CA1144923A - Herbicidal sulfonamides - Google Patents
Herbicidal sulfonamidesInfo
- Publication number
- CA1144923A CA1144923A CA000356200A CA356200A CA1144923A CA 1144923 A CA1144923 A CA 1144923A CA 000356200 A CA000356200 A CA 000356200A CA 356200 A CA356200 A CA 356200A CA 1144923 A CA1144923 A CA 1144923A
- Authority
- CA
- Canada
- Prior art keywords
- compound
- aminocarbonyl
- alkyl
- benzenedisulfonamide
- och3
- 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 description 17
- 150000003456 sulfonamides Chemical class 0.000 title description 10
- 230000002363 herbicidal effect Effects 0.000 title 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 592
- 150000001875 compounds Chemical class 0.000 claims description 147
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 66
- 238000000034 method Methods 0.000 claims description 52
- -1 CH2CH(CH)3OCH3 Chemical group 0.000 claims description 50
- 239000000460 chlorine Substances 0.000 claims description 50
- 229910052739 hydrogen Inorganic materials 0.000 claims description 37
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 34
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 34
- 229910052801 chlorine Inorganic materials 0.000 claims description 32
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 25
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 23
- 229910052794 bromium Inorganic materials 0.000 claims description 22
- 125000004206 2,2,2-trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 19
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 claims description 19
- 229910052731 fluorine Inorganic materials 0.000 claims description 17
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 14
- 150000003839 salts Chemical class 0.000 claims description 13
- 125000003342 alkenyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 11
- 125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 11
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 10
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 9
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 7
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
- 125000004793 2,2,2-trifluoroethoxy group Chemical group FC(CO*)(F)F 0.000 claims description 6
- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 4
- 125000000392 cycloalkenyl group Chemical group 0.000 claims description 4
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 4
- MSZOLFNKFJFQGO-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-(dimethylsulfamoyl)phenyl]sulfonylurea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)S(=O)(=O)N(C)C)=N1 MSZOLFNKFJFQGO-UHFFFAOYSA-N 0.000 claims description 3
- WBLIXGSTEMXDSM-UHFFFAOYSA-N chloromethane Chemical compound Cl[CH2] WBLIXGSTEMXDSM-UHFFFAOYSA-N 0.000 claims description 3
- KKMFUPRISZBEFY-UHFFFAOYSA-N 1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-3-[2-(dimethylsulfamoyl)phenyl]sulfonylurea Chemical compound COC1=NC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)S(=O)(=O)N(C)C)=N1 KKMFUPRISZBEFY-UHFFFAOYSA-N 0.000 claims description 2
- AGMLYDUHYBGONF-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-[2-[ethyl(methyl)sulfamoyl]phenyl]sulfonylurea Chemical compound CCN(C)S(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 AGMLYDUHYBGONF-UHFFFAOYSA-N 0.000 claims description 2
- BQIOODJXDKHCID-UHFFFAOYSA-N 1-(4,6-dimethylpyrimidin-2-yl)-3-[2-[ethyl(methyl)sulfamoyl]phenyl]sulfonylurea Chemical compound CCN(C)S(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 BQIOODJXDKHCID-UHFFFAOYSA-N 0.000 claims description 2
- RIZYTXUIIXXYMD-UHFFFAOYSA-N 1-[2-(diethylsulfamoyl)phenyl]sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RIZYTXUIIXXYMD-UHFFFAOYSA-N 0.000 claims description 2
- DZMNTULIPSILEL-UHFFFAOYSA-N 1-[2-(diethylsulfamoyl)phenyl]sulfonyl-3-(4,6-dimethyl-1,3,5-triazin-2-yl)urea Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(C)=N1 DZMNTULIPSILEL-UHFFFAOYSA-N 0.000 claims description 2
- BQTXYLWENOADKL-UHFFFAOYSA-N 1-[2-(dimethylsulfamoyl)phenyl]sulfonyl-3-(4,6-dimethyl-1,3,5-triazin-2-yl)urea Chemical compound CN(C)S(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(C)=N1 BQTXYLWENOADKL-UHFFFAOYSA-N 0.000 claims description 2
- HDWOTGUSDWYCRV-UHFFFAOYSA-N 1-[2-(dimethylsulfamoyl)phenyl]sulfonyl-3-(4-methoxy-6-methylpyrimidin-2-yl)urea Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)S(=O)(=O)N(C)C)=N1 HDWOTGUSDWYCRV-UHFFFAOYSA-N 0.000 claims description 2
- XIKHDZPDGFRJPE-UHFFFAOYSA-N 1-[5-chloro-2-(dimethylsulfamoyl)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(Cl)C=2)S(=O)(=O)N(C)C)=N1 XIKHDZPDGFRJPE-UHFFFAOYSA-N 0.000 claims description 2
- DFJSCEXGDWKZES-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]benzenesulfonate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)S(=O)(=O)OCC(F)(F)F)=N1 DFJSCEXGDWKZES-UHFFFAOYSA-N 0.000 claims description 2
- RWAAJSLCVQUBJH-UHFFFAOYSA-N 2,2,2-trifluoroethyl 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzenesulfonate Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)S(=O)(=O)OCC(F)(F)F)=N1 RWAAJSLCVQUBJH-UHFFFAOYSA-N 0.000 claims description 2
- DBTDEFJAFBUGPP-UHFFFAOYSA-N Methanethial Chemical compound S=C DBTDEFJAFBUGPP-UHFFFAOYSA-N 0.000 claims description 2
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims 3
- VOLGAXAGEUPBDM-UHFFFAOYSA-N $l^{1}-oxidanylethane Chemical compound CC[O] VOLGAXAGEUPBDM-UHFFFAOYSA-N 0.000 claims 1
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims 1
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims 1
- JIRAPWRULRYZPQ-UHFFFAOYSA-N 1-(4,6-dimethylpyrimidin-2-yl)-3-[2-(dimethylsulfamoyl)phenyl]sulfonylurea Chemical compound CN(C)S(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 JIRAPWRULRYZPQ-UHFFFAOYSA-N 0.000 claims 1
- KTKUEUZFWYOYBY-UHFFFAOYSA-N 1-[2-(diethylsulfamoyl)phenyl]sulfonyl-3-(4,6-dimethoxy-1,3,5-triazin-2-yl)urea Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 KTKUEUZFWYOYBY-UHFFFAOYSA-N 0.000 claims 1
- ONEMLRIMPCSMFX-UHFFFAOYSA-N 1-[2-(diethylsulfamoyl)phenyl]sulfonyl-3-(4,6-dimethylpyrimidin-2-yl)urea Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(C)=N1 ONEMLRIMPCSMFX-UHFFFAOYSA-N 0.000 claims 1
- PLRYVOXDWSQNBJ-UHFFFAOYSA-N 1-[2-(diethylsulfamoyl)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound CCN(CC)S(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 PLRYVOXDWSQNBJ-UHFFFAOYSA-N 0.000 claims 1
- XHZPFJVJJPJQBE-UHFFFAOYSA-N 1-[2-[ethyl(methyl)sulfamoyl]phenyl]sulfonyl-3-(4-methoxy-6-methylpyrimidin-2-yl)urea Chemical compound CCN(C)S(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=CC(OC)=N1 XHZPFJVJJPJQBE-UHFFFAOYSA-N 0.000 claims 1
- JKQIHOGGZAYPRZ-UHFFFAOYSA-N 1-[5-chloro-2-(dimethylsulfamoyl)phenyl]sulfonyl-3-(4-methoxy-6-methylpyrimidin-2-yl)urea Chemical compound COC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(Cl)C=2)S(=O)(=O)N(C)C)=N1 JKQIHOGGZAYPRZ-UHFFFAOYSA-N 0.000 claims 1
- MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical compound [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
- GRVDJDISBSALJP-UHFFFAOYSA-N methyloxidanyl Chemical compound [O]C GRVDJDISBSALJP-UHFFFAOYSA-N 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 12
- 239000003905 agrochemical Substances 0.000 abstract 1
- MIAUJDCQDVWHEV-UHFFFAOYSA-N benzene-1,2-disulfonic acid Chemical class OS(=O)(=O)C1=CC=CC=C1S(O)(=O)=O MIAUJDCQDVWHEV-UHFFFAOYSA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 66
- 239000000047 product Substances 0.000 description 56
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 51
- 238000006243 chemical reaction Methods 0.000 description 51
- 239000000203 mixture Substances 0.000 description 47
- 239000002904 solvent Substances 0.000 description 46
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 44
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 37
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 37
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 35
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 30
- 244000037364 Cinnamomum aromaticum Species 0.000 description 27
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- 239000003921 oil Substances 0.000 description 26
- 235000019198 oils Nutrition 0.000 description 26
- 235000009566 rice Nutrition 0.000 description 26
- 244000075850 Avena orientalis Species 0.000 description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 25
- 241000209149 Zea Species 0.000 description 25
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 24
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 21
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- 239000004480 active ingredient Substances 0.000 description 5
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- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- AJPJDKMHJJGVTQ-UHFFFAOYSA-M sodium dihydrogen phosphate Chemical compound [Na+].OP(O)([O-])=O AJPJDKMHJJGVTQ-UHFFFAOYSA-M 0.000 description 1
- HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 125000000565 sulfonamide group Chemical group 0.000 description 1
- 125000005420 sulfonamido group Chemical group S(=O)(=O)(N*)* 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- 239000006188 syrup Substances 0.000 description 1
- 235000020357 syrup Nutrition 0.000 description 1
- BFKJFAAPBSQJPD-UHFFFAOYSA-N tetrafluoroethene Chemical group FC(F)=C(F)F BFKJFAAPBSQJPD-UHFFFAOYSA-N 0.000 description 1
- ZWZVWGITAAIFPS-UHFFFAOYSA-N thiophosgene Chemical compound ClC(Cl)=S ZWZVWGITAAIFPS-UHFFFAOYSA-N 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- SYOKIDBDQMKNDQ-XWTIBIIYSA-N vildagliptin Chemical compound C1C(O)(C2)CC(C3)CC1CC32NCC(=O)N1CCC[C@H]1C#N SYOKIDBDQMKNDQ-XWTIBIIYSA-N 0.000 description 1
- 238000001238 wet grinding Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C311/00—Amides of sulfonic acids, i.e. compounds having singly-bound oxygen atoms of sulfo groups replaced by nitrogen atoms, not being part of nitro or nitroso groups
- C07C311/65—N-sulfonylisocyanates
-
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
- C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
- C07D253/06—1,2,4-Triazines
- C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
- C07D253/07—1,2,4-Triazines having 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/02—Systems containing only non-condensed rings with a three-membered ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2601/00—Systems containing only non-condensed rings
- C07C2601/12—Systems containing only non-condensed rings with a six-membered ring
- C07C2601/14—The ring being saturated
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CA000403940A CA1146548A (en) | 1979-07-20 | 1982-05-27 | Herbicidal sulfonamides |
Applications Claiming Priority (6)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5915379A | 1979-07-20 | 1979-07-20 | |
| US059,153 | 1979-07-20 | ||
| US13034280A | 1980-03-14 | 1980-03-14 | |
| US130,342 | 1980-03-14 | ||
| US06/152,022 US4310346A (en) | 1980-03-14 | 1980-05-30 | N(Substituted phenylsulfonyl) N'(substituted cyumidin-2-yl) ureas |
| US152.022 | 1980-05-30 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1144923A true CA1144923A (en) | 1983-04-19 |
Family
ID=27369593
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000356200A Expired CA1144923A (en) | 1979-07-20 | 1980-07-15 | Herbicidal sulfonamides |
Country Status (16)
| Country | Link |
|---|---|
| EP (2) | EP0070041A3 (OSRAM) |
| AU (2) | AU536787B2 (OSRAM) |
| BR (1) | BR8004382A (OSRAM) |
| CA (1) | CA1144923A (OSRAM) |
| DE (1) | DE3067433D1 (OSRAM) |
| DK (1) | DK259280A (OSRAM) |
| ES (1) | ES8105274A1 (OSRAM) |
| GB (1) | GB2057429B (OSRAM) |
| GR (1) | GR69301B (OSRAM) |
| HU (1) | HU190668B (OSRAM) |
| IE (1) | IE50022B1 (OSRAM) |
| IL (1) | IL60631A (OSRAM) |
| NZ (1) | NZ194385A (OSRAM) |
| PH (1) | PH16406A (OSRAM) |
| PT (1) | PT71580B (OSRAM) |
| TR (1) | TR21772A (OSRAM) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4443243A (en) * | 1981-07-16 | 1984-04-17 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N-triazinylureas |
| DE3466986D1 (de) * | 1983-02-04 | 1987-12-03 | Ciba Geigy Ag | N-phenylsulfonyl-n'-pyrimidinyl- and -triazinylurea |
| EP0126711B1 (de) * | 1983-05-16 | 1989-08-02 | Ciba-Geigy Ag | Herbizid wirksame und pflanzenwuchsregulierende Pyrimidin-Derivate, deren Herstellung und Verwendung |
| AU575335B2 (en) * | 1983-08-05 | 1988-07-28 | E.I. Du Pont De Nemours And Company | Benzene sulfonamides |
| JPS60146878A (ja) * | 1984-01-10 | 1985-08-02 | Nippon Tokushu Noyaku Seizo Kk | スルホニルグアニジン誘導体，その製法及び除草剤 |
| JPS60166668A (ja) * | 1984-02-10 | 1985-08-29 | Nippon Tokushu Noyaku Seizo Kk | ２−アルコキシアミノスルホニルベンゼン−スルホニルウレア誘導体、その製法及び除草剤 |
| AU585761B2 (en) * | 1984-03-07 | 1989-06-22 | E.I. Du Pont De Nemours And Company | Herbicidal fluoroethoxy triazines |
| EP0158600B1 (de) * | 1984-04-11 | 1991-04-03 | Ciba-Geigy Ag | Verfahren zur selektiven Unkrautbekämpfung in Nutzpflanzenkulturen |
| DE3516616A1 (de) * | 1984-08-30 | 1986-03-13 | Bayer Ag, 5090 Leverkusen | Benzodisultame |
| CA1226862A (en) * | 1985-02-21 | 1987-09-15 | Donald J. Dumas | Herbicidal sulfonamides |
| US4678498A (en) * | 1985-06-12 | 1987-07-07 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| GB8719730D0 (en) * | 1987-08-20 | 1987-09-30 | Vickers Plc | Radiation sensitive compounds |
| DE4439675A1 (de) * | 1994-11-07 | 1996-05-09 | Hoechst Schering Agrevo Gmbh | N-Acyl-N-alkylaminophenylsulfonylharnstoffe mit Schwefelsubstituenten, Verfahren zur Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| DE4439676A1 (de) * | 1994-11-07 | 1996-05-09 | Hoechst Schering Agrevo Gmbh | Schwefelsubstituierte Phenylsulfonylharnstoffe, Verfahren zu deren Herstellung und Verwendung als Herbizide und Pflanzenwachstumsregulatoren |
| ZA974703B (en) * | 1996-05-30 | 1997-12-30 | Bayer Ag | Substituted sulfonylamino(thio)carbonyl compounds. |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| OA05625A (fr) * | 1976-04-07 | 1981-04-30 | Du Pont | N-(hétérocyclique aminocarbonyl) aryl sulfonamides herbicides, compositions les contenant et procédés les utilisant . |
| US4257802A (en) * | 1977-10-06 | 1981-03-24 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| DK168779A (da) * | 1978-05-30 | 1979-12-01 | Du Pont | Agrikulturelle carbaminidothioater |
-
1980
- 1980-06-17 DK DK259280A patent/DK259280A/da not_active Application Discontinuation
- 1980-07-15 BR BR8004382A patent/BR8004382A/pt unknown
- 1980-07-15 CA CA000356200A patent/CA1144923A/en not_active Expired
- 1980-07-18 HU HU801806A patent/HU190668B/hu unknown
- 1980-07-18 PT PT71580A patent/PT71580B/pt unknown
- 1980-07-18 AU AU60601/80A patent/AU536787B2/en not_active Ceased
- 1980-07-18 PH PH24308A patent/PH16406A/en unknown
- 1980-07-18 EP EP82107279A patent/EP0070041A3/en not_active Withdrawn
- 1980-07-18 DE DE8080302433T patent/DE3067433D1/de not_active Expired
- 1980-07-18 IL IL60631A patent/IL60631A/xx unknown
- 1980-07-18 IE IE1495/80A patent/IE50022B1/en unknown
- 1980-07-18 GB GB8023622A patent/GB2057429B/en not_active Expired
- 1980-07-18 EP EP80302433A patent/EP0023141B1/en not_active Expired
- 1980-07-18 NZ NZ194385A patent/NZ194385A/xx unknown
- 1980-07-18 TR TR21772A patent/TR21772A/xx unknown
- 1980-07-18 ES ES493524A patent/ES8105274A1/es not_active Expired
- 1980-07-19 GR GR62499A patent/GR69301B/el unknown
-
1984
- 1984-02-23 AU AU24898/84A patent/AU2489884A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| EP0023141B1 (en) | 1984-04-11 |
| GB2057429B (en) | 1983-07-20 |
| EP0023141A2 (en) | 1981-01-28 |
| GR69301B (OSRAM) | 1982-05-14 |
| AU536787B2 (en) | 1984-05-24 |
| PH16406A (en) | 1983-09-26 |
| TR21772A (tr) | 1985-07-01 |
| EP0023141A3 (en) | 1981-04-01 |
| PT71580B (en) | 1982-02-19 |
| BR8004382A (pt) | 1981-02-24 |
| PT71580A (en) | 1980-08-01 |
| IL60631A0 (en) | 1980-09-16 |
| DK259280A (da) | 1981-01-21 |
| EP0070041A3 (en) | 1983-04-13 |
| AU6060180A (en) | 1981-01-22 |
| GB2057429A (en) | 1981-04-01 |
| HU190668B (en) | 1986-10-28 |
| EP0070041A2 (en) | 1983-01-19 |
| IE801495L (en) | 1981-01-20 |
| IE50022B1 (en) | 1986-02-05 |
| NZ194385A (en) | 1982-12-07 |
| IL60631A (en) | 1986-03-31 |
| ES493524A0 (es) | 1981-06-01 |
| DE3067433D1 (en) | 1984-05-17 |
| ES8105274A1 (es) | 1981-06-01 |
| AU2489884A (en) | 1984-07-05 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |