Structure—activity relationships in pyrethroid esters derived from substituted 2-phenoxy-3-methylbutanoic acids

Non-cyclopropane pyrethroid esters of different substituted 2-phenoxy-3-methylbutanoic acids have been synthesised using the three alcohols—3-phenoxybenzyl alcohol, α-cyano-3-phenoxybenzyl alcohol and 3, 4-methylene-dioxybenzyl alcohol. Among the 35 esters synthesised and tested against Culex quinquefasciatus Say, the Bancroftian filariasis vector, for both larvicidal and adulticidal activities, α-cyano-3-phenoxybenzyl 2-(4-fluorophenoxy)-3-methylbu-tanoate, with an LC₅₀ value of 2.5 × 10^?3 mg litre^?1 for larvicidal activity, and α-cyano-3-phenoxybenzyl-2-(4-chlorophenoxy)-3-methylbutanoate, with an LD₅₀ value of 30 times; 10^?4 ug insect^?1 for adulticidal activity, were found to be as effective as fenvalerate, a well-known non-cyclopropane pyrethroid ester. Structure-activity studies showed that the insecticidal activity is dependent on the nature and position of the substituent in the phenyl ring of the acid moiety and also on the type of alcohol moiety.     

PRO_PLANT—a computer—based decision-support system for cereal disease control1

The task of the knowledge-based advisory system PRO_PLANT is to help farmers reduce to a minimum the input of fungicides, and in later stages all pesticides, while giving as good economic returns as high-input routine sprays with their potential environmental hazards (e.g. ground and surface water contamination). The system was first developed for cereal diseases and is now (till 1994) being extended to the most important pesticide applications on field crops (cereals, maize, rape, potato, sugarbeet). It can be used by consultants or farmers as a stand-alone version. PRO_PLANT at present consists mainly of disease-specific knowledge bases for diagnosis of fungus infections in cereals and rules for optimized fungicide treatments. The scientific basis has been derived from expert knowledge and field trials over several years, and the knowledge representation is rule-based. During a consultation, information on the field, cultivar resistance, seed treatments and fungicides is considered. Necessary weather data comes from the German Weather Service via BTX or from a small home-run weather station. The prototype was first tested in 1991 and an improved version was then tested in 1992 with 40 consultants and 30 farmers. In 1993, the system will be used by the advisory service of Nordrhein-Westfalen and commercially distributed to farmers.     

The activity of amino acids produced by <Emphasis Type="Italic">Paenibacillus macerans</Emphasis> and from commercial sources against the root-knot nematode <Emphasis Type="Italic">Meloidogyne exigua</Emphasis>

The rhizobacterium Paenibacillus macerans was grown in tryptic soy broth and after separating the cells by centrifugation the activity of fractions of the supernatant was tested against Meloidogyne exigua juveniles. From HPLC analyses and spectral data, the most active fractions were found to contain alanine, glutamic acid, glycine, histidine, threonine and valine, which were probably produced by bacterial hydrolysis of proteic nutrients. Amino acids from commercial sources were then assayed to confirm these results and to evaluate their potential for the control of nematodes. LC₅₀ of 26 and 283 μg ml⁻¹ were shown for the nematicide aldicarb and L-cysteine respectively when tested on M. exigua juveniles. At a concentration 38.4 times>LC₅₀, the amino acid diminished the nematode population on coffee plants to values statistically equal to those obtained with aldicarb at a concentration 19.2 times>LC₅₀.     

Synergism—a patent view

Novel combinations of pesticides and herbicides are patentable only if they are not obvious. Proof of a synergistic effect produced by the combination is a widely accepted and important defence against an allegation of obviousness. The paper reviews various mathematical approaches to establishing this proof to the satisfaction of Patent Offices and Patent Courts.     

Herbicide antidotes—A review

The history of herbicide antidotes is reviewed, beginning with the exploration of compounds to protect wheat (Triticum aestivum L.) against barban in the early 1960s, and the later introduction of naphthalic anhydride (NA, naphthalene-1, 8-dicarboxy-licanhydride) as a seed dressing for protecting maize (Zea mays L.) against EPTC. This compound was largely replaced by Stauffer's R-25788 (N, N-diallyl-2, 2-dichloroacetamide) which has continued to be widely used in conjunction with EPTC and butylate in maize. This compound is highly specific to maize and can thus be applied in admixture with the herbicide, but has not proved of practical value on other crop species. NA on the other hand is less specific and is of potential value on sorghum [Sorghum bicolor (L.) Moench] and rice (Oryza sativa L.); experimental work continues on these crops. The only other antidote to be marketed so far is cyometrinil as a seed dressing for protecting sorghum against metolachlor and related herbicides. Other compounds are under development. Mode of action and structure-activity relations are discussed, as well as the current and future potential for antidotes in respect of the control of weed species in closely related crops, the increased options for herbicide use in minor crops and the possibility of reduced costs for broad spectrum weed control in major crops.     

Praziquantel—a new cestocidea

Praziquantel is a new chemotherapeutic agent with high activity against juvenile and adult cestodes. The juvenile cestodes tested include Hymenolepis nana, Cysticercus fasciolaris, C. pisiformis, C. tenuicollis, C. bovis. The fully effective doses range from 25–100 mg/kg host. All adult tapeworms tested (Taenia pisiformis, T. hydatigena, T. ovis, T. taenaiformis, Dipylidium caninum, Mesocestoides corti, Echinococcus multilocularis, E, granulosus) of dogs and cats and several Moniezia species of sheep were killed by doses up to 5 mg/kg host. Praziquantel is effective in vitro at very low concentrations. First studies on the mechanism of action in H. diminuta have shown that praziquantel acts on the carbohydrate metabolism of the parasite.     

土壤强还原过程产生的有机酸对土传病原菌的抑制作用

土壤强还原(reductive soil disinfestation,RSD)能有效杀灭土传病原菌,并已在日本、荷兰和美国取得一系列的推广应用,但对于RSD的杀菌机理不甚明了。本试验采用高效液相色谱和荧光定量PCR等技术研究了以玉米秸秆为有机碳源的RSD处理过程中土壤产生的有机酸种类,以及不同浓度的有机酸对土壤病原菌的抑制效果。结果表明:以玉米秸秆为有机碳源的RSD过程中主要产生了乙酸和丁酸;经50mmol/L丁酸溶液处理的土壤中立枯丝核菌、辣椒疫霉、尖孢镰刀菌及茄劳尔氏菌的数量分别为对照的3.5%、38.9%、11.5%和7.9%;10mmol/L的丁酸可以完全抑制尖孢镰刀菌菌丝的生长;5mmol/L的丁酸即可完全抑制尖孢镰刀菌的孢子萌发。本研究结合前人报道表明有机酸,尤其是乙酸和丁酸,对于RSD的杀菌机理起着重要的作用。     

Intercropping in field vegetable crops: Pest management by agrosystem diversification—an overview

Intercropping field vegetables with other species such as clovers shows insect pest suppression which may make chemical control unnecessary. Examples are given to illustrate these effects and the underlying mechanisms are discussed. Intercropping fits into environmentally acceptable and sustainable vegetable-producing practices. Both economic and ecological conditions must be fulfilled before intercropping-based commercial production methods can be developed.     

Polarography of herbicides—A preliminary survey

The polarographic behaviour of 38 herbicides was studied in 5 supporting electrolytes using single sweep derivative polarography. The 16 compounds showing the greatest polarographic activity were investigated further in order to estimate their detection limits. It is suggested that polarography might provide a useful technique for the analysis of 12 of these materials.     

Phloem translocation of strong acids—glyphosate,substituted phosphonic and sulfonic acids—in Ricinus communis L

The mobility in phloem of several substituted phosphonic acids and a sulfonic acid was studied in the castor bean plant, Ricinus communis L. For a series of¹⁴C-labelled phosphonate mono-esters applied to the petioles of mature leaves, phloem transport was modest, becoming poor over longer distances in the plant. Substituted phenylphosphonic acids were more efficiently moved in phloem; uptake from the petiole and subsequent redistribution were slow, but these dibasic compounds were very stable in plants and substantial amounts reached the roots after 72 to 120 h. Glyphosate was very efficiently transported to phloem sinks even within 24 h, with high concentrations in phloem sap. Toluene-4-sulfonic acid moved predominantly in the xylem to the mature leaves and its phloem transport was poor. Transport patterns are considered in relation to the physico-chemical properties of the compounds. Ion trapping appears to play little part in the phloem transport of these strong acids, though the good accumulation and transport in phloem of the complex molecule glyphosate cannot at present be explained.     

Suppression of <Emphasis Type="Italic">Sclerotinia sclerotiorum</Emphasis> by antifungal substances produced by the mycoparasite <Emphasis Type="Italic">Coniothyrium minitans</Emphasis>

A study was conducted to investigate production of antifungal substances (AFS) by Coniothyrium minitans (Cm), a mycoparasite of Sclerotinia sclerotiorum (Ss), in modified Czapek-Dox (MCD) broth and potato dextrose broth (PDB), and effects of AFS of Cm on mycelial growth and germination of sclerotia and ascospores of Ss and incidence of leaf blight of oilseed rape caused by Ss. Results showed that mycelial growth of Ss was reduced by 41.6 and 84.5% on 3 day-old cultures grown on potato dextrose agar (PDA) amended with 10% (v v⁻¹) of cultural filtrates of Cm grown in MCD (MCD_cm) after incubation for 6 and 15 days, respectively, and by 2.7 and 15.7% on PDA amended with 10% (v v⁻¹) of cultural filtrates of Cm grown in PDB for 6 and 15 days, respectively. In addition to retardation of mycelial growth, morphological abnormality of Ss such as hyphal swellings and cytoplasm granulation were also observed in colonies grown on PDA amended with cultural filtrates of MCD_cm. Sclerotia of Ss soaked in the filtrates of MCD_cm for 24 h remained viable, but their ability to undergo myceliogenic germination on PDA was delayed, compared to sclerotia treated with MCD. Germination of ascospores of Ss was unaffected on PDA amended with 10% of the filtrates of MCD_cm. However, germ tubes of Ss were shortened and deformed by the formation of hyphal swellings in the treatment of MCD_cm. Treatment of leaves of oilseed rape with cultural filtrates of MCD_cm reduced incidence of leaf blight caused by Ss, compared to the controls (water or MCD). This study suggests that AFS produced by Cm plays an important role in the suppression of mycelial growth and germ-tube development of ascospores of Ss and that there is potential for using AFS of Cm to control leaf blight of oilseed rape caused by ascospores of Ss.     

Treatments of soil—nematological aspects1

Treatments of soil to control plant parasitic nematodes constitute a complex problem because product losses, costs of treatments, efficiency of control and increases of yield are subject to multiple variables. To evaluate the situation, the whole system should be as carefully as possible analysed: nematode species must be identified and population densities determined; economical thresholds and the pedoclimatic conditions which affect distribution and persistence of nematicides should be investigated; rate of mortality that nematicides will induce at different doses and their side-effects on plants and environment need to be known. Although a great amount of information is available, this is often rather scattered, so much work is yet to be done. Integrated control is at present the only economical answer.     

Acetyl-CoA Carboxylase—a Graminicide Target Site

Acetyl-CoA carboxylase catalyses the first committed step in fatty acid (and acyl lipid) formation. The enzyme has been shown to exert a high degree of flux control for lipid biosynthesis in leaves and, therefore, it is not surprising that chemicals which can inhibit it effectively are successful herbicides. These chemicals belong mainly to the cyclohexanedione and aryloxyphenoxypropionate classes and are graminicides. The reason for the selectivity of these herbicides towards grasses lies in the nature of the target site, acetyl-CoA carboxylase. Recent advances in our knowledge of acetyl-CoA carboxylases from sensitive and resistant plants has revealed some important facts. Dicotyledons, which are resistant, have a multi-enzyme complex type of carboxylase in their chloroplasts while grasses have a multifunctional protein. Both divisions of plants have two isoforms of the enzyme, the second being in the cytosol. Detailed study of multifunctional forms of acetyl-CoA carboxylases, which have different sensitivities to herbicides, suggests that herbicide resistance is correlated with cooperativity of herbicide binding to the native dimeric form of the carboxylase. © 1997 SCI.     

Combating plant diseases—the Darwin connection

Although Darwin knew of plant diseases, he did not study them as part of his analysis of natural selection. Effective plant disease control has only been developed after his death. This article explores the relevance of Darwin's ideas to three problem areas with respect to diseases caused by fungi: emergence of new diseases, loss of disease resistance bred into plants and development of fungicide resistance. Darwin's concept of change through natural or artificial selection relied on selection of many small changes, but subsequent genetic research has shown that change can also occur through large steps. Appearance of new diseases can involve gene duplication, transfer or recombination, but all evidence points to both host plant resistance and fungicide susceptibility being overcome through point mutations. Because the population size of diseases such as rusts and powdery and downy mildews is so large, all possible point mutations are likely to occur daily, even during moderate epidemics. Overcoming control measures therefore reflects the overall fitness of these mutants, and much resource effort is being directed towards assessment of their fitness, both in the presence and in the absence of selection. While recent developments in comparative genomics have caused some revision of Darwin's ideas, experience in managing plant disease control measures clearly demonstrates the relevance of concepts he introduced 150 years ago. It also reveals the remarkable speed and the practical impact of adaptation in wild microorganism populations to changes in their environment, and the difficulty of stopping or delaying such adaptation. Copyright © 2009 Society of Chemical Industry     

莲子草假隔链格菌粗毒素生物活性研究

利用种子生测法,研究了莲子草假隔链格菌（Nimbya altermantherae）粗毒素对农田12种杂草的生物活性及6种作物的安全性。结果表明,该粗毒素对12种田间常见杂草种子萌发及根长、芽长均有抑制作用,且随粗毒素溶液浓度的提高抑制作用相应增强。在浓度为50μg／ml时,粗毒素对光头稗（Echinochloa colonum）、荠菜（Capsella bursa—pastoris）、升马唐（Digitaria ciliaris）的萌发表现出一定的抑制作用,在粗毒素浓度为400μg／ml时,对荠菜,千金子（Leptochloa chinensis）的萌发具有强烈的抑制作用,萌发率为0。在粗毒素浓度为50μg／ml时,对鳢肠（Eclipta prostrata）、光头稗Echinochloa colorbuln）、升马唐（Digitaria ciliaris）、蔺草（Beckmannia syzigachne）、看麦娘（Alopecurus aequalis）等杂草的根长、芽长也表现出一定的抑制作用。粗毒素对不同作物萌发的影响也有差异,对花生（Arachis hypogaea）、大豆（Glycine max）的萌发及根长的生长无抑制作用,其中对花生的根长还有一定的促进作用。粗毒素浓度小于或等于400μg／ml时,对油菜（Brassia campestris）的萌发及根长、芽长的生长无抑制作用。粗毒素对小麦（Triticum aestivum）不安全。     

Biopesticides — harmonization of registration requirements within EU Directive 91/414 — an industry view1

A range of biopesticides (including, as active substances, bacteria, viruses, fungi, nematodes, protozoa and beneficial insects) is now commercially available for control of insect pests, fungal and bacterial diseases and weeds. The term biopesticide can include pheromones, insect and plant growth regulators, plant extracts, transgenic plants and macroorganisms as well as microorganisms. However, world biopesticide sales in 1990 were estimated to be 120 million USD, representing less than 0.5% of the world's agrochemical market. Out of this, approximately 90% of the biopesticide sales are represented by the bacterium Bacillus thuringiensis for the control of insect pests. Nevertheless, biopesticide sales are estimated to be increasing at 10–25% per annum and sales by the year 2000 are estimated to reach 1000 million USD. This paper looks at the current commercial status and the constraints that are facing industry concerning changing registration, particularly in Europe, the absence of harmonized data requirements, and the increasing costs and delays in registrations that deter the development of new biopesticides.