吡唑衍生物的合成及其生物活性研究
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摘要
为寻找新的先导化合物,本文以吡螨胺的吡唑中间体为母体,设计并合成了三个系列82个新型吡唑衍生物及所需中间体,新化合物可用如下通式表示:
通式ⅠX=NO_2、H、Cl和Br,(?)为噻唑烷酮、噻唑硫酮、噁唑烷酮、咪唑、苯并咪唑、3-甲基-5-吡唑酮和3-甲基-5-吡唑酸乙酯等含氮杂环。
该系列化合物的综合生物活性试验结果知,当吡唑环4-位为溴原子时,含吡唑双杂环化合物的生物活性变化较大。TI-3-03晶体结构表明两个杂环平面互相垂直呈正交关系,由此可知,杂环之间不能产生联系,就不可能在生物活性方面互相影响,从而导致合成的双杂环化合物不可能在生物活性方面有大的提高。
诵式ⅡX=Cl和Br,R=C_1～C_8烷基,R_1=单取代基团,n=0或1。
该系列化合物的综合生物活性试验结果知,当吡唑4-位取代基为溴原子时,含吡唑双酰肼化合物有望成为具有杀菌活性的先导化合物;当吡唑4-位取代基为氯原子时,含吡唑双酰肼化合物有望成为具有杀虫活性的先导化合物。
通式ⅢX=Cl和Br,R=单取代或双取代基团。
该系列化合物的综合生物活性试验结果知,当吡唑4-位取代基为溴原子时,
Pyrazole derivatives are widely studied in the world to find out new pesticide lead compounds. Based on the intermediates of tebufenpyrad(MK-239), 82 new compounds of pyrazole derivatives have been synthesized in three serials with the general formula as follows:Formular IX=NO2, H, Cl or Br, =2-thiazolidinone, 2-thiazolidinethione, 2-oxozolidinone, lH-3-methyl-2-pyrazolin-5-one, l.H-pyrazole-3-ethyl-5-carboxylic acid, ethyl ester, lH-imidazole or 1H-benzimidazole.The results of biological tests indicated that, at 25 μg/mL, 3-methyl-2-pyrazolin-5-one, l-[(3-ethyl-l-methyl-4-bromo-lH-pyrazole-5-yl)-carbonyl]- (TI-4-04) showed inhibitory activities (45.6%) against Pyricularia oryzae. At 500 μg/mL, 3-methyl-2-pyrazolin-5-one, l-[(3-ethyl-l-methyl-4-nitro-lH -pyrazole-5-yl)-carbonyl]-(TI-3-04) showed inhibitory activities (53.85%) against Nephotettix cincticeps. The crystal structure of TI-3-03 indicates that the dihedral angles is formed between the central link and the five-membered pyrazole and oxazolidin-2-one rings [planar to 0.079 (4) *10~-10 m] of 89.2 (2)° and 11.2 (2)°, respectively, and this fact is emphasized by the orthogonal relationship between the rings [dihedral angle =90.0 (2)°], which prove that the pyrazolyl-heterocycles can not be lead compounds.Foumular IIX=C1 or Br, R=C_1~C_8 alkyl, R_1=single replaced group, n=0 or 1.The results of fungicidal activity tests indicated that, 4-bromo-pyrazolyl-biacyl hydrazine might be lead compound. The results of insecticidal activity tests indicated that, 4-chloro-pyrazolyl-biacyl hydrazine might be lead compound.Foumular IIIX=Cl or Br, R=single or double replaced group.
通式ⅠX=NO_2、H、Cl和Br,(?)为噻唑烷酮、噻唑硫酮、噁唑烷酮、咪唑、苯并咪唑、3-甲基-5-吡唑酮和3-甲基-5-吡唑酸乙酯等含氮杂环。
该系列化合物的综合生物活性试验结果知,当吡唑环4-位为溴原子时,含吡唑双杂环化合物的生物活性变化较大。TI-3-03晶体结构表明两个杂环平面互相垂直呈正交关系,由此可知,杂环之间不能产生联系,就不可能在生物活性方面互相影响,从而导致合成的双杂环化合物不可能在生物活性方面有大的提高。
诵式ⅡX=Cl和Br,R=C_1～C_8烷基,R_1=单取代基团,n=0或1。
该系列化合物的综合生物活性试验结果知,当吡唑4-位取代基为溴原子时,含吡唑双酰肼化合物有望成为具有杀菌活性的先导化合物;当吡唑4-位取代基为氯原子时,含吡唑双酰肼化合物有望成为具有杀虫活性的先导化合物。
通式ⅢX=Cl和Br,R=单取代或双取代基团。
该系列化合物的综合生物活性试验结果知,当吡唑4-位取代基为溴原子时,
Pyrazole derivatives are widely studied in the world to find out new pesticide lead compounds. Based on the intermediates of tebufenpyrad(MK-239), 82 new compounds of pyrazole derivatives have been synthesized in three serials with the general formula as follows:Formular IX=NO2, H, Cl or Br, =2-thiazolidinone, 2-thiazolidinethione, 2-oxozolidinone, lH-3-methyl-2-pyrazolin-5-one, l.H-pyrazole-3-ethyl-5-carboxylic acid, ethyl ester, lH-imidazole or 1H-benzimidazole.The results of biological tests indicated that, at 25 μg/mL, 3-methyl-2-pyrazolin-5-one, l-[(3-ethyl-l-methyl-4-bromo-lH-pyrazole-5-yl)-carbonyl]- (TI-4-04) showed inhibitory activities (45.6%) against Pyricularia oryzae. At 500 μg/mL, 3-methyl-2-pyrazolin-5-one, l-[(3-ethyl-l-methyl-4-nitro-lH -pyrazole-5-yl)-carbonyl]-(TI-3-04) showed inhibitory activities (53.85%) against Nephotettix cincticeps. The crystal structure of TI-3-03 indicates that the dihedral angles is formed between the central link and the five-membered pyrazole and oxazolidin-2-one rings [planar to 0.079 (4) *10~-10 m] of 89.2 (2)° and 11.2 (2)°, respectively, and this fact is emphasized by the orthogonal relationship between the rings [dihedral angle =90.0 (2)°], which prove that the pyrazolyl-heterocycles can not be lead compounds.Foumular IIX=C1 or Br, R=C_1~C_8 alkyl, R_1=single replaced group, n=0 or 1.The results of fungicidal activity tests indicated that, 4-bromo-pyrazolyl-biacyl hydrazine might be lead compound. The results of insecticidal activity tests indicated that, 4-chloro-pyrazolyl-biacyl hydrazine might be lead compound.Foumular IIIX=Cl or Br, R=single or double replaced group.
引文
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