By H. Geissbühler, G. T. Brooks and P. C. Kearney (Eds.)
Read or Download Synthesis of Pesticides Chemical Structure and Biological Activity Natural Products with Biological Activity. Symposia Papers Presented at the Fourth International Congress of Pesticide Chemistry, Zurich, Switzerland, July 24–28, 1978 PDF
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Additional info for Synthesis of Pesticides Chemical Structure and Biological Activity Natural Products with Biological Activity. Symposia Papers Presented at the Fourth International Congress of Pesticide Chemistry, Zurich, Switzerland, July 24–28, 1978
Example text
Fig. I. X-ray a n a l y s i s of d i m e t h y l - m a l e i c a n h y d r i d e (dotted lines show the Van d e r Waals radii of the two methyl g r o u p s ) . Crystals of DMA a r e : o r t h o r h o m b i c ; Pbca* 3 = 1 3 . 1 6 4 ( 4 ) , b = 1 0 . 8 1 4 ( 3 ) , c = 8 . 2 Â 3 ; Z = 8. 058. DMA is c o m p l e t e l y symmetrical and planar and the Van der W a a l s radii of the two methyl groups - shown with dotted lines - o v e r l a p . So there must be considerable r e p u l s i v e steric i n t e r a c t i o n between the two methyl g r o u p s .
The same compound (IX) can however be obtained in 82% yield using an amide-acid chloride adduct type synthesis by the condensation of Η,Ν-dimethylbenzamide with 3-amino-(2,-methyl)cinnamamide in the presence of phosphorus oxychloride. Dichromate oxidation followed by catalytic reduction gave the desired carboxylic acid (X). The pyrimidine analogue (XI) was synthesized in an overall yield of 20% by bromination of 2'-methyl chalcone followed by condensation with urea under acidic conditions and phosphorus oxychloride treatment of the resulting pyrimidone.
Tetrametrin (Ref. 3) is a crysanthemum acid ester of an alcohol which comes from the Diels-Alder adduct of maleic anhydride and butadiene. It is a contact insecticide. The newest derivative with a fivemembered imide structure is Sumilex (Ref. 4 ) which is a fungicide. 85 86 M. E. Baumann and H. Bosshard SYNTHESIS AND PROPERTIES OF DIMETHYL-MALEIC ANHYDRIDE In contrast to the readily available and well studied maleic and citraconic a n h y d r i d e s , dialkyl substituted maleic anhydrides such as dimethyl-maleic anhydride (DMA for short) are expensive and not yet readily available (Refs.