GB1390295A - Substituted trifluoromethyl diphenyl ethers and herbicidal uses thereof - Google Patents

Substituted trifluoromethyl diphenyl ethers and herbicidal uses thereof

Info

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
Application number
GB418073A
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Ishihara Sangyo Kaisha Ltd
Original Assignee
Ishihara Sangyo Kaisha Ltd
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Priority claimed from JP1036772A external-priority patent/JPS5033129B2/ja
Priority claimed from JP4732272A external-priority patent/JPS497427A/ja
Priority claimed from JP7694472A external-priority patent/JPS5033130B2/ja
Priority claimed from JP12166572A external-priority patent/JPS5530483B2/ja
Priority claimed from JP12336972A external-priority patent/JPS4981532A/ja
Application filed by Ishihara Sangyo Kaisha Ltd filed Critical Ishihara Sangyo Kaisha Ltd
Publication of GB1390295A publication Critical patent/GB1390295A/en
Expired legal-status Critical Current

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.
GB418073A 1972-01-27 1973-01-26 Substituted trifluoromethyl diphenyl ethers and herbicidal uses thereof Expired GB1390295A (en)

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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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

Cited By (3)

* Cited by examiner, † Cited by third party
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