Mutagenic effects of the herbicide 3′,4′-dichloropropionanilide and its degradation products

1970 ◽  
Vol 16 (5) ◽  
pp. 369-372 ◽  
Author(s):  
Ishwari Prasad
Keyword(s):  
Aspergillus Nidulans ◽  
Benzene Ring ◽  
Mutation Frequency ◽  
Degradation Products ◽  
Para Position ◽  
Ortho Position ◽  
Back Mutation ◽  
Mutagenic Effects

3′,4′-Dichloropropionanilide; its biodegradation products 3,4-dichloroaniline and 3,3′,4,4′-tetrachloroazobenzene; and related chloroaniline and chlorobenzenes were tested for effects on the back mutation frequency of the meth3 locus in Aspergillus nidulans. 3,4-Dichloroaniline was more mutagenic than 3,3′,4,4′-tetrachloroazobenzene and 3′,4′-dichloropropionanilide. Chlorine in the para position on benzene ring increased mutagenicity more than chlorine in the meta or ortho position. Chloroaniline was more mutagenic than the corresponding dichlorobenzene.

THE APPLICATION OF THE HAMMETT EQUATION TO ORTHO-SUBSTITUTED BENZENE REACTION SERIES

1960 ◽  
Vol 38 (12) ◽  
pp. 2493-2499 ◽  
Author(s):  
Marvin Charton
Keyword(s):  
Benzene Ring ◽  
Substituent Effects ◽  
Para Position ◽  
Steric Effects ◽  
Side Chain ◽  
Ortho Position ◽  
Reaction Site ◽  
Hammett Equation ◽  
Reaction Series ◽  
Electrical Effect

The Hammett equation is directly applicable to ortho-substituted benzene reaction series in which reaction site and benzene ring are separated by some group Z, apparently due to the absence of steric effects in these series. The σp values are used in the correlations. Fourteen ortho-substituted benzene reaction series have been correlated. The electrical effect of a substituent in the ortho position is found to be about 0.75 times its effect in the para position. The effect of the side-chain Z in the transmission of substituent effects is OCH2 > SCH2 > CH = CH > SeCH2 > CH2CH2.

Vicarious nucleophilic amination of nitroquinolines with 4-amino-1,2,4-triazole

2008 ◽  
Vol 86 (7) ◽  
pp. 682-685 ◽  
Author(s):  
Barbara Szpakiewicz ◽  
Maria Grzegożek
Keyword(s):  
Dimethyl Sulfoxide ◽  
Nucleophilic Substitution ◽  
Nitro Group ◽  
Para Position ◽  
Basic Medium ◽  
Ortho Position ◽  
Vicarious Nucleophilic Substitution

3-, 5-, 6-, 7- and 8-Nitroquinolines react with 4-amino-1,2,4-triazole in basic medium (potassium tert-butoxide-dimethyl sulfoxide) giving amino products of the vicarious nucleophilic substitution (VNS) of hydrogen, predominantly at ortho position to the nitro group, except 8-nitroquinoline, which reacts at para position. Additionally, furazano[3,4-f]- and furazano[3,4-h]quinoline were obtained in the case of 5- and 8- nitroquinoline, respectively. 2-Nitroquinoline was aminated to 2-quinolino(1,2,4-triazol-4-yl)amine in these conditions.Key words: nitroquinolines, vicarious nucleophilic substitution (VNS), 4-amino-1,2,4-triazole.

Preemergence Herbicidal Activities of 3-Phenoxypyridazine Derivatives

Weed Science ◽  
1972 ◽  
Vol 20 (4) ◽  
pp. 327-329 ◽  
Author(s):  
Tetsuo Takematsu ◽  
Yasutomo Takeuchi ◽  
Saburo Tamura
Keyword(s):  
Oryza Sativa ◽  
Glycine Max ◽  
Gossypium Hirsutum ◽  
Benzene Ring ◽  
Herbicidal Activity ◽  
Ortho Position ◽  
Lycopersicum Esculentum ◽  
Transplanted Rice ◽  
Phaseolus Angularis ◽  
Submerged Conditions

Preemergence herbicidal activities of 27 3-phenoxypyridazine derivatives were evaluated in pots under upland and submerged conditions. Each of the compounds containing an alkyl or halogen at the ortho position of the benzene ring showed marked herbicidal effects. The activity of some disubstituted compounds carrying one of the substituents at the ortho position was the next. Among the compounds tested, 3-(2-methylphenoxy)-, 3-(2,3-dimethylphenoxy)-, 3-(2,4-dimethylphenoxy)-, and 3-(2,6-dimethylphenoxy)-pyridazines exhibited an excellent margin of selectivity for tomato (Lycopersicum esculentum Mill.), cotton (Gossypium hirsutum L.), soybean (Glycine max (L.) Merr.), and Azuki bean (Phaseolus angularis Wight). For transplanted rice (Oryza sativa L. ‘Norin No. 29′) under submerged conditions, 3-(2-isopropylphenoxy)-and 3-(2-n-butylphenoxy)-pyridazines showed a remarkable margin of selectivity, though the herbicidal activity of both compounds was slightly inferior to that of 3-(2-methylphenoxy)-pyridazine.

scholarly journals Lack of Mutational Hot Spots during Decitabine-Mediated HIV-1 Mutagenesis

2015 ◽  
Vol 59 (11) ◽  
pp. 6834-6843 ◽  
Author(s):  
Jonathan M. O. Rawson ◽  
Sean R. Landman ◽  
Cavan S. Reilly ◽  
Laurent Bonnac ◽  
Steven E. Patterson ◽  
...  
Keyword(s):  
Hot Spots ◽  
Mutation Frequency ◽  
High Throughput Sequencing ◽  
Fold Increase ◽  
Lethal Mutagenesis ◽  
Immunodeficiency Virus ◽  
Mutagenic Effects ◽  
First Time ◽  
Hiv 1

ABSTRACTDecitabine has previously been shown to induce lethal mutagenesis of human immunodeficiency virus type 1 (HIV-1). However, the factors that determine the susceptibilities of individual sequence positions in HIV-1 to decitabine have not yet been defined. To investigate this, we performed Illumina high-throughput sequencing of multiple amplicons prepared from proviral DNA that was recovered from decitabine-treated cells infected with HIV-1. We found that decitabine induced an ≈4.1-fold increase in the total mutation frequency of HIV-1, primarily due to a striking ≈155-fold increase in the G-to-C transversion frequency. Intriguingly, decitabine also led to an ≈29-fold increase in the C-to-G transversion frequency. G-to-C frequencies varied substantially (up to ≈80-fold) depending upon sequence position, but surprisingly, mutational hot spots (defined as upper outliers within the mutation frequency distribution) were not observed. We further found that every single guanine position examined was significantly susceptible to the mutagenic effects of decitabine. Taken together, these observations demonstrate for the first time that decitabine-mediated HIV-1 mutagenesis is promiscuous and occurs in the absence of a clear bias for mutational hot spots. These data imply that decitabine-mediated G-to-C mutagenesis is a highly effective antiviral mechanism for extinguishing HIV-1 infectivity.

Substituent Effects of Phosphorus and Arsenic Containing Groups in Aromatic Substitution. IV. Nitration of Aromatic Phosphine Oxides

1975 ◽  
Vol 53 (10) ◽  
pp. 1468-1474 ◽  
Author(s):  
Edmund Malinski ◽  
Antonina Piekos ◽  
Tomasz A. Modro
Keyword(s):  
Sulfuric Acid ◽  
Benzene Ring ◽  
Phosphorus Atom ◽  
Substituent Effects ◽  
Ortho Position ◽  
Phosphine Oxides ◽  
Aromatic Substitution ◽  
Tertiary Phosphine ◽  
Aqueous Sulfuric Acid

The nitration of some tertiary phosphine oxides ArP(O)R2 in aqueous sulfuric acid has been investigated. All compounds studied react as conjugate acids. When the phosphinyl group is bonded directly to the benzene ring, high deactivation and meta-orientation is found, accompanied in most cases by some substitution at the ortho position. The substituent effects of the "quasiphosphonium" group P(OH)R2+are compared with those of structurally related systems and are discussed in terms of pπ–dπ, interactions of the oxygen and the phosphorus atom.

scholarly journals The assessment of the environmental hazard of isomers of 1,2,4-triazole phenolic derivatives for natural ecosystems

2021 ◽  
Vol 10 (1) ◽  
pp. 151-156
Author(s):  
Ekaterina Sergeevna Selezneva ◽  
Zoya Petrovna Belousova ◽  
Robert Olegovich Artyukov
Keyword(s):  
Negative Impact ◽  
Para Position ◽  
Screening Tests ◽  
Ortho Position ◽  
Natural Ecosystems ◽  
Allium Test ◽  
Minimum Concentration ◽  
Ortho Isomer ◽  
Biological Responses ◽  
Integral Assessment

Its necessary to synthesize homologues of compounds frequently used in practice and to analyze their biological activity in laboratory experiments using screening tests that provide an integral assessment of biological responses to assess the effect of anthropogenic xenobiotics with different structures on ecosystems adjacent to agricultural complexes. We analyzed alcohol solutions of 2-(1H-1,2,4-triazolyl-methyl)phenol (ortho-isomer) and 4-(1H-1,2,4-triazolyl-methyl)phenol (para-isomer) in three concentrations: 0,0001; 0,001; 0.01 mg/ml using the Allium-test. The solvent was 0,1% isopropyl alcohol; the test object was Allium fistulosum L. The duration of the experiment was 5 days. Triazolide solutions significantly inhibited seed germination at all investigated concentrations. However, no significant differences were found between the isomers and the studied concentrations. Both isomers inhibited root growth at all concentrations tested. The toxicity of a triazolide containing an OH group in the para-position didnt change over the selected concentration range. For its ortho-isomer, toxicity increased with increasing concentration, reaching the toxicity of its homologue at a dose of 0,01 mg/ml. Both tested compounds significantly inhibited the proliferation of meristem cells as compared to the control. At the same time, no differences were observed in the effect of homologues with the OH-group in the para- and ortho-position on the value of the mitotic index. However, we found a paradoxical reaction: both homologues showed maximum cytotoxicity at a minimum concentration of 0,0001 mg/ml, and cytotoxicity decreased with increasing concentration compared to control. A triazolid containing an OH group in the para-position caused a block at the metaphase and anaphase stages at the lowest concentration. The specificity of its action disappeared with an increase in concentration, which was expressed in a general prophase and metaphase block. Its ortho-isomer inhibited cell division at all concentrations at the prophase stage. Both compounds are mutagenic. The number of chromosomal aberrations depended on both the structure of the compounds and their concentration. The para-homologue is less mutagenic than ortho. In the ortho-homologue, mutagenicity decreased slightly with increasing concentration. The highest mutagenicity was found for the ortho-homologue at its lowest concentration. The paper discusses possible mechanisms of action of isomers and their negative impact on plant organisms in ecosystems.

Determination of preferred conformations of benzenetricarboxylic acids by means of genetic algorithm MNC for multi-modal search

2019 ◽  
Author(s):  
Chem Int
Keyword(s):  
Genetic Algorithm ◽  
Benzene Ring ◽  
Lower Energy ◽  
Planar Structure ◽  
Carboxyl Groups ◽  
Planar Geometry ◽  
Ortho Position ◽  
Trimesic Acid ◽  
Carboxylic Groups

The structures of benzenetricarboxylic acids: hemimellitic, trimellitic and trimesic have been investigated using genetic algorithm MNC. Calculated structures and heats of formation, using semi-empiric method AM1, are reported for all the lower-energy conformers of each species. In effect, hemimellitic acid and trimellitic in which the carboxyl groups are linked to the benzene ring in adjacent (ortho) positions assume a non-planar geometry, while trimesic acid which having no carboxylic groups in the ortho-position adopted a planar structure in the two most stable conformations.

Competitive inhibition of renal transport of p-aminohippurate by other mono-substituted hippurates

1960 ◽  
Vol 199 (3) ◽  
pp. 509-512 ◽  
Author(s):  
Alvin Essig ◽  
John V. Taggart
Keyword(s):  
Nitro Group ◽  
Benzene Ring ◽  
Electron Distribution ◽  
Competitive Inhibition ◽  
Para Position ◽  
Rabbit Kidney ◽  
Kidney Cortex ◽  
Renal Transport ◽  
Inverse Relation ◽  
Substituent Group

Competitive inhibition of PAH transport by hippurate substituted in the ortho-, meta-, or para-position by a methyl, fluoro, chloro, bromo, iodo, or nitro group has been studied with slices of rabbit kidney cortex. Meta-substituted hippurates are better inhibitors of PAH transport than are the corresponding para-substituted hippurates, which, in turn, are generally better inhibitors than the corresponding ortho-compounds. Within the meta- and para-series inhibitory effectiveness was directly related to the weight or bulk of the substituent group. An inverse relation was noted between the rate of transport and the capacity to inhibit PAH transport. No correlation was noted between inhibitory effectiveness and alteration of electron distribution on the benzene ring.

scholarly journals THE PROPORTION OF MUTANTS IN BACTERIAL CULTURES

1957 ◽  
Vol 41 (1) ◽  
pp. 119-129 ◽  
Author(s):  
John H. Northrop ◽  
M. Kunitz
Keyword(s):  
Growth Rate ◽  
Mutation Rate ◽  
Rate Constant ◽  
Growth Rates ◽  
Mutation Frequency ◽  
Growth Rate Constant ◽  
Bacterial Cultures ◽  
Frequency Rate ◽  
Back Mutation ◽  
Mutant Cells

The proportion of mutants in a growing culture of organisms will depend upon (a) the rate at which the wild cells produce them (with or without growth), (b) the back mutation rate, and (c) the growth rates of the wild and mutant cells. If the mutation rate without growth and the back mutation rate are neglected, the growth of a mutant is expressed by See PDF for Equation and the ratio of the mutant to wild by See PDF for Equation in which λ = mutation frequency rate constant, "mutation rate," A = growth rate constant of wild cells W, B = growth rate constant of mutant cells M. If the term [B – (1 – 2λ)A] is positive, the proportion of mutants increases continuously. If it is negative, the proportion of mutants reaches a constant value See PDF for Equation If mutation is assumed to occur without growth at the rate C, then the corresponding equations are (11), (12), and (14). See PDF for Equation If (B + C – A) is negative and t = ∞, See PDF for Equation If C << A, See PDF for Equation

Sign in / Sign up

Export Citation Format

Share Document