Page last updated: 2024-11-04

butyl phosphorotrithioate

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

butyl phosphorotrithioate: a herbicide [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID5125
CHEMBL ID1901047
CHEBI ID38737
SCHEMBL ID119208
MeSH IDM0049677

Synonyms (90)

Synonym
BRD-K02837237-001-02-9
phosphorotrithioic acid, s,s,s-tributyl ester
s,s,s-tributyl phosphorotrithioate
DIVK1C_006604
KBIO1_001548
SPECTRUM_001887
ai3-25812
ortho phosphate defoliant
brn 1910992
fossfall
hsdb 668
b 1776
epa pesticide chemical code 074801
tribuphos
butiphos
s,s,s-tributyltrithiophosphate
de-green
butyl phosphorotrithioate ((bus)3po)
s,s,s-tributyltrithiofosfat [czech]
tbtp
einecs 201-120-8
s,s,s-tributylphosphorotrithioate
caswell no. 864
b-1,776
fos-fall a
e-z-off d
SPECTRUM5_002004
merphos oxide
DEF ,
tribufos
CHEBI:38737 ,
78-48-8
s,s,s-tributyl trithiophosphate
butifos
butyl phosphorotrithioate
tributylphosphorotrithioate
def defoliant
NCGC00095769-01
KBIO2_002411
KBIOSS_002417
KBIO3_001927
KBIOGR_001147
KBIO2_007547
KBIO2_004979
SPECTRUM4_000684
SPECTRUM3_000844
SPECTRUM2_001843
SPECPLUS_000508
SPBIO_001626
SPECTRUM330053
BSPBIO_002427
NCGC00095769-02
NCGC00095769-03
1-bis(butylsulfanyl)phosphorylsulfanylbutane
NCGC00095769-04
NCGC00095769-05
B-1776 ,
1,2,4-tributylphosphorotrithioate
tox21_300642
NCGC00254550-01
cas-78-48-8
tox21_201934
dtxsid1024174 ,
NCGC00259483-01
dtxcid304174
CCG-39381
tribufos [iso]
s,s,s-tributyltrithiofosfat
53075g8grf ,
unii-53075g8grf
AKOS015902866
CHEMBL1901047
s,s,s,-tributylphosphorotrithioate
tribufos [mi]
b 1,776
tbpt
fosfall
chemagro b 1776
SCHEMBL119208
chemagro 1,776
merphos-oxon
merphos-oxone
ZOKXUAHZSKEQSS-UHFFFAOYSA-N
tribufos 100 microg/ml in methanol
tribufos (def)
tribufos 100 microg/ml in cyclohexane
degreen
phosphorotrithioicacid,s,s,s-tributyl ester
Q2537076
1,2,4-tributyl phosphorotrithioate

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"The oral LD50 of a compound in hens does not reliably predict the neurotoxic dose of that compound."( Consideration of dose levels for delayed neurotoxicity testing in hens: the relationship of neurotoxic dosages to acute LD50 values.
Hixson, EJ, 1983
)
0.27
"Based on 48 h LD50 estimates from topical bioassays, cypermethrin was more toxic than permethrin to Helicoverpa zea (Boddie) larvae and adults; however, the two pyrethroids did not differ significantly in their relative toxicities to Spodoptera frugiperda (J."( Toxicity of pyrethroids and effect of synergists to larval and adult Helicoverpa zea, Spodoptera frugiperda, and Agrotis ipsilon (Lepidoptera: Noctuidae).
Knowles, CO; Usmani, KA, 2001
)
0.31

Pharmacokinetics

ExcerptReferenceRelevance
" These pharmacokinetic events usually were higher with trans-cypermethrin-14C than with cis-cypermethrin-14C."( Pharmacokinetic mechanisms associated with synergism by DEF of cypermethrin toxicity in larval and adult Helicoverpa zea, Spodoptera frugiperda, and Agrotis ipsilon (Lepidoptera: Noctuidae).
Knowles, CO; Usmani, KA, 2001
)
0.31

Dosage Studied

ExcerptRelevanceReference
" The oral LD50 in rats does not predict either the oral LD50 in hens or the neurotoxic dose in hens, so there is no justification for using the rat value to predict the neurotoxic dosage in hens."( Consideration of dose levels for delayed neurotoxicity testing in hens: the relationship of neurotoxic dosages to acute LD50 values.
Hixson, EJ, 1983
)
0.27
" Peak blood levels of 14C occurred 2 hr after dosing in both groups of rats."( The effect of intestinal esterase inhibition on the in vivo absorption and toxicity of Di-n-butyl phthalate.
Carter, DE; Earnest, DL; White, RD, 1983
)
0.27
" Neurotoxic esterase (NTE) was significantly decreased from control with topical dosing of 200, 500, and 1000 mg/kg DEF and with TOCP treatments."( Induction of hepatic microsomal cytochrome P-450 and inhibition of brain, liver, and plasma esterases by an acute dose of S,S,S-tri-n-butyl phosphorotrithioate (DEF) in the adult hen.
Abou-Donia, MB; Carrington, CD; Lapadula, DM, 1984
)
0.47
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Roles (1)

RoleDescription
defoliantA herbicide which when sprayed or dusted on plants causes its leaves to fall off.
[role information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Drug Classes (1)

ClassDescription
organic thiophosphate
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (11)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
acetylcholinesteraseHomo sapiens (human)Potency17.35840.002541.796015,848.9004AID1347395; AID1347397; AID1347398; AID1347399
pregnane X receptorRattus norvegicus (Norway rat)Potency7.94330.025127.9203501.1870AID651751
RAR-related orphan receptor gammaMus musculus (house mouse)Potency4.08560.006038.004119,952.5996AID1159523
AR proteinHomo sapiens (human)Potency36.91300.000221.22318,912.5098AID1259243; AID1259247; AID743035; AID743063
nuclear receptor subfamily 1, group I, member 3Homo sapiens (human)Potency12.62520.001022.650876.6163AID1224838; AID1224839
progesterone receptorHomo sapiens (human)Potency24.05250.000417.946075.1148AID1346795
retinoid X nuclear receptor alphaHomo sapiens (human)Potency34.16450.000817.505159.3239AID1159527; AID1159531; AID588546
pregnane X nuclear receptorHomo sapiens (human)Potency15.68900.005428.02631,258.9301AID1346982; AID720659
thyroid stimulating hormone receptorHomo sapiens (human)Potency29.31130.001628.015177.1139AID1224843; AID1224895; AID1259385; AID1259395
nuclear factor of kappa light polypeptide gene enhancer in B-cells 1 (p105), isoform CRA_aHomo sapiens (human)Potency13.800619.739145.978464.9432AID1159509
v-jun sarcoma virus 17 oncogene homolog (avian)Homo sapiens (human)Potency30.33040.057821.109761.2679AID1159526; AID1159528
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (13)

Assay IDTitleYearJournalArticle
AID1110857Insecticidal activity against Tetranychus urticae LS-VL (two-spotted spider mite) larvae reared under continuous pressure of 5000 mg/L spirodiclofen for 5 months assessed as mortality treated 3-4 hr after 10 mg/L esterase inhibitor, DEF application measur2009Pest management science, Apr, Volume: 65, Issue:4
Genetic and biochemical analysis of a laboratory-selected spirodiclofen-resistant strain of Tetranychus urticae Koch (Acari: Tetranychidae).
AID1111932Inhibition of Frankliniella occidentalis ACR (western flower thrips) total esterase activity2011Pest management science, Dec, Volume: 67, Issue:12
Esterase inhibition by synergists in the western flower thrips Frankliniella occidentalis.
AID977602Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID1111931Inhibition of Frankliniella occidentalis MET (western flower thrips) total esterase activity2011Pest management science, Dec, Volume: 67, Issue:12
Esterase inhibition by synergists in the western flower thrips Frankliniella occidentalis.
AID1111934Inhibition of Frankliniella occidentalis MLFOM (western flower thrips) total esterase activity2011Pest management science, Dec, Volume: 67, Issue:12
Esterase inhibition by synergists in the western flower thrips Frankliniella occidentalis.
AID1110848Synergism factor, ratio of LC50 for Tetranychus urticae SR-VP (two-spotted spider mite) larvae to LC50 for Tetranychus urticae SR-VP larva in presence of 10 mg/L esterase inhibitor, DEF2009Pest management science, Apr, Volume: 65, Issue:4
Genetic and biochemical analysis of a laboratory-selected spirodiclofen-resistant strain of Tetranychus urticae Koch (Acari: Tetranychidae).
AID1110851Insecticidal activity against Tetranychus urticae SR-VP (two-spotted spider mite) larvae reared under continuous pressure of 5000 mg/L spirodiclofen for 5 months assessed as mortality treated 3-4 hr after 10 mg/L esterase inhibitor, DEF application measur2009Pest management science, Apr, Volume: 65, Issue:4
Genetic and biochemical analysis of a laboratory-selected spirodiclofen-resistant strain of Tetranychus urticae Koch (Acari: Tetranychidae).
AID1110854Synergism factor, ratio of LC50 for Tetranychus urticae LS-VL (two-spotted spider mite) larvae to LC50 for Tetranychus urticae LS-VL larva in presence of 10 mg/L esterase inhibitor, DEF2009Pest management science, Apr, Volume: 65, Issue:4
Genetic and biochemical analysis of a laboratory-selected spirodiclofen-resistant strain of Tetranychus urticae Koch (Acari: Tetranychidae).
AID977599Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM2013Molecular pharmacology, Jun, Volume: 83, Issue:6
Structure-based identification of OATP1B1/3 inhibitors.
AID1110845Resistance ratio of LC50 for Tetranychus urticae SR-VP (two-spotted spider mite) larvae reared under continuous pressure of 5000 mg/L spirodiclofen for 5 months in presence of 10 mg/L esterase inhibitor, DEF to LC50 for Tetranychus urticae LS-VL (two-spot2009Pest management science, Apr, Volume: 65, Issue:4
Genetic and biochemical analysis of a laboratory-selected spirodiclofen-resistant strain of Tetranychus urticae Koch (Acari: Tetranychidae).
AID1111933Inhibition of Frankliniella occidentalis FOR (western flower thrips) total esterase activity2011Pest management science, Dec, Volume: 67, Issue:12
Esterase inhibition by synergists in the western flower thrips Frankliniella occidentalis.
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
AID1159550Human Phosphogluconate dehydrogenase (6PGD) Inhibitor Screening2015Nature cell biology, Nov, Volume: 17, Issue:11
6-Phosphogluconate dehydrogenase links oxidative PPP, lipogenesis and tumour growth by inhibiting LKB1-AMPK signalling.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (81)

TimeframeStudies, This Drug (%)All Drugs %
pre-199027 (33.33)18.7374
1990's5 (6.17)18.2507
2000's23 (28.40)29.6817
2010's25 (30.86)24.3611
2020's1 (1.23)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 10.48

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index10.48 (24.57)
Research Supply Index4.47 (2.92)
Research Growth Index4.94 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (10.48)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews4 (4.65%)6.00%
Case Studies1 (1.16%)4.05%
Observational0 (0.00%)0.25%
Other81 (94.19%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Clinical Trials (4)

Trial Overview

TrialPhaseEnrollmentStudy TypeStart DateStatus
Nutritional Responses to Chronic Exercise- Versus Energy Restriction-induced Energy Deficits in Obese Adolescents [NCT03466359]50 participants (Anticipated)Interventional2018-01-08Recruiting
RCT Intervention to Reduce Stress in 0-5 Year Olds With Burns [NCT00844896]57 participants (Actual)Interventional2008-05-31Completed
Appetite Response to Exercise- Versus Energy Restriction-induced Energy Deficit in Adolescents With Obesity. [NCT04739189]20 participants (Actual)Interventional2021-08-28Completed
Appetite Response to Exercise- Versus Mixed (Exercise + Dietary Restriction)-Induced Energy Deficit in Adolescents With Obesity [NCT04734639]17 participants (Actual)Interventional2021-04-24Completed
[information is prepared from clinicaltrials.gov, extracted Sep-2024]

Trial Outcomes

TrialOutcome
NCT00844896 (9) [back to overview]Change From Baseline in Burn Outcomes Questionnaire Short Form (0-4 Year Old Version) at Six Months
NCT00844896 (9) [back to overview]Change From Baseline in Burn Outcomes Questionnaire Short Form (5-18 Year Old Version) From Six Months.
NCT00844896 (9) [back to overview]Change From Baseline in Child Stress Reaction Checklist Short Form at Six Month
NCT00844896 (9) [back to overview]Change From Baseline in Hospital Emotional Support Form From Six Months
NCT00844896 (9) [back to overview]Change From Baseline in Parenting Stress Index at Six Months
NCT00844896 (9) [back to overview]Change From Baseline in Pediatric Symptom Checklist at Six Months
NCT00844896 (9) [back to overview]Change From Baseline in PTSD Semi-Structured Interview at Six Months
NCT00844896 (9) [back to overview]Change From Baseline in Stanford Acute Stress Reaction Questionnaire at Six Months
NCT00844896 (9) [back to overview]DEF Participation

Change From Baseline in Burn Outcomes Questionnaire Short Form (0-4 Year Old Version) at Six Months

Burn Outcomes Questionnaire (American Burn Association/Shriners Hospitals for Children) Short Form (0-4 year old version). Parent-rated questionnaire that focuses on child's pain and parent's worry. Scores range from 5-24, with a higher score indicative of worse outcomes. Change in scores was measured from baseline to six month follow-up (NCT00844896)
Timeframe: Baseline and six month follow-up

Interventionunits on a scale (Mean)
DEF-only-4.9
DEF + COPE-4.5

[back to top]

Change From Baseline in Burn Outcomes Questionnaire Short Form (5-18 Year Old Version) From Six Months.

Burn Outcomes Questionnaire (American Burn Association/Shriners Hospitals for Children) Short Form (5-18 Year Old Version) is a 3-item questionnaire with scores ranging from 0-18. A higher score is indicative of worse outcomes. Used for five year olds in the study. Change in scores were observed from baseline to six month follow-up. (NCT00844896)
Timeframe: baseline and six month follow-up

Interventionunits on a scale (Mean)
DEF-only-0.2

[back to top]

Change From Baseline in Child Stress Reaction Checklist Short Form at Six Month

Child Stress Reaction Checklist Short Form is a 9-item parent-rated checklist. Scores range from 0-18 with a higher score indicative of worse outcomes. Change in scores were observed from baseline to six month follow-up (NCT00844896)
Timeframe: Baseline and six month follow-up

Interventionunits on a scale (Mean)
DEF-only0.8
DEF + COPE0.7

[back to top]

Change From Baseline in Hospital Emotional Support Form From Six Months

Hospital Emotional Support Form is a 12-question form that rates parents/caregivers need for in-hospital emotional support. Scores range from 11-24, with a lower score indicative of worse outcomes. Change in scores were observed from baseline to six month follow-up. (NCT00844896)
Timeframe: Baseline and six-month follow-up

Interventionunits on a scale (Mean)
DEF-only1.1
DEF + COPE2.0

[back to top]

Change From Baseline in Parenting Stress Index at Six Months

Parenting Stress Index is a 12-item parent-rated questionnaire which employs a 1-5 Likert scale. Scores range from 12-60, with a lower score indicative of worse outcomes and a cutoff of 15. Change in scores were observed from baseline to six month follow-up. (NCT00844896)
Timeframe: Baseline and six month follow-up

Interventionunits on a scale (Mean)
DEF-only7.1
DEF + COPE-3.3

[back to top]

Change From Baseline in Pediatric Symptom Checklist at Six Months

Pediatric Symptom Checklist is an 18-item psychosocial checklist in which symptoms are rated from 0 (never) to 2 (often) and the last question is rated as yes or no (0 or 1). Items are summed and the score can range from 0-35, with a higher score indicative of more symptoms and a worse outcome. Change in scores were observed from baseline to six month follow-up (NCT00844896)
Timeframe: Baseline and six month follow-up

Interventionunits on a scale (Mean)
DEF-only2.9
DEF + COPE1.0

[back to top]

Change From Baseline in PTSD Semi-Structured Interview at Six Months

Posttraumatic Stress Disorder Semi-Structured Interview is based on DSM-IV criteria, with a higher score indicative of increased symptoms of PTSD. The total rating was scored from 19 questions in three clusters of symptoms, with a score range of 0-38. Change in scores were observed from baseline to six month follow-up. (NCT00844896)
Timeframe: Baseline and six-month follow-up

Interventionunits on a scale (Mean)
DEF-only-1.7
DEF + COPE-1.5

[back to top]

Change From Baseline in Stanford Acute Stress Reaction Questionnaire at Six Months

Stanford Acute Stress Reaction Questionnaire is a 31-question self-report measure for acute stress in parents. Scores range from 0-155 with a higher score indicative of worse outcomes. Change in scores were observed from baseline to six month follow-up. (NCT00844896)
Timeframe: Baseline and six-month follow-up

Interventionunits on a scale (Mean)
DEF-only-9.6
DEF + COPE13.8

[back to top]

DEF Participation

Outcomes in this measure were quantified by the number of participants in either intervention (DEF-only or COPE+DEF). During the study, DEF intervention was part of the standard of care for all patients at Shriners Hospitals for Children-Boston and thus every participant in this study had been evaluated using DEF to determine distress, emotional and family support. (NCT00844896)
Timeframe: Baseline

Interventionparticipants (Number)
DEF-only29
DEF + COPE28

[back to top]