C16-18-(even numbered, C18-unsaturated)-alkylamines acetates

Endpoint summary

Description of key information

Toxicity to soil macro organisms

Acute toxicity

Noack (1999) determined the acute effects of tallow alkyl amine on earthworm Eisenia fetida according to OECD Guideline 207. Different concentrations of tallow alkyl amine (100, 180, 320, 580, 1000 mg/kg dry weight) were applied once at the beginning of the test. No significant mortality was observed in any of the tested concentrations after 14 days of exposure. As test result a LC50 > 1000 mg/kg dry weight was obtained from this study.

Long-term toxicity

The effects of amines, hydrogenated tallow alkyl amine on mortality, biomass and reproduction of Eisenia fetida were tested according to OECD 222 under a static exposure for 56 days (Noack, 2006). Natural soil (Lufa 2.2) was used as substrate, and the different concentration of the substance mixed with the substrate. The concentrations applied were 50, 100, 200, 500, and 1,000 mg/kg soil dry weight. In addition tests using control and vehicle control were performed.

The test is valid without restrictions and the results are reliable. After 28 days of exposure, no effects on survival of the adult worms were observed in all concentrations. After the following four weeks, the reproduction rate (average number of juveniles) was significantly reduced in the concentrations of 500 and 1,000 mg/kg soil compared to the control. Hence, the LOEC is 500 mg/kg soil and the NOEC 200 mg/kg soil. This NOEC can be used as a chronic endpoint representing heterotrophs (consumer) in the terrestrial environment.

 Toxicity to terrestrial plants

The growth test with terrestrial plants was conducted according to the OECD Guideline 208 by Noack (2000) using tallow alkyl amine as test substance. Test systems were a monocotyledon (oat) and two dicotyledons (red clover and radish). Seeds of each plant were exposed to different concentrations of tallow alkyl amine (1, 10, 100 mg test item per kg soil dry weight) and a control. No vehicles were used to dissolve the test substance. The toxic effects of the soil incorporated test item on the emergence of seedlings and the early stages of growth were determined by visual observations and dry weight determination. No phytotoxic effects were observed throughout the test in all replicates resulting in a LC50 (emergence) and a EC50 (growth) of > 100 mg/kg dw. As no effect on growth and emergence for all three species was observed at the highest concentration of 100 mg/kg dw. the NOEC is > 100 mg/kg dw. as well. The NOEC can be used as a chronic endpoint representing autotrophs (producer) in the terrestrial compartment.

 Toxicity to soil micro-organisms

Measured data on the toxicity to soil microorganisms are not available. But read across to the quat N-(C12-14) alkyl, N-Hydroxyalkyl, N,N-dimethylammonium chloride (HYEQS) (Clariant, 2009) can be done. HYEQS has similar sorption properties when compared to the Primary alkyl amines. In the OECD 209 test of sludge respiration inhibition (Clariant, 2010) HYEQS has an EC10 of 4 mg/L and in the OECD 216 Soil microorganism test a NOEC of > 1000 mg/kg soil dw. (Clariant, 2010bh). Coco alkyl amines having a carbon distribution with a maximum at C12-C14 has an EC10 of 5.5 mg/L in the OECD 209 test. Based on these facts a NOEC of 1000 mg/kg dw for soil micro-organisms can be justified for Coco alkyl amine in a read across approach as well (s. read-across document). This NOEC can be used as a chronic endpoint representing detritivors (decomposers) in the terrestrial compartment.

Toxicity to other terrestrial organisms

Nematodes
The results of three studies of the nematodical effect of primary fatty amines on three different species of nematode are summarized in the Table below. The tests were carried out under comparable conditions at 37°C in NaCl solution. The EC100 values determined with Ancylostoma cannium reveal an increasingly toxic effect with increasing chain length of the fatty amines (Ishizuka et al. 1971).

Table    Nematodical effect of primary fatty amines (test conditions 37°C, NaCl-solution)

Species	effect [mg/l]	C8	C10	C12	C16	C18	Reference
Toxocara canis(larvae) (dog ascarid)	3h-EC100	-	79	-	-	-	Kiuchi et al. 1987
Ancylostoma cannium(larvae) (dog hookworm)	24h-EC100	200	200	6.25	3.13	1.6	Ishizuka et al. (1971)
Ascaris lumbricoides(human ascarid)	1h-EC0 0.5h-EC100	- -	1000 -	- 1000	- -	- -	Anderson and Hurwitz (1953)

Nagase et al. (1982) exposed the nematode Bursaphelenchus lignicolus to different fatty amines in an aqueous test solution for 24 hours at 25°C (100 worms/ml; amine concentration 10 E-3 – 10 mmol/l; at chain lengths of and above 14 C atoms using solubilizer). The toxic effect on the nematodes increased from octylamine (24h-LC50 = 15.5 mg/l) to decylamine (24h-LC50 = 11.8 mg/l) and then remained constant for the longer chain homologous at 24h-LC50 = 2.1-2.3 mg/l.

However, as unsuitable test systems were used, the test results obtained for Ancylostoma cannium and Bursaphelenchus lignicolus can only give a rough indication of the nematodical effect of primary fatty amines and are therefore not used for the further assessment.

Terrestrial arthropods

For Primary alkyl amines three terrestrial trophic levels are covered with the available tests and detailed results are listed in IUCLID Section 6.3. The test organisms belong to

1) AUTOTROPHS (Producer)
Terrestrial plants, OECD 208

2) HETEROTROPHS (Consumer)
Earthworm (Eisenia fetida), OECD 207 (acute) & OECD 222 (chronic)

3) DETRITIVORS (Decomposer)
Soil microorganisms, OECD 216 (chronic) - Read across from Quaternary ammonium compounds, C12-18-alkyl(hydroxyethyl)dimethyl, chlorides (HYEQS, CAS No 85736-63-6), (Clariant, 2009)

Arthropods like Collembola folsomia (springtails) belong to Heterotrophs which are already covered by the available tests. In addition Primary alkyl amines are rapidly biodegraded in soil which ensures low exposure levels in soil. This means that further testing e.g. arthropods is not warranted.

Additional Literature

Clariant (2009): Aerobic soil transformation study with 14C-HYEQS according OECD 307, Harlan Lab, 2009

Clariant (2010): REACH Registration Dossier HYEQS, IUCLID Section 6.1.7 ‘Toxicity to microorganisms

Anderson, H.H. and Hurwitz, G.K. (1953): Dodecylamine and Ohter Agents Active Against Ascaris lumbricoides and Their Toxicity in Mammals. Arch. Exp. Pathol. Pharmakol. (219), 119-129

Ishizuka, H. et al. (1971): Fundamental Studies o Anthelmintics (18) on the Antiparasitic Effects of Monoamine Compounds upon Various Parasites in vitro. (Japanese, German short translation). Oyo Yakuri (5), 261-271

Kiuchi, F. et al. (1987): Studies on crude drugs effective on visheral larva migrans. Identification of larvicidal principles in betel nuts. Chem. Pharm. Bull (35), 2880-2886

Nagase, A. et al. (1982): Nematidical Activity of Akylamine against the Pine Wood Nematode, Bursaphelenchus lignicolus. Agric. Biol. Chem. (46), 167-172

Additional information

Category Approach for Primary alkyl amines and their salts e.g. Acetates

Primary alkyl amines were already assessed for their environmental and human health hazards and risks under the EU Existing Chemicals Regulation 793/93/EEC. Industry has provided a justification for the category approach to the German rapporteur BAuA on 2001-04-07. This justification was accepted as basis for the EU Risk assessment and is used for the REACH registration as well.

Speciation of Primary alkyl amines

In aqueous medium the unprotonated and the protonated amine are in equilibrium. The percentage of the unprotonated and the protonated amine is determined by the acid constant pKa and the given pH. In the table the percentages are given as function of pH and the pKa of 10.5 for Primary alkyl amines.

pH	Percentage Protonated amine (N+)	Percentage Unprotonated amine (N)
9	97.5%	2.5%
7	99.975%	0.025%
4	99.99997%	0.000003%

CONCLUSION:

Under environmental conditions it is not relevant if the unprotonated or the protonated amine will be introduced in an aquatic medium. The composition of the protonated and unprotonated amine is solely determined by the pKa and the ambient pH (see table above). Therefore aquatic test results from the unprotonated and protonated amine are equivalent.

Terrestrial toxicity

For all three trophic levels - producer, consumer and decomposer - chronic studies are available and the results are summarized in the table:

	Species	Guideline	Endpoint	NOEC (mg/kg dw)	Test item
PRODUCER	Plants (3 species)	OECD 208	Emergence	100	C16-18, 18u
CONSUMER	Earthworm	OECD 222	Reproduction	200	C16-18
DECOMPOSER	Soil microorganisms	OECD 216	Nitrate formation	1000	C12-18 HYEQS

These three chronic values are used to derive the PNEC soil.