U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
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
Temephos resistance in two forms of Aedes aegypti and its significance for the resistance mechanism.
2003 Dec
Microsomal transformation of organophosphorus pesticides by white rot fungi.
2003 Dec
Cotton defoliant runoff as a function of active ingredient and tillage.
2003 Nov-Dec
Genetic analysis and cross-resistance spectrum of a laboratory-selected chlorfenapyr resistant strain of two-spotted spider mite (Acari: Tetranychidae).
2004
Synergism of insecticides provides evidence of metabolic mechanisms of resistance in the obliquebanded leafroller Choristoneura rosaceana (Lepidoptera: Tortricidae).
2004 May
Lysophospholipase inhibition by organophosphorus toxicants.
2004 May 1
Enhanced esterase gene expression and activity in a malathion-resistant strain of the tarnished plant bug, Lygus lineolaris.
2004 Nov
Resistance and synergistic effects of insecticides in Bactrocera dorsalis (Diptera: Tephritidae) in Taiwan.
2004 Oct
Evaluation of mechanisms of azinphos-methyl resistance in the codling moth Cydia pomonella (L.).
2004 Oct
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 Sep
Polymorphisms in a carboxylesterase gene between organophosphate-resistant and -susceptible Aphis gossypii (Homoptera: Aphididae).
2005 Aug
Blood acylpeptide hydrolase activity is a sensitive marker for exposure to some organophosphate toxicants.
2005 Aug
Synergism and stability of acetamiprid resistance in a laboratory colony of Plutella xylostella.
2005 Aug
Serine hydrolase targets of organophosphorus toxicants.
2005 Dec 15
Platelet-activating factor acetylhydrolase: selective inhibition by potent n-alkyl methylphosphonofluoridates.
2005 Jun 1
Resistance in the mosquito, Culex quinquefasciatus, and possible mechanisms for resistance.
2005 Nov
Resistance potential of colorado potato beetle (Coleoptera: Chrysomelidae) to novaluron.
2005 Oct
Metabolic mechanisms of insecticide resistance in the western flower thrips, Frankliniella occidentalis (Pergande).
2005 Oct
Chlorpyrifos resistance in mosquito Culex quinquefasciatus.
2005 Sep
Effects of Piperonyl Butoxide on the Metabolism of DEF S,S,S-Tributyl Phosphorotrithioate) in Fingerling Channel Catfish.
2006
Mediation of pyrethroid insecticide toxicity to honey bees (Hymenoptera: Apidae) by cytochrome P450 monooxygenases.
2006 Aug
Synergism between insecticides permethrin and propoxur occurs through activation of presynaptic muscarinic negative feedback of acetylcholine release in the insect central nervous system.
2006 Jul
Complete maternal inheritance of bifenazate resistance in Tetranychus urticae Koch (Acari: Tetranychidae) and its implications in mode of action considerations.
2006 Nov
Resistance status of the Colorado potato beetle, Leptinotarsa decemlineata, to endosulfan in East Azarbaijan and Ardabil provinces of Iran.
2007
Toxicity, synergism, and neurological effects of novel volatile insecticides in insecticide-susceptible and -resistant Drosophila strains.
2007 Apr
Glutathione S-transferase conjugation of organophosphorus pesticides yields S-phospho-, S-aryl-, and S-alkylglutathione derivatives.
2007 Aug
Levels of insecticide resistance and resistance mechanisms in Aedes aegypti from some Latin American countries.
2007 Dec
Resistance to malathion in field populations of Ceratitis capitata.
2007 Dec
Esterase-mediated bifenthrin resistance in a multiresistant strain of the two-spotted spider mite, Tetranychus urticae.
2007 Feb
Resistance to spinosad in the western flower thrips, Frankliniella occidentalis (Pergande), in greenhouses of south-eastern Spain.
2007 Jul
Genetics and mechanism of resistance to deltamethrin in a field population of Spodoptera litura (Lepidoptera: Noctuidae).
2007 Oct
Characterization of a novel high-activity esterase in Tunisian populations of the mosquito Culex pipiens.
2008 Apr
Genetic characterization of resistance to deltamethrin in Plutella xylostella (Lepidoptera: Plutellidae) from India.
2008 Dec
Household vacuum cleaners vs. the high-volume surface sampler for collection of carpet dust samples in epidemiologic studies of children.
2008 Feb 21
Selection for resistance to methoxyfenozide and 20-hydroxyecdysone in cells of the beet armyworm, Spodoptera exigua.
2008 Jan
The effect of insecticide synergists on the response of scabies mites to pyrethroid acaricides.
2009
Multi-function oxidases are responsible for the synergistic interactions occurring between repellents and insecticides in mosquitoes.
2009 Apr 16
Resistance mechanisms to mitochondrial electron transport inhibitors in a field-collected strain of Tetranychus urticae Koch (Acari: Tetranychidae).
2009 Feb
A concentration addition model for the activation of the constitutive androstane receptor by xenobiotic mixtures.
2009 Jan
Biochemical mechanisms of methoxyfenozide resistance in the cotton leafworm Spodoptera littoralis.
2009 Jul
Carboxylesterase activity, cDNA sequence, and gene expression in malathion susceptible and resistant strains of the cotton aphid, Aphis gossypii.
2009 Mar
Mechanisms of resistance and cross-resistance to agrochemicals in the fairy shrimp Thamnocephalus platyurus (Crustacea: Anostraca).
2009 May 5
Vapor toxicity of three prototype volatile insecticidal compounds to house fly (Diptera: Muscidae).
2009 Nov
Variation in resistance to pyrethroids in Helicoverpa armigera from Benin Republic, West Africa.
2009 Oct
Identification of pyrethroid resistance associated mutations in the para sodium channel of the two-spotted spider mite Tetranychus urticae (Acari: Tetranychidae).
2009 Oct
Exploring the molecular basis of insecticide resistance in the dengue vector Aedes aegypti: a case study in Martinique Island (French West Indies).
2009 Oct 26
Insecticide resistance profiles and synergism in field populations of the German cockroach (Dictyoptera: Blattellidae) from Singapore.
2010 Apr
Biochemical basis of permethrin resistance in Anopheles arabiensis from Lower Moshi, north-eastern Tanzania.
2010 Jul 7
Effects of functionalized fullerenes on bifenthrin and tribufos toxicity to Daphnia magna: Survival, reproduction, and growth rate.
2010 Nov
Activity profiles of 309 ToxCast™ chemicals evaluated across 292 biochemical targets.
2011 Mar 28
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.
Name Type Language
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
FOSFALL
Brand 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 Sat Dec 16 01:27:58 GMT 2023 , Edited by admin on Sat Dec 16 01:27:58 GMT 2023
Code System Code Type Description
MESH
C006863
Created by admin on Sat Dec 16 01:27:58 GMT 2023 , Edited by admin on Sat Dec 16 01:27:58 GMT 2023
PRIMARY
MERCK INDEX
m11049
Created by admin on Sat Dec 16 01:27:58 GMT 2023 , Edited by admin on Sat Dec 16 01:27:58 GMT 2023
PRIMARY Merck Index
CHEBI
38737
Created by admin on Sat Dec 16 01:27:58 GMT 2023 , Edited by admin on Sat Dec 16 01:27:58 GMT 2023
PRIMARY
ECHA (EC/EINECS)
201-120-8
Created by admin on Sat Dec 16 01:27:58 GMT 2023 , Edited by admin on Sat Dec 16 01:27:58 GMT 2023
PRIMARY
EPA CompTox
DTXSID1024174
Created by admin on Sat Dec 16 01:27:58 GMT 2023 , Edited by admin on Sat Dec 16 01:27:58 GMT 2023
PRIMARY
ALANWOOD
tribufos
Created by admin on Sat Dec 16 01:27:58 GMT 2023 , Edited by admin on Sat Dec 16 01:27:58 GMT 2023
PRIMARY
CAS
78-48-8
Created by admin on Sat Dec 16 01:27:58 GMT 2023 , Edited by admin on Sat Dec 16 01:27:58 GMT 2023
PRIMARY
HSDB
668
Created by admin on Sat Dec 16 01:27:58 GMT 2023 , Edited by admin on Sat Dec 16 01:27:58 GMT 2023
PRIMARY
PUBCHEM
5125
Created by admin on Sat Dec 16 01:27:58 GMT 2023 , Edited by admin on Sat Dec 16 01:27:58 GMT 2023
PRIMARY
FDA UNII
53075G8GRF
Created by admin on Sat Dec 16 01:27:58 GMT 2023 , Edited by admin on Sat Dec 16 01:27:58 GMT 2023
PRIMARY