Patent Publication Number: US-2011053996-A1

Title: Use of phenyltriazoles for controlling insects and spider mites by watering, droplet application or dip application or by treating seed

Description:
The present invention relates to the use of phenyltriazoles for controlling insects and/or spider mites and/or nematodes by watering, droplet application, dip (immersion) application or by treating seed. 
     Phenyltriazoles have already been described in WO 1999/55668 and WO 2006/043635. These documents also report an insecticidal action. 
     Surprisingly, it has now been found that phenyltriazole derivatives are also highly suitable for controlling insects and spider mites by watering on the ground (known as “drenching” by persons skilled in the art), droplet application on the ground (known as “drip application” by persons skilled in the art), dip application or by treating seed. 
     Accordingly, the present invention relates to the use of phenyltriazoles for controlling insects and/or spider mites and/or nematodes by drenching, in irrigation systems as drip application or by dip application and for seed treatment. The present invention relates in particular to these application forms on artificial soilless cultivation substrates (for example rock wool, glass wool, quartz sand, gravel, expanded clay, vermiculite), outdoors or in closed systems (for example greenhouses or under cloches) and in annual (for example vegetables, spices, ornamental plants), but also perennial (for example citrus plants, conifers, ornamental plants, shrubs) crops. 
     The crops to be protected which have only been described in general terms will be described in greater detail and specified hereinbelow. Thus, as regards the use, vegetables are understood as meaning for example fruiting vegetables and inflorescences as vegetables, for example bell peppers, chillies, tomatoes, aubergines, cucumbers, pumpkins, courgettes, broad beans, runner beans, dwarf beans, peas, artichokes, maize; 
     but also leafy vegetables, for example head-forming lettuce, chicory, endives, various types of cress, of rocket, lamb&#39;s lettuce, iceberg lettuce, leeks, spinach, Swiss chard; 
     furthermore tuberous, root and stalk vegetables, for example celeriac, red beetroot, carrots, radishes, horseradish, salsify, asparagus, turnips, palm shoots, bamboo shoots, moreover allium vegetables, for example onions, leek, fennel, garlic; 
     furthermore Brassica vegetables such as cauliflower, broccoli, kohlrabi, red cabbage, white cabbage, curly kale, Savoy cabbage, Brussel sprouts, Chinese cabbage. 
     Regarding the use, perennial crops are understood as meaning citrus, such as, for example, oranges, grapefruits, tangerines, lemons, limes, Seville oranges, kumquats, satsumas; 
     but also pome fruit such as, for example, apples, pears and quinces, and stone fruit, such as, for example, peaches, nectarines, cherries, plums, quetsch, apricots; 
     furthermore grapevines, hops, olives, tea and tropical crops such as, for example, mangoes, papayas, figs, pineapples, dates, bananas, durians, kaki fruit, coconuts, cacao, coffee, avocados, lychees, maracujas, guavas, 
     moreover almonds and nuts such as, for example, hazelnuts, walnuts, pistachios, cashew nuts, para nuts, pecan nuts, butternuts, chestnuts, hickory nuts, macadamia nuts, peanuts, 
     moreover also soft fruit such as, for example, redcurrants, gooseberries, raspberries, blackberries, blueberries, strawberries, cranberries, including American cranberries, kiwi fruit. 
     Regarding the use, ornamental plants are understood as meaning annual and perennial plants, for example cut flowers such as, for example, roses, carnations, gerbera, lilies, marguerites, chrysanthemums, tulips, narcissi, anemones, poppy, amaryllis, dahlias, azaleas, mallows, 
     but also for example bedding plants, pot plants and perennials such as, for example, roses, Tagetes, violas, geraniums, fuchsias, hibiscus, chrysanthemum, busy lizzie, cyclamen, African violet, sunflowers, begonias, 
     furthermore for example bushes and conifers such as, for example, ficus, rhododendron, firs, spruces, pines, including umbrella pines, yews, juniper, oleander. 
     As regards the use, spices are understood as meaning annual and perennial plants such as, for example, aniseed, chili pepper, paprika, pepper, vanilla, marjoram, thyme, cloves, juniper berries, cinnamon, tarragon, coriander, saffron, ginger. 
     The general formula (I) provides a definition of the phenyltriazoles according to the invention which can be used insecticidally and/or acaricidally and/or nematicidally 
     
       
         
         
             
             
         
       
     
     in which
 
R 1  represents H or NH 2 ,
 
R 2  represents CH 3  or F.
 
     Preferred sub-groups of the compounds of the formula (I) are listed below. 
     In a special group of compounds of the formula (I), R 1  represents hydrogen. 
     In a further special group of compounds of the formula (I), R 1  represents NH 2 . 
     In a further special group of compounds of the formula (I), R 2  represents methyl. 
     In a further special group of compounds of the formula (I), R 2  represents fluorine. 
     A preferred sub-group of the compounds of the formula (I) are those of the formula (I-1) 
     
       
         
         
             
             
         
       
     
     A further preferred sub-group of the compounds of the formula (I) are those of the formula (I-2) 
     
       
         
         
             
             
         
       
     
     A further preferred sub-group of the compounds of the formula (I) are those of the formula (I-3) 
     
       
         
         
             
             
         
       
     
     A further preferred sub-group of the compounds of the formula (I) are those of the formula (I-4) 
     
       
         
         
             
             
         
       
     
     The compounds of the general formula (I) have a chiral sulphoxide group so that, provided further centres of chirality are absent, they form two enantiomers having R or S configuration at the sulphur: 
     
       
         
         
             
             
         
       
     
     where R 1 , R 2  have the meanings given above. 
     In the synthesis from achiral starting materials the two enantiomers are formed in equal amount so that a racemate is present. The separation of the racemate known from the literature (cf. WO 1999/055668 and WO 2006/043635) into the individual enantiomers can be carried out by preparative HPLC on a chiral stationary phase. The separation may take place, for example, on a Daical Chiralpak AD-H 250 mm×30 mm column using a mobile phase of n-heptane/ethanol/methanol 60:20:20 (v/v/V), a flow rate of 30 ml/min and UV detection at 220 nm. The two enantiomers can then be characterized by methods known from the literature, for example by X-ray structural analysis or by determining the optical rotation. 
     Accordingly, the present invention also provides the use of phenyltriazoles comprising the R or S enantiomers of the compounds of the formula (I). 
     Particularly preferred sub-groups of the compounds of the formula (I) are the respective R or S enantiomers of the formulae (I-1A), (I-1B), (I-2A), (I-2B), (I-3A), (I-3B), (I-4A), (I-4B): 
     
       
         
         
             
             
         
       
     
     The use according to the invention of the phenyltriazole derivatives is against a large variety of animal pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, in forests and in gardens and leisure facilities, against normally sensitive and resistant species and against all or some stages of development. These pests include: 
     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 siro, Aceria sheldoni, Aculops  spp.,  Aculus  spp.,  Amblyomma  spp.,  Argas  spp.,  Boophilus  spp.,  Brevipalpus  spp.,  Bryobia praetiosa, Chorioptes  spp.,  Deimanyssus gallinae, Eutetranychus  spp.,  Epitrimerus pyri, Eutetranychus  spp.,  Eriophyes  spp.,  Hemitarsonemus  spp.,  Hyalomma  spp.,  Ixodes  spp.,  Latrodectus mactans, Metatetranychus  spp.,  Oligonychus  spp.,  Ornithodoros  spp.,  Panonychus  spp.,  Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes  spp.,  Rhipicephalus  spp.,  Rhizoglyphus  spp.,  Sarcoptes  spp.,  Scorpio maurus, 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,  Acanthoscelides obtectus, Adoretus  spp.,  Agelastica alni, Agriotes  spp.,  Amphimallon solstitialis, Anobium punctatum, Anoplophora  spp.,  Anthonomus  spp.,  Anthrenus  spp.,  Apogonia  spp.,  Atomaria  spp.,  Attagenus  spp.,  Bruchidius obtectus, Bruchus  spp.,  Ceuthorhynchus  spp.,  Cleonus mendicus, Conoderus  spp., Cosmopolites spp.,  Costelytra zealandica, Curculio  spp.,  Cryptorhynchus lapathi, Dermestes  spp.,  Diabrotica  spp.,  Epilachna  spp.,  Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus  spp.,  Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus  spp.,  Lyctus  spp.,  Meligethes aeneus, Melolontha melolontha, Migdolus  spp.,  Monochamus  spp.,  Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga  spp.,  Popillia japonica, Premnotrypes  spp.,  Psylliodes chrysocephala, Ptinus  spp.,  Rhizobius ventralis, Rhizopertha dominica, Sitophilus  spp.,  Sphenophorus  spp.,  Sternechus  spp.,  Symphyletes  spp.,  Tenebrio molitor, Tribolium  spp.,  Trogoderma  spp.,  Tychius  spp.,  Xylotrechus  spp.,  Zabrus  spp. 
     From the order of the Collembola, for example,  Onychiurus armatus.    
     From the order of the Dennaptera, for example,  Forficula auricularia.    
     From the order of the Diplopoda, for example,  Blaniulus guttulatus.    
     From the order of the Diptera, for example,  Aedes  spp.,  Anopheles  spp.,  Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia  spp.,  Cochliomyia  spp.,  Cordylobia anthropophaga, Culex  spp.,  Cuterebra  spp.,  Dacus oleae, Dermatobia hominis, Drosophila  spp.,  Fannia  spp.,  Gastrophilus  spp.,  Hylemyia  spp.,  Hyppobosca  spp.,  Hypoderma  spp.,  Liriomyza  spp.,  Lucilia  spp.,  Musca  spp.,  Nezara  spp.,  Oestrus  spp.,  Oscinella frit, Pegomyia hyoscyami, Phorbia  spp.,  Stomoxys  spp.,  Tabanus  spp.,  Tannia  spp.,  Tipula paludosa, Wohlfahrtia  spp. 
     From the class of the Gastropoda, for example,  Arion  spp.,  Biomphalaria  spp.,  Bulinus  spp.,  Deroceras  spp.,  Galba  spp.,  Lymnaea  spp.,  Oncomelania  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 granulosus, Echinococcus multilocularis, Enterobius vezniicularis, 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, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus  spp.,  Trichuris trichuria, Wuchereria bancrofti.    
     It is furthermore possible to control Protozoa, such as  Eimeria.    
     From the order of the Heteroptera, for example,  Anasa tristis, Antestiopsis  spp.,  Blissus  spp.,  Calocoris  spp.,  Campylomma livida, Cavelerius  spp.,  Cimex  spp.,  Creontiades 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, Nezara  spp.,  Oebalus  spp.,  Pentomidae, Piesma quadrata, Piezodorus  spp.,  Psallus seriatus, Pseudacysta persea, Rhodnius  spp.,  Sahlbergella singularis, Scotinophora  spp.,  Stephanitis nashi, Tibraca  spp.,  Triatoma  spp. 
     From the order of the Homoptera, for example,  Acyrthosipon  spp.,  Aeneolamia  spp.,  Agonoscena  spp.,  Aleurodes  spp.,  Aleurolobus barodensis, Aleurothrixus  spp.,  Amrasca  spp.,  Anuraphis cardui, Aonidiella  spp.,  Aphanostigma pini, Aphis  spp.,  Arboridia apicalis, Aspidiella  spp.,  Aspidiotus  spp.,  Atanus  spp.,  Aulacorthum solani, Bemisia  spp.,  Brachycaudus helichrysii, Brachycolus  spp.,  Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes  spp.,  Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus  spp.,  Cryptomyzus ribis, Dalbulus  spp.,  Dialeurodes  spp.,  Diaphorina  spp.,  Diaspis  spp.,  Doralis  spp.,  Drosicha  spp.,  Dysaphis  spp.,  Dysmicoccus  spp.,  Empoasca  spp.,  Eriosorna  spp.,  Erythroneura  spp.,  Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya  spp.,  Idiocerus  spp.,  Idioscopus  spp.,  Laodelphax striatellus, Lecanium  spp.,  Lepidosaphes  spp.,  Lipaphis erysimi, Macrosiphum  spp.,  Mahanarva fimbriolata, 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, 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 anticulatus, Sogata  spp.,  Sogatella furcifera, Sogatodes  spp.,  Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis  spp.,  Toxoptera  spp.,  Trialeurodes vaporariorum, Trioza  spp.,  Typhlocyba  spp.,  Unaspis  spp.,  Viteus vitifolii.    
     From the order of the Hymenoptera, for example,  Diprion  spp.,  Hoplocampa  spp.,  Lasius  spp.,  Monomorium pharaonis  and  Vespa  spp. 
     From the order of the Isopoda, for example,  Armadillidium vulgare, Oniscus asellus  and  Porcellio scaber.    
     From the order of the Isoptera, for example,  Reticulitermes  spp. and  Odontotermes  spp. 
     From the order of the Lepidoptera, for example,  Acronicta major, Aedia leucomelas, Agrotis  spp.,  Alabama argillacea, Anticarsia  spp.,  Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomonella, Chematobia brumata, Chilo  spp.,  Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus  spp.,  Earias insulana, Ephestia kuehnielia, Euproctis chrysorrhoea, Euxoa  spp.,  Feltia  spp.,  Galleria mellonella, Helieoverpa  spp.,  Heliothis  spp.,  Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma  spp.,  Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria  spp.,  Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria  spp.,  Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris  spp.,  Plutella xylostella, Prodenia  spp.,  Pseudaletia  spp.,  Pseudoplusia includens, Pyrausta nubilalis, Spodoptera  spp.,  Theimesia gemmatalis, Tinea pellionella, Tineola bisselliella, ToiLiix viridana, Trichoplusia  spp. 
     From the order of the Orthoptera, for example,  Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa  spp.,  Leucophaea maderae, Locusta  spp.,  Melanoplus  spp.,  Periplaneta americana, Schistocerca gregaria.    
     From the order of the Siphonaptera, for example,  Ceratophyllus  spp. and  Xenopsylla cheopis.    
     From the order of the Symphyla, for example,  Scutigerella immaculata.    
     From the order of the Thysanoptera, for example,  Baliothrips biformis, Enneothrips flavens, Frankliniella  spp.,  Heliothrips  spp.,  Hercinothrips femoralis, Kakothrips  spp.,  Rhipiphorothrips cruentatus, Scirtothrips  spp.,  Taeniothrips cardamoni, Thrips  spp. 
     From the order of the Thysanura, for example,  Lepisma saccharina.    
     The phytoparasitic nematodes include, for example,  Anguina  spp.,  Aphelenchoides  spp.,  Belonoaimus  spp  Bursaphelenchus  spp.,  Ditylenchus dipsaci, Globodera  spp.,  Heliocotylenchus  spp.,  Heterodera  spp.,  Longidorus  spp.,  Meloidogyne  spp.,  Pratylenchus  spp.,  Radopholus similis, Rotylenchus  spp.,  Trichodorus  spp.,  Tylenchorhynchus  spp.,  Tylenchulus  spp.,  Xiphinema  spp. 
     The use according to the invention of the phenyltriazole derivatives can be on its own, but also in combination with other active compounds. Accordingly, compositions to be used according to the invention may, in addition to at least one phenyltriazole derivative, also comprise other active compounds, such as further systemic insecticides, attractants, sterilants, bactericides, systemic acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals. 
     The compositions to be used according to the invention may furthermore comprise synergists. Synergists are compounds which increase the action of the active compounds, without it being necessary for the synergist added to be active itself. 
     The compositions to be used according to the invention may furthermore comprise inhibitors which reduce degradation of the active compound after application. 
     All plants can be treated in accordance with the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding, such as crossing or protoplast fusion, and also parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), are treated. 
     Particularly preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention. Plant cultivars are to be understood as meaning plants having new properties (“traits”) and which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. They can be cultivars, biotypes or genotypes. 
     Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, nutrition), the treatment according to the invention may also result in superadditive (“synergistic”) effects. Thus possible are, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase of the activity of the compositions according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or higher nutritional value of the harvested products, increased storability and/or processibility of the harvested products, which exceed the effects normally to be expected. 
     The preferred transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are to be treated according to the invention include all plants which, in the genetic modification, received genetic material which imparted particularly advantageous useful properties (“traits”) to these plants. Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering, easier harvesting, accelerated maturation, higher harvest yields, higher quality and/or a higher nutritional value of the harvested products, better storability and/or processability of the harvested products. Further and particularly emphasized examples of such properties are a better defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and/or viruses, and also increased tolerance of the plants to certain herbicidally active compounds. Examples of transgenic plants which may be mentioned are the important crop plants, such as cereals (wheat, rice), maize, soya beans, potatoes, sugar beet, tomatoes, peas and other types of vegetable, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), with particular emphasis being given to maize, soya beans, potatoes, cotton, tobacco and oilseed rape. Traits that are emphasized in particular are increased defense of the plants against insects, arachnids, nematodes and slugs and snails by toxins foamed in the plants, in particular those formed in the plants by the genetic material from  Bacillus thuringiensis  (for example by the genes CryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred to as “Bt plants”). Traits that are also particularly emphasized are the increased defense of the plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and also resistance genes and correspondingly expressed proteins and toxins. Traits that are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinothricin (for example the “PAT” gene). The genes which impart the desired traits in question can also be present in combinations with one another in the transgenic plants. Examples of “Bt plants” which may be mentioned are maize varieties, cotton varieties, soya bean varieties and potato varieties which are sold under the trade names YIELD GARD® (for example maize, cotton, soya beans), KnockOut® (for example maize), StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton varieties and soya bean varieties which are sold under the trade names Roundup Ready® (tolerance against glyphosate, for example maize, cotton, soya beans), Liberty Link® (tolerance against phosphinothricin, for example oilseed rape), IMI® (tolerance against imidazolinones) and STS® (tolerance against sulphonylurea, for example maize). Herbicide-resistant plants (plants bred in a conventional manner for herbicide tolerance) which may be mentioned include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant cultivars having these genetic traits or genetic traits still to be developed, which plants will be developed and/or marketed in the future. 
     The use according to the invention of the phenyltriazole derivatives is by drenching, in irrigation systems as drip application, by dip application or, in the case of propagation material, in particular in the case of seed, furthermore by application of one or more coats. 
     Preference according to the invention is given to the treatment of seed. Thus, most of the damage to crop plants which is caused by pests occurs as early as when the seed is infested during storage and after the seed is introduced into the soil, and during and immediately after germination of the plants. This phase is particularly critical since the roots and shoots of the growing plants are particularly sensitive and even minor damage can lead to the death of the whole plant. Protecting the seed and the germinating plant by the use of suitable compositions is therefore of particularly great interest. 
     The control of pests by treating the seed of plants has been known for a long time and is the subject of continuous improvements. However, the treatment of seed entails a series of problems which cannot always be solved in a satisfactory manner. Thus, it is desirable to develop methods for protecting the seed and the germinating plant which dispense with the additional application of crop protection products after sowing or after emergence of the plants. It is furthermore desirable to optimize the amount of active compound employed in such a way as to provide optimum protection for the seed and the germinating plant from attack by pests, but without damaging the plant itself by the active compound employed. In particular, methods for the treatment of seed should also take into consideration the intrinsic insecticidal properties of transgenic plants in order to achieve optimum protection of the seed and the germinating plant with a minimum of crop protection products being employed. 
     The present invention therefore in particular also relates to a method for the protection of seed and germinating plants, from attack by pests, by treating the seed with an active compound according to the invention. The invention likewise relates to the use of phenyltriazoles for the treatment of seed for protecting the seed and the plants resulting therefrom from pests. Furthermore, the invention relates to seed which has been treated according to the invention so as to afford protection from pests. 
     One of the advantages of the present invention is that the particular systemic properties of phenyltriazole derivatives mean that treatment of the seed with these active compounds not only protects the seed itself, but also the resulting plants after emergence, from pests. In this manner, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with. 
     Furthermore, it must be considered as advantageous that according to the invention the phenyltriazoles can also be employed in particular in transgenic seed, the plants arising from this seed being capable of expressing a protein directed against pests. By treating such seed, certain pests can be controlled merely by the expression of the, for example, insecticidal protein, and additionally damage to the seed may be averted by the active compounds according to the invention. 
     The use according to the invention of the phenyltriazole derivatives is suitable for protecting seed of any plant variety as already mentioned above which is employed in agriculture, in the greenhouse, in forests or in horticulture. In particular, this takes the form of seed of maize, peanut, canola, oilseed rape, poppy, soya beans, cotton, beet (for example sugar beet and fodder beet), rice, millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables (for example tomatoes, cabbage species). The active compounds according to the invention are likewise suitable for treating the seed of fruit plants and vegetables as already mentioned above. The treatment of the seed of maize, soya beans, cotton, wheat, rice and canola or oilseed rape is of particular importance. 
     As already mentioned above, the treatment of transgenic seed with active compounds according to the invention is also of particular importance. This takes the form of seed of plants which, as a rule, comprise at least one heterologous gene which governs the expression of a polypeptide with in particular insecticidal properties. In this context, the heterologous genes in transgenic seed may be derived from microorganisms such as  Bacillus, Rhizobiwn, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus  or  Gliocladium . The present invention is particularly suitable for the treatment of transgenic seed which comprises at least one heterologous gene originating from  Bacillus  sp. and whose gene product shows activity against the European corn borer and/or the corn root worm. It is particularly preferably a heterologous gene derived from  Bacillus thuringiensis.    
     Within the context of the present invention, the phenyltriazole derivatives are applied to the seed either alone or in a suitable formulation. Preferably, the seed is treated in a state in which it is stable enough to avoid damage during treatment. In general, the seed may be treated at any point in time between harvest and sowing. The seed usually used has been separated from the plant and freed from cobs, shells, stalks, coats, hairs or the flesh of the fruits. 
     When treating the seed, care must generally be taken that the amount of the phenyltriazole derivatives applied to the seed and/or the amount of further additives is chosen in such a way that the germination of the seed is not adversely affected, or that the resulting plant is not damaged. 
     The compositions according to the invention can be applied directly, i.e. without containing any other components and undiluted. In general, it is preferred to apply the compositions to the seed in the form of a suitable formulation. Suitable formulations and methods for treating seed are known to the person skilled in the art and are described, for example, in the following documents: U.S. Pat. No. 4,272,417 A, U.S. Pat. No. 4,245,432 A, U.S. Pat. No. 4,808,430 A, U.S. Pat. No. 5,876,739 A, US 2003/0176428 A1, WO 2002/080675 A1, WO 2002/028186 A2. 
     The active compounds which can be used in accordance with the invention can be converted into the customary seed-dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other coating compositions for seed, and also ULV formulations. 
     These formulations are prepared in a known manner, by mixing the active compounds with customary additives such as, for example, customary extenders and also solvents or diluents, colorants, wetting agents, dispersants, emulsifiers, antifoams, preservatives, secondary thickeners, adhesives, gibberellins and also water. 
     Colorants which may be present in the seed-dressing formulations which can be used in accordance with the invention are all colorants which are customary for such purposes. In this context, not only pigments, which are sparingly soluble in water, but also dyes, which are soluble in water, may be used. Examples which may be mentioned are the colorants known by the names Rhodamin B, C.I. Pigment Red 112 and C.I. Solvent Red 1. 
     Suitable wetting agents which may be present in the seed-dressing formulations which can be used in accordance with the invention are all substances which promote wetting and which are conventionally used for the formulation of agrochemical active compounds. Preference is given to using alkylnaphthalenesulphonates, such as diisopropyl- or diisobutylnaphthalenesulphonates. 
     Suitable dispersants and/or emulsifiers which may be present in the seed-dressing formulations which can be used in accordance with the invention are all nonionic, anionic and cationic dispersants conventionally used for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants. Suitable nonionic dispersants which may be mentioned are, in particular, ethylene oxide/propylene oxide block polymers, alkylphenol polyglycol ethers and tristyrylphenol polyglycol ether, and their phosphated or sulphated derivatives. Suitable anionic dispersants are, in particular, lignosulphonates, polyacrylic acid salts and arylsulphonate/formaldehyde condensates. 
     Antifoams which may be present in the seed-dressing formulations which can be used in accordance with the invention are all foam-inhibiting substances conventionally used for the formulation of agrochemical active compounds. Silicone antifoams and magnesium stearate can preferably be used. 
     Preservatives which may be present in the seed-dressing formulations which can be used in accordance with the invention are all substances which can be employed for such purposes in agrochemical compositions. Dichlorophene and benzyl alcohol hemiformal may be mentioned by way of example. 
     Secondary thickeners which may be present in the seed-dressing formulations which can be used in accordance with the invention are all substances which can be employed for such purposes in agrochemical compositions. Cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica are preferred. 
     Adhesives which may be present in the seed-dressing formulations which can be used in accordance with the invention are all customary binders which can be employed in seed-dressing products. Polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and tylose may be mentioned as being preferred. 
     Gibberellins which can be present in the seed-dressing formulations which can be used in accordance with the invention are preferably the gibberellins A1, A3 (=gibberellic acid), A4 and A7; gibberellic acid is especially preferably used. The gibberellins are known (cf. R. Wegler “Chemie der Pflanzenschutz- and Schädlingsbekämpfungsmittel” [Chemistry of crop protection agents and pesticides], vol. 2, Springer Verlag, 1970, p. 401-412). 
     The seed-dressing formulations which can be used in accordance with the invention can be employed for the treatment of a wide range of seed, including the seed of transgenic plants, either directly or after previously having been diluted with water. In this context, additional synergistic effects may also occur in cooperation with the substances foamed by expression. 
     All mixers which can conventionally be employed for the seed-dressing operation are suitable for treating seed with the seed-dressing formulations which can be used in accordance with the invention or with the preparations prepared therefrom by addition of water. Specifically, a procedure is followed during the seed-dressing operation in which the seed is placed into a mixer, the specific desired amount of seed-dressing formulations, either as such or after previously having been diluted with water, is added, and everything is mixed until the formulation is distributed uniformly on the seed. If appropriate, this is followed by a drying process. 
     The application rate of the seed-dressing formulations which can be used according to the invention may be varied within a relatively wide range. It depends on the respective content of the active compounds in the formulations and on the seed. The active compound combination application rates are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed. 
    
    
     USE EXAMPLES 
     The examples below illustrate the invention, without limiting it in any way. 
     To produce a suspension concentrate, initially all liquid components are mixed with one another. In the next step, the solids are added and the mixture is stirred until a homogeneous suspension is formed. The homogeneous suspension is subjected first to coarse grinding and then to fine grinding, giving a suspension in which 90% of all solid particles have a particle size of less than 10 μm. Kelzan S and water are than added with stirring at room temperature. A homogeneous suspension concentrate is obtained. Contents are stated in % by weight. 
     Example No. 1 
       Tetranychus urticae  Test on Aubergine; Drench Application (France) 
     To produce a suitable solution, the formulated product is mixed with water and diluted to the desired concentration. 
     Approx. 3-week-old aubergine plants ( Solanum melongena ) infected with a mixed population of the greenhouse red spider mite ( Tetranychus urticae ) are watered with the respective product solution (volume of water: 50 ml/plant): The stated concentration refers to the amount of active compound per plant. 
     After the desired period of time, the effect in % is determined. 100% means that all of the spider mites have been killed; 0% means that none of the spider mites have been killed. 
     In this test, the following product showed good systemic action: 
     
       
         
           
               
             
               
                 TABLE 1 
               
             
            
               
                   
               
               
                   Tetranychus urticae  on aubergines 
               
            
           
           
               
               
               
               
            
               
                   
                   
                 Time at which the 
                   
               
               
                   
                   
                 mortality is 
                 % Activity 
               
               
                   
                 Concentration 
                 determined/days after 
                 (according to 
               
               
                 Active compound 
                 (mg of ai/plant) 
                 treatment 
                 Abbott) 
               
               
                   
               
               
                 (I-1) SC 025 
                 20 
                 23 
                 99 
               
               
                 according to the 
               
               
                 invention 
               
               
                   
               
            
           
         
       
     
     Example No. 2 
       Liriomyza  spp. Test on Tomatoes; Drench Application (France) 
     To produce a suitable solution, the formulated product is mixed with water and diluted to the desired concentration. 
     Tomato plants ( Solanum esculentum ) at the 3-leaf stage (BBCH 13) infested with a mixed population of leaf-mining flies ( Liriomyza  spp.) are watered with the respective product solution (volume of water: 50 ml/plant): The stated concentration refers to the amount of active compound per plant. 
     After the desired period of time, the effect in % is determined. 100% means that all of the leaf-mining flies have been killed; 0% means that none of the leaf-mining flies have been killed. 
     In this test, the following product showed good systemic action: 
     
       
         
           
               
             
               
                 TABLE 2 
               
             
            
               
                   
               
               
                   Liriomyza  spp. on tomatoes 
               
            
           
           
               
               
               
               
            
               
                   
                   
                 Time at which the 
                   
               
               
                   
                   
                 mortality is 
                 % Activity 
               
               
                   
                 Concentration 
                 determined/days after 
                 (according to 
               
               
                 Active compound 
                 (mg of ai/plant) 
                 treatment 
                 Abbott) 
               
               
                   
               
               
                 (I-1) SC 025 
                 20 
                 13 
                 100 
               
               
                 according to the 
               
               
                 invention 
               
               
                   
               
            
           
         
       
     
     Example No. 3 
       Phyllocnistis citrella  Test on Oranges; Drench Application (Brasil) 
     To produce a suitable solution, the formulated product is mixed with water and diluted to the desired concentration. 
     Approx. 1-year-old orange trees ( Citrus sinensis ) infested with citrus leaf-mining moths ( Phyllocnistis citrella ) are watered with the respective product solution (volume of water: 50 ml/plant): The stated concentration refers to the amount of active compound per plant. 
     After the desired period of time, the effect in % is determined. 100% means that all of the leaf-mining moths have been killed; 0% means that none of the leaf-mining moths have been killed. 
     In this test, the following product showed good systemic action: 
     
       
         
           
               
             
               
                 TABLE 3 
               
             
            
               
                   
               
               
                   Phyllocnistis citrella  on orange trees 
               
            
           
           
               
               
               
               
            
               
                   
                   
                 Time at which the 
                   
               
               
                   
                   
                 mortality is 
                 % Activity 
               
               
                   
                 Concentration 
                 determined/days after 
                 (according to 
               
               
                 Active compound 
                 (mg of ai/plant) 
                 treatment 
                 Abbott) 
               
               
                   
               
               
                 (I-1) SC 025 
                 20 
                 28 
                 77.6 
               
               
                 according to the 
               
               
                 invention 
               
               
                   
               
            
           
         
       
     
     Example No. 4 
       Toxoptera citricidus  Test on Oranges; Drench Application (Brasil) 
     To produce a suitable solution, the formulated product is mixed with water and diluted to the desired concentration. 
     Orange trees of a height of 1 m ( Citrus sinensis ) infested with a mixed population of the citrus aphid ( Toxoptera citricidus ) are watered with the respective product solution (volume of water: 50 ml/plant): The stated concentration refers to the amount of active compound per plant. 
     After the desired period of time, the effect in % is determined. 100% means that all of the aphids have been killed; 0% means that none of the aphids have been killed. 
     In this test, the following product showed good systemic action: 
     
       
         
           
               
             
               
                 TABLE 4 
               
             
            
               
                   
               
               
                   Toxoptera citricidus  on orange trees 
               
            
           
           
               
               
               
               
            
               
                   
                   
                 Time at which the 
                   
               
               
                   
                   
                 mortality is 
                 % Activity 
               
               
                   
                 Concentration 
                 determined/days after 
                 (according to 
               
               
                 Active compound 
                 (mg of ai/plant) 
                 treatment 
                 Abbott) 
               
               
                   
               
               
                 (I-1) SC 025 
                 20 
                 149 
                 90 
               
               
                 according to the 
               
               
                 invention 
               
               
                   
               
            
           
         
       
     
     Example No. 5 
       Liriomyza trifolii  Test on Tomatoes; Drench Application (Italy) 
     To produce a suitable solution, the formulated product is mixed with water and diluted to the desired concentration. 
     Tomato plants ( Solanum esculentum ) at the 4-leaf stage (BBCH 14) infested with a mixed population of leaf-mining flies ( Liriomyza trifolii ) are watered with the respective product solution (volume of water: 200 ml/plant): The stated concentration refers to the amount of active compound per plant. 
     After the desired period of time, the effect in % is determined. 100% means that all of the leaf-mining flies have been killed; 0% means that none of the leaf-mining flies have been killed. 
     In this test, the following product showed good systemic action: 
     
       
         
           
               
             
               
                 TABLE 5 
               
             
            
               
                   
               
               
                   Liriomyza trifolii  on tomatoes 
               
            
           
           
               
               
               
               
            
               
                   
                   
                 Time at which the 
                   
               
               
                   
                   
                 mortality is 
                 % Activity 
               
               
                   
                 Concentration 
                 determined/days after 
                 (according to 
               
               
                 Active compound 
                 (mg of ai/plant) 
                 treatment 
                 Abbott) 
               
               
                   
               
               
                 (I-4) SC 025 
                 5 
                 19 
                 80.9 
               
               
                 according to the 
               
               
                 invention 
               
               
                   
               
            
           
         
       
     
     Example No. 6 
       Tetranychus urticae  Test on Bush Beans; 
     Seed Application Greenhouse 
     To produce a suitable solution, the formulated product is mixed with water and diluted to the desired concentration. 
     Bush bean seed ( Phaseolus vulgaris ) is dressed with the active compound preparation and sown into soil. After about 2 weeks, the bush bean plants are infested with the greenhouse red spider mite ( Tetranychus urticae ). 
     After the desired period of time, the effect in % is determined. 100% means that all of the spider mites have been killed; 0% means that none of the spider mites have been killed. 
     In this test, the following product showed good systemic action: 
     
       
         
           
               
             
               
                 TABLE 6 
               
             
            
               
                   
               
               
                   Tetranychus urticae  on bush beans 
               
            
           
           
               
               
               
               
            
               
                   
                   
                 Time at which the 
                   
               
               
                   
                   
                 mortality is 
               
               
                   
                 Concentration 
                 determined/days after 
               
               
                 Active compound 
                 (mg of ai/plant) 
                 infestation 
                 % Activity 
               
               
                   
               
               
                 (I-4) SC 025 
                 1 
                 7 
                 100 
               
               
                 according to the 
               
               
                 invention 
               
               
                   
               
            
           
         
       
     
     Example No. 7 
       Liriomyza trifolii  Test on Bush Beans; Drench Application 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 Solvent: 
                 4 parts by weight of acetone 
               
               
                   
                 Emulsifier: 
                 1 part by weight of alkylaryl polyglycol ether 
               
               
                   
                   
               
            
           
         
       
     
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     Bush bean plants ( Phaseolus vulgaris ) are watered with the respective product solution. The stated concentration refers to the amount of active compound per plant. After about 1 week, the treated plants are infested with the leaf-mining fly ( Liriomyza trifolii ). 
     After 2 weeks, the effect in % is determined. 100% means that all of the leaf-mining flies have been killed; 0% means that none of the leaf-mining flies have been killed. 
     In this test, the following product showed good systemic action: 
     
       
         
           
               
             
               
                 TABLE 7 
               
             
            
               
                   
               
               
                   Liriomyza  tr. on bush bean 
               
            
           
           
               
               
               
               
            
               
                   
                   
                 Time at which the 
                   
               
               
                   
                   
                 mortality is 
                 % Activity 
               
               
                   
                 Concentration 
                 determined/days after 
                 (according to 
               
               
                 Active compound 
                 (mg of ai/plant) 
                 infestation 
                 Abbott) 
               
               
                   
               
               
                 (I-4) 
                 0.5 
                 14 
                 100 
               
               
                 according to the 
               
               
                 invention 
               
               
                   
               
            
           
         
       
     
     Example No. 8 
       Tetranychus urticae  Test on Bush Beans; Drench Application 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 Solvent: 
                 4 parts by weight of acetone 
               
               
                   
                 Emulsifier: 
                 1 part by weight of alkylaryl polyglycol ether 
               
               
                   
                   
               
            
           
         
       
     
     To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration. 
     Bush bean plants ( Phaseolus vulgaris ) are watered with the respective product solution. The stated concentration refers to the amount of active compound per plant. After about 1 week, the treated plants are infested with the greenhouse red spider mite ( Tetranychus urticae ). 
     After 2 weeks, the effect in % is determined. 100% means that all of the spider mites have been killed; 0% means that none of the spider mites have been killed. 
     In this test, the following product showed good systemic action: 
     
       
         
           
               
             
               
                 TABLE 8 
               
             
            
               
                   
               
               
                   Tetranychus  u. on bush bean 
               
            
           
           
               
               
               
               
            
               
                   
                   
                 Time at which the 
                   
               
               
                   
                   
                 mortality is 
                 % Activity 
               
               
                   
                 Concentration 
                 determined/days after 
                 (according to 
               
               
                 Active compound 
                 (mg of ai/plant) 
                 infestation 
                 Abbott) 
               
               
                   
               
               
                 (I-4) 
                 0.25 
                 14 
                 100 
               
               
                 according to the 
               
               
                 invention 
               
               
                   
               
            
           
         
       
     
     Example No. 9 
       Liriomyza sativae  Test on Aubergines; Drench Application (Japan) 
     To produce a suitable solution, the formulated product is mixed with water and diluted to the desired concentration. 
     Aubergine plants ( Solanum melongena ) at the 8-leaf stage (BBCH 18) infested with a mixed population of leaf-mining flies ( Liriomyza sativae ) are watered with the respective product solution (volume of water: 30 ml/plant): The stated concentration refers to the amount of active compound per plant. 
     After the desired period of time, the effect in % is determined. 100% means that all of the leaf-mining flies have been killed; 0% means that none of the leaf-mining flies have been killed. 
     In this test, the following product showed good systemic action: 
     
       
         
           
               
             
               
                 TABLE 9 
               
             
            
               
                   
               
               
                   Liriomyza sativae  on aubergines 
               
            
           
           
               
               
               
               
            
               
                   
                   
                 Time at which the 
                   
               
               
                   
                   
                 mortality is 
                 % Activity 
               
               
                   
                 Concentration 
                 determined/days after 
                 (according to 
               
               
                 Active compound 
                 (mg of ai/plant) 
                 treatment 
                 Abbott) 
               
               
                   
               
               
                 (I-4) SC 025 
                 5 
                 7 
                 100 
               
               
                 according to the 
               
               
                 invention