Fenhexamid
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Basic Info
| Common Name | Fenhexamid(F05067) |
| 2D Structure | |
| Description | Fenhexamid is a locally systemic, protectant fungicide. Fenhexamid prevents fungi from infecting plants by inhibiting spore germination and mycelial growth. The fungicide is absorbed into the outer waxy layer of plant surfaces and is protected from being washed off by rainfall or irrigation. Used for control of Botrytis diseases on grapes, greenhouse tomatoes, ornamentals and berry crops, including blackberries, blueberries, currants, loganberries, raspberries and strawberries; and Monilinia brown rot on cherries, peaches and nectarines. |
| FRCD ID | F05067 |
| CAS Number | 126833-17-8 |
| PubChem CID | 213031 |
| Formula | C14H17Cl2NO2 |
| IUPAC Name | N-(2,3-dichloro-4-hydroxyphenyl)-1-methylcyclohexane-1-carboxamide |
| InChI Key | VDLGAVXLJYLFDH-UHFFFAOYSA-N |
| InChI | 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) |
| Canonical SMILES | CC1(CCCCC1)C(=O)NC2=C(C(=C(C=C2)O)Cl)Cl |
| Isomeric SMILES | CC1(CCCCC1)C(=O)NC2=C(C(=C(C=C2)O)Cl)Cl |
| Synonyms |
Fenhexamid
126833-17-8
Elevate
Teldor
N-(2,3-Dichloro-4-hydroxyphenyl)-1-methylcyclohexanecarboxamide
Fenhexamide
KBR 2738
Decree
Fenhexamid [ISO:BSI]
UNII-Q68C3C9P1U
|
| Classifies |
Pesticide
|
| Update Date | Nov 13, 2018 17:07 |
Chemical Taxonomy
| Kingdom | Organic compounds |
| Superclass | Benzenoids |
| Class | Benzene and substituted derivatives |
| Subclass | Anilides |
| Intermediate Tree Nodes | Not available |
| Direct Parent | Anilides |
| Alternative Parents | |
| Molecular Framework | Aromatic homomonocyclic compounds |
| Substituents | Anilide - 1,2-dichlorobenzene - 3-halophenol - 2-halophenol - 3-chlorophenol - 2-chlorophenol - N-arylamide - Chlorobenzene - Halobenzene - 1-hydroxy-2-unsubstituted benzenoid - Phenol - Aryl halide - Aryl chloride - Carboxamide group - Secondary carboxylic acid amide - Carboxylic acid derivative - Organonitrogen compound - Organochloride - Organohalogen compound - Organic oxide - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Organooxygen compound - Carbonyl group - Hydrocarbon derivative - Aromatic homomonocyclic compound |
| Description | This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution. |
Properties
| Property Name | Property Value |
|---|---|
| Molecular Weight | 302.195 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 2 |
| Rotatable Bond Count | 2 |
| Complexity | 331 |
| Monoisotopic Mass | 301.064 |
| Exact Mass | 301.064 |
| XLogP | 4.4 |
| Formal Charge | 0 |
| Heavy Atom Count | 19 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Isotope Atom Count | 0 |
| Covalently-Bonded Unit Count | 1 |
ADMET
| Model | Result | Probability |
|---|---|---|
| Absorption | ||
| Blood-Brain Barrier | BBB+ | 0.9805 |
| Human Intestinal Absorption | HIA+ | 0.9914 |
| Caco-2 Permeability | Caco2+ | 0.6255 |
| P-glycoprotein Substrate | Non-substrate | 0.5260 |
| P-glycoprotein Inhibitor | Non-inhibitor | 0.9313 |
| Non-inhibitor | 0.8207 | |
| Renal Organic Cation Transporter | Non-inhibitor | 0.8275 |
| Distribution | ||
| Subcellular localization | Mitochondria | 0.8906 |
| Metabolism | ||
| CYP450 2C9 Substrate | Non-substrate | 0.6709 |
| CYP450 2D6 Substrate | Non-substrate | 0.6625 |
| CYP450 3A4 Substrate | Substrate | 0.7169 |
| CYP450 1A2 Inhibitor | Non-inhibitor | 0.6059 |
| CYP450 2C9 Inhibitor | Inhibitor | 0.6969 |
| CYP450 2D6 Inhibitor | Non-inhibitor | 0.8206 |
| CYP450 2C19 Inhibitor | Inhibitor | 0.7674 |
| CYP450 3A4 Inhibitor | Inhibitor | 0.5375 |
| CYP Inhibitory Promiscuity | High CYP Inhibitory Promiscuity | 0.7675 |
| Excretion | ||
| Toxicity | ||
| Human Ether-a-go-go-Related Gene Inhibition | Weak inhibitor | 0.9623 |
| Inhibitor | 0.5000 | |
| AMES Toxicity | Non AMES toxic | 0.7442 |
| Carcinogens | Non-carcinogens | 0.8239 |
| Fish Toxicity | High FHMT | 0.9849 |
| Tetrahymena Pyriformis Toxicity | High TPT | 0.9878 |
| Honey Bee Toxicity | Low HBT | 0.8671 |
| Biodegradation | Not ready biodegradable | 0.9882 |
| Acute Oral Toxicity | III | 0.7769 |
| Carcinogenicity (Three-class) | Non-required | 0.4239 |
| Model | Value | Unit |
|---|---|---|
| Absorption | ||
| Aqueous solubility | -4.4152 | LogS |
| Caco-2 Permeability | 1.6424 | LogPapp, cm/s |
| Distribution | ||
| Metabolism | ||
| Excretion | ||
| Toxicity | ||
| Rat Acute Toxicity | 1.8127 | LD50, mol/kg |
| Fish Toxicity | 0.5050 | pLC50, mg/L |
| Tetrahymena Pyriformis Toxicity | 0.9199 | pIGC50, ug/L |
MRLs
| Food | Product Code | Country | MRLs | Application Date | Notes |
|---|---|---|---|---|---|
| Caraway (Ajowan,) | 0820030 | European Union | 0.05* | 12/02/2016 | |
| Kales (Borecoles/collards greens/curly kales, Cow cabbages/stem kales, Cow cabbages/Jersey kales, Kohlrabies leaves (6), Rape kales/Siberian kales, Portuguese kales/tronchuda kales/Portuguese cabba... | 0243020 | European Union | 0.01* | 12/02/2016 | |
| Cresses and other sprouts and shoots (Alfalfa/lucerne sprouts, Chinese chives/oriental garlic/garlic chives sprouts, Broccoli sprouts, Daikon/Japanese radish sprouts, Ginger shoots, Mung bean sprou... | 0251040 | European Union | 50 | 12/02/2016 | |
| Peas (with pods) (Asparagus peas, Chickling vetches, Chickpeas/Bengal gram, Garden peas/green peas/mangetout/snow peas/split peas/sugar peas, Moringa/drumstick tree pods, Pigeon peas,) | 0260030 | European Union | 0.01* | 12/02/2016 | |
| Cultivated fungi (Common mushrooms/button mushrooms/champignons mushrooms, Corn smuts/ Mexican truffles, Enokitake/winter mushrooms, Fusarium venenatum, Horse mushrooms, Jew's ears/hirneola, Nameko... | 0280010 | European Union | 0.01* | 12/02/2016 | |
| Common millet/proso millet (Black fonio, Canary grass, Finger millet/African millet/koracan, Foxtail millet, Job's tears, Little millet, Pearl millet, Teff/tef, White fonio,) | 0500040 | European Union | 0.01* | 12/02/2016 | |
| Rose (Almond, Bee balm, Bitter orange/sour orange, Black locust, Cat’s foot, Chrysanthemum, Cinnamon, Clary sage, Cornflower, Cowslip/primrose, Daisy, Dyer’s broom, Elder, Field poppy, Great mullei... | 0631030 | European Union | 0.05* | 12/02/2016 | |
| Strawberry (Absinth/common wormwood, Agrimony, Alfalfa/lucerne, Aloe (leaf gel), Alpine ladies mantle, Bearberry, Bilberry/European blueberry/whortleberry, Birch, Bitter orange/sour orange, Blackbe... | 0632010 | European Union | 0.05* | 12/02/2016 | |
| Cardamom (Marjoram, Star anise,) | 0820040 | European Union | 0.05* | 12/02/2016 | |
| Peppercorn (black, green and white) (Brazilian pepper, Cubeb/tailed pepper, Grain of paradise, Long pepper/pipali, Pink pepper, Sumac, West African pepper,) | 0820060 | European Union | 0.05* | 12/02/2016 | |
| (f) poultry (Bobwhite quail, Chicken (including silkie chicken), Collared Dove, Duck, Geese, Green peafowl, Guinea fowl, Japanese quail, Muskovy duck, Mute swan, Partridge, Peafowl, Pheasant, Pigeo... | 1016000 | European Union | 0.05* | 12/02/2016 | |
| Others (2) | 1016990 | European Union | 0.05* | 12/02/2016 | |
| (g) other farmed terrestrial animals (Alpaca, Bactrian camel, Capybara, Cottontail/American rabbit, Dromedary, Eland, Elk/moose, Emu, Fallow deer, Guinea pig, Hare (farmed), Llama, Nandu/greater rh... | 1017000 | European Union | 0.05* | 12/02/2016 | |
| Pig,Liver | Japan | 2ppm | |||
| Shungiku | Japan | 30ppm | |||
| Endive | Japan | 30ppm | |||
| Chicory | Japan | 30ppm | |||
| Citrus fruits | 0110000 | European Union | 0.01* | 12/02/2016 | |
| Oranges (Bergamots, Bitter oranges/sour oranges, Blood oranges, Cara caras, Chinottos, Trifoliate oranges, Other hybrids of Citrus sinensis, not elsewhere mentioned,) | 0110020 | European Union | 0.01* | 12/02/2016 | |
| Lemons (Buddha's hands/Buddha's fingers, Citrons,) | 0110030 | European Union | 0.01* | 12/02/2016 |
References
| Title | Journal | Date | Pubmed ID |
|---|---|---|---|
| Rationally designed haptens for highly sensitive monoclonal antibody-basedimmunoanalysis of fenhexamid. | Analyst | 2018 Jul 30 | 30059081 |
| Cultivating Chlorella vulgaris and Scenedesmus quadricauda microalgae to degrade inorganic compounds and pesticides in water. | Environ Sci Pollut Res Int | 2016 Sep | 27259964 |
| The natural fenhexamid-resistant grey mould populations from strawberry inZhejiang Province are dominated by Botrytis cinerea group S. | Pest Manag Sci | 2016 Aug | 26537826 |
| Fungicide multiresidue monitoring in international wines by immunoassays. | Food Chem | 2016 Apr 1 | 26593617 |
| Influence of the use of fungicides on the volatile composition of Monastrell red wines obtained from inoculated fermentation. | Food Chem | 2015 Mar 1 | 25306363 |
| Toxicity evaluation of new agricultural fungicides in primary cultured corticalneurons. | Environ Res | 2015 Jul | 25825129 |
| Increased occurrence of pesticide residues on crops grown in protectedenvironments compared to crops grown in open field conditions. | Chemosphere | 2015 Jan | 25465948 |
| Occurrence of fungicide resistance in populations of Botryotinia fuckeliana(Botrytis cinerea) on table grape and strawberry in southern Italy. | Pest Manag Sci | 2014 Dec | 24338954 |
| Biological activity of the succinate dehydrogenase inhibitor fluopyram againstBotrytis cinerea and fungal baseline sensitivity. | Pest Manag Sci | 2012 Jun | 22262495 |
| Multiresidue pesticide analysis of wines by dispersive solid-phase extraction andultrahigh-performance liquid chromatography-tandem mass spectrometry. | J Agric Food Chem | 2009 May 27 | 19371141 |
| Effectiveness of control strategies against Botrytis cinerea in vineyard andevaluation of the residual fungicide concentrations. | J Environ Sci Health B | 2009 May | 19365756 |
| Rapid gas chromatographic method for the determination of famoxadone,trifloxystrobin and fenhexamid residues in tomato, grape and wine samples. | J Chromatogr A | 2007 May 25 | 16950327 |
| Influence of fungicides on grape yeast content and its evolution in thefermentation. | Commun Agric Appl Biol Sci | 2007 | 18399439 |
| Impact of fungicides on Aspergillus carbonarius growth and ochratoxin A production on synthetic grape-like medium and on grapes. | Food Addit Contam | 2006 Oct | 16982524 |
| Determination of fungicide residues in field-grown strawberries followingdifferent fungicide strategies against gray mold (Botrytis cinerea). | J Agric Food Chem | 2006 Feb 8 | 16448201 |
| Disappearance of fenhexamid residues during wine-making process. | Commun Agric Appl Biol Sci | 2006 | 17390774 |
| Residues of azoxystrobin, fenhexamid and pyrimethanil in strawberry followingfield treatments and the effect of domestic washing. | Food Addit Contam | 2004 Nov | 15764335 |
| Application of liquid chromatography with electrospray tandem mass spectrometryto the determination of a new generation of pesticides in processed fruits andvegetables. | J Chromatogr A | 2004 May 21 | 15146917 |
| Interaction between fenhexamid and yeasts during the alcoholic fermentation ofSaccharomyces cerevisiae. | J Agric Food Chem | 2003 Aug 13 | 12903962 |
| Processing factors and variability of pyrimethanil, fenhexamid and tolylfluanidin strawberries. | Food Addit Contam | 2003 Aug | 13129790 |
Targets
- General Function:
- Zinc ion binding
- Specific Function:
- Nuclear receptor that binds and is activated by variety of endogenous and xenobiotic compounds. Transcription factor that activates the transcription of multiple genes involved in the metabolism and secretion of potentially harmful xenobiotics, drugs and endogenous compounds. Activated by the antibiotic rifampicin and various plant metabolites, such as hyperforin, guggulipid, colupulone, and isoflavones. Response to specific ligands is species-specific. Activated by naturally occurring steroids, such as pregnenolone and progesterone. Binds to a response element in the promoters of the CYP3A4 and ABCB1/MDR1 genes.
- Gene Name:
- NR1I2
- Uniprot ID:
- O75469
- Molecular Weight:
- 49761.245 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Zinc ion binding
- Specific Function:
- Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
- Gene Name:
- AR
- Uniprot ID:
- P10275
- Molecular Weight:
- 98987.9 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Cholesterol binding
- Specific Function:
- Can bind protoporphyrin IX and may play a role in the transport of porphyrins and heme (By similarity). Promotes the transport of cholesterol across mitochondrial membranes and may play a role in lipid metabolism (PubMed:24814875), but its precise physiological role is controversial. It is apparently not required for steroid hormone biosynthesis. Was initially identified as peripheral-type benzodiazepine receptor; can also bind isoquinoline carboxamides (PubMed:1847678).
- Gene Name:
- TSPO
- Uniprot ID:
- P30536
- Molecular Weight:
- 18827.81 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
- Gene Name:
- CYP2C9
- Uniprot ID:
- P11712
- Molecular Weight:
- 55627.365 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Steroid hydroxylase activity
- Specific Function:
- Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
- Gene Name:
- CYP2C19
- Uniprot ID:
- P33261
- Molecular Weight:
- 55930.545 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Monoamine transmembrane transporter activity
- Specific Function:
- Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
- Gene Name:
- SLC6A3
- Uniprot ID:
- Q01959
- Molecular Weight:
- 68494.255 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]
- General Function:
- Tachykinin receptor activity
- Specific Function:
- This is a receptor for the tachykinin neuropeptide substance K (neurokinin A). It is associated with G proteins that activate a phosphatidylinositol-calcium second messenger system. The rank order of affinity of this receptor to tachykinins is: substance K > neuromedin-K > substance P.
- Gene Name:
- TACR2
- Uniprot ID:
- P21452
- Molecular Weight:
- 44441.705 Da
References
- Sipes NS, Martin MT, Kothiya P, Reif DM, Judson RS, Richard AM, Houck KA, Dix DJ, Kavlock RJ, Knudsen TB: Profiling 976 ToxCast chemicals across 331 enzymatic and receptor signaling assays. Chem Res Toxicol. 2013 Jun 17;26(6):878-95. doi: 10.1021/tx400021f. Epub 2013 May 16. [23611293 ]