Classifications

• • 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
  • C07D317/72—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 spiro-condensed with carbocyclic rings
• • 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
  • A01N43/04—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 one hetero atom
  • A01N43/06—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 one hetero atom five-membered rings
  • A01N43/12—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 one hetero atom five-membered rings 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
  • A01N47/12—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, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic 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
  • A01N47/18—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
  • 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
  • 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
  • A01N47/24—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing the groups, or; Thio analogues 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
  • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives 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
• • 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
  • A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
• • 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
  • A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic 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

Definitions

• the present invention relates to new benzodioxole derivatives, a process for their preparation and their use in insecticidal and acaricidal compositions as synergists.
• carbamates e.g. 2-iso-propoxy-phenyl-N-methyl carbamate or of phosphoric acid esters, e.g. 0,0-diethyl-0- [2-isopropyl-4-methyl-pyrimidin (6) yl] -thionophosphoric acid ester or of natural or synthetic pyrethroids with piperonyl ethers.
• phosphoric acid esters e.g. 0,0-diethyl-0- [2-isopropyl-4-methyl-pyrimidin (6) yl] -thionophosphoric acid ester or of natural or synthetic pyrethroids.
• piperonyl ethers such as ⁇ - [2- (2-hutoxy-ethoxy) -ethoxy] -4,5-methylenedioxy-2-propyl-toluene, known (see Bull. Org. Health Org.
• carboxylic acid esters in which R represents alkyl having 1 to 6 carbon atoms, which is optionally substituted by optionally substituted phenyl, cyclopropyl, which is optionally substituted by alkyl, alkenyl, haloalkyl or haloalkenyl, each having up to 6 carbon atoms, or for Phenyl which is optionally substituted.
• Carboxylic acid esters in which R 9 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 10 is phenyl which is optionally substituted by C 1-4 alkyl, halogen, in particular fluorine or chlorine, optionally substituted phenoxy; and optionally substituted benzyl is further substituted for furanyl, tetrahydrophthalimido, benzodioxole, which may be substituted by halogen, in particular chlorine, alkyl or alkenyl with up to 4-carbon atoms or benzyl is substituted, and also stands for cyclopentenone which is optionally substituted by C 1-4 alkyl, furfuryl, C 1-5 alkenyl.
• haloalkanes should be mentioned in particular 1,1,1-trichloro-2,2-bis (4-chloro- or 4-ethoxyphenyl) -ethane, 1,1,1-trichloro-2-hydroxy-2,2-bis- (4-chlorophenyl ) -ethane and 1,1-dichloro-2,2-bis (4-ethylphenyl) -ethane.
• insecticidal and / or acaricidal action of such active compound combinations is considerably 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 active ingredient combinations with the well-known synergist piperonyl butoxide.
• 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.
• benzodioxole derivatives according to the invention thus represent a valuable addition to the technology.
• Examples are: 5- (3.4-methylenedioxybenzyl) dioxolane 2-methyl-5- (3.4-methylenedioxybenzyl) dioxolane 2-ethyl-5- (3.4-methylenedioxybenzyl) dioxolane 2-n-propyl-5- (3.4-methylenedioxybenzyl) dioxolane 2-1-propyl-5- (3.4.-methylenedioxybenzyl) dioxolane 2-n-butyl 5- (3.4.-methylenedioxybenzyl) dioxolane 2-i-butyl-5- (3.4-methylenedioxybenzyl) dioxolane 2-t-butyl-5- (3.4-methylenedloxybenzyl) dioxolane 2-allyl-5- (3.4-methylenedioxybenzyl ) -dioxolane 2-methallyl-5- (3,4-methylenedioxybenzyl) dioxolane 2-crotyl-5- (3,4-methylenedioxybenzyl) dio
• the compounds of the formula II which serve as starting compounds for the preparation of the benzodioxole derivatives according to the invention are 3- (3,4-methylenedioxyphenyl) propanediol-1,2 and 3,4-methylenedioxybenzylethylene oxide. Both compounds are known, as are the carbonyl compounds of the formula III.
• the process for the preparation of the compounds according to the invention is optionally carried out with the use of suitable solvents or diluents.
• suitable solvents or diluents Practically all inert organic solvents can be considered as such. These include in particular aliphatic and aromatic, optionally chlorinated, hydrocarbons, such as benzene, toluene, xylene, methylene chloride, chloroform and carbon tetrachloride.
• the X are OH
• acidic catalysts e.g. Sulfuric acid or p-toluenesulfonic acid
• a catalyst such as boron trifluoride
• the reaction temperature can be varied within a wide range. Generally one works between 25 and 15o ° C, preferably between 7o and 12o ° C ..
• the reaction is generally allowed to proceed at normal pressure.
• the compounds when using 3- (3,4-methylenedioxyphenyl) propanediol-1,2 as the starting product, the compounds are preferably used in equimolar amounts.
• An excess of one or the other reaction component has no significant advantages.
• the two reaction components are reacted in one of the specified solvents in the presence of an acid catalyst at the specified temperatures.
• the resulting water is removed by azeotropic distillation.
• the carbonyl component is used in excess and thus serves as a reaction component and solvent.
• the reaction is preferably carried out in the presence of one of the specified catalysts at the specified temperatures. Working up after the reaction is carried out as usual by shaking with an organic solvent, washing, drying the organic phase and distilling off the solvent.
• the compounds according to the invention are characterized by their boiling point.
• active ingredient combinations of the benzodioxole derivatives of the formula (I) according to the invention with carbamates, carboxylic acid esters, phosphoric acid esters, cycloalkanes and haloalkanes show an excellent increase in activity compared to the individual active ingredients or their sum.
• Psylliodes chrysocephala Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Anthonomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermesthren spp., Dermesthren spp spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon ⁇ solstitialis, Costelytra zealandica.
• Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium phara onis, Vespa spp.
• Diptera e.g. Aedes spp., Anopholes app., Culex spp., Drosophila melanogaster, Musca spp.
• Fannia spp. Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia sppanus, Bibio hort , Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
• Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Chori .; Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
• the active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble powders, granules, aerosols, suspension - emulsion concentrates, seed powders, active substance-impregnated natural and synthetic substances , Fine encapsulation 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 heat mist formulations.
• formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents.
• extenders that is to say liquid solvents, pressurized liquefied gases and / or solid carriers, optionally 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.
• organic solvents can, for example, also be used as auxiliary solvents.
• liquid solvents aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, alcohols, such as butanol or glycol, and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar , 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, for example aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide; as solid carrier substances: natural rock meals, such as kaolin
• Adhesives such as carboxymethyl cellulose and 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 active substance content of the use forms prepared from the commercially available formulations can vary widely.
• 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 ingredient combinations are notable for an excellent residual action on wood and clay and for good stability to alkali on limed substrates.
• Test animals Musca domestica, Weymann strain (resistant to carbamates and phosphoric acid esters)
• 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. Will the 100 is not reached after 6 hours, the percentage of knock-down test animals is determined.

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• Life Sciences & Earth Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Pest Control & Pesticides (AREA)
• Plant Pathology (AREA)
• Health & Medical Sciences (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Environmental Sciences (AREA)
• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Heterocyclic Compounds That Contain Two Or More Ring Oxygen Atoms (AREA)

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• 1977
  • 1977-08-10 DE DE19772736017 patent/DE2736017A1/de active Pending
• 1978
  • 1978-07-31 EP EP78100554A patent/EP0000760A1/fr not_active Withdrawn
  • 1978-08-02 US US05/930,282 patent/US4199593A/en not_active Expired - Lifetime
  • 1978-08-07 IL IL7855302A patent/IL55302A0/xx unknown
  • 1978-08-08 IT IT7826603A patent/IT7826603A0/it unknown
  • 1978-08-08 TR TR19759A patent/TR19759A/xx unknown
  • 1978-08-09 BR BR7805091A patent/BR7805091A/pt unknown
  • 1978-08-09 ZA ZA00784511A patent/ZA784511B/xx unknown
  • 1978-08-09 AU AU38770/78A patent/AU3877078A/en active Pending
  • 1978-08-09 DK DK351678A patent/DK351678A/da unknown
  • 1978-08-09 JP JP9628378A patent/JPS5441877A/ja active Pending

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