Structural Characteristics of &lt;i&gt;s&lt;/i&gt;-Triazine Compounds Inducing Rhizome in &lt;i&gt;Cyperus serotinus&lt;/i&gt; ROTTB

Omokawa, Hiroyoshi; Kuramochi, Hitoshi; Kawata, Yoshinori; Konnai, Makoto

doi:10.1584/jpestics.19.25

Cited by 4 publications

(2 citation statements)

References 5 publications

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“…In cress, these symptoms roughly resembled those caused by mi totic disrupter or cellulose-biosynthesis inhibiting herbicides. As reported by Omokawa et al (1987), structurally related a-substituted benzylamino-striazines exhibited phytotoxic properties distinct from those induced by atrazine, however, depend ent on the respective enantiom er used (Omokawa and Konnai, 1992;Omokawa et al, 1994). The (S)-isomers were potent inhibitors against PET, whereas the (7?…”

Section: Effects In Darknessmentioning

confidence: 64%

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Triaziflam and Diaminotriazine Derivatives Affect Enantioselectively Multiple Herbicide Target Sites

Großmann¹,

Tresch²,

Plath³

2001

Zeitschrift Für Naturforschung C

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Diaminotriazines, Cellulose Synthesis, Mitotic Disrupter Herbicides, Photosynthetic Electron Transport InhibitorsEnantiomers of triaziflam and structurally related diaminotriazines were synthesized and their herbicidal mode o f action was investigated. The compounds caused light and darkdependent effects in multiple test systems including heterotrophic cleaver and photoautotrophic algal cell suspensions, the Hill reaction o f isolated thylakoids and germinating cress seeds. Dose-response experim ents revealed that the fSj-enantiomers of the compounds pref erentially inhibited photosystem II electron transport (PET) and algae growth with efficacies similar to that of the herbicide atrazine. In contrast, the (R )-enantiomers of the diaminotri azines were up to 100 times more potent inhibitors of growth in cleaver cell suspensions and cress seedlings in the dark than the (S)-enantiomers. The most active compound, the (R)-enantiomer of triaziflam, inhibited shoot and root elongation of cress and maize seedlings at concentrations below 1 (j.m. The meristematic root tips swelled into a club shape which is typical for the action of mitotic disrupter herbicides and cellulose biosynthesis inhibitors. Microscopic examination using histochemical techniques revealed that triaziflam (7?)-enantiomer blocks cell division in maize root tips 4 h after treatment. The chromosomes pro ceeded to a condensed state of prometaphase but were unable to progress further in the mitotic cycle. Disruption of mitosis was accompanied by a loss o f spindle and phragmoplast micotubule arrays. Concomitantly, cortical microtubules decreased which could lead to isodiametric cell growth and consequently to root swelling. In addition, a decline in cellulose deposition in cell walls was found 24 h after treatment. Compared to the (7?)-form, triaziflam (S)-enantiomer was clearly less active. The results suggest that triaziflam and related di aminotriazines affect enantioselectively multiple sites o f action which include PET inhibitory activity, mitotic disruption by inhibiting microtubule formation and inhibition of cellulose synthesis.

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Section: Effects In Darknessmentioning

confidence: 64%

“…)-isomers showed growth regulat ing effects in the dark, including inhibition of shoot and root growth and secondary rhizome induction in Cyperus serotinus (Om okawa and Konnai, 1992;Omokawa et al, 1994). The latter activity has been characterised as cytokinin-like (Omokawa et al, 1994). In the cress germination test, the (7?…”

Section: Effects In Darknessmentioning

confidence: 99%

Triaziflam and Diaminotriazine Derivatives Affect Enantioselectively Multiple Herbicide Target Sites

Großmann¹,

Tresch²,

Plath³

2001

Zeitschrift Für Naturforschung C

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Diverse Response of Plants Towards Chiral Phytotoxic Chemicals

Omokawa¹

2002

Herbicide Classes in Development

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Enantioselective Herbicidal Activity of Chiral α-Methylbenzylphenylureas againstCyperaceaeandEchinochloaPaddy Weeds

Ryoo

Kuramochi

Omokawa

1998

Bioscience, Biotechnology, and Biochemistry

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Optically active α-methylbenzylphenylureas were synthesized and tested for their herbicidal activities against barnyardgrass and Cyperaceae paddy weeds in a greenhouse to evaluate the cross intergenus phytotoxicity between rice and barnyardgrass and the enantioselective phytotoxicity to the weeds. Several compounds controlled the growth of the weeds, and a suitable enantiomer for successful weed control was dependent on the type of weed and on the substituent at the aniline moiety. The (R)-2-isoPr and (R)-2-tert-Bu derivatives significantly controlled barnyardgrass and both annual and perennial Cyperaceae paddy weeds. The (R)-2-Et and (R)-2-CF3 derivatives showed the strong herbicidal activity against perennial Cyperaceae paddy weeds, while the (S)-enantiomers of the unsubstituted and fluoro derivatives were active against barnyardgrass. The enantioselectivity of the most potent compounds was high.

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Structural Characteristics of <i>s</i>-Triazine Compounds Inducing Rhizome in <i>Cyperus serotinus</i> ROTTB

Cited by 4 publications

References 5 publications

Triaziflam and Diaminotriazine Derivatives Affect Enantioselectively Multiple Herbicide Target Sites

Triaziflam and Diaminotriazine Derivatives Affect Enantioselectively Multiple Herbicide Target Sites

Diverse Response of Plants Towards Chiral Phytotoxic Chemicals

Enantioselective Herbicidal Activity of Chiral α-Methylbenzylphenylureas againstCyperaceaeandEchinochloaPaddy Weeds

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