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. 2018 Aug 31;23(9):2203.
doi: 10.3390/molecules23092203.

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

Peiqi Chen  1   2   3 , Xiangmin Song  4   5 , Yongmei Fan  6   7 , Weihao Kong  8   9 , Hao Zhang  10 , Ranfeng Sun  11   12
Affiliations

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

Peiqi Chen et al. Molecules. .

Abstract

In order to find pesticides with insecticidal and antifungal activities, a series of novel benzoyl pyrimidinylurea derivatives were designed and synthesized. All target compounds were identified by ¹H-NMR spectroscopy and HRMS. Insecticidal and antifungal activity of these compounds were evaluated and the structure-activity relationships (SAR) were clearly and comprehensively illustrated. Compound 7, with low toxicity to zebrafish (LC50 = 378.387 µg mL-1) showed 100% inhibition against mosquito (Culex pipiens pallens) at 0.25 µg mL-1. Both compounds 19 and 25 exhibited broad-spectrum fungicidal activity (>50% inhibitory activities against 13 phytopathogenic fungi), which were better than those of the commercial pesticide pyrimethanil (>50% inhibitory activities against eight phytopathogenic fungi). Furthermore, compounds 19 and 25 exhibited protective activity against Sclerotinia sclerotiorum on leaves of Brassica oleracea L. during in vivo experiments.

Keywords: antifungal activity; benzoylpyrimidinylurea derivatives; embryo toxicity; insecticidal activity; zebrafish.

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Conflict of interest statement

The authors declare no conflict of interest.

Figures

Figure 1
Figure 1
Chemical structures of benzoylurea compounds.
Figure 2
Figure 2
Chemical structures of compounds with pyrimidine groups.
Figure 3
Figure 3
Design strategies of the target benzoylpyrimidinylurea derivatives.
Scheme 1
Scheme 1
Synthetic route for substituted 2-aminopyrimidines Ia–c, Id–f and Ig–m.
Scheme 2
Scheme 2
Synthetic route for substituted 2-aminopyrimidines In, Io and Ip.
Scheme 3
Scheme 3
Synthetic route for compounds 1–10.
Scheme 4
Scheme 4
Synthetic route for compounds 11–30.
Scheme 5
Scheme 5
Synthetic route for compounds 31 and 32.
Scheme 6
Scheme 6
Synthetic route for compounds 33–38.
See this image and copyright information in PMC

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