GB951770A - Improvements in or relating to combating pests - Google Patents

Improvements in or relating to combating pests

Info

Publication number
GB951770A
GB951770A GB14775/60A GB1477560A GB951770A GB 951770 A GB951770 A GB 951770A GB 14775/60 A GB14775/60 A GB 14775/60A GB 1477560 A GB1477560 A GB 1477560A GB 951770 A GB951770 A GB 951770A
Authority
GB
United Kingdom
Prior art keywords
dinitro
parts
nitro
preparation
trichlorobenzonitrile
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
GB14775/60A
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.)
Koninklijke Philips NV
Original Assignee
Philips Gloeilampenfabrieken NV
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 Philips Gloeilampenfabrieken NV filed Critical Philips Gloeilampenfabrieken NV
Publication of GB951770A publication Critical patent/GB951770A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00Carboxylic acid nitriles
    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00Preparation of carboxylic acid nitriles
    • C07C253/14Preparation of carboxylic acid nitriles by reaction of cyanides with halogen-containing compounds with replacement of halogen atoms by cyano groups

Abstract

Nitro-chloro-benzonitriles of the general formula: <FORM:0951770/C2/1> where p=1 or 2, and p+q=5, may be produced by a series of reactions starting from the appropriate polychloro-benzonitrile or the appropriate nitro-polychlorobenzoic acid. In Example 10, potassium nitrate is added to a solution of 2,4,6-trichlorobenzonitrile in concentrated sulphuric acid. The mixture is heated for one hour, and then poured on ice and water whereby 3,5-dinitro-2,4,6-trichlorobenzoic acid is obtained. This acid is converted, via the acid-chloride, into the corresponding benzamide, which is then heated with phosphorus ocychloride to give 3,5-dinitro-2,4,6-trichlorobenzonitrile. Example 11 describes the preparation of 2,6-dinitro-3,4,5-trichlorobenzonitrile by heating the corresponding benzamide with a mixture of phosphorus oxychloride and sodium dithionite. The Specification also relates to nitro-chloro-benzonitriles outside the scope of the above formula. In Example 3, diazotised 2,4-dinitro-6-chloroaniline is treated with potassium nickel cyanide to give 2,4-dinitro-6-chlorobenzonitrile. Example 4 describes the preparation of 2-nitro-5,6-dichloro-benzonitrile by the action of cuprous cyanide on 2,3,4-trichloronitrobenzene. Examples 1, 2, 8 and 9 relate to the preparation of three isomeric mononitro-trichlorobenzonitriles. Examples 5 and 7 relate to the preparation of 3,5-dinitro-2,6-dichlorobenzonitrile and 3,5-dinitro-4-chlorobenzonitrile, respectively. Example 6 describes the preparation of 2,5-dinitrobenzonitrile by dehydration of 2,5-dinitrobenzamide. All these compounds have use in the preparation of compositions for combating fungi and bacteria.ALSO:The invention comprises compositions for combating pests, such as fungi and bacteria, containing as an active substance a compound of the general formula <FORM:0951770/A5-A6/1> in admixture with an inert solid or liquid carrier, in which formula X represents a nitro group and Z an alkyl group containing from 1 to 5 carbon atoms, and p=1 or 2, q=1, 2, 3 or 4 when p=1, or q=0, 1, 2, 3 or 4 when p=2, and r=0, 1, 2 or 3. Specified solid carriers are: chalk, dolomite, attapulgite, china clay and pipe clay. Specific liquid carriers are: toluene, xylene, petroleum ether, acetone, methyl ethyl ketone and cyclohexanone. The compositions may incorporate insecticides, acaricides, fertilizers, surface-active agents, dispersion agents, and adhesives. A suitable dust composition may be prepared by grinding 3,5-dinitro-4-chlorobenzonitrile (5 parts), kieselguhr (10 parts) and dolomite 85 parts), together to a mean particle size of about 10 microns. A wettable powder may be produced by mixing 3,5-dinitro-2,4,6-trichlorobenzonitrile (20 parts), p dolomite (73 parts), oleylamido-methyl-taurate (2 parts), and sodium lignin sulphonate (5 parts), and grinding the mixture to a mean particle size of about 10 microns. A miscible oil may be produced by dissolving 2-nitro-4,5-dichlorobenzonitrile (10 parts) in a mixture of toluene (12 parts), methyl ethyl ketone (72 parts), and polyoxyethylenesorbitane fatty acid ester (6 parts). A dinitrobenzonitrile can also be used as active substance.ALSO:Pests such as fungi and bacteria are combated by treating seeds with a composition comprising as an active substance a compound of the general formula <FORM:0951770/A1-A3/1> in admixture with an inert solid or liquid carrier, in which formula X represents a nitro group and Z an alkyl group containing from 1 to 5 carbon atoms, and p = 1 or 2, q = 1, 2, 3 or 4 when p = 1, or q = 0, 1, 2, 3 or 4 when p = 2, and r = 0, 1, 2 or 3. From tests with the seed of garden cress and a few monocotyledonous plants it has been found that the active substances do not retard germination. A suitable dust composition may be prepared by grinding 3,5-dinitro-4-chlorobenzonitrile, kieselguhr, and dolomite together. A wettable powder may be produced by grinding 3,5-dinitro-2,4,6-trichlorobenzonitrile, dolomite, oleylamido-methyl-taurate, and sodium lignin sulphonate together. A miscible oil may be produced by dissolving 2-nitro-4,5-dichlorobenzonitrile in a mixture of toluene, methyl ethyl ketone, and polyoxyethylenesorbitane fatty acid ester. A dinitro-benzonitrile can also be used as an active substance.
GB14775/60A 1959-04-28 1960-04-27 Improvements in or relating to combating pests Expired GB951770A (en)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
NL238687 1959-04-28
NL242085 1959-08-06
NL249879 1960-03-28

Publications (1)

Publication Number Publication Date
GB951770A true GB951770A (en) 1964-03-11

Family

ID=27351015

Family Applications (2)

Application Number Title Priority Date Filing Date
GB14775/60A Expired GB951770A (en) 1959-04-28 1960-04-27 Improvements in or relating to combating pests
GB14772/60A Expired GB949619A (en) 1959-04-28 1960-04-27 Improvements in or relating to nuclear-chlorinated benzonitrile derivatives and compositions comprising the same

Family Applications After (1)

Application Number Title Priority Date Filing Date
GB14772/60A Expired GB949619A (en) 1959-04-28 1960-04-27 Improvements in or relating to nuclear-chlorinated benzonitrile derivatives and compositions comprising the same

Country Status (8)

Country Link
US (1) US3185725A (en)
BE (2) BE590254A (en)
CH (1) CH401024A (en)
DE (1) DE1143802B (en)
DK (1) DK105016C (en)
ES (1) ES257609A1 (en)
GB (2) GB951770A (en)
NL (4) NL108786C (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6399807B1 (en) 1997-07-01 2002-06-04 Bayer Aktiegesellschaft Method for production of 2,4,5-trifluoro-benzonitrile

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3535365A (en) * 1967-11-29 1970-10-20 Merck & Co Inc Preparation of 2,6-dichloro-4-methoxy-benzonitrile
DE2960235D1 (en) * 1978-06-12 1981-04-23 Nippon Kayaku Kk A process for the production of 2-chlorobenzonitrile derivatives
JPS55120549A (en) * 1979-03-09 1980-09-17 Nippon Kayaku Co Ltd Preparation of 2-chloro-6-nitrobenzonitrile
JPS5998052A (en) * 1982-11-26 1984-06-06 Sanwa Kagaku Kenkyusho:Kk Preparation of 4-chloro-2-nitrobenzonitrile
JPH0625097B2 (en) * 1988-03-19 1994-04-06 出光興産株式会社 Method for producing aromatic nitrile

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US1996007A (en) * 1933-07-27 1935-03-26 Du Pont Preparation of-2-chloro-6-nitro-benzaldoxime
US2195076A (en) * 1936-10-24 1940-03-26 Gen Aniline & Film Corp Process of replacing halogen in cyclic halogen compounds and product thereof
GB488642A (en) * 1936-11-05 1938-07-05 Ig Farbenindustrie Ag A process for the replacement of halogen in cyclic halogen compounds by the cyano group
DE843327C (en) * 1947-03-18 1952-07-07 Bayer Products Ltd Combating diseases in potato tubers
US2497060A (en) * 1948-12-31 1950-02-14 Gen Aniline & Film Corp 3,5-dihalogen-2-cyanodiphenyls
US2671798A (en) * 1949-04-09 1954-03-09 Merck & Co Inc 2, 2-diphenyl-3-methyl-4-chlorobutyronitrile and processes for preparing the same
US2690965A (en) * 1953-04-29 1954-10-05 Standard Oil Dev Co Herbicidal composition
US2744819A (en) * 1954-10-13 1956-05-08 Dow Chemical Co Method for the control of undesired grasses
US3006954A (en) * 1957-12-27 1961-10-31 Shell Oil Co Urea and thiourea compounds
US3012058A (en) * 1958-05-15 1961-12-05 Pennsalt Chemicals Corp Nitrile compounds
US3009942A (en) * 1958-07-02 1961-11-21 Heyden Newport Chemical Corp Production of trichlorobenzoic acids
US2999046A (en) * 1958-08-25 1961-09-05 Diamond Alkali Co Method of destroying fungi and nematodes employing 2, 2'-(p-xylene)-bis-[2-thiopseudourea] dihydrochloride

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6399807B1 (en) 1997-07-01 2002-06-04 Bayer Aktiegesellschaft Method for production of 2,4,5-trifluoro-benzonitrile

Also Published As

Publication number Publication date
NL242085A (en)
ES257609A1 (en) 1960-09-16
DE1143802B (en) 1963-02-21
NL104318C (en)
GB949619A (en) 1964-02-12
BE590254A (en)
BE590258A (en)
NL108786C (en)
DK105016C (en) 1966-08-08
CH401024A (en) 1965-10-31
US3185725A (en) 1965-05-25
NL238687A (en)

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