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Probing Structure-Property Relationships in a Family of Aryloxyphenoxy Propionate Herbicides Using Single Crystal X-Ray Diffraction Techniques

Published online by Cambridge University Press:  06 March 2019

Philip R. Rudolf ,
Larry Kershner  and
Jim Tai
Philip R. Rudolf
Affiliation:
Analytical Sciences; Agricultural Chemicals Process Research The Dow Chemical Company, Midland MI 48667, USA
Larry Kershner
Affiliation:
Analytical Sciences; Agricultural Chemicals Process Research The Dow Chemical Company, Midland MI 48667, USA
Jim Tai
Affiliation:
Analytical Sciences; Agricultural Chemicals Process Research The Dow Chemical Company, Midland MI 48667, USA
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Extract

Aryloxyphenoxy propionates are a widely manufactured class of highly active grass-selective herbicides for use in various crops. Examples include VERDICT (1a), FUSILADE (1b), WHIP (1c), and ASSURE (1d). Figure 1 shows the general structure of aryloxyphenoxy propionates. All of these compounds contain a chiral center and each enantiomer of the optical pair exhibits significantly different herbicidal activity. The optically active isomers can be prepared by reacting the corresponding substituted phenoxyphenol with the S-(-)methyl lactate sulfonate ester (2). However, the optical yield from this type of reaction is usually less than 85%. Optical purification can be achieved by control of the crystallization.

Type
IX. XRD Applications: Detection Levitts, Superconductors, Organics, Minerals
Information
Advances in X-Ray Analysis , Volume 35 , Issue A: First Pacific-International Congress on X-ray Analytical Methods (PICXAM). Fortieth Annual Conference on Applications of X-ray Analysis, August 7-16, 1991 , 1991 , pp. 641 - 643
Copyright
Copyright © International Centre for Diffraction Data 1991

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References

1. Trademarks of: a) DowElanco; (b) ICI/Ishihara; (c) Hoescht; (d) Nissan/DuPont/Rhone Poulenc/FBC.Google Scholar
2. For example: J. Pesticide Soi. 69, 10, 1985.Google Scholar
3. Kennard, C.H.L. and Smith, G., Chem. Aust. 399, 47, 1960.Google Scholar