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;
	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]

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]

References[]

^ ^a ^b Umetsu, Noriharu; Shirai, Yuichi (2020-05-20). "Development of novel pesticides in the 21st century". . . 45 (2): 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. Elsevier. 28 (1): 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". . . 45 (2): 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. Elsevier. 28 (1): 115211. doi:10.1016/j.bmc.2019.115211. ISSN 0968-0896. PMID 31753801.

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