E. A. Ershova

Synthesis and physiological activity of new organophosphorus pesticides of 1,3,2-oxazaphosphorinane series

Methods for the synthesis of 2-aryloxy(arylthio)- and 2-alkoxy(alkylthio)-2-thio(oxo)-1,3,2-oxazaphosphorinanes and theirN-substituted derivatives based on the reactions of the corresponding dichlorophosphates, dichlorothio-, and dithiophosphates with 3-aminopropan-1-ol or its substituted derivatives in the presence of Et3N or aqueous alkali under phase transfer catalysis conditions, as well as by the reaction of the tetramethylammonium salt of 2-hydroxy-2-thio-1,3,2-oxazaphosphorinane with alkyl- and acyl halides, by that of 2-chloro-2-thio-1,3,2-oxazaphosphorinane with sodium thiolates, and by other methods, were developed. The compounds obtained exhibit high nematocide activity but low toxicity for mammals. Some active synergists for permethrine were found among these compounds.

Synthesis of new organothiophosphorus insectoacaricides containingN-acylated amino acid fragments

Methods for the synthesis ofO-alkylS-(N-acyl-N-alkoxycarbonylalkyl)aminomethyl (methyl)thio- and -dithiophosphonates based on the reaction between alkaline-metal salts ofO-alkyl (methyl)thio- and -dithiophosphonates and N-alkoxycarbonyl-N-chloromethylglycine or -β-alanine esters and by treatment ofO-alkyl (methyl)dithiophosphonoates andN-acylated amino acids or their esters with paraform in the presence of HCl were developed. The compounds obtained exhibit high insectoacaricide activity and selectivity.

Some esters of phosphorus thioacids that contain the fragments of cyclic amino acid derivatives

ConclusionsThe reaction of the salts of phosphorus thio- and dithioacids with the 1,4-di(chloroacetyl)-and 1,4-di(chloromethyl)-2,5-diketopiperazines, and also with 1-chloromethyl-5-carbethoxy-2-pyrrolidinone, gave new thio- and dithiophosphorus compounds, which display either a moderate or weak insecticidal and acaricidal activity and a substantial toxicity for animals in a number of cases.

Synthesis, reaction with esterases, and toxicity of O-alkyl S-(carbalkoxymethylmercapto)methyl methylthiophosphonates

Conclusions1.A number of O-alkyl S-(carbalkoxymethylmercapto)methyl methylthiophosphonates was obtained by reacting the sodium salts of methylthiophosphonic acids with halo derivatives.2.It was found for the obtained compounds that increasing the size of the alkyl in the alkoxyl group on the phosphorus atom leads to an increase in the reaction rate with the esterases of warm-blooded animals and arthropoda, whereas the toxicity of the compounds decreases for the arthropoda.

Methyldithiophosphonates that contain mercaptoacetic acid moieties

Conclusions1.Some O-alkyl methyldithiophosphonates, containing mercaptoacetic acid moieties in the alkthiol radical, were synthesized by alkylating the salts of O-alkylmethyldithiophosphonic acids with halo derivatives.2.Some of the obtained compounds have a high insectoacaricidal activity, which approaches the activity of the standards Metaphos and Rogor.

SYNTHESIS AND INSECTOACARICIDE ACTIVITY OF S-BENZHYDRYL ESTERS OF PHOSPHORUS DITHIO- AND MONOTHIO ACIDS

We synthesized a number of S-benzhydryl esters of phosphorus dithioacids that possess insectoacaricidal properties, in which connection the most active ester, O-ethyl S-benzhydryl methyldithiophosphonate, has the same contact activity as Chlorophos and Rogor.