Benalaxyl is a fungicide belonging to the acylalanine class. It is a systemic fungicide that is used to control a wide range of fungal diseases in a variety of crops. Benalaxyl is known to inhibit the biosynthesis of the amino acid phenylalanine, which is an essential component of many fungal proteins. The mode of action of benalaxyl is based on the inhibition of the biosynthesis of the amino acid phenylalanine, a process that is essential for the growth of a wide range of fungi. It is effective against a wide range of fungal diseases in a variety of crops, including oomycete diseases such as Phytophthora infestans (late blight of potato and tomato) and Plasmopara viticola (downy mildew of grapevines). Benalaxyl is readily absorbed by plants and translocated throughout the plant, providing systemic protection against fungal diseases. However, benalaxyl has been linked to some negative environmental impacts, including the potential for resistance development in fungal pathogens and the potential for harm to non-target organisms. Its synthesis involves the reaction of N-methyl-N-(2-oxo-2-phenylethyl)benzamide with 2-chloro-N-methylpropionamide. The compound is typically used as a protectant or a curative treatment for fungal diseases, and is highly effective when applied to the soil or as a foliar spray. Benalaxyl is extensively studied to understand its impact on the environment and to develop more sustainable fungicides. In particular, research focuses on understanding the potential for resistance development and on identifying alternative control strategies that are less harmful to the environment.'
benalaxyl: RN given refers to (DL)-isomer; structure given in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]
benalaxyl : A racemate comprising equal amounts of (R)- and (S)-benalaxyl. [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-(phenylacetyl)alaninate : An alanine derivative that is the N-phenylacetyl 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 | 51369 |
| CHEMBL ID | 2286691 |
| CHEBI ID | 82777 |
| SCHEMBL ID | 21674 |
| MeSH ID | M0149927 |
| Synonym |
|---|
| caswell no. 471ac |
| benalaxyl [bsi:iso] |
| methyl n-phenylacetyl-n-2,6-xylyl-dl-alaninate |
| epa pesticide chemical code 127001 |
| n-(2,6-dimethylphenyl)-n-(phenylacetyl)-dl-alanine methyl ester |
| alanine, n-(2,6-dimethylphenyl)-n-(phenylacetyl)-, methyl ester, dl- |
| methyl n-(2,6-dimethylphenyl)-n-(phenylacetyl)-dl-alaninate |
| galben |
| einecs 275-728-7 |
| m 9834 |
| benalaxyl |
| 71626-11-4 |
| methyl 2-[(2,6-dimethylphenyl)-(2-phenylacetyl)amino]propanoate |
| inchi=1/c20h23no3/c1-14-9-8-10-15(2)19(14)21(16(3)20(23)24-4)18(22)13-17-11-6-5-7-12-17/h5-12,16h,13h2,1-4h3 |
| cjpqirjhizuaqp-uhfffaoysa- |
| methyl 2-(2,6-dimethyl-n-(2-phenylacetyl)anilino)propanoate |
| 2-(2,6-dimethyl-n-(1-oxo-2-phenylethyl)anilino)propanoic acid methyl ester |
| A837264 |
| methyl 2-[(2,6-dimethylphenyl)-(2-phenylethanoyl)amino]propanoate |
| l-alanine, n-(2,6-dimethylphenyl)-n-(phenylacetyl)-, methyl ester |
| alanine, n-(2,6-dimethylphenyl)-n-(phenylacetyl)-, methyl ester |
| 18th6ny90j , |
| unii-18th6ny90j |
| NCGC00255523-01 |
| tox21_301557 |
| dtxsid3041619 , |
| cas-71626-11-4 |
| dtxcid1021619 |
| FT-0602891 |
| AKOS015916308 |
| SCHEMBL21674 |
| chebi:82777 , |
| CHEMBL2286691 |
| benalaxyl, (+/-)- |
| dl-alanine, n-(2,6-dimethylphenyl)-n-(2-phenylacetyl)-, methyl ester |
| n-(2,6-dimethylphenyl)-n-(2-phenylacetyl)-alanine methyl ester |
| benalaxyl [iso] |
| benalaxyl [mi] |
| (+/-)-benalaxyl |
| methyl n-(2,6-dimethylphenyl)-n-(phenylacetyl)alaninate |
| n-(2,6-dimethylphenyl)-n-(1-carbomethoxy-ethyl)-phenylacetamide |
| methyl n-(phenylacetyl)-n-(2,6-xylyl)-dl-alaninate |
| methyl 2-[2,6-dimethyl(phenylacetyl)anilino]propanoate # |
| dl-alanine, n-(2,6-dimethylphenyl)-n-(phenylacetyl)-, methyl ester |
| W-104515 |
| benalaxyl, pestanal(r), analytical standard |
| methyl 2-(n-(2,6-dimethylphenyl)-2-phenylacetamido)propanoate |
| benalaxyl 100 microg/ml in cyclohexane |
| benalaxyl 10 microg/ml in cyclohexane |
| Q2795787 |
| n-(2,6-dimethylphenyl)-n-(phenylacetyl)-dl-alanine |
| Excerpt | Reference | Relevance |
|---|---|---|
| " In addition, the pigments chlorophyll a and chlorophyll b, antioxidant enzyme activities catalase (CAT) and superoxide dismutase (SOD) as well as lipid peroxide malondialdehyde (MDA) were determined to evaluate the different toxic effects." | ( Enantioselective toxic effects and biodegradation of benalaxyl in Scenedesmus obliquus. Diao, J; Huang, L; Lu, D; Zhou, Z, 2012) | 0.63 |
| Excerpt | Reference | Relevance |
|---|---|---|
| " The method was successfully applied to pharmacokinetic studies of BX enantiomers in rabbits." | ( Stereoselective determination of benalaxyl in plasma by chiral high-performance liquid chromatography with diode array detector and application to pharmacokinetic study in rabbits. Jia, G; Qiu, J; Wang, Q; Wang, X; Zhou, Z; Zhu, W, 2007) | 0.62 |
| 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) | 0.71 |
| 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. |
| 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) |
|---|---|---|---|---|---|---|---|
| RAR-related orphan receptor gamma | Mus musculus (house mouse) | Potency | 34.9190 | 0.0060 | 38.0041 | 19,952.5996 | AID1159521; AID1159523 |
| SMAD family member 2 | Homo sapiens (human) | Potency | 38.8952 | 0.1737 | 34.3047 | 61.8120 | AID1346859 |
| SMAD family member 3 | Homo sapiens (human) | Potency | 38.8952 | 0.1737 | 34.3047 | 61.8120 | AID1346859 |
| GLI family zinc finger 3 | Homo sapiens (human) | Potency | 65.7208 | 0.0007 | 14.5928 | 83.7951 | AID1259369; AID1259392 |
| AR protein | Homo sapiens (human) | Potency | 55.2613 | 0.0002 | 21.2231 | 8,912.5098 | AID1259243; AID1259247; AID743036; AID743042; AID743054; AID743063 |
| nuclear receptor subfamily 1, group I, member 3 | Homo sapiens (human) | Potency | 9.6885 | 0.0010 | 22.6508 | 76.6163 | AID1224839 |
| progesterone receptor | Homo sapiens (human) | Potency | 68.5896 | 0.0004 | 17.9460 | 75.1148 | AID1346795 |
| glucocorticoid receptor [Homo sapiens] | Homo sapiens (human) | Potency | 27.5357 | 0.0002 | 14.3764 | 60.0339 | AID720692 |
| retinoid X nuclear receptor alpha | Homo sapiens (human) | Potency | 13.2908 | 0.0008 | 17.5051 | 59.3239 | AID1159527; AID1159531 |
| estrogen-related nuclear receptor alpha | Homo sapiens (human) | Potency | 32.1471 | 0.0015 | 30.6073 | 15,848.9004 | AID1224841; AID1224842; AID1224848; AID1224849; AID1259401; AID1259403 |
| pregnane X nuclear receptor | Homo sapiens (human) | Potency | 10.8707 | 0.0054 | 28.0263 | 1,258.9301 | AID1346982 |
| estrogen nuclear receptor alpha | Homo sapiens (human) | Potency | 54.9410 | 0.0002 | 29.3054 | 16,493.5996 | AID743069 |
| vitamin D (1,25- dihydroxyvitamin D3) receptor | Homo sapiens (human) | Potency | 43.6412 | 0.0237 | 23.2282 | 63.5986 | AID743222 |
| thyroid stimulating hormone receptor | Homo sapiens (human) | Potency | 34.0811 | 0.0016 | 28.0151 | 77.1139 | AID1224843; AID1224895 |
| thyroid hormone receptor beta isoform 2 | Rattus norvegicus (Norway rat) | Potency | 61.1306 | 0.0003 | 23.4451 | 159.6830 | AID743065; AID743067 |
| nuclear factor erythroid 2-related factor 2 isoform 1 | Homo sapiens (human) | Potency | 54.4827 | 0.0006 | 27.2152 | 1,122.0200 | AID743202; AID743219 |
| Cellular tumor antigen p53 | Homo sapiens (human) | Potency | 27.3060 | 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 | 1 (4.17) | 18.7374 |
| 1990's | 0 (0.00) | 18.2507 |
| 2000's | 7 (29.17) | 29.6817 |
| 2010's | 16 (66.67) | 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 strong demand-to-supply ratio for research on this compound.
| This Compound (41.08) 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 | 25 (100.00%) | 84.16% |
| [information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023] | ||