GB1056235A - Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing them - Google Patents

Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing them

Info

Publication number
GB1056235A
GB1056235A GB2178364A GB2178364A GB1056235A GB 1056235 A GB1056235 A GB 1056235A GB 2178364 A GB2178364 A GB 2178364A GB 2178364 A GB2178364 A GB 2178364A GB 1056235 A GB1056235 A GB 1056235A
Authority
GB
United Kingdom
Prior art keywords
acid
quaternary ammonium
different
formula
same
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
GB2178364A
Inventor
Basil Jason Heywood
William George Leeds
Raymond Frederick Collins
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
Application filed by May and Baker Ltd filed Critical May and Baker Ltd
Priority to GB2178364A priority Critical patent/GB1056235A/en
Priority to NL6506449A priority patent/NL6506449A/xx
Priority to BE664317A priority patent/BE664317A/xx
Priority to CH732065A priority patent/CH434869A/en
Priority to FR18351A priority patent/FR1434786A/en
Priority to DE1965M0062830 priority patent/DE1542963A1/en
Publication of GB1056235A publication Critical patent/GB1056235A/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)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises quaternary ammonium derivatives of benzonitriles of the general formula <FORM:1056235/C2/1> in which X1 and X2 are the same or different and each represents a bromine or iodine atom, and R1, R2, R3 and R4 are the same or different and each represents a methyl or ethyl group. Compounds claimed per se are the tetramethyl-ammonium salts of 3,5-dibromo and 3,5-diiodo - 4 - hydroxybenzonitrile. The compounds may be prepared by reacting a soluble salt of a hydroxybenzonitrile of the general formula <FORM:1056235/C2/2> with a quaternary ammonium salt of formula <FORM:1056235/C2/3> wherein Y represents a suitable anion such as a chloride or bromide ion or by reacting a hydroxy benzonitrile of Formula 2 with a quaternary ammonium hydroxide of the formula <FORM:1056235/C2/4>ALSO:A herbicidal composition comprises as active ingredient at least one quaternary ammonium derivative of benzonitrile of the general formula: <FORM:1056235/A5-A6/1> in which X1 and X2 are the same or different and each represents a bromine or iodine atom and R1R2R3R4 are the same or different and each represents a methyl or ethyl group in association with at least one compatible diluent and/or suitable surface active agent. Many diluents and surface active agents are specified. There may also be included a quaternary ammonium salt of known phenoxy alkanoic acid herbicides, e.g. a -(4-chloro-2-methylphenoxy)propionic acid; a ,a -dichloropropionic butyric acid; 4-chloro-2-methylphenoxy-acetic acid; 2,4-dichlorophenoxyacetic acid; a -(4-chloro-2-methylphenoxy)-propionic acid; a -(2, 4-dichlorophenoxy)propionic acid; 2,4,5-trichlorophenoxyacetic acid; a -(2,4,5-trichlorophenoxy)propionic acid; a ,a -dichloropropionic acid or trichloroacetic acid. Specified active ingredients are the tetramethyl ammonium salts of 3,5-dibromo and 3,5-diiodo-4, hydroxy benzonitriles.
GB2178364A 1964-05-26 1964-05-26 Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing them Expired GB1056235A (en)

Priority Applications (6)

Application Number Priority Date Filing Date Title
GB2178364A GB1056235A (en) 1964-05-26 1964-05-26 Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing them
NL6506449A NL6506449A (en) 1964-05-26 1965-05-20
BE664317A BE664317A (en) 1964-05-26 1965-05-21
CH732065A CH434869A (en) 1964-05-26 1965-05-25 Use of quaternary ammonium salts as herbicides
FR18351A FR1434786A (en) 1964-05-26 1965-05-25 New herbicide products
DE1965M0062830 DE1542963A1 (en) 1964-05-26 1965-05-26 New herbicide

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB2178364A GB1056235A (en) 1964-05-26 1964-05-26 Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing them

Publications (1)

Publication Number Publication Date
GB1056235A true GB1056235A (en) 1967-01-25

Family

ID=10168732

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2178364A Expired GB1056235A (en) 1964-05-26 1964-05-26 Quaternary ammonium derivatives of benzonitriles and herbicidal compositions containing them

Country Status (6)

Country Link
BE (1) BE664317A (en)
CH (1) CH434869A (en)
DE (1) DE1542963A1 (en)
FR (1) FR1434786A (en)
GB (1) GB1056235A (en)
NL (1) NL6506449A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010519302A (en) * 2007-02-26 2010-06-03 ダウ アグロサイエンシィズ エルエルシー Compounds derived from herbicidal carboxylic acids and tetraalkylammonium hydroxide or (arylalkyl) trialkylammonium hydroxide
AU2019253885B2 (en) * 2007-02-26 2021-03-25 Corteva Agriscience Llc Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010519302A (en) * 2007-02-26 2010-06-03 ダウ アグロサイエンシィズ エルエルシー Compounds derived from herbicidal carboxylic acids and tetraalkylammonium hydroxide or (arylalkyl) trialkylammonium hydroxide
JP2015044813A (en) * 2007-02-26 2015-03-12 ダウ アグロサイエンシィズ エルエルシー Compounds derived from herbicidal carboxylic acids and tetraalkylammonium hydroxide or (arylalkyl) trialkylammonium hydroxide
US9167810B2 (en) 2007-02-26 2015-10-27 Dow Agrosciences Llc Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides
JP2017002066A (en) * 2007-02-26 2017-01-05 ダウ アグロサイエンシィズ エルエルシー Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides
JP2017125012A (en) * 2007-02-26 2017-07-20 ダウ アグロサイエンシィズ エルエルシー Compounds derived from herbicidal carboxylic acids and tetraalkylammonium hydroxides or (arylalkyl)trialkylammonium hydroxides
US9839217B2 (en) 2007-02-26 2017-12-12 Dow Agrosciences Llc Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl)trialkylammonium hydroxides
AU2019253885B2 (en) * 2007-02-26 2021-03-25 Corteva Agriscience Llc Compounds derived from herbicidal carboxylic acids and tetraalkylammonium or (arylalkyl) trialkylammonium hydroxides

Also Published As

Publication number Publication date
DE1542963A1 (en) 1970-05-14
FR1434786A (en) 1966-04-08
CH434869A (en) 1967-04-30
NL6506449A (en) 1965-11-29
BE664317A (en) 1965-11-22

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