GB1390295A - Substituted trifluoromethyl diphenyl ethers and herbicidal uses thereof - Google Patents
Substituted trifluoromethyl diphenyl ethers and herbicidal uses thereofInfo
- Publication number
- GB1390295A GB1390295A GB418073A GB418073A GB1390295A GB 1390295 A GB1390295 A GB 1390295A GB 418073 A GB418073 A GB 418073A GB 418073 A GB418073 A GB 418073A GB 1390295 A GB1390295 A GB 1390295A
- Authority
- GB
- United Kingdom
- Prior art keywords
- formula
- alkoxy
- alkylamino
- defined above
- halogen atom
- 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
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/27—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups
- C07C205/35—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C205/36—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system
- C07C205/38—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by etherified hydroxy groups having nitro groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton to carbon atoms of the same non-condensed six-membered aromatic ring or to carbon atoms of six-membered aromatic rings being part of the same condensed ring system the oxygen atom of at least one of the etherified hydroxy groups being further bound to a carbon atom of a six-membered aromatic ring, e.g. nitrodiphenyl ethers
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
1390295 Substituted trifluoromethyl diphenyl ethers and herbicidal uses thereof ISHIHARA SANGYO KAISHA Ltd 26 Jan 1973 [27 Jan 1972 13 May 1972 2 Aug 1972 6 Dec 1972 11 Dec 1972] 4180/73 Heading C2C The invention comprises compounds of formula wherein X represents a halogen atom, n represents an integer of 0-3; Y represents a hydrogen or a halogen atom or a C 1-4 alkyl, C 1-8 alkoxy, C 1-4 alkoxy C 1-4 alkoxy, C 2-4 alkenyloxy, C 2-4 alkynyloxy, C 1-4 alkyl mercapto, amino, C 1-4 alkylamino, di-C 1-4 alkylamino, acetylamino, allylamino, hydroxy or (2-dimethylamino)ethoxy group; and Z represents a nitro group, a halogen group or a cyano group. These compounds may be prepared by (a) reacting 1,2-dihalo-4-trifluoromethyl benzene of formula with a phenol of formula wherein X, n, and Y are as defined above and Z<SP>1</SP> represents a halogen atom or a cyano group; (b) reacting a 2-halo-4-trifluoromethyl diphenyl ether of formula wherein X, n and Y are each as defined above; with a nitrating agent or a halogenating agent to substitute the 41-position with a nitro group or a halogen atom; (c) reducing, diazotizing, and cyaniding the 4<SP>1</SP>-position of a 2-halo-4- trifluoromethyl-4<SP>1</SP>-nitro diphenyl ether of formula wherein X, n, and Y are as defined above, and; (d) reacting a compound of formula with a compound of-formula Y<SP>1</SP>H, wherein X and n are as defined above; and Y<SP>1</SP> represents a C 1-8 alkoxy, C 1-4 alkoxy C 1-4 alkoxy. C 2-4 alkenyloxy, C 2-4 alkynyloxy, C 1-4 alkylmercapto, C 1-4 alkylamino, di-C 1-4 alkylamino, an allylamino or a (2-dimethylamino)- ethoxy group; to substitute the 3<SP>1</SP> position with the radical Y<SP>1</SP>. The invention also comprises a herbicidal composition which contains as an active ingredient a compound according to the invention together with a suitable carrier.
Applications Claiming Priority (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP1036772A JPS5033129B2 (en) | 1972-01-27 | 1972-01-27 | |
JP4732272A JPS497427A (en) | 1972-05-13 | 1972-05-13 | |
JP7694472A JPS5033130B2 (en) | 1972-08-02 | 1972-08-02 | |
JP12166572A JPS5530483B2 (en) | 1972-12-06 | 1972-12-06 | |
JP12336972A JPS4981532A (en) | 1972-12-11 | 1972-12-11 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1390295A true GB1390295A (en) | 1975-04-09 |
Family
ID=27519172
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB418073A Expired GB1390295A (en) | 1972-01-27 | 1973-01-26 | Substituted trifluoromethyl diphenyl ethers and herbicidal uses thereof |
Country Status (8)
Country | Link |
---|---|
BE (1) | BE794517A (en) |
DE (1) | DE2304006C3 (en) |
FR (1) | FR2169251B1 (en) |
GB (1) | GB1390295A (en) |
IT (1) | IT978521B (en) |
MY (1) | MY7800207A (en) |
NL (1) | NL173163C (en) |
PH (1) | PH18332A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0001427A1 (en) * | 1977-10-06 | 1979-04-18 | Bayer Ag | 2,6-Dichloro-3'-fluoro-4-trifluoromethyl-6'-nitrodiphenyl ether, a process for its preparation and its application as a defoliation agent for cotton |
US4649212A (en) * | 1981-07-08 | 1987-03-10 | Ciba-Geigy Corporation | Novel phenoxyphenylamino acid derivatives, the production thereof, compositions containing them and use thereof |
US4650905A (en) * | 1983-01-11 | 1987-03-17 | Basf Aktiengesellschaft | Diphenyl ethers and their use for controlling undesirable plant growth |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4105435A (en) * | 1975-10-29 | 1978-08-08 | Ishihara Sangyo Kaisha Ltd. | Herbicidal compound, herbicidal composition containing the same, and method of use thereof |
US4173464A (en) * | 1976-05-07 | 1979-11-06 | Sumitomo Chemical Company, Limited | m-Phenoxybenzamide derivatives |
FR2355817A1 (en) * | 1976-06-21 | 1978-01-20 | Nippon Kayaku Kk | Propylthio- and propylsulphinyl-phenyl phenyl ethers - acaricides with good residual effect |
US4515988A (en) * | 1978-09-01 | 1985-05-07 | Rohm And Haas Company | Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers |
US4778914A (en) * | 1979-07-18 | 1988-10-18 | Imperial Chemical Industries Plc | Chemical intermediates |
DE2932093A1 (en) * | 1979-08-08 | 1981-02-26 | Bayer Ag | PROCESS FOR THE PRODUCTION OF 4-FLUORO-3-PHENOXY-TOLUENE |
DE3004695A1 (en) * | 1980-02-08 | 1981-08-13 | Bayer Ag, 5090 Leverkusen | METHOD FOR PRODUCING TRIFLUORMETHYLPHENYL-OXYPHENYL ETHERS |
DE3044810A1 (en) * | 1980-11-28 | 1982-07-01 | Bayer Ag, 5090 Leverkusen | SUBSTITUTED PHENOXYCIMATE ACID DERIVATIVES, METHOD FOR THE PRODUCTION THEREOF AND THE USE THEREOF AS HERBICIDES, AND INTERMEDIATE PRODUCTS AND THEIR PRODUCTION |
DE3114072A1 (en) * | 1981-04-08 | 1982-11-04 | Basf Ag, 6700 Ludwigshafen | HERBICIDES DIPHENYL ETHER, THE PRODUCTION AND USE THEREOF AS HERBICIDES |
HU193467B (en) | 1984-11-12 | 1987-10-28 | Budapesti Vegyimuevek | Fungicidal composition comprising substituted benzoic acid derivative as active substance and process for preparing the active substance |
CN1008820B (en) * | 1985-05-10 | 1990-07-18 | 施林工业产权保护股份公司 | Process for the production of 17 alpha-ethynyl-17beta-hydroxy-18-methyl-4, 15-estradien-3-one |
Family Cites Families (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE602554A (en) * | 1960-04-13 | |||
NL288695A (en) * | 1962-02-08 | |||
US3702862A (en) * | 1968-03-13 | 1972-11-14 | Sumitomo Chemical Co | Alkyl- and halo-substituted phenoxy benzonitriles |
CH493197A (en) * | 1968-03-15 | 1970-07-15 | Ciba Geigy | Pesticides |
CH493989A (en) * | 1968-05-08 | 1970-07-31 | Ciba Geigy | Herbicidal agent |
FR1602719A (en) * | 1968-11-22 | 1971-01-18 | Herbicidal diphenylether/pheny urea compos - ition | |
CA964667A (en) * | 1971-01-07 | 1975-03-18 | William L. Schall | Production of diphenyl ethers |
US3928416A (en) * | 1972-03-14 | 1975-12-23 | Rohm & Haas | Herbicidal 4-trifluoromethyl-4{40 nitrodiphenyl ethers |
-
1973
- 1973-01-25 PH PH14284A patent/PH18332A/en unknown
- 1973-01-25 BE BE794517D patent/BE794517A/en not_active IP Right Cessation
- 1973-01-25 FR FR7302634A patent/FR2169251B1/fr not_active Expired
- 1973-01-26 NL NL7301194A patent/NL173163C/en not_active IP Right Cessation
- 1973-01-26 IT IT1967173A patent/IT978521B/en active
- 1973-01-26 GB GB418073A patent/GB1390295A/en not_active Expired
- 1973-01-27 DE DE19732304006 patent/DE2304006C3/en not_active Expired
-
1978
- 1978-12-30 MY MY7800207A patent/MY7800207A/en unknown
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0001427A1 (en) * | 1977-10-06 | 1979-04-18 | Bayer Ag | 2,6-Dichloro-3'-fluoro-4-trifluoromethyl-6'-nitrodiphenyl ether, a process for its preparation and its application as a defoliation agent for cotton |
US4649212A (en) * | 1981-07-08 | 1987-03-10 | Ciba-Geigy Corporation | Novel phenoxyphenylamino acid derivatives, the production thereof, compositions containing them and use thereof |
US4650905A (en) * | 1983-01-11 | 1987-03-17 | Basf Aktiengesellschaft | Diphenyl ethers and their use for controlling undesirable plant growth |
Also Published As
Publication number | Publication date |
---|---|
FR2169251B1 (en) | 1976-05-14 |
DE2304006C3 (en) | 1981-10-22 |
FR2169251A1 (en) | 1973-09-07 |
PH18332A (en) | 1985-05-31 |
DE2304006A1 (en) | 1973-08-09 |
BE794517A (en) | 1973-07-25 |
NL173163C (en) | 1983-12-16 |
NL173163B (en) | 1983-07-18 |
MY7800207A (en) | 1978-12-31 |
DE2304006B2 (en) | 1975-10-23 |
IT978521B (en) | 1974-09-20 |
NL7301194A (en) | 1973-07-31 |
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Legal Events
Date | Code | Title | Description |
---|---|---|---|
414F | Notice of opposition given (sect. 14/1949) | ||
414A | Case decided by the comptroller ** specification amended (sect. 14/1949) | ||
SPA | Amended specification published | ||
PS | Patent sealed | ||
PE20 | Patent expired after termination of 20 years |
Effective date: 19930124 |