Alkylation of fluorophenols and phenolic aldehydes with 5-phenyl(p-tolyl)-3-chloromethylisoxazole under the Williamson reaction conditions afforded the corresponding ethers. Condensation of the resulting phenolic aldehyde derivatives and 5-phenyl(p-tolyl)isoxazole-3-carbaldehydes with p-fluoroaniline resulted in fluorine-containing azomethines. Acylation of fluorinated amines with 5-(p-tolyl)isoxazole- and 4,5- dichloroisothiazole-3-carbonyl chlorides gave rise to fluorinated amides bearing isoxazole and isothiazole fragments, representatives of which showed a synergistic effect in compositions with insecticides.
Copper(II) chloride and bromide complexes with 4,5-dihlorizotiazol-N-(2-hydroxyethyl)-3-carboxamide (L) with the compositions [CuLHal 2 ] n , where Hal = Cl – , Br – , are synthesized. The X-ray analysis revealed that the ligand is coordinated to the copper(II) atoms tridentate by the nitrogen atom of the heterocycle and two exocyclic oxygen atoms to form polymer chains. The copper bromide complex showed a synergistic effect in the compositions of insecticides Kerber and Vitan.
Reaction of 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles with substituted phenols under the conditions of Williamson reaction afforded the corresponding 3-aryloxymethyl-5-phenyl(p-tolyl)isoxazoles. Treating the latter with sodium methylate, sodium phenyl(benzyl, furfuryl)thiolates and morpholine in methanol resulted in the replacement of the chlorine atom in 3-chloromethyl-5-phenyl(p-tolyl)isoxazoles by methoxy-, phenyl-(benzyl, furfuryl)sulfanyl groups and morpholine residue.
By acylation of biphenyl and naphthalene 4,5-dichloroisothiazol-3-carbonyl chloride under Friedel-Crafts reaction conditions p -biphenyl- and 1-naphthyl-(4,5-dichloroisothiazol-3-yl) ketones, respectively, were synthesized. It was found that acylation of biphenyl in the dichloromethane medium proceeds nonselectively and leads to a mixture of para- and meta- isomers but in the nitrobenzene solution only the para- isomer is formed. By the reaction of p -biphenyl-(4,5 dichlorisothiazol-3-yl) ketone with sodium phenolate p -biphenyl (5-phenylthio-4-chlorisothiazol-3-yl) ketone was obtained.
Condensation of functionally substituted benzaldehydes and isoxazolyl-3-carbaldehyde with dimedone in the presence of catalytic amounts of triethylamine in methanol afforded functionally substituted 2,2′-arylmethylenebis(3-hydroxy-5,5-dimethylcyclohex-2-enones).
The method of synthesis was developed of esters of benzoic, 2-chlorobenzoic, 5-phenylisoxazole-3-carboxylic, 5-tolylisoxazole-3-carboxylic, and 4,5-dichloroisothiazole-3-carboxylic acids with some aliphatic and substituted aromatic alcohols. The latter were obtained by reduction of aldehydes used in perfumery.
Condensation of substituted benzaldehydes of vanillin series with dimedone in methanol solution in the presence of catalytic quantities of triethylamine afforded 2,2′-arylmethylenebis(3-hydroxy-5,5-dimethylcyclohex-2-en-1-ones. By catalytic cyclization of the latter in boiling benzene in the presence of sulfo cation exchanger FIBAN K-1 as catalyst 3,3,6,6-trimethyl-9-aryl-3,4,5,6,7,9-hexahydro-1 H -xanthene-1,8(2 H )-diones were synthesized.
By the condensation of substituted aldehydes of vanillin series with 1,3-propanediol in boiling benzene in the presence of sulfo cation exchanger FIBAN K-1 as catalyst functionally 2-R-substituted 1,3-dioxanes were synthesized.
Condensation of substituted benzaldehydes of the vanillin series with propane-1,2-diol and 3-chloropropane-1,2-diol in boiling benzene in the presence of FIBAN K-1 sulfonated cation exchanger as catalyst gave the corresponding substituted 1,3-dioxolanes.
The androstane and pregnane steroids 1-10 were verified to have insecticidal activity for larvae of the Colorado beetle Leptinotarsa decemlineata. Insect growth and development regulators were found among these compounds.
The toxicity of 7-substituted steroids 1-8 for Colorado beetle (Leptinotarsa decemlineata Say.) larvae was studied. The most active compound is 3-acetoxy-Δ5-7-ketone 2b.
Steroids 1-16, which are intermediates in the synthesis of ecdysteroids, have been shown to possess insecticidal activity for larvae of the Colorado beetle Leptinotarsa decemlineata . Active growth- and development-regulators were found among them.
The toxicity of steroids 1-11 for colorado beetle (Leptinotarsa decemlineata Say.) larvae was studied by contact-intestinal treatment. Active insect-growth regulators were found among the studied compounds.
The toxicity of steroids 1-14 for Colorado beetle (Leptinotarsa decemlineata Say.) larvae was studied by a contact-intestinal method. The most active are 3β,5α-dihydroxy-6-ketone 4a and 5α-hydroxy-3,6-diketone 8a.
Structural analogs of ecdysteroids were screened for insecticidal activity for larvae of the Colorado beetle Leptinotarsa decemlineata using a contact-feed method. High activity was found for compounds 3, 6b, 7a, and 9a.
The toxicity of 3β-chlorosteroids 1-8 for colorado beetle (Leptinotarsa decemlineata Say.) larvae was studied by a contact-intestinal method. The most active insect growth and development regulators of the studied compounds are 3β-chlorocholest-5-ene (1a), 3β-chloro-5α,6β-diol 6-formate (3b), 3β-chloro-7α-hydroxy-6-ketone (4a), and 3β-chloro-5α-bromo-Δ4-6-ketone (8).
The toxicity of steroid benzoates 4-10 for Colorado beetle ( Leptinotarsa decemlineata Say.) larvae was studied by a contact-intestinal method. The most active growth and development regulator for this insect is 3β-benzoyloxy-5-hydroxy-Δ 7 -6-ketosteroid 9a.
The toxicity of phytoecdysteroids 20-hydroxyecdysone (1),α-ecdysone (2), polypodin B (3), and poststerone (4) for larvae of colorado beetleLeptinotarsa decemlineataSay. is studied by topical and GI administration.
The toxicity of 5α-hydroxy-Δ7-6-ketosteroids for colorado beetleLeptinotarsa decemlineataSay. larvae was studied by topical and GI administration.