Metyltetraprole

Metyltetraprole
Names
	IUPAC name 1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methylphenyl]-4-methyltetrazol-5-one
Identifiers
CAS Number	1472649-01-6 ;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:141152;
ChemSpider	62285803;
PubChem CID	89881183;
UNII	44WE6KNK7M ;
CompTox Dashboard (EPA)	DTXSID601108889 ;
	InChI InChI=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 Key: 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;
Properties
Chemical formula	C19H17ClN6O2
Molar mass	396.84 g·mol−1
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Metyltetraprole is a quinone outside inhibitor fungicide sold under the brand name Pavecto by its inventor, Sumitomo Chemical.^[1] It is the only tetrazolinone fungicide and the only one in the Fungicide Resistance Action Committee's subgroup 11A.^[2]It is a inhibitor of the respiratory chain (Complex III), this making it non specific of fungus, it will inhibit all organisms with mitochondria.

Development

Metyltetraprole was developed specifically to find an a.i. with the same mode of action (a Q_oI) but with sufficiently different chemistry as to avoid "critical" Q_oI resistance increasing around the world.^[3]

Target pathogens

Metyltetraprole is highly effective against Alternaria triticina.^[1]

Resistance

Developed because of increasing resistance to the main group of Q_oIs. 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.^[2]

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 3L73 in the protein databank.

References

^ ^a ^b Umetsu, Noriharu; Shirai, Yuichi (2020-05-20). "Development of novel pesticides in the 21st century". Journal of Pesticide Science. 45 (2). Pesticide Science Society of Japan: 54–74. doi:10.1584/jpestics.d20-201. eISSN 1349-0923. ISSN 1348-589X. PMC 7581488. PMID 33132734. ISSN-L 0385-1559
^ ^a ^b FRAC (Fungicide Resistance Action Committee) (March 2021). "FRAC Code List ©*2021: Fungal control agents sorted by cross resistance pattern and mode of action (including coding for FRAC Groups on product labels)" (PDF). pp. 1–17.
^ Matsuzaki, Yuichi; Yoshimoto, Yuya; Arimori, Sadayuki; Kiguchi, So; Harada, Toshiyuki; Iwahashi, Fukumatsu (2020). "Discovery of metyltetraprole: Identification of tetrazolinone pharmacophore to overcome QoI resistance". Bioorganic & Medicinal Chemistry. 28 (1). Elsevier: 115211. doi:10.1016/j.bmc.2019.115211. ISSN 0968-0896. PMID 31753801.

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[Umetsu-Shirai-2020-1] Umetsu, Noriharu; Shirai, Yuichi (2020-05-20). "Development of novel pesticides in the 21st century". Journal of Pesticide Science. 45 (2). Pesticide Science Society of Japan: 54–74. doi:10.1584/jpestics.d20-201. eISSN 1349-0923. ISSN 1348-589X. PMC 7581488. PMID 33132734. ISSN-L 0385-1559

[FRAC-MoAs-2] FRAC (Fungicide Resistance Action Committee) (March 2021). "FRAC Code List ©*2021: Fungal control agents sorted by cross resistance pattern and mode of action (including coding for FRAC Groups on product labels)" (PDF). pp. 1–17.

[Matsuzaki-et-al-2020-3] Matsuzaki, Yuichi; Yoshimoto, Yuya; Arimori, Sadayuki; Kiguchi, So; Harada, Toshiyuki; Iwahashi, Fukumatsu (2020). "Discovery of metyltetraprole: Identification of tetrazolinone pharmacophore to overcome QoI resistance". Bioorganic & Medicinal Chemistry. 28 (1). Elsevier: 115211. doi:10.1016/j.bmc.2019.115211. ISSN 0968-0896. PMID 31753801.

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