HK (1) | HK1040713A1 (zh) |
| PL (1) | PL346857A1 (zh) |
| WO (1) | WO2000017196A1 (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102993189A (zh) * | 2011-09-15 | 2013-03-27 | 中国中化股份有限公司 | 一种含腙的三唑啉酮类化合物及其用途 |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20030187495A1 (en) | 2002-04-01 | 2003-10-02 | Cully Edward H. | Endoluminal devices, embolic filters, methods of manufacture and use |
| US20060275370A1 (en) * | 2002-07-25 | 2006-12-07 | Yih-Lin Chung | Method and compositions for treatment of epithelial damage |
| US20040093012A1 (en) | 2002-10-17 | 2004-05-13 | Cully Edward H. | Embolic filter frame having looped support strut elements |
| US20080312435A1 (en) * | 2004-11-15 | 2008-12-18 | Taisho Pharmaceutical Co., Ltd. | Imine Compound |
| US9365862B1 (en) | 2011-05-26 | 2016-06-14 | Nutech Ventures | Herbicide resistant sorghum mutants |
| US9204887B2 (en) | 2012-08-14 | 2015-12-08 | W. L. Gore & Associates, Inc. | Devices and systems for thrombus treatment |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3936623A1 (de) * | 1989-11-03 | 1991-05-08 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit ueber schwefel gebundenen substituenten |
| US5085684A (en) | 1988-05-09 | 1992-02-04 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
| 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 |
| DE3934081A1 (de) | 1989-10-12 | 1991-04-18 | Bayer Ag | Sulfonylaminocarbonyltriazolinone |
| DE3936622A1 (de) * | 1989-11-03 | 1991-05-08 | Bayer Ag | Halogenierte sulfonylaminocarbonyltriazolinone |
| US5541337A (en) | 1989-04-13 | 1996-07-30 | Bayer Aktiengesellschaft | Substituted 5-alkoxy-1,2,4-triazol-3-(thi)ones |
| US5534486A (en) | 1991-04-04 | 1996-07-09 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen |
| DE4217719A1 (de) | 1992-05-29 | 1993-12-02 | Bayer Ag | Zweifach heterocyclisch substituierte Sulfonylamino(thio)carbonylverbindungen |
| DE4234801A1 (de) | 1992-10-15 | 1994-04-21 | Bayer Ag | Sulfonylaminocarbonyltriazolinone |
| DE4411913A1 (de) * | 1994-04-07 | 1995-10-12 | Bayer Ag | Substituierte Sulfonylaminocarbonyltriazolinone |
| DE19502579A1 (de) | 1995-01-27 | 1996-08-01 | Bayer Ag | Sulfonylamino(thio)carbonyl-triazolin(thi)one |
-
1998
- 1998-09-24 DE DE19843766A patent/DE19843766A1/de not_active Withdrawn
-
1999
- 1999-09-13 WO PCT/EP1999/006753 patent/WO2000017196A1/de not_active Application Discontinuation
- 1999-09-13 CN CN99810288A patent/CN1315952A/zh active Pending
- 1999-09-13 PL PL99346857A patent/PL346857A1/xx not_active Application Discontinuation
- 1999-09-13 EP EP99969412A patent/EP1115722A1/de not_active Withdrawn
- 1999-09-13 BR BR9913918-9A patent/BR9913918A/pt not_active IP Right Cessation
- 1999-09-13 KR KR1020017002245A patent/KR20010074840A/ko not_active Application Discontinuation
- 1999-09-13 CA CA002345031A patent/CA2345031A1/en not_active Abandoned
- 1999-09-13 AU AU59777/99A patent/AU745986B2/en not_active Ceased
- 1999-09-13 JP JP2000574105A patent/JP2002526496A/ja active Pending
- 1999-09-13 US US09/787,479 patent/US6403535B1/en not_active Expired - Fee Related
-
2002
- 2002-03-27 HK HK02102369.7A patent/HK1040713A1/zh unknown
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102993189A (zh) * | 2011-09-15 | 2013-03-27 | 中国中化股份有限公司 | 一种含腙的三唑啉酮类化合物及其用途 |
| CN102993189B (zh) * | 2011-09-15 | 2015-04-08 | 中国中化股份有限公司 | 一种含腙的三唑啉酮类化合物及其用途 |
Also Published As
| Publication number | Publication date |
|---|---|
| JP2002526496A (ja) | 2002-08-20 |
| BR9913918A (pt) | 2001-06-19 |
| US6403535B1 (en) | 2002-06-11 |
| EP1115722A1 (de) | 2001-07-18 |
| CA2345031A1 (en) | 2000-03-30 |
| AU5977799A (en) | 2000-04-10 |
| DE19843766A1 (de) | 2000-03-30 |
| KR20010074840A (ko) | 2001-08-09 |
| WO2000017196A1 (de) | 2000-03-30 |
| HK1040713A1 (zh) | 2002-06-21 |
| PL346857A1 (en) | 2002-03-11 |
| AU745986B2 (en) | 2002-04-11 |
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