GB903766A - Herbicidal dichloroanilides of carboxylic acids and their preparation and use - Google Patents

Herbicidal dichloroanilides of carboxylic acids and their preparation and use

Info

Publication number
GB903766A
GB903766A GB2428/59A GB242859A GB903766A GB 903766 A GB903766 A GB 903766A GB 2428/59 A GB2428/59 A GB 2428/59A GB 242859 A GB242859 A GB 242859A GB 903766 A GB903766 A GB 903766A
Authority
GB
United Kingdom
Prior art keywords
acid
halide
dichloroanilides
carboxylic acid
acids
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
GB2428/59A
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.)
Rohm and Haas Co
Original Assignee
Rohm and Haas Co
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 Rohm and Haas Co filed Critical Rohm and Haas Co
Publication of GB903766A publication Critical patent/GB903766A/en
Expired legal-status Critical Current

Links

Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
    • A01N37/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof
    • A01N37/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group —CO—N<, e.g. carboxylic acid amides or imides; Thio analogues thereof the nitrogen atom being directly attached to an aromatic ring system, e.g. anilides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

The invention comprises 3,4-dichloroanilides of propionic, and alpha-methyl-valeric acids. The compounds may be prepared by dissolving 3,4-dichloro-aniline in a volatile, inert, organic solvent and reacting it with the appropriate carboxylic acid or its acid anhydride or halide. When an acid halide is used an alkaline reagent is supplied to take up the hydrogen halide split out. When the carboxylic acid itself is used, the mixture is heated under reflux with removal of water carried over by the azeotroping liquid. Solvents specified are naphtha, benzene, toluene, xylene, di- and trichloroethane, and dichloropropane. The reaction may be carried out at about 10 DEG to 50 DEG C. when an acyl halide or anhydride is used or at 50 DEG -150 DEG C. when a carboxylic acid is used. Examples are given.ALSO:The invention comprises herbicidal compositions containing a 3,4-dichloroanilide of propionic, or alpha-methyl valeric acid, or a mixture thereof, dispersed in a carrier. The compositions may be in the form of aqueous sprays or dusts, preferably containing a surface-active agent. An emulsifiable concentrate may be prepared from isophorone, an aromatic naphtha or xylene or toluene or mixtures thereof together with one or more solvent-emulsifying agents and the 3,4-dichloroanilides. Additional components may be e.g. methenol, methoxyethanol or butoxyethanol. Emulsifying agents mentioned are calcium dodecylbenzene sulphonate, sodium dioctylsulphosuccinate, octyl and nonyl phenoxypolyethoxy ethanol, ethylene oxide condensates of longchained alcohols, carboxylic acids, thiols, or amines, condensates of polyglycerols and fatty acids, with or without a resin-forming acid such as phthalic acid, or such compounds as oleylbenzyldimethylammonium chloride, or dodecylbenzyltrimethylammonium chloride or bromide. Finely-divided solid carriers specified are kaolin, pyrrophyllite and diatomaceous earth.
GB2428/59A 1958-02-13 1959-01-22 Herbicidal dichloroanilides of carboxylic acids and their preparation and use Expired GB903766A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US71494758A 1958-02-13 1958-02-13

Publications (1)

Publication Number Publication Date
GB903766A true GB903766A (en) 1962-08-22

Family

ID=24872124

Family Applications (1)

Application Number Title Priority Date Filing Date
GB2428/59A Expired GB903766A (en) 1958-02-13 1959-01-22 Herbicidal dichloroanilides of carboxylic acids and their preparation and use

Country Status (8)

Country Link
CH (1) CH382494A (en)
CY (1) CY271A (en)
ES (2) ES246858A1 (en)
FR (1) FR1220218A (en)
GB (1) GB903766A (en)
MY (1) MY6400024A (en)
NL (1) NL235788A (en)
OA (1) OA00109A (en)

Cited By (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1219947B (en) * 1963-05-22 1966-06-30 Bayer Ag Process for the preparation of carboxylic acid anilides
EP0062861A1 (en) * 1981-04-06 1982-10-20 Montedison S.p.A. Isophorone-free formulations of the herbicide propanyl
WO2002089575A1 (en) * 2001-04-10 2002-11-14 Clariant Gmbh Pesticidal preparations comprising copolymers
WO2012119772A1 (en) 2011-03-10 2012-09-13 Clariant International Ltd Compositions containing copolymers
US8759255B2 (en) 2009-09-10 2014-06-24 Clariant Finance (Bvi) Limited Pesticide preparations
EP1824955B1 (en) 2004-10-18 2016-03-16 Croda International Plc Surfactant compounds
CN107207415A (en) * 2015-01-19 2017-09-26 Upl 有限公司 The crystalline modification of propanil

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR1310207A (en) * 1961-01-03 1963-03-06
NL280108A (en) * 1961-06-30

Cited By (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1219947B (en) * 1963-05-22 1966-06-30 Bayer Ag Process for the preparation of carboxylic acid anilides
EP0062861A1 (en) * 1981-04-06 1982-10-20 Montedison S.p.A. Isophorone-free formulations of the herbicide propanyl
WO2002089575A1 (en) * 2001-04-10 2002-11-14 Clariant Gmbh Pesticidal preparations comprising copolymers
US7407667B2 (en) 2001-04-10 2008-08-05 Clariant Produkte (Deutschland) Gmbh Pesticidal preparations comprising copolymers
EP1824955B1 (en) 2004-10-18 2016-03-16 Croda International Plc Surfactant compounds
EP1824955B2 (en) † 2004-10-18 2019-03-06 Croda International Plc Surfactant compounds
US8759255B2 (en) 2009-09-10 2014-06-24 Clariant Finance (Bvi) Limited Pesticide preparations
WO2012119772A1 (en) 2011-03-10 2012-09-13 Clariant International Ltd Compositions containing copolymers
DE102011013556A1 (en) 2011-03-10 2012-09-13 Clariant International Ltd. Compositions containing copolymers
CN107207415A (en) * 2015-01-19 2017-09-26 Upl 有限公司 The crystalline modification of propanil
EP3247698A4 (en) * 2015-01-19 2018-07-04 UPL Limited Crystalline modification of propanil
CN114766484A (en) * 2015-01-19 2022-07-22 Upl 有限公司 Crystal modification of propanil

Also Published As

Publication number Publication date
ES246858A1 (en) 1959-08-16
FR1220218A (en) 1960-05-23
OA00109A (en) 1966-01-15
MY6400024A (en) 1964-12-31
NL235788A (en)
ES275364A2 (en) 1962-10-16
CY271A (en) 1964-01-08
CH382494A (en) 1964-09-30

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