By Philip S. Magee
content material: the invention of ivermectin and different avermectins / W.C. Campbell, R.W. Burg, M.H. Fisher, and R.A. Dybas --
Sulfonylureas : new excessive efficiency herbicides / Richard F. Sauers and George Levitt --
o-(5-oxo-2-imidazolin-2-yl)arylcarboxylates: a brand new type of herbicides / Marinus Los --
the invention and improvement of bromethalin, an acute rodenticide with a special mode of motion / Barry A. Dreikorn and George O.P. O'Doherty --
Synthesis-directing constitution : task relationships of a few fungicides inhibiting ergosterol biosynthesis / I.F. Brown, Jr., H.M. Taylor, and R.E. Hackler --
Propesticides / T. Roy Fukuto --
features of the biochemistry and toxicology of octopamine in arthropods / R.M. Hollingworth, E.M. Johnstone, and N. Wright --
Harnessing insect-specific enzymes to turn on novel proinsecticides / Glenn D. Prestwich, Ryohei Yamaoka, Seloka Phirwa, Angelo Depalma, Michael Angelastro, and Apurba ok. Gayen --
Substituted pyridazinone herbicides : structural necessities for motion on membrane lipids / Judith B. St. John, Ulrich Schirmer, Falk R. Rittig, and Hermann Bleiholder --
Insecticidal and molluscicidal actions of isobutylamides remoted from Fagara macrophylla and their man made analogs / Isao Kubo, James A. Klocke, Takeshi Matsumoto, and Tadao Kamikawa --
The layout of triazole fungicides / A.F. Marchington --
Optimization of physicochemical and biophysical homes of insecticides / I.J. Graham-Bryce --
Partitioning in pesticide mode of motion and environmental difficulties / A.J. Leo --
The remedy of ionizable compounds in quantitative structure-activity reports with targeted attention to ion partitioning / Robert A. Scherrer --
Bulk and steric parameters in binding and reactivity of bioactive compounds / Marvin Charton --
Use of STERIMOL, MTD, and MTD* steric parameters in quantitative structure-activity relationships / J. Tipker and A. Verloop --
Biphenylmethyl pyrethroids : a quantitative structure-activity dating method of pesticide layout / Ernest L. Plummer --
Regression techniques to structure-activity relationships in miticidal 2-aryl-1,3-cycloalkanediones and enol esters / A. Peter Kurtz.
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Extra info for Pesticide Synthesis Through Rational Approaches (Acs Symposium Series)
What i s evident from the above d i s c u s s i o n i s that the i m i d a z o l i n y l a r y l c a r b o x y l a t e s c o n s t i t u t e an e x c i t i n g new c l a s s of h e r b i c i d e s and that w i t h i n t h i s c l a s s , three members, AC 222,293, AC 252,925, and AC 252,214 have been shown to have s t r i k i n g l y d i f f e r e n t and u s e f u l b i o l o g i c a l p r o p e r t i e s . 1 2 AC 222,293 (Cereals) ,C00 1/ H jk-CH(CH„)„ 3 3 2 AC 252,925 ( T o t a l Vegetation ,C00H A A Τ ii ι AC 252,214 (Legumes) Control) PESTICIDE SYNTHESIS THROUGH RATIONAL APPROACHES 44 Acknowledgment s I would l i k e to acknowledge the many c o n t r i b u t i o n s made by members of Dr.
D. R. C i a r l a n t e and P. L. Orwick and the H e r b i c i d e D i s c o v e r y Group and the nmr a n a l y s i s provided by Mr. F. Heim and Dr. P. C. Mowery o f the P h y s i c a l and A n a l y t i c a l Research S e c t i o n . 1 Literature Cited 1. ch003 2. 3. 4. 5. 6. 7. 8. 9. 10. 11. 12. Suttle, J . C . ; Schreiner, D. R. J . Plant Growth Regul. 1982, 1, 139. Lawrence, A. ; Sweetser, P. B. S. Patent 3 948 937, 1976. Lawrence, L. A. S. Patent 4 038 285, 1977. Howe, R. K. S. Patent 4 135 910, 1979.
The synthesis f o r the m-toluate i s shown i n Scheme I I . Scheme I I A ,COOH π CH /· . CONH-j-CONH,, ii / \ A / /V/ CH 1. 2 sec-BuLi 2. CO. ch003 A s i m i l a r sequence s t a r t i n g w i t h m - t o l u i c a c i d then gave the £-toluate. One f u r t h e r question needed to be r e s o l v e d . The carbon atom i n AC 222,293 bearing the methyl and i s o p r o p y l group i s c h i r a l . Does a l l the b i o l o g i c a l a c t i v i t y r e s i d e i n one enantiomer? The preparation of a s u i t a b l e c h i r a l intermediate was achieved by means of an enzymatic r e s o l u t i o n : The r e s o l u t i o n of α-methylvaline had not been reported at the time t h i s work was done.