| Identification | More | [Name]
Tolclofos-methyl | [CAS]
57018-04-9 | [Synonyms]
2,6-dichloro-4-methylphenyl o,o-dimethyl phosphorothioate
Dimethyl O-(2,6-dichloro-4-methylphenyl) phosphorothioate
O-(2,6-DICHLORO-4-METHYLPHENYL) O,O-DIMETHYL PHOSPHOROTHIOATE
RIZOLEX
S-3349
TOLCLOFOS-METHYL
Basilex
Dichloro-4-methylphenyl-O,O-dimethyl phosphorothioate
o-(2,6-Dichloro-4-methylphenyl) o,o-dimethyl thiophosphate
o-(2,6-dichloro-p-tolyl)o,o-dimethylesterofphosphorothioicacid
O-(2,6-Dichloro-p-tolyl)-O,O-dimethylthiophosphate
o,o-dimethylo-(2,6-dichloro-4-methylphenyl)phosphorothioate
Phosphorothioic acid, O-(2,6-dichloro-4-methylphenyl) O,O-dimethyl ester
Phosphorothioicacid,esters,O-(2,6-dichloro-4-methylphenyl)-O,O-dimethylester
phosphorothioicacid,o-(2,6-dichloro-4-methylphenyl)o,o-dimethylester
phosphorothioicacid,o-(2,6-dichloro-p-tolyl)o,o-dimethylester
Risolex
Tolcofos-methyl
BENZTHIAZURON PESTANAL, 100 MG
tolclofos-methyl (bsi,iso) | [EINECS(EC#)]
260-515-3 | [Molecular Formula]
C9H11Cl2O3PS | [MDL Number]
MFCD00078741 | [Molecular Weight]
301.13 | [MOL File]
57018-04-9.mol |
| Safety Data | Back Directory | [Hazard Codes ]
Xi,N | [Risk Statements ]
43-50/53 | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 3077 9 / PGIII | [WGK Germany ]
3 | [RTECS ]
TF0460000 | [HS Code ]
29201900 | [Hazardous Substances Data]
57018-04-9(Hazardous Substances Data) | [Toxicity]
LD50 in male, female rats, male, female mice (mg/kg): ~5000, ~5000, 3500, 3600 orally; all >5000 dermally; ~5000, 4900, 1070, 1260 i.p.; all >5000 s.c. (Ohtsuki, Fujinami) |
| Hazard Information | Back Directory | [Uses]
Agricultural fungicide. | [Uses]
Tolclofos-methyl is a non-systemic organophosphorus fungicide
with both protective and curative activities that control soil-borne diseases
caused by Rhizoctonia solani, Corticium rolfsii, Tphula incamata and Typhula
ishikariensis in/on potatoes, sugar beet, cotton and peanuts. | [Definition]
ChEBI: An organic thiophosphate that is 2,6-dichloro-4-methylphenol in which the hydrogen of the hydroxy group group has been replaced by a dimethoxyphosphorothioyl group. Tolclofos-methyl is a phospholipid biosynthesis inhibitor and fungicide that is used for co
trolling soil-borne diseases caused by Typhula incarnata, Corticium rolfsii, Typhula ishikariensis, and Rhizoctonia solani. | [Metabolic pathway]
Tolclofos-methyl underwent common degradation and metabolic pathways
in water, soil, plants and animals. These reactions are well
documented for most organophosphorus compounds and include oxidative
desulfuration, hydroxylation/oxidation of the 4-methyl group
to the alcohol and carboxylic acid, cleavage of the P-O-aryl linkage,
O-demethylation and conjugation. In addition to the above reactions,
photolytic isomerisation to the thionate (P=S) was also observed. A
schematic presentation of the primary metabolic pathways for tolclofosmethyl
is illustrated in Scheme 1. | [storage]
Store at -20°C | [Degradation]
[14C-phenyl]Tolclofos-methyl(1) was stable to hydrolytic degradation at
pH 5, 7 and 9 at 22°C with DT50 values of 139, 417 and 238 days,
respectively. Higher temperature led to a more rapid hydrolysis and two
hydrolysis products were detected. O-Demethylation and oxidative desulfuration
were the major reactions to yield 2,6-dichloro-p-tolyl methyl
hydrogen phosphorothioate (2) and toclofos-methyl oxon (O-2,6-dichlorop-
tolyl O,O-dimethyl phosphate, 3), respectively. Cleavage of the P-O-aryl
linkage yielded 2,6-dichloro-4-methylphenol(4) as a minor degradation
product (WHO, 1994).
Tolclofos-methyl degraded in water under natural sunlight irradiation
with DT50 values of 44 days (in distilled water), 15-28 days (in natural
river and pond water) and less than 2 days in 2% acetone/water. The
major degradation reactions included oxidative desulfuration to yield
compound 3 and O-demethylation to yield compound 2. The major
photodegradation products in river and pond waters and soil thinlayer
surfaces were compounds 2, 3, 4 and the O-demethylated 3 (2,6-
dichloro-p-tolyl methyl hydrogen phosphate, 5) (Mikami et al., 1984).
In acetone solution, demethylation of the isomerisation product [2,6-
dichloro-p-tolyl O,S-dimethyl phosphorothioate (6)] yielded 2,6-dichlorop-
tolyl S-methyl hydrogen phosphorothioate (7) and 2,6-dichloro-p-tolyl
dihydrogen phosphate (8) as the major photodegradates (Mikami et al.,
1984). | [Toxicity evaluation]
Its acute oral toxicity is very low in comparison with
a thio-ester type of other organophosphorus fungicides
(edifenphos, iprobenfos, and pyrazophos). |
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