Procymidone
Procymidone Basic information
- Product Name:
- Procymidone
- Synonyms:
-
- 1,2-Cyclopropanedicarboximide, N-(3,5-dichlorophenyl)-1,2-dimethyl-
- 1,2-dimethyl-N-(3,5-dichlorophenyl)cyclopropanedicarboximide
- 3-(3,5-dichlorophenyl)-1,5-dimethyl-3-azabicyclo(3.1.0)hexane-4-dione
- 3-azabicyclo[3.1.0]hexane-2,4-dione,3-(3,5-dichlorophenyl)-1,5-dimethyl-
- DICYCLIDINE
- ISO
- BSI
- procymidone (bsi,iso,jmaf)
- CAS:
- 32809-16-8
- MF:
- C13H11Cl2NO2
- MW:
- 284.14
- EINECS:
- 251-233-1
- Product Categories:
-
- FUNGICIDE
- DicarboximidesPesticides&Metabolites
- Alpha sort
- Fungicides
- N-PAlphabetic
- P
- Pesticides
- PON - PT
- Aromatics
- Intermediates & Fine Chemicals
- Pharmaceuticals
- Mol File:
- 32809-16-8.mol
Procymidone Chemical Properties
- Melting point:
- 166-167°C
- Boiling point:
- 477.9±35.0 °C(Predicted)
- Density
- d25 1.42-1.46
- vapor pressure
- 1.8 x 10-2 Pa (25 °C)
- refractive index
- 1.6100 (estimate)
- Flash point:
- >100 °C
- storage temp.
- Sealed in dry,Room Temperature
- solubility
- Chloroform (Slightly), Ethyl Acetate (Slightly)
- pka
- -2.67±0.60(Predicted)
- Water Solubility
- 4.5 mg l-1 (25 °C)
- color
- Off-White to Pale Beige
- BRN
- 1539058
- InChIKey
- QXJKBPAVAHBARF-UHFFFAOYSA-N
- CAS DataBase Reference
- 32809-16-8(CAS DataBase Reference)
- NIST Chemistry Reference
- 3-Azabicyclo[3.1.0]hexane-2,4-dione, 3-(3,5-dichlorophenyl)-1,5-dimethyl-(32809-16-8)
- EPA Substance Registry System
- Procymidone (32809-16-8)
MSDS
- Language:English Provider:3-(3,5-Dichlorophenyl)-1,5-dimethyl-3-azabicyclo[3.1.0]hexane-2,4-dione
Procymidone Usage And Synthesis
Description
Procymidone is a moderately systemic fungicide. It is used in horticulature as a seed-dressing, pre-harvest spray or post-harvest dip for the control of various fungal diseases, such as grey mold, neck rot, brown rot, blossom blight, and twig wilt. It is applied to vegetables including onions, fruits (including peaches, plums, grapes, stone fruit, strawberries, and cherries), and ornamentals.
Uses
Systemic agricultural fungicide.
Uses
Procymidone is a systemic fungcide with both protective and curative activities used to control plant diseases such as fruit rots, grey mould on top fruits, vines and vegetables, and Sclerotinia rot of kidney beans and vegetable crops.
Definition
ChEBI: An azabicycloalkane that is 1,5-dimethyl-3-azabicyclo[3.1.0]hexane-2,4-dione in which the amino hydrogen is replaced by a 3,5-dichlorophenyl group. A fungicide widely used in horticulture as a seed dressing, pre-harvest spray or post-harvest dip for the co trol of various diseases.
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
Procymidone (1) was stable in acidic conditions (pH 2) but hydrolysed
rapidly in buffer solutions (pH 6 to 10) and in natural river and sea water
at 15, 30 and 45 °C with DTm values from 30 min to 8 days. Degradation
occurred mainly via cleavage of the cyclic imide linkage in alkaline
conditions and via cleavage of the subsequent amide linkage in acidic
conditions (Mikami and Miyamoto, 1981) to yield the intermediate acid
[2-( 3,5-dichlorophenylcarbamoyl)- 1,2 -dimet hylcyclopropanecarboxylic
acid (2) and 1,2-dimethylcyclopropane-1,2-dicarboxylica cid (3) and 3,5-
dichloroaniline (4) as terminal products (Villedieu et al., 1994,1995). Pirisi
et al. (1986) and Cabras et al. (1984) reported the formation of compound 4
and other polar decomposition products in wine during the fermentation
process.
Photodegradation of procymidone was investigated in various
solutions after exposure to sunlight. Major degradation pathways were
cleavage of the cyclic imide and the subsequent cleavage of the amide
linkage to yield compounds 3 and 4 (Mikami and Miyamoto, 1981).
Procymidone Preparation Products And Raw materials
Raw materials
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Procymidone(32809-16-8)Related Product Information
- Cyclopropane
- Chlorodimethylphenylsilane
- Dimethyl sulfide
- N,N-Dimethylformamide
- Sodium lauroylglutamate
- ETHANE
- Dimethyl phthalate
- Dimethyl sulfoxide
- Dimethyl fumarate
- Hexane
- Dimethyl ether
- Cyclopropanecarboxylic acid
- Dimethachlon
- 1-Phenyl-2-pyrrolidinone
- GARDAMIDE
- CYCLOPROPANEMETHYLAMINE HYDROCHLORIDE
- Glutarimide
- 1-METHYL-2-PIPERIDONE