CA1169426A - Herbicidal sulfonamides - Google Patents
Herbicidal sulfonamidesInfo
- Publication number
- CA1169426A CA1169426A CA000345992A CA345992A CA1169426A CA 1169426 A CA1169426 A CA 1169426A CA 000345992 A CA000345992 A CA 000345992A CA 345992 A CA345992 A CA 345992A CA 1169426 A CA1169426 A CA 1169426A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- och3
- alkyl
- dihydro
- nutsedge
- 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
- 229940124530 sulfonamide Drugs 0.000 title abstract description 4
- 230000002363 herbicidal effect Effects 0.000 title description 4
- 150000003456 sulfonamides Chemical class 0.000 title description 3
- 125000001309 chloro group Chemical class Cl* 0.000 claims description 185
- 150000001875 compounds Chemical class 0.000 claims description 92
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 83
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 61
- 244000075634 Cyperus rotundus Species 0.000 claims description 42
- 235000005853 Cyperus esculentus Nutrition 0.000 claims description 37
- 238000000034 method Methods 0.000 claims description 32
- -1 CO2B Chemical group 0.000 claims description 28
- 125000000217 alkyl group Chemical group 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 15
- 150000003839 salts Chemical class 0.000 claims description 15
- 229910052801 chlorine Inorganic materials 0.000 claims description 14
- 229910052794 bromium Inorganic materials 0.000 claims description 13
- 229910052731 fluorine Inorganic materials 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 10
- LJXQPZWIHJMPQQ-UHFFFAOYSA-N pyrimidin-2-amine Chemical compound NC1=NC=CC=N1 LJXQPZWIHJMPQQ-UHFFFAOYSA-N 0.000 claims description 10
- 101100134922 Gallus gallus COR5 gene Proteins 0.000 claims description 9
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- RVCDOSSBDXSTOW-UHFFFAOYSA-N 2-[(4-methyl-5,6-dihydrofuro[2,3-d]pyrimidin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound N=1C=2OCCC=2C(C)=NC=1NC(=O)NS(=O)(=O)C1=CC=CC=C1C(O)=O RVCDOSSBDXSTOW-UHFFFAOYSA-N 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 235000017168 chlorine Nutrition 0.000 claims description 4
- QPMQGHZMSBTQFA-UHFFFAOYSA-N 1-(4-methoxy-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl)-3-(2-nitrophenyl)sulfonylurea Chemical compound N=1C=2CCCC=2C(OC)=NC=1NC(=O)NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O QPMQGHZMSBTQFA-UHFFFAOYSA-N 0.000 claims description 3
- PSGFTRBGZCIYHW-UHFFFAOYSA-N 1-(4-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl)-3-(2-nitrophenyl)sulfonylurea Chemical compound N=1C=2CCCC=2C(C)=NC=1NC(=O)NS(=O)(=O)C1=CC=CC=C1[N+]([O-])=O PSGFTRBGZCIYHW-UHFFFAOYSA-N 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 3
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 3
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 3
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 3
- 150000002540 isothiocyanates Chemical class 0.000 claims description 3
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 2
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 2
- KGXHHUQGMUDVRT-UHFFFAOYSA-N 1-(2-chlorophenyl)sulfonyl-3-(4-methyl-5,6-dihydrofuro[2,3-d]pyrimidin-2-yl)urea Chemical compound N=1C=2OCCC=2C(C)=NC=1NC(=O)NS(=O)(=O)C1=CC=CC=C1Cl KGXHHUQGMUDVRT-UHFFFAOYSA-N 0.000 claims description 2
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000005336 allyloxy group Chemical group 0.000 claims description 2
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 2
- PWLKBUVNCBAQFD-UHFFFAOYSA-N 2-[(4-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound N=1C=2CCCC=2C(C)=NC=1NC(=O)NS(=O)(=O)C1=CC=CC=C1C(O)=O PWLKBUVNCBAQFD-UHFFFAOYSA-N 0.000 claims 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 2
- 101150009274 nhr-1 gene Proteins 0.000 claims 2
- JCXJVPUVTGWSNB-UHFFFAOYSA-N nitrogen dioxide Inorganic materials O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims 2
- 229910052717 sulfur Chemical group 0.000 claims 2
- 239000011593 sulfur Chemical group 0.000 claims 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims 1
- 125000006274 (C1-C3)alkoxy group Chemical group 0.000 claims 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 10
- 125000003118 aryl group Chemical group 0.000 abstract description 2
- 230000008635 plant growth Effects 0.000 abstract 1
- 239000000460 chlorine Substances 0.000 description 287
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 64
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 49
- 235000013350 formula milk Nutrition 0.000 description 42
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 38
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 34
- 240000007594 Oryza sativa Species 0.000 description 32
- 235000007164 Oryza sativa Nutrition 0.000 description 32
- 235000009566 rice Nutrition 0.000 description 32
- 244000037364 Cinnamomum aromaticum Species 0.000 description 30
- 235000014489 Cinnamomum aromaticum Nutrition 0.000 description 30
- 239000000203 mixture Substances 0.000 description 28
- 244000075850 Avena orientalis Species 0.000 description 27
- 240000008042 Zea mays Species 0.000 description 25
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 25
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 25
- 235000005822 corn Nutrition 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- 244000025670 Eleusine indica Species 0.000 description 23
- 235000014716 Eleusine indica Nutrition 0.000 description 23
- 241000209140 Triticum Species 0.000 description 23
- 235000021307 Triticum Nutrition 0.000 description 23
- 235000010469 Glycine max Nutrition 0.000 description 22
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 22
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 21
- 235000007320 Avena fatua Nutrition 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- 235000001602 Digitaria X umfolozi Nutrition 0.000 description 20
- 235000017898 Digitaria ciliaris Nutrition 0.000 description 20
- 235000005476 Digitaria cruciata Nutrition 0.000 description 20
- 235000006830 Digitaria didactyla Nutrition 0.000 description 20
- 235000005804 Digitaria eriantha ssp. eriantha Nutrition 0.000 description 20
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 20
- 244000068988 Glycine max Species 0.000 description 20
- 229920000742 Cotton Polymers 0.000 description 19
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 19
- 238000010992 reflux Methods 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 19
- 241000192043 Echinochloa Species 0.000 description 18
- 235000005373 Uvularia sessilifolia Nutrition 0.000 description 18
- 239000002689 soil Substances 0.000 description 18
- 240000001549 Ipomoea eriocarpa Species 0.000 description 17
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 17
- 241001506766 Xanthium Species 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 229940073584 methylene chloride Drugs 0.000 description 16
- 239000000243 solution Substances 0.000 description 16
- 239000007787 solid Substances 0.000 description 15
- 238000011282 treatment Methods 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 13
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 13
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 11
- 239000008187 granular material Substances 0.000 description 11
- 239000004615 ingredient Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 10
- 239000000725 suspension Substances 0.000 description 10
- 235000007319 Avena orientalis Nutrition 0.000 description 9
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000001704 evaporation Methods 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 8
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 8
- 241000209072 Sorghum Species 0.000 description 8
- 235000011684 Sorghum saccharatum Nutrition 0.000 description 8
- 230000008020 evaporation Effects 0.000 description 8
- 238000009472 formulation Methods 0.000 description 8
- 150000002500 ions Chemical class 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 241001355178 Setaria faberi Species 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 description 7
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 7
- 239000003085 diluting agent Substances 0.000 description 7
- USQCUKQZXOWUDF-YWZLYKJASA-N 6-chloro-n-[(3s)-1-[(2s)-1-(4-methyl-5-oxo-1,4-diazepan-1-yl)-1-oxopropan-2-yl]-2-oxopyrrolidin-3-yl]naphthalene-2-sulfonamide Chemical compound O=C([C@@H](N1C([C@@H](NS(=O)(=O)C=2C=C3C=CC(Cl)=CC3=CC=2)CC1)=O)C)N1CCN(C)C(=O)CC1 USQCUKQZXOWUDF-YWZLYKJASA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 239000001257 hydrogen Substances 0.000 description 6
- 239000000543 intermediate Substances 0.000 description 6
- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 5
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- 230000009102 absorption Effects 0.000 description 5
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- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 150000001768 cations Chemical class 0.000 description 5
- 235000011167 hydrochloric acid Nutrition 0.000 description 5
- 229960000443 hydrochloric acid Drugs 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 5
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 239000004094 surface-active agent Substances 0.000 description 5
- QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 description 4
- 240000006995 Abutilon theophrasti Species 0.000 description 4
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical class NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
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- AANWRPPCSQWSCW-UHFFFAOYSA-N 4-methoxy-5,6-dihydrofuro[2,3-d]pyrimidin-2-amine Chemical compound COC1=NC(N)=NC2=C1CCO2 AANWRPPCSQWSCW-UHFFFAOYSA-N 0.000 description 3
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- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 3
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- MXHIIXNGNJRRBT-UHFFFAOYSA-N 4-chloro-5,6-dihydrofuro[2,3-d]pyrimidin-2-amine Chemical compound ClC1=NC(N)=NC2=C1CCO2 MXHIIXNGNJRRBT-UHFFFAOYSA-N 0.000 description 2
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- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 235000017896 Digitaria Nutrition 0.000 description 2
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- 235000003403 Limnocharis flava Nutrition 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
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- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
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- HVTICUPFWKNHNG-UHFFFAOYSA-N iodoethane Chemical compound CCI HVTICUPFWKNHNG-UHFFFAOYSA-N 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- 229910052622 kaolinite Inorganic materials 0.000 description 1
- CYPPCCJJKNISFK-UHFFFAOYSA-J kaolinite Chemical compound [OH-].[OH-].[OH-].[OH-].[Al+3].[Al+3].[O-][Si](=O)O[Si]([O-])=O CYPPCCJJKNISFK-UHFFFAOYSA-J 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000001819 mass spectrum Methods 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- NIHATBFNWOQIAY-UHFFFAOYSA-N methyl 2-[(4-methyl-6,7-dihydro-5h-cyclopenta[d]pyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC(N=C1C)=NC2=C1CCC2 NIHATBFNWOQIAY-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- ZGEGCLOFRBLKSE-UHFFFAOYSA-N methylene hexane Natural products CCCCCC=C ZGEGCLOFRBLKSE-UHFFFAOYSA-N 0.000 description 1
- 230000002906 microbiologic effect Effects 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910000403 monosodium phosphate Inorganic materials 0.000 description 1
- 235000019799 monosodium phosphate Nutrition 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- DODXZJLHTDSXCR-UHFFFAOYSA-N n-(oxomethylidene)pyridine-2-sulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=N1 DODXZJLHTDSXCR-UHFFFAOYSA-N 0.000 description 1
- JRMWPPYAXFAARO-UHFFFAOYSA-N n-(sulfanylidenemethylidene)pyridine-2-sulfonamide Chemical class S=C=NS(=O)(=O)C1=CC=CC=N1 JRMWPPYAXFAARO-UHFFFAOYSA-N 0.000 description 1
- UZWDCWONPYILKI-UHFFFAOYSA-N n-[5-[(4-ethylpiperazin-1-yl)methyl]pyridin-2-yl]-5-fluoro-4-(7-fluoro-2-methyl-3-propan-2-ylbenzimidazol-5-yl)pyrimidin-2-amine Chemical compound C1CN(CC)CCN1CC(C=N1)=CC=C1NC1=NC=C(F)C(C=2C=C3N(C(C)C)C(C)=NC3=C(F)C=2)=N1 UZWDCWONPYILKI-UHFFFAOYSA-N 0.000 description 1
- HNHVTXYLRVGMHD-UHFFFAOYSA-N n-butyl isocyanate Chemical compound CCCCN=C=O HNHVTXYLRVGMHD-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 230000017074 necrotic cell death Effects 0.000 description 1
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 229910000069 nitrogen hydride Inorganic materials 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000005416 organic matter Substances 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 235000020030 perry Nutrition 0.000 description 1
- 230000002688 persistence Effects 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 230000003389 potentiating effect Effects 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- DWJMBQYORXLGAE-UHFFFAOYSA-N pyridine-2-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=N1 DWJMBQYORXLGAE-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 101150114085 soc-2 gene Proteins 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- CMXPERZAMAQXSF-UHFFFAOYSA-M sodium;1,4-bis(2-ethylhexoxy)-1,4-dioxobutane-2-sulfonate;1,8-dihydroxyanthracene-9,10-dione Chemical compound [Na+].O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=CC=C2O.CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC CMXPERZAMAQXSF-UHFFFAOYSA-M 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- HFOWWBNMJUVIMH-UHFFFAOYSA-N sulfuryl diisothiocyanate Chemical class S=C=NS(=O)(=O)N=C=S HFOWWBNMJUVIMH-UHFFFAOYSA-N 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical class NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 0.000 description 1
- YBNLWIZAWPBUKQ-UHFFFAOYSA-N trichloro(trichloromethylsulfonyl)methane Chemical compound ClC(Cl)(Cl)S(=O)(=O)C(Cl)(Cl)Cl YBNLWIZAWPBUKQ-UHFFFAOYSA-N 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 238000001665 trituration Methods 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052727 yttrium Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
- A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom 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
- C07D213/62—Oxygen or sulfur atoms
- C07D213/70—Sulfur atoms
- C07D213/71—Sulfur atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
- C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
- C07D491/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US1420179A | 1979-02-22 | 1979-02-22 | |
| US014,201 | 1979-02-22 | ||
| US6865879A | 1979-08-28 | 1979-08-28 | |
| US068,658 | 1979-08-28 | ||
| US10926280A | 1980-01-18 | 1980-01-18 | |
| US109,262 | 1980-01-18 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1169426A true CA1169426A (en) | 1984-06-19 |
Family
ID=27360040
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000345992A Expired CA1169426A (en) | 1979-02-22 | 1980-02-19 | Herbicidal sulfonamides |
Country Status (21)
| Country | Link |
|---|---|
| EP (1) | EP0015683B1 (OSRAM) |
| AR (1) | AR224258A1 (OSRAM) |
| AT (1) | ATE5320T1 (OSRAM) |
| AU (1) | AU529929B2 (OSRAM) |
| BG (1) | BG31467A3 (OSRAM) |
| BR (1) | BR8001024A (OSRAM) |
| CA (1) | CA1169426A (OSRAM) |
| DE (1) | DE3065572D1 (OSRAM) |
| DK (1) | DK37880A (OSRAM) |
| ES (1) | ES488825A0 (OSRAM) |
| FI (1) | FI800530A7 (OSRAM) |
| GR (1) | GR72794B (OSRAM) |
| IE (1) | IE49515B1 (OSRAM) |
| IL (1) | IL59443A (OSRAM) |
| NO (1) | NO800487L (OSRAM) |
| NZ (1) | NZ192933A (OSRAM) |
| PL (1) | PL126864B1 (OSRAM) |
| PT (1) | PT70859A (OSRAM) |
| TR (1) | TR20621A (OSRAM) |
| YU (1) | YU46880A (OSRAM) |
| ZW (1) | ZW4380A1 (OSRAM) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DK468979A (da) * | 1978-12-04 | 1980-06-05 | Du Pont | Agrikulturelle pyridinsulfonamider |
| DK469179A (da) * | 1979-10-22 | 1981-04-23 | Du Pont | Agrikulturelle pyridinsulfonylsothiourinstoffer |
| DK172396B1 (da) * | 1979-11-30 | 1998-05-18 | Du Pont | Thiophencarboxylsyrederivater, middel til bekæmpelse af væksten af uønsket vegetation, fremgangsmåde til bekæmpelse af uønsket vegetation samt mellemprodukter til fremstilling af de nævnte derivater |
| US4370479A (en) * | 1979-11-30 | 1983-01-25 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| BR8007727A (pt) * | 1979-11-30 | 1981-06-09 | Du Pont | Composto agricola,composicao apropriada e processo para o controle do crescimento de vegetacao indesejada |
| BR8102529A (pt) * | 1980-04-29 | 1982-01-05 | Du Pont | Compostos e composicoes herbicidas ou adequados ao controle do crescimento de vegetacao indesejavel e seus processos de preparacao;processo para o controle do crescimento de vegetacao indesejavel |
| ZA814658B (en) * | 1980-07-11 | 1983-02-23 | Du Pont | Herbicidal sulfonamides |
| US4368069A (en) * | 1980-07-11 | 1983-01-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4487626A (en) * | 1980-08-22 | 1984-12-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| BR8106972A (pt) * | 1980-11-03 | 1982-07-13 | Du Pont | Composto herbicida composicao e processo para controlar o crescimento de vegetacao indesejada |
| BR8200353A (pt) * | 1981-01-26 | 1982-11-23 | Du Pont | Composto quimico agricola composicao adequada para controlar o crescimento de vegetacao indesejada |
| US4441910A (en) * | 1981-03-24 | 1984-04-10 | E. I. Du Pont De Nemours And Company | Thiophene or furan herbicides |
| AU550945B2 (en) * | 1981-07-10 | 1986-04-10 | E.I. Du Pont De Nemours And Company | Triazolyl-(imidazolyl)-sulphonyl-ureas |
| US4443243A (en) * | 1981-07-16 | 1984-04-17 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N-triazinylureas |
| AU591450B2 (en) * | 1981-10-16 | 1989-12-07 | E.I. Du Pont De Nemours And Company | Novel phenyl-substituted sulfonamides |
| BR8300016A (pt) * | 1982-01-07 | 1983-08-30 | Du Pont | Compostos;composicao adequada e processo para controle de crescimento de vegetacao indesejada |
| BR8300034A (pt) * | 1982-01-07 | 1983-09-13 | Du Pont | Composto;composicao adequada para controlar o crescimento de vegetacao indesejada;processo para controlar o crescimento de vegetacao indesejada |
| EP0091593A1 (de) * | 1982-04-10 | 1983-10-19 | CELAMERCK GmbH & Co. KG | N-Pteridinylharnstoffe, ihre Herstellung und Verwendung |
| US4659369A (en) | 1984-08-27 | 1987-04-21 | E. I. Du Pont De Nemours And Company | Herbicidal acetals and ketals |
| AU578307B2 (en) | 1984-09-17 | 1988-10-20 | E.I. Du Pont De Nemours And Company | Herbicidal pyrazolesulfonamides |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1082189A (en) * | 1976-04-07 | 1980-07-22 | George Levitt | Herbicidal sulfonamides |
-
1980
- 1980-01-29 DK DK37880A patent/DK37880A/da not_active Application Discontinuation
- 1980-02-19 AU AU55681/80A patent/AU529929B2/en not_active Ceased
- 1980-02-19 CA CA000345992A patent/CA1169426A/en not_active Expired
- 1980-02-20 GR GR61245A patent/GR72794B/el unknown
- 1980-02-21 PT PT70859A patent/PT70859A/pt unknown
- 1980-02-21 NO NO800487A patent/NO800487L/no unknown
- 1980-02-21 ES ES488825A patent/ES488825A0/es active Granted
- 1980-02-21 ZW ZW43/80A patent/ZW4380A1/xx unknown
- 1980-02-21 YU YU00468/80A patent/YU46880A/xx unknown
- 1980-02-21 NZ NZ192933A patent/NZ192933A/xx unknown
- 1980-02-21 BR BR8001024A patent/BR8001024A/pt unknown
- 1980-02-21 DE DE8080300505T patent/DE3065572D1/de not_active Expired
- 1980-02-21 AT AT80300505T patent/ATE5320T1/de not_active IP Right Cessation
- 1980-02-21 IE IE340/80A patent/IE49515B1/en unknown
- 1980-02-21 IL IL59443A patent/IL59443A/xx unknown
- 1980-02-21 EP EP80300505A patent/EP0015683B1/en not_active Expired
- 1980-02-21 AR AR280038A patent/AR224258A1/es active
- 1980-02-21 PL PL1980222154A patent/PL126864B1/pl unknown
- 1980-02-22 TR TR20621A patent/TR20621A/xx unknown
- 1980-02-22 BG BG046726A patent/BG31467A3/xx unknown
- 1980-02-22 FI FI800530A patent/FI800530A7/fi not_active Application Discontinuation
Also Published As
| Publication number | Publication date |
|---|---|
| IL59443A (en) | 1985-03-31 |
| ES8103062A1 (es) | 1981-02-16 |
| AU529929B2 (en) | 1983-06-23 |
| AU5568180A (en) | 1980-08-28 |
| FI800530A7 (fi) | 1981-01-01 |
| BG31467A3 (bg) | 1982-01-15 |
| BR8001024A (pt) | 1980-10-29 |
| NO800487L (no) | 1980-08-25 |
| YU46880A (en) | 1983-02-28 |
| PT70859A (en) | 1980-03-01 |
| GR72794B (OSRAM) | 1983-12-05 |
| IE800340L (en) | 1980-08-22 |
| NZ192933A (en) | 1982-03-23 |
| PL222154A1 (OSRAM) | 1980-12-15 |
| DK37880A (da) | 1980-08-23 |
| ATE5320T1 (de) | 1983-12-15 |
| ES488825A0 (es) | 1981-02-16 |
| PL126864B1 (en) | 1983-09-30 |
| TR20621A (tr) | 1982-01-01 |
| ZW4380A1 (en) | 1980-09-10 |
| AR224258A1 (es) | 1981-11-13 |
| EP0015683B1 (en) | 1983-11-16 |
| IE49515B1 (en) | 1985-10-16 |
| EP0015683A1 (en) | 1980-09-17 |
| DE3065572D1 (en) | 1983-12-22 |
| IL59443A0 (en) | 1980-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |