84332-86-5

Basic information

• Product Name: CHLOZOLINATE
• Synonyms: CHLOZOLINATE;SERINAL;ethyl (RS)-3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxooxazolidine-5-carboxylate;(±)ethyl 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-5-oxazolidinecarboxylate;ethyl(±) 3-(3,5-dichlorophenyl)-5-methyl-2,4-dioxo-1,3-oxazolidine-5-carboxylate;Manderol;CHLORPICRIN PESTANAL (TRICHLORO- NITROME;CHLOZOLINATE PESTANAL.
• CAS NO: 84332-86-5
• Molecular Formula: C₁₃H₁₁Cl₂NO₅
• Molecular Weight: 332.14
• EINECS: 282-714-4
• Mol File: 84332-86-5.mol
• Article Data: 1

Chemical Properties

• Melting Point: 110-114 °C
• Boiling Point: 420.8°C at 760 mmHg
• Flash Point: 100 °C
• Appearance: /
• Density: 1.479
• Vapor Pressure: 2.74E-07mmHg at 25°C
• Refractive Index: 1.57
• Storage Temp.: 0-6°C
• PKA: -4.24±0.40(Predicted)
• Water Solubility: 2 mg l-1 (25 °C)
• CAS DataBase Reference: CHLOZOLINATE(CAS DataBase Reference)
• NIST Chemistry Reference: CHLOZOLINATE(84332-86-5)
• EPA Substance Registry System: CHLOZOLINATE(84332-86-5)

Safety Data

• Hazard Codes: Xn,N,F
• 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
• Hazardous Substances Data: 84332-86-5(Hazardous Substances Data)

Usage

Description

Chlozolinate is a systemic fungicide, characterized by its ability to control various fungal infections in a range of agricultural products. It is particularly effective against Botrytis, Monilia, and Sclerotinia, which cause fruit rot, downy mildew, and brown rot in pome and stone fruits, vines, vegetables, strawberries, and ornamentals.

Uses

Used in Agricultural Industry:
Chlozolinate is used as a dicarboximide fungicide for the control of downy mildew, brown rot, and fruit rot in a variety of crops. Its primary application is on grapes, but it also extends to other pome and stone fruits, vines, vegetables, strawberries, and ornamentals. This helps in maintaining the health and quality of these agricultural commodities, ensuring a bountiful and safe harvest.

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).

InChI:InChI=1/C13H11Cl2NO5/c1-3-20-11(18)13(2)10(17)16(12(19)21-13)9-5-7(14)4-8(15)6-9/h4-6H,3H2,1-2H3

Upstream product

• 34893-92-0 3,4-dichlorophenyl isocyanate 

Downstream Products

• 24261-46-9 3-(3,5-Dichlorophenyl)-5-methyl-5-methyl-oxazolidine-2,4-dione 

Relevant articles and documents

N-Aryl-1,3-oxazolidine-2,4-diones exerting a fungicidal, systemic action in the field

There are disclosed N-aryl-1,3-oxazolidine-2,4-diones of the formula: STR1 wherein: R=C1 -C5 alkyl; C1 -C5 haloalkyl Y=H; hydrogen, 3,4-dichloro; 3,5-dichloro; 3,5-difluoro; 3,5-dimethyl; 3,5-dimethoxy; 3,5-bis-trifluoromethyl; and A= STR2 wherein R is as previously defined. The N-aryl-1,3-oxazolidine-2,4-diones are useful fungicides, possess systemic action, and are particularly active in the field.