CA1231948A - N-phenylsulfonyl-n'-pyrimidinyl- and -triazinyl-ureas - Google Patents
N-phenylsulfonyl-n'-pyrimidinyl- and -triazinyl-ureasInfo
- Publication number
- CA1231948A CA1231948A CA000408671A CA408671A CA1231948A CA 1231948 A CA1231948 A CA 1231948A CA 000408671 A CA000408671 A CA 000408671A CA 408671 A CA408671 A CA 408671A CA 1231948 A CA1231948 A CA 1231948A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- alkyl
- compound
- alkenyl
- radical
- Prior art date
- Legal status (The legal status 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 status listed.)
- Expired
Links
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- -1 C1-C4-alkylthio Chemical group 0.000 claims abstract description 51
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 23
- 150000002367 halogens Chemical group 0.000 claims abstract description 23
- 239000002585 base Substances 0.000 claims abstract description 22
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 22
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 21
- 239000001257 hydrogen Substances 0.000 claims abstract description 21
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 21
- 239000001301 oxygen Substances 0.000 claims abstract description 21
- 150000003839 salts Chemical class 0.000 claims abstract description 20
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims abstract description 15
- 150000001412 amines Chemical class 0.000 claims abstract description 15
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims abstract description 14
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 12
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 12
- 239000011593 sulfur Chemical group 0.000 claims abstract description 12
- 150000001340 alkali metals Chemical class 0.000 claims abstract description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 8
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract description 7
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 7
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 7
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 4
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract description 4
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 4
- 125000001434 methanylylidene group Chemical group [H]C#[*] 0.000 claims abstract description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 4
- 150000002431 hydrogen Chemical group 0.000 claims abstract 16
- 125000001453 quaternary ammonium group Chemical group 0.000 claims abstract 5
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims abstract 3
- 241000196324 Embryophyta Species 0.000 claims description 40
- 239000000203 mixture Substances 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 29
- 239000004202 carbamide Substances 0.000 claims description 14
- 150000003254 radicals Chemical class 0.000 claims description 14
- 230000008635 plant growth Effects 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 10
- 230000012010 growth Effects 0.000 claims description 9
- 229910052740 iodine Inorganic materials 0.000 claims description 8
- 244000068988 Glycine max Species 0.000 claims description 7
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 6
- 235000010469 Glycine max Nutrition 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 230000001105 regulatory effect Effects 0.000 claims description 6
- 230000001276 controlling effect Effects 0.000 claims description 5
- 150000002540 isothiocyanates Chemical class 0.000 claims description 5
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 3
- 241000220485 Fabaceae Species 0.000 claims description 3
- 244000299507 Gossypium hirsutum Species 0.000 claims description 3
- 240000007594 Oryza sativa Species 0.000 claims description 3
- 235000007164 Oryza sativa Nutrition 0.000 claims description 3
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- ALZKZGUTVJXYEF-UHFFFAOYSA-N benzenesulfonylcarbamic acid Chemical compound OC(=O)NS(=O)(=O)C1=CC=CC=C1 ALZKZGUTVJXYEF-UHFFFAOYSA-N 0.000 claims description 3
- 235000009973 maize Nutrition 0.000 claims description 3
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical compound O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 claims description 3
- 235000009566 rice Nutrition 0.000 claims description 3
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 3
- ZHDSCPNAZAJOKO-UHFFFAOYSA-N [O]C(F)F Chemical compound [O]C(F)F ZHDSCPNAZAJOKO-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 235000013339 cereals Nutrition 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- FDDDEECHVMSUSB-UHFFFAOYSA-N sulfanilamide Chemical compound NC1=CC=C(S(N)(=O)=O)C=C1 FDDDEECHVMSUSB-UHFFFAOYSA-N 0.000 claims description 2
- 229940100389 Sulfonylurea Drugs 0.000 claims 5
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims 5
- 229910001860 alkaline earth metal hydroxide Inorganic materials 0.000 claims 5
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims 5
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims 2
- 239000012948 isocyanate Substances 0.000 claims 2
- 150000002513 isocyanates Chemical class 0.000 claims 2
- SEHAXLDZJMQOCZ-UHFFFAOYSA-N 1,1,1-trifluoro-2-$l^{1}-oxidanylethane Chemical compound [O]CC(F)(F)F SEHAXLDZJMQOCZ-UHFFFAOYSA-N 0.000 claims 1
- PLMLVUGRDOSMTR-UHFFFAOYSA-N 1-[2-(2-chloroethoxy)phenyl]sulfonyl-3-[4-methoxy-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]urea Chemical compound FC(F)(F)COC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 PLMLVUGRDOSMTR-UHFFFAOYSA-N 0.000 claims 1
- PCAZRKUJLUXIRM-UHFFFAOYSA-N 1-[2-(difluoromethoxy)phenyl]sulfonyl-3-[4-methoxy-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]urea Chemical compound FC(F)(F)COC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OC(F)F)=N1 PCAZRKUJLUXIRM-UHFFFAOYSA-N 0.000 claims 1
- FCWUVQZVHWDAAK-UHFFFAOYSA-N 1-[4-(difluoromethoxy)-6-methylpyrimidin-2-yl]-3-[2-(difluoromethoxy)phenyl]sulfonylurea Chemical compound CC1=CC(OC(F)F)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OC(F)F)=N1 FCWUVQZVHWDAAK-UHFFFAOYSA-N 0.000 claims 1
- 239000004615 ingredient Substances 0.000 claims 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims 1
- 150000003456 sulfonamides Chemical class 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 6
- 229910052784 alkaline earth metal Inorganic materials 0.000 abstract description 2
- 150000001342 alkaline earth metals Chemical class 0.000 abstract description 2
- 125000006726 (C1-C5) alkenyl group Chemical group 0.000 abstract 1
- 239000013543 active substance Substances 0.000 description 38
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 10
- 238000002844 melting Methods 0.000 description 10
- 230000008018 melting Effects 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- RTYZCUMXOXNVSI-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOO RTYZCUMXOXNVSI-UHFFFAOYSA-N 0.000 description 9
- 239000004094 surface-active agent Substances 0.000 description 9
- FYKAKDPHDGCKTF-UHFFFAOYSA-N OOOOOOOOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOOOOOOOO FYKAKDPHDGCKTF-UHFFFAOYSA-N 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical class C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- 238000002474 experimental method Methods 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 244000061456 Solanum tuberosum Species 0.000 description 6
- 235000002595 Solanum tuberosum Nutrition 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 235000012015 potatoes Nutrition 0.000 description 6
- 239000002244 precipitate Substances 0.000 description 6
- 239000011734 sodium Substances 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 5
- 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 5
- 239000000843 powder Substances 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- JWOLLWQJKQOEOL-UHFFFAOYSA-N OOOOOOOOOOOOO Chemical compound OOOOOOOOOOOOO JWOLLWQJKQOEOL-UHFFFAOYSA-N 0.000 description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 150000001768 cations Chemical class 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 239000000194 fatty acid Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000002736 nonionic surfactant Substances 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- OZBZONOEYUBXTD-UHFFFAOYSA-N OOOOOOOOO Chemical compound OOOOOOOOO OZBZONOEYUBXTD-UHFFFAOYSA-N 0.000 description 3
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 241000220261 Sinapis Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
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- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
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- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
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- BGVZDBCLXVQONI-UHFFFAOYSA-N 2-(difluoromethoxy)-n-(oxomethylidene)benzenesulfonamide Chemical compound FC(F)OC1=CC=CC=C1S(=O)(=O)N=C=O BGVZDBCLXVQONI-UHFFFAOYSA-N 0.000 description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 2
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- 229910021532 Calcite Inorganic materials 0.000 description 2
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- 241000518994 Conta Species 0.000 description 2
- 241000234653 Cyperus Species 0.000 description 2
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- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 2
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- 241000209140 Triticum Species 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
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- 239000003240 coconut oil Substances 0.000 description 2
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- 239000012043 crude product Substances 0.000 description 2
- DOIRQSBPFJWKBE-UHFFFAOYSA-N dibutyl phthalate Chemical compound CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 2
- 125000004786 difluoromethoxy group Chemical group [H]C(F)(F)O* 0.000 description 2
- MCWXGJITAZMZEV-UHFFFAOYSA-N dimethoate Chemical compound CNC(=O)CSP(=S)(OC)OC MCWXGJITAZMZEV-UHFFFAOYSA-N 0.000 description 2
- 239000006185 dispersion Substances 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 description 2
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 150000004679 hydroxides Chemical class 0.000 description 2
- 150000007529 inorganic bases Chemical class 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/42—One nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- 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<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/52—Two oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/56—One oxygen atom and one sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/40—Nitrogen atoms
- C07D251/42—One nitrogen atom
- C07D251/46—One nitrogen atom with oxygen or sulfur atoms attached to the two other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
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- 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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH507581 | 1981-08-06 | ||
| CH5075/81-2 | 1981-08-06 | ||
| CH2205/82-3 | 1982-04-08 | ||
| CH220582 | 1982-04-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1231948A true CA1231948A (en) | 1988-01-26 |
Family
ID=25689788
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000408671A Expired CA1231948A (en) | 1981-08-06 | 1982-08-04 | N-phenylsulfonyl-n'-pyrimidinyl- and -triazinyl-ureas |
Country Status (23)
Families Citing this family (33)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4579584A (en) * | 1981-10-13 | 1986-04-01 | Ciba-Geigy Corporation | N-phenylsulfonyl-N'-triazinylureas |
| US4780125A (en) * | 1982-09-01 | 1988-10-25 | Ciba-Geigy Corporation | N-phenylsulfonyl-N'-triazinylureas |
| US4579583A (en) * | 1982-09-08 | 1986-04-01 | Ciba-Geigy Corporation | Novel sulfonylureas |
| EP0120814B1 (de) * | 1983-03-28 | 1988-07-27 | Ciba-Geigy Ag | N-Phenylsulfonyl-N'-pyrimidinyl- und -triazinylharnstoffe |
| DE3324802A1 (de) * | 1983-07-09 | 1985-01-17 | Hoechst Ag, 6230 Frankfurt | Neue n-alkoxy- und n- alkylsulfonylaminosulfonylharnstoffe, und neue (pyrimido) triazino-thiadiazinoxide als vorprodukte |
| EP0151554A1 (de) * | 1984-02-03 | 1985-08-14 | Ciba-Geigy Ag | Neue Phenylsulfonamidderivate |
| AU570298B2 (en) * | 1984-02-21 | 1988-03-10 | E.I. Du Pont De Nemours And Company | Aryl or heterocyclic sulfonyl urea derivatives with herbicidal properties |
| AU585761B2 (en) * | 1984-03-07 | 1989-06-22 | E.I. Du Pont De Nemours And Company | Herbicidal fluoroethoxy triazines |
| DE3413565A1 (de) * | 1984-04-11 | 1985-10-24 | Bayer Ag, 5090 Leverkusen | Substituierte sulfonylharnstoffe |
| DE3582352D1 (de) * | 1984-04-11 | 1991-05-08 | Ciba Geigy Ag | Verfahren zur selektiven unkrautbekaempfung in nutzpflanzenkulturen. |
| US4981509A (en) * | 1984-05-24 | 1991-01-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4710221A (en) * | 1985-04-10 | 1987-12-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4871847A (en) * | 1984-05-24 | 1989-10-03 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| ES8609276A1 (es) * | 1984-05-24 | 1986-08-16 | Du Pont | Un procedimiento para la preparacion de nuevos compuestos de sulfonil urea. |
| EP0169815B1 (de) * | 1984-07-26 | 1988-11-02 | Ciba-Geigy Ag | N-Arylsulfonyl-N'-triazinyl- und -pyrimidinylharnstoffe |
| CA1230119A (en) | 1985-11-22 | 1987-12-08 | Craig L. Hillemann | N-2-carboxylphenylsulfonyl-n'-pyrimidin-2-yl or triazin-2-yl-urea compounds |
| US4724039A (en) * | 1985-11-22 | 1988-02-09 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| JPH0720957B2 (ja) * | 1985-11-26 | 1995-03-08 | 日産化学工業株式会社 | ピラゾ−ルスルホニルウレア誘導体、製法および除草剤 |
| US4692524A (en) * | 1986-05-02 | 1987-09-08 | Ciba-Geigy Corporation | Process for the preparation of pyrimidine derivatives |
| US5108487A (en) * | 1986-10-17 | 1992-04-28 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4927453A (en) * | 1986-10-17 | 1990-05-22 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| ATE82971T1 (de) * | 1987-07-01 | 1992-12-15 | Ciba Geigy Ag | Substituierte imidazolone mit herbizider wirkung. |
| DE3811777A1 (de) * | 1988-04-08 | 1989-10-19 | Hoechst Ag | Heterocyclisch substituierte alkyl- und alkenylsulfonylharnstoffe, verfahren zu ihrer herstellung und ihre verwendung als herbizide oder pflanzenwachstumsregulatoren |
| US4900827A (en) * | 1988-12-22 | 1990-02-13 | Ciba-Geigy Corporation | Process for the preparation of pyrimidine derivatives |
| JPH0720959B2 (ja) * | 1989-02-20 | 1995-03-08 | 呉羽化学工業株式会社 | Ｎ―置換―３―〔（２，３―ジメチルマレイミド）アミノ〕ベンゼンスルホンアミド誘導体、その製造方法及び除草剤 |
| ATE111463T1 (de) * | 1989-06-06 | 1994-09-15 | Ciba Geigy Ag | Sulfonylharnstoffe. |
| HU206024B (en) * | 1990-01-31 | 1992-08-28 | Intermed Kft | Herbicidal compositions comprising substituted sulfonylurea derivatives and optionally antidote, as well as process for producing the active ingredients |
| MY136106A (en) * | 1990-09-06 | 2008-08-29 | Novartis Ag | Synergistic composition comprising a sulfonylurea anda thiadiazolo (3,4-a)pyridazine and method of selective weed control. |
| DE4128441A1 (de) * | 1991-08-28 | 1993-03-04 | Basf Ag | Herbizide sulfonylharnstoffe, verfahren und zwischenprodukte zu ihrer herstellung |
| US5244866A (en) * | 1992-07-31 | 1993-09-14 | American Cyanamid Company | Method of inhibiting sprout growth on agronomic crops using acetohydroxy acid synthase inhibiting herbicides |
| DE4238175A1 (de) * | 1992-11-12 | 1994-05-19 | Basf Ag | Herbizide Sulfonylharnstoffe, Verfahren zur Herstellung und ihre Verwendung |
| US5847172A (en) * | 1995-06-07 | 1998-12-08 | Magainin Pharmaceuticals Inc. | Certain aminosterol compounds and pharmaceutical compositions including these compounds |
| DE10111649A1 (de) * | 2001-03-12 | 2002-09-19 | Bayer Ag | Substituierte Fluoralkoxyphenylsulfonylharnstoffe |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL121788C (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | ||||
| FR1468747A (fr) * | 1965-07-19 | 1967-02-10 | Benzène-sulfonyl-1 (pyrimidyl-2)-3 urées | |
| CA1082189A (en) * | 1976-04-07 | 1980-07-22 | George Levitt | Herbicidal sulfonamides |
| DK349479A (da) * | 1978-09-27 | 1980-03-28 | Du Pont | Sulfonamidderivater og deres anvendelse til regulering af plantevaekst |
| US4342587A (en) * | 1979-07-20 | 1982-08-03 | E. I. Du Pont De Nemours And Company | Herbicidal pyridinsulfonamides |
| US4452628A (en) * | 1979-07-26 | 1984-06-05 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4368069A (en) * | 1980-07-11 | 1983-01-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CA1330438C (en) * | 1980-07-17 | 1994-06-28 | Willy Meyer | N-phenylsulfonyl-n'-pyrimidinyl-and-triazinylureas |
-
1982
- 1982-07-26 US US06/401,583 patent/US4545811A/en not_active Expired - Lifetime
- 1982-08-02 DE DE8282810323T patent/DE3267431D1/de not_active Expired
- 1982-08-02 EP EP82810323A patent/EP0072347B1/de not_active Expired
- 1982-08-02 MA MA19769A patent/MA19609A1/fr unknown
- 1982-08-03 CS CS825801A patent/CS241510B2/cs unknown
- 1982-08-04 GR GR68951A patent/GR81400B/el unknown
- 1982-08-04 ZW ZW160/82A patent/ZW16082A1/xx unknown
- 1982-08-04 CA CA000408671A patent/CA1231948A/en not_active Expired
- 1982-08-04 IL IL66460A patent/IL66460A0/xx not_active IP Right Cessation
- 1982-08-04 TR TR21767A patent/TR21767A/xx unknown
- 1982-08-04 DD DD82242248A patent/DD203223A5/de not_active IP Right Cessation
- 1982-08-05 NZ NZ201510A patent/NZ201510A/en unknown
- 1982-08-05 BR BR8204597A patent/BR8204597A/pt not_active IP Right Cessation
- 1982-08-05 ES ES514750A patent/ES514750A0/es active Granted
- 1982-08-05 HU HU822523A patent/HU190702B/hu not_active IP Right Cessation
- 1982-08-05 AU AU86770/82A patent/AU548397B2/en not_active Ceased
- 1982-08-05 DK DK351182A patent/DK159433C/da not_active IP Right Cessation
- 1982-08-05 RO RO108379A patent/RO85266B/ro unknown
- 1982-08-06 KR KR8203541A patent/KR890002084B1/ko not_active Expired
- 1982-08-06 PH PH27686A patent/PH22230A/en unknown
- 1982-08-07 EG EG479/82A patent/EG15835A/xx active
-
1985
- 1985-06-03 US US06/740,937 patent/US4693741A/en not_active Expired - Lifetime
-
1987
- 1987-12-30 MY MY843/87A patent/MY8700843A/xx unknown
-
1989
- 1989-03-10 CY CY1436A patent/CY1436A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| ES8307761A1 (es) | 1983-08-01 |
| MA19609A1 (fr) | 1983-04-01 |
| CS241510B2 (en) | 1986-03-13 |
| DE3267431D1 (en) | 1985-12-19 |
| US4545811A (en) | 1985-10-08 |
| AU548397B2 (en) | 1985-12-12 |
| GR81400B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-12-11 |
| RO85266A (ro) | 1984-09-29 |
| DK159433B (da) | 1990-10-15 |
| TR21767A (tr) | 1985-06-25 |
| US4693741A (en) | 1987-09-15 |
| ES514750A0 (es) | 1983-08-01 |
| NZ201510A (en) | 1985-11-08 |
| CY1436A (en) | 1989-03-10 |
| HU190702B (en) | 1986-10-28 |
| DK351182A (da) | 1983-02-07 |
| EP0072347A1 (de) | 1983-02-16 |
| MY8700843A (en) | 1987-12-31 |
| DD203223A5 (de) | 1983-10-19 |
| KR890002084B1 (ko) | 1989-06-16 |
| AU8677082A (en) | 1983-02-10 |
| IL66460A0 (en) | 1982-12-31 |
| EG15835A (en) | 1986-12-30 |
| PH22230A (en) | 1988-07-01 |
| RO85266B (ro) | 1984-10-30 |
| EP0072347B1 (de) | 1985-11-13 |
| KR840001149A (ko) | 1984-03-28 |
| CS580182A2 (en) | 1985-08-15 |
| DK159433C (da) | 1991-03-18 |
| BR8204597A (pt) | 1983-07-26 |
| ZW16082A1 (en) | 1983-02-23 |
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| MKEX | Expiry |