DE2905650C2 - - Google Patents
Info
- Publication number
- DE2905650C2 DE2905650C2 DE2905650A DE2905650A DE2905650C2 DE 2905650 C2 DE2905650 C2 DE 2905650C2 DE 2905650 A DE2905650 A DE 2905650A DE 2905650 A DE2905650 A DE 2905650A DE 2905650 C2 DE2905650 C2 DE 2905650C2
- Authority
- DE
- Germany
- Prior art keywords
- mol
- water
- azaspiro
- decane
- oxa
- 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
- 230000002363 herbicidal effect Effects 0.000 claims description 8
- -1 thiol carbamate Chemical class 0.000 claims description 8
- 239000000729 antidote Substances 0.000 claims description 7
- 239000004009 herbicide Substances 0.000 claims description 7
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 19
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 18
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 12
- 239000004480 active ingredient Substances 0.000 description 11
- 150000001875 compounds Chemical class 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 238000002360 preparation method Methods 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 8
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 238000001816 cooling Methods 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 238000009331 sowing Methods 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 239000007788 liquid Substances 0.000 description 5
- 230000007935 neutral effect Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000013543 active substance Substances 0.000 description 4
- FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 229940031098 ethanolamine Drugs 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 4
- 230000002147 killing effect Effects 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- MPBDMTMCMZNPMY-UHFFFAOYSA-N 1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound CC(=O)N1CCOC11CCCCC1 MPBDMTMCMZNPMY-UHFFFAOYSA-N 0.000 description 3
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 description 3
- KBRFAFZXAHRSNP-UHFFFAOYSA-N 3,3-dimethyl-1-oxa-4-azaspiro[4.5]decane Chemical compound N1C(C)(C)COC11CCCCC1 KBRFAFZXAHRSNP-UHFFFAOYSA-N 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 3
- 239000012346 acetyl chloride Substances 0.000 description 3
- CBTVGIZVANVGBH-UHFFFAOYSA-N aminomethyl propanol Chemical compound CC(C)(N)CO CBTVGIZVANVGBH-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- JROGBPMEKVAPEH-GXGBFOEMSA-N emetine dihydrochloride Chemical compound Cl.Cl.N1CCC2=CC(OC)=C(OC)C=C2[C@H]1C[C@H]1C[C@H]2C3=CC(OC)=C(OC)C=C3CCN2C[C@@H]1CC JROGBPMEKVAPEH-GXGBFOEMSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 238000006277 sulfonation reaction Methods 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VGCXGMAHQTYDJK-UHFFFAOYSA-N Chloroacetyl chloride Chemical compound ClCC(Cl)=O VGCXGMAHQTYDJK-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000012043 crude product Substances 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- 230000000885 phytotoxic effect Effects 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 238000005292 vacuum distillation Methods 0.000 description 2
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- QQZOPKMRPOGIEB-UHFFFAOYSA-N 2-Oxohexane Chemical compound CCCCC(C)=O QQZOPKMRPOGIEB-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 244000237956 Amaranthus retroflexus Species 0.000 description 1
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 description 1
- 240000001327 Echinochloa stagnina Species 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- 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 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- 240000008114 Panicum miliaceum Species 0.000 description 1
- 235000007199 Panicum miliaceum Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 240000005498 Setaria italica Species 0.000 description 1
- 235000007226 Setaria italica Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000007244 Zea mays Nutrition 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000001944 continuous distillation Methods 0.000 description 1
- 238000010411 cooking Methods 0.000 description 1
- 230000000254 damaging effect Effects 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 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 1
- 239000003814 drug Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000009036 growth inhibition Effects 0.000 description 1
- 125000005252 haloacyl group Chemical group 0.000 description 1
- 125000001475 halogen functional group Chemical group 0.000 description 1
- DKAGJZJALZXOOV-UHFFFAOYSA-N hydrate;hydrochloride Chemical compound O.Cl DKAGJZJALZXOOV-UHFFFAOYSA-N 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 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 1
- 239000000463 material Substances 0.000 description 1
- 230000003641 microbiacidal effect Effects 0.000 description 1
- 230000003158 microbiostatic effect Effects 0.000 description 1
- 230000009526 moderate injury Effects 0.000 description 1
- 230000001338 necrotic effect Effects 0.000 description 1
- LIXFJRLISFERDN-UHFFFAOYSA-N o-ethyl n,n-dipropylcarbamothioate Chemical compound CCCN(CCC)C(=S)OCC LIXFJRLISFERDN-UHFFFAOYSA-N 0.000 description 1
- 125000000160 oxazolidinyl group Chemical group 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- 239000012264 purified product Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 230000009528 severe injury Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/04—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/52—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/06—1,3-Thiazines; Hydrogenated 1,3-thiazines not condensed with other rings
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
- C07D279/04—1,3-Thiazines; Hydrogenated 1,3-thiazines
- C07D279/08—1,3-Thiazines; Hydrogenated 1,3-thiazines condensed with carbocyclic rings or ring systems
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Toxicology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| HUME002142 HU178301B (en) | 1978-02-06 | 1978-02-06 | Herbicide compositions containing naphthaline-carboxylic acid derivatives as antidotes and carbamide derivatives and antidote compositions containing naphthaline-carboxylic acid derivatives |
| BE193625A BE874361A (fr) | 1978-02-06 | 1979-02-22 | Composition herbicide selective |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2905650A1 DE2905650A1 (de) | 1980-08-21 |
| DE2905650C2 true DE2905650C2 (en, 2012) | 1989-02-16 |
Family
ID=25651298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19792905650 Granted DE2905650A1 (de) | 1978-02-06 | 1979-02-14 | Unkrautvernichtungsmittel |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4256481A (en, 2012) |
| CH (1) | CH640108A5 (en, 2012) |
| DE (1) | DE2905650A1 (en, 2012) |
| FR (1) | FR2448857B1 (en, 2012) |
| GB (1) | GB2043447B (en, 2012) |
| LU (1) | LU80912A1 (en, 2012) |
| NL (1) | NL187256C (en, 2012) |
Families Citing this family (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5011526A (en) * | 1978-09-20 | 1991-04-30 | Ici Americas Inc. | Herbicide compositions of extended soil life |
| HU187284B (en) * | 1980-12-11 | 1985-12-28 | Mta Koezponti Kemiai Kutato In | Herbicide compositions containing antitoxines of aldehyde- and ketone-derivatives |
| CA1196917A (en) * | 1982-03-26 | 1985-11-19 | Derek A. Wood | N-substituted-tetrahydrothiazines, process for their preparation, and their use as pesticides |
| DE3403147A1 (de) * | 1984-01-31 | 1985-08-01 | Wella Ag, 6100 Darmstadt | 3-carbamoyl- und 3-thiocarbamoyl-tetrahydro-1,3-thiazin-2-thione, verfahren zu ihrer herstellung sowie diese verbindungen enthaltende hautbehandlungsmittel |
| US5051125A (en) * | 1986-03-04 | 1991-09-24 | Ici Americas Inc. | Synergistic herbicidal composition of cycloate and cyanazine |
| US4938796A (en) * | 1987-07-06 | 1990-07-03 | Ici Americas Inc. | Herbicidal compositions of acylated 1,3-dicarbonyl herbicides and antidotes therefor |
| HU210367B (en) * | 1989-04-11 | 1995-04-28 | Nitrokemia Ipartelepek | Antidoted herbicidal compositions and antidotal composition and process for their use |
| US5527762A (en) * | 1990-12-12 | 1996-06-18 | Zeneca Limited | Antidoting herbicidal 3-isoxazolidinone compounds |
| US5541148A (en) * | 1992-07-08 | 1996-07-30 | Ciba-Geigy Corporation | Selective safened herbicidal composition comprising 2-ethoxycarbonyl-3-(4,6-dimethoxypyrimidine-2-yl) oxy-pyridine and an acylsulfamoylphenyl-urea safener |
| EP0616770B1 (de) | 1993-03-22 | 1999-05-06 | Novartis AG | Selektiv-herbizides Mittel |
| EE9500018A (et) * | 1994-06-03 | 1995-12-15 | Ciba-Geigy Ag | Selektiivne herbitsiid ja meetod selle kasutamiseks |
| FR2762475B1 (fr) * | 1997-04-25 | 1999-07-16 | Nitrokemia Rt | Compositions herbicides a base de chloroacetamide et de 1,3,5-triazine et leur utilisation |
| JP3967431B2 (ja) * | 1997-09-03 | 2007-08-29 | 株式会社トクヤマ | エテニルアミド系除草剤組成物 |
| CN116283812A (zh) * | 2023-03-04 | 2023-06-23 | 徐州彰梁生化科技有限公司 | 一种苯叉酰胺生产工艺 |
Family Cites Families (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2035796A1 (de) * | 1970-07-18 | 1972-01-27 | Bayer Ag | Verfahren zum Austausch von N Nitroso |
| CA1174865A (en) * | 1971-04-16 | 1984-09-25 | Ferenc M. Pallos | Thiolcarbamate herbicides containing nitrogen containing antidote |
| US3989503A (en) * | 1972-10-13 | 1976-11-02 | Stauffer Chemical Company | Herbicidal antidote compositions with substituted oxazolidines and thiazolidines |
| HU165736B (en, 2012) * | 1972-04-13 | 1974-10-28 | ||
| US3859292A (en) * | 1972-08-15 | 1975-01-07 | Scm Corp | N-haloacyl (2-spirocycloaliphatic) oxazolidines |
| GB1420685A (en) * | 1972-08-15 | 1976-01-07 | Scm Corp | Substituted oxazolidines |
| US3881908A (en) * | 1972-08-15 | 1975-05-06 | Scm Corp | Herbicidal N-haloacyl (2-spirocycloaliphatic) oxazolidines |
| US3884671A (en) * | 1972-08-15 | 1975-05-20 | Scm Corp | Herbicidal n-haloacyl (2-alkylated) oxazolidines |
| GB1457128A (en) * | 1972-10-13 | 1976-12-01 | Stauffer Chemical Co | Substituted oxazolidines and thiazolidines |
| CH574207A5 (en, 2012) * | 1973-01-25 | 1976-04-15 | Ciba Geigy Ag | |
| US4124372A (en) * | 1973-05-02 | 1978-11-07 | Stauffer Chemical Company | Herbicidal antidote compositions with substituted oxazolidines and thiazolidines |
| GB1403876A (en) * | 1973-05-04 | 1975-08-28 | Stauffer Chemical Co | Thiazolidine derivatives and their use as herbicide antidotes |
| BR7600775A (pt) * | 1975-02-14 | 1977-05-10 | Stauffer Chemical Co | Processo para a obtencao de(tio)haloacil-(tia)oxazolidinas arisubstituidas e composicoes herbicidas sinergeticas que as contem |
| FR2310348A1 (fr) * | 1975-05-07 | 1976-12-03 | Ugine Kuhlmann | Nouveaux derives heterocycliques antidotes contre herbicides |
| HU178064B (en) * | 1978-05-31 | 1982-02-28 | Noevenyvedelmi Kutato Intezet | Antidote composition containing n-/trimethyl-cyclopentillidene /-ethanol-amine-dichloracetate and process for preparing the active material |
-
1979
- 1979-02-12 CH CH133179A patent/CH640108A5/de not_active IP Right Cessation
- 1979-02-12 LU LU80912A patent/LU80912A1/de unknown
- 1979-02-14 GB GB7905299A patent/GB2043447B/en not_active Expired
- 1979-02-14 DE DE19792905650 patent/DE2905650A1/de active Granted
- 1979-02-19 FR FR7904130A patent/FR2448857B1/fr not_active Expired
- 1979-02-27 NL NLAANVRAGE7901548,A patent/NL187256C/xx not_active IP Right Cessation
- 1979-03-02 US US06/017,034 patent/US4256481A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| GB2043447A (en) | 1980-10-08 |
| DE2905650A1 (de) | 1980-08-21 |
| NL187256C (nl) | 1991-08-01 |
| CH640108A5 (de) | 1983-12-30 |
| NL7901548A (nl) | 1980-08-29 |
| FR2448857B1 (fr) | 1982-05-28 |
| US4256481A (en) | 1981-03-17 |
| GB2043447B (en) | 1983-10-26 |
| LU80912A1 (de) | 1979-06-07 |
| FR2448857A1 (fr) | 1980-09-12 |
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