GB692546A - Improvements in or relating to methods of preparing insecticidal compounds and the insecticidal compounds resulting from said methods - Google Patents

Improvements in or relating to methods of preparing insecticidal compounds and the insecticidal compounds resulting from said methods

Info

Publication number
GB692546A
GB692546A GB33278/48A GB3327848A GB692546A GB 692546 A GB692546 A GB 692546A GB 33278/48 A GB33278/48 A GB 33278/48A GB 3327848 A GB3327848 A GB 3327848A GB 692546 A GB692546 A GB 692546A
Authority
GB
United Kingdom
Prior art keywords
compounds
give
reacted
products
matter
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
GB33278/48A
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.)
Velsicol Corp
Original Assignee
Velsicol Corp
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 Velsicol Corp filed Critical Velsicol Corp
Publication of GB692546A publication Critical patent/GB692546A/en
Expired legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C07ORGANIC CHEMISTRY
    • C07CACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C17/00Preparation of halogenated hydrocarbons
    • C07C17/26Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton
    • C07C17/30Preparation of halogenated hydrocarbons by reactions involving an increase in the number of carbon atoms in the skeleton by a Diels-Alder synthesis

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

Hexahalocyclopentadienes are reacted according to the Diels-Alder method with diolefinic compounds comprising uninuclear or condensed multinuclear partly hydrogenated aromatic ring systems in which each nucleus contains a 1 : 4-methylene bridge; the products have the skeleton <FORM:0692546/IV (b)/1> in which one of the terminal 5-membered rings has a double bond and only halogen atoms are attached to the carbon atoms in this ring. The other terminal ring also contains a double bond, and this may be further reacted with chlorine or bromine to give addition products which may then be dehydrohalogenated. The Diels-Alder reaction is carried out by heating the reactants together, with or without a solvent. Either one or two molecules of halocyclopentadiene react with the diolefine, depending on the proportions of reactants. In the examples: (1) hexachlorocyclopentadiene is reacted with bicyclo - (2 : 2 : 1) - 2 : 5 - heptadiene to give hexachlorotetracyclodecadiene and dodecachlorohexacycloheptadecadiene (in one or two stages); (2) hexachlorocyclopentadiene is reacted with 2 : 3-dicarbethoxybicyclo-(2 : 2 : 1)-2 : 5-heptadiene (obtained from dicarbethoxyacetylene and cyclopentadiene) to give dicarbethoxy - hexachlorotetracyclodecadiene; (3) hexachlorotetracyclododecadiene is additively brominated or chlorinated to give a mixture of two stereoisomeric octahalo-compounds; (4) the products of (3) are dehydrohalogenated to heptahalo-compounds. Hexabromocyclopentadiene is also mentioned as reactant. Specification 614,931 is referred to. The Specification as open to inspection under Sect. 91 includes the subject-matter of Specifications 692,545 and 692,547 and mentions compounds similar to those of the latter Specification where the epatomic component is >SO, >NH, >NR or the ionized groupings >SH, >SR, >NH2 and >NHR; R is an alkyl or aryl group, or any other group that may be attached to a nitrogen or sulphur atom. In all the types of compounds described the following may be present as substituents in any ring except that containing the six halogen atoms:-R, Cl, Br, I, OH, OR, SH, SR, NH2, NHR, NR2, NR3 (ion), COR, OCOR, COOH, COOR or CN, R being a hydrocarbon or substituted hydrocarbon group. These substituents may be present in the starting materials or may be introduced into the products. In addition, the substituents on the methano bridges may be alkylidene or cycloalkylidene, e.g. when a fulvene is used as dienophile. Compounds may be obtained from the above by loss of H2O, ROH, H2S, RSH, NH3, NH2R, NHR2 or H Hal or by tautomeric shift. Probable stereo-chemical formul are given for the products. Further reactions mentioned are: (1) 6 : 7-epoxy - hexachlorotetracyclododecene is heated with acetic acid and a catalyst (e.g. sulphuric acid) to give a hydroxyacetate; this is converted by phosphorus tribromide (or other reagent) into a bromo-acetate; the latter when treated with alkali is hydrolysed and ring-closed to a stereoisomer of the starting material; (2) 6 - keto - hexachlorotetracyclododecene reacted with p-chlorophenylmagnesium bromide gives p - chlorophenyl - hydroxy - hexachlorododecene (sic) which loses water on heating to yield p - chlorophenyl - hexachlorotetracyclododecadiene. This subject - matter does not appear in the Specification as accepted.ALSO:Insecticidal compositions contain as active ingredient one or more compounds of the structure <FORM:0692546/VI/1> in which one of the terminal 5-membered rings has only halogen atoms (chlorine or bromine) attached to the carbon atoms and contains a double bond. The compounds may be dissolved in oils and/or emulsified in water, or combined with carriers to give wettable or non-wettable dusts. They may be added to whitewashes, paints, lacquers, varnishes or waxes to give insecticidal surfaces, or used to impregnate paper or plastic materials to protect these or objects wrapped in them from insect attack. They may be used in conjunction with other insecticides. Specific compounds are hexachlorotetracyclododecadiene, dodecachlorohexacycloheptadecadiene, dicarbethoxy - hexachlorotetra-cyclododecadiene, octahalotetracyclododecene and heptahalotetracyclododecadiene. Tables are given of the activities of these compared with known insecticides. Specification 614,931 is referred to. The Specification as open to inspection under Sect. 91, includes the subject-matter of Specifications 692,545 and 692,547 and mentions some additional compounds. This subject-matter does not appear in the Specification as accepted.
GB33278/48A 1948-08-21 1948-12-24 Improvements in or relating to methods of preparing insecticidal compounds and the insecticidal compounds resulting from said methods Expired GB692546A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US692546XA 1948-08-21 1948-08-21

Publications (1)

Publication Number Publication Date
GB692546A true GB692546A (en) 1953-06-10

Family

ID=22087730

Family Applications (1)

Application Number Title Priority Date Filing Date
GB33278/48A Expired GB692546A (en) 1948-08-21 1948-12-24 Improvements in or relating to methods of preparing insecticidal compounds and the insecticidal compounds resulting from said methods

Country Status (1)

Country Link
GB (1) GB692546A (en)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2875121A (en) * 1954-12-16 1959-02-24 Velsicol Chemical Corp Insecticide formulations
US5270345A (en) * 1988-11-04 1993-12-14 Coulston International Corporation Non-bioaccumulable pesticides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2875121A (en) * 1954-12-16 1959-02-24 Velsicol Chemical Corp Insecticide formulations
US5270345A (en) * 1988-11-04 1993-12-14 Coulston International Corporation Non-bioaccumulable pesticides

Similar Documents

Publication Publication Date Title
US2606910A (en) Diels-alder adducts of hexahalo-cyclopentadiene
Ungnade et al. The chemistry of perchlorocyclopentenes and cyclopentadienes
DE2261918A1 (en) DIPHENYL ETHER AND METHOD FOR THEIR MANUFACTURE AND USE
US3036088A (en) N-(fluoroalkylthio)-imides
US3654302A (en) Tetrahydrophthalanils
US3227734A (en) Herbicidal 4-methylsulfonyl-2,6-dinitro-n,n-substituted anilines
GB692546A (en) Improvements in or relating to methods of preparing insecticidal compounds and the insecticidal compounds resulting from said methods
US3000907A (en) Chlorinated 4,5,6,7,10,10-hexachloro-4,7-endomethylene - 4,7,8,9 - tetrahydrophthalane insecticides
US3052597A (en) Sulfonyl ethylene fungicides
US2952711A (en) Hexahalocyclopentadiene-divinylbenzene adducts and method of making
US2854325A (en) Herbicidal process and composition
US2996553A (en) Condensation of hexachlorocyclopentadiene
US2793975A (en) Substituted epoxy and epithia dimethanonaphthalenes
US3944411A (en) Halogenoethyl esters of aromatic carboxylic acids as fruit abscission agents
US2418459A (en) Pest control
US3062898A (en) Preparation of 1, 2, 3, 4, 5, 6, 7, 7-octachloro-2-methylbicyclo-(2.2.1)-heptene-5
US2804420A (en) Insect toxicant
US2908723A (en) Perchlorocarbon having the empirical formula c10cl10
US2931803A (en) Fluorocarbon metalloid compounds of tetrafluoroethylene and sulfur, selenium or phosphorus and their preparation
US3378580A (en) 2-aryl-polyhalo-bicyclohept-5-enes
US2952710A (en) Novel derivatives of hexachlorocyclopentadiene
US3829435A (en) 2,5-dichlorothiazolo(5,4-d)thiazole and process for preparing same
US3462482A (en) Fluoroperhaloisopropyl benzene carboxylic acids
US3356485A (en) Herbicidal composition and method
US3405176A (en) Bromodichloroacetanilides