GB1087017A - Methylenedioxyphenyl compounds and pesticidal compositions containing them - Google Patents

Methylenedioxyphenyl compounds and pesticidal compositions containing them

Info

Publication number
GB1087017A
GB1087017A GB29023/65A GB2902365A GB1087017A GB 1087017 A GB1087017 A GB 1087017A GB 29023/65 A GB29023/65 A GB 29023/65A GB 2902365 A GB2902365 A GB 2902365A GB 1087017 A GB1087017 A GB 1087017A
Authority
GB
United Kingdom
Prior art keywords
hydrogen
oxygen
compounds
carbamate
synergist
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
GB29023/65A
Inventor
George Joseph Popjak
William Bonthrone
John Clifford Felton
Panayiotis Nicolaou Manis
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.)
Shell Internationale Research Maatschappij BV
Original Assignee
Shell Internationale Research Maatschappij BV
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 Shell Internationale Research Maatschappij BV filed Critical Shell Internationale Research Maatschappij BV
Priority to GB29023/65A priority Critical patent/GB1087017A/en
Priority to FR68369A priority patent/FR1486029A/en
Priority to CH978066A priority patent/CH479243A/en
Priority to SE09246/66A priority patent/SE326864B/xx
Priority to DE19661567134 priority patent/DE1567134A1/en
Priority to NL6609422A priority patent/NL6609422A/xx
Priority to BE683794D priority patent/BE683794A/xx
Publication of GB1087017A publication Critical patent/GB1087017A/en
Expired legal-status Critical Current

Links

Classifications

    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
    • B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
    • B01J4/00—Feed or outlet devices; Feed or outlet control devices
    • B01J4/001—Feed or outlet devices as such, e.g. feeding tubes
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
    • 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
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
    • A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
    • A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
    • A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
    • A01N43/30—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3 with two oxygen atoms in positions 1,3, condensed with a carbocyclic ring
    • 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
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
    • A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
    • A01N47/22—O-Aryl or S-Aryl esters thereof
    • 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
    • A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
    • A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
    • A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
    • 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
    • C07D317/62—Methylenedioxybenzenes or hydrogenated methylenedioxybenzenes, unsubstituted on the hetero ring with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to atoms of the carbocyclic ring
    • C07D317/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen

Landscapes

  • Life Sciences & Earth Sciences (AREA)
  • Chemical & Material Sciences (AREA)
  • Dentistry (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Pest Control & Pesticides (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention comprises compounds of the formula <FORM:1087017/C2/1> in which X represents oxygen or sulphur, R and R1 are both hydrogen when X is sulphur, or each may be hydrogen or an alkyl group when X is oxygen, and Y is hydrogen or a halogen atom. The compounds in which X is oxygen and both R and R1 are hydrogen are prepared by treating the appropriate methylenedioxybenzonitrile with an oxidizing agent, e.g. H2O2, in the presence of a base, e.g. an alkaline hydroxide. Those compounds in which X is oxygen and either or both of R1 and R are alkyl groups are made by reacting the appropriate piperonylic acid chloride with an amine NHRR1. The thioamides are prepared by reacting the nitrile with hydrogen sulphide in the presence of an organic base. The compounds in which X is oxygen are synergists for insecticidal agents (see Division A5). Examples are provided.ALSO:Insecticidal compositions comprising at least one organophosphorus or carbamate insecticide, contain, as a synergist, at least one compound of the formula <FORM:1087017/A5-A6/1> in which X is oxygen, R and R1 are hydrogen or an alkyl group and Y is hydrogen or a halogen atom. The weight ratio of synergist to insecticide is preferably 0.3:1 to 10:1. Specified insecticides are Bidrin (Trade Mark), 2-chloro-1-(2,4-dichlorophenyl) vinyl diethyl phosphate, dimethyl dichlorovinyl phosphate, N-3,4,5-trimethylphenyl-N-methyl carbamate, isolan (dimethyl-5-[1-isoPr-3-Me-pyrazolyl] carbamate). The compositions may take the form of wettable powders, dusts, granules, concentrates, solutions, emulsifiable concentrates, emulsions or aerosols and may comprise a solid or liquid carrier and/or surface active agents. Examples are provided and contain comparative data relating to known synergists.
GB29023/65A 1965-07-08 1965-07-08 Methylenedioxyphenyl compounds and pesticidal compositions containing them Expired GB1087017A (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
GB29023/65A GB1087017A (en) 1965-07-08 1965-07-08 Methylenedioxyphenyl compounds and pesticidal compositions containing them
FR68369A FR1486029A (en) 1965-07-08 1966-07-06 New methylene-dioxyphenyl compounds, their preparation and use as synergistic agents for insecticides
CH978066A CH479243A (en) 1965-07-08 1966-07-06 Insecticidal agent
SE09246/66A SE326864B (en) 1965-07-08 1966-07-06
DE19661567134 DE1567134A1 (en) 1965-07-08 1966-07-06 Insecticides
NL6609422A NL6609422A (en) 1965-07-08 1966-07-06
BE683794D BE683794A (en) 1965-07-08 1966-07-07

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
GB29023/65A GB1087017A (en) 1965-07-08 1965-07-08 Methylenedioxyphenyl compounds and pesticidal compositions containing them

Publications (1)

Publication Number Publication Date
GB1087017A true GB1087017A (en) 1967-10-11

Family

ID=10285016

Family Applications (1)

Application Number Title Priority Date Filing Date
GB29023/65A Expired GB1087017A (en) 1965-07-08 1965-07-08 Methylenedioxyphenyl compounds and pesticidal compositions containing them

Country Status (6)

Country Link
BE (1) BE683794A (en)
CH (1) CH479243A (en)
DE (1) DE1567134A1 (en)
GB (1) GB1087017A (en)
NL (1) NL6609422A (en)
SE (1) SE326864B (en)

Also Published As

Publication number Publication date
SE326864B (en) 1970-08-03
BE683794A (en) 1967-01-09
NL6609422A (en) 1967-01-09
DE1567134A1 (en) 1970-07-23
CH479243A (en) 1969-10-15

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