30/03/2010CLEAN 42576-02-3 Bifenox Dossier 20100329

30/03/2010CLEAN_42576-02-3_Bifenox_dossier_20100329.doc

Bifenox

As regards particular conditions to be taken into account on short term basis by Member States in relation to the granting of authorisations of plant protection products containing Bifenox, it was stated:

“On the basis of the proposed and supported uses (as listed in Appendix II), the following particular issues have been identified as requiring particular and short term attention from all Member States, in the framework of any authorisations to be granted, varied or withdrawn, as appropriate:

-the operator and worker safety. Conditions of use should include protective measures, where appropriate

-the potential residues of bifenox and hydroxybifenox acid (if this metabolite is toxicologically relevant) in food of animal origin and potential residues of bifenox in the rotated crops in order to perform a robust dietary risk assessment for the consumers.”

1Chemical IDENTITY

Common name / Bifenox
Chemical name (IUPAC) / Methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate
Synonym(s) / 5-(2,4-Dichlorophenoxy)-2-nitrobenzoic acid methyl ester
2,4-dichlorophenyl 3-(methoxycarbonyl)-4-nitrophenyl ether
Chemical class / Herbicides
CAS number / 42576-02-3
EU number / 255-894-7
Molecular formula / C14H9Cl2NO5
Molecular structure /
Molecular weight (g.mol-1) / 342.14
Known metabolites / Aminobifenox
Aminobifenox acid
5-hydroxybifenox acid
hydroxybifenox acid

2Existing evaluations and Regulatory information

Legislation
Annex III EQS Directive (2008/105/EC) / Not included
Existing Substances Regulation (793/93/EC) / Not applicable
Pesticides(91/414/EEC) / Included in Annex I
Biocides (98/8/EC) / Not investigated
PBT substances / Not investigated (EU)
Remark: Bifenox used to be included in the List of Substances of Potential Concern of OSPAR Convention but was deselected for the reason that it does not fulfil the P criterion.
Substances of Very High Concern (1907/2006/EC) / No
POPs (Stockholm convention) / Yes
Other relevant chemical regulation (veterinary products, medicament, ...) / Not applicable
Endocrine disrupter / Bifenox is not included in Commission Staff Working Document on implementation of the Community Strategy for Endocrine Disrupters - a range ofsubstances suspected of interfering with the hormone systems of humans and wildlife(COM (1999) 706) (E.C., 2004)

Bifenox has been included into Annex I to Directive 91/414/EC. It is used as a control of weeds in post-emergence applications in winter cereals (E.C., 2006).

The review report for the active substance Bifenox(E.C., 2006) has concluded that:

-“the residues arising from the proposed uses, consequent on application consistent with good plant ptrotection practive, have no harmful effects on human or animal health”,

-“estimates of acute dietary exposure of adults and children revealed that the Acute Reference Dose would not be exceeded”,

-“under the proposed and supported conditions of use there are no unacceptable effects on the environment, as provided for in Article 4 (1) (b) (iv) and (v) of Directive 91/414/EEC”.

“It may be expected that plant protection products containing bifenox will fulfill the safety requirements laid down in Article 5(1)(a) and (b) of Directive 91/414/EEC. This conclusion is however subject to compliance with the particular requirements in sections 4, 5, 6 and 7 of this report, as well as to the implementation of the provisions of Article 4(1) and the uniform principles laid down in Annex VI of Directive 91/414/EEC, for each bifenox containing plant protection product for which Member States will grant or review the authorisation.

Furthermore, these conclusions were reached within the framework of the uses which were proposed and supported by the main data submitter and mentioned in the list of uses supported by available data (attached as Appendix II to this review report).

Extension of the use pattern beyond those described above will require an evaluation at Member State level in order to establish whether the proposed extensions of use can satisfy the requirements of Article 4(1) and of the uniform principles laid down in Annex VI of Directive 91/414/EEC.

The following reference values have been finalised as part of this re-evaluation:

ADI 0.3 mg/Kg bw/day

With particular regard to residues, the review has established that the residues arising from the proposed uses, consequent on application consistent with good plant protection practice, have no harmful effects on human or animal health. The Theoretical Maximum Daily Intake (TMDI; excluding water and products of animal origin) for a 60 kg adult is 0.055% of the Acceptable Daily Intake (ADI), based on the FAO/WHO European Diet (August 1994).

Additional intake from water is not expected to give rise to intake problems.

Estimates of acute dietary exposure of adults and children revealed that the Acute Reference Dose (ARfD) would not be exceeded (According to the UK model :– 0.17% or 0.42% of the ARfD, respectively for adults and children).

While the consumer exposure to residues of Bifenox in wheat grain is expected to be insignificant (<1% of the ADI and ARfD, respectively), the exposure to residues in food of animal origin and in rotated crops cannot be assessed due to the lack of data.

The review has identified several acceptable exposure scenarios for operators, workers and bystanders, which require however to be confirmed for each plant protection product in accordance with the relevant sections of the above mentioned uniform principles.

The review has also concluded that under the proposed and supported conditions of use there are no unacceptable effects on the environment, as provided for in Article 4 (1) (b) (iv) and (v) of Directive 91/414/EEC.”

3Proposed Quality Standards (QS)

3.1Environmental Quality Standard (EQS)

ETOX database[*] refers to existing german Quality Criteria (Nendza, 2003)

-for protection of aquatic life = 0.01 µg/l

-for protection of human health via consumption of drinking water = 0.1 µg/l

-for protection of aquatic life from transient concentration peaks = 0.6 µg/l

QS ??? is the “critical QS” for derivation of an Environmental Quality Standard for bifenox.

Add any comment on possible residual uncertainty.

Value / Comments
Proposed AA-EQS for [biota] [µg.kg-1biota ww]
Corresponding AA-EQS in [freshwater] [µg.L-1]
Corresponding AA-EQS in [saltwater] [µg.L-1] / To be defined
To be defined
To be defined / Critical QS is QS ???
See section 4
Proposed MAC-EQS for [freshwater] [µg.L-1]
Proposed MAC-EQS for [saltwater] [µg.L-1] / To be defined
To be defined / See section 4.1

3.2Specific Quality Standard (QS)

Protection objective[†] / Unit / Value / Comments
Pelagic community (freshwater) / [µg.l-1] / To be defined / See section 4.1
Pelagic community (marine water) / [µg.l-1] / To be defined
Benthic community (freshwater) / [µg.kg-1dw] / To be defined / EqP, see section 4.1
Benthic community (marine) / [µg.kg-1dw] / To be defined
Predators (secondary poisoning) / [µg.kg-1biota ww] / To be defined / See section 4.2
[µg.l-1] / To be defined (freshwater)
To be defined (saltwater)
Human health via consumption of fishery products / [µg.kg-1biota ww] / To be defined / See section 4.3
[µg.l-1] / To be defined (freshwater)
To be defined (saltwater)
Human health via consumption of water / [µg.l-1] / To be defined

4[James1]Major uses and Environmental Emissions

4.1Uses and Quantities

Bifenox is included in Annex I of Directive 91/414/EEC and used as a “control of broad leaved weeds in post-emergence applications in winter cereals. Bifenox is especially active on difficult to control broadleaf weeds like Veronica, Viola and Galium spp. Other species like Lamium spp. are also controlled.” (E.C., 2006)

Authorisations at national level have been granted in 19 out 27 Member States (AT, BE, BG, CZ, DE, DK, ES, FI, FR, HU, IE, IT, LU, NL, PL, RO, SE, SK, UK).

4.2Estimated Environmental Emissions

No information available

5Environmental Behaviour

5.1Environmental distribution

Master reference
Water solubility (mg.l-1) / <0.1 at 20°C whatever the pH / E.C., 2006
Volatilisation / Bifenox is very slightly volatile.
Vapour pressure (Pa) / 4.74 10-8 at 20°C
1.85 10-7 at 25°C / E.C., 2006
Henry's Law constant (Pa.m3.mol-1) / >1.62 10-4 at 20°C
Adsorption / Bifenox is strongly adsorbed to soil and sediment particles.
Organic carbon – water partition coefficient (KOC) / KOC = 500 – 23000 L/kg (soils)
log KOC = 2.7 – 4.4 / E.C., 2006
Mean KOC used for assessment of PECsurfacewater = 7143 L/kg
log KOC = 3.85
Sediment – water partition coefficient (Ksed-water) / 894 / Calculated from mean KOC
Bioaccumulation / Bifenox is quite a liposoluble substance and as a fact has a bioconcentration potential.
Octanol-water partition coefficient (Kow) / log KOW = 3.64 / E.C., 2006
BCF (measured) / BCF values of 460 (fillet), 1500 (whole fish) and 2400 (viscera) were found for fish.
The BCF value of 1500 on fish is used for derivation of quality standards (BMF1 = 1, BMF2 = 1)

5.2Abiotic and Biotic degradations

Master reference
Hydrolysis / At 25°C: -at pH7: k=0.026 d-1; DT50 = 265 d
- at pH9: k=0.172 d-1; DT50 = 4 d
Bifenox is hydrolytically stable at pH 4, slightly hydrolysing at pH7 and fairly hydrolysing at pH9.
Main hydrolysis product is corresponding carboxylic acid: Bifenox acid / E.C., 2006
Photolysis / At 20°C, in pH 5 buffer with continuous artificial irradiation for 72 h: k = 0.028 h-1; DT50 = 24.4 h.
Bifenox is readily degradable by direct phototransformation.
Main photodegradation product is 2,4-dichlorophenol. / E.C., 2006
Biodegradation / Bifenox is not readily biodegradable: 11.8 – 14.0 % ThCO2 after 28 days. / E.C., 2006

6Aquatic environmental concentrations

6.1Estimated concentrations

Compartment / Distance between the crop and the water (m) / Predicted environmental concentration (PEC) / Master reference
Freshwater (µg/l) / 1 / 6.930 / E.C., 2006
3 / 2.502
30 / 0.250
- / 27.1 / Daginnus et al., 2009(1)
Marine waters (coastal and/or transitional) / - / No data available
Sediment (µg/kg) / 1 / 259.690 / E.C., 2006
3 / 93.751
30 / 9.375
Biota (freshwater) / - / No data available
Biota (marine) / - / No data available
Biota (marine predators) / - / No data available

(1) data originated from EU modelling-based prioritisation results.

6.2Measured concentrations

Compartment / Measured and quantified environmental concentrations
(nb analysis) / Master reference
Freshwater (µg/l) / cf. table above / James et al., 2009(1)
Marine waters (coastal and/or transitional) (µg/l)
WWTP effluent (µg/l) / No data available
Sediment (µg/kg dw) / Sed 2 mm / cf. table above / James et al., 2009(1)
Sed 20 µm / (0)
Sed 63µm / (0)
Biota / Invertebrates (µg/kg ww) / (0) / James et al., 2009(1)
Fish (µg/kg ww) / (0)
Marine predators / No data available

(1) data originated from EU monitoring data collection

7effects and Quality Standards

The active substance causes herbicide contact effect via cellular membrane disruption and inhibition of photosynthesis (E.C., 2006).

All data presented extracted from EU-DAR (E.C., 2006) thereafter are considerer valid. The one data extracted from US-EPA Pesticide Ecotoxicity Database (US-EPA, 2009) is considered valid because it is a “Core data”[‡].

7.1Acute and chronic aquatic ecotoxicity

ACUTE EFFECTS / Master reference
Algae & aquatic plants
(mg.l-1) / Freshwater / Scenedesmus subspicatus / 96h
EbC50 = 0.000175 ; ErC50 = 0.00019 / E.C., 2006
Navicula pelliculosa / 72h
EbC50 = 0.0049; ErC50 = 0.038
Lemna gibba / 14d
ErC50 = 0.0021
Marine / No available information
Invertebrates
(mg.l-1) / Freshwater / Daphnia magna / 48h
EC50 = 0.66 / E.C., 2006
Marine / Americamysis bahia / 96h
LC50 = 0.042 / US-EPA, 2009
Sediment / No available information
Fish
(mg.l-1) / Freshwater / Oncorhynchus mykiss / 96h
LC50 = 0.67 / E.C., 2006
Lepomis macrochirus / 96h
LC50 > 0.27
Marine / Cyprinodon variegatus / 96h
LC50 = 44 / US-EPA, 2009
CHRONIC EFFECTS / Master reference
Algae & aquatic plants
(mg.l-1) / Freshwater / Scenedesmus subspicatus / 96h
NOEC = 0.000125 / E.C., 2006
Navicula pelliculosa / 72h
NOEC = 0.00016
Lemna gibba / 14d
NOEC < 0.00045
Marine / No available information
Invertebrates
(mg.l-1) / Freshwater / Daphnia magna / 21d
NOEC = 0.00015 / E.C., 2006
Marine / No available information
Sediment / Chironomus riparius / 28d
NOEC = 0.015 / E.C., 2006
Fish
(mg.l-1) / Freshwater / Oncorhynchus mykiss / 21d
NOEC = 0.0091 / E.C., 2006
Lepomis macrochirus / 14d
NOEC = 0.13
Marine / No available information
Tentative QSwater / Relevant study for derivation of QS / Assessment factor / Tentative QS
MACfreshwater, eco / Scenedesmus subspicatus / 96h
ErC50 = 0.000190 / 10 / 1.25 10-2 µg.l-1
MACmarine water, eco / 100 / 1.25 10-3 µg.l-1
AA-QSfreshwater, eco / Scenedesmus subspicatus / 96h
NOEC = 0.000125 / 10 / 1.25 10-2 µg.l-1
AA-QSmarine water, eco / 100 / 1.25 10-3 µg.l-1
AA-QSfreshwater, sed. / - / EqP / To be defined
AA-QSmarine water, sed. / - / EqP / To be defined[James2]

7.2Secondary poisoning

Secondary poisoning of top predators / Master reference
Mammalian oral toxicity / Mouse / Oral / 2 years / Carcinogenicity / 0-50-200-1000 ppm / Decreased reticulocytes and platelets
NOAEL = 30 mg.kg-1bw.d-1
NOEC =200 mg.kg-1feed ww (CF=study specific) / E.C., 2006
Avian oral toxicity / Coturnix coturnix japonica /Oral /6 weeks /repro
NOEC= 1400 mg/kgfood
NOAEL= 290 mg.kg-1feed ww / E.C., 2006
Tentative QSbiota / Relevant study for derivation of QS / AF / Tentative QS
Biota / NOEC = 200mg.kg-1feed ww / 30 / 6667µg.kg-1biota ww
corresponding to
4.4µg.L-1(freshwater)
4.4µg.L-1(saltwater)[James3]

(1) proposal made for the purpose of this dossier, according to REACH guidance on information requirements and chemical safety assessment (ECHA, 2008)

7.3Human health

Human health via consumption of fishery products / Master reference
Mammalian oral toxicity / Mouse / Oral / 2 years / Carcinogenicity / 0-50-200-1000 ppm / Decreased reticulocytes and platelets
NOAEL : 30 mg.kg-1bw.d-1 / E.C., 2006
CMR / Bifenox is not classified for any carcinogenic, mutagenic or reprotoxic properties / E.C., 2008; IARC, 2009
Tentative QSbiota, hh / Relevant study for derivation
of QSbiota, hh / AF / Threshold level / Tentative QSbiota, hh
Human health / NOAEL : 30 mg.kg-1bw.d-1 / 100(1) / 0.3(1)
mg.kg-1bw.d-1 / 18261µg.kg-1biota ww
corresponding to
12.2µg.L-1 (freshwater)
12.2µg.L-1 (saltwater)[James4]

(1) This value and the associated assessment factor are considered valid as they were determined byE.C., 2006.

Human health via consumption of drinking water / Master reference
Existing drinking water standard(s) / 0.1 µg.L-1 (preferred regulatory standard) / Directive 98/83/EC
No guideline / WHO

8Bibliography, Sources and supportiveinformation

Daginnus K., Gottardo S., Mostrag-Szlichtyng A., Wilkinson H., Whitehouse P., Paya-Pérez a. and Zaldívar J.-M. (2009). A modelling approach for the prioritisation of chemicals under the Water Framework Directive. Ispra, Italy, European Commission, Joint Research Centre, Institute for Health and Consumer Protection.: 48.

E.C. (2004). Commission staff working document on implementation of the Community Strategy for Endocrine Disrupters - a range of substances suspected of interfering with the hormone systems of humans and wildlife (COM(1999) 706)). SEC(2004) 1372., European Commission.

E.C. (2006). Draft Assessment Report (DAR) - public version. Initial risk assessment by the rapporteur Member States Belgium for the existing active substance BIFENOX in the third stage (part A) of the review programme referred to in Article 8(2) of Council Directive 91/414/EEC.

E.C. (2008). Regulation (EC) No 1272/2008 of the European Parliament and of the Council of 16 December 2008 on classification, labelling and packaging of substances and mixtures, amending and repealing Directives 67/548/EEC and 1999/45/EC, and amending Regulation (EC) No 1907/2006 (Text with EEA relevance). Official Journal of the European Union. L353: 1355.

IARC (2009). "Agents reviewed by the IARC Monographs. Volumes 1-100A." (1-100a).

James A., Bonnomet V., Morin A. and Fribourg-Blanc B. (2009). Implementation of requirements on Priority substances within the Context of the Water Framework Directive. Contract N° 07010401/2008/508122/ADA/D2. Prioritisation process: Monitoring-based ranking., INERIS / IOW: 58.

Nendza M. (2003). Entwicklung von Umweltqualitätsnormen zum Schutz aquatischer Biota in Oberflächengewässern. Luhnstedt, UBA-FB: 35 + Annexes.

US-EPA (2009). Pesticide Ecotoxicity Database, Environmental Fate and Effects Division of the Office of Pesticide Programs, US-EPA.

1

[*]

[†]Please note that as recommended in the Technical Guidance for deriving EQS (drat version), “EQSs […] are not reported for ‘transitional and marine waters’, but either for freshwater or marine waters”. If justified by substance properties or data available, QS for the different protection objectives are given independently for transitional waters or coastal and territorial waters.

[‡]The three study categories used by the Agency to classify studies are core, supplemental, and invalid. Classification as “core data” means that all essential information was reported and the study was performed according torecommended EPA or ASTM methodology. For more details, please see

[James1]TO BE DETERMINED LATER - ON HOLD

[James2]TENTATIVE AF – TO BE DISCUSSED

[James3]TENTATIVE AF – TO BE DISCUSSED

[James4]TENTATIVE AF – TO BE DISCUSSED