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- Title
Alkyl 4-Aryl-6-amino-7- phenyl-3-(phenylimino)-4,7-dihydro- 3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylates: Synthesis and Agrochemical Studies.
- Authors
Dotsenko, Victor V.; Sinotsko, Anna E.; Strelkov, Vladimir D.; Varzieva, Ekaterina A.; Russkikh, Alena A.; Levchenko, Arina G.; Temerdashev, Azamat Z.; Aksenov, Nicolai A.; Aksenova, Inna V.
- Abstract
The reaction between dithiomalondianilide (N,N'-diphenyldithiomalondiamide) and alkyl 3-aryl-2-cyanoacrylates in the presence of morpholine in the air atmosphere leads to the formation of alkyl 6-amino-4-aryl-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]- pyridine-5-carboxylates in 37–72% yields. The same compounds were prepared in 23–65% yields by ternary condensation of aromatic aldehydes, ethyl(methyl) cyanoacetate and dithiomalondianilide. The reaction mechanism is discussed. The structure of ethyl 6-amino-4-(4-methoxyphenyl)-7-phenyl-3-(phenylimino)-4,7-dihydro-3H-[1,2]dithiolo[3,4-b]pyridine-5-carboxylate was confirmed by X-ray crystallography. Two of the prepared compounds showed a moderate growth-stimulating effect on sunflower seedlings. Three of the new compounds were recognized as strong herbicide safeners with respect to herbicide 2,4-D in the laboratory and field experiments on sunflower.
- Subjects
X-ray crystallography; HERBICIDES; AROMATIC aldehydes; MORPHOLINE; AGRICULTURAL chemicals; SUNFLOWERS
- Publication
Molecules, 2023, Vol 28, Issue 2, p609
- ISSN
1420-3049
- Publication type
Article
- DOI
10.3390/molecules28020609