DK170374B1 - 1-Carbamoyl-2-pyrazolinderivater, fremgangsmåde til fremstilling heraf, middel med herbicid og/eller plantevækstregulerende virkning indeholdende et sådant derivat, og fremgangsmåde til fremstilling af midlet, samt fremgangsmåde til bekæmpelse og/eller forebyggelse af uønsket plantevækst hermed - Google Patents

1-Carbamoyl-2-pyrazolinderivater, fremgangsmåde til fremstilling heraf, middel med herbicid og/eller plantevækstregulerende virkning indeholdende et sådant derivat, og fremgangsmåde til fremstilling af midlet, samt fremgangsmåde til bekæmpelse og/eller forebyggelse af uønsket plantevækst hermed Download PDF

Info

Publication number: DK170374B1
Authority: DK; Denmark
Prior art keywords: approx; group; pyrazoline; carbon atoms; phenyl
Prior art date: 1986-10-31

Application number

DK565787A

Other languages

Danish (da)

English (en)

Other versions

DK565787A (da

DK565787D0 (da

Inventor

Kobus Wellinga

Jacobus H H Eussen

Original Assignee

Duphar Int Res

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1986-10-31

Filing date

1987-10-28

Publication date

1995-08-14

1987-10-28 Application filed by Duphar Int Res filed Critical Duphar Int Res

1987-10-28 Publication of DK565787D0 publication Critical patent/DK565787D0/da

1988-05-01 Publication of DK565787A publication Critical patent/DK565787A/da

1995-08-14 Application granted granted Critical

1995-08-14 Publication of DK170374B1 publication Critical patent/DK170374B1/da

Links

239000003795 chemical substances by application Substances 0.000 title claims description 29
230000002363 herbicidal effect Effects 0.000 title claims description 26
238000002360 preparation method Methods 0.000 title claims description 16
230000008635 plant growth Effects 0.000 title claims description 13
238000000034 method Methods 0.000 title claims description 10
FGCBXTLVUQGHQP-UHFFFAOYSA-N 3,4-dihydropyrazole-2-carboxamide Chemical class NC(=O)N1CCC=N1 FGCBXTLVUQGHQP-UHFFFAOYSA-N 0.000 title claims description 9
230000001105 regulatory effect Effects 0.000 title claims description 7
230000001276 controlling effect Effects 0.000 title claims description 3
239000004009 herbicide Substances 0.000 title description 27
150000001875 compounds Chemical class 0.000 claims abstract description 62
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 45
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 34
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 33
125000005843 halogen group Chemical group 0.000 claims abstract description 31
125000000217 alkyl group Chemical group 0.000 claims abstract description 21
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 18
125000004453 alkoxycarbonyl group Chemical group 0.000 claims abstract description 16
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 14
125000003545 alkoxy group Chemical group 0.000 claims abstract description 12
125000004438 haloalkoxy group Chemical group 0.000 claims abstract description 11
125000001424 substituent group Chemical group 0.000 claims abstract description 11
125000004390 alkyl sulfonyl group Chemical group 0.000 claims abstract description 8
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
125000004995 haloalkylthio group Chemical group 0.000 claims abstract description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 7
125000000623 heterocyclic group Chemical group 0.000 claims abstract description 7
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 5
125000002947 alkylene group Chemical group 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 4
125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
125000004429 atom Chemical group 0.000 claims abstract description 4
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 4
125000004441 haloalkylsulfonyl group Chemical group 0.000 claims abstract description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 4
125000002768 hydroxyalkyl group Chemical group 0.000 claims abstract description 4
125000003884 phenylalkyl group Chemical group 0.000 claims abstract description 4
-1 2-methoxycarbonylphenylsulfonylcarbamoyl Chemical group 0.000 claims description 45
239000013543 active substance Substances 0.000 claims description 30
239000007788 liquid Substances 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 15
150000007530 organic bases Chemical class 0.000 claims description 13
229910052736 halogen Inorganic materials 0.000 claims description 10
150000007529 inorganic bases Chemical class 0.000 claims description 10
239000007787 solid Substances 0.000 claims description 8
125000001544 thienyl group Chemical group 0.000 claims description 6
239000002689 soil Substances 0.000 claims description 5
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 5
125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 claims description 4
125000002541 furyl group Chemical group 0.000 claims description 3
239000000546 pharmaceutical excipient Substances 0.000 claims description 3
125000003226 pyrazolyl group Chemical group 0.000 claims description 3
125000004963 sulfonylalkyl group Chemical group 0.000 claims description 3
239000004094 surface-active agent Substances 0.000 claims description 3
JYYRRIUYBHRVOV-UHFFFAOYSA-N 3-phenyl-n-[2-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydropyrazole-2-carboxamide Chemical compound FC(F)(F)C1=CC=CC=C1S(=O)(=O)NC(=O)N1C(C=2C=CC=CC=2)CC=N1 JYYRRIUYBHRVOV-UHFFFAOYSA-N 0.000 claims description 2
NEXKKBXSHXEXNR-UHFFFAOYSA-N 4-ethyl-n-[2-(trifluoromethyl)phenyl]sulfonyl-3,4-dihydropyrazole-2-carboxamide Chemical compound N1=CC(CC)CN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(F)(F)F NEXKKBXSHXEXNR-UHFFFAOYSA-N 0.000 claims description 2
125000001951 carbamoylamino group Chemical group C(N)(=O)N* 0.000 claims description 2
239000003337 fertilizer Substances 0.000 claims description 2
125000001261 isocyanato group Chemical group *N=C=O 0.000 claims description 2
JRQGVOAREBIIBL-UHFFFAOYSA-N methyl 2-[(3,4-dimethyl-3,4-dihydropyrazole-2-carbonyl)sulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N1C(C)C(C)C=N1 JRQGVOAREBIIBL-UHFFFAOYSA-N 0.000 claims description 2
BWXWIVYYYHUDTG-UHFFFAOYSA-N methyl 2-[(3-propyl-3,4-dihydropyrazole-2-carbonyl)sulfamoyl]benzoate Chemical compound CCCC1CC=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC BWXWIVYYYHUDTG-UHFFFAOYSA-N 0.000 claims description 2
YQCLCZZVTPVIAM-UHFFFAOYSA-N methyl 2-[(5-methyl-3,4-dihydropyrazole-2-carbonyl)sulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N1N=C(C)CC1 YQCLCZZVTPVIAM-UHFFFAOYSA-N 0.000 claims description 2
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
NYEBEGRKZUIXTF-UHFFFAOYSA-N n-(2-chlorophenyl)sulfonyl-3-phenyl-3,4-dihydropyrazole-2-carboxamide Chemical compound ClC1=CC=CC=C1S(=O)(=O)NC(=O)N1C(C=2C=CC=CC=2)CC=N1 NYEBEGRKZUIXTF-UHFFFAOYSA-N 0.000 claims description 2
230000000361 pesticidal effect Effects 0.000 claims description 2
239000003381 stabilizer Substances 0.000 claims description 2
125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
239000003814 drug Substances 0.000 claims 1
229940079593 drug Drugs 0.000 claims 1
235000013312 flour Nutrition 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
GDMWFMKTUXAZNE-UHFFFAOYSA-N methyl 2-[(4-ethyl-3,4-dihydropyrazole-2-carbonyl)sulfamoyl]benzoate Chemical compound N1=CC(CC)CN1C(=O)NS(=O)(=O)C1=CC=CC=C1C(=O)OC GDMWFMKTUXAZNE-UHFFFAOYSA-N 0.000 claims 1
UOJKXZHVZJOTGC-UHFFFAOYSA-N n-(2,6-difluorophenyl)sulfonyl-3-phenyl-3,4-dihydropyrazole-2-carboxamide Chemical compound FC1=CC=CC(F)=C1S(=O)(=O)NC(=O)N1C(C=2C=CC=CC=2)CC=N1 UOJKXZHVZJOTGC-UHFFFAOYSA-N 0.000 claims 1
DNXIASIHZYFFRO-UHFFFAOYSA-N pyrazoline Chemical compound C1CN=NC1 DNXIASIHZYFFRO-UHFFFAOYSA-N 0.000 claims 1
RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 abstract description 3
125000001072 heteroaryl group Chemical group 0.000 abstract 1
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 90
235000019439 ethyl acetate Nutrition 0.000 description 45
239000003921 oil Substances 0.000 description 44
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239000000243 solution Substances 0.000 description 26
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
239000002904 solvent Substances 0.000 description 11
239000000843 powder Substances 0.000 description 10
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
238000003756 stirring Methods 0.000 description 9
230000000694 effects Effects 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
238000001816 cooling Methods 0.000 description 7
230000012010 growth Effects 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
239000000126 substance Substances 0.000 description 7
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-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
235000002637 Nicotiana tabacum Nutrition 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 6
239000011541 reaction mixture Substances 0.000 description 6
244000061176 Nicotiana tabacum Species 0.000 description 5
229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
239000008187 granular material Substances 0.000 description 5
MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical class C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 description 4
235000006760 Acer pensylvanicum Nutrition 0.000 description 4
241000219312 Chenopodium Species 0.000 description 4
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241001289540 Fallopia convolvulus Species 0.000 description 4
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239000002253 acid Substances 0.000 description 4
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RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
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YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
244000248416 Fagopyrum cymosum Species 0.000 description 3
235000018914 Galinsoga parviflora Nutrition 0.000 description 3
244000214240 Galinsoga parviflora Species 0.000 description 3
229920001732 Lignosulfonate Polymers 0.000 description 3
241000227425 Pieris rapae crucivora Species 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
244000098338 Triticum aestivum Species 0.000 description 3
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150000008055 alkyl aryl sulfonates Chemical class 0.000 description 3
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WOZWUQCGXFUMKH-UHFFFAOYSA-N methyl 2-(3,4-dihydropyrazole-2-carbonylsulfamoyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N1N=CCC1 WOZWUQCGXFUMKH-UHFFFAOYSA-N 0.000 description 3
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IVEHTKDWGSILNJ-UHFFFAOYSA-N (2,6-difluorophenyl)sulfonylurea Chemical compound NC(=O)NS(=O)(=O)C1=C(F)C=CC=C1F IVEHTKDWGSILNJ-UHFFFAOYSA-N 0.000 description 2
KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
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RHPCYVNTFRAYEO-UHFFFAOYSA-N 2,6-dichloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=CC(Cl)=C1S(=O)(=O)N=C=O RHPCYVNTFRAYEO-UHFFFAOYSA-N 0.000 description 2
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NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 2
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GQPXMTMGBXOBRF-UHFFFAOYSA-N n-(benzenesulfonyl)-4-ethyl-3,4-dihydropyrazole-2-carboxamide Chemical compound N1=CC(CC)CN1C(=O)NS(=O)(=O)C1=CC=CC=C1 GQPXMTMGBXOBRF-UHFFFAOYSA-N 0.000 description 1
VMLKBZHXCGXGJJ-UHFFFAOYSA-N n-(benzenesulfonyl)-5,5-dimethyl-4h-pyrazole-1-carboxamide Chemical compound CC1(C)CC=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1 VMLKBZHXCGXGJJ-UHFFFAOYSA-N 0.000 description 1
QCNQBLJODCEKRW-UHFFFAOYSA-N n-(benzenesulfonyl)-5-methyl-3,4-dihydropyrazole-2-carboxamide Chemical compound C1CC(C)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1 QCNQBLJODCEKRW-UHFFFAOYSA-N 0.000 description 1
FIAUNDXCTCTSBL-UHFFFAOYSA-N n-(benzenesulfonyl)-5-methyl-3-phenyl-3,4-dihydropyrazole-2-carboxamide Chemical compound C1C(C)=NN(C(=O)NS(=O)(=O)C=2C=CC=CC=2)C1C1=CC=CC=C1 FIAUNDXCTCTSBL-UHFFFAOYSA-N 0.000 description 1
AYLAFWJDFIORCK-UHFFFAOYSA-N n-[(2-chlorophenyl)methylsulfonyl]-5-methyl-3,4-dihydropyrazole-2-carboxamide Chemical compound C1CC(C)=NN1C(=O)NS(=O)(=O)CC1=CC=CC=C1Cl AYLAFWJDFIORCK-UHFFFAOYSA-N 0.000 description 1
IAUPTXPSDMEOMR-UHFFFAOYSA-N n-[2-(difluoromethoxy)phenyl]sulfonyl-3,5,5-trimethyl-4h-pyrazole-1-carboxamide Chemical compound CC1(C)CC(C)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)F IAUPTXPSDMEOMR-UHFFFAOYSA-N 0.000 description 1
LTDORLBDLWNIAS-UHFFFAOYSA-N n-[2-(difluoromethoxy)phenyl]sulfonyl-3-ethyl-3,4-dihydropyrazole-2-carboxamide Chemical compound CCC1CC=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)F LTDORLBDLWNIAS-UHFFFAOYSA-N 0.000 description 1
ABCSHHGJJKAEFB-UHFFFAOYSA-N n-[2-(difluoromethoxy)phenyl]sulfonyl-3-phenyl-3,4-dihydropyrazole-2-carboxamide Chemical compound FC(F)OC1=CC=CC=C1S(=O)(=O)NC(=O)N1C(C=2C=CC=CC=2)CC=N1 ABCSHHGJJKAEFB-UHFFFAOYSA-N 0.000 description 1
JRMUACFVXJMPRL-UHFFFAOYSA-N n-[2-(difluoromethoxy)phenyl]sulfonyl-4-ethyl-3,4-dihydropyrazole-2-carboxamide Chemical compound N1=CC(CC)CN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)F JRMUACFVXJMPRL-UHFFFAOYSA-N 0.000 description 1
KAWJLNRIUOQVGT-UHFFFAOYSA-N n-[2-(difluoromethoxy)phenyl]sulfonyl-5,5-dimethyl-4h-pyrazole-1-carboxamide Chemical compound CC1(C)CC=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)F KAWJLNRIUOQVGT-UHFFFAOYSA-N 0.000 description 1
IBTUVORZJXOMDE-UHFFFAOYSA-N n-[2-(difluoromethoxy)phenyl]sulfonyl-5-methyl-3-phenyl-3,4-dihydropyrazole-2-carboxamide Chemical compound C1C(C)=NN(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)OC(F)F)C1C1=CC=CC=C1 IBTUVORZJXOMDE-UHFFFAOYSA-N 0.000 description 1
IHBDFVRPXPXHJY-UHFFFAOYSA-N n-[2-(difluoromethoxy)phenyl]sulfonyl-5-methyl-4-phenyl-3,4-dihydropyrazole-2-carboxamide Chemical compound CC1=NN(C(=O)NS(=O)(=O)C=2C(=CC=CC=2)OC(F)F)CC1C1=CC=CC=C1 IHBDFVRPXPXHJY-UHFFFAOYSA-N 0.000 description 1
KXVBWLYOCPIUAR-UHFFFAOYSA-N n-[2-(trifluoromethoxy)phenyl]sulfonyl-3,4-dihydropyrazole-2-carboxamide Chemical compound FC(F)(F)OC1=CC=CC=C1S(=O)(=O)NC(=O)N1N=CCC1 KXVBWLYOCPIUAR-UHFFFAOYSA-N 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
150000002828 nitro derivatives Chemical class 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
229910017464 nitrogen compound Inorganic materials 0.000 description 1
231100000989 no adverse effect Toxicity 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
NVGOPFQZYCNLDU-UHFFFAOYSA-N norflurazon Chemical compound O=C1C(Cl)=C(NC)C=NN1C1=CC=CC(C(F)(F)F)=C1 NVGOPFQZYCNLDU-UHFFFAOYSA-N 0.000 description 1
235000015097 nutrients Nutrition 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000008188 pellet Substances 0.000 description 1
CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
239000003209 petroleum derivative Substances 0.000 description 1
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
229910052698 phosphorus Inorganic materials 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
239000005648 plant growth regulator Substances 0.000 description 1
239000003495 polar organic solvent Substances 0.000 description 1
229920000136 polysorbate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
GKKCIDNWFBPDBW-UHFFFAOYSA-M potassium cyanate Chemical compound [K]OC#N GKKCIDNWFBPDBW-UHFFFAOYSA-M 0.000 description 1
LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 description 1
STJLVHWMYQXCPB-UHFFFAOYSA-N propiconazole Chemical compound O1C(CCC)COC1(C=1C(=CC(Cl)=CC=1)Cl)CN1N=CN=C1 STJLVHWMYQXCPB-UHFFFAOYSA-N 0.000 description 1
239000008262 pumice Substances 0.000 description 1
150000003219 pyrazolines Chemical class 0.000 description 1
125000002755 pyrazolinyl group Chemical group 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000010992 reflux Methods 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
229940081974 saccharin Drugs 0.000 description 1
235000019204 saccharin Nutrition 0.000 description 1
239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 1
229940085605 saccharin sodium Drugs 0.000 description 1
239000004576 sand Substances 0.000 description 1
238000007873 sieving Methods 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000006467 substitution reaction Methods 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
FZMKKCQHDROFNI-UHFFFAOYSA-N sulfometuron Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 FZMKKCQHDROFNI-UHFFFAOYSA-N 0.000 description 1
YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
239000000725 suspension Substances 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000002641 tar oil Substances 0.000 description 1
WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
150000003606 tin compounds Chemical class 0.000 description 1
150000003918 triazines Chemical class 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
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
150000003672 ureas Chemical class 0.000 description 1
238000005406 washing Methods 0.000 description 1

Classifications

- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/02—Acyclic alcohols with carbon-to-carbon double bonds
- C07C33/025—Acyclic alcohols with carbon-to-carbon double bonds with only one double bond
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/06—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/18—One oxygen or sulfur atom
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/54—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings condensed with carbocyclic rings or ring systems
- C07D231/56—Benzopyrazoles; Hydrogenated benzopyrazoles
- 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
- C07D405/04—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 directly linked by a ring-member-to-ring-member bond
- 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)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Photoreceptors In Electrophotography (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

DK565787A 1986-10-31 1987-10-28 1-Carbamoyl-2-pyrazolinderivater, fremgangsmåde til fremstilling heraf, middel med herbicid og/eller plantevækstregulerende virkning indeholdende et sådant derivat, og fremgangsmåde til fremstilling af midlet, samt fremgangsmåde til bekæmpelse og/eller forebyggelse af uønsket plantevækst hermed DK170374B1 (da)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
NL8602746		1986-10-31
NL8602746		1986-10-31

Publications (3)

Publication Number	Publication Date
DK565787D0 DK565787D0 (da)	1987-10-28
DK565787A DK565787A (da)	1988-05-01
DK170374B1 true DK170374B1 (da)	1995-08-14

Family

ID=19848755

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DK565787A DK170374B1 (da)	1986-10-31	1987-10-28	1-Carbamoyl-2-pyrazolinderivater, fremgangsmåde til fremstilling heraf, middel med herbicid og/eller plantevækstregulerende virkning indeholdende et sådant derivat, og fremgangsmåde til fremstilling af midlet, samt fremgangsmåde til bekæmpelse og/eller forebyggelse af uønsket plantevækst hermed

Country Status (17)

Country	Link
US (1)	US4927452A (hu)
EP (1)	EP0269141B1 (hu)
JP (1)	JPS63122671A (hu)
KR (1)	KR950013851B1 (hu)
AT (1)	ATE80621T1 (hu)
AU (1)	AU603390B2 (hu)
BR (1)	BR8705745A (hu)
CA (1)	CA1314554C (hu)
DE (1)	DE3781769T2 (hu)
DK (1)	DK170374B1 (hu)
ES (1)	ES2052549T3 (hu)
HU (1)	HU203728B (hu)
IL (1)	IL84300A (hu)
NZ (1)	NZ222321A (hu)
PH (1)	PH25315A (hu)
SU (1)	SU1560055A3 (hu)
ZA (1)	ZA878093B (hu)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5116405A (en) *	1989-11-06	1992-05-26	Nissan Chemical Industries Ltd.	Pyridinesulfonamide derivatives and herbicides
DE4029753A1 (de) *	1990-09-20	1992-03-26	Basf Ag	Sulfonamide
RU2538965C2 (ru) *	2009-01-19	2015-01-10	Эббви Инк.	Вызывающие апоптоз средства для лечения рака и иммунных и аутоиммунных заболеваний

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
PL76607B1 (hu) *	1970-09-19	1975-02-28
US3887709A (en) *	1971-09-16	1975-06-03	Zdzislaw Brzozowski	2-Pyrazoline-1-carboxamide sulfonamide derivatives useful as hypoglycemic agents

1987
- 1987-10-07 EP EP87201921A patent/EP0269141B1/en not_active Expired - Lifetime
- 1987-10-07 ES ES87201921T patent/ES2052549T3/es not_active Expired - Lifetime
- 1987-10-07 DE DE8787201921T patent/DE3781769T2/de not_active Expired - Fee Related
- 1987-10-07 AT AT87201921T patent/ATE80621T1/de not_active IP Right Cessation
- 1987-10-27 HU HU874846A patent/HU203728B/hu not_active IP Right Cessation
- 1987-10-28 SU SU874203568A patent/SU1560055A3/ru active
- 1987-10-28 NZ NZ222321A patent/NZ222321A/xx unknown
- 1987-10-28 ZA ZA878093A patent/ZA878093B/xx unknown
- 1987-10-28 BR BR8705745A patent/BR8705745A/pt not_active IP Right Cessation
- 1987-10-28 CA CA000550407A patent/CA1314554C/en not_active Expired - Fee Related
- 1987-10-28 IL IL84300A patent/IL84300A/xx not_active IP Right Cessation
- 1987-10-28 DK DK565787A patent/DK170374B1/da not_active IP Right Cessation
- 1987-10-29 AU AU80474/87A patent/AU603390B2/en not_active Ceased
- 1987-10-30 JP JP62273602A patent/JPS63122671A/ja active Pending
- 1987-10-30 PH PH36008A patent/PH25315A/en unknown
- 1987-10-30 KR KR87012082A patent/KR950013851B1/ko not_active Expired - Lifetime
1988
- 1988-11-28 US US07/277,529 patent/US4927452A/en not_active Expired - Fee Related

Also Published As

Publication number	Publication date
KR950013851B1 (en)	1995-11-17
ATE80621T1 (de)	1992-10-15
NZ222321A (en)	1990-08-28
HU203728B (en)	1991-09-30
DK565787A (da)	1988-05-01
ES2052549T3 (es)	1994-07-16
AU603390B2 (en)	1990-11-15
DE3781769D1 (de)	1992-10-22
HUT45373A (en)	1988-07-28
EP0269141A3 (en)	1990-04-04
EP0269141B1 (en)	1992-09-16
SU1560055A3 (ru)	1990-04-23
ZA878093B (en)	1988-04-26
IL84300A (en)	1991-11-21
DE3781769T2 (de)	1993-02-11
BR8705745A (pt)	1988-05-31
KR880005088A (ko)	1988-06-28
CA1314554C (en)	1993-03-16
EP0269141A2 (en)	1988-06-01
IL84300A0 (en)	1988-03-31
DK565787D0 (da)	1987-10-28
JPS63122671A (ja)	1988-05-26
US4927452A (en)	1990-05-22
AU8047487A (en)	1988-05-05
PH25315A (en)	1991-04-30

Publication	Publication Date	Title
KR100203826B1 (ko)	1999-06-15	우라실 유도체
US5494886A (en)	1996-02-27	Pyridyl sulphonyl ureas as herbicides and plant growth regulators
US5104443A (en)	1992-04-14	Heterocyclic 2-alkoxyphenoxysulfonylureas and the use thereof as herbicides or plant growth regulators
US5635451A (en)	1997-06-03	Pyridylsulfonylureas as herbicides and plant growth regulators, processes for their preparation and their use
PT87646B (pt)	1993-02-26	Processo para a preparacao duma composicao herbicida contendo triazolinonas substituidas, e de produtos intermediarios para a sua preparacao
EP0128530B1 (de)	1988-04-27	Substituierte 4,5-Dimethoxypyridazone, Verfahren zu ihrer Herstellung, diese enthaltende Herbizide und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
CA1331621C (en)	1994-08-23	Substituted 2-phenylimino-oxazolidine compounds having herbicidal activity
HU206592B (en)	1992-12-28	Herbicide and growth controlling compositions containing substituted sulfonyl-diamide derivatives as active components and process for producing the active components
HUT52761A (en)	1990-08-28	Herbicide and growth-controllong compositions containing heterocyclic substituted sulfonyl-urea derivatives as active components and process for producing the active components
US4623377A (en)	1986-11-18	1,2,3,4-tetrahydroquinolin-1-ylcarbonylimidazoles and herbicidal use thereof
EP0085785B1 (de)	1985-12-11	Substituierte 4,5-Dimethoxy-pyridazone, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
US5102443A (en)	1992-04-07	Heterocyclically substituted phenoxysulfonylureas, and the use thereof as herbicides or plant growth regulators
DK170374B1 (da)	1995-08-14	1-Carbamoyl-2-pyrazolinderivater, fremgangsmåde til fremstilling heraf, middel med herbicid og/eller plantevækstregulerende virkning indeholdende et sådant derivat, og fremgangsmåde til fremstilling af midlet, samt fremgangsmåde til bekæmpelse og/eller forebyggelse af uønsket plantevækst hermed
US4384881A (en)	1983-05-24	Herbicidally active novel benzazol-2-yloxyacetanilides
US4867782A (en)	1989-09-19	Novel herbicidal 2-sulfonyliminothiazolidines
US4963180A (en)	1990-10-16	Heterocyclic-substituted phenylsulfamates, and their use as herbicides and plant growth regulators
DE2920933A1 (de)	1980-12-04	3-aryl-5-methyl-pyrazol-4-carbonsaeureester enthaltende herbizide
US4391629A (en)	1983-07-05	2-Pyridyloxyacetanilides and their use as herbicides
HU189221B (en)	1986-06-30	Herbicide compositions and process for producing heterocyclic compounds utilizable as active agents too
EP0268295B1 (de)	1992-10-07	N-Arylsulfonyl-N'-pyrimidyl-(triazinyl)-harnstoffe
JP3065385B2 (ja)	2000-07-17	置換スルホニルアルキルスルホニル尿素、それらの製造方法および除草剤および植物生長調整剤としてのそれらの用途
CS235028B2 (en)	1985-04-16	Growth regulating and husking causing agents and method of their effective substance production
EP0161442A2 (de)	1985-11-21	Thiazolylharnstoffe, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
JPS62192353A (ja)	1987-08-22	殺菌活性を有する新規なチオ化合物
JPS6314712B2 (hu)	1988-04-01

Legal Events

Date	Code	Title	Description
1995-08-14	B1	Patent granted (law 1993)
1997-06-16	PBP	Patent lapsed