Talk:1,2,3-Benzothiadiazole

Reviewer Discussion

Three previous reviewers have declined this draft. I think that I disagree with them as to inherent notability. This is a chemical substance with a CAS number. My thinking is that chemical substances with CAS numbers, like species of animals and plants, are inherently notable without regard to general notability, because they are items of human knowledge that are of encyclopedic value in themselves. I am ready to discuss with User:Graeme Bartlett, User:Calliopejen1, and User:DGG rather than simply accepting, but I think that this draft should be accepted.

Some time ago, maybe two years, I proposed notability guidelines that would have stated that every documented species and every chemical substance with a CAS number is notable. These guidelines were not adopted, but I thought that the reason that they were not adopted is that they were thought to be unnecessary. Maybe they are necessary after all, if other reviewers decline a draft on a chemical substance because it needs more secondary sources. I think that a chemical substance is a special case where the CAS number speaks for itself. Robert McClenon (talk) 03:17, 31 August 2020 (UTC)

I defer to others here. I'm not an expert in the area. Given what you say, I'd be inclined to accept if only so the community as a whole can evaluate if needed. Calliopejen1 (talk) 03:39, 31 August 2020 (UTC)

Robert McClenon, as it happens, I not only agree with you, but argued repeatedly that every documented chemical whose structure had been determined was notable. I declined the article on the basis that this view did not prevail at the time. and in reviewing AfC, I try to be strictly conservative with respect to existing consensus--especially because I am aware that in several areas my own personal viewpoint is different from the consensus, and when acting as an admin or reviewer, I think it fair to make every effort not to impose my own position. I am very willing that the discussion should be resumed. I have therefore accepted it on this basis. It wil likely be challenged; as I am unfortunately not able to keep track of everything I work on, if it is, could you please notify me so I can defend changign the consensus in the ensuing discussion. DGG ( talk ) 04:19, 31 August 2020 (UTC)

Robert , all chemicals cannot be notable with just a CAS Number. They should have at least one use. Take the examples of my 3 articles. Methyl hexanoate is used as a flavouring agent. 2,1,3-Benzothiadiazole is used to make white lights and some dyes. This chemical is used as a pesticide. See that all of these chemicals had a use one or the other. That is how you can prove a chemical notable. Nihaal The Wikipedian (talk) 05:22, 31 August 2020 (UTC)

I always thought that the topic was notable. However the references that were supplied earlier did not show that. Databases that attempt to list every chemical, don't show that a chemical is notable. But if someone has published an article or web page on the topic, that is what we need. Graeme Bartlett (talk) 07:29, 31 August 2020 (UTC)

@Graeme Bartlett, DGG, and Robert McClenon:I have just put ScienceDirect.Nihaal The Wikipedian (talk) 10:36, 31 August 2020 (UTC)

Existence of a CAS number is NOT evidence of notability. There are probably over 200 million such substances and CAS is obliged to index them even if the only reference is in a patent for a material that has never in fact been made. In this respect, CAS is certainly not a secondary source, far less the reaching the level we usually seek for WP:NOTABILITY. While, in fact, I think that this specific chemical is notable, the article as drafted has not (yet) demonstrated that and should be kept out of main space until it does, in my opinion. Incidentally, if the compound were used as a pesticide (as claimed in the draft) it would be listed on the PPDB and certainly be notable, but I have searched by its CAS number and confirmed it is not. Michael D. Turnbull (talk) 17:16, 31 August 2020 (UTC)

Michael D. Turnbull . PPDB is a UK website. 1,2,3-Benzothiadiazole is used in the US.Nihaal The Wikipedian (talk) 12:55, 1 September 2020 (UTC)

@Nihaal The Wikipedian: PPDB is based in the UK but I can assure you covers pesticides used worldwide. What is Pubchem's ultimate source for the statement and what is the ISO common name for the compound when used as a pesticide, which is a legal requirement for all pesticides? I can't find it. Incidentally, current reference 4 is entirely lab based and has no relevance to actual use as a pesticide: all such compounds have to achieve registration in the territories in which they will be sold, see pesticide for discussion of this. Michael D. Turnbull (talk) 13:54, 1 September 2020 (UTC)

Ah! I see what has confused you now. Pubchem has a small section that says the EPA has classified the compound as a pesticide. However, if you search for benzothiadiazole on the EPA website you'll find pdf files "like this" (pdf). which are for Acibenzolar-S-methyl. If you look at the WP article on Acibenzolar-S-methyl you'll see that it contains benzothiadiazole as a substructure. As I would expect, this has a PPDB entry "here".. Michael D. Turnbull (talk) 14:18, 1 September 2020 (UTC)

Michael D. Turnbull. Speedy deletion? This may be non-notable.Nihaal The Wikipedian (talk) 11:58, 3 September 2020 (UTC)

Nihaal The Wikipedian::No, don't be put off by the challenge of writing good articles (even stubs)! There is no need to delete draft articles since they are not in the Main Space and this one in particular can certainly be substantially improved and will become notable, in my judgement. Try to make it so: take the advice already on your Talk page. It involves investigating the references in Pubchem (and elsewhere) and checking what they say before incorporating them into the draft with the citation of the actual journal article or, preferably review article which mentions the compound. There must be articles on the preparation of the compound and its use in making simple derivatives. Don't lose heart and ask me if you need specific advice about any reference. Compare the article on 2,1,3-Benzothiadiazole which has now grown into something worthwhile (albeit still a stub). Michael D. Turnbull (talk) 12:16, 3 September 2020 (UTC)

This review reference should get you started: Storr; Gilchrist, eds. (2004). "Product Class 9: 1,2,3-Thiadiazoles". Category 2, Hetarenes and Related Ring Systems. doi:10.1055/sos-SD-013-00386. ISBN 9783131122810.. Note that very many of the articles that talk about "BTH" don't mean the parent compound but instead mean Acibenzolar-S-methyl. However that review DOES refer to the parent. 1,2,3-Benzothiadiazole has been known since 1888! Michael D. Turnbull (talk) 13:58, 3 September 2020 (UTC)

@Michael D. Turnbull: ❓❓😮😮. That means this is not eligible for speedy deletion. XWikiGuy 06:32, 4 September 2020 (UTC)

Correct. It will become notable, even if I have to write it myself. But I'm encouraging you to do that, even if you've managed to confuse me by changing your moniker. Michael D. Turnbull (talk) 10:23, 4 September 2020 (UTC)

@Nihaal The Wikipedian: I have now greatly expanded the article on acibenzolar-S-methyl and in doing so I read the Chinese article you cited with "full text available open access".. The Chinese authors don't make it clear but from their references, when they say "BTH" they don't mean 1,2,3-Benzothiadiazole and are in fact referring to acibenzolar-S-methyl. Michael D. Turnbull (talk) 13:03, 5 September 2020 (UTC)

@Michael D. Turnbull, DGG, Calliopejen1, Graeme Bartlett, and Robert McClenon:. Let’s expand the article in the meanwhile. ScienceDirect May be out of our references . I have submitted this draft. It is currently waiting for review.Nihaal 06:12, 6 September 2020 (UTC)

There is nil chance of the draft being accepted in its current state. I think we are all hoping you will do the necessary expansion. Most of the key references are in old (mostly German) literature which you will find are accessible via the Houben-Weyl and Storr/Gilchrist references I have provided. BUT you must drill down to select the relevant reactions and other chemistry to include, not just rely on references to these reviews. Michael D. Turnbull (talk) 12:38, 6 September 2020 (UTC)

Michael D. Turnbull: You will see that I added 3 more links, a journal and 2 websites. The ScienceDirect and PubChem. I added patents.google.com too, just in case you were wondering. Nihaal 14:06, 7 September 2020 (UTC)

Yes, well done, now you are starting to get to a much better article. If you follow your doi for the JCS reference by Ward et al, you'll find that you can search in JCS for other articles by Ward (he is the senior author and the reference is "Part I" of his group's work). This will lead you to other parts published in the 1960s and together they show that the compound is WP:NOTABLE, as does the big review (currently reference 5). Do you have access to the full papers in JCS? They make interesting reading and allow you to get back to the very early references to the preparation of the compound, if you wish. A bit more, with some tidying up, and the article will be ready for reinstating as no longer a draft. Incidentally, I don't think the patent is worth linking, as it refers to Acibenzolar-S-methyl and a wiki-link to that article would be all that's required. It is dubious whether you can call 1,2,3-benzothiadiazole "a parent" of that fungicide, since its not made from it: it just happens to contain the same part structure. Michael D. Turnbull (talk) 14:36, 7 September 2020 (UTC)

I've just noticed that the crystal structure has been done, which is also notable and worth adding the reference Palmer, M.; Parsons, S.; Messenger, D. (2005). "CCDC 273924: Experimental Crystal Structure Determination". Cambridge Crystallographic Data Centre. doi:10.5517/cc9618s. {{cite journal}}: Cite journal requires |journal= (help) Michael D. Turnbull (talk) 14:43, 7 September 2020 (UTC)

Wait, I thought you were already told that pubchem was not itself a suitable reference in general, but rather was the starting point where you can (possibly) find actual usable references. It's already listed in the infobox. And you listed it as a reference for this chemical being an herbicide, but I do not see that term anywhere in the pubchem entry. And we have already established that many plant-related uses of the term "Benzothiadiazole" actually means Acibenzolar-S-methyl instead. By actually looking at the refs, it's obvious when the term is being misused and fooling you into writing incorrect information. Doing it once is forgiveable...we all make mistakes and it is indeed confusing. Doing it repeatedly when we keep telling you and keep having to fix what you write is headed into pure disruption. DMacks (talk) 18:02, 7 September 2020 (UTC)

@Michael D. Turnbull and DMacks: So I have used that ccdc.cam.co.uk doi website which Michael gave,to prove it is aromatic. Please add more citations to help. Acidic Carbon (Corrode) 14:18, 15 September 2020 (UTC)

Acceptance

I am going to be bold and and accept this draft with little regard to the above discussion because I think that the purpose of the encyclopedia is to document human knowledge, and that a chemical is something worth having documented knowledge about. If the policies and guidelines say otherwise, then the policies and guidelines are interfering with the first pillar and should be ignored based on the fifth pillar. If anyone wants to take it to AFD, we can go to AFD. Robert McClenon (talk) 05:32, 8 September 2020 (UTC)

For the record, here is a previous version:

https://en.wikipedia.org/w/index.php?oldid=975918023

Inaccurate text partly owing to misinterpretation of references

@Nihaal The Wikipedian and Robert McClenon:

Please be more careful when adding material to this article. ("Current version".) Now that it has been promoted to Main Space, it needs to be accurate. Currently it is riddled with errors and mis-interpretations of the references supplied. For example:

1) The compound may well react with Fluorine, Chlorine, Bromine and Iodine BUT that's not what the reference says. The bromo and chloro derivatives are mentioned but they are produced by a Sandmeyer reaction from an amino derivative, not directly from the parent.

2) Nitrogen does not react with any simple heterocycle: this is presumably a confusion regarding an amine derivative

3) The Herz reaction can be used to make derivatives of 1,2,3-Benzothiadiazole but as the reference makes clear, when applied to aniline the product contains an additional chlorine atom in the benzene ring: it is not an alternative synthesis of 1,2,3-Benzothiadiazole itself.

4) The phrase "is a part of the compound Acibenzolar-S-methyl" is misleading. The ring system is a substructure (that's a very specific chemical term) of Acibenzolar-S-methyl. If such a relationship gets mentioned at all, it is usually the other way round, when we might (in the article on Acibenzolar-S-methyl) say that it is a derivative of 1,2,3-Benzothiadiazole. There are far too many potential derivatives of a given simple heterocycle to mention any particular one in the lead part of the article. Michael D. Turnbull (talk) 13:53, 8 September 2020 (UTC)

Michael D. Turnbull. Hmm... You expand and correct it too!Acid Of Carbon 10:45, 9 September 2020 (UTC)

@Graeme Bartlett, Nihaal The Wikipedian, and DMacks: This article is getting worse, not better. Nihaal's latest "contribution" "here". regarding arsenic detectors is for a compound that is not even a 1,2,3-benzothiadiazole (never mind the parent unsubstituted material "when combined with certain chemicals"), as can be seen from the title of the citation and the front page of the reference, which shows the structure in question. I would be happy to re-write the whole article to fix all its issues (see above) but certainly won't waste my time on doing so until there is more evidence of WP:CIR in others making changes to it. Michael D. Turnbull (talk) 10:09, 18 September 2020 (UTC)

@Michael D. Turnbull: I think I've gotten the off-topic and chemically incorrect content removed. Happy to work more on it if you'd like. DMacks (talk) 16:55, 20 September 2020 (UTC)

@DMacks: I've got a draft prepared (basically, a complete re-write) that I'll add over the next day or so. Once I've done that, I'd be grateful for further additions / improvements, as we managed with the 2,1,3 isomer. Michael D. Turnbull (talk) 17:19, 20 September 2020 (UTC)

Looks great! I'm out of time for today to do anything further than say that. DMacks (talk) 14:49, 21 September 2020 (UTC)

@Michael D. Turnbull:Make sure you ping me by writing @Acid Of Carbon: rather than @Nihaal The Wikipedian:. I cannot receive the message because you write Nihaal The Wikipedian. Acidic Carbon (Corrode) (Corrosive liquid) 11:12, 22 September 2020 (UTC)

Michael D. Turnbull. The arsenic article's picture gives clarity because it says nitrous oxide,nitrogen and something that looks like benzaldehyde is added to 1,2,3-Benzothiadiazole.Acidic Carbon (Corrode) (Corrosive liquid) 13:06, 26 September 2020 (UTC)

DMacks. The Indian arsenic article in pubs.rsc.org.Acidic Carbon (Corrode) (Corrosive liquid) 13:07, 26 September 2020 (UTC)

I do not have access to the full article (doi:10.1039/C6AY03302D) but the abstract and title only talk about "Benzothiazole" structures, not "Benzothiadiazole"s. Perhaps you should post a scan of the reaction you are talking about so others can figure out what they mean. I'm very sure it's not literally "nitrogen" as the chemical N₂.DMacks (talk) 14:41, 26 September 2020 (UTC)

@Acid Of Carbon: I am a member of the RSC and have access to the full article. As the graphical abstract shows, the molecule used to detect arsenic is the Shiff base formed by reaction of 2-amino-6-nitrobenzothiazole and 4-hydroxybenzaldehyde. It has nothing to do with 1,2,3-Benzothiadiazole, (as DMacks has already confirmed). Michael D. Turnbull (talk) 15:27, 26 September 2020 (UTC)

@Michael D. Turnbull: Yes,I read Benzothiazole but saw benzothiadiazole. Benzothiazole has a chemical formula of C7H5NS. Wait, Michael,I am very confused, so I'll move to Draft:Sodium Oleate and Draft:Iron dioxide.Acidic Carbon (Corrode) (Corrosive liquid) 13:24, 27 September 2020 (UTC)