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1.
A serine-to-threonine substitution in the triazine herbicide-binding protein in potato cells results in atrazine resistance without impairing productivity. 下载免费PDF全文
A mutation of the psbA gene was identified in photoautotrophic potato (Solanum tuberosum L. cv Superior x U.S. Department of Agriculture line 66-142) cells selected for resistance to 6-chloro-N-ethyl-N'-(1-methylethyl)-1,3,5-triazine-2,4-diamine (atrazine). Photoaffinity labeling with 6-azido-N-ethyl-N'-(1-methylethyl)-1,3,5-triazine-2,4-diamine detected a thylakoid membrane protein with a M(r) of 32,000 in susceptible, but not in resistant, cells. This protein was identified as the secondary quinone acceptor of photosystem II (QB) protein. Atrazine resistance in selected cells was attributable to a mutation from AGT (serine) to ACT (threonine) in codon 264 of the psbA gene that encodes the QB protein. Although the mutant cells exhibited extreme levels of resistance to atrazine, no concomitant reductions in photosynthetic electron transport or cell growth rates compared to the unselected cells were detected. This is in contrast with the losses in productivity observed in atrazine-resistant mutants that contain a glycine-264 alteration. 相似文献
2.
Robert B. Mitchell Kenneth P. Vogel John Berdahl Robert A. Masters 《Bioenergy Research》2010,3(4):321-327
Weed interference limits switchgrass (Panicum virgatum L.) establishment from seed. Our objectives were to determine the effect of selected post-plant, preemergence herbicides on stand establishment and subsequent biomass yields of adapted upland switchgrass cultivars grown in three environments in the Central and Northern Great Plains. A separate experiment was conducted in eastern Nebraska to determine if there were any differences among switchgrass ecotypes for herbicide tolerance to the optimal herbicide combination. Herbicides applied immediately after planting were different concentrations of atrazine [Aatrex 4L®; 6-chloro-N-ethyl-N′-(1-methylethyl)-1,3,5-triazine-2,4-diamine], quinclorac (Paramount®; 3,7-Dichloro-8-quinolinecarboxylic acid), atrazine+quinclorac, imazapic {Plateau®; 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-1H-imidazol-2-yl]-5-methyl-3-pyridinecarboxylic acid}, and quinclorac+imazapic. Herbicide efficacy was determined by measuring stand frequency of occurrence and biomass yield the year after establishment. The application of quinclorac plus atrazine resulted in acceptable stands and high biomass yields. Imazapic often reduced switchgrass stands in comparison to the nontreated control and is not recommended for switchgrass establishment. In the multi-state trials, the herbicide by cultivar interaction was not significant for stands or biomass yields, indicating that the effects of herbicides on switchgrass stands and biomass yields were consistent over the upland cultivars used in the trials. No differences were detected among switchgrass lowland and upland ecotypes for tolerance to atrazine and quinclorac. Quinclorac, which provides effective control of grassy weeds, and herbicides such as atrazine which provide good broadleaf weed control are an excellent herbicide combination for establishing switchgrass for biomass production in the Great Plains and the Midwest. 相似文献
3.
Purification and Characterization of an Inducible s-Triazine Hydrolase from Rhodococcus corallinus NRRL B-15444R 总被引:8,自引:4,他引:4 下载免费PDF全文
Walter W. Mulbry 《Applied microbiology》1994,60(2):613-618
The widespread use and relative persistence of s-triazine compounds such as atrazine and simazine have led to increasing concern about environmental contamination by these compounds. Few microbial isolates capable of transforming substituted s-triazines have been identified. Rhodococcus corallinus NRRL B-15444 has previously been shown to possess a hydrolase activity that is responsible for the dechlorination of the triazine compounds deethylsimazine (6-chloro-N-ethyl-1,3,5-triazine-2,4-diamine) (CEAT) and deethylatrazine (6-chloro-N-isopropyl-1,3,5-triazine-2,4-diamine) (CIAT). The enzyme responsible for this activity was purified and shown to be composed of four identical subunits of 54,000 Da. Kinetic experiments revealed that the purified enzyme is also capable of deaminating the structurally related s-triazine compounds melamine (2,4,6-triamino-1,3,5-triazine) (AAAT) and CAAT (2-chloro-4,6-diamino-1,3,5-triazine), as well as the pyrimidine compounds 2,4,6-triaminopyrimidine (AAAP) and 4-chloro-2,6-diaminopyrimidine (CAAP). The triazine herbicides atrazine and simazine inhibit the hydrolytic activities of the enzyme but are not substrates. Induction experiments demonstrate that triazine hydrolytic activity is inducible and that this activity rises approximately 20-fold during induction. 相似文献
4.
Sandra Trenkamp Peter Eckes Marco Busch Alisdair R. Fernie 《Metabolomics : Official journal of the Metabolomic Society》2009,5(3):277-291
We conducted a comprehensive metabolic phenotyping of primary metabolism of photosynthetic tissue of Arabidopsis thaliana following spray treatment with a number of commercially used herbicides using a well established gas-chromatography mass-spectrometry
profiling method. Applying this technique we were able to identify and quantify in excess of 80 polar metabolites and based
on a combination of co-elution with standards and prediction from the mass spectra a similar number of lipophillic components
within two chromatographic runs. The herbicides selected were glufosinate, sulcotrione, AE944 [N2-(1-ethyl-3-phenylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine],
foramsulfuron, benfuresate and glyphosate. We determined causal changes in the metabolite profiles by following their time-dependent
changes using a serial sampling strategy. The resultant profiles were compared both by looking at the largest changes in a
metabolite by metabolite manner and by performance of statistical analyses. These data revealed that analysis of the polar
metabolites allows clear separation of the compounds under test. This finding is discussed in the context of current strategies
for agrochemical discovery. 相似文献
5.
6.
Li A May MP Bigelow JC 《Journal of chromatography. B, Analytical technologies in the biomedical and life sciences》2006,836(1-2):129-132
Atrazine is an herbicide which has shown potential antimalarial effects both in vitro and in vivo in rats. In order to study the metabolism of atrazine in rat livers, we developed a sensitive LC/MS/MS method for the identification of atrazine and several of its metabolites. Using this method, we identified one previously unreported metabolite with a mass of 211 Da in addition to two known metabolites. This new metabolite was confirmed to be N-ethyl-6-methoxy-N'-(1-methylethyl)-1,3,5-triazine-2,4-diamine, also known as atraton, by comparison of the LC/MS/MS mass spectra and the retention time to those of a commercial standard. 相似文献
7.
Bacterial degradation of N-cyclopropylmelamine. The steps to ring cleavage. 总被引:1,自引:0,他引:1 下载免费PDF全文
The s-triazine cyclopropylmelamine (N-cyclopropyl-1,3,5-triazine-2,4,6-triamine) was degraded to about 6 mol of NH4+/mol of substrate by a mixture of two bacteria (strains A and D, both Pseudomonas spp.) Only strain A grew with cyclopropylmelamine as sole and limiting source of nitrogen. The organism obtained 2 mol of nitrogen/mol of substrate and excreted a product that was identified as cyclopropylammelide [6-cyclopropylamino-1,3,5-triazine-2,4(1 H,3 H)-dione]. Proteins in extracts from strain A were separated on a Sephadex G-200 column. Cyclopropylmelamine was found to be deaminated in two separable steps to cyclopropylammelide via cyclopropylammeline [4-amino-6-cyclopropylamino-1,3,5-triazine-2(1 H)-one], which was identified. Strain D could not utilize cyclopropylmelamine or cyclopropylammeline, but could utilize cyclopropylammelide (or homologue) as sole and limiting source of nitrogen and obtain about 4 mol of nitrogen/mol of substrate. Proteins in cell extracts from strain D were separated on a DEAE-cellulose column. Alkylammelides were degraded quantitatively by one enzyme fraction to 1 mol of cyanuric acid plus 1 mol of alkylamine/mol of substrate. The specific activities of enzymes in extracts of the two strains were as high as the activities observed during growth. The three activities studied in the two strains were all active under aerobic and oxygen-free conditions. The reactions appear to be hydrolytic, yielding 2 mol of NH4+ plus 1 mol of cyclopropylamine and 1 mol of cyanuric acid/mol of substrate. 相似文献
8.
Forty-five 1,3,5-triazine-2,6-dione derivatives were synthesized and their plant growth-promoting activities examined by the rice (Oryza sativa) seedling test in the presence or absence of gibberellic acid (GA). For high activity in promoting the growth of rice seedlings and acting as active GA-synergists, a para-substituted or a 2,4-disubstituted phenyl group, a hydrogen atom and an alkoxy group were required in the 1-, 3- and 4-positions of the 1,3,5-triazine-2,6-dione molecule. 4-Ethoxy-1-(p-tolyl)-s-triazine-2,6(1H, 3H)-dione [TA], one of the most potent triazinones, synergized the effect of GA on the shoot elongation of different varieties of rice including normal type, dwarf mutants and chlorophyll-mutants. TA synergistically increased the growth-promoting activity of GA by both a simultaneous treatment at the same sites and separate treatments at separate sites of rice seedlings. 相似文献
9.
Pseudomonas sp. strain A grew with 2-chloro-1,3,5-triazine-4,6-diamine as the sole and growth-limiting source of nitrogen. The substrate was utilized quantitatively and concomitantly with growth and with excretion of a product which was identified as 2-chloro-4-amino-1,3,5-triazine-6(5H)-one. The reaction yielded 1 mol of organic product and 1 mol of NH4+ per mol of substrate. 相似文献
10.
2-Chloro-4-amino-1,3,5-triazine-6(5H)-one: a new intermediate in the biodegradation of chlorinated s-triazines. 下载免费PDF全文
Pseudomonas sp. strain A grew with 2-chloro-1,3,5-triazine-4,6-diamine as the sole and growth-limiting source of nitrogen. The substrate was utilized quantitatively and concomitantly with growth and with excretion of a product which was identified as 2-chloro-4-amino-1,3,5-triazine-6(5H)-one. The reaction yielded 1 mol of organic product and 1 mol of NH4+ per mol of substrate. 相似文献
11.
Hydroxylation of the Herbicide Isoproturon by Fungi Isolated from Agricultural Soil 总被引:2,自引:1,他引:1 下载免费PDF全文
Stig Rnhede Bo Jensen Sren Rosendahl Birthe B. Kragelund Ren K. Juhler Jens Aamand 《Applied microbiology》2005,71(12):7927-7932
Several asco-, basidio-, and zygomycetes isolated from an agricultural field were shown to be able to hydroxylate the phenylurea herbicide isoproturon [N-(4-isopropylphenyl)-N′,N′-dimethylurea] to N-(4-(2-hydroxy-1-methylethyl)phenyl)-N′,N′-dimethylurea and N-(4-(1-hydroxy-1-methylethyl)phenyl)-N′,N′-dimethylurea. Bacterial metabolism of isoproturon has previously been shown to proceed by an initial demethylation to N-(4-isopropylphenyl)-N′-methylurea. In soils, however, hydroxylated metabolites have also been detected. In this study we identified fungi as organisms that potentially play a major role in the formation of these hydroxylated metabolites in soils treated with isoproturon. Isolates of Mortierella sp. strain Gr4, Phoma cf. eupyrena Gr61, and Alternaria sp. strain Gr174 hydroxylated isoproturon at the first position of the isopropyl side chain, yielding N-(4-(2-hydroxy-1-methylethyl)phenyl)-N′,N′-dimethylurea, while Mucor sp. strain Gr22 hydroxylated the molecule at the second position, yielding N-(4-(1-hydroxy-1-methylethyl)phenyl)-N′,N′-dimethylurea. Hydroxylation was the dominant mode of isoproturon transformation in these fungi, although some cultures also produced traces of the N-demethylated metabolite N-(4-isopropylphenyl)-N′-methylurea. A basidiomycete isolate produced a mixture of the two hydroxylated and N-demethylated metabolites at low concentrations. Clonostachys sp. strain Gr141 and putative Tetracladium sp. strain Gr57 did not hydroxylate isoproturon but N demethylated the compound to a minor extent. Mortierella sp. strain Gr4 also produced N-(4-(2-hydroxy-1-methylethyl)phenyl)-N′-methylurea, which is the product resulting from combined N demethylation and hydroxylation. 相似文献
12.
Ma X Tan ST Khoo CL Sim HM Chan LW Chui WK 《Bioorganic & medicinal chemistry letters》2011,21(18):5428-5431
The emergence and spread of multidrug-resistant strains of Staphylococcus aureus and Mycobacterium tuberculosis are generating a threat to public health worldwide. In the current study, a series of N(1)-benzyl and N(1)-benzyloxy-1,6-dihydro-1,3,5-triazine-2,4-diamine derivatives were synthesized and investigated for their antimicrobial activity against S. aureus, and Mycobacterium smegmatis which is taxonomically related to M. tuberculosis. Most of the compounds exhibited good activity against M. smegmatis as determined by comparison of diameters of the zone of inhibition of test compounds and standard antibiotics. Compound 7o showed potent antimycobacterial activity against M. smegmatis without mammalian DHFR inhibition liability. The results from this study indicate that 1-benzyl derivatives of 1,6-dihydro-1,3,5-triazine-2,4-diamines may be used as lead compounds for the discovery of antimycobacterial agents. 相似文献
13.
Interactions of atrazine and 2,4-D with human serum albumin studied by gel and capillary electrophoresis, and FTIR spectroscopy. 总被引:10,自引:0,他引:10
M Purcell J F Neault H Malonga H Arakawa R Carpentier H A Tajmir-Riahi 《Biochimica et biophysica acta》2001,1548(1):129-138
The herbicides 6-chloro-N-ethyl-N'-(1-methylethyl)-1,3,5-triazine-2,4-diamine (atrazine) and 2,4-dichlorophenoxyacetic acid (2,4-D) are widely used in agricultural practice to fight dicotyledon weeds mainly in maize, cereals, and lucerne. As a result, these compounds are found not only in the plants, soil, and water, but also in the cultivated ground in the following years as well as in agricultural products such as fruits, milk, butter, and sugar beet. The toxicological effects of herbicides occur in vivo, when transported to the target organ through the bloodstream. It has been suggested that human serum albumin (HSA) serves as a carrier protein to transport 2,4-D to molecular targets. This study was designed to examine the interaction of atrazine and 2,4-D with HSA in aqueous solution at physiological pH with herbicide concentrations of 0.0001-1 mM, and final protein concentration of 1% w/v. Gel and capillary electrophoresis, UV-visible and Fourier transform infrared spectroscopic methods were used to determine the drug binding mode, the drug binding constant, and the protein secondary structure in aqueous solution. Structural analysis showed that different types of herbicide-HSA complexes are formed with stoichiometric ratios (drug/protein) of 3:1 and 11:1 for atrazine and 4.5:1 and 10:1 for 2,4-D complexes. Atrazine showed a weak binding affinity (K=3.50 x 10(4) M(-1)), whereas two bindings (K(1)=2.50 x 10(4) M(-1) and K(2)=8.0 x 10(3) M(-1)) were observed for 2,4-D complexes. The herbicide binding results in major protein secondary structural changes from that of the alpha-helix 55% to 45--39% and beta-sheet 22% to 24--32%, beta-anti 12% to 10--22% and turn 11% to 12--15%, in the drug-HSA complexes. The observed spectral changes indicate a partial unfolding of the protein structure, in the presence of herbicides in aqueous solution. 相似文献
14.
The physiological effects of an experimental herbicide and cellulose synthesis inhibitor, N2-(1-ethyl-3-phenylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine, called AE F150944, are described. In the aminotriazine molecular class, AE F150944 is structurally distinct from other known cellulose synthesis inhibitors. It specifically inhibits crystalline cellulose synthesis in plants without affecting other processes that were tested. The effects of AE F150944 on dicotyledonous plants were tested on cultured mesophyll cells of Zinnia elegans L. cv. Envy, which can be selectively induced to expand via primary wall synthesis or to differentiate into tracheary elements via secondary wall synthesis. The IC50 values during primary and secondary wall synthesis in Z. elegans were 3.91×10–8 M and 3.67×10–9 M, respectively. The IC50 in suspension cultures of the monocot Sorghum halapense (L.) Pers., which were dividing and synthesizing primary walls, was 1.67×10–10 M. At maximally inhibitory concentrations, 18–33% residual crystalline cellulose synthesis activity remained, with the most residual activity observed during primary wall synthesis in Z. elegans. Addition to Z. elegans cells of two other cellulose synthesis inhibitors, 1 M 2,6-dichlorobenzonitrile and isoxaben, along with AE F150944 did not eliminate the residual cellulose synthesis, indicating little synergy between the three inhibitors. In differentiating tracheary elements, AE F150944 inhibited the deposition of detectable cellulose into patterned secondary wall thickenings, which was correlated with delocalization of lignin as described previously for 2, 6-dichlorobenzonitrile. Freeze-fracture electron microscopy showed that the plasma membrane below the patterned thickenings of AE F150944-treated tracheary elements was depleted of cellulose-synthase-containing rosettes, which appeared to be inserted intact into the plasma membrane followed by their rapid disaggregation. AE F150944 also inhibited cellulose-dependent growth in the rosette-containing alga, Spirogyra pratensis, but it did not inhibit cellulose synthesis in Acetobacter xylinum or Dictyostelium discoideum, both of which synthesize cellulose via linear terminal complexes. Therefore, AE F150944 may inhibit crystalline cellulose synthesis by destabilizing plasma membrane rosettes.Abbreviations AE F150944 N2-(1-ethyl-3-phenylpropyl)-6-(1-fluoro-1-methylethyl)-1,3,5-triazine-2,4-diamine - CBI cellulose biosynthesis inhibiting - CGA CGA 325615, 1-cyclohexyl-5-(2,3,4,5,6-pentafluorophenoxy)-14,2,4,6-thiatriazin-3-amine - DCB 2,6-dichlorobenzonitrile - TE tracheary element 相似文献
15.
Two new chiral monochloro-s-triazines (MCT) were synthesized [viz N-(4-chloro-6-piperidinyl-[1,3,5]-triazine-2-yl)-l-leucine amide and N-(4-chloro-6-piperidinyl-[1,3,5]-triazine-2-yl)-l-leucine) (CDR 1 and 2, respectively)] by the nucleophilic displacement of chlorine atoms in s-triazine moiety. One of the Cl atoms was replaced with piperidine, and the second Cl atom in the 6-piperidinyl derivative
was replaced with amino acid amide (viz l-Leu–NH2) and amino acid (l-Leu). These reagents were characterized and used as CDRs for chiral separation of protein and non-protein amino acids, and
were separated on a reversed-phase C18 column. The reaction conditions were optimized for the synthesis of diastereomers using one MCT reagent. The separation method
was validated for limit of detection, linearity, accuracy, precision, and recovery. 相似文献
16.
Zahira Tber Mylène Wartenberg Jean-Eddy Jacques Vincent Roy Fabien Lecaille Dawid Warszycki Andrzej J. Bojarski Gilles Lalmanach Luigi A. Agrofoglio 《Bioorganic & medicinal chemistry》2018,26(14):4310-4319
We report herein the synthesis and biological evaluation of a new series of 2,4,6-trisubstituted 1,3,5-triazines as reversible inhibitors of human cysteine cathepsins. The desired products bearing morpholine and N-Boc piperidine, respectively, were obtained in three to four steps from commercially available trichlorotriazine. Seventeen hitherto unknown compounds were evaluated in vitro against various cathepsins for their inhibitory properties. Among them, compound 7c (4-(morpholin-4-yl)-6-[4-(trifluoromethoxy)anilino]-1,3,5-triazine-2-carbonitrile) was identified as the most potent and selective inhibitor of cathepsin S (Ki??=??2??±??0.3?nM). Also 7c impaired the autocatalytic maturation of procathepsin S. Molecular docking studies support that 7c bound within the active site of cathepsin S, by interacting with Gly23, Cys25 and Trp26 (S1 subsite), with Asn67, Gly69 and Phe70 (S2 subsite) and with Gln19 (S1′ pocket). 相似文献
17.
Jinfeng Chu 《Inorganica chimica acta》2011,376(1):350-357
In this paper, two di-substituted triazine-based ligands, 6-chloro-N,N,N′N′-tetrakis-pyridin-2-ylmethyl-[1,3,5]triazine-2,4-diamine (L1), and 6-chloro-N,N′-bis-pyridin-2-ylmethyl-N,N′-bis-thiophen-2-ylmethyl-[1,3,5]triazine-2,4-diamine (L2), have been prepared. Reaction of CuCl2·2H2O and Cu(NO3)2·3H2O with L1 and L2 results in the formation of [Cu2Cl4(L1)]·3MeOH (compound 1), [Cu4(NO3)8(L1)2]·2.07CH2Cl2·0.93MeOH (compound 2), [Cu2Cl4(L2)2] (compound 3) and [Cu(NO3)2(L2)]·CH2Cl2 (compound 4), respectively, which have been fully characterized and determined by single-crystal X-ray crystallography, FT-IR, elemental analysis, thermogravimetric measurement and magnetic susceptibility. The dinuclear compound 1 shows strong π-π interactions between the neighboring pyridine rings. The nitrate-π (1,3,5-triazine ring) interaction with the distance of 2.755 Å in compound 2, is the closest contact reported so far. Compounds 3 and 4 are mononuclear copper(II) compounds, in which none of thiophene rings coordinates with copper(II) ion. In addition, the different orientations of two thiophene rings in compounds 3 and 4 lead to the π-π and CH2Cl2-π (thiophene ring) interactions in compound 4, but not in compound 3. 相似文献
18.
Takeo Yoshida 《Phytochemistry》1976,15(11):1723-1725
A new pyrazine derivative, stizolamine (1-methyl-3-guanidino-6-hydroxymethylpyrazin-2-one), has been isolated from seeds of Stizolobium hassjoo. This amine, which has a blue fluorescence, gives guanidine, N-methyl-alanine, oxalic acid, alanine and glycine on treatment with 6 N HCl. The permanganate oxidation product of stizolamine is 4-amino-6-methylcarbamoyl-1,3,5-triazine-2-carboxylic acid. 相似文献
19.
A cyclic hydroxamate, 2,4-dihydroxy-7-methoxy-2H- 1,4-benzoxazin-3(4H)-one (DIMBOA), was isolated and identified from shoots of 6-day-old corn seedlings grown in the dark. From 100 g of plant tissue 100 mg of DIMBOA were isolated. This hydroxamate was very effective in catalysing the hydrolysis of the pyrimidinyl organophosphate insecticide, diazinon (O, O-diethyl- O-[6- methyl-2-(1-methylethyl)-4-pyrimidinyl] phosphorothioate) to 6- methyl-2-(1-methylethyl)-4-hydroxypyrimidine and diethyl phosphorothioic acid. The optimum pH for hydrolytic activity was 5 and at pH values equal to or higher than the pKa of the hydroxamic group (6.95) most of the activity was lost. 相似文献
20.
Summary Four auxins (2,4-dichlorophenoxyacetic acid [2,4-D], indole-3-acetic acid [IAA], indole-3-butyric acid [IBA], and naphthaleneacetic
acid [NAA]), and five cytokinins (N
6-[2-isopentenyl]-adenine [2iP], N
6-benzyladenine [BA], 6-furfurylaminopurine [kinetin], 1-phenyl-3-(1,2,3-thiadiazol-5-yl)-urea [TDZ], and 6-[4-hydroxy-3-methylbut-2-enylamino]purine
[zeatin]) were examined for their effects on direct embryo induction from leaf explants of Dendrobium cv. Chiengmai Pink cultured on 1/2 Murashige and Skoog (MS) medium. Whether in light or darkness, explants easily became
necrotic and no embryos were obtained on growth regulator-free or auxin-containing media after 60 d of culture. By contrast,
five cytokinins tested induced direct embryo formation from leaf explants, and explants cultured in light had a higher embryogenic
response compared with those cultured in darkness. The best condition for direct embryo induction was at 18.16 μM TDZ cultured in light for 60 d, where 33% of explants formed a mean number of 33.6 embryos per explant. During subculture
on growth regulator-free 1/2 MS medium, embryos gradually developed into plantlets. Secondary embryogenesis was occasionally
found on sheath leaves of embryos. Regenerated plantlets were successfully transplanted and grown in a greenhouse environment. 相似文献