GB1146975A - Benzimidazole derivatives and their use as pesticides - Google Patents

Benzimidazole derivatives and their use as pesticides

Info

Publication number
GB1146975A
GB1146975A GB1237665A GB1237665A GB1146975A GB 1146975 A GB1146975 A GB 1146975A GB 1237665 A GB1237665 A GB 1237665A GB 1237665 A GB1237665 A GB 1237665A GB 1146975 A GB1146975 A GB 1146975A
Authority
GB
United Kingdom
Prior art keywords
formula
alkyl
halomethylbenzimidazoles
hydrogen
prepared
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
GB1237665A
Inventor
John Frederick Harris
Raymond Sutton
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.)
Fisons Pest Control Ltd
Original Assignee
Fisons Pest Control 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 Fisons Pest Control Ltd filed Critical Fisons Pest Control Ltd
Priority to GB1237665A priority Critical patent/GB1146975A/en
Priority to BE677941D priority patent/BE677941A/xx
Priority to AT254866A priority patent/AT265251B/en
Priority to LU50683A priority patent/LU50683A1/xx
Priority to CH394866A priority patent/CH455804A/en
Priority to DE19661670678 priority patent/DE1670678A1/en
Priority to NL6603719A priority patent/NL6603719A/xx
Priority to FR54634A priority patent/FR1477792A/en
Priority to ES0324565A priority patent/ES324565A1/en
Publication of GB1146975A publication Critical patent/GB1146975A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
    • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
    • C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
    • C07D235/06—Benzimidazoles; Hydrogenated benzimidazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached in position 2
    • C07D235/10—Radicals substituted by halogen atoms or nitro radicals

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Plural Heterocyclic Compounds (AREA)

Abstract

1,146,975. 2 - Halomethylbenzimidazoles. FISONS PEST CONTROL Ltd. 28 Feb., 1966 [24 March, 1965; 25 May, 1965], Nos. 12376/65 and 22028/65. Heading C2C. [Also in Division A5] The invention comprises compounds of the formula wherein X<SP>1-3</SP> are F or Cl atoms, at least one being Cl, R<SP>1</SP> is hydrogen or an optionally substituted alkyl or aryl group and R<SP>2-5</SP> are hydrogen, halogen or alkyl, alkoxy, nitro, cyano, azido, carboxy, disubstituted amino, thiol, sulphonic acid, sulphonic acid halide, substituted alkyl, alkyl thiol, or oxygenated derivatives thereof, or a heterocyclic ring attached to the benzimidazole system through a N atom, and the salts thereof. The compounds of the above formula, and those in which each of X<SP>1-3</SP> is F, are prepared by heating an acid addition salt of an o-phenylenediamine of the formula with a trihalogenoacetic acid of the formula in the presence of phosphorus oxychloride in sufficient amount to dissolve or suspend the reactants. It is preferred to use at least 2 mols. phosphorus oxychloride per mol. of diamine salt and to effect the reaction at 60-140‹ C. Preferred acid addition salts of the diamine are the hydrochloride, sulphate and phosphate. The 2-trifluoromethylbenzimidazoles of the above formula may also be prepared by heating a compound in which at least one of X<SP>1-3</SP> is Cl with antimony trifluoride in the presence of an inert solvent. Examples relate to 2-halomethylbenzimidazoles in which the benzene moiety of the benzimidazole ring is substituted by chlorine atoms. The benzimidazoles are used as pesticides (see Division A5). Reference has been directed by the Comptroller to Specification 1,080,009.
GB1237665A 1965-03-24 1965-03-24 Benzimidazole derivatives and their use as pesticides Expired GB1146975A (en)

Priority Applications (9)

Application Number Priority Date Filing Date Title
GB1237665A GB1146975A (en) 1965-03-24 1965-03-24 Benzimidazole derivatives and their use as pesticides
BE677941D BE677941A (en) 1965-03-24 1966-03-16
AT254866A AT265251B (en) 1965-03-24 1966-03-17 Process for the preparation of new substituted benzimidazoles and their salts
LU50683A LU50683A1 (en) 1965-03-24 1966-03-17
CH394866A CH455804A (en) 1965-03-24 1966-03-18 Process for the preparation of benzimidazoles
DE19661670678 DE1670678A1 (en) 1965-03-24 1966-03-19 Process for the preparation of substituted benzimidazoles
NL6603719A NL6603719A (en) 1965-03-24 1966-03-22
FR54634A FR1477792A (en) 1965-03-24 1966-03-23 New benzimidazoles
ES0324565A ES324565A1 (en) 1965-03-24 1966-03-23 Procedure for preparing substituteed benzymidazoles. (Machine-translation by Google Translate, not legally binding)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB1237665A GB1146975A (en) 1965-03-24 1965-03-24 Benzimidazole derivatives and their use as pesticides
GB2202865 1965-05-25

Publications (1)

Publication Number Publication Date
GB1146975A true GB1146975A (en) 1969-03-26

Family

ID=26248985

Family Applications (1)

Application Number Title Priority Date Filing Date
GB1237665A Expired GB1146975A (en) 1965-03-24 1965-03-24 Benzimidazole derivatives and their use as pesticides

Country Status (7)

Country Link
BE (1) BE677941A (en)
CH (1) CH455804A (en)
DE (1) DE1670678A1 (en)
ES (1) ES324565A1 (en)
GB (1) GB1146975A (en)
LU (1) LU50683A1 (en)
NL (1) NL6603719A (en)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3755346A (en) * 1966-01-26 1973-08-28 Q Soper 2,6-bis(trifluoromethyl)-4-nitrobenzimidazole

Also Published As

Publication number Publication date
DE1670678A1 (en) 1970-12-03
BE677941A (en) 1966-09-16
LU50683A1 (en) 1966-05-17
ES324565A1 (en) 1966-12-16
NL6603719A (en) 1966-09-26
CH455804A (en) 1968-05-15

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