Talk:Benzoylurea insecticide

Disputed:- benzoylphenylurea or benzoylurea

The commercial insecticidal benzoylureas are as far as I know all benzoylphenylureas. It is often the case that a phenyl ring could be replaced by an aliphatic group with maintenance of activity, although that needn't influence this dispute. In the literature and in agrochemical and agronomical usage the insecticidal class is described as benzoylurea, although arguably the term benzoylphenylurea would have been more accurate. The term has been used now everywhere since the 1970s. The acronym BPU has also been used since the 1970s, and the P clearly refers to phenyl. Perhaps the scientists in those days considered BU too short and ambiguous for a useful acronym. Of course this is not in keeping with dropping the "phenyl" from the Benzoylphenylurea, but this is the acronym that everyone uses. Therefore I suggest we accept the nomenclature, that was assigned (or perhaps it is more accurate to say came into use) decades ago, irrespective of how arbitrarily that process took place. However it this causes confusion to the reader than a sentence or a small paragraph explaining the dichotomy could perhaps be added. Bosula (talk) 16:14, 6 October 2024 (UTC)

I agree that there are imprecise terms used in a few aspects of these chemicals. In current lit, I also see "BU" used as an abbreviation for "benzoylurea", and "BPU" defined as an abbreviation for the fuller "benzolyphenylurea" term, and the compounds often identified by the fuller term rather than the shorter one. BPUs are a subclass of BUs, so it's not wrong to call a BPU a BU. If we don't have enough to say about non-phenyl compounds, I agree it makes sense to have a single article. But calling it by the more-proper name makes it easy to expand in the future if someone wants to write about those other compounds. For now, that means we could easily have benzoylurea->benzoylphenylurea as a WP:REDIRECT, and include a note about the nomenclature (e.g., that they are often just called "benzoylurea"). That makes the article itself more self-defining but equally reachable by a less-precise albeit common synonym so the reader can find immediately the correct target. I don't support retaining confusion/imprecision unless current usage is overwhelmingly that way (again, it does not appear so).

As examples of the non-phenyl variant, doi:10.1021/acs.jmedchem.0c01771 (non-cyclic substituent, targets protein–protein interactions for anti-cancer research), and a few refs about pyridyl.

However, I strongly support having an article about the class itself (whatever its name and scope wind up being) rather than just as a subsection of the parent compound. At the time I tagged here, we also had a benzoylphenylurea article that conflated this same BPU topic with a different constitutional isomer altogether, so it was mostly another content-fork and also a different contradiction. DMacks (talk) 19:23, 6 October 2024 (UTC)

I honestly did not know until now that someone had created a page on benzoylphenylurea, which is the correct constitutional isomer of the insecticide class. This surprises me since the parent compound has no applications, and is not particularly interesting even to a chemist. There are millions of compounds that could similarly be given a page! The same disapproval can be directed to the benzoylurea page itself. Why is there no acetylurea or benzoylmethylurea page? Clearly whoever created both benzoylphenylurea and benzoylurea pages did so for the purpose of introducing the insecticide class,

Hanging a class onto the parent compound. is a most unwise thing to do. The benzoylurea class of insecticides are structurally very homogenous. This is not typical, in fact it is most unusual. If you look at most classes of pesticde or pharmaceuticals, the newer members of the class differ significantly in structure from the first introduced compound. For example with a differing heterocyclic core. The parent compound is different in each case and is of no relevance. There are bioisosteres of urea moieties, amide bonds, and phenyl rings. Good practice in Wikipedia in all cases, when introducing a class used in some application, should be not to create a page with the parent, and some physical data, and then put the interesting derivatives as a sub-topic underneath. In the case of the BPUs it is possible (but undesirable) to do that, but usually it is not possible.

The term "benzoylurea" is overwhelmingly used for that class of insecticide. Perhaps in a review article it would be stated at the beginning that the chemical structure is that of a benzoylphenylurea, but any farmer or agronomist or anyone using or interested in insecticides would only know the term "benzoylurea", and would search for that term, so that term has to be used.

I'll think about your suggestion about a separate page, DMacks, However I would prefer to delete the benzoylphenylurea page and modify and rename the benzoylurea page as "benzoylureas - insecticide class". Bosula (talk) 22:26, 6 October 2024 (UTC)

The MOS wording would be like "Benzoylurea insecticides" if that is the specific topic. Where would that leave the non-insecticidal aspects of this class? Maybe "Benzoylphenylureas" (not sure if plural or singular) that also includes a summarystyle linking out to the insecticidal page? DMacks (talk) 23:06, 6 October 2024 (UTC)

There are two problems with the non-insecticidal aspects.

Firstly if you do a sub-structure search with such a generic scaffold as benzoylurea, you will find probably thousands of papers describing some activity. Unfortunately I no longer have access to Reaxys or Scifinder and cannot make such a search myself. An encyclopedic reporting of such activities is out of the question.

Secondly we are talking about aspects and not applications. Although the activity found is genuine and could potentially serve as a starting point for a more useful compound, in practice in almost all cases the dozens of man-years of work needed to improve/optimise the compound to a useful application are never invested. Therefore it should be (and probably is) Wikipedia policy to only write about a chemical class once it does have an application, unless of course it has purely chemical interest, like cubane or polyacetylenes.

The non-insecticidal papers so far are purely research papers. If and when a new application is found, the class will almost certainly get another semi-slang name, under which it can be reported on. It should have its own page and if the name turns out to be "benzoylureas" then some means of disambiguation should be used.

The potential anticancer paper already cited here is from 1998. Later this week when I am back home and can access literature I will see if anything further came out of it. If not, as I strongly suspect to be the case, I will delete the sentence and citation. I agree with you, DMacks, that using the plural indicates a class and not the compound. One way forward would be to announce here in this talk page that if no-one has any objections until the end of October then the page will be used for the insecticide class only.

Similarly on the benzoylphenylurea page I will see if the potential anti-cancer literature cited ever came to fruition. I see that page was created by a chemistry student, who clearly was trained to think systematically about chemistry. He looked up the synthesis and put in the crystal structure. I hesitate to step on his initiative. Students should be encouraged not discouraged. But he is now 40 years old, and presumably has experienced a lot worse in his life than having a Wikipedia page deleted. I suggest writing this explanation on the benzoylphenylurea talk page with a similar warning that if there are no objections then the page will be deleted at the end of October. Bosula (talk) 11:47, 7 October 2024 (UTC)

I will do some lit searches later today/tomorrow. But as a quick, I strongly disagree with your assertion that we should only write about things that "come to fruition". I'm not entirely sure what it means, but It is not WP policy to wait for something to reach a marketable state, have demonstrated impact beyond the lab, or have positive study results. Instead, the fact that things are published in secondary sources is the threshold for a topic in general, and publications demonstrating sustained interest suggest those sorts of sources would exist. See WP:GNG. DMacks (talk) 17:53, 7 October 2024 (UTC)

Yes. I don't disagree. I am happy to accept and apply the WP criterion you state. A compound or compound class has to reach some importance to be reviewed. This is not the case for the compounds in the thousands of papers describing cytotoxic compounds that are never followed up and never tested on animals let alone in the clinic. Similarly unsubstitued benzoylurea and unsubstituted phenylbenzoylurea do not meet the criterion. I am back now and will go to the library tomorrow.

As an aside I still believe that since there are dozens of chemical classes of insecticides and an incredible variety of biological insecticides on the market, it is wrong to dilute this with compounds that are only active in the lab. in fact soon I am going to write on the insecticide:talk page that we should cut down the number of classes (all commercial) that are discussed there. Bosula (talk) 15:25, 8 October 2024 (UTC)

OK. Citation 8 (3-(Iodoacetamido)-benzoylurea) has been followed up by the same authors. They describe an improved analog (3-Iodoacetamido benzoyl ethyl ester) without the benzoyl urea (Cancer Res. 2002 Nov 1;62(21):6080-8), so the activity has nothing to do with the benzoylurea. So this should be deleted.

Citation 5 in the N-Benzoyl-N'-phenylurea page has more of a story to it. One of the analogs (SG410) showed activity in rodents (https://doi.org/10.1158/1535-7163.MCT-06-0592). A press release in 2009 (U.S. Patent Issued for Champions Biotechnology, Inc.'s Lead Oncology Drug - BioSpace ) said that Champions Biotechnology, perhaps a start-up founded by the professors who made it, were developing it. But nothing more since then (15 years), and Champions Biotechnology is now Champions Oncology and do contract research. So clearly it failed along the line somewhere and never reached the clinic, which is the fate of the vast majority of candidates. As is often the case the failure or reasons for it are not reported. There are no review articles about SG410, and no publications about any further analogs, The substituent is large (substituted pyridyl thio phenyl), so maybe that is the business end. So I suggest it doesn't meet the WP criterion, and we should take it out..... Bosula (talk) 16:25, 9 October 2024 (UTC)

Hello DMacks, What are we going to do with this dispute? Do you agree we should delete the oncology references? Bosula (talk) 19:41, 26 October 2024 (UTC)

I'm a bit late to this debate as I watch DMacks talk page, where I saw today's comment. My 2p-worth is that the title of the article should be Benzoylurea insecticide in line with Phenoxy herbicide and should describe the class: we already have articles for many of its individual members and may eventually have one for all the commercial ones. There is no doubt that the WP:COMMONNAME for the class has always been benzoylurea, not benzoylphenylurea and that's still how IRAC 2024 and BCPC refer to it. Our article can use the acronym BPU if we like (or BU) but I don't remember either acronym being widely used by my colleagues when we worked on analogues in the 1970-80s. We always called them benzoylureas or Dimilin analogues. Mike Turnbull (talk) 12:38, 31 October 2024 (UTC)

I agree we should have an article focused on this class of insecticides, since that is a notable topic, and I think the article should be titled to identify that scope. In that way, we can use whatever term is used in that scope, even if it's not a perfect match from a chemical standpoint (again, the value of having the title clarify the scope). Mike found a good parallel case and I support his proposed solution for this case here. I looked and found phenylpyrazole insecticides as another in this naming/scoping set. Content about "benzoylurea" that are unrelated to insecticidal activity could be moved to a section on talkpage for future reference if anyone is able to write enough cited content for some other page. DMacks (talk) 05:46, 6 November 2024 (UTC)

Yes. I will give it the name Mike suggests. Please see Talk:Ryanoid for a more general approach. Bosula (talk) 16:36, 6 November 2024 (UTC)