AU2009321817A1 - Use of particular enamino carbonyl compounds for selectively controlling insects - Google Patents

Abstract

The present invention relates to the use of particular enamino carbonyl compounds for selectively controlling insects, characterized in that pollinating insects are not damaged by contact with the compounds.

Description

VV.J U. uiv/uuJoJ. rI 1/rrLUU0ua.VUU -1 Use of certain enaminocarbonyl compounds for the selective control of insects The present invention relates to the use of certain enaminocarbonyl compounds for the selective control of animal pests, characterized in that pollinating insects are not harmed upon contact with the compounds. Simultaneously, the invention relates to a method of protecting pollinating insects 5 which is characterized in that certain enaminocarbonyl compounds are used for pest control. It is known to use enaminocarbonyl compounds as plant protection agents for controlling insects and acarids. Certain substituted 4-aiinobut-2-enolide compounds have already been described in EP-A-0 539 588 and WO 2007/115644, WO 2007/115643 and WO 2007/115646 as insecticidally active compounds. 10 The use of insecticidally active compounds in plant protection entails in principle the risk that these compounds are also active against beneficial insects or have an effect on the development of their brood. It is not possible to predict either from the structure or from the mechanism of action of an insecticide whether the insecticide has a harmful effect on beneficial insects or is safe for them. The beneficial insects in particular include pollinating insects such as bees or bumblebees. 15 Besides the fertilization or fecundation or pollination by pollinating insects, the control of animal pests, too, has a decisive effect on the yield of agricultural plants, which is why the use of insecticides cannot be dispensed with. If such an undesired toxicity is found, the use of these insecticides is subjected to severe regulation, or banned. Examples of insecticides which are currently classified as toxic to pollinating insects are fenoxycarb and thiamethoxam. 20 The toxicity to pollinating insects may manifest itself in different manners and at various developmental stages of the insects, and different toxicity end-points can be determined. In the case of honeybees, for example, the mortality of workers, drones or pupae, the foraging activity or the colony development, may be assessed, for example with reference to the storage of honey and pollen, the colony size (as measured by the occupied surface area of the honeycomb), the effects 25 on brood development (eggs, larvae and pupae), or the hive weight may be determined as toxicity end-points. In the case of bumblebees, for example, the flight and pollinating activity and the yield may be determined as toxicity end-points. Bees pollinate plants and thereby contribute considerably to successful harvests in agriculture. They play important roles in the ecosystem since, without pollination by bees, other animal species 30 would lack some of their food supply which they need to live. Approximately one third of food production worldwide, and probably two thirds of the most important food plants, are dependent on pollinating insects, in particular on bees. The factor "species diversity" is of particular importance here. Our indigenous wild honeybees and WUZU U3.36 rU I iLrLuUVY1uV6 iu -2 bumblebees, too, are indispensible for pollination. Surprisingly, it has been found in the present invention that certain 4-amino-2-butenolide compounds have a selective activity and therefore do not harm pollinating insects. The specific compounds according to the invention are 4-{[(6-chloropyrid-3-yl) 5 methyl](2,2-difluoroethyl)amino}furan-2(5H)-one (compound (1-5)), whose insecticidal activity was first described in WO 2007/115644; 4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl) amino} furan-2(5H)-one (compound (I-9)) and 4-{[(6-chloropyrid-3-yl)methyl](methyl)amino} furan-2(5H)-one (compound (1-10)), whose insecticidal was first described in EP-A-0 539 588. The compounds can be prepared by the processes described in W02007/115644 and 10 EP-A-0539588, and they have the following structure: CI Cl CI F /<\ \ \N N N H3N HO3 F N N N 0 0 0 (1-5) (1-9) (1-10) As has.already been mentioned, the selective activity of the compounds according to the invention, i.e. the destruction of undesired insects (animal pests), and the "safeguarding" of the pollinating insects, cannot be deduced either from the structure of the compounds or from their activity against 15 animal pests. Rather, finding the selective activity is surprising, in particular because the compounds according to the invention are active against a multiplicity of animal pests from various orders and families and because it could not have been expected that the compounds according to the invention do not harm pollinating insects, in particular those from the superfamily of the Apoidea. 20 The fact that pollinating insects are not harmed can be seen inter alia from the fact that, when they come into contact with the compounds according to the invention, their mortality and the mortality of their developmental stages is not increased, that their foraging, pollinating and flight activity is unchanged and that the brood development of pollinating insects measured by the proportion of eggs, larvae and pupae of occupied alveoli is unchanged.

-3 The present invention therefore also relates to a method of protecting pollinating insects, in particular of protecting insects from the family of the Apidae, for example Apini (honeybees, Apis) or Bombini (bumblebees, Bombus) and sphecoid wasps (Spheciformes), characterized in that at least one compound of the formula (1-5), (1-9) or (1-10) is employed for controlling animal 5 pests. The use of the compounds according to the invention for controlling the animal pests may be effected as a foliar treatment (for example atomizing, spraying, wetting, dipping, vaporizing, fogging, painting on or injecting), soil application (for example watering, atomizing, spraying, trickling on, soil injection or scattering (for example powder or soil granules)). Equally, the 10 compounds according to the invention can be applied to seed (for example by dipping, atomizing, vaporizing, fogging, scattering, brushing on, injecting or by applying one or more coats). Applications which are preferred according to the invention are foliar application and seed treatment. The protection of the pollinating insects is particularly pronounced when the compounds according 15 to the invention for controlling animal pests are used on flowering plants or in the vicinity of flowering plants or on, or in the vicinity of, plants which are visited by pollinating insects. Since many known insecticides frequently also have a more or less pronounced effect against pollinating insects, in addition to the pests, the user should generally not apply the insecticide to, or in the vicinity of, flowering plants, or, if appropriate, only after sunset, i.e. after the bees' 20 emergence period, thereby minimizing the contact of the pollinating insects with the insecticides. At the same time, it has been considered a problem that systemic insecticide applied via seed treatment may accumulate in the pollen of a plant and is thereby capable of harming pollinating insects. Surprisingly, it has been found that, when using the compounds according to the invention for 25 controlling animal pests, such protective or precautionary measures for avoiding the abovementioned harmful effects need not be taken because pollinating insects are not harmed upon contact with the compounds according to the invention. It has been found that even oral, topical or tarsal contact (i.e. contact via the limbs) at the application rates conventionally used in agriculture and forests will not harm the pollinating insects. The same was found for the brood, which is not 30 harmed by being fed pollen or nectar from plants which have previously been treated with the compounds according to the invention. Pollinating insects can come into contact with the compounds according to the invention or with other insecticides by visiting flowers which have previously been sprayed or watered with -4 compounds according to the invention or with other insecticides, or by pollinating insects coming into contact with the compounds according to the invention or with other insecticides on the paths of the experimental area, between the plants or via the air which they breathe. For the purposes of the present invention, the term "in the vicinity" comprises that radius around 5 an area treated with at least one of the compounds according to the invention in which this compound can still be detected. The present invention also relates to the use of at least one compound of the formulae (1-5), (1-9) and (1-10) according to the invention for the selective control of animal pests, where pollinating insects are not harmed upon contact with the compounds according to the invention. 10 The present invention furthermore relates to the use of at least one compound of the formulae (1-5), (1-9) and (I-10) according to the invention for the selective control of animal pests without harming pollinating insects, where the mortality of pollinating insects and of their developmental stages is not increased, the foraging, pollinating and flight activity of pollinating insects are unchanged and the brood development of pollinating insects as determined for example by the proportion of eggs, 15 larvae and pupae in the occupied alveoli is unchanged. The present invention furthermore relates to the use of at least one compound of the formulae (1-5), (1-9) and (1-10) according to the invention for the selective control of animal pests without harming pollinating insects, where the pollinating insects are selected from the superfamily of the Apoidea, for example the bees (Apiformes) and the sphecoid wasps (Spheciformes). The pollinating insects 20 are preferably selected from the family of the Apidae, for example Apini (honeybees, Apis) or Bombini (bumblebees, Bombus). The present invention furthermore relates to the use of at least one compound of the formulae (1-5), (1-9) and (I-10) according to the invention for the selective control of animal pests without harming pollinating insects, where the compounds according to the invention are applied as a foliar 25 application, soil application or seed treatment. The present invention furthermore relates to the use of at least one compound of the formulae (1-5), (1-9) and (I-10) according to the invention for the selective control of animal pests without harming pollinating insects, where the compounds according to the invention are applied to flowering plants or in the vicinity of flowering plants or on, or in the vicinity of, plants which are visited by 30 pollinating insects. The abovementioned animal pests include: -5 From the order of the Anoplura (Phthiraptera), for example Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.. From the class of the Arachnida, for example Acarus spp., Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus 5 spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Halotydeus destructor, Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Nuphersa spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, 10 Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici. From the class of the Bivalva, for example Dreissena spp.. From the order of the Chilopoda, for example Geophilus spp., Scutigera spp.. From the order of the Coleoptera, for example Acalymma vittatum, Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, 15 Anoplophora spp., Anthonomus spp., Anthrenus spp., Apion spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Cassida spp., Cerotoma trifurcata, Ceutorrhynchus spp., Chaetocnema spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Ctenicera spp., Curculio spp., Cryptorhynchus lapathi, Cylindrocopturus spp., Dermestes spp., Diabrotica spp., Dichocrocis spp., Diloboderus spp., Epilachna spp., Epitrix 20 spp., Faustinus spp., Gibbium psylloides, Hellula undalis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnostema consanguinea, Lema spp., Leptinotarsa decemlineata, Leucoptera spp., Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp., Megascelis spp., Melanotus spp., Meligethes aeneus, Melolontha spp., Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, 25 Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorrhynchus spp., Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Phyllotreta spp., Popillia japonica, Premnotrypes spp., Psylliodes spp., Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.. 30 From the order of the Collembola, for example Onychiurus armatus. From the order of the Diplopoda, for example Blaniulus guttulatus. From the order of the Diptera, for example Aedes spp., Agromyza spp., Anastrepha spp., vu LIIU/V0L FU 1/tfILUUWUU&5UU -6 Anopheles spp., Asphondylia spp., Bactrocera spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chironomus spp., Chrysomyia spp., Cochliomyia spp., Contarinia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dasyneura spp., Delia spp., Dermatobia hominis, Drosophila spp., Echinocnemus spp., Fannia spp., Gastrophilus spp., 5 Hydrellia spp., Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp.. Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia spp., Phorbia spp., Prodiplosis spp., Psila rosae, Rhagoletis spp., Stomoxys spp., Tabanus spp., Tannia spp., Tetanops spp., Tipula spp.. From the class of the Gastropoda, for example Arion spp., Biomphalaria spp., Bulinus spp., 10 Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.. From the class of the helminths, for example Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus 15 granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp.,Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp, Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, 20 Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti. Protozoans, such as Eimeria, may furthermore be controlled. From the order of the Heteroptera, for example Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Collaria spp., Creontiades 25 dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Monalonion atratum, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca 30 spp., Triatoma spp. From the order of the Homoptera, for example Acyrthosipon spp., Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella -I 7 -7 spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Cameocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, 5 Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Ferrisia spp., Geococcus coffeae, Hieroglyphus spp., Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., 10 Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, 15 Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes spp., Trioza spp., Typhlocyba spp., Unaspis spp., 20 Viteus vitifolii, Zygina spp.. From the order of the Hymenoptera, for example Athalia spp., Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.. From the order of the Isopoda, for example Armadillidium vulgare, Oniscus asellus, Porcellio scaber. 25 From the order of the Isoptera, for example Acromyrmex spp., Atta spp., Cornitermes cumulans, Microtermes obesi, Odontotermes spp., Reticulitermes spp, From the order of the Lepidoptera, for example Acronicta major, Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyelois transitella, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, 30 Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnephasia spp., Conopomorpha spp., Conotrachelus spp., Copitarsia spp., Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eldana saccharina, Ephestia kuehniella, Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp., Eupoecilia ambiguella, Euproctis spp., Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., Hedylepta spp., Helicoverpa spp., Heliothis spp., Hofinannophila pseudospretella, Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria flavofasciata, Laphygma spp., Laspeyresia molesta, Leucinodes 5 orbonalis, Leucoptera spp., Lithocolletis spp., Lithophane antennata, Lobesia spp., Loxagrotis albicosta, Lymantria spp., Lyonetia spp., Malacosoma neustria, Maruca testulalis, Mamestra brassicae, Mocis spp., Mythimna separata, Nymphula spp., Oiketicus spp., Oria spp., Orthaga spp., Ostrinia spp., Oulema oryzae, Panolis flammea, Parnara spp., Pectinophora spp., Perileucoptera spp., Phthorimaea spp., Phyllocnistis citrella, Phyllonorycter spp., Pieris spp., Platynota stultana, 10 Plusia spp., Plutella xylostella, Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Scirpophaga spp., Scotia segetum, Sesamia spp., Sparganothis spp., Spodoptera spp., Stathmopoda spp., Stomopteryx subsecivella, Synanthedon spp., Tecia solanivora, Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichoplusia spp., Tuta absoluta, Virachola spp.. 15 From the order of the Orthoptera, for example Acheta domesticus, Blatta orientalis, Blattella germanica, Dichroplus spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria. From the order of the Siphonaptera, for example Ceratophyllus spp., Xenopsylla cheopis. From the order of the Symphyla, for example Scutigerella spp.. 20 From the order of the Thysanoptera, for example Anaphothrips obscurus, Baliothrips biformis, Drepanothris reuteri, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.. From the order of the Thysanura, for example Lepisma saccharina. The plant-parasitic nematodes include, for example, Aphelenchoides spp., Bursaphelenchus spp., 25 Ditylenchus spp., Globodera spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.. The active substances of the formula (I) are not only active against plant pests, hygiene pests and stored-product pests, but also, in the veterinary medicine sector, against animal parasites (ecto- and 30 endoparasites) such as hard ticks, soft ticks, scab mites, harvest mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, bird lice and fleas. These parasites include: -9 From the order of the Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.. From the order of the Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron 5 spp., Damalina spp., Trichodectes spp., Felicola spp.. From the order Diptera and the suborders Unterordnungen Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., 10 Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.. From the order of the Siphonapterida, for example Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.. 15 From the order of the Heteropterida, for example Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.. From the order of the Blattarida, for example Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp.. From the subclass of the Acari (Acarina) and the orders of the Meta- and Mesostigmata, for 20 example Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp., Pneumonyssus spp., Stemostoma spp., Varroa spp.. From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata), for example Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., 25 Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.. When used in the method according to the invention, the application rates of the compounds according to the invention can be varied within a substantial range, depending on the route of 30 application. The application rate of the compounds according to the invention in the treatment of plant parts, for example leaves, is from 0.1 to 10 000 g/ha, preferably from I to 1000 g/ha, V.~~ %_ 1 '.'L.A14VU7UUO.,VV - 10 especially preferably from 10 to 300 g/ha (when applied by watering or trickling, the application rate may even be reduced, especially when inert substrates such as rock wool or perlite are used). For the purposes of the invention, these application rates are only mentioned by way of example and are not limiting. 5 To control pests, the compounds according to the invention are employed for protecting plants within a certain period of time after the treatment against attack by the abovementioned animal pests. The period of time within which protection is afforded generally extends to 1 to 28 days, preferably to I to 14 days, especially preferably to 1 to 10 days, very especially preferably to 1 to 7 days after the treatment of the plants with the active substance. 10 The compounds according to the invention can be employed in the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, granules for scattering, suspension/emulsion concentrates, natural substances impregnated with active substance, synthetic substances impregnated with active substance, fertilizers and microencapsulations in polymeric substances. 15 These formulations are prepared in a known manner, for example by mixing the active substances with extenders, that is to say liquid solvents and/or solid carriers, if appropriate using surface active agents, that is emulsifiers and/or dispersants and/or foam formers. The formulations are prepared either in suitable apparatuses or else before or during the application. Adjuvants which may be used are those substances which are suitable for imparting special 20 properties to the composition itself and/or to preparations derived therefrom (for example spray mixtures, seed treatments), such as certain technical properties and/or else. special biological properties. Typical adjuvants which are suitable are: extenders, solvents and carriers. Suitable extenders are, for example, water, polar and nonpolar organic chemical liquids, for example from the classes of the aromatic and nonaromatic hydrocarbons (such as paraffins, 25 alkylbenzenes, alkylnaphthalenes, chlorobenzenes), of the alcohols and polyols (which may optionally also be substituted, etherified and/or esterified), of the ketones (such as acetone, cyclohexanone), esters (also fats and oils) and (poly)ethers, of the basic and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, of the sulphones and sulphoxides (such as dimethyl sulphoxide). 30 If water is used as the extender, it is possible for example also to use organic solvents as cosolvents. Suitable liquid solvents are essentially: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic hydrocarbons and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as I %, I JL -V 1V ~ V -11 cyclohexane or paraffins, for example mineral oil fractions, mineral and vegetable oils, alcohols such as butanol or glycol, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulphoxide, and water. 5 According to the invention, a carrier means a natural or synthetic, organic or inorganic substance which may be solid or liquid and with which the active substances are mixed or associated for the purpose of better applicability, in particular for application to plants or plant parts or seed. The solid or liquid carrier is generally inert and should be agriculturally useful. Suitable solid or liquid carriers are: 10 for example ammonium salts and ground natural rocks, such as kaolins, clays, talc, chalk, quartz, attapulgite, Montmorillonite or diatomaceous earth and ground synthetic rocks such as highly dispersed silica, alumina and silicates, solid carriers for granules which are suitable are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite, and synthetic granules of inorganic and organic meals and granules of organic material 15 such as paper, sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonate and protein hydrolysates; suitable dispersants are nonionic and/or ionic substances, for example from the classes of the alcohol-POE and/or -POP 20 ethers, acid and/or POP-POE esters, alkyl aryl- and/or POP-POE ethers, fatty and/or POP-POE adducts, POE and/or POP polyol derivatives, POE and/or POP sorbitan or sugar adducts, alkyl or aryl sulphates, alkyl- or aryl-sulphonates and alkyl or aryl phosphates or the corresponding PO ether adducts. Oligomers or polymers which are also suitable are, for example, those derived from vinylic monomers, from acrylic acid, from EO and/or PO alone or in combination with, for 25 example, (poly)alcohols or (poly)amines. Lignin and its sulphonic acid derivatives, unmodified and modified celluloses, aromatic and/or aliphatic sulphonic acids and their adducts with formaldehyde may also be employed. Stickers such as carboxymethylcellulose, natural and synthetic polymers in the form of powders, granules or latices such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural 30 phospholipids such as cephalins and lecitins and synthetic phospholipids may be used in the formulations. Colorants such as inorganic pigments, for example iron oxide, titanium oxide, Prussian blue, and organic dyes, such as alizarin, azo and metal phthalocyanine dyes, and trace nutrients such as salts VVj U UU/U04 YUo 1r4I UUY/UUi5.5UU - 12 of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be used. Further additives may be fragrances, mineral or vegetable oils which can optionally be modified, waxes and nutrients (also trace nutrients), such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. 5 Other substances which may be present are stabilizers such as low-temperature stabilizers, preservatives, antioxidants, UV stabilizers or other agents which improve the chemical and/or physical stability. The active substance content of the use forms prepared from the commercially available formulations can vary within wide limits. The total active substance concentration, or the active 10 substance concentration of the individual active substances, of the use forms is in the range of from 0.00000001 to 97% by weight of active substance, preferably in the range of from 0.0000001 to 97% by weight, especially preferably in the range of from 0.000001 to 83% by weight or 0.000001 to 5% by weight and very especially preferably in the range of from 0.0001 to 1% by weight. Application is made in a customary manner adapted to suit the use forms. 15 All plants and plant parts may be treated in accordance with the invention. In this context, plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants may be plants which can be obtained by traditional breeding and optimization methods or by biotechnological and recombinant methods or combinations of these methods, including the transgenic plants and 20 including the plant varieties capable or not of being protected by plant breeders' rights. Plant parts are understood as meaning all aerial and subterranean parts and organs of the plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruiting bodies, fruits and seed, and also roots, tubers and rhizomes. The plant parts also include harvested material and vegetative and generative propagation material, for example fruits, 25 seeds, cuttings, tubers, rhizomes, slips, seed, bulbils, layers and runners. Equally, plant species and plant varieties which occur in the wild or which are obtained by traditional biological breeding methods such as hybridization or protoplast fusion, and their parts may be treated. In one variant of the invention, transgenic plants and plant varieties which have been obtained by recombinant methods, such as, for example, antisense or cosuppression technology, RNA interference - RNAi 30 technology, if appropriate in combination with traditional methods (genetically modified organisms) and their parts are treated. Description of the figures: -13 Figure 1: tunnel test/spray application/bees, acute mortality of worker bees in front of the hive, DAA: time pre- and post-application in days, 0 DAA a = 9:30, b = 15:15, c = 17:15 hours Figure 2: tunnel test/spray application/bees, acute mortality of pupae in front of the hive, DAA: 5 time pre- and post-application in days, 0 DAA a = 9:30, b= 15:15, c = 17:15 hours Figure 3: tunnel test/spray application/bees, foraging activity, DAA: time pre- and post application in days, 0 DAA a = 09:30, b = 13:00, c = 14:15, d = 15:15, e = 17:15 hours, 1 DAA a = 12:00, b = 15:30 hours Figure 4.1: tunnel test/spray application/bees, brood development, 1 day pre-application 10 Figure 4.2: tunnel test/spray application/bees, brood development, 6 days post-application Figure 4.3: tunnel test/spray application/bees, brood development, 14 days post-application Figure 4.4: tunnel test/spray application/bees, brood development, 27 days post-application Figure 5: tent test/watering application/bees, acute mortality of worker bees in front of the hive, DAA: time post-application in days, 6 DAA a = 9:30, b = 14:30 hours 15 Figure 6: tent test/watering application/bees, foraging activity, DAA: time post-application in days, 6 DAA a = 9:30, b = 14:30 Figure 7.: tent test/watering application/bumblebees, flight activity at the nest, DAA: time pre and post-application in days Figure 8: tent test/watering application/bumblebees, pollinating activity 13 and 22 days post 20 application Figure 9: greenhouse test/residue test/bees, leaf sampling I day post-application Figure 10: greenhouse test/residue test/bees, leaf sampling 3 days post-application Figure 11: greenhouse test/residue test/bees, leaf sampling 6 days post-application Figure 12: greenhouse test/residue test/bees, leaf sampling 13 days post-application 25 The invention is illustrated by the examples which follow, without imposing any limitation thereon.

vvkj U.UvUU0304 IU Ir4rUUO/UUOIUU -14 Example 1 Tunnel test/spray application/bees The test was carried out as specified by EPPO (European Plant Protection Organisation) Guideline 170, as follows: Test compound: Compound 1-5, SL 100 Reference substances: Insegar WG 25 (Fenoxycarb) Actara WG 25 (Thiamethoxam) Application rates: Compound 1-5: 75 and 150 g a.s./ha Insegar: 150 g a.s./ha Actara: 50 g a.s./ha Water volume: 400 1/ha Crop plant: Phacelia tanacetifolia Test organism: Apis mellifera (beehive with 3 honeycombs with approximately 3500 bees) Design: 50 n 2 tunnel (5m * 1Om) Replications: 3 (Actara: 2) Application: I application to flowering Phacelia during the emergence time, by means of sprayer bar Exposure time: 8 days End points: Acute mortality of worker bees and pupae in front of the beehive Foraging activity Brood development 5 Example 1.1 Acute mortality of worker bees in front of the beehive The mortality of worker bees in front of the beehive is determined by means of a dead bee trap. The trap consists of wire mesh and is arranged in front of the beehive. Individual, live bees are 10 capable of passing through the wire mesh, the transport of dead bees across the mesh is not possible, which is why dead bees accumulate in the trap.

Vvx./ 4.0o vuJ JOZ, r.1 z LrLUuy/UUo.UU -15 Table 1 (see also Figure 1) [Number of deadworker -3 0 0 1 2 3 4 5 6 11 bees] DAA DAA DAA DAA DAA DAA DAA DAA DAA DAA b c Untreated 0.7 1 0.3 0 0 0.7 2 0.3 3.3 0 Fenoxycarb 150 g a.s./ha 1 0 0 1.3 0.7 0 2 1.3 3 1 1-5 75 g a.s./ha 0.3 0 0.7 0 0.3 0.3 3.7 0.3 4.3 0 1-5 150 g a.s./ha 0.3 1.3 0.3 0 0 0 1.7 0.7 2 1.7 Thiamethoxam 50 g a.s./ha 1.6 420 45.3 152.8 229.4 50.2 891.6 2.4 9 16.5 DAA: Time pre- or post-application in days 0 DAA b= 15:15, c = 17:15 hours 5 Thiamethoxam causes a pronounced mortality of worker bees in front of the beehive. Compound 1-5 does not cause any mortality of worker bees in front of the beehive.

-16 Example 1.2 Acute mortality of pupae in front of the beehive Table 2 (see also Figure 2) [Number of -3 0 1 2 5 6 11 14 18 21 25 dead pupae] DAA DAA DAA DAA DAA DAA DAA DAA DAA DAA DAA c Untreated 0.3 0 0 0.7 0 0 0 0.3 0 0 0 Fenoxycarb 150 g a.s./ha 0 0 0 0 0 0 9 16.7 26.7 0 1 1-5 75 g a.s./ha 0 0 0 0.3 0 0 0.3 0 0 0 0 I-5 150 g a.s./ha 0 0 0 0 0 0 0 0.7 0 0 0 Thiamethoxam 50 g a.s./ha 0 0 0 0.1 0.5 0 0 0.4 0 0 0.2 5 DAA: Time pre- or post-application in days 0 DAA c = 17:15 hours Fenoxycarb causes pupal mortality in front of the beehive 11-18 days post-application. Compound I-5 does not cause any pupal mortality in front of the beehive.

--- -- II I IL IU.J"IU'VUV -17 Example 1.3 Foraging activity The bees which land on flowers are counted for one minute in an enclosed area of 2 x I n 2 . Table 3 (see also Figure 3) [Numberof -3 -2 -1 0 0 0 1 2 3 6 bees/min/m 2 ] DAA DAA DAA DAA DAA DAA DAA DAA DAA DAA a c e b Untreated 25.2 35.2 27.8 24.3 40.2 37.8 19.5 37.8 40.7 38.5 Fenoxycarb 25 33.7 27.3 26.2 38.7 46 19 32.3 38.7 38.8 150 g a.s./ha 1-5 26.5 34.8 27.3 25.5 41 42.7 18.8 33.3 40.3 37.8 75 g a.s./ha 1-5 27 34.2 26.3 28.3 40.2 39 19.2 35.7 39.3 37.5 150 g a.s./ha Thiamethoxam 24.5 35.2 26.1 26.8 0.9 0.4 0 1.5 1.6 5.4 50 g a.s./ha 5 DAA: Time pre- or post-application in days 0 DAA a = 09:30, c = 14:15, e= 17:15 hours 1 DAA b= 15:30 hours Directly after the application of thiamethoxam, the bees' foraging activity ceases almost 10 completely. The slight increase 6 days post-application cannot be attributed to foraging bees. Compound I-5 does not cause any change in foraging activity.

W, ww..V 1 I .. II..i LU u _/U OJU - 18 Example 1.4 Brood development The respective proportion of alveoli which is occupied by pollen, nectar, eggs, larvae or pupae or is empty is determined for all honeycombs of a beehive. 5 Table 4.1 (see also Figure 4.1) 1 day pre-application [%] Pollen Nectar Empty Eggs Larvae Pupae Untreated 3.9 10.6 28.3 15.3 10.3 31.7 Fenoxycarb 150 g a.s./ha 2.2 13.3 25.8 12.5 14.2 31.9 I-5 75 g a.s./ha 3.1 12.5 26.7 13.9 9.2 34.7 I-5 150 g a.s./ha 1.4 14.2 20.8 13.6 16.4 33.6 Thiamethoxam 50 g a.s./ha 2.4 12 30 17.5 9 29.1 Table 4.2 (see also Figure 4.2) 6 days post-application 1%] Pollen Nectar Empty Eggs Larvae Pupae Untreated 5 10.6 32.2 14.7 8.3 29.2 Fenoxycarb 150 g a.s./ha 6.7 20.8 29.7 12.2 0.3 30.3 1-5 75 g a.s./ha 4.4 12.5 32.8 14.7 8.3 27.2 1-5 150 g a.s./ha 3.9 14.4 29.4 15 6.1 31.1 Thiametboxam 50 g a.s./ha 3.3 19.4 30.9 11.4 6.3 28.7 6 days post-application, fenoxycarb causes a pronounced decrease in the number .of larvae. 10 Compound 1-5 does not cause any change in the brood development.

I .~ v I %_ ,I /kL t..'J7IU'.JOjU -19 Table 4.3 (see also Figure 4.3) 14 days post-application [%] Pollen Nectar Empty Eggs Larvae Pupae Untreated 5.6 8.1 33.6 20.3 17.2 15.3 Fenoxycarb 150 g a.s./ha 5.3 9.2 52.2 18.3 10.6 4.4 1-5 75 g a.s./ha 5 8.6 30.6 21.4 19.7 14.7 I-5 150 g a.s./ha 4.2 12.2 34.4 17.8 16.7 14.7 Thiamethoxam 50 g a.s./ha 1.5 9.2 51.8 19.4 7.4 10.7 14 days post-application, fenoxycarb causes a pronounced decrease in the number of pupae. Compound I-5 does not cause any change in the brood development. 5 Table 4.4 (see also Figure 4.4) 27 days post-application 1%] Pollen Nectar Empty Eggs Larvae Pupae Untreated 5.8 11.9 23.1 16.4 6.1 36.7 Fenoxycarb 150 g a.s./ha 4.7 21.9 23.1 18.6 7.2 24.4 1-5 75 g a.s./ha 3.3 13.2 20.7 16.7 6.7 39.4 I-5 150 g a.s./ha 4.2 16.4 21.9 15.3 7.2 35 Thiamethoxam 50 g a.s./ha 5.1 15.5 52 6.1 2 19.2 27 days after the application, thiamethoxam causes the number of empty alveoli to rise twofold and the number of larvae to drop sharply. Compound I-5 does not cause any change in the brood development. 10 - 20 Example 2 Tent test/watering application/bees The test was carried out as follows: Test compound: Compound 1-5, SL 300 Reference substance: Actara WG 25 (Thiamethoxam) Application rates: Compound 1-5: 20 mg a.s./plant Actara: 10 mg a.s./plant Volume of the application 25 ml/plant pot mixture: Crop plants: Lobelia erinus, Papaver nudicaule Test organism: Apis mellifera (beehive with 6 honeycombs with approximately 3000 bees) Design: 50 M 2 tent (5m * 10m) Replications: 1 Application: 1 application by watering Exposure time: 13 days/the bees were exposed to the plants 5 days post-application End points: Acute mortality of worker bees in front of the beehive Foraging activity 5 Example 2.1 Acute mortality of worker bees in front of the beehive Table 5 (see also Figure 5) [Number of dead 6 6 7 8 9 10 11 14 16 18 worker bees] DAA DAA DAA DAA DAA DAA DAA DAA DAA DAA a b Untreated 9 1 5 1 2 0 0 0 0' 0 Thiamethoxam 143 35 394 143 78 295 110 40 74 29 10 mg a.s./pl. 1-5 8 2 8 0 0 7 2 1 1 2 20 mg a.s./pl. DAA: Time post-application in days I v I % I I -A. L-VV7/ UJUOjU -21 6 DAA a = 9:30, b = 14:30 hours Thiamethoxam causes a pronounced mortality of worker bees in front of the beehive. Compound 1-5 does not cause any mortality of worker bees in front of the beehive. Example 2.2 5 Foraging activity Table 6 (see also Figure 6) [Number of 5 6 8 9 11 13 15 16 17 18 bees/min/4 m 2 ] DAA DAA DAA DAA DAA DAA DAA DAA DAA DAA DAA b Untreated 31 84 38 72 22 43 91 53 70 92 95 Thiamethoxam 10 mg a.s./pl. 28 70 23 25 19 16 14 8 15 13 6 1-5 20 mg a.s./pl. 26 73 21 70 41 31 86 43 51 98 71 DAA: Time post-application in days 6 DAA b = 14:30 hours 10 13 days after the application of thiamethoxam, the bees' foraging activity ceases almost completely. Compound I-5 does not cause any change in foraging activity. Example 3 Tent test/watering application/bumblebees The test was carried out as follows: Test compound: Compound 1-5, SL 300 Reference substances: None Application rate: Compound 1-5: 20 mg a.s./plant Crop plants: Lycopersicon esculentum, Tomato var. Bond Test organism: Bombus terrestris (Koppert) Design: 390 M 2 tent (13m * 30m) Replications: 3 vv, \JLU U/UJJOL rI ILrLvUU/UUO'UU - 22 Application: 2 applications by hosepipe (day 0 and day 14) Exposure time: 31 days/the bumblebees were exposed to the plants from day 3 after the first application up to day 34 after the first application. End points: Flight activity of bumblebees at the nest Pollinating activity of bumblebees Example 3.1 Flight activity of bumblebees at the nest The number of bumblebees which have entered or left the nest within a period of 10 minutes was 5 determined. Table 7 (see also Figure 7) [Number of bumblebees/ -1 0 6 8 13 20 23 27 34 10 min] DAA DAA DAA DAA DAA DAA DAA DAA DAA Untreated 18 15 18 20 14 15 15 14 5 1-5 20 mg a.s./pl. 13 9 11 15 11 12 14 11 6 DAA: Time after the first application in days Compound 1-5 does not cause any change in the bumblebees' flight activity. 10 Example 3.2 Pollinating activity of bumblebees In tomatoes, the stamens' colour changes as the result of visiting bumblebees (marked flowers). The number of open and of marked flowers was determined.

Tv %.fJ ~'~I U IjJU I %_ I/ LA t.AJVJ7IVVOjVV -23 Table 8 (see also Figure 8) [Number of DAA 13 DAA 22 flowers] Open flowers Marked flowers Open flowers Marked flowers Untreated 64.8 59.2 65.1 60.8 1-5 20 mg a.s./pl. 67.3 59.4 59.3 .5.3.7 DAA: Time after first application in days Compound I-5 does not cause any change in the bumblebees' pollinating activity. 5 Example 4 Greenhouse test/residue test/bees The test was carried out as follows: Test compounds: Compounds 1-9 and I-10, EC 50 Reference substance: Actara 25 WG (Thiamethoxam) Application rates: Compounds 1-9 and I-10: 100 g a.s./ha Actara: 50 g a.s./ha Crop plant: Lycopersicon esculentum Test organism: Apis mellifera Design: 180 m greenhouse Application: Spray application End points: Bee mortality after contact with treated tomato leaves In the greenhouse, the tomato plants were treated with the test compounds or the reference 10 substance (spray application, 3 replications). 1, 3, 6 and 13 days post-treatment (DAA), leaves were sampled (in each case 5 leaf samples per treatment) and placed into boxes. 10 bees were transferred into each box, and the boxes were stored under controlled conditions, the bees being fed sugar solution. 24, 48 and 72 hours after the bees' transfer, their mortality was determined.

- 24 Table 9 (see also Figure 9) Mortality [%] 24 h 48 h 72 h Untreated 8 9 11 Thiamethoxam 50 g a.s./ha 100 100 100 1-9 100 g a.s./ha 6 9 13 1-10 100 g a.s./ha 5 5 6 Mortality of bees in % after having been in contact for different periods of time with tomato leaves which had been sampled one day after the treatment of the tomato plants with the test compounds 5 or the reference substance. Table 10 (see also Figure 10) Mortality [%] 24 h 48 h 72 h Untreated 3 5 6 Thiamethoxam 50 g a.s./ha 100 100 100 1-9 100 g a.s./ha 2 3 4 1-10 100 g a.s./ha 3 7 8 Mortality of bees in % after having been in contact for different periods of time with tomato leaves which had been sampled 3 days after the treatment of the tomato plants with the test compounds or 10 the reference substance.

-25 Table 11 (see also Figure 11) Mortality [%] 24 h 48 h 72 h Untreated 3 5 7 Thiamethoxam 50 g a.s./ha 100 100 100 1-9 100 g a.s./ha 1 2 5 1-10 100 g a.s./ha 3 4 7 Mortality of bees in % after having been in contact for different periods of time with tomato leaves which had been sampled 6 days after the treatment of the tomato plants with the test compounds or 5 the reference substance. Table 12 (see also Figure 12) Mortality 1%] 24 h 48 h 72 h Untreated 14 14 16 Thiamethoxam 50 g a.s./ha 93,3 93 93,3 1-9 100 g a.s./ha 8,7 11 12 I-10 100 g a.s./ha 6,7 6,7 6,7 Mortality of bees in % after having been in contact for different periods of time with tomato leaves which had been sampled 13 days after the treatment of the tomato plants with the test compounds 10 or the reference substance.

Claims (4)

1. Use of at least one of the compounds selected from among 4-{[(6-chloropyrid

3-yl)methyl](2,2-difluoroethyl)amino}furan-2(5H)-one, 4-{[(6-chloropyrid-3-yl)methyl] (cyclopropyl)amino} furan-2(5H)-one or 4- {[(6-chloropyrid-3-yl)methyl](methyl) 5 amino}furan-2(5H)-one for the selective control of animal pests, characterized in that pollinating insects are not harmed upon contact with the compounds. 2. Method of protecting pollinating insects, characterized in that at least one of the compounds selected from among 4-{[(6-chloropyrid-3-yl)methyl](2,2-difluoroethyl) amino}furan-2(5H)-one, 4-{[(6-chloropyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H) 10 one or 4-{[(6-chloropyrid-3-yl)methyl](methyl)amino}furan-2(5H)-one is used for the selective control of animal pests. 3. Method according to Claim 2, where the pollinating insects are insects from the superfamily of the Apoidea.

4. Method according to Claim 2 or 3, characterized in that the compounds are applied as a 15 foliar application, soil application or seed treatment.

5. Method according to one of Claims 2 to 4, characterized in that the compounds are applied to flowering plants or in the vicinity of flowering plants or to, or in the vicinity of, plants which are visited by the pollinating insects.