GB951651A - Substituted benzonitriles, their preparation and compositions containing them - Google Patents
Substituted benzonitriles, their preparation and compositions containing themInfo
- 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
Links
Classifications
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; 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.
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)
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 |
-
1960
- 1960-02-17 GB GB561260A patent/GB951651A/en not_active Expired
Cited By (30)
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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