nitrophenolate mixture
Plant growth regulator
NOMENCLATURE
sodium 5-nitroguaiacolate
IUPAC name sodium 2-methoxy-5-nitrophenolate
Chemical Abstracts name 3-hydroxy-4-methoxynitrobenzene sodium salt
Other names 5 NG, sodium 5-nitroguaiacolate CAS RN [67233-85-6]
sodium o-nitrophenolate
IUPAC name sodium 2-nitrophenolate; sodium o-nitrophenolate
Chemical Abstracts name sodium o-nitrophenolate
Other names oNP CAS RN [824-39-5]
sodium p-nitrophenolate
IUPAC name sodium 4-nitrophenolate; sodium p-nitrophenolate
Chemical Abstracts name sodium p-nitrophenolate
Other names pNP CAS RN [824-78-2]
PHYSICAL CHEMISTRY
nitrophenolate mixture
Composition 'Atonik' contains 0.1% sodium 5-nitroguaiacolate, 0.2% sodium o-nitrophenolate and 0.3% sodium p-nitrophenolate.
sodium 5-nitroguaiacolate
Composition Tech. is ³99.0% pure. Mol. wt. 191.1 M.f. C7H6NNaO4 Form Red crystalline powder with a musty odour. M.p. decomposes above 145 °C V.p. 4.80 ´ 10-9 mPa (25 °C, gas saturation method) KOW logP = 1.49 (pH 4), 1.62 (pH 7), -0.25 (pH 10) S.g./density 1.55 (22 °C) Solubility In water 1.3 (pH 4), 1.8 (pH 7), 86.8 (pH 10) (all g/l). In n-heptane 2.8, o-xylene 29, 1,2-dichloroethane 39, acetone 170, methanol 53000, ethyl acetate 59 (all mg/l). Stability Stable under dry conditions. pKa 8.21 (22 °C) F.p. Highly flammable (Koenen apparatus); explosive (Hammer fall)
sodium o-nitrophenolate
Composition Tech. is ³98.1% pure. Mol. wt. 161.1 M.f. C6H4NNaO3 Form Red crystalline powder with a musty odour. M.p. decomposes above 280 °C V.p. 3.33 ´ 10-13 mPa (25 °C, gas saturation method) KOW logP = 1.70 (pH 4), 1.12 (pH 7), -1.03 (pH 10) S.g./density 1.65 (22 °C) Solubility In water 0.78 (pH 4), 2.8 (pH 7), 181.6 (pH 10) (all g/l). In n-heptane <0.2, o-xylene <0.28, 1,2-dichloroethane <0.5, acetone 1200, methanol 47000, ethyl acetate 180 (all mg/l). Stability Stable under dry conditions. pKa 7.16 (22 °C) F.p. Highly flammable (Koenen apparatus); explosive (Hammer fall)
sodium p-nitrophenolate
Composition Forms a dihydrate. Mol. wt. 161.1 M.f. C6H4NNaO3 Form Bright yellow, fine granules. M.p. loses water of crystallisation above 94 °C; decomposes above 175 °C V.p. 2.80 ´ 10-9 mPa (25 °C, gas saturation method) KOW logP = 1.82 (pH 4), 1.28 (pH 7), -0.93 (pH 10) S.g./density 1.41 (22 °C) Solubility In water 14.7 (pH 4), 13.9 (pH 7), 57.4 (pH 10) (all g/l). In n-heptane 0.094, o-xylene 1.0, 1,2-dichloroethane 2.5, acetone 2400, methanol 181000, ethyl acetate 180 (all mg/l). pKa 7.16 F.p. Highly flammable (Koenen apparatus); explosive (Hammer fall)
COMMERCIALISATION
History 'Atonik' was invented in 1952 and introduced to the market by Asahi Chemical Manufacturing Co., Ltd. Manufacturers Asahi Chemical Manufacturing
APPLICATIONS
Biochemistry Stimulates endoauxin activity (regulation of indole-3-acetic acid oxidase) and activity of enzymes involved in mineral metabolism. Uses Plant growth stimulator which is reported to increase nutrient uptake by cotton, rice, and soya beans, applied at 2 l/ha. Formulation types SL. Selected products: 'Asahi' (Asahi Chemical Manufacturing); 'Atonik' (Asahi Chemical Manufacturing)
ANALYSIS
By hplc with u.v. detection.
MAMMALIAN TOXICOLOGY
nitrophenolate mixture
Oral Acute oral LD50 for rats >5000 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Skin and eye irritant (rabbits). Skin sensitiser (guinea pigs). Inhalation Acute LC50 for rats >6.7 mg/ml air. NOEL NOEL for rats c. 525 mg 'Atonik'/kg b.w. daily. NOAEL for maternal toxicity 300 mg/kg daily; NOAEL for developmental toxicity 600 mg/kg daily. ADI 0.125 mg/kg b.w. Toxicity class WHO (a.i.) II (company classification); EPA (formulation) IV
sodium 5-nitroguaiacolate
Oral Acute oral LD50 for rats 716 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Eye irritant; very mild skin irritant (rabbits). Not a skin sensitiser (guinea pigs). Inhalation Acute LC50 for rats >2.38 mg/l (dust). Other Non-mutagenic in the Ames and mouse micronucleus tests. Negative in CHO and rec assays. Toxicity class WHO (a.i.) II (company classification); EPA (formulation) III
sodium o-nitrophenolate
Oral Acute oral LD50 for rats 960 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Eye irritant; not a skin irritant (rabbits). Not a skin sensitiser (guinea pigs). Inhalation Acute LC50 for rats >1.24 mg/l (dust). Other Non-mutagenic in the Ames and mouse micronucleus tests. Negative in CHO and rec assays. Toxicity class WHO (a.i.) II (company classification); EPA (formulation) II
sodium p-nitrophenolate
Oral Acute oral LD50 for rats 345 mg/kg. Skin and eye Acute percutaneous LD50 for rats >2000 mg/kg. Eye and skin irritant (rabbits). Not a skin sensitiser (guinea pigs). Inhalation Acute LC50 for rats >1.20 mg/l (dust). Other Non-mutagenic in the Ames and mouse micronucleus tests. Negative in CHO and rec assays. Toxicity class WHO (a.i.) II (company classification); EPA (formulation) II
ECOTOXICOLOGY
nitrophenolate mixture
Algae ErC50 >100 mg/l (for 'Atonik') Bees LD50 (contact and oral) >100 µg/bee. Worms LC50 310 mg/kg dry soil.
sodium 5-nitroguaiacolate
Birds Acute oral LD50 for bobwhite quail 2067 mg/kg. Dietary LC50 for bobwhite quail >5620 ppm. Fish LC50 (96 h) for rainbow trout 37 mg/l. Daphnia EC50 (48 h) 71.1 mg/l. Algae EbC50 for Scenedesmus subspicatus 6.2 mg/l; ErC50 for Scenedesmus subspicatus 23.6 mg/l. Bees Acute LD50 (contact) for honey bees >100 mg/bee.
sodium o-nitrophenolate
Birds Acute oral LD50 for bobwhite quail 1046 mg/kg. Dietary LC50 for bobwhite quail >5620 ppm. Fish LC50 (96 h) for rainbow trout 69 mg/l. Daphnia EC50 (48 h) >68.8 mg/l. Algae EbC50 for Scenedesmus subspicatus 4.8 mg/l; ErC50 for Scenedesmus subspicatus 64.2 mg/l. Bees Acute LD50 (contact) for honey bees >100 mg/bee.
sodium p-nitrophenolate
Birds Acute oral LD50 for bobwhite quail >2000 mg/kg. Dietary LC50 for bobwhite quail >5620 ppm. Fish LC50 (96 h) for rainbow trout 25 mg/l. Daphnia EC50 (48 h) 27.7 mg/l. Algae EbC50 for Scenedesmus subspicatus 2.5 mg/l; ErC50 for Scenedesmus subspicatus 10.8 mg/l. Bees Acute LD50 (contact) for honey bees 111 mg/bee.
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