EP0000156B1 - 2-Arylamino-3,5-dinitro-benzotrifluorides, procédé de préparation et leur utilisation comme pesticides. - Google Patents

2-Arylamino-3,5-dinitro-benzotrifluorides, procédé de préparation et leur utilisation comme pesticides. Download PDF

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Publication number
EP0000156B1
EP0000156B1 EP78100172A EP78100172A EP0000156B1 EP 0000156 B1 EP0000156 B1 EP 0000156B1 EP 78100172 A EP78100172 A EP 78100172A EP 78100172 A EP78100172 A EP 78100172A EP 0000156 B1 EP0000156 B1 EP 0000156B1
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EP
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Prior art keywords
spp
dinitro
halogen
aniline
benzotrifluoride
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
EP78100172A
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German (de)
English (en)
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EP0000156A1 (fr
Inventor
Alfons Dr. Hartmann
Erich Dr. Klauke
Ingeborg Dr. Hammann
Peter Dr. Roessler
Volker Dr. Paul
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Bayer AG
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Bayer AG
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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.
  • ortho-standing substituents XR 1 and R 2 together with the two adjacent C atoms of the phenyl nucleus can form an optionally halogen-substituted dioxanyl ring;
  • X stands for S, SO or SO 2 ,
  • R 1 can additionally stand for unsubstituted alkyl, found.
  • the new 2-arylamino-3,5-dinitro-benzotrifluoride of the formula (I) have a higher insecticidal, acaricidal, development-inhibiting, fungicidal and bactericidal potency than the chemically obvious compounds of the same direction of action known from German Offenlegungsschrift 2,509,416.
  • the substances according to the invention thus represent an enrichment of the technology.
  • the compounds II, III, IV and V to be used as starting materials are known or can be prepared by known processes.
  • Inert organic solvents are suitable as diluents for process variants a) and b).
  • 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 are suitable as acid-binding agents. Potassium hydroxide, sodium hydride or sodium hydrogen carbonate is preferably used.
  • reaction temperatures can be varied within a wide range. In general, one works between -10 and + 150 °, preferably at 10 to 40 ° 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 the use of one or the other component in excess is also possible.
  • 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 sulfoxides are employed with equimolar amounts, preferably at 10-30 0, showing the sulfones with at least twice the molar amount of hydrogen peroxide, preferably at the boiling point of the solvent to.
  • the 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 crops in the concentrations necessary to combat fungi and bacteria. For these reasons, they are suitable for use as crop protection agents to combat fungi and bacteria. Fungitoxic agents in crop protection are used to control Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, 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 pathogens.
  • 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, Helminthosotiaumiaumisumiaisumiumis speciesaria Collium, Ventium-speciesizumiaumia-speciesum speciesum Heliumthosotaria speciesum speciesum Heliumthosotaria speciesum species species species Species, Thielaviopsis basicola Xanthomonas oryzae and Pseudomonas Lachrymans.
  • 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 and the like, as well as ULV cold and warm mist 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 and the like,
  • 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 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, 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,
  • 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 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%.
  • amounts of active ingredient of 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.
  • 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.
  • Bean plants Phaseolus vulgaris which are heavily infested with all stages of development of the common spider mite or bean spider mite (Tetranychus urticae) are sprayed to runoff point with the preparation of active compound.
  • 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 would be killed.
  • active compound 2 parts by weight of active compound are mixed with the stated 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.
  • 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 substance required for the desired concentration of active substance in the culture 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 in the stated ratio 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.
  • Example 2 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 powdered potassium hydroxide at room temperature. A solution of 13.6 g (50 mmol) of 2-chloro-3,5-dinitrobenzotrifluoride 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-trifluoromethylsulfonyl-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)

Claims (5)

1. 2-Arylamino-3,5-dinitrophénylfluoroformes de formule générale
Figure imgb0036
dans laquelle:
X représente O, S, SO ou SO2,
n représente un nombre entier de 1 à 4,
R' représente un groupe alkyle substitué par un halogène et/ou un groupe halogénoalcoxy, ou un groupe phényle éventuellement substitué par un halogène ou un groupe halogénoalkyle, halogénoalcoxy, halogénoalkylmercapto, halogénoalkysulfonyle, et le restes R2 sont identiques ou différents et choisis parmi l'hydrogène, les halogènes, les groupés cyano, nitro et alkyle éventuellement substitué par un halogène et/ou un groupe halogénoalcoxy, les substituants XR' et R2 en ortho pouvant former ensemble avec les deux atomes de carbone du noyau phényle un noyau dioxannyle éventuellement halogéné; si X représente S, SO ou SO2, le reste R' peut en outre représenter un groupe alkyle non substitué.
2. Procédé pour la préparation de 2-arylamino-3,5-dinitro-phénylfluoroformes de formule générale (I) selon la revendication 1, caractérisé en ce que:
a) on fait réagir une aniline de formule générale (II)
Figure imgb0037
dans laquelle:
X, R1, R2 et n ont la signification indiquée ci-dessus, avec le 2-chloro-3,5-dinitrophénylfluoro- forme de formule (III)
Figure imgb0038
en présence d'un accepteur d'acide, ainsi éventuellement que d'un agent diluant, ou bien
b) on fait réagir un 2-amino-3,5-dinitrophénylfluoroforme de formule (IV)
Figure imgb0039
avec un composé de formule générale (V)
Figure imgb0040
dans laquelle:
X R', R2 et n ont la signification indiquée ci-dessus et Hal représente le chlore ou le brome, en présence d'un accepteur d'acide, ainsi éventuellement que d'un agent diluant, ou bien
c) on transforme un composé de formule générale (I), qui a été préparé par la méthode a) ou b) et dans lequel R1, R2 et n ont la signification indiquée ci-dessus et X représente le soufre, en composé correspondant de formule (1) dans laquelle X représente SO ou SO2, au moyens d'agents oxydants, éventuellement en présence d'un agent diluant.
3. Agents de lutte contre les parasites, caractérisés en ce qu'ils contiennent des 2-arylamino-3,5-dinitrophénylfluoroformes de formule générale (I) selon la revendication 1.
4. Utilisation des 2-arylamino-3,5-dinitrophénylfluoroformes de formule générale (I) selon la revendication 1 pour la lutte contre les parasites.
5. Procédé pour la préparation d'agents de lutte contre les parasites, caractérisé en ce que l'on mélange des 2-arylamino-3,5-dinitrophénylfluoroformes de formule générale (I) selon la revendication 1 avec des agents diluants et/ou des substances tensioactives.
EP78100172A 1977-06-24 1978-06-15 2-Arylamino-3,5-dinitro-benzotrifluorides, procédé de préparation et leur utilisation comme pesticides. Expired EP0000156B1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE2728536 1977-06-24
DE19772728536 DE2728536A1 (de) 1977-06-24 1977-06-24 Neue 2-arylamino-3,5-dinitro- benzotrifluoride

Publications (2)

Publication Number Publication Date
EP0000156A1 EP0000156A1 (fr) 1979-01-10
EP0000156B1 true EP0000156B1 (fr) 1980-11-12

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EP78100172A Expired EP0000156B1 (fr) 1977-06-24 1978-06-15 2-Arylamino-3,5-dinitro-benzotrifluorides, procédé de préparation et leur utilisation comme pesticides.

Country Status (24)

Country Link
US (1) US4459304A (fr)
EP (1) EP0000156B1 (fr)
JP (1) JPS5412333A (fr)
AR (1) AR220913A1 (fr)
AT (1) AT360275B (fr)
AU (1) AU520355B2 (fr)
BG (1) BG32412A3 (fr)
BR (1) BR7803981A (fr)
CS (1) CS199734B2 (fr)
DD (1) DD139987A5 (fr)
DE (2) DE2728536A1 (fr)
DK (1) DK284678A (fr)
EG (1) EG13494A (fr)
ES (1) ES471086A1 (fr)
HU (1) HU180204B (fr)
IL (1) IL54966A (fr)
IT (1) IT7824874A0 (fr)
NZ (1) NZ187641A (fr)
PL (1) PL113964B1 (fr)
PT (1) PT68194A (fr)
RO (1) RO75488A (fr)
SU (1) SU805934A3 (fr)
TR (1) TR19901A (fr)
ZA (1) ZA783599B (fr)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
NZ192353A (en) * 1978-12-22 1982-03-16 Ici Australia Ltd Diphenylamine derivatives herbicidal compositions
IL61776A (en) * 1980-01-08 1984-05-31 Lilly Co Eli N-(nitrophenyl)-polyfluoroethoxy-benzenamines,their preparation,fungicidal and anticoccidial methods using them
US4304791A (en) * 1980-01-08 1981-12-08 Eli Lilly And Company Benzenamines, formulations, and fungicidal method
US4341772A (en) * 1980-05-05 1982-07-27 E. I. Du Pont De Nemours And Company Agricultural phosphorus-containing sulfenamides
US4366168A (en) * 1981-09-21 1982-12-28 Eli Lilly And Company Anticoccidial combinations
EP1871743A4 (fr) * 2005-04-11 2009-12-30 Univ Murdoch Composés antiparasitaires
CN102199095B (zh) 2010-03-22 2014-04-09 中国中化股份有限公司 一种取代二苯胺类化合物及其制备与应用
KR101599300B1 (ko) 2012-03-14 2016-03-03 시노켐 코포레이션 치환 디페닐아민 화합물 및 항종양제로서의 용도
CN111825585B (zh) * 2019-09-23 2021-12-14 山东康乔生物科技有限公司 一种含苄胺结构的芳基硫化物及其合成方法和应用

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3257190A (en) * 1962-12-10 1966-06-21 Lilly Co Eli Method of eliminating weed grasses and broadleaf weeds
US3332769A (en) * 1963-10-07 1967-07-25 Lilly Co Eli Method of eliminating germinating and seedling weed grasses and broadleaf weeds
US3403180A (en) * 1963-10-07 1968-09-24 Lilly Co Eli 4-trifluoromethyl-2, 6-dinitroanilines
US3442639A (en) * 1965-12-22 1969-05-06 Lilly Co Eli Process of selectively eliminating weeds
US3716585A (en) * 1970-08-05 1973-02-13 United States Borax Chem Alkoxy trifluoromethylaniline compounds
US4041172A (en) * 1972-12-20 1977-08-09 Imperial Chemical Industries Limited Compositions and methods for combating insect pests or fungal pests of plants
US3950377A (en) * 1972-12-20 1976-04-13 Imperial Chemical Industries Limited Diphenylamine derivatives
GB1430046A (en) * 1974-03-07 1976-03-31 Ici Ltd Nitrobenzene derivatives
GB1455207A (en) * 1974-11-06 1976-11-10 Ici Ltd Substituted dinitro-diphenylamines and their pesticidal compositions
US4215145A (en) * 1978-12-05 1980-07-29 E. I. Du Pont De Nemours And Company Miticidal, fungicidal, and ovicidal sulfenamides

Also Published As

Publication number Publication date
SU805934A3 (ru) 1981-02-15
DD139987A5 (de) 1980-02-06
CS199734B2 (en) 1980-07-31
IT7824874A0 (it) 1978-06-22
BG32412A3 (en) 1982-07-15
AT360275B (de) 1980-12-29
IL54966A (en) 1981-05-20
RO75488A (fr) 1980-11-30
IL54966A0 (en) 1978-08-31
PT68194A (en) 1978-07-01
ES471086A1 (es) 1979-09-16
EP0000156A1 (fr) 1979-01-10
EG13494A (en) 1982-03-31
PL207836A1 (pl) 1979-08-13
HU180204B (en) 1983-02-28
DE2860271D1 (en) 1981-02-05
PL113964B1 (en) 1981-01-31
AU3737378A (en) 1980-01-03
NZ187641A (en) 1980-05-08
TR19901A (tr) 1980-04-21
JPS5412333A (en) 1979-01-30
ATA458978A (de) 1980-05-15
DE2728536A1 (de) 1979-01-11
BR7803981A (pt) 1979-01-16
DK284678A (da) 1978-12-25
AU520355B2 (en) 1982-01-28
ZA783599B (en) 1979-06-27
US4459304A (en) 1984-07-10
AR220913A1 (es) 1980-12-15

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