| The substituted ureas with a variety of biological activity, are widely used in pesticide and medicinal chemistry. Owing to simulative, osmotic, electronic and obstructive function of fluorine atom, fluorine-containing pesticides with small dosage, low toxicity, high efficacy, and high metabolic ability. Pyrimidine occupies a very important position in the activities of life, and has high biological activity. In this study, according to structure link way, the fluorine atom and the pyrimidine ring are introduced to both sides of the ureas bridge, and designed and synthesized thirty-four fluorine-containing phenyl pyrimidinyl urea derivatives, twenty-three of them are novel compounds.This paper mainly contains three parts as bellow.Part I:a series of N-fluorine-containing Phenyl-N’-pyrimidylurea derivatives were synthesized using a simple and convenient BTC one-pot synthetic method, the structures of all synthesized compounds were confirmed by melting point, IR,1H NMR, and elemental analysis.The structures of urea derivatives were shown: 1 R1=3-F, R2=-Cl, R3=-OCH3; 2 R1=4-F, R2=-Cl, R3=-OCH3; 3 R1=3-CF3, R2=-Cl, R3=-OCH3; 4 R1=4-CF3, R2=-Cl, R3=-OCH;5 R1=2,4-di-F, R2=-Cl, R3=-OCH; 6 R1=2,5-di-F, R2=-C1, R3=-OCH; 7 R1=4-F, R2, R3=-H; 8 R,=4-CF3, R2, R3=-H; 9 R1=2,4-di-F, R2, R3=-H; 10 R1=2,5-di-F, R2, R3=-H; 11 R1=4-F, R2=-CH3, R3=-Cl;12 R,=4-CF3, R2=-CH3, R3=-Cl;13 R1=2,4-di-F, R2=-CH3, R3=-Cl;14 R1=2,5-di-F, R2=-CH3, R3=-Cl; 15 R1=4-F, R2, R3=-OCH3;16 Ri=4-CF3, R2, R3=-OCH3; 17 R1=2,4-di-F, R2, R3=-OCH3; 18 R1=2,5-di-F, R2, R3=-OCH3; 19 R,=2-F, R2, R3=-Cl;20 R1=3-F, R2, R3=-Cl;21 R1=4-F, R2, R3=-Cl; 22 R1=2-CF3, R2, R3=-Cl; 23 R1=4-CF3, R2, R3=-Cl; 24 R,=2,4-di-F, R2, R3=-Cl; 25 R1=2,5-di-F, R2, R3=-C1;26 R,=2,6-di-F, R2, R3=-Cl; 27 R1=4-F, R2, R3=-CH3; 28 R,=4-CF3, R2, R3=-CH3; 29 R1=2,4-di-F, R2, R3=-CH3; 30 R1=2,5-di-F, R2, R3=-CH3; 31 R1=4-F, R2=-OH, R3=-CH3; 32 R1=4-CF3, R2=-OH, R3=-CH3; 33 R,=2,4-di-F, R2=-OH, R3=-CH3; 34 R1=2,5-di-F, R2 =-OH, R3=-CH3Part Ⅱ:All synthesized target compounds and 29 other urea compounds with similar structure were tested for biological activity.1) The "Rape hypocotyl elongation test method" was adopted to test the plant growth regulating activity against rape and race, screened for herbicidal activities against Amaranthus retroflexus and Setaria viridis. The results shown that compound 10 and 19 exhibit good growth-promoting activity for race, the rate at 10mg/L are 83.19% and 81.58%, respectively. The growth-promoting rate of compounds 3,53,61,63 are above 75% for rape root, the growth-promoting rate of compounds 22,47,48,63 are above 70% for rape stems.2) The "Petri dish test for herbicidal bioactivity (NY/T 1155.1-2006)" was adopted to test the herbicidal activities against Amaranthus retroflexus and Setaria viridis. For Amaranthus retroflexus, the results shown that the IC50 of compounds 17,34,37,38,39, 42,43 were below 100 mg/L against root, and the best IC50 of compounds 39 was 35.13 mg/L. The IC50 of compounds 4,34,45 were below 100mg/L against stem, and the best IC50 of compounds 4 was 64.02 mg/L. For Setaria viridis, the IC50 of compounds 7,23, 38,39 were below 50 mg/L against root, and that of compounds 15,17,26 were below 150 mg/L against stem. Even compound 23 (IC50=11.67 mg/L) and 15 (IC50=60.73 mg/L) exhibited marked herbicidal activity which was more potent than that of bensulfuron (IC50=27.45 mg/L, IC50=108.37 mg/L, respectively), a commercially available herbicide.Part Ⅲ:based on the obtained biological data, quantitative structure-activity relationship studies were performed on these compounds using comparative molecular field analysis (CoMFA), and two statistically significant CoMFA models with high predict abilities(Amaranthus retroflexus:q2=0.735, n=6, SEE=0.088,r2=0.916, F=85.308; Setaria viridis:q2=0.838, n=6, SEE=0.064, r2=0.969, F=244.73) were obtained. |
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