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1.
Crops and soils from field trials in 1967–1970 in several countries have been analysed for residues of the triazine herbicide cyanazine (‘BLADEX’ 1 Shell Registered Trade Mark. a or ‘FORTROL’a' 2-chloro-4-(1-cyano-1-methylethylamino)-6-ethylamino-1,3,5-triazine) and for its degradation products 2-chloro-4-(1-carbarmoyl-1-methylethylamino)-6-ethylamino-1,3,5-triazine ( II ), 2-chloro-4-(1-cyano-1-methylethylamino)-6-amino-1,3,5-triazine ( V ) and 2-chloro-4-(1-carbonyl-1-methylethylamino)-6-amino-1,3,5-triazine ( VI ). The time for the concentration of cyanazine in soils to fall to half the initial value was in the range 1.3 to 5 weeks with a mean value of 2.4 weeks. The rate of loss was not affected by sparse crop cover and there was some indication that the rate was greater under moist soil conditions. Residues of up to 0.5 part/million of ( II ) and up to 0.08 part/million of ( VI ) were detected in soils at 4 weeks from cyanazine application at 2 kg/ha. The residues of cyanazine and the degradation products declined rapidly and were 0.07 part/million or less at 16 weeks from treatment. Repeated annual applications did not lead to a detectable build up of residues in soil. Neither residues of cyanazine nor those of ( II ), ( V ) or ( VI ) could be detected in a wide range of crops harvested from soil treated in accordance with the likely recommendations and the limits of detectability were 0.01 to 0.04 part/million. 相似文献
2.
The breakdown of the triazine herbicide cyanazine (“BLADEX”,a 2-chloro-4-(1-cyano-1-methylethylamino)-6-ethylamino-1,3,5-triazine) has been studied in spring and winter wheat and potatoes grown under indoor conditions in soils treated at planting with up to 1.5 kg/ha of the radiolabelled herbicide. Breakdown products were mainly those formed by hydrolysis of the cyano group to give an amide ( II ) and an acid ( III ) followed by hydrolysis of the chlorine to hydroxyl ( IV ). De-N-alkylation reactions also occurred although these were less evident in soils. In wheat the chloro acid ( VII ) formed by the des-ethylation of ( III ) was more evident than in previous studies with maize. In all of the crops at harvest the residues were mainly of the hydroxy acids ( IV ) and ( VIII ); ( IV ) 2-hydroxy-4-(1-carboxy-1-methylethylamino)-6-ethyl-amino-1,3,5-triazine; ( VIII ) 2-hydroxy-4-(1-carboxy-1-methylethylamino)-6-amino-1,3,5-triazine, respectively. In potatoes and spring wheat they were present in both free and conjugated forms whereas in winter wheat they were almost entirely in conjugated forms. The compounds (IV) and (VIII) are of a low order of toxicity to animals and are not herbicidal. They are unlikely to present a residue hazard if present in field crops. 相似文献
3.
The hydrolysis of cyanazine 1 Cyanazine is the proposed common name for the herbicide sold under the Shell registered trade name BLADEX. (2-chloro-4-cyanoisopropylamino-6-ethylamino-1,3,5-triazine) has been studied using 14C-ring labelled compound over a temperature range of 25° to 75 °C and over a range of pH values from 1.5 to 12. The activation energies and the activation entropy changes during hydrolysis showed there was a different mechanism under acid and alkaline conditions. The only product identified after hydrolysis in acid solutions was 2-hydroxy-4-carboxyisopropylamino-6-ethylamino-1,3,5-triazine. In alkaline solution the same hydroxy-acid was the end-product, but 2-chloro-4-amidoisopropylamino-6-ethylamino-1,3,5-triazine was isolated as an intermediate. The variation of the specific rate constants with temperature for hydrolytic catalysis by H+, OH? was determined, thus enabling the hydrolytic half-life of cyanazine to be calculated at any pH and temperature. 相似文献
4.
A semi-open circuit system for measuring changes in net CO2 exchange (NCE) in single leaves of intact grasses following herbicide treatment is described and evaluated. There were significant differences in levels of inhibition and subsequent recovery of NCE in maize and eight weedy panicoid grasses following limited root uptake of atrazine (2-chloro-4-ethyl-amino-6-isopropylamino-1,3,5-triazine). cyanazine [2-chloro-4-(1-cyano-1-methylethylamino)-6-ethylamino-1,3,5-triazine] and cyprazine (2-chloro-4-cyclopropylamino-6-isopropyl-amino-1,3.5-triazine). Rate of NCE recovery was positively correlated (P = 0.05) with growth of seedlings in nutrient solution containing the herbicides. Rates of NCE recovery >0.9 mg CO2 per dm2 per h/h reflected rapid rates of herbicide detoxification in the leaves and a significant tolerance to preplant incorporated and postemergence applications of atra-zine, cyanazine and cyprazine. In contrast, some species, e.g. large crabgrass [Digitaria sanguinalis (L.) Scop.] and proso millet (Panicum miliaceum L.) treated with cyanazine demonstrated considerable tolerance to these treatments in spite of low NCE recovery rates indicating that factors other than foliar detoxification may play an important role in the tolerance of some grasses to 2-chloro- 1,3,5-triazine herbicides. 相似文献
5.
M.C. Giardina M. de Agazio M.T. Giardi R. Buffone 《Pesticide biochemistry and physiology》1983,19(1):11-14
The action of atrazine and its biodegradation products on the membrane transport of potassium in roots was evaluated in both sensitive and resistant plants. Excised roots of maize and oat showed inhibition of potassium uptake efficiency in the presence of 1.4 × 10?4M atrazine and 1.4 × 10?4M deethylated atrazine. Other biodegradation products such as 2-chloro-4-amino-6-ethylamino-1,3,5-triazine,2-chloro-4,6-,bisamino-1,3,5-triazine, and 2-chloro-4-amino-1,3,5-triazine showed no inhibitory effect on the K+ uptake capacity. Two maize hybrids showing different uptake efficiency were inhibited differently by atrazine. We suggest that atrazine and deethylated atrazine inhibited the K+ transport interacting directly with the plant cell membranes without discerning between resistant and sensitive plants. 相似文献
6.
Radioisotope techniques have been used to study the breakdown products that are formed from the herbicide cyanazine ( BLADEX )a, 2-chloro-4-(1-cyano-1-methylethyl-amino)-6-ethylamino-1,3,5-triazine, in soils and in maize grown in the soils under indoor conditions. In soils of different types cyanazine broke down mainly by conversion of the nitrile group to amide ( II ) and then to an acid ( III ) followed by hydrolysis of the ring chlorine to hydroxyl ( IV ). Dealkylation reactions occurred to only a limited extent in soils. In maize plants grown in treated soils the hydrolysis products, the amide ( II ) and the hydroxy acid ( IV ) were detected as well as appreciable quantities of products ( VI ) and ( VIII ) formed from these by loss of the N-ethyl group. In plants the hydroxy acids ( IV ) and ( VIII ) were present in the free form and there was also evidence for conjugates which were not identified but could be converted to these hydroxy acids, ( IV ) and ( VIII ), on treatment with acids. In these indoor studies the major residues appear to be the hydroxy acid ( IV ) in soils and ( IV ) and its dealkylated analogue ( VIII ) in plants grown in treated soils. These compounds are not herbicides and are of a low order of toxicity to mammals. 相似文献
7.
The disappearance and movement of three triazine herhicides and several of their degradation products in soil under field conditions 总被引:1,自引:0,他引:1
Several degradation products of the iriazine herbicides atrazine [2-chloro-4-ethylamino-6-isapropylainino-1,3,5-triazine], cyprazine [2-chloro-4-cyclopropylamino-6-isopropylamino-1,3,5-triazine] and cyanazine [2-chloro-4-(l-cyanomethylethyl-amimo)-6-ethylamino-1,3,5-triazine] were monitored over a 3-year period in soil Trom fields under maiTC production. The soils were predominately loamy sands and sandy clay loams. HydroKy-triazines were determined semi-quanlilatively m the soil samples by gaschromalography, after methylation. Their levels ranged Trom 0.05 to 0.5 ppm. The hydroxy-triazines were the predominant triazine residues in the field during ihe spring and autumn, N-de-ethylated atrazine [2-chloro-4-amino-6-iso-propylamino-1,3,5-triazine] persisted at relatively high levels (0.015–0.02 ppm) 12 months after the application of atrazine. Greater proportions of N-de-ethylated atrazine and cyanazine II [2-chloro-4-(1-carbamoyl-1-methyleihylamino)-6-ethyl-amino-s-iriazine] than of atrazine or cyanazine were found to move through the soil profile into subsurface drainage water (1.2–1.6 m depth). Abbau und Transport von drei Triazin-Herbiziden und einiger ihrer Abbauproduk te im Boden unter Feldhedingungen Boden von Maisfeldern wurde über eine Periode von drei Jahren auf Abbauprodukte folgender Triazin-Herbizide unter-suchi: Atrazin [2-Chlor-4-äthylamino-6-isopropylatnino-1,3,5-triazin], Cyprazin [2-Chlor-4-cyclopropylamino-6-isopropyla-mino-1,3,5-(triazin) und Cyanazin [2-Chlor-4-(1-cyanoinethy-läthylamino)-6-äthylamino-1,3,5-triazin], Bei den Böden han-delie es sich hauptsächlich um lehmige Sande und sandig-tonige Lehme Hydroxy-Triazine wurden in den Bodenproben gas-chromatogruphish nach Methylierung. semi-quantitativ be-stimmt. Ihre Konzeniration im Boden betrug zwischen 0.05 und 0.5 ppm. Die Hydroxy-Triazine waren im Frähjahr und Herbst die vorherrschenden Rücksiände, N-desäthylieries Airazin [2-Chlor-4-amino-6-isopropyIamino-1,1,5-triazin] war zwölf Monate nach der Atrazin-Applikation mit relative hohen Kon-zenirationen(0.015–0.02 ppm) vorhanden. Von N-desäthylier-tem Airazin und Cyanazin II [2-Chlor-4-(1 carbamoyl-1–methy-läthylamino)-6-äthylamino-s-triazin] wurden grössere Anteile im Boden in das unterirdische Drainagewasser transportiert (1.2–1.6 m Tiefe) als es für Atrazin oder Cyanazin der Fs Swiir Disparition et migration dans le sol, au champ, de trois triazines herhicides et de plusieurs de leurs produits de dégradalion. Plusieurs produits de dégradation des triazines herbicides suivantes: atrazine (2-chloro-4-éthylamino-6-isopropylamino-1,3,5-triazine) cyprazine (2chloro-4-cyclopropylamino-6-isopropylamino-l,3,5-triazine) et cyanazine (2-chloro-4 (l-cyanométhyléthylamino)-6-éthylamino-l,3,5-triazine) ont été contrölés dans le sol. pendant une période de trois années, dans des champs de maïs en production, Les sols étaient pour la plupart sablo-limoneux et limono-argilo-sableux, Les hydroxy-triazines ont été déterminées semi-quantalivcmeni dans les échantillons de sols, par chroma tographie gazeuse aprés méthy lation, Leursconcen [rations s'étendaienlde0.05à 0.5ppm, Les hydroxy-triazines ont été les résidus les plus imporiants dans le champ au printemps et à I'aulomne, L'alrazine N-dé-éthylée [2-chloro-4-amino-6-isopropylamino-l.3.5-triazine] a persistéà des concentralions rclativemeni élevées (0.015 à 0.02 ppm) douzemois aprés l'application de l'atrazine, Il a été conslaté que des proportions d'atrazine N-dé-éthylée et de cyanazine II [2-ehloro-4(l-carbamoyl-1-méthyléthylamino)-6-éthylamino-1,3,5-triazine] plus importantes que celles de l'atrazine ou de la cyanazine, migraient à travers le profil du sol. dans la subsurface de drainage dc l'eau (1,2 à 1.6 m de profondeur). 相似文献
8.
Adsorption of transformation products of atrazine by soil 总被引:1,自引:0,他引:1
The adsorption of atrazine and its transformation products, desisopropylatrazine (2-chloro-4-ethylamino-6-amino-l,3,5-triazine), desethyl-atrazine (2-chloro-4-amino-6-isopropylamino-l,3,5-triazine) and hydroxyatrazine (2-hydroxy-4-ethylamino-6-isopropylamino-l,3,5-triazine) to four top-soils was measured. Adsorption coefficients decreased in the order hydroxy atrazine, atrazine, desisopropylatrazine, and desethyl-atrazine: the distribution coefficient between organic matter and water (KOM) ranged from 40 to 100 dm3 kg?1 for atrazine, from 30 to 60 dm3 kg?1 for desisopropylatrazine, from 20 to 50 dm3 kg?1 for desethylatrazine and from 100 to 590 dm3 kg?1 for hydroxy atrazine. Data are discussed in the context of earlier literature. 相似文献
9.
The metabolism of cyanazine (2-chloro-4-(1-cyano-1-methyl-ethylamino)-6-ethylamino- 1,3,5-triazine) by corn (Zea mays, L.), fall panicum (Panicum dichotomiflorum Michx.), and green foxtail (Setaria viridis L.) was compared. Cyanazine metabolism by plants at the four-leaf stage was examined by thin-layer chromatography following foliar or root treatments with 14C-cyanazine. Five days following foliar 14C-cyanazine applicalion, fall panicum and green foxtail contained a larger number of water- and chloroform-soluble metabolites than corn, whereas, following root treatment, the opposite was true. Corn rapidly hydrolysed the nitrile group and hydroxylated the two-position on the triazine ring. Accumulation of the dealkylated cyanazine was evident in green foxtail, the most susceptible of the species studied. Metabolism of cyanazine supplied to the roots appeared to differ from foliar treatments in the weed species as more unchanged cyanazine was recovered. Rapid metabolism of cyanazine by corn roots provided evidence for an active cyanazine detoxication mechanism in the roots. 相似文献
10.
Romualdo Muoz Antonio Martinez-Martinez Alfonso Ros-Barcelo Ma Angeles Pedreo 《Pest management science》1990,28(3):283-288
The molecular action of herbicides with a triazine structure, such as atrazine (2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine) and metribuzin (4-amino-6-tert-butyl-3-methylthio-1,2,4-triazin-5(4H)-one), has been related to their inhibition of the electron carrier system between chloroplastic photosystems II and I. This report provides evidence that 4-amino-6-methyl-3-phenylamino-1,2,4-triazin-5(4H)-one, a recently synthesised triazine, structurally analogous to metribuzin, causes a powerful inhibition of the cell-wall lignification catalysed by peroxidase from lupin. The two reactions involved in this lignification process are: oxidative polymerisation of coniferyl alcohol and the generation of hydrogen peroxide at the expense of NADH oxidation. 相似文献
11.
W. J. Allender 《Pest management science》1990,29(2):183-186
A method is described for the measurement of simazine [2-chloro-4,6-bis(ethylamino)-1,3,5-triazine] residues in chickpeas (Cicer arietinum). Ground chickpea samples were extracted with dichloromethane, followed by clean-up on alumina. Gas-liquid chromatography using metribuzin [4-amino- 6-tert-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5-one] as internal standard with thermionic detection was used to quantify simazine residues. The limit of detection was 0.02 mg kg?1 and the recoveries of simazine from chickpea samples (0.1–4 mg kg-1) averaged 92%. 相似文献
12.
Triazine herbicide residues were monitored in the rivers Adour, Danube, Garonne, Herault, Loire, Marne, Oise, Rhine, and Rh?ne from spring 1976 to fall 1977 to determine whether the continued use of the compounds resulted in accumulations of undesirable residues in the streams. Samples were generally collected monthly or bimonthly and analyzed for the parent compounds atrazine, simazine, terbumeton, terbuthylazine, and dealkylated metabolites GS 26571 (2-amino-4-etert-butylamino-6-methoxy-1,3,5-triazine) and G 30033 (2-amino-4-chloro-6-ethylamino-1,3,5-triazine). The compounds were extracted into dichloromethane and quantitated by gas chromatography (GC) with nitrogen-specific detection. Selected results were verified by GC with mass fragmentographic detection. Limit of detection was usually 0.4 mg/m3; 80 percent of all results were below 0.4 mg/m3, 14 percent were 0.4-1 mg/m3, 6 percent were 1-10 mg/m3, and 0.3 percent were higher than 10 mg/m3. Detectable residues were mainly atrazine from the downstream sampling sites. Residues usually peaked during June. 相似文献
13.
2-z-Substituted benzylamino-4-substituted-amino-6-chloro-1,3, 5-triazines are herbicidal compounds showing leaf-burning and/or growth inhibition with concomitant greening and stunting. Effects of chiral 1,3,5-triazine compounds in a light-independent seedling root elongation test with Echinochloa crus-galli var. frumentacea Wight demonstrated an interaction between chirality and root growth inhibition. The test compounds inhibited root growth, and this inhibition was due to interference with a system or systems other than photosynthesis. 4-(R)-sec-butylamino-2-(α,α-dimethylbenzyl)amino-6-chloro-1,3, 5-triazine showed the highest inhibitory activity, and 4-methylamino-2-(R)-a-methylbenzylamino-6-chloro-1,3,5-triazine was second. The chiral requirement for a strong inhibition of root growth was the (R)-configuration, contrasting with the requirement for the (S)-configuration for an inhibition of photosystem II. 相似文献
14.
Francesco Tafuri Maurizio Patumi Cesare Marucchini Mario Businelli 《Pest management science》1982,13(6):665-669
Gas-chromatographic analyses of extracts of soil samples from plots, treated with a 50% atrazine wettable powder at dose rates of 2 and 4 kg a.i. ha?1, showed the presence of a new atrazine degradation product. This product was isolated, concentrated and purified by column chromatography and high-performance liquid chromatography. The chromatographic properties of this material were identical with those of a product isolated from a 0.02% methanolic solution of 2-amino-4-chloro-6-isopropyl-amino-1,3,5-triazine that had been stored under laboratory conditions. A combined gas-liquid chromatographic/mass spectrometric assay identified the new product in soil as 2-isopropylamino-4-methoxy-6-methylamino-1,3,5-triazine. 相似文献
15.
A cytokinin-like effect of chiral 2-α-methylbenzylamino-4-alkylamino-6-chloro-1,3,5-triazines was found using a rhizome-inducing assay with Cyperus serotinus Rottb. tubers. C. serotinus tubers germinated in distilled water yielded plantlets with roots and leaves. Secondary rhizomes were normally not observed within the regular 14-day incubation time in water culture, whereas after increasing incubation periods a very short rhizome appeared (controls). 6-Benzylaminopurine (BA) significantly stimulated rhizome induction, while other plant hormones were inactive. The (R)-isomers of the 1, 3, 5-triazine compounds also stimulated induction of the rhizomes, whereas the (S)-isomers did not. The described rhizome induction system seems to be suitable as a cytokinin bioassay. The (R)-1, 3, 5-triazine compounds showing rhizome-inducing activity (RI activity) inhibited root formation and plant growth at high concentrations with symptoms which were very similar to those of BA. Therefore, the (R)-isomers appear to act as cytokinins in the rhizome induction assay. 相似文献
16.
Kazuya Koizumi Nobuhiro Kuboyama Kohtaro Tomono Akira Tanaka Aiko Ohki Hitoshi Kohno Ko Wakabayashi Peter Bger 《Pest management science》1999,55(6):642-645
New fluoroalkyl-substituted 1,3,5-triazine derivatives were synthesized and screened for herbicidal activity using a greenhouse pot test. Surprisingly, a series of 2-alkyl-4-fluoroalkyl-6-aralkylamino-1,3,5-triazines e.g. 6-(4-bromobenzylamino)-2-methyl-4-trifluoromethyl-1,3,5-triazine was found to possess strong pre- and post-emergence herbicidal activities, although the conventional herbicidal 1,3,5-triazines generally should have a 2-substituted-4,6-diamino-1,3,5-triazine structure for herbicidal activity. Our compounds show strong Photosynthetic Electron Transport inhibitory activity (PI50 c 7). Although their herbicidal effect is considered to be caused by a process similar to that for the conventional 1,3,5-triazine herbicide atrazine, they can control atrazine-resistant Chenopodium album effectively, and will thus form promising trial compounds for new triazine herbicide design. 相似文献
17.
Francesco Tafuri Luciano Scarponi Piero Perucci P. Lodovico Giusquiani 《Pest management science》1981,12(4):449-454
The effect of some 1,3,5-triazine herbicides, on the rate of oxidative decarboxylation of tryptophan by peroxidase from corn seedlings, varied with the concentration. Atrazine was stimulatory in vivo at 10-6M but not at 108 M or lower, whereas terbutryne was inhibitory at 10-6M but not at 10-8M or below. Prometryne inhibited enzyme activity at 10-6M and stimulated it at 10-10M and at 1012M, while simazine caused stimulation at 10-6M and inhibition at 10?10M and 10?12M. Atraton reduced enzyme activity at 10?6M and 10?8M but had no effect at 10?10M and 10?12M. When peroxidase activity was assayed in acetone-dried powders from seeds, harvested from fields that had received typical atrazine applications, the quantities of tryptophan consumed were significantly less than the quantity determined in the control powder. From the results obtained, by incorporating dealkylated and 2-hydroxy metabolites of atrazine at 10?6M into the culture solutions, it seems possible that the inhibition observed may have been due to the presence of 4-amino-6-ethylamino-1, 3, 5-triazin-2-ol and/or 4, 6-diamino-1, 3, 5-triazin-2-ol residues in seeds from treated plots, even if, in previously reported experiments, analyses had not detected their presence. 相似文献
18.
Separate populations of Senecio vulgaris were found that evolved partial tolerance to s-triazine herbicides and others that were totally resistant (plastid resistance). In plants from the susceptible, tolerant, and resistant populations, about one half of applied [14C]atrazine (2-chloro-4-ethylamino-6-isopropylamino-s-triazine) was rapidly N-dealkylated to the des-ethyl and des-isopropyl products. These products were relatively inactive in inhibiting photosystem II and did not compete with atrazine. After 6 days, less than 25% of the applied [14C]atrazine was metabolized to water-soluble degradation products but they were not 2-hydroxy derivatives. Less than 2% of the applied atrazine was incorporated into methanol-insoluble residues. The results on metabolism do not explain the tolerance of Senecio to atrazine. However, our results show that N-dealkylation of the s-triazines is more active than previously reported. 相似文献
19.
MOSHE J. PINTHUS 《Weed Research》1972,12(3):241-247
Summary. The effects of pre-sowing treatments with terbutryne (4-ethylamino-2- niethylthio-6-t-butylamino-1,3,5-triazine) and with simazine (2-chloro-4,6-bisethyl-amino-1,3,5-triazine) on seedling mortality of wheat grown from regular seed and from seed containing about 40 ppm chlormequat (2-chloroethyl trimethylammonium chloride), due to a late chlormequat treatment of the seed-parent, were tested in two pot experiments. In another pot experiment the effects of pre-sowing and post-emergence treatments of terbutryne on dry matter accumulation and moisture content in SPT (= Seed-Parent Treated) and regular wheat seedlings were examined.
No significant differences in simazine resistance between regular and SPT seed were found. However, there was a marked and significant increase in terbutryne resistance of SPT over regular seeds, which was expressed by a longer period to 50% seedling mortality as well as by a lower daily increase in mortality. Growth retardation, caused by pre- sowing as well as by post-emergence terbutryne treatments, was appreciably less in the SPT seedlings than in the regular ones. The higher terbutryne resistance of the SPT seedlings may be attributable to their higher moisture content induced by the chlormequat.
Effet du traitement des pieds meres avec le chlorméquat sur la résistance des plantules de blé a la terbutryne et à la simazine 相似文献
No significant differences in simazine resistance between regular and SPT seed were found. However, there was a marked and significant increase in terbutryne resistance of SPT over regular seeds, which was expressed by a longer period to 50% seedling mortality as well as by a lower daily increase in mortality. Growth retardation, caused by pre- sowing as well as by post-emergence terbutryne treatments, was appreciably less in the SPT seedlings than in the regular ones. The higher terbutryne resistance of the SPT seedlings may be attributable to their higher moisture content induced by the chlormequat.
Effet du traitement des pieds meres avec le chlorméquat sur la résistance des plantules de blé a la terbutryne et à la simazine 相似文献
20.
Summary. The rates of degradation of three triazine and two uracil herbicides were followed at 13·2 and 31·2°C in one soil. Soil was treated with 8 ppm of 2-chloro-4-ethyl-amino-6-isopropylamino-1,3,5-triazine (atrazine), 2-chloro-4,6-bisethylamino-1,3,5-triazine (simazine), 2-mcthylthio-4-ethylamino-6-isopropylamino-1,3,5-triazine (ametryne), 3-sec-butyl-5-bromo-6-methyluracil (bromacil) and 3-tert-butyl-5-chloro-6-methyluracil (terbacil) and monthly samples analysed chemically to determine the amounts remaining. Evaluation of the rate constant at two temperatures permitted calculation of the energy of activation from the Arrhenius equation. It was determined to a first approximation that soil degradation followed a first order rate law with no lag period and that the rate could be related to molecular structure. The energies of activation in kcals/mole were: atrazine 10-8, simazine 9-2, ametryne 6-1, bromacil 3-0, and terbacil 6-1. These values suggest breakage of the common carbon-chlorine bond in atrazine and simazine but breakage of a different bond in ametryne. Examination of bond energies and known mechanisms of breakdown for triazines supported the hypothesis of breakage of the bond at the two position. The data on decomposition of the uracils indicate that the carbon-halogen bond was broken in each molecule. Dégradation des triazines et des uraciles herbicides dans le sol Résumé. Les taux de dégradation de trois triazines et de deux uraciles herbicides ont été observés α 13,2 et 31,2° C dans un sol. Ce sol a été traitéà la concentration de 8 ppm avec la 2-chloro-4-éthyIainino-6-isopropylamino-1,3,5-triazine (atrazine), la 2-chloro-4,6-biséthylamino-l,3,5-triazine (simazine), la 2 méthylthio-4-éthylamino-6-isopropylamino-1,3,5-triazine (amétryne), le 3-sec-butyl-5-bromo-6-méthyluracile (bromacil) et le 3-tert-butyl-5-chloro-6-méthyluracile (terbacil). Des échunlillons ont été analysés chimiquement tous les mois pour déterminer les résidus. L'évaluation du taux constant à deux températures a permis le calcul de l'energie d'activation d'aprés l'équation d'Arrhenius. Selon une premiére approximation, la dégradation a suivi une loi de taux de premier ordre sans période de retard et le taux peut être reliéà la structure moléculaire. Les énergies d'activation en kcals/mole furent: atrazine 10,8, simazine 9,2, amétryne 6,1, bromacil 3,0 et terbacil 6,1. Ces valeurs suggérent une rupture d'une liaison carbone-chlore dans I'atrazine et la simazine mais la rupture d'une liaison différente dans l'amétryne. L'examen des énergies de liaison et des mécanismes connus de dégradation pour les triazines amène à formuler l'hypothése de la rupture d'une liaison en position deux. Les résultats relatifs aux uraciles indiquent tjue la liaison carbone-halogéne a été rompue dans chaque molécule. Der Abbau von Triazin- und Uracilherbiziden im Boden Zusammenfassung. Die Abbaurate von 3 Triazin- und 2 Uracilherbiziden im Boden wurde bei 13,2 und 3l,2°C untersucht. Aus dem mit 8 ppm 2-Chlor-4-athylamino-6-isopropylamino-1,3,5-triazin (Atrazin),2-Chlor-4,6-bisathylamino-[3,5-lriazin (Simazin), 2-Methyllhio-4-athylamino-6-isopropylamino-1,3,5-triazin (Ametryn), 3-scc-Butyl-5-brom-6-methyluracil (Bromacil) und 3-tert-Butyl-5-chlor-6-methyluracil (Terbacil) behandelten Bodenrückständen wurden monatlich Proben entnommen und chemisch die Rückstände erniittelt. Die Bestimmung der Geschwindigkeitskonslantcn bei zwei Temperaturen eriaubte die Borechnung der Aktivicrungscnergic nach der Arrhenischen Gleichung. In erster Annäierung verlief der Abbau als Prozcss erster Ordnung ohne Latenzphase und die Abbaurate stand in Beziehung zur Struktur des Molekuls. Die Aktivierungsenergie betrug fur Atrazin 10,8, Simazin 9,2, Ametryn 6,1, Bromacit 3,0 und Terbacil 6,1 kcal/Mol. Diese Werte lassen für Simazin und Atrazin einen Bruchder der bcide Herbizide gemeinsamen Kohlensloff-Chlorbindung vermuten, wahrend im Falle des Ametryn eine andere Bindung hiervon betroffen war. Die Prufung der Bindungsenergien und der bekannten Abbau me chanismen bei Triazinen unterstCitzcn die Hypothcse, dass der Bruch in der 2-Position erfolgte. Die Ergebnisse fur die Uracile deuten darauf hin, dass bei beiden Moleküien der Abbau an der Kohlenstoff-Halogenbindung ansetzte. 相似文献