Studies on the chiral isomers of fonofos and fonofos oxon: I. Toxicity and antiesterase activities

The toxicity of the (R)_P and (S)_P chiral isomers and racemates of fonofos and fonofos oxon to insects and white mice were determined. (R)_P-Fonofos and (S)_P-fonofos oxon were 2- to 12-fold more toxic to house flies, mosquito larvae, and mice than were the corresponding enantiomers. The racemates were intermediate in toxicity. Stereoselectivity also was observed in the in vitro inhibition of house fly-head and bovine erythrocyte acetylcholinesterase, horse serum cholinesterase, chymotrypsin, trypsin, and a variety of esterases. In all cases the (S)_P-oxon was a more potent inhibitor than the (R)_P-oxon with k₁ ratios of $\text{(S)}{}_{\mathrm{<mtext>P</mtext>}}\text{(R)}{}_{\mathrm{<mtext>P</mtext>}}$ ranging from 4- to 60-fold. Further, differences in levels of house fly-head, mouse brain, and blood cholinesterase obtained from house flies and mice treated with the enantiomers and racemates of fonofos and fonofos oxon were observed. Differences in toxicity of the enantiomers and racemates to house flies and mice were more closely related to in vivo than to in vitro cholinesterase inhibition.     

Insecticidal,repellent and fungicidal properties of novel trifluoromethylphenyl amides

Twenty trifluoromethylphenyl amides were synthesized and evaluated as fungicides and as mosquito toxicants and repellents. Against Aedes aegypti larvae, N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-3,5-dinitrobenzamide (1e) was the most toxic compound (24 h LC₅₀ 1940 nM), while against adults N-(2,6-dichloro-4-(trifluoromethyl)phenyl)-2,2,2-trifluoroacetamide (1c) was most active (24 h LD₅₀ 19.182 nM, 0.5 μL/insect). However, the 24 h LC₅₀ and LD₅₀ values of fipronil against Ae. aegypti larvae and adults were significantly lower: 13.55 nM and 0.787 × 10⁻⁴ nM, respectively. Compound 1c was also active against Drosophila melanogaster adults with 24 h LC₅₀ values of 5.6 and 4.9 μg/cm² for the Oregon-R and 1675 strains, respectively. Fipronil had LC₅₀ values of 0.004 and 0.017 μg/cm² against the two strains of D. melanogaster, respectively. In repellency bioassays against female Ae. aegypti, 2,2,2-trifluoro-N-(2-(trifluoromethyl)phenyl)acetamide (4c) had the highest repellent potency with a minimum effective dosage (MED) of 0.039 μmol/cm² compared to DEET (MED of 0.091 μmol/cm²). Compound N-(2-(trifluoromethyl)phenyl)hexanamide (4a) had an MED of 0.091 μmol/cm² which was comparable to DEET. Compound 4c was the most potent fungicide against Phomopsis obscurans. Several trends were discerned between the structural configuration of these molecules and the effect of structural changes on toxicity and repellency. Para- or meta- trifluoromethylphenyl amides with an aromatic ring attached to the carbonyl carbon showed higher toxicity against Ae. aegypti larvae, than ortho- trifluoromethylphenyl amides. Ortho- trifluoromethylphenyl amides with trifluoromethyl or alkyl group attached to the carbonyl carbon produced higher repellent activity against female Ae. aegypti and Anopheles albimanus than meta- or para- trifluoromethylphenyl amides. The presence of 2,6-dichloro- substitution on the phenyl ring of the amide had an influence on larvicidal and repellent activity of para- trifluoromethylphenyl amides.     

Insecticidal activity and microsomal metabolism of biooxidizable lindane analogs

The insecticidal activity of lindane analogs, in which some chlorine atoms were replaced by other groups susceptible to microsomal oxidative metabolism, was determined against mosquitos, house flies, and German cockroaches. When tested with a synergist, piperonyl butoxide, one of the methylthio analogs was as active as lindane, whereas several others were also highly active. By examining the ratio of synergized and unsynergized LD₅₀ values (synergistic ratio value), the highly insecticidal methylthio, methoxy, and methyl analogs appear to undergo metabolic detoxication effectively in house flies. By means of in vitro metabolism experiments using microsomal fraction from house fly abdomen, the methoxy, ethoxy, and methylthio analogs were shown to be metabolized rapidly at similar rates. The synergized insecticidal activities of these compounds against various insect species relate linearly with each other, suggesting that the oxidative degradation is inhibited by the synergist to a similar extent and that the transport process to the site of action is not a limiting factor in determining the relative insecticidal activity.     

Insecticidal properties of benzofuran-2-carboxylic acid derivatives

A series of amides and esters of substituted benzo[b]furan-2-carboxylic acids have been synthesised, and their activity against adult sweet potato weevils, Cylas formicarius elegantulus (Summer) studied. The topical insecticidal potency of these compounds was compared in acetone solution and in a mixture of piperonyl butoxide (PB) and acetone (0·05+99·95 by volume). The compounds were much more active when administered in the acetone/PB mixture, and exhibited 48-h LD₅₀ values ranging from 1·7 to 26·6 μg per insect. The most active compound, 2-(3,5-dimethylpyrazol-1-ylcarbonyl)-6-methoxy-3-methylbenzofuran, was equiactive with technical grade dimethoate (in acetone/PB) on a weight basis. © 1998 SCI     

15种昆虫生长调节剂对库蚊幼虫的杀虫活性

浸渍法表明,定虫隆、氟幼脲是试验杀虫剂中对尖音库蚊淡色亚种幼虫杀虫活性最高的.定虫隆、氟幼脲、氟虫脲、氟铃脲、农梦特舜口除虫脲的杀虫活性分别是抑食肼的2 740倍、2 100倍、1 763倍、1 283倍、1 229倍和573倍.     

新杀虫剂HNPC-A9908对几种鳞翅目昆虫的杀虫活性

采用农药生测标准操作程序 (SOP)测定了HNPC-A9908对几种鳞翅目昆虫的毒力及其作用方式。室内生测结果表明 ,HNPC-A990 8对粘虫具有良好的杀虫活性 ,其综合毒力LC₅₀、触杀毒力LD₅₀和胃毒毒力LC₅₀分别为7 71mg/L、400×10^-3μg/头和82.34mg/L ;对斜纹夜蛾的综合毒力为 280.57mg/L。田间小区试验结果表明 ,HNPC-A9908对菜青虫表现出良好的防治效果 ,有效用药量为 10、30、50g/667m² 时 ,药后 1、3、7、10d的防治效果分别为 88.18%～98.39%、100%、96.79%～100%和 88.16%～100%。此外 ,HNPC-A9908对甜菜夜蛾和棉铃虫也具有一定的防治效果     

57种南药植物粗提物对螺旋粉虱杀虫活性初步研究

测试了57种南药植物粗提物对螺旋粉虱成虫的杀虫活性.结果表明,在5 mg/mL浓度下,57种南药植物粗提物对螺旋粉虱成虫表现出较好的触杀活性.其中长春花、艾纳香、刺篱木、薄荷、广藿香、曼陀罗6种南药植物粗提物对成虫的触杀活性在60％以上,活性最好的是长春花粗提物,对成虫的触杀活性为67.3％.毒力测定结果表明:薄荷粗提物对成虫的EC50值最小,为3.308 9 mg/mL.因此薄荷对螺旋粉虱表现出较好的抑制活性,具有进一步研究开发的价值.     

Acephate and methamidophos residue behavior in Florida citrus, 1976.

The half-life of acephate and its hydrolysate, methamidophos, in the rind of Temple and Valencia oranges, and grapefruit, lemons, and tangerines was 10.3 days and 10.5 days, respectively. Half-lives of acephate and methamidophos in citrus pulp were 15.0 days and 6.1 days, respectively based on 7-, 14-, and 21-day data. Seven days after treatment, acephate and methamidophos reached maximum levels in rind and pulp. Acephate residue levels in rind were less than 3.0 ppm 14 days after treatment; acephate residues in pulp were less than 3.0 ppm throughout the experiment. Methamidophos residue levels averaged less than 0.25 ppm after 21 days.     

三峡地区5种中国特有植物的杀虫和抗菌活性

测定了三峡地区5种中国特有植物的杀虫和抗菌活性,结果表明：10 mg/g的狭叶金粟兰（Chloranthus angustifolius）和裸芸香（Psilopeganum sinense）甲醇提取物对家蝇（Musca domestica）成虫24 h的致死率分别为90.30 %和62.22 %;10 mg/mL的疏花水柏枝（Myricaria laxiflora）、裸芸香和狭叶金粟兰的甲醇提取物对斜纹夜蛾（Spodoptera litura）3龄幼虫24 h的拒食率分别为96.74 %、83.56 %和76.74 %;10 mg/mL狭叶金粟兰甲醇提取物对荔枝霜疫霉（Peronophythora litchii）、黄瓜疫霉（Phytophthora melonis）、稻瘟菌（Magnaporthe oryzae）和稻纹枯菌（Rhizoctonia solani）的抑菌率均为100 %,对香蕉炭疽菌（Colletotrichum musae）和西瓜枯萎菌（Fusarium oxysporum f.sp.niveum）的抑菌率分别为83.67 %和74.97 %;裸芸香对稻瘟菌、荔枝霜疫霉和黄瓜疫霉的抑菌率分别为100 %、95.36 %和89.01 %。     

含酰腙结构的新型吡唑酰胺衍生物对小菜蛾的生物活性

采用浸虫法、夹毒叶片法和叶碟法分别测定了13个含酰腙结构的新型吡唑酰胺衍生物对小菜蛾3龄幼虫的触杀、胃毒和拒食活性。结果表明:该类化合物对小菜蛾3龄幼虫具有较高的胃毒和拒食活性,其中苯环上含有氯原子、且酰腙一端的取代基含有杂原子且体积较小的化合物 H7的胃毒和拒食活性最好,明显高于对照药剂毒死蜱。H7 72 h胃毒作用LC50值为0.6 mg/L(毒死蜱的LC50值为7.4 mg/L);有10个化合物的拒食活性高于毒死蜱,其中 H7 48 h的拒食中浓度(AFC50) 最低,为0.6 mg/L,明显低于毒死蜱(AFC50=6.5 mg/L)。供试化合物对小菜蛾3龄幼虫均无触杀活性。     

艳山姜叶挥发油对赤拟谷盗的杀虫活性

为开发新型仓储防护剂,研究艳山姜Alpinia zerumbet叶子挥发油的化学成分及其对仓储害虫赤拟谷盗Tribolium castaneum的杀虫活性。通过GC-MS分析了艳山姜叶挥发油的化学成分,并通过熏蒸、触杀试验测试挥发油及单体成分的活性。艳山姜叶挥发油中鉴定出31种化合物,主要成分为邻伞花烃(14.86%)、桉油精(8.44%)、芳樟醇(8.28%)、氧化石竹烯(7.62%)、柠檬烯(7.29%)、莰烯(7.23%)、α-蒎烯(6.40%)和左旋樟脑(6.20%)。通过生物活性筛选,艳山姜叶挥发油对赤拟谷盗成虫具有触杀毒性(LD_(50)值为6.59μg/头)和熏蒸毒性(LC_(50)为5.19mg/L)。挥发油中的主要化合物莰烯、柠檬烯和桉油精对赤拟谷盗均有一定的触杀毒性,LD_(50)分别为5.13、14.97和18.83μg/头。莰烯对赤拟谷盗还显示出较强的熏蒸活性,LC_(50)为4.10mg/L。因此,艳山姜叶挥发油及其活性化合物在应用于赤拟谷盗的防治方面有潜力。     

Insecticidal properties of some allethrin isomers used in coil formulations against mosquitoes

Previous studies have been made on the relative efficacy of the eight possible stereoisomers of allethrolonyl chrysanthemate. Some of these compounds and their mixtures have been classified according to their knockdown activity against Aedes aegypti. Two techniques were used, the contact method recommended by WHO and the method described by Katsuda and Ogami to study the effect on mosquitoes of the smoke from burning coils. Results show that on Aedes aegypti, the relative knockdown activity of the various stereoisomers of allethrin was about the same with both methods. The d trans chrysanthemate of d allethrolone (S-Bioallethrin) was the most effective.     

Insecticidal activities of leaf and twig essential oils from Clausena excavata against Aedes aegypti and Aedes albopictus larvae

BACKGROUND: The current study investigates, for the first time, the mosquito larvicidal activities of leaf and twig essential oils from Clausena excavata Burm. f. and their individual constituents against Aedes aegypti L. and Aedes albopictus Skuse larvae. The yields of essential oils obtained from hydrodistillation were compared, and their constituents were determined by GC‐MS analyses. RESULTS: The LC₅₀ values of leaf and twig essential oils against fourth‐instar larvae of Ae. aegypti and Ae. albopictus were 37.1–40.1 µg mL^?1 and 41.1–41.2 µg mL^?1 respectively. This study demonstrated that C. excavata leaf and twig essential oils possess mosquito larvicidal activity, inhibiting the growth of mosquito larvae for both species at a low concentration. In addition, results of larvicidal assays showed that the effective constituents in leaf and twig essential oils were limonene, γ‐terpinene, terpinolene, β‐myrcene, 3‐carene and p‐cymene. The LC₅₀ values of these constituents against both mosquito larvae were below 50 µg mL^?1. Among these effective constituents, limonene had the best mosquito larvicidal activity, with LC₅₀ of 19.4 µg mL^?1 and 15.0 µg mL^?1 against Ae. aegypti and Ae. albopictus larvae respectively. CONCLUSION: The findings suggested that the essential oils from Clausena excavata leaf and twig and their effective constituents may be explored as a potential natural larvicide. Copyright © 2008 Society of Chemical Industry     

Cholinesterase inhibition by methamidophos and its subsequent reactivation

Methamidophos (O,S-dimethylphosphoramidothioate, Monitor) is an organophosphorus, cholinesterase-inhibiting insecticide. The rate constant (k_i) for inhibiting rat plasma cholinesterase (ChE) was 1.57 ± 0.03 × 10³M^?1 min^?1, for rat erythrocyte ChE was 8.86 ± 1.10 × 10³M^?1 min^?1, and for rat brain ChE was 6.58 ± 0.42 M^?1 min^?1. Brain and plasma cholinesterases spontaneously recovered from over 90% inhibition at 30 min to 50% inhibition in 4 and 14 hr, respectively. Pralidoxime increased the rate of reactivation in vitro. In vivo, rats poisoned with methamidophos exhibited signs of cholinergic stimulation. The LD₅₀ of ip methamidophos in male rats was 15 ± 0.7 mg/kg. Pralidoxime (60 mg/kg) and atropine (10 mg/kg) given with the methamidophos increased the LD₅₀ to 52 ± 4.9 mg/kg and 60 ± 0.4 mg/kg, respectively. In rats given 12.5 mg methamidophos (an LD₂₀), ChE activity was depressed 95 ± 12.5% in plasma, 92 ± 0.6% in stomach, and 88 ± 1% in brain at 1 hr after injection. At 48 hr after injection ChE activity had returned to 60% or more of control values in each of the tissues. Administration of a single dose of 60 mg/kg of pralidoxime along with methamidophos did not increase ChE activities at the times and places it was measured.     

二化螟对杀虫单和甲胺磷抗性监测及田间抗性动态

二化螟Chilo suppressalis(Walker)是一种重要的钻蛀性水稻害虫,严重危害水稻生产,特别是杂交水稻的大面积推广以后,其发生和为害呈上升的趋势。近年来,在很多稻区杀虫单和甲胺磷对二化螟田间防效下降,可能是抗药性产生和发展的结果。1999年,作者临测了浙江五个地区和贵州贵阳地区二化螟对杀虫单和甲胺磷的抗性水平,并定点监测     

Insecticidal and repellent properties of nine volatile constituents of essential oils against the American cockroach,Periplaneta americana (L.)

The toxic and repellent properties of nine major constituents of essential oils, comprising benzene derivatives and terpenes, were evaluated against Periplaneta americana (L.). Contact and fumigant toxicities to adult females and repellency to nymphs were determined. The decreasing order of knockdown activity via contact was methyl-eugenol>isosafrole=eugenol>safrole. The killing effect via contact was in the order eugenol=methyl-eugenol=isosafrole>safrole. Fumigant toxicity was only observed for safrole and isosafrole, with safrole being the more potent. Isoeugenol and the tested terpenes had neither contact nor fumigant toxic effect. The decreasing order of repellency to nymphs was safrole>isosafrole>methyl-eugenol=α-pinene> eugenol>isoeugenol. The benzene derivatives were generally more toxic and repellent to P. americana than the terpenes. The distance of the side chain double bond from the aromatic ring and the substitution of a methoxy group to these compounds appeared to be important determinants of their toxicity and repellency. © 1998 Society of Chemical Industry     

13种生物杀虫剂对草地贪夜蛾2龄幼虫的杀虫活性

<正>草地贪夜蛾Spodoptera frugiperda属鳞翅目夜蛾科灰翅夜蛾属Spodoptera,俗称秋黏虫,是一种重要的世界级入侵性农业害虫。原产于美洲的热带和亚热带,具有迁飞能力强、食性广和繁殖能力强等特点。该害虫主要通过取食生长点、根部、叶片、花丝、     

Insecticidal activity of N-arylalkylbenzhydrolpiperidines

Benzhydrolpiperidine (BZP) insecticides represent a novel class of chemistry. Their specificity and efficacy as well as their low mammalian toxicity give them excellent potential for commercialization. Several N-arylalkylbenzhydrolpiperidines were tested for activity against a variety of insects in the laboratory and greenhouse. These tests were used to select compounds for field trials and determine rates of application for field tests. The BZP compounds have good activity against Lepidoptera, with modest Coleoptera activity. They are toxic by oral administration and have about 100-fold lower activity by topical exposure. A methyl carbamate BZP, F4265, was the most active compound, with LC50 values of 6 mg litre(-1) or less for most Lepidopteran species tested. F4265 was active in a variety of field trials at 112-224gAI ha(-1). Whole-plant testing methods conducted in the greenhouse were effective in determining field test rates.     

Insecticidal and repellent activities of insecticide-sucrose solutions to Culex pipiens molestus (Diptera: Culicidae) under laboratory and field conditions

BACKGROUND: Culex pipiens molestus Forskal has been reported as a dominant species in underground structures of urban areas in the Republic of Korea (ROK) during all seasons and becomes bothersome to humans in late autumn and winter. Most Cx. pipiens molestus in septic tanks are controlled in the ROK using larvicides such as Bt and IGR. However, there are a number of problems associated with larvicides, such as high cost and requirement for frequent use. In the present work, a new control method for Cx. pipiens molestus in septic tanks by using mixtures of sucrose solution with insecticides was investigated. RESULTS: The insecticidal and repellent activities of ten insecticides were evaluated for best control of Cx. pipiens molestus in septic tanks. Firstly, differences in susceptibilities to insecticides were evaluated in topical assays by forced direct contact bioassay and in a screened wire cage by free direct contact bioassay. The difference in insecticide susceptibility in the mosquitoes was the result of repellency by the insecticides. In three septic tanks, the density of Culex mosquitoes was sharply reduced by a deltamethrin–sucrose solution kit. CONCLUSIONS: The results demonstrated the potential for mosquito control by deltamethrin–sucrose solution, and the study offers basic information related to mosquito control in septic tanks. Copyright © 2011 Society of Chemical Industry