Crystal structure and thermodynamic properties of myclobutanil
Graphical abstract
Introduction
Myclobutanil (C15H17N4Cl; CASRN: 88671-89-0), chemically named α-butyl-α-(4-chlorophenyl)-1H-1,2,4-triazole-1-propane nitrile, is a high-efficiency, low toxicity and wide spectrum triazole fungicides [1]. It is used in control of Ascomycetes, Fungi Imperfecti and Basidiomycetes on a wide variety of crops [2], [3]. For example, it used for a foliar treatment to control the scab in apples and pears; powdery mildew in apples, pears, stone fruit, vines, cucurbits and ornamentals; rust in ornamentals, stone fruit and perennial grasses grown for seed; and various diseases in wheat; it also used for a seed treatment to control the seed- and soil-borne diseases in crops such as barley, wheat maize, cotton and rice.
In this paper the crystal structure of myclobutanil was reported. The specific molar heat capacity (Cp,m) of myclobutanil was determined by continuous Cp mode of micro-calorimeter and theoretical calculation.
Section snippets
Materials
Myclobutanil was obtained from Jiangsu Greenscie Chemical Co., Ltd. The colourless single crystal of myclobutanil (CCDC 907765) was obtained by recrystallisation from absolute ethyl alcohol. The mass fraction purity of single crystal of myclobutanil was measured by high performance liquid chromatography (HPLC type Shimadzu LC-10AT, infusion pump type LC-10ATvp, detector type SPD-10Avp, the mobile phase is acetonitrile and water with 60% (V/V)) and found to be above 0.999 (Table 1). The melting
Crystal structure
Single-crystal analysis shows the compound crystallises in monoclinic space group P21/c, with Z = 4. Myclobutanil is a chiral molecule (Fig. 2), R- and S-myclobutanil through hydrogen bond of C8H8A⋯Cl (Table 4) forms a 0D structure (Fig. 3), indicating the myclobutanil is a racemate. From Fig. 4, one can see that each 0D structure is crossed connected with four 0D structure through hydrogen bond of C3H3A···N1 and halogen bond of C13Cl⋯N1 to from a 2D structure. The distance of adjacent 0D
Conclusions
Crystal structure of myclobutanil belongs to monoclinic system with space group P21/c, with Z = 4, it is a racemate. Its low melting point is mainly due to its 3D structure is formed by the weak intermolecular hydrogen bonds and halogen bond. The Cp,m equation of myclobutanil is Cp,m/(J·K−1·mol−1) = −26.21315 + 1.30468 (T/K) from T = (283.15 to 353.15) K and the Cp,m is 362.78 J·K−1·mol−1 at T = 298.15 K. The relative deviations of Cp,m, HT − H298.15 K and ST − S298.15 K are almost equivalency at each temperature,
Note
All the uncertainties in the text are standard uncertainties.
Acknowledgments
This work was supported by New Century Excellent Talents in University of Ministry of Education of China (No. NCET-12-1047), the National Natural Science Foundation of China (Nos. 21373161, 21543016), the Provincial Natural Science Foundation of Shaanxi (No. 2014JQ2068) and the Startup Foundation for Advanced Talents of Yulin University (No. 14GK28).
References (19)
- et al.
Chem. Phys. Lett
(2001) - et al.
Parallel Comput.
(2011) - et al.
J. Chem. Thermodyn.
(2015) - et al.
Russ. J. Chem. Thermodyn.
(2016) - et al.
J. Agric. Food Chem.
(2012) - et al.
Plant Dis.
(2011) - et al.
Pest Manage. Sci.
(2008) - et al.
CRC Handbook of Chemistry and Physics
(2005) - “Pesticide Properties Data Base” data are provided by the University of Hertfordshire, Hertfordshire, GBR,...
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