CN1145068A - 取代的磺酰氨基羰基三唑啉酮及其作为除草剂的应用 - Google Patents
取代的磺酰氨基羰基三唑啉酮及其作为除草剂的应用 Download PDFInfo
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- CN1145068A CN1145068A CN95192459A CN95192459A CN1145068A CN 1145068 A CN1145068 A CN 1145068A CN 95192459 A CN95192459 A CN 95192459A CN 95192459 A CN95192459 A CN 95192459A CN 1145068 A CN1145068 A CN 1145068A
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- 239000004009 herbicide Substances 0.000 title abstract description 8
- PRZRAMLXTKZUHF-UHFFFAOYSA-N 5-oxo-n-sulfonyl-4h-triazole-1-carboxamide Chemical class O=S(=O)=NC(=O)N1N=NCC1=O PRZRAMLXTKZUHF-UHFFFAOYSA-N 0.000 title abstract 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 78
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000001301 oxygen Substances 0.000 claims abstract description 25
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 25
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 23
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 125000003118 aryl group Chemical group 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 6
- 239000005864 Sulphur Chemical group 0.000 claims abstract description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 3
- -1 aromatic alkyl sulfurio Chemical class 0.000 claims description 146
- 239000000460 chlorine Substances 0.000 claims description 67
- 229910052801 chlorine Inorganic materials 0.000 claims description 67
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 61
- 229910052731 fluorine Inorganic materials 0.000 claims description 55
- 239000011737 fluorine Substances 0.000 claims description 55
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 53
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 46
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 33
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 32
- 229910052794 bromium Inorganic materials 0.000 claims description 32
- 238000002360 preparation method Methods 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 22
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 20
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 18
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 16
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 16
- 229960005437 etoperidone Drugs 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 14
- 238000006243 chemical reaction Methods 0.000 claims description 13
- 230000002363 herbicidal effect Effects 0.000 claims description 12
- 150000002431 hydrogen Chemical class 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 239000002253 acid Substances 0.000 claims description 9
- 125000003545 alkoxy group Chemical group 0.000 claims description 9
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 claims description 8
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 8
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 8
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 7
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 claims description 7
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 7
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 claims description 6
- 150000001336 alkenes Chemical class 0.000 claims description 6
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 6
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 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 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 6
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 6
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 6
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 6
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 6
- 125000001544 thienyl group Chemical group 0.000 claims description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000002603 chloroethyl group Chemical group [H]C([*])([H])C([H])([H])Cl 0.000 claims description 5
- 230000000269 nucleophilic effect Effects 0.000 claims description 5
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 4
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 4
- NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 125000003368 amide 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
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([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
- 125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 4
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 4
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 4
- 125000006125 ethylsulfonyl group Chemical group 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
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 4
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 4
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 claims description 4
- LFGREXWGYUGZLY-UHFFFAOYSA-N phosphoryl Chemical group [P]=O LFGREXWGYUGZLY-UHFFFAOYSA-N 0.000 claims description 4
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 2
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 2
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- OSRQXDWAPKNWKH-UHFFFAOYSA-N NS([O])(=O)=O Chemical compound NS([O])(=O)=O OSRQXDWAPKNWKH-UHFFFAOYSA-N 0.000 claims description 2
- NLLHXVBITYTYHA-UHFFFAOYSA-N Nitrofor Chemical compound CCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O NLLHXVBITYTYHA-UHFFFAOYSA-N 0.000 claims description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 2
- ODFJOVXVLFUVNQ-UHFFFAOYSA-N acetarsol Chemical compound CC(=O)NC1=CC([As](O)(O)=O)=CC=C1O ODFJOVXVLFUVNQ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000002905 alkanoylamido group Chemical group 0.000 claims description 2
- 125000006323 alkenyl amino group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims description 2
- 125000002102 aryl alkyloxo group Chemical group 0.000 claims description 2
- 125000001769 aryl amino group Chemical group 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 2
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 2
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 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
- 125000006003 dichloroethyl group Chemical group 0.000 claims description 2
- 125000006006 difluoroethoxy group Chemical group 0.000 claims description 2
- 229950001891 iprotiazem Drugs 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 2
- 125000001624 naphthyl group Chemical group 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000005920 sec-butoxy group Chemical group 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 2
- 125000003652 trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 2
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
- IZBNNCFOBMGTQX-UHFFFAOYSA-N etoperidone Chemical compound O=C1N(CC)C(CC)=NN1CCCN1CCN(C=2C=C(Cl)C=CC=2)CC1 IZBNNCFOBMGTQX-UHFFFAOYSA-N 0.000 claims 4
- 125000005336 allyloxy group Chemical group 0.000 claims 1
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- 230000002508 compound effect Effects 0.000 claims 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 claims 1
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- 239000002585 base Substances 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical class CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 13
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
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- 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
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- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
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- C07D249/12—Oxygen or sulfur atoms
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
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- 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
- C07D249/14—Nitrogen atoms
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Abstract
本发明涉及式(I)的新的取代的磺酰氨基羰基三唑啉酮、式I化合物的盐类，制备新化合物的方法和它们作为除草剂的应用，式(I)中Q代表氧、硫或-(N)(R4)-基，R3代表各自至少二取代，其中的一个取代基不同于烷基的芳基或芳烷基，并且R1、R2和R4代表氢或不同的取代基。
Description
本发明涉及新的取代的磺酰氨基羰基三唑啉酮、它们的多种制备方法和作为除草剂的应用。
已知某些磺酰氨基羰基三唑啉酮，如4，5-二甲基-2-(2-氯-苯磺酰-氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮表现出除草的特性(参见EP-A341489，还可参见EP-A422469、EP-A425948、EP-A431291)。但这些化合物的效力并非在各个方面都令人满意。
已发现通式(I)的新型磺酰氨基羰基三唑啉酮和式(I)化合物的盐类。
其中
Q代表氧、硫或-N(R4)-基；
R1代表氢、羟基、氨基或亚烷基氨基，或代表各自任选取代的选自烷基、烯基、炔基、环烷基、芳烷基、芳基、烷氧基、烯氧基、烷基氨基、环烷基氨基、二烷基氨基和链烷酰氨基的一个基团；
R2代表氢、羟基、巯基、氨基或卤素，或代表各自任选取代的选自烷基、环烷基、烯基、环烯基、芳烷基、芳基、烷氧基、烯氧基、炔氧基、环烷基氧基、芳氧基、芳烷基氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烯硫基、炔硫基、环烷基硫基、芳硫基、芳烷基硫基、烷基氨基、烯基氨基、芳基氨基、芳烷基氨基、二烷基氨基、吖丙啶子基、吡咯烷子基、哌啶子基和吗啉代的一个基团；
R3代表各自至少二取代，其中的一个取代基不同于烷基的芳基或芳烷基；
R4代表氢、羟基、氨基、氰基或烷氧羰基，代表任选取代的烷基、烯基、炔基、烷氧基、烯氧基、芳烷氧基、芳氧基或二烷氧基(硫代)磷酰基、或代表Q1-R5，其中
Q1代表-CO-或SO2-，并且
R5代表各自任选取代的烷基、环烷基或芳基。
式(I)的新型磺酰氨基羰基三唑啉酮可由下述方法获得，(a)适宜时在酸受体存在下，并且适宜时在稀释剂存在下，使通式(II)的氯磺酰氨基羰基三唑啉酮
其中
R1和R2具有上述的定义，与通式(III)的亲核化合物反应；
R3-Q-H (III)
其中
Q和R3具有上述的定义或者
(b)适宜时在稀释剂存在下使通式(IV)的三唑啉酮
其中
R1和R2具有上述的定义，与氯磺酰基异氰酸酯反应，并且适宜时在酸受体存在下并且适宜时在稀释剂存在下将生成的与前相同的式(II)氯磺酰氨基羰基三唑啉酮不经中间分离直接与前面通式(III)的亲核化合物反应；并且，适宜时将方法(a)或(b)所得的式(I)化合物按习用方法转化为盐类。
制备式(I)新型化合物的更为可能的方法在下面列出，其中Q、R1、R2和R3各自具有前述的定义：
(c)式(V)的异氰酸酯与式(IV)的三唑啉酮反应：
(d)式(VI)氨基磺酰基化合物与式(VII)的氧基羰基三唑啉酮(R：烷基、芳烷基或芳基)反应：
(e)式(VIII)的磺酰基尿烷与式(IV)的三唑啉酮反应(R：烷基、芳烷基或芳基)：
值得注意的是通式(I)的新型磺酰氨基羰基三唑啉酮所具有的强有力的除草剂活性。
与相似结构的、已知的4，5-二甲基-2-(2-氯-苯磺酰-氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮相比，式(I)的新型化合物令人惊异地表现出更强的除草作用。
本发明优选这样的式.(I)化合物，其中
Q代表氧、硫或-N(R4〕-基；
R1代表氢、羟基或氨基，代表C2-C10亚烷基氨基，代表任选被氟、氯、溴、氰基、C1-C4-烷氧基、C1-C4-烷基羰基或C1-C4-烷氧羰基取代的C1-C6-烷基、代表各自任选被氟、氯和/或溴取代的C3-C6-烯基或C3-C6-炔基，代表任选被氟、氯、溴和/或C1-C4-烷基取代的C3-C6-环烷基，代表任选被氟、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-羰基取代的苯基-C1-C3-烷基，代表任选被氟、氯、溴、氰基、硝基、C1-C4-烷基、三氟甲基、C1-C4-烷氧基、氟-和/或氯-取代的C1-C3-烷氧基、C1-C4-烷硫基、氟-和/或氯-取代的C1-C3烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基和/或C1-C4-烷氧-羰基取代的苯基，代表任选被氟、氯、氰基、苯基、C1-C4烷氧基或C1-C4-烷氧-羰基取代的C1-C6-烷氧基，代表C3-C6-烯氧基，代表任选被氟、氰基、C1-C4-烷氧基或C1-C4烷氧-羰基取代的C1-C4-烷基氨基、C3-C6-环烷基氨基或二-(C1-C4-烷基)-氨基，或代表C1-C6-链烷酰氨基；
R2代表氢、羟基、巯基、氨基或卤素，代表任选被氟、氯、溴、氰基、C3-C6-环烷基、C1-C4-烷氧基、C1-C4-烷硫基或-C1-C4-烷氧-羰基取代的C1-C6-烷基或C2-C6-烯基，代表任选被氟、氯、溴和/或C1-C4-烷基取代的C3-C6-环烷基，代表环己烯基，代表任选被氟、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-羰基取代的苯基-C1-C3-烷基，代表任选被氟、氯、溴、氰基、硝基、C1-C4-烷基、三氟甲基、C1-C4-烷氧基、氟-和/或氯-取代的C1-C3-烷氧基、C1-C4-烷硫基、氟-和/或氯-取代的C1-C3-烷硫基、C1-C4-烷基-亚磺酰基、C1-C4-烷基磺酰基和/或C1-C4-烷氧-羰基取代的苯基，代表任选被氟、氯、氰基、C3-C6-环烷基、C1-C4-烷氧基或C1-C4-烷氧-羰基取代的C1-C6-烷氧基，代表C3-C6-烯氧基、C3-C6-炔氧基或C3-C6-环烷基氧基，代表各自任选被氟、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氧基或苄氧基，代表各自任选被氟、氯、氰基、C1-C4-烷氧基或C1-C4-烷氧-羰基取代的C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C3-C6-烯硫基、C3-C6-炔硫基或C3-C6-环烷基硫基，代表各自任选被氟、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硫基或苯甲硫基，代表C1-C6-烷基氨基或C3-C6-烯基氨基，代表各自任选被氟、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氨基或苄基氨基，代表二-(C1-C4-烷基)-氨基，或代表各自任选被C1-C4-烷基取代的吖丙啶子基、吡咯烷子基或吗啉代；
R3代表苯基、萘基、苯基-C1-C4-烷基或萘基-C1-C4-烷基，它们各自被卤素、甲酰基、氰基、羧基或硝基；被C1-C4-烷基、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(它们各自任选被卤素、氰基、C1-C4-烷氧基或C1-C4-烷氧羰基取代)；被C1-C4-烷基磺酰氧基、C1-C4-烷基氨基磺酰氧基、二-(C1-C4-烷基)氨基磺酰氧基、C1-C4卤代烷基磺酰氧基、二-(C1-C4-烷基)氨基羰基或C1-C4-烷基氨基羰氧基；被C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基(它们各自任选被卤素或C1-C4-烷基取代)；被苯基、苯氧基、苯硫基、苯基亚磺酰基、苯基磺酰基、苯基磺酰氧基、苯基氨基、苯基羰基或苯基-C1-C4-烷基(它们各自任选被卤素、氰基、硝基、C1-C4烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、、C1-C4-卤代烷硫基、C1-C4-烷氧-羰基或C1-C4-烷氧基-氨基取代)；或被C1-C4-烷基-羰基、C3-C6-环烷基羰基或C1-C4-烷氧羰基(它们各自任选被卤素、C3-C6-环烷基或C1-C4-烷氧基取代)至少二(相同或不同)取代，其中的一个取代基不同于烷基；
R4代表氢、羟基、氨基或氰基，代表C1-C6-烷基、C3-C6-烯基或C3-C6-炔基，它们各自任选被卤素、氰基、羧基、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-烷基氨基、二-(C1-C4-烷基)-氨基或C1-C4烷氧-羰基取代，代表C1-C4-烷氧-羰基、代表C1-C6-烷氧基、C3-C6-烯氧基、苄氧基、苯氧基或二-(C1-C4-烷基)-(硫代)磷酰基，或代表Q1-R5基，其中
Q1代表-CO-或-SO2-，并且
R5代表任选被卤素或C1-C4-烷氧基取代的C1-C6-烷基，代表任选被卤素或C1-C4-烷基取代的C3-C6-环烷基，或代表任选被卤素、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基取代的苯基。
本发明另外优选其中Q、R1、R2和R3定义与前面所给优选定义相同的式(I)化合物的盐类，包括钠盐、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、C5-或C6-环烷基-铵盐和二-(C1-C2-烷基)-苄基-铵盐。
本发明特别优选这样的式(I)的化合物，其中
Q代表氧或
基；
R1代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、二氯甲基、氟乙基、氯乙基、二氟乙基、二氯乙基、三氟乙基、三氯乙基、氯二氟乙基、四氟乙基、氰甲基、氰乙基、甲氧基甲基、乙氧基甲基、甲氧基乙基或乙氧基乙基，代表烯丙基、氯烯丙基、二氯烯丙基或炔丙基、代表环丙基、苄基或苯基，代表甲氧基、乙氧基或正或异丙氧基，代表烯丙基氧基或正、异或仲丁氧基，代表甲氨基、乙氨基、或正或异丙基氨基，或代表环丙基氨基、二甲基氨基、二乙基氨基或乙酰氨基；
R2代表氯、溴、甲基、乙基、正或异丙基、正、异、仲或叔丁基、二氟甲基、三氟甲基、二氯甲基、三氯甲基、氰甲基、氰乙基、环丙基甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲硫基甲基、乙硫基甲基、甲硫基乙基或乙硫基乙基，代表环丙基、二氟环丙基或二氯环丙基、代表苯基或苄基，代表甲氧基、乙氧基或正或异丙氧基，代表二氟甲氧基、三氟甲氧基、氟乙氧基、二氟乙氧基或三氟乙氧基，代表环丙基甲氧基，代表甲氧基甲氧基、乙氧基甲氧基、甲氧基乙氧基或乙氧基乙氧基，代表苯氧基或苄氧基，代表甲硫基、乙硫基或正或异丙硫基，代表氟乙硫基、二氟乙硫基或三氟乙硫基、烯丙基硫基、炔丙基硫基、环丙基甲硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、苯硫基或苄硫基，代表甲氨基、乙氨基、正或异丙氨基、苯基氨基或苄基氨基，代表二甲基氨基、二乙基氨基、二丙基氨基、甲基乙基氨基或甲基丙基氨基，代表吖丙啶子基或代表各自任选被甲基或乙基取代的吡咯烷子基、哌啶子基或吗啉代；
R3代表苯基、苯甲基或苯乙基，其2位和6位上被氟、氯、溴、甲酰基、氰基、羧基或硝基；被甲基、乙基、正或异丙基、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(它们各自任选被氟、氯、氰基、甲氧基、乙氧基、甲氧羰基或乙氧羰基取代)；被甲基磺酰氧基、乙基磺酰氧基、甲氨基磺酰氧基、乙氨基磺酰氧基、二甲氨基磺酰氧基、二乙氨基磺酰氧基、三氟甲基磺酰氧基、二甲氨基羰基或二乙氨基羰基；被环己基或环己基甲基(它们各自任选被氯、甲基或乙基取代)；被苯基、苯氧基、苯硫基、苯磺酰基、苯磺酰氧基、苯氨基、苯基羰基、苯甲基或苯乙基(它们各自任选被氟、氯、氰基、硝基、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲硫基、乙硫基、三氟甲硫基、甲氧羰基或乙氧羰基取代)；或被乙酰基、丙酰基、正或异丁酰基、环丙基羰基、甲氧羰基或乙氧羰基(它们各自任选被氟、氯、环戊基、环己基、甲氧基或乙氧基取代)(相同或不同)取代，其中的一个取代基不同于烷基；
R4代表氢、氰基、氰甲基、氰乙基、二氟甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲氧羰基甲基、乙氧羰基甲基、甲氧羰基乙基、乙氧羰基乙基、烯丙基、炔丙基、甲氧羰基、乙氧羰基、甲氧基、乙氧基、烯丙基氧基或苄氧基，或代表Q1-R5基，其中
Q1代表-CO-或-SO2-，并且
R5代表各自任选被氟、氯、甲氧基或乙氧基取代的甲基、乙基或丙基，代表各自任选被氟、氯、甲基或乙基取代的环丙基、环丁基、环戊基或环己基，或代表任选被氟、氯、溴、甲基、乙基、三氟甲基、甲氧基或乙氧基取代的苯基。
前面所列基团的一般定义或那些优选范围的定义适用于式(I)的最终产物，同时在相应的方法中也适用于制备过程各自要求的起始化合物和/或中间体。这些基团定义在它们之间可随意组合，那些优选范围所给的定义也是如此。
在没有特意指明情况下，基团定义中述及的烃基，如烷基、烯基或炔基，以及与杂原子组合的烃基，如烷氧基、烷硫基或烷基氨基均为直链或支链。
一般情况下，卤素代表氟、氯、溴或碘，优选氟、氯或溴，特别指氟或氯。
在实施本发明方法(a)时，如果例如用2-氯磺酰氨基羰基-4-乙氧基-5-乙基-2，4-二氢-3H-1，2，4-三唑-3-酮和2-氨基-3-氟-苯乙酮作为起始化合物，则反应过程可用下式概述：
在实施本发明方法(b)时，如果例如用4-乙基-5-乙硫基-2，4-二氢-3H-1，2，4-三唑-3-酮和氯磺酰基异氰酸酯，并随后用2-氨基-6-氟-苯甲酸甲酯作为起始化合物，则反应过程可用下式概述：
在制备式(I)化合物的本发明方法(a)中作为起始化合物使用的氯磺酰氨基羰基三唑啉酮由式(II)统一定义。
在式(II)中，R1和R2优选或特别具有在上述描述式(I)新化合物时已提及的R1和R2的优选或特别优选的定义。
可被提及的式(II)起始化合物的实例如下：
4，5-二甲基-、4，5-二乙基-、4-乙基-5-甲基-、5-乙基-4-甲基-、4-甲基-5-丙基-、4-乙基-5-丙基-、4-环丙基-5-乙基-、5-环丙基-4-甲基-、5-环丙基-4-乙基-、4-甲基-5-氯-、4-乙基-5-氯-、4-甲基-5-溴-、4-乙基-5-溴-、4-环丙基-5-氯-、4-环丙基-5-溴-、4-甲氧基-5-甲基-、4-乙氧基-5-甲基-、4-乙氧基-5-乙基-、4-甲氧基-5-乙基-、4-甲基-5-甲氧基-、4-乙基-5-甲氧基-、4-甲基-5-乙氧基-、4-乙基-5-乙氧基-、4-甲基-5-甲硫基-、4-甲基-5-乙硫基-、4-乙基-5-甲硫基-、4-乙基-5-乙硫基-、4-环丙基-5-甲氧基-、4-环丙基-5-乙氧基-、4-环丙基-5-甲硫基-、4-环丙基-5-乙硫基-、4-甲氧基-5-环丙基-、4-乙氧基-5-环丙基-、4-甲氧基-5-乙氧基-、4，5-二甲氧基-、4，5-二乙氧基-、4-甲基-5-二甲氨基-、4-乙基-5-二甲氨基-和4-环丙基-5-二甲氨基-2-氯磺酰氨基羰基-2，4-二氢-3H-1，2，4-三唑-3-酮。
通式(II)的氯磺酰氨基羰基三唑啉酮未见于文献；作为新化合物，它们是一项在先申请(参见DE-P423480/LeA29398，1992年10月15日)的主题。
使通式(IV)的三唑啉酮
其中
R1和R2具有上述的定义与氯磺酰基异氰酸酯反应得到式(II)的化合物，反应适宜时在例如二氯甲烷等稀释剂存在下，于-20℃-+50℃温度进行，后处理按习用方法进行(参看制备实施例)。
制备式(I)化合物的新方法(a)和(b)中作为起始化合物使用的亲核化合物由式(III)统一定义。
在式(III)中，Q和R3优选或特别具有在上述描述式(I)新化合物时己提及的Q和R3的优选或特别优选的定义。
式(III)起始化合物为已知有机合成化学品。
制备式(I)化合物的新方法(a)和(b)中作为起始化合物使用的三唑啉酮由式(IV)统一定义。
在式(IV)中，R1和R2优选或特别优选具有在上述描述式(I)新化合物时已提及的R1和R2的优选或特别优选的定义。
式(IV)起始化合物是已知的，并/或可由本身已知的方法制备(参看EP-A283876、EP-A294666、EP-A301946、EP-A298371、EP-A341489、EP-A399294、EP-A398096、EP-A422469、EP-A425948、EP-A431291、EP-A477646、DE-OS4110795)。
实施制备式(I)新化合物的新方法(a)和(b)时最好使用稀释剂。实际上所有的惰性有机溶剂在此都适于作为稀释剂使用。可优选使用的溶剂包括任选卤代的脂族和芳香烃类，例如戊烷、己烷、庚烷、环己烷、石油醚、汽油、挥发油、苯、甲苯、二甲苯、二氯甲烷、二氯乙烷、氯仿、四氯甲烷、氯苯和邻二氯苯；醚类，例如二乙醚和二丁基醚、乙二醇二甲基醚和二甘醇二甲基醚、四氢呋喃和二噁烷；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、环丁砜和六甲基磷酰三胺。
在新方法(a)和(b)中，所有此类反应习用的酸结合剂都可用作酸受体。可优选使用碱金属氢氧化物，例如氢氧化钠和钾；碱土金属氢氧化物，例如氢氧化钙；碱金属碳酸盐和碱金属醇化物，例如碳酸钠和钾，以及叔丁醇钠和钾；另外还有碱性氮化合物，例如三甲胺、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-二甲基苯甲胺、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)、l，8-二氮杂双环-〔5，4，0〕-十一-7-烯(DBU)和1，4-二氮杂双环-〔2，2，2〕-辛烷(DABCO)。
在新方法(a)和(b)中，反应温度可在相当宽的范围内变化。反应一般在-20℃-+80℃，优选-10℃-+50℃温度实施。
新方法(a)和(b)一般在常压下实施。但也可能在增压或减压下实施。
在实施新方法(a)和(b)时，各自所需的起始化合物一般按大约等摩尔量使用。但也可能使各自使用组分中的一种的用量较大过量。反应一般在酸受体存在下在适宜的稀释剂中进行，且反应混合物各自在所需的温度下搅拌数小时。新方法(a)和(b)的后处理各自按习用方法进行(参看制备实施例)。
适宜时，可将通式(I)的新化合物制成盐类。这些盐类用简单的成盐方法获得，例如将式(I)化合物溶于或分散在诸如二氯甲烷、丙酮、叔丁基甲基醚或甲苯等一种合适的溶剂中并加入合适的碱即可得到盐类。适宜时，经较长时间的搅拌后通过浓缩或吸滤将盐类析出。
本发明的化合物可作为脱叶剂、干燥剂、茎叶破坏剂(Krautabtotungsmittel)，尤其是除草剂使用。就最广义的草类而言，可理解为生长在不该生长之处的所有植物。本发明的物质是充当灭生性除草剂还是选择性除草剂主要由所用的量决定。
本发明的活性化合物用可于诸如下列植物：
以下各属双子叶杂草：芸苔属，独行菜属，猪殃殃属，繁缕属，母菊属，春黄菊属，牛膝菊属，荨麻属，千里光属，苋属、马齿苋属，齿苋属，苍耳属，旋花属，番诸属，蓼属，田菁属，豚草属，蓟属，飞廉属，苦苣菜属，茄属，焊菜属，水松叶属，母草属，野芝麻属，婆婆纳属，茼麻属，剌酸模属，曼陀罗属，堇菜属，鼬瓣花属，罂粟属，矢车菊属，三叶草属，毛莨属和蒲公英属。
以下各属双子叶栽培作物：棉属，大豆属，慕菜属，胡罗卜属，菜豆属，豌豆属，茄属，亚麻属，番薯属，巢菜属，菸草属，番茄属，花生属，蓴菜属，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，蜀黍属，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，翦股颖属，看麦娘属和野豚鼠草属(Apera)。
以下各属单子叶栽培作物：稻属，玉蜀黍属，小麦属，大麦属，燕麦属，黑麦属，蜀黍属，黍属，甘蔗属，风梨属，天门冬属和葱属。
然而，本发明的活性化合物的用途绝不仅限于以上各属，而也以同样的方式扩展到其它植物。
因浓度而异，这类化合物适合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的灭生性除草。同样，这类化合物也可用于多年生栽培植物如造林、装饰性园林、果树园、葡萄园、桔园、坚果园、香蕉园、咖啡园、茶园、橡胶园、油棕园、可可园、软果园和酒花田除草，草坪、草地和牧场除草，以及一年生栽培植物的选择性除草。
式(I)的新化合物特别适合在单子叶作物栽培的出苗前和出苗后过程中用于单子叶杂草和双子叶杂草的选择性除草。
除此之外，新的活性化合物(I)尤其对稻瘟病(Pyricu L ariaOryzae)和麦类白粉病(Erysiphe graminis)还表现出称之为叶上昆虫杀灭效应和杀真菌剂效应等有趣的副作用。
活性化合物可调制成常规的制剂，如溶液剂、乳液剂、可湿性粉剂、悬浮液剂、粉末剂、尘剂、糊剂、可溶性粉剂、颗粒剂、悬浮液/乳液浓缩液剂、浸泡了活性化合物的天然和合成材料，以及聚合物材料的微胶囊剂。
这些制剂用已知方法制成，例如可通过下述方法：任选使用表面活性剂(即乳化剂和/或分散剂和/或起泡剂)将活性化合物和稀释剂(即液体溶剂和/或固体载体)混合。
如果采用水作稀释剂，则也可使用(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)、氯化芳族化合物或氯代脂族烃类(如氯苯、二氯乙烷或二氯甲烷)、脂族烃类(如环己烷或烷属烃，如石油馏分、矿物油和植物油)、醇类(如丁醇或乙二醇及它们的醚或酯)、酮类(如丙酮、甲基乙基酮、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)和水。
适用的固体载体有：如铵盐和研碎的天然矿物(例如高岭土、粘土、滑石粉、白垩、石英、绿坡缕石、蒙脱土或硅藻土)和研碎的合成矿物(如高分散度硅石、氧化铝和硅酸盐)；适用的固体颗粒载体有：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)及合成的无机颗粒和有机粉，和有机材料颗粒(如锯末、椰壳、玉米棒碎块和烟叶杆)；适用的乳化剂和/或起泡剂有：如非离子型和阴离子型乳化剂(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、及蛋清水解产物)；适用的分散剂有：如亚硫酸纸浆废液、甲基纤维素。
在制剂中可使用粘合剂，如羧甲基纤维素和粉状、颗粒状或胶乳状天然和合成高聚物，如阿拉伯胶、聚乙烯醇和聚乙酸乙烯酯以及天然磷脂，如脑磷脂和卵磷脂以及合成磷脂。其它添加剂可为矿物油和植物油。
可使用着色剂，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)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至95％(重量)，优选0.5至90％(重量)的活性化合物。
除草时，本发明的活性化合物以其本身或以其制剂形式，也可与可能用到的已知除草剂的混合物形式制成制剂或容器混合料使用。
混合物适用的除草剂是已知的除草剂，例如酰替苯胺类，如二氟酚(diflufenican)和敌稗；芳基羧酸类，如二氯吡啶甲酸、麦草畏和毒莠定；芳氧基链烷酸类，如2，4-D(2，4-滴)、2，4-DB(2，4-滴丁酸)、2，4-DP(2，4-滴丙酸)、氟氯吡啶(fluroxypyr)、MCPA(2甲4氯)、MCPP(2甲4氯丙酸)和木草畏(triclopyr)；芳氧基-苯氧基链烷酸酯，如禾草灵(diclofop-methyl)，乙基酚丙酸(fenoxaprop-ethyl)，禾草枯(fulazifop-buryl)，甲基海酚丙(haloxyfop-methyl)和2-〔4-〔(6-氯-2-喹喔啉基)氧〕苯氧基〕丙酸乙酯(quizalofop-ethyl)，azinone类，例如5-氨基-4-氯-2-苯基哒嗪-3(2H)-酮(Chloridazon)和哒草灭；氨基甲酸酯类，例如氯苯胺灵、异苯敌、苯敌草和苯胺灵、氯乙酰替苯胺类，例如草不绿、灭草胺、去草胺、甲吡唑安(metazachlor)，甲代隆，氯苯胺和毒草胺；二硝基苯胺类，例如黄草消、芽草平和氟乐灵；二苯醚类，例如氟草灭，治草醚，氟糖酚(fluoroglycofen)，虎威，halosafen，乳酚(lactofen)和氟草胺；脲类，例如绿麦隆，敌草隆，伏草隆，异丙隆，利谷隆和噻唑隆；羟胺类，例如枯杀达，乙氧定(clethodim)、环氧定(cycloxydim)，禾莠净和烷氧定(tralkoxydim)；咪唑啉酮类，例如咪唑乙畏(imazethapyr)，咪唑甲苯(imazamethabenz)，咪唑吡啶(imazapyr)和咪唑喹啉(imazaquin)；腈类，例如溴苯腈，敌草腈和碘苯腈、氧乙酰胺类，例如mefenacet；磺酰脲类，例如amidosulfuron，甲基苯磺隆(bensulfuron-methyl)，乙基氯默隆(chlorimuron-ethyl)，阔草脲，cinosulfuron，甲基甲磺隆(metoulfuron-methyl)，nicosulfuron，primisulfuron，乙基吡唑杀隆(pyrazosulfuron-ethyl)，甲基西酚杀隆(thifensulfuron-methyl)，三硫隆(triasulfuron)和甲三苯隆(tribenuron-methyl)；硫代氨基甲酸酯类，例如苏达灭，草灭特，燕麦敌，扑草灭，esprocarb，草达灭，扑硫成(prosulphocarb)，杀草丹和野麦畏；三嗪类，例如阿特拉津，草净津，西玛津，西草净，去草净和特丁津(terbuthylazine)；三嗪酮类，例如敌草灵(hexazinone)，灭它通(metamitron)和赛克津；及其它除草剂，例如氨基三唑，benfuresate，噻草平，辛甲灵(cinmethylin)，氯马腙(clomazone)，氯吡啶(clopyralid)，燕麦清(difenzoquat)，dithiopyr，草定完，卤吡咯酮(fluorochloridone)，glufosinate，草甘膦，异恶苯(isozaben)，草利达(pyridate)，quinchlorac，quinmerac，sulphosate和2-(3，5-二氯(苯基)-2-(2，2，2-三氯乙基)环氧乙烷(tridiphabe)。
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、植物营养剂及土壤结构改良剂的混合物也可以使用。
活性化合物的使用形式可以是它们的制剂形式或经进一步稀释制得的使用形式，如待用的溶液、悬浮液、乳液、粉剂、糊剂和颗粒剂。使用时可以习用方法进行，例如浇水、喷撒、喷雾或散布。
本发明的活性化合物可在植物出苗前或出苗后使用。也可将它们在播种前加到土壤中使用。
活性化合物的用量可在一个相当大的范围内变化。它主要取决于预期效果的性质。一般情况下，用量为每公顷土壤表面1g-10kg活性化合物，优选每公顷5g-2kg。
新活性化合物的制备和应用以下述实施例说明。制备实施例实施例1(方法(a))
首先将2.85g(0.01mol)2-氯磺酰氨基羰基-4-甲基-5-乙氧基-2，4-二氢-3H-1，2，4-三唑-3-酮引入150ml二氯甲烷中，并在20℃下将3.26g(0.02mol)2-氨基-3-甲基-苯基-乙基酮加到此混合物中。反应混合物在20℃下搅拌2小时。然后用每次50ml的水洗涤三次，经硫酸钠干燥并过滤。滤液在水泵真空下浓缩，并将剩余物在乙醇中重结晶。
得到3.58g(理论值的87％)2-(2-甲基-6-丙酰基-苯基氨基-磺酰氨基羰基)-4-甲基-5-乙氧基-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点134℃。
类似于实施例1，并依照新制备方法的一般描述可制得例如下表1中所列的式(I)化合物。
表1 式(I)化合物的制备实施例(表1中，“D”代表“熔化时分解”)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
续表1
续表1
续表1续表1式(II)的起始化合物实施例(II-1)
首先将28.8g(0.2mol)5-乙氧基-4-甲基-2，4-二氢-3H-1，2，4-三唑-3-酮引入250ml二氯甲烷中，并将混合物冷至-10℃。加入28.3g(0.20mol)氯磺酰基异氰酸酯，并将反应混合物在没有冷却下搅拌30分钟。然后在水泵真空下小心地蒸去溶剂。
得到53g(理论值的93％)2-氯磺酰氨基羰基-5-乙氧基-4-甲基-2，4-二氢-3H-1，2，4-三唑-3-酮结晶剩余物，熔点106℃。
实施例(II-2)
首先将22.6g(0.20mol)4，5-二甲基-2，4-二氢-3H-1，2，4-三唑-3-酮引250ml二氯甲烷中，并将混合物冷至-10℃。然后加入28.3g(0.20mol)氯磺酰基异氰酸酯并将混合物在由-5℃至-10℃温度下搅拌20分钟，开始时形成清亮溶液，随后产物以结晶形式析出。通过吸滤将其分离出来。
得到45g(理论值的88％)2-氯磺酰氨基羰基-4，5-二甲基-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点150℃(分解)。
实施例(II-3)
将9.9g(72mmol)氯磺酰基异氰酸酯在-10℃至0℃的温度下缓慢加到于250ml二氯甲烷中的10g(72mmol)5-二甲氨基-4-甲基-2，4-二氢-3H-1，2，4-三唑-3-酮中。搅拌30分钟后，反应混合物已达到室温(20℃)。然后在水泵真空下蒸馏除去溶剂。
得到19.1g(理论值的94％)2-氯磺酰氨基羰基-5-二甲氨基-4-甲基-2，4-二氢-3H-1，2，4-三唑-3-酮无定形剩余物。式(III)的起始化合物
实施例(III-1)
在冰冷却同时将32.0g(0.25mol)2-氯苯胺加到溶于200ml二氯乙烷的33.8g(0.29mol)氯化硼(III)中。然后在0℃下连续加入22.0g(0.32mol)丁腈和38g(0.28mol)氯化铝。混合物加热回流15小时，并在冷却后将其倒在冰水上；随后分出有机相，将其用硫酸钠干燥并蒸馏。
得到12g(理论值的24％-)2-氯-6-丙基羰基-苯胺，沸点105℃(2mbar)。
实施例(III-2)
将30g(0.25mol)氯化硼(III)在0℃-+5℃温度下加到250ml二氯乙烷中，并在0℃-+5℃温度下将26.8g(0.25mol)2-甲基-苯胺滴加到此混合物中。然后在0℃-+5℃温度下滴加25g(0.375mol)环丙基氰化物，紧接着分批计量加入36g(0.275mol)氯化铝(III)。随后将反应混合物加热回流约15小时，使之冷却后将其倒到约1升冰水中。搅拌混合物直至固体组分溶解，此后分出有机相，用硫酸钠干燥并过滤。滤液在水泵真空下浓缩，用挥发油消化使剩余物产生结晶，并通过吸滤将产物分离出来。
得到58g(理论值的66％)2-环丙基羰基-6-甲基苯胺，熔点64℃应用实施例实施例A出苗前试验
溶剂：5份重量的丙酮
乳化剂：1份重量的烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时，将1份重量的活性化合物与所述量的溶剂混合，加入所述量的乳化剂并将浓缩液用水稀释至所需浓度。
将试验植物的种子播种在普通土壤中。24小时后，土壤用活性化合物制剂浇灌使每个单位面积的用水量保持恒定。制剂中活性化合物的浓度不具重要意义，关键是单位面积所用活性化合物的量。三星期后，与未经处理的对照物的生长相比较，以％杀灭率评定对植物的杀灭程度。下述符号代表：
0％＝没有杀灭作用(与未经处理的对照物相同)
100％＝全部杀灭
被测活性化合物、它们的施用量，试验植物和所得试验结果列于下表A中。
表A中，活性化合物的序号系指上述制备实施例的序号(参看实施例1和表1)。表A：出苗前试验/温室活性 小麦 玉米 猪殃 牛膝 马齿 芸苔属 茄属化合物 施加量 殃属 菊属 苋属序号 (kg/ha)1 125 0 80 100 100 95 95 9523 30 0 0 95 95 95 95 9024 60 0 40 95 95 95 95 9536 125 0 50 70 100 95 90 90103 125 0 0 95 100 70 90 95108 125 0 0 95 95 80 80 95111 250 0 0 95 95 95 95 95114 125 0 10 95 95 90 95 95118 125 0 0 95 95 80 90 95132 125 0 0 90 95 60 95 95134 125 0 0 95 95 80 95 95135 60 20 0 80 95 70 80 60138 250 0 40 95 95 95 80 95141 125 0 0 80 70 90 80 90143 125 20 0 70 95 90 70 90148 30 0 30 80 95 95 90 95174 125 0 10 70 90 80 90 90204 125 30 0 95 95 95 95 95206 125 0 0 90 100 95 95 95216 30 0 60 90 95 50 90 90试验B出苗后试验
溶剂：5份重量丙酮
乳化剂：1份重量的烷芳基聚乙二醇醚
制备活性化合物的适宜制剂时，将1份重量的活性化合物与所述量的溶剂混合，加入所述量的乳化剂并将浓缩液用水稀释至所需浓度。
用活性化合物制剂对高度为5-15cm的试验植物进行喷撒使单位面积撒上特定量的所需活性化合物。喷撒液的浓度如此选择，使所需的具体活性化合物量按2,000L水/ha施用。三星期后，与未经处理的对照物的生长相比较，以％杀灭率评定对植物的杀灭程度。
下述符号代表：
0％＝无杀灭作用(与未经处理的对照物相同)
100％＝全部杀灭
被测活性化合物，它们的施用量、试验植物和所得试验结果列于下表B中。
表B中，活性化合物序号系指上述制备实施例的序号。表B：出苗后试验/温室活性 小麦 玉米 苋属 猪殃 马蹄草 番薯属 茄属化合物 施加量 殃属序号 (kg/ha)103 60 0 15 70 95 60 70 95108 125 0 50 80 95 70 90 95120 60 0 10 90 40 70 90 90123 30 0 40 95 90 95 90 90124 60 0 5 80 90 100 20 90126 60 0 5 40 60 90 30 90131 125 0 10 90 70 40 60 80132 125 0 5 95 90 95 50 100134 125 0 0 95 90 95 80 100174 30 0 0 100 95 95 50 95216 15 0 70 100 80 70 80 95229 125 0 15 90 80 95 60 70
Claims (9)
1.通式(I)的取代的磺酰氨基羰基三唑啉酮和式(I)化合物的盐类，
其中
Q代表氧、硫或-N(R4)-基；
R1代表氢、羟基、氨基或亚烷基氨基，或代表各自任选取代的选自烷基、烯基、炔基、环烷基、芳烷基、芳基、烷氧基、烯氧基、烷基氨基、环烷基氨基、二烷基氨基和链烷酰氨基的一个基团；
R2代表氢、羟基、巯基、氨基或卤素，或代表各自任选取代的选自烷基、环烷基、烯基、环烯基、芳烷基、芳基、烷氧基、烯氧基、炔氧基、环烷基氧基、芳氧基、芳烷基氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、烯基硫基、炔基硫基、环烷基硫基、芳基硫基、芳烷基硫基、烷基氨基、烯基氨基、芳基氨基、芳烷基氨基、二烷基氨基、吖丙啶子基、吡咯烷子基、哌啶子基和吗啉代的一个基团；
R3代表各自至少二取代，其中的一个取代基不同于烷基的芳基或芳烷基；
R4代表氢、羟基、氨基、氰基或烷氧羰基，代表任选取代的烷基、烯基、炔基、烷氧基、烯氧基、芳烷氧基、芳氧基或二烷氧基(硫代)磷酰基、或代表Q1-R5，其中
Q1代表-CO-或SO2-，并且
R5代表各自任选取代的烷基、环烷基或芳基。
2.根据权利要求1的式(I)的化合物，其特征在于
Q代表氧、硫或-N(R4)-基；
R1代表氢、羟基或氨基，代表C2-C10亚烷基氨基，代表任选被氟、氯、溴、氰基、C1-C4-烷氧基、C1-C4-烷基羰基或C1-C4-烷氧羰基取代的C1-C6-烷基、代表各自任选被氟、氯和/或溴取代的C3-C6-烯基或C3-C6-炔基，代表任选被氟、氯、溴和/或C1-C4-烷基取代的C3-C6-环烷基，代表任选被氟、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-羰基取代的苯基-C1-C3-烷基，代表任选被氟、氯、溴、氰基、硝基、C1-C4-烷基、三氟甲基、C1-C4-烷氧基、氟-和/或氯-取代的C1-C3-烷氧基、C1-C4-烷硫基、氟-和/或氯-取代的C1-C3烷硫基、C1-C4-烷基亚磺酰基、C1-C4-烷基磺酰基和/或C1-C4-烷氧-羰基取代的苯基，代表任选被氟、氯、氰基、苯基、C1-C4烷氧基或C1-C4-烷氧-羰基取代的C1-C6-烷氧基，代表C3-C6-烯氧基，代表任选被氟、氰基、C1-C4-烷氧基或C1-C4烷氧-羰基取代的C1-C4-烷基氨基、C3-C6-环烷基氨基或二-(C1-C4-烷基)-氨基，或代表C1-C6-链烷酰氨基；
R2代表氢、羟基、巯基、氨基或卤素，代表任选被氟、氯、溴、氰基、C3-C6-环烷基、C1-C4-烷氧基、C1-C4-烷硫基或-C1-C4-烷氧-羰基取代的C1-C6-烷基或C2-C6-烯基，代表任选被氟、氯、溴和/或C1-C4-烷基取代的C3-C6-环烷基，代表环己烯基，代表任选被氟、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-羰基取代的苯基-C1-C3-烷基，代表任选被氟、氯、溴、氰基、硝基、C1-C4-烷基、三氟甲基、C1-C4-烷氧基、氟-和/或氯-取代的C1-C3-烷氧基、C1-C4-烷硫基、氟-和/或氯-取代的C1-C3-烷硫基、C1-C4-烷基-亚磺酰基、C1-C4-烷基磺酰基和/或C1-C4-烷氧-羰基取代的苯基，代表任选被氟、氯、氰基、C3-C6-环烷基、C1-C4-烷氧基或C1-C4-烷氧-羰基取代的C1-C6-烷氧基，代表C3-C6-烯氧基、C3-C6-炔氧基或C3-C6-环烷基氧基，代表各自任选被氟、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氧基或苄氧基，代表各自任选被氟、氯、氰基、C1-C4-烷氧基或C1-C4-烷氧-羰基取代的C1-C6-烷硫基、C1-C6-烷基亚磺酰基、C1-C6-烷基磺酰基、C3-C6-烯硫基、C3-C6-炔硫基或C3-C6-环烷基硫基，代表各自任选被氟、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硫基或苯甲硫基，代表C1-C6-烷基氨基或C3-C6-烯基氨基，代表各自任选被氟、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氨基或苄基氨基，代表二-(C1-C4-烷基)-氨基，或代表各自任选被C1-C4-烷基取代的吖丙啶子基、吡咯烷子基或吗啉代；
R3代表苯基、萘基、苯基-C1-C4-烷基或萘基-C1-C4-烷基，它们各自被卤素、甲酰基、氰基、羧基或硝基；被C1-C4-烷基、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(它们各自任选被卤素、氰基、C1-C4-烷氧基或C1-C4-烷氧羰基取代)；被C1-C4-烷基磺酰氧基、C1-C4-烷基氨基磺酰氧基、二-(C1-C4-烷基)氨基磺酰氧基、C1-C4卤代烷基磺酰氧基、二-(C1-C4-烷基)氨基羰基或C1-C4-烷基氨基羰氧基；被C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基(它们各自任选被卤素或C1-C4-烷基取代)；被苯基、苯氧基、苯硫基、苯基亚磺酰基、苯基磺酰基、苯基磺酰氧基、苯基氨基、苯基羰基或苯基-C1-C4-烷基(它们各自任选被卤素、氰基、硝基、C1-C4烷基、C1-C4-卤代烷基、C1-C4-烷氧基、C1-C4-卤代烷氧基、C1-C4-烷硫基、、C1-C4-卤代烷硫基、C1-C4-烷氧-羰基或C1-C4-烷氧基-氨基取代)；或被C1-C4-烷基-羰基、C3-C6-环烷基羰基或C1-C4-烷氧基羰基(它们各自任选被卤素、C3-C6-环烷基或C1-C4-烷氧基取代)至少二(相同或不同)取代，其中的一个取代基不同于烷基；
R4代表氢、羟基、氨基或氰基，代表C1-C6-烷基、C3-C6-烯基或C3-C6-炔基，它们各自任选被卤素、氰基、羧基、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-烷基氨基、二-(C1-C4-烷基)-氨基或C1-C4烷氧-羰基取代，代表C1-C4-烷氧-羰基、代表C1-C6-烷氧基、C3-C6-烯氧基、苄氧基、苯氧基或二-(C1-C4-烷氧基)-(硫代)磷酰基，或代表Q1-R5基，其中
Q1代表-CO-或-SO2-，并且
R5代表任选被卤素或C1-C4-烷氧基取代的C1-C6-烷基，代表任选被卤素或C1-C4-烷基取代的C3-C6-环烷基，或代表任选被卤素、C1-C4-烷基、C1-C4-卤代烷基或C1-C4-烷氧基取代的苯基。
3.根据权利要求1的式(I)的化合物，其特征在于Q代表氧或
基；
R1代表甲基、乙基、正或异丙基、正、异、仲或叔丁基、二氯甲基、氟乙基、氯乙基、二氟乙基、二氯乙基、三氟乙基、三氯乙基、氯二氟乙基、四氟乙基、氰甲基、氰乙基、甲氧基甲基、乙氧基甲基、甲氧基乙基、或乙氧基乙基，代表烯丙基、氯烯丙基、二氯烯丙基或炔丙基、代表环丙基、苄基或苯基，代表甲氧基、乙氧基或正或异丙氧基，代表烯丙基氧基或正、异或仲丁氧基，代表甲氨基、乙氨基、或正或异丙基氨基，或代表环丙基氨基、二甲基氨基、二乙基氨基或乙酰氨基；
R2代表氯、溴、甲基、乙基、正或异丙基、正、异、仲或叔丁基、二氟甲基、三氟甲基、二氯甲基、三氯甲基、氰甲基、氰乙基、环丙基甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲硫基甲基、乙硫基甲基、甲硫基乙基或乙硫基乙基，代表环丙基、二氟环丙基或二氯环丙基、代表苯基或苄基，代表甲氧基、乙氧基或正或异丙氧基，代表二氟甲氧基、三氟甲氧基、氟乙氧基、二氟乙氧基或三氟乙氧基，代表环丙基甲氧基，代表甲氧甲氧基、乙氧甲氧基、甲氧乙氧基或乙氧乙氧基，代表苯氧基或苄氧基，代表甲硫基、乙硫基或正或异丙硫基，代表氟乙硫基、二氟乙硫基或三氟乙硫基、烯丙基硫基、炔丙基硫基、环丙基甲硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基、乙基磺酰基、苯硫基或苄硫基，代表甲氨基、、乙氨基、正或异丙氨基、苯基氨基或苄基氨基，代表二甲基氨基、二乙基氨基、二丙基氨基、甲基乙基氨基或甲基丙基氨基，代表吖丙啶子基或代表各自任选被甲基或乙基取代的吡咯烷子基、哌啶子基或吗啉代；
R3代表苯基、苯甲基或苯乙基，其2位和6位上被氟、氯、溴、甲酰基、氰基、羧基或硝基；被甲基、乙基、正或异丙基、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(它们各自任选被氟、氯、氰基、甲氧基、乙氧基、甲氧羰基或乙氧羰基取代)；被甲基磺酰氧基、乙基磺酰氧基、甲氨基磺酰氧基、乙氨基磺酰氧基、二甲基氨基磺酰氧基、二乙氨基磺酰氧基、三氟甲基磺酰氧基、二甲基氨基羰基或二乙基氨基羰基；被环己基或环己基甲基(它们各自任选被氯、甲基或乙基取代)；被苯基、苯氧基、苯硫基、苯磺酰基、苯磺酰氧基、苯氨基、苯基羰基、苯甲基或苯乙基(它们各自任选被氟、氯、氰基、硝基、甲基、乙基、三氟甲基、甲氧基、乙氧基、二氟甲氧基、三氟甲氧基、甲硫基、乙硫基、三氟甲硫基、甲氧羰基或乙氧羰基取代)；或被乙酰基、丙酰基、正或异丁酰基、环丙基羰基、甲氧羰基或乙氧羰基(它们各自任选被氟、氯、环戊基、环己基、甲氧基或乙氧基取代)(相同或不同)取代；
R4代表氢、氰基、氰甲基、氰乙基、二氟甲基、甲氧基甲基、乙氧基甲基、甲氧基乙基、乙氧基乙基、甲氧羰基甲基、乙氧羰基甲基、甲氧羰基乙基、乙氧羰基乙基、烯丙基、炔丙基、甲氧羰基、乙氧羰基、甲氧基、乙氧基、烯丙氧基或苄氧基，或代表Q1-R5基，其中
Q1代表-CO-或-SO2-，并且
R5代表各自任选被氟、氯、甲氧基或乙氧基取代的甲基、乙基或丙基，代表各自任选被氟、氯、甲基或乙基取代的环丙基、环丁基、环戊基或环己基，或代表任选被氟、氯、溴、甲基、乙基、三氟甲基、甲氧基或乙氧基取代的苯基。
4.权利要求1、2和3的式(I)化合物的盐类，包括钠盐、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、C5-或C6-环烷基-铵盐和二-(C1-C2-烷基)-苄基-铵盐。
5.制备权利要求1的式(I)的取代磺酰氨基羰基三唑啉酮的方法，其特征在于
(a)适宜时在酸受体存在下，并且适宜时在稀释剂存在下，使通式(II)的氯磺酰氨基羰基三唑啉酮
其中
R1和R2具有权利要求1中给出的定义，与通式(III)的亲核化合物反应，R3-Q-H (III)
其中
Q和R3具有权利要求1中给出的定义；或者
(b)适宜时在稀释剂存在下使通式(IV)的三唑啉酮
其中
R1和R2具有权利要求1中给出的定义，与氯磺酰基异氰酸酯反应，并且适宜时在酸受体存在下并且适宜时在稀释剂存在下将生成的式(II)氯磺酰氨基羰基三唑啉酮不经中间分离直接与通式(III)的亲核化合物反应，并且，适宜时将方法(a)或(b)所得的式(I)的化合物按习用方法转化为盐类。
6.除草剂组合物，其特征为内含至少一种权利要求1的式(I)的化合物。
7.权利要求1的通式(I)化合物在控制不良植物生长中的应用。
8.除草方法，其特征在于使权利要求1的通式(I)化合物作用于草类或其生长环境。
9.制备除草剂组合物的方法，其特征在于将权利要求1的通式(I)化合物与稀释剂和/或表面活性剂混合。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEP4411913.5 | 1994-04-07 | ||
| DE4411913A DE4411913A1 (de) | 1994-04-07 | 1994-04-07 | Substituierte Sulfonylaminocarbonyltriazolinone |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1145068A true CN1145068A (zh) | 1997-03-12 |
Family
ID=6514782
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN95192459A Pending CN1145068A (zh) | 1994-04-07 | 1995-03-27 | 取代的磺酰氨基羰基三唑啉酮及其作为除草剂的应用 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US5861358A (zh) |
| EP (1) | EP0754179A1 (zh) |
| JP (1) | JPH09511510A (zh) |
| CN (1) | CN1145068A (zh) |
| AU (1) | AU2136595A (zh) |
| BR (1) | BR9507294A (zh) |
| CA (1) | CA2187215A1 (zh) |
| DE (1) | DE4411913A1 (zh) |
| HU (1) | HUT76496A (zh) |
| WO (1) | WO1995027703A1 (zh) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
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| USRE39607E1 (en) | 1995-07-11 | 2007-05-01 | Bayer Aktiengesellschaft | Herbicidal sulphonylamino(thio) carbonyl compounds |
| DE19525162A1 (de) * | 1995-07-11 | 1997-01-16 | Bayer Ag | Sulfonylamino(thio)carbonylverbindungen |
| DE19615900A1 (de) * | 1996-04-22 | 1997-10-23 | Bayer Ag | Substituierte Sulfonylamino(thio)carbonyl-triazolin(thi)one |
| ZA974703B (en) * | 1996-05-30 | 1997-12-30 | Bayer Ag | Substituted sulfonylamino(thio)carbonyl compounds. |
| DE19843766A1 (de) * | 1998-09-24 | 2000-03-30 | Bayer Ag | Substituierte Thiazol(in)ylidenaminosulfonylamino(thio)carbonyl-triazolinone |
| ES2399241T3 (es) * | 2004-11-18 | 2013-03-26 | Synta Pharmaceuticals Corporation | Compuestos de triazol que modulan la actividad de HSP90 |
| EP1717228A1 (de) * | 2005-04-28 | 2006-11-02 | Bayer CropScience GmbH | Sulfonylamino(thio)carbonylverbindungen als Herbizide oder Pflanzenwachstumsregulatoren |
| US7662813B2 (en) | 2005-08-18 | 2010-02-16 | Synta Pharmaceuticals Corp. | Triazole compounds that modulate HSP90 activity |
| EP2032545A2 (en) * | 2006-05-25 | 2009-03-11 | Synta Pharmaceuticals Corporation | Compounds that modulate hsp90 activity and methods for identifying same |
| EP2560640A1 (en) | 2010-04-19 | 2013-02-27 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of a hsp90 inhibitory compounds and a egfr inhibitor |
| JP2014532712A (ja) | 2011-11-02 | 2014-12-08 | シンタ ファーマシューティカルズ コーポレーション | トポイソメラーゼｉ阻害剤とｈｓｐ９０阻害剤の組合せを使用する癌療法 |
| WO2013067165A1 (en) | 2011-11-02 | 2013-05-10 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with platinum-containing agents |
| CA2854188A1 (en) | 2011-11-14 | 2013-05-23 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with braf inhibitors |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3934081A1 (de) * | 1989-10-12 | 1991-04-18 | Bayer Ag | Sulfonylaminocarbonyltriazolinone |
| US5057144A (en) * | 1988-05-09 | 1991-10-15 | Bayer Aktiengesellschaft | Sulphonylaminocarbonyltriazolinones |
| 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 |
-
1994
- 1994-04-07 DE DE4411913A patent/DE4411913A1/de not_active Withdrawn
-
1995
- 1995-03-27 AU AU21365/95A patent/AU2136595A/en not_active Abandoned
- 1995-03-27 EP EP95914315A patent/EP0754179A1/de not_active Withdrawn
- 1995-03-27 CA CA002187215A patent/CA2187215A1/en not_active Abandoned
- 1995-03-27 WO PCT/EP1995/001149 patent/WO1995027703A1/de not_active Application Discontinuation
- 1995-03-27 US US08/718,326 patent/US5861358A/en not_active Expired - Fee Related
- 1995-03-27 BR BR9507294A patent/BR9507294A/pt not_active Application Discontinuation
- 1995-03-27 HU HU9602749A patent/HUT76496A/hu unknown
- 1995-03-27 JP JP7526043A patent/JPH09511510A/ja not_active Ceased
- 1995-03-27 CN CN95192459A patent/CN1145068A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| US5861358A (en) | 1999-01-19 |
| DE4411913A1 (de) | 1995-10-12 |
| HU9602749D0 (en) | 1996-11-28 |
| EP0754179A1 (de) | 1997-01-22 |
| CA2187215A1 (en) | 1995-10-19 |
| HUT76496A (en) | 1997-09-29 |
| JPH09511510A (ja) | 1997-11-18 |
| WO1995027703A1 (de) | 1995-10-19 |
| AU2136595A (en) | 1995-10-30 |
| BR9507294A (pt) | 1997-10-07 |
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