No abstract

Fluorinated organic compounds represent a growing and important family of commercial chemicals. Introduction of fluorine into active ingredients has become an effective way to develop modern crop protection products. Given the particular properties of fluorine and high efficiency and selectivity of diamide insecticides, we designed and synthesized 27 anthranilic diamides analogues containing fluoro-sustituted phenylpyrazole. A preliminary bioassay indicated that most target compounds exhibited good biological activity against Mythimna separata and Plutella xylostella. Compound IIIf containing a 2,4,6-trifluoro-substituted benzene ring showed 43% insecticidal activity against M. separata at 0.1 mg L −1 , while the control chlorantraniliprole was 36%. The activity of IIIe against P. xylostella at 10 −5 mg L −1 was 94%, compared with that of the control being 70%. Thus, introduction of fluorine into diamide insecticides was useful for increasing activity. Insect electrophysiology studies showed that the calcium concentration in the nerve cells of third M. separata larvae was elevated by IIIf, which further confirmed that ryanodine receptor (RyR) was its potential target.

Poor solubility and dissolution property of pharmaceuticals largely limits their bioavailability and efficacy, and development of a multicomponent crystal is one of the effective approaches to potentially address the issue. Herein we investigated the structure and property relationship of multicomponent crystal aiming to improve the pharmaceutical property, using the Biopharmaceutics Drug Disposition Classification System class II antipsychotic drug Aripiprazole (APZ) as model compound. We reported six new discovered multicomponent crystals of APZ salts with all pharmaceutically acceptable coformers. The comprehensive characterizations were done using X-ray diffraction, differential scanning calorimetry, thermogravimetric analysis, and X-ray photoelectron spectroscopy (XPS) techniques. Four multicomponent crystals were structurally solved for the first time by single-crystal X-ray diffraction, demonstrating the proton transfer from the carboxyl group of acids to APZ piperazine. Molecular interactions, crystal packing, and structure similarity analyses performed by Hirshfeld surface and CrystalCMP confirmed the charge-assisted H-bonding sites and structural similarity among the solved crystal structures. The XPS characterization of the other two multicomponent crystals corroborates the salt form as evidenced by the significant chemical shift toward higher binding energy; the pharmaceutical properties including stability, hygroscopicity, and dissolution behavior of all multicomponent crystals were examined by dynamic vapor sorption and high-performance liquid chromatography. It was found all six multicomponent crystals display high stability and low hygroscopicity but divergent dissolution behavior. The variations of these physicochemical properties were further rationalized from their crystal structures and intermolecular interactions.

An acceptor molecule with an asymmetric backbone, CC10, has been designed, which achieved a power conversion efficiency of 11.78%.