Category: 3336-34-3

Kapustin, A. I. published the artcileSimultaneous application of 2M-4XM (Tropotox) and superphosphate in clover cultivation, HPLC of Formula: 3336-34-3, the publication is Khim. v Sel’sk. Khoz. (1965), 3(11), 41-4, database is CAplus.

Herbicidal activity of Tropotox (I) in combination with superphosphate was studied on a 2-year-old cultivation of pink clover. The soil on the lot was soddy podzolic, sandy-silty clay, containing 4% of humus, 6 mg. of P and, 16 mg. of K/100 g. of soil, 75% saturated with alk. materials, pH 5.6. I at 4 kg./ha. was most effective against dicotyledonous perennials, e.g. yellow thistle and bindweed (reduced to half the control amount). Combination of I (4 kg./ha.) and superphosphate (10 kg./ha. of P₂O₅) was even more effective, killing 85% of the above weeds. I was also effective against dicotyledonous annuals, but in combination with superphosphate its effectiveness dropped. During the first 5-10 days after application of I, the growth of clover was slightly suppressed, but it then continued in a normal manner. I at 4 kg./ha. alone and in mixture with 10 kg. superphosphate/ha. does not affect the quality of clover seeds. At large doses of I (6 kg./ha.), the seed were impaired.

Khim. v Sel’sk. Khoz. published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, HPLC of Formula: 3336-34-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Mulder, A. H. published the artcileInhibitory action of 2,6-dichloro-3-hydroxybenzonitrile and 2,6-dichloro-4-hydroxybenzonitrile on the beating of heart cells in tissue culture. Antagonism of oligomycin, Synthetic Route of 3336-34-3, the publication is Biochimica et Biophysica Acta, Enzymology and Biological Oxidation (1966), 128(2), 391-3, database is CAplus.

The effects of 2,6-dichloro-3-hydroxybenzonitrile (I) and 2,6-dichloro-4-hydroxy-benzonitrile (II), uncouplers of oxidative phosphorylation, on the beating of heart cells were studied and compared with those obtained with 2,4-dinitrophenol (III). Concentrations of I, II, and III necessary to arrest beating were 0.3, 0.24, and 0.41 mM, resp. Oligomycin, when added 5 min. after these phenols had arrested the beating of the cells, partially restored the beating of I- or III-arrested cells, and completely restored the beating of II-arrested cells. ATP, to varying degrees, restored the beating of the phenol-arrested cells. III-treated cells started beating within 60 sec. after ATP addition, whereas I-treated cells began to beat 2-3 min. after ATP addition Cultures pretreated with II did not respond to ATP during the time of observation (6 min.). When II-inhibited cells were treated with oligomycin (20 γ/ml.) 6 min. after ATP addition, they started to beat again. A rise in frequency by ATP addition after oligomycin treatment was also observed on I-and III-inhibited cells. The differences in response to ATP additions by cells pretreated with these phenols probably reflect the quantitative differences in induction of ATPase in the living cells. The antagonism of oligomycin to the 2,6-dichlorobenzonitriles is in good agreement with the previous conclusion that the compounds act on the mitochondria and not on the cytoplasmic constituents of the living cell.

Biochimica et Biophysica Acta, Enzymology and Biological Oxidation published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, Synthetic Route of 3336-34-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Beynon, Kenneth I. published the artcileBreakdown of the herbicide chlorthiamid-14C. II. Glasshouse studies of breakdown in soils and in crops grown in the soils, Synthetic Route of 3336-34-3, the publication is Journal of the Science of Food and Agriculture (1968), 19(12), 727-32, database is CAplus.

Plants were grown to harvest in a glasshouse in soils treated once with chlorthiamid-14C(2,6-dichlorothiobenzamide) at dosage levels (1-3 lb./acre active mols.) near those recommended for com. field use. Rice plants (stems and leaves) grown in soil treated at 1 lb./acre contained dichlobenil (2,6-dichlorobenzonitrile, 0.03 ppm.) and 2,6-dichlorobenzamide (0.06 ppm.) and the grain itself showed a total residue of 14C-labeled components of only 0.06 ppm. (expressed as equivalent weight of chlorthiamid) at harvest. Winter wheat plants (stalks and leaves) grown in medium loam treated at 1.2 lb./acre contained residues of 2,6-dichlorobenzamide and free and conjugated 3-hydroxy-2,6-dichlorobenzamide, together with traces of sugar conjugates of 3-hydroxy- and 4-hydroxy-2,6-di-chlorobenzonitrile. The fruit of apple grown in a glasshouse in soil treated once at 1.5 lb./acre, showed no detectable residue (<0.004 ppm.) in spite of total residues of up to 2.4 ppm. in the leaves. The latter probably resulted from sublimation of dichlobenil from the soil. Such a mode of uptake would be unlikely to lead to as much residue in the leaves under field conditions. Traces of dichlobenil (0.005 ppm.), 2,6-dichlorobenzamide (0.02 ppm.) with larger amounts of glycosides of 3-hydroxy-2,6-dichlorobenzamide (1.3 ppm.) and 3-hydroxy- and 4-hydroxy-2,6-dichlorobenzonitriles (0.6 ppm. and 0.5 ppm., resp.) were identified in the leaves at harvest. All of the breakdown products of chlorthiamid that have been identified are of low acute oral mammalian toxicity.

Journal of the Science of Food and Agriculture published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, Synthetic Route of 3336-34-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wit, J. G. published the artcileMetabolism of the herbicide 2,6-dichlorobenzonitrile in rabbits and rats, Application In Synthesis of 3336-34-3, the publication is Biochemical Journal (1966), 698-706, database is CAplus and MEDLINE.

cf. preceding abstract. The metabolism of 2,6-dichlorobenzonitrile was studied in rabbits and rats. Oral administration caused an increased urinary excretion of glucuronides and ethereal sulfates. There was also an indication of mercapturic acid formation. 2,6-Dichloro-3-hydroxybenzonitrile and its 4-hydroxy analog were identified as metabolites in the urine. A small amount of the unchanged substance was recovered from the feces. By using 2,6-dichlorobenzonitrile-¹⁴C, the phenolic metabolites were determined quant. and some other possible metabolic routes were excluded. Incubation of 2,6-dichlorobenzonitrile with enzyme preparations (papain and high-speed supernatant of rat-liver homogenate plus glutathione) gave no indications for a reaction with thiol compounds

Biochemical Journal published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C15H14Cl2S2, Application In Synthesis of 3336-34-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Wit, J. G. published the artcileMonophenolic metabolites of the herbicide, 2,6-dichlorobenzonitrile, in animals as uncouplers of oxidative phosphorylation, Safety of 2,6-Dichloro-3-hydroxybenzonitrile, the publication is Biochemical Journal (1966), 707-10, database is CAplus and MEDLINE.

Both monophenolic metabolites of 2,6-dichlorobenzonitrile (2,6-dichloro-3-hydroxybenzonitrile and its 4-hydroxy analog) added to starved yeast cells incubated with a limited quantity of glucose caused a significant rise in O consumption of the cells. The same compounds induce ATPase activity in isolated intact rat liver mitochondria. The possible role of the hydroxylation of 2,6-dichlorobenzonitrile in mammals, in relation to hepatic injury, is discussed.

Biochemical Journal published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C6H10O2S, Safety of 2,6-Dichloro-3-hydroxybenzonitrile.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Fisher, D. E. published the artcileFate of Banvel T, ioxynil, Tordon, and trifluralin in the dairy cow, Computed Properties of 3336-34-3, the publication is Journal of Dairy Science (1965), 48(12), 1711-15, database is CAplus.

The metabolic fate of 5 ppm. of 4 orally administered herbicides was determined by gas chromatography on neutron activation analysis of total I in the feces, urine, rumen contents, and milk of dairy cows. No residues of Banvel T (2-methoxy-3,5,6-trichlorobenzoic acid), ioxynil (3,5-diiodo-4-hydroxybenzonitrile), or trifluralin (α,α,α-trifluoro-2,6-dinitro-N,N-dipropyl-p-toluidine) were found in the milk. Banvel T and Tordon (4-amino-3,5,6-trichloropicolinic acid) were eliminated unchanged in the urine. No ioxynil or a possible metabolite, 3,5-diiodo-4-hydroxybenzoic acid, was found in the milk, urine, or feces by gas chromatography, but neutron activation analysis of total I indicated that substantial amounts of ioxynil and a metabolite, possibly 3-iodo-4-hydroxybenzonitrile, were present. Trifluralin completely disappeared during 24 hrs. in an artificial rumen, possibly due to nitro reduction

Journal of Dairy Science published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, Computed Properties of 3336-34-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Griffiths, M. H. published the artcileThe comparative metabolism of 2,6-dichlorothiobenzamide (Preflx) and 2,6-dichlorobenzonitrile in the dog and rat, Related Products of nitriles-buliding-blocks, the publication is Biochemical Journal (1966), 98(3), 770-81, database is CAplus and MEDLINE.

A single oral dose of either 2,6-dichlorothiobenzamide-¹⁴C (I) or 2,6-dichlorobenzonitrile-¹⁴C (II) fed to rats is almost entirely eliminated in 4 days; 84.8-100.5% of ¹⁴C from I is excreted 67.3-79.7% in the urine; 85.8-97.2% of ¹⁴C from II is excreted, 72.3-80.7% in the urine. Only 0.37% of the I dose and 0.25 ± 0.03% of the II dose are present in the carcass plus viscera after gut removal. Rats do not show sex differences in the pattern of elimination of the resp. metabolites of the two herbicides. The rates of elimination of ¹⁴C from the two compounds in the 24-hr. and 48-hr. urines are not different from one another. After oral administration to dogs, 85.9-106.1% of ¹⁴C from I is excreted, 66.6-80.9% in the urine, and 86.8-92.5% of ¹⁴C from II is excreted, 60.0-70.1% in the urine. Dogs do not show sex differences in the pattern of eliminating the metabolites of either I or II. Dogs and rats do not show species differences in the patterns of elimination of the two herbicides. I and II are completely metabolized; unchanged I and II are absent from the urine and feces, and from the carcasses when elimination is complete. In the hydrolyzed urine of rats dosed with either I or II, 2,6-dichloro-3-hydroxybenzonitrile accounts for approx. 42% of the ¹⁴C, a further 10-11% is accounted for by 2,6-dichlorobenzamide, 2,6-dichlorobenzoic acid, 2,6-dichloro-3- and -4-hydroxybenzoic acid and 2,6-dichloro-4-hydroxybenzonitrile collectively, and 25-30% by six polar constituents, of which two are S-containing amino acids. In the unhydrolyzed urines of rats dosed with either I or II, there are present free 2,6-dichloro-3- and -4-hydroxybenzonitrile, their glucuronide conjugates, ester glucuronides of the principal aromatic acids that are present in the hydrolyzed urines, and two S-containing metabolites analogous to mercapturic acids or premercapturic acids.

Biochemical Journal published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, Related Products of nitriles-buliding-blocks.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Sikka, Harish C. published the artcileUptake and metabolism of dichlobenil by emersed aquatic plants, HPLC of Formula: 3336-34-3, the publication is Journal of Agricultural and Food Chemistry (1974), 22(2), 230-4, database is CAplus and MEDLINE.

14C-nitrile-labeled dichlobenil (2,6-dichlorobenzonitrile)(I) [1194-65-6] was readily absorbed and translocated by roots of the immersed aquatic plants, alligator weed (Alternanthera philoxeroides) and parrot feather (Myriophyllum brasiliense). Parrot feather metabolized I principally to 3-hydroxy-2,6-dichlorobenzonitrile [3336-34-3], 2,6-dichlorobenzamide [2008-58-4], and 2,6-dichlorobenzoic acid [50-30-6], whereas alligator weed did not metabolize I.

Journal of Agricultural and Food Chemistry published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C15H10O2, HPLC of Formula: 3336-34-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Bakke, J. E. published the artcileMetabolism of 2,6-dichlorobenzonitrile, 2,6-dichlorothiobenzamide in rodents and goats, Application In Synthesis of 3336-34-3, the publication is Xenobiotica (1988), 18(9), 1063-75, database is CAplus and MEDLINE.

Twelve ¹⁴C-labeled metabolites were isolated from either urine or bile from either rats (11 metabolites) or goats (7 metabolites) given single oral doses of 2,6-dichlorobenzo[¹⁴C]nitrile (DCBN). Five of these metabolites were also excreted in urine from rats dosed orally with 2,6-dichlorothiobenz[¹⁴C]-amide (DCTBA). All metabolites from either DCBN or DCTBA were benzonitriles with the following ring substituents: Cl₂, OH (three isomers); Cl₂, (OH)₂; Cl, (OH)₂; Cl, OH, SH; Cl, OH, SCH₃; SCH₃, SOCH₃, OH; Cl₂, S-(N-acetyl)cysteine; Cl, S-(N-acetyl)cysteine; Cl, OH, S-(N-acetyl)cysteine. The thiobenzamide moiety of DCTBA was converted to the nitrile in all the excreted urinary metabolites. No hydrolysis of the nitrile in DCBN to either an amide or an acid was detected. Urine was the major route for excretion; however, enterohepatic circulation occurred. Whole-body autoradiog. of ¹⁴C-DCBN and ¹⁴C-DCTBA in mice showed the presence of bound residues in the mucosa of the nasal cavity, trachea, tongue, esophagus, the kidney, liver, and the intestinal contents.

Xenobiotica published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C7H3Cl2NO, Application In Synthesis of 3336-34-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts

Van Genderen, H. published the artcileToxicological properties of the herbicide dichlobenil, 2,6-dichlorobenzonitrile, in warm-blooded animals, SDS of cas: 3336-34-3, the publication is Mededelingen Rijksfaculteit Landbouwwetenschappen, Gent (1966), 31(3), 1026-31, database is CAplus.

After oral administration of 100 mg. dichlobenil/kg. body weight, rabbits converted approx. 23% into 2,6-dichloro-3-hydroxybenzonitrile (I) and 2% into the 4-hydroxy analog (II). Rats excreted, resp., 22% and 9% of I and II. In mice the i.p. LD50 for I and II was 83 mg./kg. and 50 mg./kg., resp. The oral toxicity for mice and rabbits was very much lower. The effects of I and II were studied on the respiration of bakers’ yeast, on the ATPase induction in isolated mitochondria, on the contraction of isolated rat diaphragm, and on single beating rat heart cells in tissue culture. It was concluded that I and II, like other chlorophenols, were uncoupling agents of oxidative phosphorylation with approx. the same potency as 2,4-dinitrophenol. Liver function tests with dichlobenil showed different results for rats and rabbits. The effect on the liver of the rat seemed to be reversible, but, at a critical dose level for the rabbit, it was irreversible. It was suggested that in the rat liver cells the conjugation of the phenols to glucuronides and sulfates could keep pace with their formation.

Mededelingen Rijksfaculteit Landbouwwetenschappen, Gent published new progress about 3336-34-3. 3336-34-3 belongs to nitriles-buliding-blocks, auxiliary class Chloride,Nitrile,Benzene,Phenol, name is 2,6-Dichloro-3-hydroxybenzonitrile, and the molecular formula is C8H10S, SDS of cas: 3336-34-3.

Referemce:
https://en.wikipedia.org/wiki/Nitrile,
Nitriles – Chemistry LibreTexts