Abstract
Background: The development of new antifungal agents has always been a hot research topic in pesticide development. In this study, a series of derivatives of natural compound β-pinene were prepared, and the antifungal activities of these derivatives were evaluated. The purpose of this work is to develop some novel molecules as promising new fungicides. Methods: Through a variety of chemical reactions, β-pinene was transformed into a series of β-pinene-based derivatives containing amide moieties and acylthiourea moieties. The antifungal activities of these derivatives against five plant pathogens including Colletotrichum gloeosporioides, Fusarium proliferatum, Alternaria kikuchiana, Phomopsis sp. and Phytophthora capsici were tested; preliminary structure–activity relationship was discussed. Results: Some derivatives exhibited moderate or significant antifungal activity due to the fusion of the amide moiety or the acylthiourea moiety with the pinane skeleton. The structure–activity relationship analysis showed that the fluorine atom and the strong electron withdrawing nitro group, or trifluoromethyl group on the benzene ring of the derivatives had a significant effect on the improvement of the antifungal activity against Colletotrichum gloeosporioides, Fusarium proliferatum, Alternaria kikuchiana and Phomopsis sp. Meanwhile, the introduction of an ethyl group at the meta-position on the benzene ring of the derivatives could improve the antifungal activity against Phytophthora capsici. Compounds 4e, 4h, 4q, 4r exhibited broad-spectrum antifungal activity against the tested strains. Compound 4o had significant antifungal activity against Phytophthora capsici (IC50 = 0.18 μmol/L). These derivatives were expected to be used as precursor molecules for novel pesticide development in further research.
Highlights
During the growth of crops, various plant diseases occur; 70% to 80% of plant diseases are caused by phytopathogenic fungi infection [1,2]
Based on the substructure splicing principle, a series amide moiety derivatives andacylthiourea acylthiourea and acylthiourea derivatives were synthesized by splicing anofamide or an derivatives were by splicing an amide moiety or an acylthiourea moiety onto the pinane skeleton
The results of antifungal activity test showed that compared with the raw material β-pinene and the intermediate compound myrtanyl acid, β-pinene-based derivatives that were synthesized by the blend of amide group and pinane skeleton or the blend of acylthiourea group and pinane skeleton exerted better antifungal activity against plant pathogens
Summary
During the growth of crops, various plant diseases occur; 70% to 80% of plant diseases are caused by phytopathogenic fungi infection [1,2]. Chemical antifungal agents can effectively kill or inhibit the growth of plant pathogenic fungi, and play a vital role in protecting human health, increasing crop yields, and food preservation [4,5]. Molecules 2019, 24, x FOR PEER REVIEW and play a vital role in protecting human health, increasing crop yields, and food preservation [4,5]. The antifungal activities of these derivatives against five plant pathogens including Colletotrichum gloeosporioides, Fusarium proliferatum, Alternaria kikuchiana, Phomopsis sp. The structure–activity relationship analysis showed that the fluorine atom and the strong electron withdrawing nitro group, or trifluoromethyl group on the benzene ring of the derivatives had a significant effect on the improvement of the antifungal activity against Colletotrichum gloeosporioides, Fusarium proliferatum, Alternaria kikuchiana and Phomopsis sp. The introduction of an ethyl group at the meta-position on the benzene ring of the derivatives could improve the antifungal activity against Phytophthora capsici
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