CA1167847A - Herbicidal sulfonamides - Google Patents
Herbicidal sulfonamidesInfo
- Publication number
- CA1167847A CA1167847A CA000385595A CA385595A CA1167847A CA 1167847 A CA1167847 A CA 1167847A CA 000385595 A CA000385595 A CA 000385595A CA 385595 A CA385595 A CA 385595A CA 1167847 A CA1167847 A CA 1167847A
- Authority
- CA
- Canada
- Prior art keywords
- och3
- compound
- methyl
- benzenesulfonamide
- methylsulfonyl
- 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 11
- 150000003456 sulfonamides Chemical class 0.000 title description 10
- 230000002363 herbicidal effect Effects 0.000 title description 2
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 162
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 58
- -1 OCH2CH2OCH3 Chemical group 0.000 claims description 28
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 claims description 25
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 23
- 238000000034 method Methods 0.000 claims description 22
- 229910052739 hydrogen Inorganic materials 0.000 claims description 18
- 150000003839 salts Chemical class 0.000 claims description 11
- 230000012010 growth Effects 0.000 claims description 10
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- JCXJVPUVTGWSNB-UHFFFAOYSA-N Nitrogen dioxide Chemical compound O=[N]=O JCXJVPUVTGWSNB-UHFFFAOYSA-N 0.000 claims description 2
- WMIWQLODHBEHAD-UHFFFAOYSA-N 1-(4,6-dimethoxy-1,3,5-triazin-2-yl)-1-methyl-3-(2-methylsulfonylphenyl)sulfonylurea Chemical compound COC1=NC(OC)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)S(C)(=O)=O)=N1 WMIWQLODHBEHAD-UHFFFAOYSA-N 0.000 claims 1
- FFKYZSAWFHRDJF-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-1-methoxy-3-(2-methylsulfonylphenyl)sulfonylurea Chemical compound N=1C(OC)=CC(OC)=NC=1N(OC)C(=O)NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O FFKYZSAWFHRDJF-UHFFFAOYSA-N 0.000 claims 1
- BMKXDNGMJLWSAD-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-1-methyl-3-(2-methylsulfonylphenyl)sulfonylurea Chemical compound COC1=CC(OC)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)S(C)(=O)=O)=N1 BMKXDNGMJLWSAD-UHFFFAOYSA-N 0.000 claims 1
- FQOJOBBRFKQIAL-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-1-methyl-3-(2-propylsulfonylphenyl)sulfonylurea Chemical compound CCCS(=O)(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)N(C)C1=NC(OC)=CC(OC)=N1 FQOJOBBRFKQIAL-UHFFFAOYSA-N 0.000 claims 1
- BXQNLBRBUIGZSB-UHFFFAOYSA-N 1-(4,6-dimethylpyrimidin-2-yl)-1-methoxy-3-(2-methylsulfonylphenyl)sulfonylurea Chemical compound N=1C(C)=CC(C)=NC=1N(OC)C(=O)NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O BXQNLBRBUIGZSB-UHFFFAOYSA-N 0.000 claims 1
- GZABPJIDVPJQPW-UHFFFAOYSA-N 1-(4,6-dimethylpyrimidin-2-yl)-1-methyl-3-(2-methylsulfonylphenyl)sulfonylurea Chemical compound N=1C(C)=CC(C)=NC=1N(C)C(=O)NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O GZABPJIDVPJQPW-UHFFFAOYSA-N 0.000 claims 1
- RUPMQWLVRLEOIZ-UHFFFAOYSA-N 1-methoxy-1-(4-methoxy-6-methylpyrimidin-2-yl)-3-(2-methylsulfonylphenyl)sulfonylurea Chemical compound N=1C(C)=CC(OC)=NC=1N(OC)C(=O)NS(=O)(=O)C1=CC=CC=C1S(C)(=O)=O RUPMQWLVRLEOIZ-UHFFFAOYSA-N 0.000 claims 1
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- NCAIGTHBQTXTLR-UHFFFAOYSA-N phentermine hydrochloride Chemical compound [Cl-].CC(C)([NH3+])CC1=CC=CC=C1 NCAIGTHBQTXTLR-UHFFFAOYSA-N 0.000 description 1
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- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Substances [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 1
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- 230000003389 potentiating effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 125000000246 pyrimidin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=C1[H] 0.000 description 1
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- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
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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
- RBWSWDPRDBEWCR-RKJRWTFHSA-N sodium;(2r)-2-[(2r)-3,4-dihydroxy-5-oxo-2h-furan-2-yl]-2-hydroxyethanolate Chemical compound [Na+].[O-]C[C@@H](O)[C@H]1OC(=O)C(O)=C1O RBWSWDPRDBEWCR-RKJRWTFHSA-N 0.000 description 1
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- 150000005846 sugar alcohols Polymers 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000002653 sulfanylmethyl group Chemical group [H]SC([H])([H])[*] 0.000 description 1
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- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 229910002029 synthetic silica gel Inorganic materials 0.000 description 1
- ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
- 229960000278 theophylline Drugs 0.000 description 1
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- 150000003568 thioethers Chemical class 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D521/00—Heterocyclic compounds containing unspecified hetero rings
-
- 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
- C07D239/70—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings condensed with carbocyclic rings or ring systems
- C07D239/72—Quinazolines; Hydrogenated quinazolines
- C07D239/74—Quinazolines; Hydrogenated quinazolines with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, attached to ring carbon atoms of the hetero ring
- C07D239/76—N-oxides
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)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US18717480A | 1980-09-15 | 1980-09-15 | |
| US187,174 | 1980-09-15 | ||
| US257,585 | 1981-05-07 | ||
| US06/257,585 US4371391A (en) | 1980-09-15 | 1981-05-07 | Herbicidal sulfonamides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1167847A true CA1167847A (en) | 1984-05-22 |
Family
ID=26882794
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000385595A Expired CA1167847A (en) | 1980-09-15 | 1981-09-10 | Herbicidal sulfonamides |
Country Status (13)
Families Citing this family (27)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4655822A (en) * | 1977-10-06 | 1987-04-07 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4501607A (en) * | 1978-09-27 | 1985-02-26 | E. I. Du Pont De Nemours And Company | Herbicidal triazine sulfonamides |
| US4645529A (en) * | 1979-04-04 | 1987-02-24 | E. I. Du Pont De Nemours And Company | Herbicidal thiophenesulfonamides |
| CA1330438C (en) * | 1980-07-17 | 1994-06-28 | Willy Meyer | N-phenylsulfonyl-n'-pyrimidinyl-and-triazinylureas |
| US4443245A (en) * | 1981-07-13 | 1984-04-17 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N'-triazinylureas |
| US4443243A (en) * | 1981-07-16 | 1984-04-17 | Ciba-Geigy Corporation | N-Phenylsulfonyl-N-triazinylureas |
| US4528024A (en) * | 1981-09-09 | 1985-07-09 | E. I. Du Pont De Nemours And Company | Herbicidal alkyl sulfones |
| US4454334A (en) * | 1981-09-29 | 1984-06-12 | E. I. Du Pont De Nemours And Company | Benzylsulfonyl isocyanates |
| US4543120A (en) * | 1982-08-12 | 1985-09-24 | E. I. Du Pont De Nemours And Company | Alkyl sulfonyl sulfonamides |
| DE3472557D1 (en) * | 1983-01-04 | 1988-08-11 | Du Pont | Herbicidal n-hydroxy-n'-sulfonylguanidines and sulfonamide inner salts |
| DE3322280A1 (de) * | 1983-06-16 | 1985-01-03 | Schering AG, 1000 Berlin und 4709 Bergkamen | Substituierte sulfonylharnstoffe, verfahren zur herstellung dieser verbindungen sowie diese enthaltende mittel mit herbizider und pflanzenwuchsregulierender wirkung |
| DE3324800A1 (de) * | 1983-07-09 | 1985-01-17 | Hoechst Ag, 6230 Frankfurt | Neue heterocyclisch substituierte sulfonylharnstoffe |
| US4604131A (en) * | 1983-08-05 | 1986-08-05 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| DE3330603A1 (de) * | 1983-08-25 | 1985-03-21 | Hoechst Ag, 6230 Frankfurt | Neue 2-amino-alkenylsulfonylharnstoffe |
| US4761373A (en) * | 1984-03-06 | 1988-08-02 | Molecular Genetics, Inc. | Herbicide resistance in plants |
| US5304732A (en) * | 1984-03-06 | 1994-04-19 | Mgi Pharma, Inc. | Herbicide resistance in plants |
| US6211439B1 (en) | 1984-08-10 | 2001-04-03 | Mgi Pharma, Inc | Herbicide resistance in plants |
| DE3431932A1 (de) * | 1984-08-30 | 1986-03-06 | Bayer Ag, 5090 Leverkusen | Verfahren zur herstellung von 1-(2-oxyaminosulfonylphenylsulfonyl)-3- heteroaryl-harnstoffen |
| US4820337A (en) * | 1984-08-30 | 1989-04-11 | Bayer Aktiengesellschaft | 1-(2-oxyaminosulphonylphenylsulphonyl)-3-triazinyl-ureas |
| DE3621320A1 (de) * | 1986-06-26 | 1988-01-07 | Bayer Ag | 3-substituierte 1-(2-halogenalkoxy-benzolsulfonyl)-3-heteroaryl-(thio)harnstoffe |
| DE3518876A1 (de) * | 1984-08-30 | 1986-03-13 | Bayer Ag, 5090 Leverkusen | 1-(2-oxyaminosulfonylphenylsulfonyl)-3-heteroaryl-harnstoffe |
| GR1000753B (el) * | 1989-08-07 | 1992-12-30 | Basf Ag | Αποφυλλωτικο μεσο για τη βαμβακια. |
| 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 |
| DE4038430A1 (de) * | 1990-12-01 | 1992-06-04 | Basf Ag | Herbizide n-((1,3,5-triazin-2-yl)-aminocarbonyl) benzolsulfonamide |
| DE4206146A1 (de) * | 1992-02-28 | 1993-09-02 | Basf Ag | Herbizide n-((1,3,5-triazin-2-yl)aminocarbonyl)benzolsulfonamide |
| DE4238175A1 (de) * | 1992-11-12 | 1994-05-19 | Basf Ag | Herbizide Sulfonylharnstoffe, Verfahren zur Herstellung und ihre Verwendung |
| DE10111649A1 (de) * | 2001-03-12 | 2002-09-19 | Bayer Ag | Substituierte Fluoralkoxyphenylsulfonylharnstoffe |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1082189A (en) * | 1976-04-07 | 1980-07-22 | George Levitt | Herbicidal sulfonamides |
| US4225337A (en) * | 1978-10-27 | 1980-09-30 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4257802A (en) * | 1977-10-06 | 1981-03-24 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4238621A (en) * | 1979-04-13 | 1980-12-09 | E. I. Du Pont De Nemours And Company | Intermediates for herbicidal sulfonamides |
| DK349479A (da) * | 1978-09-27 | 1980-03-28 | Du Pont | Sulfonamidderivater og deres anvendelse til regulering af plantevaekst |
| US4302241A (en) * | 1979-07-02 | 1981-11-24 | E. I. Du Pont De Nemours And Company | Agricultural sulfonamides |
| US4310346A (en) * | 1980-03-14 | 1982-01-12 | E. I. Du Pont De Nemours And Company | N(Substituted phenylsulfonyl) N'(substituted cyumidin-2-yl) ureas |
| 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 |
| US4301286A (en) * | 1979-08-20 | 1981-11-17 | E. I. Du Pont De Nemours And Company | Herbicidal O-alkyl sulfonylisoureas |
| US4332611A (en) * | 1980-07-11 | 1982-06-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
-
1981
- 1981-05-07 US US06/257,585 patent/US4371391A/en not_active Expired - Fee Related
- 1981-09-10 CA CA000385595A patent/CA1167847A/en not_active Expired
- 1981-09-11 BR BR8105806A patent/BR8105806A/pt unknown
- 1981-09-11 EP EP81304170A patent/EP0048143A1/en not_active Withdrawn
- 1981-09-14 NZ NZ198341A patent/NZ198341A/en unknown
- 1981-09-14 GR GR66048A patent/GR75780B/el unknown
- 1981-09-14 RO RO105301A patent/RO84024B1/ro unknown
- 1981-09-14 PL PL23302381A patent/PL233023A1/xx unknown
- 1981-09-14 AU AU75226/81A patent/AU7522681A/en not_active Abandoned
- 1981-09-14 IL IL63822A patent/IL63822A0/xx unknown
- 1981-09-14 DK DK408981A patent/DK408981A/da not_active Application Discontinuation
- 1981-09-14 ES ES505464A patent/ES505464A0/es active Granted
- 1981-09-14 PT PT73670A patent/PT73670B/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| US4371391A (en) | 1983-02-01 |
| RO84024A2 (ro) | 1984-05-12 |
| NZ198341A (en) | 1984-11-09 |
| DK408981A (da) | 1982-03-16 |
| EP0048143A1 (en) | 1982-03-24 |
| BR8105806A (pt) | 1982-06-08 |
| PL233023A1 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1982-08-16 |
| PT73670A (en) | 1981-10-01 |
| RO84024B1 (ro) | 1984-06-30 |
| AU7522681A (en) | 1982-03-25 |
| ES8301936A1 (es) | 1983-01-01 |
| IL63822A0 (en) | 1981-12-31 |
| GR75780B (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1984-08-02 |
| ES505464A0 (es) | 1983-01-01 |
| PT73670B (en) | 1984-05-08 |
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Legal Events
| Date | Code | Title | Description |
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| MKEX | Expiry |