Chemical structures and insecticidal, acaricidal activities of 6-alkylthio-2-pyridyl alkanesulfonates

• Published in: Journal of Pesticide Science Vol. 14; no. 1; pp. 11 - 12
• Main Authors: KATO, S, MATSUI, A, ISHIDA, S
• Format: Journal Article
• Language: English
• Published: Tokyo Pesticide Science Society of Japan 1989; Japan Science and Technology Agency
• Subjects: acaricidas; acaricide; acaricides; accion de los plaguicidas; action des pesticides; Biological and medical sciences; chemical structure; estructura quimica; Fundamental and applied biological sciences. Psychology; Generalities; insecticidas; insecticide; insecticides; pesticide actions; Phytopathology. Animal pests. Plant and forest protection; Protozoa. Invertebrates; structure chimique; Alkanesulfonate; Insecticide; New product; Nitrogen heterocycle; Insecta; Chemical structure; Screening test; Biological activity; Pyridine derivatives; Organic synthesis; Arachnida; Acaricide; Pest; Acari; Structure activity relation; Arthropoda; Invertebrata
• ISSN: 0385-1559; 1348-589X; 1349-0923
• DOI: 10.1584/jpestics.14.11

6-Alkylthio-2-pyridyl alkanesulfonates, and their sulfoxides and sulfones were synthesized, and their lethal activity was tested to five species of insects and mites. Methanesulfonates, with 6-alkyl-thio, -sulfinyl and -sulfonyl substituents having one to six carbon atoms, showed remarkable insecticidal activity to Nephotettix cincticeps, Nilaparvata lugens and Culex pipiens. Insecticidal activity of 6-alkylthio-2-pyridyl methanesulfonates to strains of Nephotettix cincticeps susceptible and resistant to organophosphates and carbamates was related parabolically to the hydrophobicity of the molecule, the optimum alkyl-thio substituents being C3-C4 alkyl groups. In a series of 6-iso-butylthio-2-pyridyl alkanesulfonates and their sulfoxides and sulfones, the methane-, ethane- and chloromethane-sulfonates showed stronger insecticidal activity than higher alkanesulfonates. The 6-n-propyl-sulfinyl-, -sulfonyl-, 6-iso-butyl-sulfinyl- and -sulfonyl-2-pyridyl methanesulfonates and the 6-iso-butylsulfonyl-substituted ethanesulfonate showed strong inhibitory activity against acetylcholinesterase preparations from the susceptible and resistant strains of Nephotettix cincticeps.