Importance of considering pesticide stereoisomerism--proposal of a scheme to apply Directive 91/414/EEC framework to pesticide active substances manufactured as isomeric mixtures.

An important gap has been detected in the application of the European framework for the evaluation of pesticide active substances constituted by enantiomeric and other kind of stereoisomeric mixtures. Up to date, little attention has been paid to the different biological properties of these compounds. Considering efficacy, toxicity, environmental fate and behaviour and ecotoxicity of separated isomers is necessary to fulfil Directive 91/414/EEC objectives of health and environment protection. Here, a critical review of this question for pesticide active substances is presented. An evaluative scheme for considering this question in the framework of Directive 91/414/EEC is also proposed.

[1]  J. Miyamoto,et al.  Stereoselective formation of a cholesterol ester conjugate from fenvalerate by mouse microsomal carboxyesterase(s). , 1986, Journal of biochemical toxicology.

[2]  J. Miyamoto,et al.  Chirality in agrochemicals. , 1998 .

[3]  Antonius Kettrup,et al.  Enantiomeric Selectivity in the Environmental Degradation of Dichlorprop As Determined by High-Performance Capillary Electrophoresis , 1996 .

[4]  H. A. Kuiper,et al.  Chirality in synthetic agrochemicals: bioactivity and safety considerations , 1999 .

[5]  J. W. Cook.  Methods of Organic Chemistry , 1954, Nature.

[6]  S. Fanali,et al.  Stereoselective analysis of acid herbicides in natural waters by capillary electrophoresis , 1999, Electrophoresis.

[7]  仁孝 高野,et al.  (E)-1-(2,4-Dichlorophenyl)-4,4-dimethyl-2-(1,2,4-triazol-1-yl)-1-penten-3-ol (S-3308L) の光学異性体の抗菌性および植物成長調節活性 , 1986 .

[8]  François-René Bourgeois,et al.  The optical isomers of α‐cyano‐3‐phenoxybenzyl 3‐(1,2‐dibromo‐2,2‐dichloroethyl)‐2,2‐dimethylcyclo‐propanecarboxylate and their insecticidal activities , 1980 .

[9]  G. R. Tombo,et al.  Chirality and Crop Protection , 1991 .

[10]  A. Yoshitake,et al.  Substrate specificity for formation of cholesterol ester conjugates from fenvalerate analogues and for granuloma formation. , 1988, Xenobiotica; the fate of foreign compounds in biological systems.

[11]  W. Giger,et al.  Environmental Fate of Chiral Pollutants – the Necessity of Considering Stereochemistry , 1997, CHIMIA.

[12]  J. Miyamoto,et al.  Differential metabolism of fenvalerate and granuloma formation. I. Identification of a cholesterol ester derived from a specific chiral isomer of fenvalerate. , 1986, Toxicology and applied pharmacology.

[13]  H. Buser,et al.  Environmental behavior of acetamide pesticide stereoisomers. 2. Stereo- and enantioselective degradation in sewage sludge and soil. , 1995, Environmental science & technology.

[14]  H. Ohkawa,et al.  Stereoselectivity in metabolism of the optical isomers of cyanofenphos (O-p-cyanophenyl O-ethyl phenylphosphonothioate) in rats and liver microsomes. , 1977 .

[15]  H.-R. Buser,et al.  ENANTIOSELECTIVE ANALYSES OF PERSISTENT AND MODERN PESTICIDES. A STEP TOWARD SUSTAINABLE AGRICULTURE , 1997 .

[16]  C. D. S. Tomlin,et al.  The Pesticide Manual , 2003 .

[17]  H. Buser,et al.  Conversion Reactions of Various Phenoxyalkanoic Acid Herbicides in Soil. 1. Enantiomerization and Enantioselective Degradation of the Chiral 2-Phenoxypropionic Acid Herbicides , 1997 .

[18]  R. Crossley.  The relevance of chirality to the study of biological activity , 1993 .