Synthetic bis- and mono-chalcones with insecticide effects on Spodoptera frugiperda (Lepidoptera: Noctuidae)

Abstract

This is the first report on the antifeedant, toxic and nutritional effects produced by the synthetic chalcones on the lepidopteran Spodoptera frugiperda followed by structure-activity relationship. Bis (5a-c) and mono (8a-d) chalcones have been synthesized via Claisen-Schmidt condensation and have been purified and characterized. The mono chalcones 8b and 8d displayed toxic effects on early larval instars when incorporated to the larval diet at 100?µg per g of diet (40 and 60%, respectively) and low adults emergency with malformations leading to death. The remaining chalcones 8a, 8c, 5a, 5b and 5c do not displayed toxic effects at the same dose. The evaluation of nutritional indices indicated that 8a and 8c were the only tested chalcones to produce decrease in the growth rate and to reduce the efficiency with which larvae converted ingested food into biomass.     

2-酰氧基环己烷基磺酰胺的组合合成与杀菌活性

为了快速获得具有杀菌活性的先导化合物,按照苯环上取代基的性质,将18个N-取代苯基-2-羟基环己烷基磺酰胺分成8个大小不等的原料库(A),分别与过量的2-乙氧基乙酰氯(B1)和4-氟苯甲酰氯(B2)反应,获得16个2-酰氧基环己烷基磺酰胺类组合库。通过气相色谱-质谱联用仪(GC-MS)和红外光谱分析了组合库中36个化合物的结构和含量。以番茄灰霉病菌Botrytis cinerea Pers.为供试靶标,菌丝生长速率法测试结果表明:当A的苯环上含有多个Cl或CF3等吸电子基团时,与B1反应生成的组合库的活性普遍较高,其中活性组合库A5B1、A6B1和A7B1的杀菌活性均高于对照药剂腐霉利;黄瓜离体叶片试验表明,活性组合库A6B1和A7B1的防效也与腐霉利相当。在组合库生物活性筛选中化合物的结构、含量和数量是影响筛选结果的3个因素,其中结构为主要因素。     

Photostabilization of biocontrol agents by berberine

We studied the photostabilizing effect of the isoquinoline alkaloid berberine on the following three model photounstable biocontrol agents: the bacterium Bacillus thuringiensis ( Bt ), the baculovirus Spodoptera littoralis nucleopolyhedrosis virus ( SlNPV ), and the entomopathogenic fungus Beauveria bassiana . The photoprotection provided by berberine was evaluated following various periods of simulated sunlight-UV irradiation. Insecticidal activity of Bt and SlNPV , as well as the rate of B. bassiana spore germination served as parameters for the photostabilizing effects. Only a berberine- Bt complex is effective, as practically no photostabilization was evident by just mixing the two components. The UV-sensitive SlNPV and B. bassiana spores were considerably photostabilzed by berberine. The role of the cationic nature of the berberine molecule and the importance of its absorbance spectrum in photostabilization of biocontrol agents are discussed.     

香豆素类化合物对朱砂叶螨的触杀活性及定量构效关系研究

采用玻片浸渍法,测定并筛选了25种具有代表性的香豆素类化合物对朱砂叶螨Tetranychus cinnabarinus雌成螨的触杀活性,并构建了一个预测能力较强的定量构效关系(QSAR)模型。结果表明:所有供试化合物对朱砂叶螨均具有触杀活性,且随着处理时间的延长活性升高。处理48 h后,LC50值低于1000 mg/L的化合物有8个,分别是3-(2-苯并咪唑)-7-(二乙氨基)香豆素(1)、3-(2-苯并噻唑)-7-(二乙氨基)香豆素(2)、3-氨基香豆素(3)、3-乙酰基香豆素(4)、4-甲氧基香豆素(5)、6-硝基香豆素(8)、6,7-二甲氧基香豆素(13)和7,8-二羟基香豆素(21),其中化合物1、2、3、5和13的杀螨活性优于药剂对照螺螨酯或与其活性相当;活性最好的化合物为13,处理48 h和72 h后LC50值分别为284.8和122.2 mg/L,其毒力约为螺螨酯的2倍。通过计算得到25种香豆素类化合物的34种物化参数,以此为描述子,经过SPSS相关性剔除、逐步回归分析和校正,得到一个以扭转力、取向力、总能量和分子半径为自变量的QSAR模型,该模型复相关系数R达到0.987,复判定系数R2也达到0.967,通过F检验证明上述模型具有较高的预测能力。     

Use of Mechanical Power for Rotary Weeding

Suppressive soils and plant disease.

Edited by R. W. Schneider. American Phytopathological Society, St. Paul, Minnesota, 1982. ISBN 0 89054 048 9. Pp. 88. Price APS members US $8.00, nonmembers US $9.00.

Annual review of phytopathology.

Volume 20. Edited by R. G. Grogan, G. A. Zentmyer and E. B. Cowling.

Annual Reviews Inc., Palo Alto, California, 1982. ISBN 8243 1320 8. Price US$ 22.00 (USA), US$ 25.00 (elsewhere).

The locust and grasshopper agricultural manual.

Centre for Overseas Pest Research, London, 1982. ISBN 0 85135 120 4. Pp.690. Price £50.00.

CRC handbook of pest management in agriculture.

Edited by D. Pimental. CRC Press, Inc., Boca Raton, Florida, USA, 1982. Three volumes. ISBN 0 8493 3841 7 (Vol. I). Vol. I. Pp. 597, price US$ 86.00 (US$ 99.00 outside US). Vol. II. Pp. 501, price US$ 76.00 (US$ 87.00 outside US). Vol. III. Pp. 656, price US$ 86.00 (US$ 99.00 outside US).

Weed science: principles and practices.

G. C. Klingman and F. M. Ashton with editorial assistance of L. J. Noordhoff. Second Edition. John Wiley — Interscience, New York, 1982. ISBN 0 471 08487 5. Pp. 449. Price £19.00.

Biology and ecology of weeds.

Edited by W. Holzer and M. Numata. Geobotany Series 2. Dr. W. Junk Publishers, The Hague, 1982. ISBN 90 6193 682 9. Pp.461. Price US$ 99.50.

Plantas daninhas do Brasil.

H. Lorenzi. Published by the author, Nova Odessa, S. P., Brasil, 1982. Pp. 425.

Integrated weed management systems technology for crop production and protection.

Proceedings of a Symposium of the Weed Science Society of America, Las Vegas, February 1981. Supplement to Weed Science volume 30, 1982. Pp. 54.

Weeds and weed control in Asia.

Food and Fertiliser Technology Centre, Taipei, Taiwan (FFTC Book Series No. 20), 1981. Pp. 259.

Building a sustainable society.

L. R. Brown. W. W. Norton &; Co., New York and London, 1982. ISBN 0 393 01482 7. Pp. 433. Price US $14.95     

Progeny production of Steinernema abbasi in lepidopterous larvae

Progeny production of a new entomopathogenic nematode Steinernema abbasi in various lepidopterous prepupae was investigated. Most dauer juveniles (DJs) developed in the greater wax moth, Galleria mellonella (234 000) but the bollworms Helicoverpa virescens (220 000) and Spodoptera exigua (166 000) were also good hosts. Progeny production was independent of the number of nematodes invading the host between the doses of 40 and 230 DJs. The infectivity of DJs declined when they were stored for 3 months but at 30°C approximately 11% of the DJs were still infective. S. abbasi is a nematode of the semi-arid tropics and it would be possible to use the nematode to target pests in these areas if it can be produced satisfactorily locally.     

米尔贝霉素类似物的合成及杀螨杀蚜活性

为寻找高活性的米尔贝霉素衍生物,以伊维菌素为原料,经脱糖、羟基保护、氧化、还原胺化、脱保护等将其转变为13-氨基米尔贝霉素类似物,通过三组分反应设计合成了一系列米尔贝霉素磺酰脒类化合物(7a~7i),并初步测定了其对朱砂叶螨Tetranychus cinnabarinus和豆蚜Aphis craccivora的室内活性。结果表明:各衍生物对朱砂叶螨和豆蚜均有较好的触杀活性,其中7f、7h和7i对朱砂叶螨24 h的LC50值分别为1.04×10–2、9.60×10–4和1.44×10–2 mg/L;7i对豆蚜24 h的LC50值为7.81 mg/L。米尔贝霉素13位氨基上磺酰化的结构修饰有助于提高米尔贝霉素类化合物的杀螨、杀蚜活性。     

新型含苯并咪唑的(S,S)-2,8-二氮杂双环[4.3.0]壬烷类衍生物的合成及生物活性

通过N-烷基化反应合成了一系列新型含苯并咪唑的(S,S)-2,8-二氮杂双环[4.3.0]壬烷类衍生物,中间体化合物通过环化反应和酰化反应合成得到。所有新型化合物的结构均通过熔点测定、核磁共振氢谱和高分辨质谱确认。生物活性测试结果显示,目标化合物拥有中等的抗植物真菌活性,对东方粘虫Mythimna separata Walker和蚊幼虫Culex pipiens pallens具有中等到良好的杀虫活性。其中化合物6e和6f对油菜菌核Sclerotinia sclerotiorum、马铃薯晚疫Phytophthora infestans、小麦赤霉Fusarium graminearum等真菌具有良好的抗菌活性。化合物6e和6k在200mg/L下对东方粘虫的致死率为100%,化合物6h和6k在2mg/L下对蚊幼虫的致死率为75%。     

山蒟中脂肪链酰胺类化合物的分离及杀虫活性

采用提取、萃取及柱层析等方法,从山蒟Piper hancei Maxim甲醇提取物的石油醚和氯仿萃取相中分离到6个脂肪链酰胺类化合物,通过核磁共振、质谱并结合相关文献比对,其结构被分别鉴定为已知化合物chingchengenamide A( C1 )、N-异丁基-反-2-反-4-癸二烯酰胺( C2 )、假荜拨酰胺A( C3 )、荜茇宁( C4 )、N-p-香豆酰酪胺( C5 )和N-反式-阿魏酰酪胺( C6 ),其中 C1 为首次从山蒟中获得。利用幼虫浸液法测试了各化合物对白纹伊蚊Aedes albopictus和致倦库蚊Culex pipiens quinquefasciatus幼虫的12 h杀虫活性。结果表明:在20 mg/L下,化合物 C1 对白纹伊蚊的杀虫活性较高,其校正死亡率为100%,LC₅₀值为5.37 mg/L;化合物 C1 、 C2 、 C3 和 C4 对致倦库蚊的杀虫活性较高,20 mg/L下的校正死亡率分别为100%、88.5%、100%和100%,LC₅₀值分别为1.03、9.68、3.08和2.87 mg/L。     

Recommendations for the Use of Herbicides

Management of Pests and pesticides: Farmers’ Perceptions and Practices. Editors Joyce Tait and Banpot Napompeth, Boulder, Col.: Westview Press 1987. ISBN 0–8133–7174–0, £33 paperback.

Termites in Buildings. Their Biology and Control. R. Edwards and A. Mill. Rentokil Library, 1987, ISBN 0906 5640 69 £24–50.

Pesticide Science and Biotechnology. Proceedings of the Sixth International Congress of Pesticide Chemistry. Ottawa, Canada, 10–15 August 1986. Edited by R. Greenhalgh and T. R. Roberts. IUPAC/Blackwell Scientific Publications, 1987 (602 pp + xiii).

Breeding for Resistance to Diseases and Insect Pests. By D. P. Singh. 222 pp + xi. ISBN 0 387 16970 9. Springer Verlag. 1986. Price $7900.

Pest Control Safe for Bees: A Manual and Directory for the Tropics and Subtropics. By M. Adey, P. Walker and P. T. Walker, 1986. International Bee Research Association, London. Price £12–20.

The Cocoa Pod Borer: An Introduction and Abstracts. Compiled by Lim Guan Soon et al. Malaysian Plant Protection Society, Box 12351 Kuala Lumpur. 1987. 103 pp. ISBN 967–9942–07–4.

Pentachlorophenol. Environmental Health Criteria, No. 71, World Health Organization, Geneva, 1987. 236 pages, ISBN 92 4 154271 3. Price: Sw.fr. 18—/US$1080.

Ecology and Control of Perennial Weeds in Latin America. FAO Plant Production and Protection Paper No. 4. Food and Agriculture Organization, Rome. 1986, 339 pp. ISBN 92–5–102446–4.

Proceedings of the 2nd International Workshop on Leaf hoppers and Planthoppers of Economic Importance. Edited by M. R. Wilson and L. R. Nault. CAB International Institute of Entomology. 1987. 368 pp. ISBN 0–900301–03–1.

Breeding for Durable Resistance in Perennial Crops. FAO Plant Production and Protection Paper No. 70 (1986). 130 pp.

Ascochyta Blight Resistance in Chickpea. Proceedings of a training course, PARC/ICARDA, 3–10 March, 1984, Islamabad, Pakistan. ICARDA, 1986, 123 pp.     

含哌啶噻唑结构的乙酰氨基衍生物的合成及杀菌活性

为了寻找高效的杀菌活性物质,以哌啶噻唑结构为母体,甘氨酸为连接基团,通过重氮化、氯化、成环和缩合等步骤合成了14个含哌啶噻唑结构的乙酰氨基衍生物,通过核磁共振氢谱 (1H NMR)、碳谱(13C NMR)及高分辨质谱 (HRMS)对化合物的结构进行确证。初步杀菌活性测定结果表明:甘氨酸作为连接基团对化合物杀菌活性的提高具有积极影响,其中,化合物 7a 、 7c 和 7g 在25 mg/L剂量下对黄瓜灰霉病菌的抑制率为68.7%、71.6%和67.2%,化合物 7a 、 7g 和 7i 对马铃薯晚疫病菌的抑制率分别为50.8%、61.9% 和55.8%。     

Possibilities of Biological Control of Liver Flukes

A survey was conducted to gain insight into the perceptions of Lesotho's farmers with regard to insect pests of maize and sorghum, to identify management practices that could impact on stalk-borer numbers and to shed light on other farming practices such as variety selection and crop residue management. Field studies were conducted to determine the incidence and distribution of Busseola fusca (Lepidoptera: Noctuidae) and Chilo partellus (Lepidoptera: Pyralidae) larvae in sorghum and maize residues and to determine the effect of certain crop residue management practices on stalk-borer survival. Results indicated that farmers regard stalk-borers as important pests that sometimes need to be controlled. However, most farmers never apply control measures, mainly due to lack of resources. Residues of maize and sorghum plants are largely used as animal fodder with maize being cut and fed to animals after harvest. Sorghum crop residues are largely left on fields after harvest to be used by free-grazing animals. While stacks of maize stalks were not important in the winter survival of B. fusca larvae, stacking of sorghum ensures winter survival of C. partellus larvae. Detasselling of maize plants is commonly done at plant senescence and the upper halves of plants are fed to animals. Detasselling of maize plants had no effect on the number of borer larvae in plants at harvest.     

Presence–absence sampling for Tetranychus urticae and its predator Neoseiulus californicus (Acari: Tetranychidae; Phytoseiidae) on strawberries

The use of snails as biocontrol agents against other snails and against aquatic weeds is reviewed, evaluating their success and their impacts on non-target organisms. The predatory snail Euglandina rosea (and other species), although widely used against Achatina fulica (the giant African land snail) on Pacific and Indian Ocean islands, has not been shown to control A. fulica but has seriously impacted endemic island species. The facultative predator Rumina decollata , used in California against Helix aspersa (brown garden snail), is widely considered to be environmentally benign. However, evidence of its effectiveness is weak and it will also consume native snails. Ampullariid and thiarid freshwater snails have been used as competitors (and incidental predators) of snail vectors of human schistosomes, the parasites causing schistosomiasis (bilharzia). Successful control has been reported but impacts on native biotas have been essentially ignored. Ampullariids have been used in attempts to control aquatic weeds, sometimes successfully, but again with little consideration of impacts on native biota. Most snails have generalist feeding habits. Thus they are inappropriate biocontrol agents because of their potential nontarget effects. Rarely has adequate pre-release testing of snails been undertaken and post-release monitoring of non-target impacts has always been incidental. The use of non-native snails for biocontrol purposes is poorly regulated; many introductions are unofficial and sometimes illegal. Use of snails as biocontrol agents, if implemented, must be based on adequate pre-release testing, post-release monitoring and genuine concern for preservation of native biodiversity.     

杠柳杀虫活性成分的分离

采用柱层析分离、高效液相色谱切分和生物活性追踪法,从杠柳 Periploca sepium 根皮甲醇提取物中分离出2个具有杀虫活性的化合物(G1和G2),经鉴定其分别为已知物杠柳新苷D和F。生物活性测定结果表明,化合物G1和G2 对3龄粘虫 Mythimna separata 48 h的胃毒致死中浓度(LC50)分别为0.39和0.34 mg/mL, 对小菜蛾 Plutella xyllostella 48 h的胃毒LC50值分别为1.21和1.39 mg/mL。     

3-取代苯亚甲基-6,7-亚甲二氧基-4-色满酮的合成及抑菌活性

以芝麻酚为起始原料,经过醚化、傅克酰基化、羟醛缩合等反应,设计合成了21个未见文献报道的6,7-亚甲二氧基-4-色满酮类化合物（d1~d21）,其结构均经核磁共振氢谱、碳谱以及红外光谱和质谱确认。初步抑菌活性测定结果表明:在50 mg/L下,中间体色满酮及所有目标化合物对8种供试植物病原菌均有不同程度的抑制作用,其中色满酮对番茄灰霉病菌Botrytis cinerea和烟草赤星病菌Alteraria alternate的抑制率分别为87.9%和56.7%,目标化合物d1和d6对水稻稻瘟病菌Mangnaporthe grisea的抑制率分别为72.2%和52.5%,d6对玉米弯胞病菌Curvulavia lunata和d9对苹果腐烂病菌Valsa mali的抑制率均在70%以上。     

N-(2-三氟甲基-4-氯苯基)-2-吡唑酰氨基环己烷基磺酰胺类化合物的合成与杀菌活性

吡唑酰胺类杀菌剂是近年新农药开发的热点。本研究采用EDCI/HOBt酰胺化法合成了14个结构新颖的N-(2-三氟甲基-4-氯苯基)-2-吡唑酰氨基环己烷基磺酰胺类化合物 ( 3a ~ 3n ),其结构均经1H NMR、13C NMR、质谱和元素分析确认,并用X-射线衍射法确定了化合物 3g 的单晶结构和立体构型。菌丝生长速率法试验结果表明,化合物 3a 、 3e 和 3j 对番茄灰霉病菌Botrytis cinerea KZ-9的EC₅₀值分别为4.28、10.08和11.31 mg/L,抑菌活性不及对照药剂啶酰菌胺和腐霉利;但在孢子萌发试验中,目标化合物表现出与对照药剂相近的抑菌活性,在10 mg/L下有7个化合物对灰霉病菌孢子萌发的抑制率超过了85%;在番茄活体盆栽试验中,化合物 3e 在200 mg/L下对番茄叶片及其花上灰霉病菌的防治效果分别为77.5%和65.2%,高于对照药剂啶酰菌胺 (防效分别为59.8%和30.3%),有进一步研究的价值。     

Insecticidal Control of Pineus sp. (Homoptera: Adelgidae) in East Africa

Village Republics: economic conditions for collective action in South India. R. Wade, 1988. Cambridge, Cambridge University Press, ISBN 0–521–30146–7

Shared Wealth and Symbol: Food, Culture and Society in Oceania and Southeast Asia. L. Manderson (ed), 1986. Cambridge University Press. ISBN 0–521–32354–1 (hardback).

Peasant Economics: farm households and agrarian development. F. Ellis, 1985. Cambridge, Cambridge University Press. ISBN 0–521–31008–3 £11.95 (paperback) 0–521–32446–7 £35.00 (hardback)

Agricultural Pests of India and South East Asia. A. S. Atwal. Kaljani Publishers, India 1986, pp. 529 + XII Rupees 175.00

A Farmer's Primer on Growing Soybean on Riceland. By R. K. Pandey, 1987. International Rice Research Institute and International Insitute of Tropical Agriculture. 216p. ISBN 971–104–168–5.

Liquid Calibration Handbook. By C. W. Kroon. Thomson Publications. 2nd. Edition, 1987, pp. 221. U.S. $25.00.

3rd Gallagher World Wildlife Power Fencing Conference. Gallagher Electronics Ltd., Private Bag, Hamilton, New Zealand

Integrated Pest Control in Viticulture (£25), Integrated Tsetse Fly Control (£22.50). Integrated and Biological Control in Protected Crops (£22.50). Published for the E.E.C. by A. A. Balkema, Rotterdam, 1987.     

Synthesis and bioactivity of novel sulfone derivatives containing 2,4-dichlorophenyl substituted 1,3,4-oxadiazole/thiadiazole moiety as chitinase inhibitors

The paper reported the synthesis and antifungal properties and mechanism of action of a series of 2-substituted methylthio-5-(2,4-dichlorophenyl)-1,3,4-oxadiazole/thiadiazole and their corresponding sulfones. The preliminary biological test showed these compounds exhibit moderate to good antifungal activity. Particularly, the compounds 7g and 7c inhibited mycelia growth by approximately 50% (EC₅₀) at 2.6–59.2 μg/mL and 17.2–54.4 μg/mL respectively against nine kinds of fungi. The extent of inhibition induced by 7c on Rhizoctonia solani and underlying mechanism of action were studied in vitro. Docking simulation was performed to position selected compounds into the active site of family 18 chitinases. Variation in d-GlcNAc content and chitinase activity indicated that 7c can act as chitinase inhibitor for controlling fungal pathogens in plants.     

含单氟甲氧基的双酰胺类化合物的合成及杀虫活性

以2,3-二氯吡啶为起始原料,经肼基化、环合、氧化、取代、水解、环合和胺解反应,合成了15个文献未见报道的新型含单氟甲氧基的吡唑邻甲酰氨基苯甲酰胺类化合物,其结构通过核磁共振氢谱和高分辨质谱确认。初步的杀虫活性测试结果显示,所有目标化合物在100 mg/L下对粘虫Oriental armyworm的致死率均为100%,当测试浓度降低至4 mg/L时,化合物 8a 、 8d 、 8g 、 8k 和 8n 的致死率仍为100%,值得进一步研究。     

Infiltration-excess runoff properties of dryland floodplain soil types under simulated rainfall conditions

The study estimated infiltration-excess runoff properties of three floodplain soil-types under aquifer water management at Anglo American Kolomela Iron Ore mine in Postmasburg, Northern Cape Province of South Africa. Rainstorm regimes of amounts 60 (high), 30 (medium), and 15 (low) mm with respective intensities of 1.61, 0.52, and 0.27?mm min^?1 were simulated on 1 m² plot with 1% slope. Infiltration-excess runoff properties were affected by a rainstorm, but not soil-type. When combined with rainstorm, soil-type affected accumulative run-off rates. High rainstorm had different (p?≤?0.05) accumulative runoff rates (0.1–0.61?mm min^?1) and increased with clay content. Different response times of 4, 10, and 17?min for respective high, medium, and low rainstorms were quickest on higher clay plus silt content and bulk-density under high and lower rainstorms, respectively. Lower rainstorms had similar effects on accumulative runoff rates (0.01–0.05?mm min^?1), total runoff yield (0.59–18?mm), and runoff coefficients (4.29–18%). Under the high rainstorm, total runoff yields (11.4–25.8?mm) and runoff coefficients (19–42.9%) were different and increased with clay plus fine-silt content. Although simulated rainstorms had constant intensities, results showed high rainstorms to be of primal influence on infiltration-excess runoff. Clay plus silt content and bulk-density influenced infiltration-runoff properties for respective high and lower rainstorms. Apart from rainstorm characteristics, surface clay plus silt content and bulk-density are important for harnessing surface runoff in floodplains for aquifer recharge.