The effect of diflubenzuron [1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea] on soybean [Glycine max (L.) Merr.] photosynthesis,respiration, and leaf ultrastructure

The effect of the insecticide diflubenzuron [1-(4-chlorophenyl)-3-(2,6-difluorobenzoyl)urea] on photosynthesis, respiration, and leaf ultrastructure of soybean [Glycine max (L.) Merr., cv. Swift] was examined on plants treated at the second trifoliate leaf stage with 0, 0.067, and 0.269 kg of active ingredien/ha of diflubenzuron. Photosynthesis and respiration were measured with an infrared CO₂ analyzer in an open flow system prior to diflubenzuron application and at 4, 24, 48, and 96 hr after treatment with diflubenzuron. Diflubenzuron had no effect on soybean photosynthesis at any rate examined. Respiration was stimulated by the high rate (0.269 kg/ha) in a transitory manner. Tissue samples removed from both old and new leaves, 9 days after diflubenzuron application, were used for the ultrastructure study with the transmission electron microscope. The lower trifoliate leaves contained more starch grains than the upper ones being formed after treatment, but no aberrations or degradation of leaf ultrastructure due to diflubenzuron treatment were evident.     

(Z)-2-(1H-1,2,4-三唑-1-基)-1-(2,3,4-三甲氧基苯)乙酮肟酯的合成和结构表征

合成了8个(Z)-2-(1H-1,2,4-三唑-1-基)-1-(2,3,4-三甲氧基苯)乙酮肟酯新化合物,经元素分析、IR、1H NMR、MS对其结构进行了表征。讨论了目标化合物的合成方法和立体化学结果。     

3-丙烯酰胺类化合物的合成及杀虫活性

以3,4-亚甲二氧基苯酚(芝麻酚)为原料,经醚化、Vilsmeier反应、Horner反应、酰胺化等步骤制备了12个未见文献报道的3-(3,4-亚甲二氧基-6-烷氧基)丙烯酰胺类化合物,所有化合物的结构均经红外光谱、质谱、1H NMR确证。初步的杀虫活性测试结果表明:化合物 5a~5l 对粘虫3龄幼虫均有一定的杀虫活性,其中化合物 5h和5j 在150 mg/L质量浓度下对粘虫3龄幼虫的校正死亡率分别为50.0%和66.7%。     

Inhibition of acetyl-coenzyme a carboxylase by the novel grass-selective herbicide 3-(2,4-dichlorophenyl)-perhydroindolizine-2,4-dione

The novel herbicidal compound 3-(2,4-dichlorophenyl)-perhydroindolizine-2,4-dione which is active as a pre- and post-emergence grass-selective herbicide is a new type of inhibitor of plant acetyl-coenzyme A carboxylase (ACCase; E.C. 6.4.1.2). This has been demonstrated by in-vitro experiments using isolated corn enzyme. Besides an I₅₀ value of 4.7 μM under the assay conditions used, a mixed-type inhibitory activity on the enzyme is established. The compound is inactive on rat liver A CCase enzyme and shows decreased activity (pI₅₀ less than 3.0) on the spinach enzyme.     

啶菌噁唑对番茄灰霉病菌的抑菌作用研究

采用生物测定方法研究了啶菌噁唑对番茄灰霉病菌Botrytis cinerea不同发育阶段的影响。结果表明:其对菌落扩展、芽管伸长、分生孢子产生和菌核形成均具有显著的抑制活性,其中啶菌噁唑对P-9菌株菌丝生长和芽管伸长的EC50值分别为0.193和0.154 μ g/mL,0.5 μ g/mL的啶菌噁唑对菌丝生长和芽管伸长的抑制率大于77%,对分生孢子和菌核萌发的抑制率分别低于10％和40%,表明药剂对分生孢子萌发无明显抑制作用。紫外吸收分析显示,啶菌 NFDA1 唑可破坏细胞的膜结构,促使菌体核酸和蛋白外渗。离体叶片毒力测定结果表明,120 μ g/mL的啶菌 NFDA1 唑可有效抑制番茄灰霉病病斑扩展,抑制率达83.74%。     

20-(S)-喜树碱7-C-取代衍生物的合成及杀松材线虫活性研究

为研究喜树碱(CPT)类化合物的杀线虫活性,以喜树碱为原料,经烷基化、氧化、酯化等步骤合成了13个7-C-取代的20-(S)-喜树碱衍生物,其中化合物 14 未见文献报道,所有衍生物的结构经红外光谱(FT-IR)、核磁共振氢谱(1H NMR)和液-质联用(LC-MS)等分析手段进行了表征。采用浸渍法测定了化合物对松材线虫Bursaphelenchus xylophilus的毒杀活性。结果表明:与母体化合物喜树碱相比,7-C-取代的20-(S)-喜树碱衍生物具有更强的杀线虫活性,其中化合物7-苄基喜树碱、7-甲酰基喜树碱、7-苯甲酰氧甲基喜树碱在24 h的致死中浓度(LC50值)分别为2.28、2.21和1.37 mg/L,明显高于母体化合物喜树碱的LC50值12.18 mg /L。     

Uncoupling and inhibition properties of 3,4-seco-friedelan-3-oic acid isolated from Maytenus imbricata

3,4-Seco-friedelan-3-oic acid was isolated from Maytenus imbricata (Celastraceae). At low concentrations it inhibited non-cyclic electron transport and ATP synthesis in spinach chloroplasts, i.e., it behaved as a Hill reaction inhibitor, and at high concentrations it acts as an uncoupler by enhancing uncoupled electron transport and Mg²⁺-ATPase activity. 3,4-Seco-friedelan-3-oic acid did not inhibit PSII electron transport from DPC to DCPIP_ox and photosystem I activity, but it enhanced from TMQH₂ to MV, corroborating its action as uncoupler. It inhibits electron flow through PSII from water to sodium silicomolybdate. The whole results indicate that the 3,4-seco-friedelan-3-oic acid target is at the OEC complex enzyme, the donor side of PSII. The fluorescence decay data shows the formation of the K-band, which match this result, acting as inhibitor at the donor side of PSII and it as an uncoupler.     

Impacts of hypersaline water on the biotransformation and toxicity of fenthion on rainbow trout (Oncorhynchus mykiss), striped bass (Morone saxatilis X Morone chrysops) and tilapia (Oreochromis mossambicus)

Hypersaline water derived from agricultural practices primarily in arid landscapes can impact fisheries in streams receiving run-off from fields. Previous studies have indicated significant elevation in the toxicity of thio-ether pesticides by hypersaline water in certain species of euryhaline fish due to enhanced formation of sulfoxide metabolites which may be more toxic than the parent compounds. The objectives of this study were to evaluate the effects of salinity on the toxicity of the thio-ether organophosphate pesticide, fenthion in three species of euryhaline fish: rainbow trout (Oncorhynchus mykiss), striped bass (Morone saxatilis X Morone chrysops), tilapia (Oreochromis mossambicus) and determine whether a relationship was observed between toxicity and enantioselective sulfoxidation. Stereochemical formation and total sulfoxide formation did not mirror acute toxicity in the three species exposed in fresh or hypersaline conditions. Mortality of striped bass and rainbow trout due to fenthion exposure was enhanced by hypersaline treatments and a trend towards increased toxicity was observed in tilapia. In liver microsomes of rainbow trout, inhibition of cytochrome P450 (CYP) caused a respective 7- and 3-fold increase in sulfoxide formation in liver microsomes fresh and saltwater fish, and a significant increase in the formation of the (+)R-sulfoxide. CYP inhibition also caused a significant elevation of the (+)R-sulfoxide in freshwater striped bass, but not in hypersaline-treated bass. The results indicated contribution by CYP in the sulfoxidation of fenthion as well as the formation of other metabolites in all three species. In summary, hypersaline conditions impacted fenthion toxicity under conditions that appeared to be independent of fenthion sulfoxide formation indicating a much more complex mechanism of action for compounds with phosphorothioate and thio-ether structural features potentially involving multiple oxidative pathways.     

赤霉素GA4+7种子引发处理对玉米光合作用及产量的影响

研究了外源赤霉素处理玉米种子对其光合特性的影响,可为通过外源激素调控玉米生长和种子加工技术开发提供依据。以玉米种子‘郑单958’为材料,设置10、60、120 mg/L 3个质量浓度的GA4+7[m（GA4）:m（GA7）=40:60]进行浸种后回干的引发处理,以常规不处理的种子为对照,测定了大田试验玉米叶片光合参数、叶绿素荧光参数、叶面积及光合产物积累量及光合色素含量。结果表明:GA4+7种子引发处理可提高玉米叶片的净光合速率、气孔导度、胞间CO2浓度、单株叶面积、干物质积累量以及光合色素含量,同时可降低叶绿素a与叶绿素b比值,有效降低初始荧光（F0）,增大最大荧光（Fm）、PSⅡ的光能转换效率（Fv/Fm）和实际量子效率（F/Fm'）,提高百粒重和籽粒产量,其中以60 mg/L的GA4+7处理（G2）效果最明显。在三叶期、七叶期与拔节期,G2处理玉米的净光合速率分别比对照提高74.3%、42.6%和39.6%（差异显著,P0.05）,单株叶面积分别提高30.9%、48.5%和24.1%（差异显著,P0.05）,干物质积累量分别增加19.6%、46.9%和52.9%（差异显著,P0.05）,总叶绿素含量分别提高21.5%、12.1%和11.1%（差异显著,P0.05）,百粒重和籽粒产量显著高于对照,分别提高6.0%和9.7%（P0.05）。     

加州新小绥螨对朱砂叶螨的控制作用

为明确加州新小绥螨Neoseiulus californicus（McGregor）国内种群对朱砂叶螨Tetranychus cinnabarinus（Boisduval）的控制潜力,应用功能反应、数值反应及实验种群生命表参数评价了该捕食螨对朱砂叶螨的控制能力。加州新小绥螨对朱砂叶螨的功能反应能很好地拟合Holling Ⅱ方程。在25℃,加州新小绥螨雌成螨对朱砂叶螨卵、幼螨、若螨和成螨的功能反应参数a/T_h值分别为42.4195、81.6275、54.3044和17.9399,对朱砂叶螨幼螨、若螨和卵的控制力高于成螨。在19~31℃,加州新小绥螨对朱砂叶螨雌成螨日均捕食量和对猎物的控制能力a/T_h随温度升高而增大,在31℃时达最大值,分别为10.80头和29.5364。在28℃时,加州新小绥螨的净增殖率和内禀增长率分别为26.1522和0.2213。表明加州新小绥螨国内种群表现出重要的生物防治潜能。     

N-(7-氟-3-氧-3,4-二氢-苯并噁嗪-6-基-)乙酰胺类化合物的合成及除草活性

为了寻找高效、安全的具有除草活性的新化合物,利用2-取代乙酰氯和2H苯并噁嗪-3-酮反应合成了9个N-(7-氟-3-氧-3,4-二氢苯并噁嗪-6-基-)乙酰胺类化合物,其结构经元素分析、IR、1H NMR确证。初步除草活性测试表明:在有效剂量75 g/hm2下,化合物 5d 芽后茎叶处理对刺苋Amaranthus spinosus等4种杂草显示出90%以上的抑制率。     

Fate of prothiofos (O-2,4-dichlorophenyl O-ethyl S-propyl phosphorodithioate) in rats

The fate of prothiofos (O-2,4-dichlorophenyl O-ethyl S-propyl phosphorodithioate) were studied in male rats 1, 3, 8, 24, 48, and 120 hr after oral administration. In the determination of prothiofos by gas chromatography-mass spectrometry, pentadeuteroethoxy-labeled prothiofos was used as the internal standard and the carrier of residual prothiofos. Prothiofos was rapidly absorbed from the small intestine and had substantially disappeared from the gastrointestinal tract within 24 hr after dosing. The residual concentrations of prothiofos in all organs analyzed, reached a maximum at 3 hr after dosing, and then diminished exponentially. The major urinary metabolites were 2,4-dichlorophenol (21% of administered prothiofos), its conjugated substances (26%), O-2,4-dichlorophenyl O-ethyl hydrogen phosphorothioate (14%), and O-2,4-dichlorophenyl O-ethyl hydrogen phosphate (25%). While prothiofos was found in the feces (3.8%), prothiofos oxygen analog (prothiofos-oxon) was scarcely detected in any excreta. Results obtained with a single dosing of prothiofos-oxon indicated that the oxygen analog formed from prothiofos in vivo was rapidly degraded through cleavage of the PS bond and the liberation of 2,4-dichlorophenol. The low mammalian toxicity of prothiofos is probably due to depropylthiolation in the molecule.     

2-(2-氨基噻唑-4-基)-(Z)-甲氧亚氨基乙酸酯的酰胺及亚胺衍生物的合成及抑菌活性

以乙酰乙酸甲(乙)酯为原料,合成了2-(2-氨基噻唑-4-基)-(Z)-甲氧亚氨基乙酸酯的酰胺和亚胺两类共13个衍生物,其中10个化合物未见文献报道,所有化合物的结构均经核磁共振氢谱(1H NMR)、红外光谱(IR)和电喷雾电离质谱(ESI-MS)确证。初步杀菌活性测试结果表明,所有化合物在质量浓度200 mg/L下对6种供试植物病原菌均有不同程度的抑制作用,其中化合物 mk-1 在200 mg/L下对小麦赤霉病菌Fusarium graminearum的抑制率达81.4%。     

The neurotoxicity of O-(2,5-dichlorophenyl) O-methyl phenylphosphonothionate,an impurity and photoproduct of leptophos (phosvel) insecticide

The neurotoxic effects of leptophos and three degradation products of leptophos have been evaluated in white leghorn pullets. The data derived demonstrate that desbromo leptophos and leptophos oxon are approximately three and two times, respectively, more effective neurotoxic agents than leptophos in the white leghorn pullet.     

Metabolism of 1,1-bis-(p-ethoxyphenyl)-2-nitropropane in the house fly and the cluster caterpillar

Some aspects of the metabolism of a new insecticide, 1,1-bis-(p-ethoxyphenyl)-2-nitropropane have been investigated in the house fly, Musca domestica and the cluster caterpillar, Spodoptera litura. In the house fly the compound was deethylated and after 24 hr exposure, 1-(p-ethoxyphenyl)-1-(p-hydroxyphenyl)-2-nitropropane and 1,1-bis-(p-hydroxyphenyl)-2-nitropropane were isolated. From evidence given below it is probable that conjugates of these compounds were also present. Feeding of the insecticide to S. litura resulted in the excretion of mainly unchanged insecticide although a small percentage was converted to a polar compound tentatively identified as 1,1-bis-(p-hydroxyphenyl)-2-propanone.     

Prevention of progeny formation in Drosophila melanogaster by 1-arylimidazole-2(3H)-thiones

Effects of 1-arylimidazole-2(3H)-thiones (AITs) and 1-(substituted benzyl)imidazole-2(3H)-thiones (BITs) were tested on progeny formation in Drosophila melanogaster. Some AITs showed inhibitory activities at laying eggs and delayed eclosion by 1 day. The inhibitory activity was nullified by adding octopamine (OA) or noradrenaline (NA) to the medium for progeny formation in D. melanogaster. The effect of AIT on the contents of OA and NA was analyzed in adults of D. melanogaster by high-performance liquid chromatography with electrochemical detection. Flies fed with AIT decreased OA and NA levels and increased TA content. Taken together, the inhibitory activity of AIT could be due to inhibition of tyramine β-hydroxylase and dopamine β-hydroxylase.     

美国白蛾性信息素(9Z,12Z)-十八碳二烯醛及(9Z,12Z,15Z)-十八碳三烯醛的合成

采用仿生合成法制备了美国白蛾Hyphantria cunea性信息素的两个主要成分,(9Z,12Z)-十八碳二烯醛和(9Z,12Z,15Z)-十八碳三烯醛。其结构均经IR、1H NMR、GC-MS波谱分析确证。     

Biotransformation of clomazone in rice (Oryza sativa) and early watergrass (Echinochloa oryzoides)

Rice (Oryza sativa), a relatively tolerant species, and early watergrass (Echinochloa oryzoides; EWG), a relatively susceptible species, were exposed to ¹⁴C-labeled clomazone to determine accumulation, biotransformation, and mass balance. On a total mass basis, rice absorbed more clomazone than EWG (p < 0.05), but on a nmol/g basis, there was no significant difference between the two species (p > 0.05). Rice contained more extractable ¹⁴C residues (7.7 ± 0.5 vs. 4.8 ± 0.5 nmol in rice vs. EWG, respectively; p < 0.5), but the concentration in EWG was significantly higher (4.2 ± 0.5 vs. 1.8 ± 0.1 nmol/g in EWG vs. rice, respectively; p < 0.01). More metabolized residue was measured in EWG compared to rice (84.1% vs. 67.9%; p < 0.01). Both species produced hydroxylated forms, β-d-glucoside conjugates, and several other unidentified polar metabolites, but EWG generally produced higher metabolite concentrations. The concentration of the suspected active metabolite, 5-ketoclomazone, was significantly higher in EWG vs. rice (21 ± 2 vs. 5.7 ± 0.5 pmol/g, respectively; p < 0.01). Differences in sensitivity to clomazone between rice and EWG appear to be due to differential metabolism, but in this case the more susceptible EWG qualitatively and quantitatively metabolized more clomazone than the more tolerant rice. This is consistent with the action of a metabolically activated herbicide. This metabolic difference could be exploited to develop herbicide safeners for use with clomazone.     

新型含哒嗪酮环酰肼类化合物的合成和生物活性研究

哒嗪酮杂环是具有良好生物活性的重要结构片段,在前期研究基础之上,在3(2H)-哒嗪酮的5位上引入酰肼活性基团,设计合成了13个未见文献报道的含哒嗪酮环酰肼类化合物,所有化合物结构均通过1H NMR、IR、元素分析确证。初步生物活性测试结果表明,部分化合物对蚜虫Aphis fabae具有一定的杀虫活性,其中 7d 在500 mg/L普筛浓度时,蚜虫死亡率达73.9%,但对粘虫Mythimna separata和红蜘蛛Tetranchus urticae的生物活性不明显。 关键词; 哒嗪酮;酰肼;合成;生物活性     

紫草色素对番茄叶霉病菌的室内抑菌活性研究

室内研究了新疆紫草色素对番茄叶霉病菌Fulvia fulva (Cooke) Cifferri的生物活性。新疆紫草色素用石油醚提取,分别用平板表面萌发法和菌落生长速率法测定其对番茄叶霉病菌孢子萌发、孢子芽管长度及菌丝生长的影响。并在离体条件下测定了其对番茄叶霉病的防治效果。结果表明,新疆紫草色素对番茄叶霉病菌抑制作用明显,其中抑制孢子萌发EC50为17.4 μg/mL,抑制孢子萌发芽管长度的EC50为1.0 μg/mL,抑制菌丝生长的EC50为200.4 μg/mL;浓度为800 μg/mL时对番茄叶霉病的离体防治效果达到90.5％。