Dataset Information

Synthesis of Novel 6-Aryloxy-4-chloro-2-phenylpyrimidines as Fungicides and Herbicide Safeners.

ABSTRACT: Fenclorim is a commercial herbicide safener with fungicidal activity used for chloroacetanilide herbicides, which might be suitable as a lead compound for screening novel fungicides. However, little has been reported so far on the structure-activity relationship of fungicidal activities of fenclorim or its analogues. Here, a series of 4-chloro-6-substituted phenoxy-2-phenylpyrimidine derivatives was synthesized by a substructure splicing route using fenclorim as a lead compound. The structures of synthesized derivatives were characterized by 1H NMR, 13C NMR, and HRMS. Their fungicidal and herbicide safening activities were then evaluated. The results revealed that compound 11 had the best fungicidal activity against Sclerotinia sclerotiorum and Thanatephorus cucumeris, which was better than that of the control pyrimethanil. Moreover, compounds 3, 5, and 25 exhibited excellent safening activities against fresh weight, plant height, and root length, respectively. Such activities were significantly improved when compared to fenclorim. In summary, these findings look promising for the preparation of new fungicides and herbicide safeners based on the structure of fenclorim.

SUBMITTER: Deng X

PROVIDER: S-EPMC7513367 | biostudies-literature | 2020 Sep

REPOSITORIES: biostudies-literature

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Synthesis of Novel 6-Aryloxy-4-chloro-2-phenylpyrimidines as Fungicides and Herbicide Safeners.

Deng Xile X Zheng Wenna W Jin Can C Bai Lianyang L

ACS omega 20200910 37

Fenclorim is a commercial herbicide safener with fungicidal activity used for chloroacetanilide herbicides, which might be suitable as a lead compound for screening novel fungicides. However, little has been reported so far on the structure-activity relationship of fungicidal activities of fenclorim or its analogues. Here, a series of 4-chloro-6-substituted phenoxy-2-phenylpyrimidine derivatives was synthesized by a substructure splicing route using fenclorim as a lead compound. The structures o ...[more]

PMID: 32984721

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Project description:Despite the emergence of novel biotechnological and biological solutions, agrochemicals continue to play an important role in crop protection. Fungicide resistance is becoming a major problem; numerous cases of fungicide resistance have occurred worldwide in the last decade, resulting in the loss of several fungicides. The discovery of new molecules has therefore assumed critical importance in crop protection. In our quest for biologically active molecules, we herein report the synthesis of a series of twenty-one 3-Iodochromone derivatives (4a-4u), in a two-step process by condensation of 2-hydroxyacetophenone derivatives (2a-2u) with N,N-dimethylformamidedimethylacetal yielding enaminones (3a-3u), followed by cyclization with iodine to corresponding 3-iodochromones. Characterization of these compounds was done by IR, 1H NMR, 13C NMR, and LC-HRMS techniques. All synthesized compounds were screened for their fungicidal activity against Sclerotium rolfsii. Among these 6,8-Dichloro-3-iodochromone 4r was found to be most active (ED50 = 8.43 mg L-1). 2D-Quantitative Structural Activity Relationship (2D-QSAR) analysis was also performed by generating three different models viz., Multiple Linear Regression (MLR, Model 1), Principal Component Regression (PCR, Model 2), and Partial Least Squares (PLS, Model 3). Predictive power and statistical significance of these models were assessed with external and internal validation and leave one-out cross-validation was used for verification. In QSAR study, MLR (Model 1) was found to be best having correlation coefficient (r2) 0.943, cross-validated correlation coefficient (q2) 0.911 and r2pred 0.837. It was observed that DeltaEpsilonC, T_2_Cl_6, T_2_F_6, T_T_F_3, and ZCompDipole are the major descriptors which influence the fungicidal activity of 3-Iodochromone derivatives. The physicochemical parameters were estimated by the VLifeMDS 4.6 software. The QSAR study results will be helpful for structure optimization to improve the activity.

Dataset Information

Synthesis of Novel 6-Aryloxy-4-chloro-2-phenylpyrimidines as Fungicides and Herbicide Safeners.

Publications

Synthesis of Novel 6-Aryloxy-4-chloro-2-phenylpyrimidines as Fungicides and Herbicide Safeners.

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