The Effect of C-4 Substituent of 2-phenylimino-1,3-thiazolines on the Antifungal Activity Against Rice Blast
- The Effect of C-4 Substituent of 2-phenylimino-1,3-thiazolines on the Antifungal Activity Against Rice Blast
- 임정섭; 한민수; 남기달; 최경자; 한호규
- 2-페닐이미노-1,3-티아졸린; 구조-활성관계; 신농약 개발; 농약 살균제; 벼도열병; 2-phenylimino-1,3-thiazoline; structure-activity relationship; development of agrochemicals; fungicide; rice blast
- Issue Date
- VOL 13, NO 2, 63-69
- New morpholinylcarbonylmethyl-2-phenylimino-1,3-thiazolines 2(X=O) and piperidinylcarbonylmethyl-2-phenylimino-
1,3-thiazolines 3(X=C) to which morpholinyl or piperidinyl functional group were introduced at C-4 side chain
of the 2-phenylimino-1,3-thiazoline scaffold were synthesized to investigate the effect of NH hydrogen of
2-phenylimino-1,3-thiazoline-4-acetanilide derivatives on the antifungal property against rice blast. Synthesized
30 compounds were screened against 6 kinds of typical plant fungi. Treatment of ketene dimer with chlorine
followed by the reaction of morphorine or piperidine without isolation of the intermediate acetoacetylchloride gave γ-chloro-β-keto derivatives. These were reacted with thioureas to give morpholinylcarbonylmethyl-2-phenylimino-
1,3-thiazolines and piperidinylcarbonylmethyl-2-phenylimino-1,3-thiazolines respectively in good yield (27-98%).
The compound 3j, in which two fluorine atoms are substituted at ortho and para position of phenyl group of
2-phenylimino moiety and piperidinyl group is substituted at C-4, showed the highest antifungal activity (100
ppm, 90%). This result suggested that the substituent at C-4 of the 2-phenylimino-1,3-thiazolines may play
a supplementary role to show the antifungal activity against rice blast.
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