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call loadScript javascripts\jsmol\core\package.js call loadScript javascripts\jsmol\core\core.z.js -- required by ClazzNode call loadScript javascripts\jsmol\J\awtjs2d\WebOutputChannel.js Jmol JavaScript applet jmolApplet0_object__215569230472901__ initializing getValue debug = null getValue logLevel = null getValue allowjavascript = null AppletRegistry.checkIn(jmolApplet0_object__215569230472901__) call loadScript javascripts\jsmol\core\corestate.z.js viewerOptions: { "name":"jmolApplet0_object","applet":true,"documentBase":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:28854","platform":"J.awtjs2d.Platform","fullName":"jmolApplet0_object__215569230472901__","display":"jmolApplet0_canvas2d","signedApplet":"true","appletReadyCallback":"Jmol._readyCallback","statusListener":"[J.appletjs.Jmol.MyStatusListener object]","codeBase":"https://www.ebi.ac.uk/chebi/javascripts/jsmol/","syncId":"215569230472901","bgcolor":"#000" } (C) 2012 Jmol Development Jmol Version: 13.2.7 $Date: 2013-10-01 11:35:15 -0500 (Tue, 01 Oct 2013) $ java.vendor: j2s java.version: 0.0 os.name: j2s Access: ALL memory: 0.0/0.0 processors available: 1 useCommandThread: false appletId:jmolApplet0_object (signed) starting HoverWatcher_1 getValue emulate = null defaults = "Jmol" getValue boxbgcolor = null getValue bgcolor = #000 backgroundColor = "#000" getValue ANIMFRAMECallback = null getValue APPLETREADYCallback = Jmol._readyCallback APPLETREADYCallback = "Jmol._readyCallback" getValue ATOMMOVEDCallback = null getValue CLICKCallback = null getValue ECHOCallback = null getValue ERRORCallback = null getValue EVALCallback = null getValue HOVERCallback = null getValue LOADSTRUCTCallback = null getValue MEASURECallback = null getValue MESSAGECallback = null getValue MINIMIZATIONCallback = null getValue PICKCallback = null getValue RESIZECallback = null getValue SCRIPTCallback = null getValue SYNCCallback = null getValue STRUCTUREMODIFIEDCallback = null getValue doTranslate = null language=en_US getValue popupMenu = null getValue script = null Jmol applet jmolApplet0_object__215569230472901__ ready call loadScript javascripts\jsmol\core\corescript.z.js call loadScript javascripts\jsmol\J\script\FileLoadThread.js starting QueueThread0_2 script 1 started starting HoverWatcher_3 starting HoverWatcher_4 The Resolver thinks Mol Marvin 03190714063D starting HoverWatcher_5 Time for openFile( Marvin 03190714063D 19 19 0 0 0 0 999 V2000 -1.8338 -1.9731 -1.4670 C 0 0 0 0 0 0 0 0 0 4 0 0 -0.9160 -2.4736 -0.5226 C 0 0 0 0 0 0 0 0 0 3 0 0 -0.4272 -0.2003 0.2186 C 0 0 0 0 0 0 0 0 0 1 0 0 -0.2221 -1.5949 0.3334 C 0 0 0 0 0 0 0 0 0 2 0 0 -1.3925 0.2933 -0.6845 C 0 0 0 0 0 0 0 0 0 6 0 0 -2.0858 -0.5887 -1.5319 C 0 0 0 0 0 0 0 0 0 5 0 0 0.2883 0.6244 0.8678 O 0 0 0 0 0 0 0 0 0 0 0 0 0.8661 -2.2439 1.4615 Cl 0 0 0 0 0 0 0 0 0 0 0 0 1.4455 1.1287 0.4096 C 0 0 0 0 0 0 0 0 0 0 0 0 2.0545 2.0163 1.3693 C 0 0 0 0 0 0 0 0 0 0 0 0 -2.6244 -3.0294 -2.5271 Cl 0 0 0 0 0 0 0 0 0 0 0 0 3.1537 1.7786 1.8464 O 0 0 0 0 0 0 0 0 0 0 0 0 1.4876 3.0474 1.7099 O 0 0 0 0 0 0 0 0 0 0 0 0 -0.7441 -3.4806 -0.4662 H 0 0 0 0 0 0 0 0 0 0 0 0 -1.5776 1.2981 -0.7469 H 0 0 0 0 0 0 0 0 0 0 0 0 -2.7606 -0.2110 -2.2012 H 0 0 0 0 0 0 0 0 0 0 0 0 1.2803 1.6927 -0.5139 H 0 0 0 0 0 0 0 0 0 0 0 0 2.1377 0.3134 0.1691 H 0 0 0 0 0 0 0 0 0 0 0 0 1.8703 3.6027 2.2757 H 0 0 0 0 0 0 0 0 0 0 0 0 1 11 1 0 0 0 0 2 1 4 0 0 0 0 3 7 1 0 0 0 0 4 3 4 0 0 0 0 2 4 4 0 0 0 0 4 8 1 0 0 0 0 3 5 4 0 0 0 0 6 5 4 0 0 0 0 1 6 4 0 0 0 0 7 9 1 0 0 0 0 9 10 1 0 0 0 0 10 12 2 0 0 0 0 10 13 1 0 0 0 0 2 14 1 0 0 0 0 5 15 1 0 0 0 0 6 16 1 0 0 0 0 9 17 1 0 0 0 0 9 18 1 0 0 0 0 13 19 1 0 0 0 0 M END): 17 ms reading 19 atoms ModelSet: haveSymmetry:false haveUnitcells:false haveFractionalCoord:false 1 model in this collection. Use getProperty "modelInfo" or getProperty "auxiliaryInfo" to inspect them. Default Van der Waals type for model set to Babel 19 atoms created ModelSet: not autobonding; use forceAutobond=true to force automatic bond creation Script completed Jmol script terminated
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| 2,4-Dichlorophenoxyacetic acid is an organic compound with the chemical formula Cl2C6H3OCH2CO2H. It is usually referred to by its ISO common name 2,4-D. It is a systemic herbicide that kills most broadleaf weeds by causing uncontrolled growth, but most grasses such as cereals, lawn turf, and grassland are relatively unaffected.
2,4-D is one of the oldest and most widely available herbicides and defoliants in the world, having been commercially available since 1945, and is now produced by many chemical companies since the patent on it has long since expired. It can be found in numerous commercial lawn herbicide mixtures, and is widely used as a weedkiller on cereal crops, pastures, and orchards. Over 1,500 herbicide products contain 2,4-D as an active ingredient. |
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Read full article at Wikipedia
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| InChI=1S/C8H6Cl2O3/c9-5-1-2-7(6(10)3-5)13-4-8(11)12/h1-3H,4H2,(H,11,12) |
| OVSKIKFHRZPJSS-UHFFFAOYSA-N |
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environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
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EC 1.1.1.25 (shikimate dehydrogenase) inhibitor
An EC 1.1.1.* (oxidoreductase acting on donor CH-OH group, NAD+ or NADP+ acceptor) inhibitor that interferes with the action of shikimate dehydrogenase (EC 1.1.1.25).
synthetic auxin
A synthetic compound exhibiting auxin activity.
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agrochemical
An agrochemical is a substance that is used in agriculture or horticulture.
phenoxy herbicide
Any member of the class of herbicides whose members contain a phenoxy or substituted phenoxy group.
defoliant
A herbicide which when sprayed or dusted on plants causes its leaves to fall off.
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View more via ChEBI Ontology
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Outgoing
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2,4-D
(CHEBI:28854)
has role
agrochemical
(CHEBI:33286)
2,4-D
(CHEBI:28854)
has role
defoliant
(CHEBI:23582)
2,4-D
(CHEBI:28854)
has role
EC 1.1.1.25 (shikimate dehydrogenase) inhibitor
(CHEBI:77484)
2,4-D
(CHEBI:28854)
has role
environmental contaminant
(CHEBI:78298)
2,4-D
(CHEBI:28854)
has role
phenoxy herbicide
(CHEBI:60575)
2,4-D
(CHEBI:28854)
has role
synthetic auxin
(CHEBI:26841)
2,4-D
(CHEBI:28854)
is a
chlorophenoxyacetic acid
(CHEBI:23152)
2,4-D
(CHEBI:28854)
is a
dichlorobenzene
(CHEBI:23697)
2,4-D
(CHEBI:28854)
is conjugate acid of
(2,4-dichlorophenoxy)acetate
(CHEBI:19351)
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Incoming
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(2,4-dichlorophenoxy)acetate
(CHEBI:19351)
is conjugate base of
2,4-D
(CHEBI:28854)
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(2,4-dichlorophenoxy)acetic acid
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(2,4-Dichlorphenoxy)essigsäure
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ChEBI
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2,4-D
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KEGG COMPOUND
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2,4-D acid
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ChemIDplus
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2,4-Dichlorophenoxyacetate
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KEGG COMPOUND
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2,4-Dichlorophenoxyacetic acid
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KEGG COMPOUND
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2,4-Dichlorphenoxyessigsäure
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ChEBI
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acide 2,4-dichloro phenoxyacetique
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ChemIDplus
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Hedonal
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NIST Chemistry WebBook
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Trinoxol
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NIST Chemistry WebBook
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1214242
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Reaxys Registry Number
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Reaxys
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51306
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Gmelin Registry Number
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Gmelin
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94-75-7
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CAS Registry Number
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KEGG COMPOUND
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94-75-7
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CAS Registry Number
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ChemIDplus
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94-75-7
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CAS Registry Number
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NIST Chemistry WebBook
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Fanous A, Weiland F, Lück C, Görg A, Friess A, Parlar H (2007)
A proteome analysis of Corynebacterium glutamicum after exposure to the herbicide 2,4-dichlorophenoxy acetic acid (2,4-D).
Chemosphere 69, 25-31 [PubMed:17568655]
[show Abstract]
The herbicide 2,4-dichlorophenoxy acetic acid (2,4-D) induces a wide spectrum of toxic responses in living organisms. In this study, we analyzed the stress-induced responses of Corynebacterium glutamicum cells on protein level upon treatment with 2,4-D. For this, growing C. glutamicum cells were exposed to sublethal concentrations of 2,4-D, and changes of the gene expression profiles in comparison to non-exposed organisms were analyzed by two-dimensional gel electrophoresis and mass spectrometry. 2,4-D induced the over-expression of at least six C. glutamicum proteins, four of which could be identified by MALDI-TOF-MS. One protein (Cg2521; long-chain acyl-CoA synthetase) was related to the energy metabolism, and two proteins were involved in cell envelope synthesis (Cg2410; glutamine-dependent amidotransferase, and Cg1672; glycosyltransferase). The last induced protein was the ABC type transport system (Cg2695, ATPase component). The newly observed proteins, except for the ABC transport system, were not in general stress-related proteins, but were specifically expressed upon 2,4-D exposure and, therefore, can be used as respective biomarkers. Moreover, since these proteins seem to play a pivotal role in the adaptation of the cell to 2,4-D, they may help to gain deeper insight into the damage mechanisms of 2,4-D induced in the living cell. | Farenhorst A, Reimer M, Londry K, Saiyed I (2006)
2,4-Dichlorophenoxy acetic acid mineralization in amended soil.
Journal of environmental science and health. Part. B, Pesticides, food contaminants, and agricultural wastes 41, 509-522 [PubMed:16785163]
[show Abstract]
The application of municipal biosolid or liquid hog manure to agricultural soils under laboratory conditions at 20 degrees C influenced the fate of the herbicide 2,4-D [2,4-(dichlorophenoxy)acetic acid] in soil. When 2,4-D was added to soil at agronomic rates immediately after the addition of manure or biosolids to a coarse-textured soil, the percentage of 2,4-D mineralized at 100 days was about 47% for both treatments, compared to only 31% for control soils without amendments. The enhanced 2,4-D mineralization as a result of amendment addition was due to an increased heterotrophic microbial activity, with the greatest increases in soil respiration occurring for soils amended with biosolids. When additions of 2,4-D were delayed for one, two, or four weeks after the amendments were applied, the additions of amendments generally reduced 2,4-D mineralization in soil, particularly for manure, indicating that the effect of amendments on enhancing soil microbial activities diminished over time. In contrast, the mineralization of 2,4-D in control soils was less dependent on when 2,4-D was applied in relation to pre-incubations of soil for zero, one, two, or four weeks. The effect of manure on decreasing 2,4-D mineralization in specific soils was as large as the effect of soil texture on differences in 2,4-D mineralization across soils. Because manure was not found to impact 2,4-D sorption by soil, it is possible that 2,4-D mineralization decreased because 2,4-D transformation products were strongly sorbed onto organic carbon constituents in manure-amended soils and were therefore less accessible to microorganisms. Alternatively, microorganisms were less likely to metabolize the herbicide because they preferentially consumed the type of organic carbon in manure that is a weak sorbent for 2,4-D. | Sameshima K, Kobae H, Fofana D, Yoshidome K, Nishi J, Miyata K (2004)
Effects of pure 2,4-dichlorophenoxyacetic acid on cultured rat embryos.
Congenital anomalies 44, 93-96 [PubMed:15198722]
[show Abstract]
2,4-dichlorophenoxyacetic acid (2,4-D), a plant growth regulator, has been used worldwide as a herbicide. Previously we evaluated the prenatal developmental effects of 2,4-D by feeding it to pregnant rats and found that it is maternally toxic and embryolethal, and it induces urogenital malformations in rat fetuses. In the study presented here, we investigated the effects of pure 2,4-D on rat embryos in whole embryo culture. Rat embryos on day 9.5 of gestation were cultured for 48 h at several concentration levels with pure 2,4-D (50-500 microg/mL). 2,4-D caused a concentration-related increase in the incidence of each malformation. Significant decreases in the number of somites were observed at a concentration of 100 microg/mL or more. At the concentration of 100 microg/mL, there was normal yolk sac circulation. This result suggests that 2,4-D has a detrimental effect on somite development and directly damages developing embryos. | Nakazawa H, Takahashi N, Inoue K, Ito Y, Goto T, Kato K, Yoshimura Y, Oka H (2004)
Rapid and simultaneous analysis of dichlorvos, malathion, carbaryl, and 2,4-dichlorophenoxy acetic acid in citrus fruit by flow-injection ion spray ionization tandem mass spectrometry.
Talanta 64, 899-905 [PubMed:18969687]
[show Abstract]
A simple method for the rapid and simultaneous analysis of dichlorvos (DDVP), malathion, carbaryl, and 2,4-dichlorophenoxy acetic acid (2,4-D) in citrus fruit, which uses flow-injection ion spray ionization tandem mass spectrometry, has been developed for the first time. The method involves the combined use of stable isotopically labeled internal standards (DDVP-d(6), malathion-d(10), carbaryl-d(7), and 2,4-D-d(5)) and a multiple reaction monitoring technique. The average recoveries for the pesticides at the same concentrations as their tolerance levels (DDVP: 0.1-0.2mugg(-1); malathion: 0.5-4.0mugg(-1); carbaryl: 1.0mugg(-1); 2,4-D: 1.0-2.0mugg(-1)) ranged from 90 to 119% with the relative standard deviation (R.S.D.) ranging from 1.0 to 13.1% (n = 5). Analysis time, including sample preparation and determination, was only 15min. The present method is effective for screening DDVP, malathion, carbaryl, and 2,4-D in citrus fruit. | Di Paolo O, de Duffard AM, Duffard R (2001)
In vivo and in vitro binding of 2,4-dichlorophenoxyacetic acid to a rat liver mitochondrial protein.
Chemico-biological interactions 137, 229-241 [PubMed:11566291]
[show Abstract]
2,4-dichlorophenoxyacetic acid (2,4-D) is a hormonal herbicide widely used in the world because of its efficacy in the control of broadleaf and woody plants. In this study we have demonstrated in vivo covalent binding of the phenoxyherbicide 2,4-D to a single protein of 52 kD (from rat liver mitochondrial preparation) detected through immunoblotting studies with the specific antiserum for 2,4-D. The direct involvement of 2,4-D in the formation of the adduct has also been demonstrated in vitro, using liver mitochondrial preparations exposed to 14C-UL-2,4-D. Radiolabeled protein separated by SDS-PAGE and afterwards electroeluted showed a single labeled protein of 52 kD. When mitochondria exposed to radiolabeled xenobiotic were devoid of their outer membrane, the specific activity observed suggest that protein involved in covalent interaction belongs to the inner mitochondrial membrane. We propose that covalent binding of the phenoxyherbicide 2,4-D to a very specific single protein of 52 kD observed in vitro and in vivo may be related to known alterations of the mitochondrial function. | Kaioumova D, Süsal C, Opelz G (2001)
Induction of apoptosis in human lymphocytes by the herbicide 2,4-dichlorophenoxyacetic acid.
Human immunology 62, 64-74 [PubMed:11165716]
[show Abstract]
Dimethylammonium salt of 2,4-dichlorophenoxyacetic acid (DMA-2,4-D) is a widely used herbicide that is considered moderately toxic. In the present study we found that DMA-2,4-D is able to cause apoptosis in peripheral blood lymphocytes of healthy individuals and Jurkat T cells. Apoptosis induced by DMA-2,4-D was dose and time dependent, independent of Fas, TNF receptor 1 or the aromatic hydrocarbon receptor, and involved disruption of the mitochondrial transmembrane potential and activation of caspase-9. ZVAD-FMK, a broad-spectrum inhibitor of caspases, blocked DMA-2,4-D-induced apoptosis completely. While an inhibitor of caspase-9, as well as caspase-9 and caspase-3 inhibitors in combination, strongly blocked DMA-2,4-D-induced apoptosis, an inhibitor of caspase-3 had a moderate inhibitory effect. Unlike Fas-mediated apoptosis, the initiator caspase, caspase-8, was not involved in DMA-2,4-D-induced apoptosis. Transfection of Jurkat cells with Bcl-2 prevented DMA-2,4-D-induced disruption of the mitochondrial transmembrane potential and led to a complete blockage of apoptosis. Our data indicate that DMA-2,4-D kills human lymphocytes by initiating apoptosis via a direct effect on mitochondria. The activation of caspases occurs downstream of mitochondrial damage, and the dysfunction of mitochondria appears to be sufficient for triggering all downstream events leading to apoptosis. | Amer SM, Aly FA (2001)
Genotoxic effect of 2,4-dichlorophenoxy acetic acid and its metabolite 2,4-dichlorophenol in mouse.
Mutation research 494, 1-12 [PubMed:11423340]
[show Abstract]
The cytogenetic effect of 2,4-dichlorophenoxy acetic acid (2,4-D) and its metabolite 2,4-dichlorophenol (2,4-DCP) was studied in bone-marrow, germ cells and sperm head abnormalities in the treated mice. Swiss mice were treated orally by gavage with 2,4-D at 1.7, 3.3 and 33 mg kg(-1)BW (1/200, 1/100 and 1/10 of LD(50)). 2,4-DCP was intraperitoneally (i.p.) injected at 36, 72 and 180 mg kg(-1)BW (1/10, 1/5, 1/2 of LD(50)). A significant increase in the percentage of chromosome aberrations in bone-marrow and spermatocyte cells was observed after oral administration of 2,4-D at 3.3 mg kg(-1)BW for three and five consecutive days. This percentage increased and reached 10.8+/-0.87 (P<0.01) in bone-marrow and 9.8+/-0.45 (P<0.01) in spermatocyte cells after oral administration of 2,4-D at 33 mg kg(-1)BW for 24 h. This percentage was, however, lower than that induced in bone-marrow and spermatocyte cells by mitomycin C (positive control). 2,4-D induced a dose-dependent increase in the percentage of sperm head abnormalities. The genotoxic effect of 2,4-DCP is weaker than that of 2,4-D, as indicated by the lower percentage of the induced chromosome aberrations (in bone-marrow and spermatocyte cells) and sperm head abnormalities. Only the highest tested concentration of 2,4-DCP (180 mg kg(-1)BW, 1/2 LD(50)) induced a significant percentage of chromosome aberrations and sperm head abnormalities after i.p. injection. The obtained results indicate that 2,4-D is genotoxic in mice in vivo under the conditions tested. Hence, more care should be given to the application of 2,4-D on edible crops since repeated uses may underlie a health hazard. | Forgács E, Cserháti T, Barta I (2000)
The binding of amino acids to the herbicide 2,4-dichlorophenoxy acetic acid.
Amino acids 18, 69-79 [PubMed:10794133]
[show Abstract]
The interaction of amino acids with the herbicide 2,4-dichlorophenoxyacetic acid (2,4-D) was studied by charge-transfer chromatography carried out on diatomaceous layers covered with different amount of 2,4-D and the effect of salts on the strength of interaction was elucidated. It was established that Arg, His, Lys, Orn, Phe and Trp binds to 2,4-D, the binding process is of saturation character. Principal component analysis proved that the concentration of 2,4-D exerts the highest impact on the interaction and the effect of salts is of secondary importance. The results suggest that these amino acid residues may account for the binding of 2,4-D to proteins and can play a considerable role in the detoxification processes by forming conjugates with 2,4-D. | Buse EL, Laties GG (1993)
Ethylene-Mediated Posttranscriptional Regulation in Ripening Avocado (Persea americana) Mesocarp Discs.
Plant physiology 102, 417-423 [PubMed:12231832]
[show Abstract]
Discs of avocado (Persea americana) fruit (15 x 3 mm thick) kept in a stream of moist air ripen within 72 h. Following cutting, a modest evolution of wound ethylene that dissipates in 24 h is followed by a burst of autocatalytic ethylene production associated with a respiratory climacteric, much as in the intact fruit. Aminoethoxyvinylglycine (AVG), an inhibitor of ethylene synthesis, and 2,5-norbornadiene (NBD) and Ag+, inhibitors of ethylene action, inhibit disc ripening, as does 2,4-dichlorophenoxyacetic acid (2,4-D), a synthetic auxin. On the other hand, none of the foregoing agents except Ag+, at concentrations that delay or prevent ripening, suppress the induction of four ripening-related genes encoding cellulase, polygalacturonase (PG), cytochrome P-450 oxidase (P-450), and ethylene-forming enzyme (EFE, or 1-aminopropane-1-carboxylic acid oxidase), respectively. Whereas Ag+ fully inhibits the production of cellulase and PG mRNAs, it has little effect on the induction of EFE and P-450 mRNAs. Cellulase and PG enzyme activities are absent in extracts of discs treated with AVG, NBD, or 2,4-D, as are antigenically detectable cellulase and PG proteins. The strong appearance of ripening-related mRNAs in discs inhibited from softening by ethylene antagonists suggests posttranscriptional control by ethylene. Similarly, inhibition of ripening by 2,4-D without suppression of mRNA induction suggests translational control. Whether ethylene inhibits transcription or postttranscriptional events or both depends on its concentration. | Reuber MD (1983)
Carcinogenicity and toxicity of 2,4-dichlorophenoxy-acetic acid.
The Science of the total environment 31, 203-218 [PubMed:6362003]
[show Abstract]
2,4-Dichlorophenoxyacetic acid (2,4-D) is carcinogenic in male and female rats and probably also in mice. Male and female rats ingesting 2,4-D developed increased incidences of malignant neoplasms. Lymphosarcomas were increased in rats of both sexes, and neoplasms of the mammary gland in female rats. Male rats also had carcinomas of the endocrine organs. 2,4-D isooctyl ester was carcinogenic for the lymphoreticular system in female mice. 2,4-D and 2,4-dichlorophenol also were promoters of neoplasms of the skin in mice. Male mice given 2,4-D isopropyl ester developed an increased incidence of neoplasms of the lung. 2,4-D also is mutagenic and teratogenic in animals and causes poisoning in animals and human beings. |
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2014-10-29
