The Biotic Challenge

Pest pressure can vary tremendously from one agroecosystem to another, even where the same crops and pests are present. For example, outbreak conditions of B. tabaci persisted for many years in the lower desert valleys of California, such as the Imperial Valley, but barely rose to the level of occasional pest in the San Joaquin Valley situated 500 km to the northwest. Both regions grow cotton, vegetables and alfalfa, but the San Joaquin Valley accumulates only half the degree-days and many...

Biotic Degradation

Under laboratory aerobic conditions, the degradation of methoxyfenozide is relatively slow.40 In laboratory studies based on US EPA guidelines, 14C-labelled methoxyfenozide was incubated in four US soils kept in the dark at 25 C for 365 days. The DT50 values (dissipation time for 50 loss) obtained were greater than the duration of the study indicating that methoxyfenozide degraded slowly under lab conditions (336 to > 365 days). The decline pattern for the slowest...

Ecological Risk Assessment

Pyrethroids are extremely toxic to many aquatic organisms, and thus could pose a substantial ecological risk (see section 3.10). In this section, we have employed a species sensitivity distribution from the USEPA's Ecotox Database125 for permethrin using 41 aquatic species based on 96 hour LC50s (see Figure 3.4). Species sensitivity distributions are used to calculate the concentrations at which a specified proportion of species will be affected, referred to as the hazardous concentration (HC)...

Mechanism of Viral Infection

Most insect viruses gain access to the insect host by ingestion of contaminated food, as none of them are able to penetrate the insect tissues through the insect cuticle (exoskeleton). Still, there are some other alternative ways of infection, such as the internal or external contamination of the host eggs, and by the contaminated ovipositor of parasites.83 Particularly for baculoviruses, insect hosts ingest the OBs present on the food (leaves, for instance), and once in the insect midgut the...

Classification of Carbamate Insecticides

Carbamates are usually classified according to the substituent on the NH-moiety, and they fall into two major groups N-methyl and N-arylcarbamates, which exhibit insecticidal (both contact and systemic) and herbicidal activities, respectively. A more precise classification of the insecticidal N-methyl carba-mates is indicated below, and some significant examples from a commercial point of view are depicted in Figure 2.6 - Aryl N-methylcarbamate insecticides (e.g. 66, 67) - N,N-dimethylcarbamate...

Cucurbit Crops

Methoxyfenozide was first registered in South Korea in 1998 lepidopteran pests of economic importance in cucurbit crops oxyfenozide is registered in eight countries for cucurbit crop crops which use methoxyfenozide include cucumber, melons, and watermelon, to control pests such as Diaphania hyalinata D. nitidalis (Stoll) and several Spodoptera spp. (see Table 6. to control several Currently, meth-use. Key cucurbit vegetable sponge (L.) pickleworm, 15). Specificity of Table 6.16 Methoxyfenozide...

Confined Rotational Crops

Mustard, radish and wheat crops were planted at 30, 90 and 365 days (nominal) into a sandy loam soil previously treated with either ring-labeled or t-butyl-labeled methoxyfenozide at a rate of 2.2 kg ai (active ingredient) ha-1. Immature and mature crops were sampled. The total radioactive residue levels were < 0.05-0.3mgkg-1 in all crops, except wheat forage and straw, which were 1-3mgkg-1. In general, total radioactive residue levels decreased significantly with increasing plant-back...

Bunyavirus Bunyamwera La Crosse

Bunyaviruses, such as the Bunyamwera, Ilesha and Bwamba species, are found in Sub-Saharan Africa. Syndromes are dengue-like. Reservoir host is unknown vectors Aedes mosquitoes. 2. Bunyavirus of the California group Bunyaviruses of the California group are especially known in North America encephalitis of California. Reservoir hosts rodents, deer vector Aedes. Group C and Guama viruses are distributed in Central and South America. Syndromes are dengue-like. Reservoir hosts rodents vector Culex...

Insecticides Prior to the Chemical

To our knowledge, the first documented compendium of insecticide substances is the Egyptian Ebers Papyrus (ca. 1600 BC).6 Another example of historical reports concerning the control of insect pests can be found in ancient Chinese civilizations, where fire was used to destroy plagues of migratory locust (Locusta migratoria manilensis).7 Pre-Roman civilizations already reported the burning of brimstone (sulfur)6 as an insecticide and purifying agent. Such an application was also described by...

Floriculture Turfgrass Ornamental Plants and Forestry

Spinosad is registered for use on many noncrop plants. A major use is to control thrips species including Frankliniella occidentalis, Scirtothrips dorsalis (yellow tea thrips chilli thrips) and Thrips spp. on floricultural crops grown in greenhouses, plastic tunnels, shadehouses or outdoors. Spinosad is also used to control several species of lepidopterous larvae, Liriomyza spp. and ephydrid flies (shore flies). In turfgrass, spinosad is used primarily to control lepidopterous larvae, including...

Granular Baits

Granular bait formulations of spinosad (Conserve Fire Ant Bait and Justice Fire Ant Bait) have been developed to control Solenopsis invicta (red imported fire ant) and Solenopsis richteri (black imported fire ant). These baits are applied primarily as mound treatments to control fire ants in agricultural, ornamental plant production and residential settings. Spinosad bait formulations have also been developed for control of adult Musca domestica. Elector Bait Granular Fly Control, produced by...

Animal Metabolism

ADME (absorption, distribution, metabolism and elimination) studies in rats indicate spinosad and spinetoram are rapidly absorbed, extensively distributed among tissues and extensively metabolized. Highest spinetoram concentrations were found in the gastrointestinal tract, fat, carcass and liver.130 For spinosad, key tissues were perirenal fat, liver, kidneys and thyroid.103,127 Fecal excretion was the major route of elimination, while urine was a minor route. Rat metabolism studies for...

Mode of Action

The mode of action of the BAH insecticides has been described at the whole insect, tissue, cell and molecular levels.3,5 The BAH insecticides manifest their toxicity by binding to the EcR present in all arthropods. Despite the broad susceptibility of arthropods to this mode of action, methoxyfenozide, tebufe-nozide and chromafenozide are especially toxic to lepidopteran larvae and have some sublethal effects on lepidopteran adults (see section 6.4). The main reason for this selective toxicity...

Seedling Box Application with Neonicotinoids

Seedling (or nursery) box application with neonicotinoid insecticides in rice gives an excellent control of rice pests, such as hopper species and rice water weevils.93,94 For example, imidacloprid (tradename Admire in Japan) revolutionized the nursery box application (approx. 0.5 to 1.0 g box 1) as a one-shot application, which gives season long control of hoppers and viral infection, so that no field application is necessary. In addition, three nursery box formulations have been developed...

The Spinosyn Insecticides

CHLORIDIS,2 C. B. CLEVELAND,1 C. V. DEAMICIS,1 L. E. GOMEZ,1 D. L. PAROONAGIAN,1 L. A. PAVAN,3 T. C. SPARKS1 AND G. B. WATSON1 1 Dow AgroSciences LLC, 9330 Zionsville Rd., Indianapolis, IN 46268, USA 2Dow AgroSciences LLC, 2 Kalymnou St., 55133 Thessaloniki, Greece 3 Dow AgroSciences LLC, Caixa Postal 226, Mogi Mirim, SP, Brazil, CEP 13800-970

Spinosyn Mode of Action

Spinosad and spinetoram share a common insecticidal mode of action that involves a novel site on the nicotinic acetylcholine (nACh) receptor. Although many of the studies conducted to determine the spinosyn mode of action employed only spinosyn A, the actions of spinosyn D, spinosad and spinetoram have been equivalent to those of spinosyn A in all studies where comparisons were made. Also, insect strains resistant to spinosad exhibit resistance to spin-etoram, providing further evidence for a...

Biocontrol Options

There is perhaps a tendency to think of biological control as a specialized field of entomology, more as an academic pursuit rather than as a tactic to be incorporated into an IPM program. In some respects this is one of the beauties of biocontrol, in that it is already in place and working on behalf of pest management without having to be consciously applied. Unfortunately among non-specialists there is too often a lack of appreciation for the background role that natural enemies play in...

Spray Applications to Plants

The most common application method to crop plants is the use of pressurized spray equipment to distribute spinosad or spinetoram in aqueous suspension over the above-ground surfaces of plants. Depending on the crop and local practices, these applications are typically made with hand-operated or powered backpack sprayers, truck mounted low-volume sprayers, tractor-powered boom sprayers and airblast sprayers, or aircraft. Formulated spinosad products applied as foliar sprays are sold in various...

Transmission of plague

Plague is due to a Gram negative enterobacterium, Yersinia pestis, and it is a disease of rodents transmitted by fleas in the form of bubonic plague. This disease is still endemic in several regions of the world due to the fact that it is a zoonosis primarily infecting rodents (e.g. rats and other wild rodents). Its emergence in humans depends both on the frequency of infection among rodents and the promiscuity of human with these animals. From 1989 to 2003, 38 310 human cases and 2845 deaths...

Plant Virus Vector Control by Neonicotinoids

Phytopathogenic viral and bacterial diseases are of increasing importance worldwide, impacting on the quality and the yield of infested crops. For example, it has been calculated that 1 cm2 of potato leaf can contain around 20 x 109 potato X viruses. Plant viruses can be transmitted by plant-feeding sucking insects. Common virus vectors are aphids, whiteflies, thrips and leafhoppers, whereas bacterial diseases are particularly transmitted by leafhoppers and psyllids. Aphids and other sucking...

Metabolism

In mammals and birds, pyrethroids augment the electrical activity in the brain, spinal column and peripheral neurons which underlie the induced paresthesia, convulsions, and tremors.38 The low toxicity of pyrethroids is attributed to their rapid metabolism in the blood and liver, with more than 90 of pyrethroids being excreted as metabolites in urine within 24 hours after exposure.80 82 Indeed, although extensively used, there are relatively few reports of human, domestic animal or wild animal...

Commercial Use of Entomopathogenic Viruses

Several strategies have been followed for the commercial use of insect viruses as biological control agents of pests. The selection of the most suitable strategy depends on the target species, in terms of feeding habits, behavior and the type of damage caused. The goal expected after the application of the viral agent should also be taken into account, such as reducing the plant damage (in terms of yield or cosmetic damage) or the elimination of the insect pest population. The inoculation...

Synergists

Yamamoto93 defined synergism as where the interaction of two or more toxins is such that their combined effect is greater than simply the sum of their individual toxicities. For pesticide formulations, synergists are typically nontoxic compounds at the dosage applied, but which enhance the toxicity of the active pesticide ingredient. The main route of detoxification of insecticides is through CYP-mediated detoxification. The CYP enzymes bind molecular oxygen and receive electrons from NADPH to...

Semi Synthetic Spinosyns

Spinetoram is the published ISO common name for the semi-synthetic spinosyn mixture derived by making chemical modifications (described in section 5.9.2) to a mixture consisting predominantly of spinosyn J (see Figure 5.2 structure 5.3) and spinosyn L (see Figure 5.2 structure 5.4). There are two small, but significant, structural differences between spinetoram and spinosad. First, the two primary components of spinetoram, 3'-O-ethyl-5,6-dihydro spinosyn J (see Figure 5.2 structure 5.5) and...

Conclusions

Green chemistry, as it relates to the manufacture and use of insecticides, implies minimizing waste, using non-hazardous and renewable raw materials, efficient chemical synthesis, and creating products that have minimal environmental and nontarget organism effects.148 150 The spinosyn insecticides minimize waste and increase efficiency in agricultural production by reducing the losses caused by many important insect pests in almost all food and fiber crops. Because of the microbial origin of...

Flavivirus Yellow Fever Dengue Japanese Encephalitis

The YF remains a serious endemic disease and a constant threat in Sub-Saharan Africa and South America (including Trinidad). It does not prevail in Asia, Oceania, nor the Indian Ocean. The incidence of YF varies greatly from one year to another in 1997, the WHO considered an annual incidence of YF of 200 000 cases, with 30 000 deaths per year. Many YF infections are mild, but the disease can cause severe, life-threatening illness. Symptoms can include high fever, chills, headache, muscle aches,...

References

Furlong, Agric. Human Values, 2007, 24, 281. 2. A. Bravo, S. S. Gill and M. Soberon, in Comprehensive Molecular Insect Science, ed. L. I. Gilbert, K. Iatrou and S. S. Gill, Elsevier B.V., The Netherlands, 2005, p. 175. 3. R. H. ffrench-Constant, A. Dowling and N. R. Waterfield, Toxicon, 2007, 49, 436. 4. M. Gohar, K. Faegri, S. Perchat, S. Ravnum, O. A. 0kstad, M. Gominet, A. B. Kolsto and D. Lereclus, PLoS ONE, 2008, 3, e2793. 5. A. Bravo, S. S. Gill and M. Soberon,...

Physical Properties

Pyrethrins and pyrethroids are highly nonpolar chemicals that have low water solubility and volatility, high octanol-water partition coefficients, and a high affinity to bind to soil and sediment particles (see Table 3.3). Pyrethrins and pyrethroids are rapidly degraded via photochemical reactions which result from isomerization of the substituents on the cyclopropane ring, oxidation of the acid and alcohol moieties, dehalogenation of dihalovinyl derivatives, and decarboxylation occurring in...

Abiotic Degradation

Studies following the US EPA and Organization for Economic Cooperation and Development (OECD) guidelines for hydrolysis at 25 C in the dark showed that methoxyfenozide is not degraded by hydrolysis. It was stable in sterile buffers at pH 5, 7 and 9 (ref. 40). 6.5.3.2.2 Aqueous Photolysis. Methoxyfenozide was stable to aqueous photolysis in sterile deionized water buffered at pH 7 in studies based on US EPA guidelines. In irradiated natural pond water (25 C, with 12 hours...

Introduction

Methoxyfenozide is widely used to control lepidopteran pests in vegetables because of its fit in IPM programs as well as its differentiated mode of action for Table 6.13 Methoxyfenozide global use parameters in tropical fruits. Table 6.13 Methoxyfenozide global use parameters in tropical fruits. aRefer to local methoxyfenozide labels for specific recommendations for crops, pests and rates in the country of interest. bLitchi. aRefer to local methoxyfenozide labels for specific recommendations...

Commercial Use of Fungi as Bioinsecticide

Entomopathogenic fungi have been successfully used as biological control agents against a great number of insect pests. Similar to other biological control agents, such as parasitoids and predators, fungi have been used following inundative and inoculative strategies, as well as classical biological control. The inundative strategy is based on the use of fungi for the repetitive and massive release of the inocula to control existing pest populations, similar to the use of chemical insecticides....

Chemical Structure of Neonicotinoids

Abbreviation Cyclic Chemistry

As a result of the efficient MoA given by the nAChR as target there is no cross-resistance to conventional long-established insecticide classes, such as chlorinated hydrocarbons, organophosphates, carbamates, pyrethroids and several other chemical classes of insecticides used to control insect pests on major crops. Since the introduction of imidacloprid in 1991, neonicotinoids represent a fairly new class of chemistry classified in the same MoA class (nAChR agonists, group 4A) by IRAC.1 Figure...

Use In Europe As An Extract Of Sophora Flavescens Bioinsecticides

The scientific literature continues to document the biological diversity of plant secondary metabolites that are known to affect pest insects. Botanicals have a long history of use and are referenced in recordings from ancient civilizations and folklore.1,2 Likewise, the natural history of insect-plant chemical interactions spans the past 400 million years, or as some authors like to say, terrestrial plants have engaged in chemical warfare against insects and other herbivores over that vast...

Modifications at C21 of the Tetracycle

Most of the spinosyns produced by Saccharopolyspora spinosa have an ethyl group at position C21 on the tetracycle.12,22 The C21 position was difficult to access synthetically so other approaches were taken to provide access to this region of the molecule. Modification of the starter unit for the PKS pathway provided a means to incorporate new substituents at position C21, including n-propyl, isopropyl, cyclopropyl, cyclobutyl, etc. (see Table 5.1).24 Some of these modifications at the C21...

Human and Mammalian Toxicology

The endpoints and study results for mammalian toxicology are summarized in Tables 6.1-6.3. Table 6.1 Acute toxicity of methoxyfenozide. Table 6.1 Acute toxicity of methoxyfenozide. Table 6.2 Short- and long-term mammalian toxicological studies. Study type Results (mgkg 1 day 1) References systemic effects no skin irritation. dog (with 4 week recovery) changes in hematological parameters were present after 4 weeks of treatment complete recovery from effects was demonstrated after 4 weeks of...

Mammalian Toxicity

A full battery of acute, subchronic, chronic, reproduction, developmental, neurotoxicity and mutagenicity genotoxicity tests exists for spinosad and spin-etoram. The structural similarity of spinosad and spinetoram results in highly similar toxicity profiles in mammalian systems. The majority of mammalian toxicological studies are summarized in Table 5.5. Key points for the mammalian toxicity of spinosad and spinetoram are (1) low acute toxicity for Table 5.4 Publically available regulatory...

Cyclohexane Derived Insecticides

The most significant example of insecticides within chlorinated cyclohexane derivatives is g-HCH 16, one of the eight possible stereoisomers of 1,2,3,4,5,6-hexachlorocyclohexane (HCH), sometimes misnamed benzene hexachloride, and the only one with important insecticidal properties.48 The insecticidal activities of g-HCH were discovered in 1943, almost 120 years after its initial synthesis by Michael Faraday (1825). The structural difference between the hexachlorinated isomers is the number and...

Oilseeds

Methoxyfenozide was first registered in Colombia and Indonesia in 1998 for lepidopteran pest control in cotton and soybean, respectively. Currently, it is Table 6.18 Methoxyfenozide global use parameters in cereal crops. Table 6.18 Methoxyfenozide global use parameters in cereal crops. aRefer to local methoxyfenozide labels for specific recommendations for crops, pests and rates in the country of interest. aRefer to local methoxyfenozide labels for specific recommendations for crops, pests and...

Diversity of Bt Toxins

Cry toxins produced by Bacillus thuringiensis are classified by their primary amino acid sequence and have been divided in at least 67 groups (Cry1 to Cry67) comprised by more than 500 different gene sequences (see http www.biols.susx.ac.uk Home Neil_Crickmore Bt index.html).2,5 The 8-endotoxins are organized in four main groups that are not related phylogenetically the three domain Cry toxins (3d-Cry), the mosquitocidal-like Cry toxins (Mtx-like), the binary-like Cry toxins (Bin-like) and the...

Ecotoxicology 671 Aquatic Toxicity

The endpoints for several aquatic invertebrate species are summarized in Table 6.4. Chronic studies indicated that methoxyfenozide is slightly toxic to the water flea, Daphnia magna and moderately toxic to the mysid shrimp, Mysidopsis bahia. The greatest toxicity was observed in midge larvae, Chironomus riparius Meigen, with a NOEC (No Observed Effect Concentration) for adult emergence of 18 mgail-1, based on the initial overlying water concentration. Results of a microcosm study demonstrated...

Neonicotinoids as Resistance Management Tools

Neonicotinoid insecticides all belong to the same mode of action class, and cross-resistance to the established chemistry of other modes of action such as pyrethroids, organophosphates, carbamates or fiproles is not reported. Neo-nicotinoids are therefore considered to be useful tools in resistance management strategies. Even though neonicotinoid insecticides have been used for a prolonged period of time (since 1991), there has been little resistance development in some well-known high risk...

Animal Health

Spinosad has been developed by Elanco Animal Health for a number of significant animal health uses that involve either direct application to animals, application to animal production premises, or bait applications (as described in section 5.10.3.2) to control adult Musca domestica. For sheep, spinosad is marketed under the Extinosad brand and is applied as a plunge dip, shower, or handgun spray to control Bovicola ovis (sheep biting louse) infestations. Spinosad is also used as handgun spray...

General Morphology

The development cycle of mosquitoes includes two phases (see Figure 1.1) (1) an aquatic phase, with the succession of immature stages, such as eggs, larvae (four stages) and pupae, and (2) an air phase with the male and female adults. The eggs are ovoid and measure approximately 0.5 mm. They are laid either on the surface of water (e.g. Anopheles and Culex) or near the surface of water (e.g. Aedes). The eggs may be laid separately (e.g. Anopheles and Aedes) or close together in the form of an...

Spectrum of Arthropod Pest Activity

The spinosyns have demonstrated toxicity to a wide range of arthropod pest species. Table 5.2 lists the orders and families of arthropod pest species that Table 5.2 Taxonomic distribution spinosyns. of arthropod pests susceptible to the Acari mites, ticks Anoplura sucking lice Blattodea cockroaches Coleoptera beetles, weevils Diptera flies, gnats, midges, mosquitoes Hemiptera true bugs, aphids, psyllids, whiteflies, leafhoppers, planthoppers, scales Hymenoptera ants, sawflies Isoptera termites...

Stone Fruits

Since its first registration on stone fruits in Argentina in 1999, additional registrations for methoxyfenozide have been granted in the US and several European countries. The stone fruit crops where methoxyfenozide is used include apricot, cherry, nectarine, peach, plum and prune. Targeted pests include G. molesta C. pomonella and other tortricid species including fruittree leafroller, Archips argyrospila (Walker) omnivorous leafroller, Platynota stul-tana Walsingham and A. velutinana...

Neural Network Approach

While Hansch-style multiple linear regression techniques proved useful for quantifying spinosyn structure-activity relationships on the basis of molecular properties, other QSAR approaches provided the means to predict specific directions for synthesis of analogs with improved insecticidal activity. The use of artificial neural network (ANN) algorithms, a form of artificial intelligence, is a relatively new approach for solving QSAR problems.36,37 An ANN-based approach was used to analyze the...

Basic and Applied Aspects of Neonicotinoid Insecticides

4.2 Target-Site Selectivity of Neonicotinoids 133 4.3 Chemical Structure of Neonicotinoids 134 4.3.1 Structural Diversity of Neonicotinoids 135 4.3.2 Green Technologies for Manufacturing of Neonicotinoids 136 4.3.2.1 Dinotefuran - (R,S)-3-(Hydroxymethyl)-tetrahydrofuran Intermediate 136 4.3.2.2 Clothianidin - O-Methyl-N-nitroisourea Intermediate 137 4.3.3 Physico-Chemical Properties of Neonicotinoids 138 4.3.3.1 Penetration and Translocation of 4.4 Biological Profile of Neonicotinoids 141 4.4.1...

Movement in Plant Tissues

The spinosyns have demonstrated significant translaminar and systemic mobility in plants. Spinosad and spinetoram control larvae of Liriomyza spp. and the early larval instars of some lepidopterous larvae by moving through the upper epidermis into the mesophyll tissue within treated leaves.111,112 Spinosad movement through the leaf epidermis can be increased with the addition of penetrating surfactants to the spray mixture.112 Once in the mesophyll, spinosyn residues do not appear to move out...

Structural Diversity of Neonicotinoids

Considering their pharmacophore moieties -N-C(E) X-Y , neonicotinoid insecticides can be classified as N-nitro-guanidines (imidacloprid, thiamethoxam, clothianidin and dinotefuran), nitromethylenes (nitenpyram) and N-cyano-amidines (acetamiprid and thiacloprid).16 The overall chemical structure of both ring systems and non-cyclic commercial neonicotinoids consists of different segments (1)-(3) (see Figure 4.1).17 19 This chemical structure affects some of the principles of green chemistry in...

Overview of Global Uses and Labels 691 Introduction

Methoxyfenozide first was registered in several countries in Central and South America by R& H in 1998 and 1999 for use on pome fruits, stone fruits, fodder and feed commodities. The first registration of methoxyfenozide in the US was in September 2000 for use on pome fruits followed by cotton in the same year. In 2001, methoxyfenozide was acquired by DAS and subsequent Table 6.7 Methoxyfenozide formulations and trade names. Registered Intrepid , Runner , Prodigy , Integro 240 gl-1 SC...

Seed Treatment Application with Neonicotinoids

Updake Insecticide Treated Seeds

Protection of the environment is an important motivator for continuing to develop new products and methods for seed treatment. This innovative method has additional benefits which make it not only interesting for economic reasons but also from an ecological point of view. The advantages are self evident the ai is only found where activity is desired. Compared with broadcast spraying or in-furrow treatment with granules, seed treatment effectively reduces the treated area considerably, e.g. from...

Phytotonic Effects of Neonicotinoids

Plant growth and productivity, as well as product quality, are greatly influenced by the environmental stress factors to which plants are continuously exposed.102 Stress impairs the energy balance of crops, resulting in more energy consumption for cell repair and less energy generation for growth. The optimal growth, development and maximum yield potential are therefore considered far from that achieved in the field or greenhouse (see Figure 4.11). In recent years, it was found that some...

Entomopathogenic Fungi

Within the great diversity of niches and habitats occupied by fungi in nature, some can be found as parasites and pathogens of a great number of living organisms, including insects. Entomopathogenic fungi are those causing infective diseases in insects, and may constitute important biotic factors that control insect population densities within certain levels in nature.94 There are more than 700 species of entomopathogenic fungi reported to date, from obligate to opportunistic pathogens some...

Environmental Fate

Existing lab studies for 14C-labeled spinosyns in prototype environmental compartments include aerobic and anaerobic soil metabolism, aqueous photolysis, hydrolysis, aqueous aerobic and anaerobic degradation, and adsorption desorption to soils. Field studies have focused on field degradation rates in soil and studies with formulated products and aquatic systems. Key points for the environmental fate of spinosad and spinetoram are (1) photolysis is the major route of degradation for spinosad and...

Jans Parlar In

Fernandez-Bolanos and M. V. Gil, Green Chem., 2005, 7, 431. 2. J. E. Casida and G. B. Quistad, Annu. Rev. Entomol., 1998, 43, 1. 3. P. Warrior, Pest Manag. Sci., 2000, 56, 681. 4. W. Olkowski, S. Daar and H. Olkowski, The Gardener's Guide to Common-sense Pest Control, The Taunton Press, 1995, Newtown, CT, USA, p. 22. 5. S. Horstadius, Biol. J. Linnean Soc., 1974, 6, 269. 6. E. Panagiotakopulu, P. C. Buckland and P. M. Day, J. Archaeol. Sci., 1995, 22, 705. 7. R. L. Metcalf and...

Target Site Selectivity of Neonicotinoids

In contrast to the naturally occurring alkaloid (S)-(-)-nicotine isolated as botanical insecticide from Nicotiana species IRAC (Insecticide Resistance Action Committee) Mode of Action (MoA) classification nAChR agonists, group 4B , neonicotinoid insecticides act selectively on the insect central nervous system (CNS) as an agonist of the post-synaptic nAChRs, their molecular target site.1 3 There is a distinct difference in the selective toxicity between (S)-(-)-nicotine and neonicotinoid...

Use of Spinosad and Spinetoram for Arthropod Pest Management

The first spinosad registration for agricultural crop use was in Korea in 1996, followed by the US registration for use on cotton in 1997. Spinosad is now widely registered around the world to manage a broad spectrum of arthropod pests in a variety of agricultural, horticultural, forestry, animal health, public health, stored grain and residential environments. The first spinetoram registrations for agricultural crop use were granted in New Zealand, USA and Canada in 2007. Although spinetoram...

Overcoming Abiotic and Biotic Stress

Stress in plants can be of two types (1) Abiotic - arising from fluctuations in their physical or chemical environment (such as cold, heat, excessive light, elevated salt levels in soil, ozone in air, oxygen deficiency, flooding or drought, or mechanical damage) or (2) Biotic - imposed by insect pests, weed and pathogens (fungi, viruses, bacteria). Most yield losses, however, are attributed to abiotic stress. The response of Trimax-treated (Trimax is an optimized imidacloprid formulation)...

Treatment of Seeds and Seedlings

In Japan, it is standard practice to apply granular formulations of insecticides and fungicides to rice nursery boxes, the shallow trays where rice seedlings are grown before being transplanted into flooded paddies. Spinosad, either alone or in combination with other insecticides and or fungicides, is registered in Japan for this purpose. Immediately before transplanting, spinosad granules are applied at a rate of 50 g of formulated product per nursery box (which delivers 75 g of spinosad per...

Plant Metabolism

Methoxyfenozide is metabolized in plants by the formation of a free phenol and products that result from the oxidation of the alkyl substituents. In addition, two polar carbohydrate conjugates have been identified in rotational crops. The parent compound is the residue of primary concern for dietary exposure assessments and tolerance setting. Studies carried out to elucidate the metabolic pathway of methoxyfenozide in plants are described in further detail in this section. The metabolism,...

Resistance

The fact that pyrethrins, pyrethroids and DDT share a common mode of action, and therefore a common binding domain on the sodium channel, has important implications for the continued use of pyrethrins and pyrethroids in pest management. Resistance to insecticides may cost more than 1.4 billion per year in the USA alone.101 Selection for resistance to either class of insecticides will lead to resistance to both, which has been extensively documented in mosquitoes.102 Pyrethroids are currently...

Stored Grain Protection

Spinosad has been developed to control insect pests in stored grain. The spectrum of stored grain pests controlled by spinosad under commercial conditions is still under study, but it is clear from research trials that adult and or immature Rhyzopertha dominica (lesser grain borer), Prostephanus truncatus (larger grain borer), Cryptolestes ferrugineus (rusty grain beetle), Tribolium castaneum (red flour beetle), Tribolium confusum (confused flour beetle), Ory-zaephilus surinamensis (sawtoothed...

Bt Commercial Products

Bt products are presented in different types of formulations depending on their target pests, such as liquid concentrates, wettable powders, ready-to-use dusts and granules. Most of these products are composed of spore-crystal preparations derived from wild-type strains as B. thuringiensis var. kurstaki (Btk) HD1 and HD73 strains that express some Cry1A and Cry2Aa proteins (i.e. Biobit, Condor, Cutlass, Dipel, Full-Bac, Javelin, M-Peril and MVP products) that are highly effective in the control...

Mosquito Control

Spinosad controls the larvae of many important species in the mosquito genera Aedes, Culex, Ochlerotatus and Anopheles.146 Several new spinosad formulations have been developed by Clarke Mosquito Control Products or Dow AgroSciences to control mosquito larvae in diverse aquatic environments, such as artificial and natural containers, temporary flooded areas, swampy woodlands, marshes, sewage lagoons, storm water and drainage canals, catch basins and coastal impoundments. These formulations can...

The Bisacylhydrazine Insecticides213

Gomez, Kerry Hastings, Harvey A. Yoshida, James E. Dripps, Jason Bailey, Sandra Rotondaro, Steve Knowles, Doris L. Paroonagian, Tarlochan Singh Dhadialla and Raymond Boucher 6.2 Synthesis and Design 214 6.4 Effects on Insect Population Dynamics and 6.4.1 Sublethal and Ovicidal Effects on Adults 6.4.1.1 Sublethal Effects 216 6.4.1.2 Ovicidal Effects 217 6.4.2 Speed of Kill on Larvae 218 6.5 Environmental Effects 218 6.5.2 Metabolism and Bioaccumulation 219 6.5.2.1 Plant Metabolism 219...

Production of Spinosad

Spinosad is produced directly from the fermentation of a strain of Saccharo-polyspora spinosa. Production strains of S. spinosa have been selected for increased titers of spinosyns A and D, however, no genetic engineering techniques have been used in this process and no genetically-modified organisms are used in the production process. After fermentation, the spinosyn A and D mixture is extracted from the fermentation broth, precipitated and dried to create technical spinosad, which is then...

Plant Metabolism and Crop Residues

Several metabolic pathways are involved in the breakdown of spinosad and spinetoram in plants. Fundamental understanding of these degradation paths is gained from Nature of Residue (NOR) studies in plants conducted with active ingredient uniformly 14C-labeled in the macrolide (14C-spinosyn A, 14C-spinosad D, 14C-XDE-175-J or 14C-XDE-175-L). Studies with grapes, apple fruit and apple leaves have compared exposed and control (covered) plant tissues and concluded that photolysis plays a dominant...

Preparation of Organophosphorus Insecticides

The synthesis of organophosphorus insecticides involves numerous different reactions. In most cases, the preparation starts by treating phosphorous with sulfur or chlorine to give diphosphorus pentasulfide or phosphorus trichloride, respectively. Subsequently, they are transformed into the main intermediates 58-64 depicted in Scheme 2.4.97 As an example, phenyl phosphorothionates 65 can be made by treatment of dialkyl phosphorochloridothionates 64 with phenols in basic medium (see Scheme 2.4)....

Modern Agriculture and Pest Forcing 931 The Pesticide Connection

Estimates of crop losses due to all pests (animals, weeds, pathogens) is rather staggering when considered in the context of the powerful management tools that are available to fight back. Global losses of soybean, wheat and cotton are estimated to be 26-29 , but are even higher for maize, rice, and potatoes at 31, 37 and 40 , respectively.19 Such losses demonstrate not only the tremendous diversity of organisms that compete with humans for food resources, but the impracticality of devising...

Oil Dispersion Technology

Recently, Bayer CropScience has developed a completely new formulation technology O-TEQ (oil dispersion, OD) for foliar application of both imidacloprid (Confidor OD 200)and thiacloprid (Biscaya OD 240).96 98 This formulation type is defined as a stable suspension of ai(s) in a water immiscible fluid, which may contain other dissolved ai(s), intended for dilution with water before use''.99 The main characteristics related to this aspect are outlined in Figure 4.9. O-TEQ can be seen as a vehicle...

Synthesis and Design

The discovery of the first nonsteroidal, insecticidal BAH (RH-5489)1 revealed a broad spectrum of activity against lepidopteran, coleopteran and dipteran insects. Extensive work with this new class of chemistry, which involved synthesis guided by structure-activity relationship (SAR) analysis of over 4000 BAH analogs, led to the discovery of the three insecticides selected for commercialization at R& H tebufenozide, methoxyfenozide and halofenozide. The synthetic routes of these three...

Overview of Regulatory Studies for Spinosad and Spinetoram

Dow AgroSciences has conducted hundreds of proprietary regulatory studies on spinosad and spinetoram. The majority of these studies were performed according to national or international regulatory guidelines.116 118 The studies encompass mammalian toxicity, ecotoxicology, environmental fate (lab and field), crop metabolism and field residue trials. Information on environmental fate is used to predict potential off-target movement and resultant environmental concentrations. Crop residue studies...

Versatile Application Methods for Neonicotinoids

Due to their remarkable physico-chemical properties (see section 4.3.3), neo-nicotinoid insecticides have a high degree of versatility, not seen to the same extent in other insecticidal classes. Most neonicotinoids can be used as foliar sprays, seed-coating treatments (see section 4.5.1) and via soil application. At present, approximately 60 of all neonicotinoid applications are soil seed treatments and most spray applications are especially targeted against pests attacking crops such as...

Annual Horticultural and Agronomic Crops

The most significant use pattern for spinosad and spinetoram is the control of insect pests attacking vegetable crops grown outdoors and in greenhouses. Spinosad or spinetoram are registered for use in more than 100 annual horticultural crops including bulb vegetables, brassica vegetables, sweet corn, cucurbits, solanaceous fruiting vegetables, leafy vegetables, potato, sweet-potato, root vegetables, strawberry and pineapple. The key insect pests controlled by spinosad and spinetoram in several...

Cyclodiene Insecticides

Preparation Reaction Heptachlor

Cyclodiene insecticides are comprised of compounds obtained by a Diels-Alder reaction, and were first marketed after World War II. The key synthetic intermediate is hexachlorocyclopentadiene 26 that can be obtained by chlorination of cyclopentadiene 25, but also from pentane, cyclopentane or neopentane see Scheme 2.2 .68 A Diels-Alder cycloaddition between cyclopentadiene and 26 gave an intermediate called chlordene 27, whose chlorination afforded mainly a mixture of cis- and trans- isomers on...

Green Technologies for Manufacturing of Neonicotinoids

Green chemistry utilizes a set of 12 principles that reduces or eliminates the use or generation of hazardous substances in the design, manufacture and application of chemical products.24 The design of greener processes is also under consideration in the manufacture of neonicotinoid insecticides and their intermediates. This can be exemplified in case of the two N-nitro-guanidines dinotefuran and clothianidin. 4.3.2.1 Dinotefuran - R,S -3- Hydroxymethyl -tetrahydrofuran Intermediate From a...

Pesticide Options

For all of their negative connotations, pesticides remain an indispensable part of pest management. Pesticide modes of action have continued to expand despite perennial concerns expressed as early as the 1970s about the finite number of active ingredients remaining to be discovered and the tremendous cost of development of each new insecticide.66 Nonetheless, whole new insecticide classes have been discovered and commercialized since that time, as insecticides in general have become safer and...