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Metyltetraprole

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]

Metyltetraprole
Names
IUPAC name
1-[2-[[1-(4-chlorophenyl)pyrazol-3-yl]oxymethyl]-3-methylphenyl]-4-methyltetrazol-5-one
Identifiers
  • 1472649-01-6 Y
3D model (JSmol)
  • Interactive image
ChEBI
  • CHEBI:141152
ChemSpider
  • 62285803
  • 89881183
UNII
  • 44WE6KNK7M Y
  • 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
  • CC1=C(C(=CC=C1)N2C(=O)N(N=N2)C)COC3=NN(C=C3)C4=CC=C(C=C4)Cl
Properties
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).

Development edit

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

Target pathogens edit

Metyltetraprole is highly effective against Alternaria triticina.[1]

Resistance edit

Developed because of increasing resistance to the main group of QoIs. See §Development above.

Cross-resistance edit

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 edit

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 edit

  1. ^ 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
  2. ^ 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.
  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.

metyltetraprole, quinone, outside, inhibitor, fungicide, sold, under, brand, name, pavecto, inventor, sumitomo, chemical, only, tetrazolinone, fungicide, only, fungicide, resistance, action, committee, subgroup, names, iupac, name, chlorophenyl, pyrazol, oxyme. 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 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 Y 3D model JSmol Interactive image ChEBI CHEBI 141152 ChemSpider 62285803 PubChem CID 89881183 UNII 44WE6KNK7M Y 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 2H3Key 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 C 19H 17Cl N 6O 2 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 Contents 1 Development 2 Target pathogens 3 Resistance 3 1 Cross resistance 4 Binding Mode 5 ReferencesDevelopment editMetyltetraprole was developed specifically to find an a i with the same mode of action a QoI but with sufficiently different chemistry as to avoid critical QoI resistance increasing around the world 3 Target pathogens editMetyltetraprole is highly effective against Alternaria triticina 1 Resistance editDeveloped because of increasing resistance to the main group of QoIs See Development above Cross resistance edit 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 editThe 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 edit 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 c 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 amp Medicinal Chemistry 28 1 Elsevier 115211 doi 10 1016 j bmc 2019 115211 ISSN 0968 0896 PMID 31753801 nbsp This agriculture article is a stub You can help Wikipedia by expanding it vte Retrieved from https en wikipedia org w index php title Metyltetraprole amp oldid 1170205603, wikipedia, wiki, book, books, library,

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