A metastable polymorphic form of the antifungal anilinopyrimidine active pyrimethanil

Abstract

A second metastable polymorphic form of the anti­fungal anilino­pyrimidine active pyrimethanil was isolated from an attempted co-crystallization experiment with meso-erythriol in dimethyl sulfoxide (DMSO). The origin of the polymorphic behaviour is revealed in that the conformation of each dimer present in the asymmetric unit of the structure is unique and determined by the rotation of the second mol­ecule in the dimer with respect to the first.

Two polymorphic forms of the oxathiin systemic fungicide active carboxine

“…There is currently no report of any crystal structure of this important fungicide in the literature although the material has been reported to be dimorphic based upon the observation of two distinct melting points, 91.5-92.5 C and 98-100 C (Worthing, 1979). As part of an ongoing program into the preparation of co-crystal forms of agrichemical active materials to enhance or adapt their physicochemical properties (Eberlin & Frampton, 2017), it was pertinent to investigate the possible crystal structures of this active material. Given that there is just one hydrogen-bond donor and three possible acceptor groups it was deemed necessary to probe the nature of the hydrogen-bonding interactions present in the two distinct forms, thus directing the choice of prospective coformers for a screen.…”

Investigation of Novel Pesticides with Insecticidal and Antifungal Activities: Design, Synthesis and SAR Studies of Benzoylpyrimidinylurea Derivatives

“…More importantly, the 2-aminopyrimidinyl unit is commonly found in the chemical structure of antifungal compounds. For example, the antifungal activity of commercial pyrimethanil ( Figure 2 ) against Alternaria kikuchiana Tanaka was 100% at 0.1 µg mL −1 [ 9 , 10 , 11 , 12 ]. Compound F (EC 50 = 1.03 µg mL −1 ) exhibited better antifungal activity against Phytophthora capsici than dimethomorph (EC 50 = 4.26 µg mL −1 ) ( Figure 2 ) [ 13 ].…”

“…Based on our previous works [ 4 , 5 , 6 , 7 , 8 ] and the literature [ 9 , 10 , 11 , 12 , 13 , 14 ], in order to find new pesticides with powerful insecticidal and antifungal properties, we were interested in introducing pyrimidine group into the benzoylurea backbone to design a series of benzoylpyrimidinylurea derivatives ( Figure 3 ). Therefor target compounds 1 – 38 were synthesized and their insecticidal and antifungal activities were evaluated.…”

Measurement and Correlation of the Solubility of Pyrimethanil in Seven Monosolvents and Two Different Binary Mixed Solvents

“…The solid-state forms of PYL have been widely studied. In addition to a large number of inorganic or organic salts and cocrystalline species with other fungicides, two solvent-free forms have been reported. , Form I is the thermodynamically stable form at room temperature…”

“…In addition to a large number of inorganic or organic salts and cocrystalline species with other fungicides, two solvent-free forms have been reported. 8,9 Form I is the thermodynamically stable form at room temperature. 10 Our objectives are (1) to investigate the solubility of pyrimethanil (form I) in seven commonly used organic solvents and two binary solvents from 283.15 to 323.15 K at atmospheric pressure by a gravimetric method, (2) to correlate the experimental solubility data in the monosolvents with the NRTL model, the Apelblat model, and the Wilson model and in the mixed solvents with the NRTL model and the modified Jouyban−Acree model (the Apel-JA equation), and (3) to study the relationship between the multiple morphologies of the obtained PYL crystals with respect to the composition of the solvents during evaporation crystallization at room temperature at 0.1 MPa.…”