SEARCH · PubMed Health

Results for “Nitro Compounds”

Explore indexed PubMed citations for clinical trials, systematic reviews and public health research. Read source abstracts and follow each citation to its original PubMed record.

Quote a phrase for an exact phrase match. Source license links do not imply unrestricted reuse.

At least 1,171 records · Page 65Linked to original sources

PubMed2005

Assessment of cross-resistance potential to neonicotinoid insecticides in Bemisia tabaci (Hemiptera: Aleyrodidae).

Laboratory bioassays were carried out with four neonicotinoid insecticides on multiple strains of Bemisia tabaci (Gennadius) to evaluate resistance and cross-resistance patterns. Three imidacloprid-resistant strains and field populations from three different locations in the southwestern USA were compared in systemic uptake bioassays with acetamiprid, dinotefuran, imidacloprid and thiamethoxam. An imidacloprid-resistant strain (IM-R) with 120-fold resistance originally collected from Imperial Valley, California, did not show cross-resistance to acetamiprid, dinotefuran or thiamethoxam. The Guatemala-resistant strain (GU-R) that was also highly resistant to imidacloprid (RR=109-fold) showed low levels of cross-resistance when bioassayed with acetamiprid and thiamethoxam. However, dinotefuran was more toxic than either imidacloprid or thiamethoxam to both IM-R and GU-R strains as indicated by low LC50s. By contrast, a Q-biotype Spanish-resistant strain (SQ-R) of B. tabaci highly resistant to imidacloprid demonstrated high cross-resistance to the two related neonicotinoids. Field populations from Imperial Valley (California), Maricopa and Yuma (Arizona), showed variable susceptibility to imidacloprid (LC50s ranging from 3.39 to 115 microg ml(-1)) but did not exhibit cross-resistance to the three neonicotinoids suggesting that all three compounds would be effective in managing whiteflies. Yuma populations were the most susceptible to imidacloprid. Dinotefuran was the most toxic of the four neonicotinoids against field populations. Although differences in binding at the target site and metabolic pathways may influence the variability in cross-resistance patterns among whitefly populations, comparison of whitefly responses from various geographic regions to the four neonicotinoids indicates the importance of ecological and operational factors on development of cross-resistance to the neonicotinoids.

Animals↗

PubMed1988

Role of chemical concentration and second carbon sources in acclimation of microbial communities for biodegradation.

A study was conducted to determine the role of concentration of the test chemical, of a second organic compound, and of mutation in the acclimation period before the mineralization of organic compounds in sewage. The acclimation period for the mineralization in sewage of 2 micrograms of 4-nitrophenol (PNP) per liter increased from 6 to 12 days in the presence of 10 mg of 2,4-dinitrophenol per liter. The extension of the acclimation period was equivalent to the time required for mineralization of 2,4-dinitrophenol. In contrast, the time for acclimation for the degradation of 2 micrograms of PNP per liter was reduced when 10 or 100 mg of phenol per liter was added. Lower phenol levels increased the acclimation period to 8 days. The length of the acclimation period for PNP mineralization decreased as the initial concentration of PNP increased from 2 micrograms to 100 mg/liter. The acclimation period for phenol mineralization was lengthened as the phenol concentration increased from 100 to 1,400 mg/liter. The length of the acclimation period for PNP and phenol biodegradation was reproducible, but it varied among replicates for the biodegradation of other nitro-substituted compounds added to sewage or lake water, suggesting that a mutation was responsible for acclimation to these other compounds. The acclimation period may thus reflect the time required for the destruction of toxins, and it also may be affected by the concentration of the test compound or the presence of other substrates.

2,4-Dinitrophenol↗

PubMed2002

Nicotinic acetylcholine receptor binding of imidacloprid-related diaza compounds with various ring sizes and their insecticidal activity against Musca domestica.

Fifteen 5-substituted 1-(6-chloro-3-pyridylmethyl)-2-nitromethylene-1,3- diazacyclohexanes and three other related compounds having a five- or seven-membered ring were synthesized and their biological activities were measured in vivo and in vitro. The insecticidal (in vivo) activity was evaluated against houseflies Musca domestica L under synergistic conditions with propargyl propyl phenyl phosphonate and piperonyl butoxide. The binding activity of each compound to nicotinic acetylcholine receptor in vitro was measured using [125I] alpha-bungarotoxin. The insecticidal activities of the unsubstituted diazacyclohexane analogues were slightly higher than those of the imidazolidine analogues, but the enlargement of ring size to diazacycloheptane lowered the activity. Substitution of 1,3-diazacyclohexane or imidazolidine rings was not generally favourable for the activity, but the unsubstituted 1,3-diazacyclohexane analogue showed the highest binding activity. Ring substitutions and ring enlargement decreased the activity 100-30,000-fold.

Animals↗

PubMed2001

1-Amino-2-nitraminoethane.

The molecule of title compound, C(2)H(7)N(3)O(2), has a zwitterionic structure. All non-H atoms, apart from the terminal N atom of the NH(3) group, lie in the same plane, with a maximum deviation of 0.056 (1) A for the amine N atom of the nitramine group, whereas the deviation of the terminal N atom of the NH(3) group from the same plane is 1.222 (2) A. Intermolecular hydrogen bonds within the crystal form a three-dimensional network.

Crystallography, X-Ray↗

PubMed2001

Determination of imidacloprid, metalaxyl, myclobutanil, propham, and thiabendazole in fruits and vegetables by liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry.

Imidacloprid, metalaxyl, myclobutanil, propham, and thiabendazole have been simultaneously determined in strawberries, oranges, potatoes, pears, and melons by matrix solid-phase dispersion (MSPD) followed by liquid chromatography-atmospheric pressure chemical ionization-mass spectrometry (LC-APCI-MS) in positive-ion mode. The samples were homogenized with C8 bonded silica as MSPD sorbent, placed in a glass column, and eluted with dichloromethane. Chromatographic separation of the compounds was achieved on a reversed-phase LC column using a methanol-ammonium formate (50 mmol L(-1)) gradient as a mobile phase. Samples were screened by monitoring the protonated molecular ion at m/z 256 for imidacloprid, 280 for metalaxyl, 289 for myclobutanil, and 202 for thiabendazole, and the main fragment at m/z 138 for propham. Positive samples were confirmed by multiple-ion monitoring. The repeatability (<20%) and recovery (>57%) of the method were good, and limits of detection (<0.05 mg kg(-1)) were adequate.

Antinematodal Agents↗

PubMed2003

Topical toxicity of two acetonic fractions of Trichilia havanensis Jacq. and four insecticides to larvae and adults of Chrysoperla carnea (Stephens) (Neuroptera: Chrysopidae).

The toxicity of botanical origin compounds such as two acetonic fractions of the seed kernels of the Meliacea Trichilia havanensis Jacq with insecticide properties (azadirone (F12) and the mixture F18 [1,7+3,7-di-O-acethylhavanensin (4:1)], three insecticides commercially available (imidacloprid, natural pyrethrins+PBO, triflumuron) and phloxine B, were tested in the laboratory. Topical bioassays using third instar and newly emerged adults of the lacewing Chrysoperla carnea (Stephens) at the maximum field recommended rate in Spain for commercials and at 1,000 ppm of active ingredient for T. havanensis acetone fractions and phloxine-B, were carried out. Imidacloprid and triflumuron were very toxic to third instar larvae inhibiting adult emergence, being the rest of insecticides harmless. Fecundity and fertility were not affected by the non-toxic compounds. Concerning adults, only imidacloprid and natural pyrethrins killed them significantly 24 hours after treatment. Phloxine B, triflumuron and T. havanensis fractions were harmless and did not cause any effect on fecundity and fertility with the exception of triflumuron, which reduced considerably the egg hatch. It can be concluded that T. havanensis acetonic fractions and phloxine B were non-toxic to larvae and adults of C. carnea when treated topically, whereas triflumuron, natural pyrethrins and imidacloprid affected one or more of the evaluated parameters under our conditions.

Acetone↗

PubMed1975

Genetic characterization of adenine-3 mutants induced by 4-nitroquinoline 1-oxide and 4-hydroxyaminoquinoline 1-oxide in Neurospora crassa.

Specific locus mutations induced by the chemical carcinogens, 4-nitroquinoline 1-oxide (4NQO) and 4-hydroxyaminoquinoline 1-oxide (4HAQO), have been characterized to obtain a presumptive identification of the genetic alterations at the molecular level. One hundred eighty-four 4NQO-induced and 219 4HAQO-induced ad-3 mutants of Neurospora crassa obtained in previous studies were studied with a series of genetic tests that permits determination of their genotype and the frequencies of point mutations and multilocus deletions. These tests have shown that the spectrum of ad-3 mutations among 4NQO-induced mutants is similar to that of 4HAQO-induced mutants. None of the 4NQO- or 4HAQO-induced mutants is a multilocus deletion mutant. The ratio of ad-3A to ad-3B mutants is the same in the two samples, as well as the frequencies of complementing ad-3B mutants. These data suggest, then, that the mechanism of mutation induction by 4NQO in N. crassa is identical to that of 4HAQO. It is not clear, however, whether 4NQO is mutagenic per se or reduction of 4NQO to 4HAQO is the first step involved in the mutagenesis of this compound in Neurospora. The heterotaryon tests have shown that the relatively high frequencies of 4NQO- or 4HAQO-induced ad-3B mutants show allelic complementation and that most of the complementing ad-3B mutants (74% of 4NQO induced and 71% of 4HAQO induced) have nonpolarized complementation patterns. From this we conclude that both agents induce predominantly base-pair substitution mutations in N. crassa. The results are in agreement with our other studies which show that potent chemical carcinogens induce predominantly base-pair substitution mutations in N. crassa.

Adenine↗

PubMed1994

A new glibenclamide-insensitive neuroselective hyperpolarizing agent.

We describe a novel compound, (-)-N-(2-ethoxyphenyl)-N'-(1,2,3-trimethylpropyl)-2-nitroethene-1, 1-diamine), Bay x9227, that demonstrates dose-dependent hyperpolarizing activity of remarkable potency (EC50 3 picomolar) and selectivity for CNS neurons and clonal neurotypic cells compared to smooth muscle cells. Single cell membrane potential measurements were obtained in physiologic buffer using the fluorescent probe, bisoxonol. Unlike K+ATP-channel activators including its (+)-enantiomer (Hoffman et al., 1993, Biochem. Biophys. Res. Commun. 190(2), 551), this activity was insensitive to glibenclamide antagonism. These data suggest a novel pharmacologic site for effecting neuroselective hyperpolarization.

Animals↗

PubMed1993

Effects on thyroid hormone metabolism and depletion of lung vitamin A in rats by airborne particulate matter.

Thyroxine (T4) and vitamin A are important regulators of normal epithelial differentiation and proliferation and might act in the promotion phase of carcinogenesis. Thyroid hormone and vitamin A metabolism are linked by a common plasma carrier protein, transthyretin (TTR). Polychlorinated biphenyls (PCBs) and related organochlorine compounds deplete vitamin A and thyroxine by interaction with TTR and alteration of their metabolism in hepatic and other organs. In the present report an outdoor airborne particulate matter (APM) extract was tested for both interaction with thyroid hormone and vitamin A metabolism, in order to address the question of whether APM has the potency to deplete vitamin A and thyroid hormones. Furthermore, studies were performed to characterize compounds present in APM that interact with TTR. A third aim was to compare the interaction of APM extracts with TTR and thyroxine-binding globulin (TBG), the major carrier protein for thyroxine in humans. Results showed that a single treatment of rats with an outdoor APM extract depleted plasma thyroxine and triiodothyronine levels and increased plasma retinol levels gradually over the time period studied, while liver retinol, lung retinol, and retinyl palmitate levels were depleted by 30-50%. As outdoor APM was able to inhibit T4-TTR binding in vitro, this suggests that the reduction in thyroxine levels in vivo is caused by the same phenomenon. Experiments showed that the neutral fraction of the APM extract accounted for most of the inhibitory activity on T4-TTR binding. Polycyclic aromatic hydrocarbons and nitrated derivatives are not likely to be responsible for the activity of the neutral fraction, because several representatives of these compounds showed no or very little interaction with TTR. Pentachlorophenol, a compound with known inhibitory activity on T4-TTR binding, was detected in the organic acid fraction of both a cigarette smoke sample and an outdoor APM sample. Finally, it was shown that several indoor and outdoor APM extracts only interact with TTR, but not with TBG. As APM has the potency to deplete lung vitamin A in vivo and vitamin A might have a protective effect in the process of lung carcinogenesis, APM might increase the susceptibility for the development of lung cancer.

Aerosols↗

PubMed1984

Absorption of 3-nitropropanol (miserotoxin aglycone) from the compound stomach of cattle.

Miserotoxin, the toxic component of certain Astragalus spp. (Leguminosae), was rapidly hydrolyzed to 3-nitropropanol (NPOH) in the rumen of cattle dosed with timber milkvetch (A. miser var. serotinus). The aglycone showed a rapid rate of disappearance from the rumen with an average half-life of 1.24 h. In contrast to the passage of Co-EDTA, which showed an exponential rate of increase in the abomasum, NPOH was not detected in abomasal fluid collected from dosed cattle. Rapid absorption of NPOH from the rumen was shown by plasma levels of 3-nitropropionic acid (NPA) and inorganic nitrite, but conversion of NPOH to NPA was not observed to any significant extent in the rumen.

1-Propanol↗

PubMed2004

Antioxidant effects of taurine, vitamin C, and vitamin E on oxidative damage in hippocampus caused by the administration of 3-nitropropionic acid in rats.

The administration of 3-nitropropionic acid increases reactive oxygen species (ROS). Antioxidant defense mechanisms buffer these ROS converting them into non-damaging compounds. Taurine and vitamins C and E are antioxidants that play a role in the defense against cellular damage. This study examines the antioxidant effect of taurine, vitamin C, and vitamin E on acute hippocampal damage caused by 3-NP. Animals treated with 3-NP increased lipid peroxidation levels and astrocytic damage in the hippocampus. Administration of taurine, vitamin C, and vitamin E partially protected from oxidative damage, indicate that while all substances had antioxidant effects, only taurine showed morphological protection in surviving cells.

Animals↗

PubMed1975

The identification and analysis of the metabolic products of mephentermine.

Phentermine (Ib), N-hydroxymephentermine (Ic) and N-hydroxyphentermine (Id) were identified as metabolic products after in vitro incubation of mephentermine (Ia) with rabbit liver microsomal fractions. Compounds Ia, Ib and Ic were also identified as excretion products in the urine of a human subject given a single dose of mephentermine (Ia) sulphate. Derivatization with acetic anhydride, trifluoroacetic anhydride and the trimethylsilyl donor reagent N,O-bis-(trimethylsilyl)-trifluoroacetamide (BSTFA) or hexamethyldisilazane (HMDS) were used for qualitative identification of the metabolic products Ib-Id by g.l.c.-mass spectrometry and for quantitative determination of Ia-Id after extraction from rabbit hepatic homogenates. The synthesis of N-hydroxymephentermine (Ic) and the properties of the metabolic products are reported.

Adult↗

PubMed1981

Mutagenicity of aminocarbazoles and nitrocarbazoles.

The mutagenic activity of all 4 isomeric aminocarbazoles and 4 nitrocarbazoles was evaluated in Salmonella typhimurium tester strains TA98. TA100 and TA1535. All compounds were assayed both in the presence and absence of liver homogenate from Aroclor-treated rats. Among the aminocarbazoles, 2-aminocarbazole was found to be most active in both tester strains, although somewhat less active than 2-aminofluorene. 3-Aminocarbazole was the only other isomer that was mutagenic towards TA98 at the dose levels employed (5--200 micrograms). 4-Aminocarbazole was moderately active in TA100, and 1-aminocarbazole was inactive in both TA98 and TA100. Similar differences in mutagenic potency and specificity towards the tester strains were observed for the related series of nitrocarbazoles.

Amines↗

PubMed1984

Pyridonecarboxylic acids as antibacterial agents. 2. Synthesis and structure-activity relationships of 1,6,7-trisubstituted 1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids, including enoxacin, a new antibacterial agent.

The title compounds having nitro, amino, cyano, chloro, or fluoro as the C-6 substituent were prepared. Introduction of the chloro and cyano groups at C-6 was accomplished by the Sandmeyer reaction of 6-amino-1,8-naphthyridine derivatives 9 via their 6-diazonium salts. The reaction was extended to the synthesis of the 6-fluoro analogues, involving the Balz-Schiemann reaction of the diazonium tetrafluoroborate. Furthermore, a series of the 1-ethyl, 1-vinyl, 1-(2-fluoroethyl), and 1-(difluoromethyl) analogues of 7-substituted 6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acids was prepared. 1-Pyrrolidinyl and, particularly, N-substituted or unsubstituted 1-piperazinyl groups were introduced as the C-7 variants. As a result of this study, 1-ethyl-6-fluoro-1,4-dihydro-4-oxo-7-(1-piperazinyl)-1, 8-naphthyridine-3-carboxylic acid (named enoxacin, originally AT-2266) was found to show the most broad and potent in vitro antibacterial activity, an excellent in vivo efficacy on systemic infections, and a weak acute toxicity. Structure-activity relationships of compounds with variations of substituents at C-1, C-6, and C-7 are also discussed.

Animals↗

PubMed2000

Cyclohexadienone diazeniumdiolates from nitric oxide addition to phenolates.

Sterically hindered phenols react with nitric oxide under basic condititons to give either cyclohexadienone diazeniumdiolates or oximates. Phenols with 2,6-di-tert-butyl and 4-methyl (butylated hydroxy toluene, BHT), 4-ethyl, or 4-methoxy methylene substituents yield the corresponding 2,6-di-tert-butyl-2, 5-cyclohexadienone-4-alkyl-4-diazeniumdiolate salts (4-methyl 1a, 4-ethyl 3a, 4-methoxymethylene 5a). Phenols with 2,6-di-tert-butyl and 4-methylene (2,6-di-tert-butylphenol) substituents yield 4-methoxymethylenediazeniumdiolate (5a) together with 2, 6-di-tert-butyl benzoquinone oximate (6a), while phenols with 2, 6-di-tert-butyl and 4-methylenedimethylamino or hydrogen substituents yield exclusively 2,6-di-tert-butyl benzoquinone oximate (6a). Alkylation of the silver salts of 1a, or treating the O(2)-protonated diazeniumdiolate with diazomethane, both yield mixtures of O(1)- and O(2)-methylated isomers. All the compounds exhibit exothermic thermal decomposition except the quinuclidinium (1e, 3e, 5e) and triethylenediammonium (1f) salts which decompose endothermically. Three of the compounds namely "O(2)-protonated" (Z)-1-[4-(2, 6-di-tert-butyl-4-methyl-cyclohexadienonyl)]diazen-1-ium+ ++-1, 2-diolinic acid (1b), O(2)-methyl (Z)-1-[4-(2, 6-di-tert-butyl-4-methyl-cyclohexadienonyl)]diazen-1-ium+ ++-1,2-diolate (1c), and "O(2)-protonated" (Z)-1-[4-(2, 6-di-tert-butyl-4-methoxymethylenecyclohexadienonyl)]diazen- 1-ium-1, 2-diolinic acid (5b) were characterized by single-crystal X-ray diffraction studies. The diazeniumdiolate framework in all the structures is coplanar with considerable pi-bonding delocalized over the O-N-N-O framework.

Calorimetry, Differential Scanning↗

PubMed1991

Synthesis of a series of nitrothiophenes with basic or electrophilic substituents and evaluation as radiosensitizers and as bioreductively activated cytotoxins.

A series of 2- and 3-nitrothiophene-5-carboxamides bearing N-(omega-aminoalkyl) side chains has been prepared by treatment of the thiophenecarbonyl chloride with the appropriate (protected) omega-aminoalkylamine. Analogous N-(oxiranylmethyl)nitrothiophene-5-carboxamides have been synthesized by epoxidation of the corresponding N-allylamide. Compounds in both classes were evaluated in vitro both as radiosensitizers of hypoxic mammalian cells and as selective bioreductively activated cytotoxins. The most potent radiosensitizers were those agents with strong tertiary amine bases or oxiranes in the side chain. Studies in vivo showed that 2-methyl-N-[2-(dimethyl-amino)ethyl]-3-nitrothiophene-5- carboxamide caused slight radiosensitization of the KHT sarcoma in mice given 0.34 mmol kg-1. However, administration of this and related tertiary amines at higher doses was precluded by systemic toxicity.

Animals↗

PubMed2003

Asymmetric chloronicotinyl insecticide, 1-[1-(6-chloro-3-pyridyl)ethyl]-2-nitroiminoimidazolidine: preparation, resolution and biological activities toward insects and their nerve preparations.

The asymmetric chloronicotinyl insecticide, 1-[1-(6-chloro-3-pyridyl)ethyl]-2-nitroiminoimidazolidine, was prepared, and the absolute configurations of the enantiomers were determined by an X-ray analysis. The insecticidal activity against the housefly measured with metabolic inhibitors showed the (S) enantiomer to be slightly more active than the (R) isomer. Electrophysiological measurements on the American cockroach central nerve cord showed the compounds to elicite the impulses and subsequently blocked them. The neuroblocking potency of the (S) isomer was 5.9 microM, while that of the (R) isomer was as high as 73 microM. The molar concentrations required for 50% inhibition of the specific binding of [3H]imidacloprid to the housefly head membrane preparation were respectively 0.19 microM and 0.95 microM for the (S) and (R) isomers. This enatioselectivity ratio was smaller than 35 for nicotine isomers but greater than 2 for epibatidine isomers.

Animals↗

PubMed1991

Reduction of nitroaromatic compounds by anaerobic bacteria isolated from the human gastrointestinal tract.

Human intestinal microbial flora were screened for their abilities to reduce nitroaromatic compounds by growing them on brain heart infusion agar plates containing 1-nitropyrene. Bacteria metabolizing 1-nitropyrene, detected by the appearance of clear zones around the colonies, were identified as Clostridium leptum, Clostridium paraputrificum, Clostridium clostridiiforme, another Clostridium sp., and a Eubacterium sp. These bacteria produced aromatic amines from nitroaromatic compounds, as shown by thin-layer chromatography, high-pressure liquid chromatography, and biochemical tests. Incubation of three of these bacteria with 1-nitropyrene, 1,3-dinitropyrene, and 1,6-dinitropyrene inactivated the direct-acting mutagenicity associated with these compounds. Menadione and o-iodosobenzoic acid inhibited nitroreductase activity in all of the isolates, indicating the involvement of sulfhydryl groups in the active site of the enzyme. The optimum pH for nitroreductase activity was 8.0. Only the Clostridium sp. required added flavin adenine dinucleotide for nitroreductase activity. The nitroreductases were constitutive and extracellular. An activity stain for the detection of nitroreductase on anaerobic native polyacrylamide gels was developed. This activity stain revealed only one isozyme in each bacterium but showed that the nitroreductases from different bacteria had distinct electrophoretic mobilities.

Chromatography, High Pressure Liquid↗