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57018-04-9

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57018-04-9 Usage

Uses

Different sources of media describe the Uses of 57018-04-9 differently. You can refer to the following data:
1. Agricultural fungicide.
2. 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An organic thiophosphate that is 2,6-dichloro-4-methylphenol in which the hydrogen of the hydroxy group group has been replaced by a dimethoxyphosphorothioyl group.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.

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).

Check Digit Verification of cas no

The CAS Registry Mumber 57018-04-9 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,7,0,1 and 8 respectively; the second part has 2 digits, 0 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 57018-04:
(7*5)+(6*7)+(5*0)+(4*1)+(3*8)+(2*0)+(1*4)=109
109 % 10 = 9
So 57018-04-9 is a valid CAS Registry Number.
InChI:InChI=1/C9H11Cl2O3PS/c1-6-4-7(10)9(8(11)5-6)14-15(16,12-2)13-3/h4-5H,1-3H3

57018-04-9 Well-known Company Product Price

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  • Sigma-Aldrich

  • (31209)  Tolclofos-methyl  PESTANAL®, analytical standard

  • 57018-04-9

  • 31209-250MG

  • 709.02CNY

  • Detail

57018-04-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name tolclofos-methyl

1.2 Other means of identification

Product number -
Other names Tolclofos-methyl

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:57018-04-9 SDS

57018-04-9Synthetic route

2,6-dichloro-4-methylophenol
2432-12-4

2,6-dichloro-4-methylophenol

dimethyl chlorothiophosphate
2524-03-0

dimethyl chlorothiophosphate

sodium sulfate
7757-82-6

sodium sulfate

tolclofos-methyl
57018-04-9

tolclofos-methyl

Conditions
ConditionsYield
With potassium carbonate In water; toluene
2,6-dichloro-4-methylophenol
2432-12-4

2,6-dichloro-4-methylophenol

dimethyl chlorothiophosphate
2524-03-0

dimethyl chlorothiophosphate

tolclofos-methyl
57018-04-9

tolclofos-methyl

Conditions
ConditionsYield
With copper(l) chloride; sodium hydroxide In water; toluene at 45 - 50℃; for 4.5h;
tolclofos-methyl
57018-04-9

tolclofos-methyl

Mono-demethyl tolclofos-methyl

Mono-demethyl tolclofos-methyl

Conditions
ConditionsYield
With potassium dimethyldithiocarbamate In ethanol Ambient temperature;100%
tolclofos-methyl
57018-04-9

tolclofos-methyl

brucine
357-57-3

brucine

A

C23H26N2O4*C8H9Cl2O3PS

C23H26N2O4*C8H9Cl2O3PS

B

C23H26N2O4*C8H9Cl2O3PS

C23H26N2O4*C8H9Cl2O3PS

Conditions
ConditionsYield
In acetonitrile for 2h; Heating; Yield given. Yields of byproduct given;
tolclofos-methyl
57018-04-9

tolclofos-methyl

2,6-dichloro-4-methylphenyl methyl phosphorochloridothionate
96790-20-4

2,6-dichloro-4-methylphenyl methyl phosphorochloridothionate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 100 percent / potassium dimethyldithiocarbamate / ethanol / Ambient temperature
2: 33 percent / PCl5 / CH2Cl2 / Ambient temperature
View Scheme

57018-04-9Relevant articles and documents

PROCESS FOR PRODUCTION OF PURIFIED O-(2,6-DICHLORO-4-METHYL-PHENYL) O,O-DIMETHYL PHOSPHOROTHIOATE

-

Page/Page column 4, (2011/10/12)

A process for producing a purified O—(2,6-dichloro-4-methylphenyl)—O,O-dimethyl phosphorothioate, the process comprising: the first step of bringing a crude O—(2,6-dichloro-4-methylphenyl)—O,O-dimethyl phosphorothioate into contact with an acid; and the second step of recovering the purified O—(2,6-dichloro-4-methylphenyl)—O,O-dimethyl phosphorothioate from the mixture obtained in the first step.

Composition for controlling harmful bio-organisms and method for controlling harmful bio-organisms using the same

-

, (2008/06/13)

A composition for controlling harmful bio-organisms comprising (a) at least one imidazole compound represented by formula (I): wherein R represents a lower alkyl group or a lower alkoxy group; and n represents an integer of 1 to 5, as an active ingredient, and (b) at least one inorganic phosphorus compound and/or at least one fungicide for Phycomycetes as an active ingredient or (c) a spreader as an activity-enhancing ingredient, and a method for controlling harmful bio-organisms comprising applying the composition for controlling harmful bio-organisms onto harmful bio-organisms.

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