Two fenclorim derivatives (compounds 6 and 7) were synthesized by linking active sub-structures using fenclorim as the lead compound. The chemical structures of the two compounds were confirmed by NMR spectroscopy, high resolution mass spectrometry, and X-ray diffraction analysis. Their fungicidal activity against six plant fungal strains was tested. Compounds 6 and 7 both crystallized in the monoclinic system, with a P21/c space group (a = 8.4842(6) Å, b = 24.457(2) Å, c = 8.9940(6) Å, V = 1855.0(2) Å3, Z = 4) and Cc space group (a = 10.2347(7) Å, b = 18.3224(10) Å, c = 7.2447(4) Å, V = 1357.50(14) Å3, Z = 4), respectively. The crystal structure of compound 6 was stabilized by C–H···N and C–H···O hydrogen bonding interactions and N–H···N hydrogen bonds linked the neighboring molecules of compound 7 to form a three-dimensional framework. Compound 6 displayed the most excellent activity, which is much better than that of pyrimethanil against Botrytis cinerea in vivo. Additionally, compound 6 exhibited greater in vitro activity against Pseudoperonospora cubensis compared to that of pyrimethanil. Moreover, compound 7 exhibited strong fungicidal activity against Erysiphe cichoracearum at 50 mg/L in vitro, while pyrimethanil did not. Compounds 6 and 7 could be used as new pyrimidine fungicides in the future.
C 6 H 8 F 3 N 5 O 2 ,monoclinic, P2 1 /n (no. 14), a =5.718 (1)
Source of materialGuanidinenitrate and1,3-malononitrile reactinthe presence of sodium alkoxide in drye thanolw ithin6 hy ielding2 ,4,6-tri aminopyrimidine. 2,4,6-Pyrimidinetriamine (1.25g) and trifluoroacetic acid (765 mL) were suspended in 15mLofwater. After dissolution in the heat the mixture was kept overnight at room temperature, whereupon the crystals of the title compound were collectedand dried.
Experimental detailsHatoms were included at calculated positions and treated as ridinga toms,w ithC -H distance of 0.93 Åa nd N-Hd istanceo f 0.874-0.915Åand refinedinariding-modelapproximation with U iso (H) =1.2U eq (C,N).
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