Enantioselective effects of optically active alpha-methylbenzyl-s-triazine on the root growth of rice [Oryza sativa] and Echinochloa plants and their herbicidal activity

"The chiral requirement on the alpha-methylbenzyl moiety of 2,4-diamio-6-chloro-s-triazine for sufficient inhibition of root growth was similar towards both rice and barnyard millet. With the monoalkylamino series, the most suitable configuration was markedly changed by the substituent on the o...

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Bibliographic Details
Published in:Bioscience, biotechnology, and biochemistry biotechnology, and biochemistry, 2002-09, Vol.66 (9), p.1959-1962
Main Authors: "Omokawa, H. (Utsunomiya Univ. (Japan)), Tabei, A.
Format: Article
Language:English
Subjects:
Biological and medical sciences
Chemical control
ECHINOCHLOA
Echinochloa - drug effects
Echinochloa - growth & development
enantioselectivity
Fundamental and applied biological sciences. Psychology
GROWTH INHIBITORS
herbicidal activity
HERBICIDES
Herbicides - chemistry
Herbicides - pharmacology
Molecular Structure
Optical Rotation
optically active s-triazine
Oryza - drug effects
Oryza - growth & development
ORYZA SATIVA
Parasitic plants. Weeds
PESTICIDE SELECTIVITY
Pfeiffer's rule
PHOTOSENSITIVITY
Phytopathology. Animal pests. Plant and forest protection
Plant Roots - drug effects
Plant Roots - growth & development
ROOTS
Species Specificity
Stereoisomerism
TRIAZINES
Triazines - chemistry
Triazines - pharmacology
Weeds
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Summary:"The chiral requirement on the alpha-methylbenzyl moiety of 2,4-diamio-6-chloro-s-triazine for sufficient inhibition of root growth was similar towards both rice and barnyard millet. With the monoalkylamino series, the most suitable configuration was markedly changed by the substituent on the other amino moiety. However, for the dialkylamino series, the (S)-enantiomer was an active inhibitor. Clear species selectivity between rice and barnyard millet was observed in the series for the (R)-enantiomers, providing high herbicidal activity toward Echinochloa plants and safety toward rice. The enantioselectivity against barnyard millet increased with increasing inhibitory activity of the active enantiomers, following Pfeiffer's rule. R-EtNH (3) controlled the growth of barnyardgrass with leaf-burning (LB) under paddy conditions, and S-EtNH (4) and S-Et2N (20) controlled the growth without LB. The RS-EtNH derivative is an interesting inhibitor controlling the growth of barnyardgrass from the just-germinated stage (by the (R)-enantiomer) to early-middle growth stage (by the (S)-enantiomer)."
ISSN:0916-8451
1347-6947
DOI:10.1271/bbb.66.1959