ACTIVITY:
Herbicide
(triazine)
CAS Name:
N-[2-(3,5-dimethylphenoxy)-1-methylethyl]-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine
Structure:
Regulatory
Information
(only comprehensive for the US) |
US
EPA Registered: |
No |
Other
Information |
Molecular
Formula: |
C17H24
F N5O |
Entry
Year: |
1994 |
Inventing
Company: |
Idemitsu
Kosan |
Other
Names: |
IDH-1105
|
Of
special interest: |
PAN
Data |
October
2001 - Glossary of
Pesticide Chemicals- A listing of
pesticides subject to analysis of residues in foods and feeds
by the US Food and Drug Administration. |
Adverse
Effects:
As
of Oct 2003: No data available |
June
14, 2001 - Implementation
of the Community Strategy for Endocrine Disruptors - a
range of substances suspected of interfering with the hormone
systems of humans and wildlife. Communication from the Commission
to the Council and the European Parliament. Commission of
the European Communities, Brussels COM (2001) 262 final.
This
document presents a "priority list of substances for
further evaluation of their role in endocrine disruption.
During 2000, a candidate list of 553 man-made substances and
9 synthetic/natural hormones has been identified."
Category
included on the Endocrine Disruptor Liist |
Triazines |
While
only the broad category "Triazines" was included in
the Commission's list, the organofluorine pesticide Triaziflam
is a "Triazine" herbicide. |
http://www.ncbi.nlm.nih.gov:80/entrez/query.fcgi?cmd=Retrieve&db=PubMed&list_uids=11531090&dopt=Abstract
Z Naturforsch
[C]. 2001 Jul-Aug;56(7-8):559-69.
Triaziflam
and Diaminotriazine derivatives affect enantioselectively
multiple herbicide target sites.
Grossmann
K, Tresch S, Plath P.
BASF
Agricultural
Center Limburgerhof, Germany. Klaus.Grossmann@basf-ag.de
Enantiomers
of triaziflam and structurally related diaminotriazines were
synthesized and their herbicidal mode of action was investigated.
The compounds caused light and dark-dependent effects in multiple
test systems including heterotrophic cleaver and photoautotrophic
algal cell suspensions, the Hill reaction of isolated thylakoids
and germinating cress seeds. Dose-response experiments revealed
that the (S)-enantiomers of the compounds preferentially 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 diaminotriazines 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 microM. 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 (R)-enantiomer blocks cell division
in maize root tips 4 h after treatment. The chromosomes proceeded
to a condensed state of prometaphase but were unable to progress
further in the mitotic cycle. Disruption of mitosis was accompanied
by a loss of 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 (R)-form, triaziflam
(S)-enantiomer was clearly less active. The results suggest
that triaziflam and related diaminotriazines affect enantioselectively
multiple sites of action which include PET inhibitory activity,
mitotic disruption by inhibiting microtubule formation and
inhibition of cellulose synthesis. |
|