Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D319/00—Heterocyclic compounds containing six-membered rings having two oxygen atoms as the only ring hetero atoms
  • C07D319/04—1,3-Dioxanes; Hydrogenated 1,3-dioxanes
  • C07D319/08—1,3-Dioxanes; Hydrogenated 1,3-dioxanes condensed with carbocyclic rings or ring systems
• • 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
  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
  • A01N33/18—Nitro compounds
• • 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
  • A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
  • A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
  • A01N33/18—Nitro compounds
  • A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
• • 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
  • A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
  • A01N37/34—Nitriles

Definitions

• the present invention relates to new 2-arylamino-3,5-dinitro-benzotrifluoride, processes for their preparation and their use as pesticides.
• the new 2-arylamino-3,5-dinitro-benzotrifluorides of the formula (I) have a higher insecticidal, acaricidal, development-inhibiting, fungicidal and bactericidal potency than the chemically obvious compounds of the same action known from German Offenlegungsschrift 2,509,416.
• the substances according to the invention thus represent an enrichment of technology.
• reaction sequence can be represented by the following formula:
• the compounds II, III, IV and V to be used as starting materials are known or can be prepared by known processes
• A13 diluents for process variants a) and b) are inert organic solvents. Dimethylformamide or tetrahydrofuran are preferably used. Sometimes it is also advantageous to work in aqueous suspension.
• bases such as alkali or alkaline earth metal hydroxides, carbonates or hydrides.
• bases such as alkali or alkaline earth metal hydroxides, carbonates or hydrides.
• Potassium hydroxide, sodium hydride or sodium hydrogen carbonate is preferably used.
• reaction temperatures can be varied within a wide range. you work between -10 and + 150 °, preferably at 10 to 10 °, if an organic solvent is used, and at 100 °, when working in aqueous suspension. In the latter case, the temperature can be increased by using a pressure vessel.
• the reactants are usually used in equimolar amounts, but it is possible to use one or the other component in excess. .
• the preparation method c it is preferred to work in glacial acetic acid as the solvent and to use hydrogen peroxide as the oxidizing agent.
• the reaction is carried out with equimolar amounts, preferably at 10-30 °, and to prepare the sulfones with at least twice the molar amount of hydrogen peroxide, preferably at the boiling point of the solvent.
• Otiorrhynchus sulcatus Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilia, Hypera postica, Dermestes spp., Trogoderma app., Anthrenus app., Attagenua spp., Lyctus spp., Meligethes aeneua, Ptinua app., Niptus hololeucua, Gibbol., Gibbol. Tenebrio molitor, Agriotes app., Conoderua spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
• Bibio hortulanus 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., Anblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.,. Chori ., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
• Plant parasitic nematodes include Pratylenchus spp., Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp.
• the active substances according to the invention have a strong fungitoxic and bacteriotoxic effect. They do not damage cultivated plants in the concentrations necessary to combat fungi and bacterias. For these reasons, it is suitable for use as a crop protection agent for combating fungi and bacteria. Fungitoxic coats in crop protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Bygomycetes, Ascomycetes, Basidiomycetes, Deuteromycetes.
• the active compounds according to the invention have a broad spectrum of activity and can be used against parasitic fungi which attack above-ground parts of plants or attack the plants from the ground, and against seed-borne disease-causing agents.
• the compounds according to the invention act against fungi and bacteria which attack various crop plants, such as Pythium species, Phytophthora species, Fusarium species, Verticillium alboatrum, Phialophora cinerescens, Sclerotinia sclerotiorum, Botrytis species, Cochliobolus miyabeanus, Mycosphaerella musicola, Cercospora personata, Helminthosotaria species species, Helminthosotaria species species Venturia inaequalis, Rhizoctonia species, Thielaviopsis basicola, Xanthomonas oryzae and Pseudomonas Lachrymans.
• crops plants such as Pythium species, Phytophthora species, Fusarium species, Verticillium alboatrum, Phialophora cinerescens, Sclerotinia sclerotiorum, Botrytis species, Cochliobolus miy
• the compounds according to the invention act both against cereal diseases, e.g. Puccinia recondita, Erysiphe graminis, Tilletia caries as well as against rice diseases, e.g. Pyriculania oryzae, Pellicularia sasakii.
• cereal diseases e.g. Puccinia recondita, Erysiphe graminis, Tilletia caries
• rice diseases e.g. Pyriculania oryzae, Pellicularia sasakii.
• the active ingredients 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 ingredient-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, dusts, foams, pastes, soluble powders, granules, aerosols, suspension emulsion concentrates, seed powders, active ingredient-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
• 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 alkyl phthalins, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethlene 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 solvents such as dimethylformamide, and dimethyl as well as 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 carriers: natural rock flour, such as kaolin, clay, talc, chalk
• 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, for example 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.
• inorganic pigments for example 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 compounds 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 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 ingredients When used against hygiene pests and pests of stored products, the active ingredients are distinguished by an excellent residual action on wood and clay and by a good stability to alkali on limed substrates.
• the active compound concentrations in the use forms can be varied within a substantial range. They are generally between 0.1 and 0.00001 percent by weight, preferably between 0.05 and 0.0001%.
• active compound 0.001 to 50 g per kilogram of seed, preferably 0.01 to 10 g, are generally required.
• active ingredient For soil treatment, amounts of active ingredient from 1 to 1000 g per cbm of soil, preferably from 10 to 200 g, are required.
• the kill is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
• cabbage leaves (Brassica oleracea) are sprayed to runoff point and populated with horseradish leaf beetle larvae (Phaedon Cochleariae).
• the kill is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
• active compound 2 parts by weight of active compound are mixed with the one specified. Amount of solvent, emulsifier and enough water to form a 1% mixture which is diluted with water to the desired concentration.
• Egg clutches with 30 eggs on filter paper are moistened with 1 ml active ingredient solution of the specified concentration in ppm (parts per million) and observed in plastic cans until the young larvae hatch.
• the young larvae are fed with corn leaves that have been sprayed with the specified concentration of the active ingredient solution on the same day as the eggs.
• egg clutches are treated in the same way with solvent and emulsifier of the appropriate concentration and fed with corn leaves. The results are shown in the table below.
• active compound 4 parts by weight of active compound are mixed with the stated amount of solvent, emulsifier and enough water to produce a 1% mixture which is diluted with water to the desired concentration.
• the eggs of the test animals are placed on a bowl of artificial feed into which the selected concentration of the active ingredient mixture is incorporated, so that the specified amount of active ingredient in ppm (parts per million) is reached.
• the development up to the hatching of the flies is observed.
• the amount of active ingredient required for the desired active ingredient concentration in the nutrient medium is mixed with the stated amount of the solvent mixture.
• the concentrate is mixed more thoroughly with the liquid nutrient medium, cooled to 42 ° C, and poured into Petri dishes with a diameter of 9 cm. Control plates are also set up without admixture.
• the plates are inoculated with the fungus species listed in the table and two bacteria and incubated at about 21 ° C.
• the evaluation takes place after 4 - 10 days depending on the growth rate of the organisms.
• the radial growth on the treated culture media is compared with the growth on the control culture media.
• the pathogen growth is rated with the following key figures:
• a suspension of 27.0 g (0.1 mol of 2-chloro-3,5-dinitro-benzotrifluoride and 17.7 g (0.1 mol) of 4-trifluoromethoxy-aniline in 200 ml of water is heated to boiling.
• 9.3 g (0.11 mol) of sodium bicarbonate are added over a period of 30 minutes and the mixture is heated under reflux for a further 2 hours and left to stand at room temperature overnight, during which a yellow, crystalline solid separates out, after suction and washing with petroleum ether, 36.8 g of 2- (4-trifluoromethoxy-anilino) -3,5-dinitro-benzotrifluoride, mp. 104 °.
• a solution of 11.2 g (50 mmol) of 4-trifluoromethylsulfonyl-aniline in 100 ml of dry dimethylformamide is mixed in portions with 5.6 g (100 mmol) of pulverized potassium hydroxide at room temperature.
• a solution of 13.6 g (50 mmol) of 2-chloro-3,5-dinitrobeazotrifluoride in 80 ml of dry dimethylformamide is then added dropwise at 25 °. The mixture is stirred at room temperature overnight, filtered, 100 ml of glacial acetic acid are added to the filtrate and the mixture is discharged onto ice.
• 11.5 g of 2- (4-trifluoromethylsullonyl-anilino) -3,5-dinitro-benzotrifluoride are suctioned off in the form of yellow crystals. Mp 172 °.

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

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Citations (1)

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• 1977
  • 1977-06-24 DE DE19772728536 patent/DE2728536A1/de not_active Withdrawn
• 1978
  • 1978-06-15 EP EP78100172A patent/EP0000156B1/fr not_active Expired
  • 1978-06-15 DE DE7878100172T patent/DE2860271D1/de not_active Expired
  • 1978-06-19 PT PT68194A patent/PT68194A/pt unknown
  • 1978-06-19 BG BG040141A patent/BG32412A3/xx unknown
  • 1978-06-20 TR TR19901A patent/TR19901A/xx unknown
  • 1978-06-21 IL IL54966A patent/IL54966A/xx unknown
  • 1978-06-21 EG EG383/78A patent/EG13494A/xx active
  • 1978-06-21 NZ NZ187641A patent/NZ187641A/xx unknown
  • 1978-06-22 SU SU782627200A patent/SU805934A3/ru active
  • 1978-06-22 PL PL1978207836A patent/PL113964B1/pl unknown
  • 1978-06-22 IT IT7824874A patent/IT7824874A0/it unknown
  • 1978-06-22 AU AU37373/78A patent/AU520355B2/en not_active Expired
  • 1978-06-22 CS CS784126A patent/CS199734B2/cs unknown
  • 1978-06-22 JP JP7493978A patent/JPS5412333A/ja active Pending
  • 1978-06-23 DK DK284678A patent/DK284678A/da unknown
  • 1978-06-23 AR AR272705D patent/AR220913A1/es active
  • 1978-06-23 RO RO7894450A patent/RO75488A/fr unknown
  • 1978-06-23 DD DD78206241A patent/DD139987A5/de unknown
  • 1978-06-23 BR BR787803981A patent/BR7803981A/pt unknown
  • 1978-06-23 AT AT458978A patent/AT360275B/de not_active IP Right Cessation
  • 1978-06-23 HU HU78BA3668A patent/HU180204B/hu unknown
  • 1978-06-23 ZA ZA00783599A patent/ZA783599B/xx unknown
  • 1978-06-23 ES ES471086A patent/ES471086A1/es not_active Expired
• 1979
  • 1979-03-28 US US06/024,845 patent/US4459304A/en not_active Expired - Lifetime

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