Table 2.

The calculated lipophilicities (log P/Clog P), electronic σ parameters and IC₅₀ [μmol/L] values related to PET inhibition in spinach chloroplasts of naphthalene-2-carboxamides 20–38c in comparison with 3-(3,4-dichlorophenyl)-1,1-dimethylurea (DCMU) standard. NF = not found in literature, ND = not determined due to precipitation during the experiment or interaction with 2,6-dichlorophenol-indophenol (DCIPP).

Comp.	R1	R2	PET inhibition IC50 [μmol/L]	log P ACD/Log P	σ [35]
20	i-Pr	H	353	2.97 ± 0.28	−0.19 [36]
21	–C12H25	H	845	7.94 ± 0.28	NF
22	–(CH2)4–		ND	2.10 ± 0.23	NF
23	–(CH2)5–		ND	2.67 ± 0.23	NF
24	c-Pn	H	ND	3.59 ± 0.28	−0.20 [36]
25	c-Hx	H	ND	4.15 ± 0.28	−0.15 [36]
26	c-Hp	H	216	4.21 ± 0.28	NF
27	c-Oc	H	688	5.28 ± 0.28	NF
28	Ph	H	20.7	3.85 ± 0.29	0.60 [36]/0
29	Bn	H	7.5	3.87 ± 0.28	0.22 [36]
30	–C2H4Ph	H	ND	4.28 ± 0.29	0.08 [36]
31b	3-OH-Ph	H	ND	3.50 ± 0.31	0.12
31c	4-OH-Ph	H	ND	3.11 ± 0.30	−0.37
32a	2-OCH3-Ph	H	763.0	3.75 ± 0.32	−0.39 [37]
32b	3-OCH3-Ph	H	306.2	4.01 ± 0.32	0.12
32c	4-OCH3-Ph	H	ND	3.80 ± 0.32	−0.27
33a	2-CH3-Ph	H	ND	4.31 ± 0.30	NF
33b	3-CH3-Ph	H	ND	4.31 ± 0.30	−0.07
33c	4-CH3-Ph	H	ND	4.31 ± 0.30	−0.17
34a	2-F-Ph	H	ND	3.82 ± 0.40	0.24 [38]
34b	3-F-Ph	H	ND	4.34 ± 0.41	0.34
34c	4-F-Ph	H	ND	4.30 ± 0.41	0.06
35a	2-Cl-Ph	H	ND	4.36 ± 0.32	0.20 [38]
35b	3-Cl-Ph	H	81.0	4.88 ± 0.33	0.37
35c	4-Cl-Ph	H	ND	4.84 ± 0.32	0.23
36a	2-Br-Ph	H	ND	4.54 ± 0.40	0.21 [38]
36b	3-Br-Ph	H	102.8	5.06 ± 0.41	0.39
36c	4-Br-Ph	H	ND	5.02 ± 0.41	0.23
37b	3-CF3-Ph	H	309.4	5.20 ± 0.39	0.43
37c	4-CF3-Ph	H	ND	4.86 ± 0.37	0.74
38a	2-NO2-Ph	H	ND	4.10 ± 0.34	0.80 [38]
38b	3-NO2-Ph	H	633.3	4.24 ± 0.34	0.71
38c	4-NO2-Ph	H	260.0	4.31 ± 0.34	1.26
DCMU	–	–	1.9	–	–