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Details

Stereochemistry ACHIRAL
Molecular Formula C16H20O6P2S3
Molecular Weight 466.469
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TEMEFOS

SMILES

COP(=S)(OC)OC1=CC=C(SC2=CC=C(OP(=S)(OC)OC)C=C2)C=C1

InChI

InChIKey=WWJZWCUNLNYYAU-UHFFFAOYSA-N
InChI=1S/C16H20O6P2S3/c1-17-23(25,18-2)21-13-5-9-15(10-6-13)27-16-11-7-14(8-12-16)22-24(26,19-3)20-4/h5-12H,1-4H3

HIDE SMILES / InChI
Molecular Formula C16H20O6P2S3
Molecular Weight 466.469
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Temefos (Diphos, Temephos) is an organophosphate larvicide, used to treat water infested with disease-carrying insects including mosquitoes, midges, and black fly larvae. Temefos affects the central nervous system through inhibition of cholinesterase, results in death before reaching the adult stage. Diphos has been used in trials studying the treatment of Plasmodium Falciparum Malaria. Temephos was first registered in the United States in 1965 by American Cyanamid Company for a number of uses including citrus fruits, pet collars, and mosquito control. A Registration Standard was issued in August, 1981. In response to EPA's 1991 Data Call-In, American Cyanamid dropped all uses except the mosquito larvicide use in non-potable waters and requested a low volume minor use waiver for relief from the data requirements associated with that use.

CNS Activity

Originator

American Cyanamid
37
Curator's Comment: Temephos was first registered in the United States in 1965 by American Cyanamid Company for a number of uses including citrus fruits, pet collars, and mosquito control.

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Not Provided
511
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Trend of temephos resistance in Aedes (Stegomyia) mosquitoes in Thailand during 2003-2005.
2007-06
Larvicidal effects of a neem (Azadirachta indica) oil formulation on the malaria vector Anopheles gambiae.
2007-05-22
Efficacy of Bacillus thuringiensis israelensis, VectoBac WG and DT, formulations against dengue mosquito vectors in cement potable water jars in Cambodia.
2007-03
Larvicidal efficacy and biological stability of a botanical natural product, zedoary oil-impregnated sand granules, against Aedes aegypti (Diptera, Culicidae).
2007-03
Ethnoveterinary medicines used for ruminants in British Columbia, Canada.
2007-02-26
Sublethal effects of mosquito larvicides on swimming performance of larvivorous fish Melanotaenia duboulayi (Atheriniformes: Melanotaeniidae).
2007-02
Abate distribution and dengue control in rural Cambodia.
2007-02
Differential sensitivity to Bacillus thuringiensis var. israelensis and temephos in field mosquito populations of Ochlerotatus cataphylla (Diptera: Culicidae): toward resistance?
2007-01
Laboratory bioefficacy of CREEK 1.0G (temephos) against Aedes (Stegomyia) aegypti (Linnaeus) larvae.
2006-12
Effect of Novaluron (Rimon 10 EC) on the mosquitoes Anopheles albimanus, Anopheles pseudopunctipennis, Aedes aegypti, Aedes albopictus and Culex quinquefasciatus from Chiapas, Mexico.
2006-12
Larvicidal activity of some Labiatae (Lamiaceae) plant extracts from Turkey.
2006-12
Evaluation of temephos and chlorpyrifos-methyl against Culex pipiens (Diptera: Culicidae) larvae in septic tanks in Antalya, Turkey.
2006-11
Use of bioassay and microplate assay to detect and measure insecticide resistance in field populations of Culex pipiens from filariasis endemic areas of Egypt.
2006-09
Laboratory evaluation of susceptibility of natural subpopulations of Aedes aegypti larvae to temephos.
2006-09
Effects of temephos and temperature on Wolbachia load and life history traits of Aedes albopictus.
2006-09
Uganda's successful Guinea Worm Eradication Program.
2006-07
Effects of climate and different management strategies on Aedes aegypti breeding sites: a longitudinal survey in Brasília (DF, Brazil).
2006-07
A steep decline of malaria morbidity and mortality trends in Eritrea between 2000 and 2004: the effect of combination of control methods.
2006-04-24
Susceptibility status of some culicine mosquitoes to insecticides in Rajahmundry town of Andhra Pradesh, India.
2006-03
Transmission of Onchocerca volvulus and prospects for the elimination of its vector, the blackfly Simulium neavei in the Mpamba-Nkusi focus in Western Uganda.
2006-03
Response of Aedes aegypti (Diptera: Culicidae) larvae to three xenobiotic exposures: larval tolerance and detoxifying enzyme activities.
2006-02
Bionomics of Anopheles stephensi Liston in the malarious area of Hormozgan province, southern Iran, 2002.
2006-02
Insecticide susceptibility of mosquitoes invading tsunami-affected areas of Thailand.
2006
Susceptibility of Aedes aegypti and Aedes albopictus to temephos in four study sites in Kuala Lumpur City Center and Selangor State, Malaysia.
2005-12
Weekly variation on susceptibility status of Aedes mosquitoes against temephos in Selangor, Malaysia.
2005-12
Patterns of insecticide resistance in larval Culex pipiens populations in Israel: dynamics and trends.
2005-12
Effectiveness of methoprene, an insect growth regulator, against temephos-resistant Aedes aegypti populations from different Brazilian localities, under laboratory conditions.
2005-09
Insecticide susceptibility of Aedes aegypti and Aedes albopictus across Thailand.
2005-09
Monitoring of insecticides resistance in main malaria vectors in a malarious area of Kahnooj district, Kerman province, southeastern Iran.
2005-09
[Residual effect of commercial applications of larvicides temefos and Bacillus thuringiensis israelensis on Aedes aegypti larvae in recipients with water renewal].
2005-08-06
Effectiveness of dengue control practices in household water containers in Northeast Thailand.
2005-08
Residual effect of two Bacillus thuringiensis var. israelensis products assayed against Aedes aegypti (Diptera: Culicidae) in laboratory and outdoors at Rio de Janeiro, Brazil.
2005-07-16
Efficacy of a Bacillus thuringiensis israelensis tablet formulation, vectobac DT, for control of dengue mosquito vectors in potable water containers.
2005-07
Insecticide resistance development in Culex quinquefasciatus (Say), Aedes aegypti (L.) and Aedes albopictus (Skuse) larvae against malathion, permethrin and temephos.
2005-06
Evaluation of various control agents against mosquito larvae in rice paddies in Taiwan.
2005-06
Sequential release and residual activity of temephos applied as sand granules to water-storage jars for the control of Aedes aegypti larvae (Diptera: Culicidae).
2005-06
[Cross resistance to pyrethroids in Aedes aegypti from Cuba induced by the selection with organophosphate malathion].
2005-04-27
[Levels of resistance to insecticides and their mechanisms in 2 strains of Aedes aegypti from Panama].
2005-04-27
[Status of resistance to insecticides and resistance mechanisms in larvae from Playa municipality collected during the intensive campaign against Aedes aegypti in Havana City, 2001-2002].
2005-04-27
[Resistance to insecticides in larvae and adults of Aedes aegypti, Havana City: prevalence of A4 esterasa associated with resistance to temephos].
2005-04-27
Bottle and biochemical assays on temephos resistance in Aedes aegypti in Thailand.
2005-03
[Aedes aegypti resistance to temefos in counties of Ceará State].
2005-01-04
[Efficient and permanent impact of two insecticides with the active ingredient, temephos, on mosquitoes (Diptera: Culicidae) larvae.].
2005
Insecticide susceptibility and selection for resistance in a population of Aedes aegypti from Ratchaburi province, Thailand.
2004-12
Efficacy of different organophosphate and synthetic pyrethroid insecticides to the larvae of malaria vector Anopheles stephensi, Liston.
2004-10
Study on susceptibility status in aquatic and adult stages of Aedes aegypti and Ae. albopictus against insecticides at international airports of south India.
2004-09
Surveillance of dengue vector at thiruvananthapuram (Kerala) International Airport.
2004-06
Laboratory bio-assay of temephos and fenthion against some vector species of public health importance.
2004-06
Studies on persistence of temephos in sandy loam soil under field and laboratory conditions.
2004-04
Larval habitats of main malaria vectors in Hormozgan province and their susceptibility to different larvicides.
2004
Patents

Patents

JP2008509189A
189

Sample Use Guides

In Vivo Use Guide
Curator's Comment: In other mammals, temephos produces signs and symptoms typical of cholinesterase inhibition at moderate levels of exposure (500 mg/kg). Death does not occur unless very large doses of the compound are administered. The LD50 of temephos ranges from 2,000 to 13,000 mg/kg for rats and is 4,700 mg/kg for mice. The LD50 for a 2% powder formulation of temephos in dogs and cats is greater than 5,000 mg/kg for both species.
Humans ingested 256 mg/kg of Temefos for five days and 64 mg/kg for four months without any symptoms or detectable effects on blood enzyme activity.
Route of Administration: Oral
In Vitro Use Guide
Regarding the cytostatic effect in human lymphocytes, temephos (10 uM) caused a significant decrease in the percentage of binucleated cells and in the nuclear division index as well as an increase in the apoptotic cell frequency, which was not the case for HepG2 cells.
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:33:03 GMT 2025
Edited
by admin
on Mon Mar 31 17:33:03 GMT 2025
Record UNII
ONP3ME32DL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TEMEPHOS
ISO   MI  
Preferred Name English
TEMEFOS
HSDB   INN   MART.   USAN   WHO-DD  
USAN   INN  
Official Name English
NEPHIS
Brand Name English
temefos [INN]
Common Name English
O,O'-(THIODI-P-PHENYLENE) O,O,O',O'-TETRAMETHYL BIS(PHOSPHOROTHIOATE)
Common Name English
O,O'-(THIODI-4,1-PHENYLENE) BIS(O,O-DIMETHYL PHOSPHOROTHIOATE)
Common Name English
AC-52160
Code English
DIFOS
Brand Name English
TEMEPHOS [ISO]
Common Name English
MOSQ
Brand Name English
DIPHOS
Brand Name English
PHOSPHOROTHIOIC ACID, O,O'-(THIODI-4,1-PHENYLENE) O,O,O',O'-TETRAMETHYL ESTER
Common Name English
ABATHION
Brand Name English
O,O,O',O'-TETRAMETHYL O,O'-THIODI-P-PHENYLENE BIS(PHOSPHOROTHIOATE)
Common Name English
ECOPRO 1707
Brand Name English
Temefos [WHO-DD]
Common Name English
NSC-755842
Code English
AZAI-SS
Brand Name English
PROCIDA
Brand Name English
LAVIFOS
Brand Name English
BIOTHION
Brand Name English
TEMEFOS [MART.]
Common Name English
ENT-27165
Code English
TEMEFOS [HSDB]
Common Name English
EI-52160
Code English
TEMEFOS [USAN]
Common Name English
TEMEPHOS [MI]
Common Name English
DIFENPHOS
Brand Name English
ABATE
Brand Name English
BIOTHON
Brand Name English
O,O,O',O'-TETRAMETHYL O,O'-(THIODI-4,1-PHENYLENE) BIS(THIOPHOSPHATE)
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 59001
Created by admin on Mon Mar 31 17:33:03 GMT 2025 , Edited by admin on Mon Mar 31 17:33:03 GMT 2025
NCI_THESAURUS C737
Created by admin on Mon Mar 31 17:33:03 GMT 2025 , Edited by admin on Mon Mar 31 17:33:03 GMT 2025
Code System Code Type Description
CHEBI
38954
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PRIMARY
HSDB
956
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PRIMARY
EPA CompTox
DTXSID1032484
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PRIMARY
PUBCHEM
5392
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PRIMARY
FDA UNII
ONP3ME32DL
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PRIMARY
ChEMBL
CHEMBL1355821
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PRIMARY
DRUG BANK
DB12231
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PRIMARY
INN
3561
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PRIMARY
EVMPD
SUB10881MIG
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PRIMARY
CHEBI
30669
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PRIMARY
NSC
755842
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PRIMARY
SMS_ID
100000082465
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PRIMARY
ECHA (EC/EINECS)
222-191-1
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PRIMARY
MERCK INDEX
m10548
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PRIMARY Merck Index
NCI_THESAURUS
C80606
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PRIMARY
ALANWOOD
temephos
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PRIMARY
CAS
3383-96-8
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PRIMARY
WIKIPEDIA
TEMEFOS
Created by admin on Mon Mar 31 17:33:03 GMT 2025 , Edited by admin on Mon Mar 31 17:33:03 GMT 2025
PRIMARY
Related Record Type Details
Structure of TEMEFOS
ACTIVE MOIETY
NIH
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