Naturally occurring cyanohydrins,analogues and derivatives as potential insecticides

Several naturally occurring cyanohydrins were tested for fumigation toxicity to two insect species, the house fly (Musca domestica L) and the lesser grain borer (Rhyzopertha dominica (F)). Synthetic analogues of these compounds were tested as well. Most of the cyanohydrins tested were more toxic as fumigants to M domestica and R dominica than chloropicrin; some compounds were nearly as toxic as dichlorvos. Naturally occurring cyanohydrins were among the most toxic tested. © 2000 Society of Chemical Industry     

Glucosinolate aglucones and analogues: insecticidal properties and a QSAR

Naturally occurring aglucones of three glucosinolates (sinigrin, glucotropaeolin, and epi-progoitrin) were tested for fumigation activity against the house fly, Musca domestica, and the lesser grain borer, Rhizopertha dominica. A total of eight natural aglucones were evaluated in the bioassays. Two aglucones of sinigrin showed efficacy against both species which was comparable with that of a commercial fumigant, chloropicrin. None of the aglucones tested was comparable in activity to dichlorvos. Aglucones of glucotropaeolin were also insecticidal, but not to the same level as the sinigrin aglucones. The aglucones of epi-progoitrin were only slightly effective as fumigants. A quantitative structure–activity relationship (QSAR) was developed for synthetic analogues of the sinigrin and glucotropaeolin aglucones. An electronic parameter, σ*, provided the best predictor of activity in R. dominica, whereas a hydrophobicity parameter, π, best predicted activity in M. domestica. © 1998 Society of Chemical Industry     

Insecticidal properties of monoterpenoid derivatives to the house fly (diptera: Muscidae) and red flour beetle (coleoptera: Tenebrionidae)

Monoterpenoid derivatives were synthesized and their insecticidal activities were evaluated against red flour beetles, Tribolium castaneum (Herbst), in fumigant bioassays and against house flies Musca domestica (L.) in topical, fumigant, and ovicidal bioassays. Acetate derivatives and haloacetate derivatives were compared with each other, and with the parent monoterpenoid to determine structure-activity relationships. Acetate derivatives were more active than the propionate derivatives of cyclic monoterpenoids in the topical, fumigant, and ovicidal bioassays. Pivalates were topically more insecticidal than acetates to adult house flies, while the acetates had the greater ovicidal activity. Acetates and pivalates were more effective than haloacetates in the topical, red flour beetle fumigation and ovicidal bioassays. Fluoroacetates of cyclic monoterpenoids were the most effective house fly fumigants, followed by acetates, and trichloroacetates. Several derivatives were produced that displayed enhanced activity relative to the parent alcohols or phenols.     

Fumigant combinations for Cyperus esculentum L control

The phase-out of methyl bromide as a soil fumigant has stimulated research into the use of other soil fumigants for weed control. Methyl bromide, methyl iodide, propargyl bromide, 1,3-dichloropropene (1,3-D) and metam-sodium were tested alone and in combination with chloropicrin in laboratory experiments to determine their efficacy against Cyperus esculentus L (yellow nutsedge) tubers. Propargyl bromide and metam-sodium were the most efficacious fumigants tested, with EC50 values of 3.7 and 6.5 microM, respectively. The relative potencies of methyl iodide and chloropicrin were not significantly different but were 2.6 and 2.9 times more potent than methyl bromide, respectively. The EC50 values for all fumigants other than 1,3-D were significantly lower than that of methyl bromide. Combining each fumigant with 17% chloropicrin resulted in a synergistic interaction. The greatest increase in potency between the expected result and the actual result was a relative potency of 3.8 with the methyl bromide/chloropicrin combination. The smallest increase in efficacy was with propargyl bromide and chloropicrin, with a relative potency of 1.5. There was no significant difference between the EC50 values of methyl bromide/chloropicrin and methyl iodide/chloropicrin combinations. Combining 1,3-D with 17% chloropicrin resulted in an EC50 value for C. esculentus control similar to that of methyl iodide applied alone.     

Dose response of weeds to methyl iodide and methyl bromide

Labonuory bioassay and field experiments were conducted to characterize the dose response of weeds to methyl iodide and methyl bromide as soil fumigants. The patterns in potency of both fumigants and in sensitivity of diffcretit weed species to the fumigants were distinguished with the use of logistic dose-response models. Similar to its response to methyl hromide fumigation. Amaranthus retrofleus L. was the most sensitive to methyl iodide fumigation. Cyperus rotundtis L. was the least sensitive to methyl iodide fumigation, whereas Portuloca oleracea L. was the least sensitive to methyl hromide. Lolium multiflorum Lam. Abutilon theophrasti Medik. Chenopodium album L. P. ateracea . Brassica kaber (D.C.) L.C. Wheeler and Cyperus escuden-tus L. were similar in sensitivity to methyl iodide. Methyl iodide was as potent as methyl bromide for A. retroflexus but more potent than methyl bromide for L. multiflorum , A. theophrasti. C. album. P. oleracea. B. kaber, C. esculentus and C. rotundus. The dose response for weeds in the field was similar to that obtained in laboratory bioassays. Under fieid conditions. 280 kg ha^-1 methyl iodide killed all species tested except Solanum nigrum L Methyl iodide appears to be a suitable replacement for meihyl bromide because it can be used in situations simitar to methyl bromide fumigation, has superior efficacy against a broad spectrum of pests and has a low potential for degrading the earth's ozone lavers.     

氯化苦熏蒸对土壤反硝化作用及nirS型反硝化细菌群落结构的影响

探究氯化苦熏蒸对土壤反硝化作用的影响及机制。采用理化分析和DGGE方法分析了氯化苦熏蒸后土壤反硝化及nirS型反硝化细菌群落结构。不同浓度氯化苦熏蒸对土壤nirS型反硝化细菌群落均匀度无影响,而对nirS型反硝化细菌多样性和丰富度指数的影响为高浓度中浓度低浓度对照。对土壤反硝化作用的影响表现为,经500 mg/kg氯化苦熏蒸的土壤在培养初期(0 d)反硝化率比对照降低10.55%,土壤反硝化作用被显著抑制。2周后3种浓度氯化苦均抑制土壤反硝化作用, 4周后土壤的反硝化作用缓慢恢复。500 mg/kg浓度氯化苦对土壤反硝化强度的影响与nirS型反硝化细菌群落结构变化不同,说明土壤反硝化作用的强弱并非完全决定于土壤nirS型反硝化细菌。     

四种熏蒸剂对辣椒疫霉和南方根结线虫的毒力

为明确不同熏蒸剂对土传病原菌辣椒疫霉Phytophthora capsici和南方根结线虫Meloidogyne incognita的毒力,采用密闭熏蒸法测定了4种土壤熏蒸剂氯化苦、棉隆、威百亩、1,3-二氯丙烯的毒力及1,3-二氯丙烯和氯化苦复配的联合毒力。结果表明:氯化苦、棉隆、威百亩、1,3-二氯丙烯对辣椒疫霉的EC₅₀分别为0.12、2.44、8.30、8.45 mg/L; 对南方根结线虫的EC₅₀ 分别为1.23、0.22、0.30、0.18 mg/L。1,3-二氯丙烯和氯化苦以2:1、1:1、1:2比例复配时对辣椒疫霉的EC₅₀ 分别为1.13、0.24、0.14 mg/L;对南方根结线虫的EC₅₀分别为0.19、0.32、0.61 mg/L。结合经济效益和多种病害兼治的原则,推荐使用1,3-二氯丙烯与氯化苦1:1配比,可兼治辣椒疫病和根结线虫病。     

气相色谱法测定蔬菜水果中的氯化苦残留

氯化苦土壤熏蒸是防治土传病害的有效措施。采用石油醚对蔬菜、水果样品进行超声波提取,以气相色谱电子捕获检测器测定氯化苦残留。结果表明,在浓度为0.008 ~2 mg/L范围内,线性相关系数r=0.999 4。氯化苦的添加浓度在0.02 ~1 mg/kg范围内,平均回收率为92.2% ~111%,相对标准偏差(RSD)为1.9% ~7.2%,均在农药残留测定允许范围内。该方法的最小检出量(LOD)为0.008 mg/kg,最低检测浓度(LOQ)为0.02 mg/kg。采用本方法对土壤熏蒸处理施用氯化苦后(PHI≥50 d)的甜瓜、草莓、大姜、茄子、菠菜收获期样品进行测定,均未检出氯化苦残留。     

Extraction of allyl isothiocyanate from horseradish (Armoracia rusticana) and its fumigant insecticidal activity on four stored‐product pests of paddy

BACKGROUND: Isothiocyanates (ITCs) extracted from Armoracia rusticana Gaertn., May & Scherb. have been shown previously to have insecticidal activity. Allyl isothiocyanate (AITC), a major component of ITCs with high volatility, was therefore extracted using different methods and tested as a fumigant against four major pest species of stored products, maize weevil Sitophilus zeamais (Motsch.), lesser grain borer Rhizopertha dominica (F.), Tribolium ferrugineum (F.) and book louse Liposcelis entomophila (Enderlein). RESULTS: Whereas there was no significant difference between hydrodistillation and supercritical carbon dioxide fluid extraction in extraction rate for AITC from A. rusticana, both methods resulted in higher extraction efficiency than water extraction. AITC fumigation showed strong toxicity to the four species of stored‐product pests. Adult mortality of 100% of all four pest species, recorded after 72 h exposure to AITC fumes at an atmospheric concentration of 3 µg mL^?1, showed no significant difference from that of insects exposed to phosphine at 5 µg mL^?1, the recommended dose for phosphine. CONCLUSIONS: The results suggest good insecticidal efficacy of AITC against the four stored‐product pests, with non‐gaseous residuals on stored products. AITC obtained from A. rusticana may be an alternative to phosphine and methyl bromide against the four pest species. Copyright © 2009 Society of Chemical Industry     

Fumigant activity of plant essential oils and components from horseradish (Armoracia rusticana), anise (Pimpinella anisum) and garlic (Allium sativum) oils against Lycoriella ingenua (Diptera: Sciaridae)

Plant essential oils from 40 plant species were tested for their insecticidal activities against larvae of Lycoriella ingénue (Dufour) using a fumigation bioassay. Good insecticidal activity against larvae of L. ingenua was achieved with essential oils of Chenopodium ambrosioides L., Eucalyptus globulus Labill, Eucalyptus smithii RT Baker, horseradish, anise and garlic at 10 and 5 microL L(-1) air. Horseradish, anise and garlic oils showed the most potent insecticidal activities among the plant essential oils. At 1.25 microL L(-1), horseradish, anise and garlic oils caused 100, 93.3 and 13.3% mortality, but at 0.625 microL L(-1) air this decreased to 3.3, 0 and 0% respectively. Analysis by gas chromatography-mass spectrometry led to the identification of one major compound from horseradish, and three each from anise and garlic oils. These seven compounds and m-anisaldehyde and o-anisaldehyde, two positional isomers of p-anisaldehyde, were tested individually for their insecticidal activities against larvae of L. ingenua. Allyl isothiocyanate was the most toxic, followed by trans-anethole, diallyl disulfide and p-anisaldehyde with LC(50) values of 0.15, 0.20, 0.87 and 1.47 microL L(-1) respectively.     

Efficacy of methyl iodide and synergy with chloropicrin for control of fungi

Efficacy of soil fumigation with methyl bromide and methyl iodide against Botrytis cinerea, Colletotrichum gloeosporioides, Fusarium oxysporum, Gliocladium virens, Phytophthora citricola, Phytophthora citrophthora, Pythium ultimum, Rhizoctonia solani and Verticillium dahliae was determined in laboratory experiments in closed fumigation chambers. Pythium ultimum was the most sensitive fungal species with EC₅₀ values for methyl bromide and methyl iodide of 15.5 and 8.6 µM , respectively. R solani was the least sensitive with EC₅₀ values of 253.4 and 161.4 µM for methyl bromide and methyl iodide, respectively. Relative potency ([methyl bromide]/[methyl iodide]) values ranged from 5.2 for P citricola to 1.5 for F oxysporum. Methyl iodide was 2.7 more efficacious than methyl bromide averaged over all fungal species. Methyl bromide/chloropicrin and methyl iodide/chloropicrin applied jointly were 2.2 and 2.8 times more efficacious, respectively, against F oxysporum than when the compounds were applied singly. Combining methyl bromide and methyl iodide with chloropicrin resulted in a significant synergistic increase in activity against F oxysporum. © 2000 Society of Chemical Industry     

Management of five stored-product insects in wheat with pirimiphos-methyl and pirimiphos-methyl plus synergized pyrethrins

Hard red winter wheat was treated with pirimiphos-methyl at 4, 6 and 8 mg kg(-1), synergized pyrethrins at 0.38, 0.75, 1.13 and 1.5 mg kg(-1), and combinations of the two insecticides, to conduct laboratory bioassays against four beetle pests of stored grain, red flour beetle Tribolium castaneum (Herbst), rusty grain beetle Cryptolestes ferrugineus (Stephens), lesser grain borer Rhyzopertha dominica (F), and rice weevil Sitophilus oryzae (L), and one moth pest, Indianmeal moth Plodia interpunctella (Hubner). Beetle adults and P interpunctella larvae survived well on control wheat, producing a large number of progeny (65-1037 insects per container). Kernel damage in control wheat among the insect species ranged from 9 to 99%. On pirimiphos-methyl-treated wheat, mortality of R dominica adults was > or =72%, but that of the other beetle species and P interpunctella larvae was 100%. Progeny were not produced on pirimiphos-methyl-treated wheat, and the kernel damage was negligible (< or =1%). Synergized pyrethrins were ineffective against the five insect pests. Pirimiphos-methyl combined with synergized pyrethrins was not superior to pirimiphos-methyl alone against the five insect pests. Pirimiphos-methyl is not registered in the USA for use on wheat, but our results suggest that it could be a viable grain protectant at rates of 4-8 mg kg(-1).     

Long-term effectiveness of grain protectants and structural treatments against Liposcelis decolor (Pearman) (Psocoptera: Liposcelididae), a pest of stored products

Numerous strains of the psocid pest, Liposcelis decolor (Pearman) were collected from farms and central storages and interbred to form three representative strains from three major grain-growing states of Australia: Queensland, South Australia and New South Wales. These were tested against the grain protectants and structural treatments currently registered for use in Australia. Recently, L decolor has become an important pest of stored grain in Australia, particularly in the eastern and southern parts. There is no published information available on management of this pest and the current pest-management strategy, based predominantly on phosphine fumigation, has failed to control infestations of this pest in numerous grain storages in Australia. Alternative methods of control such as use of contact insecticides were explored in the present work to supplement phosphine fumigation to manage this new pest. From eight grain protectants tested as admixtures, only chlorpyrifos-methyl, bioresmethrin plus piperonyl butoxide, and fenitrothion were found to provide long term (3-9 months) protection against all three strains of L decolor. Chlorpyrifos-methyl gave the best protection, providing a minimum of 7.5 to a maximum of 9 months protection, depending on the strains tested. Three structural treatments, azamethiphos, azamethiphos plus carbaryl and permethrin provided long-term control (8-9 months) of all three strains of L decolor on galvanised steel surfaces, with permethrin delivering 9 months protection against all strains. However, all of these treatments failed to provide long-term control of any strains on concrete surfaces. We conclude that chlorpyrifos-methyl as a grain admixture can be incorporated into fumigation strategies to optimise the control of L decolor infestations. Structural treatments, such as permethrin can be used to support a fumigation strategy in storages made of galvanised steel.     

棉隆及氯化苦对几种生姜土传病原物的毒力

以侵染生姜的茎腐病菌Pythium myriotylum Drechsler、姜瘟病菌Ralstonia solanacearum和南方根结线虫Meloidagrne incognila为指示病原物,比较了两种土壤处理剂棉隆和氯化苦的熏蒸毒力。采用密闭玻璃容器熏蒸,结合菌丝生长速率法测得棉隆和氯化苦对生姜茎腐病菌的EC50值分别为0.284 和0.096 mg/L,EC90值分别为18.106 和0.312 mg/L。通过密封盘内摇床振荡(25 ℃,45 r/min)培养(24 h),结合菌悬液比色法评价了两药剂对姜瘟病菌的毒力。结果表明:氯化苦的活性较高,EC50和EC90值分别为0.176和1.280 mg/L,而棉隆的毒力较低,其EC50和EC90值分别达1 984和5 701 mg/L。采用线虫悬浮液密闭熏蒸法处理48 h,发现棉隆对南方根结线虫的EC50和EC90值分别为0.175和0.634 mg/L,氯化苦毒力略低于棉隆,其EC50和EC90值分别为1.211和3.772 mg/L。     

Effect of soil physical factors on methyl iodide and methyl bromide

Production and importation of methyl bromide is scheduled to be banned by 2001. Methyl iodide was evaluated as a possible replacement soil fumigant. The effects of soil moisture, temperature, soil texture and fumigation time on the efficacy of methyl iodide for the control of two common weeds, Abutilon theophrasti and Lolium multiflorum, were characterized and compared with those of methyl bromide. The optimal soil moisture for methyl iodide to kill both weed species in sandy soils was 14% water content (w/w). Greater efficacy was obtained when the temperature during fumigation was above 20°C. Compared to methyl bromide, the efficacy of methyl iodide was more consistent in different soils. Time to 100% mortality of weeds was 24 h for methyl iodide fumigation and 36 h for methyl bromide when 200 μM of fumigant was used. On a molar basis methyl iodide was consistently more effective than methyl bromide across the range of environmental factors tested. In terms of application technology and spectrum of activity, methyl bromide can be directly replaced by methyl iodide. © 1998 SCI     

林丹粉剂拌合储粮防治害虫的研究——不同拌合方式的防虫效果及残留量

本試驗是1962年結合生产进行的。結果表明,粮堆中拌合百万分之5的林丹粉剂,以全部拌合防治效果最好;分层或表层拌合的,防治效果较差。无論那种拌合方式都可以有效地防治麦蛾;在原始害虫不多的情况下,对米象、长角谷盜和谷蠹也有良好防治效果,但对防治鋸谷盜和米虱,效果不明显。用百万分之5的林丹粉剂拌合小麦,加工后,林丹的残留量在机制粉中为百万分之1.1—2.5,石磨制粉中为百万分之1.7—3.9,麸皮中为百万分之4.8—10.4。表层拌合的小麦加工成面粉后,为百万分之0.3,麸皮中为百万分之1.2。全部拌合的稻谷加工后,大米及米糠中分別为百万分之0.57—1.0和4.6—12.0,分层拌合的稻谷加工品中則分別为百万分之0.42和2.0。全部拌合的玉米,加工成玉米粉后为百万分之1.9—3.7。上述拌合浓度,对种子发芽率没有影响。     

Subsurface drip application of alternative fumigants to methyl bromide for controlling nematodes in replanted grapevines

BACKGROUND: Many California grape growers use preplant fumigation to ensure uniform and healthy grapevine establishment in replant situations. A field study was conducted to evaluate the performance of subsurface drip‐applied chemical alternatives to methyl bromide on plant‐parasitic nematodes, plant vigor and fruit yield during the 6 year period following replanting. RESULTS: Subsurface drip fumigation with 1,3‐dichloropropene plus chloropicrin and with iodomethane plus chloropicrin had generally similar nematicide activity as methyl bromide in three grape types, while sodium azide was less effective. The combination of 1,3‐dichloropropene plus chloropicrin enhanced vine vigor similarly to methyl bromide. However, all plots treated with alternative fumigants produced less fruit yield than methyl bromide over the 4 years of evaluation. CONCLUSION: Subsurface drip fumigation with alternative chemicals to methyl bromide generally provided adequate management of plant‐parasitic nematodes during the vine establishment period. However, further research is required to increase the performance of alternative chemicals against other components of the replant problem, as grape yield in vines grown in the alternative treatments was lower than in methyl bromide. Copyright © 2011 Society of Chemical Industry     

Permeation of soil fumigants through agricultural plastic films

Plastic films are used in soil fumigation to control fumigant emission into the atmosphere. In previous studies it was shown that the plastic films are permeable to fumigant vapors. Virtually impermeable films (VIF) have been developed to reduce such emission and to increase the efficacy of pest control. A rapid, accurate, sensitive and simple method to measure the permeability of plastic films to soil fumigants that was developed in the present study is described in this paper. The method uses a static, closed system in which the tested film is fixed between two cells. The fumigant is sampled by a solid-phase microextraction method and measured quantitatively by gas chromatography. The method was used to assess the permeability of two plastic films — a low-density polyethylene film (LDPE) and a VIF — to commercial soil fumigants formulated individually or in mixtures. All the tested fumigants permeated through the commonly used LDPE film, in the following descending order of permeability: methyl isothiocyanate (MITC), methyl bromide (MBr), 1,3-dichloropropene (1,3-D; Telone), chloropicrin (CP). The VIF was impermeable to all the tested fumigants except MITC, the permeation of which was reduced by 40%. The permeation of some fumigants through LDPE films was influenced by the formulation used. The permeation of CP was increased when it was combined with MBr in Bromopic. With Telopic, a mixture of 1,3-D and CP, the permeation of 1,3-D through LDPE film was 62% greater than that of Telone, whereas that of CP was not affected. The permeation rates of both MBr and CP were 25–30% greater when they were formulated as a mixture in Bromopic than when they were formulated individually. The formulation of fumigants as mixtures of two components did not affect their permeability through VIF. This study showed that differences in the suitability of plastic films for soil fumigation can be measured easily in a laboratory. It also showed that the VIP was more effective than LDPE in reducing losses of fumigant to the atmosphere, thus allowing more efficient use of fumigants to manage soilborne pests. The presented method helps us to choose the most adequate film for optimizing fumigation efficacy, and reducing costs and environmental risks. http://www.phytoparasitica.org posting Sept. 17, 2006.     

Biological approaches for control of root pathogens of strawberry

ABSTRACT Soil fumigation with methyl bromide plus chloropicrin is used as a preplant treatment to control a broad range of pathogens in high-value annual crop production systems. In California, fumigation is used on approximately 10,125 ha of strawberry production to control pathogens ranging from Verticillium dahliae to root pruning pathogens such as Pythium, Rhizoctonia, or Cylindrocarpon spp. In addition to pathogen control, fumigation also causes an enhanced growth response of the plant and reduces weed pressure. The development of successful, long-term cost effective biocontrol strategies most likely will require the development of an integrated systems approach that incorporates diverse aspects of the crop production system. Although application of single microbial inoculants may provide some level of control for specific production problems, it will be a challenge to provide the broad spectrum of activity needed in production fields.     

Adaptation of soil solarization to the integrated management of soilborne pests of tomato under humid conditions

ABSTRACT Soil solarization was shown to be cost effective, compatible with other pest management tactics, readily integrated into standard production systems, and a valid alternative to preplant fumigation with methyl bromide under the tested conditions. Solarization using clear, photoselective, or gas-impermeable plastic was evaluated in combination with metham sodium, 1,3-dichloropropene + chloropicrin, methyl bromide + chloropicrin, pebulate, or cabbage residue. Strip solarization, applied to 20-cm-high, 0.9-m-wide beds, was conducted to achieve compatibility with standard production practices and resulted in soil temperatures 2 to 4 degrees C above those temperatures resulting when using conventional flatbed solarization. Soil temperatures were 1 to 2 degrees C higher at the edges of the raised beds, eliminating any border effects associated with solarization. Following a 40- to 55-day solarization period, the plastic was painted white and used as a production mulch for a subsequent tomato crop. The incidence of Southern blight and the density of Paratrichodorus minor and Criconemella spp. were lower (P < 0.05) in solarized plots. No differences (P < 0.05) in the incidence of Fusarium wilt and the density of nutsedge and Helicotylenchus spp. were observed between plots receiving solarization and plots fumigated with a mixture of methyl bromide + chloropicrin. The severity of root galling was lower (P < 0.05) when soil solarization was combined with 1,3-dichloropropene + chloropicrin (16.2 + 3.4 g/m(2)) and a gas-impermeable film. The incidence of bacterial wilt was not affected by soil treatments. Marketable yields in plots using various combinations of soil solarization and other tactics were similar (P < 0.05) to yields obtained in plots fumigated with methyl bromide + chloropicrin. The results were validated in several large scale field experiments conducted by commercial growers.