Syntheses, Antifeedant Activity, and QSAR Analysis of New Oxa(thia)diazolyl 3(2H)-Pyridazinones

Abstract

Twenty-eight new oxa(thia)diazolyl 3(2H)-pyridazinone derivatives were synthesized. Some compounds showed good chronic growth activities against the armyworm, Pseudaletia separata (Walker). Their EC50 values were determined in vivo. Nineteen 2-tert-butyl-4-chloro-5-[5'-aryl-2'-(1',3',4'-oxadiazolyl)methoxy]-3(2H)-pyridazinones were quantitatively analyzed using the QSAR procedure. The partial least squares method was applied to find relationships between activity and the physicochemical data. The results showed that dipole moment, molar refractivity, and log P are identified as critical parameters for chronic growth effects.

Design, synthesis and QSAR study of novel 8-(3-(trifluoromethyl) phenyl)-6-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-ones

“…Compound 3 was synthesized by chlorination of 4-(3-(trifluoromethyl)phenyl)-6-methyl pyridazin-3(2H)-one at 70-75 and the higher temperature will decrease its yield. 14,15,16,17,18 The key intermediate 8-(3-(trifluoromethyl)phenyl)-6-methyl- [1,2,4]triazolo [4,3-b] pyridazin-3(2H)-one (5) was prepared by 3 and NH 2 NHCO 2 C 2 H 5 in 1-butanol 19 and it was reacted with compound 4 in the presence of NaH to give 1a-1o as shown in Scheme 1. 2 The 1 H NMR spectral data of the synthesized compounds were found in agreement with the assigned molecular structures and their physicochemical parameters used in present study are given in Table 1.…”

“…[1][2] It was also noticed that lots of pyridazine compounds showed good herbicidal activity and some are being used at present. [3][4][5] In addition, many commercial phytoene desaturase inhibitors contained a heterocycle moiety substituted by a 3-trifluoromethylphenyl group, which was important for their herbicidal activity. 6 Considering that the method of montage of active substructures has been extensively utilized to find potential agrochemicals( such as 2-(4-aryloxyphenoxy)propanoates) [7][8] and to…”

“…

AbstractA series of novel 8-(3-(trifluoromethyl)phenyl)-6-methyl- [1,2,4]triazolo [4,3-b]pyridazin-3(2H)-one derivatives were designed, synthesized and evaluated for their bioactivities. Some of them provided > 80 % inhibition of chlorophyll of Spirodela polyrhiza or > 70 % inhibition of growth of Spirodela polyrhiza at 10 µg/ml.

…”

One‐pot Synthesis of 5‐{[Bis(azolylmethylthio)]methylene}pyrimidine‐2,4,6‐(1H,3H,5H)‐triones

“…A broad singlet was observed at $10 ppm due to NH which disappeared on deuteration. The structures of the compounds 5-8 were further confirmed by 13 C-NMR spectra.…”

Quantitative Aggregation–Activity Relationship (QAAR): Supermolecular View, Dimer as the Simplest Aggregation State and Monomolecule

“…The quality of each regression model was evaluated, using a squared correlation coefficient (r 2 ), crossvalidation squared correlation coefficient (XVr 2 ), and predicted sum of squares (PRESS). The crossvalidation squared correlation coefficient XVr 2 is a measure of the predictive ability of the equation [38].…”