A fungicide
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Fenhexamid

Item No. 36222

Technical Information
Formal Name
N-(2,3-dichloro-4-hydroxyphenyl)-1-methyl-cyclohexanecarboxamide
CAS Number
126833-17-8
Synonyms
  • KBR 2738
Molecular Formula
C14H17Cl2NO2
Formula Weight
Purity
≥98%
Formulation
A solid
DMF: 5 mg/mlDMSO: 3 mg/mlEthanol: slightly soluble
SMILES
O=C(C1(CCCCC1)C)NC2=C(Cl)C(Cl)=C(C=C2)O
InChi Code
InChI=1S/C14H17Cl2NO2/c1-14(7-3-2-4-8-14)13(19)17-9-5-6-10(18)12(16)11(9)15/h5-6,18H,2-4,7-8H2,1H3,(H,17,19)
InChi Key
VDLGAVXLJYLFDH-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Fenhexamid is a fungicide.1,2 It inhibits germ-tube elongation and mycelial growth of several strains of the plant pathogenic fungus B. cinerea (EC50s = 0.13-8.3 and 0.03-16.5 µM, respectively).1 Fenhexamid inhibits 3-ketoreductase (IC50 = 3 µM for the B. cinerea enzyme), is an estrogen receptor α (ERα) agonist (EC50 = 9 µM in a yeast reporter assay), and inhibits the androgenic effect of dihydrotestosterone in MDA-kb2 cells (IC20 = 2.02 µM).1,3,4 It increases the proliferation and migration of BG1 ovarian cancer cells when used at a concentration of 10 µM.5 In field studies, fenhexamid applied at 842 g AI/ha provides 27.3 and 13.9% disease control for lettuce drop caused by S. minor or S. sclerotiorum, respectively.2 Formulations containing fenhexamid have been used as fungicides in agriculture.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Debieu, D., Bach, J., Montesinos, E., et alRole of sterol 3-ketoreductase sensitivity in susceptibility to the fungicide fenhexamid in Botrytis cinerea and other phytopathogenic fungi. Pest. Manag. Sci. 69(5), 642-651 (2013).

    2. Matheron, M.E., and Porchas, M. Activity of boscalid, fenhexamid, fluazinam, fludioxonil, and vinclozolin on growth of Sclerotinia minor and S. sclerotiorum and development of lettuce drop. Plant Dis. 88(6), 665-668 (2004).

    3. Teng, Y., Manavalan, T.T., Hu, C., et alEndocrine disruptors fludioxonil and fenhexamid stimulate miR-21 expression in breast cancer cells. Toxicol. Sci. 131(1), 71-83 (2013).

    4. Orton, F., Rosivatz, E., Scholze, M., et alWidely used pesticides with previously unknown endocrine activity revealed as in vitro antiandrogens. Environ. Health Perspect. 119(6), 794-800 (2011).

    5. Go, R.-E., Kim, C.-W., and Choi, K.-C. Effect of fenhexamid and cyprodinil on the expression of cell cycle- and metastasis-related genes via an estrogen receptor-dependent pathway in cellular and xenografted ovarian cancer models. Toxicol. Appl. Pharmacol. 289(1), 48-57 (2015).