CN1195347A - 取代的芳基磺酰氨基(硫代)羰基三唑啉(硫)酮 - Google Patents
取代的芳基磺酰氨基(硫代)羰基三唑啉(硫)酮 Download PDFInfo
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- CN1195347A CN1195347A CN 96196762 CN96196762A CN1195347A CN 1195347 A CN1195347 A CN 1195347A CN 96196762 CN96196762 CN 96196762 CN 96196762 A CN96196762 A CN 96196762A CN 1195347 A CN1195347 A CN 1195347A
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- -1 Substituted aryl sulphonyl amino (thio) carbonyl triazolin Chemical compound 0.000 title claims abstract description 231
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 37
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 34
- 239000005864 Sulphur Substances 0.000 claims abstract description 31
- 239000001301 oxygen Substances 0.000 claims abstract description 29
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 23
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 14
- 150000002367 halogens Chemical class 0.000 claims abstract description 14
- 239000001257 hydrogen Substances 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 14
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 11
- 150000003839 salts Chemical class 0.000 claims abstract description 11
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000004104 aryloxy group Chemical group 0.000 claims abstract description 8
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 8
- 125000003302 alkenyloxy group Chemical group 0.000 claims abstract description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000004414 alkyl thio group Chemical group 0.000 claims abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 4
- 125000000623 heterocyclic group Chemical group 0.000 claims abstract description 4
- 125000006323 alkenyl amino group Chemical group 0.000 claims abstract description 3
- 125000005108 alkenylthio group Chemical group 0.000 claims abstract description 3
- 125000001691 aryl alkyl amino group Chemical group 0.000 claims abstract description 3
- 125000005110 aryl thio group Chemical group 0.000 claims abstract description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 claims abstract description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims abstract description 3
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 3
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims abstract description 3
- 125000005366 cycloalkylthio group Chemical group 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 34
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 32
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 32
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 31
- 241000196324 Embryophyta Species 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 19
- 229910052801 chlorine Inorganic materials 0.000 claims description 19
- 239000000203 mixture Substances 0.000 claims description 17
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 14
- 150000002576 ketones Chemical class 0.000 claims description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 14
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical group [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims description 14
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 11
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 11
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 9
- 229910052794 bromium Inorganic materials 0.000 claims description 9
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 8
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 8
- GDOPTJXRTPNYNR-UHFFFAOYSA-N methylcyclopentane Chemical compound CC1CCCC1 GDOPTJXRTPNYNR-UHFFFAOYSA-N 0.000 claims description 8
- 229930192474 thiophene Natural products 0.000 claims description 8
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 7
- 239000011737 fluorine Substances 0.000 claims description 7
- 229910052731 fluorine Inorganic materials 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000001544 thienyl group Chemical group 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000004429 atom Chemical group 0.000 claims description 6
- 125000002541 furyl group Chemical group 0.000 claims description 6
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 claims description 6
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 5
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 claims description 5
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 4
- MJBPUQUGJNAPAZ-UHFFFAOYSA-N Butine Natural products O1C2=CC(O)=CC=C2C(=O)CC1C1=CC=C(O)C(O)=C1 MJBPUQUGJNAPAZ-UHFFFAOYSA-N 0.000 claims description 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 4
- 125000002905 alkanoylamido group Chemical group 0.000 claims description 4
- 125000004171 alkoxy aryl group Chemical group 0.000 claims description 4
- 125000006319 alkynyl amino group Chemical group 0.000 claims description 4
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 4
- 125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 4
- 125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 4
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 4
- 229910052799 carbon Inorganic materials 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
- 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
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 4
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 4
- QFXZANXYUCUTQH-UHFFFAOYSA-N ethynol Chemical group OC#C QFXZANXYUCUTQH-UHFFFAOYSA-N 0.000 claims description 4
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 4
- MDQRDWAGHRLBPA-UHFFFAOYSA-N fluoroamine Chemical compound FN MDQRDWAGHRLBPA-UHFFFAOYSA-N 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 4
- 125000002112 pyrrolidino group Chemical group [*]N1C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 4
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 claims description 3
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 3
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 claims description 3
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 3
- JSLZUBLGGPEVQN-DIPNUNPCSA-N (2r)-4-methyl-2-propan-2-yl-2-[2-[4-[4-[2-(3,4,5-trimethoxyphenyl)ethyl]piperazin-1-yl]butoxy]phenyl]-1,4-benzothiazin-3-one Chemical compound COC1=C(OC)C(OC)=CC(CCN2CCN(CCCCOC=3C(=CC=CC=3)[C@@]3(C(N(C)C4=CC=CC=C4S3)=O)C(C)C)CC2)=C1 JSLZUBLGGPEVQN-DIPNUNPCSA-N 0.000 claims description 2
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 2
- 125000006799 (C2-C6) alkenylamino group Chemical group 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 2
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 2
- QRWSUXGRFSTIRN-UHFFFAOYSA-N S1CCCC1.[O] Chemical compound S1CCCC1.[O] QRWSUXGRFSTIRN-UHFFFAOYSA-N 0.000 claims description 2
- MJYGPNBYCMSMFL-UHFFFAOYSA-N [O].C1CCOC1 Chemical compound [O].C1CCOC1 MJYGPNBYCMSMFL-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 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
- 229910021529 ammonia Inorganic materials 0.000 claims description 2
- 125000004391 aryl sulfonyl group Chemical group 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
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical class NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 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
- 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 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000011575 calcium Substances 0.000 claims description 2
- 229910052791 calcium Inorganic materials 0.000 claims description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 claims description 2
- 125000001352 cyclobutyloxy group Chemical group C1(CCC1)O* 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
- 125000006317 cyclopropyl amino group Chemical group 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
- 125000003700 epoxy group Chemical group 0.000 claims description 2
- 150000002240 furans Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 229950001891 iprotiazem Drugs 0.000 claims description 2
- 239000011777 magnesium Substances 0.000 claims description 2
- 229910052749 magnesium Inorganic materials 0.000 claims description 2
- 125000003566 oxetanyl group Chemical group 0.000 claims description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 claims description 2
- 239000011591 potassium Substances 0.000 claims description 2
- 229910052700 potassium Inorganic materials 0.000 claims description 2
- 239000011734 sodium Substances 0.000 claims description 2
- 229910052708 sodium Inorganic materials 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-O sulfonium Chemical compound [SH3+] RWSOTUBLDIXVET-UHFFFAOYSA-O 0.000 claims description 2
- 125000002030 1,2-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([*:2])C([H])=C1[H] 0.000 claims 1
- 125000003320 C2-C6 alkenyloxy group Chemical group 0.000 claims 1
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims 1
- 125000003968 arylidene group Chemical group [H]C(c)=* 0.000 claims 1
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims 1
- VKFAUCPBMAGVRG-UHFFFAOYSA-N dipivefrin hydrochloride Chemical compound [Cl-].C[NH2+]CC(O)C1=CC=C(OC(=O)C(C)(C)C)C(OC(=O)C(C)(C)C)=C1 VKFAUCPBMAGVRG-UHFFFAOYSA-N 0.000 claims 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 3
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 2
- 125000006193 alkinyl group Chemical group 0.000 abstract 2
- 150000002431 hydrogen Chemical class 0.000 abstract 2
- 125000004659 aryl alkyl thio group Chemical group 0.000 abstract 1
- 125000002102 aryl alkyloxo group Chemical group 0.000 abstract 1
- 125000001769 aryl amino group Chemical group 0.000 abstract 1
- 125000000732 arylene group Chemical group 0.000 abstract 1
- 125000005549 heteroarylene group Chemical group 0.000 abstract 1
- 125000005844 heterocyclyloxy group Chemical group 0.000 abstract 1
- 125000004468 heterocyclylthio group Chemical group 0.000 abstract 1
- 239000002585 base Substances 0.000 description 34
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 26
- 238000002360 preparation method Methods 0.000 description 19
- 239000007858 starting material Substances 0.000 description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- 239000002904 solvent Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 8
- 244000025254 Cannabis sativa Species 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 239000000843 powder Substances 0.000 description 6
- 235000005781 Avena Nutrition 0.000 description 5
- 244000075850 Avena orientalis Species 0.000 description 5
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 5
- 241000209149 Zea Species 0.000 description 5
- 239000000975 dye Substances 0.000 description 5
- 239000000706 filtrate Substances 0.000 description 5
- 229910052500 inorganic mineral Inorganic materials 0.000 description 5
- 235000010755 mineral Nutrition 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229910052938 sodium sulfate Inorganic materials 0.000 description 5
- 235000011152 sodium sulphate Nutrition 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 241000219198 Brassica Species 0.000 description 4
- DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 4
- 235000021506 Ipomoea Nutrition 0.000 description 4
- 241000207783 Ipomoea 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 241000207763 Solanum Species 0.000 description 4
- 235000002634 Solanum Nutrition 0.000 description 4
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 150000002148 esters Chemical class 0.000 description 4
- 230000002363 herbicidal effect Effects 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
- 229940032021 tetramune Drugs 0.000 description 4
- 241000219318 Amaranthus Species 0.000 description 3
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- 241000234653 Cyperus Species 0.000 description 3
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 3
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- 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
- 239000011148 porous material Substances 0.000 description 1
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 1
- 235000015320 potassium carbonate Nutrition 0.000 description 1
- GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
- MFOUDYKPLGXPGO-UHFFFAOYSA-N propachlor Chemical compound ClCC(=O)N(C(C)C)C1=CC=CC=C1 MFOUDYKPLGXPGO-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 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
- 239000003531 protein hydrolysate Substances 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- UBQKCCHYAOITMY-UHFFFAOYSA-N pyridin-2-ol Chemical compound OC1=CC=CC=N1 UBQKCCHYAOITMY-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
- 239000002994 raw material Substances 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
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- 239000008234 soft water Substances 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 description 1
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- 229910021653 sulphate ion Inorganic materials 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 125000002053 thietanyl group Chemical group 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- 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
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/12—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/38—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< where at least one nitrogen atom is part of a heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
- C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
- C07D409/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及式(Ⅰ)新的取代芳基磺酰氨基(硫代)羰基三唑啉(硫)酮,其中Ar是可被取代的亚芳基或杂亚芳基;Q1是氧或硫,Q2是氧或硫,R1是氢、羟基、氨基、亚烷基氨基或可被取代的下述基团:烷基、链烯基、链炔基、烷氧基、链烯氧基、烷基氨基、二烷基氨基、链烷酰氨基、环烷基、环烷基烷基、芳基、芳烷基;R2是氢、羟基、巯基、氨基、卤素或可被取代的下述基团:烷基、链烯基、链炔基、烷氧基、链烯氧基、链炔氧基、烷硫基、链烯硫基、链炔硫基、烷基氨基、链烯基氨基、链炔基氨基、二烷基氨基、链烷酰氨基、氮丙啶基、吡咯烷基、哌啶子基、吗啉代、环烷基、环烯基、环烷氧基、环烷硫基、环烷基氨基、环烷基烷基、环烷基烷氧基、环烷基烷硫基、环烷基烷基氨基、芳基、芳氧基、芳硫基、芳氨基、芳烷基、芳烷氧基、芳烷硫基、芳烷基氨基、杂环氧基、杂环硫基;或R1和R2连在一起可以是支链的链烷二基;和R3是可被取代的杂环基;和式(Ⅰ)化合物的盐,该新化合物的制备方法和它们作为除草剂的用途。
Description
本发明涉及新的取代的芳基磺酰氨基(硫代)羰基三唑啉(硫)酮化合物,多种制备这些化合物的方法及它们作为除草剂的用途。
已经知道的是,某些磺酰氨基羰基三唑啉酮类具有除草性能(参见EP-A341489、EP-A422469、EP-A425948、EP-A431291、EP-A507171)。然而,这些化合物的活性在各方面都不能满足要求。
因此,本发明提供了如下通式(I)的新的取代的芳基磺酰氨基(硫代)羰基三唑啉(硫)酮及式(I)化合物的盐:其中Ar 分别代表任选取代的亚芳基或杂亚芳基,Q1 代表氧或硫,Q2 代表氧或硫,R1 代表氢、羟基、氨基、亚烷基氨基或分别代表任选取代的下述基:
烷基、链烯基、链炔基、烷氧基、链烯氧基、烷基氨基、二烷基氨
基、链烷酰氨基、环烷基、环烷基烷基、芳基、芳烷基,R2 代表氢、羟基、巯基、氨基、卤素或分别代表任选取代的下述基:
烷基、链烯基、链炔基、烷氧基、链烯氧基、链炔氧基、烷硫基、
链烯硫基、链炔硫基、烷基氨基、链烯基氨基、链炔基氨基、二烷
基氨基、链烷酰氨基、氮丙啶基、吡咯烷子基、哌啶子基、吗啉代、
环烷基、环烯基、环烷氧基、环烷硫基、环烷基氨基、环烷基烷基、
环烷基烷氧基、环烷基烷硫基、环烷基烷基氨基、芳基、芳氧基、
芳硫基、芳氨基、芳烷基、芳烷氧基、芳烷硫基、芳烷基氨基、杂
环氧基、杂环硫基,或R1和R2一起代表任选支链烷二基,而R3代表任选取代的杂环基。
在如下情况下可得到通式(I)新的取代的芳基磺酰氨基(硫代)羰基三唑啉(硫)酮:
Q1、R1和R2各自如上定义,与如下通式(III)取代的异(硫代)氰酸芳基磺酰酯反应:
R3-O-CO-Ar-SO2-N=C=Q2 (III)其中
Ar、Q2和R3各自如上定义,或
(b)如果合适在一种酸接受体存在下,以及如果合适在一种稀释剂存在下,使如下通式(IV)的三唑啉(硫)酮衍生物:其中
Q1、Q2、R1和R2各自如上定义,而
Z代表卤素、烷氧基、芳氧基或芳基烷氧基,与如下通式(V)的磺酰胺反应:
R3-O-CO-Ar-SO2-NH2 (V)其中
Ar和R3各自如上定义,或
(c)如果合适在一种酸接受体存在下,以及如果合适在一种稀释剂存在下,使如下通式(II)的三唑啉(硫)酮:其中
Q1、R1和R2各自如上定义,与如下通式(VI)取代的芳基磺酰胺衍生物反应:
R3-O-CO-Ar-SO2-NH-CQ2-Z (VI)其中
Ar、Q2和R3各自如上定义,而
Z代表卤素、烷氧基、芳氧基或芳基烷氧基,或
(d)如果合适在一种反应助剂存在下,以及如果合适在一种稀释剂存在下,使如下通式(II)的三唑啉(硫)酮:其中
Q1、R1和R2各自如上定义,与如下通式(VII)取代的芳基磺酰卤反应:
R3-O-CO-Ar-SO2-X (VII)其中
Ar和R3各自如上所定义,而X代表卤素和如下通式(VIII)的金属(硫代)氰酸盐:
MQ2CN (VIII)其中
Q2如上所定义,而
M代表碱金属或一当量的碱土金属,如果合适将由方法(a)、(b)、(c)或(d)得到的式(I)化合物通过常规方法转化成盐。
通式(I)的新的磺酰氨基(硫代)羰基三唑啉(硫)酮具有优良的除草活性。
本发明优选提供式(I)化合物,其中Ar 代表亚苯基或亚萘基,它们各自任选地被卤素、氰基、硝基取代,
被C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4-烷
基亚磺酰、C1-C4-烷基磺酰、二(C1-C4-烷基)氨基磺酰
或N-C1-C4-烷氧基-N-C1-C4-烷基氨基磺酰(它们各
自任选地被氟和/或氯所取代)所取代,或代表5或6个环原子的杂亚
芳基,其中至少一个环原子是氧、硫或氮并且一个或两个以上任选
为氮,该原子任选被卤素、氰基、硝基取代、被C1-C4-烷基或
C1-C4-烷氧基(它们各自任选被氟和/或氯所取代)取代,Q1 代表氧或硫,Q2 代表氧或硫,R1 代表氢、羟基、氨基、代表C2-C10-亚烷基氨基,代表任选氟-、
氯-、溴-、氰基-、C1-C4-烷氧基-、C1-C4-烷基羰基-
或C1-C4-烷氧基羰基-取代的C1-C6-烷基,代表分别任选
由氟-、氯-、和/或溴取代的C2-C6-链烯基或C2-C6-链炔
基,代表分别任选由氟-、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-烷基氨基或
C1-C6-链烷酰氨基,代表C3-C6-链烯氧基、代表二(C1-C4
-烷基)氨基、代表分别任选由氟-、氯-、溴-、氰基-和/或
C1-C4-烷基取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4
-烷基,或代表分别任选由氟-、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
基或苯基-C1-C4-烷基,R2 代表氢、羟基、巯基、氨基、氟、氯、溴、碘,代表任选由氟-、
氯-、溴-、氰基-、C1-C4-烷氧基-、C1-C4-烷基羰基-
或C1-C4-烷氧基-羰基-取代的C1-C6-烷基,代表分别任选由
氟-、氯-、和/或溴-取代的C2-C6-链烯基或C2-C6-链炔
基,代表分别任选由氟-、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-烷硫
基、C1-C6-烷基氨基或C1-C6-链烷酰氨基,代表C2-C6-
链烯氧基、C2-C6-链炔氧基、C2-C6-链烯硫基、C2-C6-
链炔硫基、C2-C6-链烯基氨基或C2-C6-链炔基氨基、代表
二(C1-C4-烷基)氨基、代表分别任选由甲基-、和/或乙基取
代的氮丙啶基、吡咯烷子基、哌啶子基或吗啉代,代表分别任选由
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-环烷氧基、C3-C6-环
烷硫基、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-烷硫基或C3-C6-环烷基-C1-C4-烷基氨基,
或代表分别任选由氟-、氯-、溴-、氰基-、硝基-、C1-C4
-烷基-、三氟甲基-和/或C1-C4-烷氧基取代的取代苯基、苯
基-C1-C4-烷基、苯氧基、苯基-C1-C4-烷氧基、苯硫基、
苯基-C1-C4-烷硫基、苯基氨基或苯基-C1-C4-烷基氨基,
或代表分别任选由氟-、氯-、溴-、氰基、硝基-、C1-C4-
烷基-、三氟甲基-和/或C1-C4-烷氧基取代的杂环氧基或杂环
硫基,在各种情况下该杂环基成分选自环氧乙烷基、氧杂环丁基
(oxetanyl)、呋喃基、四氢呋喃基、噻环丁基(thietanyl)、噻
吩基、四氢噻吩基,或R1和R2一起代表任选具有3-11个碳原子的支链烷二基,以及R3 代表分别任选由卤素-或C1-C4-烷基取代的氧杂环丁基、噻环
丁基、呋喃基、四氢呋喃基、噻吩基或四氢噻吩基。
此外,本发明优先地提供了其中Ar、Q1、Q2、R1、R2和R3各为如上优选方式所定义的式(I)化合物的钠、钾、镁、钙、铵、C1-C4-烷基铵、二(C1-C4-烷基)铵、三(C1-C4-烷基)铵、四(C1-C4-烷基)铵、三(C1-C4-烷基)锍、C5-或C6-环烷基铵和二(C1-C2-烷基)苄基铵盐。
本发明特别地提供了式(I)化合物,其中Ar 代表分别任选由氟-、氯-、溴-、氰基-、硝基-、甲基-、
乙基-、正-或异-丙基-、三氟甲基-、甲氧基-、乙氧基-、
二氟甲氧基-、三氟甲氧基-、甲硫基-或乙硫基-取代的1,2-
亚苯基(邻亚苯基)、吡啶-2,3-二基、噻吩-2,3-二基或吡
唑-4,5-二基,Q1 代表氧或硫,Q2 代表氧或硫,R1 代表氢、羟基、氨基,代表C3-C8-亚烷基氨基,代表分别任选
由氟-、氯-、氰基-、甲氧基-或乙氧基-取代的甲基、乙基、
正-或异丙基-、正-、异-、仲-或叔-丁基,代表分别任选由
氟-、氯-或溴-取代的丙烯基、丁烯基、丙炔基或丁炔基,代表
分别任选氟-、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、甲氨
基、乙氨基、正-或异-丙氨基、正-、异-、仲-或叔-丁氨基,
代表丙烯氧基或丁烯氧基,代表二甲氨基或二乙氨基,代表分别任
选氟-、氯-、甲基-和/或乙基-取代的环丙基、环丁基、环戊基、
环己基、环丙甲基、环丁甲基、环戊甲基或环己甲基,或代表分别
任选氟-、氯-、甲基-、三氟甲基-和/或甲氧基-取代的苯基或
苄基,R2 代表氢、羟基、巯基、氨基、氟、氯、溴,代表分别任选氟-、
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,代表分别任选氟-、氯-、
或溴-取代的丙烯基、丁烯基、丙炔基或丁炔基,代表分别任选氟-、
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、甲硫基、乙硫基、
正或异丙硫基、正,异,仲或叔丁硫基、甲基氨基、乙基氨基、
正-或异丙基氨基、正,异,仲或叔丁基氨基,代表丙烯氧基、丁
烯氧基、丙炔氧基、丁炔氧基、丙烯硫基、丁烯硫基、丙炔硫基、
丁炔硫基、丙烯氨基、丁烯氨基、丙炔氨基、或丁炔氨基,代表二
甲氨基、二乙氨基或二丙氨基,代表分别任选由氟-、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、环丙氧基、环丁氧基、环戊氧基、环己氧基、环丙硫基、
环丁硫基、环戊硫基、环己硫基、环丙氨基、环丁氨基、环戊氨基、
环己氨基、环丙甲基、环丁甲基、环戊甲基、环己甲基、环丙甲氧
基、环丁甲氧基、环戊甲氧基、环己甲氧基、环丙甲硫基、环丁甲
硫基、环戊甲硫基、环己甲硫基、环丙甲氨基、环丁甲氨基、环戊
甲氨基或环己甲氨基,或代表分别任选由氟-、氯-、甲基-、三
氟甲基-和/或甲氧基-取代的苯基、苄基、苯氧基、苄氧基、苯硫
基、苄硫基、苯基氨基或苄基氨基,或代表分别任选由氟-、氯-、
甲基-三氟甲基-和/或甲氧基-取代的氧杂环丁氧基、呋喃氧基、
四氢呋喃氧基、噻吩氧基或四氢噻吩氧基,或R1和R2一起代表任选具有3-11个碳原子的支链烷二基,以及R3 代表分别任选由氟-、氯-、甲基-或乙基-取代的氧杂环丁基、
噻环丁基、呋喃基、四氢呋喃基、噻吩基或四氢噻吩基。
以上所列出的一般或优选的基团限定对式(I)的最终产物,以及还有同样地对各个制备场合下所需的原料或中间体均有效。这些基团的限定可根据需要彼此结合,即包括给定的优选化合物范围之间的结合。
例如,使用2-(噻环丁-3-基-氧基-羰基)苯磺酰胺和2氯羰基-4-二甲氨基-5-甲基-2,4-二氢-3H-1,2,4-三唑-3-硫酮作为起始物料,本发明方法(b)的反应过程可由如下反应流程图来说明:
例如,使用4-乙基-5-乙硫基-2,4-二氢-3H-1,2,4-三唑-3-酮和2-(3-噻环丁氧基羰基)苯磺酰氯及氰酸钾作为起始物料,本发明方法(d)的反应过程可由如下反应流程图来说明:
式(II)提供了对用作制备式(I)化合物的本发明的方法(a)、(c)和(d)中起始物料的三唑啉(硫)酮的一般定义。在式(II)中,Q1、R1和R2各自优选或最优选的含义已在上面给出,它们与本发明式(I)化合物中所述的优选或最优选的Q1、R1和R2的含义相同。
通式(II)的三唑啉(硫)酮是已知的和/或可通过已知方法本身制得(参见Arch.Pharm.301(1968),827;同前,307(1974),889;法国化学会通报(Bull.Soc.Chim.France)1962,1365;同前,1975,1191;化学学报(德)(Chem.Ber.)90(1957),909-921;同前,98(1965),3025-3099;同前,102(1969),755;杂环化学(J.Heterocycl.Chem.)15(1978),237-240;印度化学会志(J.Indian Chem.Soc.)6(1929),565;利比西化学年鉴(Liebigs Ann.Chem.)637(1960),135;化学月报(奥)(Monatshefte Chemie)123(1992),257;四面体(Tetrahedron)32(1976),2347-2352;瑞士化学会志(Helv.Chim.Acta.)63(1980),841-859;化学会志(J.Chem.Soc.)C1967,746-751;同前,1970,26-34;化学会志(J.Chem.Soc.)Perkin I 1973,2644;Fen Fak.Derg.,Seri A(Ege Univ.)7(1984),在化学文摘(Chem.Abstracts)101:90846m中引用的1-6;EP-A283876;EP-A294666;EP-A298371;EP-A301946;EP-A305844;EP-A341489;EP-A362633;EP-A370293;EP-A391187;EP-A398096;EP-A398097;EP-A399294;EP-A415196;EP-A422469;EP-A425948;EP-A431291;EP-A477646;EP-A502307;EP-A503437;EP-A505819;EP-A511569;EP-A513621;DE-A2336827;DE-A3839206;DE-A3916208;DE-A3916930;DD-P64970;WO-A93/04050;制备实施例)。
式(III)提供了另外用作制备式(I)化合物的本发明方法(a)中起始物料的取代异(硫代)氰酸芳基磺酰酯的一般限定。在式(III)中,Ar、Q2和R3各自优选或最优选的含义已在上面给出,它们与本发明式(I)化合物中所述的优选或最优选的Ar、Q2和R3的含义相同。
式(III)的起始物料是已知的和/或可由已知方法本身制得(参见EP-A496701、EP-A558445)。
式(IV)提供了用作制备通式(I)化合物的本发明方法(b)中起始物料的三唑啉(硫)酮衍生物的一般限定。在式(IV)中Q1、Q2、R1和R2各自优选或最优选的含义已在上面给出,它们与本发明式(I)化合物中所述的优选或最优选的Q1、Q2、R1和R2的含义相同;Z优选代表氟、氯、溴、甲氧基、乙氧基、苄氧基、苯氧基、卤素-或硝基-苯氧基,特别是甲氧基、苯氧基或4-硝基苯氧基。
某些式(IV)的起始物料还没有在文献中公开,并构成了通常确定的在先专利申请的主题部分。
如果合适在一种酸接受体,例如氢氧化钠或氢氧化钾、叔丁醇钠或叔丁醇钾存在时,并且如果合适在一种稀释剂,例如二氯甲烷、四氢呋喃或二甲氧基乙烷和/或水存在下,在温度0℃和100℃之间,使如下通式(II)的三唑啉(硫)酮:其中
Q1、R1和R2如上定义,与如下通式(IX)的碳酸衍生物反应
Z-CO-Z1 (IX)其中
Z为如上所定义的并且
Z1代表卤素、烷氧基、芳烷氧基或芳氧基(并且具有如Z相同的优选含义),可得到通式(IV)的化合物。
式(V)提供了另外用作制备通式(I)化合物的本发明方法(b)中起始物料的磺酰胺的一般定义。在式(V)中,Ar和R3各自优选或最优选的含义已在上面给出,它们与本发明式(I)化合物中所述的优选或最优选的Ar和R3的含义相同。
式(V)的起始物料是已知的和/或可由已知方法本身制得(参见EP-A496701、EP-A558445)。
式(VI)提供了用作制备式(I)化合物的本发明方法(c)中起始物料的取代的芳基磺酰胺衍生物的一般定义。在式(VI)中,Ar、Q2和R3各自优选或最优选的含义已在上面给出,它们与本发明式(I)化合物中所述的优选的或最优选的Ar、Q2和R3的含义相同;Z优选代表氟、氯、溴、甲氧基、乙氧基、苄氧基、苯氧基、卤素-或硝基-苯氧基、特别是甲氧基、苯氧基或4-硝基-苯氧基。
式(VI)的起始物料是已知的和/或可由已知方法本身制得。
式(VII)提供了用作制备式(I)化合物的本发明方法(d)中起始物料的取代芳基磺酰卤的一般定义。在式(VII)中,Ar和R3各自优选或最优选的含义已在上面给出,它们与本发明式(I)化合物中所述的优选或最优选的Ar和R3的含义相同;X优选代表氟、氯或溴,特别是氯。
式(VII)的起始物料是已知的和/或可由已知方法本身制得(参见EP-A496701、EP-A558445)。
本发明制备式(I)新化合物的方法(a)、(b)、(c)和(d)优选地使用稀释剂进行。关于这一点,合适的稀释剂实际上是所有的惰性有机溶剂。这些溶剂优选包括脂族和芳族,任选卤代烃类,如戊烷、己烷、庚烷、环己烷、石油醚、汽油、石油英、苯、甲苯、二甲苯、二氯甲烷、氯化乙烯、氯仿、四氯甲烷、氯苯、和O-二氯苯;醚类,如乙醚和二丁醚、乙二醇二甲醚和二甘醇二甲醚、四氢呋喃和二噁烷;酮类,如丙酮,甲基·乙基酮、甲基·异丙基酮和甲基·异丁基酮;酯类,如乙酸甲酯和乙酸乙酯;腈类,如乙腈和丙腈;酰胺类,如二甲基甲酰胺、二甲基乙酰胺和N-二甲基吡咯烷酮,以及还有二甲亚砜、四氢噻吩砜和六甲基磷酰三胺。
作为本发明方法(a)、(b)、(c)和(d)中的反应助剂和/或酸接受体,可使用通常能用于这些反应的所有酸结合剂。优选碱金属氢氧化物,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、碱金属碳酸盐和醇盐,如碳酸钠和碳酸钾、叔丁醇钠和叔丁醇钾、以及还有碱性氮化合物,如三甲胺、三乙胺、三丙胺、三丁胺、二异丁胺、二环己胺、乙基二异丙胺、乙基二环己胺、N,N-二甲基苄胺、N,N-二甲基苯胺、吡啶、2-甲基-、3-甲基-、4-甲基-、2,4-二甲基-、2,6-二甲基-、2-乙基-、4-乙基-和5-乙基-2-甲基吡啶、1,5-二氮杂二环[4,3,0]壬-5-烯(DBN)、1,8-二氮杂二环-[5,4,0]-十一-7-烯(DBU)和1,4-二氮杂二环-[2,2,2]-辛烷(DABCO)。
本发明方法(a)、(b)、(c)和(d)的反应温度可在较宽范围内变化。反应通常是在-20℃-+150℃之间温度下进行,优选温度为0℃-+100℃之间。
本发明方法(a)、(b)、(c)和(d)通常是在常压下进行。然而,也可在升压或减压下进行操作。
为进行本发明方法(a)、(b)、(c)和(d)每种场合下所需的起始物料,通常是以接近等摩尔量使用。然而,也可在每种场合下较大过量使用一种组分。反应通常是在有一种酸接受体存在下,在一种合适的稀释剂中进行,并将该反应混合物在所需的特定温度下搅拌若干小时。本发明方法(a)、(b)、(c)和(d)的操作,在各自场合下,用常规方法进行(参见制备实施例)。
如有需要,可制备本发明通式(I)化合物的盐。这些盐可通过形成盐的常规方法,例如通过将式(I)化合物溶解或分散在一种合适的溶剂中,例如二氯甲烷、丙酮、叔丁基甲基醚或甲苯,并添加一种合适的碱,以简便的方式制得。然后如有必要在长时间搅拌后可将这些盐用抽吸浓缩或过滤进行分离。
本发明的活性化合物可用作脱叶剂、干燥剂、除秸剂以及,特别是用作除莠剂。在广义上,有关杂草要理解为在不希望的地点生长的所有植物。本发明的物质是充当完全的还是选择性的除草剂,基本上取决于所用的量。
例如,本发明的活性化合物可用于如下植物方面:
双子叶属杂草: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)、牛膝属(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)、番薯属(Ipomoea)、蓼属(Polygonum)、田菁属(Sesbania)、豚草属(Ambrosia)、蓟属(Cirsium)、飞蠊属(Carduus)、苦苣菜属(Sonchus)、茄属(Solanum)、蔊菜属(Rorippa)、水松草属(Rotala)、母草属(Lindernia)、野芝麻属(Lamium)、婆婆纳属(Veronica)、苘麻属(Abutilon)、Emex、曼陀罗属(Datura)、堇菜属(Viola)、鼬瓣花属(Galeopsis)、罂粟属(Papaver)、矢车菊属(Centaurea)、三叶草属(Trifolium)、毛茛属(Ranunculus)和蒲公英(Taraxacum)。
双子叶属作物:棉属(Gossypium)、大豆属(Glycine)、甜菜属(Beta)、胡萝卜属(Daucus)、菜豆属(Phaseolus)、豌豆属(Pisum)、茄属(Solanum)、亚麻属(Linum)、番薯属(Ipomoea)、巢菜属(Vicia)、烟草属(Nicotiana)、番茄属(Lycopersicon)、花生属(Arachis)、芸苔属(Brassica)、莴苣属(Lactuca)、黄瓜属(Cucumis)和南瓜属(Cucurbita)。
单子叶属杂草: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)、毒麦属(Lolium)、雀麦属(Bromus)、燕麦属(Avena)、莎草属(Cyperus)、高粱属(Sorghum)、冰草属(Agropyron)、狗牙根属(Cynodon)、雨火花属(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。
单子叶属作物:稻属(Oryza)、玉蜀黍属(Zea)、小麦属(Triticum)、大麦属(Hordeum)、燕麦属(Avena)、黑麦属(Scale)、高粱属(Sorghum)、黍属(Panicum)、甘蔗属(Saccharum)、凤梨属(Ananas)、天门冬属(Asparagus)和葱属(Allium)。
然而,本发明的活性化合物用途决不限于这些属,而也以相同的方式扩大到其他植物。
这些化合物,取决于浓度,适于例如在工业地带和铁路轨道上,以及在有或没有植树的小路和广场上完全控制杂草。同样地,这些化合物可用来控制多年生作物,例如森林、装饰植物、果园、葡萄园、柑桔树林、坚果果园、香蕉种植园、咖啡种植园、茶叶种植园、橡胶种植园、油棕榈种植园、椰子种植园、软水果种植园和啤酒花田地、草坪、草皮和牧草地中的杂草,以及用于选择性控制一年生作物中的杂草。
本发明的式(I)化合物特别适于选择性控制在幼苗出现前和幼苗出现后,单子叶和双子叶作物中的单子叶和双子叶杂草。
这些活性化合物可被转化成常规制剂,如溶液、乳液、可湿粉末、悬浮液、粉末、粉尘剂、膏糊、可溶性粉末、颗粒、悬浮液-乳液浓缩物、浸渍活性化合物的天然和合成材料,以及极细的聚合物质胶囊。
这些制剂可用常规方法制得,例如将活性化合物与液体溶剂和/或固体载体等扩充剂混合,任选地同时使用乳化剂和/或分散剂和/或起泡剂等表面活性剂。
当使用水作为扩充剂时,也可使用例如有机溶剂作为辅助溶剂。主要的合适液体溶剂如下:芳族化合物,如二甲苯、甲苯或烷基萘。氯化芳族化合物和氯化脂族烃类,如氯苯、氯乙烯或二氯甲烷、脂族烃类,如环己烷或石蜡,例如石油馏份、矿物和植物油类、醇类、如丁醇或乙二醇及它们的醚类和酯类,酮类,如丙酮、甲基·乙基酮、甲基·异丁基酮或环己酮、强极性溶剂,如二甲基甲酰胺和二甲亚砜,以及水。
合适的固体载体如下:
例如铵盐和磨碎的天然矿物,如高岭土、粘土、滑石、石灰石、石英、硅镁土、蒙脱石或硅藻土、和磨碎的合成矿物,如细碎的二氧化硅、氧化铝和硅酸盐,合适的颗粒固体载体为:例如破碎和分级的天然岩石,如方解石、大理石、浮石、海泡石和白云石,以及合成的无机和有机粉颗粒,和有机材料颗粒,如锯屑、椰子壳、玉米穗轴和烟草茎;合适的乳化剂和/或起炮剂为:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯、聚氧乙烯脂肪族醇醚,如烷芳基聚乙二醇醚、烷基磺酸盐、烷基硫酸盐、芳基磺酸盐以及蛋白质水解产物;合适的分散剂为:例如木质亚硫酸盐废液和甲基纤维素。
增粘剂,如羧甲基纤维素以及粉末、颗粒或乳胶状的天然和合成聚合物,如阿拉伯树胶、聚乙烯醇和聚乙酸乙烯酯、以及天然磷脂,如脑磷脂和卵磷脂,以及合成的磷脂可用于制剂。另外的添加剂可以是矿物和植物油类。
可使用着色剂,如无机颜料,例如氧化铁、二氧化钛和普鲁士蓝、以及有机染料,如茜素染料,偶氮染料和金属酞菁染料,以及微量养分,如铁、锰、硼、铜、钴、钼和锌的盐类。
制剂通常含有0.1-95%(重量)活性化合物,优选的为0.5和90%之间。
为控制杂草,本发明活性化合物(化合物本身或其制剂形式)也可与已知除草剂混合物使用,可以配成当场使用剂型、或可制成桶装混合物。
这些混合物的可能组分为已知的除草剂,例如N-酰苯胺类,如吡氟草胺和敌稗;芳基羧酸类,如二氯吡啶甲酸、麦草畏和毒莠定;芳氧基链烷酸类,如2,4-滴、2,4-滴丁酸、2,4-滴丙酸氰草烟、2甲4氯、2甲4氯丙酸和缘草定;芳氧基-苯氧基链烷酸酯类,如禾草灵(diclofop-methyl)、噁唑禾草灵(fenoxaprop-ethyl)、吡氟禾草灵(fluazifop-butyl)、吡氟氯禾灵(haloxyfop-methyl)和喹禾灵(quizalofop-ethyl);吡啶酮类,如杀草敏和达草灭;氨基甲酸酯类,如氯苯胺灵、甜菜安、苯敌草和苯胺灵;氯乙酰替苯胺类;如草不绿、乙草胺、去草胺、吡草胺、异丙甲草胺、丙草安如毒草安;二硝基苯胺类,如黄草消、二甲戊乐灵和氟乐灵;二苯醚类,如三氟羧草醚、治草醚、乙羧氟草醚、氟黄胺草醚、halosafen、乳氟禾草灵和乙氧氟草醚;脲类,如绿麦隆、敌草隆、伏草隆、异丙隆、利谷隆和噻唑隆;羟胺类,如禾草天、烯草酮、噻草酮、稀乐定和肟草酮;咪唑啉酮类,如咪草烟、咪草酯、灭草烟和灭草喹;腈类,如溴苯腈、敌草腈和碘苯腈;羟乙酰胺类,如苯噻草胺;磺酰脲类,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;硫代氨基甲酸酯类,如丁草特、灭草特、燕麦敌、茵达灭、禾草畏、草达灭、苄草丹、杀草丹和野燕畏;三嗪类,如莠去津、氰草津、西玛津、西草净、特丁净和特丁津;三嗪酮类,如环嗪酮、苯嗪草酮和嗪草酮;其他类,如杀草强、呋草黄、灭草松、环庚草醚、异噁草酮、二氯吡啶酸、defenzoquat、氟硫草定、乙呋草黄、氟咯草酮、草胺膦、草甘膦、异噁草胺、哒草特、二氯喹啉酸、喹草酸、草硫膦和灭草环。
也可以是与其他已知活性化合物,如杀菌剂、杀虫剂、杀螨剂、杀线虫剂、驱鸟剂、植物养料和改善土壤结构试剂的混合物。
因此能以它们的制剂形式使用或通过进一步稀释其制得的使用形式使用这些活性化合物,如即用溶液、悬浮液、乳剂、粉末、膏糊和颗粒。它们以常规方式被使用,例如通过灌溉、喷射、雾化或散射。
本发明的活性化合物既可在植物幼苗出现前也可在出现后使用。它们也可在播种前掺入土壤。
所用活性化合物的量可在很大范围内变化。基本上取决于所需效果。通常,所用的量为每公顷土壤表面10g-10kg活性化合物,优选为每公顷50g-5kg。
(方法(d))
将2.3g(8毫摩尔)四氢呋喃-3-基2-氯磺酰苯甲酸酯、1.2g(8毫摩尔)4-甲基-5-甲硫基-2,4-二氢-3H-1,2,4-三唑-3-酮、1.0g(8毫摩尔)氰酸钠和100ml乙腈的混合物在搅拌下回流加热约15小时。然后将该混合物使用水泵真空浓缩,用二氯甲烷和盐酸水溶液(pH1)振荡残渣,分离有机相,用硫酸钠干燥并过滤。用水泵真空浓缩滤液,用乙醚浸提残渣并通过用抽吸过滤分离出晶状产物。
将2.8g(10毫摩尔)氧杂环丁烷-3-基2-氯磺酰苯甲酸酯、1.3g(10毫摩尔)5-乙基-4-甲基-2,4-二氢-3H-1,2,4-三唑-3-酮、1.3g(20毫摩尔)氰酸钠和50ml乙腈的混合物在回流下加热90分钟。随后将该混合物用水泵真空浓缩,并用二氯甲烷和1N盐酸搅动残渣。然后用硫酸钠干燥有机相并过滤。浓缩滤液,用异丙醇浸提残渣并通过用抽吸过滤分离所生成的晶状产物。
得到1.7g(理论值的41%)熔点为137℃的5-乙基-4-甲基-2-〔2-(氧杂环丁烷-3-基-氧羰基)-苯基磺酰-氨基羰基〕-2,4-二氢-3H-1,2,4-三唑-3-酮。
通过实施例1和2的方法,以及按照本发明制备方法的一般描述,也可以制备如下表1所列出的式(I)和式(Ia)化合物。表1:式(Ia)化合物的实例实例号 Q1 Q2 R1 R2 R3 熔点
(℃)
3 O O CH3 OC2H5
127
6 O O CH3 OCH3
7 O O CH3 OC2H5
148
(℃)9 O O CH3 OC3H7-i
10 O O CH3 OC4H9-n
11 O O CH3 OC4H9-i
12 O O CH3 OC4H9-s
13 O O CH3 OC6H5
14 O O CH3 O-CH2-CH=CH2 15 O O CH3 SCH3
12316 O O CH3 SC2H5
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)17 O O CH3 SC3H7-n
18 O O CH3 SC3H7-i
19 O O CH3 S-CH2-CH=CH2 20 O O CH3
21 O O CH3 SCH2CH2F
22 O O CH3 SCH2CHF2
23 O O CH3 SCH2CF3
24 O O CH3 N(CH3)2
25 O O CH3 SCH2F
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)26 O O CH3 SCH2Cl
27 O O CH3 SCH2CH2Cl
28 O O CH3 Cl
29 O O CH3 Br
30 O O CH3 CH3
31 O O CH3 C4H9-n
32 O O CH3
33 O O CH3 CH=CH-CH3
34 O O CH3 CH2OC2H5
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)35 O O CH3 CH2-CH=CH2
36 O O CH3 CH2OCH3
37 O O CH3 OCH2CF3
38 O O CH3 OCH2CHF2
39 O O CH3 OCH2CF2CHF2
40 O O CH3
41 O O CH3 OCH2CH2OCH3
42 S O CH3 OC2H5
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)43 O S CH3 OC2H5 44 S S CH3 OC2H5 45 O O C2H5 OC2H5 46 O O C2H5 C2H5 47 O O C2H5 n-C3H7 48 O O C2H5 i-C3H7 49 O O C2H5 OCH3
50 O O C2H5 OC2H5 51 O O C2H5 OC3H7-n
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)52 O O C2H5 OC3H7-i
53 O O C2H5 OC4H9-n
54 O O C2H5 OC4H9-i
55 O O C2H5 OC4H9-s
56 O O C2H5 OC6H5
57 O O C2H5 O-CH2-CH=CH2 58 O O C2H5 SCH3
59 O O C2H5 SC2H5
60 O O C2H5 SC3H7-n
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)61 O O C2H5 SC3H7-i
62 O O C2H5 S-CH2-CH=CH2
63 O O C2H5
64 O O C2H5 SCH2CH2F
65 O O C2H5 SCH2CHF2
66 O O C2H5 SCH2CF3
67 O O C2H5 N(CH3)2
68 O O C2H5 SCH2F
69 O O C2H5 SCH2Cl
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)70 O O C2H5 SCH2CH2Cl
71 O O C2H5 Cl
72 O O C2H5 Br
73 O O C2H5 CH3
74 O O C2H5 C4H9-n
75 O O C2H5
76 O O C2H5 CH=CH-CH3
77 O O C2H5 CH2OC2H5
78 O O C2H5 CH2-CH=CH2
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)79 O O C2H5 CH2OCH3
80 O O C2H5 OCH2CF3
81 O O C2H5 OCH2CHF2
82 O O C2H5 OCH2CF2CHF2
83 O O C2H5
84 O O C2H5 OCH2CH2OCH3
85 S O C2H5 OC2H5
86 O S C2H5 OC2H5
87 O O
OC2H5
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)88 O O
C2H5
89 O O
n-C3H7
90 O O
i-C3H7
91 O O
OCH3
92 O O
OC2H5
93 O O
OC3H7-n
94 O O
OC3H7-i
95 O O
OC4H9-n
96 O O
OC4H9-i
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)97 O O
OC4H9-s
98 O O
OC6H5
99 O O
O-CH2-CH=CH2
100 O O
SCH3
101 O O
SC2H5
102 O O
SC3H7-n
103 O O
SC3H7-i
104 O O
S-CH2-CH=CH2
105 O O
实例号 Q1 Q2 R1 R2 R3 熔点
(℃)106 O O
SCH2CH2F
107 O O
SCH2CHF2
108 O O
SCH2CF3
109 O O
N(CH3)2
110 O O
SCH2F
111 O O
SCH2Cl
112 O O
SCH2CH2Cl
113 O O
Cl
114 O O
Br
表l: (续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)115 O O
CH3
116 O O
C4H9-n
117 O O
l18 O O
CH=CH-CH3
119 O O
CH2OC2H5
120 O O
CH2-CH=CH2
121 O O
CH2OCH3
122 O O
OCH2CF3
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)123 O O
OCH2CHF2
124 O O
OCH2CF2CHF2
125 O O
126 O O
OCH2CH2OCH3
127 S O
OC2H5
128 O S
OC2H5
129 O O OCH3 OC2H5
130 O O OCH3 C2H5
131 O O OCH3 n-C3H7
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)132 O O OCH3 i-C3H7
133 O O OCH3 OCH3
134 O O OCH3 OC2H5
135 O O OCH3 OC3H7-n
136 O O OCH3 OC3H7-i
137 O O OCH3 OC4H9-n
138 O O OCH3 OC4H9-i
139 O O OCH3 OC4H9-s
140 O O OCH3 OC6H5
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)141 O O OCH3 O-CH2-CH=CH2
142 O O OCH3 SCH3
143 O O OCH3 SC2H5
144 O O OCH3 SC3H7-n
145 O O OCH3 SC3H7-i
146 O O OCH3 S-CH2-CH=CH2
147 O O OCH3
148 O O OCH3 SCH2CH2F
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)149 O O OCH2 SCH2CHF2
150 O O OCH3 SCH2CF3
151 O O OCH3 N(CH3)2
152 O O OCH3 SCH2F
153 O O OCH3 SCH2Cl
154 O O OCH3 SCH2CH2Cl
155 O O OCH3 Cl
156 O O OCH3 Br
157 O O OCH3 CH3
表1:(续)实例号 Q1 Q2 R1 R2 R3158 O O OCH3 C4H9-n
159 O O OCH3
160 O O OCH3 CH=CH-CH3
161 O O OCH3 CH2OC2H5
162 O O OCH3 CH2-CH=CH2
163 O O OCH3 CH2OCH3
164 O O OCH3 OCH2CF3
165 O O OCH3 OCH2CHF2
166 O O OCH3 OCH2CF2CHF2
表1:(续)实例号 Q1 Q2 R1 R2 R3167 O O OCH3
168 O O OCH3 OCH2CH2-
OCH3
169 S O OCH3 OC2H5
170 O S OCH3 OC2H5
171 O O OC2H5 OC2H5
172 O O OC2H5 C2H5
173 O O OC2H5 n-C3H7
174 O O OC2H5 i-C3H7
175 O O OC2H5 OCH3
表1:(续)实例号 Q1 Q2 R1 R2 R3176 O O OC2H5 OC2H5
177 O O OC2H5 OC3H7-n
178 O O OC2H5 OC3H7-i
179 O O OC2H5 SCH3
180 O O OC2H5 SC2H5
181 O O OC2H5 N(CH3)2
182 O O OC2H5 SCH2F
183 O O OC2H5 SCH2Cl
184 O O OC2H5 SCH2CH2Cl
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)185 O O OC2H5 Cl
186 O O OC2H5 Br
187 O O OC2H5 CH3
188 O O OC2H5
189 O O OC2H5 CH=CH-CH3
190 O O OC2H5 CH2OC2H5
191 O O OC2H5 CH2-CH=CH2
192 O O OC2H5 CH2OCH3
193 O O N(CH3)2 C2H5
表1:(续)实例号 Q1 Q2 R1 R2 R3 熔点
(℃)194 O O N(CH3)2 n-C3H7
195 O O N(CH3)2 CH3
196 O O N(CH3)2 OCH3
197 O O N(CH3)2 OC2H5
198 O O N(CH3)2 OC3H7-n
199 O O N(CH3)2 SCH3
200 O O CH3 C2H5
159
在-10℃时,将3.4g吡啶的20ml二氯甲烷溶液在搅拌下逐滴添加到9.46g(39毫摩尔)2-氯磺酰-苯甲酰氯、3.5g(39毫摩尔)3-羟甲基四氢呋喃和100ml二氯甲烷的混合物中,然后在20℃下将该反应混合物搅拌约6小时。随后用水泵真空将该混合物浓缩、用二氯甲烷如盐酸水溶液(pH1)振荡残渣、分离有机相,用硫酸钠干燥并过滤。用水泵真空仔细地将溶剂由滤液中蒸馏掉。
得到8.2g(理论值的72.5%)四氢呋喃-3-基2-氯磺酰甲磺酸酯油状残渣,可直接用于进一步反应。实施例(VII-2)步骤1
将68.3g(0.20摩尔)双-(2-氯羰基苯基)二硫化物、29.6g(0.40摩尔)3-羟基氧杂环丁烷、42.5g(0.42摩尔)三乙胺和500ml二氯乙烷的混合物在20℃下搅拌15小时。然后添加200ml 1N盐酸并分离有机相,用水洗涤,用硫酸钠干燥并过滤。用水泵真空浓缩滤液,用乙醚浸提残渣并通过用抽吸过滤分离得到的晶状产物。
得到48.6g(理论值的58%)熔点为143℃的双-[2-(氧杂环丁烷-3-基-氧羰基)苯基〕二硫化物。步骤2
在-5℃-0℃下,将11.2g氯约15分钟同期引入10.5g(25毫摩尔)双-[2-(氧杂环丁烷-3-基氧羰基)苯基〕二硫化物、12.9g乙酸钠和100ml 50%的浓乙酸水溶液的混合物中。在0℃下将该反应混合物再搅拌15分钟然后与150ml二氯甲烷混合。然后分离二氯甲烷相,用冰水洗涤,用硫酸钠干燥并过滤。用水泵真空浓缩滤液并通过硅胶柱色谱将残渣提纯两次(第一次操作用二氯甲烷,第二次操作用乙酸乙酯)。得到10.4g(理论值的75%)淡黄色油状氧杂环丁烷-3-基2-氯磺酰甲磺酸酯。1H NMR(CDCl3,TMS,δ):4.9(m,2H),5.0(m,2H),5.8(m,1H),7.8(m,3H),8.2(m,1H)ppm。使用实施例实施例A幼苗出现前试验溶剂:丙酮5重量份乳化剂:烷芳基聚乙二醇醚1重量份
为制备合适的活性化合物制品,将1重量份活性化合物与上述量溶剂混合,添加上述量的乳化剂并用水稀释该浓缩物至所需浓度。
将试验植物的种子播种在正常土壤中。24小时后,用活性化合物制品灌溉该土壤。有利的是保持每单位面积的水量恒定。制品中活性化合物的浓度并不重要,只有每单位面积所用的活性化合物量是关键。
三周以后,通过与未处理对照物的发育比较,以%损害评定对植物的损害程度。
下列数值表示:
0%=无作用(像未处理的对照物)
100%=完全破坏
在这一试验中,本发明的式(I)化合物显示出优良的抗杂草活性(参见表A)。实施例B幼苗出现后试验溶剂:丙酮5重量份乳化剂:烷芳基聚乙二醇醚1重量份
为制备合适的活性化合物制品,将1重量份活性化合物与上述量溶剂混合,添加上述量的乳化剂并用水将浓缩物稀释至所需浓度。
以每单位面积施用所希望的特定量活性化合物的方式用活性化合物制品喷射高度为5-15cm的试验植物。选择喷射液体的浓度,以使得将所需的特定量活性化合物施用在1000l水/公顷中。
三周后,通过与未处理的对照物发育比较,以%损害评定植物的损害程度。
下列数值表示:
0%=无作用(像未处理的对照物)
100%=完全破坏
在这一试验中,本发明的式(I)化合物显示出优良的抗杂草活性(参见表B)。表A:苗前试验/温室
表B:苗后试验/温室
活性化合物(以制备实施例号表示) | 施用率(g/公顷) | 玉米 | 看麦娘属 | 莎草属 | 狗毛草属 | 苋属 | 芥属 |
(7) | 250 | 10 | 80 | - | 70 | 100 | - |
(201) | 250 | - | 80 | 95 | 80 | 70 | 100 |
(202) | 250 | 0 | 80 | 100 | 70 | - | 70 |
活性化合物(以制备实施例号表示) | 施用率(g/公顷) | 玉米 | 看麦娘属 | Avena fatua | 芥属 |
(201) | 250 | 10 | 80 | 80 | 100 |
Claims (9)
1.如下通式(I)取代的芳基磺酰氨基(硫代)羰基三唑啉(硫)酮及式(I)化合物的盐:其中Ar 分别代表任选取代的亚芳基或杂亚芳基,Q1 代表氧或硫,Q2 代表氧或硫,R1 代表氢、羟基、氨基、亚烷基氨基或分别代表任选取代的下述基:
烷基、链烯基、链炔基、烷氧基、链烯氧基、烷基氨基、二烷基氨
基、链烷酰氨基、环烷基、环烷基烷基、芳基、芳烷基,R2 代表氢、羟基、巯基、氨基、卤素或分别代表任选取代的下述基:
烷基、链烯基、链炔基、烷氧基、链烯氧基、链炔氧基、烷硫基、
链烯硫基、链炔硫基、烷基氨基、链烯基氨基、链炔基氨基、二烷
基氨基、链烷酰氨基、氮丙啶基、吡咯烷子基、哌啶子基、吗啉代、
环烷基、环烯基、环烷氧基、环烷硫基、环烷基氨基、环烷基烷基、
环烷基烷氧基、环烷基烷硫基、环烷基烷基氨基、芳基、芳氧基、
芳硫基、芳氨基、芳烷基、芳烷氧基、芳烷硫基、芳烷基氨基、杂
环氧基、杂环硫基,或R1和R2一起代表任选支链烷二基,而R3代表任选取代的杂环基。
2.按照权利要求1的式(I)化合物,其特征在于其中Ar 代表亚苯基或亚萘基,它们各自任选被卤素、氰基、硝基取代,被
C1-C4-烷基、C1-C4-烷氧基、C1-C4-烷硫基、C1-C4
-烷基亚磺酰、C1-C4-烷基磺酰、二(C1-C4-烷基)氨基
磺酰或N-C1-C4-烷氧基-N-C1-C4-烷基氨基磺酰(它
们各自任选被氟和/或氯所取代)所取代,或代表5或6个环原子的
杂亚芳基,其中至少一个环原子是氧、硫或氮,并且一个或两个以
上任选为氮,该原子任选地被卤素、氰基、硝基取代、被C1-C4
-烷基或C1-C4-烷氧基(它们各自任选地被氟和/或氯所取代)
取代,Q1 代表氧或硫,Q2 代表氧或硫,R1 代表氢、羟基、氨基、代表C2-C10-亚烷基氨基,代表任选由氟-、
氯-、溴-、氰基-、C1-C4-烷氧基-、C1-C4-烷基羰基-
或C1-C4-烷氧基羰基取代的C1-C6-烷基,代表分别任选由
氟-、氯-、和/或溴取代的C2-C6-链烯基或C2-C6-链炔基,
代表分别任选由氟-、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-烷基氨基、或
C1-C6-链烷酰氨基,代表C3-C6-链烯氧基、代表二(C1-
C4-烷基)氨基、代表分别任选由氟-、氯-、溴-、氰基-和/
或C1-C4-烷基取代的C3-C6-环烷基或C3-C6-环烷基-
C1-C4-烷基,或代表分别任选氟-、氯-、溴-、氰基-、硝
基-、C1-C4-烷基-、三氟甲基-、和/或C1-C4-烷氧基取
代的苯基或苯基-C1-C4-烷基,R2 代表氢、羟基、巯基、氨基、氟、氯、溴、碘,代表任选由氟-、
氯-、溴-、氰基-、C1-C4-烷氧基-、C1-C4-烷基羰基
-或C1-C4-烷氧基羰基取代的C1-C6-烷基,代表分别任选
由氟-、氯-、和/或溴-取代的C2-C6-链烯基或C2-C6-链
炔基,代表分别由任选氟-、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-烷硫
基、C1-C6-烷基氨基或C1-C6-链烷酰氨基,代表C2-C6-
链烯氧基、C2-C6-链炔氧基、C2-C6-链烯硫基、C2-C6-
链炔硫基、C2-C6-链烯基氨基或C2-C6-链炔基氨基、代表
二(C1-C4-烷基)氨基、代表分别任选由甲基-、和/或乙基取
代的氮丙啶基、吡咯烷子基、哌啶子基或吗啉代,代表分别任选由
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-环烷氧基、C3-C6-环
烷硫基、C3-C6-环烷氨基、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-烷硫基或C3-C6-环烷基-C1-C4-烷基氨基,或代
表分别任选由氟-、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-C1
-C4-烷基、苯氧基、苯基-C1-C4-烷氧基、苯硫基、苯基-
C1-C4-烷硫基、苯基氨基或苯基-C1-C4-烷基氨基,或代
表分别任选由氟-、氯-、溴-、氰基-、硝基-、C1-C4-烷
基-、三氟甲基-和/或C1-C4-烷氧基取代的杂环氧基或杂环硫
基,在各种情况下该杂环基成分选自环氧乙烷基、氧杂环丁烷基、
呋喃基、四氢呋喃基、噻环丁基、噻吩基、四氢噻吩基,或R1和R2一起代表任选具有3-11个碳原子的支链烷二基,以及R3代表分别任选由卤素-或C1-C4-烷基取代的氧杂环丁基、噻环
丁基、呋喃基、四氢呋喃基、噻吩基或四氢噻吩基,以及式(I)化合物的钠、钾、镁、钙、铵、C1-C4-烷基铵、二(C1-C4-烷基)铵、三(C1-C4-烷基)铵、四(C1-C4-烷基)铵、三(C1-C4-烷基)锍、C5-或C6-环烷基铵和二(C1-C2-烷基)苄基铵盐。
3.按照权利要求1的式(I)化合物,其特征在于其中Ar 代表分别任选由氟-、氯-、溴-、氰基-、硝基-、甲基-、
乙基-、正-或异-丙基-、三氟甲基-、甲氧基-、乙氧基-、
二氟甲氧基-、三氟甲氧基-、甲硫基-或乙硫基-取代的1,2-
亚苯基(邻亚苯基)、吡啶-2,3-二基、噻吩-2,3-二基或吡
唑-4,5-二基,Q1 代表氧或硫,Q2 代表氧或硫,R1 代表氢、羟基、氨基,代表C3-C8-亚烷基氨基,代表分别任选
由氟-、氯-、氰基-、甲氧基-或乙氧基-取代的甲基、乙基、
正-或异丙基-、正-、异-、仲-或叔-丁基,代表分别任选由
氟-、氯-或溴-取代的丙烯基、丁烯基、丙炔基或丁炔基,代表
分别任选氟-、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、甲氨
基、乙氨基、正-或异-丙氨基、正-、异-、仲-或叔-丁氨基,
代表丙烯氧基或丁烯氧基,代表二甲氨基或二乙氨基,代表分别任
选氟-、氯-、甲基-和/或乙基-取代的环丙基、环丁基、环戊基、
环己基、环丙甲基、环丁甲基、环戊甲基或环己甲基,或代表分别
任选氟-、氯-、甲基-、三氟甲基-和/或甲氧基-取代的苯基或
苄基,R2代表氢、羟基、巯基、氨基、氟、氯、溴,代表分别任选氟-、
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,代表分别任选氟-、氯-、
或溴-取代的丙烯基、丁烯基、丙炔基或丁炔基,代表分别任选氟-、
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、甲硫基、乙硫基、
正或异丙硫基、正,异,仲或叔丁硫基、甲氨基、乙氨基、正或异
丙氨基、正,异,仲或叔丁氨基,代表丙烯氧基、丁烯氧基、丙炔
氧基、丁炔氧基、丙烯硫基、丁烯硫基、丙炔硫基、丁炔硫基、丙
烯氨基、丁烯氨基、丙炔氨基、或丁炔氨基,代表二甲氨基、二乙
氨基或二丙氨基,代表分别任选由氟-、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、
环丙氧基、环丁氧基、环戊氧基、环己氧基、环丙硫基、环丁硫基、
环戊硫基、环己硫基、环丙氨基、环丁氨基、环戊氨基、环己氨基、
环丙甲基、环丁甲基、环戊甲基、环己甲基、环丙甲氧基、环丁甲
氧基、环戊甲氧基、环己甲氧基、环丙甲硫基、环丁甲硫基、环戊
甲硫基、环己甲硫基、环丙甲氨基、环丁甲氨基、环戊甲氨基或环
己甲氨基,或代表分别任选由氟-、氯-、甲基-、三氟甲基-和
/或甲氧基-取代的苯基、苄基、苯氧基、苄氧基、苯硫基、苄硫基、
苯基氨基或苄基氨基,或代表分别任选由氟-、氯-、甲基-三氟
甲基-和/或甲氧基-取代的氧杂环丁氧基、呋喃氧基、四氢呋喃氧
基、噻吩氧基或四氢噻吩氧基,或R1和R2一起代表任选具有3-11个碳原子的支链烷二基,以及R3代表分别任选由氟-、氯-、甲基-或乙基-取代的氧杂环丁基、噻
环丁基、呋喃基、四氢呋喃基、噻吩基或四氢噻吩基。
5.制备权利要求1式(I)化合物的方法,其特征在于
(a)如果合适,在一种反应助剂存在下,以及如果合适在一种稀释剂存在下,使如下通式(II)的三唑啉(硫)酮:其中
Q1、R1和R2各自如权利要求1中定义,与如下通式(III)的取代的异(硫代)氰酸芳基磺酸酯反应:
R3-O-CO-Ar-SO2-N=C=Q2 (III)其中
Ar、Q2和R3各自如权利要求1中定义,或
Q1、Q2、R1和R2各自如上定义,而Z代表卤素、烷氧基、芳氧基或芳基烷氧基,与如下通式(V)的磺酰胺反应:
R3-O-CO-Ar-SO2-NH2 (V)其中
Ar和R3各自如上定义,或
Q1、R1和R2各自如上定义,与如下通式(VI)的取代的芳基磺酰胺衍生物反应:
R3-O-CO-Ar-SO2-NH-CQ2-Z (VI)其中
Ar、Q2和R3各自如上定义,而Z代表卤素、烷氧基、芳氧基或芳基烷氧基,或
Q1、R1和R2各自如上定义,与如下通式(VII)取代的芳基磺酰卤反应:
R3-O-CO-Ar-SO2-X (VII)其中
Ar和R3各自如上所定义,而X代表卤素和如下通式(VIII)的金属(硫代)氰酸盐:
MQ2CN (VIII)其中
Q2如上所定义,而
M代表一种碱金属或一 当量的碱土金属,并且如果合适将由方法(a)、(b)、(c)或(d)得到的式(I)化合物通过常规方法转化成盐。
6.除草剂,其特征在于所述的除草剂含有至少一种权利要求1的式(I)化合物或其盐。
7.权利要求1的通式(I)化合物或其盐,用于控制不希望的植物生长。
8.控制杂草的方法,其特征在于使权利要求1的通式(I)化合物或其盐作用在杂草或其生长场所。
9.制备除草剂的方法,其特征在于将权利要求1通式(I)的化合物或其盐与扩充剂和/或表面活性剂混合。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE19525974.2 | 1995-07-17 | ||
DE1995125974 DE19525974A1 (de) | 1995-07-17 | 1995-07-17 | Substituierte Arylsulfonylamino(thio)carbonyltriazolin(thi)one |
Publications (1)
Publication Number | Publication Date |
---|---|
CN1195347A true CN1195347A (zh) | 1998-10-07 |
Family
ID=7767020
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN 96196762 Pending CN1195347A (zh) | 1995-07-17 | 1996-07-04 | 取代的芳基磺酰氨基(硫代)羰基三唑啉(硫)酮 |
Country Status (7)
Country | Link |
---|---|
EP (1) | EP0840734A1 (zh) |
JP (1) | JPH11509219A (zh) |
CN (1) | CN1195347A (zh) |
AU (1) | AU6518896A (zh) |
CA (1) | CA2227012A1 (zh) |
DE (1) | DE19525974A1 (zh) |
WO (1) | WO1997003980A1 (zh) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE19933260A1 (de) | 1999-07-15 | 2001-01-18 | Bayer Ag | Substituierte Thien-3-yl-sulfonylamino(thio)carbonyl-triazolin(thi)one |
Family Cites Families (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3936622A1 (de) * | 1989-11-03 | 1991-05-08 | Bayer Ag | Halogenierte sulfonylaminocarbonyltriazolinone |
DE3815765A1 (de) * | 1988-05-09 | 1989-11-23 | Bayer Ag | 2-sulfonylaminocarbonyl-2,4-dihydro-3h-1,2,4- triazol-3-one einschliesslich 4,5-kondensierter, bicyclischer derivate, verfahren und neue zwischenprodukte zu ihrer herstellung und ihre verwendung als pflanzenbehandlungsmittel |
DE3934081A1 (de) * | 1989-10-12 | 1991-04-18 | Bayer Ag | Sulfonylaminocarbonyltriazolinone |
DE3936623A1 (de) * | 1989-11-03 | 1991-05-08 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit ueber schwefel gebundenen substituenten |
DE4110795A1 (de) * | 1991-04-04 | 1992-10-08 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit ueber sauerstoff gebundenen substituenten |
DE4131842A1 (de) * | 1991-09-25 | 1993-04-01 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit zwei ueber sauerstoff gebundenen substituenten |
DE4435547A1 (de) * | 1994-10-05 | 1996-04-11 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit über Sauerstoff und Schwefel gebundenen Substituenten |
-
1995
- 1995-07-17 DE DE1995125974 patent/DE19525974A1/de not_active Withdrawn
-
1996
- 1996-07-04 EP EP96924877A patent/EP0840734A1/de not_active Withdrawn
- 1996-07-04 AU AU65188/96A patent/AU6518896A/en not_active Withdrawn
- 1996-07-04 CA CA 2227012 patent/CA2227012A1/en not_active Abandoned
- 1996-07-04 JP JP9506228A patent/JPH11509219A/ja active Pending
- 1996-07-04 WO PCT/EP1996/002932 patent/WO1997003980A1/de not_active Application Discontinuation
- 1996-07-04 CN CN 96196762 patent/CN1195347A/zh active Pending
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WO1997003980A1 (de) | 1997-02-06 |
EP0840734A1 (de) | 1998-05-13 |
CA2227012A1 (en) | 1997-02-06 |
JPH11509219A (ja) | 1999-08-17 |
DE19525974A1 (de) | 1997-01-23 |
AU6518896A (en) | 1997-02-18 |
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