Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
  • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
  • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
• • 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
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
• • 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
  • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
  • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
  • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
  • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
  • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
  • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
  • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
  • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D271/00—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms
  • C07D271/02—Heterocyclic compounds containing five-membered rings having two nitrogen atoms and one oxygen atom as the only ring hetero atoms not condensed with other rings
  • C07D271/10—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles
  • C07D271/113—1,3,4-Oxadiazoles; Hydrogenated 1,3,4-oxadiazoles with oxygen, sulfur or nitrogen atoms, directly attached to ring carbon atoms, the nitrogen atoms not forming part of a nitro radical
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

• R 1 represents alkyl, cycloalkyl, aryl, aralkyl, heteroaryl, which may optionally be substituted
• R 2 represents optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted hetaryl or R 1 and R 2 together with the nitrogen atom to which they are attached form a cycle
• pyrimidinyl Pyrrolyl, isothiazolyl, oxazolyl, thienyl, furyl, pyridazinyl, pyrazinyl, isoxazolyl, thiazolyl, pyridyl, imidazolyl, benzimidazolyl.
• the optionally substituted radicals of the general formulas can carry one or more, preferably 1 to 3, in particular 1 or 2 identical or different substituents.
• Examples of preferred substituents are:
• Halogen preferably fluorine, chlorine and bromine, iodine, especially fluorine, chlorine and bromine; Haloalkoxy and haloalkylthio, and their oxides, preferably having 1 to 4, in particular 1 or 2, carbon atoms and preferably 1 to 9, in particular 1 to 5, halogen atoms, the halogen atoms being the same or different and, as halogen atoms, preferably fluorine, chlorine or bromine, in particular fluorine are such as trifluoromethoxy, trifluoroethoxy, difluoromethoxy, pentafluoroethoxy, tetrafluoroethoxy, trifluorochloroethoxy, trifluoromethylthio; Alkoxy preferably having 1 to 4, in particular 1 or 2, carbon atoms, such as methoxy, ethoxy, n- and i-propyloxy and n-, i-, see- and t-butyloxy; Alkylthio
• Oxygen, sulfur and nitrogen are preferred as heteroatoms.
• exemplary and preferred are pyrimidinyl, pyrrolyl, isothiazolyl, oxazolyl, thienyl, Pyridazinyl, pyrazinyl, isoxazolyl, thiazolyl, pyridyl and imidazolyl called.
• one of the following groups can be used as a substituent for alkyl:
• substituents for cycloalkyl which may be mentioned are: alkyl, alkoxy, alkylthio which may be substituted, unsubstituted or substituted aryl, aryloxy or arylthio.
• substituents for aryl and hetaryl include and are preferably the above-mentioned and additionally optionally substituted alkyl, optionally substituted aryl or hetaryl.
• Formula (I) provides a general definition of the 2-dichloromethyl-1,3,4-oxadiazoles to be used according to the invention.
• Preferred compounds of the formula (I) are those X stands for a direct bond or for one of the following groupings: -O-, -S-, -S (O) -, -SO 2 -, -NH- or -NR 2 - R 1 represents optionally substituted C 1 -C 15 Alkyl, optionally substituted C 3 -C 8 -cycloalkyl, optionally substituted phenyl or optionally substituted heteroaryl,
• R 2 represents optionally substituted C 1 -C 15 alkyl, optionally substituted C 3 -C 8 cycloalkyl, optionally substituted phenyl or optionally substituted heteroaryl and the substituents for alkyl, cycloalkyl, phenyl and hetaryl each have the meanings given above or
• R 1 and R 2 together with the nitrogen atom to which they are attached form a 5- or 6-membered cycle.
• R 1 for methyl, ethyl, n-propyl, i-propyl, n-butyl, sec.-butyl, i-butyl, t.-butyl, i-pentyl, hexyl, undecyl, methoxy, ethoxy, methylthiomethyl, trifluoromethyl, cyclopropyl , Cyclohexyl, 9-dodecenyl, undecenyl; furthermore for unsubstituted or single, double or triple, identically or differently substituted by chlorine or methoxy-substituted phenoxymethyl, phenoxyethyl or 2-phenoxyethyl; further for phenyl, benzyl, phenyl, furyl, pyridyl, imidazolyl or benzimidazolyl or substituted by methyl, ethyl, t-butyl, chlorine, trifluoromethyl, methoxy,
• X stands for a direct bond or for oxygen and sulfur and R 1 stands for optionally substituted alkyl having 1 to 6 carbon atoms, the following being suitable as substituents: halogen, in particular fluorine and / or chlorine; optionally substituted alkenyl having 1 to 6 carbon atoms, the substituents being alkyl or halogen, in particular fluorine or chlorine; optionally substituted cycloalkyl having 3 to 6 carbon atoms, the substituents being in particular alkyl substituents and alkoxy substituents and haloalkyl and haloalkoxy substituents having 1 to 4 carbon atoms; optionally substituted aryl, in particular optionally substituted phenyl with 1 to 2 substituents defined in aryl; optionally substituted phenoxy, phenylthio with in particular 1 to 2 substituents defined in aryl; by optionally with alkyl, alkoxy and alkylthio with 1 to 6 carbon atoms, haloalkyl,
• phenyl furthermore stands for optionally substituted phenyl, the substituents being halogen, in particular chlorine, fluorine; Alkyl of 1 to 6 carbon atoms such as methyl, ethyl, propyl, isopropyl, butyl, t-butyl; Alkoxy and alkylthio with 1 to 6 carbon atoms such as methoxy, ethoxy, i-propoxy, methylmercapto; Haloalkyl with 1 to 4 carbon atoms such as dichloromethyl, trifluoromethyl; Haloalkoxy with 1 to 4 carbon atoms such as trifluoromethoxy; Haloalkylthio with 1 to 4 carbon atoms such as, for example, trifluoromethylthio and their oxides, such as, for example, trifluoromethylsulfonyl, phenyl and phenoxy with the above-mentioned substituents are suitable;
• R 1 and X have the meaning given above, optionally in the presence of a diluent and in the presence of a water-releasing agent, or if
• R 1 and X have the meaning given above, with 2,2-dichloro-N- (1-methylethyl) ethanimidoyl chloride of the formula (IV) optionally cyclized in the presence of a solvent.
• N'-dichloroacetyl-6-chloronicotinic acid hydrazide and polyphosphoric acid (PPA) are used as the water-releasing agent, the course of the reaction of the preparation process (A) can be represented by the following formula:
• the course of the reaction in preparation process (B) can be represented by the following formula:
• Formula (II) provides a general definition of the compounds required as starting materials for carrying out production process (A).
• R 1 and X preferably have those meanings which have already been mentioned as preferred for these radicals in the description of the substances of the formula (I) to be used according to the invention.
• the compounds of the formula (II) are largely known or can be prepared in a simple, analogous manner by known processes (cf., for example, Tetrahedron Lett, (23), 2333-2335, 1972; Bull. Soc. Chim. Fr., (3 -4, Pt.2), 333-336, 1977; J. Heterocycl. Chem., 17 (4), 625-629, 1980; Justus Liebigs Ann.
• R 1 and X and n preferably represent those meanings which already exist in the description of the substances to be used according to the invention Formula (I) were mentioned as preferred for these radicals.
• the compounds of formula (III) are generally known compounds of organic chemistry.
• the 2,2-dichloro-N- (1-methylethyl) ethanimidoyl chloride which is furthermore required as starting material for carrying out process (B) according to the invention is also known (US Pat. No. 4,781,752).
• the processes (A) and (B) according to the invention for the preparation of the new 2-dichloromethyl-1,3,4-oxadiazoles of the formula (I) can be carried out in a customary manner by generally known processes in which the compounds of the formula (II ) or (III) in an inert organic solvent, such as toluene, 1,2-dichlorobenzene, xylene or dimethylacetamide at temperatures between 20 ° C and 170 ° C, preferably 30 ° C and 140 ° C, optionally on a water separator, with a water-releasing agents, such as, for example, phosphorus oxychloride, polyphosphoric acid, p-toluenesulfonic acid, 2,2-dichloro-N- (1-methylethyl) -ethanimidoyl chloride or dichloroacetyl chloride, heated (cf. Preparation Examples).
• an inert organic solvent such as toluene, 1,2-dich
• the active substances are suitable for controlling animal pests, preferably nematodes and acarids, which are found in agriculture, in forests and in the hygiene sector. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• the pests mentioned above include in particular:
• Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocorptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Chori ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
• the active compounds according to the invention act not only against plant, hygiene and stored product pests, but also in the veterinary sector against animal parasites (ectoparasites and endoparasites) such as tick ticks, leather ticks, space mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, Hair lice, featherlings, height and endoparasitic worms. For example, they show excellent activity against ticks, such as Boophilus microphus.
• the active compounds according to the invention are notable for high nematicidal and acaricidal activity.
• the active compounds according to the invention also show leaf-insecticidal activity.
• the active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.
• formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is to say emulsifiers and / or foam-generating agents.
• organic solvents can, for example, also be used as auxiliary solvents.
• auxiliary solvents include aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral fumes and vegetable oils, 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 solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• aromatics such as xylene, toluene or alkylnaphthalenes
• chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzen
• Solid carrier materials are suitable: e.g. ammonium salts and natural rock powder, such as kaolins, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powder, such as highly disperse silica, aluminum oxide and silicates, as solid carrier materials for granules are possible: e.g.
• suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
• suitable emulsifiers and / or foam-generating agents are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
• dispersants for example lingnine sulfite liquor and methyl cellulose.
• Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
• Other additives can be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocy blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
• inorganic pigments e.g. Iron oxide, titanium oxide, ferrocy blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc are used.
• the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
• the active compounds according to the invention can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.
• a mixture with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.
• the active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.
• the active compounds according to the invention can be applied both before and after emergence of the plants.
• the amount of active ingredient used can vary over a wide range. It essentially depends on the type of effect desired. In general, the application rates are between 0.01 and 10 kg of active ingredient per hectare of soil, preferably between 0.05 and 5 kg per ha.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• the lettuce roots are examined for nematode infestation (root galls) and the effectiveness of the active ingredient is determined in%.
• the efficiency is 100% if the infestation is completely avoided, it is 0% if the infestation is just as high as that of the control plants in untreated, but equally contaminated soil.
• the active ingredients 1, 2, 3, 7, 8, 10 and 15 showed an efficiency of at least 95% at an active ingredient concentration of 20 ppm.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
• 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)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)

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• 1993
  • 1993-04-29 DE DE19934314037 patent/DE4314037A1/de not_active Withdrawn
• 1994
  • 1994-04-18 WO PCT/EP1994/001195 patent/WO1994024868A1/de not_active Application Discontinuation
  • 1994-04-18 EP EP94914397A patent/EP0696171A1/de not_active Ceased
  • 1994-04-18 AU AU78799/94A patent/AU7879994A/en not_active Abandoned
  • 1994-04-18 JP JP6522518A patent/JPH08509214A/ja active Pending

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