Synthesis, Fungicidal Activity, and Effects on Fungal Polyamine Metabolism of Novel Cyclic Diamines

A number of novel, cyclic diamines were synthesized and examined for fungicidal activity as part of a continuing program of work on polyamine analogues. The novel synthetic cyclic diamines trans-1,2-bis(diethylaminomethyl)cyclopentane (compound 1) and trans-5,6-bis(aminomethyl)bicyclo[2.2.1]hept-2-e...

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Bibliographic Details
Published in:Journal of agricultural and food chemistry 1997-06, Vol.45 (6), p.2341-2344
Main Authors: Havis, Neil D, Walters, Dale R, Cook, Fiona M, Robins, David J
Format: Article
Language:English
Subjects:
AMINAS
AMINE
AMINES
Biological and medical sciences
Chemical control
Control
FONGICIDE
Fundamental and applied biological sciences. Psychology
Fungal plant pathogens
FUNGICIDAS
FUNGICIDES
MILDEWS
MILDIOU OIDIUM
MILDIU
PESTICIDAL PROPERTIES
Phytopathology. Animal pests. Plant and forest protection
PROPIEDADES PLAGUICIDAS
PROPRIETE DES PESTICIDES
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Summary:A number of novel, cyclic diamines were synthesized and examined for fungicidal activity as part of a continuing program of work on polyamine analogues. The novel synthetic cyclic diamines trans-1,2-bis(diethylaminomethyl)cyclopentane (compound 1) and trans-5,6-bis(aminomethyl)bicyclo[2.2.1]hept-2-ene (compound 2) and the synthetic cyclic diamine 1,2-bis(dimethylaminomethyl)-4,5-dimethylcyclohexa-1,4-diene (compound 3) controlled the important crop pathogen Erysiphe graminis DC f.sp. hordei Marchal. Since E. graminis cannot be cultured in vitro, the effects of the three diamines on polyamine biosynthesis were studied using the fungal pathogen Pyrenophora avenae Ito & Kuribay. All three compounds were effective in reducing the growth of P. avenae in vitro and in altering polyamine levels. However, whereas compound 1 reduced concentrations of all three polyamines, compound 2 increased spermidine 2-fold and compound 3 had little effect on spermidine and spermine concentrations but reduced putrescine concentration by 69%. These changes in polyamine concentrations could not be correlated with changes in activities of biosynthetic enzymes. It seems therefore that although these novel cyclic diamines alter fungal polyamine metabolism, their effects on the growth of P. avenae may not be related to depletion of cellular polyamines. Keywords: Polyamines; cyclic diamines; fungicide; powdery mildew
ISSN:0021-8561
1520-5118
DOI:10.1021/jf9608534