By Elin M. Ulrich, Candice N. Morrison (auth.), David M. Whitacre (eds.)
Reviews of Environmental infection and Toxicology makes an attempt to supply concise, serious experiences of well timed advances, philosophy and important parts of comprehensive or wanted pastime within the overall box of xenobiotics, in any section of our surroundings, in addition to toxicological implications.
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Example text
Acetochlor, metolachlor, and propisochlor have a bond with restricted rotation leading to atropisomers, which typically are not identified by the MOE software. Amiprofos-methyl, bilanafos, butamifos, DMPA (O-2,4-dichlorophenyl O-methyl isopropylphosphor-amidothioate), fosamine, and glufosinate have a chiral phosphorous atom, and NC-330 has a chiral sulfur atom. Prototropy (transfer of a proton) between the =O and –OH on the chiral phosphorus atom of glufosinate may be rapidly equilibrated under certain pH conditions, rendering the tautomers difficult if not impossible to distinguish by enantioselective techniques.
The mode of action of many herbicides is to interfere with chiral plant hormones controlling growth, so it is not surprising that the absolute configuration of the pesticide plays a role in efficacy (Naber and van Rensen 1988). The degradation of dichlorprop and mecoprop by soil microbes is enantioselective because two different enzymes each metabolize one enantiomer (Zipper et al. 1996; Nickel et al. 1997; Kohler et al. 1998; Zipper et al. 1998; Müller and Babel 1999). These two examples demonstrate how the degradation is different between stereoisomers, and this, when combined with stereospecific toxicity, can affect not only efficacy, but also exposure and risk to humans and other nontarget organisms in the environment.
Ulrich et al. We have included the herbicide 2,4-D [(2,4-dichlorophenoxy)acetic acid] in Table 3 and Fig. 4 as an example of an acid herbicide that can be paired with chiral esters or salts, but the herbicide itself is not chiral. Any achiral acid herbicide that is paired with such chiral moieties will be chiral as long as the bonding is sustained. , ester hydrolysis). For clarity, please see footnotes in the tables for such compounds. , 3,4-DP; 2-(3,4-dichlorophenoxy)propanoic acid], but these pesticides may contain additional chiral centers (and thus stereoisomers) that depend on the formulation.
