EP0000537B1 - Insektizide und akarizide Mittel, deren Verwendung und Verfahren zu deren Herstellung - Google Patents

Insektizide und akarizide Mittel, deren Verwendung und Verfahren zu deren Herstellung Download PDF

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Publication number
EP0000537B1
EP0000537B1 EP78100424A EP78100424A EP0000537B1 EP 0000537 B1 EP0000537 B1 EP 0000537B1 EP 78100424 A EP78100424 A EP 78100424A EP 78100424 A EP78100424 A EP 78100424A EP 0000537 B1 EP0000537 B1 EP 0000537B1
Authority
EP
European Patent Office
Prior art keywords
spp
alkyl
oder
methyl
für
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
EP78100424A
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German (de)
English (en)
French (fr)
Other versions
EP0000537A1 (de
Inventor
Volker Dr. Mues
Wolfgang Dr. Behrenz
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.)
Bayer AG
Original Assignee
Bayer 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 Bayer AG filed Critical Bayer AG
Publication of EP0000537A1 publication Critical patent/EP0000537A1/de
Application granted granted Critical
Publication of EP0000537B1 publication Critical patent/EP0000537B1/de
Expired legal-status Critical Current

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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
    • 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
    • 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
    • C07D317/52—Radicals substituted by halogen atoms or nitro 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
    • C07D317/50—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
    • 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
    • C07D317/58—Radicals substituted by nitrogen atoms
    • 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
    • G—PHYSICS
    • G06—COMPUTING; CALCULATING OR COUNTING
    • G06F—ELECTRIC DIGITAL DATA PROCESSING
    • G06F5/00—Methods or arrangements for data conversion without changing the order or content of the data handled
    • G06F5/06—Methods or arrangements for data conversion without changing the order or content of the data handled for changing the speed of data flow, i.e. speed regularising or timing, e.g. delay lines, FIFO buffers; over- or underrun control therefor
    • G06F5/10—Methods or arrangements for data conversion without changing the order or content of the data handled for changing the speed of data flow, i.e. speed regularising or timing, e.g. delay lines, FIFO buffers; over- or underrun control therefor having a sequence of storage locations each being individually accessible for both enqueue and dequeue operations, e.g. using random access memory

Definitions

  • the present invention relates to new insecticidal and acaricidal synergistic active ingredient combinations of partially known benzodioxoles and other known pesticidal, in particular insecticidal, active ingredients.
  • R 7 is hydrogen, alkyl having 1 to 6 carbon atoms, haloalkyl having 1 to 4 carbon atoms and up to 3 halogen atoms, nitrile or ethynyl are preferred.
  • R 8 is phenyl, which is optionally substituted by C 1-4 -alkyl, halogen, in particular fluorine or chlorine, optionally halogen- or methyl-substituted phenoxy, optionally substituted benzyl, furthermore furanyl, tetrahydrophthalimido, Benzodioxol, which is optionally substituted by halogen, in particular chlorine, alkyl or alkenyl having up to 4 carbon atoms or benzyl, and also represents cyclopentonone, which may be substituted by C 1-4 alkyl, furfuryl, C 1-5 alkenyl is substituted.
  • the insecticidal and / or acaricidal action of the active compound combinations according to the invention is substantially higher than the action of the individual components or the sum of the actions of the individual components. It is also significantly higher than the effect of the already known combination of active ingredients from 2-iso-propoxy-phenyl-N-methyl-carbamate and piperonyl butoxide.
  • the benzodioxole derivatives which can be used according to the invention show excellent synergistic activity not only with one class of active substance, but with active substances from a wide variety of chemical groups.
  • synergistic mixtures containing benzodioxole derivatives according to the invention thus represent a valuable enrichment of technology.
  • 6-chloromethyl compounds used as intermediates can be prepared by the processes specified in US Pat. Nos. 2,485,600 and 2,485,680.
  • the carbamates (group A) of the formula (11) to be used as mixed components include: 2-methylphenyl, 2-ethyphenyl, 2-n-propylphenyl, 2-methoxyphenyl, 2-ethoxyphenyl, 2-iso-propoxyphenyl -, 4-methylphenyl, 4-ethylphenyl, 4-n-propylphenyl, 4-methoxyphenyl, 4-ethoxyphenyl, 4-n-propoxyphenyl, 3,4,5-trimethylphenyl, 1-naphthyl, 2 3-dihydro-2,2-dimethyl-7-benzofuranyl-, 2- [1,3-dioxolane (2) yl-phenyl] - or 2,2-dimethyl-1,3-benzodioxole (4) yl- N-methyl-carbamate and the corresponding -N-methyl-N-acetyl-, -N-methyl-N-trifluoromethylthio-, -N-
  • the new active ingredient combinations of the benzodioxole derivatives of the formula (I) which can be used according to the invention with carbamates, carboxylic acid esters, phosphoric acid esters and / or haloalkanes show an outstanding increase in activity compared to the individual active ingredients or their sum.
  • Diprion spp. Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp. From the order of the Diptera z.
  • B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomox ., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipul
  • the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, seed pu ders, active substance-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals, etc. as well as ULV cold and warm fog formulations.
  • customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, seed pu ders, active substance-impregnated natural and synthetic substances, very fine encapsulations in polymeric substances and in coating compositions for seeds, also in formulations with fuel sets, such as smoking cartridges, cans, spirals,
  • formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carrier substances, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents.
  • extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carrier substances, if appropriate using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • surface-active agents that is to say emulsifiers and / or dispersants and / or foam-generating agents.
  • water e.g. organic solvents can also be used as auxiliary solvents.
  • aromatics such as xylene, toluene, or alkylnaphthalenes
  • chlorinated aromatics or chlorinated aliphatic hydrogen sulfides such as chlorobenzenes, chloroethylene or methylene chloride
  • aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions alcohols, such as butanol or glycol, and also ether and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulfoxide, and water; liquefied gaseous extenders or carriers mean liquids which are gaseous at normal temperature and under normal pressure, e.g.
  • Aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carriers: natural rock flour, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flours, such as highly disperse silica, aluminum oxide and silicates; as solid carriers for granules: broken and fractionated natural rocks such as calcite, marble, pumice, sepiblite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foaming agents: nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.
  • Adhesives such as carboxymethyl cellulose, natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, can be used in the formulations.
  • Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.
  • the active compound combinations according to the invention are used in the form of their commercially available formulations and / or the use forms prepared from these formulations.
  • the total active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
  • the active substance concentration of the use forms can be from 0.0000001 to 100% by weight of active substance, preferably between 0.01 and 10% by weight.
  • the application takes place in a customary manner adapted to the application forms.
  • the active substance combinations When used against hygiene pests and pests of stored products, the active substance combinations are notable for an excellent residual action on wood and clay and for good stability to alkali on limed substrates.
  • Test animals Phosphoric acid ester-resistant Musca domestica (Weymann strain)
  • Solutions are prepared from the active ingredients, synergists and mixtures of active ingredients and synergists, and 2.5 ml of these are pipetted into Petri dishes on filter paper discs with a diameter of 9.5 cm. The filter paper absorbs the solutions. The petri dishes remain open until the solvent has completely evaporated. Then 25 test animals are placed in the Petri dishes and covered with a glass lid.
  • the condition of the test animals is checked continuously for up to 6 hours. The time required for a 100% knock-down effect is determined. If the LT 100 is not reached after 6 hours, the% salt of the test animals that have knocked down is determined.

Landscapes

  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Theoretical Computer Science (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Physics & Mathematics (AREA)
  • Health & Medical Sciences (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • General Physics & Mathematics (AREA)
  • General Engineering & Computer Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
EP78100424A 1977-07-28 1978-07-18 Insektizide und akarizide Mittel, deren Verwendung und Verfahren zu deren Herstellung Expired EP0000537B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2734108 1977-07-28
DE19772734108 DE2734108A1 (de) 1977-07-28 1977-07-28 Insektizide und akarizide mittel

Publications (2)

Publication Number Publication Date
EP0000537A1 EP0000537A1 (de) 1979-02-07
EP0000537B1 true EP0000537B1 (de) 1980-12-10

Family

ID=6015066

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100424A Expired EP0000537B1 (de) 1977-07-28 1978-07-18 Insektizide und akarizide Mittel, deren Verwendung und Verfahren zu deren Herstellung

Country Status (15)

Country Link
US (1) US4229445A (it)
EP (1) EP0000537B1 (it)
JP (1) JPS5426330A (it)
AT (1) AT360277B (it)
AU (1) AU3837178A (it)
BR (1) BR7804832A (it)
CS (1) CS197328B2 (it)
DE (2) DE2734108A1 (it)
DK (1) DK334778A (it)
IL (1) IL55215A0 (it)
IT (1) IT7826144A0 (it)
NZ (1) NZ187944A (it)
PT (1) PT68319A (it)
TR (1) TR19891A (it)
ZA (1) ZA784267B (it)

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2816190A1 (de) 1978-04-14 1979-10-25 Bayer Ag Neue benzodioxolderivate
JPH08925Y2 (ja) * 1993-04-26 1996-01-17 株式会社フォンタァジュ 照明パネル
JP5066915B2 (ja) * 2006-04-03 2012-11-07 住友化学株式会社 １，３−ベンズジオキソール化合物とその用途
CN107108425B (zh) * 2014-12-23 2021-04-27 安西娅芳香剂私人有限公司 用于合成烷氧基取代的苯甲醛的有效工艺
CN105503814B (zh) * 2015-12-07 2018-11-20 东北制药集团股份有限公司 一种洋茉莉醛的制备方法

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2521811A (en) * 1947-03-26 1950-09-12 Us Ind Chemicals Inc Amine derivatives of chloromethyl dihydrosafrol
GB1085645A (en) * 1964-06-09 1967-10-04 Kenya Pyrethrum Board Insecticidal compositions
FR1441954A (fr) * 1964-07-24 1966-06-10 Shell Int Research Compositions insecticides
GB1046209A (en) * 1964-07-24 1966-10-19 Shell Int Research Insecticidal compositions
FR2112069B1 (it) * 1970-09-11 1973-12-21 Ciba Geigy Ag
US3962415A (en) * 1971-09-14 1976-06-08 Airwick Industries, Inc. Insecticide evaporator comprising DDVP with synergized benzodioxole compound as stabilizer
GB1392100A (en) * 1972-09-13 1975-04-23 Beecham Group Ltd Insecticides

Also Published As

Publication number Publication date
IT7826144A0 (it) 1978-07-26
NZ187944A (en) 1980-03-05
DK334778A (da) 1979-01-29
BR7804832A (pt) 1979-04-10
EP0000537A1 (de) 1979-02-07
US4229445A (en) 1980-10-21
CS197328B2 (en) 1980-04-30
ATA544378A (de) 1980-05-15
PT68319A (de) 1978-08-01
AU3837178A (en) 1980-01-31
DE2734108A1 (de) 1979-02-08
ZA784267B (en) 1979-07-25
AT360277B (de) 1980-12-29
JPS5426330A (en) 1979-02-27
DE2860292D1 (en) 1981-02-19
TR19891A (tr) 1980-04-09
IL55215A0 (en) 1978-09-29

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