Furalaxyl is a fungicide used to control oomycete diseases in a variety of crops, including potatoes, tomatoes, cucumbers, and grapes. It is a member of the oxathiin carboxamide class of fungicides. Furalaxyl is a systemic fungicide, meaning that it is absorbed by the plant and translocated throughout the plant, protecting the plant from fungal infection. It is effective against a wide range of oomycetes, including Phytophthora infestans, the causal agent of late blight of potato. Furalaxyl is synthesized by a multi-step process that involves the reaction of furfural with 2-chloro-N-(2,6-dimethylphenyl)-acetamide. Furalaxyl is a potent inhibitor of the mitochondrial respiration of oomycetes. It is thought to act by inhibiting the enzyme succinate dehydrogenase, which is essential for the electron transport chain in the mitochondria. The inhibition of mitochondrial respiration leads to the death of the fungal cells. Furalaxyl is an important fungicide because it is effective against a wide range of oomycetes, including Phytophthora infestans, the causal agent of late blight of potato. Late blight is a devastating disease that can cause significant crop losses. Furalaxyl is also relatively safe for use on crops and is not known to have any significant environmental impacts. Furalaxyl is studied because it is an important fungicide that is used to control oomycete diseases in a variety of crops. Research into furalaxyl is focused on understanding its mode of action, developing new and more effective fungicides, and minimizing the environmental impacts of its use.'
furalaxyl: Industrial Fungicide; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
furalaxyl : A racemate comprising equal amounts of (R)- and (S)-furalaxyl. A systemic fungicide with protective and curative properties. It is effective against damping-off and root rot diseases caused by Pythium and Phytophthora fungi which inhabit the soil and infect many ornamental flowers, shrubs and trees. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
methyl N-(2,6-dimethylphenyl)-N-2-furoylalaninate : An alanine derivative that is the N-furoyl derivative of methyl N-(2,6-dimethylphenyl)alaninate [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]
| ID Source | ID |
|---|---|
| PubMed CID | 42504 |
| CHEMBL ID | 3183557 |
| CHEBI ID | 82787 |
| SCHEMBL ID | 22528 |
| MeSH ID | M0472651 |
| Synonym |
|---|
| alanine, n-(2-furoyl)-n-(2,6-xylyl)-, methyl ester, dl- |
| n-(2,6-dimethylphenyl)-n-(2-furanylcarbonyl)-dl-alanine methyl ester |
| methyl n-(2,6-dimethylphenyl)-n-(2-furylcarbonyl)-dl-alaninate |
| dl-alanine, n-(2,6-dimethylphenyl)-n-(2-furanylcarbonyl)-, methyl ester |
| cga 38140 |
| methyl n-(2,6-dimethylphenyl)-n-(2-furanylcarbonyl)-dl-alaninate |
| methyl n-(2-furoyl)-n-(2,6-xylyl)-dl-alaninate |
| fongarid |
| furalaxyl [bsi:iso] |
| einecs 260-875-1 |
| methyl n-(2,6-dimethylphenyl)-n-(2-furoyl)-dl-alaninate |
| a 5430 |
| fonganil |
| 57646-30-7 |
| furalaxyl |
| methyl 2-[n-(furan-2-carbonyl)-2,6-dimethylanilino]propanoate |
| A-5430 , |
| tox21_302489 |
| dtxsid4047543 , |
| cas-57646-30-7 |
| dtxcid2027543 |
| NCGC00256891-01 |
| unii-9oy703a81o |
| 9oy703a81o , |
| AKOS015903108 |
| SCHEMBL22528 |
| furalaxyl [iso] |
| CHEBI:82787 , |
| methyl n-(2,6-dimethylphenyl)-n-2-furoylalaninate |
| cga-38140 |
| fongaride |
| CIEXPHRYOLIQQD-UHFFFAOYSA-N |
| methyl n-(2,6-dimethylphenyl)-n-(2-furanylcarbonyl)-dl-alanine |
| methyl 2-(2-furoyl-2,6-dimethylanilino)propanoate # |
| methyl n-(2,6-dimethylphenyl)-n-(2-furylcarbonyl)-dlalaninate |
| W-111142 |
| methyl 2-[n-(furan-2-carbonyl)-2,6-dimethyl-anilino]propanoate |
| CHEMBL3183557 |
| furalaxyl, pestanal(r), analytical standard |
| furalaxyl 10 microg/ml in cyclohexane |
| FT-0716026 |
| CS-0067501 |
| methyl 2-(n-(2,6-dimethylphenyl)furan-2-carboxamido)propanoate |
| Q19280071 |
| dl-alanine, n-(2,6-dimethylphenyl)-n-(2-furanylcarbonyl)-, methyl ester (9ci) |
| HY-118578 |
Furalaxyl is a chiral pesticide and widely used in modern agriculture as racemate mixture.
| Excerpt | Reference | Relevance |
|---|---|---|
| "Furalaxyl is a chiral pesticide and widely used in modern agriculture as racemate mixture. " | ( Enantiomerization and stereoselectivity in bioaccumulation of furalaxyl in Tenebrio molitor larvae. Gao, Y; Guo, B; Hao, W; Wang, H; Xu, Q; Yin, J; Zhu, F, 2017) | 2.14 |
| Excerpt | Relevance | Reference |
|---|---|---|
| " A significant dose-response effect between (R, S)-benalaxyl and global methylation level was observed." | ( Acylamino acid chiral fungicides on toxiciepigenetics in lambda DNA methylation. Chang, J; Guo, B; Hao, W; Wang, H; Xu, Q; Yin, J; Zhu, F, 2017) | 0.46 |
| " Though the two furalaxyl enantiomers exhibited low-capacity of bioaccumulation in Tenebrio molitor larvae, bioaccumulation of rac-furalaxyl was enantioselective with a preferential accumulation of S-furalaxyl at 10mg/kg dosage exposure." | ( Enantiomerization and stereoselectivity in bioaccumulation of furalaxyl in Tenebrio molitor larvae. Gao, Y; Guo, B; Hao, W; Wang, H; Xu, Q; Yin, J; Zhu, F, 2017) | 1.04 |
| Class | Description |
|---|---|
| alanine derivative | An amino acid derivative resulting from reaction of alanine at the amino group or the carboxy group, or from the replacement of any hydrogen of alanine by a heteroatom. The definition normally excludes peptides containing alanine residues. |
| aromatic amide | An amide in which the amide linkage is bonded directly to an aromatic system. |
| carboxamide | An amide of a carboxylic acid, having the structure RC(=O)NR2. The term is used as a suffix in systematic name formation to denote the -C(=O)NH2 group including its carbon atom. |
| furans | Compounds containing at least one furan ring. |
| methyl ester | Any carboxylic ester resulting from the formal condensation of a carboxy group with methanol. |
| [compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res] | |
| Protein | Taxonomy | Measurement | Average (µ) | Min (ref.) | Avg (ref.) | Max (ref.) | Bioassay(s) |
|---|---|---|---|---|---|---|---|
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 17.2114 | 0.0007 | 14.5928 | 83.7951 | AID1259369; AID1259392 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 15.3397 | 0.0010 | 22.6508 | 76.6163 | AID1224839 |
| progesterone receptor | Homo sapiens (human) | Potency | 68.5199 | 0.0004 | 17.9460 | 75.1148 | AID1346795 |
| retinoic acid nuclear receptor alpha variant 1 | Homo sapiens (human) | Potency | 18.5038 | 0.0030 | 41.6115 | 22,387.1992 | AID1159552; AID1159555 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 53.0804 | 0.0015 | 30.6073 | 15,848.9004 | AID1224849; AID1259403 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 10.8597 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 23.7101 | 0.0002 | 29.3054 | 16,493.5996 | AID743080; AID743091 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 27.2783 | 0.0023 | 19.5956 | 74.0614 | AID651631 |
| [prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023] | |||||||
| Timeframe | Studies, This Drug (%) | All Drugs % |
|---|---|---|
| pre-1990 | 0 (0.00) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 1 (14.29) | 29.6817 |
| 2010's | 6 (85.71) | 24.3611 |
| 2020's | 0 (0.00) | 2.80 |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||
According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be moderate demand-to-supply ratio for research on this compound.
| This Compound (23.37) All Compounds (24.57) |
| Publication Type | This drug (%) | All Drugs (%) |
|---|---|---|
| Trials | 0 (0.00%) | 5.53% |
| Reviews | 0 (0.00%) | 6.00% |
| Case Studies | 0 (0.00%) | 4.05% |
| Observational | 0 (0.00%) | 0.25% |
| Other | 7 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||