新型含2(1H)-喹啉酮的甲氧基丙烯酸酯类

以(E)-2-[2'-(bromo-methyl)phenyl]3-甲氧基丙烯酸甲酯和2(1H)-喹啉酮类化合物为原料,通过醚化等反应,合成了11个新型含2(1H)-喹啉酮结构的甲氧基丙烯酸酯类化合物,其结构经红外、电喷雾串联质谱(ESI-MS)和核磁共振氢谱确证。初步生物活性测试结果表明:在100 mg/L质量浓度下,部分目标化合物对烟草赤星病菌Alternaria alternata等6种病原菌具有一定的抑菌活性,其中5a对水稻稻瘟病菌Pyricularia grisea的抑菌率达100%。     

5-取代苯甲酰基脲-3-哒嗪酮衍生物的合成及昆虫生长调节活性

哒嗪酮是一类具有良好生物活性的杂环,为进一步发现具有昆虫生长调节活性的新型化合物,依据前期研究成果,在3(2H)-哒嗪酮的5位上引入苯甲酰基脲活性基团,设计合成了17个5-取代苯甲酰基脲-3(2H)-哒嗪酮衍生物,并通过两种方法制备得到了目标化合物,结构均通过1H NMR、IR和元素分析确证。初步生物活性研究结果表明,部分化合物如 6a、BPU-4 在200 mg/L时对3龄蝗蝻Locusta migratoria manilensis Linne(Meyen)有较好的生物活性,使蝗蝻因不能正常蜕皮变态而死亡,表现出明显的昆虫生长调节剂(IGRs)类化合物的作用特征。     

坡柳种子中坡柳皂苷A的分离鉴定及其对小菜蛾的拒食活性

采用小孔树脂、凝胶SephadexLH-20、反相色谱ODS及制备型高效液相色谱 (Pre-HPLC) 等分离技术,从坡柳Dodonaea viscosa (Linn.) Jacq. Enum. 种子乙醇提取物中分离获得1个活性化合物。通过质谱及核磁共振等波谱技术,鉴定其为新的齐墩果烷型三萜皂苷类化合物21-epoxyangeloyl-15,16,28-tirhydroxy-22-(2-methylbutanoyl)-Olean-12-en-3-(O-α-L-arabinofuranosyl-(1→3)-O-[β-D-glucopyranosyl-(1→2)]-β-D-glucuronide,命名为坡柳皂苷A,英文名dodoneaviscoside A。生物活性测定结果表明,其对小菜蛾Plutella xylostella (L.) 3龄幼虫具有较好的非选择性拒食活性,24 h拒食中浓度 (AFC₅₀) 为207.4 μg/mL。值得进一步研究。     

Insect growth regulator effects of azadirachtin and neem oil on survivorship, development and fecundity of Aphis glycines (Homoptera: Aphididae) and its predator, Harmonia axyridis (Coleoptera: Coccinellidae)

BACKGROUND: Aphis glycines Matsumura, an invasive insect pest in North American soybeans, is fed upon by a key biological control agent, Harmonia axyridis Pallas. Although biological control is preferentially relied upon to suppress insect pests in organic agriculture, approved insecticides, such as neem, are periodically utilized to reduce damaging pest populations. The authors evaluated direct spray treatments of two neem formulations, azadirachtin and neem seed oil, under controlled conditions for effects on survivorship, development time and fecundity in A. glycines and H. axyridis. RESULTS: Both azadirachtin and neem seed oil significantly increased aphid nymphal mortality (80 and 77% respectively) while significantly increasing development time of those surviving to adulthood. First-instar H. axyridis survival to adulthood was also significantly reduced by both neem formulations, while only azadirachtin reduced third-instar survivorship. Azadirachtin increased H. axyridis development time to adult when applied to both instars, while neem oil only increased time to adult when applied to first instar. Neither neem formulation affected the fecundity of either insect. CONCLUSIONS: Results are discussed within the context of future laboratory and field studies aimed at clarifying if neem-derived insecticides can be effectively integrated with biological control for soybean aphid management in organic soybeans.     

Isolation,characterization and insect growth inhibitory activity of major turmeric constituents and their derivatives against Schistocerca gregaria (Forsk) and Dysdercus koenigii (Walk)

Curcuminoids, the major colouring constituents of Curcuma longa (turmeric) rhizome powder, comprise mainly three closely related curcumins (I, II and III). A simple method has been devised for their efficient extraction and separation. Their structures have been confirmed by ¹H NMR spectroscopy and unique mass fragmentation pattern. Curcumin‐I, the major constituent has been converted to five alkyl ether derivatives, which have been tested along with the parent compounds and other extractives for insect growth inhibitory activity against Schistocerca gregaria and Dysdercus koenigii nymphs. At 20 µg per nymph, benzene extract and dibutyl curcumin‐I were the most active (60% inhibition) against S gregaria, whereas at 50 µg per nymph these substances exhibited moderate growth‐inhibitory activity (45%) against D koenigii nymphs. At these concentrations, turmeric oil caused 50–60% nymphal mortality in both test insects. The insect control activity of most of the turmeric products was comparable to or better than that of a commercial neem formulation. © 2000 Society of Chemical Industry     

Plant growth inhibitory activity and active substances with allelopathic potential of cogongrass (Imperata cylindrica) rhizome

Cogongrass (Imperata cylindrica [L.] Raeusch.) is a perennial rhizomatous grass that belongs to the Poaceae and is widely distributed in tropical, subtropical and temperate regions over the world. The grass is strongly invasive and is suggested to have allelopathic potential. However, limited information is available on allelopathic substances in cogongrass rhizomes. Therefore, the allelopathic potential and substances in cogongrass rhizomes were investigated. The extracts of cogongrass rhizomes inhibited the root and shoot growth of barnyard grass, ryegrass, timothy, cress, lettuce and alfalfa. After bioassay‐guided separations of the extracts, four growth inhibitory substances, 5‐methoxyflavone, 5,2′‐dimethoxyflavone, methyl caffeate and abscisic acid, were isolated. 5‐Methoxyflavone, 5,2′‐dimethoxyflavone and methyl caffeate significantly inhibited the root and shoot growth of cress at concentrations of ≥0.03–0.3 m mol L^?1 and their concentrations required for 50% growth inhibition were 0.079–0.24, 0.23–1.1 and 0.59–0.88 m mol L^?1, respectively. The other isolated substance, abscisic acid, has been reported to have strong growth inhibitory activity. Its concentrations required for 50% growth inhibition on cress were 0.31–0.61 μ mol L^?1. The present study suggests that cogongrass rhizomes might have allelopathic potential and that those four substances might contribute to that potential.     

Persistence and residual activity of an organophosphate, pirimiphos-methyl, and three IGRs, hexaflumuron, teflubenzuron and pyriproxyfen, against the cowpea weevil, Callosobruchus maculatus (Coleoptera: Bruchidae)

Three insect growth regulators (IGR), the chitin synthesis inhibitors (CSI) teflubenzuron and hexaflumuron and the juvenile hormone mimic (JHM) pyriproxyfen, as well as the organophosphate (OP) pirimiphos-methyl, were evaluated for their activity against the cowpea weevil, Callosobruchus maculatus (F), in cowpea seeds stored for up to 8 months post-treatment. The initial activity data showed that, based on LC50 level, teflubenzuron had strong ovicidal activity (LC50 = 0.056 mg kg(-1)) followed by pirimiphos-methyl (1.82 mg kg(-1)) and pyriproxyfen (91.9 mg kg(-1)). The residual activity data showed that none of the IGRs tested had strong activity when applied at 200 mg kg(-1) in reducing the oviposition rates of C maculatus at various storage intervals up to 8 months post-treatment. However, teflubenzuron reduced adult emergence (F1 progeny), achieving control ranging from 96.2% at 1 month to 94.3% at 8 months. Hexaflumuron showed a similar trend in its residual activity, ranging between 93.8% control at 1 month to 88.2% control at 8 months post-treatment. However, pyriproxyfen was more active than the CSIs tested and caused complete suppression (100% control) of adult emergence at all storage intervals. Unlike the IGRs tested, pirimiphos-methyl applied at 25 mg kg(-1) was more effective in reducing oviposition rates of C maculatus up to 8 months post-treatment. A strong reduction of adult emergence was also observed at various bimonthly intervals (98.6% control at 1 month to 91.6% control at 8 months post-treatment). The persistence of hexaflumuron and pirimiphos-methyl in cowpea seeds was also studied over a period of 8 months. The loss of hexaflumuron residue in treated cowpeas (200 mg kg(-1)) was very slow during the first month post-treatment (4.43%). At the end of 8 months, the residue level had declined significantly to 46.4% of the initial applied rate. The loss of pirimiphos-methyl residue in treated cowpeas (25 mg kg(-1)) was relatively high during the first month post-treatment (36.7%) and increased to 81.6% after 8 months.     

芳香植物气味及提取液对茶尺蠖行为的影响

为了明确芳香植物对茶尺蠖Ectropisobliqua的驱避、拒食作用和获得应用于茶园茶尺蠖"推-拉"策略的植物材料,利用"Y"型嗅觉仪室内测定其成虫对芳香植物气味的趋性反应,并采用叶碟法测定芳香植物提取液对其幼虫的拒食作用及营养干扰效果。丁香罗勒、迷迭香、柠檬桉和芸香植株挥发物及甲醇提取液对茶尺蠖雌、雄成虫有显著的驱避效果。猫薄荷、迷迭香和鼠尾草的2 00 mg/mL甲醇提取液对茶尺蠖3龄幼虫表现出显著拒食活性,24 h后的选择性拒食率分别为93.85%、86.00%和77.32%,非选择性拒食率分别为85.77%、87.00%和88.05%。其中,迷迭香处理的幼虫生长率最低,仅为0.12 mg/天,对幼虫的相对取食量、食物利用率和食物转化率等营养指标有影响。研究表明,10种芳香植物中迷迭香具有显著的行为调控功能,是构建茶尺蠖"推-拉"策略的理想材料。     

Protein digestibility, protease activity, and post-embryonic development of the velvetbean caterpillar (Anticarsia gemmatalis) exposed to the trypsin-inhibitor benzamidine

Protein digestibility, proteolytic activity, and post-embryonic development of Anticarsia gemmatalis (Hübner) (Lepidoptera: Noctuidae) were assessed in larvae reared on artificial diet containing 0.00, 0.25, 0.50, and 0.75% (w/w) of the synthetic trypsin inhibitor benzamidine. Diet consumption was affected by the inhibitor when the insects were exposed to 0.50% benzamidine showing a 4-day delay and a 70%-higher peak of consumption. Larva weight gain was also affected by benzamidine and again the results of 0.50% benzamidine were unexpected due to the worst performance of the insects at this inhibitor concentration and not at 0.75% benzamidine. These patterns of consumption and weight gain were however consistent with the results of protein digestibility, which affects larvae mortality and adult emergence. The insect proteolytic activity was also affected by benzamidine, particularly at 0.50%. These results indicate that the insects are able to circumvent the potentially harmful effects of the inhibitor since at the highest concentration the negative impact is mitigated.     

Effect of GRAS compounds on mycelial growth, pectic enzyme activity and disease severity of postharvest pathogens on rambutan (Nephelium lappaceum)

The GRAS compounds cinnamaldehyde (at 30 ppm), acetaldehyde (at 70 ppm), benzalde-hyde (at 50 ppm) and potassium metabisulphite (at 250 ppm) either completely inhibited or significantly reduced thein vitro mycelial growth ofGliocephalotrichum microchlamydosponim,Colletotrichum gloeosporioides andBotryodiplodia theobromae, the causative fungi of brown spot, anthracnose and stem end rot, respectively, of rambutan fruits,Nephelium lappaceum. The four compounds also significantly reduced the severity of all three diseases and the activity of pectic lyase and polygalacturonase enzymes secreted by the three fungi.     

吡虫啉胁迫对褐飞虱共生解脂假丝酵母抗性及敏感菌株生长的影响

为明确吡虫啉对褐飞虱共生解脂假丝酵母Candida lipolytica抗性及敏感菌株生长的影响,通过菌株培养、菌落观察和菌丝镜检等方法,比较了褐飞虱共生解脂假丝酵母不同菌株在含不同质量浓度吡虫啉的固体培养基上的菌落数,以及在液体培养基中的生长量差异。结果发现:不同质量浓度吡虫啉对褐飞虱共生解脂假丝酵母敏感和抗性菌株菌落生长均有抑制作用,且吡虫啉浓度越高,抑制作用越强。经500、1 000和2 000 mg/L吡虫啉处理4 d后,敏感菌株的菌落数量分别为对照的46.61%、27.58%和6.25%,均与对照差异显著;500和1 000 mg/L处理组抗性菌株菌落数量与对照无显著差异,而2 000 mg/L处理组与对照差异显著。经吡虫啉处理后,敏感菌株假菌丝形态变得不规则,部分假菌丝不舒展、萎缩或弯曲、顶端出现膨大,酵母出现空泡等,且吡虫啉浓度越高,不规则程度越明显;抗性菌株的假菌丝形态也有类似变化,但与敏感菌株相比,其菌丝体不规则形态的比例明显下降。500 mg/L吡虫啉处理对敏感和抗性菌株的生长量及菌丝干重均无明显影响,1 000和2 000 mg/L吡虫啉对不同菌株前期生长的抑制作用明显,但对后期生长影响不明显。研究表明,吡虫啉对褐飞虱共生解脂假丝酵母抗性菌株生长的影响显著小于对敏感菌株的影响。     

Comparative effects of lindane and deltamethrin on mortality, growth, and cellulase activity in earthworms (Eisenia fetida)

Laboratory tests were conducted to compare the effects of various concentrations of lindane and deltamethrin on mature earthworms (Eisenia fetida) cultured in artificial soil during typical acute (14d) and subchronic (42d) exposure periods. The effects of the two pesticides on earthworm mortality, growth inhibition, and cellulase activity were determined for different exposure durations. The toxicity order for earthworm mortality from the 14-day exposure was lindane > deltamethrin, with median lethal concentrations (LC₅₀) of 162.1 and 432.9 mg kg⁻¹, respectively. Earthworms exposed to deltamethrin showed dose-dependent toxic effects on growth and cellulase activity only from the acute exposures, whereas lindane’s effects on these activities were seen correlated with both the acute and subchronic doses. Also, changes in biomass and cellulase activity during the subchronic exposure period appear to be a more sensitive parameter than the LC₅₀ value in assessing pesticidal injury.     

Increased activity and reduced sensitivity of acetylcholinesterase associated with malathion resistance in a field population of the oriental migratory locust, Locusta migratoria manilensis (Meyen)

The susceptibility to malathion, and the activity and sensitivity of acetylcholinesterase (AChE, EC 1.1.1.7) were compared between two populations of the oriental migratory locust, Locusta migratoria manilensis (Meyen) collected from Wudi County of Shandong Province in East China and Huangliu County of Hainan Province in South China. Huangliu population showed 8.5-fold resistance to malathion compared with Wudi population. AChE from Huangliu population showed 4.8-fold higher activity than that from Wudi population toward the model substrate acetylthiocholine (ATC). Kinetic studies indicated that AChE from Huangliu population had 2.6-fold lower affinity, but 5.0-fold higher catalytic activity toward ATC than AChE from Wudi population. Significantly increased activity of AChE in Huangliu population was also confirmed by non-denaturing polyacrylamide gel electrophoresis. Inhibition kinetics revealed that AChE from Huangliu population was 9.8-, 2.4-, 8.0- and 7.7-fold less sensitive to inhibition by paraoxon, malaoxon, chlopyrifos oxon, demeton-S-methyl, respectively, than that from Wudi population. Our studies revealed that a mild resistance to malathion in Huangliu population was associated with reduced sensitivity and increased catalytic activity of AChE. Our results suggest that alterations of AChE may play an important role conferring or contribute to malathion resistance in Huangliu population of the locust.     

Cry1Ac毒蛋白对亚洲玉米螟生长发育和种群增长的影响

以含不同浓度的Cry1Ac毒蛋白的人工饲料(不加毒蛋白为对照)饲喂亚洲玉米螟幼虫,采用实验种群生命表的方法,测定了Cry1Ac毒蛋白对亚洲玉米螟的控害作用。结果显示,含2 000.0ng/g Cry1Ac毒蛋白的人工饲料处理该虫第5天的幼虫存活率为0;200.0、20.0 ng/g CrylAc毒蛋白处理第10、15天的幼虫存活率、化蛹率、成蛾率、净增长率和种群增长指数均显著低于对照,且高浓度处理显著低于低浓度处理;200.0 ng/g CrylAc毒蛋白处理的世代平均周期和种群加倍时间显著长于其它处理;而200.0 ng/g CrylAc毒蛋白处理的周限增长率显著小于2.0、0.2 ng/g处理。表明微量的Cry1Ac毒蛋白对亚洲玉米螟的种群增长有显著影响,且随着浓度的增加控制作用增强。     

博落回中季铵类苯并啡啶类生物碱的提取及其硫酸氢盐的抗菌活性和急性毒性

采用酸提碱沉的方法,从博落回中提取并制备了苯并啡啶类生物碱(QBAs)——血根碱(sanguinarine)和白屈菜红碱(chelerythrine)的硫酸氢盐;采用高效液相色谱法测定了2种生物碱的含量;初步测定了其硫酸氢盐对几种常见病原菌的抗菌活性,并对其急性毒性进行了研究。结果表明:所制备的QBAs硫酸氢盐中血根碱和白屈菜红碱的质量分数均在60%以上。生物测定结果表明,该生物碱的硫酸氢盐对葡萄叶斑病菌Cercospora viticola、葡萄黑豆病菌Elsinoe ampelina、葡萄炭疽病菌Colletotrichum gloeosporioides、葡萄褐斑病菌Cercospora viticola、稻瘟病菌Pvricularia oryzae、小麦赤霉病菌Gibberella zeae和辣椒疫霉Phytophythora capsici均具有较强的抑制作用,EC50值在3.35～10.08 μg/mL之间。其急性毒性属低毒,对皮肤有弱致敏性,但对眼睛有重度刺激性。博落回中QBAs硫酸氢盐制备方法稳定,具有较强的抗菌活性,可考虑开发成低毒、环境友好型植物源杀菌剂。     

Bio-potency of serine proteinase inhibitors from Acacia senegal seeds on digestive proteinases, larval growth and development of Helicoverpa armigera (Hübner)

Proteinase inhibitors (AsPIs) with high activity against serine proteinases were purified from seeds of the tree legume, Acacia senegal by ammonium sulfate precipitation followed by DEAE-Sephadex A-25 column and evaluated against Helicoverpa armigera larvae by in vitro and in vivo methods. The molecular weight of AsPIs was found to be approximately 19.58 ± 1.00 and 21.23 ± 1.00 kDa for PI and 18.16 ± 1.00 kDa for PII on sodium dodecyl sulfate-polyacrylamide gel electrophoresis. The AsPIs (5 μg/ml) inhibited approximately 70% of midgut trypsin and 61% of elastase-like chymotrypsin. In vitro studies showed that AsPIs have remarkable inhibitory activity towards total gut proteolytic enzymes followed by trypsin and chymotrypsin. The IC₅₀ of AsPIs for midgut trypsin was 0.1 μg/ml and for chymotrypsin was 2.0 μg/ml. The inhibition of gut proteinase enzymes was of the non-competitive type. In larval feeding studies, AsPIs were found to retard growth and development of H. armigera and also affects the fecundity of the pest. The results advocate the use of AsPIs in transgenic technology to develop plant resistance to H. armigera.