title: Synthesis and bioactivity of pyrazole acyl thiourea derivatives.
abstract: Sixteen novel pyrazole acyl thiourea derivatives 6 were synthesized from monomethylhydrazine (phenylhydrazine) and ethyl acetoacetate. The key 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl chloride intermediates 4 were first generated in four steps through cyclization, formylation, oxidation and acylation. Thess were then reacted with ammonium thiocyanate in the presence of PEG-400 to afford 5-chloro-3-methyl-1-substituted-1H-pyrazole-4-carbonyl isothiocyanates 5. Subsequent reaction with fluorinated aromatic amines resulted in the formation of the title compounds. The synthesized compound were unequivocally characterized by IR, ¹H-NMR, ¹³C-NMR and elemental analysis and some of the synthesized compounds displayed good antifungal activities against Gibberella zeae, Fusarium oxysporum, Cytospora mandshurica and anti-TMV activity in preliminary antifungal activity tests.
authors.affiliation: State Key Laboratory Breeding Base of Green Pesticide and Agricultural Bioengineering, Key Laboratory of Green Pesticide and Agriculture Bioengineering, Ministry of Education, Guizhou University, Guiyang 550025, China.
authors.forename: Jian
authors.initials: J
authors.lastname: Wu
authors.forename: Qing
authors.initials: Q
authors.lastname: Shi
authors.forename: Zhuo
authors.initials: Z
authors.lastname: Chen
authors.forename: Ming
authors.initials: M
authors.lastname: He
authors.forename: Linhong
authors.initials: L
authors.lastname: Jin
authors.forename: Deyu
authors.initials: D
authors.lastname: Hu
mesh_terms: D000090:Acetoacetates / Q000737:chemistry; D000215:Acylation; D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D000998:Antiviral Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D003500:Cyclization; D005670:Fusarium / Q000187:drug effects* / Q000254:growth & development; D005874:Gibberella / Q000187:drug effects* / Q000254:growth & development; D006845:Hydrocarbons, Fluorinated / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D010084:Oxidation-Reduction; D010659:Phenylhydrazines / Q000737:chemistry; D011092:Polyethylene Glycols / Q000737:chemistry; D011720:Pyrazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D013329:Structure-Activity Relationship; D013861:Thiocyanates / Q000737:chemistry; D013890:Thiourea / Q000031:analogs & derivatives / Q000138:chemical synthesis* / Q000494:pharmacology; D014027:Tobacco Mosaic Virus / Q000187:drug effects* / Q000502:physiology
chemical_list: D000090:Acetoacetates; D000935:Antifungal Agents; D000998:Antiviral Agents; D006845:Hydrocarbons, Fluorinated; D010659:Phenylhydrazines; D011720:Pyrazoles; D013861:Thiocyanates; C030299:phenylhydrazine; D011092:Polyethylene Glycols; C026976:thiocyanic acid; D013890:Thiourea; C024840:ethyl acetoacetate