Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C251/00—Compounds containing nitrogen atoms doubly-bound to a carbon skeleton
  • C07C251/72—Hydrazones
• • 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
  • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
  • A01N43/647—Triazoles; Hydrogenated triazoles
  • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
• • 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
  • C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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 ring carbon atoms
  • C07D249/12—Oxygen or sulfur atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
  • C07D405/04—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

• the present invention relates to the new compounds of the formula I in which (R) n is hydrogen or 1 to 4 identical or different radicals of the group consisting of halogen, nitro, cyano, (C 1 -C 6 ) alkyl, (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkylthio (where the alkyl, alkoxy and alkylthio groups may themselves be substituted by one or more halogen atoms) or a phenyl or phenoxy group (which in turn may be substituted by halogen, alkyl or alkoxy can) or a benzene ring ankondensi ey methylenedioxy group, and R 1 is straight or branched (C 1 -C 18) alkyl, (C 1 -C 6) alkoxyalkyl, di- (C 1 -C 4 alkoxyäthyl), di (C 1 -C 4 ) alkylaminoethyl or (C 5
• the compounds are obtained by using compounds of the formula wherein R 2 is an alkyl radical, cyclized by means of phosgene or a low molecular weight carbonic acid ester, the compounds of the formula obtained saponified to the corresponding acids and the latter decarboxylated.
• the method according to the invention is characterized by a surprisingly smooth course.
• the fact that the amidrazones of formula II can be cyclized smoothly and under very mild conditions with phosgene or carbonic acid esters is particularly surprising.
• ring closure with phosgene or carbonic acid ester was only to be expected under much more vigorous conditions than the ones described.
• the decarboxylation of the free acids to the compounds of the formula I- which proceeded particularly easily and without the use of catalysts, was likewise not to be expected.
• the reaction II ⁇ III is preferably carried out at temperatures from -20 ° to +6 0 ° C.
• the cyclization with phosgene is carried out in the presence of bases as acid-binding agents and proton-free solvents.
• bases are, for example, triethylamine, trimethylamine, N, N-dimethylaniline or pyridine.
• proton-free solvents are benzene, ether, acetone, Dioxane THF and the like in question.
• the order of addition of the reactants is not critical. You can e.g. Place all reactants at a lower temperature and then warm to the reaction temperature. You can also use one or two reactants - e.g. submit the compound of formula II and the base - in whole or in part and add phosgene and optionally the rest of the reactants at the reaction temperature. In general, the reactants are used in approximately stoichiometric amounts or with a slight excess of one component.
• the base required for the phosgenation (preferably a tertiary amine) is preferably used in a stoichiometric excess of up to 15% and phosgene or carbonic acid ester in an excess of up to 20%.
• the compound of formula III formed can be isolated by filtering off the salts by distilling off the solvent. It is saponified with aqueous or aqueous-alcoholic alkali, preferably NaOH, optionally also without removal of the solvent, the alkali salts of the free acid which are soluble in the aqueous phase initially being formed.
• the free acid is obtained by acidifying the aqueous phase and can be obtained by simple heating, preferably in an organic solvent or by heating the aqueous suspension to temperatures of 80 ° to 150 ° C., preferably 90 ° to 120 ° C., or at the boiling point of the solvent or suspension agent used are decarboxylated.
• the triazolone of formula I obtained can be isolated by removing the solvent (for example suction or distillation) and, if appropriate, further purified (for example by recrystallization).
• amidrazones of the formula II are obtained in a manner known per se, for example by reacting phenyldiazonium salts with ⁇ -haloacetoacetic esters and further reaction of the ⁇ -halogen- ⁇ -phenylhydrazono-glyoxylic acid ester of the formula obtained with amines of the formula R 1 -NH 2 in a manner known per se. (Literature: C. r. 134, 1213 (1902); J. Chem. Soc. 87, 1859 (1905); Ber. 50, 1482 (1917))
• the compounds of formula I are valuable pesticides. They have above all insecticidal, in particular acaricidal and ovicidal, and in some cases also fungicidal and herbicidal properties and can be used alone or in a mixture with other crop protection agents.
• the compounds according to the invention are distinguished. due to its very good activity against those spider mite strains that have become resistant to chlorinated hydrocarbons and phosphoric acid derivatives. As is well known, this resistance is becoming an increasingly serious problem in many countries and growing regions.
• the activity against eggs is also particularly good, with the residue effect which prevents the reconstruction of populations being emphasized.
• the ovicidal effect also extends to eggs from various types of insects.
• the invention therefore also relates to crop protection agents which are characterized by a content of compounds of the formula I.
• Wettable powders are preparations which are uniformly dispersible in water and which, in addition to the active ingredient, contain a diluent or inert substance, as well as wetting agents, e.g. polyoxyethylated alkylphenols, polyoxyethylated oleyl or stearylamines, alkyl or alkylphenyl sulfonates and dispersants, e.g. sodium lignosulfonate, 2,2'-di-naphthylmethane-6,6'-disulfonic acid sodium or oleylmethyl-tauric acid sodium.
• wetting agents e.g. polyoxyethylated alkylphenols, polyoxyethylated oleyl or stearylamines, alkyl or alkylphenyl sulfonates and dispersants, e.g. sodium lignosulfonate, 2,2'-di-naphthylmethan
• Emulsifiable concentrates are made by dissolving the weight in an organic solvent, e.g. Receive butane cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics.
• organic solvent e.g. Receive butane cyclohexanone, dimethylformamide, xylene or higher-boiling aromatics.
• Dispersions are obtained by suspending the active ingredient in an organic solvent, such as paraffinic mineral oils, liquid triglycerides and / or liquid aromatic esters.
• organic solvent such as paraffinic mineral oils, liquid triglycerides and / or liquid aromatic esters.
• Dusts are obtained by grinding the active ingredient with finely divided, solid substances, e.g. Talcum natural clays, such as kaolin, bentonite, pyrophillite or diatomaceous earth.
• Talcum natural clays such as kaolin, bentonite, pyrophillite or diatomaceous earth.
• the commercially available are used optionally diluted in the usual way, for example in the case of wettable powders, dispersions and emulsifiable concentrates using water. Dust-like preparations and sprayable solutions are no longer diluted with other inert substances before use.
• the application rate required varies with the external conditions such as temperature, humidity and others. It can fluctuate within wide limits.
• An emulsifiable concentrate is obtained from:
• a wettable powder easily dispersible in water is obtained by:
• a dispersion concentrate that is easily dispersible in water is obtained by stepping mixes and ground in a attritor to a fineness of less than 5 microns.
• the sprayed plants were then placed in the greenhouse at approx. 20 ° C.
• the microscopic inspection 8 days after the spraying showed that all movable and immobile stages of the population, including the eggs, had been killed.
• Apple trees infested with resistant fruit tree spider mites (Metatetranychus ulmi, strain "Dardar") were treated with the aqueous suspension of an emulsion concentrate of the compounds listed in Table II until they started to drip. After the plants had been placed in the greenhouse at about 20 ° C., they were checked after 8 days.

Landscapes

• 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)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Plural Heterocyclic Compounds (AREA)

Applications Claiming Priority (2)

Publications (1)

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Cited By (9)

Families Citing this family (5)

• 1977
  • 1977-06-03 DE DE19772725148 patent/DE2725148A1/de active Pending
• 1978
  • 1978-05-26 ES ES470219A patent/ES470219A1/es not_active Expired
  • 1978-06-01 IL IL7854831A patent/IL54831A0/xx unknown
  • 1978-06-01 EP EP78100026A patent/EP0000014A1/de not_active Withdrawn
  • 1978-06-01 IT IT24121/78A patent/IT1094947B/it active
  • 1978-06-02 ZA ZA00783182A patent/ZA783182B/xx unknown
  • 1978-06-02 JP JP6587278A patent/JPS543071A/ja active Pending
  • 1978-06-02 SU SU782623269A patent/SU791199A3/ru active
  • 1978-06-02 BR BR787803552A patent/BR7803552A/pt unknown

Non-Patent Citations (1)

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