Synthesis of 3,4‐Dialkyl‐5‐(1‐oxo‐ethyl)‐3H‐thiazole‐2‐thiones Derivatives and Their Pesticidal Activity

By interaction of N‐methyl(ethyl)‐dithiocarbamate sodium salt with 3‐chloro‐pentane‐2,4‐dion the 1‐(3‐alkyl‐4‐methyl‐2‐thioxo‐2,3‐dihydro‐thiazol‐5‐yl)‐ethanones 1 , 2 and corresponding oximes 7 , 8 were synthesized. On the basis of the mentioned compounds hydrazono ( 3 , 4 ), ureayl and thioureayl ( 5 , 6 ) derivatives, substituted oximes ( 9 , 10 ) and azinyl oximes ( 11 , 12 ) were obtained. The structures of synthesized compounds were confirmed by proton nuclear magnetic resonance spectroscopy and elemental analysis. The pesticidal activities of synthesized compounds were studied. Some of the synthesized compounds simultaneously have shown growth stimulant and fungicidal activity.     

Syntheses based on 3,4-dimethyl-2-thioxothiazoline-5-carboxylic acid hydrazide and azide

Treatment of 3,4-dimethyl-2-thioxothiazoline-5-carboxylic acid hydrazide with NH₄SCN and PhCONCS gave the corresponding thiosemicarbazides, arylsulfochlorides yielded the arylsulfonylhydrazides, and diazotization conditions gave the corresponding azide. The interactions of the latter with different nucleophiles have been studied and a series of novel carbamic acid, urea, and semicarbazide derivatives containing a thiazoline fragment have been prepared. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 430–436, March, 2006.     

Synthesis and Biological Activity of New 3-Pyrazolyl-6-hydrazinylpyridazine Derivatives

Russian Journal of General Chemistry - A new series of pyrazolylpyridazine derivatives was obtained on the basis of 3-pyrazol-1-yl-6-hydrazinylpyridazine. Biological screening has identified a...     

Synthesis and growth regulatory activity of pyrazolesulfanyl‐ and isoxazolesulfanyl‐1H‐[1,2,4]triazoles and their azinyl derivatives

By cyclocondensation of 3‐(1H‐[1,2,4]triazol‐3‐ylsulfanyl)‐pentane‐2,4‐dion with hydroxylamine, hydrazine, methylhidrazine, and arylsulfonyl‐hydrazides, the 3‐(3,5‐dimethyl‐isoxazol‐4‐ylsulfanyl)‐1H‐[1,2,4]triazole ( 2 ) and 3‐(3,5‐dimethyl‐1‐R‐pyrazol‐4‐ylsulfanyl)‐1H‐[1,2,4]triazoles ( 3a , 3b , 3c , 3d ) are synthesized. Under the action of quaternary ammonium salts of azines with limited heating in acetone they form a series of compounds ( 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4h ), which molecules simultaneously contain three different heterocyclic rings. Structures of compounds were confirmed by ¹H and ¹³C NMR, MS, and elemental analysis. The plants growth regulatory activities of compounds 4a , 4b , 4c , 4d , 4e , 4f , 4g , 4h were investigated. Data of biological tests testify that these compounds can be of interest to search for new growth stimulators. J. Heterocyclic Chem., (2010).     

Synthesis of Novel 2‐Amino‐(2‐thioxo‐3‐alkyl‐4‐methyl‐3H‐thiazol‐5‐yl)‐[1,3,4]thiadiazole Derivatives and Their Growth Stimulant Activity

On the base of synthesized 2‐amino and 2‐ethylamino‐(2‐thioxo‐3‐alkyl‐4‐methyl‐3H‐thiazol‐5‐yl)‐[1,3,4]thiadiazoles, their alkyl, acetyl, and alkylacetylamino derivatives are obtained. The alkylation of 2‐ethylamino derivatives can occur at both exo and endo nitrogen atoms of amidine group, and the acetylation takes place exclusively at the exocyclic nitrogen atom. At acetylation of 2‐amino‐[1,3,4]thiadiazoles, only exo substitution is observed. At the further alkylation of these products, a mixture of exo‐ and endo‐substituted forms is obtained. At preliminary screening, the synthesized compounds have shown expressed growth stimulant properties. The activity of the most active derivatives was in the range of 65–100%, compared with that of heteroauxin.     

Synthesis and fungicidal activity of novel 1,3‐disubstituted 1H‐diazirine derivatives

A convenient method for synthesis of novel 1‐[pyrimidinyl], 1‐[1,3,5‐triazin‐2‐carbonyl], and 1‐[thiazol‐5‐carbonyl] derivatives of 3‐thioxo‐diaziridine 1 , 3 , 5 , and 7 from corresponding hydrazides, CS2, and KOH is elaborated. The highest reaction yield was observed when these initial reagents were taken in molar ratio of 1:1.7:2.0, respectively. By alkylation of compounds 1 , 3 , 5 , and 7 that proceeds exclusively at sulfur atom, the 3‐sulfanyl derivatives of 1‐[pyrimidinyl]‐, 1‐[1,3,5‐triazin‐2‐carbonyl]‐, and 1‐[thiazol‐5‐carbonyl]‐diazirines 2 , 4 , 6 , and 8 were formed. The structures of synthesized compounds were confirmed by proton and carbon nuclear magnetic resonance (NMR), mass spectra (MS), and elemental analysis. The fungicidal activities of S‐substituted derivatives were studied. Data of preliminary biological tests testify that these compounds can be of interest in search for new fungicides. J. Heterocyclic Chem., (2010).     

Synthesis of New Thiazolo[3,2-b][1,2,4]triazole Derivatives and Preliminary Evaluation of Their Biological Activity

Russian Journal of General Chemistry - Heterocyclization of 3-[(1H-1,2,4-triazol-3-yl)thio]pentane-2,4-dione afforded 1-(6-methylthiazolo[3,2-b][1,2,4]-triazol-5-yl)ethan-1-one, the reactions of...     

Synthesis and Plant Growth Stimulating Action of 2-Amino-6-methylpyrimidine-4(3H)-thione Derivatives

Russian Journal of General Chemistry - A series of new pyrimidine derivatives, including those containing an azole or azine heterocycle linked through a sulfur atom or a thiomethylene group, was...     

Synthesis and Biological Activity of New 2-{[6-Methyl-2-(pyrrolidin-1-yl)pyrimidin-4-yl]oxy}acetohydrazide Derivatives

Russian Journal of General Chemistry - The reaction of 6-methyl-2-(pyrrolidin-1-yl)pyrimidin-4(3H)-one with methyl chloroacetate, followed by hydrazinolysis, gave...     

Synthesis of azinylthioureas and their heterocyclization using α-chloroacetoacetic ester

Treatment of aminopyrimidines with a mixture of PhCOCl and NH₄SCN and subsequent debenzoylation of the N-benzoyl-N′-(4,6-substituted pyrimidin-2-yl)thioureas obtained gave pyrimidinyl-2-thioureas. The heterocyclization of the azinyl-2-thioureas with α-chloroacetoacetic ester gave ethyl 2-(4,6-substituted azin-2-yl)aminothiazole-5-carboxylates. __________ Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 3, pp. 437–440, March, 2006.