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. 2011 Jun 17;8(6):2265–2303. doi: 10.3390/ijerph8062265

Table 1.

Effects of different groups of endocrine disruptorpesticides and their chemical structures (adapted from [65]).

Pesticides [66] Chemical structure Endocrine Disruptor Effects Biomonitoring in human samples
2,4-D (H)
M(g/Mol) = 221
pKa = 2.73
logP: 2.81		 graphic file with name ijerph-08-02265i1.jpg Synergistic androgenic effects when combined with testosterone [67] U: <LOD–598 ng/mL [68]
S : 0.07–0.56 μg/g creatinine [69]
Acephate (I)
M(g/Mol) = 183.2
pKa = 8.35
logP: −0.85		 graphic file with name ijerph-08-02265i2.jpg Disruption of hormone expression in the hypothalamus [70] U: <LOD–0.26 ng/mL [68]
H.S: 7.2 μg/mL [71] **
Acetochlor (H)
M(g/Mol) = 269.8
pKa = n.a
logP: 4.14		 graphic file with name ijerph-08-02265i3.jpg Interaction with uterine estrogen receptors, alteration of thyroid hormone dependant gene expression [72,73] U: <LOD–10.9 ng/mL [68]
S: 0.08–0.10 μg/g creatinine [69]
Alachlor (H)
M(g/Mol) = 269.8
pKa = 0.62
logP: 3.09		 graphic file with name ijerph-08-02265i4.jpg Competitive binding to estrogen and progesterone receptors. Interaction with the pregnane X cellular receptor, interfering with the production of enzymes responsible for steroid hormone metabolism [13,74] U: <LOD–305 ng/mL [68]
S: 0.31–0.72 μg/g creatinine [69]
Aldicarb (I)
M(g/Mol) = 190.3
pKa = n.a
logP: 1.15		 graphic file with name ijerph-08-02265i5.jpg Inhibition of 17 beta-estradiol and progesterone activity [13,75]
Aldrin (I)
M(g/Mol) = 364.9
pKa = n.a
logP: 6.5		 graphic file with name ijerph-08-02265i6.jpg Competitive binding to androgen receptors [76] H.S: 2.17–372 μg/L [77,78]
H.M: mean 0.03 mg/L ± 0.03 [79]
A.T: 25.6–137.2 ng/g lipid [78]
Atrazine (H)
M(g/Mol) = 215.7
PKa = 4.14, 10.7
logP: −0.97		 graphic file with name ijerph-08-02265i7.jpg Androgen inhibition, weak estrogenic effect.
Disruption of the hypothalamic control of lutenising hormone and prolactin levels. Induction of aromatase activity, increase estrogen production.
Adrenal glands damages and reduction of steroid hormone metabolism [13,80–83]		 U: <LOD–9.2 ng/mL [68,84]
H.S: mean 2 pg/g [76,85]
S: 0.07–0.17 μg/g creatinine [69]
Bendiocarb (I)
M(g/Mol) = 223.2
pKa = 8.8
logP: 1.7		 graphic file with name ijerph-08-02265i8.jpg Weak estrogen effect [13]
Benomyl (F)
M(g/Mol) = 290.3
pKa = 4.48
logP: 1.4		 graphic file with name ijerph-08-02265i9.jpg Increase of estrogen production and aromatase activity [86]
Bioallethrin (I)
M(g/Mol) = 302.4
pKa = n.a
logP: 4.68		 graphic file with name ijerph-08-02265i10.jpg Inhibition of estrogen-sensitive cells proliferation [87] M: 0.61–1.79 μg/mL [88]
H: 1.08–2.74 μg/mL [88]
Bitertanol (F)
M(g/Mol) = 337.4
pKa = n.a
logP: 4.1		 graphic file with name ijerph-08-02265i11.jpg Inhibition of aromatase activity, decrease of estrogens production and increase of androgens availability [89]
Bupirimate (F)
M(g/Mol) = 316.4
pKa = 4.4
logP: 3.68		 graphic file with name ijerph-08-02265i12.jpg Activation of Pregnane X cellular receptor [11]
Captan (F)
M(g/Mol) = 300.6
pKa = n.a
logP: 2.5		 graphic file with name ijerph-08-02265i13.jpg Inhibition of estrogen action [90]
Carbaryl (I)
M(g/Mol) = 201.2
pKa = 10.4
logP: 2.36		 graphic file with name ijerph-08-02265i14.jpg Weak estrogen effect [13]
Carbendazim (F)
M(g/Mol) = 191.2
pKa = 4.2
logP: 1.48		 graphic file with name ijerph-08-02265i15.jpg Increase of estrogen production and aromatase activity [86]
Carbofuran (I)
M(g/Mol) = 221.2
pKa = n.a
logP: 1.8		 graphic file with name ijerph-08-02265i16.jpg Increase of progesterone, cortisol and estradiol level and decrease of testosterone one [91] M.S: 0.007–17.63 ng/g [92]
U.C: 0.007–13.97 ng/g [92]
Chlorothalonil (F)
M(g/Mol) = 265.9
pKa = n.a
logP: 2.94		 graphic file with name ijerph-08-02265i17.jpg Activation of androgen-sensitive cells proliferation [93] M.S: 0.007–25.31 ng/g [92]
U.C: 0.007–25.12 ng/g [92]
H.S: mean 6 pg/g [85]
Chlordane (I)
M(g/Mol) = 409.8
pKa = n.a
logP: 2.78		 graphic file with name ijerph-08-02265i18.jpg Competitive binding to androgen receptors [76] Anti-estrogenic effect, inhibition of estradiol binding [13] M.P: 0–2.7 ng/g lipid [94]
B.S: <LOD–0.9 ng/g lipid [95]
H.M: 0.02–437 ng/g lipid [79,96–99]
FF: 0.1–0.3 ng/L [100]
Chlordecone (I)
M(g/Mol) = 490.6
pKa = n.a
logP: 4.5		 graphic file with name ijerph-08-02265i19.jpg Binding to estrogen and androgen receptors [90,101,102]
Chlorfenviphos (I)
M(g/Mol) = 359.6
pKa = n.a
logP: 1.36		 graphic file with name ijerph-08-02265i20.jpg Weak estrogen effect [103]
Chlorpyrifos methyl (I)
M(g/Mol) = 322.5
pKa = n.a
logP: 4		 graphic file with name ijerph-08-02265i21.jpg Antagonist to androgen activity [104] U : <LOD–57.7 ng/mL* [68,84]
M.S: 0.0007–10.1 ng/g [92]
U.C: 0.0007–1.84 ng/g [92]
H.S: mean 9 pg/g [85]
H: 1.77–2.16 1.83 μg/mL [88]
Cypermethrin (I)
M(g/Mol) = 416.3
pKa = n.a
logP: 5.3		 graphic file with name ijerph-08-02265i22.jpg Estrogenic effect [105,106] U: 0.5–100.4 μg/g * [107]
M: 1.85–2.43 μg/mL [88]
Cyproconazole (F)
M(g/Mol) = 291.8
pKa = n.a
logP:3.09		 graphic file with name ijerph-08-02265i23.jpg Inhibition of aromatase activity, decrease of estrogens production and increase of androgens availability [89]
DDT and metabolites (I)
M(g/Mol) = 354.5
pKa = n.a
logP:6.91		 graphic file with name ijerph-08-02265i24.jpg Competitive binding to androgen receptors, activation of androgen-sensitive cells proliferation.
Stimulation of estrogen receptor production, estrogen receptor agonist and PR antagonist [76,93,108,109]		 M.P: 0.2–3588 ng/g lipid [94]
B.S: <LOD–40.9 ng/g lipid [95]
HM: 3.9–4700 ng/g lipid [110,96–99,111]
A.F: 0.1–0.63 mg/L [112]
M: 1.1–2.8 μg/mL [88]
H: 0.17–0.65 μg/mL [88,113]
M.B: 0–6168 ng/g lipid [110,114]
H.S: 12.5–814.9 ng/mL [77]
U.C: 189–3296 ng/g lipid [110]
Deltamethrin (I)
M(g/Mol) = 505.2
pKa = n.a
logP: 4.6		 graphic file with name ijerph-08-02265i25.jpg Weak estrogenic activity [8] U: 0.5–57.7 μg/g * [107]
Diazinon (I)
M(g/Mol) = 304.4
pKa = 2.6
logP: 3.69		 graphic file with name ijerph-08-02265i26.jpg Estrogenic effect [115] S: 1.84–4.96 μg/g creatinine * [69]
H.S: mean 2 pg/g [85]
Dichlorvos (I)
M(g/Mol) = 221
pKa = n.a
logP: 1.9		 graphic file with name ijerph-08-02265i27.jpg Weak androgen-receptor antagonist [8]
Dicofol (I)
M(g/Mol) = 370.5
pKa = n.a
logP: 4.3		 graphic file with name ijerph-08-02265i28.jpg Inhibition of androgen synthesis, increase of estrogens synthesis, binding to estrogen receptor [90,83]
Dieldrin (I)
M(g/Mol) = 380.9
pKa = n.a
logP: 3.7		 graphic file with name ijerph-08-02265i29.jpg Competitive binding to androgen receptors, estrogenic effect, stimulation of estrogen receptor production [8,76,108,116] H.M: <0.1–64 ng/g lipid [111]
Diflubenzuron (I)
M(g/Mol) = 310.7
pKa = n.a
logP: 3.89		 graphic file with name ijerph-08-02265i30.jpg Pregnane X cellular receptor activation [11] H.S: 1.21–356.4 μg/L [77,78]
H.M: mean 0.66 mg/L ± 1.75 [79]
A.T: 17.01–84.05 [78]
Dimethoate (I)
M(g/Mol) = 229.3
pKa = n.a
logP: 0.704		 graphic file with name ijerph-08-02265i31.jpg Disruption of thyroid hormones action. Increase of insulin blood concentration, decrease of luteinizing hormone blood concentration [117,118]
Diuron (H)
M(g/Mol) = 233.1
pKa = n.a
logP: 2.87		 graphic file with name ijerph-08-02265i32.jpg Inhibition of androgens action [83]
Endosulfan (I)
M(g/Mol) = 406.9
pKa = n.a
logP: 4.75		 graphic file with name ijerph-08-02265i33.jpg Competitive binding to androgen receptors, estrogenic effect, stimulation of estrogen receptor production, inhibition of aromatase activity [8,76,109,116] H.S: 8.85 547.6 μg/L [77,78]
A.T: 21.4 417.6 ng/g lipid [78]
Endrin (I)
M(g/Mol) = 380.9
pKa = n.a
logP: 3.2		 graphic file with name ijerph-08-02265i34.jpg Competitive binding to androgen receptors [76] H.M: mean 0.65 mg/L ± 1.63 [79]
H.S: 1.21 6.35 μg/L [78]
A.T: 47.43 148.13 ng/g lipid [78]
Epoxyconazole (F)
M(g/Mol) = 329.8
pKa = n.a
logP: 3.3		 graphic file with name ijerph-08-02265i35.jpg Inhibition of aromatase activity, decrease of estrogen production and increase available androgens [89,119]
Fenarimol (F)
M(g/Mol) = 331.2
pKa = n.a
logP: 3.69		 graphic file with name ijerph-08-02265i36.jpg Antagonist of androgenic action. Potential aromatase inhibition. Pregnane X cellular receptor activation [8,11,120]
Fenbuconazole (F)
M(g/Mol) = 336.8
pKa = n.a
logP: 3.79		 graphic file with name ijerph-08-02265i37.jpg Inhibition of thyroid hormones production, Pregnane X cellular receptor activation [11,13]
Fenitrothion (I)
M(g/Mol) = 277.2
pKa = n.a
logP: 3.32		 graphic file with name ijerph-08-02265i38.jpg Competitive binding to androgen receptor, inhibition of estrogens action [90,121] H.S: 4.5 μg/mL [71] **
Fenoxycarb (I)
M(g/Mol) = 301.3
pKa = n.a
logP: 4.07		 graphic file with name ijerph-08-02265i39.jpg Interference with testosterone metabolism [122]
Fenvalerate (I)
M(g/Mol) = 419.9
pKa = n.a
logP: 5.01		 graphic file with name ijerph-08-02265i40.jpg Inhibition of estrogen-sensitive cells proliferation, antagonist of the progesterone action [86,123]
Fluvalinate (I)
M(g/Mol) = 502.9
pKa = n.a
logP: 3.85		 graphic file with name ijerph-08-02265i41.jpg Binding to human sex hormone, Inhibition of progesterone production [124,125]
Flusilazole (F)
M(g/Mol) = 315.4
pKa = 2.5
logP: 3.87		 graphic file with name ijerph-08-02265i42.jpg Inhibition of aromatase activity, decrease of estrogens production, increase of available androgens [89]
Flutriafol (F)
M(g/Mol) = 301.3
pKa = 2.3
logP: 2.3		 graphic file with name ijerph-08-02265i43.jpg Weak estrogen inhibition [119]
Glyphosphate (H)
M(g/Mol) = 168.1
pKa = 0.78; 2.34; 5.96; 10.98
logP: −3.2		 graphic file with name ijerph-08-02265i44.jpg Disruption of aromatase activity, preventing the production of estrogens [126] U: 1.1–2.1 ng/mL [84]
HCB (F)
M(g/Mol) = 284.8
pKa = n.a
logP: 3.93		 graphic file with name ijerph-08-02265i45.jpg Severely disruption of thyroid hormone production. Enhancement of androgen action at low doses, but inhibition at high levels [127,128] M.P: 1.6–44.3 ng/g lipid [94]
B.S: 7.4–37.2 ng/g lipid [95]
H.M: 0.4–472 ng/g lipid [79,96–99]
H.S: 12.5–393.3 μg/L [77]
H 1.2–15.9 pg/mg [113]
F.F: 0.11–0.2 ng/L [100]
A.F: [112]
HCH (lindane) (I)
M(g/Mol) = 290.8
pKa = n.a
logP: 3.61		 graphic file with name ijerph-08-02265i46.jpg Reduction of oestrous cycles and luteal progesterone concentrations. Increase of insulin and estradiol blood serum concentrations, decrease thyroxine concentrations. Competitive binding to AR, ER and PR [117,129] M.P: 0.4–2839 ng/g lipid [94]
B.S: <LOD–134 ng/g lipid [95]
H.M: 4.7–8700 ng/g lipid [80,110,96–99]
H.S: 1.08–265.8 μg/L [77,78]
H: 50.7–235 pg/mg [113]
A.T: 17.44–113.31 ng/g lipid [78]
M.B: 1.9–386.6 ng/g lipid [110, 114]
A.F: 0.1–0.26 ng/mL [112]
U.C: 4–130 ng/g lipid [110]
Heptachlor (I)
M(g/Mol) = 373.3
pKa = n.a
logP: 5.44		 graphic file with name ijerph-08-02265i47.jpg Binding to cellular estrogen and androgen receptors [130,131] M.P: 0.2–5.2 ng/g lipid [94]
B.S: <LOD–0.9 ng/g lipid [95]
Human serum: 12.5–139.1 μg/L [77]
H.M: mean 0.07 mg/L ± 0.34 [79]
Hexaconazole (F)
M(g/Mol) = 314.2
pKa = 2.3
logP: 3.9		 graphic file with name ijerph-08-02265i48.jpg Inhibition of aromatase activity, decrease of the estrogens production and increase of available androgens [89]
Isoproturon (H)
M(g/Mol) = 206.3
pKa = n.a
logP: 2.5		 graphic file with name ijerph-08-02265i49.jpg Pregnane X cellular receptor activation [11]
Iprodione (F)
M(g/Mol) = 330.2
pKa = n.a
logP: 3.1		 graphic file with name ijerph-08-02265i50.jpg Increase weakly aromatase activity, and estrogen production [8]
Linuron (H)
M(g/Mol) = 249.1
pKa = n.a
logP: 3		 graphic file with name ijerph-08-02265i51.jpg Competitive binding to androgen receptor, thyroid receptor agonist [131,132]
Malathion (I)
M(g/Mol) = 330.4
pKa = n.a
logP: 2.75		 graphic file with name ijerph-08-02265i52.jpg Inhibition of catecholamine secretion, binding to thyroid hormone receptors [13,133] U: <LOD–3195 ng/mL [68] *
M: 2.92–5.38 μg/mL [88]
H: 1.62–2.12 μg/mL [88]
S: 0.37–0.92 μg/g creatinine [69]
Methiocarb (H)
M(g/Mol) = 225.3
pKa = n.a
logP: 3.18		 graphic file with name ijerph-08-02265i53.jpg Inhibition of androgen activity and increase of estrogen one [8]
Methomyl (I)
M(g/Mol) = 162.2
pKa = n.a
logP: 1.24		 graphic file with name ijerph-08-02265i54.jpg Weak increase of aromatase activity and estrogen production [8,13]
Methoxychlor (I)
M(g/Mol) = 345.7
pKa = n.a
logP: 5.83		 graphic file with name ijerph-08-02265i55.jpg Strong estrogenic effect. Competitive binding to androgen receptor, interaction with the pregnane X cellular receptor [13,74,76] H.S: 0.38–0.39 μg/L [78]
A.T: 29.86–155.58 ng/g lipid [78]
Metolachlor
M(g/Mol) = 283.8
pKa = n.a
logP: 3.4		 graphic file with name ijerph-08-02265i56.jpg Pregnane X cellular receptor activation [11] U: <LOD–4.5 ng/mL [68,84]
H.S: mean 2 pg/g [85]
M.S: 0.007–1.96 ng/g [92]
U.C: 0.007–2.37 ng/g [92]
S: 0.20–0.48 μg/g creatinine [69]
Metribuzin (H)
M(g/Mol) = 214.3
pKa = 0.99
logP: 1.65		 graphic file with name ijerph-08-02265i57.jpg Hyperthyroidism, alteration of somatotropin levels [134]
Mirex (I)
M(g/Mol) = 545.5
pKa = n.a
logP: 5.28		 graphic file with name ijerph-08-02265i58.jpg Weak estrogen effect [13] M.P: 0.2–1.5 ng/g lipid [94]
B.S: <LOD–7.2 ng/g lipid [95]
H.M: 0.2–1.7 ng/g lipid [98]
Molinate (H)
M(g/Mol) = 187.3
pKa = n.a
logP: 2.86		 graphic file with name ijerph-08-02265i59.jpg Reproductive tract damage, reduction of fertility [13]
Myclobutanil (F)
M(g/Mol) = 288.8
pKa = 2.3
logP: 2.89		 graphic file with name ijerph-08-02265i60.jpg Weak estrogen and androgen inhibition, Binding to estrogen and androgen receptors, aromatase inhibition [89,90,119]
Nitrofen (H)
M(g/Mol) = 284.1
pKa = n.a
logP: 3.4		 graphic file with name ijerph-08-02265i61.jpg Estrogen and androgen inhibition [90]
Oxamyl (I)
M(g/Mol) = 219.3
pKa = n.a
logP: −0.44		 graphic file with name ijerph-08-02265i62.jpg Weak estrogen effect [13]
Parathion (I)
M(g/Mol) = 291.3
pKa = n.a
logP: 3.83		 graphic file with name ijerph-08-02265i63.jpg Inhibition of catecholamine secretion, increase of melatonin synthesis, inhibition of gonadotrophic hormone [13] U: <LOD–84 ng/mL * [68]
Penconazole (F)
M(g/Mol) = 284.2
pKa = 1.51
logP: 3.72		 graphic file with name ijerph-08-02265i64.jpg Weak estrogenic effect. Inhibition of aromatase activity, decrease of estrogens production and increase androgens availability [89,119]
Pentachlorophenol (H, F, I)
M(g/Mol) = 266.3
pKa = 4.73
logP: 3.32		 graphic file with name ijerph-08-02265i65.jpg Weak estrogenic and anti-androgenic affect [13] A.F : 0.15–0.54 ng/mL [135]
Permethrin (I)
M(g/Mol) = 391.3
pKa = n.a
logP: 6.1		 graphic file with name ijerph-08-02265i66.jpg Inhibition of estrogen-sensitive cells proliferation [87,106] U: 1–150 μg/g * [107]
Phenylphenol (F)
M(g/Mol) = 170.2
pKa = 9.97
logP:3.09		 graphic file with name ijerph-08-02265i67.jpg Estrogen agonist [136] A.F: 0.1–0.17 ng/mL [135]
Prochloraz (F)
M(g/Mol) = 376.7
pKa = 3.8
logP: 3.53		 graphic file with name ijerph-08-02265i68.jpg Activation of Pregnane X cellular receptor.
Antagonist to cellular androgen and estrogen receptors, agonist to Ah receptor and inhibition of aromatase activity [8,11,120,137]
Procymidone (F)
M(g/Mol) = 284.1
pKa = n.a
logP: 3.3		 graphic file with name ijerph-08-02265i69.jpg Competitive binding to androgen receptor [131]
Propamocarb (F)
M(g/Mol) = 188.3
pKa = 9.5
logP: 0.84		 graphic file with name ijerph-08-02265i70.jpg Weak increase of aromatase activity and estrogen production [8]
Propanil (H)
M(g/Mol) = 318.1
pKa = n.a
logP: 2.29		 graphic file with name ijerph-08-02265i71.jpg Increase of cellular response to estrogen [138]
Propazine (H)
M(g/Mol) = 229.8
pKa = 1.7
logP: 3.95		 graphic file with name ijerph-08-02265i72.jpg Induction of aromatase activity and increase of estrogen production [81]
Propiconazole (F)
M(g/Mol) = 342.2
pKa = 1.09
logP: 3.72		 graphic file with name ijerph-08-02265i73.jpg Weak estrogen and aromatase activity inhibition.
Decrease estrogens production and increase of androgens availability [89,119]
Propoxur (I)
M(g/Mol) = 209.2
pKa = n.a
logP: 0.14		 graphic file with name ijerph-08-02265i74.jpg Weak estrogenic effect [13] M: 0.24–1.50 μg/mL [88]
C.B: 0.77 μg/mL [88]
H: 0.22–0.42 μg/mL [88]
M.B: 0.67–0.77 μg/mL [88]
Prothiophos (I)
M(g/Mol) = 345.3
pKa = n.a
logP: 5.67		 graphic file with name ijerph-08-02265i75.jpg Estrogenic effect [115]
Pyridate (H)
M(g/Mol) = 378.9
pKa = n.a
logP: 0.5		 graphic file with name ijerph-08-02265i76.jpg Binding to estrogen and androgen receptors [90]
Pyrifenox (F)
M(g/Mol) = 295.2
pKa = 4.61
logP: 3.4		 graphic file with name ijerph-08-02265i77.jpg Weak estrogen inhibition [119]
Pyripyroxifen (I)
M(g/Mol) = 321.4
pKa = 6.87
logP: 5.37		 graphic file with name ijerph-08-02265i78.jpg Estrogenic effect [115]
Resmethrin (I)
M(g/Mol) = 338.4
pKa = n.a
logP: 5.43		 graphic file with name ijerph-08-02265i79.jpg Binding to sex hormone [124]
Simazine (H)
M(g/Mol) = 201.7
pKa = 1.62
logP: 2.3		 graphic file with name ijerph-08-02265i80.jpg Induction of aromatase activity, increase of estrogen production [81]
Sumithrin (I)
M(g/Mol) = 350.5
pKa = n.a
logP: 6.01		 graphic file with name ijerph-08-02265i81.jpg Increase of estrogen-sensitive cells proliferation, antagonist of the progesterone action [87,123]
Tebuconazole (F)
M(g/Mol) = 307.8
pKa = n.a
logP: 3.7		 graphic file with name ijerph-08-02265i82.jpg Inhibition of aromatase activity, decrease the estrogens production and increase androgens availability [89]
Tetramethrin (I)
M(g/Mol) = 331.4
pKa = n.a
logP: 4.6		 graphic file with name ijerph-08-02265i83.jpg Estrogen-antagonistic effects in females only [139]
Tolchlofos-methyl (I)
M(g/Mol) = 301.1
pKa = n.a
logP: 4.56		 graphic file with name ijerph-08-02265i84.jpg Competitive binding to cellular estrogen receptors [120]
Toxaphene (I)
M(g/Mol) = 411.8
pKa = n.a
logP: 3.3		 graphic file with name ijerph-08-02265i85.jpg Increase of estrogen-sensitive cells proliferation.
Inhibition of corticosterone synthesis in the adrenal cortex [13,116]
Triadimefon (F)
M(g/Mol) = 293.8
pKa = n.a
logP: 3.18		 graphic file with name ijerph-08-02265i86.jpg Estrogenic effect, inhibition of aromatase activity, decrease of estrogens production and increase androgens availability [90]
Triadimenol (F)
M(g/Mol) = 295.8
pKa = n.a
logP: 3.18		 graphic file with name ijerph-08-02265i87.jpg Estrogenic effect, inhibition of aromatase activity, decrease of estrogens production and increase androgens availability [89,90]
Tribenuron-methyl (H)
M(g/Mol) = 395.4
pKa = 4.7
logP: 0.78		 graphic file with name ijerph-08-02265i88.jpg Weak estrogenic effect [8]
Trichlorfon (I)
M(g/Mol) = 257.4
pKa = n.a
logP: 0.43		 graphic file with name ijerph-08-02265i89.jpg Alteration of thyroid function [140]
Trifluralin (H)
M(g/Mol) = 335.3
pKa = n.a
logP: 5.27		 graphic file with name ijerph-08-02265i90.jpg Interaction withs pregnane X cellular receptor, interference steroid hormone metabolism [74] M.S: 0.00–8.5 ng/g [92]
U.C: 0.007–4.42 ng/g [92]
Vinclozolin (F)
M(g/Mol) = 286.1
pKa = n.a
logP: 3.02		 graphic file with name ijerph-08-02265i91.jpg Competitive binding to androgen receptor Interactions with pregnane X cellular receptor, interference with steroid hormone metabolism. [8,74,131]

(H): Herbicide, (F): Fungicide, (I): Insecticide, (AFA): Antifouling agent, (T): Termiticide, U: urine, S: semen, H.S: human serum, H.M human milk, M: mecomium, H = hair, A.T: adipose tissues, F.F: follicular fluid, M.P: maternal plasma, U.C: umbilical cord.

*

Measured by the presence of its metabolite.

**

Case of poisoning patient.