metyltetraprole
{{Short description|Fungicide}}
{{Chembox
| ImageFile = Metyltetraprole.png
| IUPACName = 1-[2-[
|Section1={{Chembox Identifiers
| CASNo = 1472649-01-6
| CASNo_Ref = {{cascite|correct|CAS}}
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 44WE6KNK7M
| ChEBI = 141152
| ChemSpiderID = 62285803
| PubChem = 89881183
| StdInChI=1S/C19H17ClN6O2/c1-13-4-3-5-17(26-19(27)24(2)22-23-26)16(13)12-28-18-10-11-25(21-18)15-8-6-14(20)7-9-15/h3-11H,12H2,1-2H3
| StdInChIKey = XUQQRGKFXLAPNV-UHFFFAOYSA-N
| SMILES = CC1=C(C(=CC=C1)N2C(=O)N(N=N2)C)COC3=NN(C=C3)C4=CC=C(C=C4)Cl
}}
|Section2={{Chembox Properties
| C=19|H=17|Cl=1|N=6|O=2
}}
|Section8={{Chembox Related
}}
}}
Metyltetraprole is a quinone outside inhibitor fungicide sold under the brand name Pavecto by its inventor, Sumitomo Chemical.{{cite journal | last1=Umetsu | first1=Noriharu | last2=Shirai | first2=Yuichi | title=Development of novel pesticides in the 21st century | journal=Journal of Pesticide Science | publisher=Pesticide Science Society of Japan | volume=45 | issue=2 | date=2020-05-20 | issn=1348-589X | doi=10.1584/jpestics.d20-201 | pages=54–74 | pmid=33132734 | eissn=1349-0923| pmc=7581488 }} ISSN-L [http://portal.issn.org/resource/ISSN-L/0385-1559 0385-1559] It is the only tetrazolinone fungicide and the only one in the Fungicide Resistance Action Committee's subgroup 11A.
Development
Metyltetraprole was developed specifically to find an a.i. with the same mode of action (a Q{{sub|o}}I) but with sufficiently different chemistry as to avoid "critical" Q{{sub|o}}I resistance increasing around the world.{{cite journal | last1=Matsuzaki | first1=Yuichi | last2=Yoshimoto | first2=Yuya | last3=Arimori | first3=Sadayuki | last4=Kiguchi | first4=So | last5=Harada | first5=Toshiyuki | last6=Iwahashi | first6=Fukumatsu | title=Discovery of metyltetraprole: Identification of tetrazolinone pharmacophore to overcome QoI resistance | journal=Bioorganic & Medicinal Chemistry | publisher=Elsevier | volume=28 | issue=1 | year=2020 | issn=0968-0896 | doi=10.1016/j.bmc.2019.115211 | page=115211| pmid=31753801 | doi-access=free }}
Target pathogens
Metyltetraprole is highly effective against Alternaria triticina.
Resistance
Developed because of increasing resistance to the main group of Q{{sub|o}}Is. See Development above.
=Cross-resistance=
It does not suffer cross-resistance with the resistance against 11 conferred by the cytochrome b mutation G143A. Cross-resistance against F129L is unassessed.{{cite web | url=http://www.frac.info/docs/default-source/publications/frac-code-list/frac-code-list-2021--final.pdf | title=FRAC Code List ©*2021: Fungal control agents sorted by cross resistance pattern and mode of action (including coding for FRAC Groups on product labels) | date=March 2021 | author=FRAC (Fungicide Resistance Action Committee) | pages=1–17 | access-date=2021-06-16 | archive-date=2021-11-05 | archive-url=https://web.archive.org/web/20211105005300/https://www.frac.info/docs/default-source/publications/frac-code-list/frac-code-list-2021--final.pdf | url-status=dead }}
Binding Mode
The structure of the tetrazolinone pharmacophore is very similar to the triazolone pharmacophore of an inhibitor developed by AgoEva, for which the binding mode has been elucidated in the structure deposited as [https://www.rcsb.org/structure/3l73 3L73] in the protein databank.