CA1157877A - Phenoxy- et thiophenoxynitriles utilises comme herbicides - Google Patents
Phenoxy- et thiophenoxynitriles utilises comme herbicidesInfo
- Publication number
- CA1157877A CA1157877A CA000343782A CA343782A CA1157877A CA 1157877 A CA1157877 A CA 1157877A CA 000343782 A CA000343782 A CA 000343782A CA 343782 A CA343782 A CA 343782A CA 1157877 A CA1157877 A CA 1157877A
- Authority
- CA
- Canada
- Prior art keywords
- phenoxy
- compound
- group
- propanoate
- trifluoromethyl
- 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
- 239000004009 herbicide Substances 0.000 title abstract description 6
- 150000001875 compounds Chemical class 0.000 claims abstract description 114
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 8
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 3
- 125000005843 halogen group Chemical group 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000004434 sulfur atom Chemical group 0.000 claims abstract description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 32
- 241001233957 eudicotyledons Species 0.000 claims description 30
- 239000000460 chlorine Substances 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 17
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical compound CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 14
- 238000011282 treatment Methods 0.000 claims description 12
- -1 halo-alkyl radical Chemical group 0.000 claims description 9
- QLNJFJADRCOGBJ-UHFFFAOYSA-N propionamide Chemical compound CCC(N)=O QLNJFJADRCOGBJ-UHFFFAOYSA-N 0.000 claims description 8
- 229940080818 propionamide Drugs 0.000 claims description 8
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 8
- 235000013339 cereals Nutrition 0.000 claims description 7
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 239000011149 active material Substances 0.000 claims description 5
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- CIUQDSCDWFSTQR-UHFFFAOYSA-N [C]1=CC=CC=C1 Chemical compound [C]1=CC=CC=C1 CIUQDSCDWFSTQR-UHFFFAOYSA-N 0.000 claims description 2
- 125000001188 haloalkyl group Chemical group 0.000 claims description 2
- 150000003254 radicals Chemical class 0.000 claims description 2
- BYJAJQGCMSBKPB-UHFFFAOYSA-N 3-hydroxybutanenitrile Chemical compound CC(O)CC#N BYJAJQGCMSBKPB-UHFFFAOYSA-N 0.000 claims 3
- NHSSTOSZJANVEV-UHFFFAOYSA-N 2-hydroxybutanenitrile Chemical compound CCC(O)C#N NHSSTOSZJANVEV-UHFFFAOYSA-N 0.000 claims 1
- FXHRDEQPODSZQL-UHFFFAOYSA-N 3-hydroxypentanenitrile Chemical compound CCC(O)CC#N FXHRDEQPODSZQL-UHFFFAOYSA-N 0.000 claims 1
- LBIZNKINTCCMEK-UHFFFAOYSA-N 4-hydroxyhexanenitrile Chemical compound CCC(O)CCC#N LBIZNKINTCCMEK-UHFFFAOYSA-N 0.000 claims 1
- DNSISZSEWVHGLH-UHFFFAOYSA-N butanamide Chemical compound CCCC(N)=O DNSISZSEWVHGLH-UHFFFAOYSA-N 0.000 claims 1
- LTYRAPJYLUPLCI-UHFFFAOYSA-N glycolonitrile Chemical compound OCC#N LTYRAPJYLUPLCI-UHFFFAOYSA-N 0.000 claims 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims 1
- 125000001424 substituent group Chemical group 0.000 claims 1
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- 238000004821 distillation Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 229940117927 ethylene oxide Drugs 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 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
- 230000002363 herbicidal effect Effects 0.000 description 1
- 229940035429 isobutyl alcohol Drugs 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
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 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
- 239000012074 organic phase Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- 239000003981 vehicle Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7901020 | 1979-01-16 | ||
| FR7901020A FR2446812A1 (fr) | 1979-01-16 | 1979-01-16 | Phenoxy- et thiophenoxynitriles et leurs applications en tant qu'herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1157877A true CA1157877A (fr) | 1983-11-29 |
Family
ID=9220811
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA000343782A Expired CA1157877A (fr) | 1979-01-16 | 1980-01-16 | Phenoxy- et thiophenoxynitriles utilises comme herbicides |
Country Status (15)
| Country | Link |
|---|---|
| JP (1) | JPS55113754A (fr) |
| AR (1) | AR228248A1 (fr) |
| BE (1) | BE881166A (fr) |
| BR (1) | BR8000277A (fr) |
| CA (1) | CA1157877A (fr) |
| DE (1) | DE3001433A1 (fr) |
| ES (1) | ES488513A0 (fr) |
| FR (1) | FR2446812A1 (fr) |
| GB (1) | GB2041926B (fr) |
| IT (1) | IT1140513B (fr) |
| NL (1) | NL8000264A (fr) |
| OA (1) | OA06436A (fr) |
| PT (1) | PT70701A (fr) |
| SE (1) | SE8000367L (fr) |
| ZA (1) | ZA80263B (fr) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2473514A2 (fr) * | 1980-01-15 | 1981-07-17 | Produits Ind Cie Fse | Phenoxy- et thiophenoxynitriles et leurs applications en tant qu'herbicides |
| JPS5978154A (ja) * | 1982-10-27 | 1984-05-04 | Kanesho Kk | 選択性除草剤 |
| ES2043625T3 (es) * | 1986-08-29 | 1994-01-01 | Shell Int Research | Derivados de acido ariloxicarboxilico, su preparacion y empleo. |
| US5942640A (en) * | 1998-04-20 | 1999-08-24 | American Cyanamid Company | Process for the manufacture of N-(1-cyanoalkyl)-2-phenoxypropionamide derivatives |
| AU2560300A (en) * | 1999-02-20 | 2000-09-04 | Astrazeneca Ab | Acetamido acetonitrile derivatives as inhibitors of cathepsin l and/or cathepsins |
| AU2002224942A1 (en) * | 2000-12-20 | 2002-07-01 | Syngenta Participations Ag | N-acyl aminoacetonitriles having pesticidal properties |
| EP1640360A4 (fr) * | 2003-06-27 | 2007-06-20 | Sumitomo Chemical Co | Amides et procede de regulation de maladies vegetales au moyen de ceux-ci |
Family Cites Families (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1041982A (en) * | 1963-09-30 | 1966-09-07 | Boots Pure Drug Co Ltd | Herbicidal compounds and compositions |
| CA992988A (en) * | 1971-06-25 | 1976-07-13 | Don R. Baker | N-(1,1 SUBSTITUTED ACETONITRILO)-.alpha.-(3,5-SUBSTITUTED PHENOXY) ALKYL AMIDES AND THEIR USE AS HERBICIDES |
| FR2161683A5 (en) * | 1971-11-17 | 1973-07-06 | Abbott Lab | Aryloxy acetamido acetonitriles - plant growth regulants |
| DE2433067B2 (de) * | 1974-07-10 | 1977-11-24 | a- [4-(4" Trifluormethylphenoxy)-phenoxy] -propionsäuren und deren Derivate, Verfahren zu ihrer Herstellung und diese enthaltende herbizide Mittel Hoechst AG, 6000 Frankfurt | Alpha- eckige klammer auf 4-(4' trifluormethylphenoxy)-phenoxy eckige klammer zu -propionsaeuren und deren derivate, verfahren zu ihrer herstellung und diese enthaltende herbizide mittel |
| CS185694B2 (en) * | 1974-07-17 | 1978-10-31 | Ishihara Sangyo Kaisha | Herbicidal agent |
| US4052432A (en) * | 1974-11-18 | 1977-10-04 | Stauffer Chemical Company | N-(1,1 Substituted acetonitrilo)-α-(3,5-substituted phenoxy) alkyl amides |
| CA1071233A (fr) * | 1975-06-26 | 1980-02-05 | Don R. Baker | Les phenoxyalkylamides et leur utilisation comme acaricides |
| DE2628384C2 (de) * | 1976-06-24 | 1984-09-27 | Hoechst Ag, 6230 Frankfurt | 2-(4-Phenoxyphenoxy)- bzw. 2-(4-Benzylphenoxy)-propionsäurederivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Pflanzenbehandlungsmittel |
| US4119433A (en) * | 1977-07-05 | 1978-10-10 | Stauffer Chemical Company | 3-Halo-5-(lower alkoxy) phenoxy alkyl amides |
| AR220917A1 (es) * | 1977-10-26 | 1980-12-15 | Stauffer Chemical Co | Compuestos de n-sustituido-2-(4 sustituido-3,5-dimetilfenoxi)butiramida utiles como anublicidas y composicion que los contiene |
| EP0003517B1 (fr) * | 1978-02-03 | 1981-03-25 | Ciba-Geigy Ag | Ester cyanométhylique de l'acide 4-(paratrifluorométhylephénoxy)-alpha-phénoxypropionique; procédé de préparation; composition contenant ce composé herbicide, et son application |
| JPS54117027A (en) * | 1978-02-28 | 1979-09-11 | Nippon Soda Co Ltd | Phenoxypropionic acid and herbicide containing the same |
-
1979
- 1979-01-16 FR FR7901020A patent/FR2446812A1/fr not_active Withdrawn
-
1980
- 1980-01-16 AR AR279648A patent/AR228248A1/es active
- 1980-01-16 ES ES488513A patent/ES488513A0/es active Granted
- 1980-01-16 SE SE8000367A patent/SE8000367L/xx not_active Application Discontinuation
- 1980-01-16 IT IT19233/80A patent/IT1140513B/it active
- 1980-01-16 GB GB8001516A patent/GB2041926B/en not_active Expired
- 1980-01-16 JP JP265580A patent/JPS55113754A/ja active Pending
- 1980-01-16 DE DE19803001433 patent/DE3001433A1/de not_active Withdrawn
- 1980-01-16 PT PT70701A patent/PT70701A/fr unknown
- 1980-01-16 ZA ZA00800263A patent/ZA80263B/xx unknown
- 1980-01-16 BE BE2/58335A patent/BE881166A/fr not_active IP Right Cessation
- 1980-01-16 CA CA000343782A patent/CA1157877A/fr not_active Expired
- 1980-01-16 NL NL8000264A patent/NL8000264A/nl not_active Application Discontinuation
- 1980-01-16 BR BR8000277A patent/BR8000277A/pt unknown
- 1980-01-16 OA OA56996A patent/OA06436A/fr unknown
Also Published As
| Publication number | Publication date |
|---|---|
| JPS55113754A (en) | 1980-09-02 |
| GB2041926A (en) | 1980-09-17 |
| ES8103573A1 (es) | 1981-03-16 |
| IT1140513B (it) | 1986-10-01 |
| DE3001433A1 (de) | 1980-07-17 |
| IT8019233A0 (it) | 1980-01-16 |
| SE8000367L (sv) | 1980-07-17 |
| ES488513A0 (es) | 1981-03-16 |
| NL8000264A (nl) | 1980-07-18 |
| FR2446812A1 (fr) | 1980-08-14 |
| BR8000277A (pt) | 1980-10-21 |
| ZA80263B (en) | 1981-01-28 |
| GB2041926B (en) | 1983-07-20 |
| OA06436A (fr) | 1981-07-31 |
| PT70701A (fr) | 1980-02-01 |
| AR228248A1 (es) | 1983-02-15 |
| BE881166A (fr) | 1980-07-16 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |