. 2021 Oct 13;96(1):121–134. doi: 10.1007/s00204-021-03159-0

Table 2.

Identified and confirmed metabolites (n = 24) of seven dosed neonicotinoids and neonicotinoid-like compounds (NNIs) including name, molecular formula, retention time (t_R), and confidence level of their identification based on Schymanski et al. (2014)

	Dosed substance	Identified substances and metabolites in urine
	Dosed substance	Name	Molecular formula	t_R (min)	Confidence level
Classical neonicotinoids	IMI	IMI	C₉H₁₀ClN₅O₂	8.5	1
		4-OH-IMI	C₉H₁₀ClN₅O₃	7.7	1^a
		5-OH-IMI	C₉H₁₀ClN₅O₃	7.7	1^a
		IMI-olefin	C₉H₈ClN₅O₂	7.4	1
	THIAC	THIAC	C₁₀H₉ClN₄S	9.9	1
		OH-THIAC-olefin	C₁₀H₇ClN₄OS	10.4	3
		OH-THIAC/THIAC-sulfoxide (3)	C₁₀H₉ClN₄OS	8.8/8.9 + 10.5	3
		THIAC-amide	C₁₀H₁₁ClN₄OS	8.3	3
		6-CNA-gly	C₈H₇ClN₂O₃	6.3	4
		‘C₁₁H₁₅ClN₄O₃S’	C₁₁H₁₅ClN₄O₃S	6.8	4
	ACE	ACE	C₁₀H₁₁ClN₄	7.9	1
		DME-ACE	C₉H₉ClN₄	7.3	1
		6-CNA-gly	C₈H₇ClN₂O₃	6.2	4
	THIAM	THIAM	C₈H₁₀ClN₅O₃S	7.4	1
		CLO	C₆H₈ClN₅O₂S	8.2	1
		DME-CLO	C₅H₆ClN₅O₂S	7.7	1
		Cys-THIAM	C₁₁H₁₆N₆O₅S₂	3.6	3
	CLO	CLO	C₆H₈ClN₅O₂S	8.2	1
		DME-CLO	C₅H₆ClN₅O₂S	7.7	1
		CLO-urea	C₆H₈ClN₃OS	6.7	2b
		Cys-CLO	C₉H₁₄N₆O₄S₂	4.9	3
NNI-like compounds	FLUP	FLUP	C₁₂H₁₁ClF₂N₂O₃	9.5	1
		OH-FLUP (3)	C₁₂H₁₁ClF₂N₂O₄	9.2, 9.3 + 9.8	3
		DFE-FLUP	C₁₀H₉ClN₂O₂	7.6	2b
		6-CNA-gly	C₈H₇ClN₂O₃	6.3	2b
		DCP-FLUP	C₆H₇F₂NO₂	5.1	2b
	SULF	SULF	C₁₀H₁₀F₃N₃OS	9.9/10.1	1

The number of detected isomers is given in parentheses behind the corresponding name. Confidence level (and required information). 1: confirmed structure (MS, MS², retention time, reference standard); 2a: probable structure (MS, MS², library MS²); 2b: probable structure (MS, MS², experimental data); 3: tentative candidate (MS, MS², experimental data); 4: unequivocal molecular formula (MS isotope/adduct); 5: exact mass of interest (MS)

^aA separate isocratic method showed the formation of both, 4- and 5-OH-IMI (see text)