CHLOZOLINATE Chemical Properties

Melting point:

110-114 °C

Boiling point:

420.8±55.0 °C(Predicted)

Density 

1.479

vapor pressure 

1.3 x 10^-5 Pa (25 °C)

Flash point:

100 °C

storage temp. 

0-6°C

pka

-4.24±0.40(Predicted)

Water Solubility 

2 mg l^-1 (25 °C)

Safety Information

Hazard Codes 

Xn,N,F

Risk Statements 

40-51/53-67-65-50/53-38-11-20

Safety Statements 

36/37-61-62-60-33-25-16-9

RIDADR 

UN3077 9/PG 3

WGK Germany 

2

HS Code 

29251900

CHLOZOLINATE Usage And Synthesis

Uses

Chlozolinate controls fruit rot, downy mildew and brown rot in pome and stone fruits, vines, vegetables, strawberries and ornamentals caused by Botrytis, Monilia and Sclerotinia, efc.

Uses

Chlozolinate is a dicarboximide fungicide which is used primarily on grapes.

Definition

ChEBI: Ethyl 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-1,3-oxazolidine-5-carboxylate is the ethyl ester of 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-1,3-oxazolidine-5-carboxylic acid. It is a dichlorobenzene, an oxazolidinone, a dicarboximide and an ethyl ester.

General Description

Chlozolinate is a systemic fungicide, used for the control of downy mildew, brown rot, and fruit rot in agricultural commodities.

Metabolic pathway

The fungicides, chlozolinate, vinclozolin, and procymidone, are added to wine after fermentation and the degradation products are isolated and identified. Chlozolinate undergoes a rapid hydrolytic loss of the ethoxycarbonyl substituent to give an oxazolidine that further undergoes hydrolytic cleavage to give 3' ,5' -dichloro-2-hydroxypropanilide. The oxazolidine ring of vinclozolin undergoes a similar hydrolysis reaction to give the corresponding anilide, 3' ,5'-dichloro-2-hydroxy-2-methylbut-3-eneanilide. Both of these anilides are stable in wine for 150 days. A different degradation behavior is observed with procymidone and leads to the formation of 3,5- dichloroaniline, which, in turn, breaks down in wine.

Degradation

Chlozolinate (1) hydrolysed rapidly at 25 °C in alkaline solution with DTm values of 6 hours (pH 6.8) and 16 min (pH 8.3). Three hydrolytic degradation reactions were observed. The first reaction involved the cleavage of the ethyl ester to yield the corresponding carboxylic acid (2). Compound 2 underwent decarboxylation to yield 3-(3,5-dichlorophenyl)-5-methyloxazolidine- 2,4-dione (3). The third reaction involved the opening of the oxazolidinedione ring to yield 3',5'-dichloro-2-hydroxypropanilide(4) (Villedieu et al., 1994,1995).
Chlozolinate degraded rapidly in wine during the vinification process (DT₅₀ 0.35 and 0.14 day at pH 3 and 4, respectively). Decarboxylation resulted in the formation of compound 3 as the major product (Cabras et al., 1984; Pirisi et al., 1986; Gennari et al., 1992).

CHLOZOLINATE(84332-86-5)Related Product Information

• Trifloxystrobin
• Chlorothalonil
• (R)-Chlozolinate