| benalaxyl-M (Ref: IR 6141) |
 |
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SUMMARY
Benalaxyl-M is a fungicide that has EU approval for use and is widely used. It has a low aqueous solubility and is quite volatile. Based on its chemical properties it would not be expected to leach to groundwater. It is moderately persistent in soil systems but may be persistent in water. It is moderately toxic to mammals, birds, most aquatic organisms, honey bees and earthworms. GENERAL INFORMATION 
for benalaxyl-M
Description: A common fungicide used to control fungal infections on a variety of crops
Example pests controlled: Downy mildew; Powdery mildew; Late blight; Grey mould
Example applications: Tomatoes; Potatoes; Grapes
Availability status: Current
Introduction & key dates: 2003
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | Portugal |
| Date inclusion expires | 30/04/2024 |
Approved for use (
) or known to be used (
) in the following European countries: 
AT |
BE |
BG |
CY |
CZ |
DE |
DK |
EE |
EL |
ES |
FI |
FR |
HR |
HU |
IE |
IT |
LT |
LU |
LV |
MT |
NL |
PL |
PT |
RO |
SE |
SI |
SK |
UK |
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General status:
| Pesticide type | Fungicide | |||
| Substance group | Phenylamide | |||
| Minimum active substance purity | 950 | |||
| Known relevant impurities | EU dossier : None declared | |||
| Substance origin | Synthetic | |||
| Mode of action | A systemic fungicide with protective, curative and eradication action. Disrupts fungal nucleic acid synthesis - RNA ploymerase 1. | |||
| CAS RN | 98243-83-5 | |||
| EC number | - | |||
| CIPAC number | 766 | |||
| US EPA chemical code | - | |||
| Chiral molecule | Chiral, a specific isomer or a derivative of a chiral molecule | |||
| Chemical formula | C20H23NO3 | |||
| SMILES | O=C(N(c1c(cccc1C)C)[C@@H](C(=O)OC)C)Cc2ccccc2 | |||
| International Chemical Identifier key (InChIKey) | CJPQIRJHIZUAQP-MRXNPFEDSA-N | |||
| International Chemical Identifier (InChI) | 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/t16-/m1/s1 | |||
| Structure diagram/image available? | Yes | |||
| Molecular mass (g mol-1) | 325.40 | |||
| PIN (Preferred Identification Name) | methyl N-(phenylacetyl)-N-(2,6-xylyl)-D-alaninate | |||
| IUPAC name | methyl N-(phenylacetyl)-N-(2,6-xylyl)-D-alaninate | |||
| CAS name | methyl N-(2,6-dimethylphenyl)-N-(phenylacetyl)-D-alaninate | |||
| Other status information | Potential groundwater pollutant | |||
| Herbicide Resistance Classification (HRAC) | Not applicable | |||
| Herbicide Resistance Classification (WSSA) | Not applicable | |||
| Insecticide Resistance Classification (IRAC) | Not applicable | |||
| Fungicide Resistance Classification (FRAC) | 4 | |||
| Examples of recorded resistance | - | |||
| Physical state | White crystalline solid | |||
| Related substances & organisms | - | |||
Formulations:
| Property |
Value | |||
| Example manufacturers & suppliers of products using this active now or historically |
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| Example products using this active |
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| UK LERAP status | No UK approval for use or outside scope | |||
| Formulation and application details | - | |||
ENVIRONMENTAL FATE
for benalaxyl-M
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 33 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 17074 | A5 - n-Heptane | - | |
| 500000 | A5 - Methanol | - | ||
| 500000 | A5 - 1,2-Dichloromethane | - | ||
| 500000 | A5 - Acetone | - | ||
| Melting point (oC) | 76 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 280 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 4.79 X 1003 | Calculated | - |
| Log P | 3.68 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 1.17 | L3 | - | |
| Dissociation constant (pKa) at 25oC | N/a | - | - | |
| Note: No dissociation | ||||
| Vapour pressure at 25oC (mPa) | 0.0595 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 2.33 X 10-04 | A5 | Non-volatile | |
| Henry's law constant at 20oC (dimensionless) | 2.41 X 10-07 | Calculated | Non-volatile | |
GUS leaching potential index  |
0.43 | Calculated | Low leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 9.34 X 10-03 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | High | |
| Maximum UV-vis absorption L mol-1 cm-1 | Max at: 252.7nm; 258.6nm; 264.6nm & 274.1nm; No absorbance >290nm | A5 | - | |
| Surface tension (mN m-1) | 59.82 | A5 | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Soil degradation (days) (aerobic) | DT50 (typical) | 80 | L3 | Moderately persistent |
| DT50 (lab at 20oC) | 98.5 | A5 | Moderately persistent | |
| DT50 (field) | 44 | A5 | Moderately persistent | |
| DT90 (lab at 20oC) | 294 | A5 | - | |
| DT90 (field) | 178 | A5 | - | |
| Note | EU dossier lab studies DT50 range 49.0 to 207 days, DT90 range 148 to 484 days | |||
| Plant matrix DT50 (days) | Value | - | - | - |
| Note | - | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | Stable | L3 | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | L3 | - |
| Note | Stable pH 4 to pH 7, DT50 at pH 9: 301 days at 25 degC, 11 days at 50 degC | |||
| Water-sediment DT50 (days) | 125 | A5 | Slow | |
| Water phase only DT50 (days) | 38 | A5 | Stable | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | L3 | Non-mobile |
| Koc | 7175 | |||
| Notes and range | Koc range 2005-12346 mL/g 4 soils | |||
| Freundlich | Kf | 66.4 | A5 | Non-mobile |
| Kfoc | 6063 | |||
| 1/n | 0.98 | |||
| Notes and range | EU dossier Kf range 45.51-74.91, Kfoc range 2005-12346, 1/n range 0.92-1.04, soils=4 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 91/414 relevancy |
|
| methyl N-(malonyl)-N-(2,6-xylyl)-Dalaninate |
Soil | 0.241 | Major fraction, Relevant | |
| N-(malonyl)-N-(2,6-xylyl)-D-alanine |
Soil | 0.285 | Major fraction, Relevant | |
| N-(phenylacteyl)-N-(2,6-xylyl)-D-alanine |
Soil | 0.333 | Major fraction, Relevant | |
| 2-((carboxyacetyl)((2R)-1-methoxy-1-oxo-2-propanyl)amino)-3-methylbenzoic acid | Soil | - | ||
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| Ethylene thiourea | - | - | - | - |
| methyl N-(formyl)-N-(2,6-xylyl)-DLalaninate (Ref: B-F4) |
- | Groundwater | - | - |
| 2-{(carboxyacetyl)[(1RS)-1-carboxyethyl]amino}-3-methylbenzoic acid (Ref: B-F7) |
- | Groundwater | - | - |
| 2-{(carboxyacetyl)[(2RS)-1-methoxy-1-oxo-2-propanyl]amino}-3-methylbenzoic acid (Ref: B-F8) |
- | Groundwater | - | - |
| methyl N-(malonyl)-N-(2,6-xylyl)-DLalaninate (Ref: B-M1) |
- | Groundwater | - | - |
| N-(malonyl)-N-(2,6-xylyl)-DL-alanine (Ref: B-M2) |
- | Groundwater | - | - |
| methyl N-(formyl)-N-(2,6-xylyl)-Dalaninate (Ref: R-isomer of B-F4) |
- | Groundwater | - | - |
| 2-{(carboxyacetyl)[(1R)-1-carboxyethyl]amino}-3-methylbenzoic acid (Ref: R-isomer of B-F7) |
- | Groundwater | - | - |
| 2-{(carboxyacetyl)[(2R)-1-methoxy-1-oxo-2-propanyl]amino}-3-methylbenzoic acid (Ref: R-isomer of B-F8) |
- | Groundwater | - | - |
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 57 | A5 | Low potential |
| CT50 (days) | 0.25 | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 2000 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | 4.4 | L3 Rat, 2 year | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2000 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 775.2 mg kg-1 BW | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | 4.9 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 0.49 | A5 Oncorhynchus mykiss | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 22.8 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.2 | A5 Daphnia magna | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, sediment (mg kg-1) | - | - | - | |
| Aquatic plants - Acute 7 day EC50, biomass (mg l-1) | - | - | - | |
| Non-target plants | - | - | - | |
| - | - | - | ||
| Algae - Acute 72 hour EC50, growth (mg l-1) | 16.5 | A5 Scenedemus subspicatus | Low | |
| Algae - Chronic 96 hour NOEC, growth (mg l-1) | - | - | - | |
| Honeybees | Contact acute 48 hour LD50 (μg bee-1) | > 100 | A5 | Low |
| Oral acute 48 hour LD50 (μg bee-1) | > 104 | A5 | Low | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | 236 | A5 corr | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | 26 | A5 corr | Moderate | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | >172.2 | Mortality A5 Typhlodromus pyri |
- |
| % Effect | - | - | - | |
| Other arthropod (2) | LR50 g ha-1 | >2745.6 | Mortality A5 Aphidius rhopalosiphi |
- |
| % Effect | - | - | - | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 1.65 mg kg-1 soil |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for benalaxyl-M
General:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Threshold of Toxicological Concern (Cramer Class) |
High (class III) | - | - | |
| Mammals - Acute oral LD50 (mg kg-1) | > 2000 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | > 2000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 4.42 | A5 Rat, 4 hr (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.04 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | None allocated | A5 | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.06 | A5 Rat, SF=100 | - | |
| Dermal penetration studies (%) | 2.5-29% | A5, Concentration dependant | - | |
| Dangerous Substances Directive 76/464 | - | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Very low risk estimated | ||
| Occupational | PPC/PPE advised | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water MAC (μg l-1) | - | - | - | |
Health issues:
| Carcinogen | Mutagen | Endocrine disrupter | Reproduction / development effects | Cholinesterase inhibitor | Neurotoxicant | |||
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| Respiratory tract irritant | Skin irritant | Skin sensitiser | Eye irritant | Phototoxicant | ||||
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| General human health issues | Possible liver toxicant | |||||||
: Yes, known to cause a problem
: No, known not to cause a problem
: Possibly, status not identified
- : No data found
Handling issues:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| General |
Not oxidising or explosive | |||
| CLP classification 2013 | None allocated at this time | |||
| EC Risk Classification |
N - Dangerous for the environment: R51/53 | |||
| EC Safety Classification |
- | |||
| WHO Classification | NL | - | Not listed | |
| US EPA Classification (formulation) | - | - | ||
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
| Language | Name |
| English | benalaxyl-M |
| French | benalaxil-M |
| German | Benalaxyl-M |
| Danish | benalaxyl-M |
| Italian | benalaxil-M |
| Spanish | benalaxil-M |
| Greek | - |
| Slovenian | benalaksil-M |
| Polish | benalaksyl-M |
| Swedish | - |
| Hungarian | benalaxyl-M |
| Dutch | - |
Record last updated: Wednesday 09 December 2015
Contact: aeru@herts.ac.uk