GB1067031A - 4-hydroxybenzonitrile derivatives - Google Patents

4-hydroxybenzonitrile derivatives

Info

Publication number
GB1067031A
GB1067031A GB36310/62A GB3631062A GB1067031A GB 1067031 A GB1067031 A GB 1067031A GB 36310/62 A GB36310/62 A GB 36310/62A GB 3631062 A GB3631062 A GB 3631062A GB 1067031 A GB1067031 A GB 1067031A
Authority
GB
United Kingdom
Prior art keywords
halogen
hydroxybenzonitrile
chloro
nitro
compositions
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
GB36310/62A
Inventor
Basil Jason Haywood
William George Leeds
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.)
May and Baker Ltd
Original Assignee
May and Baker 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 to NL298303D priority Critical patent/NL298303A/xx
Priority to BE637794D priority patent/BE637794A/xx
Application filed by May and Baker Ltd filed Critical May and Baker Ltd
Priority to GB36401/63A priority patent/GB1067032A/en
Priority to GB36310/62A priority patent/GB1067031A/en
Priority to SE10438/63A priority patent/SE333139B/en
Priority to IL19943A priority patent/IL19943A/en
Priority to CH1147463A priority patent/CH432120A/en
Priority to AT453069A priority patent/AT299165B/en
Priority to AT753863A priority patent/AT282252B/en
Priority to AT453169A priority patent/AT299166B/en
Priority to AT452869A priority patent/AT295509B/en
Priority to AT452969A priority patent/AT299164B/en
Priority to DK447363AA priority patent/DK125261B/en
Priority to BR153023/63A priority patent/BR6353023D0/en
Priority to BR153021/63A priority patent/BR6353021D0/en
Priority to DE1542943A priority patent/DE1542943C3/en
Priority to FR948507A priority patent/FR1375311A/en
Priority to ES291919A priority patent/ES291919A1/en
Priority to BR153022/63A priority patent/BR6353022D0/en
Priority to NL63298303A priority patent/NL141757B/en
Priority to OA51851A priority patent/OA01646A/en
Publication of GB1067031A publication Critical patent/GB1067031A/en
Priority to MY197094A priority patent/MY7000094A/en
Priority to DK61972AA priority patent/DK126645B/en
Priority to NL7214839.A priority patent/NL157298B/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention comprises compounds of formula <FORM:1067031/C2/1> in which R1, R2 are H or halogen, R3 is halogen, R4 is H (including alkali, alkaline earth, ammonia and amine-e.g. diethanolamine, triethanolamine-salts thereof), acyl or alkoxycarbonyl and R5 is H, halogen or NO2; provided that 1 or 2 of R1, R2, R5 is H, and when R3=R5, either R1 or R2 is halogen. Exemplified compounds prepared by largely standard procedures are 3-chloro-5-nitro-4-hydroxybenzonitrile and its acetate, trichloroacetate, 2,2-dichloropropionate, octanoate, benzoate and benzenesulphonate; 3,5-chlorobromo, -chloroiodo- and -bromoiodo-4-hydroxybenzonitriles and their acetates; 2,5-dichloro - 4 - hydroxybenzonitrile and its 3-nitro derivative; 2,3,5- and 2,3,6-tri-chloro-4 -hydroxybenzonitriles; and 3-bromo-or -iodo-5-nitro-4 -hydroxybenzonitrile.ALSO:Herbicdal compounds have the formula <FORM:1067031/A5-A6/1> in which R1, R2 are H or halogen, R3 is halogen, R4 is H (including alkali, alkaline earth, ammonia and amine salts thereof), acyl or alkoxycarbonyl and R5 is H, halogen or NO2; provided that 1 or 2 of R1, R2 R5 is H, and when R3=R5 either R1 or R2 is halogen. Compositions may take the form of aerosols, dusts, granules, wettable powders and aqueous, organic or aqueous-organic compositions including emulsifiable concentrates. In addition to the usual adjuvants, the compositions may contain other herbicidally active compounds, e.g. 4-(2\sv,4\sv-dichloro- or 4\sv-chloro-2\sv-methylphenoxy)butyric acid and the analogous phenoxyacetic and phenoxypropionic acids; 2,2-dichloropropionic acid, trichloroacetic acid, 3-amino-1, 2, 4-triazole and 4-chlorobut-2-ynyl N-(3\sv-chlorophenyl) carbamate.
GB36310/62A 1962-09-24 1962-09-24 4-hydroxybenzonitrile derivatives Expired GB1067031A (en)

Priority Applications (24)

Application Number Priority Date Filing Date Title
NL298303D NL298303A (en) 1962-09-24
BE637794D BE637794A (en) 1962-09-24
GB36401/63A GB1067032A (en) 1962-09-24 1962-09-24 4-hydroxybenzonitrile derivatives
GB36310/62A GB1067031A (en) 1962-09-24 1962-09-24 4-hydroxybenzonitrile derivatives
SE10438/63A SE333139B (en) 1962-09-24 1963-04-24 BENSONITRIL DERIVATIVES, USED AS HERBICIDES
IL19943A IL19943A (en) 1962-09-24 1963-09-17 Benzonitrile derivatives
CH1147463A CH432120A (en) 1962-09-24 1963-09-17 Herbicidal composition based on benzonitrile derivatives
AT452969A AT299164B (en) 1962-09-24 1963-09-19 Process for the preparation of benzonitrile derivatives
AT753863A AT282252B (en) 1962-09-24 1963-09-19 Herbicidal agent
AT453169A AT299166B (en) 1962-09-24 1963-09-19 Process for the preparation of benzonitrile derivatives
AT452869A AT295509B (en) 1962-09-24 1963-09-19 Process for the preparation of benzonitrile derivatives
AT453069A AT299165B (en) 1962-09-24 1963-09-19 Process for the preparation of benzonitrile derivatives
DK447363AA DK125261B (en) 1962-09-24 1963-09-23 Herbicide.
FR948507A FR1375311A (en) 1962-09-24 1963-09-24 New herbicidal compositions based on benzonitrile derivatives
BR153021/63A BR6353021D0 (en) 1962-09-24 1963-09-24 HERBICIDE COMPOSITES CONTAINING BENZONITRILLA DERIVATIVES AS AN ACTIVE INGREDIENT
DE1542943A DE1542943C3 (en) 1962-09-24 1963-09-24 Benzonitrile derivatives and herbicidal compositions containing them
BR153023/63A BR6353023D0 (en) 1962-09-24 1963-09-24 HERBICIDAL COMPOSITIONS CONTAINING BENZONITRILLA DERIVATIVES AND PROCESS TO PRODUCE DERIVATIVE SAVINGS
ES291919A ES291919A1 (en) 1962-09-24 1963-09-24 Procedure for the preparation of a herbicide composition (Machine-translation by Google Translate, not legally binding)
BR153022/63A BR6353022D0 (en) 1962-09-24 1963-09-24 HERBICIDIC COMPOSITIONS BASED ON BENZONITRIL DERIVATIVES
NL63298303A NL141757B (en) 1962-09-24 1963-09-24 PROCEDURE FOR THE PREPARATION OF HERBICIDE PREPARATIONS AND PROCEDURE FOR THE PREPARATION OF COMPOUNDS WORKING AS HERBICIDE.
OA51851A OA01646A (en) 1962-09-24 1964-12-31 New herbicidal compositions based on benzonitrile derivatives.
MY197094A MY7000094A (en) 1962-09-24 1970-12-31 4-hydroxybenzonitrile derivatives
DK61972AA DK126645B (en) 1962-09-24 1972-02-10 Herbicidal active benzonitrile derivatives.
NL7214839.A NL157298B (en) 1962-09-24 1972-11-02 PROCESS FOR PREPARING HERBICIDE PREPARATIONS ON THE BASIS OF BENZONITRILES SUBSTITUATED BY A HALOGENATOM AND A HYDROXYL OR ACYLOXY GROUP, AND PROCESS FOR PREPARING THESE BENZONITRILE DERIVATIVES.

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
GB36310/62A GB1067031A (en) 1962-09-24 1962-09-24 4-hydroxybenzonitrile derivatives
GB109263 1963-01-09
GB1242263 1963-03-28

Publications (1)

Publication Number Publication Date
GB1067031A true GB1067031A (en) 1967-04-26

Family

ID=27253824

Family Applications (2)

Application Number Title Priority Date Filing Date
GB36310/62A Expired GB1067031A (en) 1962-09-24 1962-09-24 4-hydroxybenzonitrile derivatives
GB36401/63A Expired GB1067032A (en) 1962-09-24 1962-09-24 4-hydroxybenzonitrile derivatives

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB36401/63A Expired GB1067032A (en) 1962-09-24 1962-09-24 4-hydroxybenzonitrile derivatives

Country Status (13)

Country Link
AT (5) AT295509B (en)
BE (1) BE637794A (en)
BR (3) BR6353023D0 (en)
CH (1) CH432120A (en)
DE (1) DE1542943C3 (en)
DK (2) DK125261B (en)
ES (1) ES291919A1 (en)
GB (2) GB1067031A (en)
IL (1) IL19943A (en)
MY (1) MY7000094A (en)
NL (2) NL141757B (en)
OA (1) OA01646A (en)
SE (1) SE333139B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4637830A (en) * 1981-04-24 1987-01-20 Ciba-Geigy Corporation Herbicidal concentrates

Families Citing this family (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3628943A (en) * 1969-03-26 1971-12-21 Bengt Hjalmar Gullfeldt Herbicidal composition and method of combating undesirable plant growth
HU179000B (en) * 1977-07-13 1982-07-28 Chinoin Gyogyszer Es Vegyeszet Process for preparing new malonic acid esters
US4332613A (en) * 1979-12-26 1982-06-01 Union Carbide Corporation Solutions of bromoxynil and ioxynil
US4349488A (en) * 1981-11-03 1982-09-14 Great Lakes Chemical Corporation Process for producing esters of 3,5-dibromo-4-hydroxybenzonitrile
DE3360680D1 (en) * 1982-04-28 1985-10-10 Chinoin Gyogyszer Es Vegyeszet New benzonitrile derivatives, method for their preparation and herbicidal compositions
CA1207792A (en) * 1982-10-05 1986-07-15 Leslie V. Hunt Herbicidal use of trimethylamine and triethylamine salts of 3,5-dibromo-4-hydroxybenzonitrile
GB2128090B (en) * 1982-10-05 1986-06-25 May & Baker Ltd New herbicidal method
FR2591069B1 (en) * 1985-12-09 1988-03-18 Produits Ind Cie Fse HERBICIDE PRODUCTS BASED ON BROMOXYNIL ESTERS AND / OR IXXYNIL
IL92189A0 (en) * 1988-11-10 1990-07-26 Ciba Geigy Ag Solid herbicidal preparations
GB8909380D0 (en) * 1989-04-25 1989-06-14 Marks A H & Co Ltd Water soluble pesticide solution
CN114573478A (en) * 2022-03-11 2022-06-03 南京先进生物材料与过程装备研究院有限公司 Method for preparing bromoxynil octanoate

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4637830A (en) * 1981-04-24 1987-01-20 Ciba-Geigy Corporation Herbicidal concentrates

Also Published As

Publication number Publication date
BE637794A (en)
CH432120A (en) 1967-03-15
AT299164B (en) 1972-06-12
AT299165B (en) 1972-06-12
DK126645B (en) 1973-08-06
DE1542943A1 (en) 1972-04-06
NL298303A (en)
AT295509B (en) 1972-01-10
BR6353023D0 (en) 1973-06-05
OA01646A (en) 1969-09-20
DE1542943C3 (en) 1976-01-08
ES291919A1 (en) 1963-11-16
SE333139B (en) 1971-03-08
AT282252B (en) 1970-06-25
AT299166B (en) 1972-06-12
IL19943A (en) 1968-09-26
NL141757B (en) 1974-04-16
MY7000094A (en) 1970-12-31
BR6353022D0 (en) 1973-06-05
DE1542943B2 (en) 1975-04-30
BR6353021D0 (en) 1973-06-05
DK125261B (en) 1973-01-29
GB1067032A (en) 1967-04-26

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