Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C9H21O2PS3 |
| Molecular Weight | 288.431 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOP(=S)(OCC)SCSC(C)(C)C
InChI
InChIKey=XLNZEKHULJKQBA-UHFFFAOYSA-N
InChI=1S/C9H21O2PS3/c1-6-10-12(13,11-7-2)15-8-14-9(3,4)5/h6-8H2,1-5H3
| Molecular Formula | C9H21O2PS3 |
| Molecular Weight | 288.431 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
Terbufos (S-tert-butylthiomethyl O,O-diethyl phosphorodithioate), a systemic insecticide, is the fourth most commonly used organophosphate insecticide (OP) in the United States, with an estimated 3 to 5 million pounds applied in 2001. First registered for use in the United States in 1974, terbufos was initially used to control insects and nematodes on corn. Currently, terbufos is also registered for use on sugar beets, sorghum, and bananas; terbufos is not registered for residential use or in public health applications. Terbufos is metabolized and activated to its neurotoxic form via oxidative desulfuration. This active form of terbufos irreversibly inhibits acetylcholinesterase, leading to the accumulation of acetylcholine and the classic signs and symptoms associated with muscarinic and nicotinic receptor overstimulation. The United States Environmental Protection Agency (USEPA) classifies terbufos in toxicity category I (high acute toxicity), but as group E for carcinogenicity (evidence of non-carcinogenicity for humans). This group E carcinogenicity classification is based largely on the lack of carcinogenic effects in two animal studies and lack of mutagenicity in several short-term genotoxicity assays. Primarily formulated as granules, Terbufos is applied at planting in a band or directly to the seed furrow. Terbufos is not approved for use in the European Union.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cleanup of gloves contaminated with granular terbufos and tefluthrin. | 2002 Apr |
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| Persistence and retention of active ingredients in four granular cholinesterase-inhibiting insecticides in agricultural soils of the lower Fraser River valley, British Columbia, Canada, with implications for wildlife poisoning. | 2002 Feb |
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| Insecticides in Chinese medicinal plants: survey leading to jacaranone, a neurotoxicant and glutathione-reactive quinol. | 2003 Apr 23 |
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| Study of the mechanism of Flavobacterium sp. for hydrolyzing organophosphate pesticides. | 2003 Dec |
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| Microsomal transformation of organophosphorus pesticides by white rot fungi. | 2003 Dec |
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| Emergence of adult northern and western corn rootworms (Coleoptera: Chrysomelidae) following reduced soil insecticide applications. | 2003 Jun |
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| Oat cover cropping and soil insecticides in an integrated sugarbeet root maggot (Diptera: Otitidae) management program. | 2003 Oct |
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| Secondary poisoning of eagles following intentional poisoning of coyotes with anticholinesterase pesticides in western Canada. | 2004 Apr |
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| [Inhibitory effect of zinc on beta-hexosaminidase release from RBL-2H3 cells by synthetic chemicals]. | 2004 Apr |
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| The potential of pesticides to contaminate the groundwater resources of the Axios river basin in Macedonia, Northern Greece. Part I. Monitoring study in the north part of the basin. | 2004 Apr 5 |
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| Low-dose agrochemicals and lawn-care pesticides induce developmental toxicity in murine preimplantation embryos. | 2004 May |
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| Acetylcholinesterase and neuropathy target esterase activity in female and male rats exposed to pesticide terbufos. | 2005 Jul |
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| Current-use and legacy pesticide history in the Austfonna Ice Cap, Svalbard, Norway. | 2005 Nov 1 |
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| Lessons learned for the assessment of children's pesticide exposure: critical sampling and analytical issues for future studies. | 2005 Oct |
|
| [Detecting organophosphorus pesticide in water environment using an enzyme biosensor]. | 2006 Aug |
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| Water quality and macroinvertebrate community response following pesticide applications in a banana plantation, Limon, Costa Rica. | 2006 Aug 15 |
|
| Relative rate constants of contaminant candidate list pesticides with hydroxyl radicals. | 2006 Jul 15 |
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| Pesticides associated with wheeze among commercial pesticide applicators in the Agricultural Health Study. | 2006 Jun 15 |
|
| Pesticide/herbicide pollutants in the Kafue River and a preliminary investigation into their biological effect through catalase levels in fish. | 2006 Nov |
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| Pesticides in surface drinking-water supplies of the northern Great Plains. | 2007 Aug |
|
| Nucleophilic reactions of phorate and terbufos with reduced sulfur species under anoxic conditions. | 2007 May 2 |
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| Depression and pesticide exposures among private pesticide applicators enrolled in the Agricultural Health Study. | 2008 Dec |
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| Parallel assessment of male reproductive function in workers and wild rats exposed to pesticides in banana plantations in Guadeloupe. | 2008 Jul 30 |
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| Incident diabetes and pesticide exposure among licensed pesticide applicators: Agricultural Health Study, 1993-2003. | 2008 May 15 |
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| Longitudinal trends in organophosphate incidents reported to the National Pesticide Information Center, 1995-2007. | 2009 Apr 20 |
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| Oxidation of selected organophosphate pesticides during chlorination of simulated drinking water. | 2009 Feb |
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| The watershed as a conceptual framework for the study of environmental and human health. | 2009 Feb 18 |
|
| Postmortem blood concentrations of organophosphorus pesticides. | 2009 Jan 30 |
|
| Pesticide exposure and respiratory health of indigenous women in Costa Rica. | 2009 Jun 15 |
|
| Impact of pesticides use in agriculture: their benefits and hazards. | 2009 Mar |
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| Titanium dioxide-mediated heterogeneous photocatalytic degradation of terbufos: parameter study and reaction pathways. | 2009 Mar 15 |
|
| Pesticide sequestration in passive samplers (SPMDs): considerations for deployment time, biofouling, and stream flow in a tropical watershed. | 2009 Oct |
|
| A review of pesticide exposure and cancer incidence in the Agricultural Health Study cohort. | 2010 Aug |
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| Childhood brain tumors, residential insecticide exposure, and pesticide metabolism genes. | 2010 Jan |
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| Determination of multiresidue pesticides in green tea by using a modified QuEChERS extraction and ion-trap gas chromatography/mass spectrometry. | 2010 Jul-Aug |
|
| Pesticide use and cutaneous melanoma in pesticide applicators in the agricultural heath study. | 2010 Jun |
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| Occupational exposure to terbufos and the incidence of cancer in the Agricultural Health Study. | 2010 Jun |
|
| Simultaneous extraction of trace organophosphorous pesticides from plasma sample by automated solid phase extraction and determination by gas chromatography coupled with pulsed flame photometric detector. | 2010 May 20 |
|
| A low concentration of atrazine does not influence the acute toxicity of the insecticide terbufos or its breakdown products to Chironomus tepperi. | 2010 Nov |
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| Pesticide use modifies the association between genetic variants on chromosome 8q24 and prostate cancer. | 2010 Nov 15 |
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| Acute human lethal toxicity of agricultural pesticides: a prospective cohort study. | 2010 Oct 26 |
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| Fenthion and terbufos induce DNA damage, the expression of tumor-related genes, and apoptosis in HEPG2 cells. | 2011 Aug |
|
| Comparative study of human and mouse pregnane X receptor agonistic activity in 200 pesticides using in vitro reporter gene assays. | 2011 Feb 27 |
|
| Xenobiotic-metabolizing gene variants, pesticide use, and the risk of prostate cancer. | 2011 Oct |
|
| The Interaction between Pesticide Use and Genetic Variants Involved in Lipid Metabolism on Prostate Cancer Risk. | 2012 |
|
| DNA methylation alterations in response to pesticide exposure in vitro. | 2012 Aug |
|
| Risk of total and aggressive prostate cancer and pesticide use in the Agricultural Health Study. | 2013 Jan 1 |
|
| Pesticide exposure and inherited variants in vitamin d pathway genes in relation to prostate cancer. | 2013 Sep |
|
| Non-hodgkin lymphoma risk and insecticide, fungicide and fumigant use in the agricultural health study. | 2014 |
Patents
Sample Use Guides
Terbufos (TBF) was orally administered to Sprague-Dawley rats, where female rats were received 0, 0.1, 0.4 and 0.8mg/kg TBF for 2 days and male rats 0, 0.1, 0.5 and 1.0mg/kg TBF for 3 days for dose-dependent study. Age-matched female and male rats also received equally 0.5mg/kg TBF for 2 days and sacrificed 0, 6, 12, 24 and 72h after the last dose for time-dependent study. In the dose-dependent study, mortality was 25% in 1.0mg/kg TBF group of male and 50% in 0.4 and 0.8mg/kg TBF groups of female rats, resulting in about two-fold higher in female than male.
Route of Administration:
Oral
In Vitro Use Guide
Curator's Comment: The study aimed to investigate the toxic effect of terbufos on testicular cells and to explore the mechanism of toxicity on a cellular level. The cytotoxic effects of terbufos on mouse immortalized spermatogonia (GC-1), spermatocytes (GC-2), Leydig (TM3), and Sertoli (TM4) cell lines were assessed by MTT assays, caspase activation, flow cytometry, TUNEL assay, Western blot, and cell cycle analysis.
The exposure to different concentrations of terbufos ranging from 50 to 800 uM for 6 h caused significant death in all the used testicular cell lines.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 17:24:19 GMT 2023
by
admin
on
Fri Dec 15 17:24:19 GMT 2023
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| Record UNII |
M83BN0F8R9
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| Record Status |
Validated (UNII)
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| Record Version |
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EPA PESTICIDE CODE |
105001
Created by
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13071-79-9
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Terbufos
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M83BN0F8R9
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C012568
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6444
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235-963-8
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25670
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m10571
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38960
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DTXSID2022254
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C163707
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terbufos
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