Guanidine, N,N'''-1,3-propanediylbis-, N-coco alkyl derivs.

Endpoint summary

Additional information

EPISuite predictions:

Substance name: 39947_Guanidine,C12-C16(even numbered),N,N'''-1,3-propanediylbis derivatives acetate

EC number: 308-757-1

CAS number: 98246 -84 -5

  

Chemical structures and SMILES notations for C12 analogue

1 -(C12 -18 -(even numbered))-alkyl-tetrahydropyrimidin-2(1H)-imine acetate salt

N=C1NCCCN1CCCCCCCCCCCC

  

1-(3-((C12-18-(even numbered))-alkyl-amino)propyl)guanidine acetate salt

NC(=N)NCCCNCCCCCCCCCCCC

  

1-(C12-18-(even numbered))-alkyl-1-(3-guanidinopropyl) guanidine acetate salt

NC(=N)NCCCN(CCCCCCCCCCCC)C(=N)N

  

QSAR Biodeg predictions (in EPA's EPISuite):

Table 1. Predictions in EPISuite for 1-(C12-18-(even numbered))-alkyl-tetrahydropyrimidin-2(1H)-imine acetate salt considering even-numbered C12-C18 chain lengths

 

	C12	C14	C16	C18
Biowin1 (Linear model prediction)	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast
Biowin2 (Non-linear model prediction	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast	Does not biodegrade fast
Biowin3 (Ultimate biodegradation timeframe)	Weeks	Weeks	Weeks	Weeks-months
Biowin4 (Primary biodegradation timeframe)	Days-Weeks	Days-Weeks	Days-Weeks	Days-Weeks
Biowin5 (MITI linear model prediction)	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast
Biowin6 (MITI Non-linear model prediction)	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast
Biowin7 (Anaerobic model prediction)	Does not biodegrade fast	Does not biodegrade fast	Does not biodegrade fast	Biodegrades fast

 

Table 2. Predictions in EPISuite for 1-(3-((C12-18-(even numbered))-alkyl-amino)propyl)guanidine acetate salt

	C12	C14	C16	C18
Biowin1 (Linear model prediction)	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast
Biowin2 (Non-linear model prediction	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast	Does not biodegrade fast
Biowin3 (Ultimate biodegradation timeframe)	Weeks	Weeks	Weeks	Weeks-months
Biowin4 (Primary biodegradation timeframe)	Days-Weeks	Days-Weeks	Days-Weeks	Days-Weeks
Biowin5 (MITI linear model prediction)	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast
Biowin6 (MITI Non-linear model prediction)	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast
Biowin7 (Anaerobic model prediction)	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast	Biodegrades fast

 

Table 3. Predictions in EPISuite for 1-(C12-18-(even numbered))-alkyl-1-(3-guanidinopropyl) guanidine acetate salt

	C12	C14	C16	C18
Biowin1 (Linear model prediction)	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast
Biowin2 (Non-linear model prediction	Biodegrades Fast	Does not biodegrade fast	Does not biodegrade fast	Does not biodegrade fast
Biowin3 (Ultimate biodegradation timeframe)	Weeks	Weeks-Months	Weeks-Months	Weeks-Months
Biowin4 (Primary biodegradation timeframe)	Days-Weeks	Days-Weeks	Days-Weeks	Days-Weeks
Biowin5 (MITI linear model prediction)	Does not biodegrade fast	Does not biodegrade fast	Does not biodegrade fast	Does not biodegrade fast
Biowin6 (MITI Non-linear model prediction)	Does not biodegrade fast	Does not biodegrade fast	Does not biodegrade fast	Does not biodegrade fast
Biowin7 (Anaerobic model prediction)	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast	Biodegrades Fast

 

GENERAL REMARKS

Issues in Biodegradation testing of the registration substance

The registration substance is toxic to microorganisms and therefore the test concentration in biodegradation tests have to be sufficiently low to ensure the viability of the inoculum.This means that 14C test item would be the test material of choice. As the registration substance is a UVCB the preparation of a representative 14C material is not feasible. Therefore cold material has to be used which poses a considerable analytical challenge at very low concentration. On the other hand results from similar mono-constituent 14C substances can be reasonably used for read-across.

Read across substances

The registration substance has structural elements like long-chain ammonium and alkyl guanidinium salts. Such structural elements are present in long-chain primary alkyl amines and in guanidinium salts. In the following read-across substances are listed which are all REACH registered and where the substance data can be found on the Dissemination site of ECHA ( http://echa.europa.eu/

information-on-chemicals) or at the EU ESIS site ( http://esis.jrc.ec.europa.eu):

Gudanidinium nitrate, CAS No, 506 -93 -4

1-Hexadecanamine, CAS No. 143 -27 -1

Cocoylamines (C12 -14 Primary alkyl amines), CAS No. 61788 -46 -3

C20 -22 alkyl trimethyl ammonium chloride, CAS No. 68607-24-9

BIODEGRADATION IN WATER: SCREENING TESTS

The registration substance is toxic to microorganisms and the required minimum test concentration of e.g. 5 mg/L in a test on ready biodegradation is too high to allow conditions which are not influencing the viability of the inoculum. As it is not feasible to prepare 14C material of the registration substance (see above) a test at lower concentration could not be performed. Instead read-across is used to justify the conclusion that the registration substance is readily biodegradable:

14C-C22 alkyl trimethyl ammonium chloride (see IUCLID Chapter 5.2.1):

OECD 301 B CO2 Evolution test, 0.2 mg/L test conc.: 80% 14CO2 formation after 28d

C12 -14 alkyl amines (see IUCLID Chapter 5.2.1):

OECD 301B CO2 Evolution test, 13 mg/L test conc. : >60% CO2 formation after 29d, readily biodegradable

Guanidinium nitrate (see ESIS web, CAS 506 -93 -4)

14C Guanidinium nitrate (no concentration given) was incubated with industrial sewage as inoculum and showed 68% 14CO2 formation after 1.3 days.

CONCLUSION

Based on the available facts (see above), it can be concluded that the registration substance is likely to be readily biodegrable if the concentration of the registration substance is low enough to ensure the viability of the inoculum.

BIODEGRADATION IN WATER & SEDIMENT

SEWAGE TREATMENT PLANT SIMULATION TEST

An OECD 303A STP Simulation test is carried out with cold registration substance. This is a considerable analytical challenge as low test concentration is warranted due to the high toxicity for microoganisms. For the time being read-across is used (see IUCLID Chapter 5.2.2):

C20 -22 alkyl trimethyl ammonium chloride (see IUCLID Chapter 5.2.2)

OECD 303 A: Mean elimination: 99%, mean biodegradation: 92.2% (6.9% sorbed to sludge, 1% to effluent)

Cocoylamines (C12 -14 Primary alkyl amines, see IUCLID Chapter 5.2.2)

OECD 303A: Mean elimination: 99.8%, mean biodegradation: not measured

SIMULATION TEST ON BIODEGRADATION IN SEDIMENT

It is reasonable to use the DT50 of the soil biodegradation simulation test for sediment as well (see REACH Guidance) and therefore no OECD 308 Sediment simulation test is warranted.

OECD 307: highest DT50 soil is 45.5 d at 12 deg C

CONCLUSION

STP

The results from the OECD303A with C20 -22 ATQ is used as worst case for the registration substance resulting in 92.2% biodegradation, 6.9% sorption to sewage sludge and 1% discharge in effluent.

SEDIMENT

The DT50 of 45.5 d from an OECD 307 soil study with C20 -22 alkyl trimethyl ammonium chloride is used a worst case for the registration substance.

BIODEGRADATION IN SOIL

For a Soil biodegradation simulation test according OECD 307 14C material is mandatory to achieve reliable results. As mentioned before the registration substance is a multi-constituent and the synthesis of a representative 14C material not feasible. Therefore read-across is the only way to conclude on soil biodegradation:

14C-C22 alkyl trimethyl ammonium chloride (see IUCLID Chapter 5.2.3)

OECD 307: highest DT50 is 45.5 d at env. temperature 12 deg C is used in exposure assessment of the registration substance

14C-1 -Hexadecanamine (see IUCLDI Chapter 5.2.3)

OECD 307: highest DT50 is 17 d at env. temperature 12 deg C

CONCLUSION

EPISuite predicts ready biodegradabiliy. In addition both read-across substances show rapid degradation in soil. The worst case result from the OECD 307 carried out with 14C-C22 alkyl trimethylammonium chloride which is DT50 45.4 d at 12 deg C is used in exposure assessment of the registration substance.