Crystal structure of trans-3-chloro-4-[4-methyl-2-(1H-1,2,4-triazol-1- ylmethyl)-1,3-dioxolan-2-yl]phenyl-4-chlorophenyl ether, C19H17Cl2N3O3

Abstract

C 19 H 17 Cl 2 N 3 O 3 ,monoclinic, C2/c (no. 15), a =25.792(7) Å, b =10.020(3) Å, c =15.054(4) Å, b =93.337(5)°, Source of materialThetitle compound is easily available by aliterature known synthesis [1]. It was recrystallized from am ethyl tert. butyle ther solution at room temperature to give colourless crystals suitable for single-crystal X-ray diffraction. Experimental detailsHa toms were positioned geometrically with C-H =0 .93, 0.97 and 0.96 Åfor aromatic, methylene and methyl, respectively, and constrained to ride on their parent atoms, with U iso (H) =1.2 (1.5 for methyl)times U eq (C). Difenoconazoleisanimportant representative of atriazole derivative, which has been used as the most efficient triazole fungicide [5,6]. But alot of waste residues are formed in the process of production. In order to get deeper insight into the reaction mechanism and to optimize the production process, the title compound wass eparated andi ts structure was characterized. As shown in thefigure,fourrings exist in the molecular structure. Two benzene rings and triazol ring are planar, while the dioxolan ring is bent. The dihedral angle between two benzene rings is 80.6°ow-ing to rotating and bending of the ether bond. The dioxolan ring adopts an envelope conformation, with the C17 atom deviating from the C18/O2/C13/O3 plane by 0.248(2) Å.Z. Kristallogr.

Uma Abordagem Sobre a Cultura Do Maracujazeiro E O Manejo Químico E Biológico Da Antracnose

“…-1,3-dioxolan-2-ylphenyl 4-chlorophenyl ether) é um fungicida sistêmico de amplo espectro do grupo químico do triazol, amplamente utilizados no controle de doenças fúngicas em culturas agrícolas (DONG et al, 2013;QUANGLIANG et al, 2014). Esses fungicidas foram sintetizados como inibidores da desmetilização (DMI) direcionada ao esterol 14α-desmetilase, uma importante enzima que regula a biossíntese do ergosterol, inibindo o crescimento fúngico, apresentando efeito protetivo e curativo (WANG et al, 2008;DONG et al, 2013;PRICE et al, 2015;HE et al, 2019).…”

Simultaneous Enhancement of Thermal Stability and Preferred Isomer Enrichment in Difenoconazole: the Dual Facets of Cocrystal Engineering

“…In recent years, difenoconazole (DZ; cis – trans -3-chloro-4-(4-methyl-2-(1H-1,2,4-triazol-yl methyl)-1,3-dioxolan-2-yl) phenyl 4-chlorophenyl ether), a racemic mixture, has gained prominence in the fungicide market due to its efficacy and versatility, which acts by inhibiting demethylation during ergosterol biosynthesis (Figure ). − At present, scholarly pursuits regarding DZ predominantly concentrate on aspects such as formulation development, − investigation of pesticide residues, − and the examination of its stereoselective bioactivity. , Most studies use high-performance liquid chromatography (HPLC) with a chiral column to separate DZ stereoisomers, , but this method requires advanced equipment and is costly. Among the four stereoisomers of DZ, the ( 2S,4S )-DZ is identified as the most toxic and least biologically active, while the ( 2R,4S )-DZ emerges as the least toxic and most active, suggesting that employing cis -DZ or a high proportion of cis -DZ instead of the commercially available mixed stereoisomers could potentially increase the bioactivity and reduce environmental pollution .…”