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PubMed2000

Low resistance against novel 2-benzylamino-1,3,5-triazine herbicides in atrazine-resistant Chenopodium album plants.

The effects of nine novel 2-benzylamino-1,3,5-triazines on photosynthetic reactions were measured in thylakoids isolated from wild-type and atrazine-resistant plants of Chenopodium album. The resistant plants have a mutation of serine for glycine at position 264 of the D1 protein. The measurement of oxygen evolution and chlorophyll a fluorescence induction indicated a 2-4-fold stronger inhibition by the 6-trifluoromethyl analogues of Photosystem II-dependent electron flow than atrazine. Analogues having a 6-methyl-, 6-monofluoromethyl or 6-difluoromethyl substitution were weak inhibitors, indicating that the 6-trifluoro group is very important for strong inhibition. All the nine novel 2-benzylamino-1,3,5-triazines were almost as active in wild-type as in atrazine-resistant thylakoids, indicating that the benzylamino substitution may be important for the lack of resistance in the atrazine-resistant plants.

Journal Article↗

PubMed2004

1,3,5-Triazine-based tricopper(II) complexes: structure and magnetic properties of threefold-symmetric building blocks.

Two new trinuclear complexes 1 and 2 that are composed of the three-directional ligand 2,4,6-tris(di-2-pyridylamino)-1,3,5-triazine (dipyatriz) and copper(II) chloride as well as a 1D polymeric zigzag system 3 assembled from trimetallic type 2 building blocks have been prepared and structurally characterized. While the triazine-N are not involved in metal coordination, each ligand bidentately binds to three copper ions via its three pairs of pyridine-N donors, and five-coordination of the copper is completed by chloride or dmso solvent molecules. Variable-temperature magnetic studies reveal weak antiferromagnetic coupling. Magnetic properties of the trinuclear entities and of the bis(micro-chloro) bridged pseudo-dimeric copper(II) subunits in 3 can be rationalized on the basis of the structural findings.

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PubMed2006

Distinctive structural features of hydroxyamino-1,3,5-triazine ligands leading to enhanced hydrolytic stability of their titanium complexes.

Three bis(homoleptic) titanium complexes of hydroxyamino-1,3,5-triazine ligands were synthesized and characterized, and their kinetic behavior in THF-water solutions was studied at various pH conditions using UV-vis, based on the characteristic Ti-O band at 380 nm. One of these complexes, , was analyzed by X-ray crystallography. Due to the characteristic electronic structure of the triazine rings, high electron density on the nitrogen atoms leads to strong N-Ti bonds, as indicative by the 2.0 A coordinative bond lengths in the X-ray structure. Consequently, these complexes exhibit high hydrolytic stability over a wide pH range, where hydrolysis was observed to be promoted by basic conditions. At neutral pH, t(1/2) was estimated to be >200 h, whereas at pH = 5.5, no hydrolysis was observed for a period of at least three days.

Journal Article↗

PubMed1999

1H-pyrazolo[2,3-d][1,2,4]triazine-3,7-diones as a new class of human leukocyte elastase inhibitors.

A novel series of 1H-2-phenyl-substituted-pyrazolo[2,3-d][1,2,4]triazine-3,7-diones (3a-g) as potential inhibitors of Human Leukocyte Elastase (HLE) are reported, the acyl-pyrazole being probably involved in the inhibition mechanism of the serino-protease enzymes. The most potent inhibitor both in vivo and in vitro was 2-o-methoxyphenyl-5-methyl-6-nitro-pyrazolo[2,3-d][1,2,4]triazine-3,7-di one (3e), which significantly suppressed the HLE-induced pulmonary injury in rats when administered orally (100 mg/kg, 3 h prior to HLE administration.

Animals↗

PubMed1984

Triazine herbicide resistance in the photosynthetic bacterium Rhodopseudomonas sphaeroides.

The photoaffinity herbicide azidoatrazine (2-azido-4-ethylamino-6-isopropylamino-s-triazine) selectively labels the L subunit of the reaction center of the photosynthetic bacterium Rhodopseudomonas sphaeroides. Herbicide-resistant mutants retain the L subunit and have altered binding properties for methylthio- and chloro-substituted triazines as well as altered equilibrium constants for electron transfer between primary and secondary electron acceptors. We suggest that a subtle alteration in the L subunit is responsible for herbicide resistance and that the L subunit is the functional analog of the 32-kDa Q(B) protein of chloroplast membranes.

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PubMed2004

An efficient route to novel 4,5-di- and 2,4,5-tri substituted imidazoles from imidazo[1,5-a]-1,3,5-triazine (5,8-diaza-7,9-dideazapurine) derivatives.

Two new types of imidazole derivatives: N-(2-R1-5-R2-1H-imidazol-4-yl) thioureas 7a-g and N-(2-R1-5-R2-1H-imidazol-4-yl) formamides 8b,c,g were obtained in high yields by the hydrolytic degradation of 6-R1-8-R2-2-thioxo-2,3-dihydroimidazo[1,5-a]-1,3,5-triazin-4(1H)-ones 5a-g and 6-R1-8-R2-imidazo[1,5-a]-1,3,5-triazin-4(3H)-ones 6b,c,d, respectively. The tautomeric preferences of the new imidazoles were determined.

Imidazoles↗

PubMed1992

Pleiotropy in Triazine-Resistant Brassica napus: Ontogenetic and Diurnal Influences on Photosynthesis.

Studies were conducted that supported the hypothesis that the mutation to the psbA plastid gene that confers S-triazine resistance (R) in Brassica napus also results in an altered diurnal pattern of photosynthetic carbon assimilation (A) relative to that of the susceptible (S) wild type, and that these patterns change over the ontogeny of a plant. Photosynthetic photon flux density, under closely controlled environmental conditions, was incrementally increased and decreased on either side of the midday maxima of 1150 to 1300 mumol quanta m(-2) s(-1). In all experiments, A approximately tracked the increasing and decreasing diurnal light levels. Younger (3- to 4-leaf) R plants had greater photosynthetic rates early and late in the diurnal light period, whereas those of S plants were greater during midday as well as during the photoperiod as a whole. These relative photosynthetic characteristics of R and S plants changed in several ways with ontogeny. As the plants aged during the vegetative phase of development, S plants gradually assimilated more carbon in the early, and then in the late, part of the day. At the end of the vegetative phase of development, R plant carbon assimilation was less relative to S plants at most times of the day, and was never greater. This relationship between the two biotypes dramatically changed with the onset of the reproductive phase (8(1/2) to 9(1/2) leaf) of plant development: R plants assimilated more carbon than S plants during all periods of the diurnal light period with the exception of the late part of the day. In addition to these differences in A, R plant stomatal function differed from that in S plants. R plant leaves were always cooler than S plant leaves under the same environmental and diurnal conditions. Correlated with this difference in leaf temperature were equal or greater total conductances to water vapor and intercellular CO(2) partial pressures in R compared to S leaves in most instances. These studies indicate a more complex pattern of photosynthetic carbon assimilation than previously observed. The photosynthetic superiority of one biotype relative to the other was a function of the time of day and the age of the plant. These studies also suggest that R plants may have an adaptive advantage over S plants in certain unfavorable ecological niches independent of the presence of S-triazine herbicides, such as cool, low-light environments early and late in the day, as well as late in the plants' development. This advantage could result in R biotypes appearing in populations of a species in greater numbers than plastidic mutation alone could cause.

Journal Article↗

PubMed1993

A serine-to-threonine substitution in the triazine herbicide-binding protein in potato cells results in atrazine resistance without impairing productivity.

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.

Amino Acid Sequence↗

PubMed1987

Triazine Resistance without Reduced Vigor in Phalaris paradoxa.

A triazine-resistant (R) biotype of Phalaris paradoxa L. (hood canarygrass) was superior to a triazine-susceptible (S) biotype in seed-germinability and seedling emergence. It was equal or superior to the S-biotype in growth under noncompetitive conditions. Rates of CO(2) uptake by R-plants were similar to those of S-plants, except at very low photon flux densities, where S-plants exhibited higher rates of CO(2) uptake. Fluorescence induction curves of chloroplasts isolated from R-plants indicated an alteration in photosystem II. Analysis of the light dependence of electron transport shows a reduction in quantum yield (Q(y)) in R- compared to S-chloroplasts. The same analysis, however, shows for R-chloroplasts an increase in the light-saturated electron transport rate (V(max)). The increase in V(max) compensates for the reduction of Q(y) over a wide range of photon flux densities, which may explain the similarity between R- and S-biotypes in photosynthetic potential and growth.

Journal Article↗

PubMed1992

Regulation of Photosynthesis in Triazine-Resistant and -Susceptible Brassica napus.

The response of photosynthetic carbon assimilation and chlorophyll fluorescence quenching to changes in intercellular CO(2) partial pressure (C(i)), O(2) partial pressure, and leaf temperature (15-35 degrees C) in triazine-resistant and -susceptible biotypes of Brassica napus were examined to determine the effects of the changes in the resistant biotype on the overall process of photosynthesis in intact leaves. Three categories of photosynthetic regulation were observed. The first category of photosynthetic response, ribulose-1,5-bisphosphate carboxylase/oxygenase (Rubisco)-limited photosynthesis, was observed at 15, 25, and 35 degrees C leaf temperatures with low C(i). When the carbon assimilation rate was Rubisco-limited, there was little difference between the resistant and susceptible biotypes, and Rubisco activity parameters were similar between the two biotypes. A second category, called feedback-limited photosynthesis, was evident at 15 and 25 degrees C above 300 microbars C(i). The third category, photosynthetic electron transport-limited photosynthesis, was evident at 25 and 35 degrees C at moderate to high CO(2). At low temperature, when the response curves of carbon assimilation to C(i) indicated little or no electron transport limitation, the carbon assimilation rate was similar in the resistant and susceptible biotypes. With increasing temperature, more electron transport-limited carbon assimilation was observed, and a greater difference between resistant and susceptible biotypes was observed. These observations reveal the increasing importance of photosynthetic electron transport in controlling the overall rate of photosynthesis in the resistant biotype as temperature increases. Photochemical quenching of chlorophyll fluorescence (q(P)) in the resistant biotype never exceeded 60%, and triazine resistance effects were more evident when the susceptible biotype had greater than 60% q(P), but not when it had less than 60% q(P).

Journal Article↗

PubMed2002

3-Amino-1,2,4-triazine.

In the crystal structure of 3-amino-1,2,4-triazine, C(3)H(4)N(4), the molecules form hydrogen-bonded chains that are almost parallel to the b axis (3.2 degrees), and which are inclined to the a and c axes by approximately 21 and approximately 69 degrees, respectively. The distortion of the 1,2,4-triazine ring in the crystal is compared with gas-phase ab initio molecular-orbital calculations.

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PubMed2003

Two new dimeric cadmium(II) and zinc(II) sulfate complexes with 2,4,6-tris(2-pyridyl)-1,3,5-triazine and 2,2:6',2"-terpyridine.

The structures of two new sulfate complexes are reported, namely di-mu-sulfato-kappa(3)O,O':O"-bis(aqua[2,4,6-tris(2-pyridyl)-1,3,5-triazine-kappa(3)N(1),N(2),N(6)]cadmium(II)) tetrahydrate, [Cd(2)(SO(4))(2)(C(16)H(12)N(6))(2)(H(2)O)(2)].4H(2)O, and di-mu-sulfato-kappa(2)O:O'-bis[(2,2':6',2"-terpyridine-kappa(3)N(1),N(1'),N(1"))zinc(II)] dihydrate, [Cd(2)(SO(4))(2)(C(15)H(11)N(3))(2)].2H(2)O, the former being the first report of a Cd(tpt) complex [tpt is 2,4,6-tris(2-pyridyl)-1,3,5-triazine]. Both compounds crystallize in the space group P-1 and form centrosymmetric dimeric structures. In the cadmium complex, the metal center is heptacoordinated in the form of a pentagonal bipyramid, while in the zinc complex, the metal ion is in a fivefold environment, the coordination geometry being intermediate between square pyramidal and trigonal bipyramidal. Packing of the dimers leads to the formation of planar structures strongly linked by hydrogen bonding.

Journal Article↗

PubMed2002

The triazine hydrolase gene trzN from Nocardioides sp. strain C190: cloning and construction of gene-specific primers.

Using oligonucleotides derived from the N-terminal sequence of a triazine hydrolase from Nocardioides sp. strain C190, two DNA fragments containing trzN were cloned into Escherichia coli and their nucleotide sequences were determined. The 456-amino acid polypeptide predicted from the 1356-bp trzN ORF displayed significant similarity to triazine hydrolases from Pseudomonas and Rhodococcus isolates and belonged to the same amidohydrolase family. The trzN gene was flanked by two DNA sequences possessing 57 and 69% identity, respectively, at the protein level to Rhodococcus erythropolis sequences for a transposase and a transposase helper protein. Amplification primers specific to trzN were tested in soils inoculated with strain C190. The results demonstrated that the primers were specific to trzN, and could detect populations at 10(8) cfu g(-1) soil using 250-mg soil samples.

Actinomycetales↗

PubMed1993

Isolation and Characterization of a Novel Atrazine Metabolite Produced by the Fungus Pleurotus pulmonarius, 2-Chloro-4-Ethylamino-6-(1-Hydroxyisopropyl)Amino-1,3,5-Triazine.

The white rot fungus Pleurotus pulmonarius exhibited metabolism of atrazine (2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine) in liquid culture, producing the dealkylated metabolites desethylatrazine, desisopropylatrazine, and desethyl-desisopropylatrazine. A fourth, unknown metabolite was also produced. It was isolated and was identified as 2-chloro-4-ethylamino-6-(1-hydroxyisopropyl)amino-1,3,5-triazine by gas chromatography-mass spectrometry, Fourier transformed infrared spectroscopy, and H nuclear magnetic resonance analysis. The structure of this metabolite was confirmed by chemical synthesis of the compound and comparison with the fungally produced metabolite.

Journal Article↗

PubMed1993

Mineralization of the s-triazine ring of atrazine by stable bacterial mixed cultures.

Enrichment cultures containing atrazine (2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine) at a concentration of 100 ppm (0.46 mM) as a sole nitrogen source were obtained from soils exposed to repeated spills of atrazine, alachlor, and metolachlor. Bacterial growth occurred concomitantly with formation of metabolites from atrazine and subsequent biosynthesis of protein. When ring-labeled [14C]atrazine was used, 80% or more of the s-triazine ring carbon atoms were liberated as 14CO2. Hydroxyatrazine may be an intermediate in the atrazine mineralization pathway. More than 200 pure cultures isolated from the enrichment cultures failed to utilize atrazine as a nitrogen source. Mixing pure cultures restored atrazine-mineralizing activity. Repeated transfer of the mixed cultures led to increased rates of atrazine metabolism. The rate of atrazine degradation, even at the elevated concentrations used, far exceeded the rates previously reported in soils, waters, and mixed and pure cultures of bacteria.

Atrazine↗

PubMed1995

Cloning and expression of the s-triazine hydrolase gene (trzA) from Rhodococcus corallinus and development of Rhodococcus recombinant strains capable of dealkylating and dechlorinating the herbicide atrazine.

We used degenerate oligodeoxyribonucleotides derived from the N-terminal sequence of the s-triazine hydrolase from Rhodococcus corallinus NRRL B-15444R in an amplification reaction to isolate a DNA segment containing a 57-bp fragment from the trzA gene. By using the nucleotide sequence of this fragment, a nondegenerate oligodeoxyribonucleotide was synthesized and used to screen a genomic library of R. corallinus DNA for fragments containing trzA. A 5.3-kb PstI fragment containing trzA was cloned, and the nucleotide sequence of a 2,450-bp region containing trzA was determined. No trzA expression was detected in Escherichia coli or several other gram-negative bacteria. The trzA gene was subcloned into a Rhodococcus-E. coli shuttle vector, pBS305, and transformed into several Rhodococcus strains. Expression of trzA was demonstrated in all Rhodococcus transformants. Rhodococcus sp. strain TE1, which possesses the catabolic gene (atrA) for the N-dealkylation of the herbicides atrazine and simazine, was able to dechlorinate the dealkylated metabolites of atrazine and simazine when carrying the trzA gene on a plasmid. A plasmid carrying both atrA and trzA was constructed and transformed into three atrA- and trzA-deficient Rhodococcus strains. Both genes were expressed in the transformants. The s-triazine hydrolase activity of the recombinant strains carrying the trzA plasmid were compared with that of the R. corallinus strain from which it was derived.

Amino Acid Sequence↗

PubMed1993

[Studies on as-triazine derivatives. XIX. Synthesis of 2,3-diarylpyrazine 2,3-diarylpyridine derivatives as blood platelet aggregation inhibitors].

4,5-Diphenyl-2-ethoxypyrimidine (1), 3,4-diphenyl-6-ethoxypyridazine (2) and 2,3-diphenyl-5-ethoxypyrazine (3) were evaluated for inhibitory activity towards arachidonic acid-induced aggregation of rabbit blood platelet in vitro. 2,3-Diphenyl-5-ethoxypyrazine (3) exhibited significant inhibitory activity. Thus, various 5-substituted 2,3-bis(4-methoxyphenyl)pyrazines were synthesized by the nucleophilic substitution reaction of 5-chloro-2,3-bis(4-methoxyphenyl)pyrazine (9). In a similar manner, substituted 2,3-bis(4-methoxyphenyl)pyridines were prepared from 2,3-bis(4-methoxyphenyl)-6-methylsulfonylpyridine (17), which was synthesized by the cycloaddition retro Diels-Alder reaction of 5,6-bis(4-methoxyphenyl)-3-methylsulfonyl-1,2,4-triazine (16) with norbornadiene. Among the compounds prepared, 6-isopropoxy-2,3-bis(4-methoxyphenyl)-pyrazine (10f) showed the most potent inhibitory activity, which was more than the activity of anitrazafen[5,6-bis(4-methoxyphenyl)-3-methyl-1,2,4-triazine.

Animals↗

PubMed1999

Reproductive disturbance caused by an S-triazine herbicide in pigs.

The aim of the study was to assess the effect of subacute treatment with a low dose of atrazine (1,3,5-triazine-2,4-diamine, 6-chloro-N-ethyl-N'-(1-methyl-ethyl), an s-triazine herbicide, on endocrine oestrus regulation in gilts. A group of nine gilts (F1 generation of Swedish Landrace x Large Yorkshire) were treated with 1 mg atrazine/kg body mass daily, mixed to the feed for 19 days before the onset of expected oestrus. Blood samples were obtained by cranial vena cava puncture three times daily at 3-h intervals on five post-treatment days, i.e. before and during oestrus. The serum concentration of oestradiol-17 beta (E2) was determined by the fluoroimmunochemical method. On Day -2 before the onset of expected oestrus, a significantly lower (P < 0.001) E2 concentration was measured in the serum of treated gilts (31.25 +/- 1.95 and 39.32 +/- 1.38 pg/mL) than in the control pigs (51.43 +/- 1.29 and 68.59 +/- 2.99 pg/mL). In contrast, the E2 concentration measured in the serum of treated animals was significantly higher (P < 0.001) on the day of the expected onset of oestrus and on the subsequent two days (35.43 +/- 1.85, 53.92 +/- 1.98 and 60.32 +/- 2.35 pg/mL, respectively) than in the control animals (13.52 +/- 1.79, 21.53 +/- 1.35 and 20.05 +/- 1.46 pg/mL, respectively). Insufficient serum E2 concentration of the treated gilts resulted in a failure of expected oestrus, as indicated also by the state of dioestrus demonstrated by histopathological examination of the uterus.

Animals↗