Conversion of fungicide cyprodinil to salts with organic acids: preparation, characterization, advantages

Abstract

BACKGROUND: As an effective strategy to improve the basic properties of drugs, salt formation was less used in the field of pesticides than the medicine field. It is worth trying to improve the inherent shortcomings of cyprodinil (high K ow values; polymorphism) in this way to enhance its practicality.RESULTS: Eight cyprodinil salts (CYP-Salts) were prepared. The properties of CYP-Salts, including solubility in various solvents, polymorphic behavior, soil absorption, photolysis in aquatic water, in vitro fungicidal activity and curative activity, were assessed. It was observed that compared with those of cyprodinil, CYP-Salts had lower soil adsorption, while also having lower log K ow values and could be more easily photodegraded in water. That is, CYP-Salts have lower impacts on water bodies and aquatic organisms than cyprodinil. Three CYP-Salts showed higher in vitro antifungal activities and curative activity. CYP-Salts have enhanced practicality, as they could avoid possible agglomeration caused by recrystallization.CONCLUSION: Salt forming enhanced the properties of Cyprodinil in many aspects. CYP-Salts may potentially become a better substitute for cyprodinil. This study offers a more economical and effective strategy to prepare better alternatives to existing fungicides.

The Effect of Terbinafine and Its Ionic Salts on Certain Fungal Plant Pathogens

“…The instruments and analytical methods were meticulously chosen to ensure an accurate and precise characterization of the compounds being examined. The 1 H NMR and 13 C NMR spectra were recorded using a Bruker Ascend TM 500 MHz NMR spectrometer (Bruker, Germany). The infrared (IR) spectra were obtained using an IRTracer-100 infrared spectrometer (Shimadzu, Japan).…”

“…1 H NMR (500 MHz, DMSO-d6) δ 8.26 (dd, J = 8.1, 1.6 Hz, 1H), 7.93 (dd, J = 7.6, 1.9 Hz, 1H), 7.87 (d, J = 8.0 Hz, 1H), 7.61-7.43 (m, 4H), 6.07 (dt, J = 15.9, 6.7 Hz, 1H), 5.76 (dt, J = 15.9, 1.5 Hz, 1H), 4.02 (s, 2H), 3.24 (d, J = 6.7 Hz, 2H), 2.19 (s, 3H), 1.20 (s, 9H). 13…”

“…The following supporting information can be downloaded at: https://www.mdpi.com/article/10.3390/molecules28124722/s1, Figures S1-S15: the 1 H NMR, 13 C NMR, and FT-IR spectra of the TISs, Figure S16: the CMC (mM) determination for the prepared TISs at 25 • C, Figure S17: the photos of the in vitro antifungal activities of terbinafine and its salts against (a) V. mali., (b) B.…”

“…Additionally, pyrimethanil 2-hydroxybenzoate demonstrates reduced volatilization and photodegradation compared to its parent pyrimethanil, thus mitigating its environmental impact [ 12 ]. The storage stability of cyprodinil is also enhanced by eliminating cyprodinil polymorphs in its salt form [ 13 ]. Terbinafine, containing a tertiary amine in its structure and a pKa of 7.12 [ 14 ], is highly esterophilic and may exhibit poor water solubility.…”