CN1198159A - 磺酰基氨基(硫代)羰基化合物 - Google Patents
磺酰基氨基(硫代)羰基化合物 Download PDFInfo
- Publication number
- CN1198159A CN1198159A CN96196753.6A CN96196753A CN1198159A CN 1198159 A CN1198159 A CN 1198159A CN 96196753 A CN96196753 A CN 96196753A CN 1198159 A CN1198159 A CN 1198159A
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- China
- Prior art keywords
- amino
- essentially
- alkyl
- group
- perhaps
- Prior art date
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- -1 sulphonylamino(thio) carbonyl Chemical class 0.000 title claims abstract description 347
- 230000002363 herbicidal effect Effects 0.000 title claims description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 90
- 125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 53
- 238000000034 method Methods 0.000 claims abstract description 46
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 40
- 239000001301 oxygen Substances 0.000 claims abstract description 38
- 239000001257 hydrogen Substances 0.000 claims abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 27
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 24
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 24
- 150000002431 hydrogen Chemical class 0.000 claims abstract description 16
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 12
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 239000005864 Sulphur Substances 0.000 claims abstract description 10
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 10
- 150000003839 salts Chemical class 0.000 claims abstract description 10
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 7
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 6
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 5
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims abstract description 5
- 239000000460 chlorine Substances 0.000 claims description 98
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 25
- 241000196324 Embryophyta Species 0.000 claims description 24
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 22
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
- 229910052794 bromium Inorganic materials 0.000 claims description 22
- 229910052801 chlorine Inorganic materials 0.000 claims description 22
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 22
- 239000000203 mixture Substances 0.000 claims description 21
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 150000001345 alkine derivatives Chemical group 0.000 claims description 18
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 18
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 16
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 16
- 239000002253 acid Substances 0.000 claims description 15
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 14
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 12
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 12
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 12
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 11
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 10
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims description 10
- ZHNUHDYFZUAESO-UHFFFAOYSA-N formamide Substances NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims description 10
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 9
- 150000001728 carbonyl compounds Chemical class 0.000 claims description 9
- TWBIDQDUOXHFSN-UHFFFAOYSA-N C[CH]C=O Chemical compound C[CH]C=O TWBIDQDUOXHFSN-UHFFFAOYSA-N 0.000 claims description 8
- 125000004429 atom Chemical group 0.000 claims description 8
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 8
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 6
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 5
- 125000004104 aryloxy 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
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 5
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 5
- SMDGVPQREIZILS-UHFFFAOYSA-N $l^{1}-oxidanylmethylbenzene Chemical compound [O]CC1=CC=CC=C1 SMDGVPQREIZILS-UHFFFAOYSA-N 0.000 claims description 4
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- NPDLYUOYAGBHFB-WDSKDSINSA-N Asn-Arg Chemical group NC(=O)C[C@H](N)C(=O)N[C@H](C(O)=O)CCCN=C(N)N NPDLYUOYAGBHFB-WDSKDSINSA-N 0.000 claims description 4
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 4
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 4
- 125000000319 biphenyl-4-yl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims description 4
- 125000006309 butyl amino group Chemical group 0.000 claims description 4
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 4
- 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 4
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 4
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 4
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 claims description 4
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 3
- 150000003863 ammonium salts Chemical class 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 230000012010 growth Effects 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- UJGVUACWGCQEAO-UHFFFAOYSA-N 1-ethylaziridine Chemical compound CCN1CC1 UJGVUACWGCQEAO-UHFFFAOYSA-N 0.000 claims description 2
- LGUDIRINVIYGGY-UHFFFAOYSA-N C(C)(CC)OOC=CC Chemical compound C(C)(CC)OOC=CC LGUDIRINVIYGGY-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 2
- NRAINUFKKPBZQY-UHFFFAOYSA-N [O]C1CC1 Chemical compound [O]C1CC1 NRAINUFKKPBZQY-UHFFFAOYSA-N 0.000 claims description 2
- GYAPJISEIGCPQO-UHFFFAOYSA-N [O]C1CCC1 Chemical compound [O]C1CCC1 GYAPJISEIGCPQO-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 2
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 2
- 125000005108 alkenylthio group Chemical group 0.000 claims description 2
- 125000004647 alkyl sulfenyl group Chemical group 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- IYABWNGZIDDRAK-UHFFFAOYSA-N allene Chemical compound C=C=C IYABWNGZIDDRAK-UHFFFAOYSA-N 0.000 claims description 2
- 229910052728 basic metal Inorganic materials 0.000 claims description 2
- 150000003818 basic metals Chemical class 0.000 claims description 2
- 150000001555 benzenes Chemical class 0.000 claims description 2
- 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 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- 125000000596 cyclohexenyl group Chemical group C1(=CCCCC1)* 0.000 claims description 2
- 125000002433 cyclopentenyl group Chemical group C1(=CCCC1)* 0.000 claims description 2
- VCZIFQMEDXLHEA-UHFFFAOYSA-N cyclopentylperoxycyclohexane Chemical compound C1(CCCC1)OOC1CCCCC1 VCZIFQMEDXLHEA-UHFFFAOYSA-N 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
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 2
- 125000004914 dipropylamino group Chemical group C(CC)N(CCC)* 0.000 claims description 2
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical compound FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 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
- 239000000376 reactant Substances 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical compound NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 claims description 2
- 230000019086 sulfide ion homeostasis Effects 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 230000008635 plant growth Effects 0.000 claims 1
- 229920001228 polyisocyanate Polymers 0.000 claims 1
- 239000005056 polyisocyanate Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 abstract description 4
- 239000004009 herbicide Substances 0.000 abstract description 2
- HMAZJTPKLYHRBT-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)sulfonyl-1,5-dimethylpyrazole-3-carboxamide Chemical compound COC1=CC=C(OC)C(S(=O)(=O)NC(=O)C2=NN(C)C(C)=C2)=C1 HMAZJTPKLYHRBT-UHFFFAOYSA-N 0.000 abstract description 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 3
- 125000000547 substituted alkyl group Chemical group 0.000 abstract 2
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 abstract 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- PZSBGXZHOBIBPI-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)sulfonyl-3,4-diethoxy-5-oxo-1,2,4-triazole-1-carboxamide Chemical compound O=C1N(OCC)C(OCC)=NN1C(=O)NS(=O)(=O)C1=CC(OC)=CC=C1OC PZSBGXZHOBIBPI-UHFFFAOYSA-N 0.000 abstract 1
- RBTQQRAQCLQQJE-UHFFFAOYSA-N n-(2,5-dimethoxyphenyl)sulfonyl-3,4-dimethoxy-5-oxo-1,2,4-triazole-1-carboxamide Chemical compound O=C1N(OC)C(OC)=NN1C(=O)NS(=O)(=O)C1=CC(OC)=CC=C1OC RBTQQRAQCLQQJE-UHFFFAOYSA-N 0.000 abstract 1
- 239000002585 base Substances 0.000 description 49
- 238000002360 preparation method Methods 0.000 description 42
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 23
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 23
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 239000003999 initiator Substances 0.000 description 15
- 238000005160 1H NMR spectroscopy Methods 0.000 description 14
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
- 239000000243 solution Substances 0.000 description 14
- 239000002994 raw material Substances 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 230000000694 effects Effects 0.000 description 11
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 238000000967 suction filtration Methods 0.000 description 8
- 239000000706 filtrate 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
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000012948 isocyanate Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000002689 soil Substances 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 235000005781 Avena Nutrition 0.000 description 4
- 244000075850 Avena orientalis Species 0.000 description 4
- 244000025254 Cannabis sativa Species 0.000 description 4
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 4
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 4
- 241000209117 Panicum Species 0.000 description 4
- 235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 4
- 235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 4
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 4
- 241000207763 Solanum Species 0.000 description 4
- 235000002634 Solanum Nutrition 0.000 description 4
- 241000209072 Sorghum Species 0.000 description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 238000001914 filtration Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
- 235000015320 potassium carbonate Nutrition 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
- 229910052938 sodium sulfate Inorganic materials 0.000 description 4
- 235000011152 sodium sulphate Nutrition 0.000 description 4
- ICLNDJFVFRPPNI-UHFFFAOYSA-N 2-methyl-6-propan-2-yloxyaniline Chemical compound CC(C)OC1=CC=CC(C)=C1N ICLNDJFVFRPPNI-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- 230000008029 eradication Effects 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 239000008187 granular material Substances 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000005204 segregation Methods 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 3
- 229940124530 sulfonamide Drugs 0.000 description 3
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 3
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- UNAHYJYOSSSJHH-UHFFFAOYSA-N oryzalin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(N)(=O)=O)C=C1[N+]([O-])=O UNAHYJYOSSSJHH-UHFFFAOYSA-N 0.000 description 1
- NDLPOXTZKUMGOV-UHFFFAOYSA-N oxo(oxoferriooxy)iron hydrate Chemical compound O.O=[Fe]O[Fe]=O NDLPOXTZKUMGOV-UHFFFAOYSA-N 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- 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
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000001556 precipitation Methods 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
- YORCIIVHUBAYBQ-UHFFFAOYSA-N propargyl bromide Chemical compound BrCC#C YORCIIVHUBAYBQ-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
- 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
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 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
- 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
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 239000012047 saturated solution Substances 0.000 description 1
- 238000012216 screening Methods 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
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 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
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000004575 stone Substances 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 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
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 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 class 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 class 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
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 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
- AISMNBXOJRHCIA-UHFFFAOYSA-N trimethylazanium;bromide Chemical compound Br.CN(C)C AISMNBXOJRHCIA-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
Classifications
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- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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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
- 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
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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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
- A01N43/82—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 three ring hetero atoms
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- 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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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C249/00—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton
- C07C249/04—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes
- C07C249/12—Preparation of compounds containing nitrogen atoms doubly-bound to a carbon skeleton of oximes by reactions not involving the formation of oxyimino groups
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- C—CHEMISTRY; METALLURGY
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- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/78—Halides of sulfonic acids
- C07C309/86—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
- C07C309/87—Halides of sulfonic acids having halosulfonyl groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton containing singly-bound oxygen atoms bound to the carbon skeleton
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- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/22—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms
- C07C311/29—Sulfonamides, the carbon skeleton of the acid part being further substituted by singly-bound oxygen atoms having the sulfur atom of at least one of the sulfonamide groups bound to a carbon atom of a six-membered aromatic ring
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- C07C311/65—N-sulfonylisocyanates
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- C07C331/00—Derivatives of thiocyanic acid or of isothiocyanic acid
- C07C331/16—Isothiocyanates
- C07C331/32—Isothiocyanates having isothiocyanate groups acylated
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- 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
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- 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
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- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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Abstract
本发明涉及式(Ⅰ)新的磺酰基氨基(硫代)羰基化合物,其中A代表一个单键,氧原子,硫原子或N－R基团,其中R代表氢、烷基、链烯基、炔烃基或环烷基,Q代表氧原子或硫原子,R1代表氢或甲酰基或者代表在各种情况下可有可无地被取代的烷基、链烯基、炔烃基、烷基羰基、烷氧基羰基、烷基磺酰基、环烷基、环烷基羰基或环烷基磺酰基,R2代表氰基或卤原子或者代表在各种情况下可有可无地被取代的烷基、链烯基、炔烃基、烷氧基、链烯基氧基或炔烃基氧基,和R3代表在各种情况下可有可无地被取代的五元杂环基,五元杂环五个原子中至少有一个原子是氧、硫或氮,而且其它成环原子中还可以有1至3个原子可以是氮,和式(Ⅰ)化合物的盐,排除先前已知的化合物4,5－二甲氧基－2－(2,5－二甲氧基－苯基磺酰基氨基羰基)－2,4－二氢－3H－1,2,4－三唑－3－酮、4,5－二乙氧基－2－(2,5－二甲氧基—苯基磺酰基氨基羰基)－2,4－二氢－3H－1,2,4－三唑－3－酮和N－(2,5－二甲氧基－苯基磺酰基)－1,5－二甲基－1H－吡唑－3－甲酰胺。也涉及该新化合物的制备方法和新的中间体,以及涉及其作为除草剂的用途。
Description
本发明涉及新的磺酰基氨基(硫代)羰基化合物，涉及其制备的几种方法和新的中间体，以及涉及其作为除草剂的用途。
已知一些磺酰基氨基羰基化合物，例如化合物4，5-二甲氧基-2-(2-甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二甲氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮和N-(2，5-二甲氧基-苯基磺酰基)-1，5-二甲基-1H-吡唑-3-甲酰胺具有除草性能(参见EP-341489、EP-422469、EP-425948、EP-431291、EP-507171、EP-534266、DE-4029753)。但是这些化合物的作用并不是在各方面都令人满意。
现在发现通式(I)新的磺酰基氨基(硫代)羰基化合物，
其中A 代表一个单键，氧原子，硫原子或N-R基团，其中R代表氢、烷基、链烯基、炔烃基或环烷基，Q 代表氧原子或硫原子，R1 代表氢或甲酰基或者代表在各种情况下可有可无地被取代的烷基、链烯基、炔烃基、烷基羰基、烷氧基羰基、烷基磺酰基、环烷基、环烷基羰基或环烷基磺酰基，R2 代表氰基或卤原子或者代表在各种情况下可有可无地被取代的烷基、链烯基、炔烃基、烷氧基、链烯基氧基或炔烃基氧基，和R3 代表在各种情况下可有可无地被取代的五元杂环基，五元杂环五个原子中至少有一个原子是氧、硫或氮，而且其它成环原子中还可以有1至3个原子可以是氮，和式(I)化合物的盐，排除先前已知的化合物4，5-二甲氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮和N-(2，5-二甲氧基-苯基磺酰基)-1，5-二甲基-1H-吡唑-3-甲酰胺。
如果进行下面的反应，则会得到通式(I)新的磺酰基氨基(硫代)羰基化合物：(a)在可有可无地存在一种酸受体和可有可无地存在一种稀释剂下，通式(II)氨基磺酰基化合物
其中A、R1和R2具有上面给出的定义，与通式(III)(硫代)羧酸衍生物反应
其中Q和R3具有上面给出的定义，Z 代表卤原子、烷氧基、芳基氧基或芳基烷氧基，或者(b)可有可无地存在一种反应助剂和可有可无地存在一种稀释剂下，通式(IV)磺酰基异(硫代)氰酸盐
其中A、Q、R1和R2具有上面给出的定义，与通式(V)杂环反应，
H-R3 (V)其中R3具有上面给出的定义，或者(c)可有可无地存在一种反应助剂和可有可无地存在一种稀释剂下，通式(VI)氯代磺酰基化合物其中A、R1和R2具有上文给出的定义，与通式(V)杂环
H-R3 (V)其中R3具有上文给出的定义和通式(VII)金属(硫代)氰酸盐反应
MQCN (VII)其中Q 具有上文给出的定义，和M 代表碱金属或碱土金属等同物，或者(d)可有可无地存在一种酸受体和可有可无地存在一种稀释剂下，通式(VI)氯代磺酰基化合物其中A、R1和R2具有上面给出的定义，与通式(VIII)(硫代)甲酰胺反应其中Q和R3具有上面给出的定义，或者(e)可有可无地存在一种酸受体和可有可无地存在一种稀释剂下，通式(IX)磺酰基氨基(硫代)羰基化合物，
其中A、Q、R1和R2具有上面给出的定义，和Z 代表卤原子、烷氧基、芳基氧基或芳基烷氧基，与通式(V)杂环反应
H-R3 (V)其中R3具有上面给出的定义，或者(f)可有可无地存在一种稀释剂，通式(V)杂环
H-R3 (V)其中R3具有上面给出的定义，与氯代磺酰基异(硫代)氰酸盐反应，而且该反应生成的加成物在可有可无地存在一种酸受体和可有可无地存在一种稀释剂下就地与通式(X)苯衍生物反应
其中A、R1和R2具有上面给出的定义，而且，如果需要，可以通过常规方法将通过方法(a)、(b)、(c)、(d)、(e)或(f)得到的式(I)化合物转化成盐。
通式(I)新的磺酰基氨基(硫代)羰基化合物具有强的除草活性。
本发明优选涉及式(I)化合物，其中A 代表一个单键、氧原子、硫原子或N-R基团，其中R代表氢原子、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔烃基或C3-C6-环烷基，Q 代表氧原子或硫原子，R1 代表氢或甲酰基或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-、苯基-或C1-C4-烷氧基取代的各种情况下最多有6个碳原子的烷基、链烯基、炔烃基、烷基羰基、烷氧基羰基或烷基磺酰基，或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-或C1-C4-烷基取代的C3-C6-环烷基、C3-C6-环烷基羰基或C3-C6-环烷基磺酰基，R2代表氰基、氟、氯或溴，或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-或C1-C4-烷氧基取代的各种情况下最多有6个碳原子的烷基、链烯基、炔烃基、烷氧基，链烯基氧基或炔烃基氧基，和R3代表各种情况下可有可无地被取代的下式杂环基，
其中：Q1、Q2和Q3各自代表氧原子或硫原子，和R4代表氢、羟基、氨基或氰基，或者代表C2-C10-亚烷基氨基，或代表可有可无地被氟-、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，或者代表在各种情况下可有可无地被氟-、氯-、和/或溴取代的C2-C6-链烯基或C2-C6-炔烃基，或代表各种情况下可有可无地被氟-、氯-、溴-、氰基-、C1-C4-烷氧基或C1-C4-烷氧基羰基取代的C1-C6-烷氧基、C1-C6-烷基氨基或C1-C6-烷基羰基氨基，或者代表C3-C6-链烯氧基，或者代表二(C1-C4-烷基)-氨基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、氰基-和/或C1-C4-烷基取代的C3-C6-环烷基、C3-C6-环烷基氨基或C3-C6-环烷基-C1-C4-烷基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、氰基-、硝基-、C1-C4-烷基-、三氟甲基-和/或C1-C4-烷氧基取代的苯基，苯基氨基或苯基-C1-C4-烷基，R5代表氢、羟基、巯基、氨基、氰基、氟、氯、溴或碘，或者代表可有可无地被氟-、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，或者代表在各种情况下可有可无地被氟-、氯-、和/或溴-取代的C2-C6-链烯基或C2-C6-炔烃基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、C1-C4-烷氧基-或C1-C4-烷氧基羰基-取代的C1-C6-烷氧基、C1-C6-烷基硫基、C1-C6-烷基氨基或C1-C6-烷基羰基氨基，或者代表C3-C6-链烯基氧基、C3-C6-炔烃基氧基、C3-C6-链烯基硫基、C3-C6-炔烃基硫基、C3-C6-链烯基氨基或C3-C6-炔烃基氨基，或者代表二(C1-C4-烷基)-氨基，或者代表在各种情况下可有可无地被甲基-和/或乙基取代的氮丙啶子基、吡咯烷子基、哌啶子基或吗啉代，或者代表各种情况下可有可无地被氟-、氯-、溴-、氰基-和/或C1-C4-烷基取代的C3-C6-环烷基、C5-C6-环烯基、C3-C6-环烷基氧基、C3-C6-环烷基硫代、C3-C6-环烷基氨基、C3-C6-环烷基-C1-C4-烷基、C3-C6-环烷基-C1-C4-烷氧基、C3-C6-环烷基-C1-C4-烷基硫代或C3-C6-环烷基-C1-C4-烷基氨基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、氰基-、硝基-、C1-C4-烷基-、三氟甲基-、C1-C4-烷氧基-和/或C1-C4-烷氧基羰基取代的苯基、苯基-C1-C4-烷基、苯氧基、苯基C1-C4-烷氧基、苯基硫基、苯基-C1-C4-烷基硫基、苯基氨基或苯基-C1-C4-烷基氨基，或者R4和R5一起代表可有可无地支链化的具有3至11个碳原子的链烷烃双基，还有R6、R7和R8是相同的或不同的，并且代表氢、氰基、氟、氯或溴，或者代表在各种情况下可有可无地被氟-、氯-、溴-或C1-C4-烷氧基取代的、各种情况下最多有6个碳原子的烷基、链烯基、炔烃基、烷氧基、链烯基氧基、炔烃基氧基、烷基硫基、链烯基硫基、炔硫基、烷基亚磺酰基和烷基磺酰基，或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-或C1-C4-烷基取代的具有3至6个碳原子的环烷基，排除先前已知的化合物4，5-二甲氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮和N-(2，5-二甲氧基-苯基磺酰基)-1，5-二甲基-1H-吡唑-3-甲酰胺。
本发明还优选涉及其中A、Q、R1、R2和R3具有作为优选的给定定义的式(I)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、C5-或C6-环烷基-铵盐和二(C1-C2-烷基)-苄基铵盐。
本发明特别涉及式(I)化合物，其中A 代表一个单键、氧原子或N-R基团，其中R代表氢、甲基、乙基、正-或异-丙基、正-、异-或仲丁基、丙烯基、丁烯基、丙炔基、丁炔基、环丙基、环丁基、环戊基或环己基，Q 代表氧或硫，R1 代表氢或甲酰基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、甲氧基-或乙氧基-取代的甲基、乙基、正-或异-丙基、正-、异-或仲丁基、丙烯基、丁烯基、丙炔基、丁炔基、乙酰基、丙酰基、丁酰基、甲氧基羰基、乙氧基羰基、正-或异-丙氧基羰基、甲基磺酰基、乙基磺酰基、正-或异丙基磺酰基、正-、异-、仲-或叔丁基磺酰基，或者代表在各种情况下被氟-、氯-或甲基任选取代的环丙基、环丙基羰基或环丙基磺酰基，R2 代表氰基、氟、氯或溴，或代表各种情况下可有可无地被氟-、氯-、甲氧基-或乙氧基取代的甲基、乙基、正-或异-丙基、正-、异-或仲丁基、丙烯基、丁烯基、丙炔基、丁炔基、甲氧基、乙氧基、正-或异-丙氧基、正-、异-或仲丁氧基、丙烯基氧基、丁烯基氧基、丙炔基氧基或丁炔基氧基，和R3 代表在各种情况下可有可无地被取代的下式的杂环基，其中Q1、Q2和Q3各自代表氧原子或硫原子，和R4代表氢、羟基或氨基，或者代表C3-C8亚烷基氨基，或者代表在各种情况下可有可无地被氟-、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，或者代表在各种情况下可有可无地被氟-、氯-或溴取代的丙烯基、丁烯基、丙炔基或丁炔基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲氧基、乙氧基、正-或异-丙氧基、正-、异-、仲-或叔丁氧基、甲基氨基、乙基氨基、正-或异-丙基氨基、正-、异-、仲-或叔丁基氨基，或者代表丙烯基氧基或丁烯基氧基，或者代表二甲基氨基或二乙基氨基，或者代表在各种情况下可有可无地被氟-、氯-、甲基-和/或乙基取代的环丙基、环丁基、环戊基、环己基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、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在各种情况下可有可无地被氟-、氯-、甲基-、三氟甲基和/或甲氧基取代的苯基或苄基，R5 代表氢、羟基、巯基、氨基、氟、氯或溴，或者代表在各种情况下可有可无地被氟-、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，或者代表在各种情况下可有可无地被氟-、氯-或溴取代的乙烯基、丙烯基、丁烯基、丙炔基或丁炔基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲氧基、乙氧基、正-或异-丙氧基、正-、异-、仲-或叔丁氧基、甲基硫基、乙基硫基、正-或异丙基硫基、正-、异-、仲-或叔丁基硫基、甲基氨基、乙基氨基、正-或异-丙基氨基、正-、异-、仲-或叔丁基氨基，或者代表丙烯基氧基、丁烯基氧基、丙炔基氧基、丁炔基氧基、丙烯基硫基、丙二烯基硫基、丁烯基硫基、丙炔基硫基、丁炔基硫基、丙烯基氨基、丁烯基氨基、丙炔基氨基或丁炔基氨基，或者代表二甲基氨基、二乙基氨基或二丙基氨基，或者代表在各种情况下可有可无地被氟-、氯-、甲基-和/或乙基取代的环丙基、环丁基、环戊基、环己基、环戊烯基、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、环己基硫基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环丙基甲基硫基、环丁基甲基硫基、环戊基甲基硫基、环己基甲基硫基、环丙基甲基氨基、环丁基甲基氨基、环戊基甲基氨基或环己基甲基氨基，或者代表各种情况下可有可无地被氟-、氯-、甲基-、三氟甲基-、甲氧基-和/或甲氧基羰基取代的苯基、苄基、苯氧基、苄基氧基、苯基硫基、苄基硫基、苯基氨基或苄基氨基，或者R4和R5一起代表可有可无地支化的有3至11个碳原子的链烷烃双基，以及R6、R7和R8是相同的或不同的，并且代表氢、氰基、氟、氯或溴，或者代表在各种情况下可有可无地被氟-、氯-、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、丙烯基、丁烯基、丙炔基、丁炔基、甲氧基、乙氧基、正-或异-丙氧基、正-、异-、仲-或叔丁氧基、丙烯基氧基、丁烯基氧基、丙炔基氧基、丁炔基氧基、甲基硫基、乙基硫基、正-或异-丙基硫基、正-、异-、仲-或叔丁基硫基、丙烯基硫基、丁烯基硫基、丙炔基硫基、丁炔基硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基，或者代表环丙基，排除先前已在的化合物4，5-二甲氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮和N-(2，5-二甲氧基-苯基磺酰基)-1，5-二甲基-1H-吡唑-3-甲酰胺。
本发明化合物特别优选的组是下面式(I)化合物，其中A 代表一个单键，Q 代表氧原子或硫原子，R1 代表甲基、乙基、正-或异丙基，R2 代表在各种情况下在5或6-位上的氯或甲基，和R3 代表下式可有可无地被取代的三唑啉基
其中：Q1代表氧或硫，和R4代表各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲基、乙基、正-或异丙基，或代表丙烯基或丙炔基，或代表甲氧基、乙氧基、正-或异-丙氧基，或代表环丙基，和R5代表氢、氯或溴，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲基、乙基、正-或异-丙基，或者代表在各种情况下可有可无地被氟和/或氯取代的丙烯基或丙炔基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲氧基、乙氧基、正-或异-丙氧基、甲基硫基、乙基硫基、正-或异丙基硫基，或者代表丙烯基氧或环丙基。
上述列出的基团的定义，不管是一般定义还是优选范围中列出的定义，都不仅适用于式(I)终产物，也相应地适用于各制备中所需要的起始物和/或中间体。这些基团定义可以根据需要相互组合，因此包括所指出的优选范围之间的相互组合。
例如，使用2-氟-6-甲氧基-苯磺酰胺和5-乙氧基-4-甲基-2-苯氧羰基-2，4-二氢-3H-1，2，4-三唑-3-硫酮为起始物，本发明(a)反应过程可以通过下面的反应式详细说明：
例如，使用2-乙氧基-6-甲基-苯基磺酰基-异硫氰酸盐和5-乙基-4-甲氧基-2，4-二氢-3H-1，2，4-三唑-3-酮为起始物，本发明方法(b)的反应过程可以通过下面的反应式详细说明：
例如，使用2-甲氧基-3-甲基-苯磺酰氯、5-乙基硫基-4-甲氧基-2，4-二氢-3H-1，2，4-三唑-3-酮和氰酸钾为起始物，则本发明方法(c)的反应过程可以通过下面的反应式详细说明：
例如，使用2-乙氧基-4-氟-苯磺酰氯和5-甲基-1，2，4-噁二唑-3-甲酰胺为起始物，则本发明方法(d)反应过程可以通过下面反应式来详细说明：
例如，使用N-(2-氯-6-丙氧基-苯基磺酰基)-O-甲基-尿烷和4-甲基-5-甲基硫基-2，4-二氢-3H-1，2，4-三唑-3-酮为起始物，则本发明方法(e)的反应过程可以通过下面反应式来详细说明：
例如，使用5-氯-4-乙基-2，4-二氢-3H-1，2，4-三唑-3-酮和氯代磺酰基异氰酸盐和之后2-乙氧基-6-甲基苯胺为起始物，则本发明方法(f)的反应过程可以通过下面反应式来详细说明：
式(II)给出了在本发明制备式(I)化合物的方法(a)中要用作起始物的氨基磺酰基化合物的通式定义。在式(II)中，A、R1和R2优选或特别具有上文中已经指出的，与描述本发明制备的式(I)化合物相关的，分别作为优选或特别优选的A、R1和R2的那些定义。
式(II)的起始原料是已知的和/或可以用实质上已知的方法制备(参见EP 216504、DE 3208189、EP44807、EP 23422)。
文献中还未公开的，也是本发明目的的新的物质是通式(IIa)的磺酰胺，
其中A1 代表乙基、正-或异丙基、正-、异-、仲-或叔丁基、三氟甲基、氟代乙基、氯乙基、二氟乙基、三氟乙基、氯代三氟乙基、甲氧基乙基、乙氧基乙基、烯丙基、炔丙基或苄基，和A2 代表甲基、乙基、正-或异-丙基、正-、异-、仲-或叔丁基。
如果式(VIa)磺酰氯其中A1和A2具有上面给出的定义，可有可无地在一种稀释剂例如在水的存在下，在0℃和50℃之间的温度下与氨反应，则得到式(IIa)新的磺酰胺(参见制备各实施例)。
式(II)的起始原料一般也可以通过式(IIb)苯酚衍生物其中A和R2具有上面给出的定义与式(XI)烷基化试剂反应而获得，
X-R1 (XI)其中R1 具有上面给出的定义，X代表卤原子或R1-O-SO2-O-基团，反应条件是可有可无地存在一种酸受体，例如碳酸钾，和可有可无地存在一种稀释剂，例如甲苯，反应温度在10℃和150℃之间(参见制备实施例)。
需要作为母体的式(IIb)苯酚衍生物是已知的和/或可以用实质上已知的方法制备(参见EP 44807，Metallober flache〔MetalSurface〕-Angew。Elektrochemie 27(1973)，217-227，化学文摘79：86733；制备实施例)。
也需要用作母体的式(XI)烷基化试剂是已知的合成化学品。
式(III)给出了本发明制备式(I)化合物的方法(a)中也要被用作起始物的(硫代)羧酸衍生物的通式定义。在式(III)中。Q和R3优选或特别具有上面已经指明的，与描述本发明制备的式(I)化合物相关的分别作为优选或特别优选的Q和R3的定义；Z优选代表氟、氯、溴、C1-C4-烷氧基、苯氧基或苄基氧基，特别是代表氯、甲氧基、乙氧基或苯氧基。
式(III)的起始原料是已知的和/或可以由实质上已知的方法制备(参见EP 459244、EP341489、EP 422469、EP 425948、EP431291、EP 507171、EP 534266)。
式(IV)给出在本发明制备式(I)化合物的方法(b)中要被用作起始原料的磺酰基异(硫代)氰酸盐通式定义。在式(IV)中、A、Q、R1和R2优选或特别具有上面已经指明的，与描述本发明制备的式(I)化合物相关的，作为优选的或特别优选的A、Q、R1和R2的定义。
式(IV)的起始原料是已知的和/或可以用实质上已知的方法制备(参见EP 23422、EP 216504)。
文献中未公开过的，也是本发明目的的新的物质是通式(IVa)磺酰基异(硫代)氰酸盐
其中Q 代表氧或硫，A1 代表乙基、正-或异丙基、正-、异-、仲-或叔丁基、三氟甲基、氟乙基、氯乙基、二氟乙基、三氟乙基、氯代三氟乙基、甲氧基乙基、乙氧基乙基、烯丙基、炔丙基或苄基，和A2代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基。
如果上面的式(IIa)磺酰胺与碳酰氯或硫代碳酰氯在可有可无地存在异氰酸烷基酯例如异氰酸丁酯，可有可无地存在一种反应助剂，例如二氮杂双环[2.2.2]辛烷，并存在一种稀释剂例如甲苯、二甲苯或氯苯下，在80℃和150℃的温度下反应，反应完全后减压蒸馏掉挥发成份，则得到式(IVa)新的磺酰基异(硫代)氰酸盐。
式(V)给出了本发明制备式(I)化合物的方法(b)、(c)、(e)和(f)中也被用作起始物的杂环的通式定义。在式(V)中，R3优选或特别具有上面已经指明的，与描述本发明制备的式(I)化合物相关的作为优选或特别优选的R3的定义。
式V的起始原料是已知的和/或可以用实质上已知的方法制备(参见EP 341489、EP 422469、EP 425948、EP 431291、EP 507171、EP 534266)。
式(VI)给出了本发明制备式(I)化合物的方法(c)和(d)中用作起始物的氯代磺酰基化合物的通式定义。在式(VI)中， A、R1和R2优选或特别具有上面已经指明的，与描述本发明制备的式(I)化合物相关的作为优选或特别优选的A、R1和R2的定义。
式(VI)的起始原料是已知的和/或可以用实质上已知的方法制备(参见EP 511826、DE 3208189、EP 23422)。
文献中未公开的，也是本发明一个目的的新的物质是式(VIa)磺酰氯，
其中A1 代表乙基、正-或异丙基、正-、异-、仲或叔丁基、三氟甲基、氟乙基、氯乙基、二氟乙基、三氟乙基、氯代三氟乙基、甲氧基乙基、乙氧基乙基、烯丙基、炔丙基或苄基，A2 代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基。
如果式(XII)苯胺衍生物
其中A1和A2具有上面给出的定义，在存在盐酸条件下，在-10℃和+10℃之间的温度下，与碱金属亚硝酸盐例如亚硝酸钠反应，这样得到的重氮盐溶液在存在一种稀释剂，例如二氯甲烷或1，2-二氯乙烷，和存在一种催化剂，例如氯化亚铜(I)，且可有可无地存在另一种催化剂，例如十二烷基三甲基铵溴化物，在-10℃和+50℃之间的温度下，与二氧化硫反应，可得到式(VIa)新的磺酰氯化合物(参见制备实施例)。
需要用作母体的式(XII)苯胺衍生物是已知的和/或可以通过实质上已知的方法制备(参见EP 511826、US 4992091、EP 185128、DE2405479，制备实施例)。
上述新的式(IIa)、(IVa)和(VIa)苯磺酸衍生物可以用下面的式(XIII)综合定义：
E 代表-NH2，-N＝C＝Q或-Cl，其中Q 代表O或S，以及A1 代表乙基、正-或异丙基、正-、异-、仲-或叔丁基、三氟甲基、氟乙基、氯乙基、二氟乙基、三氟乙基、氯代三氟乙基、甲氧基乙基、乙氧基乙基、烯丙基、炔丙基或苄基，和A2 代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基。
式(VIII)给出了本发明制备式(I)化合物的方法(d)中用作起始物的(硫代)甲酰胺的通式定义。在式(VIII)中，Q和R3优选或特别优选具有上面已经指明的，与描述本发明制备的式(I)化合物相关的，作为优选或特别优选的Q和R3的定义。
式(VIII)的起始原料是已知的和/或可以用实质上已知的方法制备(参见EP 459244)。
式(IX)给出了本发明制备式(I)化合物的方法(e)中用作起始物的磺酰基氨基(硫代)羰基化合物的通式定义。在式(IX)中，A、Q、R1和R2优选或特别具有上文中已经指明的，与描述本发明制备的式(I)化合物相关的作为优选的或特别优选的A、Q、R1和R2的定义；Z优选代表氟、氯、溴、C1-C4-烷氧基、苯氧基或苄基氧基，特别是代表氯、甲氧基、乙氧基或苯氧基。
式(X)给出了本发明制备式(I)化合物的方法(f)中用作起始物的苯的衍生物的通式定义。在式(X)中，A、R1和R2优选或特别具有上面已经指明的，与描述本发明制备的式(I)化合物相关的，作为优选或特别优选的A、R1和R2的定义。
式(X)的起始原料是已知的和/或可以通过实质上已知的方法制备(参见EP 511826、US 4992091、EP 185128、DE 2405479，制备实施例)。
制备本发明式(I)新的化合物的本发明方法(a)、(b)、(c)、(d)、(e)和(f)优选使用稀释剂进行。本说明书中合适的稀释剂实际上是所有惰性有机溶剂。优选包括脂肪族和芳香族的，可有可无地被卤化的烃，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、二氯乙烷、氯仿、四氯甲烷、氯苯和邻二氯苯；醚，例如二乙醚和二丁醚、乙二醇二甲基醚和二乙二醇二甲基醚、四氢呋喃和二噁烷；酮，例如丙酮、甲乙酮、甲基异丙基酮和甲基异丁基酮；酯，例如乙酸甲酯和乙酸乙酯；腈，例如乙腈和丙腈；酰胺，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)、(d)、(e)和(f)中的反应助剂和/或作为酸受体，可以使用所有通常用于该类反应的酸结合剂。合适的实施例中优选的是碱金属氢氧化物，例如氢氧化钠和氢氧化钾，碱土金属氢氧化物，例如氢氧化钙，碱金属碳酸盐和醇酸盐，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、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]-十一-7-烯(DBU)和1，4-二氮杂双环-[2.2.2]-辛烷(DABCO)。
本发明方法(a)、(b)、(c)、(d)、(e)和(f)中的反应温度可以在相当宽的范围内变化。一般在-20℃和+150℃之间的温度下进行，优选在0℃和+100℃之间的温度下进行。
本发明方法(a)、(b)、(c)、(d)、(e)和(f)一般在大气压下进行。但是也可以在高压或低压下进行。
为了进行本发明(a)、(b)、(c)、(d)、(e)和(f)，各种情况下需要的起始物一般以大约等摩尔量使用，但是也可以在各种情况下以相当大的过量使用其中之一反应物，反应一般在一种合适的稀释剂中在存在一种酸受体下进行，反应混合物在具体所要求的温度下搅拌数小时。用常规方法在各种情况下在本发明方法(a)、(b)、(c)、(d)、(e)和(f)中进行后处理(参见制备实施例)。
如果需要，可以制备本发明通式(I)化合物的盐，这样的盐通过成盐的常规方法以简单方式获得，例如将式(I)化合物溶解或分散于合适的溶剂中，例如二氯甲烷、丙酮、叔丁基甲基醚或甲苯，并加入一种合适的碱。然后，如果需要，在长时间搅拌后，通过浓缩或抽滤而分离到盐。
本发明活性化合物可以用作脱叶剂，干燥剂，破坏阔叶植物的药剂，特别是作为除草剂。广义上来说，所谓杂草应该理解为在不期望其生长的地点生长的所有植物。本发明物质是以全除草剂还是以选择性除草剂作用主要取决于所使用的量。
例如，与下面的植物相关，可以使用本发明活性化合物：
双子叶杂草种类：芥属(Sinapis)、独行菜属(Lepidium)、猪殃殃属(Galium)、繁缕属(Stellaria)、母菊属(Matricaria)、春黄菊属(Anthemis)、辣子草(Galinsoga)、藜属(Chenopodium)、荨麻属(Urtica)、千里光属(Senecio)、苋属(Amaranthus)、马齿苋属(Portulaca)、苍耳属(Xanthium)、旋花属(Convolvulus)、甘薯属(Ipomoea)、蓼属(Polygonum)、田菁属(Sesbania)、豚草属(Ambrosia)、蓟属(Cirsium)、飞廉属(Carduus)、苦苣菜属(Sonchus)、茄属(Solanum)、蔊菜属(Rorippa)、水松叶属(Rotala)、母草属(Lindernia)、野芝麻属(Lamium)、婆婆纳属(Veronica)、苘麻属(Abutilon)、刺果(Emex)、曼陀罗属(Datura)、堇菜属(Viola)、鼬瓣花属(Galeopsis)、罂粟属(Papaver)、矢车菊属(Centaurea)、车轴草属(Trifolium)、毛莨属(Ranunculus)和蒲公英属(Taraxacum)。
双子叶作物种类：棉属(Gossypium)、Glycine、Beta、胡萝卜属(Daucus)、菜豆属(Phaseolus)、Pisum、茄属(Solanum)、亚麻属(Linum)、甘薯属(Ipomoea)、巢菜属(Vicia)、烟草属(Nicotiana)、番茄属(Lycopersicon)、花生属(Arachis)、芥属(Brassica)、莴苣属(Lactuca)、Cucumis和臭瓜属(Cucurbita)。
单子叶杂草种类：稗属(Echinochloa)、狗毛草属(Setaria)、黍属(Panicum)、马唐属(Digitaria)、梯牧草属(Phleum)、早熟禾属(Poa)、羊茅属(Festuca)、蟋蟀草属(Eleusine)、臂形草属(Brachiaria)、黑麦属(Lolium)、雀麦属(Bromus)、燕麦属(Avena)、莎草属(Cyperus)、蜀黍属(Sorghum)、冰草属(Agropyron)、Cynodon、雨久花属(Monochoria)、飘拂草属(Fimbristylis)、慈姑属(Sagittaria)、荸荠属(Eleocharis)、藨草属(Scirpus)、雀稗属(Paspalum)、Ischaemum、尖瓣花属(Sphenoclea)、龙爪茅属(Dactyloctenium)、翦股颖属(Agrostis)、看麦娘属(Alopecurus)和Apera。
单子叶作物种类：稻属(Oryza)、Zea、Triticum、大麦属(Hordeum)、燕麦属(Avena)、黑麦属(Scale)、蜀黍属(Sorghum)、黍属(Panicum)、甘蔗属(Saccharum)、波罗属(Ananas)、Asparagus和葱属(Allium)。
但是，本发明活性化合物的用途无论如何不受这些种类的限制，也以相同方式扩展到其它植物。
根据浓度，本发明化合物适于例如在工业领域和铁路枕木，轨道和有或没有种植树的广场全部杀死杂草。也就是说，本发明化合物可以用来杀灭长年生作物中的杂草，例如造林、装饰树种植、果园、葡萄园、柑桔园、坚果园、香蕉种植园、咖啡种植园、茶叶种植园、橡胶种植园、油棕种植园、可可种植园、软果种植园和蛇麻草田、草场和牧场，并用来选择性除灭年生作物中的杂草。
本发明式(I)化合物优选适于除单子叶和双子叶阔叶杂草，可以在出苗前或出苗后除草。当在土壤上和在植物地上部分使用时，这些化合物显示出强的除草活性和广谱作用。
活性化合物可以转化成常规制剂，例如溶液、乳剂、可湿粉剂、混悬剂、粉剂、粗粉剂、糊剂、可溶粉剂、颗粒剂、混悬-乳油，浸有活性化合物的天然和合成材料，非常细的聚合物质中的胶囊。
用已知方法制备这些制剂，例如将活性化合物与增充剂混合，所述增充剂是液体溶剂和/或固体载体，可有可无地使用表面活性剂，所述表面活性剂是乳化剂和/或分散剂和/或成泡剂。
在使用水作为增充剂的情况下，有机溶剂，例如，可以用作辅助溶剂。作为液体溶剂，合适的主要有：芳烃，如二甲苯、甲苯或烷基萘，氯化的芳烃和氯化的脂肪烃，例如氯苯、氯乙烯或二氯甲烷、脂肪烃，例如环己烷或石蜡，例如石油级分、矿物油和植物油，醇，例如丁醇或乙二醇，以及它们的醚类和酯类，酮，例如丙酮、甲乙酮、甲基异丁基酮或环己酮、强极性溶剂，例如二甲基甲酰胺和二甲亚砜，以及水。
作为固体载体合适的有：
例如铵盐和研细的天然矿物，例如高岭土、粘土、滑石、白垩、石英、硅镁土、蒙脱石或硅藻土，和研细的合成矿物，例如高度分散的硅石、矾土，和硅酸盐，作为适于颗粒剂的固体载体，合适的有：例如磨细的和筛分的天然岩石，例如方解石、大理石、浮石、海泡石和白云石，以及合成的无机粉和有机粉的颗粒，和有机材料的颗粒，例如木屑、椰子壳、玉米芯和烟草梗；作为乳化剂和/或起炮剂，合适的有：例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，例如烷基芳基聚乙二醇醚、磺酸烷基酯、硫酸烷基酯、磺酸芳基酯以及白蛋白水解产物；作为分散剂，合适的有：例如木素一亚磺酸废液和甲基纤维素。
制剂中可以使用粘合剂，例如羧甲基纤维素、粉末、颗粒或乳胶形式的天然的和合成的聚合物，例如阿拉伯树胶、聚乙烯醇，聚乙酸乙烯酯、以及天然磷脂，例如脑磷脂或卵磷脂，和合成的磷脂。其它的添加剂有矿物油和植物油。
可以使用着色剂，例如无机颜料，例如氧化铁、氧化钛和普鲁士蓝、和有机染料，例如茜素染料，偶氮染料和金属酞菁染料，和痕量营养成分，例如铁盐、锰盐、硼盐、铜盐、钴盐、钼盐和锌盐。
制剂中一般含有0.1至95％重量比的活性化合物，优选含有0.5至90％。
为了控制杂草，本发明活性化合物或者其制剂形式，也可以作为与已知的除草剂的混合物，完成制剂或可能的罐混制剂而被使用。
混合物中可能的成分是已知的除草剂，例如酰苯胺类，例如吡氟草胺和敌稗；芳基羧酸，例如二氯吡啶酸、dicamba和毒莠定；芳基氧基链烷酸，例如2，4-D、2，4-DB、2，4-DP、氟草烟、MCPA、MCPP和绿草定；芳基氧基-苯氧基-链烷酸酯，例如禾草灵、噁唑禾草灵、吡氟禾草灵、吡氟氯禾灵和喹禾灵；吖嗪酮(azinonea)，例如杀草敏和达草伏；氨基甲酸酯，例如氯苯胺灵、甜菜安、甜菜宁和苯胺灵；乙酰氯苯胺；例如甲草胺、乙草胺、丁草胺、吡草胺、丙草安、丙草胺和毒草胺；二硝基苯胺，例如安磺灵、二甲戊乐灵和氟乐灵；二苯醚类，例如三氟羧甲醚、甲羧除草醚、乙羧氟草醚、氟黄胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚；脲，例如绿麦隆、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，例如咪草烟、咪草酯、灭草烟和灭草喹；腈类，例如溴苯腈、敌草腈，碘苯腈；氧化乙酰胺类，例如苯噻草胺；磺酰脲类，例如amidosulphuron、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；氨基甲酸硫羟酯类，例如丁草特、灭草特、野燕畏、EPTC、禾草畏、草达灭、苄草丹、杀草丹和野燕畏；三嗪类，例如莠去津、氰草津、西玛津、西玛通、特丁净和terbutylazine；三嗪酮类，例如环嗪酮、苯嗪草酮，嗪草酮；其它，例如杀草强、呋草黄、灭草松、环庚草醚、异噁草酮、二氯吡啶酸、双苯唑快、氟硫草定、乙呋草黄、氟咯草酮、草胺膦、草甘膦、isoxaben、哒草特、二氯喹啉酸、喹草酸、草硫磷和灭草环。
也可能是与其它活性化合物的混合物，所述其它已知活性化合物是例如杀真菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物营养剂和改善土壤结构的试剂。
活性化合物可以以其制剂的形式或以由其进一步稀释而制备的使用形式来使用，例如即用型溶液、混悬剂、乳剂、粉剂、糊剂和颗粒剂，以常规方式使用，例如通过灌溉、撒播、雾化、喷施。
本发明活性化合物可以在植物出苗前或出苗后施用。也可以在耕种前加到土壤中。
使用的活性化合物的量可以在一个基本范围内变化。主要取决于所期望作用的性质。一般情况下，使用的量是每公顷土壤表面施用1至10kg活性化合物，优选为5g-5kg/ha。
本发明活性化合物的制备和应用可以由下面的实施例看出。制备实施例：实施例1
(方法(a))
2.5g(10mmol)5-乙氧基-4-甲基-2-苯氧基羰基-2，4-二氢-3H-1，2，4-三唑-3-酮，2.3g(10mmol)2-异丙氧基-6-甲基-苯磺酰胺，1.5g(10mmol)二氮杂双环[5.4.0]-十一碳-7-烯(DBU)和50ml乙腈的混合物在20℃搅拌5小时。然后在水泵抽真空下浓缩，残余物与50ml 1N盐酸搅拌，将混合物抽滤，滤出的产物与二乙醚搅拌，再次吸滤混合物。
得到2.4g(理论值60％)5-乙氧基-4-甲基-2-(2-异丙氧基-6-甲基-苯基磺酰基-氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点155℃。实施例2(方法(c))
1.7g(10mmol)4-甲基-5-炔丙基硫基-2，4-二氢-3H-1，2，4-三唑-3-酮，1.3g(20mmol)氰酸钠，2.5g(10mmol)2-甲基-6-正丙氧基-苯磺酰氯和50ml乙腈混合物回流下加热3小时。之后，水泵抽真空浓缩，残余物与1N盐酸搅拌，每次用50ml二氯甲烷将混合物萃取三次。浓缩合并的有机萃取液，残余物溶解于异丙醇，抽滤离析结晶产物。
得到2.2g(理论值52％)4-甲基-5-炔丙基硫基-2-(2-甲基-6-正丙氧基-苯基磺酰基-氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点151℃。实施例3(万法(d))
3.2g(25mmol)5-甲基-1，2，4-噁二唑-3-甲酰胺，4.2g(75mmol)氢氧化钾(粉末)和200ml二噁烷混合物在60℃下搅拌30分钟。然后在水泵抽真空下将其浓缩至大约其一半体积，在大约20℃滴加7g(30mmol)2-乙氧基-6-甲基-苯磺酰氯的10ml二噁烷溶液。然后将反应混合物在20℃搅拌大约15小时以上。之后，水泵抽真空浓缩，残余物与50ml 1N盐酸搅拌，吸滤离析结晶产物。得到4.0g(理论值49％)N-(2-乙氧基-6-甲基-苯基磺酰基)-5-甲基-1，2，4-噁二唑-3-甲酰胺，熔点168℃。实施例4
(方法(f))
向冷却到5℃的50ml二氯甲烷中1.4g(10mmol)5-乙氧基-4-甲基-2，4-二氢-3H-1，2，4-三唑-3-酮的溶液中加入1.7g(12mmol)氯代磺酰基异氰酸盐，然后同样在5℃下滴加10ml二氯甲烷中1.5g(10mmol)2-乙氧基-6-甲基-苯胺和1.0g(10mmol)三乙胺的溶液。之后，反应混合物在大约20℃下搅拌15小时。接着加入100ml 1N盐酸，充分搅拌后，分离有机相，用硫酸钠干燥并过滤。水泵真空浓缩滤液，残余物溶解于异丙醇中，抽滤离析结晶产物。
得到1.8g(理论值45％)5-乙氧基-4-甲基-2-(2-乙氧基-6-甲基-苯基氨基磺酰基-氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点147℃。
类似于实施例1至4，并根据本发明制备方法概括性描述，也可以，例如，制备下面表1中列出的式(I)化合物。
表1：式(I)化合物的实施例实施例号A Q R1 (位置) R3
R2 熔点(℃)5 - O n-C3H7 (6-)CH3 
1176 - O C2H5 (6-)Cl
1567 - O C2H5 (6-)CH3 1108 - O C2H5 (6-)CH3 1419 - O C2H5 (6-)CH3 
162
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)10 - O n-C3H7 (6-)CH3 
12611 - O n-C3H7 (6-)CH3 
15012 - O n-C3H7 (6-)CH3 12913 - O CH3 (6-)CH3 
15314 - O CH3 (6-)CH3 
167
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)15 - O CH3 (6-)CH3 16716 - O i-C3H7 (6-)CH3 
12517 - O i-C3H7 (6-)CH3 13118 - O C2H5 (5-)CH3 
22219 - O C2H5 (5-)CH3 
139
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)20 - O C2H5 (4-)CH3 18921 - O C2H5 (5-)CH3 13122 - O -C2H4- (6-)CH3
OC2H5
11823 - O -CH2CH2Cl (6-)CH3
13724 - O -CH2CH2Cl (6-)CH3
149
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)25 - O i-C3H7 (5-)CH3 
12526 - O i-C3H7 (5-)CH3 
14027 - O n-C3H7 (5-)CH3 
11928 - O n-C3H7 (5-)CH3 
13429 - O n-C3H7 (5-)CH3 110
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)30 - O C2H5 (6-)CH3 
10831 - O C2H5 (6-)CH3 17332 - O C2H5 (6-)CH3 
11933 - O C2H5 (6-)CH3 12134 - O C2H5 (6-)CH3 109
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)35 - O C2H5 (6-)CH3 
11136 - O n-C3H7 (6-)CH3 9137 - O n-C3H7 (6-)CH3 13038 - O n-C3H7 (6-)CH3 12639 - O n-C3H7 (6-)CH3 101
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)40 - O n-C3H7 (6-)CH3 
15241 - O n-C3H7 (6-)CH3 10042 - O n-C3H7 (6-)CH3 12043 - O n-C3H7 (6-)CH3 
11744 - O n-C3H7 (6-)CH3 
126
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)45 - O n-C3H7 (6-)CH3 
11346 - O i-C3H7 (6-)CH3 
13047 - O i-C3H7 (6-)CH3 
13948 - O i-C3H7 (6-)CH3 12149 - O i-C3H7 (6-)CH3 119
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)50 - O i-C3H7 (6-)CH3 
12851 - O i-C3H7 (6-)CH3 
13452 - O i-C3H7 (6-)CH3 
13053 - O i-C3H7 (6-)CH3 
11754 - O i-C3H7 (6-)CH3 134
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)55 - O i-C3H7 (6-)CH3 
14156 - O i-C3H7 (6-)CH3 
13257 - O i-C3H7 (6-)CH3 
16658 - O i-C3H7 (6-)CH3 
11859 - O i-C3H7 (6-)CH3 
150
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)60 - O i-C3H7 (6-)CH3 14461 - O i-C3H7 (6-)CH3 
17062 - O i-C3H7 (6-)CH3 12063 - O n-C3H7 (6-)CH3 
12464 - O n-C3H7 (6-)CH3 
12565 - O n-C3H7 (6-)CH3 
116实施例号A Q R1 (位置) R3
R2 熔点(℃)66 - O n-C3H7 (6-)CH3 
15267 - O n-C3H7 (6-)CH3 
14368 - O C2H5 (6-)CH3 
16069 - O C2H5 (6-)CH3 13370 - O C2H5 (6-)CH3 97
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)71 - O C2H5 (6-)CH3 9672 - O C2H5 (6-)CH3 
15673 - O C2H5 (6-)CH3 14574 - O C2H5 (6-)CH3 12075 - O C2H5 (6-)CH3 
125
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)76 - O C2H5 (6-)CH3 
14077 - O H (6-)CH3 
8878 - O C2H5 (5-)CH3 
13079 - O n-C3H7 (6-)CH3 14180 - O n-C3H7 (6-)CH3 98
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)81 - O n-C3H7 (6-)CH3 14182 - O n-C3H7 (6-)CH3 10183 - O n-C3H7 (6-)CH3 
13684 - O n-C3H7 (6-)CH3 9685 - O n-C3H7 (6-)CH3 9086 - O n-C3H7 (6-)CH3 136
表1-续实施例号 A Q R1 (位置) R3
R2 熔点(℃)87 - O C2H5 (6-)CH3 
12288 - O C2H5 (6-)CH3 
15489 - O i-C3H7 (6-)CH3 13990 - O C2H5 (6-)CH3 
14291 - O C2H5 (6-)CH3 
153
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)92 - O C2H5 (6-)CH3 
14593 - O C2H5 (6-)CH3 
13294 - O C2H5 (6-)CH3 14195 - O C2H5 (6-)CH3 
13096 - O CH3 (5-)CH3 
15697 - O CH3 (5-)CH3 
177
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)98 - O CH3 (4-)CH3 
11599 - O CH3 (4-)CH3 166100 - O CH3 (3-)CH3 162101 - O CH3 (3-)CH3 
143102 - O CH3 (3-)CH3 165
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)103 - O CHF2 (5-)CH3 176104 - O CHF2 (5-)CH3 119105 - O CHF2 (5-)CH3 126106 - O CHF2 (5-)CH3 
151107 - O CHF2 (5-)CH3 188
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)108 - O CHF2 (5-)CH3 137109 - O CHF2 (5-)CH3 117110 - O CHF2 (5-)CH3 155111 - O CHF2 (4-)CH3 152112 - O CHF2 (4-)CH3 
176113 - O CHF2 (4-)CH3 
108
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)114 - O CHF2 (6-)CH3 
163115 - O CHF2 (6-)CH3 
136116 - O CHF2 (6-)CH3 
118117 - O CHF2 (6-)CH3 
104118 - O CHF2 (5-)CH3 
98119 - O CHF2 (6-)CH3 128
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)120 - O CHF2 (6-)CH3 
165121 - O CHF2 (6-)CH3 
155122 - O CHF2 (6-)CH3 105123 - O CHF2 (6-)CH3 
81124 - O CHF2 (6-)CH3 
174
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)125 - O CHF2 (5-)CH3 
150126 - O CHF2 (6-)CH3 124127 - O CHF2 (6-)CH3 
200128 - S n-C3H7(6-)CH3 
160129 - S n-C3H7(6-)CH3 148130 - S C2H5 (6-)CH3 141
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)131 - S C2H5 (6-)CH3 125132 - S C2H5 (6-)CH3 
158133 - S i-C3H7 (6-)CH3 155134 - S n-C3H7 (6-)CH3 
153135 - S n-C3H7 (6-)CH3 
131
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)136 - S n-C3H7 (6-)CH3 
120137 - O C2H5 (6-)Cl
149138 - O C2H5 (6-)Cl
99139 - O CH3 (6-)Cl
176140 - O CH3 (6-)Cl
192
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)141 - O C2H5 (6-)Cl
144142 - O CH3 (6-)Cl
114143 - O C2H5 (6-)Cl
144144 - O CH3 (6-)Cl
157145 - O C2H5 (6-)Cl
142
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)146 - O CH3 (6-)Cl
191147 - O C2H5 (6-)Cl
116148 - O CH3 (6-)Cl
205149 - O CH3 (6-)Cl
147150 - O C2H5 (6-)Cl
117
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)151 - O CH3 (6-)Cl
149152 - O CH3 (6-)Cl
176153 - O CH3 (6-)Cl
150154 - O CH3 (6-)Cl
146155 - O CH3 (6-)Cl
191156 - O CH3 (6-)Cl
127
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)157 - O CH3 (6-)Cl
174158 - O n-C3H7 (6-)Cl
117159 - O n-C3H7 (6-)Cl
134160 - O n-C3H7 (6-)Cl
115161 - O n-C3H7 (6-)Cl
137
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)162 - O n-C3H7 (6-)Cl
125163 - O n-C3H7 (6-)Cl
119164 - O H (6-)Cl
147165 - O n-C3H7 (6-)Cl
148166 - O i-C3H7 (6-)Cl
143
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)167 - O i-C3H7 (6-)Cl
122168 - O CH3 (6-)Cl
165169 - O n-C3H7 (5-)Cl
154170 - O n-C3H7 (5-)Cl
136171 - O n-C3H7 (5-)Cl
128
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)172 - O CH3 (6-)Cl
143173 - O i-C3H7 (6-)Cl
136174 - O i-C3H7 (6-)Cl
121175 - O i-C3H7 (6-)Cl
158176 - O i-C3H7 (6-)Cl
141
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)177 - O i-C3H7 (6-)Cl
127178 - O i-C3H7 (6-)Cl
143179 - O i-C3H7 (6-)Cl
129180 - O i-C3H7 (6-)Cl
95181 - O n-C3H7 (6-)CH3 
74182 - O n-C3H7 (6-)CH3 
114
表1-续实施例号 A Q R1 (位置) R1
R2 熔点(℃)183 - O n-C3H7 (6-)CH3 140184 - O n-C3H7 (6-)CH3 
159185 - O n-C3H7 (6-)CH3 107186 - O n-C3H7 (6-)CH3 
132187 - O n-C3H7 (6-)CH3 
132
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)188 - O n-C3H7 (6-)CH3 
110189 - O CH3 (6-)CH3 
159190 - O n-C3H7 (6-)CH3 
138191 - O n-C3H7 (6-)CH3 
147192 - O n-C3H7 (6-)CH3 114193 - O n-C3H7 (6-)CH3 125
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)194 - O n-C3H7 (6-)CH3 126195 - O n-C3H7 (6-)CH3 151196 - O n-C3H7 (6-)CH3 121197 - O n-C3H7 (6-)CH3 147198 NH O C2H5 (6-)CH3 135199 - O i-C3H7 (6-)CH3 263(钠盐)
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)200 - O C2H5 (6-)CH3 
119201 - O C2H5 (6-)CH3 146202 - O C2H5 (6-)CH3 
128203 - O C2H5 (6-)CH3 186204 - O C2H5 (6-)CH3 239
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)205 - O C2H5 (6-)CH3 152206 - O C2H5 (6-)CH3 155207 - O C2H5 (6-)CH3 145(Na盐)208 - O i-C3H7 (6-)CH3 209(Na盐)209 - O C2H5 (6-)CH3 147(Na盐)
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)210 - O C2H5 (6-)CH3 140211 - O C2H5 (6-)CH3 
118212 - O C2H5 (6-)CH3 
156213 - O C2H5 (6-)CH3 110214 - O C2H5 (6-)CH3 
133215 - O i-C3H7 (6-)CH3 138
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)216 - O i-C3H7 (6-)CH3 
154217 - O i-C3H7 (6-)CH3 
149218 - O i-C3H7 (6-)CH3 112219 - O i-C3H7 (6-)CH3 
162220 - O i-C3H7 (6-)CH3 
99221 - O i-C3H7 (6-)CH3 
146
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)222 - O C2H5 (6-)CH3 
134223 - O CH3 (6-)CH3 
199224 - O CH3 (6-)CH3 
176225 - O CH3 (6-)CH3 145226 - O i-C3H7 (6-)CH3 
133
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)227 NH O n-C3H7 (5-)CH3 
127228 - O i-C3H7 (6-)CH3 
144229 - O i-C3H7 (6-)CH3 141230 - O i-C3H7 (6-)CH3 152231 - O i-C3H7 (6-)CH3 132232 - O i-C3H7 (6-)CH3 147
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)233 - O i-C3H7 (6-)CH3 
163234 - O i-C3H7 (6-)CH3 102235 - O C2H5 (6-)CH3 
121236 - O C2H5 (6-)CH3 
113237 - O C2H5 (6-)CH3 
145238 - O C2H5 (6-)CH3 137
表1-续实施例号A Q R1 (位置) R3No R2 熔点(℃)239 - O C2H5 (6-)CH3 172240 - O C2H5 (6-)CH3 
148241 - O C2H5 (6-)CH3 
157242 - O C2H5 (6-)CH3 
186243 NH O CH3 (6-)OCH3 
170244 - O CHF2 (5-)CH3
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)245 - S i-C3H7 (6-)CH3 
160246 - O CH3 (6-)CF3 205247 - S CH3 (6-)CF3 
92248 - S CH3 (6-)CF3 154249 - S CH3 (6-)CF3 157250 - O C2H5 (6-)CF3 176
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)251 - O n-C3H7-n (6-)CF3 166252 - O i-C3H7 (6-)CF3 
190253 - O CH3 (6-)CF3 203254 - O CH3 (6-)CF3 156255 - O CH3 (6-)CF3 
170256 - O CH3 (6-)CF3 
198
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)257 - O CH3 (6-)CF3 213258 - O CH3 (6-)CF3 
152259 - O CH3 (6-)CF3 
187260 - O CH3 (6-)CF3 210261 - O CH3 (6-)CF3 
172
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)262 - O CH3 (6-)CF3 
145263 - O CH3 (6-)CF3 136264 - O CH3 (6-)CF3 
153265 - O CH3 (6-)CF3 136266 - O CH3 (6-)CF3 210
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)267 - O CH3 (6-)CF3 147268 - O CH3 (6-)CF3 
169269 - O CH3 (6-)CF3 215270 - O CH3 (6-)CF3 
138271 - O CH3 (6-)CF3 
182272 - S C2H5 (6-)CF3 112
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)273 - S C2H5 (6-)CF3 167274 - S C2H5 (6-)CF3 
152275 - S n-C3H7 (6-)CF3 119276 - S n-C3H7 (6-)CF3 
157277 - S n-C3H7 (6-)CF3 154
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)278 - S i-C3H7 (6-)CF3 
137279 - S i-C3H7 (6-)CF3 
167280 - S i-C3H7 (6-)CF3 
137281 - O C2H5 (6-)CF3 
154282 - O C2H5 (6-)CF3 
160
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)283 - O C2H5 (6-)CF3 139284 - O C2H5 (6-)CF3 
134285 - O C2H5 (6-)CF3 142286 - O C2H5 (6-)CF3 120287 - O n-C3H7 (6-)CF3 
130
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)288 - O n-C3H7 (6-)CF3 
127289 - O n-C3H7 (6-)CF3 116290 - O n-C3H7 (6-)CF3 
126291 - O n-C3H7 (6-)CF3 113292 - O i-C3H7 (6-)CF3 
151
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)293 - O i-C3H7 (6-)CF3 
157294 - O i-C3H7 (6-)CF3 
171295 - O i-C3H7 (6-)CF3 137296 - O i-C3H7 (6-)CF3 
125297 - O n-C3H7 (6-)CF3 
109
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)298 - O n-C3H7 (6-)CF3 138299 - O i-C3H7 (6-)CF3 
130300 - O C2H5 (6-)CF3 165301 - O i-C3H7 (6-)CF3 148302 - O i-C3H7 (6-)CF3 
147
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)303 - O i-C3H7 (6-)CF3 
172304 - O i-C3H7 (6-)CF3 
147305 - O i-C3H7 (6-)CF3 136306 - O C2H5 (6-)CF3 
124307 - O C2H5 (6-)CF3 
98
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)308 - O C2H5 (6-)CF3 
125309 - O C2H5 (6-)CF3 
179310 - O C2H5 (6-)CF3 
153311 - O C2H5 (6-)CF3 171312 - O n-C3H7 (6-)CF3 
113
表1-续实施例号A Q R1 (位置) R3
R2 熔点(℃)313 - O n-C3H7 (6-)CF3 
138314 - O n-C3H7 (6-)CF3 110315 - O n-C3H7 (6-)CF3 
134316 - O i-C3H7 (6-)CF3 
167317 - O i-C3H7 (6-)CF3 
120
表1-续实施 A Q R1 (位置) R3例号 R2 熔点(℃)318 - O i-C3H7 (6-)CF3 117319 - O i-C3H7 (6-)CF3 160320 - O i-C3H7 (6-)CF3 154321 - O i-C3H7 (6-)CF3 159322 - O n-C3H7 (6-)CF3 141
表1-续实施 A Q R1 (位置) R3例号 R2 熔点(℃)323 - O i-C3H7 (6-)CF3 146324 - O i-C3H7 (6-)CF3 134325 - O i-C3H7 (6-)CF3 168326 - O CH3 (6-)C3H7-n
158327 - O CH3 (6-)C3H7-n
172
表1-续实施 A Q R1 (位置) R3例号 R2 熔点(℃)328 - O CH3 (6-)C3H7-n
147329 - O C2H5 (6-)CF3
66330 - O C2H5 (6-)CH3
134331 - O C2H5 (6-)CH3
149332 - O n-C3H7 (6-)CH3
114333 - O H (6-)Cl
102
表1-续实施 A Q R1 (位置) R3例号 R2 熔点(℃)334 - O H (6-)Cl
143335 - O
(6-)Cl
130336 - O -CH2C6H5 (6-)Cl
143337 - O -CH2C6H5 (6-)Cl
99338 - O -CH2C≡CH (6-)Cl
161
表1-续实施 A Q R1 (位置) R3例号 R2 熔点(℃)339 - O n-C3H7 (6-)CH3 
133340 - O H (6-)CH3 100341 - O H (6-)CH3 
147342 - O -CH2C6H5 (6-)CH3 157343 - O
(6-)CH3 
150
表1-续实施 A Q R1 (位置) R3例号 R2 熔点(℃)344 - O -CH2C≡CH (6-)CH3 
172345 - O i-C3H7 (6-)CH3 
263(Na盐)346 - O C2H5 (6-)CH3 
136347 - O i-C3H7 (6-)CH3 
113348 - O i-C3H7 (6-)CH3 
175349 - O i-C3H7 (6-)CH3 135
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)350 - O i-C3H7 (6-)CH3 78351 - O i-C3H7 (6-)CH3 
125352 - O i-C3H7 (6-)CH3 
140353 - O CH3 (6-)CH3 
161354 - O CH3 (6-)CH3 
142355 - O CH3 (6-)CH3 124
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)356 - O CH3 (6-)CH3 
153357 - O CH3 (6-)CH3 
170358 - O CH3 (6-)CH3 
116359 - O CH3 (6-)CH3 
120360 - O CH3 (5-)Cl
172
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)361 - O CH3 (5-)Cl
175362 - O CH3 (5-)Cl
192363 - O CH3 (5-)Cl
195364 - O CH3 (5-)Cl
174365 - O CH3 (5-)Cl
160366 - O CH3 (5-)Cl
214
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)367 - O CH3 (5-)Cl
185368 - O CH3 (5-)Cl
191369 NH O CH3 (6-)CH3 161370 NH O i-C3H7 (6-)CH3 132371 NH O CH3 (6-)OCH3 
151372 NH O CH3 (6-)CH3 161
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)373 NH O i-C3H7 (6-)CH3 
128374 NH O CH3 (6-)CH3 
140375 - S i-C3H7 (6-)CH3 108376 - O CHF2 (4-)CH3 131377 - O CH3 (6-)CF3 187378 - O CH3 (6-)CF3 154
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)379 - O CH3 (6-)C2H5 179380 - O CH3 (6-)C2H5 
178381 - O CH3 (6-)C2H5 167382 - O C2H5 (6-)C2H5 135383 - O C2H5 (6-)C2H5 146
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)384 - O C2H5 (6-)C2H5 174385 - O CH3 (6-)C2H5 130386 - O CH3 (6-)C2H5 
195387 - O CH3 (6-)C2H5 
183388 - O C2H5 (6-)C3H7-n
135
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)389 - O C2H5 (6-)C3H7-n
149390 - O CH3 (6-)C3H7-n
193391 - O CH3 (6-)C3H7-n
125392 - O CH3 (6-)C3H7-n
182393 - O C2H5 (6-)C3H7-n
120
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)394 - O C2H5 (6-)C3H7-n
158395 - O i-C3H7 (6-)CH3 
180396 - O n-C4H9 (6-)CH3 132397 - O n-C4H9 (6-)CH3 
143398 - O n-C4H9 (6-)CH3 
106
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)399 - O n-C4H9 (6-)CH3 
98400 - O n-C4H9 (6-)CH3 140401 - O CH3 (6-)CH3 147402 - O CH3 (6-)CH3 123403 - O CH3 (6-)CH3 185404 - O CH3 (6-)CH3 
154
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)405 NH O i-C3H7 (6-)CH3 
150406 - O C2H5 (6-)C2H5 
135407 - O C2H5 (6-)C2H5 
134408 - O C2H5 (6-)C2H5 
178409 - O C3H7-i (6-)C2H5 109
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)410 - O C3H7-i (6-)C2H5 125411 - O C3H7-i (6-)C2H5 
161412 - O C3H7-i (6-)C2H5 
114413 - O C3H7-i (6-)C2H5 142414 - O C3H7-i (6-)C2H5 
124415 - O CH3 (6-)C2H5 175(Na盐)
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)416 - O C2H5 (6-)C3H7-n
126417 - O C2H5 (6-)C3H7-n
121418 - O CH3 (6-)C3H7-n
109419 - O CH3 (6-)C3H7-n
145420 - O CH3 (6-)C3H7-n
126
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)421 - O CH3 (6-)C3H7-n
130422 - O CH3 (6-)C3H7-n
155423 - O CH3 (6-)C3H7-n
133424 - O CH3 (6-)C3H7-n
145425 - O -SO2CH3 (6-)CH3 
95426 - O -SO2CH3 (6-)CH3 
153
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)427 - O C4H9-n (6-)CH3 
154428 - O -CH2C≡CH (6-)CH3 167429 - O -CH2C≡CH (6-)CH3 170430 - O -CH2C≡CH (6-)CH3 153431 - O C4H9-i (6-)CH3 123432 - O C4H9-i (6-)CH3 
145
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)433 - O C4H9-i (6-)CH3 
143434 - O C3H7-i (6-)CH3 
138435 - O C3H7-i (6-)CH3 
161436 - O C3H7-i (6-)CH3 128437 - O C3H7-i (6-)CH3 177438 - O C3H7-i (6-)CH3 
165
表1-续实施 A Q R1 (位置) R3例号 R2 熔点(℃)439 - O CH3 (6-)CH3 
157440 - O CH3 (6-)CH3 
168441 - O CH3 (6-)CH3 164442 - O CH3 (6-)CH3 125443 - O CH3 (6-)CH3 
162444 - O CH3 (6-)OCH3 
154
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)445 - S CH3 (4-)C3H7-i
116446 - S CH3 (4-)C3H7-i
110447 - S CH3 (4-)C3H7-i
134448 - O CH3 (4-)C3H7-i
152449 - O CH3 (4-)C3H7-i
159450 - O CH3 (4-)C3H7-i
150
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)451 - O C2H5 (6-)OCH3 107452 - O C2H5 (6-)OCH3 
104453 - O C2H5 (6-)OCH3 
100454 - S C2H5 (6-)OCH3 
103455 - S C2H5 (6-)OCH3 
95
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)456 - S C2H5 (6-)OCH3 
105457 - O C2H5 (6-)OC2H5 
130458 - O C2H5 (6-)OC2H5 100459 - O C3H7-i (6-)OC3H7-i
114460 - O C3H7-i (6-)OC3H7-i
125461 - S C3H7-i (6-)OC3H7-i
143
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)462 - O C2H5 (6-)OC2H5 120463 - O -CF2CHFCl (6-)CH3
124464 - O -CF2CHFCl (6-)CH3
115465 - O -CF2CHFCl (6-)CH3
150466 - O CH3 (3-)CH3
178
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)467 - O CH3 (3-)Cl
188468 - O C2H5 (3-)Cl
159469 - O CH3 (3-)F
176470 - O C2H5 (6-)CF3 
124471 - O C2H5 (6-)CF3 
34
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)472 - O C2H5 (6-)CF3 68473 - O C3H7-i (6-)CF3 
41474 - O C2H5 (6-)CF3 127475 - O H (6-)CF3 
125476 - S C2H5 (6-)CH3 
214(Na salt)
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)477 NH O C2H5 (6-)CH3 
128478 NH O C2H5 (6-)CH3 148479 NH O C3H7-n (6-)CH3 127480 NH O C3H7-n (6-)CH3 57481 NH O C2H5 (6-)CH3 
125
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)482 NH O C3H7-n (6-)CH3 115483 NH O C3H7-n (6-)CH3 151484 NH O C2H5 (5-)CH3 132485 NH O C2H5 (5-)CH3 106486 NH O C2H5 (5-)CH3 163
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)487 NH O C2H5 (5-)CH3 
137488 - O C2H5 (6-)C3H7-i
166489 - O C2H5 (6-)C3H7-i
169490 - O C2H5 (6-)C3H7-i
130491 NH O
148
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)492 NH O
(6-)CH3 
138493 NH O
(6-)CH3 
147494 - O
(6-)CH3 124495 - O
(6-)CH3 152496 - O
(6-)CH3 141
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)497 - O
(6-)CH3 127498 - O
(6-)CH3 
144499 - O
(6-)CH3 107500 - O C3H7-n (6-)CH3 265(Na盐)501 - O C2H5 (6-)CH3 
269(Na盐)
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)502 - O C3H7-i (6-)CH3 
237(Na盐)503 - O
(6-)CH3 73504 - O C3H7-i (6-)CH3 220(Na盐)505 - O C3H7-i (6-)CH3 140506 - O C4H9-s (6-)CH3 120
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)507 - O C4H9-s (6-)CH3 117508 - O C4H9-s (6-)CH3 128509 - O C4H9-s (6-)CH3 232510 - O C4H9-s (6-)CH3 
268511 - O C4H9-s (6-)CH3 130
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)512 - O C4H9-s (6-)CH3 137513 - O C4H9-s (6-)CH3 
145514 - O C4H9-s (6-)CH3 164515 - O C4H9-s (6-)CH3 89516 - O C4H9-s (6-)CH3 86
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)517 - O C4H9-s (6-)CH3 
98518 - O C4H9-s (6-)CH3 122519 - O C4H9-s (6-)CH3 
135520 - O C2H5 (6-)CH3 142521 - O CH3 (6-)CH3 
157
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)522 - O C3H7-n (6-)CH3 
126523 - O C4H9-s (6-)CH3 
140524 - O C2H5 (6-)CH3 
164525 - O CH3 (6-)CH3 
166526 - O C3H7-n (6-)CH3 
145
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)527 - O CH3 (6-)CH3 239(Na盐)528 - O C3H7-n (6-)CH3 206(Na盐)529 - O C2H5 (6-)CH3 211(Na盐)530 - O CH3 (6-)C3H7-i
166531 - O CH3 (6-)C3H7-i
178
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)532 - O C3H7-i (6-)C3H7-i
131533 - O C3H7-i (6-)C3H7-i
130534 - O C3H7-i (6-)C3H7-i
133535 - O C3H7-i (6-)C3H7-i
116536 - O CH3 (6-)C3H7-i
192
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)537 - O CH3 (6-)C3H7-i
200538 - O CH3 (6-)C3H7-i
200539 - O CH3 (6-)C3H7-i
105540 - O CH3 (6-)C3H7-i
154541 - O CH3 (6-)C3H7-i
152
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)542 - O C3H7-n (6-)C3H7-i
132543 - O C3H7-n (6-)C3H7-i
129544 - O C3H7-n (6-)C3H7-i
179545 - O CH3 (6-)C3H7-i
174(Na盐)546 - O C3H7-n (6-)C3H7-i
158(Na盐)
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)547 - O C2H5 (6-)C3H7-i
200548 - O C2H5 (6-)C3H7-i
147549 - O C2H5 (6-)C3H7-i
149550 - O C2H5 (6-)C3H7-i
136551 - O C2H5 (6-)C3H7-i
134
表1-续
A Q R1 (位置) R3实施例号 R2 熔点(℃)552 - O C3H7-i (6-)C3H7-i
175553 - O C3H7-i (6-)C3H7-i
147554 - O C3H7-i (6-)C3H7-i
167555 - O C3H7-i (6-)C3H7-i
173556 - O C3H7-i (6-)CH3
188
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃557 NH O CH3 (6-)CH3 
181558 NH O C3H7-i (6-)CH3 
136559 - O CH3 (6-)CH3 241(Na盐)560 NH O C3H7-n (6-)CH3 
129561 - O C3H7-i (6-)OCH3 
94
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃562 - O C3H7-i (6-)OCH3
80563 - O C3H7-i (6-)OC2H5
68564 - O C3H7-i (6-)OC2H5
91565 - O C3H7-n (6-)OCH3
123566 - O C3H7-n (6-)OCH3
104
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃567 - O C3H7-n (6-)OCH3
90568 - S C3H7-n (6-)OCH3
107569 - O C3H7-n (6-)OCH3
70570 - O C2H5 (6-)OC2H5
132571 - S CH3 (6-)OCH3
150
表1-续
A O R1 (位置) R3实施例号 R2 熔点℃572 - O C2H5 (6-)OCH3
127573 - O C3H7-i (6-)OC3H7-i
110574 - S C3H7-n (6-)OC3H7-n
130575 - S C3H7-n (6-)OC3H7-n
135576 - S C3H7-n (6-)OC3H7-n
199(Na盐)
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃577 - O C2H5 (6-)OC2H5
173578 - O C2H5 (6-)OCH3
168579 - O C3H7-n (6-)OC3H7-n
125580 - O C3H7-n (6-)OC2H5
140581 - O C3H7-n (6-)OCH3
115
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃582 - S C3H7-n (6-)OCH3
111583 - S C3H7-n (6-)OCH3
138584 - O C3H7-i (6-)OCH3
127585 - O C3H7-i (6-)OC2H5
142586 - O C3H7-i (6-)OC2H5
143
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃587 - O C2H5 (6-)OCH3
104588 - O C2H5 (6-)OCH3
118589 - O C2H5 (6-)OCH3
70590 - O C2H5 (6-)OCH3
110591 - O C2H5 (6-)OCH3
156
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃592 - O C3H7-n (6-)OCH3
140593 - O C3H7-n (6-)OCH3
148594 - O C3H7-n (6-)OCH3
145595 - O C2H5 (6-)OCH3
120596 - O C2H5 (6-)OCH3
100
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃597 - O C2H5 (6-)OCH3
130598 - O C2H5 (6-)OCH3
103599 - O C2H5 (6-)OCH3
104600 - O C3H7-n (6-)OCH3
185601 - O C3H7-n (6-)OCH3
100
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃602 - O C3H7-n (6-)OCH3
138603 - O C3H7-n (6-)OCH3
106604 - O C3H7-n (6-)OCH3
112605 - O C3H7-n (6-)OCH3
140606 - O C3H7-n (6-)OCH3
160
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃607 - O C3H7-n (6-)OCH3
180608 - O C3H7-n (6-)OCH3
142609 - O C3H7-n (6-)OCH3
158610 - O C3H7-n (6-)OCH3
134611 - O C3H7-i (6-)OCH3
140
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃612 - O C3H7-i (6-)OCH3
142613 - O C3H7-i (6-)OCH3
148614 - O C3H7-i (6-)OCH3
146615 - O C3H7-i (6-)OCH3
104616 - O C2H5 (6-)OC2H5
123
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃617 - O C3H7-n (6-)OC3H7-n
123618 - O C3H7-n (6-)OC3H7-n
82619 - O C3H7-n (6-)OC3H7-n
81620 - S C3H7-n (6-)OC3H7-n
88621 - S C2H5 (6-)OCH3
145
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃622 - S C2H5 (6-)OC2H5
147623 - S C3H7-n (6-)OCH3
205624 - S C3H7-n (6-)OC2H5
202625 - S C3H7-i (6-)OC3H7-i
152626 - S C2H5 (6-)OC2H5
168
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃627 - S C3H7-n (6-)C3H7-n
145628 - S C3H7-n (6-)OCH3
158629 - S C3H7-i (6-)OC3H7-i
155630 - O C3H7-i (6-)OCH3
145631 - O C3H7-i (6-)OCH3
111
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃632 - O C3H7-i (6-)OCH3
122633 - O C3H7-i (6-)OCH3
171634 - O C3H7-i (6-)OCH3
160635 - O C3H7-i (6-)OCH3
142636 - O C2H5 (6-)OC2H5
106
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃637 - O C2H5 (6-)OC2H5
106638 - O C2H5 (6-)OC2H5
159639 - O C2H5 (6-)OC2H5
148640 - O C2H5 (6-)OC2H5
126641 - O C2H5 (6-)OC2H5
111
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃642 - O C2H5 (6-)OC2H5
171643 - O C2H5 (6-)OC2H5
127644 - O C2H5 (6-)OC2H5
148645 - O C2H5 (6-)OC2H5
123646 - O C3H7-n (6-)OC3H7-n
138
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃647 - O C3H7-n (6-)OC3H7-n
95648 - O C3H7-n (6-)OC3H7-n
130649 - O C3H7-n (6-)OC3H7-n
74650 - O C3H7-n (6-)OC3H7-n
109651 - O C3H7-n (6-)OC3H7-n
75
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃652 - O C3H7-n (6-)OC3H7-n
147653 - O C3H7-n (6-)OC3H7-n
99654 - O C3H7-n (6-)OC3H7-n
102655 - O C3H7-n (6-)OC3H7-n
98656 - O C3H7-i (6-)OC3H7-i
138
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃657 - O C3H7-i (6-)OC3H7-i
127658 - O C3H7-i (6-)OC3H7-i
160659 - O C3H7-i (6-)OC3H7-i
115660 - O C3H7-i (6-)OC3H7-i
108661 - O C3H7-i (6-)OC3H7-i
154
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃662 - O C3H7-i (6-)OC3H7-i
144663 - O C2H4OC2H5 (6-)OCH3
124664 - O C2H4OC2H5 (6-)OCH3
138665 - O C4H9-n (6-)OCH3
130666 - O C4H9-n (6-)OCH3
132
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃667 - O C3H7-i (6-)OC3H7-i
100668 - O C3H7-i (6-)OC3H7-i
108669 - O C3H7-i (6-)OC3H7-i
130670 - O C3H7-i (6-)OC3H7-i
133671 - O C3H7-i (6-)OC3H7-i
125
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃672 - O C3H7-i (6-)OC3H7-i
108673 - O C3H7-i (6-)OC3H7-i
110674 - O C4H9-n (6-)OCH3
144675 - O C4H9-n (6-)OCH3
116676 - O C4H9-n (6-)OCH3
139
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃677 - O C4H9-n (6-)OCH3 
174678 - O C4H9-n (6-)OCH3 149679 - O C4H9-n (6-)OCH3 104680 - O C4H9-n (6-)OCH3 
98681 - O C4H9-n (6-)OCH3 
112
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃682 - O C4H9-n (6-)OCH3 
100683 - O C4H9-n (6-)OCH3 
92684 - O C4H9-n (6-)OCH3 115685 - O C4H9-n (6-)OCH3 99686 - O C4H9-n (6-)OCH3 
102
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃687 - O C4H9-n (6-)OCH3 
106688 - O C2H4OC2H5 (6-)OCH3 120689 - O C2H4OC2H5 (6-)OCH3 98690 - O C2H4OC2H5 (6-)OCH3 138691 - O C4H9-i (6-)OC2H5 118
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃692 - O C2H4OC2H5 (6-)OCH3 138693 - O C2H4OC2H5 (6-)OCH3 94694 - O C2H4OC2H5 (6-)OCH3 
94695 - O C2H4OC2H5 (6-)OCH3 65696 - O C2H4OC2H5 (6-)OCH3 
60
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃697 - O C2H4OC2H5 (6-)OCH3 
104698 - O C4H9-n (6-)OC4H9-n
104699 - O C4H9-n (6-)OC4H9-n
137700 - O C4H9-n (6-)OC4H9-n
70701 - O C4H9-n (6-)OC4H9-n
110
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃702 - O C4H9-n (6-)OC4H9-n
102703 - O C3H7-i (6-)OC3H7-i
137704 - O C3H7-i (6-)OCH3
160705 - O C3H7-n (6-)OC3H7-n
94706 - O C3H7-n (6-)OC2H5
155
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃707 - O C3H7-n (6-)OC2H5 130708 - O C3H7-n (6-)OC2H5 142709 - O C3H7-n (6-)OC2H5 
85710 - O C3H7-n (6-)OC2H5 
106711 - O C3H7-n (6-)OC2H5 
87
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃712 - S C3H7-i (6-)OCH3
120713 - S C4H9-n (6-)OCH3
143714 - S C3H7-i (6-)OC3H7-i
152715 - S C2H4OC2H5 (6-)OCH3
112716 - S C3H7-i (6-)OCH3
130
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃717 - S C3H7-i (6-)OCH3
165718 - S C3H7-i (6-)OC3H7-i
161719 - S C4H9-n (6-)OCH3
111720 - S C2H5 (6-)OCH3
156721 - S C2H4OC2H5 (6-)OCH3
137
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃722 - S CH3 (6-)OCH3
163723 - S C3H7-n (6-)OCH3
113724 - S C3H7-n (6-)OCH3
130725 - S C4H9-n (6-)OCH3
154726 - S C3H7-i (6-)OC3H7-i
157
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃727 - S C3H7-n (6-)OC3H7-n
142728 - S C2H5 (6-)OC2H5
162729 - S CH3 (6-)OCH3
157730 - S C2H5 (6-)OCH3
108731 - S CH3 (6-)OCH3
172
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃732 - S CH3 (6-)OCH3
147733 - S C3H7-n (6-)OC3H7-n
160734 - S C3H7-n (6-)OC3H7-n
103735 - O C3H7-n (6-)OC3H7-n
172736 - S C2H5 (6-)OC2H5
137
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃737 - S C2H5 (6-)OC2H5
156738 - S C2H4OC2H5 (6-)OCH3
103739 - S C3H7-i (6-)OC3H7-i
134740 - S C4H9-n (6-)OC4H9-n
87741 - S C4H9-n (6-)OC4H9-n
110
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃742 - S C4H9-n (6-)OC4H9-n
88743 - S C4H9-n (6-)OC4H9-n
98744 - S C4H9-n (6-)OC4H9-n
98745 - S C4H9-n (6-)OC4H9-n
88746 - S C4H9-n (6-)OC4H9-n
104
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃747 - S C4H9-n (6-)OC4H9-n
75748 - O C2H5 (6-)OC2H5
145749 - S C3H7-i (6-)OC2H5
131750 - S C3H7-i (6-)OC2H5
158751 - S C3H7-i (6-)OC2H5
132
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃752 - S C3H7-i (6-)OC2H5 
142753 - S C3H7-i (6-)OC2H5 130754 - S C3H7-i (6-)OC2H5 170755 - S C3H7-n (6-)OC2H5 152756 - S C3H7-n (6-)OC2H5 138
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃757 - S C3H7-n (6-)OC2H5 130758 - S C3H7-n (6-)OC2H5 150759 - S C3H7-n (6-)OC2H5 156760 - S C3H7-n (6-)OC2H5 110761 - S C3H7-n (6-)OC2H5 120
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃762 - S C4H9-n (6-)OC4H9-n
104763 - S C3H7-i (6-)OCH3
105764 - S C3H7-n (6-)OC3H7-n
120765 - S C3H7-n (6-)OCH3
135766 - S C3H7-n (6-)OC3H7-n
116
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃767 - S C3H7-i (6-)OC3H7-i
110768 - S C2H4OC2H5 (6-)OCH3
95769 - S C3H7-i (6-)OCH3
112770 - O C3H7-i (6-)OC2H5
70771 - O C3H7-i (6-)OC2H5
132
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃772 - O C3H7-i (6-)OC2H5 75773 - O C3H7-i (6-)OC2H5 118774 - O C3H7-i (6-)OC2H5 
85775 - O C3H7-i (6-)OC2H5 130776 - O C3H7-i (6-)OC2H5 120
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃777 - O C3H7-i (6-)OC2H5 124778 - O C3H7-i (6-)OC2H5 
130779 - O C3H7-i (6-)OC2H5 
100780 - O C2H5 (6-)OCH3
172781 - O C2H5 (6-)OCH3
164
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃782 - O C3H7-i (6-)OC3H7-i
118783 - O C3H7-i (6-)OC3H7-i
88784 - O C4H9-s (6-)OCH3
124785 - O C4H9-s (6-)OCH3
100786 - O C4H9-n (6-)OC2H5
106
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃787 - O C4H9-n (6-)OC2H5 
108788 - O C4H9-n (6-)OC2H5 
105789 - O C4H9-s (6-)OCH3
112790 - O C4H9-n (6-)OC2H5 
80791 - O C4H9-s (6-)OCH3
130
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃792 - O C4H9-n (6-)OC2H5 120793 - O C4H9-n (6-)OC2H5 
95794 - O C4H9-n (6-)OC2H5 
96795 - O C4H9-s (6-)OCH3
130796 - O C4H9-s (6-)OCH3
118
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃797 - O C4H9-s (6-)OCH3
134798 - O C4H9-s (6-)OCH3
118799 - O C4H9-n (6-)OC2H5 90800 - O C4H9-s (6-)OCH3
78801 - O C4H9-s (6-)OCH3
112
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃802 - O C4H9-s (6-)OCH3
78803 - O C4H9-s (6-)OCH3
80804 - O C4H9-n (6-)OC4H9-n
55805 - O C4H9-n (6-)OC4H9-n
100806 - O C4H9-n (6-)OC4H9-n
92
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃807 - O C3H7-n (6-)OC2H5 
74808 - O C3H7-n (6-)OC2H5 
143809 - O C3H7-n (6-)OC2H5 102810 - O C3H7-n (6-)OC2H5 95811 - O C4H9-n (6-)OC4H9-n
82
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃812 - O C4H9-n (6-)OC2H5 
92813 - O C4H9-n (6-)OCH3
90814 - O C4H9-n (6-)OCH3
124815 - O C4H9-n (6-)OCH3
85816 - O C4H9-n (6-)OCH3
90
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃817 - O C2H4OC2H5 (6-)OCH3 90818 - O
(6-)OCH3
165819 - O
(6-)OCH3
130820 - O
(6-)OCH3
149821 - O C4H9-s (6-)OC4H9-s
125
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃822 - O
(6-)OCH3 
112823 - O
(6-)OCH3 156824 - O
(6-)OCH3 148825 - O
(6-)OCH3 
145826 - O
(6-)OCH3 
156
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃827 - O
(6-)OCH3 
126828 - O
(6-)OCH3 134829 - O
(6-)OCH3 
114830 - O
(6-)OCH3 141831 - O C4H9-i (6-)OC2H5 
125
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃832 - O C4H9-i (6-)OC2H5 128833 - O C4H9-i (6-)OC2H5 
106834 - O C4H9-i (6-)OC2H5 88835 - O C4H9-i (6-)OC2H5 
112836 - O C4H9-i (6-)OC2H5 
125
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃837 - O C4H9-i (6-)OC2H5 106838 - O H (6-)OH
172839 - O C4H9-i (6-)OCH3
102840 - O C4H9-i (6-)OCH3
114841 - O C4H9-i (6-)OCH3
124
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃842 - O C4H9-i (6-)OCH3 
98843 - O C4H9-i (6-)OCH3 146844 - O C4H9-i (6-)OCH3 97845 - O C4H9-i (6-)OCH3 117846 - O C4H9-i (6-)OCH3 
142
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃847 - O C4H9-i (6-)OCH3 
109848 - S C2H5 (6-)OCH3 138849 - S C2H5 (6-)OCH3 135850 - S C2H5 (6-)OCH3 155851 - S C2H5 (6-)OCH3 160
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃852 - S C4H9-s (6-)OCH3 108853 - S C4H9-s (6-)OCH3 143854 - S C4H9-s (6-)OCH3 
105855 - S C4H9-s (6-)OCH3 65856 - S C4H9-s (6-)OCH3 114
表1-续
A O R1 (位置) R3实施例号 R2 熔点℃857 - O C2H5 (3-)CH3
179858 - S C4H9-s (6-)OCH3 146859 - S C3H7-i (6-)OCH3 
146860 - S C4H9-n (6-)OCH3 132861 - S C4H9-n (6-)OCH3 112
表 1-续
A Q R1 (位置) R3实施例号 R2 熔点℃862 - S C4H9-n (6-)OCH3
100863 - S C4H9-n (6-)OCH3
138864 - S C3H7-i (6-)OC2H5 
155865 - S C3H7-i (6-)OC2H5 
140866 - S C4H9-n (6-)OCH3
140
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃867 - O C4H9-i (6-)OCH3
131868 - O C4H9-i (6-)OCH3
135869 - O C4H9-i (6-)OCH3
137870 - O C4H9-n (6-)OC4H9-n
123871 - O C4H9-n (6-)OC2H5
118
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃872 - O
(6-)OCH3
164873 - O C3H7-i (6-)OCH3
150874 - O C3H7-i (6-)OC3H7-i
148875 - O C3H7-n (6-)OCH3
147876 - O C2H5 (6-)OC2H5 108
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃877 - O C3H7-i (6-)OC3H7-i
108878 - O C3H7-i (6-)OC3H7-i
148879 - O C2H5 (6-)OC2H5
176880 - O C3H7-n (6-)OCH3
144881 - O C3H7-i (6-)OC3H7-i
167
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃882 - O C2H5 (6-)OC2H5 135883 - O C3H7-n (6-)OCH3
100884 - O C2H5 (6-)OC2H5 158885 - O C3H7-n (6-)OCH3
108
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃886 - O C3H7-i (6-)OC3H7-i
164887 - O C3H7-i (6-)OC3H7-i
157888 - O C3H7-n (6-)OCH3
113889 - O C3H7-1 (6-)OC3H7-i
132890 - O C3H7-n (6-)OCH3
92
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃891 - O C3H7-i (6-)OC3H7-i
141892 - O C3H7-i (6-)OC3H7-i
159893 - O C2H5 (6-)OC2H5
139894 - O C2H5 (6-)OC2H5
150895 - O C3H7-n (6-)OCH3
126
表1-续
A O R1 (位置) R3实施例号 R2 熔点℃896 - O C3H7-i (6-)CH3 148897 - O C3H7-i (6-)CH3 
157898 - O C3H7-i (6-)CH3 125899 NH O CH3 (6-)OCH3 182900 NH O CH3 (6-)OCH3 175
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃901 - O CF3 (6-)CH3
198(Na salt)902 - O CF3 (6-)CH3
129903 - O CF3 (6-)CH3
149904 - O CF3 (6-)CH3
163905 - O CF3 (6-)C2H5 
121
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃906 - O C3H7-i (6-)CH3 
170907 - O C3H7-i (6-)CH3 125908 - O C3H7-i (6-)CH3 
129909 - O C3H7-i (6-)CH3 156910 - O CH3 (6-)OCH3 
157911 - O CH3 (6-)OCH3 177
表1-续
A Q R1 (位置) R3实施例号 R2 熔点℃912 - O CH3 (6-)OCH3 
172913 - O C3H7-i (6-)CH3
132914 - O C3H7-i (6-)CH3
153915 - O C3H7-i (6-)CH3
150916 - O C3H7-i (6-)CH3
110
表1-续实施例号 A O R1 (位置) R3
R2 熔点℃917 - O C3H7-i (6-)CH3 131918 - O C3H7-i (6-)CH3 
133919 - O CH3 (6-)OCH3 
153920 - O C3H7-i (6-)CH3 
122921 - O C3H7-i (6-)CH3 147
表1-续实施例号A Q R1 (位置) R3
R2 熔点℃922 - O CH3 (6-)OCH3 
160923 - O CH3 (6-)OCH3 182924 - O CH3 (6-)OCH3 
142925 - O CH3 (6-)OCH3 178926 - O C3H7-i (6-)CH3 
151
表1-续实施例号A Q R1 (位置) R3
R2 熔点℃927 - O CH3 (6-)OCH3 
178928 - O CH3 (6-)OCH3 
130929 - O CH3 (6-)OCH3 
124930 - O CH3 (6-)OCH3 
153931 - O CH3 (6-)OCH3 
157
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃932 - O CH3 (6-)OCH3 
114933 - O CH3 (6-)OCH3 130934 - O C3H7-i (6-)CH3
151935 - O C3H7-i (6-)CH3
153936 - O CH3 (6-)OCH3 
167
表1-续实施例号 A Q R1 (位置) R3
R2 熔点℃937 - O CF2Cl (6-)CH3
180(Na salt)938 - O CH3 (6-)OCH3
157(Na salt)939 NH O CH2CH2F (6-)CH3
163940 NH O CH2CHF2 (6-)CH3
160941 NH O CF2CHFCl (6-)CH3
88
表1-续实施例号A Q R1 (位置) R3
R2 熔点℃942 - O CH2CH2F (6-)CH3 178943 - O CH2CH2F (6-)CH3 
135944 - O CH2CH2F (6-)CH3 
127945 - O CH2CH2F (6-)CH3 
139946 - O CH2CH2F (6-)CH3 280(Na salt)
表1-续实施例号A Q R1 (位置) R3
R2 熔点℃947 - O CH2CH2F (6-)CH3 171948 - O CH2CH2F (6-)CH3 
144949 - O CH2CHF2 (6-)CH3 273(Na salt)950 - O CH2CHF2 (6-)CH3 181951 - O CH2CHF2 (6-)CH3 142
表1-续实施例号A Q R1 (位置) R3
R2 熔点℃952 - O CH2CHF2 (6-)CH3
114953 - O CH2CHF2 (6-)CH3
108954 - O CH2CHF2 (6-)CH3
185955 - O CH2CHF2 (6-)CH3
150956 - O CF3 (6-)C2H5 
143(Na salt)
表1-续实施例号A Q R1 (位置) R3
R2 熔点℃957 - O CF3 (6-)CH3 155958 - O CF3 (6-)CH3 112959 - O CF3 (6-)CH3 166960 - O CF3 (6-)CH3 137961 - O CF3 (6-)CH3 
132
表1-续实施例号A Q R1 (位置) R3
R2 熔点℃962 - O CF3 (6-)CH3 172963 - O CF3 (6-)CH3 139964 - O CF3 (6-)CH3 
130965 - O C2H5 (3-)CH3 184可以例如如下制备表1中列出的化合物，如实施例9：(方法(b))
1.4g(0.01mol)5-乙氧基-4-甲基-2，4-二氢-3H-1，2，4-三唑-3-酮和2.4g(0.01mol)2-乙氧基-6-甲基-苯基磺酰基异氰酸盐在50ml乙腈中在20℃下搅拌15小时。蒸馏出溶剂，残余物与二乙醚搅拌，抽滤滤出沉淀。
得到3.3g(理论值85％)5-乙氧基-4-甲基-2-(2-乙氧基-6-甲基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮，熔点160℃。式(II)或(IIa)的起始原料：实施例(II-1)
64.6g(0.26mol)2-异丙氧基-6-甲基-苯磺酰氯在350ml25％强度氨水溶液中在20℃搅拌12小时。接着抽滤分离结晶产物
得到54g(理论值90％)2-异丙氧基-6-甲基-苯磺酰胺，熔点78℃。实施例(II-2)
1.9g(10mmol) 2-羟基-6-甲基-苯磺酰胺，1.2g(10mmol)炔丙基溴(以80％强度甲苯溶液的形式)和1.4g(10mmol)碳酸钾在回流下加热2小时，然后过滤混合物，水泵真空下浓缩滤液，残余物溶解于石油醚中，由此溶液抽滤分离得到的结晶产物。
得到2.1g(理论值93％)6-甲基-2-炔丙基氧基-苯磺酰胺，熔点129℃。实施例(II-3)
在20℃，搅拌下向32.3g(0.15mol)2-乙氧基-6-甲基苯磺酰胺的300ml二氯甲烷的溶液中滴加188ml1摩尔溴化硼(III)的二氯甲烷溶液，反应混合物在20℃下搅拌30分钟。然后自0℃至5℃(冰冷却)滴加300ml甲醇。加热到20℃后，反应混合物在水泵真空下浓缩，残余物与乙酸乙酯搅拌，用水洗涤得到的溶液，硫酸钠干燥，过滤水泵真空下浓缩滤液，残余物与石油醚搅拌结晶，并抽滤分离结晶产物。
得到20.3g(理论值72％)2-羟基-6-甲基-苯磺酰胺，熔点126℃。
类似于实施例(II-1)至(II-3)，并根据本发明制备方法的概括描述，也可以例如制备下面表2中列出的式(II)或(IIa)化合物。表2：式(II)化合物的实施例实施例号 A R1 (位置)
R2 熔点(℃)II-4 - C2H5 (6-)CH3 104II-5 - n-C3H7 (6-)CH3 63II-6 - -CH2CH2Cl (6-)CH3 102II-7 - CH3 (6-)CH3 132II-8 - -CH2C6H5 (6-)CH3 131II-9 - -CH2COOCH3 (6-)CH3 90II-10 - CH3 (6-)C3H7-n 108II-11 - C2H5 (6-)C3H7-n 80II-12 - C2H5 (5-)CH3 131II-13 - CH3 (6-)Cl 166II-14 - C2H5 (6-)Cl 121
表1-续实施例号 A R1 (位置)
R2 熔点(℃)II-15 - H (6-)Cl 118II-16 - i-C3H7 (6-)Cl 85II-17 - -CH2CH＝CH2 (6-)Cl 106II-18 - -CH2C＝CH (6-)Cl 181II-19 - CF3 (5-)ClII-20 - CHF2 (5-)CH3 127II-21 - CHF2 (6-)CH3 89II-22 - CH3 (5-)C(CH3)3 160II-23 - CH3 (5-)ClII-24 - CHF2 (4-)CH3 153II-25 - -CF2CHFCl (6-)CH3 85II-26 - C2H5 (6-)CH2Cl式(IV)的起始原料实施例(IV-1)
21.5g(0.1mol)2-乙氧基-6-甲基-苯磺酰胺和10g(0.1mol)异氰酸正丁酯在100ml氯苯中加热至沸腾。在回流温度下，通入4小时光气。减压下浓缩澄清溶液，精馏残余物。在0.8毫巴的压力和135-140℃的顶空温度下，馏出2-乙氧基-6-甲基-苯基磺酰基异氰酸盐，其在接收器中固化。
得到7.9g 2-乙氧基-6-甲基-苯基磺酰基异氰酸盐，为无色产物，熔点40℃。式(VI)或(VIa)的起始原料：实施例(VI-1)
47.8g(0.29mol)2-异丙氧基-6-甲基苯胺溶解于87ml 1N盐酸和145ml浓盐酸的混合物中，将该溶液冷却到-5℃。在-5℃至0℃下，在搅拌下滴加22g(0.32mol)亚硝酸钠的87ml水溶液，并在大约0℃下将混合物再搅拌1小时。用氨基磺酸去除过量的亚硝酸盐后，在-5℃至0℃将得到的重氮盐溶液滴加到二氧化硫的175ml 1.2-二氯乙烷的饱和溶液中。大约30分钟后，加入1.7g氯化亚铜(I)和1.7g十二烷基-三甲铵溴化物，让反应混合物在大约60分钟中升至室温，再经1小时加热到大约40℃，并在该温度下搅拌大约12小时。在大约20℃时，加入14.2g 35％强度过氧化氢溶液，将混合物搅拌大约30分钟，接着与300ml二氯甲烷搅拌，分离有机相，用水洗涤，硫酸钠干燥并过滤、通过水泵真空蒸馏自滤液中小心去除溶剂。
得到65.9g(理论值90％)2-异丙氧基-6-甲基-苯磺酰氯，为亮棕色油状残余物。1H-NMR(CDCl3，TMS，δppm)：1.47(d，J＝6.1Hz，2xCH3)；2.68(s，CH3)；4.79(sept.，J＝6.1Hz，1H)；6.83(d，J＝7.5Hz，1H)；6.95(d，J＝8.4Hz，1H)；7.45(pseudo t，J＝8.3Hz，1H)。
类似于实施例(VI-1)，也可以例如制备下面表3中列出的式(VI)或(VIa)化合物。表3：式(VI)化合物的实施例实施例号A R1 (位置) 物理数据
R2VI-2 - CH3 (6-)CH3 Fp：52℃VI-3 - C2H5 (6-)CH3 1H-NMR(CDCl3，TMS，δ，ppm)1.55
(t，J＝6,97HZ，CH3)，2,69(s，CH3)，
4,24(q，J＝6,97Hz，CH2)，6,87(d，
J＝7,68Hz，1H)，6,95(d，J＝8,34Hz，
1H)，7,46(pseudo t，J＝8，1Hz，1H)VI-4 - n-C3H7 (6-)CH3 1H-NMR(CDCl3，TMS，δ，ppm)1.33
(t，J＝7,38Hz，CH3)，1,95(m，CH2)，
2,69(s，CH3)，4,12(t，J＝6,3Hz，
CH2)，6,86(d，J＝7,69Hz，1H)，6,94
(d，J＝8,37Hz，1H)，7,46(pseudc t，
J＝7,8Hz，1H)
表3-续实施例号 A R1 (位置) 物理数据
R2VI-5 - -CH2CH2Cl (6-)CH3 1H-NMR(CDCl3，TMS，δ，ppm)：2,71
(s，CH3)，3,94(t，J＝6,1Hz，CH2)，
4,41(t，J＝6,1Hz，CH2)，6,96(t，J＝7,1
Hz，2H)，7,5(t，J＝7,8Hz，1H)VI-6 - -CH2CH2OC2H5(6-)CH3 1H-NMR(CDCl3，TMS，δ，ppm)：1,23
(t，J＝7Hz，CH3)，2,69(s，CH3)，3,65
(q，J＝7Hz，CH2)，3,91(t，J＝5,16Hz
CH2)，4,30(t，J＝5,16Hz，CH2)，6,89
(d，J＝7,7Hz，1H)，7,0(d，J＝8,3Hz
1H)，7,47(pseudo t，J＝8,1Hz，1H)VI-7 - C2H5 (5-)CH3 1H-NMR(CDCl3，TMS，δ，ppm)1,53
(t，J＝7Hz，CH3)，2,36(s，CH3)，4,25
(q，J＝7Hz，CH2)，7,0(d，J＝8,53Hz，
1H)，7,45(d，J1＝8,53Hz，J2＝2,15Hz，
1H)，7,75(d，J＝2,15Hz，1H)VI-8 - n-C3H7 (5-)CH3 1H-NMR(CDCl3，TMS，δ，ppm)：1,08
(t，J＝7,38Hz，CH3)，1,85(m，CH2)，
2,23(s，CH3)，3,99(t，J＝6,5Hz)，6,74
(d，J＝8,2Hz，1H)，6,92(m，1H)，7,34
(d，J＝1,65Hz，1H)VI-9 - i-C3H7 (5-)CH3 1H-NMR(CDCl3，TMS，δ，ppm)：1,45
(d，J＝6,06，2xCH3)，2,35(s，CH3)，
4,77(sept，J＝6,06Hz，1H)，6,99(d，
J＝8,57Hz，1H)，7,43(dd，J1＝8,56Hz，
1H，J2＝2,1Hz，1H)，7,74(d，J＝2,1
Hz，1H)
表3-续实施例号 A R1 (位置) 物理数据
R2VI-10 - C2H5 (6-)CH2Cl (Oil)VI-11 - -CF2CHFCl (6-)CH3 1H-NMR(CDCl3，TMS，δ，ppm)：2,78
(s，CH3)，6,46(td，CHFCl)，7,2-7,6
(Ar-H)VI-12 - CHF2 (6-)CH3 1H-NMR(CDCl3，TMS，δ，ppm)：2,76
(s，CH3)，6,61(t，CHF2)，7,27-7,59
(Ar-H)VI-13 - CH3 (5-)C(CH3)3 Fp：62℃VI-14 - CHF2 (4-)CH3 1H-NMR(CDCl3，TMS，δ，ppm)：2,50
(s，CH3)，6,68(t，CHF2)，7,05-7,92
(Ar-H)VI-15 - CHF2 (5-)CH3 1H-NMR(CDCl3，TMS，δ，ppm)：2,45
(s，CH3)，6,64(t，CHF2)，7,35-7,86
(AR-H)VI-16 - -CH2CH2Cl (6-)CH3VI-17 - -CH2CH＝CH2(6-)CH3VI-18 - -CH2C＝CH (6-)CH3VI-19 - -CH2C6H5 (6-)CH3式(X)的起始原料：实施例(X-1)
步骤1：制备2-异丙氧基-6-甲基-硝基苯
153g(1.0mol)3-甲基-2-硝基-苯酚，172.5g(1.25mol)碳酸钾，170g(1.0mol)2-碘-丙烷和400ml丙酮在回流下加热12小时。接着在水泵真空下浓缩，残余物与400ml二氯甲烷搅拌，过滤混合物，用二氯甲烷洗涤过滤的产物。水泵真空蒸馏从滤液中小心去除溶剂。
得到183.4g 2-异丙氧基-6-甲基-硝基苯，为黄色油状残余物。1H-NMR(CDCl3，TMS，δppm)：1.33(d，J＝6.1Hz，2xCH3)；2.28(s，CH3)；4.6(sept.，J＝6.1Hz，1H)；6.8(d，J＝7.7Hz，1H)；6.87(d，J＝8.4Hz，1H)；7.26(pseudo t，J＝8.1Hz，1H)。步骤2：制备2-异丙氧基-6-甲基苯胺
在40至60巴的氢压力下，在存在9.5g阮内镍下在1升乙酸乙酯中将183.3g(0.94mol)2-异丙氧基-6-甲基-硝基苯氢化5小时。然后过滤混合物，并通过水泵真空蒸馏从滤液中小心去除溶剂。
得到139.4g(理论值90％)2-异丙氧基-6-甲基-苯胺，为橙色油状残余物。1H-NMR(CDCl3，TMS，δppm)：1.36(d，J＝6.1Hz，2xCH3)；2.16(s，CH3)；3.72(s，NH2)，4.51(sept.，J＝6.1Hz，1H)；6.65-6.70(m，3H)。应用实施例
在应用实施例中，使用下面指定的化合物为对比物质：4，5-二甲氧基-2-(2-甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮(EP 534266中公开)；4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮(EP 534266中公开)。实施例A苗前试验溶剂： 5份重量丙酮乳化剂： 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适制剂，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，用水将乳油稀释到所需浓度。
试验植物的种子种到正常土壤中，24小时后，用活性化合物制剂灌溉土壤。希望每单位面积保持恒定量的水。制剂中活性化合物的浓度并不重要，只有每单位面积施用的活性化合物的量是决定性的。
三星期后，与未处理的对照物的生长相比以损伤百分率测定对植物损伤的程度。数值表示：
0％＝没有作用(象未处理的对照物)
100％＝完全损伤。
在该项试验中，例如制备实施例1、7-21、23-41、46-49、51、54、55、57、60、62、65、68、72-74、76、78、79、88、89、199、207、209、222和901的化合物具有非常强的杀阔叶杂草的作用。实施例B苗后试验溶剂： 5份重量丙酮乳化剂： 1份重量烷基芳基聚乙二醇醚
为了制备活性化合物的合适制剂，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，用水将乳油稀释到所需浓度。
以一种方式用活性化合物的制剂对高5-15cm的试验植物喷雾，使每单位面积施用具体量的所期活性化合物。选择喷雾液浓度，使以2000升水/ha施用具体量的所期活性化合物。三星期后，与未处理对照物的生长相比较以损伤百分率测定对植物损伤的程度。数值表示：
0％＝没有作用(象未处理的对照物)
100％＝完全损伤。
在该项试验中，例如制备实施例1、7-10、12、13、15、16、17、25、30、31、38、40、41、46和47的化合物具有非常强的杀阔叶杂草的作用。
Claims (10)
1.通式(I)磺酰基氨基(硫代)羰基化合物，
其中：A 代表一个单键，氧原子，硫原子或N-R基团，其中R代表氢、烷基、链烯基、炔烃基或环烷基，Q 代表氧原子或硫原子，R1 代表氢或甲酰基或者代表在各种情况下可有可无地被取代的烷基、链烯基、炔烃基、烷基羰基、烷氧基羰基、烷基磺酰基、环烷基、环烷基羰基或环烷基磺酰基，R2 代表氰基或卤原子或者代表在各种情况下可有可无地被取代的烷基、链烯基、炔烃基、烷氧基、链烯基氧基或炔烃基氧基，和R3 代表在各种情况下可有可无地被取代的五元杂环基，五元杂环五个原子中至少有一个原子是氧、硫或氮，而且其它成环原子中还可以有1至3个原子可以是氮，和式(I)化合物的盐，排除先前已知的化合物4，5-二甲氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮和N-(2，5-二甲氧基-苯基磺酰基)-1，5-二甲基-1H-吡唑-3-甲酰胺。
2.权利要求1的式(I)化合物，特征在于在这些化合物中：A 代表一个单键、氧原子、硫原子或N-R基团，其中R代表氢原子、C1-C6-烷基、C2-C6-链烯基、C2-C6-炔烃基或C3-C6-环烷基，Q 代表氧原子或硫原子，R1 代表氢或甲酰基或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-、苯基-或C1-C4-烷氧基取代的、各种情况下最多有6个碳原子的烷基、链烯基、炔烃基、烷基羰基、烷氧基羰基或烷基磺酰基，或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-或C1-C4-烷基取代的C3-C6-环烷基、C3-C6-环烷基羰基或C3-C6-环烷基磺酰基，R2代表氰基、氟、氯或溴，或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-或C1-C4-烷氧基取代的、各种情况下最多有6个碳原子的烷基、链烯基、炔烃基、烷氧基，链烯基氧基或炔烃基氧基，和R3 代表各种情况下可有可无地被取代的下式杂环基，
其中：Q1、Q2和Q3各自代表氧原子或硫原子，和R4 代表氢、羟基、氨基或氰基，或者代表C2-C10-亚烷基氨基，或代表可有可无地被氟-、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，或者代表在各种情况下可有可无地被氟-、氯-、和/或溴取代的C2-C6-链烯基或C2-C6-炔烃基，或代表各种情况下可有可无地被氟-、氯-、溴-、氰基-、C1-C4-烷氧基或C1-C4-烷氧基羰基取代的C1-C6-烷氧基、C1-C6-烷基氨基或C1-C6-烷基羰基氨基，或者代表C3-C6-链烯氧基，或者代表二(C1-C4-烷基)-氨基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、氰基-和/或C1-C4-烷基取代的C3-C6-环烷基、C3-C6-环烷基氨基或C3-C6-环烷基-C1-C4-烷基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、氰基-、硝基-、C1-C4-烷基-、三氟甲基-和/或C1-C4-烷氧基取代的苯基，苯基氨基或苯基-C1-C4-烷基，R5代表氢、羟基、巯基、氨基、氰基、氟、氯、溴或碘，或者代表可有可无地被氟-、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，或者代表在各种情况下可有可无地被氟-、氯-、和/或溴-取代的C2-C6-链烯基或C2-C6-炔烃基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、C1-C4-烷氧基-或C1-C4-烷氧基羰基-取代的C1-C6-烷氧基、C1-C6-烷基硫基、C1-C6-烷基氨基或C1-C6-烷基羰基氨基，或者代表C3-C6-链烯基氧基、C3-C6-炔烃基氧基、C3-C6-链烯基硫基、C3-C6-炔烃基硫基、C3-C6-链烯基氨基或C3-C6-炔烃基氨基，或者代表二(C1-C4-烷基)-氨基，或者代表在各种情况下可有可无地被甲基-和/或乙基取代的氮丙啶子基、吡咯烷子基、哌啶子基或吗啉代，或者代表各种情况下可有可无地被氟-、氯-、溴-、氰基-和/或C1-C4-烷基取代的C3-C6-环烷基、C5-C6-环烯基、C3-C6-环烷基氧基、C3-C6-环烷基硫代、C3-C6-环烷基氨基、C3-C6-环烷基-C1-C4-烷基、C3-C6-环烷基-C1-C4-烷氧基、C3-C6-环烷基-C1-C4-烷基硫代或C3-C6-环烷基-C1-C4-烷基氨基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、氰基-、硝基-、C1-C4-烷基-、三氟甲基-、C1-C4-烷氧基-和/或C1-C4-烷氧基羰基取代的苯基、苯基-C1-C4-烷基、苯氧基、苯基C1-C4-烷氧基、苯基硫基、苯基-C1-C4-烷基硫基、苯基氨基或苯基-C1-C4-烷基氨基，或者R4和R5一起代表可有可无地支链化的具有3至11个碳原子的链烷烃双基，还有R6、R7和R8是相同的或不同的，并且代表氢、氰基、氟、氯或溴，或者代表在各种情况下可有可无地被氟-、氯-、溴-或C1-C4-烷氧基取代的、各种情况下最多有6个碳原子的烷基、链烯基、炔烃基、烷氧基、链烯基氧基、炔烃基氧基、烷基硫基、链烯基硫基、炔硫基、烷基亚磺酰基和烷基磺酰基，或者代表在各种情况下可有可无地被氰基-、氟-、氯-、溴-或C1-C4-烷基取代的具有3至6个碳原子的环烷基，排除先前已知的化合物4，5-二甲氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮和N-(2，5-二甲氧基-苯基磺酰基)-1，5-二甲基-1H-吡唑-3-甲酰胺，和式(I)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、C5-或C6-环烷基-铵盐和二(C1-C2-烷基)-苄基铵盐。
3.权利要求1的式(I)化合物，特征在于在这些化合物中：A 代表一个单键、氧原子或N-R基团，其中R代表氢、甲基、乙基、正-或异-丙基、正-、异-或仲丁基、丙烯基、丁烯基、丙炔基、丁炔基、环丙基、环丁基、环戊基或环己基，Q 代表氧或硫，R1 代表氢或甲酰基，或者代表在各种情况下可有可无地被氟-、氯-、溴-、甲氧基-或乙氧基-取代的甲基、乙基、正-或异-丙基、正-、异-或仲丁基、丙烯基、丁烯基、丙炔基、丁炔基、乙酰基、丙酰基、丁酰基、甲氧基羰基、乙氧基羰基、正-或异-丙氧基羰基、甲基磺酰基、乙基磺酰基、正-或异丙基磺酰基、正-、异-、仲-或叔丁基磺酰基，或者代表在各种情况下被氟-、氯-或甲基任选取代的环丙基、环丙基羰基或环丙基磺酰基，R2代表氰基、氟、氯或溴，或代表各种情况下可有可无地被氟-、氯-、甲氧基-或乙氧基取代的甲基、乙基、正-或异-丙基、正-、异-或仲丁基、丙烯基、丁烯基、丙炔基、丁炔基、甲氧基、乙氧基、正-或异-丙氧基、正-、异-或仲丁氧基、丙烯基氧基、丁烯基氧基、丙炔基氧基或丁炔基氧基，和R3 代表在各种情况下可有可无地被取代的下式的杂环基，
其中Q1、Q2和Q3各自代表氧原子或硫原子，和R4代表氢、羟基或氨基，或者代表C3-C8亚烷基氨基，或者代表在各种情况下可有可无地被氟-、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，或者代表在各种情况下可有可无地被氟-、氯-或溴取代的丙烯基、丁烯基、丙炔基或丁炔基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲氧基、乙氧基、正-或异-丙氧基、正-、异-、仲-或叔丁氧基、甲基氨基、乙基氨基、正-或异-丙基氨基、正-、异-、仲-或叔丁基氨基，或者代表丙烯基氧基或丁烯基氧基，或者代表二甲基氨基或二乙基氨基，或者代表在各种情况下可有可无地被氟-、氯-、甲基-和/或乙基取代的环丙基、环丁基、环戊基、环己基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、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在各种情况下可有可无地被氟-、氯-、甲基-、三氟甲基和/或甲氧基取代的苯基或苄基，R5代表氢、羟基、巯基、氨基、氟、氯或溴，或者代表在各种情况下可有可无地被氟-、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，或者代表在各种情况下可有可无地被氟-、氯-或溴取代的乙烯基、丙烯基、丁烯基、丙炔基或丁炔基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲氧基、乙氧基、正-或异-丙氧基、正-、异-、仲-或叔丁氧基、甲基硫基、乙基硫基、正-或异丙基硫基、正-、异-、仲-或叔丁基硫基、甲基氨基、乙基氨基、正-或异-丙基氨基、正-、异-、仲-或叔丁基氨基，或者代表丙烯基氧基、丁烯基氧基、丙炔基氧基、丁炔基氧基、丙烯基硫基、丙二烯基硫基、丁烯基硫基、丙炔基硫基、丁炔基硫基、丙烯基氨基、丁烯基氨基、丙炔基氨基或丁炔基氨基，或者代表二甲基氨基、二乙基氨基或二丙基氨基，或者代表在各种情况下可有可无地被氟-、氯-、甲基-和/或乙基取代的环丙基、环丁基、环戊基、环己基、环戊烯基、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、环己基硫基、环丙基氨基、环丁基氨基、环戊基氨基、环己基氨基、环丙基甲基、环丁基甲基、环戊基甲基、环己基甲基、环丙基甲氧基、环丁基甲氧基、环戊基甲氧基、环己基甲氧基、环丙基甲基硫基、环丁基甲基硫基、环戊基甲基硫基、环己基甲基硫基、环丙基甲基氨基、环丁基甲基氨基、环戊基甲基氨基或环己基甲基氨基，或者代表各种情况下可有可无地被氟-、氯-、甲基-、三氟甲基-、甲氧基-和/或甲氧基羰基取代的苯基、苄基、苯氧基、苄基氧基、苯基硫基、苄基硫基、苯基氨基或苄基氨基，或者R4和R5一起代表可有可无地支化的有3至11个碳原子的链烷烃双基，以及R6、R7和R8是相同的或不同的，并且代表氢、氰基、氟、氯或溴，或者代表在各种情况下可有可无地被氟-、氯-、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、丙烯基、丁烯基、丙炔基、丁炔基、甲氧基、乙氧基、正-或异-丙氧基、正-、异-、仲-或叔丁氧基、丙烯基氧基、丁烯基氧基、丙炔基氧基、丁炔基氧基、甲基硫基、乙基硫基、正-或异-丙基硫基、正-、异-、仲-或叔丁基硫基、丙烯基硫基、丁烯基硫基、丙炔基硫基、丁炔基硫基、甲基亚磺酰基、乙基亚磺酰基、甲基磺酰基或乙基磺酰基，或者代表环丙基，排除先前已在的化合物4，5-二甲氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮、4，5-二乙氧基-2-(2，5-二甲氧基-苯基磺酰基氨基羰基)-2，4-二氢-3H-1，2，4-三唑-3-酮和N-(2，5-二甲氧基-苯基磺酰基)-1，5-二甲基-1H-吡唑-3-甲酰胺。
4.权利要求1的式(I)化合物，特征在于在这些化合物中A 代表一个单键，Q 代表氧原子或硫原子，R1 代表甲基、乙基、正-或异丙基，R2 代表在各种情况下在5或6-位上的氯或甲基，和R3 代表下式可有可无地被取代的三唑啉基
其中：Q1 代表氧或硫，和R4 代表各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲基、乙基、正-或异丙基，或代表丙烯基或丙炔基，或代表甲氧基、乙氧基、正-或异-丙氧基，或代表环丙基，和R5代表氢、氯或溴，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲基、乙基、正-或异-丙基，或者代表在各种情况下可有可无地被氟和/或氯取代的丙烯基或丙炔基，或者代表在各种情况下可有可无地被氟-、氯-、氰基-、甲氧基-或乙氧基取代的甲氧基、乙氧基、正-或异-丙氧基、甲基硫基、乙基硫基、正-或异丙基硫基，或者代表丙烯基氧或环丙基。
5.制备权利要求1式(I)化合物的方法，特征在于(a)在可有可无地存在一种酸受体和可有可无地存在一种稀释剂下，通式(II)氨基磺酰基化合物
其中A、R1和R2具有权利要求1给出的定义，与通式(III)(硫代)羧酸衍生物反应
其中Q和R3具有权利要求1给出的定义，Z 代表卤原子、烷氧基、芳基氧基或芳基烷氧基，或者(b)可有可无地存在一种反应助剂和可有可无地存在一种稀释剂下，通式(IV)磺酰基异(硫代)氰酸酯
其中A、Q、R1和R2具有上面给出的定义，与通式(V)杂环反应，
H-R3 (V)其中R3具有上面给出的定义，或者(c)可有可无地存在一种反应助剂和可有可无地存在一种稀释剂下，通式(VI)氯代磺酰基化合物其中A、R1和R2具有上文给出的定义，与通式(V)杂环
H-R3 (V)其中R3具有上文给出的定义以及通式(VII)金属(硫代)氰酸盐反应
MQCN (VII)其中Q 具有上文给出的定义，和M 代表碱金属或碱土金属等同物，或者(d)可有可无地存在一种酸受体和可有可无地存在一种稀释剂下，通式(VI)氯代磺酰基化合物
其中A、R1和R2具有上面给出的定义，与通式(VIII)(硫代)甲酰胺反应
其中Q和R3具有上面给出的定义，或者(e)可有可无地存在一种酸受体和可有可无地存在一种稀释剂下，通式(IX)磺酰基氨基(硫代)羰基化合物，其中A、Q、R1和R2具有上面给出的定义，和Z 代表卤原子、烷氧基、芳基氧基或芳基烷氧基，与通式(V)杂环反应
H-R3 (V)其中R3 具有上面给出的定义，或者(f)可有可无地存在一种稀释剂，通式(V)杂环
H-R3 (V)其中R3具有上面给出的定义，与氯代磺酰基异(硫代)氰酸酯反应，而且该反应生成的加成物在可有可无地存在一种酸受体和可有可无地存在一种稀释剂下就地与通式(X)苯衍生物反应
其中A、R1和R2具有上面给出的定义，而且，如果需要，可以通过常规方法将通过方法(a)、(b)、(c)、(d)、(e)或(f)得到的式(I)化合物转化成盐。
6.除草组合物，特征在于含有至少一种权利要求1的式(I)化合物或其一种盐。
7.权利要求1的通式(I)的化合物或其盐抑制不希望植物的生长的用途。
8.除草方法，特征在于使权利要求1的通式(I)化合物或其盐作用于杂草或杂草生长地。
9.制备除草组合物的方法，特征在于权利要求1的通式(I)的化合物或其盐与增充剂和/或表面活性剂混合。
10.式(XIII)苯磺酸衍生物其中E 代表-NH2，-N＝C＝Q或-Cl，其中Q 代表O或S，以及A1 代表乙基、正-或异丙基、正-、异-、仲-或叔丁基、三氟甲基、氟乙基、氯乙基、二氟乙基、三氟乙基、氯代三氟乙基、甲氧基乙基、乙氧基乙基、烯丙基、炔丙基或苄基，和A2 代表甲基、乙基、正-或异丙基、正-、异-、仲-或叔丁基。
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19525162.8 | 1995-07-11 | ||
| DE19525162A DE19525162A1 (de) | 1995-07-11 | 1995-07-11 | Sulfonylamino(thio)carbonylverbindungen |
| PCT/EP1996/002826 WO1997003056A1 (de) | 1995-07-11 | 1996-06-28 | Herbizide sulfonylamino(thio)carbonylverbindungen |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011015276A Division CN1252047C (zh) | 1995-07-11 | 2001-01-17 | 苯磺酸衍生物 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN1198159A true CN1198159A (zh) | 1998-11-04 |
| CN1086696C CN1086696C (zh) | 2002-06-26 |
Family
ID=7766505
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN96196753.6A Expired - Fee Related CN1086696C (zh) | 1995-07-11 | 1996-06-28 | 磺酰基氨基(硫代)羰基化合物 |
| CNB011015276A Expired - Fee Related CN1252047C (zh) | 1995-07-11 | 2001-01-17 | 苯磺酸衍生物 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CNB011015276A Expired - Fee Related CN1252047C (zh) | 1995-07-11 | 2001-01-17 | 苯磺酸衍生物 |
Country Status (13)
| Country | Link |
|---|---|
| US (2) | US6251831B1 (zh) |
| EP (2) | EP1344771A1 (zh) |
| JP (1) | JP4084414B2 (zh) |
| CN (2) | CN1086696C (zh) |
| AR (1) | AR002810A1 (zh) |
| AU (1) | AU703153B2 (zh) |
| BR (1) | BR9609902A (zh) |
| CA (1) | CA2226669C (zh) |
| DE (2) | DE19525162A1 (zh) |
| ES (1) | ES2202457T3 (zh) |
| HK (1) | HK1016167A1 (zh) |
| WO (1) | WO1997003056A1 (zh) |
| ZA (1) | ZA965841B (zh) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115872909A (zh) * | 2022-12-27 | 2023-03-31 | 沈阳有色金属研究院有限公司 | 一种硫化矿捕收剂n-苯磺酰基-o-烷基硫代氨基甲酸酯及其制备方法和应用 |
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
| 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 |
| BE1012386A3 (fr) * | 1999-01-15 | 2000-10-03 | Univ Liege | Derives de sulfonamides benzeniques et leurs utilisations. |
| DE19946853A1 (de) * | 1999-09-30 | 2001-04-05 | Bayer Ag | Substituierte Arylketone |
| DE10031825A1 (de) | 2000-06-30 | 2002-01-10 | Bayer Ag | Selektive Herbizide auf Basis von Arylsulfonylaminocarbonyltriazolinonen |
| DE10111649A1 (de) * | 2001-03-12 | 2002-09-19 | Bayer Ag | Substituierte Fluoralkoxyphenylsulfonylharnstoffe |
| DE10117673A1 (de) * | 2001-04-09 | 2002-10-10 | Bayer Ag | Substituierte Fluoralkoxyphenylsulfonylamino(thio)carbonyl-triazolin(thi)one |
| DE10143083A1 (de) * | 2001-09-03 | 2003-03-20 | Bayer Cropscience Ag | Selektive Herbizide auf Basis von substituierten Arylsulfonylaminocarbonyltriazolinonen und Safenern |
| DE10201391A1 (de) | 2002-01-16 | 2003-07-31 | Bayer Cropscience Ag | Verwendung von Alkoholethoxylaten als Penetrationsförderer |
| JP4954083B2 (ja) * | 2004-11-18 | 2012-06-13 | シンタ ファーマスーティカルズ コーポレイション | Ｈｓｐ９０活性を調節するトリアゾール化合物 |
| EP1717228A1 (de) | 2005-04-28 | 2006-11-02 | Bayer CropScience GmbH | Sulfonylamino(thio)carbonylverbindungen als Herbizide oder Pflanzenwachstumsregulatoren |
| CA2618628C (en) | 2005-08-18 | 2014-11-18 | 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 |
| CA2853806C (en) | 2011-11-02 | 2020-07-14 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with platinum-containing agents |
| CA2853799A1 (en) | 2011-11-02 | 2013-05-10 | Synta Pharmaceuticals Corp. | Cancer therapy using a combination of hsp90 inhibitors with topoisomerase i inhibitors |
| CA2854188A1 (en) | 2011-11-14 | 2013-05-23 | Synta Pharmaceuticals Corp. | Combination therapy of hsp90 inhibitors with braf inhibitors |
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| US4452628A (en) | 1979-07-26 | 1984-06-05 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CA1330438C (en) | 1980-07-17 | 1994-06-28 | Willy Meyer | N-phenylsulfonyl-n'-pyrimidinyl-and-triazinylureas |
| US4443245A (en) | 1981-07-13 | 1984-04-17 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N'-triazinylureas |
| MA19680A1 (fr) | 1982-01-11 | 1983-10-01 | Novartis Ag | N- arylsulfonyl - n' - pyrimidinylurees. |
| DE3936622A1 (de) * | 1989-11-03 | 1991-05-08 | Bayer Ag | Halogenierte sulfonylaminocarbonyltriazolinone |
| US5085684A (en) | 1988-05-09 | 1992-02-04 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having substituents which are bonded via sulphur |
| DE4131842A1 (de) * | 1991-09-25 | 1993-04-01 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit zwei ueber sauerstoff gebundenen substituenten |
| US5300480A (en) * | 1989-04-13 | 1994-04-05 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyltriazolinones having two substituents bonded via oxygen |
| US5057144A (en) | 1988-05-09 | 1991-10-15 | Bayer Aktiengesellschaft | Sulphonylaminocarbonyltriazolinones |
| US5238910A (en) | 1989-11-03 | 1993-08-24 | Bayer Aktiengesellschaft | Herbicidal halogenated sulphonylaminocarbonyltriazolinones |
| DE4029753A1 (de) * | 1990-09-20 | 1992-03-26 | Basf Ag | Sulfonamide |
| DE4038430A1 (de) | 1990-12-01 | 1992-06-04 | Basf Ag | Herbizide n-((1,3,5-triazin-2-yl)-aminocarbonyl) benzolsulfonamide |
| US5534486A (en) | 1991-04-04 | 1996-07-09 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen |
| CA2066932A1 (en) | 1991-04-29 | 1992-10-30 | Robert E. Rosen | Phosphousulfonate herbicides |
| DE4206145A1 (de) | 1992-02-28 | 1993-09-02 | Basf Ag | Herbizide n-((pyrimidin-2-yl)aminocarbonyl)benzolfulfonamide |
| DE4234801A1 (de) | 1992-10-15 | 1994-04-21 | Bayer Ag | Sulfonylaminocarbonyltriazolinone |
| DE4334791A1 (de) | 1993-10-13 | 1995-04-20 | Bayer Ag | Bibenzylsynthase-Gene |
| DE4411913A1 (de) * | 1994-04-07 | 1995-10-12 | Bayer Ag | Substituierte Sulfonylaminocarbonyltriazolinone |
| US5693590A (en) | 1994-08-30 | 1997-12-02 | Rohm And Haas Company | Compositions containing phosphosulfonate herbicides and dichloroacetamide safeners |
| DE4435547A1 (de) * | 1994-10-05 | 1996-04-11 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit über Sauerstoff und Schwefel gebundenen Substituenten |
| US5670691A (en) | 1994-10-18 | 1997-09-23 | Rohm And Haas Company | Method for making a substituted benzene compound |
| IL115499A (en) * | 1994-10-18 | 1999-12-22 | Rohm & Haas | Preparation of 2,6-disubstituted benzensulfonate and certain derivatives thereof |
| DE19502579A1 (de) | 1995-01-27 | 1996-08-01 | Bayer Ag | Sulfonylamino(thio)carbonyl-triazolin(thi)one |
| DE19508119A1 (de) | 1995-03-08 | 1996-09-12 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit Halogenalkylthio-Substituenten |
| DE19508118A1 (de) | 1995-03-08 | 1996-09-12 | Bayer Ag | Sulfonylaminocarbonyltriazoline mit Halogenalkoxy-Substituenten |
| DE19517505A1 (de) | 1995-05-12 | 1996-11-14 | Bayer Ag | Sulfonylamino(thio)carbonyltriazolin(thi)one mit Aryloxy- oder Arylthio-Substituenten |
| DE19525162A1 (de) | 1995-07-11 | 1997-01-16 | Bayer Ag | Sulfonylamino(thio)carbonylverbindungen |
| DE19608445A1 (de) * | 1996-03-05 | 1997-09-11 | Bayer Ag | Substituierte Arylsulfonyl(thio)harnstoffe |
| AU2852397A (en) | 1996-07-22 | 1998-01-29 | Rohm And Haas Company | Herbicidal method utilizing phosphosulfonate herbicides and oxime ether safeners |
| BR9706774B1 (pt) | 1996-09-24 | 2009-01-13 | composto de n-(triazolazinil) arilsulfonamida, composiÇço herbicida, mÉtodo de controle de vegetaÇço indesejÁvel e compostos de cloreto de piridina-3-sulfonila e de 2-amino [1,2,4] triazol [1,5-c] pirimidina. |
-
1995
- 1995-07-11 DE DE19525162A patent/DE19525162A1/de not_active Withdrawn
-
1996
- 1996-06-28 EP EP03011479A patent/EP1344771A1/de not_active Withdrawn
- 1996-06-28 ES ES96924805T patent/ES2202457T3/es not_active Expired - Lifetime
- 1996-06-28 AU AU65146/96A patent/AU703153B2/en not_active Ceased
- 1996-06-28 CA CA002226669A patent/CA2226669C/en not_active Expired - Fee Related
- 1996-06-28 WO PCT/EP1996/002826 patent/WO1997003056A1/de active IP Right Grant
- 1996-06-28 JP JP50545697A patent/JP4084414B2/ja not_active Expired - Fee Related
- 1996-06-28 CN CN96196753.6A patent/CN1086696C/zh not_active Expired - Fee Related
- 1996-06-28 EP EP96924805A patent/EP0842157B1/de not_active Expired - Lifetime
- 1996-06-28 DE DE59610689T patent/DE59610689D1/de not_active Expired - Lifetime
- 1996-06-28 BR BR9609902A patent/BR9609902A/pt not_active IP Right Cessation
- 1996-07-10 ZA ZA965841A patent/ZA965841B/xx unknown
- 1996-07-11 AR ARP960103542A patent/AR002810A1/es unknown
-
1998
- 1998-12-30 US US09/223,246 patent/US6251831B1/en not_active Ceased
-
1999
- 1999-03-17 HK HK99101110A patent/HK1016167A1/xx not_active IP Right Cessation
-
2001
- 2001-01-17 CN CNB011015276A patent/CN1252047C/zh not_active Expired - Fee Related
- 2001-04-20 US US09/838,812 patent/US6525211B1/en not_active Expired - Fee Related
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115872909A (zh) * | 2022-12-27 | 2023-03-31 | 沈阳有色金属研究院有限公司 | 一种硫化矿捕收剂n-苯磺酰基-o-烷基硫代氨基甲酸酯及其制备方法和应用 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE19525162A1 (de) | 1997-01-16 |
| US6251831B1 (en) | 2001-06-26 |
| AU703153B2 (en) | 1999-03-18 |
| DE59610689D1 (de) | 2003-10-02 |
| AU6514696A (en) | 1997-02-10 |
| EP0842157A1 (de) | 1998-05-20 |
| HK1016167A1 (en) | 1999-11-03 |
| BR9609902A (pt) | 1999-06-29 |
| CA2226669C (en) | 2006-10-17 |
| WO1997003056A1 (de) | 1997-01-30 |
| JPH11508595A (ja) | 1999-07-27 |
| CA2226669A1 (en) | 1997-01-30 |
| JP4084414B2 (ja) | 2008-04-30 |
| ES2202457T3 (es) | 2004-04-01 |
| EP1344771A1 (de) | 2003-09-17 |
| EP0842157B1 (de) | 2003-08-27 |
| CN1316418A (zh) | 2001-10-10 |
| CN1252047C (zh) | 2006-04-19 |
| CN1086696C (zh) | 2002-06-26 |
| AR002810A1 (es) | 1998-04-29 |
| ZA965841B (en) | 1997-01-31 |
| US6525211B1 (en) | 2003-02-25 |
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