Substituent Effect on Photosynthesis of N^2-α-Substituted Benzyl-N^4-alkyl-2,4-diamino-6-chloro-s-triazines and Their Phytotoxic Property(Pesticide Chemistry)

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• The influence of substituents on the activities of a series of N^2-α-substituted benzyl-N^4-alkyl-2,4-diamino-6-chloro-s-triazines as inhibitors of photosystem II (PSII) was examined, and the phytotoxic differences between them and atrazine, as to the photosynthesis in leaf disks, mesophyll cells, intact chloroplasts and broken chloroplasts of spinach, and as to seedling-growth, were discussed. The inhibitory activity of the N^2-α,α-dimethylbenzyl-N^4-ethyl derivative (6), which was comparable on that of atrazine, was lower than those of the N^2-α-alkylbenzyl analogues (1〜5). The N^4-n-alkyl-N^2-α-methylbenzyl derivatives, in spite of the carbon length of the alkyl group, exhibited more potent activity than atrazine, but an α or β substitution of the N^4-n-alkyl group caused a decrease in the activity with a few exceptions. These data may imply that the space of the binding site on PSII surrounding both the N^2 and N^4 amino groups is relatively large. The binding between the receptor site and the N^4 amino group, however, is easily influenced by a slight structural change in an inhibitor. The herbicidal compounds, N^2-α-methylbenzyl-N^4-ethyl (1), N^2-α,α-dimethylbenzyl-N^4-1-methylpropyl (30) and N^2-α-methylbenzyl-N^4,N^4-diethyl (42) derivatives, exhibited potent inhibitory activity in the seedling growth test under dark/light conditions, whereas atrazine was very poor. The inhibitory activity of compound (1) toward photosynthesis was poor with leaf disks, compared to atrazine, whereas, the order of their activities was the reverse for plant preparations such as abaxial epidermis peeled leaf disks, mesophyll cells, intact chloroplasts and broken chloroplasts. It was indicated that a change in the phytotoxic symptom in the whole plant assay would be correlated to the permeability of the compound through the plant membrane(s).

• 社団法人日本農芸化学会の論文
• 1989-10-23

著者

• Kobayashi Izumi

  Central Research Laboratories Idemitsu Kosan Co. Ltd.

• Konnai Makoto

  Weed Science Center, Utsunomiya University

• OMOKAWA Hiroyoshi

  Weed Science Research Institute, Faculty of Agriculture, Utsunomiya University

• Omokawa Hiroyoshi

  Weed Science Research Institute Faculty Of Agriculture Utsunomiya University

• Omokawa Hiroyoshi

  Weed Control Research Institute Faculty Of Agriculture Utsunomiya University

• Konnai Makoto

  Weed Science Research Institute Faculty Of Agriculture Utsunomiya University

• Konnai Makoto

  Weed Control Research Institute Faculty Of Agriculture Utsunomiya University

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