Vinclozolin

Vinclozolin

Names
IUPAC name (RS)-3-(3,5-Dichlorophenyl)-5-methyl- 5-vinyloxazolidine-2,4-dione
Other names Vinclozoline
Identifiers
CAS Number	50471-44-8 Y
3D model (Jmol)	Interactive image
ChEBI	CHEBI:9986 N
ChEMBL	ChEMBL513221 Y
ChemSpider	36278 Y
ECHA InfoCard	100.051.437
KEGG	C10981 Y
PubChem	39676
InChI InChI=1S/C12H9Cl2NO3/c1-3-12(2)10(16)15(11(17)18-12)9-5-7(13)4-8(14)6-9/h3-6H,1H2,2H3 Y Key: FSCWZHGZWWDELK-UHFFFAOYSA-N Y InChI=1/C12H9Cl2NO3/c1-3-12(2)10(16)15(11(17)18-12)9-5-7(13)4-8(14)6-9/h3-6H,1H2,2H3 Key: FSCWZHGZWWDELK-UHFFFAOYAN
SMILES O=C2OC(C(=O)N2c1cc(Cl)cc(Cl)c1)(C=C)C
Properties
Chemical formula	C12H9Cl2NO3
Molar mass	286.11 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

Vinclozolin (trade names Ronilan, Curalan, Vorlan, Touche) is a common dicarboximide fungicide used to control diseases, such as blights, rots and molds in vineyards, and on fruits and vegetables such as raspberries, lettuce, kiwi, snap beans, and onions. It is also used on turf on golf courses. Two common fungi that vinclozolin is used to protect crops against are Botrytis cinerea and Sclerotinia sclerotiorum. First registered in 1981, vinclozolin is widely used but its overall application has declined. As a pesticide, vinclozolin is regulated by the United States Environmental Protection Agency (U.S. EPA). In addition to these restrictions within the United States, as of 2006 the use of this pesticide was banned in several countries, including Denmark, Finland, Norway, and Sweden. It has gone through a series of tests and regulations in order to evaluate the risks and hazards to the environment and animals. Among the research, a main finding is that vinclozolin has been shown to be an endocrine disruptor with antiandrogenic effects.

Vinclozolin is manufactured by the chemical company BASF and has been registered for use in the United States since 1981. The following is a compilation of data indicating the national use of vinclozolin per crop (lbs AI/yr) in 1987: apricots, 124; cherries, 3,301; green beans, 13,437; lettuce, 24,779; nectarines, 1,449; onions, 829; peaches, 15,203; plums, 163; raspberries, 3,247; and strawberries, 41,006. In 1997, two applications totaling 285 pounds each, were applied to kiwifruit in California to prevent the gray mold and soft rot caused by Botrytis cinerea. In general, the United States has seen an overall decline in the national use of vinclozolin. In 1992, a total of approximately 135,000 pounds were used. However, in 1997 this number dropped to 122,000 and in 2002 it was down to 55,000 pounds.

The following chemical reactions are used to make vinclozolin: One method combines methyl vinyl ketone, sodium cyanide, 3,5-dichloroaniline, and phosgene. This process involves formation of the cyanohydrin, followed by hydrolysis of the nitrile. Vinclozolin is also prepared by the reaction of 3,5-dichlorophenyl isocyanate with an alkyl ester of 2-hydroxy-2-vinylpropionic acid. Ring closure is achieved at elevated temperature.