Talk:Organophosphate

Untitled

I have removed some rather biased matter which is not in agreement with the majority of scientists. It was about BSE, I suggest that until the editors who added the comments can offer up some evidence to support their I quote

'An organic farmer, Mark Purdy discovered that BSE and type-3 CJD is caused not by a new form of infection called a prion but is caused by poisoning by organo-phosphate fertilisers. {{DiseaseDisorder infobox | '

See [1] for a counterblast aginst this point of view

Cadmium 20:19, 9 January 2006 (UTC)

I find your comments do not adhere to wikipedia's "neutral point of veiw" policy and that both side of an aurgument should be presented for the reader. If you have evidence that "the majority of scientists" agree with your point of view please provide it. Apart from that comments relating to OP's relationship with BSE are irrelevent and inapropriate within the context of this article.

Either both sides should be presented or neither side !

That is not completely true. If a point-of-view is unsupported by outside evidence (WP:NOR, WP:V, WP:CITE) or held by a very small minority (WP:NPOVUW) then it would be allright to not bring this point of view. Please provide evidence, then disagree on policy. JFW | T@lk 17:43, 15 February 2006 (UTC)

I hate to quote your own reference but . ."the task is to represent the majority (scientific) view as the majority view and the minority (sometimes pseudoscientific) view as the minority view; and, moreover, to explain how scientists have received pseudoscientific theories. This is all in the purview of the task of describing a dispute fairly."(WP:NPOVUW) : If majority scientific views were treated as fact, and it was allright not to bring the point of view of small minorities - the world would still be flat ! I am not disagreeing with policy - only your interpretation of it.

Where's your source, mate? JFW | T@lk 23:09, 15 February 2006 (UTC)

Origional Hypothosis of Mark Purdey [2]; Report of Phillips Enquiry [3] - From Findings & Conclusions of Phillips Enquiry - "It remains possible that environmental factors, including toxic chemicals, may additionally be implicated in susceptibility to prion disease."[4] Dlm4473 (talk · contribs)

"Additional", eh? But I think a report in Med Hypoth should be linked as an academic reference. I think it may be notable enough for mention, unless Cadmium disagrees. JFW | T@lk 13:51, 16 February 2006 (UTC)

I don't think the Phillips enquiry cite lends credence to, nor refutes Purdey's theory. I'm leaving it out for now. JFW | T@lk 13:59, 16 February 2006 (UTC)

No Problem with that, happy with latest edit - i am not trying to push Purdey's hypothosis but i do believe that alternative theories should be given the light of day - letting the reader evaluate the merits of the case for themselves in absence of 'proof'. Statements along the lines of "The organophosphates are not linked to BSE (AKA Mad cow disease)" do little for education or for Wikipedia's credibility. Thanks for your time on this JFW.

Now of course you pushed the Purdey view. If you hadn't been there to push it would not have been here. The fact that the EU science committee bothered to address this issue is enough for me to show that there is at least an element of notability. With both views represented we have now arrived at WP:NPOV. I think. JFW | T@lk 16:22, 16 February 2006 (UTC)

I have removed the absurd suggestion that organophosphate compounds are essential to life. In particular the word is not used in the wikipedia article on DNA. DNA is not an organophosphate compound. I strongly suspect that this was added by a troll. John2o2o2o (talk) 21:16, 24 April 2017 (UTC)

Poison

It would be good if the use of Organophosphate as raticide were cited.

Leo McAllister 16:38, 26 November 2006 (UTC)

"British scientists experimented with an anticholinergic organophosphate of their own, called diisopropylfluorophosphate (DFP), during"   I changed the word anticholinergic to cholinercic because OP's are definitely not anticholinergics.

The article is too vague and too scare-mongering

Isn'd DNA an organophosphate, based on the definition given in this alarmist article? And solvents like trimethylphosphate? And lots of biosynthetic intermediates?--Smokefoot 03:15, 23 August 2007 (UTC)

yeah that's kind of a good point. i think most pharmacologists know what you're talking about when you say organophosphate, but you're right, lots of harmless biomolecules are technically OPs. this article is really about OP toxins/pesticides which are really a pretty small (but well-characterized/studied) family of molecules. anyone have suggestions for a more precise definition? Roadnottaken 18:34, 23 August 2007 (UTC)

I think the article should define organophosphates broadly: OP(OR)3, and then note that while the definition technically includes biomolecules like DNA (although the phosphate group in DNA only has 2 OR groups, not 3) the term is used almost exclusively to refer to pesticides, nerve toxins, and related chemicals, including small molecules in which one or more oxygens has been replaced by sulfurs. Note that molecules such as glyphosate which have an O=P-OR linkage but also possess an unesterified hydroxyl group on the same O=P are not generally refered to as organophosphates. Yilloslime 18:47, 23 August 2007 (UTC)

What this article really needs are good sources to back up the definition. I just did a very quick search and didn't find anything definitive, but from a quick search 1) I could not find any referring to DNA and similar biomolecules as organophosphates. 2) All the organophosphates I found were not esters of phosphoric acid, but had P-C or P-S bonds. I suspect that the definition as OP(OR)3 is wrong; while these would obviously be "organic" and "phosphates", they don't seem to take the label "organophosphates", just as not all compounds containing carbon and metals are called "organometallic", but rather require a bond between a metal and carbon or another "organic-like" element. --Itub 11:08, 24 August 2007 (UTC)

You are probably correct - the definitions are vague and confusing (A related argument hovers over the definition of organometallic compounds as you allude to, some consider titanium isopropoxide organometallic whereas hard-core organametallickers typically use the term "metallo-organic"). I get the sense that the present article started as a review of sarin and related organophosphorus compounds by the hands of well-intentioned editors who are unfamiliar with phosphorus chemistry. So, I figured if we are going to be vague and focus on the bad stuff, we should be vague and focus on the good stuff too. It is useful or instructive for readers to see that closely related compounds are good and bad, depending on the application and the specific substituents. Regardless: DNA and RNA are pretty clearly polyesters of phosphoric acid. I have no sense of ownership so feel free to edit away. --Smokefoot 12:46, 24 August 2007 (UTC)

Things like Sarin, VX, and the whole V-series of nerve agents are actually organophosphonates and thiophosphonates, not organophosphates because of the above-mentioned P-C bond. (See organophosphorus compounds.) Other toxins, like chlorpyrifos is a thiophosphate. I suspect that the P-C or P=S bonds lend the reactivity to these compounds that make them so toxic. Could we get a chemist to weigh-in on this? I don't think the article is alarmist but it may be mis-titled. An article about all compounds containing carbon and phosphorous is ridiculously broad so perhaps this article just needs to be re-labled... Roadnottaken 16:08, 24 August 2007 (UTC)

I am a chemist. As I said before, though perphaps not clearly, there is more than one way of defining the term. Technically according to IUPAC, etc, only triesters of phosphoric acid are organophosphates. But practically, the term is harderly ever--if at all--applied to DNA and other biomolecules, and while at the same time it is applied to pesticides and related compounds that are not strictly of the formula OP(OR)3. For example, the EPA and everyone else refers to chlorpyrifos, diazinon, and even pesticides with O=P-C connectivity as "organophophates," even though these compounds are more properly classified as phosphorothioates, thiophosphates, phosphonates, or some other more specific term. I think the article should definitely address both "POVs," but I'd argue that for most people coming to wikipedia to find out what the heck an organophosphate is, the "common usage" definition is going to be much more informative. After all, if you google or news.google the term "organophosphate," all your top hits relate to pesticides and/or toxicity. Yilloslime 17:04, 24 August 2007 (UTC)

I haven't been able to find any IUPAC definition for organophosphate. In organic nomenclature, the esters of phosphoric acid would be called "phosphates". Organophosphates is a common name for a class of molecules that are not really phosphates, but such is life. ;-) --Itub 16:01, 26 August 2007 (UTC)

Organophosphates Banned

Organophosphates are no longer used by the pest control industry. In fact the best product on the market for ant control (Termidor) is less toxic in it's mixed form than table salt. 68.7.195.20 (talk) 05:20, 9 April 2008 (UTC)

Sugar Phosphates?

Should sugar phosphates be included in this article? Albmont (talk) 13:13, 12 December 2009 (UTC)

Organophosphates error

Organophosphates ARE NOT organophosphorus compounds as they do not contain any carbon-phosphorus bond. —Preceding unsigned comment added by 87.205.45.223 (talk) 07:24, 25 June 2010 (UTC)

New study results on pre-natal exposure

Sorry, I don't have time to update the article, but here is one story on the results of the study. There are a lot more out there published today. [5] --ChrisRuvolo (t) 21:58, 21 April 2011 (UTC)

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Citations

To potentially cite:

• http://www.sciencedirect.com/science/article/pii/S0161813X13001514

-- phoebe / (talk to me) 14:49, 19 March 2016 (UTC)

Reverts

Kingofaces43 I'd argue that WP:MEDRS applies more to sources about actual medical information, rather than scientific and forensic detection of different types of nerve gases, as there's no way it'd influence someone who was uninformed about the field to make an uninformed decision about the type of nerve gas they were poisoned with. As for the Kim Jong Nam poisoning, it deserves to be in the wikipedia article as I believe readers benefit from reading that, because it demonstrates the most notable recent applications of organophosphate nerve gases.

Also, pretty sure WP:BRD means you don't edit and discuss - reverting with a reason of WP:BRD is funny.

IP, the expectation here is that when an edit is reverted, someone needs to gain consensus for it on the talk page (essentially BRD). In this case, the content is relates to human physiology and requires MEDRS sources. Even if it wasn't MEDRS, it is still scientific content, and we prefer not to use primary journal articles per WP:SCIRS. Kingofaces43 (talk) 17:28, 14 March 2018 (UTC)

`Primary sources should generally not be used for medical content – as such sources often include unreliable or preliminary information, for example early in vitro results which don't hold in later clinical trials.` In this case, because the section is explicitly about research, I think it's better than nothing. Furthermore, because it's unlikely to be misused, the argument that it might be misused isn't very strong. The article is about organophosphates - any civilian who isn't an expert in nerve agents shouldn't try to deal with them themselves. MEDRS doesn't preclude this item's inclusion in the article, and I think it's useful to the kind of people who would read it.

As for the other section, again, if someone's reading the article they'll probably want to know that. — Preceding unsigned comment added by 47.156.233.252 (talk) 17:59, 14 March 2018 (UTC)

For instance, unreliable or preliminary information, for example early in vitro results which don't hold in later clinical trials. doesn't really apply here, as anyone reading it understands that it's preliminary research about distinguishing between types of organophosphates and/or that atropine (mentioned many times in the article) has a moderate level of effectiveness in eyes. — Preceding unsigned comment added by 47.156.233.252 (talk) 18:12, 14 March 2018 (UTC)

Kingofaces43

MEDRS/SCIRS strongly caution against the use of primary sources in about as strong of language as we can, and that's the community consensus. If you want to change that, you'll need to change the guidelines. As for the second section, organophosphates are not even mentioned in the source. In addition to WP:RECENTISM, we need sources that give WP:WEIGHT to the event under the context of this article. It has appropriate mention elsehwhere, but here we would need sources specifically discussing the use of organophosphates as a whole as human nerve agents. Kingofaces43 (talk) 15:37, 15 March 2018 (UTC)

Community consensus applies to things of medical interest - it's hard to argue that the article is of medical interest, or that the included material will be read by someone unfamiliar with organophosphates attempting to treat poisoning. Guidelines should be interpreted as they apply to the material, not as hard rules - because there's no danger from including it, nor a risk of misunderstanding, I'd suggest including it. I have no preference for the assassination. Please respond to my interpretation of the guideline instead of simply referring to the guideline itself. — Preceding unsigned comment added by 47.156.233.252 (talk) 22:19, 16 March 2018 (UTC)

As already explained, this is content relating to human health. MEDRS pretty ubiquitously applies to pesticide topics when human health is involved, and we still look prefer secondary sources when it isn't about human health for nearly any science topic. Again, if there are any secondary sources like reviews that demonstrate the primary sources carry some weight in the scientific community and are worth mentioning here, that can be discussed. Primary sources do not cut it here though.

Also, please remember to sign your comments so sinebot doesn't need to. Edits to talk pages often don't show up on watchlists when a bot has to take an action there. Kingofaces43 (talk) 20:05, 17 March 2018 (UTC)

Please respond to my interpretation of the guideline instead of simply referring to the guideline itself. — Preceding unsigned comment added by 47.156.233.252 (talk) 22:49, 17 March 2018 (UTC)

I already responded. Content related to human health regardless of application more or less needs secondary sources. If you are unfamiliar with why, the guideline provides plenty of guidance that doesn’t need to be rehashed here. Kingofaces43 (talk) 13:48, 18 March 2018 (UTC)

Right, and the guideline's reasoning doesn't apply exactly to this scenario, so this specific information might actually be valuable to readers, guideline or not. — Preceding unsigned comment added by 47.156.233.252 (talk) 01:20, 19 March 2018 (UTC)

Unclear definition of organophosphates

The article is completely useless in its present form: If the definition of organophosphates in the first paragraph is right and it includes substances in our bodies like DNA and RNA, a clear distinction between the general class and organophosphate pesticides (dangerous substances) needs to be made. If the definition is wrong and excludes most organic substances with phosphate groups, this needs to be changed in the first paragraph!

This is not meant as an insult for the authors, I appreciate the work and the information in the article. But it should be clear what the actual topic/definition is, otherwise the information is not helpful, and might even be misleading or wrong.

I completely agree that at least in the beginning the article makes no clear distinction between naturally occurring organophosphates and synthetic ones, leaving the reader to guess if DNA is maybe used as a flame retardant XD (oversimplifying here, but try to read it like a you are 12 and you might see what i mean). Since this is such a diverse group of compounds it should be clearly visible when a specific subgroup is discussed. --Hakunamenta (not logged in right now because im at work.)141.5.11.5 (talk) 13:30, 21 October 2022 (UTC)

Natural vs. synthetic isn't really the distinction to make (i.e., avoiding chemophobia issues), but nebulousness is further compounded by organophosphate insecticides and herbicides being confused as being the same class of pesticide. Like any other chemical, it really depends on specific use, so if clarifications are needed (the current text makes the inference pretty clear) then it should be mentioned what specific uses are being discussed where.

Terminal oxygen vs. terminal sulfur

The article states that thiophosphoryl esters with the P=S moiety do not inhibit AChE & are not used as insecticides. But the diazinon article identifies it as a thiophosphoryl ester with the =S & it is used as an insecticide. Can anyone clarify? --D Anthony Patriarche (talk) 23:50, 30 May 2019 (UTC)

I am going to remove that entire section. It's been nearly a year since the above post and no one has cared enough to add any citations or justifications to the almost useless claim that thiophosphoryl cmpds are less toxic than "similar" phosphoryl ones. Parathion is extremely toxic to humans and is a thiophosphoryl triester (but admitedly, I've no idea what the toxicity is of the **analogous** phosphate triester).174.130.70.61 (talk) 19:41, 29 April 2020 (UTC)

Read parathion more carefully.... Simon de Danser (talk) 05:25, 16 May 2020 (UTC)

Synthesis via the esterification of phosphoric acid

The article currently states that these compounds can be made via the direct esterification of phosphoric acid:

OP(OH)₃ + ROH → OP(OH)₂(OR) + H₂O

OP(OH)₂(OR) + R'OH → OP(OH)(OR)(OR') + H₂O

OP(OH)(OR)(OR') + R"OH → OP(OR)(OR')(OR") + H₂O

Seems straightforward enough - but why can I not find a single reference for this reaction? Frustratingly, I also can't find any which state that it's impossible. At a guess, phosphoric acid dehydrates into anhydrides like pyrophosphoric acid much more readily that carboxylic acids do, which might make the process too difficult to bother with? Project Osprey (talk) 15:20, 7 February 2023 (UTC)