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Revision as of 14:03, 16 November 2011 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{chembox}} taken from revid 460940101 of page Carbophenothion for the Chem/Drugbox validation project (updated: 'ChEBI').  Latest revision as of 17:55, 7 September 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits removed Category:Chloroarenes; added Category:4-Chlorophenyl compounds using HotCat 
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{{ambox | text = This page contains a copy of the infobox ({{tl|chembox}}) taken from revid of page ] with values updated to verified values.}}
{{Chembox {{Chembox
| Verifiedfields = changed | Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 460939012
| verifiedrevid = 460946327
| Name = Carbophenothion
| ImageFile =Carbophenothion.svg | Name = Carbophenothion
| ImageFile = Carbophenothion.svg
| ImageSize =
| PIN = ''S''-<nowiki/>{methyl} ''O'',''O''-diethyl phosphorodithioate
| IUPACName = ''S''-4-chlorophenylthiomethyl O,O-diethyl phosphorodithioate<ref name="sitem">{{cite web|url=http://sitem.herts.ac.uk/aeru/footprint/en/Reports/120.htm|title=Chemical report|publisher=University of Hertfordshire|location=UK|accessdate=October 28, 2011}}</ref>
| OtherNames = Stauffer R 1303
| SystematicName = ''S''-<nowiki>methyl] O,O-diethyl phosphorodithioate</nowiki><ref name="sitem"/>
| Section1 = {{Chembox Identifiers
| OtherNames =Stauffer R 1303
| CASNo = 786-19-6
| Section1 = {{Chembox Identifiers
| CASNo_Ref = {{cascite|correct|CAS}}
| Abbreviations =
| CASNo = 786-19-6 | EINECS = 212-324-1
| CASNo_Ref = {{cascite|correct|CAS}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| EINECS = 212-324-1
| EINECSCASNO =
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 452866 | ChEMBL = 452866
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
Line 22: Line 18:
| StdInChIKey = VEDTXTNSFWUXGQ-UHFFFAOYSA-N | StdInChIKey = VEDTXTNSFWUXGQ-UHFFFAOYSA-N
| PubChem = 13081 | PubChem = 13081
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 12536 | ChemSpiderID = 12536
| UNII_Ref = {{fdacite|correct|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 998NGA2Q61 | UNII = 998NGA2Q61
| SMILES = Clc1ccc(SCSP(=S)(OCC)OCC)cc1 | SMILES = Clc1ccc(SCSP(=S)(OCC)OCC)cc1
| InChI = 1S/C11H16ClO2PS3/c1-3-13-15(16,14-4-2)18-9-17-11-7-5-10(12)6-8-11/h5-8H,3-4,9H2,1-2H3 | InChI = 1S/C11H16ClO2PS3/c1-3-13-15(16,14-4-2)18-9-17-11-7-5-10(12)6-8-11/h5-8H,3-4,9H2,1-2H3
| ChEBI_Ref = {{ebicite|changed|EBI}}
| RTECS =
| ChEBI = 554299
| MeSHName =
| ChEBI_Ref = {{ebicite|changed|EBI}} | KEGG_Ref = {{keggcite|correct|kegg}}
| ChEBI = <!-- blanked - oldvalue: 554299 -->
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG =
| ATCCode_prefix =
| ATCCode_suffix =
| ATC_Supplemental =
}} }}
| Section2 = {{Chembox Properties | Section2 = {{Chembox Properties
| C=11|H=16|Cl=1|O=2|P=1|S=3 | C=11 | H=16 | Cl=1 | O=2 | P=1 | S=3
| Odor = mercaptan-like
| Appearance =
| Appearance = colorless to yellow-brown
| Density =
| MeltingPt = | MeltingPt = unknown
| BoilingPtC = 82
| Melting_notes =
| BoilingPt_notes = 0.01 mmHg
| BoilingPt =
| Density = 1.271 g/cm<sup>3</sup>
| Boiling_notes =
| Solubility = Insoluble | Solubility = Insoluble<ref>Carbophenothion, solubility in water</ref>
| LogP = 5.1
| SolubleOther =
| Solvent =
| LogP =
| VaporPressure =
| HenryConstant =
| AtmosphericOHRateConstant =
| pKa =
| pKb =
}} }}
| Section7 = {{Chembox Hazards | Section7 = {{Chembox Hazards
|MainHazards = Highly toxic
| GHSPictograms = {{GHS02}} {{GHS06}} {{GHS environment}}
| GHSPictograms = {{GHS02}} {{GHS06}} {{GHS environment}}
| ExternalMSDS =
| ExternalSDS =
| EUClass =
| EUIndex = | FlashPtC = -18
| MainHazards =
| NFPA-H =
| NFPA-F =
| NFPA-R =
| NFPA-O =
| RPhrases = {{R11}} {{R24/25}} {{R38}} {{R50/53}} {{R65}} {{R67}}<ref name="chemicalbook">{{cite web|url=http://www.chemicalbook.com/ProductChemicalPropertiesCB3252912_EN.htm|title=Chemicalbook product entry|accessdate=June 24, 2011}}</ref>
| SPhrases = {{S28}} {{S36/37}} {{S45}} {{S60}} {{S61}} {{S62}}<ref name="chemicalbook" />
| RSPhrases =
| FlashPt = {{convert|-18|C|F}}
| Autoignition =
| ExploLimits =
| LD50 =
| PEL =
}}
| Section8 = {{Chembox Related
| OtherAnions =
| OtherCations =
| OtherFunctn =
| Function =
| OtherCpds =
}} }}
}} }}
'''Carbophenothion''' also known as '''Stauffer R 1303''' as for the manufacturer, ],<ref name="edu">{{cite web|url=http://pmep.cce.cornell.edu/profiles/insect-mite/cadusafos-cyromazine/carbophenothion/insect-prof-carbophe.html|title=carbophenothion (Trithion) Chemical Fact Sheet 5/84|access-date=October 29, 2011|publisher=]}}</ref> is an ] ]. It was used as a ] for ]<ref name="cc">{{cite web|url=http://cameochemicals.noaa.gov/chemical/4904|title=Cameochemicals data page|publisher=]|author=CAMEO Chemicals|access-date=October 29, 2011}}</ref> under the name of '''Trithion'''.<ref name="PiP">{{cite web|url=http://pmep.cce.cornell.edu/profiles/extoxnet/carbaryl-dicrotophos/carbophenothion-ext.html|title=Extension Toxicology Network page|access-date=June 24, 2011}}</ref> Carbophenothion was used as an ] and ].<ref name="sitem">{{cite web|url=http://sitem.herts.ac.uk/aeru/footprint/en/Reports/120.htm |title=Chemical report |publisher=University of Hertfordshire |location=UK |access-date=October 28, 2011 |url-status=dead |archive-url=https://web.archive.org/web/20120415104549/http://sitem.herts.ac.uk/aeru/footprint/en/Reports/120.htm |archive-date=April 15, 2012 }}</ref> Although not used anymore it is still a ] in the ].<ref name="PiP" /> The ] is identified in the ] as an ] according to the ].<ref name="gov-right-know">{{Cite journal | publisher = ] | title = 40 C.F.R.: Appendix A to Part 355—The List of Extremely Hazardous Substances and Their Threshold Planning Quantities | url = http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | edition = July 1, 2008 | access-date = October 29, 2011 | archive-url = https://web.archive.org/web/20120225051612/http://edocket.access.gpo.gov/cfr_2008/julqtr/pdf/40cfr355AppA.pdf | archive-date = February 25, 2012 | url-status = dead }}</ref>

== Introduction and History ==
Carbophenothion is a highly ] ] ] and ]. Organophosphates are ]s and disrupt the signal transduction at the cholinergic synapse.<ref>Hartley, D. and H. Kidd (eds.). ''The Agrochemicals Handbook. 2nd ed. Lechworth'', Herts, England: The Royal Society of Chemistry, 1987., p. A061/Aug 87</ref> It is classified as ] (RUP) by the ] (EPA).<ref name=":0">Oregon State University. (1996). EXTOXNET. Retrieved March, 2016. http://extoxnet.orst.edu/pips/carbophe.htm</ref><ref name=":1">Mergel M. (2010). Toxipedia. Retrieved March, 2016 http://www.toxipedia.org/display/toxipedia/Carbophenothion</ref> Carbophenothion is used in different brands like Trithion. This pesticide contains 80% carbophenothion as its only active ingredient. Because of the widespread use of those organophosphates in the nineties in the US, it was the most common cause of agricultural poisonings.<ref>U.S. Congress, Office of Technology Assessment, ''Neurotoxicity: identifying and controlling poisons of the nervous system''',''''' OTA-BA-436 (Washington, DC: U.S. Government Printing Office, April 1990)</ref>

An example of the toxicity of carbophenothion was the poisoning of seven family members. The flour which they used in their food was probably contaminated with carbophenothion. The members became ill four to six hours after ingestion. The symptoms were nausea and vomiting, besides this one family member lost his consciousness. All the family members regained full strength after six days.<ref name=":2">National Institutes of Health. (2003). TOXNET. Retrieved March, 2016 http://toxnet.nlm.nih.gov/cgi-bin/sis/search2/r?dbs+hsdb:@term+@rn+@rel+786-19-6</ref>

Since carbophenothion is highly toxic, it may only be used by certified applicators and the people directly supervised by them. A two-day safety waiting interval between the application is required to prevent unnecessary skin exposure.<ref name=":0" /> The compound is synthetically produced. The pure compound is a colorless to yellow-brown liquid, and is soluble in most industrial solvents.<ref name=":1" /> It is miscible with most organic compounds, like ]s, ]s and ]s.<ref name=":3">International Programme on Chemical Safety. (1972). IPCS INCHEM. Retrieved March, 2016 http://www.inchem.org/documents/jmpr/jmpmono/v072pr05.htm</ref>

In 1972 carbophenothion was evaluated at the Joint Meeting of Pesticide Residues (JMPR). During this meeting temporary tolerances were recommended for food, like several fruits, nuts and milk in the form of an ] (ADI). In 1975 these tolerances were re-evaluated and because the data on which the ADI's were based was not available the ADI's were withdrawn. The use of carbophenothion at that time did not indicate a need for additional maximum residue limits for crops, compared to the meeting in 1972.<ref name=":2" /> The latest meeting of the JMPR about this compound took place in 1980.

== Structure and Properties ==
Carbophenothion is an aromatic organophosphate with a chloride attached. It appears at room temperature as a colorless to yellow-brown liquid. It has a mild ]-like odor (rotten eggs). Its boiling point is 82&nbsp;°C and its melting point is unknown. It is relatively stable to heat (below 82&nbsp;°C).<ref name=":0" /><ref name=":4">National Center for Biotechnology information, U.S. National Library of Medicine. (2014). Pubchem. Retrieved March, 2016 https://pubchem.ncbi.nlm.nih.gov/compound/13081#section=GHS-Classification</ref>

Carbophenothion is ] and therefore insoluble in water. It is non-corrosive but can be oxidized to ] Carbophenothion can be degraded in the atmosphere by a reaction with photochemically produced ]s. The half life of this reaction is estimated to be about two hours. This reaction does not occur very often, due to the low ] of carbophenothion (3.0 × 10<sup>−7</sup> mm Hg at 20&nbsp;°C). It is not susceptible to direct ] because it absorbs very little UV light and none above 310&nbsp;nm. A more important fate may be ].<ref name=":4" /><ref>National Center for Biotechnology information, U.S. National Library of Medicine. (2014). Pubchem. Retrieved March, 2016 https://pubchem.ncbi.nlm.nih.gov/compound/13081#section=Ecological-Information</ref>

== Synthesis ==
Carbophenothion can be synthesized in two steps from 4-chlorothiophenol, ], ] and sodium O,O-diethyl dithiophosphate. First 4-chlorothiophenol can react with hydrogen chloride and formaldehyde to {{chem name|chloromethyl-4-chlorophenylsulfide}}. In the second step {{chem name|chloromethyl-4-chlorophenylsulfide}} reacts with sodium O,O-diethyl dithiophosphate to carbophenothion and ].<ref>Unger, T. A. (1996). ''Pesticide Synthesis Handbook:'' Elsevier Science, page 345.</ref> Both reactions occur spontaneously and are shown in the figure below.

]

== Mechanism of Action ==
Carbophenothion's mechanism of action is the same as its mechanism of toxicity, which acts through inhibition of ], an essential enzyme in the production of neurotransmitters containing choline-based esters (for example ]). Inability to produce these ]s causes failure in neuron cell signal transduction. This has widespread effects (see adverse effects) and can be lethal.<ref name=":0" />

Effectiveness of carbophenothion is enhanced by its very long residual activity and easy uptake by insects. Carbophenothion's mainly lipophilic character causes it to linger on the plants it is applied on and in the surrounding ground for extended periods of time. This makes it effective against eggs laid on treated plants. Another advantage of its lipophilic character is that it readily enters insects through sheer contact.<ref name=":0" />

== Metabolism ==
]
The ] of carbophenothion in human beings, is comparable to the metabolism in mice, insects and plants. There is little data of the quantitative degradation of carbophenothion to oxidative and hydrolytic compounds in mammals. It was found that in the rat more than 75% of the administered dose was excreted in the urine within 24 hours. Carbophenothion is therefore estimated to be rapidly excreted in humans as well.<ref name=":3" /> The compound is most toxic when it is not metabolized. The acute toxicity of the majority of the metabolites of carbophenothion have been studied in rats. They are considerably less toxic and thus show that metabolism of carbophenothion does probably not involve bioactivation but rather ]. The two main products of this metabolism are ] and ].<ref name=":5">International Programme on Chemical Safety. (1980). IPCS INCHEM. Retrieved March, 2016 http://www.inchem.org/documents/jmpr/jmpmono/v080pr06.htm</ref> Five oxidative products have been identified: the oxygen analogue of the carbophenothion, the sulphoxide and its oxygen analogue and finally sulphones and its oxygen analogue, all of which are depicted on the right.

The first major route of degradation of carbophenothion in rats is sulfoxidation, as displayed on the right. This product can be further transformed into 4-chlorobenzenesulphinic and 4-chlorobenzenesulphonic acid. A second major route involves the formation of 4-chlorothiophenol, which is further transformed via ] and ring-] to 4-Chloro-3-hydroxyphenyl methyl sulfone. This is then converted in approximately equal proportions to ] and ] conjugates.<ref name=":6">International Programme on Chemical Safety. (1977). IPCS INCHEM. Retrieved March, 2016 http://www.inchem.org/documents/jmpr/jmpmono/v077pr11.htm</ref> Furthermore, there are metabolites that presumably arise from the cleavage of the P-S bond such as 4-chlorophenylsulphinylmethyl methyl sulphone. An overview of the metabolites and their occurrence as has been studied in rats can be found in the table below.
{| class="wikitable"
!Metabolite
!Percentage in urine
|-
|4-chlorobenzenesulphinic acid
|46.8%
|-
|4-chloro-3-hydroxyphenylmethyl sulphone*
|23.9%
|-
|unidentified
|13.9%
|-
|4-chlorobenzenesulphonic acid
|5.3%
|-
|4-chlorobenzenemethiosulphuric acid
|3.0%
|-
|4-chlorothio-phenyl-S-glucuronide
|2.8%
|-
|4-chlorophenylsulphonylmethyl methyl sulphone
|1.9%
|-
|4-chlorophenylmethyl sulphone
|1.7%
|-
|4-chlorophenylsulphinylmethyl methyl sulphone
|0.7%
|}
One study on rats found that during 48 hours 66% of the administered carbophenothion was excreted in the urine and according to other experiments it takes approximately six days before complete excretion was achieved.<ref>FAO, WHO et al, (1978). ''Pesticides residues in food.'' p55 . Rome: Food and agriculture organization of the united nations .</ref> Other studies say that even after 14 days there was a detectable level of the oxidation product present.<ref>Gunsalus I.C. et al, (1971). Degradation of Synthetic Organic Molecules in the Biosphere: Natural, Pesticidal, and various other man-made compounds. Washington DC: National Academy of Sciences.</ref>

== Efficacy and Adverse Effects ==

=== Efficacy ===
Carbophenothion is used as an insecticide and acaricide, which main use is to protect ], but it is also used to protect cotton against ]s (plant lice) and ]s. Furthermore, it is used in combination with ] as well to function as a pesticide against numerous other pests on fruits, nuts, vegetables, ], ] and others. Besides this it is used to control parasites on animals.<ref name=":0" /><ref name=":6" /><ref>Dikshith T.S.S., (2008). ''Hazardous Chemicals: Chemicals safety management and global regulations.'' Boca Raton: CRC Press Taylor & Francis Group.</ref> Trithion, Garrathion and Lethox are three examples of pesticide brands that work with carbophenothion (Trithion is carbophenothion).

=== Adverse Effects ===

==== Effects on humans ====
Humans exposed to carbophenothion show a wide variety of symptoms. It produces illness typical of ]. ], ], ] and excessive ] are some common examples. When someone is exposed via inhalation, he or she may suffer from ] and a tight feeling in the chest. As carbophenothion affects the activity of the nerves and the brain, symptoms like mental confusion, profound weakness and drowsiness are observed as well. When someone is exposed by absorption through the skin, they get muscle contractions as well. The only long-term effect found in humans so far is a reduction of the amount of red blood cells and increase of the ]. These last two phenomenons only have been found in females.<ref name=":0" /> Other studies on long-term effects only have been performed on animals and statements about possible extrapolations have not been made so far.

==== Effects on Animals ====
Carbophenothion is not only very toxic to humans, but to other animals as well. For a lot of different animals the ], the dose at which 50% of the animals died, is determined. In the table below <ref name=":0" /> the LD50 for certain types of birds and aquatic organisms are stated. It is highly toxic for ]s, marine organisms, ]s, bees, wildlife as well, but no exact values are known.<ref name=":0" />
{| class="wikitable"
! Type of animal
! species
! LD50
|-
|'''Bird'''
|European starling
|5.6&nbsp;mg/kg
|-
|
|Canada goose
|29–35&nbsp;mg/kg
|-
|
|Mallard ducks
|121&nbsp;mg/kg
|-
|
|Japanese quail
|56.8&nbsp;mg/kg
|-
|'''Aquatic organism'''
|Rainbow trout
|56 ppb
|-
|
|bluegill sunfish
|13 ppb
|-
|
|pink shrimp
|0.47 ppb
|-
|
|sheepshead minnow
|17 ppb
|}
Long term effects were examined as well. Exposure of carbophenothion has a negative effect on reproductivity, at least in rats. When a dose of carbophenothion of 1–2&nbsp;mg/kg/day was given to three following generations, this resulted in increased stillbirths and decreased rat pups’ survival.<ref>Pesticide Management Education Program. (1995). EXTOXNET. Retrieved March, 2016. http://pmep.cce.cornell.edu/profiles/extoxnet/carbaryl-dicrotophos/carbophenothion-ext.html</ref> Furthermore, a study on 10-14 adult hens who were given a daily dose of carbophenothion for 24 days showed signs of ] influence, e.g. ], ]tion and ], loss of body weight and hampered egg production.<ref name=":5" />

==Toxicity==
Carbophenothion can be absorbed into the body by inhalation of its ], through the skin and by ingestion. Exposure via ingestion is highly toxic, but absorption through the skin is nearly as toxic. Acute toxicity happens as most effects occur soon after uptake in the body. Carbophenothion affects the nervous system by inhibiting ]. There are no signs of chronic or ]ic effects.<ref name=":0" />

The ] has classified carbophenothion as Category I - highly toxic.<ref name=":0" /> The toxicity in man has not yet been studied very well. There has been one study where five people were administered carbophenothion 0.8&nbsp;mg/kg/day for 30 days. There were no effects reported on plasma or red blood cell cholinesterase activity.<ref name=":3" /> These results were insufficient to determine the ADI. Later on, these results were even questioned because of an experiment with dogs which proved that a dose of 0.125&nbsp;mg/kg/day already had effects. The estimate of temporary ADI for man is now set at 0 - 0.005&nbsp;mg/kg. This is based on the ] of rats of 5 ppm in the diet equivalent to 0.25&nbsp;mg/kg/day.<ref name=":3" /> The estimated fatal oral dose is 0.6 g for a 150&nbsp;lb. (70&nbsp;kg) person.<ref name=":4" /> The LD50 for humans is unknown.

==References==
{{reflist|30em}}

==External links==
{{refbegin}}
* {{cite web|url=http://toxipedia.org/display/toxipedia/Carbophenothion|title=Toxipedia page|access-date=June 24, 2011}}
{{refend}}


{{Insecticides}}
{{Acetylcholine metabolism and transport modulators}}

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