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1.
The [4 + 3] cycloaddition of the proper furans with the oxyallyl cation, generated in situ from 2,4-dibromopentan-3-one, produced a series of 8-oxabicyclo [3.2.1]oct-6-en-3-ones. Exposure of the oxabicycles to ozone afforded the corresponding 8,9,10,11-tetraoxatricyclo[5.2.1.1 (2,6)]undecan-4-ones in variable yields (7-100%). The phytotoxic properties of these ozonides (or 1,2,4-trioxolanes) and their oxabicycle precursors were evaluated as the ability to interfere with the growth of Sorghum bicolor and Cucumis sativus seedlings. Among oxabicycles, the highest inhibitory activity was shown by compounds possessing a alpha,beta-unsaturated carbonyl moiety. A differential sensitivity of the two crops was evident with ozonides. The most active compounds were also tested against the weed species Ipomoea grandifolia and Brachiaria decumbens. To the best of our knowledge, this is the first article describing ozonides as potential herbicides.  相似文献   

2.
Starting from (+)- and (-)-perillyl alcohols, via Claisen rearrangement and iodolactonization, four enantiomeric pairs of gamma-lactones were obtained. The structures of compounds were established by both spectroscopic and crystallographic methods. The lactones were tested for antifeeding activity toward grain storage pests-the granary weevil beetle (Sitophilus granarius L.), the khapra beetle (Trogoderma granarium Ev.), and the confused flour beetle (Tribolium confusum Duv.). The results of the tests proved that two compounds, (1R,4R, 6R)-(-)-4-(1-methylethenyl)-9-oxabicyclo[4.3.0]nonan-8-one (8a) and its enantiomer (8b), are very active antifeedants against all of the above tested species. The lactone 8b is also active against the peach-potato aphid (Myzus persicae Sulz.). The activity depends on the absolute configurations of compound chiral centers. Additionally, the lactones 8a and 8b are characterized by interesting fragrances.  相似文献   

3.
A series of 2-(substituted phenoxyacetoxy)alkyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-ones IIa-s were designed and synthesized on the basis of the previous work for the modification of alkylphosphonates I, and their structures were confirmed by (1)H NMR, (31)P NMR, (13)C NMR, IR, MS, and elemental analysis. Their herbicidal activities against seven species of weeds were evaluated in a greenhouse. A part of the title compounds such as IIa-g, IIk, IIo, and IIr exhibited significant postemergence herbicidal activity against Abutilon theophrasti , Brassica juncea , Amaranthus retroflexus , and Eclipta prostrate at a dosage of 150 g ai/ha. Structure-activity relationship analyses indicated that the introduction of a phosphorus-containing heterocyclic ring had a favorable effect on herbicidal activity, and their herbicidal activity could be further increased by a reasonable combination of X, Y, and R in parent structure II. It could be found that the title compounds IIa 2-[(2,4-dichlorophenoxy)acetoxy](methyl)methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one and IIr 2-[(4-chloro-2-methyl-phenoxy)acetoxy](methyl)methyl-5,5-dimethyl-1,3,2-dioxaphosphinan-2-one possess high activity and a broad spectrum against all of the test broadleaf weeds with 70-100% inhibition effect at a dosage of 75 g ai/ha, and the title compounds IIa and IIr are safe for corn and wheat at a dosage of 150 g ai/ha. Furthermore, the title compound IIa possesses low rat toxicity. These results suggest that the title compounds IIa and IIr could be potential and selective postemergence herbicides for further development.  相似文献   

4.
Avena fatua L. (wild oat) and Lolium rigidum Gaud. (rigid ryegrass) are highly problematic weeds affecting a wide variety of cereal crops worldwide. The fact that both of these weeds have developed resistance to several herbicide groups made them optimal candidates as target organisms for ongoing research about the potential application of allelochemicals and analogue compounds as natural herbicide models. Benzoxazinones, a family of natural allelochemicals present in corn, wheat, and rye, including 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one and 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one, together with some degradation products, found in crop soils as well as in other systems, and some synthetic analogues of them were tested on wild oat and rigid ryegrass seeds; the results were statistically treated, and some structure-activity relationships, useful in further development of natural herbicide models, were elucidated. The most active compounds were the synthetic benzoxazinone 2-acetoxy-(2H)-1,4-benzoxazin-3(4H)-one and the degradation product 2-aminophenoxazin-3-one, with highly significant inhibition on the development of both weeds. The ecological role of these compounds is discussed by considering both degradability and phytotoxicity. The bioactivity of aminophenoxazines has been correlated by their aqueous solubility-lipophilicity predicted by means of computational methods.  相似文献   

5.
A series of 2-substituted-8-(4,6-dimethoxypyrimidin-2-yloxy)-4-methylphthalazin-1-one derivatives, 7a-7w, were designed via an ortho-substituent cyclization strategy to discover a new herbicidal lead structure. These compounds were synthesized by a seven-step route using 3-hydroxy-acetophenone as a starting material. Determination of the Ki values against wild-type A. thaliana acetohydroxyacid synthase (AHAS) (EC 4.1.3.18) indicated that some of the compounds displayed good enzyme inhibition activity comparable to that of KIH-6127. The further preliminary bioassay data on weeds showed that the synthesized compounds exhibited typical injury symptoms of AHAS-inhibiting herbicides, and some of them showed broad-spectrum and high herbicidal activities in postemergence treatments against Echinochloa crusgalli, Digitaria sanguinalis, Setaria viridis, Brassica juncea, Amaranthus retroflexus, and Chenopodium album at an application rate of 150 g ai/ha. To our knowledge, this is the first report of methylphthalazin-1-one derivatives as AHAS inhibitors.  相似文献   

6.
The utility of benzoxazinones and some of their synthetic derivatives in the search for new leads for herbicide model development has been widely discussed. As the benzoxazinone skeleton contains three different potential areas for functionalization (C-2, N-4, and aromatic protons H-5, H-6, H-7, and H-8), and the first two have already been optimized, the main objective of this work was the substitution of aromatic protons for different substituent types and the study of the effects of the prepared chemicals on selected standard target species (STS) and weeds. Thus, different combinations of aromatic substituents, including methoxy, methoxycarbonyl, fluorine, chlorine, and trifluoromethyl, were introduced at different positions. Phytotoxicity results were successfully correlated with steric and electronic molecular parameters, the resulting molecular volume (V) and dipole moment (mu) being the most influential ones. Halogenations at C-6 and fluorination at C-7 were the most successful modifications. Compounds 6-fluoro-(2H)-1,4-benzoxazin-3(4H)-one (6F-D-DIBOA), 7-fluoro-(2H)-1,4-benzoxazin-3(4H)-one (7F-D-DIBOA), and 6-chloro-(2H)-1,4-benzoxazin-3(4H)-one (6Cl-D-DIBOA) had the highest phytotoxic activities. The dose-response profiles on wheat and two of its most common weeds (Lolium rigidum Gaud. and Avena fatua L.) were compared by means of a proposed selectivity index, which displayed 7F-D-DIBOA as the most selective of the tested benzoxazinones.  相似文献   

7.
A new analytical method based on the use of pressurized liquid extraction (PLE) followed by solid-phase extraction with LiChrolut RP C18 cartridges was evaluated for the sample preparation, extraction, and cleanup of eight naturally occurring benzoxazinone derivatives, 2-beta-D-glucopyranosyloxy-4-hydroxy-1,4-benzoxazin-3-one, 2-beta-D-glucopyranosyloxy-4-hydroxy-7-methoxy-1,4-benzoxazin-3-one, 2,4-dihydroxy-1,4-benzoxazin-3-one (DIBOA), 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one, 2-hydroxy-1,4-benzoxazin-3-one, 2-hydroxy-7-methoxy-1,4-benzoxazin-3-one, benzoxazolin-2-one, and 6-methoxybenzoxazolin-2-one in plant samples. Afterward, liquid chromatography-electrospray mass spectrometry, using the selected ion monitoring mode and internal standard (2-MeO-DIBOA, indoxyl-beta-D-glucoside, and quercetin-3-O-rutinoside) quantification method was performed. This paper demonstrates the effectiveness of the PLE method, in conjunction with sensitive and specific mass spectrometric detection, for the quantitative recovery of compounds of the benzoxazinone class from plants. The recoveries of the analytes ranged from 66 to 110% with coefficients of variation ranging from 1 to 14%. This method gave detection limits between 1 and 27 microg/g. The method was applied to foliage and roots of three different wheat cultivars, and the analytes were detected in the range of 11-3261 microg/g of dry weight.  相似文献   

8.
Five optically active and sixteen racemic lactones (nine of them new) of bicyclo[4.3.0]nonane structure were synthesized. IC(50) values for the following phytopathogens were determined: Aspergillus ochraceus AM 456, Fusarium culmorum AM 282, Fusarium oxysporum AM 13, Fusarium tricinctum AM 16. Effect of compound structures, especially stereogenic centers, on fungistatic activity has been discussed. The highest fungistatic activity was observed for trans-7,8-dibromo-cis-3-oxabicyclo[4.3.0]nonan-2-one (3c), IC(50) = 30.1 μg/mL (0.10 μM/mL), and cis-7,8-epoxy-cis-3-oxabicyclo[4.3.0]nonan-2-one (3b), IC(50) = 72.2 μg/mL (0.47 μM/mL), toward F. oxysporum AM 13.  相似文献   

9.
Analyses of the neutral lipids from Vanilla species before saponification resulted in the identification of a new product family in this genus: long-chain gamma-pyrone compounds with an aliphatic chain containing a cis double bond at the n-9 position. These compounds represent 7-8% of the neutral lipids in mature beans. Using NMR and gas chromatography/mass spectrometry, three gamma-pyrones have been identified, including 2-(10-nonadecenyl)-2, 3-dihydro-6-methyl-4H-pyran-4-one, 2-(12-heneicosenyl)-2, 3-dihydro-6-methyl-4H-pyran-4-one, and 2-(14-tricosenyl)-2, 3-dihydro-6-methyl-4H-pyran-4-one. The major constituent was 2-(14-tricosenyl)-2,3-dihydro-6-methyl-4H-pyran-4-one, which represented 70.3% of the gamma-pyrone fraction. The variability of this compound family has been studied in relation to bean maturity in V. fragrans and V. tahitensis beans. This compound family has not been found either in leaves or in stems or in V. madagascariensis beans.  相似文献   

10.
To deduce the structure of the large array of compounds arising from the transformation pathway of 6-methoxybenzoxazolin-2-one (MBOA), the combination of isotopic substitution and liquid chromatography analysis with mass spectrometry detection was used as a powerful tool. MBOA is formed in soil when the cereal allelochemical 2,4-dihydroxy-7-methoxy-1,4-benzoxazin-3-one (DIMBOA) is exuded from plant material to soil. Degradation experiments were performed in concentrations of 400 microg of benzoxazolinone/g of soil for MBOA and its isotopomer 6-trideuteriomethoxybenzoxazolin-2-one ([D3]-MBOA). Previously identified metabolites 2-amino-7-methoxyphenoxazin-3-one (AMPO) and 2-acetylamino-7-methoxyphenoxazin-3-one (AAMPO) were detected. Furthermore, several novel compounds were detected and provisionally characterized. The environmental impact of these compounds and their long-range effects are yet to be discovered. This is imperative due to the enhanced interest in exploiting the allelopathic properties of cereals as a means of reducing the use of synthetic pesticides.  相似文献   

11.
Volatile organic compounds (VOCs) in fermented honeybush, Cyclopia subternata, were sampled by means of a high-capacity headspace sample enrichment probe (SEP) and analyzed by gas chromatography-mass spectrometry (GC-MS). Stereochemistry was determined by means of enantioselective GC-MS with derivatized β-cyclodextrin columns as chiral selectors. A total of 183 compounds, the majority of which are terpenoids (103; 56%), were identified by comparing their mass spectra and retention indices with those of reference compounds or tentatively identified by comparison with spectral library or literature data. Of these compounds, 37 were determined by gas chromatography-olfactometry (GC-O), using detection frequency (DF) and aroma extract dilution analysis (AEDA), to be odor-active (FD ≥ 2). (E)-β-Damascenone, (R/S)-linalool, (E)-β-damascone, geraniol, (E)-β-ionone, and (7E)-megastigma-5,7,9-trien-4-one were identified with the highest FD factors (≥512). The odors of certain compounds, that is, (6E,8Z)-megastigma-4,6,8-trien-3-one, (6E,8E)-megastigma-4,6,8-trien-3-one, (7E)-megastigma-5,7,9-trien-4-one, 10-epi-γ-eudesmol, epi-α-muurolol, and epi-α-cadinol, were perceived by GC-O assessors as typically honeybush-like.  相似文献   

12.
李大婧  卓成龙  刘霞  刘春泉 《核农学报》2011,25(5):969-974,1003
采用固相微萃取（SPME）与气相色谱-质谱（GC-MS）联用技术,分析微波烫漂和速冻后新大粒1号黑毛豆仁挥发性风味成分的变化。结果表明：黑毛豆仁鲜样、微波烫漂和速冻处理后分别检测到31、34和32种挥发性风味成分,主要为醇类、醛类、酮类化合物。1-辛烯-3-酮、己醛、（E,Z）-2,6-壬二烯醛、1-戊烯-3-酮、（E...  相似文献   

13.
Compounds with a (2H)-1,4-benzoxazin-3(4H)-one skeleton have attracted the attention of phytochemistry researchers since 2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA) and 2,4-dihydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one (DIMBOA) were isolated from plants belonging to the Poaceae family. These compounds exhibit interesting biological properties, such as phytotoxic, antimicrobial, antifeedant, antifungal, and insecticidal properties. These chemicals, in addition to a wide variety of related compounds involved in their metabolism, detoxification mechanisms, and degradation on crop soils and other systems, have high interest and in some cases potential agronomic utility. This paper presents a complete review of the methods employed for their synthetic obtention in addition to some of the authors' own contributions to their chemistry. The degradation and phytotoxicity experiments carried out in ongoing research into the potential agronomic utility of these compounds required large amounts of them, which were obtained from natural sources. This paper presents a modified methodology to access DIMBOA from Zea mays cv. Apache and to obtain 2-O-beta-D-glucopyranosyl-2,4-dihydroxy-(2H)-1,4-benzoxazin-3(4H)-one (DIBOA-Glc) and DIBOA from Secale cereale L. New synthetic methodologies were employed for the obtention of the lactams 2-hydroxy-(2H)-1,4-benzoxazin-3(4H)-one and 2-hydroxy-7-methoxy-(2H)-1,4-benzoxazin-3(4H)-one and the malonamic acids N-(2-hydroxyphenyl)malonamic acid and N-(2-hydroxy-7-methoxyphenyl)malonamic acid. The aminophenoxazines 2-amino-7-methoxyphenoxazin-3-one and 2-acetamido-7-methoxyphenoxazin-3-one have been synthesized in the authors' laboratory by novel procedures. All of the methodologies employed allowed the desired compounds to be obtained in high yield and in an easy-to-scale manner.  相似文献   

14.
为了安全防除抗草铵膦转基因马铃薯田间杂草,以转Bar基因马铃薯为试验材料,分析比较了有效成分1 440 g·hm-2灭草松(T1)、99 g·hm-2 11%砜嘧磺隆·精喹禾灵(T2)、1 440 g·hm-2灭草松+ 99 g·hm-2 11%砜嘧磺隆·精喹禾灵复配剂(T3)、1 695 g·hm-2草铵膦(T4)、923 g·hm-2草甘膦(T5)和清水(CK)处理下杂草防效、马铃薯生长指标、块茎产量及品质特性和药剂残留情况。结果表明,草甘膦在杀灭杂草的同时,也杀死了马铃薯植株,受害率达100%;灭草松、11%砜嘧磺隆·精喹禾灵和草铵膦对马铃薯均未产生药害,但因对杂草的防效不同而导致达到的增产效果差异显著。药后45 d时,灭草松和11%砜嘧磺隆·精喹禾灵复配剂(T3)对阔叶杂草的株、鲜重防效较灭草松单独处理(T1)分别提高35.13和38.71个百分点,较11%砜嘧磺隆·精喹禾灵单独处理(T2)分别提高23.88和16.29个百分点,对禾本科杂草的株、鲜重防效较T1分别提高78.36和80.92个百分点,较T2分别提高11.85和8.23个百分点,马铃薯单株产量较CK、T1和T2分别增加58.39%、35.52%和11.44%。草铵膦(T4)对阔叶和禾本科杂草的株、鲜重防效都显著高于T1、T2和T3,单株产量较CK、T1、T2和T3分别增加67.40%、43.24%、17.79%和5.6%。因此,用有效成分1 695 g·hm-2的草铵膦可以高效防治转Bar基因马铃薯田间杂草,但为了防止转Bar基因马铃薯连作时,因靶标除草剂草铵膦作用单一而诱导杂草产生草铵膦抗性的风险,建议用有效成分 1 440 g·hm-2 的灭草松和99 g·hm-2 11%砜嘧磺隆·精喹禾灵复配剂与草铵膦轮换防治杂草。本研究为转Bar基因马铃薯大面积种植中田间杂草的科学防治提供了科学依据。  相似文献   

15.
Three active components were identified by bioassay-guided fractionation of bitter orange ( Citrus aurantium L.) fruit peel petroleum ether extract. Silica gel fractionation of the extract yielded a fraction that inflicted up to 96% mortality to adults of the olive fruit fly Bactrocera oleae (Gmelin) three days post-treatment. Subsequent HPLC purification of the active fraction resulted in the isolation of three components, eluted in fractions F 222, F 224, and F 226, that induced adult mortality. Considering the data obtained from UV, FTIR, MS, and (1)H NMR spectra, they were identified as 7-methoxy-8-(3'-methyl-2'-butenyl)-2 H-1-benzopyran-2-one (osthol), 4-methoxy-7 H-furo[3,2- g]benzopyran-7-one (bergapten), and 4-(( E)-3'-methyl-5'-(3',3'-dimethyloxiran-2'-yl)pent-2'-enyloxy)-7 H-furo[3,2- g][1]benzopyran-7-one (6',7'-epoxybergamottin). Our results are in concordance with those reported in the literature and were further verified by direct comparison to authentic components. 6',7'-Epoxybergamottin was toxic when tested individually, while bergapten and osthol were found to act synergistically to 6',7'-epoxybergamottin.  相似文献   

16.
The volatile compounds of guava wine were isolated by continuous solvent extraction and analyzed by GC-FID and GC-MS. A total of 124 volatile constituents were detected, and 102 of them were positively identified. The composition of guava wine included 52 esters, 24 alcohols, 11 ketones, 7 acids, 6 aldehydes, 6 terpenes, 4 phenols and derivatives, 4 lactones, 4 sulfur-compounds, and 5 miscellaneous compounds. The aroma-active areas in the gas chromatogram were screened by application of the aroma extract dilution analysis and by odor activity values. Twelve odorants were considered as odor-active volatiles: (E)-β-damascenone, ethyl octanoate, ethyl 3-phenylpropanoate, ethyl hexanoate, 3-methylbutyl acetate, 2-methyltetrahydrothiophen-3-one, 2,5-dimethyl-4-methoxy-3(2H)-furanone, ethyl (E)-cinnamate, ethyl butanoate, (E)-cinnamyl acetate, 3-phenylpropyl acetate, and ethyl 2-methylpropanoate.  相似文献   

17.
Before natural plant allelochemicals can be exploited as biological pesticides against weeds and for disease control, more than the effect on target organisms needs to be known. This study presents results of aquatic biotests using four organisms, namely, a water flea, a freshwater alga, a soil alga, and a luminescent bacterium. The tested substances were 10 benzoxazinone derivatives, 3 of them known to be wheat allelochemicals, benzoxazolin-2(3H)-one (BOA), 6-methoxybenzoxazolin-2(3H)-one (MBOA), and 2,4-dihydroxy-7-methoxy-2H-1,4-benzoxazin-3-one (DIMBOA), and 7 identified degradation intermediates and metabolites. For comparison, two commercial pesticide formulations (BAS, Betanal) were tested by applying the same set of biotests. The data set produced could be seen as an ecotoxicological evaluation for effects of allelochemicals against nontarget organisms and as a base for further risk assessment.  相似文献   

18.
Seedless triploid watermelons have increased in popularity since the early 1990s, and the demand for seedless fruit is on the rise. Sweetness and sugars are crucial breeding focuses for fruit quality. Volatiles also play an important role; yet, we found no literature for seedless varieties and no reports using solid-phase microextraction (SPME) in watermelon. The objective of this experiment was to identify volatile and semivolatile compounds in five seedless watermelon varieties using carboxen divinylbenzene polydimethylsiloxane solid-phase microextraction (SPME) with gas chromatography-mass spectrometry (GC-MS). Fully ripe watermelon was squeezed through miracloth to produce rapid juice extracts for immediate headspace SPME GC-MS. Aldehydes, alcohols, ketones, and one furan (2-pentyl furan, a lipid oxidation product) were recovered. On the basis of total ion count peak area, the most abundant compounds in five varieties were 3-nonen-1-ol/(E,Z)-2,6-nonadienal (16.5-28.2%), (E)-2-nonenal (10.6-22.5%), and (Z)-6-nonenal (2.0-11.3%). Hexanal was most abundant (37.7%) in one variety (Petite Perfection) [corrected] The most abundant ketone was 6-methyl-5-hepten-2-one (2.7-7.7%). Some sensory attributes reported for these compounds are melon, citrus, cucumber, orange, rose, floral, guava, violet, vegetable, green, grassy, herbaceous, pungent, fatty, sweet, and waxy. Identifying and relating these compounds to sensory attributes will allow for future monitoring of the critical flavor compounds in seedless watermelon after processing and throughout fresh-cut storage.  相似文献   

19.
为探讨未浸果和浸果处理(氯吡脲10 mg·L-1)对贵长猕猴桃果实产量品质、氨基酸和香气成分的影响,本试验测定了采收期果实产量参数和可食期营养品质,并采用高效液相色谱法(HPLC)和固相微萃取-色谱-质谱联用法(SPME-GC-MS)分别分析了可食期果实氨基酸和香气成分。结果表明,10 mg·L-1氯吡脲浸果处理可有效促进贵长猕猴桃果实产量形成及干物质和可溶性固形物含量增加,显著降低果实果形指数和硬度以及维生素C、可滴定酸和可溶性蛋白含量(P<0.05),影响果实的外观和耐贮性。此外,10 mg·L-1氯吡脲浸果极显著增加果实脯氨酸和甜味氨基酸含量(P<0.01),而果实总氨基酸、鲜味氨基酸、苦味氨基酸和芳香族氨基酸含量显著降低(P<0.05)。 贵长猕猴桃果实香气成分主要为酯类、醇类、醛类、烯烃和烷烃,共70种成分。其中,未浸果果实香气成分主要为丁酸乙酯、丁酸甲酯、苯甲酸甲酯和苯甲酸乙酯等,浸果果实主要为丁酸乙酯、苯甲酸甲酯、丁酸甲酯和(E)-2-己烯醛等。10 mg·L-1氯吡脲浸果增加了醛类、醇类、烯烃和烷烃在果实香气成分中的占比,提高了香气的多样性。本研究为贵长猕猴桃的深加工提供了理论依据。  相似文献   

20.
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