50471-44-8

Basic information

• Product Name: VINCLOZOLIN
• Synonyms: vinchlozoline;Vinclozalin;vinclozoline;RONILAN;RONILAN(R);VORLAN;VINCLOZOLIN;3-(3,5-DICHLOROPHENYL)-5-ETHENYL-5-METHYL-2,4-OXAZOLIDINEDIONE
• CAS NO: 50471-44-8
• Molecular Formula: C12H9Cl2NO3
• Molecular Weight: 286.11
• EINECS: 256-599-6
• Product Categories: Organics;OxazolesAnalytical Standards;DicarboximidesPesticides;OxazolesPesticides&Metabolites;Q-ZAnalytical Standards;VMethod Specific;2000/60/EC;Alpha sort;Alphabetic;European Community: ISO and DIN;Fungicides;Pesticides;Agro-Products;Aromatics;Heterocycles
• Mol File: 50471-44-8.mol

Chemical Properties

• Melting Point: 108℃
• Boiling Point: 369.9 °C at 760 mmHg
• Flash Point: 2 °C
• Appearance: Vinclozolin is a colorless crystal with a slight aromatic odor
• Density: 1.51 g/cm3
• Vapor Pressure: 1.15E-05mmHg at 25°C
• Refractive Index: 1.6100 (estimate)
• Storage Temp.: APPROX 4°C
• PKA: -3.43±0.40(Predicted)
• Water Solubility: 3.4 mg l-1 (20 °C)
• Merck: 13,10046
• BRN: 8331312
• CAS DataBase Reference: VINCLOZOLIN(CAS DataBase Reference)
• NIST Chemistry Reference: VINCLOZOLIN(50471-44-8)
• EPA Substance Registry System: VINCLOZOLIN(50471-44-8)

Safety Data

• Hazard Codes: T,N,Xn,F
• Statements: 60-61-40-43-51/53-36-20/21/22-11
• Safety Statements: 53-45-61-36-26-16-36/37
• RIDADR: UN3077 9/PG 3
• WGK Germany: 3
• RTECS: RP8530000
• Hazardous Substances Data: 50471-44-8(Hazardous Substances Data)

Usage

Uses

Used in Agricultural Industry:
VINCLOZOLIN is used as a fungicide for controlling fruit rot, brown rot, mould, and blight in various crops such as vines, fruits, vegetables, oilseed rape, ornamentals, hops, turf, and strawberries. Its application helps to protect these crops from the damaging effects of fungal infections, ensuring healthier and more productive harvests.

Air & Water Reactions

Hydrolysis rapidly occurs under alkaline conditions

Reactivity Profile

A halogenated dicarboximide. Organic amides/imides react with azo and diazo compounds to generate toxic gases. Flammable gases are formed by the reaction of organic amides/imides with strong reducing agents. Amides are very weak bases (weaker than water). Imides are less basic yet and in fact react with strong bases to form salts. That is, they can react as acids. Mixing amides with dehydrating agents such as P2O5 or SOCl2 generates the corresponding nitrile. The combustion of these compounds generates mixed oxides of nitrogen (NOx).

Trade name

BAS-352-F?; BAS-35204-F?; CURALAN?; FLOTILLA?; FUMITE RONALIN?; MASCOT? contact turf fungicide; ORNALIN?[C]; POWERDRIVE?; RONILAN?; RONILAN-DF?; RONALINE-FL?; TOUCHE?; VINCHLOZOLINE?; VINCLOZOLINE?; VORLAND?

Safety Profile

Low toxicity by ingestion and inhalation. Mutation data reported. When heated to decomposition it emits very toxic fumes of Cland NOx.

Purification Methods

Crystallise the fungicide from Me2CO/H2O. Its solubility at 20o (w/w%) is 44 (Me2CO), 32 (CHCl3), 25 (EtOAc) and 10 (H2O). It irritates the eyes and skin. [GP 2,207,576 1973, Chem Abstr 79 137120 1973.]

Degradation

Vinclozolin (1) was rapidly hydrolysed in alkaline solution. The hydrolytic DT50, values in pH 5, 7 and 9 solution at 25 °C were 45 days, 13.4 hours and 1.6 hours, respectively (Melkebeke et al., 1986). Szeto et al. (1989a) and Villedieu et al. (1994, 1995) reported that the opening of the oxazolidinedione ring by attack of the hydroxyl ion on the two carbonyl groups is the primary hydrolysis mechanism to yield 2-{[3,5- dichlorophenyl)carbamoyl]-oxy}-2-methyl-3-butenoica cid (2) and 3'5'- dichloro-2-hydroxy-2-methylbut-3-enanilide(3) as major products. The formation of compound 3 was likely via the intermediate N-(2-hydroxy- 2-methyl-1-oxo-buten-3-yl)-3,5-dichlorophenyl-1-carbamic acid (4). 3,5- Dichloroaniline (5) was reported as a minor hydrolysis product. The proposed hydrolytic degradation pathway of vinclozolin is presented in Scheme 1. Compound 3 was also reported as the primary degradation product of vinclozolin in wine (pH 3-4, 30 °C) whereas 3,5- dichloroaniline (5) was not detected in the wine samples (Cabras et al., 1984; Pirisi et al., 1986). The degradation rate of vinclozolin in aqueous solution at λ> 290 nm was slower than at λ>230 nm; furthermore, the addition of humic and fulvic acids catalysed the aqueous photodegradation reaction (DT50 8 hours) to yield compound 5 and 3,5-dichlorophenyl isocyanate (6) as primary degradation products (see Scheme 1; Hustert and Moza, 1997). Schwack et al. (1995) reported the photolytic reactions of vinclozolin in various organic solvents. Addition of the solvent molecules to the vinyl moiety and dechlorination products were observed as major photodegradation reactions.

InChI: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

Upstream product

• 34893-92-0 3,4-dichlorophenyl isocyanate 
• 152723-53-0 3-(3,5-dichlorophenyl)-5-methyl-5-vinyloxazolidine-2,4-dione 
• 72531-53-4 isobutyl 2-hydroxy-2-vinylpropionate 
• 25216-51-7 3,5-dichlorophenyl-carbamic acid isobutyl ester 
• 13142-57-9 1-(3,5-Dichlorophenyl)urea 

Downstream Products

• 83792-61-4 N-(3,5-Dichlorophenyl)-2-hydroxy-2-methylbut-3-enanilide 
• 92-52-4 biphenyl 
• 25217-43-0 methyl (3,5-dichlorophenyl)carbamate 
• 83015-12-7 methyl N-(3,5-dimethoxyphenyl)carbamate 
• 1016-70-2 3-(3-chlorophenyl)-5-methyloxazolidine-2,4-dione 
• 24261-46-9 3-(3,5-Dichlorophenyl)-5-methyl-5-methyl-oxazolidine-2,4-dione 
• 119726-05-5 3-(3,5-dichlorophenyl)-5-methyl-5-(1,2-dihydroxyethyl)-1,3-oxazolidine-2,4-dione 
• 119209-27-7 2-[[(3,5-dichlorophenyl)-carbamoyl]oxy]-2-methyl-3-butenoic acid 
• 626-43-7 3,5-Dichloroaniline 

Relevant articles and documents

Chiral separation and enantioselective degradation of vinclozolin in soils

Vinclozolin is a chiral fungicide with potential environmental problems. The chiral separation of the enantiomers and enantioselective degradation in soil were investigated in this work. The enantiomers were separated by high-performance liquid chromatography (HPLC) on Chiralpak IA, IB, and AZ-H chiral columns under normal phase and the influence of the mobile phase composition on the separation was also studied. Complete resolutions were obtained on all three chiral columns under optimized conditions with the same elution order of (+)/(-). The residual analysis of the enantiomers in soil was conducted using accelerate solvent extraction followed by HPLC determination. The recoveries of the enantiomers ranged from 85.7-105.7% with relative standard deviation (SD) of 0.12-3.83%, and the limit of detection (LOD) of the method was 0.013 μg/g. The results showed that the degradations of vinclozolin enantiomers in the soils followed first-order kinetics. Preferential degradation of the (-)-enantiomer was observed only in one soil with the largest |ES| value of 0.047, and no obvious enantioselective degradation was observed in other soils. It was found that the persistence of vinclozolin in soil was related to pH values based on the half-lives. The two enantiomers disappeared about 8 times faster in basic soils than that in neutral or acidic soils.

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.

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

Acylated 5-aminopyrazoles and the use thereof to combat animal parasites

The present invention relates to new acylated 5-aminopyrazoles of the formula (I) STR1 in which R1, R2, R3, R4 and R5 have the meaning given in the description, to processes for their preparation and to their use as pesticides.

Substituted tetrahydro-5-nitro-pyrimidines

The present invention relates to novel substituted in that one tetrahydro-5-nitro-pyrimidine of the formula (I), according to claim 1, STR1 in which n, R1, R2 have the meaning given in the description, to a process for its preparation and to its use for combating animal pests, especially insects, arachnids and nematodes, which are encountered in agricultural, in forestry, in the protection of stored products and of materials and, in the hygiene sector.

Fungicidal composition for seed dressing

The present invention relates to a fungicidal composition intended for the protection of the multiplication products of cultivated plants, containing: (a) 2-(4-chlorobenzylidene)-5,5-dimethyl-1-(1H-1,2,4-triazol-1-ylmethyl)-1-cyclopentanol; (b) one or more fungicides suitable for the protection of the said multiplication products, optionally one or more insecticides, (c), an agriculturally acceptable inert vehicle and an agriculturally acceptable surfactant. The invention also relates to a method for protecting the multiplication products of plants against fungal diseases using these compositions.