SU969162A3 - Способ получени производных 1,2,4-оксадиазола (его вариант) - Google Patents
Способ получени производных 1,2,4-оксадиазола (его вариант) Download PDFInfo
- Publication number
- SU969162A3 SU969162A3 SU792707604A SU2707604A SU969162A3 SU 969162 A3 SU969162 A3 SU 969162A3 SU 792707604 A SU792707604 A SU 792707604A SU 2707604 A SU2707604 A SU 2707604A SU 969162 A3 SU969162 A3 SU 969162A3
- Authority
- SU
- USSR - Soviet Union
- Prior art keywords
- general formula
- phenyl
- alkyl
- oxadiazole
- lower alkyl
- Prior art date
Links
- 150000005071 1,2,4-oxadiazoles Chemical class 0.000 title claims abstract description 5
- 238000000034 method Methods 0.000 title description 4
- 230000004048 modification Effects 0.000 title 1
- 238000012986 modification Methods 0.000 title 1
- -1 halogeno-C1-C3-alkyl Chemical group 0.000 claims abstract description 22
- 150000001875 compounds Chemical class 0.000 claims abstract description 8
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 5
- 150000002367 halogens Chemical class 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 125000003545 alkoxy group Chemical group 0.000 claims description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
- 230000003993 interaction Effects 0.000 claims description 3
- SFZULDYEOVSIKM-UHFFFAOYSA-N chembl321317 Chemical compound C1=CC(C(=N)NO)=CC=C1C1=CC=C(C=2C=CC(=CC=2)C(=N)NO)O1 SFZULDYEOVSIKM-UHFFFAOYSA-N 0.000 claims description 2
- 238000002474 experimental method Methods 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims 4
- 239000002253 acid Substances 0.000 claims 3
- WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 claims 2
- 150000004820 halides Chemical class 0.000 claims 2
- 150000008064 anhydrides Chemical class 0.000 claims 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 claims 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims 1
- 150000002391 heterocyclic compounds Chemical class 0.000 claims 1
- 239000012948 isocyanate Substances 0.000 claims 1
- 150000002513 isocyanates Chemical class 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 12
- 244000105624 Arachis hypogaea Species 0.000 abstract description 3
- 230000000694 effects Effects 0.000 abstract description 3
- 235000020232 peanut Nutrition 0.000 abstract description 3
- 229920000742 Cotton Polymers 0.000 abstract description 2
- 241000219146 Gossypium Species 0.000 abstract description 2
- 244000020551 Helianthus annuus Species 0.000 abstract description 2
- 235000003222 Helianthus annuus Nutrition 0.000 abstract description 2
- 240000004658 Medicago sativa Species 0.000 abstract description 2
- 235000017587 Medicago sativa ssp. sativa Nutrition 0.000 abstract description 2
- 240000007594 Oryza sativa Species 0.000 abstract description 2
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 2
- 240000004713 Pisum sativum Species 0.000 abstract description 2
- 235000010582 Pisum sativum Nutrition 0.000 abstract description 2
- 241000219793 Trifolium Species 0.000 abstract description 2
- 240000008042 Zea mays Species 0.000 abstract description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 2
- 235000009566 rice Nutrition 0.000 abstract description 2
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 abstract 2
- 125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 abstract 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 abstract 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 abstract 1
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 abstract 1
- 244000068988 Glycine max Species 0.000 abstract 1
- 235000010469 Glycine max Nutrition 0.000 abstract 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 abstract 1
- 235000013339 cereals Nutrition 0.000 abstract 1
- 125000004093 cyano group Chemical group *C#N 0.000 abstract 1
- 235000009973 maize Nutrition 0.000 abstract 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 20
- VEUMBMHMMCOFAG-UHFFFAOYSA-N 2,3-dihydrooxadiazole Chemical compound N1NC=CO1 VEUMBMHMMCOFAG-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000019439 ethyl acetate Nutrition 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 239000000203 mixture Substances 0.000 description 7
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
- 230000006378 damage Effects 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- QAEDZJGFFMLHHQ-UHFFFAOYSA-N trifluoroacetic anhydride Chemical compound FC(F)(F)C(=O)OC(=O)C(F)(F)F QAEDZJGFFMLHHQ-UHFFFAOYSA-N 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 229940088623 biologically active substance Drugs 0.000 description 3
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 3
- 235000019341 magnesium sulphate Nutrition 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- BBVIDBNAYOIXOE-UHFFFAOYSA-N 1,2,4-oxadiazole Chemical compound C=1N=CON=1 BBVIDBNAYOIXOE-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- 244000056139 Brassica cretica Species 0.000 description 2
- 235000003351 Brassica cretica Nutrition 0.000 description 2
- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 240000003768 Solanum lycopersicum Species 0.000 description 2
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 230000002363 herbicidal effect Effects 0.000 description 2
- 235000010460 mustard Nutrition 0.000 description 2
- WCPAKWJPBJAGKN-UHFFFAOYSA-N oxadiazole Chemical compound C1=CON=N1 WCPAKWJPBJAGKN-UHFFFAOYSA-N 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- LJGHYPLBDBRCRZ-UHFFFAOYSA-N 3-(3-aminophenyl)sulfonylaniline Chemical group NC1=CC=CC(S(=O)(=O)C=2C=C(N)C=CC=2)=C1 LJGHYPLBDBRCRZ-UHFFFAOYSA-N 0.000 description 1
- SFWRWZSCYBJCMH-UHFFFAOYSA-N 3-(3-nitrophenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound [O-][N+](=O)C1=CC=CC(C=2N=C(ON=2)C(F)(F)F)=C1 SFWRWZSCYBJCMH-UHFFFAOYSA-N 0.000 description 1
- JJBDWBUEPCGFMN-UHFFFAOYSA-N 3-phenyl-1,2,4-oxadiazole Chemical compound O1C=NC(C=2C=CC=CC=2)=N1 JJBDWBUEPCGFMN-UHFFFAOYSA-N 0.000 description 1
- VPQUXMJGCDXDFA-UHFFFAOYSA-N 3-tert-butyl-1,2,4-oxadiazole Chemical compound CC(C)(C)C=1N=CON=1 VPQUXMJGCDXDFA-UHFFFAOYSA-N 0.000 description 1
- XDOXQQBUPUADQB-UHFFFAOYSA-N 5-(trifluoromethyl)-1,2,4-oxadiazole Chemical compound FC(F)(F)C1=NC=NO1 XDOXQQBUPUADQB-UHFFFAOYSA-N 0.000 description 1
- YIIMEMSDCNDGTB-UHFFFAOYSA-N Dimethylcarbamoyl chloride Chemical compound CN(C)C(Cl)=O YIIMEMSDCNDGTB-UHFFFAOYSA-N 0.000 description 1
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 206010003549 asthenia Diseases 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 235000008429 bread Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005119 centrifugation Methods 0.000 description 1
- 125000000068 chlorophenyl group Chemical group 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 235000005822 corn Nutrition 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 235000021374 legumes Nutrition 0.000 description 1
- HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- ZAIHFKLUPWFUGH-UHFFFAOYSA-N n'-hydroxy-3-nitrobenzenecarboximidamide Chemical compound ON=C(N)C1=CC=CC([N+]([O-])=O)=C1 ZAIHFKLUPWFUGH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000008207 working material Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
- C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
- C07D271/06—1,2,4-Oxadiazoles; Hydrogenated 1,2,4-oxadiazoles
-
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
-
- 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
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/20—N-Aryl derivatives 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
- A01N47/08—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<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Chemical & Material Sciences (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- General Health & Medical Sciences (AREA)
- Environmental Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Organic Chemistry (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19782801509 DE2801509A1 (de) | 1978-01-12 | 1978-01-12 | 1,2,4-oxadiazolderivate, verfahren zur herstellung dieser verbindungen sowie diese enthaltende selektive herbizide mittel |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| SU969162A3 true SU969162A3 (ru) | 1982-10-23 |
Family
ID=6029492
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SU792707604A SU969162A3 (ru) | 1978-01-12 | 1979-01-11 | Способ получени производных 1,2,4-оксадиазола (его вариант) |
Country Status (27)
| Country | Link |
|---|---|
| US (1) | US4243409A (OSRAM) |
| JP (1) | JPS54100376A (OSRAM) |
| AT (1) | AT362614B (OSRAM) |
| AU (1) | AU527548B2 (OSRAM) |
| BE (1) | BE873447A (OSRAM) |
| BG (1) | BG30169A3 (OSRAM) |
| CA (1) | CA1118426A (OSRAM) |
| CH (1) | CH637647A5 (OSRAM) |
| CS (1) | CS204045B2 (OSRAM) |
| DD (1) | DD141405A5 (OSRAM) |
| DE (1) | DE2801509A1 (OSRAM) |
| DK (1) | DK542178A (OSRAM) |
| ES (1) | ES476468A1 (OSRAM) |
| FR (1) | FR2414504A1 (OSRAM) |
| GB (1) | GB2012764B (OSRAM) |
| GR (1) | GR73141B (OSRAM) |
| HU (1) | HU180987B (OSRAM) |
| IE (1) | IE47724B1 (OSRAM) |
| IL (1) | IL56339A (OSRAM) |
| IT (1) | IT1110393B (OSRAM) |
| LU (1) | LU80775A1 (OSRAM) |
| NL (1) | NL7811925A (OSRAM) |
| PL (1) | PL113006B1 (OSRAM) |
| PT (1) | PT69058A (OSRAM) |
| RO (1) | RO76592A (OSRAM) |
| SU (1) | SU969162A3 (OSRAM) |
| YU (1) | YU301778A (OSRAM) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2430098C2 (ru) * | 2005-12-22 | 2011-09-27 | Грюненталь Гмбх | Замещенные производные оксадиазола и их применение в качестве лигандов опиоидных рецепторов |
| RU2495030C2 (ru) * | 2006-09-08 | 2013-10-10 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы получения 1,2,4-оксадиазолбензойных кислот |
| RU2512293C1 (ru) * | 2012-12-13 | 2014-04-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Ярославский государственный технический университет" | Способ получения этил 1,2,4-оксадиазол-5-карбоксилатов |
| RU2643807C1 (ru) * | 2010-11-12 | 2018-02-06 | Сионоги Энд Ко., Лтд. | Кристаллы производных 6,7-ненасыщенного-7-карбамоилморфинана и способ их получения |
| RU2674448C1 (ru) * | 2017-07-12 | 2018-12-10 | Марина Владимировна Тарасенко | 3-(3-аминофенил)-5-(проп-1-ен-2-ил)-1,2,4-оксадиазол |
| RU2754735C1 (ru) * | 2020-12-14 | 2021-09-06 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Ярославский государственный технический университет" ФГБОУВО "ЯГТУ" | Способ получения 3,5-дизамещенных 1,2,4-оксадиазолов, содержащих алкенильный фрагмент |
Families Citing this family (16)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3148291A1 (de) * | 1981-12-05 | 1983-06-09 | Basf Ag, 6700 Ludwigshafen | Harnstoffderivate, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses |
| US4857099A (en) * | 1982-02-12 | 1989-08-15 | American Cyanamid Company | Terrestrial and aquatic herbicidal methods |
| US4426527A (en) | 1982-02-12 | 1984-01-17 | Ppg Industries, Inc. | 3-[5- Or 3-substituted-1,2,4-oxadiazol-3- or -5-yl]-1-substituted-4-substituted-5-substituted or unsubstituted-2-imidazolidinones |
| JPS58150576A (ja) * | 1982-03-03 | 1983-09-07 | Sumitomo Chem Co Ltd | 新規な１，２，４−オキサジアゾ−ル誘導体 |
| IT1163183B (it) * | 1983-03-29 | 1987-04-08 | Anic Spa | Composti eterociclici ad attivita' erbicida |
| US4488897A (en) * | 1983-09-06 | 1984-12-18 | Stauffer Chemical Company | Dichloromethyl oxadiazole herbicide antidotes |
| DE3445205A1 (de) * | 1984-12-12 | 1986-06-12 | Bayer Ag, 5090 Leverkusen | N-(3-chlor-1,2,4-oxadiazol-5-yl)-harnstoffe |
| EP0276432A3 (de) * | 1986-12-12 | 1988-10-26 | Ciba-Geigy Ag | Schädlingsbekämpfungsmittel |
| DE19643037A1 (de) * | 1996-10-18 | 1998-04-23 | Boehringer Ingelheim Kg | Neue Oxadiazole, Verfahren zu ihrer Herstellung sowie deren Verwendung als Arzneimittel |
| ES2293980T3 (es) * | 2000-01-13 | 2008-04-01 | Amgen Inc. | Agentes antibacterianos. |
| EP3371177A1 (en) | 2015-11-02 | 2018-09-12 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| BR112018009539B1 (pt) | 2015-11-13 | 2022-05-24 | Basf Se | Uso de compostos da fórmula i, compostos, mistura, composição agroquímica, uso dos compostos e método para combater fungos nocivos fitopatogênicos |
| AR106679A1 (es) | 2015-11-13 | 2018-02-07 | Basf Se | Oxadiazoles sustituidos para combatir hongos fitopatógenos |
| US10674727B2 (en) | 2015-11-19 | 2020-06-09 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
| BR112018012954B1 (pt) * | 2015-12-25 | 2022-04-26 | Sumitomo Chemical Company, Limited | Compostos de oxadiazol, uso dos mesmos, agente e método para controle de doenças de planta e composição que os compreende |
| AU2017250397A1 (en) | 2016-04-11 | 2018-10-11 | Basf Se | Substituted oxadiazoles for combating phytopathogenic fungi |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| NL254547A (OSRAM) | 1959-08-05 | |||
| US3218331A (en) * | 1962-04-17 | 1965-11-16 | Union Carbide Corp | Preparation of substituted oxadiazoles |
| FR1395890A (fr) * | 1963-03-22 | 1965-04-16 | Chinoin Gyogyszer Es Vegyeszet | Procédé de préparation de dérivés de l'oxadiazole |
| NL132134C (OSRAM) * | 1963-03-22 | |||
| US3632599A (en) * | 1967-04-28 | 1972-01-04 | Basf Ag | Substituted 1 2 4-oxadiazolidine-3 5-diones |
| GB1051322A (OSRAM) * | 1967-08-09 | |||
| US3575997A (en) * | 1968-07-24 | 1971-04-20 | Squibb & Sons Inc | Novel nematocides and herbicides |
| FR2076487A5 (OSRAM) * | 1970-01-16 | 1971-10-15 | Rhone Poulenc Sa | |
| JPS5012088A (OSRAM) * | 1973-05-31 | 1975-02-07 | ||
| GB1490406A (en) * | 1974-07-22 | 1977-11-02 | Squibb & Sons Inc | Oxadiazoles |
| US4003909A (en) * | 1974-07-22 | 1977-01-18 | E. R. Squibb & Sons, Inc. | [(1,2,4-Oxadiazol-3-yl)phenyl]carbamic or thiocarbamic acid esters |
| JPS51128434A (en) * | 1975-01-10 | 1976-11-09 | Commw Scient Ind Res Org | Method of controlling plant growth and killing it |
-
1978
- 1978-01-12 DE DE19782801509 patent/DE2801509A1/de not_active Withdrawn
- 1978-11-30 DK DK542178A patent/DK542178A/da not_active Application Discontinuation
- 1978-12-06 NL NL7811925A patent/NL7811925A/xx not_active Application Discontinuation
- 1978-12-21 YU YU03017/78A patent/YU301778A/xx unknown
- 1978-12-29 IL IL56339A patent/IL56339A/xx unknown
- 1978-12-29 ES ES476468A patent/ES476468A1/es not_active Expired
-
1979
- 1979-01-04 US US06/001,157 patent/US4243409A/en not_active Expired - Lifetime
- 1979-01-08 GB GB79587A patent/GB2012764B/en not_active Expired
- 1979-01-08 JP JP33279A patent/JPS54100376A/ja active Pending
- 1979-01-09 CS CS79208A patent/CS204045B2/cs unknown
- 1979-01-09 BG BG042001A patent/BG30169A3/xx unknown
- 1979-01-10 PT PT69058A patent/PT69058A/pt unknown
- 1979-01-10 DD DD79210409A patent/DD141405A5/de unknown
- 1979-01-10 AU AU43263/79A patent/AU527548B2/en not_active Ceased
- 1979-01-10 LU LU80775A patent/LU80775A1/de unknown
- 1979-01-10 PL PL1979212703A patent/PL113006B1/pl unknown
- 1979-01-10 RO RO7996238A patent/RO76592A/ro unknown
- 1979-01-10 GR GR58063A patent/GR73141B/el unknown
- 1979-01-10 IT IT19176/79A patent/IT1110393B/it active
- 1979-01-11 HU HU79SCHE668A patent/HU180987B/hu unknown
- 1979-01-11 CA CA000319464A patent/CA1118426A/en not_active Expired
- 1979-01-11 FR FR7900595A patent/FR2414504A1/fr active Granted
- 1979-01-11 SU SU792707604A patent/SU969162A3/ru active
- 1979-01-11 AT AT21379A patent/AT362614B/de not_active IP Right Cessation
- 1979-01-12 BE BE0/192873A patent/BE873447A/xx not_active IP Right Cessation
- 1979-01-12 CH CH31579A patent/CH637647A5/de not_active IP Right Cessation
- 1979-01-12 IE IE50/79A patent/IE47724B1/en unknown
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| RU2430098C2 (ru) * | 2005-12-22 | 2011-09-27 | Грюненталь Гмбх | Замещенные производные оксадиазола и их применение в качестве лигандов опиоидных рецепторов |
| RU2495030C2 (ru) * | 2006-09-08 | 2013-10-10 | ПиТиСи ТЕРАПЬЮТИКС, ИНК. | Способы получения 1,2,4-оксадиазолбензойных кислот |
| RU2643807C1 (ru) * | 2010-11-12 | 2018-02-06 | Сионоги Энд Ко., Лтд. | Кристаллы производных 6,7-ненасыщенного-7-карбамоилморфинана и способ их получения |
| US9951082B2 (en) | 2010-11-12 | 2018-04-24 | Shionogi & Co., Ltd. | Crystal of 6,7-unsaturated-7-carbamoyl morphinan derivative and method for producing the same |
| RU2512293C1 (ru) * | 2012-12-13 | 2014-04-10 | Федеральное государственное бюджетное образовательное учреждение высшего профессионального образования "Ярославский государственный технический университет" | Способ получения этил 1,2,4-оксадиазол-5-карбоксилатов |
| RU2674448C1 (ru) * | 2017-07-12 | 2018-12-10 | Марина Владимировна Тарасенко | 3-(3-аминофенил)-5-(проп-1-ен-2-ил)-1,2,4-оксадиазол |
| RU2754735C1 (ru) * | 2020-12-14 | 2021-09-06 | Федеральное государственное бюджетное образовательное учреждение высшего образования "Ярославский государственный технический университет" ФГБОУВО "ЯГТУ" | Способ получения 3,5-дизамещенных 1,2,4-оксадиазолов, содержащих алкенильный фрагмент |
Also Published As
| Publication number | Publication date |
|---|---|
| AU527548B2 (en) | 1983-03-10 |
| CS204045B2 (en) | 1981-03-31 |
| CA1118426A (en) | 1982-02-16 |
| DD141405A5 (de) | 1980-04-30 |
| JPS54100376A (en) | 1979-08-08 |
| ATA21379A (de) | 1980-10-15 |
| NL7811925A (nl) | 1979-07-16 |
| RO76592A (ro) | 1981-04-30 |
| BG30169A3 (en) | 1981-04-15 |
| DE2801509A1 (de) | 1979-07-19 |
| IT7919176A0 (it) | 1979-01-10 |
| HU180987B (en) | 1983-05-30 |
| GB2012764A (en) | 1979-08-01 |
| GB2012764B (en) | 1982-06-23 |
| ES476468A1 (es) | 1979-04-16 |
| YU301778A (en) | 1983-01-21 |
| CH637647A5 (de) | 1983-08-15 |
| AT362614B (de) | 1981-06-10 |
| IE47724B1 (en) | 1984-05-30 |
| PL113006B1 (en) | 1980-11-29 |
| PL212703A1 (pl) | 1979-09-10 |
| FR2414504A1 (fr) | 1979-08-10 |
| LU80775A1 (de) | 1979-05-16 |
| IL56339A0 (en) | 1979-03-12 |
| IT1110393B (it) | 1985-12-23 |
| IE790050L (en) | 1979-07-12 |
| US4243409A (en) | 1981-01-06 |
| PT69058A (de) | 1979-02-01 |
| IL56339A (en) | 1982-05-31 |
| GR73141B (OSRAM) | 1984-02-08 |
| FR2414504B1 (OSRAM) | 1983-10-21 |
| DK542178A (da) | 1979-07-13 |
| BE873447A (fr) | 1979-07-12 |
| AU4326379A (en) | 1979-07-19 |
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