GB951651A - Substituted benzonitriles, their preparation and compositions containing them - Google Patents

Substituted benzonitriles, their preparation and compositions containing them

Info

Publication number
GB951651A
GB951651A GB561260A GB561260A GB951651A GB 951651 A GB951651 A GB 951651A GB 561260 A GB561260 A GB 561260A GB 561260 A GB561260 A GB 561260A GB 951651 A GB951651 A GB 951651A
Authority
GB
United Kingdom
Prior art keywords
chloro
benzonitrile
group
yield
tolyloxy
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
GB561260A
Inventor
John Yates
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.)
Shell Research Ltd
Original Assignee
Shell Research 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 Shell Research Ltd filed Critical Shell Research Ltd
Priority to GB561260A priority Critical patent/GB951651A/en
Publication of GB951651A publication Critical patent/GB951651A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C317/00Sulfones; Sulfoxides

Landscapes

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

Abstract

The invention relates to benzonitrile derivatives of the formula: <FORM:0951651/C2/1> in which X is a chlorine or bromine atom, Z is an oxygen or sulphur atom or a sulphinyl (SO) or sulphonyl (SO2) group and R is a hydrocarbon group which may be substituted by halogen or by a trifluoromethyl, nitro, amino, acylamino, hydroxy, hydrocarbyloxy, carboxy or hydrocarbyloxycarbonyl group or by a group -OCH2CH2OR1, in which R1 is a hydrogen atom or an alkyl group of 1-4 carbon atoms. The compounds are prepared by treating 2-chloro-or 2-bromo-6-nitrobenzonitrile with a compound of the formula MZ1R, in which M is an alkali metal or ammonium and Z1 is oxygen or sulphur, or with a mixture of a compound HZ1R and an alkali-metal hydroxide or hydride or ammonia or ammonium hydroxide; if Z in the formula above is to be a sulphinyl group, the resulting thio derivative is then oxidized or, if Z is to be a sulphonyl group, the thio or the sulphinyl derivative is oxidized. In typical examples, 2-chloro-6-nitrobenzonitrile is reacted (1) with phenol and sodium methoxide to yield 2-chloro-6-phenoxybenzonitrile, (2) with p-methoxyphenol and sodium hydride to yield 2-chloro -6- (4-methoxy phenoxy) benzonitrile, (3) with sodium 3-methoxycarbonylphenoxide to yield 2-chloro -6- (3-methoxycarbonylphenoxy) benzonitrile, (4) with 1-naphthol and sodium hydride to yield 2-chloro -6- (1-naphthyloxy) benzonitrile, (5) with methanol and potassium hydroxide to yield 2-chloro-6-methoxybenzonitrile, (6) with thiophenol and sodium hydride to yield 2-chloro -6- phenylthiobenzonitrile, (7) with allyl thiol and sodium hydride to yield 2-chloro-(6-allylthio)benzonitrile, and (8) ethyl thioglycollate sodium salt and sodium hydride to yield 2-chloro -6- (ethoxycarbonylmethylthio) benzonitrile. The reactions may be effected at 120-250 DEG C., preferably in a solvent, a number of which are specified. Examples are given also in which 2-chloro -6- phenylthiobenzonitrile is oxidized to the corresponding sulphinyl compound with hydrogen peroxide and acetic acid and to the corresponding sulphonyl compound with a larger proportion of hydrogen peroxide. Other examples describe the preparation of 2-chloro-6-(2, 4-dichlorophenoxy) benzonitrile, 2-chloro-6-(3-nitrophenoxy) benzonitrile, 2-chloro -6- (2-and 3-methoxy phenoxy) benzonitrile, 2-chloro-6-(3-trifluoromethylphenoxy) benzonitrile, 2-chloro -6- (3-carboxyphenoxy) benzonitrile, 2-chloro -6- (4-aminophenoxy) benzonitrile, 2-chloro -6- (4-acetylaminophenoxy) benzonitrile, 2-chloro -6- (2- and 4-chlorophenoxy) benzonitrile, 2-chloro -6- (3- and 4-tolyloxy) benzonitrile, 2-chloro -6- (2-naphthyloxy) benzonitrile, 2-chloro -6- allyloxybenzonitrile, 2-chloro -6-isopropoxy- and -6- isobutoxybenzonitrile, 2-chloro -6- (2-methoxyethoxy) benzonitrile, 2-chloro -6- (2-hydroxyethoxy) benzonitrile, 2-chloro -6- benzyloxybenzonitrile, 2-chloro -6-(4-tolylthio) benzonitrile, 2-chloro -6- (4-chlorophenylthio) benzonitrile, 2-chloro -6- (benzylthio) benzonitrile, 2-chloro -6- (4-chlorobenzylthio) benzonitrile, 2-chloro -6- ethylsulphonylbenzonitrile and 2-chloro -6- (4-chlorobenzylsulphonyl) benzonitrile. Other radicals R are also specified. Apart from 2-chloro -6- methoxybenzonitrile, the products are claimed as new compounds. The products are useful as herbicides, some being toxic to plant seeds and some to growing plants when applied as a foliar spray or as a soil drench. 2-chloro -6- allylthiobenzonitrile, 2-chloro -6- (3-nitrophenoxy) benzonitrile and 2-chloro -6- (3-tolyloxy) benzonitrile are useful also as fungicides. 2-Chloro -6- (3-tolyloxy) benzonitrile is useful also as an insecticide. 2-Chloro -6- (2, 4-dichlorophenyl) benzonitrile and 2-chloro -6- (3-tolyloxy) benzonitrile are useful also for combatting aquatic snails which are carriers for bilharziasis. For all these purposes the products may be prepared as solid compositions, wettable powders, dusts, emulsions, solutions or emulsifiable concentrates with the aid of solid or liquid carriers and (or) surface-active agents, a number of each of which are specified. Experimental results of the application of some of the products are given. Specification 861,898 is referred to.ALSO:Herbicidal and pesticidal compositions comprise benzonitrile derivatives of the formula <FORM:0951651/A5-A6/1> in which X is a chlorine or bromine atom, Z is an oxygen or sulphur atom or a sulphinyl (SO) or sulphonyl (SO2) group and R is a hydrocarbon group which may be substituted by halogen or by a trifluoromethyl, nitro, amino, acylamino, hydroxy, hydrocarbyloxy, carboxy or hydrocarbyloxycarbonyl group or by a group -OCH2CH2OR1, in which R1 is a hydrogen atom or an alkyl group of 1-4 carbon atoms (see Division C2). The products are applied as a foliar spray or as a soil drench. 2 - Chloro - 6 - allylthiobenzonitrile, 2 - chloro-6 - (3 - nitrophenoxy)benzonitrile and 2 - chloro - 6 - (3 - tolyloxy)benzonitrile are useful also as fungicides. 2-Chloro-6-(3-tolyloxy) benzonitrile is useful also as an insecticide. 2 - Chloro - 6 - (2,4 - dichlorophenyl)benzonitrile and 2 - chloro - 6 - (3 - tolyloxy)benzonitrile are useful also for combating aquatio snails which are carriers for bilharziasis. For all these purposes the products may be prepared as solid compositions, wettable powders, dusts, emulsions, solutions or emulsifiable concentrates with the aid of solid or liquid carriers and (or) surface-active agents, a number of each of which are specified. Experimental results of the application of some of the products are given.
GB561260A 1960-02-17 1960-02-17 Substituted benzonitriles, their preparation and compositions containing them Expired GB951651A (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
GB561260A GB951651A (en) 1960-02-17 1960-02-17 Substituted benzonitriles, their preparation and compositions containing them

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB561260A GB951651A (en) 1960-02-17 1960-02-17 Substituted benzonitriles, their preparation and compositions containing them

Publications (1)

Publication Number Publication Date
GB951651A true GB951651A (en) 1964-03-11

Family

ID=9799362

Family Applications (1)

Application Number Title Priority Date Filing Date
GB561260A Expired GB951651A (en) 1960-02-17 1960-02-17 Substituted benzonitriles, their preparation and compositions containing them

Country Status (1)

Country Link
GB (1) GB951651A (en)

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3950379A (en) * 1972-03-14 1976-04-13 Rohm And Haas Company 2-Cyano-diphenyl ethers
US4029493A (en) 1973-02-23 1977-06-14 Mobil Oil Corporation Substituted phenoxybenzonitriles as herbicides
EP0004257A1 (en) * 1978-03-09 1979-09-19 Sanofi S.A. Benzonitrile derivative, process for its preparation and its application
EP0033984B1 (en) * 1980-01-23 1984-06-06 Duphar International Research B.V New sulphonyl compounds, method of preparing the new compounds, as well as aphicidal compositions on the basis of the new compounds
USRE32215E (en) * 1971-02-11 1986-07-22 Rhone-Poulenc Agrochimie Substituted phenoxybenzoic acids compositions of the same and herbicidal use thereof
USRE32216E (en) * 1969-04-25 1986-07-29 Rhone-Poulenc Agrochimie Salts of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof
USRE32243E (en) * 1969-04-25 1986-09-09 Rhone-Poulenc Agrochimie Esters of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof
US4681622A (en) * 1973-09-19 1987-07-21 Rhone-Poulenc Agrochimie Substituted phenoxybenzoic acids and derivatives thereof as herbicides
AU2005202839B2 (en) * 2004-01-14 2009-02-05 Nargis Abdul Gani To investigate the potential of using beetle odours to deter slugs in vining peas
EP2323997A2 (en) * 2008-07-31 2011-05-25 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US9371317B2 (en) 2013-02-19 2016-06-21 Senomyx, Inc. Sweet flavor modifier
US9420814B2 (en) 2012-08-06 2016-08-23 Senomyx, Inc. Sweet flavor modifier
US9603848B2 (en) 2007-06-08 2017-03-28 Senomyx, Inc. Modulation of chemosensory receptors and ligands associated therewith
WO2020138228A1 (en) * 2018-12-25 2020-07-02 学校法人東京理科大学 Jasmonic acid endogeny promoting agent, and method for promoting jasmonic acid endogeny
US11945813B2 (en) 2018-08-07 2024-04-02 Firmenich Incorporated 5-substituted 4-amino-1H-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof

Cited By (30)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
USRE32216E (en) * 1969-04-25 1986-07-29 Rhone-Poulenc Agrochimie Salts of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof
USRE32243E (en) * 1969-04-25 1986-09-09 Rhone-Poulenc Agrochimie Esters of substituted phenoxybenzoic acids, compositions of the same and herbicidal use thereof
USRE32215E (en) * 1971-02-11 1986-07-22 Rhone-Poulenc Agrochimie Substituted phenoxybenzoic acids compositions of the same and herbicidal use thereof
US3950379A (en) * 1972-03-14 1976-04-13 Rohm And Haas Company 2-Cyano-diphenyl ethers
US4029493A (en) 1973-02-23 1977-06-14 Mobil Oil Corporation Substituted phenoxybenzonitriles as herbicides
US4681622A (en) * 1973-09-19 1987-07-21 Rhone-Poulenc Agrochimie Substituted phenoxybenzoic acids and derivatives thereof as herbicides
EP0004257A1 (en) * 1978-03-09 1979-09-19 Sanofi S.A. Benzonitrile derivative, process for its preparation and its application
FR2419282A1 (en) * 1978-03-09 1979-10-05 Labaz NEW DERIVATIVE OF BENZONITRILE, ITS PREPARATION PROCESS AND ITS APPLICATION
EP0033984B1 (en) * 1980-01-23 1984-06-06 Duphar International Research B.V New sulphonyl compounds, method of preparing the new compounds, as well as aphicidal compositions on the basis of the new compounds
AU2005202839B2 (en) * 2004-01-14 2009-02-05 Nargis Abdul Gani To investigate the potential of using beetle odours to deter slugs in vining peas
US9603848B2 (en) 2007-06-08 2017-03-28 Senomyx, Inc. Modulation of chemosensory receptors and ligands associated therewith
EP2323997A4 (en) * 2008-07-31 2013-05-01 Senomyx Inc Processes and intermediates for making sweet taste enhancers
US10087154B2 (en) 2008-07-31 2018-10-02 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US8586733B2 (en) 2008-07-31 2013-11-19 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
CN102171197A (en) * 2008-07-31 2011-08-31 西诺米克斯公司 Processes and intermediates for making sweet taste enhancers
US9382196B2 (en) 2008-07-31 2016-07-05 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US10570105B2 (en) 2008-07-31 2020-02-25 Firmenich Incorporated Processes and intermediates for making sweet taste enhancers
EP3085699A3 (en) * 2008-07-31 2016-11-23 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
EP2323997A2 (en) * 2008-07-31 2011-05-25 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US10308621B2 (en) 2008-07-31 2019-06-04 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US9732052B2 (en) 2008-07-31 2017-08-15 Senomyx, Inc. Processes and intermediates for making sweet taste enhancers
US9420814B2 (en) 2012-08-06 2016-08-23 Senomyx, Inc. Sweet flavor modifier
US9687015B2 (en) 2012-08-06 2017-06-27 Senomyx, Inc. Sweet flavor modifier
US9745293B2 (en) 2012-08-06 2017-08-29 Senomyx, Inc. Sweet flavor modifier
US9371317B2 (en) 2013-02-19 2016-06-21 Senomyx, Inc. Sweet flavor modifier
US9695162B2 (en) 2013-02-19 2017-07-04 Senomyx, Inc. Sweet flavor modifier
US9475803B2 (en) 2013-02-19 2016-10-25 Senomyx, Inc. Sweet flavor modifier
US11945813B2 (en) 2018-08-07 2024-04-02 Firmenich Incorporated 5-substituted 4-amino-1H-benzo[c][1,2,6]thiadiazine 2,2-dioxides and formulations and uses thereof
WO2020138228A1 (en) * 2018-12-25 2020-07-02 学校法人東京理科大学 Jasmonic acid endogeny promoting agent, and method for promoting jasmonic acid endogeny
JPWO2020138228A1 (en) * 2018-12-25 2021-11-11 学校法人東京理科大学 Jasmonic acid endogenous promoter and jasmonic acid endogenous promoter

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