DE4092524C2 - Substituierte Phenylsulfonyltriazinylharnstoffe, deren Salze und Mittel mit pflanzenwachstumsregelierender Wirkung - Google Patents
Substituierte Phenylsulfonyltriazinylharnstoffe, deren Salze und Mittel mit pflanzenwachstumsregelierender WirkungInfo
- Publication number
- DE4092524C2 DE4092524C2 DE4092524A DE4092524A DE4092524C2 DE 4092524 C2 DE4092524 C2 DE 4092524C2 DE 4092524 A DE4092524 A DE 4092524A DE 4092524 A DE4092524 A DE 4092524A DE 4092524 C2 DE4092524 C2 DE 4092524C2
- Authority
- DE
- Germany
- Prior art keywords
- urea
- dimethylamino
- triazin
- salt
- compound
- 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 - Fee Related
Links
- 150000003839 salts Chemical class 0.000 title claims description 75
- 230000008635 plant growth Effects 0.000 title description 8
- 230000001105 regulatory effect Effects 0.000 title 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 139
- 239000004202 carbamide Substances 0.000 claims description 138
- -1 2- Chlorobenzenesulfonyl Chemical group 0.000 claims description 125
- 239000004480 active ingredient Substances 0.000 claims description 11
- 239000011734 sodium Substances 0.000 claims description 10
- 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 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- 229910052708 sodium Inorganic materials 0.000 claims description 9
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 7
- 229910052700 potassium Inorganic materials 0.000 claims description 7
- 239000011591 potassium Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 6
- LALPXGBCMOGESK-UHFFFAOYSA-N azane 3-methylpentan-3-ol Chemical compound N.CCC(C)(O)CC LALPXGBCMOGESK-UHFFFAOYSA-N 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims 2
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 51
- 238000002844 melting Methods 0.000 description 50
- 230000008018 melting Effects 0.000 description 50
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 48
- 150000001875 compounds Chemical class 0.000 description 38
- 238000000354 decomposition reaction Methods 0.000 description 35
- 241000196324 Embryophyta Species 0.000 description 29
- 230000012010 growth Effects 0.000 description 21
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 description 20
- 159000000000 sodium salts Chemical class 0.000 description 17
- 240000008042 Zea mays Species 0.000 description 16
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 16
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 15
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- 125000004317 1,3,5-triazin-2-yl group Chemical group [H]C1=NC(*)=NC([H])=N1 0.000 description 6
- HCCNBKFJYUWLEX-UHFFFAOYSA-N 7-(6-methoxypyridin-3-yl)-1-(2-propoxyethyl)-3-(pyrazin-2-ylmethylamino)pyrido[3,4-b]pyrazin-2-one Chemical compound O=C1N(CCOCCC)C2=CC(C=3C=NC(OC)=CC=3)=NC=C2N=C1NCC1=CN=CC=N1 HCCNBKFJYUWLEX-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 6
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
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- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 6
- 229940126545 compound 53 Drugs 0.000 description 6
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- 235000005822 corn Nutrition 0.000 description 5
- 230000035784 germination Effects 0.000 description 5
- IXORZMNAPKEEDV-UHFFFAOYSA-N gibberellic acid GA3 Natural products OC(=O)C1C2(C3)CC(=C)C3(O)CCC2C2(C=CC3O)C1C3(C)C(=O)O2 IXORZMNAPKEEDV-UHFFFAOYSA-N 0.000 description 5
- 239000003448 gibberellin Substances 0.000 description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
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- LALCDSDHLXWTTL-UHFFFAOYSA-N 2-chloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=CC=C1S(=O)(=O)N=C=O LALCDSDHLXWTTL-UHFFFAOYSA-N 0.000 description 4
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- 230000015572 biosynthetic process Effects 0.000 description 4
- HVQWYKPSNHGIDD-UHFFFAOYSA-N methyl 2-isocyanatosulfonylbenzoate Chemical compound COC(=O)C1=CC=CC=C1S(=O)(=O)N=C=O HVQWYKPSNHGIDD-UHFFFAOYSA-N 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- CSCPPACGZOOCGX-MICDWDOJSA-N 1-deuteriopropan-2-one Chemical compound [2H]CC(C)=O CSCPPACGZOOCGX-MICDWDOJSA-N 0.000 description 3
- LYDQIFZADSUDGM-UHFFFAOYSA-N 2,5-dichloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=C(Cl)C(S(=O)(=O)N=C=O)=C1 LYDQIFZADSUDGM-UHFFFAOYSA-N 0.000 description 3
- RHPCYVNTFRAYEO-UHFFFAOYSA-N 2,6-dichloro-n-(oxomethylidene)benzenesulfonamide Chemical compound ClC1=CC=CC(Cl)=C1S(=O)(=O)N=C=O RHPCYVNTFRAYEO-UHFFFAOYSA-N 0.000 description 3
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 3
- 229940100389 Sulfonylurea Drugs 0.000 description 3
- 244000098338 Triticum aestivum Species 0.000 description 3
- 229940125782 compound 2 Drugs 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 230000002401 inhibitory effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- OSFBJERFMQCEQY-UHFFFAOYSA-N propylidene Chemical group [CH]CC OSFBJERFMQCEQY-UHFFFAOYSA-N 0.000 description 3
- 238000009331 sowing Methods 0.000 description 3
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- 230000004936 stimulating effect Effects 0.000 description 3
- 230000000638 stimulation Effects 0.000 description 3
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 3
- 239000000725 suspension Substances 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- 210000002700 urine Anatomy 0.000 description 3
- KCZIUKYAJJEIQG-UHFFFAOYSA-N 1,3,5-triazin-2-amine Chemical class NC1=NC=NC=N1 KCZIUKYAJJEIQG-UHFFFAOYSA-N 0.000 description 2
- WUTBRBBUURJOOS-UHFFFAOYSA-N 2-nitro-n-(oxomethylidene)benzenesulfonamide Chemical compound [O-][N+](=O)C1=CC=CC=C1S(=O)(=O)N=C=O WUTBRBBUURJOOS-UHFFFAOYSA-N 0.000 description 2
- 235000011305 Capsella bursa pastoris Nutrition 0.000 description 2
- 240000008867 Capsella bursa-pastoris Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000021307 Triticum Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- WRJWRGBVPUUDLA-UHFFFAOYSA-N chlorosulfonyl isocyanate Chemical compound ClS(=O)(=O)N=C=O WRJWRGBVPUUDLA-UHFFFAOYSA-N 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
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- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
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- UAOUIVVJBYDFKD-XKCDOFEDSA-N (1R,9R,10S,11R,12R,15S,18S,21R)-10,11,21-trihydroxy-8,8-dimethyl-14-methylidene-4-(prop-2-enylamino)-20-oxa-5-thia-3-azahexacyclo[9.7.2.112,15.01,9.02,6.012,18]henicosa-2(6),3-dien-13-one Chemical compound C([C@@H]1[C@@H](O)[C@@]23C(C1=C)=O)C[C@H]2[C@]12C(N=C(NCC=C)S4)=C4CC(C)(C)[C@H]1[C@H](O)[C@]3(O)OC2 UAOUIVVJBYDFKD-XKCDOFEDSA-N 0.000 description 1
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- JAXFJECJQZDFJS-XHEPKHHKSA-N gtpl8555 Chemical compound OC(=O)C[C@H](N)C(=O)N[C@@H](CCC(O)=O)C(=O)N[C@@H](C(C)C)C(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@@H]1C(=O)N[C@H](B1O[C@@]2(C)[C@H]3C[C@H](C3(C)C)C[C@H]2O1)CCC1=CC=C(F)C=C1 JAXFJECJQZDFJS-XHEPKHHKSA-N 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- ZLVXBBHTMQJRSX-VMGNSXQWSA-N jdtic Chemical compound C1([C@]2(C)CCN(C[C@@H]2C)C[C@H](C(C)C)NC(=O)[C@@H]2NCC3=CC(O)=CC=C3C2)=CC=CC(O)=C1 ZLVXBBHTMQJRSX-VMGNSXQWSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000010871 livestock manure Substances 0.000 description 1
- RENRQMCACQEWFC-UGKGYDQZSA-N lnp023 Chemical compound C1([C@H]2N(CC=3C=4C=CNC=4C(C)=CC=3OC)CC[C@@H](C2)OCC)=CC=C(C(O)=O)C=C1 RENRQMCACQEWFC-UGKGYDQZSA-N 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 235000019713 millet Nutrition 0.000 description 1
- APVPOHHVBBYQAV-UHFFFAOYSA-N n-(4-aminophenyl)sulfonyloctadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 APVPOHHVBBYQAV-UHFFFAOYSA-N 0.000 description 1
- UJYAZVSPFMJCLW-UHFFFAOYSA-N n-(oxomethylidene)benzenesulfonamide Chemical class O=C=NS(=O)(=O)C1=CC=CC=C1 UJYAZVSPFMJCLW-UHFFFAOYSA-N 0.000 description 1
- IOMMMLWIABWRKL-WUTDNEBXSA-N nazartinib Chemical compound C1N(C(=O)/C=C/CN(C)C)CCCC[C@H]1N1C2=C(Cl)C=CC=C2N=C1NC(=O)C1=CC=NC(C)=C1 IOMMMLWIABWRKL-WUTDNEBXSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 231100000926 not very toxic Toxicity 0.000 description 1
- 229940078552 o-xylene Drugs 0.000 description 1
- PIDFDZJZLOTZTM-KHVQSSSXSA-N ombitasvir Chemical compound COC(=O)N[C@@H](C(C)C)C(=O)N1CCC[C@H]1C(=O)NC1=CC=C([C@H]2N([C@@H](CC2)C=2C=CC(NC(=O)[C@H]3N(CCC3)C(=O)[C@@H](NC(=O)OC)C(C)C)=CC=2)C=2C=CC(=CC=2)C(C)(C)C)C=C1 PIDFDZJZLOTZTM-KHVQSSSXSA-N 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical class OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 239000005648 plant growth regulator Substances 0.000 description 1
- 230000008092 positive effect Effects 0.000 description 1
- 159000000001 potassium salts Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 230000005082 stem growth Effects 0.000 description 1
- NVBFHJWHLNUMCV-UHFFFAOYSA-N sulfamide Chemical group NS(N)(=O)=O NVBFHJWHLNUMCV-UHFFFAOYSA-N 0.000 description 1
- 229940124530 sulfonamide Drugs 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
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
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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/SU1990/000067 WO1991013880A1 (en) | 1990-03-07 | 1990-03-07 | Substituted penylsulphonyltriazinylurea and salts thereof and means for stimulating and suppressing plant growth based on them |
| CA002036334A CA2036334C (en) | 1990-03-07 | 1991-02-14 | Substituted phenylsulphonyltriazinylureas, salts thereof and agent for plant growth stimulation and inhibition based thereon |
| CS91442A CS44291A3 (en) | 1990-03-07 | 1991-02-20 | Agent for plant growth promoting and inhibiting |
| CN91102096.9A CN1064388A (zh) | 1990-03-07 | 1991-03-05 | 用于促进和抑制植物生长的制剂 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE4092524C2 true DE4092524C2 (de) | 1996-09-12 |
Family
ID=27168867
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE4092524A Expired - Fee Related DE4092524C2 (de) | 1990-03-07 | 1990-03-07 | Substituierte Phenylsulfonyltriazinylharnstoffe, deren Salze und Mittel mit pflanzenwachstumsregelierender Wirkung |
| DE19904092524 Pending DE4092524T (enrdf_load_stackoverflow) | 1990-03-07 | 1990-03-07 |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19904092524 Pending DE4092524T (enrdf_load_stackoverflow) | 1990-03-07 | 1990-03-07 |
Country Status (9)
| Country | Link |
|---|---|
| JP (1) | JPH05501415A (enrdf_load_stackoverflow) |
| CN (1) | CN1064388A (enrdf_load_stackoverflow) |
| AU (1) | AU631474B2 (enrdf_load_stackoverflow) |
| CA (1) | CA2036334C (enrdf_load_stackoverflow) |
| CH (1) | CH683341A5 (enrdf_load_stackoverflow) |
| CS (1) | CS44291A3 (enrdf_load_stackoverflow) |
| DE (2) | DE4092524C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2673181B1 (enrdf_load_stackoverflow) |
| GB (1) | GB2251613B (enrdf_load_stackoverflow) |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2040180C1 (ru) * | 1992-09-04 | 1995-07-25 | Латвийская фирма "КАРЕ" | Гербицидный синергитический состав |
| WO2000044226A1 (de) * | 1999-01-27 | 2000-08-03 | Aventis Cropscience Gmbh | Formulierung von herbiziden |
| DE19963383A1 (de) | 1999-12-28 | 2001-07-05 | Aventis Cropscience Gmbh | Formulierung von Herbiziden und Pflanzenwachstumsregulatoren |
| CN105439970A (zh) * | 2015-10-16 | 2016-03-30 | 南开大学 | 一类可控土壤降解速度的磺酰脲类新结构的发现与应用 |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127405A (en) * | 1976-04-07 | 1978-11-28 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| EP0009419A1 (en) * | 1978-09-27 | 1980-04-02 | E.I. Du Pont De Nemours And Company | Agricultural sulfonamides, and preparation and use thereof |
| US4348219A (en) * | 1980-07-11 | 1982-09-07 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| EP0164669A2 (de) * | 1984-06-13 | 1985-12-18 | Röhm Gmbh | Verfahren zum Überziehen von Arzneiformen |
| US4786316A (en) * | 1984-07-13 | 1988-11-22 | E. I. Du Pont De Nemours And Company | Herbicidal ortho-sulfamoyl sulfonamides |
Family Cites Families (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4231784A (en) * | 1979-05-10 | 1980-11-04 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| CS226915B1 (en) * | 1981-11-24 | 1984-04-16 | Varkonda Stefan | Plant growth regulating composition |
| US4780127A (en) * | 1982-03-25 | 1988-10-25 | Stauffer Chemical Company | Certain 2-(substituted benzoyl)-1,3-cyclohexanediones and their use as herbicides |
| ZA831626B (en) * | 1982-08-25 | 1983-11-30 | Velsicol Chemical Corp | New triazine compositions of matter |
| 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 |
| DE3413490A1 (de) * | 1984-04-10 | 1985-10-17 | Bayer Ag, 5090 Leverkusen | 2-(alkoximinoalkyloxycarbonyl)-phenylsulfonylharnstoffe |
| EP0164269B1 (en) * | 1984-06-07 | 1990-04-18 | E.I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| AU611191B2 (en) * | 1987-07-27 | 1991-06-06 | E.I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| ATE92922T1 (de) * | 1988-03-24 | 1993-08-15 | Du Pont | Fluoroalkoxyaminotriazine zur kontrolle von unkraut in zuckerruebenfeldern. |
| JP2738010B2 (ja) * | 1988-07-15 | 1998-04-08 | 日産化学工業株式会社 | ピラゾール誘動体及び選択性除草剤 |
| JP2764931B2 (ja) * | 1988-08-05 | 1998-06-11 | 日産化学工業株式会社 | 安息香酸類の製法 |
-
1990
- 1990-03-07 JP JP3500742A patent/JPH05501415A/ja active Pending
- 1990-03-07 CH CH3286/91A patent/CH683341A5/de not_active IP Right Cessation
- 1990-03-07 AU AU68891/91A patent/AU631474B2/en not_active Ceased
- 1990-03-07 DE DE4092524A patent/DE4092524C2/de not_active Expired - Fee Related
- 1990-03-07 DE DE19904092524 patent/DE4092524T/de active Pending
-
1991
- 1991-02-14 CA CA002036334A patent/CA2036334C/en not_active Expired - Fee Related
- 1991-02-20 CS CS91442A patent/CS44291A3/cs unknown
- 1991-02-26 FR FR9102282A patent/FR2673181B1/fr not_active Expired - Fee Related
- 1991-03-05 CN CN91102096.9A patent/CN1064388A/zh active Pending
- 1991-11-07 GB GB9123657A patent/GB2251613B/en not_active Expired - Fee Related
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127405A (en) * | 1976-04-07 | 1978-11-28 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| EP0009419A1 (en) * | 1978-09-27 | 1980-04-02 | E.I. Du Pont De Nemours And Company | Agricultural sulfonamides, and preparation and use thereof |
| US4348219A (en) * | 1980-07-11 | 1982-09-07 | E. I. Du Pont De Nemours And Company | Herbicidal sulfonamides |
| EP0164669A2 (de) * | 1984-06-13 | 1985-12-18 | Röhm Gmbh | Verfahren zum Überziehen von Arzneiformen |
| US4786316A (en) * | 1984-07-13 | 1988-11-22 | E. I. Du Pont De Nemours And Company | Herbicidal ortho-sulfamoyl sulfonamides |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9123657D0 (en) | 1992-01-02 |
| GB2251613A (en) | 1992-07-15 |
| CN1064388A (zh) | 1992-09-16 |
| FR2673181B1 (fr) | 1994-02-11 |
| CH683341A5 (de) | 1994-02-28 |
| GB2251613B (en) | 1993-11-17 |
| DE4092524T (enrdf_load_stackoverflow) | 1992-04-23 |
| JPH05501415A (ja) | 1993-03-18 |
| CA2036334A1 (en) | 1992-08-15 |
| CS44291A3 (en) | 1992-12-16 |
| AU6889191A (en) | 1991-10-10 |
| FR2673181A1 (fr) | 1992-08-28 |
| CA2036334C (en) | 1997-03-18 |
| AU631474B2 (en) | 1992-11-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8181 | Inventor (new situation) |
Free format text: SOROKIN, VLADIMIR IOSIFOVIC KUZNECOVA, GALINA VLADIMIROVNA RUSAKOVA, NATAL JA IONOVNA CYBALOVA, LJUBOV ALEKSANDROVNA MELIKHOVA, IRINA NIKOLAEVNA GRANINA, TAT JANA JEVGEN EVNA DROZD, VIKTOR NIKOLAJEVIC SAPOVALOV, ALEKSANDR ALEKSEJEVIC LOJ, NELLJ PAVLOVNA SVAREVA, TAT JANA ANATOL EVNA, MOSKAU/MOSKVA, SU PETUNOVA, ANGELIKA ALEKSANDROVNA, ST. PETERSBURG, SU COMLJAK, JULIAN DMITRIJEVIC, L VOVSKAJA OBLAST , OBROSINO, SU KRAVCENKO, NIKOLAJ SIDOROVIC MILYJ, VLADIMIR VLADIMIROVIC, CAR KOV, SU BARASKIN, |
|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8339 | Ceased/non-payment of the annual fee |