60168-88-9

Basic information

• Product Name: Fenarimol
• Synonyms: (2-Chlorophenyl)(4-chlorophenyl)5-pyrimidinylmethanol;(2-Chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanol;.alpha.-(2-chlorophenyl)-.alpha.-(4-chlorophenyl)-5-Pyrimidinemethanol;2,4’-dichloro-alpha-(pyrimidin-5-yl)benzhydrylalcohol;5-Pyrimidinemethanol, alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-;alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethano;alpha-(2-Chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanol;Bloc
• CAS NO: 60168-88-9
• Molecular Formula: C₁₇H₁₂Cl₂N₂O
• Molecular Weight: 331.2
• EINECS: 262-095-7
• Product Categories: FA - FLPesticides;Alpha sort;E-GAlphabetic;F;Fungicides;Pesticides&Metabolites;Pyrimidines;Alphabetic
• Mol File: 60168-88-9.mol

Chemical Properties

• Melting Point: 117-119°C
• Boiling Point: 0°C
• Flash Point: 0°C
• Appearance: Pure white crystalline solid
• Density: 1.3886 (rough estimate)
• Vapor Pressure: 4.02E-08mmHg at 25°C
• Refractive Index: 1.5490 (estimate)
• Storage Temp.: 0-6°C
• Solubility: Chloroform (Slightly), Methanol (Slightly)
• PKA: 2.58
• Water Solubility: 14.6 mg l-1 (pH 3), 13.7 mg l-1 (pH 7), 13.8 mg l-1 (pH 10) at 25 °C
• Merck: 13,3986
• BRN: 5972869
• CAS DataBase Reference: Fenarimol(CAS DataBase Reference)
• NIST Chemistry Reference: Fenarimol(60168-88-9)
• EPA Substance Registry System: Fenarimol(60168-88-9)

Safety Data

• Hazard Codes: Xn;N,N,Xn
• Statements: 51/53-62-63-64
• Safety Statements: 36/37-61
• RIDADR: UN 3017/3077
• WGK Germany: 2
• RTECS: UV9279400
• Hazardous Substances Data: 60168-88-9(Hazardous Substances Data)

Usage

Reactivity Profile

Fenarimol produces toxic gases when heated to decomposition.

Safety Profile

Moderately toxic by ingestion. Experimental reproductive effects. Mutation data reported. When heated to decomposition it emits toxic fumes of Cland NOx.

Metabolic pathway

The primary dissipation mechanism of fenarimol in the environment involves photolysis on plants/soil surfaces and water. More than 80 photoproducts have been observed, resulting from the reduction of the pyrimidine ring, hydrolysis, ring migration and cleavage of the phenyl and pyrimidine ring moieties. Under laboratory conditions in the dark, fenarimol is relatively persistent in soil, but a more rapid dissipation was observed under field conditions with DT50 values of 18-140 days, attributed to photolysis of fenarimol on the soil surface. Fenarimol degrades in/on plant foliage/fruit surfaces mainly by photochemical processes. In animals, fenarimol is metabolised extensively to yield hydroxylated, cleavage and dechlorination products. The primary photolytic and metabolic pathways of fenarimol are presented in Schemes 1 and 2.

Degradation

Fenarimol(1) is stable in sterile buffered water in the dark at pH 3,6 and 9 at 25 °C, 37 °C and 52 °C for 28 days (Decker and Sullivan, 1975) but is readily degraded via photolysis. The photolytic DT50 in distilled water under natural sunlight and clear sky conditions at 40°N in mid-summer was approximately 12 hours (Day, 1975). The primary aqueous photolysis reaction involved the migration of the pyrimidine ring to one of the chlorophenyl rings, followed by the oxidation of the carbinol moiety to the corresponding ketone to yield 4-chloro-2-(5-pyrimidyl)-2'-chlorobenzophenone (2). Fenarimol was extensively photodegraded on solid surfaces. More than 80 photodegradation products were formed when fenarimol was exposed to sunlight on a stainless steel surface for up to 200 hours (Althaus and Bewley, 1978a). All photoproducts were formed at very low levels (less than 3% each) and 14 were identified. An abbreviated photogradation pathway of fenarimol is presented in Scheme 1. These products were generated from the following reactions: the migration of the pyrimidine ring to one of the chlorophenyl rings, followed by the oxidation of the carbinol moiety to yield compound 2; cleavage of either one of the chlorophenyl (to yield 3,4) or pyrimidine rings (5,6); aryl hydroxylation of one of the chlorophenyl rings (7); carbinol dehydroxylation reaction to yield 8 and a bridged fluorene product (9) from the dechlorination reaction. Various cleavage products (carboxylic acids) derived from the chlorophenyl (10-13) and the pyrimidine moieties (14) were also observed.

InChI:InChI=1/C17H12Cl2N2O/c18-13-7-5-11(6-8-13)16(22)12-9-20-17(21-10-12)14-3-1-2-4-15(14)19/h1-10,16,22H

Upstream product

• 4595-59-9 5-bromopyrimidine 
• 85-29-0 2,4'-dichlorobenzophenone 
• 103686-55-1 (4-chlorophenyl)(pyrimidin-5-yl)methanone 
• 694-80-4 2-bromo-1-chlorobenzene 
• 1401217-87-5 5-(4-chlorobenzyl)pyrimidine 
• 89523-62-6 (4-chlorophenyl)zinc(II) chloride 

Downstream Products

• 816417-09-1 (+/-)-5-[(2-chlorophenyl)-(4'-chlorophenyl)pyrimidin-5-yl-methoxy]pentanoic acid 
• 816417-08-0 (+/-)-6-[(2-chlorophenyl)-(4'-chlorophenyl)pyrimidin-5-yl-methoxy]hexanoic acid 
• 93765-38-9 5-[(2-chlorophenyl)(4-chlorophenyl)methyl]pyrimidine 
• 1374583-88-6 (4-chlorophenyl)(2-chlorophenyl)pyrimidin-5-yl N-Oxide methanol 
• 1448777-08-9 (2-chlorophenyl)(4-chlorophenyl)(2-isopropylpyrimidin-5-yl)methanol 

Relevant articles and documents

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