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Details

Stereochemistry ACHIRAL
Molecular Formula C12H27OPS3
Molecular Weight 314.511
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TRIBUFOS

SMILES

CCCCSP(=O)(SCCCC)SCCCC

InChI

InChIKey=ZOKXUAHZSKEQSS-UHFFFAOYSA-N
InChI=1S/C12H27OPS3/c1-4-7-10-15-14(13,16-11-8-5-2)17-12-9-6-3/h4-12H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C12H27OPS3
Molecular Weight 314.511
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Tribufos is an organophosphate defoliant used for cotton crops. It is specifically used to defoliate cotton in preparation for machine harvesting. Tribufos inhibits CB1 in vivo, without cholinergic poisoning signs, by 50% at 50 mg/kg intraperitoneally with a recovery half-time of 3-4 days, indicating covalent derivatization.

CNS Activity

Curator's Comment: Tribufos can cause cholinesterase inhibition in humans; that is, it can overstimulate the nervous system causing nausea, dizziness, confusion, and at very high exposures (e.g., accidents or major spills), respiratory paralysis and death.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
52.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.
2011-03-28
Effects of functionalized fullerenes on bifenthrin and tribufos toxicity to Daphnia magna: Survival, reproduction, and growth rate.
2010-11
Biochemical basis of permethrin resistance in Anopheles arabiensis from Lower Moshi, north-eastern Tanzania.
2010-07-07
Insecticide resistance profiles and synergism in field populations of the German cockroach (Dictyoptera: Blattellidae) from Singapore.
2010-04
Vapor toxicity of three prototype volatile insecticidal compounds to house fly (Diptera: Muscidae).
2009-11
Exploring the molecular basis of insecticide resistance in the dengue vector Aedes aegypti: a case study in Martinique Island (French West Indies).
2009-10-26
Variation in resistance to pyrethroids in Helicoverpa armigera from Benin Republic, West Africa.
2009-10
Identification of pyrethroid resistance associated mutations in the para sodium channel of the two-spotted spider mite Tetranychus urticae (Acari: Tetranychidae).
2009-10
Biochemical mechanisms of methoxyfenozide resistance in the cotton leafworm Spodoptera littoralis.
2009-07
Mechanisms of resistance and cross-resistance to agrochemicals in the fairy shrimp Thamnocephalus platyurus (Crustacea: Anostraca).
2009-05-05
Multi-function oxidases are responsible for the synergistic interactions occurring between repellents and insecticides in mosquitoes.
2009-04-16
Carboxylesterase activity, cDNA sequence, and gene expression in malathion susceptible and resistant strains of the cotton aphid, Aphis gossypii.
2009-03
Resistance mechanisms to mitochondrial electron transport inhibitors in a field-collected strain of Tetranychus urticae Koch (Acari: Tetranychidae).
2009-02
A concentration addition model for the activation of the constitutive androstane receptor by xenobiotic mixtures.
2009-01
The effect of insecticide synergists on the response of scabies mites to pyrethroid acaricides.
2009
Genetic characterization of resistance to deltamethrin in Plutella xylostella (Lepidoptera: Plutellidae) from India.
2008-12
Characterization of a novel high-activity esterase in Tunisian populations of the mosquito Culex pipiens.
2008-04
Household vacuum cleaners vs. the high-volume surface sampler for collection of carpet dust samples in epidemiologic studies of children.
2008-02-21
Selection for resistance to methoxyfenozide and 20-hydroxyecdysone in cells of the beet armyworm, Spodoptera exigua.
2008-01
Levels of insecticide resistance and resistance mechanisms in Aedes aegypti from some Latin American countries.
2007-12
Resistance to malathion in field populations of Ceratitis capitata.
2007-12
Genetics and mechanism of resistance to deltamethrin in a field population of Spodoptera litura (Lepidoptera: Noctuidae).
2007-10
Glutathione S-transferase conjugation of organophosphorus pesticides yields S-phospho-, S-aryl-, and S-alkylglutathione derivatives.
2007-08
Resistance to spinosad in the western flower thrips, Frankliniella occidentalis (Pergande), in greenhouses of south-eastern Spain.
2007-07
Toxicity, synergism, and neurological effects of novel volatile insecticides in insecticide-susceptible and -resistant Drosophila strains.
2007-04
Esterase-mediated bifenthrin resistance in a multiresistant strain of the two-spotted spider mite, Tetranychus urticae.
2007-02
Resistance status of the Colorado potato beetle, Leptinotarsa decemlineata, to endosulfan in East Azarbaijan and Ardabil provinces of Iran.
2007
Complete maternal inheritance of bifenazate resistance in Tetranychus urticae Koch (Acari: Tetranychidae) and its implications in mode of action considerations.
2006-11
Mediation of pyrethroid insecticide toxicity to honey bees (Hymenoptera: Apidae) by cytochrome P450 monooxygenases.
2006-08
Synergism between insecticides permethrin and propoxur occurs through activation of presynaptic muscarinic negative feedback of acetylcholine release in the insect central nervous system.
2006-07
Effects of Piperonyl Butoxide on the Metabolism of DEF S,S,S-Tributyl Phosphorotrithioate) in Fingerling Channel Catfish.
2006
Serine hydrolase targets of organophosphorus toxicants.
2005-12-15
Resistance in the mosquito, Culex quinquefasciatus, and possible mechanisms for resistance.
2005-11
Resistance potential of colorado potato beetle (Coleoptera: Chrysomelidae) to novaluron.
2005-10
Metabolic mechanisms of insecticide resistance in the western flower thrips, Frankliniella occidentalis (Pergande).
2005-10
Chlorpyrifos resistance in mosquito Culex quinquefasciatus.
2005-09
Polymorphisms in a carboxylesterase gene between organophosphate-resistant and -susceptible Aphis gossypii (Homoptera: Aphididae).
2005-08
Blood acylpeptide hydrolase activity is a sensitive marker for exposure to some organophosphate toxicants.
2005-08
Synergism and stability of acetamiprid resistance in a laboratory colony of Plutella xylostella.
2005-08
Platelet-activating factor acetylhydrolase: selective inhibition by potent n-alkyl methylphosphonofluoridates.
2005-06-01
Enhanced esterase gene expression and activity in a malathion-resistant strain of the tarnished plant bug, Lygus lineolaris.
2004-11
Resistance and synergistic effects of insecticides in Bactrocera dorsalis (Diptera: Tephritidae) in Taiwan.
2004-10
Evaluation of mechanisms of azinphos-methyl resistance in the codling moth Cydia pomonella (L.).
2004-10
Effects of insecticides and defoliants applied alone and in combination for control of overwintering boll weevil (Anthonomus grandis; Coleoptera: Curculionidae)--laboratory and field studies.
2004-09
Lysophospholipase inhibition by organophosphorus toxicants.
2004-05-01
Synergism of insecticides provides evidence of metabolic mechanisms of resistance in the obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae).
2004-05
Genetic analysis and cross-resistance spectrum of a laboratory-selected chlorfenapyr resistant strain of two-spotted spider mite (Acari: Tetranychidae).
2004
Cotton defoliant runoff as a function of active ingredient and tillage.
2003-12-17
Temephos resistance in two forms of Aedes aegypti and its significance for the resistance mechanism.
2003-12
Microsomal transformation of organophosphorus pesticides by white rot fungi.
2003-12
Patents

Sample Use Guides

Mice: Tribufos inhibits CB1 in vivo, without cholinergic poisoning signs, by 50% at 50 mg/kg intraperitoneally with a recovery half-time of 3-4 days.
Route of Administration: Intraperitoneal
Tribufos inhibited mouse liver FAAH with IC 50 value of 52 uM.
Substance Class Chemical
Created
by admin
on Mon Mar 31 20:51:38 GMT 2025
Edited
by admin
on Mon Mar 31 20:51:38 GMT 2025
Record UNII
53075G8GRF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
FOSFALL
Preferred Name English
TRIBUFOS
ISO   MI  
Common Name English
B 1,776
Code English
BUTYL PHOSPHOROTRITHIOATE
Systematic Name English
S,S,S-TRIBUTYL PHOSPHOROTRITHIOATE
Systematic Name English
CHEMAGRO B 1776
Common Name English
TBPT
Common Name English
PHOSPHOROTRITHIOIC ACID, S,S,S-TRIBUTYL ESTER
Common Name English
DEF
Common Name English
S,S,S-TRIBUTYL TRITHIOPHOSPHATE
Systematic Name English
TRIBUFOS [MI]
Common Name English
TBTP
Common Name English
BUTYL PHOSPHOROTRITHIOATE ((BUS)3PO)
Common Name English
BUTIPHOS
Common Name English
TRIBUFOS [ISO]
Common Name English
B-1776
Code English
Classification Tree Code System Code
EPA PESTICIDE CODE 74801
Created by admin on Mon Mar 31 20:51:38 GMT 2025 , Edited by admin on Mon Mar 31 20:51:38 GMT 2025
Code System Code Type Description
MESH
C006863
Created by admin on Mon Mar 31 20:51:38 GMT 2025 , Edited by admin on Mon Mar 31 20:51:38 GMT 2025
PRIMARY
MERCK INDEX
m11049
Created by admin on Mon Mar 31 20:51:38 GMT 2025 , Edited by admin on Mon Mar 31 20:51:38 GMT 2025
PRIMARY Merck Index
CHEBI
38737
Created by admin on Mon Mar 31 20:51:38 GMT 2025 , Edited by admin on Mon Mar 31 20:51:38 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-120-8
Created by admin on Mon Mar 31 20:51:38 GMT 2025 , Edited by admin on Mon Mar 31 20:51:38 GMT 2025
PRIMARY
EPA CompTox
DTXSID1024174
Created by admin on Mon Mar 31 20:51:38 GMT 2025 , Edited by admin on Mon Mar 31 20:51:38 GMT 2025
PRIMARY
ALANWOOD
tribufos
Created by admin on Mon Mar 31 20:51:38 GMT 2025 , Edited by admin on Mon Mar 31 20:51:38 GMT 2025
PRIMARY
CAS
78-48-8
Created by admin on Mon Mar 31 20:51:38 GMT 2025 , Edited by admin on Mon Mar 31 20:51:38 GMT 2025
PRIMARY
HSDB
668
Created by admin on Mon Mar 31 20:51:38 GMT 2025 , Edited by admin on Mon Mar 31 20:51:38 GMT 2025
PRIMARY
PUBCHEM
5125
Created by admin on Mon Mar 31 20:51:38 GMT 2025 , Edited by admin on Mon Mar 31 20:51:38 GMT 2025
PRIMARY
FDA UNII
53075G8GRF
Created by admin on Mon Mar 31 20:51:38 GMT 2025 , Edited by admin on Mon Mar 31 20:51:38 GMT 2025
PRIMARY