TOLYLFLUANID Property

Melting point:

96°C

Boiling point:

93℃

Density 

1.5132 (rough estimate)

vapor pressure 

2 x 10^-5 Pa (20 °C)

refractive index 

1.6000 (estimate)

storage temp. 

-20°C

solubility 

soluble in DMSO, Methanol

Colour Index 

45430

Water Solubility 

0.9 mg l^-1 (20 °C)

pka

-5.06±0.50(Predicted)

BRN 

2949607

LogP

3.900

EPA Substance Registry System

Tolylfluanid (731-27-1)

Safety

Hazard Codes 

T,N,T+

Risk Statements 

23-36/37/38-43-48/20-50/53-50-48/23-26

Safety Statements 

24-26-37-38-45-60-61-63-36/37/39-28

RIDADR 

2588

WGK Germany 

3

RTECS 

WO6560000

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

731-27-1(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Danger

Hazard statements

H315Causes skin irritation

H317May cause an allergic skin reaction

H319Causes serious eye irritation

H330Fatal if inhaled

H335May cause respiratory irritation

H372Causes damage to organs through prolonged or repeated exposure

H400Very toxic to aquatic life

Precautionary statements

P273Avoid release to the environment.

P280Wear protective gloves/protective clothing/eye protection/face protection.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

P314Get medical advice/attention if you feel unwell.

TOLYLFLUANID Chemical Properties,Usage,Production

Uses

Tolylfluanid is used to control a wide range of fungal diseases on apples, grapes, strawberries and other fruit and storage diseases on many crops.

Uses

Tolylfluanid may be used as a reference standard for the determination of the analyte in nutraceutical formulations using dispersive liquid-liquid microextraction(DLLME) coupled with gas chromatography-mass spectrometry method.

Definition

ChEBI: A member of the class of sulfamides that is dichlofluanid in which the hydrogen at the para position of the phenyl group is replaced by a methyl group. A fungicide first marketed in 1971 and used in the cultivation of fruit and vegetables, as ell as in wood preservatives, it is no longer approved for use in the European Union.

Metabolic pathway

Tolylfluanid contains an unstable dichlorofluoromethylthio (sulfenyl) moiety that has been shown to undergo rapid hydrolytic and metabolic degradation to dimethylaminosulfotoluidide (2). By analogy with captan, presumably the dichlorofluoromethylthio moiety can be transferred to the sulfur atoms of cellular thiols such as cysteine and glutathione. Thus, in the presence of thiols tolylfluanid is probably cleaved at the N-S bond to form thiophosgene or its monofluoro analogue (3) and other gaseous products such as hydrogen sulfide, hydrogen chloride and carbonyl sulfide. Thiophosgene or its monofluoro analogue is rapidly hydrolysed by water. The dichlorofluoromethylthio group and thiophosgene may be intermediates in the formation of addition products, for example addition to cysteine affords thiazolidine-2-thione-4-carboxylica cid (4). A thiazolidine derivative of glutathione may also be formed. The main metabolic reactions in all media were cleavage of the N-S bond to give dimethylaminosulfotoluidide (2) followed by hydroxylation of the phenyl ring and oxidation of the methyl substituent on the phenyl ring. Glucoside conjugates were detected in plants and the cysteine adduct, thiazolidine-2- thione-4-carboxylic acid (4), was formed in rats.

Degradation

Tolylfluanid is hydrolysed rapidly in alkaline conditions. The hydrolytic DT₅₀ is about 12 days, 29 hours and <10 minutes at pH 4,7 and 9, respectively, at 22 °C. In the environment, hydrolysis is faster than photolysis (PM; PSD, 1995). Tolylfluanid does not absorb light of wavelength >295 nm and so photodegradation is unlikely to occur in the absence of photosensitisers.