BG61518B2 - N-фенилсулфонил-n'-триазинилкарбамиди - Google Patents
N-фенилсулфонил-n'-триазинилкарбамиди Download PDFInfo
- Publication number
- BG61518B2 BG61518B2 BG096470A BG9647092A BG61518B2 BG 61518 B2 BG61518 B2 BG 61518B2 BG 096470 A BG096470 A BG 096470A BG 9647092 A BG9647092 A BG 9647092A BG 61518 B2 BG61518 B2 BG 61518B2
- Authority
- BG
- Bulgaria
- Prior art keywords
- compound
- azinylurea
- phenylsulfonyl
- oxygen
- och
- Prior art date
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- -1 C1-C4alkylthio Chemical group 0.000 claims abstract description 49
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 20
- 239000001301 oxygen Substances 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 19
- 239000001257 hydrogen Substances 0.000 claims abstract description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims abstract description 16
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 16
- 239000011593 sulfur Chemical group 0.000 claims abstract description 16
- 150000002431 hydrogen Chemical group 0.000 claims abstract description 15
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 13
- 150000002367 halogens Chemical group 0.000 claims abstract description 13
- 150000003839 salts Chemical class 0.000 claims abstract description 13
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims abstract description 11
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 10
- 125000006729 (C2-C5) alkenyl group Chemical group 0.000 claims abstract description 8
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 6
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims abstract description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims abstract description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 5
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims abstract 3
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims abstract 2
- 150000001875 compounds Chemical class 0.000 claims description 70
- 239000000203 mixture Substances 0.000 claims description 42
- 238000000034 method Methods 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- PWLRSGUSOOXHPW-UHFFFAOYSA-N 1-[2-(2-methoxyethoxy)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 PWLRSGUSOOXHPW-UHFFFAOYSA-N 0.000 claims description 4
- VENWCFBYRISXKV-UHFFFAOYSA-N 1-[2-(2-methoxyethylsulfanyl)phenyl]sulfonyl-3-(4-methoxy-6-methyl-1,3,5-triazin-2-yl)urea Chemical compound COCCSC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 VENWCFBYRISXKV-UHFFFAOYSA-N 0.000 claims description 4
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- 239000011737 fluorine Substances 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 claims description 3
- XFSILWLJLNQFKE-UHFFFAOYSA-N 1-(4-ethoxy-6-methoxy-1,3,5-triazin-2-yl)-3-[2-(2-methoxyethoxy)phenyl]sulfonylurea Chemical compound COC1=NC(OCC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCOC)=N1 XFSILWLJLNQFKE-UHFFFAOYSA-N 0.000 claims description 2
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 2
- 239000004202 carbamide Substances 0.000 claims 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- 239000002585 base Substances 0.000 abstract description 15
- 150000001412 amines Chemical class 0.000 abstract description 9
- 230000012010 growth Effects 0.000 abstract description 8
- 230000001105 regulatory effect Effects 0.000 abstract description 4
- 229910052751 metal Inorganic materials 0.000 abstract description 2
- 239000002184 metal Substances 0.000 abstract description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 abstract 1
- 229910052783 alkali metal Inorganic materials 0.000 abstract 1
- 150000001340 alkali metals Chemical class 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 241000196324 Embryophyta Species 0.000 description 17
- 238000006243 chemical reaction Methods 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 239000000843 powder Substances 0.000 description 11
- 150000003254 radicals Chemical class 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
- 239000000243 solution Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
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- 150000003456 sulfonamides Chemical class 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
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- 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 5
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
- 239000008187 granular material Substances 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
- 239000002736 nonionic surfactant Substances 0.000 description 5
- 230000008635 plant growth Effects 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
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- 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
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
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- 150000001342 alkaline earth metals Chemical class 0.000 description 3
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- 150000001768 cations Chemical class 0.000 description 3
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- 230000000694 effects Effects 0.000 description 3
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- 230000002401 inhibitory effect Effects 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
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- SWJHEODPUMMCGP-UHFFFAOYSA-N n-(2-methoxyethoxy)benzenesulfonamide Chemical compound COCCONS(=O)(=O)C1=CC=CC=C1 SWJHEODPUMMCGP-UHFFFAOYSA-N 0.000 description 3
- PVESSTKZXPQBAM-UHFFFAOYSA-N n-(2-methoxyethylsulfanyl)benzenesulfonamide Chemical compound COCCSNS(=O)(=O)C1=CC=CC=C1 PVESSTKZXPQBAM-UHFFFAOYSA-N 0.000 description 3
- 239000011591 potassium Substances 0.000 description 3
- 229910052700 potassium Inorganic materials 0.000 description 3
- 229920005552 sodium lignosulfonate Polymers 0.000 description 3
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- 235000011152 sodium sulphate Nutrition 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
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- 230000004580 weight loss Effects 0.000 description 3
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical group COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 2
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- RJALAXYQXQWPDF-UHFFFAOYSA-N 1-(4-ethoxy-6-methyl-1,3,5-triazin-2-yl)-3-[2-(2-methoxyethoxy)phenyl]sulfonylurea Chemical compound CCOC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCOC)=N1 RJALAXYQXQWPDF-UHFFFAOYSA-N 0.000 description 1
- GHNQJEQKGTWWMT-UHFFFAOYSA-N 1-(4-ethyl-6-methoxy-1,3,5-triazin-2-yl)-3-[2-(2-methoxyethoxy)phenyl]sulfonylurea Chemical compound COC1=NC(CC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCOC)=N1 GHNQJEQKGTWWMT-UHFFFAOYSA-N 0.000 description 1
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- SMSHHKNNPMVPMK-UHFFFAOYSA-N 2-(2-methoxyethoxy)-n-(oxomethylidene)benzenesulfonamide Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)N=C=O SMSHHKNNPMVPMK-UHFFFAOYSA-N 0.000 description 1
- 125000004974 2-butenyl group Chemical group C(C=CC)* 0.000 description 1
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- BUXTXUBQAKIQKS-UHFFFAOYSA-N sulfuryl diisocyanate Chemical compound O=C=NS(=O)(=O)N=C=O BUXTXUBQAKIQKS-UHFFFAOYSA-N 0.000 description 1
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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
-
- 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
- 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
- C07D251/14—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 hydrogen or carbon atoms directly attached to at least one ring carbon atom
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Health & Medical Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Amplifiers (AREA)
- Magnetic Resonance Imaging Apparatus (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Spinning Or Twisting Of Yarns (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH5481/80A CH657849A5 (en) | 1980-07-17 | 1980-07-17 | N-Phenylsulfonyl-N'-pyrimidinyl- and -triazinyl ureas |
| CH821680 | 1980-11-05 | ||
| CH399181 | 1981-06-17 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| BG61518B2 true BG61518B2 (bg) | 1997-10-31 |
Family
ID=27174660
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG096468A BG60335B2 (bg) | 1980-07-17 | 1992-06-15 | N-фенилсулфонил-n'-триазинил карбамиди |
| BG096470A BG61518B2 (bg) | 1980-07-17 | 1992-06-15 | N-фенилсулфонил-n'-триазинилкарбамиди |
Family Applications Before (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| BG096468A BG60335B2 (bg) | 1980-07-17 | 1992-06-15 | N-фенилсулфонил-n'-триазинил карбамиди |
Country Status (25)
| Country | Link |
|---|---|
| US (11) | US4510325A (hr) |
| EP (3) | EP0044808B1 (hr) |
| KR (1) | KR850000495B1 (hr) |
| AT (3) | ATE17431T1 (hr) |
| AU (1) | AU545208B2 (hr) |
| BG (2) | BG60335B2 (hr) |
| BR (3) | BR8104619A (hr) |
| CA (2) | CA1330438C (hr) |
| CY (1) | CY1438A (hr) |
| DD (2) | DD215461A5 (hr) |
| DE (3) | DE3172974D1 (hr) |
| DK (4) | DK163664C (hr) |
| EG (1) | EG15401A (hr) |
| ES (2) | ES504013A0 (hr) |
| GR (1) | GR74308B (hr) |
| IL (3) | IL63324A (hr) |
| KE (1) | KE3819A (hr) |
| MA (1) | MA19205A1 (hr) |
| MX (3) | MX170995B (hr) |
| MY (2) | MY8600581A (hr) |
| NZ (1) | NZ197733A (hr) |
| PH (1) | PH18233A (hr) |
| RO (1) | RO83456B (hr) |
| TR (1) | TR21355A (hr) |
| ZW (1) | ZW16681A1 (hr) |
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|---|---|---|---|---|
| GB791923A (en) * | 1955-08-08 | 1958-03-12 | Ici Ltd | New sulphonamides |
| FR1468747A (fr) * | 1965-07-19 | 1967-02-10 | Benzène-sulfonyl-1 (pyrimidyl-2)-3 urées | |
| US4154753A (en) * | 1966-01-12 | 1979-05-15 | Imperial Chemical Industries Limited | Fluorinated compounds containing functional groups |
| IL40344A0 (en) * | 1971-09-22 | 1972-11-28 | Du Pont | Substituted benzenesulfonamides,their preparation and their use for controlling mites |
| CA1082189A (en) * | 1976-04-07 | 1980-07-22 | George Levitt | Herbicidal sulfonamides |
| US4169719A (en) * | 1976-04-07 | 1979-10-02 | E. I. Du Pont De Nemours And Co. | Herbicidal sulfonamides |
| US4190432A (en) * | 1977-08-01 | 1980-02-26 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4339266A (en) * | 1977-10-06 | 1982-07-13 | 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 |
| DK401978A (da) * | 1977-10-06 | 1979-04-07 | Du Pont | Herbicide sulfonamider |
| US4141916A (en) * | 1978-02-13 | 1979-02-27 | The Dow Chemical Company | 3,4,5-Trichloro-N,N-Di(loweralkyl)-2-((chloromethyl)thio)benzenesulfonamides |
| DK163123C (da) * | 1978-05-30 | 1992-06-09 | Du Pont | Benzensulfonylurinstoffer til anvendelse som herbicider eller plantevaekstregulatorer, praeparat indeholdende dem samt deres anvendelse |
| 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 |
| 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 |
| 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 |
| DK455480A (da) * | 1979-11-30 | 1981-05-31 | Du Pont | Fremgangsmaade til fremstilling af herbicide n- (substituerede heterocycliske aminocarbonyl)-aromatiske sulfonamider |
| AU543161B2 (en) * | 1980-03-07 | 1985-04-04 | E.I. Du Pont De Nemours And Company | Pyrimidine or s.triazine derivatives |
| US4368069A (en) * | 1980-07-11 | 1983-01-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4348220A (en) * | 1980-07-11 | 1982-09-07 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4370480A (en) * | 1980-07-11 | 1983-01-25 | E. I. Du Pont De Nemours And Company | Herbicidal ureas and isoureas |
| CA1330438C (en) * | 1980-07-17 | 1994-06-28 | Willy Meyer | N-phenylsulfonyl-n'-pyrimidinyl-and-triazinylureas |
| US4487626A (en) * | 1980-08-22 | 1984-12-11 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| US4371391A (en) * | 1980-09-15 | 1983-02-01 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
-
1980
- 1980-07-15 CA CA000381786A patent/CA1330438C/en not_active Expired - Lifetime
-
1981
- 1981-07-01 MA MA19405A patent/MA19205A1/fr unknown
- 1981-07-13 DE DE8181810281T patent/DE3172974D1/de not_active Expired
- 1981-07-13 DE DE8181810283T patent/DE3160818D1/de not_active Expired
- 1981-07-13 EP EP81810282A patent/EP0044808B1/de not_active Expired
- 1981-07-13 AT AT81810282T patent/ATE17431T1/de active
- 1981-07-13 EP EP81810281A patent/EP0044807B1/de not_active Expired
- 1981-07-13 EP EP81810283A patent/EP0044809B1/de not_active Expired
- 1981-07-13 AT AT81810283T patent/ATE4526T1/de not_active IP Right Cessation
- 1981-07-13 AT AT81810281T patent/ATE16555T1/de not_active IP Right Cessation
- 1981-07-13 DE DE8181810282T patent/DE3173493D1/de not_active Expired
- 1981-07-15 EG EG402/81A patent/EG15401A/xx active
- 1981-07-15 IL IL8163324A patent/IL63324A/xx not_active IP Right Cessation
- 1981-07-15 RO RO104891A patent/RO83456B/ro unknown
- 1981-07-15 IL IL8179463A patent/IL79463A/xx unknown
- 1981-07-15 ZW ZW166/81A patent/ZW16681A1/xx unknown
- 1981-07-15 PH PH25917A patent/PH18233A/en unknown
- 1981-07-16 TR TR21355A patent/TR21355A/xx unknown
- 1981-07-16 AU AU73036/81A patent/AU545208B2/en not_active Expired
- 1981-07-16 NZ NZ197733A patent/NZ197733A/en unknown
- 1981-07-16 DD DD81231843A patent/DD215461A5/de not_active IP Right Cessation
- 1981-07-16 GR GR65532A patent/GR74308B/el unknown
- 1981-07-16 KR KR1019810002603A patent/KR850000495B1/ko active
- 1981-07-16 ES ES504013A patent/ES504013A0/es active Granted
- 1981-07-16 DD DD81269168A patent/DD220601A5/de not_active IP Right Cessation
- 1981-07-16 DK DK318681A patent/DK163664C/da not_active IP Right Cessation
- 1981-07-17 BR BR8104619A patent/BR8104619A/pt not_active IP Right Cessation
- 1981-07-17 BR BR8104617A patent/BR8104617A/pt unknown
- 1981-07-17 MX MX005729A patent/MX170995B/es unknown
- 1981-07-17 BR BR8104618A patent/BR8104618A/pt unknown
- 1981-07-17 MX MX819558U patent/MX6981E/es unknown
- 1981-07-17 MX MX005728A patent/MX170994B/es unknown
-
1982
- 1982-09-13 US US06/417,743 patent/US4510325A/en not_active Expired - Lifetime
- 1982-09-24 US US06/423,344 patent/US4476321A/en not_active Expired - Lifetime
- 1982-12-16 ES ES518258A patent/ES8401950A1/es not_active Expired
-
1983
- 1983-01-17 US US06/458,691 patent/US4444583A/en not_active Expired - Lifetime
- 1983-01-17 US US06/458,696 patent/US4425154A/en not_active Expired - Lifetime
- 1983-01-17 US US06/458,594 patent/US4514212A/en not_active Expired - Lifetime
- 1983-01-17 US US06/458,693 patent/US4561878A/en not_active Expired - Lifetime
- 1983-01-17 US US06/458,695 patent/US4479821A/en not_active Expired - Lifetime
- 1983-01-17 US US06/458,694 patent/US4537619A/en not_active Expired - Lifetime
- 1983-01-17 US US06/458,584 patent/US4419121A/en not_active Expired - Lifetime
- 1983-03-23 CA CA000424330A patent/CA1205482A/en not_active Expired
-
1985
- 1985-01-22 US US06/693,481 patent/US4629810A/en not_active Expired - Lifetime
- 1985-08-02 US US06/761,941 patent/US4681619A/en not_active Expired - Lifetime
-
1986
- 1986-07-21 IL IL8679463A patent/IL79463A0/xx unknown
- 1986-12-30 MY MY581/86A patent/MY8600581A/xx unknown
-
1987
- 1987-12-30 MY MY138/87A patent/MY8700138A/xx unknown
-
1988
- 1988-05-11 KE KE3819A patent/KE3819A/xx unknown
-
1989
- 1989-03-10 CY CY1438A patent/CY1438A/xx unknown
-
1990
- 1990-06-13 DK DK144190A patent/DK165182C/da not_active IP Right Cessation
-
1991
- 1991-11-20 DK DK189391A patent/DK164901C/da not_active IP Right Cessation
-
1992
- 1992-01-08 DK DK002392A patent/DK166082C/da not_active IP Right Cessation
- 1992-06-15 BG BG096468A patent/BG60335B2/bg unknown
- 1992-06-15 BG BG096470A patent/BG61518B2/bg unknown
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