CN1196054A - 含有杂环(烷)氧基取代基的磺酰氨基(硫)羰基三唑啉(硫)酮类 - Google Patents
含有杂环(烷)氧基取代基的磺酰氨基(硫)羰基三唑啉(硫)酮类 Download PDFInfo
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- CN1196054A CN1196054A CN96196813A CN96196813A CN1196054A CN 1196054 A CN1196054 A CN 1196054A CN 96196813 A CN96196813 A CN 96196813A CN 96196813 A CN96196813 A CN 96196813A CN 1196054 A CN1196054 A CN 1196054A
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- Prior art keywords
- alkyl
- represent
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- chlorine
- fluorine
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- 125000000623 heterocyclic group Chemical group 0.000 title claims abstract description 8
- 230000002363 herbicidal effect Effects 0.000 title claims description 6
- XLIUPWCZVUDHFH-UHFFFAOYSA-N S(=O)(=O)=NSC(=O)N1N=NCC1 Chemical compound S(=O)(=O)=NSC(=O)N1N=NCC1 XLIUPWCZVUDHFH-UHFFFAOYSA-N 0.000 title 1
- -1 hydroxy, amino Chemical group 0.000 claims abstract description 99
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 239000001301 oxygen Substances 0.000 claims abstract description 46
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 46
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 43
- 239000001257 hydrogen Substances 0.000 claims abstract description 43
- 238000000034 method Methods 0.000 claims abstract description 43
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 36
- 239000005864 Sulphur Substances 0.000 claims abstract description 36
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 29
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 14
- 150000003839 salts Chemical class 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 8
- 125000003118 aryl group Chemical group 0.000 claims abstract description 8
- 125000003342 alkenyl group Chemical group 0.000 claims abstract description 6
- 125000003282 alkyl amino group Chemical group 0.000 claims abstract description 6
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims abstract description 5
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims abstract description 5
- 125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 5
- 125000004663 dialkyl amino group Chemical group 0.000 claims abstract description 5
- 125000001072 heteroaryl group Chemical group 0.000 claims abstract description 3
- 239000000460 chlorine Substances 0.000 claims description 123
- 229910052801 chlorine Inorganic materials 0.000 claims description 123
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 122
- 229910052731 fluorine Inorganic materials 0.000 claims description 121
- 239000011737 fluorine Substances 0.000 claims description 121
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims description 119
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 68
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 67
- 229910052794 bromium Inorganic materials 0.000 claims description 67
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 44
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 35
- 150000002431 hydrogen Chemical class 0.000 claims description 35
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 26
- 238000002360 preparation method Methods 0.000 claims description 23
- 241000196324 Embryophyta Species 0.000 claims description 21
- 238000006243 chemical reaction Methods 0.000 claims description 21
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 20
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 19
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002576 ketones Chemical class 0.000 claims description 17
- 239000000203 mixture Substances 0.000 claims description 16
- 150000002367 halogens Chemical class 0.000 claims description 15
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 14
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 14
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 14
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 12
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 10
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 10
- 150000003863 ammonium salts Chemical class 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000004104 aryloxy group Chemical group 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 6
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 6
- 125000001160 methoxycarbonyl group Chemical group [H]C([H])([H])OC(*)=O 0.000 claims description 6
- XSROQCDVUIHRSI-UHFFFAOYSA-N thietane Chemical compound C1CSC1 XSROQCDVUIHRSI-UHFFFAOYSA-N 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 5
- 125000003830 C1- C4 alkylcarbonylamino group Chemical group 0.000 claims description 4
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 4
- 125000002905 alkanoylamido group Chemical group 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000005336 allyloxy group Chemical group 0.000 claims description 4
- 125000000051 benzyloxy group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])O* 0.000 claims description 4
- 125000002541 furyl group Chemical group 0.000 claims description 4
- 125000003566 oxetanyl group Chemical group 0.000 claims description 4
- 125000004076 pyridyl group Chemical group 0.000 claims description 4
- 125000005958 tetrahydrothienyl group Chemical group 0.000 claims description 4
- 125000001544 thienyl group Chemical group 0.000 claims description 4
- 125000005034 trifluormethylthio group Chemical group FC(S*)(F)F 0.000 claims description 4
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
- WQJONRMBVKFKOB-UHFFFAOYSA-N cyanatosulfanyl cyanate Chemical compound N#COSOC#N WQJONRMBVKFKOB-UHFFFAOYSA-N 0.000 claims description 3
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 3
- 229940124530 sulfonamide Drugs 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
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims description 2
- 125000002861 (C1-C4) alkanoyl group Chemical group 0.000 claims description 2
- WIHIUTUAHOZVLE-UHFFFAOYSA-N 1,3-diethoxypropan-2-ol Chemical compound CCOCC(O)COCC WIHIUTUAHOZVLE-UHFFFAOYSA-N 0.000 claims description 2
- WNXJIVFYUVYPPR-UHFFFAOYSA-N 1,3-dioxolane Chemical compound C1COCO1 WNXJIVFYUVYPPR-UHFFFAOYSA-N 0.000 claims description 2
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 claims description 2
- IQBDNAFWMWZTMD-UHFFFAOYSA-N N#CO.[S] Chemical compound N#CO.[S] IQBDNAFWMWZTMD-UHFFFAOYSA-N 0.000 claims description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 claims description 2
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-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
- 229910052728 basic metal Inorganic materials 0.000 claims description 2
- 150000003818 basic metals Chemical class 0.000 claims description 2
- 125000004369 butenyl group Chemical group C(=CCC)* 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
- 125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 2
- 159000000007 calcium salts Chemical class 0.000 claims description 2
- 125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 2
- 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 2
- 125000004210 cyclohexylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
- 125000004851 cyclopentylmethyl group Chemical group C1(CCCC1)C* 0.000 claims description 2
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 2
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 2
- ZZVUWRFHKOJYTH-UHFFFAOYSA-N diphenhydramine Chemical group C=1C=CC=CC=1C(OCCN(C)C)C1=CC=CC=C1 ZZVUWRFHKOJYTH-UHFFFAOYSA-N 0.000 claims description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 2
- 125000000031 ethylamino group Chemical group [H]C([H])([H])C([H])([H])N([H])[*] 0.000 claims description 2
- 125000006125 ethylsulfonyl group Chemical group 0.000 claims description 2
- 125000001153 fluoro group Chemical group F* 0.000 claims description 2
- 229950001891 iprotiazem Drugs 0.000 claims description 2
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 claims description 2
- 125000005928 isopropyloxycarbonyl group Chemical group [H]C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 claims description 2
- 159000000003 magnesium salts Chemical class 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 2
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 2
- 125000006216 methylsulfinyl group Chemical group [H]C([H])([H])S(*)=O 0.000 claims description 2
- 239000001103 potassium chloride Substances 0.000 claims description 2
- 235000011164 potassium chloride Nutrition 0.000 claims description 2
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 claims description 2
- 125000005493 quinolyl group Chemical group 0.000 claims description 2
- 159000000000 sodium salts Chemical class 0.000 claims description 2
- 125000002769 thiazolinyl group Chemical group 0.000 claims description 2
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 2
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 2
- 108010021119 Trichosanthin Proteins 0.000 claims 1
- 230000008635 plant growth Effects 0.000 claims 1
- 125000000547 substituted alkyl group Chemical group 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 3
- 125000005236 alkanoylamino group Chemical group 0.000 abstract 1
- 125000003302 alkenyloxy group Chemical group 0.000 abstract 1
- 125000006193 alkinyl group Chemical group 0.000 abstract 1
- 125000004415 heterocyclylalkyl group Chemical group 0.000 abstract 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
- 239000013067 intermediate product Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 description 26
- 239000002994 raw material Substances 0.000 description 20
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000000047 product Substances 0.000 description 10
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- 239000003921 oil Substances 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
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-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
- 230000006378 damage Effects 0.000 description 6
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- 239000000243 solution Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 5
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 5
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- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 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
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- 150000002148 esters Chemical class 0.000 description 4
- 229940043265 methyl isobutyl ketone Drugs 0.000 description 4
- 238000001953 recrystallisation Methods 0.000 description 4
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- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 4
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- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 2
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 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 compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
- 150000003918 triazines Chemical class 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
- 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
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
- C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
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- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- 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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- 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
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- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Abstract
新的式(Ⅰ)标题化合物和式(Ⅰ)化合物的盐,它们的制备方法和新的中间体,以及作为除草剂的用途,其中Q1代表氧或硫,Q2代表氧或硫,R1代表氢,羟基,氨基或C1-C6-亚烷基氨基,或在每一种情况任意代表选自烷基,链烯基,炔基,烷氧基,烯氧基,烷氨基,二烷氨基,链烷酰氨基,环烷基,环烷基烷基,环烷基氨基,芳基和芳烷基的取代的基团,及R2在每一种情况代表取代的杂环基或杂环基烷基,及R3代表任意取代的烷基,芳烷基,芳基或杂芳基。
Description
本发明涉及新的含有杂环(烷)氧基取代基的磺酰氨基(硫)羰基三唑啉(硫)酮类,其多种制备方法和用于制备它们的新的中间体,及将其用作除草剂的应用。
已知某些磺酰氨基羰基三唑啉酮类具有除草性质(参考EP-341489,EP-A-425 984,EP-A-422 469,EA-A-431 291,EP-A-507171)。但是,这些化合物的作用不是在每个方面都令人满意。
现在已经发现通式(I)新的含有杂环(烷)氧基取代基的磺酰氨基(硫)羰基三唑啉(硫)酮类及式(I)化合物的盐其中Q1代表氧或硫,Q2代表氧或硫,R1代表氢,羟基,氨基或亚烷基氨基或在各种情况下代表任意取代的下列基团:烷基,链烯基,炔基,烷氧基,烯氧基,烷氨基,二烷氨基,链烷酰氨基,环烷基,环烷基烷基,环烷基氨基,芳基和芳烷基,R2在各种情况下代表任意取代的杂环基或杂环基烷基,及R3在各种情况下代表任意取代的烷基,芳烷基,芳基和杂芳基。
通式I新的含有杂环(烷)氧基取代基的磺酰氨基(硫)羰基三唑啉(硫)酮类用下列方法得到:(a)通式(II)的三唑啉(硫)酮其中Q1,R1和R2如上定义与通式(III)的磺酰基异(硫)氰酸酯任意在反应助剂和稀释剂的存在下反应
R3-SO2-N=C=Q2 (III)其中Q2和R3如上定义,或(b)通式(IV)的三唑啉(硫)酮衍生物其中Q1,Q2,R1和R2如上定义,及Z代表卤素,烷氧基,芳烷氧基或芳氧基与通式(V)的磺酰胺任意在酸受体和稀释剂的存在下反应,
R3-SO2-NH2 (V)其中R3如上定义,或(c)通式(II)的三唑啉(硫)酮其中Q1,R1和R2如上定义与通式(VI)的磺酰胺衍生物任意在酸受体和稀释剂的存在下反应,
R3-SO2-NH-CO2-Z (VI)其中Q2,R3如上定义,及Z代表卤素,烷氧基,芳烷氧基或芳氧基,或(d)通式(II)的三唑啉(硫)酮其中Q1,R1和R2如上定义与通式(VII)的磺酰卤
R3-SO2-X (VII)其中R3如上定义,X代表卤素和与通式(VIII)的(硫)氰酸金属盐
MQ2CN (VIII)其中Q2如上定义及M代表碱金属或碱土金属等价物,任意在反应助剂和稀释剂的存在下反应,如果需要,用常规方法将从方法(a),(b),(c)或(d)得到的式(I)化合物转化为盐。
通式(I)新的含有杂环(烷)氧基取代基的磺酰氨基(硫)羰基三唑啉(硫)酮类具有很强除草活性。
本发明涉及优选的式(I)化合物,其中Q1代表氧或硫,Q2代表氧或硫,R1代表氢,羟基,氨基或C1-C6-亚烷基氨基,或任意代表氟,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,或在每一种情况任意代表氟,氯和/或溴取代的C2-C6-链烯基或C2-C6-炔基,或代表C1-C6-烷氧基或C3-C6-烯氧基,或在每一种情况任意代表氟和/或氯取代的C1-C6-烷氨基,二(C1-C4-烷基)-氨基或C1-C4-链烷酰氨基,或在每一种情况任意代表氟,氯,溴和/或C1-C4-烷基取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,或在每一种情况任意代表氟,氯,溴,氰基,硝基,C1-C4-烷基,三氟甲基,C1-C4-烷氧基和/或C1-C4-烷氧基-羰基-取代的苯基或苯基-C1-C4-烷基,R2在每一种情况代表卤素和/或C1-C4-烷基取代的氧杂环丁烷基,硫杂环丁烷基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,吡啶基,嘧啶基,氧杂环丁烷基-C1-C4-烷基,硫杂环丁烷基-C1-C4烷基,呋喃基-C1-C4-烷基,四氢呋喃基-C1-C4-烷基,噻吩基-C1-C4-烷基,四氢噻吩基-C1-C4-烷基,吡啶基-C1-C4-烷基或嘧啶基-C1-C4-烷基,及R3代表基团其中R4和R5相同或不同,并且代表氢,氟,氯,溴,碘,硝基或C1-C6-烷基(可任意被氟,氯,溴,氰基,羧基,C1-C4-烷氧羰基,C1-C4-烷基氨基-羰基,二-(C1-C4-烷基)-氨基-羰基,羟基,C1-C4-烷氧基,甲酰氧基,C1-C4-烷基-羰氧基,C1-C4-烷氧基-羰氧基,C1-C4-烷基氨基-羰氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基,C1-C4-烷基磺酰基,二-(C1-C4-烷基)-氨基-磺酰基,C3-C6-环烷基或苯基取代),或代表C2-C6-链烯基(可任意被氟,氯,溴,氰基,C1-C4-烷氧基-羰基,羧基或苯基取代),或代表C2-C6-炔基(可任意被氟,氯,溴,氰基,C1-C4-烷氧基-羰基,羧基或苯基取代),或代表C1-C4-烷氧基(可任意被氟,氯,溴,氰基,羧基,C1-C4-烷氧基-羰基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基取代),或代表C1-C4-烷硫基(可任意被氟,氯,溴,氰基,羧基,C1-C4-烷氧基-羰基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基取代),或代表C2-C6-烯氧基(可任意被氟,氯,溴,氰基,或C1-C4-烷氧基-羰基取代),或代表C2-C6-烯硫基(可任意被氟,氯,溴,氰基,硝基,C1-C3-烷硫基或C1-C4-烷氧基-羰基取代),C3-C6-炔氧基或C3-C6-炔硫基,或代表基团-S(O)p-R6,其中p代表数1或2和R6代表C1-C4-烷基(可任意被氟,氯,溴,氰基,或C1-C4-烷氧基-羰基取代),C3-C6-链烯基,C3-C6-炔基,C1-C4-烷氧基,C1-C4-烷氧基-C1-C4-烷基氨基,C1-C4-烷基氨基,二-(C1-C4-烷基)-氨基或苯基,或代表基团-NHOR7,其中R7代表C1-C12-烷基(可任意被氟,氯,氰基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基,C1-C4-烷基磺酰基,C1-C4-烷基-羰基,C1-C4-烷氧基-羰基,C1-C4-烷基氨基-羰基或二-(C1-C4-烷基)-氨基-羰基取代),或代表C3-C6-链烯基(可任意被氟,氯或溴取代),C3-C6-炔基,C3-C6-环烷基,C3-C6-环烷基-C1-C2-烷基或苯基-C1-C2-烷基(可任意被氟,氯,硝基,氰基,C1-C4-烷基,C1-C4-烷氧基或C1-C4-烷氧基-羰基取代),或代表二苯甲基,或代表苯基(可任意被氟,氯,硝基,氰基,C1-C4-烷基,三氟甲基,C1-C4-烷氧基,C1-C2-氟代烷氧基,C1-C4-烷硫基,三氟甲硫基或C1-C4-烷氧基-羰基取代),R4和/或R5还代表苯基或苯氧基,或代表C1-C4烷基羰基氨基,C1-C4-烷氧基-羰基氨基,C1-C4-烷基氨基-羰基-氨基或二-(C1-C4-烷基)-氨基-羰基氨基,或代表基团-CO-R8,其中R8代表氢,C1-C6-烷基,C3-C6-环烷基,C1-C6-烷氧基,C3-C6-环烷氧基,C3-C6-链烯氧基,C1-C4-烷硫基,C1-C4-烷基氨基,C1-C4-烷氧基氨基,C1-C4-烷氧基-C1-C4-烷基-氨基或二-(C1-C4-烷基)-氨基(可任意被氟和/或氯取代),R4和/或R5还代表三甲基甲硅烷基,噻唑啉基,C1-C4-烷基磺酰氧基,或二-(C1-C4-烷基)-氨基磺酰氨基或代表基团
-CH=N-R9,其中R9任意代表氟,氯,氰基,羧基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基取代的C1-C6-烷基,或任意代表氟或氯取代的苄基,或任意代表氟或氯取代的C3C6-链烯基或C3-C6-炔基,或任意代表氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,三氟甲基,三氟甲氧基或三氟甲硫基取代的苯基,或任意代表氟,和/或氯取代的C1-C6-烷氧基,C3-C6-烯氧基,C3-C6-炔氧基或苄氧基,或代表氨基,C1-C4-烷基氨基,二(C1-C4-烷基)氨基,苯基氨基,C1-C4-烷基-羰基氨基,C1-C4-烷氧基羰基氨基或C1-C4-烷基-磺酰氨基,或任意代表氟,氯,溴或甲基取代的苯基磺酰氨基,及R3代表基团其中R10代表氢或C1-C4-烷基,R11和R12相同或不同,并且代表氢,氟,氯,溴,硝基,氰基,C1-C4-烷基(任意被氟和/或氯取代),C1-C4-烷氧基(任意被氟和/或氯取代),羧基,C1-C4-烷氧基-羰基,二甲氨基羰基,C1-C4-烷基-磺酰基或二(C1-C4-烷基)氨基磺酰基;及R3还代表基团其中R13和R14相同或不同,并且代表氢,氟,氯,溴,硝基,氰基,C1-C4-烷基(任意被氟和/或氯取代),C1-C4-烷氧基(任意被氟和/或氯取代);及R3还代表基团其中R15和R16相同或不同,并且代表氢,氟,氯,溴,硝基,氰基,C1-C4-烷基(任意被氟和/或氯取代),C1-C4-烷氧基(任意被氟和/或氯取代),或代表C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(任意被氟和/或氯取代),或代表氨基磺酰基或单-(C1-C4-烷基)氨基磺酰基,或代表二-(C1-C4-烷基)氨基磺酰基,或C1-C4-烷氧基-羰基或二甲氨基羰基;及R3还代表基团其中R17和R18相同或不同,并且代表氢,氟,氯,溴,C1-C4-烷基(任意被氟和/或氯取代)或C1-C4-烷氧基(任意被氟和/或氯取代),或代表C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(任意被氟和/或氯取代),或代表二-(C1-C4-烷基)-氨基磺酰基;及R3还代表基团其中R19和R20相同或不同,并且代表氢,氟,氯,溴,氰基,硝基,C1-C4-烷基(任意被氟和/或氯取代),C1-C4-烷氧基(任意被氟和/或氯取代),C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(任意被氟和/或氯取代),二-(C1-C4-烷基)-氨基磺酰基,C1-C4-烷氧基-羰基或二甲氨基羰基;及A代表氧,硫或基团N-Z1,其中
Z1代表氢,C1-C4-烷基(任意被氟,氯,溴,或氰基取代),C3-C6-环烷基,苄基,苯基(任意被氟,氯,溴,或硝基取代),C1-C4-烷基羰基,C1-C4-烷氧基羰基或二(C1-C4-烷基)氨基羰基;及R3还代表基团其中R21和R22相同或不同,并且代表氢,C1-C4-烷基,卤素,C1-C4-烷氧基羰基,C1-C4-烷氧基,或C1-C4-卤代烷氧基,Y1代表硫或基团N-R23,其中
R23代表氢或C1-C4-烷基;及R3还代表基团其中R24代表氢,C1-C4-烷基,苄基,吡啶基,喹啉基或苯基,R25代表氢,卤素,氰基,硝基,C1-C4-烷基(任意被氟和/或氯取代),C1-C4-烷氧基(任意被氟和/或氯取代),二氧杂环戊烷基或C1-C4-烷氧基-羰基,及R26代表氢,卤素或C1-C4-烷基。
本发明还优选涉及式(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)-锍盐,C5-或C6-环烷基-铵盐和二-(C1-C2-烷基)-苄基-铵盐,其中Q1,Q2,R1,R2和R3如上述优选定义。
本发明涉及的具体式(I)化合物,其中Q1代表氧或硫,Q2代表氧或硫,R1在每一种情况任意代表氟,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,或在每一种情况任意代表氟,氯或溴取代的丙烯基,丁烯基,丙炔基或丁炔基,或代表甲氧基,乙氧基,正或异-丙氧基,或代表烯丙氧基,或代表甲氨基,乙氨基,正或异-丙氨基,正,异,仲或叔丁氨基,二甲氨基或二乙氨基,或在每一种情况代表氟,氯,溴,甲基或乙基取代的环丙基,环丁基,环戊基,环己基,环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,或在每一种情况任意代表氟,氯,溴,氰基,甲基,三氟甲基或甲氧基取代的苄基或苯基,R2在每一种情况代表氟和/或氯,甲基和/或乙基取代的氧杂环丁烷基,硫杂环丁烷基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,氧杂环丁烷甲基,硫杂环丁烷甲基,呋喃甲基,四氢呋喃甲基,噻吩甲基或四氢噻吩甲基,及R3代表基团其中R4代表氟,氯,溴,甲基,乙基,正或异-丙基,三氟甲基,甲氧基,乙氧基,正或异丙氧基,正或异丁氧基,二氟甲氧基,三氟甲氧基,2-氯-乙氧基,2,2,2-三氟乙氧基,1,1,2,2-四氟-乙氧基,1,1,2,2,2 五氟-乙氧基,2-甲氧基-乙氧基,甲硫基,乙硫基,正或异丙硫基,正或异丁硫基,2-氟-乙硫基,烯丙氧基,炔丙氧基,甲基-亚磺酰基,乙基亚磺酰基,甲基磺酰基,乙基磺酰基,二甲氨基磺酰基,二乙氨基磺酰基,N-甲氧基-N-甲氨基磺酰基,苯基,苯氧基,甲氧基羰基,乙氧基羰基,正或异丙氧基羰基,及R5代表氢,氟,氯,溴,甲基,乙基,正或异丙基,三氟甲基,甲氧基,乙氧基,正或异-丙氧基,二氟甲氧基,三氟甲氧基,甲硫基或乙硫基;及R3还代表基团其中R10代表氢,R11代表氟,氯,溴,甲基,甲氧基,二氟甲氧基,三氟甲氧基,乙氧基,甲氧基羰基,乙氧基羰基,甲基磺酰基或二甲氨基磺酰基,及R12代表氢;及R3还代表基团其中R代表甲基,乙基,正或异-丙基,或R3代表基团其中R24代表甲基,乙基,正或异-丙基,苯基或吡啶基,R25代表氢,氟,氯或溴,R26代表氟,氯,溴,甲氧基羰基或乙氧基羰基。
上面给出的一般性或优选范围的基团定义,不仅适用于式(I)的终产物,而且适用于每一制备方法中相应的起始原料和/或中间体。根据需要,这些基团定义可以相互结合,因此包括优选化合物的所述范围之结合。
即使没有特别指出,上述基团定义中的烃基,如烷基,链烯基或炔基,单独的或与杂原子结合的基团如烷氧基,烷硫基或烷氨基均为直链或支链的。
卤素一般代表氟,氯,溴或碘,优选氟,氯或溴,特别是氟或氯。
例如,用N-甲氧基羰基-2-甲氧基-苯磺酰胺和5-(四氢-2-呋喃基-甲氧基)-4-甲基-2,4-二氢-3H-1,2,4-三唑-3-酮作为起始原料,本发明方法(c)的反应过程可用以下反应式表示:
在制备本发明式(I)化合物的方法(a),(c)和(d)中所用起始原料三唑啉(硫)酮类的一般定义由式(II)给出。
在式(II)中,Q1,R1和R2优选或特别优选具有上述对于本发明式(I)化合物中的Q1,R1和R2优选或特别优选的相同之定义。
通式(II)三唑啉(硫)酮类是文献中还没有公开过的新物质,它们为本申请的一部分。
新的通式(II)三唑啉(硫)酮类通过以下方法获得:通式(IX)的(硫)肼基甲酸酯其中Q1如上定义,及R27代表任意取代的烷基(优选甲基,乙基,甲氧基乙基或乙氧基乙基)或代表苯基与通式(X)的烷基亚氨基碳酸二酯其中R1和R2如上定义,及G代表烷基(优选甲基或乙基)或与R2定义相同,任意在稀释剂,例如甲醇,和任意在反应助剂,例如新戊酸存在下,在温度0℃到100℃之间反应,并将在该反应中形成的通式(XI)化合物其中Q1,R1,R2和R27如上定义在任意经过中间体分离后任意在稀释剂,例如甲醇,和任意在反应助剂例如甲醇钠的存在下,在温度20℃到150℃之间进行环化缩合反应(参考制备实施例)。
在制备本发明式(I)化合物的方法(a)中所用起始原料磺酰基异(硫)氰酸酯的一般定义由式(III)给出。
在式(III)中,Q2和R3优选或特别优选具有上述对于本发明式(I)化合物中的Q2和R3优选或特别优选的相同之定义。
起始原料式(III)是已知的和/或可用本身已知方法制备,特别是(参考US-P 4 127 405,US-P 4 169 719,US-P 4 371 391,EP A 7 687,EP-A13 480,EP-A 21 641,EP-A 23 141,EP-A 23 422,EP-A 30 139,EP-A 35893,EP-A 44 808,EP-A 44 809,EP-A 48 143,EP-A 51 466,EP-A 64 322,EP-A 70 041,EP-A 173 312)。
在制备本发明式(I)化合物的方法(b)中所用起始原料三唑啉(硫)酮类衍生物的一般定义由式(IV)给出。在式(IV)中,Q1,Q2,R1和R2优选或特别优选具有上述对于本发明式(I)化合物中的Q1,Q2,R1和R2优选或特别优选的相同之定义,并且Z优选代表氟,氯,溴,甲氧基,乙氧基,苄氧基,苯氧基,卤代或硝基苯氧基,特别是甲氧基,苯氧基或4-硝基-苯氧基。
起始原料通式(IV)是文献中还没有公开过的新物质,同样,它们为本申请的一部分。
Z-CQ2-Z1 (XII)Q2和Z如上定义Z1代表卤素(特别是氯),烷氧基(特别是甲氧基),芳烷氧基(特别是苄氧基)或芳氧基(特别是苯氧基),任意在酸接受体,例如氢化钠或氢化钾,氢氧化钠或氢氧化钾,叔丁醇钠或叔丁醇钾,和任意在稀释剂,例如四氢呋喃或二甲氧基乙烷存在下,或在包括水和有机溶剂,例如二氯甲烷或氯仿的两相系统中,在温度0℃到100℃之间反应。
在制备本发明式(I)化合物的方法(b)中所用起始原料磺酰胺的一般定义由式(V)给出。在式(V)中,R3优选或特别优选具有上述对于本发明式(I)化合物中的R3优选或特别优选的相同之定义。
起始原料式(V)是已知的和/或可用本身已知的方法制备(参见US-P4 127 405,US-P 4 169 719,US-P 4 371 391,EP-A 7 687,EP-A 13 480,EP-A 21 641,EP-A 23 141,EP-A 23 422,EP-A 30 139,EP-A 35 893,EP-A 44 808,EP-A 44 809,EP-A 48 143,EP-A 51 466,EP-A 64 322,EP-A 70 041,EP-A 173 312)。
在制备本发明式(I)化合物的方法(c)中所用起始原料磺酰胺衍生物的一般定义由式(VI)给出。在式(VI)中,Q2和R3优选或特别优选具有上述对于本发明式(I)化合物中的Q2和R3优选或特别优选的相同之定义;并且Z优选代表氟,氯,溴,甲氧基,乙氧基,苄氧基,或苯氧基,特别是甲氧基或苯氧基。
起始原料式(VI)是已知的和/或可用本身已知的方法制备。
在制备本发明式(I)化合物的方法(d)中所用起始原料磺酰卤的一般定义由式(VII)给出。在式(VII)中,R3优选或特别优选具有上述对于本发明式(I)化合物中的R3优选或特别优选的相同之定义;X优选代表氟,氯或溴,特别是氯。
起始原料式(VII)是已知的和/或可用本身已知的方法制备。
制备本发明新的式(I)化合物的方法(a),(b),(c)和(d)优选在使用稀释剂情况下进行。在本文中适当的稀释剂实际上是惰性有机溶剂。这些溶剂优选为脂肪的,芳香的,任意卤代的烃类,如戊烷,己烷,庚烷,环己烷,石油醚,汽油,轻石油,苯,甲苯,二甲苯,二氯甲烷,二氯乙烷,氯仿,四氯甲烷,氯苯和邻-二氯苯;醚类如乙醚和二丁基醚,乙二醇二甲醚和二乙二醇二甲醚,四氢呋喃和二噁烷;酮类如丙酮,甲乙酮,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,例如乙腈和丙腈;酰胺类,例如二甲基甲酰胺,二甲基乙酰胺和N-甲基-吡咯烷酮,和二甲基亚砜,四氢噻吩砜和六甲基磷酰胺。
作为反应助剂和/酸接受体,在本发明方法(a),(b),(c)和(d)中可以使用所有在这类反应中通常使用的酸结合试剂。适当的实例优选为碱金属氢氧化物如氢氧化钠和氢氧化钾,碱土金属氢氧化物,例如氢氧化钙,碱金属碳酸盐和碱金属醇盐,如碳酸钠和碳酸钾,叔丁醇钠和叔丁醇钾,及碱性氮化合物,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)和(d)的反应温度可以在相当大的范围内变化。一般该方法在温度-20℃-+100℃之间,优选温度在0℃-+80℃之间进行。
本发明方法(a),(b),(c)和(d)一般在常压下进行,但是也可能在加压或减压下进行。
为了进行本发明方法(a),(b),(c)和(d),各种情况所需的起始原料一般以约等摩尔量使用。但是,各种情况使用的组分之一也可以是相对过量的。这类反应一般在适当的稀释剂中,在酸接受体的存在下进行,并且将反应混合物在具体所需的温度下搅拌数小时。根据常规方法处理本发明方法(a),(b),(c)和(d)中每一种情况的产物(参考制备实施例)。
如果需要,从本发明通式(I)化合物可制备其盐。这种盐用盐形成的常规方法以简单的方式得到,例如将式(I)化合物溶解或分散在适当溶剂中,例如二氯甲烷,丙酮,叔丁基甲基醚或甲苯,并且加入适当的碱。然后经过任意一段时间的搅拌后用浓缩或吸滤法分离该盐。
本发明活性化合物可用作破坏阔叶植物的脱叶剂,干燥剂,特别是除草剂。从最广义上讲,杂草应理解为生长在不需要地域的所有植物。本发明物质根据具体用量用作全部或选择性除草剂。
本发明活性化合物例如可用于下列植物:双子叶杂草属:欧白芥属,独行菜属,猪殃殃属,繁缕属,母菊属,春黄菊属,牛膝菊属,藜属,荨麻属,千里光属,苋属,马齿苋属,苍耳属,旋花属,番薯属,蓼属,田菁属,豚草属,蓟属,飞廉属,苦苣菜属,茄属,焊菜属,节节菜属,母草属,野芝麻属,油桐属,苘麻属,刺酸模属,曼陀罗属,堇菜属,鼬瓣花属,罂粟属,矢车菊属,车轴草属,毛莨属和蒲公英属。双子叶培植属:棉属,大豆属,甜菜属,胡萝卜属,菜豆属,豌豆属,茄属,亚麻属,番薯属,野豌豆属,烟草属,番茄属,落花生属,芥属,莴苣属,香瓜属和南瓜属。单子叶杂草属:稗属,狗尾草属,黍属,马唐属,梯牧草属,早熟禾属,羊茅属,蟋蟀草属,臂形草属,黑麦草属,雀麦属,燕麦属,莎草属,高粱属,冰草属,狗牙根属,雨久花属,飘拂草属,慈姑属,荸荠属,镳草属,雀稗属,鸭嘴草属,尖瓣花属,龙爪茅属,剪股颖属,看麦娘属和Apera。单子叶养殖属:稻属,玉蜀黍属,小麦属,大麦属,燕麦属,黑麦属,高粱属,黍属,甘蔗属,凤梨属,天门冬属和葱属。但是,本发明活性化合物的用途不以任何方式限定于这些植物种属,而以同样方式应用于其它植物。
根据使用的浓度,本发明化合物适用于除去所有杂草,例如工业园区,铁道旁,和有或没有树木种植的道路和区域。同样,本发明化合物可用于除去多年生种植园的杂草,例如林区,树木绿化带,果园,葡萄园,柑橘林,坚果园,香蕉种植园,咖啡种植园,茶叶种植园,橡胶种植园,油棕榈种植园,可可种植园,软水果种植园和蛇麻草地(hopfields),赛马场和牧场,和选择性除去一年生种植植物的杂草。
本发明式(I)化合物特别适用于选择性除去苗前和苗后单子叶和双子叶作物中的单子叶和双子叶杂草。
本发明活性化合物可被转化为常规制剂,如溶液,乳剂,可湿性粉剂,悬浮剂,粉剂,粉尘剂,糊剂,可溶性粉剂,粒剂,悬浮-乳化浓缩剂,用活性化合物浸渗的天然和合成的物质,聚合物中非常精细的胶囊。
这些制剂用常规方法制备,例如将活性化合物和增容剂混合,增容剂是液体溶剂和/或固体载体,任意加有表面活性剂,即乳化剂和/或分散剂和/或发泡剂。
如果使用水作增容剂,也可以使用有机溶剂作辅助溶剂。适宜的液体溶剂主要包括:芳香烃,如二甲苯,甲苯或烷基萘,氯代芳香烃和氯代脂肪烃,如氯苯,氯乙烯或二氯甲烷,脂肪烃如环己烷或石蜡,例如石油馏分,矿物油和植物油,醇类如丁醇或乙二醇以及醚类和酯类,酮类,如丙酮,甲乙酮,甲基异丁基酮或环己酮,强极性溶剂,如二甲基甲酰胺和二甲亚砜,及水。
适宜的固体载体包括:例如铵盐和研磨的天然矿物,如高岭土,粘土,滑石,白垩,石英,绿坡缕石,蒙脱土或硅藻土,研细的合成无机物,如高分散二氧化硅,氧化铝和硅酸盐,适于粒剂的固体载体有:例如,破碎和研碎的天然物质如方解石,大理石,浮石,海泡石和白云石,以及合成的无机和有机粗粉颗粒,和有机原料的颗粒,如木屑,椰子壳,玉米棒子和烟草杆;适宜的乳化剂和/或发泡剂有:例如非离子和阴离子乳化剂,如聚氧乙烯脂肪酸酯,聚氧乙烯脂肪醇醚,例如烷基芳基聚乙二醇醚,烷基磺酸盐,烷基硫酸盐芳基磺酸盐以及白蛋白水解产物;适宜的分散剂有:例如木素亚硫酸盐废母液和甲基纤维素。
可以在制剂中使用的粘合剂如羧甲基纤维素,和粉末,颗粒形式的天然及合成的聚合物或胶乳,如阿拉伯胶,聚乙烯醇和聚乙烯乙酸酯,以及天然磷脂,如脑磷脂和卵磷脂,及合成磷脂。添加剂还可以是矿物油和植物油。
可以使用着色剂如无机颜料,例如氧化铁,氧化钛和普鲁士蓝,及有机染料,如茜素染料,偶氮染料和金属酞菁染料,和使用痕量营养素如铁盐,锰盐,硼盐,铜盐,钴盐,钼盐和锌盐。
制剂中通常含有0.1-95%(重量),优选0.5-90%的活性化合物。
为了除草,本发明化合物可以其自身或制剂形式与已知除草剂混合使用,完全配好的制剂或罐装混合物均可。
混合物中适宜的共用组分是已知的除草剂,例如酰替苯胺类,例如diflufenican和敌稗;芳基羧酸,例如二氯吡啶甲酸,麦草畏和毒莠定;芳氧基链烷羧酸,例如2,4-D,2,4-DB,2,4-DP,氟草定,MCPA,MCPP和绿草定;芳氧基-苯氧基链烷羧酸酯,例如禾草灵,fenoxaprop-ethyl,吡氟禾草灵,吡氟乙草灵和喹禾灵;吖嗪酮类,例如杀草敏和达草灭;氨基甲酸酯类,例如氯苯胺灵,desmedipham,苯敌草,苯胺灵;氯腈类,例如甲草胺,乙草胺,丁草胺,metazachlor,异丙甲草胺,丙草胺和毒草胺;二硝基苯胺类,例如黄草消,二甲戊乐灵和氟乐灵;二苯醚类,例如三氟羧草醚,甲羧除草醚,fluoroglycofen,氟磺胺草醚,halosafen,克阔乐和乙氧氟草醚;脲类,例如绿麦隆,敌草隆,氟草隆,异丙隆,利谷隆和噻唑隆;羟基胺类,例如alloxydim,clethodim,cycloxydim,稀禾定和tralkoxydim;咪唑酮类,例如普杀特,imazamethabenz,imazapyr和imazaquin;腈类,例如溴苯腈,敌草腈和碘苯腈;氧乙酰胺类,例如mefenacet;磺酰脲类,例如amidosulfuron,苄嘧黄隆,chlorimuron-ethyl,绿黄隆,cinosulfuron,甲黄隆,nicosulfuron,primisulfuron,吡嘧黄隆,thifensulfuron-methyl,triasulfuron和tribenuron-methyl;硫代氨基甲酸酯类,例如丁酸酯,草灭特,野麦敌,扑草灭,esprocarb,草灭达,prosulfocarb,杀草丹和燕麦畏;三嗪类,例如莠去津,氰草津,西玛津,西草净,去草净和terbutylazine;三嗪酮类,例如环嗪酮,metamitron和嗪草酮;其它类,例如氨基三唑类,benfuresate,灭草松,恶庚草烷,广灭灵,clopyralid,燕麦枯,dithiopyr,ethofumesate,fluorochloridone,glufosinate,草甘膦,isoxaben,哒草特,快杀稗,quinmerac,sulphosate和tridiphane.
也可以使用与其它已知活性化合物,如杀真菌剂,杀虫剂,杀螨剂,杀线虫剂,鸟驱除剂,植物营养素和改善土壤结构的药剂的混合物。
活性化合物可以以其制剂形式,或通过进一步稀释配制成使用形式,如配好备用的溶液,悬浮液,乳液,粉剂,糊剂和粒剂。它们可以用常规方式,例如浇灌,喷洒,喷雾和散播使用。
本发明活性化合物可以在植物的苗前或苗后施用。也可以在播种前将它们混合在土壤中。
本发明活性化合物的用量可以在非常大的范围内变化。其主要依据所需作用的性质。一般该活性化合物的用量为每公顷土壤表面1g-10kg之间,优选每公顷5g-2kg之间。
将1.3g(7mmol)4-甲基-5-(3-四氢呋喃基-氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮,2.24g(8.4mmol)2-三氟甲氧基苯磺酰基异氰酸酯和60ml乙腈的混合物,在约20℃搅拌16小时。在水泵抽真空下浓缩,将剩余物与异丙醇/石油醚(体积约3/7)一起搅拌并,通过吸滤分离在该方法中得到的结晶产物。
将2.5g(10mmol)2-溴-苯磺酰胺溶解在40ml乙腈中,并在搅拌下加入3.2g(10mmol)4-甲基-2-苯氧羰基-5-(3-四氢呋喃基-氧基)-2,4-二氢-3H-l,2,4-三唑-3-酮和1.6g(10mmol)二氮杂双环十一碳烯(DBU)。将该混合物在20℃搅拌12小时,然后在水泵抽真空下浓缩,将剩余物溶解在二氯甲烷中,并用浓度10%的盐酸洗涤该混合物,用硫酸钠干燥并过滤。在水泵抽真空下浓缩滤液,将剩余物用异丙醇/石油醚(1/5)吸收并通过吸滤分离所得结晶产物。
得到3.5g(理论值的78%)2-(2-溴-苯磺酰基-氨基羰基)-4-甲基-5-(3-四氢呋喃基-氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点191℃。
用类似实施例1或2的方法,也可以根据本发明制备方法的一般性描述,制备表1中所列的式(I)化合物。表1:式(I)化合物的实施例表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)表1(续)起始原料式(II)实施例(II-1)步骤1:
将233g(2.65mol)3-羟基-四氢呋喃在50mbar水泵抽真空下和750ml甲苯中共沸脱水。然后在冰冷却下,在约20分钟内加入18g(0.60mol)氢化钠(纯度80%)。30分钟后,用冰冷却到50℃,在约30分钟内滴加176g(2.41mol)异硫氰酸甲酯。然后在50℃将反应混合物搅拌约2小时以上。接着在冰冷却下,用71.2g浓度30.7%盐酸(0.60mol HCl)中和,最后在100mbar共沸脱水并过滤,并将滤液浓缩至约500g。步骤2:
先在40℃油泵抽真空下加入782g(2.65mol)二丁锡二甲醇盐,然后在约30分钟内滴加步骤1得到的产物的溶液。在该滴加过程中,蒸除甲醇并将温度升至约80℃。接着用氮气代替空气并将反应混合物在100℃搅拌16小时。然后在油泵抽真空下进行精馏。蒸出43g最初馏分后,得到290ml主要馏分(在1mbar/60℃)。气相色谱分析表明,该主要馏分由203.5g(1.28mol)甲基亚氨基-碳酸O-甲酯O-(3-四氢呋喃基)酯和75.2g(0.35mol)甲基亚氨基-碳酸O,O-双(四氢呋喃基)酯组成。步骤3:
先在0℃加入261g(1.63mol)2-乙氧基乙基肼基甲酸酯,并立即加入所有步骤2的已经冷却至0℃的产物混合物。然后在约20分钟间隔内,分几份加入1.66g新戊酸,并将该混合物在20℃搅拌16小时,在45℃搅拌30分钟以上。加入299g浓度30%甲醇-甲醇钠(1.66mol甲醇钠)溶液后,将混合物在55℃再搅拌3小时。冷却后,在冰冷却下用197g浓度30.7%盐酸(1.66mol HCl)中和反应混合物,然后在水泵抽真空下浓缩。剩余物从750ml甲苯中重结晶得到209g产物混合物,气相色谱分析表明,由含量51%的4-甲基-5-甲氧基-2,4-二氢-3H-1,2,4-三唑-3-酮和含量43%4-甲基-5-(3-四氢呋喃基-氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮组成。将产物混合物从400ml水中重结晶得到50g 4-甲基-5-甲氧基-2,4-二氢-3H-1,2,4-三唑-3-酮,为结晶产物。蒸发浓缩母液并将剩余物从400ml甲苯中重结晶。该产物从甲醇中再重结晶得到83g(0.45mol)4-甲基-5-(3-四氢呋喃基-氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点164℃。
在搅拌及20℃-30℃将6.9g(44mmol)氯甲酸苯酯滴加到7.4g(40mmol)4-甲基-5-(3-四氢呋喃基-氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮,1.8g(44mmol)氢氧化钠,0.2g四丁基氯化铵,50ml水和50ml二氯甲烷的混合物中,并将反应混合物在20℃搅拌12小时。接着分出有机相,用水洗涤,用硫酸钠干燥并过滤。在水泵抽真空下浓缩滤液,用石油醚吸收剩余物,并通过吸滤分离该方法中得到的结晶产物。
得到11.8g(理论值的97%)4-甲基-2-苯氧羰基-5-(3-四氢呋喃基-氧基)-2,4-二氢-3H-1,2,4-三唑-3-酮,熔点98℃。
也可以用类似实施例(IV-1)的方法制备下列表3中所列的式(IV)化合物。表3:式(IV)化合物的实施例表3(续)表3(续)表3(续)表3(续)表3(续)表3(续)表3(续)应用实施例实施例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
为了制备适当的活性化合物的制剂,将1份(重量)活性化合物与上述量的溶剂混合,加入上述量的乳化剂并用水将浓溶液稀释至所需浓度。
将试验植物的种子种在正常土壤中,24小时后,用活性化合物的制剂给土壤浇水。需保持每单位面积恒量的水。制剂中活性化合物浓度并不重要,只有每单位面积施用的活性化合物的量是决定性的。
3星期后,与未处理对照组比较,植物的损伤程度用%损伤计算。数字表示:0%=无作用(如未处理对照组)100%=全部毁灭
在该试验中,本发明式(I)化合物对杂草显示很强作用(参见表A)。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
为了制备适当的活性化合物的制剂,将1份(重量)活性化合物与上述量的溶剂混合,加入上述量的乳化剂并用水将浓溶液稀释至所需浓度。
将高5-15cm试验植物用活性化合物的制剂喷洒,所述喷洒方式是按每单位面积所需施用活性化合物的特定量进行。选择喷洒液体一定浓度,使所需施用活性化合物的特定量为1,000l水/公顷。
3星期后,与未处理对照组比较,植物的损伤程度用%损伤计算。数字表示:0%=无作用(如未处理对照组)100%=全部毁灭
在该试验中,本发明式(I)化合物对杂草显示很强作用(参见表B)。表A:苗前试验/温室活性化合物g ai./ha 看麦 雀麦属 莎草属 黑麦 苋属 决明属 藜属 婆婆的实施例号 娘属 草属 纳属(34)[参见表1] 500 100 100 100 100 100 100 100 100表B:苗后试验/温室活性化合物 g ai./ha 苋属 茄属 繁缕属 苍耳属的实施例号(34)[参见表1] 500 95 95 90 95
Claims (10)
1.通式(I)的含有杂环(烷)氧基取代基的磺酰氨基(硫)羰基三唑啉(硫)酮类及式(I)化合物的盐其中Q1代表氧或硫,Q2代表氧或硫,R1代表氢,羟基,氨基或亚烷基氨基或在每一种情况代表任意取代的下列基团:烷基,链烯基,炔基,烷氧基,烯氧基,烷氨基,二烷氨基,链烷酰氨基,环烷基,环烷基烷基,环烷基氨基,芳基和芳烷基,R2在每一种情况代表任意取代的杂环基或杂环基烷基,及R3在每一种情况代表任意取代烷基,芳烷基,芳基和杂芳基。
2.根据权利要求1的式(I)化合物,其特征在于在这些化合物中Q1代表氧或硫,Q2代表氧或硫,R1代表氢,羟基,氨基或C1-C6-亚烷基氨基,或任意代表氟,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,或在每一种情况任意代表氟,氯,和/或溴取代的C2-C6-链烯基或C2-C6-炔基,或代表C1-C6-烷氧基或C3-C6-烯氧基,或在每一种情况任意代表氟和/或氯取代的C1-C6-烷氨基,二(C1-C4-烷基)-氨基或C1-C4-链烷酰氨基,或在每一种情况任意代表氟,氯,溴和/或C1-C4-烷基取代的C3-C6-环烷基或C3-C6-环烷基-C1-C4-烷基,或在每一种情况任意代表氟,氯,溴,氰基,硝基,C1-C4-烷基,三氟甲基,C1-C4-烷氧基和/或C1-C4-烷氧基-羰基取代的苯基或苯基-C1-C4-烷基,R2在每一种情况代表卤素和/或C1-C4-烷基取代的氧杂环丁烷基,硫杂环丁烷基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,吡啶基,嘧啶基,氧杂环丁烷基-C1-C4-烷基,硫杂环丁烷基-C1-C4烷基,呋喃基-C1-C4-烷基,四氢呋喃基-C1-C4-烷基,噻吩基-C1-C4-烷基,四氢噻吩基-C1-C4-烷基,吡啶基-C1-C4-烷基或嘧啶基-C1-C4-烷基,及R3代表基团其中R4和R5相同或不同,并且代表氢,氟,氯,溴,碘,硝基或C1-C6-烷基(可任意被氟,氯,溴,氰基,羧基,C1-C4-烷氧羰基,C1-C4-烷基氨基-羰基,二-(C1-C4-烷基)-氨基-羰基,羟基,C1-C4-烷氧基,甲酰氧基,C1-C4-烷基-羰氧基,C1-C4-烷氧基-羰氧基,C1-C4-烷基氨基-羰氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基,C1-C4-烷基磺酰基,二-(C1-C4-烷基)-氨基-磺酰基,C3-C6-环烷基或苯基取代),或代表C2-C6-链烯基(可任意被氟,氯,溴,氰基,C1-C4-烷氧基-羰基,羧基或苯基取代),或代表C2-C6-炔基(可任意被氟,氯,溴,氰基,C1-C4-烷氧基-羰基,羧基或苯基取代),或代表C1-C4-烷氧基(可任意被氟,氯,溴,氰基,羧基,C1-C4-烷氧基-羰基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基取代),或代表C1-C4-烷硫基(可任意被氟,氯,溴,氰基,羧基,C1-C4-烷氧基-羰基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基取代),或代表C2-C6-烯氧基(可任意被氟,氯,溴,氰基,或C1-C4-烷氧基-羰基取代),或代表C2-C6-烯硫基(可任意被氟,氯,溴,氰基,硝基,C1-C3-烷硫基或C1-C4-烷氧基-羰基取代),C3-C6-炔氧基或C3-C6-炔硫基,或代表基团-S(O)p-R6,其中p代表数1或2和R6代表C1-C4-烷基(可任意被氟,氯,溴,氰基,或C1-C4-烷氧基-羰基取代),C3-C6-链烯基,C3-C6-炔基,C1-C4-烷氧基,C1-C4-烷氧基-C1-C4-烷基氨基,C1-C4-烷基氨基,二-(C1-C4-烷基)-氨基或苯基,或代表基团-NHOR7,其中R7代表C1-C12-烷基(可任意被氟,氯,氰基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基,C1-C4-烷基磺酰基,C1-C4-烷基-羰基,C1-C4-烷氧基-羰基,C1-C4-烷基氨基-羰基或二-(C1-C4-烷基)-氨基-羰基取代),或代表C3-C6-链烯基(可任意被氟,氯或溴取代),C3-C6-炔基,C3-C6-环烷基,C3-C6-环烷基-C1-C2-烷基或苯基-C1-C2-烷基(可任意被氟,氯,硝基,氰基,C1-C4-烷基,C1-C4-烷氧基或C1-C4-烷氧基-羰基取代),或代表二苯甲基,或代表苯基(可任意被氟,氯,硝基,氰基,C1-C4-烷基,三氟甲基,C1-C4-烷氧基,C1-C2-氟代烷氧基,C1-C4-烷硫基,三氟甲硫基或C1-C4-烷氧基-羰基取代),R4和/或R5还代表苯基或苯氧基,或代表C1-C4烷基羰基氨基,C1-C4-烷氧基-羰基氨基,C1-C4-烷基氨基-羰基-氨基或二-(C1-C4-烷基)-氨基-羰基氨基,或代表基团-CO-R8,其中R8代表氢,C1-C6-烷基,C3-C6-环烷基,C1-C6-烷氧基,C3-C6-环烷氧基,C3-C6-链烯氧基,C1-C4-烷硫基,C1-C4-烷基氨基,C1-C4-烷氧基氨基,C1-C4-烷氧基-C1-C4-烷基-氨基或二-(C1-C4-烷基)-氨基(可任意被氟和/或氯取代),R4和/或R5还代表三甲基甲硅烷基,噻唑啉基,C1-C4-烷基磺酰氧基,或二-(C1-C4-烷基)-氨基磺酰氨基或代表基团
-CH=N-R9,其中R9任意代表氟,氯,氰基,羧基,C1-C4-烷氧基,C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基取代的C1-C6-烷基,或任意代表氟或氯取代的苄基,或任意代表氟或氯取代的C3-C6-链烯基或C3-C6-炔基,或任意代表氟,氯,溴,C1-C4-烷基,C1-C4-烷氧基,三氟甲基,三氟甲氧基或三氟甲硫基取代的苯基,或任意代表氟,和/或氯取代的C1-C6-烷氧基,C3-C6-烯氧基,C3-C6-炔氧基或苄氧基,或代表氨基,C1-C4-烷基氨基,二(C1-C4-烷基)氨基,苯基氨基,C1-C4-烷基-羰基氨基,C1-C4-烷氧基羰基氨基或C1-C4-烷基-磺酰氨基或任意代表氟,氯,溴或甲基取代的苯基磺酰氨基,及R3代表基团其中R10代表氢或C1-C4-烷基,R11和R12相同或不同,并且代表氢,氟,氯,溴,硝基,氰基,C1-C4-烷基(任意被氟和/或氯取代),C1-C4-烷氧基(任意被氟和/或氯取代),羧基,C1-C4-烷氧基-羰基,二甲氨基羰基,C1-C4-烷基-磺酰基或二(C1-C4-烷基)氨基磺酰基;及R3还代表基团其中R13和R14相同或不同,并且代表氢,氟,氯,溴,硝基,氰基,C1-C4-烷基(任意被氟和/或氯取代),C1-C4-烷氧基(任意被氟和/或氯取代);及R3还代表基团其中R15和R16相同或不同,并且代表氢,氟,氯,溴,硝基,氰基,C1-C4-烷基(任意被氟和/或氯取代),C1-C4-烷氧基(任意被氟和/或氯取代),或代表C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(任意被氟和/或氯取代),或代表氨基磺酰基或单-(C1-C4-烷基)氨基磺酰基,或代表二-(C1-C4-烷基)氨基磺酰基,或C1-C4-烷氧基-羰基或二甲氨基羰基;及R3还代表基团其中R17和R18相同或不同,并且代表氢,氟,氯,溴,C1-C4-烷基(任意被氟和/或氯取代)或C1-C4-烷氧基(任意被氟和/或氯取代),或代表C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(任意被氟和/或氯取代),或代表二-(C1-C4-烷基)-氨基磺酰基;及R3还代表基团其中R19和R20相同或不同,并且代表氢,氟,氯,溴,氰基,硝基,C1-C4-烷基(任意被氟和/或氯取代),C1-C4-烷氧基(任意被氟和/或氯取代),C1-C4-烷硫基,C1-C4-烷基亚磺酰基或C1-C4-烷基磺酰基(任意被氟和/或氯取代),二-(C1-C4-烷基)-氨基磺酰基,C1-C4-烷氧基-羰基或二甲氨基羰基;及A代表氧,硫或基团N-Z1,其中
Z1代表氢,C1-C4-烷基(任意被氟,氯,溴,或氰基取代),C3-C6-环烷基,苄基,苯基(任意被氟,氯,溴,或硝基取代),C1-C4-烷基羰基,C1-C4-烷氧基羰基或二(C1-C4-烷基)氨基羰基;及R3还代表基团其中R21和R22相同或不同,并且代表氢,C1-C4-烷基,卤素,C1-C4-烷氧基羰基,C1-C4-烷氧基,或C1-C4-卤代烷氧基,Y1代表硫或基团N-R23,其中
3.根据权利要求1的式(I)化合物,其特征在于在这些化合物中Q1代表氧或硫,Q2代表氧或硫,R1在每一种情况任意代表氟,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,或在每一种情况任意代表氟,氯或溴取代的丙烯基,丁烯基,丙炔基或丁炔基,或代表甲氧基,乙氧基,正或异-丙氧基,或代表烯丙氧基,或代表甲氨基,乙氨基,正或异-丙氨基,正,异,仲或叔丁氨基,二甲氨基或二乙氨基,或在每一种情况代表氟,氯,溴,甲基或乙基任意取代的环丙基,环丁基,环戊基,环己基,环丙基甲基,环丁基甲基,环戊基甲基或环己基甲基,或在每一种情况任意代表氟,氯,溴,氰基,甲基,三氟甲基或甲氧基取代的苄基或苯基,R2在每一种情况代表氟和/或氯,甲基和/或乙基取代的氧杂环丁烷基,硫杂环丁烷基,呋喃基,四氢呋喃基,噻吩基,四氢噻吩基,氧杂环丁烷甲基,硫杂环丁烷甲基,呋喃甲基,四氢呋喃甲基,噻吩甲基或四氢噻吩甲基,及R3代表基团其中R4代表氟,氯,溴,甲基,乙基,正或异-丙基,三氟甲基,甲氧基,乙氧基,正或异丙氧基,正或异丁氧基,二氟甲氧基,三氟甲氧基,2-氯-乙氧基,2,2,2-三氟乙氧基,1,1,2,2-四氟-乙氧基,1,1,2,2,2-五氟-乙氧基,2-甲氧基-乙氧基,甲硫基,乙硫基,正或异丙硫基,正或异丁硫基,2-氟-乙硫基,烯丙氧基,炔丙氧基,甲基-亚磺酰基,乙基亚磺酰基,甲基磺酰基,乙基磺酰基,二甲氨基磺酰基,二乙氨基磺酰基,N-甲氧基-N-甲基-氨基磺酰基,苯基,苯氧基,甲氧基羰基,乙氧基羰基,正或异丙氧基羰基,及R5代表氢,氟,氯,溴,甲基,乙基,正或异丙基,三氟甲基,甲氧基,乙氧基,正或异-丙氧基,二氟甲氧基,三氟甲氧基,甲硫基或乙硫基;及R3还代表基团其中R10代表氢,R11代表氟,氯,溴,甲基,甲氧基,二氟甲氧基,三氟甲氧基,乙氧基,甲氧基羰基,乙氧基羰基,甲基磺酰基或二甲氨基磺酰基,及R12代表氢;及R3还代表基团其中R代表甲基,乙基,正或异-丙基,或R3代表基团其中R24代表甲基,乙基,正或异-丙基,苯基或吡啶基,R25代表氢,氟,氯或溴,R26代表氟,氯,溴,甲氧基羰基或乙氧基羰基。
R3-SO2-N=C=Q2 (III)其中Q2和R3如上定义,或(b)通式(IV)的三唑啉(硫)酮衍生物其中Q1,Q2,R1和R2如上定义,及Z代表卤素,烷氧基,芳烷氧基或芳氧基与通式(V)的磺酰胺任意在酸受体和稀释剂的存在下反应,
R3-SO2-X (VII)其中R3如上定义,X代表卤素和与通式(VIII)的(硫)氰酸金属盐
MQ2CN (VIII)其中Q2如上定义及M代表碱金属或碱土金属等价物,任意在反应助剂和稀释剂的存在下反应,如果需要,用常规方法将从方法(a),(b),(c)或(d)得到的式(I)化合物转化为盐。
5.除草组合物,其特征在于至少含有一种权利要求1的式(I)化合物或其一种盐。
6.权利要求1的通式(I)化合物或其盐在除去不需要的植物生长中的用途。
7.除去杂草的方法,其特征在于使权利要求1的通式(I)化合物或其盐对这些杂草或其生长地起作用。
8.制备除草组合物的方法,其特征在于将权利要求1的通式(I)化合物或其盐与增容剂和/或表面活性剂混合。
10.通式(IV)的三唑啉(硫)酮衍生物,其中Q1代表氧或硫,Q2代表氧或硫,R1代表氢,羟基,氨基或亚烷基氨基,或在每一种情况任意代表选自烷基,链烯基,炔基,烷氧基,烯氧基,烷氨基,二烷氨基,链烷酰氨基,环烷基,环烷基烷基,环烷基氨基,芳基和芳烷基的取代基团,及R2在每一种情况代表取代的杂环基或杂环基烷基,及Z代表卤素,烷氧基,芳烷氧基或芳氧基。
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DE19525973.4 | 1995-07-17 | ||
DE19525973A DE19525973A1 (de) | 1995-07-17 | 1995-07-17 | Sulfonylamino(thio)carbonyltriazolin(thi)one mit Heterocyclyl-(alk)oxy-Substituenten |
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EP (1) | EP0842171B1 (zh) |
JP (1) | JPH11509207A (zh) |
CN (1) | CN1196054A (zh) |
AR (1) | AR002863A1 (zh) |
BR (1) | BR9609567A (zh) |
CA (1) | CA2226891A1 (zh) |
DE (2) | DE19525973A1 (zh) |
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DE4110795A1 (de) * | 1991-04-04 | 1992-10-08 | Bayer Ag | Sulfonylaminocarbonyltriazolinone mit ueber sauerstoff gebundenen substituenten |
US5534486A (en) * | 1991-04-04 | 1996-07-09 | Bayer Aktiengesellschaft | Herbicidal sulphonylaminocarbonyl triazolinones having substituents bonded via oxygen |
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1995
- 1995-07-17 DE DE19525973A patent/DE19525973A1/de not_active Withdrawn
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1996
- 1996-07-04 US US08/981,972 patent/US6001776A/en not_active Expired - Fee Related
- 1996-07-04 CN CN96196813A patent/CN1196054A/zh active Pending
- 1996-07-04 DE DE59605762T patent/DE59605762D1/de not_active Expired - Fee Related
- 1996-07-04 EP EP96924878A patent/EP0842171B1/de not_active Expired - Lifetime
- 1996-07-04 WO PCT/EP1996/002933 patent/WO1997003981A1/de active IP Right Grant
- 1996-07-04 BR BR9609567A patent/BR9609567A/pt not_active Application Discontinuation
- 1996-07-04 CA CA002226891A patent/CA2226891A1/en not_active Abandoned
- 1996-07-04 JP JP9506040A patent/JPH11509207A/ja active Pending
- 1996-07-04 ES ES96924878T patent/ES2150682T3/es not_active Expired - Lifetime
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EP0842171B1 (de) | 2000-08-16 |
DE19525973A1 (de) | 1997-01-23 |
DE59605762D1 (en) | 2000-09-21 |
AU6518996A (en) | 1997-02-18 |
AU700589B2 (en) | 1999-01-07 |
WO1997003981A1 (de) | 1997-02-06 |
ZA966030B (en) | 1997-01-31 |
CA2226891A1 (en) | 1997-02-06 |
US6001776A (en) | 1999-12-14 |
EP0842171A1 (de) | 1998-05-20 |
BR9609567A (pt) | 1999-03-02 |
AR002863A1 (es) | 1998-04-29 |
JPH11509207A (ja) | 1999-08-17 |
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