| methoxyfenozide (Ref: RH 2485) |
 |
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SUMMARY
An insectide approved for use in the EU and many other countries on a broad range of fruit and vegetables. It has a low aqueous solubility and a low volatility. Based on its chemical properties there is a high risk of leaching to groundwater and under some conditions it may be persistent in soil systems. It has a low oral toxicity to mammals and no significant risk issues to human health have been identified. It has a low toxicity to birds and honeybees but is relatively more toxic to aquatic species and earthworms. GENERAL INFORMATION 
for methoxyfenozide
Description: An insecticide used to control various insects including moths and butterflies
Example pests controlled: Codling moth; Lesser appleworm; Oriental fruit moth; Leafrollers; Loopers; Cotton bollworm; Armyworm; Bud moths
Example applications: Leafy vegetables; Fresh herbs; Lettuce; Salads; Herbs; Brassicas; Cotton; Pome fruit; Grapes; Sweetcorn; Maize; Peppers; Aubergines
Efficacy & activity: The effectiveness of methoxyfenozide for the approved uses has been deminstrated via field trials and extensive use.
Availability status: Current
Introduction & key dates: 1996, first reported; 1998, first marketed
EC Regulation 1107/2009 (repealing 91/414):
| Status | Approved |
| Dossier rapporteur/co-rapporteur | UK/Slovakia |
| Date inclusion expires | 31/07/2019 |
| EU Candidate for substitution (CfS) | No |
| Listed in EU database | Yes |
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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Also used in: Australia, USA, Argentina, Brazil, Colombia, Israel, Japan, Mexico, Korea
Chemical structure:
| Isomerism | - |
| Chemical formula | C22H28N2O3 |
| Canonical SMILES | CC1=CC(=CC(=C1)C(=O)N(C(C)(C)C)NC(=O)C2=C(C(=CC=C2)OC)C)C |
| Isomeric SMILES | No data |
| International Chemical Identifier key (InChIKey) | QCAWEPFNJXQPAN-UHFFFAOYSA-N |
| International Chemical Identifier (InChI) | InChI=1S/C22H28N2O3/c1-14-11-15(2)13-17(12-14)21(26)24(22(4,5)6)23-20(25)18-9-8-10-19(27-7)16(18)3/h8-13H,1-7H3,(H,23,25) |
| Structure diagram/image available? | Yes |
General status:
| Pesticide type | Insecticide | |||
| Substance group | Diacylhydrazine | |||
| Minimum active substance purity | 970 g/kg | |||
| Known relevant impurities | EU dossier - butylhydrazine | |||
| Substance origin | Synthetic | |||
| Mode of action | A moulting accelerator that is an agonist of the hormone 20-hydroxyecdysone | |||
| CAS RN | 161050-58-4 | |||
| EC number | - | |||
| CIPAC number | 656 | |||
| US EPA chemical code | 121027 | |||
| PubChem CID | 105010 | |||
| Molecular mass (g mol-1) | 368.47 | |||
| PIN (Preferred Identification Name) | - | |||
| IUPAC name | N-tert-butyl-N'-(3-methoxy-o-toluoyl)-3,5-xylohydrazide | |||
| CAS name | 3-methoxy-2-methylbenzoic acid 2-(3,5-dimethylbenzoyl)-2-(1,1-dimethylethyl)hydrazide | |||
| Other status information | - | |||
| Relevant Environmental Water Quality Standards | - | |||
| Herbicide Resistance Classification (HRAC) | Not applicable | |||
| Herbicide Resistance Classification (WSSA) | Not applicable | |||
| Insecticide Resistance Classification (IRAC) | 18A | |||
| Fungicide Resistance Classification (FRAC) | Not applicable | |||
| Examples of recorded resistance | Cydia pomonella Deraeocoris brevis Spodoptera exigua |
|||
| Physical state | White powder | |||
| 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 | None | |||
| Formulation and application details | Often supplied as a soluble concentrate that is mixed with water and used as a foliar spray. | |||
ENVIRONMENTAL FATE
for methoxyfenozide
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Solubility - In water at 20oC (mg l-1) | 3.3 | A5 | Low | |
| Solubility - In organic solvents at 20oC (mg l-1) | 115000 | A5 - Methanol | - | |
| 69000 | A5 - Acetone | - | ||
| 28000 | A5 - Dichloromethane | - | ||
| 600 | A5 - Xylene | - | ||
| Melting point (oC) | 185 | A5 | - | |
| Boiling point (oC) | Decomposes before boiling | A5 | - | |
| Degradation point (oC) | 262.9 | A5 | - | |
| Flashpoint (oC) | Not expected to self ignite; Not highly flammable | A5 | - | |
| Octanol-water partition coefficient at pH 7, 20oC | P | 5.25 X 1003 | Calculated | - |
| Log P | 3.72 | A5 | High | |
| Bulk density (g ml-1)/Specific gravity | 0.634 | A5 | - | |
| Dissociation constant (pKa) at 25oC | 12.20 | A5 | - | |
| Note: | ||||
| Vapour pressure at 20oC (mPa) | 1.33 X 10-02 | A5 | Low volatility | |
| Henry's law constant at 25oC (Pa m3 mol-1) | 1.64 X 10-04 | A5 | Non-volatile | |
GUS leaching potential index  |
4.35 | Calculated | High leachability | |
| SCI-GROW groundwater index (μg l-1) for a 1 kg ha-1 or 1 l ha-1 application rate |
Value | 2.21 X 10+00 | Calculated | - |
| Note | - | |||
| Potential for particle bound transport index |
- | Calculated | Medium | |
| Maximum UV-vis absorption L mol-1 cm-1 | pH 7: 216nm=12819, 280nm=2503, 290nm=1561 pH 2: 216nm=12881, 279nm=2916, 290nm=1912 pH 10: 225nm=11312, 276nm=2937, 290nm=1548 |
A5 | - | |
| Surface tension (mN m-1) | 58.0 | A5 at 20 degC, 99.4% | - | |
Degradation:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
General biodegradability | - |
| Soil degradation (days) (aerobic) | DT50 (typical) | 456 | A5 | Very persistent |
| DT50 (lab at 20oC) | 456 | A5 | Very persistent | |
| DT50 (field) | 68 | A4 | Moderately persistent | |
| DT90 (lab at 20oC) | 1905 | A5 | - | |
| DT90 (field) | 717 | A3 | - | |
| DT50 modelling endpoint | - | - | - | |
| Note | EU 2016 dossier lab studies range DT50 81->1000 days, DT90 range 290-6340 days, Soils=14; EU 2004 dossier lab studies range 336-1100 days, DT90 range 1618 – 5302 days, field study range 39-133 days, DT90 range 434->1000 days; Other sources: 683 days (DW4) | |||
| Dissipation rate RL50 on plant matrix | Value | - | - | - |
| Note | - | |||
| Dissipation rate RL50 on and in plant matrix | Value | 5.3 | R4 | - |
| Note | Published literature RL50 range 4.3-6.2 days, 2 field & undercover grown crops, various matrices, n=2 | |||
| Aqueous photolysis DT50 (days) at pH 7 | Value | Stable | A5 | - |
| Note | - | |||
| Aqueous hydrolysis DT50 (days) at 20oC and pH 7 | Value | Stable | C4 | - |
| Note | Stable pH 5 to pH 9, 25 degC | |||
| Water-sediment DT50 (days) | 208.6 | A5 | Slow | |
| Water phase only DT50 (days) | - | - | - | |
Soil adsorption and mobility:
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Linear | Kd | - | A4 | Moderately mobile |
| Koc | 402 | |||
| Notes and range | EU 2004 dossier Koc range 200-922 mL/g; Other sources: 365 mL/g (DW3) | |||
| Freundlich | Kf | 2.87 | A5 | Moderately mobile |
| Kfoc | 231 | |||
| 1/n | 0.936 | |||
| Notes and range | EU 2016 dossier Kf range 1.53-6.2 mL/g, kfoc range 132-365 mL/g, 1/n range 0.85-1.00, Soils=16 | |||
| pH sensitivity | No | |||
Key metabolites:
| Metabolite | Formation medium | Estimated maximum occurrence fraction | 1107/2009 relevancy |
|
| (N-(3-methoxy-2-methylbenzoyl)-N-(3-carboxy-5-methylbenzoyl)-N-tert-butylhydrazine) (Ref: RH-131154) |
Soil | 0.158 | Major fraction; Relevant | |
Other known metabolites:
| Metabolite name and reference | Aliases | Formation medium / Rate | Estimated maximum occurrence fraction | Metabolising enzymes |
| - | desmethylated methoxyfenozide; methoxyfenozide metabolite M14 | Animal (Urinary, Faeces); Rat; Water/sediment | - | - |
| - | hydroxy methyl methoxyfenozide; methoxyfenozide metabolite M24 | Animal (Urinary, Faeces) | - | - |
| 3,5-dimethylbenzoic acid N-tert-butyl-N‘-(3-hydroxy-2-methylbenzoyl)-hydrazide | RH-117236 | - | - | - |
ECOTOXICOLOGY
for methoxyfenozide
| Property |
Value | Source/Quality Score/Other Information |
Interpretation |
|
| Bio-concentration factor | BCF (l kg-1) | 11 | A5 Whole fish | Low potential |
| CT50 (days) | Not available | - | ||
| Mammals - Acute oral LD50 (mg kg-1) | > 5000 | A5 Rat | Low | |
| Mammals - Short term dietary NOEL | (mg kg-1) | > 10 | L2 Rat, 2 year | High |
| (ppm diet) | - | - | ||
| Birds - Acute LD50 (mg kg-1) | > 2250 | A5 Colinus virginianus | Low | |
| Birds - Short term dietary (LC50/LD50) | > 5620 mg kg feed-1 | A5 Colinus virginianus | - | |
| Fish - Acute 96 hour LC50 (mg l-1) | > 4.2 | A5 Oncorhynchus mykiss | Moderate | |
| Fish - Chronic 21 day NOEC (mg l-1) | 2.4 | A5 Pimephales promelas | Moderate | |
| Aquatic invertebrates - Acute 48 hour EC50 (mg l-1) | 3.7 | A5 Daphnia magna | Moderate | |
| Aquatic invertebrates - Chronic 21 day NOEC (mg l-1) | 0.39 | A5 Daphnia magna | Moderate | |
| Aquatic crustaceans - Acute 96 hour LC50 (mg l-1) | 1.2 | F3 Americamysis bahia | Moderate | |
| Sediment dwelling organisms - Acute 96 hour LC50 (mg l-1) | - | - | - | |
| Sediment dwelling organisms - Chronic 28 day NOEC, static, water (mg l-1) | 0.018 | A5 Chironomus riparius | Moderate | |
| 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) | > 3.4 | A5 Pseudokirchneriella subcapitata | Moderate | |
| 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) | > 100 | A5 | Low | |
| Unknown mode acute 48 hour LD50 (μg bee-1) | - | - | - | |
| Earthworms - Acute 14 day LC50 (mg kg-1) | > 607 | A5 Eisenia foetida | Moderate | |
| Earthworms - Chronic 14 day NOEC, reproduction (mg kg-1) | - | - | - | |
| Other soil macro-organisms - e.g. Collembola | LR50 / EC50 / NOEC / % Effect | - | - | - |
| Other arthropod (1) | LR50 g ha-1 | - | - | - |
| % Effect | Harmless | AA2 Typhlodromus pyri | - | |
| Other arthropod (2) | LR50 g ha-1 | - | - | - |
| % Effect | Harmless | AA2 Chrysoperla carnea | - | |
| Soil micro-organisms | Nitrogen mineralisation: No significant adverse effect Carbon mineralisation: No significant adverse effect |
A5 Dose: 1.96 kg ha-1, 28 days |
- | |
| Mesocosm study data | NOEAEC mg l-1 | - | - | - |
| NOEAEC mg l-1 | - | - | - | |
HUMAN HEALTH AND PROTECTION
for methoxyfenozide
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) | > 5000 | A5 Rat | Low | |
| Mammals - Dermal LD50 (mg kg-1 body weight) | 5000 | A5 Rat | - | |
| Mammals - Inhalation LC50 (mg l-1) | > 4.3 | A5 Rat, 4 hr (nose only) | - | |
| Other Mammal toxicity endpoints | - | - | ||
| ADI - Acceptable Daily Intake (mg kg-1bw day-1) | 0.1 | A5 Rat, SF=100 | - | |
| ARfD - Acute Reference Dose (mg kg-1bw day-1) | 0.1 | A5 Dog, SF=100 | - | |
| AAOEL - Acute Acceptable Operator Exposure Level (mg kg-1 bw day-1) | 0.06 | A5 Dog, SF=100 | - | |
| AOEL - Acceptable Operator Exposure Level - Systemic (mg kg-1bw day-1) | 0.06 | A5 Dog, SF=100 | - | |
| Dermal penetration studies (%) | 0.5-8 | A5 concentration dependent | - | |
| Dangerous Substances Directive 76/464 | [Acceptable for proposed uses, PPE/PPC advised] | - | - | |
| Exposure Limits | - | - | - | |
| Exposure Routes | Public | Low for propsoed uses | ||
| Occupational | - | |||
| European MRLs | Click here for the EU MRL pesticide database | |||
| Drinking Water Standards | - | - | - | |
| 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 | Potential endocrine effects on thyroid and adrenal glands at high doses Possible liver toxicant |
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: 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 explosive or oxidising | |||
| CLP classification 2013 | Health: H315, H319 Environment: H412 |
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| EC Risk Classification |
N - Dangerous for the environment: R51/53 | |||
| EC Safety Classification |
- | |||
| WHO Classification | U | - | Unlikely to present an acute hazard | |
| US EPA Classification (formulation) | IV | - | Caution - Not acutely toxic | |
| UN Number | - | |||
| Waste disposal & packaging |
- | |||
TRANSLATIONS
for methoxyfenozide
| Language | Name |
| English | methoxyfenozide |
| French | methoxyfenozide |
| German | Methoxyfenozid |
| Danish | methoxyfenozid |
| Italian | metossifenozide |
| Spanish | metoxifenocida |
| Greek | - |
| Slovenian | metoksifenozid |
| Polish | metoksyfenozyd |
| Swedish | - |
| Hungarian | metoxifenozid |
| Dutch | - |
Record last updated: Monday 29 October 2018
Contact: aeru@herts.ac.uk