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1.
The degradation in soil of the major constituents of a 1,3-dichloropropene-1,2-dich-loropropane nematicide has been studied under laboratory and outdoor conditions. In sealed glass containers, ( Z)- and ( E)-1,3-dichloropene- 2-14C were converted in soil into the corresponding 3-chloroallyl alcohols and these alcohols were in part strongly bound to the soil. The ( Z)- and ( E)-3-chloroacrylic acids were also found as minor products. More polar products were detected and these released the chloroacrylic acids in 20–30% yield upon hydrolysis. Although the 1,3-dichloropropenes were lost by volatilisation from soil stored in open glass jars outdoors, they also underwent degradation to the same products that were detected in sealed containers. There was evidence of only slight degradation of 1,2-dichloropropane- 2-14C (4 % or less of the applied radioactivity remained unextracted from a loam soil after 5 months). When soil treated with the 1,2-dichloropropane was stored outdoors in an open glass container, less than 1 % of the original radiolabel remained in the soil after 10 days under these conditions due to volatilisation of the applied material. In a separate experiment potatoes were grown in soil 6 months after treatment with a mixture of both ( Z)- and ( E)-1,3-dichloropropene- 2-14C and 1,2-dichloropropane- 2-14C. Although 5 % of the applied radiolabel remained in the soil at potato harvest the potato tubers contained only a very small residue (0.007 mg/kg).  相似文献   

2.
A series of methyl esters of N-substituted (Z)- and (E)-maleamic acids were synthesized and their effect on food intake measured on fifth-instar nymphs of Triatoma infestans. Suppression of food intake was found only for the (Z)-isomers. The initial reaction rate of the synthesized compounds with glutathione (GSH) was calculated from the reaction in vitro of the (Z)-isomers. No reaction was observed with the (E)-isomers. Good correlation between the suppression of food intake, measured by its ED50 (effective dose that inhibited feeding of 50% of the population) and the initial reaction rate with GSH and the hydrophobic parameter π, was found. © of SCI.  相似文献   

3.
BACKGROUND: The banana moth, Opogona sacchari Bojer, is a polyphagous agricultural pest in many tropical areas of the world. The identification of an attractant for male O. sacchari could offer new methods for detection, study and control. RESULTS: A compound extracted from female O. sacchari elicited responses from antennae of male moths. This compound was identified as a 2/3,(Z)13‐octadecadienal by gas chromatography‐mass spectrometry. An analog, 2/3,(Z)13‐octadecadienol, was also detected in some extracts at roughly a 1:20 ratio (alcohol:aldehyde) but did not elicit responses from antennae of male moths. Electroantennograms of synthetic candidate dienals found the strongest responses from (Z, Z)‐2,13‐octadecadienal and (E, Z)‐2,13‐octadecadienal. In field trials, (E, Z)‐2,13‐octadecadienal attracted more male O. sacchari than (Z, Z)‐2,13‐octadecadienal. Attraction was not improved for either of these compounds when the corresponding stereoisomeric alcohol was added at ratios of 1:1, 1:10 or 1:100 (alcohol:aldehyde). Jackson sticky traps containing 250 µg lures of (E, Z)‐2,13‐octadecadienal caught as many males as did traps holding virgin females. CONCLUSION: (E, Z)‐2,13‐octadecadienal has been identified as an attractant for O. sacchari males and can be used as a monitoring lure of populations of this moth. Copyright © 2010 Society of Chemical Industry  相似文献   

4.
铜绿丽金龟对寄主植物挥发物的触角电生理及行为反应   总被引：2，自引：0，他引：2  
为深入了解铜绿丽金龟的取食行为,探索开发安全高效的植物源引诱剂,应用昆虫触角电位反应仪和Y型嗅觉仪测试其对不同寄主植物挥发物的趋向行为差异,并根据室内行为结果配制诱剂进行大田试验。结果表明:铜绿丽金龟雄虫对水杨酸甲酯和(1,1’-联环戊基)-2-酮的触角电位反应(electroantennography,EAG)值显著高于其它试剂;石竹烯和水杨酸甲酯能引起雌虫触角较强的电位反应;乙酸顺式-3-己烯酯和石竹烯分别对雄虫和雌虫有较高的嗅觉选择反应率,分别达0.95和0.94。综合EAG和嗅觉试验结果,选择对雌、雄虫均有较好引诱效果的反式-2-己烯醛、乙酸顺式-3-己烯酯、石竹烯、(1,1’-联环戊基)-2-酮和水杨酸甲酯进行田间试验,最终筛选到铜绿丽金龟雄虫的最适引诱剂为每诱芯360 mg乙酸顺式-3-己烯酯,雌虫的最适引诱剂为每诱芯360 mg石竹烯,日诱虫量分别可达33.00±1.53头和29.33±1.45头。  相似文献   

5.
The performance of a newly developed column method for pesticide transformation rate measurements in the subsoil was tested using (Z)- and (E)-3-chloroallyl alcohol as model compounds. Sandy anaerobic water-saturated subsoil was collected at between 1·8 and 2·3 m below the surface of a flower-bulb field. Transformation rates were measured using subsoil columns that were filled in situ and were compared with the transformation rates in laboratory incubation systems. In the column experiment the half-life ranged from 0·5 to 5·2 days for (Z)-3-chloroallyl alcohol and from 1·0 to 5·5 days for (E)-3-chloroallyl alcohol. The capacity of the saturated subsoil for transformation of both isomers increased in the course of the column experiment. In the incubation experiment the 3-chloroallyl alcohols were transformed gradually in the first three days, with a half-life of 1·9 days for both isomers. Thereafter the transformation rate accelerated. The general conclusion is that the column method yields results similar to those of the incubation method for these rapidly transforming compounds.  相似文献   

6.
When infested with Fusarium sp., the cereals Triticum aestivum L. emend. Fiori et Paol. cv. ‘Bombona’, Avena sativa L. cv. ‘Deresz’, and Hordeum vulgare L. cv. ‘Rastik’ can emit volatile organic compounds (VOCs). The VOCs differ both qualitatively and quantitatively from those emitted by non-infested wheat, oat, and barley plants. We detected increased amounts of VOCs released by green leaves (green leaf volatiles – GLVs): (Z)-3-hexenal, (E)-2-hexenal, (Z)-3-hexen-1-ol, (E)-2-hexen-1-ol, (Z)-3-hexen-1-yl acetate, 1-hexyl acetate as well as the other VOCs like (Z)-ocimen, linalol, linaloloxide, benzyl acetate, indole, and β-caryophyllene. The lipoxygenase pathway resulted in the highest release of GLVs in comparison to the other biochemical pathways of volatile production. As a result of Fusarium infestation, the amounts of VOCs varied between tested cereals. We also subjected uninfested wheat, barley, and oat plants to infested wheat plants, and found that these cereals released larger amounts of VOCs compared to control plants. Emitted amounts of VOCs were significantly higher the shorter the distance between uninfested and infested plants.  相似文献   

7.
A mixture of (Z)-11-hexadecenal (Z11–16: Ald), (E)-11-hexadecenal (E11–16: Ald), (Z)-13-octadecenal (Z13–18: Ald), and (E)-13-octadecenal (E13–18: Ald) on rubber septa (100∶10∶100∶10 μg, respectively) was superior to virgin females in attracting maleCryptoblabes gnidiella Mill. (Lepidoptera: Pyralidae) to traps. A dichloromethane extract of 200 female ovipositors was separated into fractions by gas-liquid chromatography (GLC) on OV-101 and Hi-Eff 8BP. Two fractions had significant electroantennogram (EAG) activity, and had the retention times ofZ11–16∶Ald andZ13–18∶Ald on each GLC column. These fractions contained insufficient material for further chemical work. SyntheticZ11–16∶Ald andZ13–18∶Ald had the greatest EAG activity of a series of monounsaturated 12?, 14?, 16?, and 18-carbon alcohols, acetates, and aldehydes. Various ratios ofZ11–16∶Ald andZ13–18∶Ald were tested in traps, and a 1∶1 mixture was the most attractive. Addition of small amounts of the correspondingE isomers significantly increased trap catches.  相似文献   

8.
BACKGROUND: In recent years, many studies have been carried out on the behavioural and electrophysiological responses of Cydia pomonella (L.) to host volatile emissions, to find alternative attractants to the sex pheromone for pest monitoring. These studies have focused on apple and pear, and very little has been done on walnut. In the present work, the diurnal and seasonal variation in walnut volatile emissions and the electrophysiological response of C. pomonella have been studied. RESULTS: Ninety compounds were detected in walnut emissions, mainly monoterpenes and sesquiterpenes. The most abundant compound was β‐pinene, which, together with (Z)‐3‐hexenyl acetate, (E)‐β‐ocimene, limonene, germacrene D, 1,8‐cineole, sabinene, (E)‐β‐farnesene, (E)‐β‐caryophyllene, β‐myrcene and β‐phellandrene, constituted between 81.9 and 90.5% of the total chromatographic area. Differences between seasonal periods were significant for 39 compounds, and between daytimes for 14 compounds. Discernible and consistent EAD responses were detected to 11 walnut‐origin compounds, and confirmed with synthetics to seven of them. Except for alloocimene, pinocarvone and caryophyllene oxide, all these compounds are also emitted by apple. CONCLUSION: Walnut volatile emissions differ widely from apple ones, but both share many compounds that are EAD‐active in C. pomonella. However, among EAD‐active compounds there are three walnut‐specific ones, which should be further tested in behavioural assays. Copyright © 2008 Society of Chemical Industry  相似文献   

9.
Nineteen novel N-acetyl-2,2-dialkyloxazolidines ( 2 ) and N-acetyl-2-alkyl-4,4-dimethyloxazolidines ( 3 ) were synthesized from commercially available carbonyl compounds and ethanolamine or 2-amino-2-methyl-1-propanol. Their bioactivity against laboratory-reared mosquitoes was compared in patch tests to known N-acetyl-2-alkyloxazolidines ( 1 ) and N,N-diethyl-m-toluamide (deet insect repellent). Isomeric composition measurements by [13C]NMR spectroscopy favoured the Z rotational isomer for samples of 2 (91–96% Z) and the E rotational isomer for samples of 3 (66–71% E), in agreement with molecular mechanics calculations on rotational isomers of model oxazolidines. Samples of 1 were previously shown to exist in solution mostly as the Z isomer (60–70% Z). Within the optimal molecular weight range for these experimental chemicals, the duration of repellency against Aedes aegypti (L.), Anopheles quadrimaculatus Say and Anopheles albimanus Wiedemann generally followed the order: 1 > 2 >deet> 3 . Bioassay data are discussed in relation to the equilibrium populations of rotational isomers for substituted N-acetyloxazolidines.  相似文献   

10.
Two fatty acids, (2E,4Z)-decadienoic acid and (2E,4Z,7Z)-decatrienoic acid, the latter being described for the first time as a natural product, were detected in the culture filtrate of Streptomyces viridochromogenes Tü 6105 by HPLC-diode array screening, purified by chromatographic methods and structurally elucidated by NMR techniques. Both metabolites show strong herbicidal activity against Lemna minor and Lepidium sativum. The herbicidal activities of the isolated compounds were compared with those of similar fatty acids and derivatives. © 1999 Society of Chemical Industry  相似文献   

11.
1,3‐Dichloropropene (1,3‐D), which consists of two isomers, (Z)‐ and (E)‐1,3‐D, is considered to be a viable alternative to methyl bromide, but atmospheric emission of 1,3‐D is often associated with deterioration of air quality. To minimize environmental impacts of 1,3‐D, emission control strategies are in need of investigation. One approach to reduce 1,3‐D emissions is to accelerate its degradation by incorporating organic amendments into the soil surface. In this study, we investigated the ability of four organic amendments to enhance the rate of degradation of (Z)‐ and (E)‐1,3‐D in a sandy loam soil. Degradation of (Z)‐ and (E)‐1,3‐D was well described by first‐order kinetics, and rates of degradation for the two isomers were similar. Composted steer manure (SM) was the most reactive of the organic amendments tested. The half‐life of both the (Z)‐ and (E)‐isomers in unamended soil at 20 °C was 6.3 days; those in 5% SM‐amended soil were 1.8 and 1.9 days, respectively. At 40 °C, the half‐life of both isomers in 5% SM‐amended soil was 0.5 day. Activation energy values for amended soil at 2, 5 and 10% SM were 56.5, 53.4 and 64.5 kJ mol?1, respectively. At 20 °C, the contribution of degradation from biological mechanisms was largest in soil amended with SM, but chemical mechanisms still accounted for more than 58% of the (Z)‐ and (E)‐1,3‐D degradation. The effect of temperature and amendment rate upon degradation should be considered when describing the fate and transport of 1,3‐D isomers in soil. Use of organic soil amendments appears to be a promising method to enhance fumigant degradation and reduce volatile emissions. Published in 2001 for SCI by John Wiley & Sons, Ltd  相似文献   

12.
Bioassays have shown that sand freshly contaminated by ovipositing females of the gregarious desert locust Schistocerca gregaria (Forskal) is more effective in inducing further oviposition from conspecifics than contaminated sand stored for three or six months, which contrasts with results obtained previously with Locusta migratoria (Reiche & Farmaire). The activity of contaminated sand correlated with the levels of three unsaturated aliphatic ketones, (Z)-6-octen-2-one, (E,E)-3,5-octadien-2-one and its geometric isomer (E,Z)-3,5-octadien-2-one present in the volatile emissions from the sand.  相似文献   

13.
Derivatives of 2‐ethyl‐1,3,4(2H)‐isoquinolinetrione in which the 4‐keto group has been modified to (Z)‐oxime, (E)‐ and (Z)‐O‐methyl oxime, (Z)‐N,N‐dimethyl hydrazone, cyano‐imine and dicyanomethylene moieties have been prepared and evaluated as redox mediator herbicides. All of the compounds have the free‐radical properties required to function as redox mediators, as determined by cyclic voltammetry, though only the O‐methyl oximes, the N,N‐dimethyl hydrazone and the cyano‐imine have reduction potentials in the range required to stimulate the light‐dependent consumption of oxygen at photosystem I in isolated chloroplasts. The O‐methyl oximes and the cyano‐imine are fast‐acting post‐emergence herbicides, producing symptoms of rapid desiccation; the (E)‐O‐methyl oxime is the most active herbicide, being somewhat more potent than the parent isoquinolinetrione. Hydrolysis studies indicate that it is unlikely that any compound generates the parent isoquinolinetrione in vivo. Attempts to explain differences between in vitro and in vivo activities using hydrolytic stabilities and physical properties were unsuccessful, and it was concluded that these factors probably play a less significant role in moderating the herbicidal activity of isoquinolinetrione derivatives than originally thought. © 2000 Society of Chemical Industry  相似文献   

14.
The hydrolysis of [14C] fenpropathrin ( I ) [(RS)-α-cyano-3-phenoxybenzyl 2,2,3,3-tetramethylcyclopropanecarboxylate] was studied in buffer solutions at pH 1.9–10.4, and in natural river and sea water at 25, 40, 55 and 65°C under laboratory conditions. The hydrolysis of I proceeded predominantly through neutral (pH independent) and base-catalysed processes in the regions below pH 3.9 and above pH 7.0, respectively, whereas both reactions occurred between pH 3.9 and 7.0. The rates of hydrolysis of I in buffer solutions were similar to those in one sample of river and one sample of sea water. If this obtains generally, it may be expected that the half-life of I in natural waters, normally within the range pH 5–9, will range from 1.54 to 1080 days at 40°C, 11.3 to 8520 days at 25°C and, by extrapolation of the data obtained in buffer solutions, 106 to 83 000 days at 10°C. The rate constants for hydrolysis of I in aqueous media can be expressed by: Where log kN = 9.60–(5.56 × 103 T?1) and log kB = 7.32–(2.56 × 103 T?1). The calculated rate constants were in good accord with the observed values in buffer solutions. Cleavage of the ester linkage was more rapid than hydration of the cyano group at any pH and temperature tested.  相似文献   

15.
Kinetic measurements of the hydrolysis rates of flamprop-methyl, flamprop-ethyl,a flamprop-isopropyl and benzoylprop-ethyl have been carried out and the hydrolysis products analysed. The similarity of the data to that obtained from the hydrolysis of alkyl acetates show that these esters are hydrolysed by bimolecular acyl bond fission in both acidic and basic media. No buffer or salt effects on the rates were observed. The hydroxyl ion rates were approximately 10000 times faster than the protoncatalysed rates, so that optimum stability is found in solutions of pH 4. Equations are given to calculate hydrolysis rates when the pH exceeds 4 at ambient temperatures.  相似文献   

16.
BACKGROUND: The codling moth is the most serious pest of deciduous tree fruit (apples, pears, crabapples, walnuts, quince) worldwide. The high frequency of insecticide treatments per season has resulted in breakdown of codling moth control owing to insecticide resistance. As an alternative, integrated pest management includes mating disruption to achieve population suppression in orchards. Under this scheme, the sex pheromone of the codling moth, (E, E)‐8,10‐dodecadien‐1‐ol (codlemone), is released from dispensers in crops to hinder mating by luring males. Increasing the attractiveness of codlemone formulations to codling moth males can be regarded as a key to increasing the efficacy of mating disruption. With this aim, the effects of adding plant volatiles on the behavioural responses of codling moth males to codlemone were tested. RESULTS: Adding R(+)‐limonene, linalool, (E)‐β‐farnesene or ethyl (E, Z)‐2,4‐decadienoate to codlemone significantly increases the proportion of males flying to the pheromone source in a wind tunnel. The response level is equivalent to that of males responding to females releasing codlemone. Using real‐time recordings, it is shown how these four plant products also shorten the response time of males to codlemone under the behavioural criteria time to activation, time till upwind flight is induced and time to pheromone source contact. CONCLUSION: Shortening the response time and increasing source location by males of dispensers releasing codlemone with R(+)‐limonene, linalool, (E)‐β‐farnesene or ethyl (E, Z)‐2,4‐decadienoate added would enhance mating disruption through better engagement of males with dispensers, to the detriment of females. Copyright © 2011 Society of Chemical Industry  相似文献   

17.
The extent of the risk of (Z)- and (E)-1,3-dichloropropene and their transformation products (Z)- and (E)-3-chloroallyl alcohol causing a hazard to the quality of groundwater pumped up for public water supply from below flower-bulb fields has been evaluated. The 1,3-dichloropropenes were incubated at 10°C in water-saturated subsoil material from three such fields. A first stage with gradual transformation was followed by a second stage with comparatively rapid transformation and after three months negligible amounts remained. The 3-chloroallyl alcohols were incubated at 15°C in soils from the root zone of the same fields. Complete transformation had occurred in about a week or even less. The 3-chloroallyl alcohols were also incubated in the water-saturated subsoil material at 10°C. Again, a first stage with gradual transformation was followed by a second stage with fast transformation. In most instances, the concentrations had fallen to a very low level within three months. It was concluded that it is unlikely that residues in the upper groundwater would permeate into the deeper groundwater pumped up for public water supply.  相似文献   

18.
The effects of host-plant volatiles (HPVs) on male oriental fruit moth, Grapholita molesta (Busck) (Lepidoptera: Tortricidae), and response to sex pheromone trap were studied in a pear orchard. Two HPVs compounds, (Z)-3-hexenyl acetate and 1-undecanol, combined with sex pheromone of G. molesta in traps were tested. The results showed that most of the male moths were captured in the traps baited with the sex pheromone combined with these two HPVs compounds than by the pheromone alone. Also, more males were captured by the trap containing pheromone plus (Z)-3-hexenyl acetate than by the one containing 1-undecanol. It appeared that these HPVs act as sex pheromone synergists to enhance the attraction of male G. molestato pheromone traps, since males were not captured in the traps baited only with (Z)-3-hexenyl acetate and/or 1-undecanol.  相似文献   

19.
The rates of dissipation in soil and chloride-ion release, of the main components of dichloropropane-dichloropropene mixtures used as nematicides, were studied in sealed glass containers at different temperatures and moisture conditions. Half-lives of (Z)- and (E)-1,3-dichloropropenes at 20°C in soils were found to vary from 3 to 25 days; those of 1,2-dichloropropane and 2,3-dichloropropene were about four times and twice as long, respectively. The dissipation rates changed by a factor of about 2 per 10°C change in temperature. Judging from the release rates of waterextractable inorganic chloride in the soil (0-4% per week), the total degradation of all components applied at normal field rates was extremely slow. This indicated the formation of residues containing covalently bound chlorine. Only in ‘enrichment cultures’ was complete degradation indicated.  相似文献   

20.
Acetamiprid, (NI-25; (E)-N1-[(6-chloro-3-pyridyl)methyl]-N2-cyano-N1-methylacetamidine), is a novel neonicotinoid insecticide having an N-cyanoacetamidine structure as its characteristic feature. The [1H] and [13C]-NMR spectra indicated the existence of two different structures in acetamiprid at room temperature in solution. The measurement of CH-NOE and C–C coupling constants proved the E-configuration at the cyanoimino group in both existing structures. The [13C] chemical shifts of N-CH3 and the long range C–H coupling in the formamidine analogue of acetamiprid suggested that there exist two conformers generated by the rotation of C–C single bond in the amidine moiety. Dynamic NMR spectra of acetamiprid and the computer simulation of the two-site exchange demonstrated that the two conformers change slowly to each other at room temperature. The conformational analysis by semi-empirical molecular orbital calculations using MNDO-PM3 method predicted four conformers as energy-minimum structures, among which two E-conformers were more stable than Z-conformers. One of the E-conformers in which two methyl groups are in cis configuration was superimposable onto the structure of imidacloprid, which is a known neonicotinoid insecticide having more rigid structure. This E-conformer was assumed as the active conformation of acetamiprid on the basis of the molecular similarity in terms of steric and electrostatic properties. © 1997 SCI  相似文献   

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