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WO2018055478A1 - Procédé de lutte contre les insectes résistants aux insecticides - Google Patents

Procédé de lutte contre les insectes résistants aux insecticides Download PDF

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Publication number
WO2018055478A1
WO2018055478A1 PCT/IB2017/055413 IB2017055413W WO2018055478A1 WO 2018055478 A1 WO2018055478 A1 WO 2018055478A1 IB 2017055413 W IB2017055413 W IB 2017055413W WO 2018055478 A1 WO2018055478 A1 WO 2018055478A1
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WIPO (PCT)
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spp
insects
resistant
methyl
insecticide
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Inventor
Tatjana Sikuljak
Matthias Pohlman
Ralph Paulini
Concepcion MOLINA
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BASF China Co Ltd
BASF SE
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BASF China Co Ltd
BASF SE
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof

Definitions

  • the present invention relates to a method of controlling insects, that are resistant to one or more insecticide(s).
  • IRAC Insecticide Resistance Action Committee
  • resistance may be defined as 'a heritable change in the sensitivity of a pest population that is reflected in the repeated fail- ure of a product to achieve the expected level of control when used according to the label recommendation for that pest species' (www.irac-online.org).
  • Cross-resistance occurs when resistance to one insecticide confers resistance to another insecticide, even where the insect has not been exposed to the latter product.
  • pest insect populations are usually large in size and they breed quickly, there is always a risk that insecticide resistance may evolve, especially when insecticides are misused or over-used.
  • Natural selection by an insecticide allows some naturally occurring, pre-adapted insects with resistance genes to survive and to passon the resistance trait to their offspring.
  • selection for the resistant individuals persists so the proportion of resistant insects in the population increases, while susceptible individuals are eliminated by the insecticide. Under this permanent selection pressure, resistant insects outnumber susceptible ones and the insecticide is no longer effective.
  • the speed with which resistance develops depends on several factors, including how fast the insects reproduce, the mi- gration and host range of the pest, the availability of nearby susceptible populations, the persistence and specificity of the crop protection product, and the rate, timing and number of applications made. Resistance increases e.g. in greenhouses, where insects or mites reproduce quickly and when there is little or no immigration of susceptible individuals and the user may spray frequently (http://www.irac-online.org/about/resistance/).
  • the insecticide resistant insects can detoxify by destroying or excretion in comparison to normal non-resistant insects, e.g. due to their metabolism such as their enzyme systems. Metabolic resistance is very often dependent on the structure of the active ingredient. Therefore the metabolic resistance is most likely overcome by actives with a different chemical structure.
  • Another resistance mechanism is a modification of the target structure (protein, receptor, ion channel, etc.) of the insecticide. The insecticidal activity is reduced by a change in the binding site, e.g. due to point mutations, which are passed on. Further, there is also resistance due to behavioral change and penetration resistance (the outer shell of the insect developed barriers that slow down the penetration of insecticides in the body of the insect). In resistant pests a combination of several of these resistance mechanisms can be found.
  • a resistance mechanism that is responsible for the resistance of a pest to a particular insecticide these pests also faces a new insecticide resistant making (cross-) resistance, is difficult because of the different resistance mechanisms be fore-seen. Particularly in cases where the mechanism of action of the new insecticide is not known, or where the resistance by mechanisms other than by changing the binding site, for example by metabolic resistance is mediated, the prediction of a cross-resistance is difficult.
  • IRM Insecticide Resistance Management
  • IRM The most important measure in the context of IRM is to reduce the selection pressure for resistant pests. This is achieved by the alternate use of various chemical classes of insecticides with different mechanisms of action, whereby the development of resistance can be slowed or prevented entirely.
  • IPM The main principle of IPM is to integrate a wide range of pest management tools to prevent pests from reaching damaging levels in crops, thereby reducing reliance on any single method.
  • tools include biologicals (protection or release of parasitoids, predators and pathogens), agricultural methods such as crop hygiene, trap-crops, monitoring, use of genetic modified organisms like resistant plant varieties, transgenic plants and, of course, the correct application of insecticides.
  • the neonicotinoids represent the fastest-growing class of insecticides introduced to the market since the commercialization of pyrethroids (Nauen & Denholm, 2005: Archives of Insect Biochemistry and Physiology 58:200-215) and are extremely valuable insect control agents not least because they had exhibited little or no cross-resistance to the older insecticide classes, which suffer markedly from resistance problems. They showed many years to be imperishable to development of resistance, but due to the grown and extensive use of such neonicotinoid insecticides for the control of agriculturally important crop pests and also in the control of cat and dog fleas, resistance started to be observed.
  • the selectivity of neonicotinoid compounds for insect species has been attributed to their bind- ing on nicotinic acetylcholine receptors in which the negatively charged nitro- or cyano-groups of neonicotinoid compounds interact with a cationic subsite within insect nicotinic acetylcholine receptors.
  • Resistance to neonicotinoids can arise either through nAChR subtypes expression, detoxification mechanisms and/or structural alterations of target-site proteins. Consequently, a number of derivatives and analogues of imidacloprid have been generated to date.
  • Nilaparvata lugens is a primary insect pest of rice crops.
  • neonicotinoid insecticide refers to any insecticidal compound that acts at the insect nicotinic acetylcholine receptor, and in particular refers to those compounds classified as neonicotinoid insectides according to Yamamoto (1996, Agrochem Jpn 68:14-15).
  • Examples of neonicotinoid insecticides include those in Group 4A of the IRAC (insecticide resistance action committee, Crop Life) mode of action classification scheme, e.g. acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, and thiamethoxam, as well as any compound having the same mode of action.
  • control of resistant pests is particularly relevant in cases where the mode of action of an insecticide is not known or where the resistance is mediated by mechanisms other than by changing the binding site.
  • the present invention is based on the surprising finding that a compound selected from the chemical class of pyripyropene derivatives, especially the compound of formula (I) shown herein below, can be successfully used to control pests, which are resistant to known insecticides.
  • the present invention is further also based on the surprising finding that a compound selected from the chemical class of pyripyropene derivative, especially the compound of formula (I), can be successfully used to control insecticide resistant populations of arthropods, in particular insects, and more particular insects from the order Hemiptera, Lepidoptera, Coleoptera or Dip- tera, and also insects from the order Thysanoptera or Homoptera.
  • a method of controlling insects which are resistant to an insecticide comprises applying to said insecticide resistant insects at least one pesticidally active pyripyropene derivative of formula (I):
  • the method for control of resistant pests is used against pests having developed a resistance against cyclo dienes, organophosphates, carbamates, formamidines, pyrethroids, spinosyns, neonicotinoids, insect growth regulators and antifeedants.
  • the methods are effective against pests which have developed resistance against pyrethroids and/or chloronicotinyls, the so-called CNI or neonicotinoids.
  • the methods relate to controlling neonicotinoid resistant insects in the order Hemip- terea, Lepidoptera, Coleoptera, Diptera, Thysanoptera or Homoptera, especially Hemiptera.
  • Methods of the invention find particular use in controlling resistant insects in crops of useful plants.
  • One embodiment of the invention there provides a method of controlling species of insects which have shown resistancy effects against insecticides, in particular from the order of Hemiptera with their suborder of Homoptera and Heteroptera, but also from the orders Thysanoptera, Lepidoptera, Coleoptera or Diptera.
  • the method of the present invention control pests of the suborder of suchenorrhyn- cha, such as cicadas, leafhoppers, treehoppers, planthoppers and froghoppers and of the suborder of sternorrhyncha, especially aphids, whiteflies and scale insects.
  • the suborder of suchenorrhyn- cha such as cicadas, leafhoppers, treehoppers, planthoppers and froghoppers and of the suborder of sternorrhyncha, especially aphids, whiteflies and scale insects.
  • the method of the present invention may further control pests of the suborder heteroptera in- eluding bugs, such as shield bugs, seed bugs, assassin bugs, flower bugs, sweetpotato bugs and the water bugs.
  • pests of the suborder heteroptera in- eluding bugs such as shield bugs, seed bugs, assassin bugs, flower bugs, sweetpotato bugs and the water bugs.
  • plants exhibiting aphid damage can have a variety of symptoms, such as decreased growth rates, mottled leaves, yellowing, stunted growth, curled leaves, browning, wilting, low yields and death.
  • the removal of sap creates a lack of vigour in the plant, and aphid sa- liva is toxic to plants. Aphids frequently transmit disease-causing organisms like plant viruses to their hosts.
  • honeydew The coating of plants with honeydew can contribute to the spread of fungi which can damage plants.
  • Honeydew produced by aphids has been observed to reduce the effectiveness of fungicides as well.
  • the invention relates to a method, in which the pyripyropene derivative of formula (I) itself and its stereoisomers, salts, tautomers or N-oxides, especially it salts, and it mixtures.
  • Pyripyropene A has inhibitory activity against ACAT (acyl-CoA: cholesterol acyltransferase) and was to be applied, for example, to the treatment of diseases induced by cholesterol accumulation, as described in Japanese Patent No. 2993767 (Japanese Patent Laid-Open Publication No. 360895/1992) and Journal of Antibiotics (1993), 46 15 (7), 1 168-9.
  • ACAT acyl-CoA: cholesterol acyltransferase
  • pyripyropene A has insecticidal activity against larvae of Helicoverpa zea.
  • WO 2004/060065 dis- closes that pyripyropene A has insecticidal activity against Plutella xylostella L larvae and Te- nebrio molitorL. None of these documents, however, provides a specific description on insecticidal activity of pyripyropene A against other pests.
  • Pyripyropene A (pyripyropene pesticide of formula II herein below), produced e.g. by the method described in Journal of Society of Synthetic Organic Chemistry, Japan (1998), Vol. 56, No. 6, pp. 478-488 or WO 94/09417, may for example be used as starting material for preparing further pyripyropene derivatives.
  • Pyripyropene A may optionally also be used in the methods of the present inventions.
  • the pyripyropene derivative of formula (I) itself and its combined application with other insecticides are known to have shown activity against certain crop damaging insect pests
  • the compounds of formula I and some of their selected mixtures with pesticidally active compounds (II) have not yet been described for solving discussed problems as mentioned above.
  • Afidopyropene or the "pyripyropene derivative of formula (I)” or the “compound of formula I” as well “pyripyropene A”, or “compound of formula (II)” and “compound II”, and the terms “compound ⁇ ) for methods according to the (present) invention", “compound(s) according to the (present) invention” or which all compound(s) are applied in methods and uses according to the pre- sent invention comprise the compound(s) as defined herein as well as a known stereoisomer, salt, tautomer or N-oxide thereof (including a polymorphic crystalline form, a co-crystal or a solvate of a compound or a stereoisomer, salt, tautomer or N-oxide thereof).
  • the compounds according to the present invention may be provided as such or as mixtures with at least one mixing partner such as an insecticide, fungicide or biopesticide, or as compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof. Suitable formulations will be described further below.
  • the compound of the formula (I) may have one or more centers of chirality, in which case they are present as mixtures of enantiomers or diastereomers.
  • the invention provides both the pure enantiomers or pure diastereomers of the compounds of formula (I), and their mixtures and the use according to the invention of the pure enantiomers or pure diastereomers of the compound of formula (I) or its mixtures.
  • Suitable compounds of the formula (I) also include all possible geometrical stereoisomers (cis/trans isomers) and mixtures thereof. Cis/trans isomers may be pre- sent with respect to an alkene, carbon-nitrogen double-bond, nitrogen-sulfur double bond or amide group.
  • stereoisomer(s) encompasses both optical isomers, such as enantiomers or diastereomers, the latter existing due to more than one center of chirality in the molecule, as well as geometrical isomers (cis/trans isomers).
  • Salts of the compounds of the present invention are preferably agriculturally and veterinarily acceptable salts. They can be formed in a customary method, e.g. by reacting the compound with an acid if the compound of the present invention has a basic functionality or by reacting the compound with a suitable base if the compound of the present invention has an acidic functionality.
  • suitable "agriculturally useful salts” or “agriculturally acceptable salts” are especially the salts of those cations or the acid addition salts of those acids whose cations and anions, respectively, do not have any adverse effect on the action of the compounds according to the present invention.
  • Suitable cations are in particular the ions of the alkali metals, preferably lithium, sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and also ammonium (NH4 + ) and substituted ammonium in which one to four of the hydrogen atoms are replaced by Ci-C4-alkyl, Ci-C4-hydroxyalkyl, Ci-C4-alkoxy, Ci-C4-alkoxy-Ci-C4-alkyl, hydroxy-Ci-C4-alkoxy- Ci-C4-alkyl, phenyl or benzyl.
  • substituted ammonium ions comprise methylammo- nium, isopropylammonium, dimethylammonium, diisopropylammonium, trimethylammonium, tet- ramethylammonium, tetraethylammonium, tetrabutylammonium, 2-hydroxyethylammonium, 2- (2-hydroxyethoxy)ethyl-ammonium, bis(2-hydroxyethyl)ammonium, benzyltrimethylammonium and benzyltriethylammonium, furthermore phosphonium ions, sulfonium ions, preferably tri(C C 4 -alkyl)sulfonium, and sulfoxonium ions, preferably tri(Ci-C4-alkyl)sulfoxonium.
  • Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae I with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • the compound of the formula (I) may be present in the form of their N-oxides.
  • N- oxide includes any compound of the present invention which has at least one tertiary nitrogen atom that is oxidized to an N-oxide moiety.
  • N-oxides of compounds (I) can in particular be prepared by oxidizing the ring nitrogen atom(s) of the pyridine ring and/or the pyrazole ring with a suitable oxidizing agent, such as peroxo carboxylic acids or other peroxides.
  • a suitable oxidizing agent such as peroxo carboxylic acids or other peroxides.
  • the compounds of the present invention may be amorphous or may exist in one ore more different crystalline states (polymorphs) which may have different macroscopic properties such as stability or show different biological properties such as activities.
  • the present invention includes both amorphous and crystalline compounds of formula (I), their enantiomers or diastereomers, mixtures of different crystalline states of the respective compound of formula (I), its enantiomers or diastereomers, as well as amorphous or crystalline salts thereof.
  • co-crystal denotes a complex of the compounds according to the invention or a stereoisomer, salt, tautomer or N-oxide thereof, with one or more other molecules (preferably one molecule type), wherein usually the ratio of the compound according to the invention and the other molecule is a stoichiometric ratio.
  • solvate denotes a co-complex of the compounds according to the invention, or a stereoisomer, salt, tautomer or N-oxide thereof, with solvent molecules.
  • the solvent is usually liquid. Examples of solvents are methanol, ethanol, toluol, xylol.
  • a preferred solvent which forms solvates is water, which solvates are referred to as "hydrates".
  • a solvate or hydrate is usually characterized by the presence of a fixed number of n molecules solvent per m molecules compound according to the invention.
  • Agronomically acceptable salts of the compounds I can be formed in a customary manner, e.g. by reaction with an acid of the anion in question.
  • resistance therefore means that the original activitiy of a pesticide against the target organisms (arthropods, insects) decreases or is even lost, due to genetic adaptation of the target organism.
  • “Resistant” to an insecticide is understood to mean resistant to at least one insecticide, i.e. the insect may be resistant to only one, but also to several insecticides.
  • the resistance may be also against an insecticidal effect which is due to a genetic modification of a plant (modified or transgenic plant), which caused a resistance of the plant or crop to certain pests, especially insect pests, in susceptible insects.
  • insecticidal proteins especially those mentioned herein, especially those known from the bacterial genus Bacillus, particularly from Bacillus thuringiensis, such as endotoxins, e. g. CrylA(b), CrylA(c), CrylF, CrylF(a2), CryllA(b), CrylllA, CrylllB(bl ) or Cry9c; vegetative insecticidal proteins (VIP), e. g. VIP1 , VIP2, VIP3 or VIP3A; insecticidal proteins of bacteria colonizing nematodes, for example Photorhabdus spp. or Xenorhabdus spp., and so on.
  • VIP1 , VIP2, VIP3 or VIP3A vegetative insecticidal proteins
  • insecticidal proteins of bacteria colonizing nematodes for example Photorhabdus spp. or Xenorhabdus spp., and so on.
  • Methods and uses of the invention as described herein may also involve a step of assessing whether insects are resistant to certain insecticides.
  • This step will in general involve collecting a sample of insects from the area (e.g. crop, field, habitat) to be treated, before actually applying a compound of formula I, and testing (for example using any suitable phenotypic, biochemical or molecular biological technique applicable) for resistance/sensitivity.
  • a method of controlling insects which are resistant to an insecticide comprises applying a composition comprising a pyripyropene derivative, such as a compound of formula I (afidopyropen) or formula II (pyripyro- pene A), especially afidopyropen, in free form or in agrochemically acceptable salt form to said resistant insects.
  • a pyripyropene derivative such as a compound of formula I (afidopyropen) or formula II (pyripyro- pene A)
  • afidopyropen in free form or in agrochemically acceptable salt form
  • a method of controlling insects from the order Hemiptera, Lepidoptera, Coleoptera, or Diptera, which are resistant to an insecticide comprises applying a composition comprising a pyripyropene derivative, such as a compound of formula I (afidopyropen) or formula II (pyripyropene A), especially afidopyropen, in free form or in agrochemically acceptable salt form to said resistant insects.
  • a pyripyropene derivative such as a compound of formula I (afidopyropen) or formula II (pyripyropene A)
  • a method of controlling insects from the order Hemiptera, especially from the families of Aleyrodoidea, Aphididae and Delphaci- dae, which are resistant to an insecticide comprises applying a composition comprising a pyripyropene derivative, such as a compound of formula I (afidopyropen) or formula II (pyripyropene A), especially afidopyropen, in free form or in agrochemically acceptable salt form to said resistant insects.
  • a pyripyropene derivative such as a compound of formula I (afidopyropen) or formula II (pyripyropene A)
  • a method of controlling insects which are resistant to a neonicotinoid insecticide comprises applying a composition comprising a pyripyropene derivative, such as a compound of formula I (afidopyropen) or formula II (pyripyropene A), especially afidopyropen, in free form or in agrochemically acceptable salt form to said resistant insects.
  • a pyripyropene derivative such as a compound of formula I (afidopyropen) or formula II (pyripyropene A)
  • afidopyropen in free form or in agrochemically acceptable salt form
  • a method of controlling insects which are resistant to a pyrethroid insecticide comprises applying a composition comprising a pyripyropene derivative, such as a compound of formula I (afidopyropen) or formula II (pyripyropene A), especially afidopyropen, in free form or in agrochemically acceptable salt form to said resistant insects.
  • a pyripyropene derivative such as a compound of formula I (afidopyropen) or formula II (pyripyropene A)
  • afidopyropen in free form or in agrochemically acceptable salt form
  • a method of controlling insects which are resistant to an organophosphate insecticide such as primicarb, which method comprises applying a composition comprising a pyripyropene derivative, such as a compound of formula I (afidopyropen) or formula II (pyripyropene A), especially afidopyropen, in free form or in agrochemically acceptable salt form to said resistant insects.
  • a pyripyropene derivative such as a compound of formula I (afidopyropen) or formula II (pyripyropene A)
  • afidopyropen in free form or in agrochemically acceptable salt form
  • a method of controlling insects which are resistant to a feeding blocker insecticide such as pymetrozine, which method comprises applying a composition comprising a pyripyropene derivative, such as a compound of formula I (afidopyropen) or formula II (pyripyropene A), especially afidopyropen, in free form or in agrochemically acceptable salt form to said resistant insects.
  • a pyripyropene derivative such as a compound of formula I (afidopyropen) or formula II (pyripyropene A)
  • a method of controlling insects from the order Hemiptera, especially from the families of Aleyrodoidea, Aphididae and Delphaci- dae, which are resistant to a neonicotinic insecticide comprises applying a composition comprising a pyripyropene derivative, such as a compound of formula I (afidopyropen) or formula II (pyripyropene A), especially afidopyropen, in free form or in agrochemically ac- ceptable salt form to said resistant insects.
  • a pyripyropene derivative such as a compound of formula I (afidopyropen) or formula II (pyripyropene A)
  • the invention also provides a method of protecting a crop of useful plants, wherein said crop is susceptible to and/or under attack from such insects.
  • Such a method involves applying to said crop, treating a plant propagation material of said crop with, and/or applying to said insects, a composition comprising a pyripyropene derivative in free form or in agrochemically acceptable salt form.
  • the pyripyropene derivative may also be used in a resistance management strategy with a view to controlling resistance to the neonicotinoid class of insecticides.
  • Such a RM strategy may involve applying a composition comprising a mixture of a neonicotinoid and a pyripyropene derivative, or alternating applications of a composition comprising a pyri- pyropene derivative and a composition comprising a neonicotinoid insecticide, either by application alternation (including different types of application, such as treatment of plant propagation material, e.g. in seed treatment, and foliar spray), or seasonal/crop alternation basis (e.g. use the pyripyropene derivative on a first crop/for control in a first growing season, and use a neonicotinoid insecticide for a subsequent crop/growing season, or vice versa), and this forms yet a further aspect of the invention.
  • application alternation including different types of application, such as treatment of plant propagation material, e.g. in seed treatment, and foliar spray
  • seasonal/crop alternation basis e.g. use the pyripyropene derivative on a first crop/for control in a
  • the neonicotinoid would be e.g. thiamethoxam or imidacloprid.
  • the compounds of the present invention are effective through both contact and ingestion. Furthermore, the compounds of the present invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.
  • the compounds of the present invention can be applied as such or in form of compositions comprising them as defined above. Furthermore, the compounds of the present invention can be applied together with a mixing partner as defined above or in form of compositions comprising said mixtures as defined above.
  • the components of said mixture can be applied simultaneously, jointly or separately, or in succession, that is immediately one after another and thereby creating the mixture "in situ" on the desired location, e.g. the plant, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
  • the application can be carried out both before and after the infestation of the crops, plants, plant propagation materials, such as seeds, soil, or the area, material or environment by the pests.
  • Suitable application methods include inter alia soil treatment, seed treatment, in furrow application, and foliar application.
  • Soil treatment methods include drenching the soil, drip irrigation (drip application onto the soil), dipping roots, tubers or bulbs, or soil injection.
  • Seed treatment techniques include seed dressing, seed coating, seed dusting, seed soaking, and seed pelleting.
  • furrow applications typically include the steps of making a furrow in cultivated land, seeding the furrow with seeds, applying the pesticidally active compound to the furrow, and closing the furrow.
  • Foliar application refers to the application of the pesticidally active compound to plant foliage, e.g. through spray equipment.
  • pheromones for specific crops and pests are known to a skilled person and publicly available from databases of pheromones and semiochemicals, such as http://www.pherobase.com.
  • the term "contacting” includes both direct contact (applying the compounds/compositions directly on the animal pest or plant - typically to the foliage, stem or roots of the plant) and indirect contact (applying the compounds/compositions to the locus, i.e. habitat, breeding ground, plant, seed, soil, area, material or environment in which a pest is growing or may grow, of the animal pest or plant).
  • animal pest includes arthropods, gastropods, and nematodes.
  • Preferred animal pests according to the invention are arthropods, preferably insects and arachnids, in particular insects.
  • Insects, which are of particular relevance for crops, are typically referred to as crop insect pests.
  • the term "crop” refers to both, growing and harvested crops.
  • plant includes cereals, e.g. durum and other wheat, rye, barley, triticale, oats, rice, or maize (fodder maize and sugar maize / sweet and field corn); beet, e.g. sugar beet or fodder beet; fruits, such as pomes, stone fruits or soft fruits, e.g.
  • iceberg lettuce chic- ory, cabbage, asparagus, cabbages, carrots, onions, garlic, leeks, tomatoes, potatoes, cucurbits or sweet peppers; lauraceous plants, such as avocados, cinnamon or camphor; energy and raw material plants, such as corn, soybean, rapeseed, sugar cane or oil palm; tobacco; nuts, e.g. walnuts; pistachios; coffee; tea; bananas; vines (table grapes and grape juice grape vines); hop; sweet leaf (also called Stevia); natural rubber plants or ornamental and forestry plants, such as flowers (e.g.
  • Preferred plants include potatoes sugar beets, tobacco, wheat, rye, barley, oats, rice, corn, cotton, soybeans, rapeseed, legumes, sunflowers, coffee or sugar cane; fruits; vines; ornamentals; or vegetables, such as cucumbers, tomatoes, beans or squashes.
  • plant is to be understood as including wild type plants and plants, which have been modified by either conventional breeding, or mutagenesis or genetic engineering, or by a combination thereof.
  • Plants which have been modified by mutagenesis or genetic engineering, and are of particular commercial importance, include alfalfa, rapeseed (e.g. oilseed rape), bean, carnation, chicory, cotton, eggplant, eucalyptus, flax, lentil, maize, melon, papaya, petunia, plum, poplar, potato, rice, soybean, squash, sugar beet, sugarcane, sunflower, sweet pepper, tobacco, tomato, and cereals (e.g. wheat), in particular maize, soybean, cotton, wheat, and rice.
  • rapeseed e.g. oilseed rape
  • bean carnation
  • chicory cotton
  • eggplant eucalyptus
  • flax flax
  • lentil eucalyptus
  • melon melon
  • papaya petunia
  • plum poplar
  • potato rice
  • soybean zucchini
  • sugar beet sugarcane
  • sunflower sweet pepper
  • sweet pepper tobacco, tomato
  • the one or more mutagenized or integrated genes are preferably selected from pat, epsps, cryl Ab, bar, cryl Fa2, cryl Ac, cry34Ab1 , cry35AB1 , cry3A, cryF, cryl F, mcry3a, cry2Ab2, cry3Bb1 , cry1 A.105, dfr, barnase, vip3Aa20, barstar, als, bxn, bp40, asnl , and ppo5.
  • the mutagenesis or integration of the one or more genes is performed in order to improve certain properties of the plant.
  • Such properties include abiotic stress tolerance, altered growth/yield, disease resistance, herbicide tolerance, insect resistance, modified product quality, and pollination control.
  • herbicide tolerance e.g. imidazolinone tolerance, glyphosate tolerance, or glufosinate tolerance
  • mutagenesis for example Clearfield® oilseed rape being tolerant to imidazoli- nones, e.g. imazamox.
  • genetic engineering methods have been used to render plants, such as soybean, cotton, corn, beets and oil seed rape, tolerant to herbicides, such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
  • herbicides such as glyphosate and glufosinate, some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
  • glyphosate and glufosinate some of which are commercially available under the trade names RoundupReady® (glyphosate) and LibertyLink® (glufosinate).
  • herbicides such as glyphosate and glufosinate
  • RoundupReady® glyphosate
  • LibertyLink® glufosinate
  • insect resistance is of importance, in particular lepidopteran insect resistance and coleopteran insect resistance.
  • Plants may be modified by mutagenesis or genetic engineering either in terms of one property (singular traits) or in terms of a combination of properties (stacked traits). Stacked traits, e.g. the combination of herbicide tolerance and insect resistance, are of increasing importance.
  • the pesticidal activity of the compounds of the present inven- tion may be enhanced by the insecticidal trait of a modified plant. Furthermore, it has been found that the compounds of the present invention are suitable for preventing insects to become resistant to the insecticidal trait or for combating pests, which already have become resistant to the insecticidal trait of a modified plant. Moreover, the compounds of the present invention are suitable for combating pests, against which the insecticidal trait is not effective, so that a com- plementary insecticidal activity can advantageously be used.
  • plant propagation material refers to all the generative parts of the plant such as seeds and vegetative plant material such as cuttings and tubers (e.g. potatoes), which can be used for the multiplication of the plant. This includes seeds, roots, fruits, tubers, bulbs, rhizomes, shoots, sprouts and other parts of plants. Seedlings and young plants, which are to be transplanted after germination or after emergence from soil, may also be included. These plant propagation materials may be treated prophylactically with a plant protection compound either at or before planting or transplanting.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like, and means in a preferred embodiment true seeds.
  • pesticidally effective amount means the amount of active ingredient needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidally effective amount can vary for the various com-pounds/compo- sitions used in the invention.
  • a pesticidally effective amount of the compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • the quantity of active ingredient ranges from 0.0001 to 500 g per 100 m2, preferably from 0.001 to 20 g per 100 m2.
  • the rate of application of the active ingredients of this invention may be in the range of 0.0001 g to 4000 g per hectare, e.g. from 1 g to 2 kg per hectare or from 1 g to 750 g per hectare, desirably from 1 g to 100 g per hectare, more desirably from 10 g to 50 g per hectare, e.g., 10 to 20 g per hectare, 20 to 30 g per hectare, 30 to 40 g per hectare, or 40 to 50 g per hectare.
  • the compounds of the present invention are particularly suitable for use in the treatment of seeds in order to protect the seeds from insect pests, in particular from soil-living insect pests, and the resulting seedling's roots and shoots against soil pests and foliar insects.
  • the present invention therefore also relates to a method for the protection of seeds from insects, in particular from soil insects, and of the seedling's roots and shoots from insects, in particular from soil and foliar insects, said method comprising treating the seeds before sowing and/or after pregermina- tion with a compound of the present invention.
  • the protection of the seedling's roots and shoots is preferred. More preferred is the protection of seedling's shoots from piercing and sucking insects, chewing insects and nematodes.
  • seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking, seed pelleting, and in-furrow application methods.
  • seed treatment application of the active compound is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
  • the present invention also comprises seeds coated with or containing the active compound.
  • coated with and/or containing generally signifies that the active ingredient is for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product is (re)planted, it may absorb the active ingredient.
  • Suitable seed is for example seed of cereals, root crops, oil crops, vegetables, spices, orna- mentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, melons, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
  • the active compound may also be used for the treatment of seeds from plants, which have been modified by mutagenisis or genetic engineering, and which e.g. tolerate the action of herbicides or fungicides or insecticides. Such modified plants have been described in detail above.
  • Conventional seed treatment formulations include for example flowable concentrates FS, solutions LS, suspoemulsions (SE), powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF. These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pregerminated the latter. Preferably, the formulations are applied such that germination is not included.
  • the active substance concentrations in ready-to-use formulations are preferably from 0.01 to 60% by weight, more preferably from 0.1 to 40 % by weight.
  • a FS formulation is used for seed treatment.
  • a FS formulation may comprise 1-800 g/l of active ingredient, 1-200 g/l Surfactant, 0 to 200 g/l antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • Especially preferred FS formulations of the compounds of the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredient, from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g.
  • a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
  • a binder sticker /adhesion agent
  • a preservative such as a biocide, antioxidant or the like
  • the application rates of the compounds of the invention are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, more preferably from 1 g to 1000 g per 100 kg of seed and in particular from 1 g to 200 g per 100 kg of seed, e.g. from 1 g to 100 g or from 5 g to 100 g per 100 kg of seed.
  • the invention therefore also relates to seed comprising a compound of the present invention, or an agriculturally useful salt thereof, as defined herein.
  • the amount of the compound of the pre- sent invention or the agriculturally useful salt thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
  • the method according to the invention is a method of controlling insects, which are resistant to an insecticide, which method comprises applying to said insecticide resistant insects at least one pesticidally active pyripyropene derivative of formula (I), wherein the insecticide to which the insect is resistant is from the following list of pesticides, grouped and numbered according the Mode of Action Classification of the Insecticide Resistance Action Committee (IRAC):
  • IRAC Insecticide Resistance Action Committee
  • Acetylcholine esterase (AChE) inhibitors from the class of AChE
  • a carbamates for example aldicarb, alanycarb, bendiocarb, benfuracarb, butocar-boxim, butoxycarboxim, carbaryl, carbofuran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pi-rimicarb, propoxur, thi- odicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of
  • organophosphates for example acephate, azamethiphos, azinphos-ethyl, az-inphosme- thyl, cadusafos, chlorethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos, chlorpyrifos-methyl, coumaphos, cyanophos, demeton-S-methyl, diazinon, dichlorvos/ DDVP, dicrotophos, dimetho- ate, dimethylvinphos, disulfoton, EPN, ethion, ethopro-phos, famphur, fenamiphos, fenitrothion, fenthion, fosthiazate, heptenophos, imicyafos, isofenphos, isopropyl O- (methoxyaminothio- phosphoryl) salicylate, isoxathion, mala-thion
  • M .3A pyrethroids for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans alle-thrin, bifen- thrin, bioallethrin, bioallethrin S-cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta- cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cyper-methrin, alpha-cyperme- thrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, fenpropathrin, f
  • M .3B sodium channel modulators such as DDT or methoxychlor
  • Nicotinic acetylcholine receptor agonists from the class of
  • M .4A neonicotinoids for example acteamiprid, chlothianidin, dinotefuran, imidacloprid, niten- pyram, thiacloprid and thiamethoxam; or the compounds
  • M .4A.2 1-[(6-chloro-3-pyridyl)methyl]-2-nitro-1-[(E)-pentylideneamino]guanidine; or
  • the method according to the invention is a method of controlling insects, which are resistant to an insecticide, which method comprises applying to said insecticide resistant insects at least one pesticidally active pyripyropene derivative of formula (I), wherein the insecticide to which the insect is resistant is a neonicotinoid compound.
  • the insecticide to which the insect is resistant is bifenthrin and/or imidacloprid.
  • the invention relates to a method of protecting a crop of useful plants susceptible to and/or under attack by insects, which are resistant to an insecticide, which method comprises applying to said crop, treating a plant propagation material of said crop with, and/or applying to said insecticide resistant insects, a compound of formula I as defined herein.
  • the invention relates to a method of controlling resistance to one or more insecticides in insects, which comprises alternately applying a compound of formula I as defined herein, and the insecticide, towards which the insects are resistant, to said insects or to a crop of useful plants susceptible to and/or under attack from said insects.
  • the methods are also preferred, wherein the insecticide resistant insect is from the order Hemiptera, Lepidoptera, Coleoptera or Diptera.
  • the methods are especially preferred, wherein the insecticide resistant insect is from the order selected from thrips, hoppers and whitefly.
  • the compounds of the present invention are especially suitable for efficiently combating animal pests such as arthropods, gastropods and nematodes including but not limited to:
  • insects from the order of Lepidoptera for example Achroia grisella, Acleris spp. such as A. fim- briana, A. gloverana, A. variana; Acrolepiopsis assectella, Acronicta major, Adoxophyes spp. such as A. cyrtosema, A. orana; Aedia leucomelas, Agrotis spp. such as A. exclamationis, A. fucosa, A. ipsilon, A. orthogoma, A. segetum, A.
  • Argyresthia conjugella Ar- gyroploce spp., Argyrotaen/a spp.
  • A. velutinana Athetis mindara, Austroasca viridigrisea, Autographa gamma, Autographa nigrisigna, Barathra brassicae, Bedell/a spp., Bonagota salubri- cola, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp. such as C. murinana, C.
  • Cactoblastis cactorum Cadra cautella, Ca lingo brazi liens is, Caloptilis theivora, Capua reticulana, Carposina spp. such as C. niponensis, C. sasakii; Cephus spp., Chaetocnema aridula, Cheimatobia brumata, Chilospp. such as C. Indicus, C. suppressalis, C. partellus; Choreut/s par/ana, Choristoneura spp. such as C. conflictana, C. fumiferana, C. lon- gicellana, C. murinana, C. occidentalis, C.
  • kuehniella kuehniella; Epinotia aporema, Epiphyas postvittana, Erannis tiliaria, Erionota thrax, Etiella spp., Eulia spp., Eupoecilia amb/guella, Euproct/s chrysorrhoea, Euxoa spp., Evetria bouliana, Faronta albilinea, Felt/a spp. such as F. subterranean; Galleria mellonella, Gracillaria spp., Grapholita spp. such as G. funebrana, G. molesta, G.
  • Mamestra spp. such as M. brassicae, M. configurata; Mamstra brassicae, Manduca spp. such as M. quinquemaculata, M. sexta; Marasmia spp, Marmara spp., Maruca testulalis, Megalopyge la- nata, Melanchra picta, Melanitis leda, Mods spp. such as M. lapites, M.
  • operculella Phylloc- nistis citrella, Phyllonorycter spp. such as P. blancardella, P. crataegella, P. issikii, P. ringoniella; P/ ' eris spp. such as P. brassicae, P. rapae, P. napi; Pilocrocis tripunctata, Plathypena scabra, Platynota spp. such as P. flavedana, P. idaeusalis, P.
  • stultana Platyptilia carduidactyla, Plebejus argus, Plod/a interpunctella, Plus/a spp, Plutella maculipennis, Plutella xylostella, Pont/ ' a pro- tod/ ' ca, Prays spp., Prodenia spp., Proxenus lepigone, Pseudaletia spp. such as P. sequax, P.
  • insects from the order of Coleoptera for example Acalymma vittatum, Acanthoscehdes obtectus, Adoretus spp., Agelastica alni, Agrilus spp. such as A. anx/ ' us, A. planipennis, A. sinuatus; Agri- otes spp. such as A. fuscicollis, A. lineatus, A. obscurus; Alphitobius diaperinus, Amphimallus solstitialis, Anisandrus dispar, Anisoplia austriaca, Anobium punctatum, Anomala diverenta, Anomala rufocuprea, Anoplophora spp. such as A.
  • Anthonomus spp. such as A. eugenii, A. grandis, A. pomorum; Anthrenus spp., Aphthona euphoridae, Apion spp., Apogonia spp., Athous haemorrhoidalis, Atomaria spp. such as A. linearis; Attagenus spp., Aulacophora femoralis, Blastophagus piniperda, Blitophaga undata, Bruchidius obtectus, Bruchus spp. such as B. lentis, B. pisorum, B.
  • vespertinus Conotrachelus nenuphar, Cosmopolites spp., Costelytra zealandica, Crioceris asparagi, Cryptolestes ferrugineus, Cryptorhynchus lapathi, Cten/ ' cera spp. such as C. destructor; Curculio spp., Cylindrocopturus spp., Cyclocephala spp., Dactyl/spa balyi, Dectes texanus, Dermestes spp., Diabrotica spp. such as D. undecimpunc- tata, D. speciosa, D. longicornis, D. sem > i punctata, D.
  • Diaprepes abbreviates, D/ ' cho- crocis spp., Dicladispa armigera, Diloboderus abderus, Diocalandra frumenti (Diocalandra st/g ' - maticollis), Enaphalodes rufulus, Epilachna spp. such as E varivestis, E vigintioctomaculata; Epitrix spp.
  • E hirtipennis such as E hirtipennis, E similaris; Eutheola humilis, Eutinobothrus brasiliensis, Faustinus cubae, Gibbium psyllo/des, Gnathocerus cornutus, Hellula undalis, Heteronychus ara- tor, Hylamorpha elegans, Hylobius abietis, Hylotrupes bajulus, Hypera spp. such as H. brun- neipennis, H.
  • hypomeces squamosus Hypothenemus spp., Ips typographus, Lach- nosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp. such as L. bilineata, L. melanopus; Leptinotarsa spp. such as L. decemlineata; Leptispa pygmaea, Limonius californicus, Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp. such as L.
  • Saperda Candida Scolytus schevyrewi, Scyphophorus acu- punctatus, Sitona lineatus, Sitophilus spp. such as S. granaria, S. oryzae, S. zeamais; Sphenoph- orus spp. such as S. levis; Stegobium paniceum, Sternechus spp. such as S. subsignatus; Strophomorphus ctenotus, Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tenebrioides mauretanicus, Tr/bolium spp. such as T.
  • Trogoderma spp. Tychius spp.
  • Xylotrechus spp. such as X. pyrrhoderus
  • Zabrus spp. such as Z. tenebrioides
  • insects from the order of Diptera for example Aedes spp. such as A. aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp. such as A. albimanus, A. crucians, A. freeborni, A. gambiae, A. leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A.
  • Aedes spp. such as A. aegypti, A. albopictus, A. vexans; Anastrepha ludens, Anopheles spp. such as A. albimanus, A. crucians, A. freeborni, A. gambiae, A. leucosphyrus, A. maculipennis, A. minimus, A. quadrimaculatus, A.
  • quinquefasciatus C. tarsalis, C. tritaeniorhynchus
  • Culicoides furens, Culiseta inornata, Culiseta melanura, Cuterebra spp. Dacus cucurbitae, Dacus oleae, Dasineura brassicae, Dasi- neura oxycoccana, Delia pp. such as D. antique, D. coarctata, D. platura, D. radicum
  • Dermato- bia hominis, Drosophila spp. such as D. suzukii, Fann/ ' a spp. such as F. canicularis
  • G. intestinalis such as G. intestinalis; Geomyza tipunctata, Gloss/ha spp. such as G. fuscipes, G. morsitans, G. pa I pa I is, G. tachinoides; Haematobia irritans, Haplodiplosis equestris, Hippelates spp., Hyle- myia spp. such as H. platura; Hypoderma spp. such as H. lineata; Hyppobosca spp., Hydrellia philippina, Leptoconops torrens, Liriomyza spp. such as L sativae, L. trifolii; Lucilia spp. such as L. caprina, L. cuprina, L.
  • Lycoria pectoral is, Mansonia ti til Ian us, Mayetiola spp. such as M. destructor; Musca spp. such as M. autumnalis, M. domestica; Muscina stabulans, Oestrus spp. such as O. ovis; Opomyza florum, Oscinella spp. such as O. frit; Orseolia oryzae, Pegomya hysocyami, Phlebotomus argentipes, Phorbia spp. such as P. antiqua, P. brassicae, P.
  • insects from the order of Thysanoptera for example, Basothrips biformis, Dichromothrips corbetti, Dichromothrips ssp., Echinothrips americanus, Enneothrips flavens, Frankliniella spp. such as F. fusca, F. occidentalis, F. tritici; Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Micro- cephalothrips abdominalis, Neohydatothrips samayunkur, Pezothrips kellyanus, Rhipiphorothrips cruentatus, Scirtothrips spp. such as S.
  • insects from the order of Hemiptera for example, Acizzia jamatonica, Acrosternum spp. such as A. hilare; Acyrthosipon spp. such as A. onobrychis, A. p/ ' sum; Adelges lar/c/s, Adelges tsugae, Adelphocor/s spp., such as A. rap/dus, A.
  • Brachycaudus spp. such as B. cardui, B. helichrysi, B. persicae, B. prunicola
  • Brachycolus spp. Brachycorynella asparagi, Brevicoryne brassicae, Cacopsylla spp. such as C. fulguralis, C.
  • Diaspis spp. such as D. bromeliae; Dichelops furcatus, Diconocoris hewetti, Doralis spp., Drey- fusia nordmannianae, Dreyfusia piceae, Drosicha spp., Dysaphis spp. such as D. plantaginea, D. pyri, D. radicola; Dysaulacorthum pseudosolani, Dysdercus spp. such as D. cingulatus, D. inter- minims; Dysmicoccus spp., Edessa spp., Geocoris spp., Empoasca spp.
  • Idiocerus spp. Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lecanoideus floccissimus, Lepi- dosaphes spp. such as L ulmi; Leptocor/sa spp., Leptoglossus phyllopus, Lipaphis erysimi, Lygus spp. such as L hesperus, L. lineolaris, L.
  • Macrosiphum spp. such as M. rosae, M. avenae, M.
  • Pter- omalus spp. Pulvinaria amygdali, Pyrilla spp., Quadraspidiotus spp., such as Q. perniciosus; Quesada gigas, Rastrococcus spp., Reduvius senilis, Rhizoecus americanus, Rhodnius spp., Rhopalomyzus ascalonicus, Rhopalosiphum spp. such as R. pseudobrassicas, R. insertum, R. maidis, R.
  • T. accerra, T. perditor Tibraca spp., Tomaspis spp., Tox- optera spp. such as T. aurantii; Trialeurodes spp. such as T. abutilonea, T. ricini, T. vaporariorum; Triatoma spp., Trioza spp., Typhlocyba spp., Unaspis spp. such as U. citri, U. yanonensis; and Viteus vitifolii,
  • Paravespula spp. such as P. germanica, P. pennsylvanica, P. vulgaris; Pheidole spp. such as P. megacepha la ; Pogonomyrmex spp. such as P. barbatus, P. californicus, Polistes rubiginosa, Prenolepis impairs, Pseudomyrmex gracilis, Schelipron spp., Sirex cyaneus, Solenopsis spp. such as S. geminata, S.invicta, S.
  • Insects from the order Orthoptera for example Acheta domesticus, Calliptamus italicus, Chor- toicetes termini fera, Ceuthophilus spp., Diastrammena asynamora, Dociostaurus maroccanus, Gryllotalpa spp. such as G. africana, G. gryllotalpa; Gryllus spp., Hieroglyphus daganensis, Kraussaria angulifera, Locusta spp. such as L migrator/a, L. pardalina; Melanoplus spp. such as M. bivittatus, M. femurrubrum, M. mexicanus, M. sanguinipes, M.
  • Pests from the Class Arachnida for example Acari.e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma spp. (e.g. A. americanum, A. variegatum, A. maculatum), Ar- gas spp. such as A. persicu), Boophilus spp. such as B. annulatus, B. decoloratus, B. microplus, Dermacentor spp. such as D.silvarum, D. andersoni, D. variabilis, Hyalomma spp. such as H. truncatum, Ixodes spp. such as /. ricinus, I.
  • Amblyomma spp. e.g. A. americanum, A. variegatum, A. maculatum
  • Ar- gas spp. such as A. persicu
  • Boophilus spp. such as B
  • rubicund us I. scapularis, I. holocyclus, I. pacificus, Rhipicephalus sanguineus, Ornithodorus spp. such as O. moubata, O. hermsi, O. turicata, Orni- thonyssus bacoti, Otobius megnini, Dermanyssus gallinae, Psoroptes spp. such as P. ovis, Rhipicephalus spp. such as R. sanguineus, R. appendiculatus, Rhipicephalus evertsi, Rhizogiyphus spp., Sarcoptes spp. such asS.
  • Halotydeus destructor Family Demodicidae with species such as Demodex spp.; Family Trombicidea including Trombicula spp.; Family Cellyssidae including Ornothonyssus spp.; Family Pyemotidae including Pyemotes tritici, Tyrophagus putrescentiae, Family Acaridae including Acarus siro, Family Araneida including Latrodectus mactans, Tegenaria agrestis, Chi- racanthium sp, Lycosa sp Achaearanea tepidariorum and Loxosceles reclusa; Pests from the Phylum Nematoda, for example, plant parasitic nematodes such as root-knot nematodes, Meloidogyne spp.
  • M. hapla such as M. hapla, M. incognita, M. javanica; cyst-forming nematodes, Globodera spp. such as G. rostochiensis; Heterodera spp. such as H. avenae, H. glycines, H. schachtii, H. trifolii; Seed gall nematodes, Angu/na spp.; Stem and foliar nematodes, Aphelenchoides spp. such as A. besseyi; Sting nematodes, Belonolaimus spp. such as B. longi- caudatus; Pine nematodes, Bursaphelenchus spp.
  • B. lignicolus such as B. lignicolus, B. xylophilus
  • Ring nematodes such as B. lignicolus, B. xylophilus
  • Mesocriconema spp./ Stem and bulb nematodes such as Z?. destructor, D.
  • brachyurus such as . brachyurus, P. neglec- tus, P. penetrans, P. curvitatus, P. goodeyi; Burrowing nematodes, Radopholus spp. such as ?. similis; Rhadopholus spp./ Rhodopholus spp./ Reniform nematodes, Rotylenchus spp. such as ?. robustus, R. reniformis; Scutellonema spp./ Stubby-root nematode, Trichodorus spp. such as 7 " . obtusus, T. primitivus; Paratrichodorus spp. such as .
  • Insects from the order Isoptera for example Calotermes flavicollis, Coptotermes spp. such as C formosanus, C. gestroi, C. acinaciformis; Cornitermes cumulans, Cryptotermes spp. such as C brew ' s, C. cavifrons; Globitermes sulfureus, Heterotermes spp. such as H. aureus, H. longiceps, H. tenuis; Leucotermes flavipes, Odontotermes spp., Incisitermes spp. such as /. /77/ 7or, /. Snyder, Marginitermes hubbardi, Mastotermes spp. such as darwiniensis Neocapritermes spp.
  • Neotermes spp. such as /V. opacus, N. parvus; Neotermes spp., Procornitermes spp., Zootermopsis spp. si/c 7 as Z angusticollis, Z. nevadensis, Reticulitermes spp. such as ?. hesperus, R. tibialis, R. speratus, R. flavipes, R. grassei, R. lucifugus, R. santonensis, R. virginicus; Termes natalensis,
  • Insects from the order Siphonoptera for example Cediopsylla simples, Ceratophyllus spp., Cten- ocephalides spp. such as C. fells, C. canis, Xenopsylla cheopis, Pulex irritans, Trichodectes ca- nis, Tunga penetrans, and Nosopsyllus fasciatus,
  • Thysanura for example Lepisma saccharina , Ctenolepisma urbana, and Thermobia domestica
  • Pests from the class Chilopoda for example Geophilus spp., Scutigera spp. such as Scutigera coleoptrata,
  • Pests from the class Diplopoda for example Blaniulus guttulatus, Julus spp., Narceus spp.
  • Pests from the class Symphyla for example Scutigerella immaculata
  • Insects from the order Collembola for example Onychiurus spp., such as Onychiurus armatus, Pests from the order Isopoda for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber,
  • Pedicuius spp. such as Pedicuius humanus capitis, Pedicuius humanus corporis, Pedicuius humanus humanus; Pthirus pubis, Haematopinus spp. such as Haematopinus eurysternus, Haematopinus su/ ' s, Linognathus spp. such as Linognathus vituli; Bovicola bovis, Menopon gallinae, Menacanthus stramineus and So- lenopotes capillatus, Trichodectes spp.,
  • Examples of further pest species which may be controlled by compounds of fomula (I) include: from the Phylum Mollusca, class Bivalvia, for example, Dre/ ' ssena spp.; class Gastropoda, for example, Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea canaliclata, Succinea spp.; from the class of the helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancy- lostoma spp., Ascaris lubricoides, Ascaris spp., Brug/ ' a malayi, Brug/ ' a timori, Bunostomum spp., Chaberti
  • pest species which may be controlled by compounds of formula (I) include: Anisoplia austriaca, Apamea spp., Austroasca viridigrisea, Baliothrips biformis, Caenorhabditis elegans, Cephus spp., Ceutorhynchus napi, Chaetocnema aridula, Chilo auricilius, Chilo indicus , Chilo polychrysus, Chortiocetes termini fera, Cnaphalocroci medinalis, Cnaphalocrosis spp., Col/ ' as eurytheme, Collops spp., Cornitermes cumulans, Creontiades spp., Cyclocephala spp., Dalbulus ma/ ' d/s, Deraceras reticulatum , Diatrea saccharalis, Dichelops furcatus, Dicladispa ar- migera ,
  • Diloboderus abderus such as Diloboderus abderus; Edessa spp., Epinotia spp., Formici- dae, Geocor/s spp., Glob/ ' termes sulfureus, Gryllotalpidae, Halotydeus destructor, Hipnodes bi- color, Hydrellia philippina, Julus spp., Laodelphax spp., Leptocorsia acuta , Leptocorsia ora tori us , Liogenys fuscus, Luc/ilia spp., Lyogenys fuscus, Mahanarva spp., Maladera matrida, Ma- rasmia spp., Mastotermes spp., Mealybugs, Megascelis ssp, Metamasius hemipterus, M/ ' cro- theca spp., Mods lat/p '
  • Orseolia oryzae such as Orseolia oryzae; Oxycaraenus hyalinipennis, Plus/ ' a spp., Pomacea canaliculate, Procornitermes ssp, Procornitermes triacifer, Psylloides spp., Rachiplusia spp., Rhodopholus spp., Scaptocoris casta nea, Scaptocoris spp., Scirpophaga spp. such as Scirpophaga incertulas , Scirpophaga innotata; Scotinophara spp. such as Scotinophara coarc- tata; Sesamia spp.
  • the methods of the invention are particularly applicable to the control of resistant insects (and resistance in insects) of the family Aphididae, such as: Acyrthosiphum pisum, Aphis citricola, Aphis craccivora, Aphis fabae, Aphis frangu-lae, Aphis glycines, Aphis gossypii, Aphis nasturtii, Aphis pomi, Aphis spiraecola, Aulacorthum solan/, ' Brachycaudus helichrysi, Brevicoryne brassi- cae, Diuraphis noxia, Dysaphis devecta, Dysaphis plantaginea, Eriosoma lanigerum, Hyalopte- rus pruni, Li-paphis erysimi, Macrosiphum avenae, Macrosiphum euphorbiae, Macrosiphum ro-
  • the methods of the invention are particularly applicable for the control of neonicotinoid resistant insects (and the neonicotinoid resistance in such insects) of these families.
  • neonicotinoid resistant aphids include Acyrthosiphum pisum, Aphis citricola, Aphis craccivora, Aphis fabae, Aphis frangulae, Aphis glycines, Aphis gossypii, Aphis nasturtii, Aphis pomi, Aphis spiraecola, Aulacorthum solan/, ' Brachycaudus helichrysi, Brevicoryne brassicae, Diuraphis noxia, Dysaphis devecta, Dysaphis plantaginea, Eriosoma lanigerum, Hyalopterus pruni, Lipaphis erysimi, Macrosiphum avenae, Macrosiphum euphorbiae,
  • Macrosiphum rosae Myzus cerasi F, Myzus nicotianae, Myzus persicae, Nasonovia ribisnigri, Pemphigus bursar/us, Phorodon humuli, Rhopalosiphum insertum Wa, Rhopalosiphum A/ ' d/s Fitch, Rhopalosiphum pad/ ' L, Schizaphis graminum Rond., Sitobion avenae, Toxoptera aurantii, Toxoptera citricola, and Phylloxera vitifoliae.
  • a resistant aphid controlled by the compound of the invention is also resistant to pyrethroid insecticides, such as Lambda-cyhalothrin.
  • the insect may be resistant to neonicotionid insecticide and/or pyrethroid insecticides.
  • the compounds of the present invention including their stereoisomers, salts, tautomers and N-ox- ides, are particularly useful for controlling chewing-biting pests, in particular insects from the or- der of Lepidoptera and Coleoptera.
  • the compounds of the present invention are particularly useful for controlling sucking or piercing insects, in particular insects from the order Diptera.
  • the insecticide resistant insect is from the order Lepidoptera, Coleoptera or Diptera.
  • the insecticide resistant insect is from the order Lepidop- tera and is selected from Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gem- matalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandio- sella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella
  • the insecticide resistant insect is from the order Cole- optera (beetles) and is selected from Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Am- phimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aph- thona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blastophagus piniperda, Blitoph- aga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata, Ceuthorrhynchus assimilis, Ceuthorrhynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris aspar
  • the insecticide resistant insect is a potato beetle, more specifically the Colorado potato beetle.
  • the insecticide resistant insect is from the order Diptera and is selected from Aedes aegypti, Aedes albop/ctus, Aedes vexans, Anastrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimacula- tus, Call/phora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens
  • the insecticide resistant insect is selected from thrips, hoppers and whitefly.
  • the insecticide resistant insect is one or more of Tuta absolute, P/ ' eris rapae, Trichoplusia ni, Plutella xylostella, Spodoptera littoral is, Spodoptera frugiperda, Crocidolomia pavonana, Cnaphalocerus medinalis, Sesamia in- ferens, Chilo suppressalis, Pyrausta furnacalis, Thermesia gem ma talis, Liriomyza sp., Lepti no- tarsus decemlineata, Epitrixsp., Phyllotreta cruciferae, Meligethes aeneus, Hypera brunneipen- nis; Nilaparvata lugens, Nephotettix v/ ' rens; Acyrthosiphum p/ ' sum, Bemisia tabaci,
  • the insecticide resistant insect is one or more of Tuta absolute, P/ ' eris rapae, Trichoplusia ni, Plutella xylostella, Chilo suppressalis, Liriomyza sp., Leptinotarsus decemlineata, Epitrixsp., Phyllotreta cruciferae, Franklinella occidentalis, Bemisia tabaci, Bemisia argentifolii, Agrotis ypsilon.
  • the insecticide resistant insect is one or more oft Agrotis ypsilon, Heliothis virescens, Plutella xylostella, Agriotes lineatus, Diabrotica virgifera, Hypera brunneipennis, Leptinotarsus decemlineata, Phyllotreta striolata.
  • the invention also relates to agrochemical compositions comprising an auxiliary and at least one compound of the present invention or a mixture thereof.
  • An agrochemical composition comprises a pesticidally effective amount of a compound of the present invention or a mixture thereof.
  • the term "pesticidally effective amount” is defined below.
  • the compounds of the present invention or the mixtures thereof can be converted into customary types of agro-chemical compositions, e. g. solutions, emulsions, suspensions, dusts, powders, pastes, granules, pressings, capsules, and mixtures thereof.
  • Examples for composi-tion types are suspensions (e.g. SC, OD, FS), emulsifiable concentrates (e.g. EC), emulsions (e.g. EW, EO, ES, ME), capsules (e.g.
  • compositions types are defined in the "Catalogue of pesticide formulation types and international coding system", Technical Monograph No. 2, 6th Ed. May 2008, CropLife International.
  • compositions are prepared in a known manner, such as described by Mollet and Grube- mann, Formulation technology, Wiley VCH, Weinheim, 2001 ; or Knowles, New developments in crop protection product formulation, Agrow Reports DS243, T&F Informa, London, 2005.
  • auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants, tackifi-ers and binders.
  • suitable auxiliaries are solvents, liquid carriers, solid carriers or fillers, surfac-tants, dispersants, emulsifiers, wetters, adjuvants, solubilizers, penetration enhancers, protec-tive colloids, adhesion agents, thickeners, humectants, repellents, attractants, feeding stimu-lants, compatibilizers, bactericides, anti-freezing agents, anti-foaming agents, colorants,
  • Suitable solvents and liquid carriers are water and organic solvents, such as mineral oil fractions of medium to high boiling point, e.g. kerosene, diesel oil; oils of vegetable or animal origin; aliphatic, cyclic and aromatic hydrocarbons, e. g. toluene, paraffin, tetrahydronaphthalene, alkylated naphthalenes; alcohols, e.g. ethanol, propanol, butanol, benzylalcohol, cyclohexanol; glycols; DMSO; ketones, e.g. cyclohexanone; esters, e.g.
  • mineral oil fractions of medium to high boiling point e.g. kerosene, diesel oil
  • oils of vegetable or animal origin oils of vegetable or animal origin
  • aliphatic, cyclic and aromatic hydrocarbons e. g. toluene, paraffin, tetrahydronaphthalene, alkylated
  • lactates carbonates, fatty acid esters, gamma-butyrolactone; fatty acids; phosphonates; amines; amides, e.g. N-methylpyrrolidone, fatty acid dimethylamides; and mixtures thereof.
  • Suitable solid carriers or fillers are mineral earths, e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide; polysaccharide powders, e.g. cellulose, starch; fertilizers, e.g. ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas; products of vegetable origin, e.g. cereal meal, tree bark meal, wood meal, nutshell meal, and mixtures thereof.
  • mineral earths e.g. silicates, silica gels, talc, kaolins, limestone, lime, chalk, clays, dolomite, diatomaceous earth, bentonite, calcium sulfate, magnesium sulfate, magnesium oxide
  • polysaccharide powders e.g. cellulose, starch
  • Suitable surfactants are surface-active compounds, such as anionic, cationic, nonionic and amphoteric surfactants, block polymers, polyelectrolytes, and mixtures thereof. Such surfactants can be used as emusifier, dispersant, solubilizer, wetter, penetration enhancer, protective colloid, or adjuvant. Examples of surfactants are listed in McCutcheon's, Vol.1 : Emulsifiers & Detergents, McCutcheon's Directories, Glen Rock, USA, 2008 (International Ed. or North American Ed.).
  • Suitable anionic surfactants are alkali, alkaline earth or ammonium salts of sulfonates, sul-fates, phosphates, carboxylates, and mixtures thereof.
  • sulfonates are alkylaryl-sul- fonates, diphenylsulfonates, alpha-olefin sulfonates, lignine sulfonates, sulfonates of fatty acids and oils, sulfonates of ethoxylated alkylphenols, sulfonates of alkoxylated arylphenols, sulfonates of condensed naphthalenes, sulfonates of dodecyl- and tridecylbenzenes, sulfonates of naphthalenes and alkylnaphthalenes, sulfosuccinates or sulfosuccinamates.
  • Examples of sul- fates are sulfates of fatty acids and oils, of ethoxylated alkylphenols, of alcohols, of ethox-ylated alcohols, or of fatty acid esters.
  • Examples of phosphates are phosphate esters.
  • Exam-pies of carboxylates are alkyl carboxylates, and carboxylated alcohol or alkylphenol eth-oxylates.
  • Suitable nonionic surfactants are alkoxylates, N-subsituted fatty acid amides, amine oxides, es- ters, sugar-based surfactants, polymeric surfactants, and mixtures thereof.
  • alkox- ylates are compounds such as alcohols, alkylphenols, amines, amides, arylphenols, fatty acids or fatty acid esters which have been alkoxylated with 1 to 50 equivalents.
  • Ethylene oxide and/or propylene oxide may be employed for the alkoxylation, preferably ethylene oxide.
  • Exam-pies of N-subsititued fatty acid amides are fatty acid glucamides or fatty acid alkanolamides.
  • esters are fatty acid esters, glycerol esters or monoglycerides.
  • sugar-based surfactants are sorbitans, ethoxylated sorbitans, sucrose and glucose esters or alkylpolygluco- sides.
  • polymeric surfactants are homo- or copolymers of vinylpyrrolidone, vinylal- cohols, or vinylacetate.
  • Suitable cationic surfactants are quaternary surfactants, for example quaternary ammonium compounds with one or two hydrophobic groups, or salts of long-chain primary amines.
  • Suitable amphoteric surfactants are alkylbetains and imidazolines.
  • Suitable block polymers are block polymers of the A-B or A-B-A type comprising blocks of polyethylene oxide and polypropylene oxide, or of the A-B-C type comprising alkanol, polyethylene oxide and polypropylene oxide.
  • Suita- ble polyelectrolytes are polyacids or polybases. Examples of polyacids are alkali salts of poly- acrylic acid or polyacid comb polymers. Examples of polybases are polyvinylamines or polyeth- yleneamines.
  • Suitable adjuvants are compounds, which have a neglectable or even no pesticidal activity themselves, and which improve the biological performance of the compounds of the present in- vention on the target.
  • examples are surfactants, mineral or vegetable oils, and other auxilaries. Further examples are listed by Knowles, Adjuvants and additives, Agrow Reports DS256, T&F Informa UK, 2006, chapter 5.
  • Suitable thickeners are polysaccharides (e.g. xanthan gum, carboxymethylcellulose), anorgan-ic clays (organically modified or unmodified), polycarboxylates, and silicates.
  • Suitable bactericides are bronopol and isothiazolinone derivatives such as alkylisothiazoli-nones and benzisothiazolinones.
  • Suitable anti-freezing agents are ethylene glycol, propylene glycol, urea and glycerin.
  • Suitable anti-foaming agents are silicones, long chain alcohols, and salts of fatty acids.
  • Suitable colorants are pigments of low water solubility and water-sol- uble dyes.
  • examples are inorganic colorants (e.g. iron oxide, titan oxide, iron hexacyanofer- rate) and organic colorants (e.g. alizarin-, azo- and phthalocyanine colorants).
  • Suitable tackifiers or binders are polyvinylpyrrolidons, polyvinylacetates, polyvinyl alcohols, pol- yacrylates, biological or synthetic waxes, and cellulose ethers.
  • composition types and their preparation are:
  • a compound I or II according to the invention 10-60 wt% of a compound I or II according to the invention and 5-15 wt% wetting agent (e.g. alcohol alkoxylates) are dissolved in water and/or in a water-soluble solvent (e.g. alcohols) up to
  • the active substance dissolves upon dilution with water.
  • a compound I or II according to the invention 5-25 wt% of a compound I or II according to the invention and 1 -10 wt% dispersant (e. g. polyvinylpyrrolidone) are dissolved in up to 100 wt% organic solvent (e.g. cyclohexanone). Dilution with water gives a dispersion.
  • dispersant e. g. polyvinylpyrrolidone
  • Emulsifiable concentrates 15-70 wt% of a compound I or II according to the invention and 5-10 wt% emulsifiers (e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate) are dissolved in up to 100 wt% water- insoluble organic solvent (e.g. aromatic hydrocarbon). Dilution with water gives an emulsion, iv) Emulsions (EW, EO, ES)
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • emulsifiers e.g. calcium dodecylbenzenesulfonate and castor oil ethoxylate
  • 20-40 wt% water-insoluble organic solvent e.g. aromatic hydrocarbon
  • a compound I or II according to the invention are comminuted with addition of 2-10 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate), 0,1-2 wt% thickener (e.g. xanthan gum) and up to 100 wt% water to give a fine active substance suspension. Dilution with water gives a stable suspension of the active sub-stance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 01-2 wt% thickener e.g. xanthan gum
  • 50-80 wt% of a compound I or II according to the invention are ground finely with addition of up to 100 wt% dispersants and wetting agents (e.g. sodium lignosulfonate and alcohol ethoxylate) and prepared as water-dispersible or water-soluble granules by means of technical appliances (e. g. extrusion, spray tower, fluidized bed). Dilution with water gives a stable dispersion or solution of the active substance.
  • dispersants and wetting agents e.g. sodium lignosulfonate and alcohol ethoxylate
  • 50-80 wt% of a compound I or II according to the invention are ground in a rotor-stator mill with ad-dition of 1-5 wt% dispersants (e.g. sodium lignosulfonate), 1 -3 wt% wetting agents (e.g. alco- hoi ethoxylate) and up to 100 wt% solid carrier, e.g. silica gel. Dilution with water gives a stable dis-persion or solution of the active substance.
  • 1-5 wt% dispersants e.g. sodium lignosulfonate
  • 1 -3 wt% wetting agents e.g. alco- hoi ethoxylate
  • solid carrier e.g. silica gel
  • a compound I or II according to the invention are comminuted with addition of 3-10 wt% dispersants (e.g. sodium lignosulfonate), 1-5 wt% thickener (e.g. car-boxymethylcellulose) and up to 100 wt% water to give a fine suspension of the active sub-stance. Dilution with water gives a stable suspension of the active substance.
  • dispersants e.g. sodium lignosulfonate
  • 1-5 wt% thickener e.g. car-boxymethylcellulose
  • 5-20 wt% of a compound I or II according to the invention are added to 5-30 wt% organic solvent blend (e.g. fatty acid dimethylamide and cyclohexanone), 10-25 wt% surfactant blend (e.g. alkohol ethoxylate and arylphenol ethoxylate), and water up to 100 %.
  • organic solvent blend e.g. fatty acid dimethylamide and cyclohexanone
  • surfactant blend e.g. alkohol ethoxylate and arylphenol ethoxylate
  • An oil phase comprising 5-50 wt% of a compound I or II according to the invention, 0-40 wt% water insoluble organic solvent (e.g. aromatic hydrocarbon), 2-15 wt% acrylic monomers (e.g. methylmethacrylate, methacrylic acid and a di- or triacrylate) are dispersed into an aqueous solution of a protective colloid (e.g. polyvinyl alcohol). Radical polymerization initiated by a radi-cal initiator results in the formation of poly(meth)acrylate microcapsules.
  • an oil phase comprising 5-50 wt% of a compound I or II according to the invention, 0-40 wt% water insolu-ble organic solvent (e.g.
  • an isocyanate monomer e.g. diphenylme- thene-4,4'-diisocyanatae
  • a protective colloid e.g. polyvinyl alcohol
  • the addition of a polyamine results in the formation of a polyurea microcapsule.
  • the monomers amount to 1 -10 wt%. The wt% relate to the total CS composition.
  • Dustable powders (DP, DS)
  • 1 -10 wt% of a compound I or II according to the invention are ground finely and mixed intimately with up to 100 wt% solid carrier, e.g. finely divided kaolin.
  • 0.5-30 wt% of a compound I or II according to the invention is ground finely and associated with up to 100 wt% solid carrier (e.g. silicate). Granulation is achieved by extrusion, spray-drying or the fluidized bed.
  • solid carrier e.g. silicate
  • a compound I or II according to the invention are dissolved in up to 100 wt% organic solvent, e.g. aromatic hydrocarbon.
  • compositions types i) to xi) may optionally comprise further auxiliaries, such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • auxiliaries such as 0.1 -1 wt% bactericides, 5-15 wt% anti-freezing agents, 0.1-1 wt% anti-foaming agents, and 0.1-1 wt% colorants.
  • the agrochemical compositions generally comprise between 0.01 and 95%, preferably between 0.1 and 90%, and most preferably between 0.5 and 75%, by weight of active sub-stance.
  • the active substances are employed in a purity of from 90% to 100%, preferably from 95% to 100% (according to NMR spectrum).
  • oils, wetters, adjuvants, fertilizer, or micronutrients, and other pesticides may be added to the active substances or the compositions comprising them as premix or, if appropriate not until immedi- ately prior to use (tank mix).
  • pesticides e.g. herbicides, insecticides, fungicides, growth regulators, safeners
  • These agents can be admixed with the compositions according to the invention in a weight ratio of 1 :100 to 100:1 , preferably 1 :10 to 10:1.
  • the user applies the composition according to the invention usually from a predosage de-vice, a knapsack sprayer, a spray tank, a spray plane, or an irrigation system.
  • the agrochemical composition is made up with water, buffer, and/or further auxiliaries to the desired applica- tion concentration and the ready-to-use spray liquor or the agrochemical composition according to the invention is thus obtained.
  • 20 to 2000 liters, preferably 50 to 400 liters, of the ready-to-use spray liquor are applied per hectare of agricultural useful area.
  • composition according to the invention such as parts of a kit or parts of a binary or ternary mixture may be mixed by the user himself in a spray tank and further auxiliaries may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components may be mixed by the user in a spray tank and further auxiliaries and additives may be added, if appropriate.
  • either individual components of the composition according to the invention or partially premixed components e. g. components comprising compounds of the present invention and/or mixing partners as defined above, can be applied jointly (e.g. after tank mix) or consecutively.
  • the present invention also relates to a mixture of at least one compound of the present invention with at least one mixing partner as defined herein after.
  • Preferred weight ratios for such binary mixtures are from 5000:1 to 1 :5000, preferably from 1000:1 to 1 :1000, more preferably from 100:1 to 1 :100, particularly preferably from 10:1 to 1 :10.
  • components I and II may be used in equal amounts, or an excess of component I, or an excess of component II may be used.
  • Mixing partners can be selected from pesticides, in particular insecticides, nematicides, and acaricides, fungicides, herbicides, plant growth regulators, fertilizers, and the like.
  • Preferred mixing partners are insecticides, nematicides and fungicides.
  • M .1 Acetylcholine esterase (AChE) inhibitors from the class of: M.1 A carbamates, for example aldicarb, alanycarb, bendiocarb, benfuracarb, butocarboxim, butoxycarboxim, carbaryl, carbofu- ran, carbosulfan, ethiofencarb, fenobucarb, formetanate, furathiocarb, isoprocarb, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, xylylcarb and triazamate; or from the class of M.1 B organophosphates, for example acephate, azamethiphos, azinphos-ethyl, azinphosmethyl, cadusafos, chlorethoxyfos, chlorf
  • GABA-gated chloride channel antagonists such as: M.2A cyclodiene organochlorine compounds, as for example endosulfan or chlordane; or M.2B fiproles (phenylpyrazoles), as for example ethiprole, fipronil, flufiprole, pyrafluprole and pyriprole;
  • M .3 Sodium channel modulators from the class of M.3A pyrethroids for example acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S- cylclopentenyl, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda- cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha-cypermethrin, beta-cypermethrin, theta- cypermethrin, zeta-cypermethrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate, etofenprox, f
  • M.3B sodium channel modulators such as DDT or methoxychlor
  • M .6 Chloride channel activators from the class of avermectins and milbemycins, for example abamectin, emamectin benzoate, ivermectin, lepimectin or milbemectin;
  • M .7 Juvenile hormone mimics such as M.7A juvenile hormone analogues as hydroprene, ki- noprene and methoprene; or others as M.7B fenoxycarb or M.7C pyriproxyfen;
  • M .8 miscellaneous non-specific (multi-site) inhibitors for example M.8A alkyl halides as methyl bromide and other alkyl halides, or M.8B chloropicrin, or M.8C sulfuryl fluoride, or M.8D borax, or M .8E tartar emetic;
  • M .9 Selective homopteran feeding blockers for example M.9B pymetrozine, or M.9C floni- camid;
  • M .10 Mite growth inhibitors for example M.10A clofentezine, hexythiazox and diflovidazin, or M .10B etoxazole;
  • M .1 1 Microbial disruptors of insect midgut membranes for example bacillus thuringiensis or bacillus sphaericus and the insecticdal proteins they produce such as bacillus thuringiensis subsp. israelensis, bacillus sphaericus, bacillus thuringiensis subsp. aizawai, bacillus thuringiensis subsp. kurstaki and bacillus thuringiensis subsp. tenebrionis, or the Bt crop proteins: CrylAb, CrylAc, Cryl Fa, Cry2Ab, mCry3A, Cry3Ab, Cry3Bb and Cry34/35Ab1 ;
  • M .12 Inhibitors of mitochondrial ATP synthase for example M.12A diafenthiuron, or M.12B or- ganotin miticides such as azocyclotin, cyhexatin or fenbutatin oxide, or M.12C propargite, or M .12D tetradifon;
  • Nicotinic acetylcholine receptor (nAChR) channel blockers for example nereistoxin analogues as bensultap, cartap hydrochloride, thiocyclam or thiosultap sodium;
  • benzoylureas as for example bistriflu- ron, chlorfluazuron, diflubenzuron, flucycloxuron, flufenoxuron, hexaflumuron, lufenuron, novalu- ron, noviflumuron, teflubenzuron or triflumuron;
  • M .16 Inhibitors of the chitin biosynthesis type 1 as for example buprofezin;
  • Ecdyson receptor agonists such as diacylhydrazines, for example methoxyfenozide, tebufenozide, halofenozide, fufenozide or chromafenozide;
  • Octopamin receptor agonists as for example amitraz
  • M .20 Mitochondrial complex III electron transport inhibitors for example M.20A hydramethyl- non, or M.20B acequinocyl, or M .20C fluacrypyrim;
  • M .21 Mitochondrial complex I electron transport inhibitors for example M.21 A METI acaricides and insecticides such as fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad or tolfenpyrad, or M.21 B rotenone; M .22 Voltage-dependent sodium channel blockers, for example M.22A indoxacarb, or M .22B metaflumizone, or M.22B.1 : 2-[2-(4-Cyanophenyl)-1 -[3-(trifluoromethyl)phenyl]ethylidene]-N-[4- (difluoromethoxy)phenyl]-hydrazinecarboxamide or M.22B.2: N-(3-Chloro-2-methylphenyl)-2-[(4- chlorophenyl)[4-[methyl(methylsulfonyl)amino
  • M .23 Inhibitors of the of acetyl CoA carboxylase such as Tetronic and Tetramic acid derivatives, for example spirodiclofen, spiromesifen or spirotetramat;
  • M .24 Mitochondrial complex IV electron transport inhibitors for example M.24A phosphine such as aluminium phosphide, calcium phosphide, phosphine or zinc phosphide, or M.24B cya-nide; M .25 Mitochondrial complex II electron transport inhibitors, such as beta-ketonitrile derivatives, for example cyenopyrafen or cyflumetofen;
  • M .28 Ryanodine receptor-modulators from the class of diamides, as for example flubendia- mide, chlorantraniliprole (rynaxypyr®), cyantraniliprole (cyazypyr®), tetraniliprole, or the phthalamide compounds M.28.1 : (R)-3-Chlor-N 1- ⁇ 2-methyl-4-[1 ,2,2,2 -tetrafluor-1- (trifluormethyl)ethyl]phenyl ⁇ -N2-(1 -methyl-2-methylsulfonylethyl)phthalamid and M.28.2: (S)-3- Chlor-N 1 - ⁇ 2-methyl-4-[1 ,2,2,2 -tetrafluor-1 -(trifluormethyl)ethyl]phenyl ⁇ -N2-(1 -methyl-2- methylsulfonylethyl)phthalamid, or the compound M.28.3: 3-bromo-N- ⁇ 2-
  • M .29. insecticidal active compounds of unknown or uncertain mode of action as for example afidopyropen , afoxolaner, azadirachtin, amidoflumet, benzoximate, bifenazate, broflanilide, bromopropylate, chinomethionat, cryolite, dicloromezotiaz , dicofol, flufenerim, flometoquin, fluensulfone, fluhexafon, fluopyram, flupyradifurone, fluralaner , metoxadiazone, piperonyl butoxide, pyflubumide, pyridalyl, pyrifluquinazon, sulfoxaflor, tioxazafen, triflumezopyrim, or the compounds M .29.3: 1 1 -(4-chloro-2,6-dimethylphenyl)-12-hydroxy-1 ,4-dio
  • M .29.14a 1 -[(6-Chloro-3-pyridinyl)methy1]-1 ,2,3,5,6 J-hexahydro-5-methoxy-7-methy1-8-nitro- imidazo[1 ,2-a]pyridine; or M.29.14b) 1 -[(6-Chloropyridin-3-yl)methyl]-7-methyl-8-nitro- 1 ,2,3,5,6,7-hexahydroimidazo[1 ,2-a]pyridin-5-ol; or the compounds
  • M .29.16a 1 -isopropyl-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; or M.29.16b) 1 - (1 ,2-dimethylpropyl)-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide; M.29.16c) N ,5- dimethyl-N-pyridazin-4-yl-1 -(2,2,2-trifluoro-1 -methyl-ethyl)pyrazole-4-carboxamide; M .29.16d) 1 - [1 -(1 -cyanocyclopropyl)ethyl]-N-ethyl-5-methyl-N-pyridazin-4-yl-pyrazole-4-carboxamide;
  • M .29.16e N-ethyl-1 -(2-fluoro-1 -methyl-propyl)-5-methyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M.29.16f 1 -(1 ,2-dimethylpropyl)-N,5-dimethyl-N-pyridazin-4-yl-pyrazole-4- carboxamide
  • M.29.16h N-methyl-1-(2-fluoro-1-methyl-propyl]-5-methyl-N-pyridazin-4-yl- pyrazole-4-carboxamide
  • the M.4 neonicotinoid cycloxaprid is known from WO2010/069266 and WO201 1/069456, the neonicotinoid M.4A.2, sometimes also to be named as guadipyr , is known from
  • WO2013/003977 and the neonicotinoid M.4A.3 (approved as paichongding in China) is known from WO2007/101369.
  • the metaflumizone analogue M.22B.1 is described in CN 10171577 and the analogue M.22B.2 in CN 102126994.
  • the phthalamides M.28.1 and M.28.2 are both known from WO2007/101540.
  • the anthranilamide M.28.3 is described in WO2005/077934.
  • the hydra- zide compound M.28.4 is described in WO2007/043677.
  • the anthranilamides M.28.5a) to M .28.5d) and M.28.5h) are described in WO 2007/006670, WO2013/024009 and
  • WO2013/024010 the anthranilamide ⁇ .28.5 ⁇ ) is described in WO201 1/085575, M .28.5j) in WO2008/134969, M.28.5k) in US201 1/046186 and M.28.5I) in WO2012/034403.
  • the diamide compounds M.28.6 and M.28.7 can be found in CN 102613183.
  • the spiroketal-substituted cyclic ketoenol derivative M.29.3 is known from WO2006/089633 and the biphenyl-substituted spiro- cyclic ketoenol derivative M .29.4 from WO2008/06791 1.
  • the triazoylphenylsulfide M .29.5 is described in WO2006/043635, and biological control agents on the basis of bacillus firmus are described in WO2009/124707.
  • the compounds M.29.6a) to M.29.6i ) listed under M.29.6 are described in WO2012/029672, and M.29.6j) and M.29.6k) in WO2013/129688.
  • the nematicide M .29.8 is known from WO2013/055584.
  • the isoxazoline M.29.9.a) is described in
  • WO2013/050317 The isoxazoline M.29.9.b) is described in WO2014/126208.
  • the pyridalyl- type analogue M.29.10 is known from WO2010/060379.
  • the carboxamides broflanilide and M .29.1 1 .b) to M.29.1 1 .h) are described in WO2010/018714, and the carboxamides ⁇ .29.1 1 ⁇ ) to M .29.1 1 .p) in WO2010/127926.
  • the pyridylthiazoles M.29.12.a) to M.29.12.C) are known from WO2010/006713, M.29.12.d) and M.29.12.e) are known from WO2012/000896, and M.29.12.f) to M.29.12.ITI) from WO2010/129497 .
  • the compounds M.29.14a) and M.29.14b) are known from WO2007/101369.
  • the pyrazoles M.29.16.a) to M .29.16h) are described in
  • Inhibitors of complex III at Qo site e. g. strobilurins: azoxystrobin (A.1 .1 ), coumethoxy- strobin (A.1 .2), coumoxystrobin (A.1 .3), dimoxystrobin (A.1 .4), enestroburin (A.1.5), fenamin- strobin (A.1 .6), fenoxystrobin/flufenoxystrobin (A.1.7), fluoxastrobin (A.1.8), kresoxim-methyl (A.1.9), mandestrobin (A.1 .10), metominostrobin (A.1.1 1 ), orysastrobin (A.1.12), picoxy.strobin (A.1.13), pyraclostrobin (A.1 .14), pyrametostrobin (A.1 .15), pyraoxystrobin (A.1 .16), tri- floxystrobin (A.1.17),
  • inhibitors of complex II e. g. carboxamides: benodanil (A.3.1 ), benzovindiflupyr (A.3.2), bixafen (A.3.3), boscalid (A.3.4), carboxin (A.3.5), fenfuram (A.3.6), fluopyram (A.3.7), flutolanil (A.3.8), fluxapyroxad (A.3.9), furametpyr (A.3.10), isofetamid (A.3.1 1 ), isopyrazam (A.3.12), mepronil (A.3.13), oxycarboxin (A.3.14), penflufen (A.3.14), penthiopyrad (A.3.15), sedaxane (A.3.16), tecloftalam (A.3.17), thifluzamide (A.3.18), N-(4'-trifluoromethylthiobiphenyl-2-yl)-3 difluoromethyl-1-methyl-1 H pyrazole-4-car
  • respiration inhibitors e. g. complex I, uncouplers: diflumetorim (A.4.1 ), (5,8-difluoro- quinazolin-4-yl)- ⁇ 2-[2-fluoro-4-(4-trifluoromethylpyridin-2-yloxy)-phenyl]-ethyl ⁇ -amine (A.4.2); nitrophenyl derivates: binapacryl (A.4.3), dinobuton (A.4.4), dinocap (A.4.5), fluazinam (A.4.6); ferimzone (A.4.7); organometal compounds: fentin salts, such as fentin-acetate (A.4.8), fentin chloride (A.4.9) or fentin hydroxide (A.4.10); ametoctradin (A.4.1 1 ); and silthiofam (A.4.12); B) Sterol biosynthesis inhibitors (SBI fungicides) C14 demethylase inhibitors (DM I fungide
  • Delta14-reductase inhibitors aldimorph (B.2.1 ), dodemorph (B.2.2), dodemorph-acetate (B.2.3), fenpropimorph (B.2.4), tridemorph (B.2.5), fenpropidin (B.2.6), piperalin (B.2.7), spirox- amine (B.2.8);
  • Inhibitors of 3-keto reductase fenhexamid (B.3.1 );
  • phenylamides or acyl amino acid fungicides benalaxyl (C.1.1 ), benalaxyl-M (C.1 .2), kiral- axyl (C.1.3), metalaxyl (C.1.4), metalaxyl-M (mefenoxam, C.1.5), ofurace (C.1 .6), oxadixyl (C.1 .7);
  • tubulin inhibitors such as benzimidazoles, thiophanates: benomyl (D1.1 ), carbendazim (D1.2), fuberidazole (D1.3), thiabendazole (D1 .4), thiophanate-methyl (D1.5); triazolopyrim- idines: 5-chloro-7 (4 methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)-[1 ,2,4]triazolo[1 ,5 a]pyrimidine (D1.6);
  • diethofencarb (D2.1 ), ethaboxam (D2.2), pencycuron (D2.3), fluopicolide (D2.4), zoxamide (D2.5), metrafenone (D2.6), pyriofenone (D2.7);
  • methionine synthesis inhibitors (anilino-pyrimidines): cyprodinil (E.1.1 ), mepanipyrim (E.1.2), pyrimethanil (E.1 .3); protein synthesis inhibitors: blasticidin-S (E.2.1 ), kasugamycin (E.2.2), kasugamycin hy- drochloride-hydrate (E.2.3), mildiomycin (E.2.4), streptomycin (E.2.5), oxytetracyclin (E.2.6), polyoxine (E.2.7), validamycin A (E.2.8);
  • fluoroimid F.1.1
  • iprodione F.1.2
  • procymidone F.1 .3
  • vinclozolin F.1 .4
  • fenpiclonil F.1 .5
  • fludioxonil F.1.6
  • G protein inhibitors quinoxyfen (F.2.1 );
  • Phospholipid biosynthesis inhibitors edifenphos (G.1.1 ), iprobenfos (G.1.2), pyrazophos (G.1 .3), isoprothiolane (G.1.4);
  • lipid peroxidation dicloran (G.2.1 ), quintozene (G.2.2), tecnazene (G.2.3), tolclofos-methyl (G.2.4), biphenyl (G.2.5), chloroneb (G.2.6), etridiazole (G.2.7);
  • phospholipid biosynthesis and cell wall deposition dimethomorph (G.3.1 ), flumorph (G.3.2), mandipropamid (G.3.3), pyhmorph (G.3.4), benthiavalicarb (G.3.5), iprovalicarb (G.3.6), valifenalate (G.3.7) and N-(1-(1-(4-cyano-phenyl)ethanesulfonyl)-but-2-yl) carbamic acid-(4- fluorophenyl) ester (G.3.8);
  • inorganic active substances Bordeaux mixture (H.1 .1 ), copper acetate (H.1.2), copper hydroxide (H.1.3), copper oxychloride (H.1 .4), basic copper sulfate (H.1 .5), sulfur (H.1 .6);
  • thio- and dithiocarbamates ferbam (H.2.1 ), mancozeb (H.2.2), maneb (H.2.3), metam (H.2.4), metiram (H.2.5), propineb (H.2.6), thiram (H.2.7), zineb (H.2.8), ziram (H.2.9);
  • organochlorine compounds e. g. phthalimides, sulfamides, chloronitriles: anilazine (H.3.1 ), chlorothalonil (H.3.2), captafol (H.3.3), captan (H.3.4), folpet (H.3.5), dichlofluanid (H.3.6), dichlorophen (H.3.7), hexachlorobenzene (H.3.8), pentachlorphenole (H.3.9) and its salts, phthalide (H.3.10), tolylfluanid (H.3.1 1 ), N (4-chloro-2-nitro-phenyl)-N-ethyl-4-methyl- benzenesulfonamide (H.3.12);
  • organochlorine compounds e. g. phthalimides, sulfamides, chloronitriles
  • guanidines and others guanidine (H.4.1 ), dodine (H.4.2), dodine free base (H.4.3), guazatine (H.4.4), guazatine-acetate (H.4.5), iminoctadine (H.4.6), iminoctadine-triacetate (H.4.7), iminoctadine-tris(albesilate) (H.4.8), dithianon (H.4.9), 2,6-dimethyl-1 H,5H- [1 ,4]dithiino[2,3-c:5,6-c']dipyrrole-1 ,3,5,7(2H ,6H)-tetraone (H .4.10);
  • inhibitors of glucan synthesis validamycin (1.1 .1 ), polyoxin B (1.1.2);
  • melanin synthesis inhibitors pyroquilon (1.2.1 ), tricyclazole (1.2.2), carpropamid (1.2.3), di- cyclomet (1.2.4), fenoxanil (1.2.5);
  • bronopol K.1 .1
  • chinomethionat K.1.2
  • cyflufenamid K.1 .3
  • cymoxanil K.1.4
  • dazomet K.1.5
  • debacarb K.1.6
  • diclomezine K.1 .7
  • difenzoquat K.1.8
  • difenzoquat-methylsulfate K.1.9
  • diphenylamin K.1 .10
  • fenpyrazamine K.1.1 1
  • flumetover K.1 .12
  • flusulfamide K.1.13
  • flutianil K.1.14)
  • methasulfocarb K.1 .15
  • nitrapyrin K.1.16)
  • nitrothal-isopropyl K.1.18
  • oxathiapiprolin K.1.19
  • tolprocarb K.1.20
  • oxin-copper K.1 .21
  • fungicides described by common names, their preparation and their activity e.g. against harmful fungi is known (cf.: http://www.alanwood.net/pesticides/); these substances are commercially available.
  • fungicides described by lUPAC nomenclature, their preparation and their pesticidal activity is also known (cf. Can. J. Plant Sci. 48(6), 587-94, 1968; EP A 141 317; EP-A 152 031 ; EP-A 226 917; EP A 243 970; EP A 256 503; EP-A 428 941 ; EP-A 532 022; EP-A 1 028 125; EP-A 1 035 122; EP A 1 201 648; EP A 1 122 244, JP 2002316902; DE 19650197; DE 10021412; DE 102005009458; US 3,296,272; US 3,325,503; WO 98/46608; WO 99/14187; WO 99/24413; WO 99/27783; WO 00/29404; WO 00/46148; WO 00/65913; WO 01/54501 ; WO 01/56358; WO 02/22583; WO 02/40431
  • Biopesticides have been defined as a form of pesticides based on micro-organisms (bacteria, fungi, viruses, nematodes, etc.) or natural products (compounds, such as metabolites, proteins, or extracts from biological or other natural sources) (U.S. Environmental Protection Agency: http://www.epa.gov/pesticides/biopesticides/). Biopesticides fall into two major classes, microbi- al and biochemical pesticides:
  • Microbial pesticides consist of bacteria, fungi or viruses (and often include the metabolites that bacteria and fungi produce). Entomopathogenic nematodes are also classified as microbial pesticides, even though they are multi-cellular.
  • Biochemical pesticides are naturally occurring substances or or structurally-similar and functionally identical to a naturally-occurring substance and extracts from biological sources that control pests or provide other crop protection uses as defined below, but have non-toxic mode of actions (such as growth or developmental regulation, attractents, repellents or defence activators (e.g. induced resistance) and are relatively non-toxic to mammals.
  • Biopesticides for use against crop diseases have already established themselves on a variety of crops. For example, biopesticides already play an important role in controlling downy mildew diseases. Their benefits include: a 0-Day Pre-Harvest Interval, the ability to use under moderate to severe disease pressure, and the ability to use in mixture or in a rotational program with other registered pesticides.
  • Biopesticidal seed treatments are e.g. used to control soil borne fungal pathogens that cause seed rots, damping-off, root rot and seedling blights. They can also be used to control internal seed borne fungal pathogens as well as fungal pathogens that are on the surface of the seed.
  • Many biopesticidal products also show capacities to stimulate plant host defenses and other physiological processes that can make treated crops more resistant to a variety of biotic and abiotic stresses or can regulate plant growth. Many biopesticidal products also show capacities to stimulate plant health, plant growth and/or yield enhancing activity.
  • biopesticides in conjunction with which the compounds of the present invention can be used, is intended to illustrate the possible combinations but does not limit them:
  • Microbial pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity Ampelomyces quisqualis, Aspergillus flavus, Aureobasidium pullulans, Bacillus altitudinis, B. amyloliquefaciens, B. mega teri urn, B. mojavensis, B. mycoides, B. pumilus, B. simplex, B. sol/sals/, B. subtil is, B. subtil is var. amyloliquefaciens, Candida oleophila, C.
  • Biochemical pesticides with fungicidal, bactericidal, viricidal and/or plant defense activator activity harpin protein, Reynoutria sachalinensis extract;
  • Microbial pesticides with insecticidal, acaricidal, molluscidal and/or nematicidal activity Agrobacterium radio bacter, Bacillus cere us, B. firm us, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ssp. tenebrionis, Beau- veria bass/ana, B.
  • Agrobacterium radio bacter Bacillus cere us, B. firm us, B. thuringiensis, B. thuringiensis ssp. aizawai, B. t. ssp. israelensis, B. t. ssp. galleriae, B. t. ssp. kurstaki, B. t. ss
  • brongniartii Burkholderia spp., Chromobacterium subtsugae, Cydia pomon el- la granulovirus (CpGV), Cryptophlebia leucotreta granulovirus (CrleGV), Flavobacterium spp., Helicoverpa armigera nucleopolyhedrovirus (HearNPV), Helicoverpa zea nucleopolyhedrovirus (HzNPV), Helicoverpa zea single caps/ ' d nucleopolyhedrovirus (HzSNPV), Heterorhabditis bac- teriophora, I sari a fumoso rosea, Lecanicillium longisporum, L.
  • HearNPV Helicoverpa armigera nucleopolyhedrovirus
  • HzNPV Helicoverpa zea nucleopolyhedrovirus
  • HzSNPV Helicoverpa
  • Microbial pesticides with plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity Azospirillum amazonense, A. brasilense, A. lipoferum, A. irakense, A. halopraeferens, Bradyrhizobium spp., B. elkanii, B. japonicum, B. liaoningense, B. lupini, Delftia acidovorans, Glomus intra radices, Mesorhizobium spp., Rhizobium leg urn i- nosarum bv. phaseoli, R. I. bv. trifolii, R. I. bv. viciae, R. tropic/, ' Sinorhizobium meliloti.
  • the biopesticides from group L1 ) and/or L2) may also have insecticidal, acaricidal, molluscidal, pheromone, nematicidal, plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity.
  • the biopesticides from group L3) and/or L4) may also have fungicidal, bactericidal, viricidal, plant defense activator, plant stress reducing, plant growth regulator, plant growth promoting and/or yield enhancing activity.
  • the biopesticides from group L5) may also have fungicidal, bactericidal, viricidal, plant defense activator, insecticidal, acaricidal, molluscidal, pheromone and/or nematicidal activity.
  • RhizoVital® 42 from AbiTEP GmbH, Germany
  • B. amyloliquefaciens ssp. plantarum MBI600 isolated from faba bean in Sutton Bonington, Nottinghamshire, U .K. at least before 1988 also called 1430; NRRL B 50595; US 2012/0149571 A1 ; e. g. Integral® from BASF Corp., USA
  • NRRL B 21661 e. g. Serenade® MAX from Bayer Crop Science LP, USA
  • B. pumilus INR-7 otherwise referred to as BU F22 and BU-F33 isolated at least before 1993 from cucumber infested by Erwinia tracheiphila (NRRL B-50185, NRRL B-50153; US 8,445,255), B. pumilus KFP9F isolated from the rhizosphere of grasses in South Africa at least before 2008 (NRRL B-50754; WO 2014/029697; e. g. BAC-UP or FUSION-P from BASF Agricultural
  • B. pumilus QST 2808 was isolated from soil collected in Pohnpei, Federated States of Micronesia, in 1998 (NRRL B 30087; e. g. Sonata® or Ballad® Plus from Bayer Crop Science LP, USA), B. simplex ABU 288 (NRRL B-50304; US 8,445,255), B. subtilis FB17 also called UD 1022 or UD10-22 isolated from red beet roots in North America (ATCC PTA-1 1857; System. Appl. Microbiol. 27, 372-379, 2004; US 2010/0260735; WO
  • B. t. ssp. tenebrionis NB-176-1 a mutant of strain NB-125, a wild type strain isolated in 1982 from a dead pupa of the beetle Tenebrio molitor (DSM 5480; EP 585 215 B1 ; e. g. Novodor® from Valent Biosciences, Switzerland), Beauveria bass/ana GHA (ATCC 74250; e. g. BotaniGard® 22WGP from Laverlam Int. Corp., USA), B. bassiana JW-1 (ATCC 74040; e. g. Naturalis® from CBC (Europe) S.r.l., Italy), B. bassiana PPRI 5339 isolated from the larva of the tortoise beetle Conchyloctenia punctata (NRRL 50757; e. g.
  • SEMIA 5079 isolated from soil in Cerrados region, Brazil by Embrapa-Cerrados used in commercial inoculants since 1992 (CPAC 15; e. g. GELFIX 5 or ADHERE 60 from BASF Agricultural Specialties Ltd., Brazil), B. japonicum SEMIA 5080 obtained under lab condtions by Embrapa-Cerrados in Brazil and used in commercial inoculants since 1992, being a natural variant of SEMIA 586 (CB1809) originally isolated in U.S.A. (CPAC 7; e. g.
  • HearN PV Helicoverpa armigera nucleopolyhedrovirus
  • HSSNPV single capsid nucleopolyhedrovirus
  • ABA- NPV-U e.g. Heligen® from AgBiTech Pty Ltd., Queensland, Australia
  • Heterorhabditis bacteriophora e. g. Nemasys® G from BASF Agricultural Specialities Limited, UK
  • Isaria fumosorosea Apopka-97 isolated from mealy bug on gynra in Apopka, Florida, U.S.A.
  • Reynoutria sachalinensis extract (EP 0307510 B1 ; e. g. Regalia® SC from Marrone Biolnnovations, Davis, CA, USA or Milsana® from BioFa AG, Germany), Steinernema carpocapsae (e. g. Millenium® from BASF Agricultural Specialities Limited, UK), S. feltiae ⁇ e. g. Nemashield® from BioWorks, Inc., USA; Nemasys® from BASF Agricultural Specialities Limited, UK), Streptomyces microflavus RRL B-50550 (WO
  • Trichoderma asperelloides JM41 R isolated in South Africa NRRL 50759; also referred to as T. fertile, e. g. Trichoplus® from BASF
  • T. harzianum l-22 also called KRL-AG2 (ATCC 20847; BioControl 57, 687-696, 2012; e. g. Plantshield® from BioWorks Inc., USA or SabrExTM from Advanced Biological Marketing Inc., Van Wert, OH, USA).
  • the solid material (dry matter) of the biopesticides (with the exception of oils such as Neem oil) are considered as active components (e.g. to be obtained after drying or evaporation of the extraction or suspension medium in case of liquid formulations of the microbial pesticides).
  • the weight ratios and percentages used herein for a biological extract such as Quillay extract are based on the total weight of the dry content (solid material) of the respective extract(s).
  • the total weight ratios of compositions comprising at least one microbial pesticide in the form of viable microbial cells including dormant forms can be determined using the amount of CFU of the respective microorganism to calclulate the total weight of the respective active component with the following equation that 1 x 1010 CFU equals one gram of total weight of the respective active component.
  • Colony forming unit is measure of viable microbial cells, in particular fungal and bacterial cells.
  • CFU may also be understood as the number of (juvenile) individual nematodes in case of (entomopathogenic) nematode biopesticides, such as Steinernema feltiae.
  • the applica-tion rates preferably range from about 1 x 106 to 5 x 1015 (or more) CFU/ha, preferably from about 1 x 108 to about 1 x 1013 CFU/ha, and even more preferably from about 1 x 109 to about 1 x 1012 CFU/ha.
  • (entomopathogenic) nematodes as microbial pesticides (e. g.
  • the application rates preferably range inform about 1 x 105 to 1 x 1012 (or more), more preferably from 1 x 108 to 1 x 101 1 , even more preferably from 5 x 108 to 1 x 1010 individuals (e. g. in the form of eggs, juvenile or any other live stages, preferably in an infetive juvenile stage) per ha.
  • the application rates with respect to plant propagation material preferably range from about 1 x 106 to 1 x 1012 (or more) CFU/seed.
  • the concentration is about 1 x 106 to about 1 x 109 CFU/seed.
  • the application rates with respect to plant propagation material also preferably range from about 1 x 107 to 1 x 1014 (or more) CFU per 100 kg of seed, preferably from 1 x 109 to about 1 x 1012 CFU per 100 kg of seed.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

La présente invention concerne un procédé de lutte contre les insectes qui sont résistants à un ou plusieurs insecticides.
PCT/IB2017/055413 2016-09-26 2017-09-08 Procédé de lutte contre les insectes résistants aux insecticides Ceased WO2018055478A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP16190613 2016-09-26
EP16190613.6 2016-09-26

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WO2018055478A1 true WO2018055478A1 (fr) 2018-03-29

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115426885A (zh) * 2020-03-20 2022-12-02 拜耳公司 针对难靶向昆虫物种的包含多种杆状病毒的组合物

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1889540A1 (fr) * 2005-06-01 2008-02-20 Meiji Seika Kaisha Ltd. Agent antiparasitaire
WO2013107795A2 (fr) * 2012-01-17 2013-07-25 Syngenta Participations Ag Mélanges pesticides contenant des pyrrolidinediones spirohétérocycliques
WO2016038067A1 (fr) * 2014-09-10 2016-03-17 Basf Se Utilisation d'afidopyropène dans des plantes génétiquement modifiées

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP1889540A1 (fr) * 2005-06-01 2008-02-20 Meiji Seika Kaisha Ltd. Agent antiparasitaire
WO2013107795A2 (fr) * 2012-01-17 2013-07-25 Syngenta Participations Ag Mélanges pesticides contenant des pyrrolidinediones spirohétérocycliques
WO2016038067A1 (fr) * 2014-09-10 2016-03-17 Basf Se Utilisation d'afidopyropène dans des plantes génétiquement modifiées

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115426885A (zh) * 2020-03-20 2022-12-02 拜耳公司 针对难靶向昆虫物种的包含多种杆状病毒的组合物

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