GB824600A - Insecticidally active acetals containing the methylenedioxybenzene ring system and their production - Google Patents

Insecticidally active acetals containing the methylenedioxybenzene ring system and their production

Info

Publication number
GB824600A
GB824600A GB601058A GB601058A GB824600A GB 824600 A GB824600 A GB 824600A GB 601058 A GB601058 A GB 601058A GB 601058 A GB601058 A GB 601058A GB 824600 A GB824600 A GB 824600A
Authority
GB
United Kingdom
Prior art keywords
ether
vinyl
alkyl
propyl
insecticides
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
GB601058A
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.)
BASF SE
Original Assignee
BASF SE
Badische Anilin and Sodafabrik AG
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 BASF SE, Badische Anilin and Sodafabrik AG filed Critical BASF SE
Publication of GB824600A publication Critical patent/GB824600A/en
Expired legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D407/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00
    • C07D407/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings
    • C07D407/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having oxygen atoms as the only ring hetero atoms, not provided for by group C07D405/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
    • C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
    • C07D317/44—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D317/46—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 ortho- or peri-condensed with carbocyclic rings or ring systems condensed with one six-membered ring
    • C07D317/48—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring
    • C07D317/50—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/54—Radicals substituted by oxygen atoms

Landscapes

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

Abstract

The invention comprises acetals of the general formula <FORM:0824600/IV (b)/1> wherein R represents methyl, R1 represents alkyl, phenyl or a saturated aliphatic hydrocarbon radical interrupted by one or more oxygen atoms combined in ether-like fashion, or R and R1 together represent a chain of 3 or 4 CH2 groups which may be substituted by one or more alkyl and/or alkoxy groups. They may be prepared by reacting a -unsaturated cyclic or open-chain ethers with 1 - (a - hydroxyethyl) - 2 - propyl-4,5-methylenedioxybenzene which may itself be prepared by catalytic hydrogenation of 1-acetyl-2-propyl-4,5-methylenedioxybenzene. An acidic catalyst is advantageously used. Temperatures mentioned are in the range about 15-120 DEG C. Solvents may be present, e.g. ethers such as diethyl ether, tetrahydrofuran or dioxan or hydrocarbons such as butane, hexane, cyclohexane or benzene and its homologues. The products are said to be insecticides and insecticide synergists. In examples, acetals are prepared by reacting 1-(a -hydroxyethyl) - 2 - propyl - 4,5 - methylendioxybenzene with: (1) vinyl ethyl diglycol ether in the presence of boron trifluoride etherate in ethereal solution; (2) 2,3-dihydrofuran in the presence of HC1 in ethereal solution; (3) 2,3-dihydropyran in the presence of HC1 in aqueous solution; (4) 2-ethoxy-4-methyl-2,3-dihydropyran in the presence of boron trifluoride in ethereal solution; and (5) 2,3-dihydrofuran in the presence of HCl in tetrahydrofuran solution. Other unsaturated ethers suitable as starting materials include other 2-alkoxy-2,3-dihydropyrans and -furans, vinyl butyl ether, vinyl ethyl glycol ether, vinyl methyl triglycol ether, vinyl butyl diglycol ether and vinyl phenyl ether. Other suitable catalysts are inorganic acids such as H2SO4 and AlCl3, ZnCl2 and SbCl3. Specification 632,589 is referred to.ALSO:Compounds stated to be insecticides and to be especially suited as additives to other insecticides especially those of the pyrethrum class have the formula <FORM:0824600/VI/1> wherein R represents methyl, R1 represents alkyl, phenyl or a saturated aliphatic hydrocarbon radical interrupted by one or more oxygen atoms combined in ether-like fashion, or R and R1 together represent a chain of 3 or 4 CH2 groups which may be substituted by one or more alkyl and/or alkoxy groups. (Preparation in Group IV (b)).
GB601058A 1957-03-23 1958-02-25 Insecticidally active acetals containing the methylenedioxybenzene ring system and their production Expired GB824600A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
DEB44036A DE1081898B (en) 1957-03-23 1957-03-23 Process for the preparation of ª ‡ - (2-propyl-4, 5-methylenedioxy-phenyl) -aethyl-acetals

Publications (1)

Publication Number Publication Date
GB824600A true GB824600A (en) 1959-12-02

Family

ID=6967220

Family Applications (1)

Application Number Title Priority Date Filing Date
GB601058A Expired GB824600A (en) 1957-03-23 1958-02-25 Insecticidally active acetals containing the methylenedioxybenzene ring system and their production

Country Status (4)

Country Link
CH (1) CH370096A (en)
DE (1) DE1081898B (en)
GB (1) GB824600A (en)
NL (1) NL102188C (en)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS6036565A (en) * 1983-08-09 1985-02-25 Asahi Glass Co Ltd Curable resin composition
GB8702717D0 (en) * 1987-02-06 1987-03-11 Ici Plc Insecticidal compounds

Also Published As

Publication number Publication date
NL102188C (en)
CH370096A (en) 1963-06-30
DE1081898B (en) 1960-05-19

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