<?xml version="1.0" encoding="UTF-8"?>
<compound>
  <version>1.0</version>
  <creation_date>2010-04-08 22:08:05 UTC</creation_date>
  <update_date>2025-11-18 23:10:40 UTC</update_date>
  <accession>FDB008464</accession>
  <name>Fenvalerate</name>
  <description>Agricultural, public health and animal husbandry insecticide

Fenvalerate is an insecticide. It is a mixture of four optical isomers which have different insecticidal activities. The 2-S alpha (or SS) configuration is the most insecticidally active isomer. Fenvalerate consists of about 23% of this isomer.</description>
  <synonyms>
    <synonym>&amp;alpha;-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)isovalerate</synonym>
    <synonym>a-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)-3-methylbutyrate</synonym>
    <synonym>Agrofen</synonym>
    <synonym>alpha-Cyano-3-phenoxybenzyl 2-(4-chlorophenyl)isovalerate</synonym>
    <synonym>Aqmatrine</synonym>
    <synonym>Asana</synonym>
    <synonym>Belmark</synonym>
    <synonym>Cyano(3-phenoxyphenyl)methyl 4-chloro-a-(1-methylethyl)benzeneacetate, 9CI</synonym>
    <synonym>Ectrin</synonym>
    <synonym>Esfenvalerate</synonym>
    <synonym>Evercide 2362</synonym>
    <synonym>Fenaxin</synonym>
    <synonym>Fenkem</synonym>
    <synonym>Fenkill</synonym>
    <synonym>Fenoxin</synonym>
    <synonym>Fenval</synonym>
    <synonym>Fenvalerate</synonym>
    <synonym>Phenoxin</synonym>
    <synonym>Phenvalerate</synonym>
    <synonym>Pydrin</synonym>
    <synonym>Sumicidin</synonym>
  </synonyms>
  <chemical_formula>C25H22ClNO3</chemical_formula>
  <average_molecular_weight>419.9</average_molecular_weight>
  <monisotopic_moleculate_weight>419.128821282</monisotopic_moleculate_weight>
  <iupac_name>cyano(3-phenoxyphenyl)methyl 2-(4-chlorophenyl)-3-methylbutanoate</iupac_name>
  <traditional_iupac>tirade</traditional_iupac>
  <cas_registry_number>51630-58-1</cas_registry_number>
  <smiles>CC(C)C(C(=O)OC(C#N)C1=CC(OC2=CC=CC=C2)=CC=C1)C1=CC=C(Cl)C=C1</smiles>
  <inchi>InChI=1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3</inchi>
  <inchikey>NYPJDWWKZLNGGM-UHFFFAOYSA-N</inchikey>
  <taxonomy>
    <description> belongs to the class of organic compounds known as pyrethroids. These are organic compounds similar to the pyrethrins. Some pyrethroids containing a chrysanthemic acid esterified with a cyclopentenone (pyrethrins), or with a phenoxybenzyl group.</description>
    <direct_parent>Pyrethroids</direct_parent>
    <kingdom>Organic compounds</kingdom>
    <super_class>Lipids and lipid-like molecules</super_class>
    <class>Fatty Acyls</class>
    <sub_class>Fatty acid esters</sub_class>
    <molecular_framework>Aromatic homomonocyclic compounds</molecular_framework>
    <alternative_parents>
      <alternative_parent>Aryl chlorides</alternative_parent>
      <alternative_parent>Benzyloxycarbonyls</alternative_parent>
      <alternative_parent>Carbonyl compounds</alternative_parent>
      <alternative_parent>Carboxylic acid esters</alternative_parent>
      <alternative_parent>Chlorobenzenes</alternative_parent>
      <alternative_parent>Diarylethers</alternative_parent>
      <alternative_parent>Diphenylethers</alternative_parent>
      <alternative_parent>Hydrocarbon derivatives</alternative_parent>
      <alternative_parent>Monocarboxylic acids and derivatives</alternative_parent>
      <alternative_parent>Nitriles</alternative_parent>
      <alternative_parent>Organic oxides</alternative_parent>
      <alternative_parent>Organochlorides</alternative_parent>
      <alternative_parent>Organopnictogen compounds</alternative_parent>
      <alternative_parent>Phenol ethers</alternative_parent>
      <alternative_parent>Phenoxy compounds</alternative_parent>
      <alternative_parent>Phenylpropanes</alternative_parent>
    </alternative_parents>
    <substituents>
      <substituent>Aromatic homomonocyclic compound</substituent>
      <substituent>Aryl chloride</substituent>
      <substituent>Aryl halide</substituent>
      <substituent>Benzenoid</substituent>
      <substituent>Benzyloxycarbonyl</substituent>
      <substituent>Carbonitrile</substituent>
      <substituent>Carbonyl group</substituent>
      <substituent>Carboxylic acid derivative</substituent>
      <substituent>Carboxylic acid ester</substituent>
      <substituent>Chlorobenzene</substituent>
      <substituent>Diaryl ether</substituent>
      <substituent>Diphenylether</substituent>
      <substituent>Ether</substituent>
      <substituent>Halobenzene</substituent>
      <substituent>Hydrocarbon derivative</substituent>
      <substituent>Monocarboxylic acid or derivatives</substituent>
      <substituent>Monocyclic benzene moiety</substituent>
      <substituent>Nitrile</substituent>
      <substituent>Organic nitrogen compound</substituent>
      <substituent>Organic oxide</substituent>
      <substituent>Organic oxygen compound</substituent>
      <substituent>Organochloride</substituent>
      <substituent>Organohalogen compound</substituent>
      <substituent>Organonitrogen compound</substituent>
      <substituent>Organooxygen compound</substituent>
      <substituent>Organopnictogen compound</substituent>
      <substituent>Phenol ether</substituent>
      <substituent>Phenoxy compound</substituent>
      <substituent>Phenylpropane</substituent>
      <substituent>Pyrethroid skeleton</substituent>
    </substituents>
    <external_descriptors>
      <external_descriptor>Pyrethroid insecticides</external_descriptor>
      <external_descriptor>Pyrethroid pesticides</external_descriptor>
      <external_descriptor>aromatic ether</external_descriptor>
      <external_descriptor>carboxylic ester</external_descriptor>
      <external_descriptor>monochlorobenzenes</external_descriptor>
    </external_descriptors>
  </taxonomy>
  <state>Liquid</state>
  <predicted_properties>
    <property>
      <kind>logp</kind>
      <value>6.30</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>logs</kind>
      <value>-5.71</value>
      <source>ALOGPS</source>
    </property>
    <property>
      <kind>solubility</kind>
      <value>8.16e-04 g/l</value>
      <source>ALOGPS</source>
    </property>
  </predicted_properties>
  <experimental_properties>
    <property>
      <kind>melting_point</kind>
      <value>39.5-53.7 oC</value>
    </property>
  </experimental_properties>
  <property>
    <kind>logp</kind>
    <value>6.61</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_acidic</kind>
    <value>10.62</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>pka_strongest_basic</kind>
    <value>-3.7</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>iupac</kind>
    <value>cyano(3-phenoxyphenyl)methyl 2-(4-chlorophenyl)-3-methylbutanoate</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>average_mass</kind>
    <value>419.9</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>mono_mass</kind>
    <value>419.128821282</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>smiles</kind>
    <value>CC(C)C(C(=O)OC(C#N)C1=CC(OC2=CC=CC=C2)=CC=C1)C1=CC=C(Cl)C=C1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formula</kind>
    <value>C25H22ClNO3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchi</kind>
    <value>InChI=1S/C25H22ClNO3/c1-17(2)24(18-11-13-20(26)14-12-18)25(28)30-23(16-27)19-7-6-10-22(15-19)29-21-8-4-3-5-9-21/h3-15,17,23-24H,1-2H3</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>inchikey</kind>
    <value>NYPJDWWKZLNGGM-UHFFFAOYSA-N</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polar_surface_area</kind>
    <value>59.32</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>refractivity</kind>
    <value>116.33</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>polarizability</kind>
    <value>43.1</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>rotatable_bond_count</kind>
    <value>8</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>acceptor_count</kind>
    <value>2</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>donor_count</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>physiological_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <property>
    <kind>formal_charge</kind>
    <value>0</value>
    <source>ChemAxon</source>
  </property>
  <pathways>
  </pathways>
  <spectra>
    <spectrum>
      <type>Specdb::NmrOneD</type>
      <spectrum_id>3117</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::EiMs</type>
      <spectrum_id>396</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>9918</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>121053</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>127380</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::CMs</type>
      <spectrum_id>145868</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10553</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10554</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>10555</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11111</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11112</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>11113</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17225</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17226</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17227</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17783</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17784</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>17785</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2773814</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2773815</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2773816</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2905425</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2905426</spectrum_id>
    </spectrum>
    <spectrum>
      <type>Specdb::MsMs</type>
      <spectrum_id>2905427</spectrum_id>
    </spectrum>
  </spectra>
  <hmdb_id>HMDB31791</hmdb_id>
  <pubchem_compound_id/>
  <chemspider_id/>
  <kegg_id/>
  <chebi_id>5014</chebi_id>
  <biocyc_id/>
  <het_id/>
  <wikipidia/>
  <vmh_id/>
  <fbonto_id/>
  <foodb_id/>
  <general_references>
    <reference>#&lt;Reference:0x000055ce31805840&gt;</reference>
    <reference>#&lt;Reference:0x000055ce31805688&gt;</reference>
  </general_references>
  <foods>
  </foods>
  <flavors>
  </flavors>
  <enzymes>
  </enzymes>
  <health_effects>
  </health_effects>
</compound>
