CHLOZOLINATE

CHLOZOLINATE Basic information
Product Name:CHLOZOLINATE
Synonyms:CHLOZOLINATE;SERINAL;ethyl (RS)-3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxooxazolidine-5-carboxylate;chlozolinate (bsi,iso);ethyl 3-(3,5-dichlorophenyl)-5- methyl-2,4-dioxo-5-oxazolidinecarboxyate;chlozolinate (ISO) ethyl (RS)-3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-oxazolidine-5-carboxylate;Chlozolinate solution;5-Oxazolidinecarboxylic acid, 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-, ethyl ester, (+-)-
CAS:84332-86-5
MF:C13H11Cl2NO5
MW:332.14
EINECS:282-714-4
Product Categories:
Mol File:84332-86-5.mol
CHLOZOLINATE Structure
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)
Fp 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
MSDS Information
CHLOZOLINATE Usage And Synthesis
UsesChlozolinate is a dicarboximide fungicide which is used primarily on grapes.
UsesChlozolinate 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.
DefinitionChEBI: 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 DescriptionChlozolinate is a systemic fungicide, used for the control of downy mildew, brown rot, and fruit rot in agricultural commodities.
Metabolic pathwayThe 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.
DegradationChlozolinate (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 Preparation Products And Raw materials
Trifloxystrobin Chlorothalonil (R)-Chlozolinate

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