Tolfenpyrad

HCID 10110536CAS 129558-76-5
Substructure searchFind similar structures

Basic information

Standard SMILES
CCc1nn(C)c(C(=O)NCc2ccc(Oc3ccc(C)cc3)cc2)c1Cl
InChIKey
WPALTCMYPARVNV-UHFFFAOYSA-N
Molecular formula
C21H22ClN3O2
Average molar mass
383.9 g/mol
Monoisotopic mass
383.14005462

Overview

Tolfenpyrad is an aromatic amide obtained by formal condensation of the carboxy group of 4-chloro-3-ethyl-1-methylpyrazole-5-carboxylic acid with the amino group of 1-[4-(4-methylphenoxy)phenyl]methylamine. It has a role as an agrochemical, an antifungal agent, a mitochondrial NADH:ubiquinone reductase inhibitor and an EC 1.3.5.1 [succinate dehydrogenase (quinone)] inhibitor. It is a pyrazole insecticide, an aromatic ether, an organochlorine compound and an aromatic amide.

Names & identifiers

Preferred name
Tolfenpyrad
IUPAC
4-chloro-3-ethyl-1-methyl-N-[[4-(4-methylphenoxy)phenyl]methyl]pyrazole-5-carboxamide
English name
TOLFENPYRAD
Molecular formula
C21H22ClN3O2
Molecular weight
383.87

Names & synonyms

tolfenpyrad129558-76-5OHA74571QT4-chloro-3-ethyl-1-methyl-N-(4-(p-tolyloxy)benzyl)pyrazole-5-carboxamideDTXSID6057952CHEBI:386284-chloro-3-ethyl-1-methyl-N-((4-(4-methylphenoxy)phenyl)methyl)-1H-pyrazole-5-carboxamide4-CHLORO-3-ETHYL-1-METHYL-N-[4-(P-TOLYLOXY)BENZYL]PYRAZOLE-5-CARBOXAMIDE4-chloro-3-ethyl-1-methyl-N-[4-(4-methylphenoxy)benzyl]-1H-pyrazole-5-carboxamide4-Chloro-3-ethyl-1-methyl-N-{[4-(4-methylphenoxy)phenyl]methyl}-1H-pyrazole-5-carboxamide4-chloro-3-ethyl-1-methyl-N-(4-(4-methylphenoxy)benzyl)-1H-pyrazole-5-carboxamideRefChem:190289
Show more names
omi-88HATI-HATIolfenpyra2-ethanediolTolfenapyradTOLFENPYRAD STANDARDC17591500 Tolfenpyradtolfenpyrad (bsi, pa iso)
DTXCID4031720603-342-4Tolfenpyrad [ISO]MFCD082738504-chloro-5-ethyl-2-methyl-N-[[4-(4-methylphenoxy)phenyl]methyl]pyrazole-3-carboxamideMMV6889344-chloro-3-ethyl-1-methyl-N-(4-(p-tolyloxy)benzyl)-1H-pyrazole-5-carboxamide4-Chloro-3-ethyl-1-methyl-N-(4-(p-tolyloxy)-benzyl)-1H-pyrazole-5-carboxamide

Database identifiers

CAS
129558-76-5
PubChem CID
10110536
DTXSID
DTXSID6057952
ChEMBL
CHEMBL2229099
ChEBI
CHEBI:38628
UNII
OHA74571QT
EC Number
603-342-4
Nikkaji
J1.215.839D

Properties

Computed structural properties

XLogP
4.7
Topological polar surface area
56.2 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
3
Rotatable bonds
6
Heavy atoms
27

Experimental & physicochemical properties

Pesticides · 3 items

Agrochemicals -> Pesticide active substances

Active substance -> EU Pesticides database: Not approved

Pesticide (Tolfenpyrad) -> USDA PDB

Physicochemical properties

Melting point
87 · 87~89℃
Boiling point
540 · 540.0±50.0 °C(Predicted)
Density
1.21 · 1.21±0.1 g/cm3(Predicted)
storage temp.
0 · 0-6°C
solubility
Chloroform (Slightly), DMSO (Slightly)
pka
13.11 · 13.11±0.46(Predicted)

Safety & regulation

GHS classification

GHS Classification · 6 items

Danger

H302+H332 (78.8%): Harmful if swallowed or if inhaled [Warning Acute toxicity, oral; acute toxicity, inhalation]

P260, P261, P264, P270, P271, P273, P301+P317, P304+P340, P317, P319, P330, P391, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 85 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Danger

H301: Toxic if swallowed [Danger Acute toxicity, oral]

Hazard information

Regulatory InformationTolfenpyrad is listed in the dataset of EPA Human Health Benchmarks for Pesticides under the Safe Drinking Water Act (40 eCFR 141)
Hazard Classes and Categories · 3 items

Acute Tox. 4 (97.6%)

Acute toxicity (Oral) - Category 3

Acute toxicity (Oral) - Category 3

Toxicology

RAIS Toxicity Values · 4 items

0.1

OPP

0.006

OPP

EPA Human Health Benchmarks for Pesticides · 6 items

Tolfenpyrad

0.1

700

Children

0.006

40

Safety data

wgk
3
ridadr
UN 3077 9 / PGIII
risk_code
20/22-50/53
Signal word
Warning
Symbol(GHS)
GHS07,GHS09
hazard_code
Xn,N

Chemistry & industry

Applications · 2 items

DescriptionTolfenpyrad is a pyrazole insecticide developed by Mitsubishi Chemical. It was first approved in 2002 in Japan under the trade name of Hachi-hachi. It has broad insecticidal activity against a variety of pests such as Hemiptera, Coleoptera, Diptera, Lepidoptera, Thysanoptera and Acarina. It is especially effective against pests that are resistant to existing insecticides such as organophosphates and carbametes, because it supposedly possesses a new mode of action: inhibition of Complex I in the respiratory electron-transfer chain of mitochondria. It is applied for vegetables particularly cruciferous leafy varieties, cucurbits, cole crops, tea, fruits & nuts, selected row crops, and indoor ornamentals except cut flowers.

UsesTolfenpyrad

Suppliers50 total

湖北博杰生物科技有限公司0713-2060728 15629612610
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
Dayang Chem (Hangzhou) Co.,Ltd.+86-0571-88938639 17705817739 · [email protected]
梯希爱（上海）化工贸易有限公司021-61109150 · [email protected]

Additional notes

DefinitionChEBI: An aromatic amide obtained by formal condensation of the carboxy group of 4-chloro-3-ethyl-1-methylpyrazole-5-carboxylic acid with the amino group of 1-[4-(4-methylphenoxy)phenyl]methylamine.

Related reactions

7 records
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Linked notes

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