Fenarimol

HCID 43226
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Basic information

CAS
60168-88-9
Standard SMILES
OC(c1ccc(Cl)cc1)(c1cncnc1)c1ccccc1Cl
InChIKey
NHOWDZOIZKMVAI-UHFFFAOYSA-N
Molecular formula
C17H12Cl2N2O
Average molar mass
331.2 g/mol
Monoisotopic mass
330.03266836

Overview

Pure white crystalline solid. Used as a fungicide. Irritates skin and mucous membranes.

Names & identifiers

Preferred name
Fenarimol
IUPAC
(2-chlorophenyl)-(4-chlorophenyl)-pyrimidin-5-ylmethanol
English name
Fenarimol
Molecular formula
C17H12Cl2N2O
Molecular weight
331.2

Names & synonyms

FENARIMOL60168-88-9RubiganRimidinDTXSID2032390EL 222FENARIalpha-(2-Chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanolO088GU930Q2,4'-Dichloro-alpha(pyrimidin-5-yl)benzhydryl alcoholDTXCID0012390(+-)-2,4'-Dichloro-alpha-(pyrimidin-5-yl)benzhydryl alcohol
Show more names
BlocEL-222BLOC(R)RUBIGAN-4RUBIGAN(R)RUBIGAN12ECFenarimol Standard
CHEBI:83686(2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol5-Pyrimidinemethanol, alpha-(2-chlorophenyl)-alpha-(4-chlorophenyl)-RefChem:140102CHEBI:4998(2-Chlorophenyl)-alpha-(4-chlorophenyl)-5-pyrimidinemethanol262-095-7(2-Chlorophenyl)(4-chlorophenyl)(pyrimidin-5-yl)methanol

Database identifiers

CAS
60168-88-9
PubChem CID
43226
DTXSID
DTXSID2032390
ChEMBL
CHEMBL28971
ChEBI
CHEBI:83686
UNII
O088GU930Q
EC Number
262-095-7
Nikkaji
J18.180C

Properties

Computed structural properties

XLogP
3.6
Topological polar surface area
46 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
3
Heavy atoms
22

Experimental & physicochemical properties

Pesticides · 4 items

Fungicides

Active substance -> EU Pesticides database: Not approved

Fungicides

Pesticide (Fenarimol) -> USDA PDB

LogP2.62
Endocrine DisruptorsPotential endocrine disrupting compound
Melting Point117 - 119 °C
Physical Description · 2 items

Pure white crystalline solid. Used as a fungicide. Irritates skin and mucous membranes.

Solid

Collision Cross Section · 3 items

176.0 Ų [M-H]- [CCS Type: DT; Buffer gas: N2; Ionization: ESI-; Dataset: TOXCAST; Source Identifier: DTXSID2032390]

175.92 Ų [M-H]-

173.78 Ų [M]+ [CCS Type: TW; Buffer gas: N2; Ionization: GC-APCI+]

Physicochemical properties

Melting point
117 · 117-119°C
Boiling point
0 °C · 0°C
Density
1.3886 · 1.3886 (rough estimate)
vapor pressure
6.5 x · 6.5 x 10-5 Pa at 25 °C
refractive index
1.549 · 1.5490 (estimate)
Flash point
0 °C · 0°C

Safety & regulation

GHS classification

GHS Classification · 6 items

Warning

H361fd: Suspected of damaging fertility; Suspected of damaging the unborn child [Warning Reproductive toxicity]

P203, P260, P263, P264, P270, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Warning

H361 (84.7%): Suspected of damaging fertility or the unborn child [Warning Reproductive toxicity]

P203, P260, P263, P264, P270, P273, P280, P318, P391, P405, and P501 (click each P-code to see the statement)

Hazard information

Regulatory Information · 4 items

Regulation (EC) No 1107/2009 (amended)

Fenarimol is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)

2006/134/EC

Fenarimol: Does not have an individual approval but may be used under an appropriate group standard

Other Safety InformationIMAP assessments - 5-Pyrimidinemethanol, .alpha.-(2-chlorophenyl)-.alpha.-(4-chlorophenyl)-: Human health tier I assessment
DOT LabelPoison Flammable Liquid
Fire HazardsExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Health HazardsExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Reactive GroupAlcohols and Polyols

Safety & protection

Fire FightingExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
First AidExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Nonfire Spill ResponseExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Isolation and EvacuationExcerpt from ERG Guide 131 [Flammable Liquids - Toxic]:
Personal Protective Equipment (PPE)Excerpt from ERG Guide 131 [Flammable Liquids - Toxic]:

Toxicology

Toxicity Summary · 1 item

Fenarimol is an antiandrogen. It has effects on the reproductive organs and prostate gene expression levels. Studies suggested that the adverse effects of Fenarimol in males are mediated at least partialy via antagonism or androgen receptor.

Carcinogen ClassificationNo indication of carcinogenicity to humans (not listed by IARC).
RAIS Toxicity Values · 2 items

0.006

OPP

EPA Human Health Benchmarks for Pesticides · 5 items

Fenarimol

0.006

40

General Population

Human Health Benchmarks for Pesticides - 2021 Update

Safety data

PPE
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
2
tsca
TSCA listed
rtecs
UV9279400
ridadr
UN 3017/3077
Toxicity
LD50 in mice, rats (mg/kg): 4500, 2500 orally (Beraud)

Chemistry & industry

Pharmacology

MeSH Pharmacological ClassificationChemicals that kill or inhibit the growth of fungi in agricultural applications, on wood, plastics, or other materials, in swimming pools, etc.
Cellular LocationsMembrane

Uses & manufacturing

Use ClassificationFungicides
General Manufacturing Information5-Pyrimidinemethanol, .alpha.-(2-chlorophenyl)-.alpha.-(4-chlorophenyl)-: ACTIVE
Applications · 5 items

DescriptionFenarimol is a foliar pyrimidine fungicide with systemic, curative and protective action. It has a moderate aqueous solubility but is soluble in many organic solvents. It is not considered to be volatile. Fenarimol may be very persistent in soils and aquatic systems depending upon local conditions. It is moderately toxic to most terrestrial and aquatic species. It’s oral toxicity to humans is low but there are concerns about potential chronic effects relating to reproduction/development and it is considered to be an endocrine disrupter.

UsesPlant fungicide.

UsesFenarimol is a pyrimidine based fungicide which acts against rusts, blackspot and mildew fungi and it works by inhibiting the fungus’s biosynthesis of important steroid molecules.

UsesFenarimol is a broad spectrum pyrimidine carbinol fungicide with protective, curative and eradicative activities against powdery mildew (Erysiphe spp., Pudusphaera leucutricha, Uncinula necatur, Sphaerutheca spp., Leveillula spp.) and scab (Venturia spp.) in many crops. It also controls powdery mildew (Sphaerutheca pannusa) in ornamentals and Fusarium patch (Micruduccium niuale), Take-all patch (Laefisaria fuciformis), Dollar spot (Sderutina humeucavpa) and red thread (Gaeumannumyces graminis) in turf and amenity grasses.

General DescriptionPure white crystalline solid. Used as a fungicide. Irritates skin and mucous membranes.

Upstream & downstream products

Suppliers63 total

上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
广州佳途科技股份有限公司81960175 18933936954 · [email protected]
河南赢创生物科技有限公司16650615803 · [email protected]
杭州品高化工有限公司0571-87658025 · [email protected]
宁波季诺化学品有限公司0574-87314919 057487319282 · [email protected]
Additional notes · 1 item

DefinitionChEBI: (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol is a member of the class of pyrimidines that is pyrimidin-5-ylmethanol in which one of the hydrogens attached to the carbon bearing the hydroxy group is replaced by a 2-chlorophenyl group while the other is replaced by a 4-chlorophenyl group. It is a tertiary alcohol, a member of monochlorobenzenes and a member of pyrimidines.

Related reactions

1 records
New reaction record

Compound notes

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