32809-16-8

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-;n-(3,5-dichlorophenyl)-1,2-dimethyl-2-cyclopropanedicarboximide;s7131;sp751011;PROMIDON
• CAS NO: 32809-16-8
• Molecular Formula: C13H11Cl2NO2
• Molecular Weight: 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;NULL
• Mol File: 32809-16-8.mol

Chemical Properties

• Melting Point: 166-167°C
• Boiling Point: 477.9 ºC at 760 mmHg
• Flash Point: >100 °C
• Appearance: Off-White to Pale Beige Solid
• Density: d25 1.42-1.46
• Vapor Pressure: 2.7E-09mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Ethyl Acetate (Slightly)
• PKA: -2.67±0.60(Predicted)
• Water Solubility: 4.5 mg l-1 (25 °C)
• BRN: 1539058
• CAS DataBase Reference: Procymidone(CAS DataBase Reference)
• NIST Chemistry Reference: Procymidone(32809-16-8)
• EPA Substance Registry System: Procymidone(32809-16-8)

Safety Data

• WGK Germany: 2
• RTECS: GZ2150000
• Hazardous Substances Data: 32809-16-8(Hazardous Substances Data)

Usage

Uses

Used in Horticulture:
Procymidone is used as a seed-dressing, pre-harvest spray, and post-harvest dip for the control of various fungal diseases such as grey mold, neck rot, brown rot, blossom blight, and twig wilt.
Used in Vegetable Production:
Procymidone is used as a protective and curative fungicide for vegetables, including onions, to manage plant diseases and enhance crop health.
Used in Fruit Production:
Procymidone is used as a fungicide for fruits such as peaches, plums, grapes, stone fruit, strawberries, and cherries, helping to control fruit rots and other fungal infections.
Used in Ornamental Plant Production:
Procymidone is used as a fungicidal agent for ornamental plants, providing protection against diseases and maintaining their aesthetic appeal.
Used as a Systemic Agricultural Fungicide:
Procymidone is used as a systemic fungicide with both protective and curative activities, effective in controlling plant diseases like fruit rots, grey mould on top fruits, vines, and vegetables, as well as Sclerotinia rot of kidney beans and other vegetable crops.

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).

InChI:InChI=1/C13H11Cl2NO2/c1-12-6-13(12,2)11(18)16(10(12)17)9-4-7(14)3-8(15)5-9/h3-5H,6H2,1-2H3

Downstream Products

• 34893-92-0 3,4-dichlorophenyl isocyanate 
• 626-43-7 3,5-Dichloroaniline 
• 884-79-7 3-phenyl-1,5-dimethyl-3-azabicyclo-<3.1.0>hexane-2,4-dione 

Relevant articles and documents

Substituted imide derivatives

The present invention relates to novel substituted imide derivatives of the general formula (I) in which R1 represents optionally substituted cycloalkyl, R2 represents optionally substituted alkyl or optionally substituted cycloalkyl, R3 represents alkyl, alkoxy, alkylthio, amino, alkylamino or dialkylamino and R4 represents cyano or nitro, and to processes for their preparation and to their use for controlling animal pests and as herbicides.

Pyrazolyl benzyl ether derivatives containing a fluoromethoxyimino group and use thereof as pesticides

The invention relates to novel pyrazolyl benzyl ethers, to a plurality of processes for their preparation and to their use for controlling harmful organisms.

Pyrimidine derivatives, process and intermediate products for their preparation and pesticides or fungicides containing these derivatives

Pyrimidine compounds I wherein X is C(CO2CH3)═NOCH3, C(CONHCH3)═NOCH3, C(CO2CH3)═CHOCH3, C(CO2CH3)═CHCH3or N(CO2CH3)—OCH3; R1, R2are hydrogen, alkyl, haloalkyl or alkoxy; A is R3is hydrogen, alkyl, haloalkyl, phenoxyalkyl, cycloalkyl, cyano, alkoxy, hydroxyl or halogen; R4is hydrogen, optionally substituted alkyl, alkenyl, alkynyl, haloalkenyl, haloalkynyl, cycloalkyl or alkoxy; Y is hydrogen, hydroxyl, halogen, optionally substituted aryl, hetaryl, cycloalkyl, cycloalkenyl, heterocyclyl, alkyl, alkenyl, alkynyl, haloalkyl, alkoxy, aryloxy, arylthio, hetaryloxy, hetarylthio, cycloalkyloxy or alkylthio, or their salt, their synthesis and intermediates therefore, and their activity against fungi or animal pests.

Iminoacetic acid amides and their use as pest control agents

PCT No. PCT/EP96/04345 Sec. 371 Date Apr. 15, 1998 Sec. 102(e) Date Apr. 15, 1998 PCT Filed Oct. 7, 1996 PCT Pub. No. WO97/14673 PCT Pub. Date Apr. 24, 1997Iminoacetamides of the formula (I) in which A represents a single bond or optionally substituted alkylene, Q represents oxygen or sulphur, R1 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R2 represents respectively optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, R3 represents hydrogen or respectively optionally substituted alkyl, alkenyl, alkinyl or cycloalkyl, R4 represents respectively optionally substituted cycloalkyl, cycloalkenyl, aryl or heterocyclcyl a process for their preparation, pesticidal compositions containing them, and their use for controlling pests.

Use of aminoisothiazoles as microbicides

PCT No. PCT/EP97/06854 Sec. 371 Date Jun. 16, 1999 Sec. 102(e) Date Jun. 16, 1999 PCT Filed Dec. 9, 1997 PCT Pub. No. WO98/27816 PCT Pub. Date Jul. 2, 1998Aminoisothiazoles of the formula I, where R is hydrogen or C1-C4 alkyl and X is halogen, NO2, CN or SCN, and metal complexes and acid addition salts thereof are used as microbicides for protecting industrial materials from being attacked and destroyed by microorganisms.

2-and 2,5-substituted phenylketoenols

PCT No. PCT/EP97/03973 Sec. 371 Date Jan. 28, 1999 Sec. 102(e) Date Jan. 28, 1999 PCT Filed Jul. 23, 1997 PCT Pub. No. WO98/05638 PCT Pub. Date Feb. 12, 1998The invention relates to novel phenyl-substituted cyclic ketoenols of the formula (I) in which Het represents one of the groups in which A, B, D, G, X and Z are each as defined in the description, to a plurality of processes and intermediates for their preparation, and to their use as pesticides.

Fluoropyrazole-biphenylamide fungicides

PCT No. PCT/EP98/04663 Sec. 371 Date Feb. 10, 2000 Sec. 102(e) Date Feb. 10, 2000 PCT Filed Jul. 25, 1998 PCT Pub. No. WO99/09013 PCT Pub. Date Feb. 25, 1999The invention relates to biphenylamides having general formula (I), and their salts, in which R1 is H or F; R2 is H, halogen, alkyl, halogen methyl, alkoxy, alkylthio; R3 is CH3, CHF2, CF3. The invention also relates to agents containing biphenylamnides, the production of biphenylamides and their use in combating parasitic fungus.

Microbicidal benzotriazoles

Novel benzotriazoles of the formula STR1 in which R, X1, X2, X3, X4 and Y have the meanings given in the description, and their acid addition salts and metal salt complexes, a process for the preparation of these substances and their use as microbicides in crop protection and in material protection.

Halogen alkenyl azolyl microbicides

Novel halogenoalkenyl-azolyl derivatives of the formula STR1 in which R1 represents optionally substituted alkyl, optionally substituted alkenyl, optionally substituted cycloalkyl, optionally substituted aryl or represents optionally substituted heteroaryl, R2 represents alkyl, halogenoalkyl, 1-hydroxyalkyl, 2-hydroxyalkyl, 1-hydroxyhalogenalkyl, 1-alkenyl or 2-alkenyl, X1 represents fluorine, chlorine, bromine or iodine, X2 represents fluorine, chlorine, bromine or iodine, and Y represents nitrogen or a CH group, and addition products thereof with acids or metal salts are very active as microbicides in plant protection and in the protection of materials.

Substituted biphenyl oxazolines

The invention relates to new substituted biphenyloxazolines of the formula (I) STR1 in which R1 represents C1 -C6 -halogenoalkylthio and R2 represents hydrogen, or R1 and R2 together with the carbon atoms to which they are bonded form a halogen-substituted 5- or 6-membered heterocyclic ring, X represents hydrogen, halogen, C1 -C6 -alkyl or C1 -C6 -alkoxy, and m represents 0, 1 or 2, to processes for their preparation, to new intermediates, and to the use of the substituted biphenyloxazolines for combating animal pests, with the exception of the compound of the formula STR2