ChemicalBook--->CAS DataBase List--->71626-11-4

71626-11-4

71626-11-4 Structure

71626-11-4 Structure
IdentificationBack Directory
[Name]

Benalaxyl
[CAS]

71626-11-4
[Synonyms]

m9834
GALBEN
TF 3675
Benalaxyi
BENALAXYL
farmoplant
BENALAXYL 0.92
benalaxyl (bsi,iso)
Benalaxyl 250mg [71626-11-4]
BENALAXYL PESTANAL (METHYL-N-PHENYLACETY
methyln-phenylacetyl-n-2,6-xylyl-dl-alaninate
N-(2,6-dimethylphenyl)-N-(phenylacetyl)-DL-alanine
N-(2,6-DIMETHYLPHENYL)-N-(PHENYLACETYL)-DL-ALANINE ESTER
methyl-N-phenylacetyl-N-2,6-dimethyl phenyl-DL-alaninate
methyln-(2,6-dimethylphenyl)-n-(phenylacetyl)-dl-alaninate
DL-alanine N-(2,6-methylphenyl)-N-(phenylacetyl)-methyl ester
n-(2,6-dimethylphenyl)-n-(phenylacetyl)-dl-alaninemethylester
METHYL2-(N-PHENYLACETYL-N-(2,6-DIMETHYLPHENYL)AMINO)PROPANOATE
n-(2,6-dimethylphenyl)-n-(phenylacetyl)-,methylester,dl-alanin
Alanine, N-(2,6-dimethylphenyl)-N-(phenylacetyl)-, methyl ester
(±)-N-(2,6-Dimethylphenyl)-N-(phenylacetyl)alanine methyl ester
benalaxyl methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)-DL-alaninate
[EINECS(EC#)]

275-728-7
[Molecular Formula]

C20H23NO3
[MDL Number]

MFCD00143652
[MOL File]

71626-11-4.mol
[Molecular Weight]

325.4
Chemical PropertiesBack Directory
[Melting point ]

78-80°C
[Boiling point ]

463.59°C (rough estimate)
[density ]

1.2700
[vapor pressure ]

6.6 x 10-5 Pa (25 °C)
[refractive index ]

1.5614 (estimate)
[storage temp. ]

0-6°C
[solubility ]

Chloroform (Slightly), Methanol (Slightly)
[form ]

neat
[pka]

1.52±0.50(Predicted)
[Water Solubility ]

28.6 mg l-1 (20 °C)
[Merck ]

13,1028
[BRN ]

3001587
[Henry's Law Constant]

8.5×101 mol/(m3Pa) at 25℃, Duchowicz et al. (2020)
[Major Application]

agriculture
environmental
[InChI]

1S/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
[InChIKey]

CJPQIRJHIZUAQP-UHFFFAOYSA-N
[SMILES]

COC(=O)C(C)N(C(=O)Cc1ccccc1)c2c(C)cccc2C
[NIST Chemistry Reference]

Benalaxyl(71626-11-4)
[EPA Substance Registry System]

Alanine, N-(2,6-dimethylphenyl)-N-( phenylacetyl)-, methyl ester(71626-11-4)
Hazard InformationBack Directory
[Usage]

An acylamino acid fungicide.
[Description]

Benalaxyl is a fungicide that is widely used but now being phased out in many countries. It has a moderate aqueous solubility, is quite volatile and a low potential for bioaccumulation. It is non-mobile, moderately persistent in soil systems but may be persistent in water systems. It is moderately toxic to mammals but would not be expected to bioaccumulate. It is moderately toxic to most aquatic organisms, honeybees and earthworms but less so to birds.
[Chemical Properties]

The pure product is a colorless solid. MPa 78-80°C, relative density 1.27 (25°C), vapor pressure 0.67×10-3 Pa (25°C). Solubility at 25°C: acetone >500 g/kg, chloroform >500 g/kg, cyclohexanone >400 g/kg, hexane <50 g/kg, xylene >300 g/kg, dimethylformamide >500 g/kg, water 37 mg/L. Partition coefficient 2500. It is stable to heat and light and is stable in buffer solutions with a pH of 4-9. It readily hydrolyzes in concentrated alkaline media.
[Uses]

Agricultural fungicide.
[Uses]

An acylamino acid fungicide.
[Uses]

Benalaxyl is used for the control of Oomycetes on a wide range of crops, fruit, flowers, ornamentals and turf.
[Definition]

ChEBI: Methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)alaninate is an alanine derivative that is the N-phenylacetyl derivative of methyl N-(2,6-dimethylphenyl)alaninate It is an alanine derivative, an aromatic amide, a carboxamide and a methyl ester.
[Production Methods]

Benalaxyl is commercially produced through a multi-step chemical synthesis process, beginning with the formation of its core phenylamide structure. The active ingredient, methyl N-phenylacetyl-N-2,6-xylyl-DL-alaninate, is synthesized by reacting phenylacetic acid derivatives with substituted xylylamine and alanine esters under controlled conditions. This process yields a racemic mixture of enantiomers, typically formulated as a suspension concentrate or granules for agricultural use.
[Mechanism of action]

Systemic with protective, curative and eradicant action. Disrupts fungal nucleic acid synthesis - RNA ploymerase 1
[Metabolic pathway]

The fate of 14C-benalaxyl as affected by mancozeb is determined on the surface and in the tissues of grape leaves 7 days after the single foliar application of a mixture with mancozeb. The main oxidative scheme with rat liver microsomes is quite similar to that observed in plants. The only differences are represented by a further hydroxylation on the second ortho methyl group, and only traces of the meta hydroxylation take place on the xylene ring.
[Degradation]

Benalaxyl is stable in aqueous media over a wide pH range but it is hydrolysed in concentrated alkali. Its DT50 at pH 9 and 25 °C is 86 days (PM). It is reasonably stable to sunlight in aqueous solution. When irradiated in solution with UV light (254 nm) it is degraded with a half-life of 55 minutes (Pirisi et al., 1996). Products were compounds 2 and 3 (see Scheme 1) which are common also to metalaxyl and furalaxyl. These were detected in a non-labelled study. Under simulated sunlight its half-life was 167 days.
[Pesticide Type]

Fungicide
Safety DataBack Directory
[Hazard Codes ]

N
[Risk Statements ]

50/53
[Safety Statements ]

60-61
[RIDADR ]

UN 3077
[WGK Germany ]

2
[RTECS ]

AY5993200
[HS Code ]

29242990
[Storage Class]

11 - Combustible Solids
[Hazard Classifications]

Aquatic Acute 1
Aquatic Chronic 1
[Toxicity]

LD50 in rats (mg/kg): 4200 orally; 1100 i.p.; LC50 (96 hr) in rainbow trout: 3.75 mg/l (Bergamaschi)
Raw materials And Preparation ProductsBack Directory
[Raw materials]

Nickel-->Cyclohexane-->2,6-Dimethylaniline-->Methyl propionate-->Methyl acetate-->Phenylacetyl chloride-->methyl N-(2,6-dimethylphenyl)-DL-alaninate
[Preparation Products]

Benalaxyl-M
Spectrum DetailBack Directory
[Spectrum Detail]

Benalaxyl(71626-11-4)MS
Benalaxyl(71626-11-4)1HNMR
Benalaxyl(71626-11-4)13CNMR
Benalaxyl(71626-11-4)IR1
Benalaxyl(71626-11-4)IR2
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