Patent Publication Number: US-2010113437-A1

Title: Active Compound Combinations Having Insecticidal and regular, utility

Description:
The present invention relates to novel active compound combinations consisting, firstly, of known cyclic ketoenols and, secondly, of further known insecticidally active compounds, which combinations are highly suitable for controlling animal pests such as insects and unwanted acarids. 
     It is already known that certain cyclic ketoenols have herbicidal, insecticidal and acaricidal properties. The activity of these compounds is good; however, it is sometimes unsatisfactory at low application rates. 
     1H-3-Arylpyrrolidine-2,4-dione derivatives (WO 98/05638) and their cis-isomers (WO 04/007448) are known to have insecticidal and/or acaricidal activity. 
     Furthermore known are mixtures of compounds from WO 98/05638 with other insecticides and/or acaricides: WO 01/89300, WO 02/00025, WO 02/05648, WO 02/17715, WO 02/19824, WO 02/30199, WO 02/37963, WO 05/004603, WO 05/053405, DE-A-05008033, DE-A-10342673. However, the activity of these mixtures is not always satisfactory. 
     It has now been found that active compound combinations comprising a compound of the formula (I) or (II) 
     
       
         
         
             
             
         
       
     
     and
 
A) benzoylureas, preferably
 
1. chlorfluazuron
 
     
       
         
         
             
             
         
       
     
     known from DE-A-2 818 830
         and/or
 
2. diflubenzuron
       

     
       
         
         
             
             
         
       
     
     known from DE-A 2 123 236
         and/or
 
3. lufenuron
       

     
       
         
         
             
             
         
       
     
     known from EP-A-179 022
         and/or
 
4. teflubenzuron
       

     
       
         
         
             
             
         
       
     
     known from EP-A-052 833
         and/or
 
5. triflumuron
       

     
       
         
         
             
             
         
       
     
     known from DE-A-2 601 780
         and/or
 
6. novaluron
       

     
       
         
         
             
             
         
       
     
     known from U.S. Pat. No. 4,980,376
         and/or
 
7. flufenoxuron
       

     
       
         
         
             
             
         
       
     
     known from EP-A 161 019
         and/or
 
8. hexaflumuron
 
9. bistrifluoron
       

     
       
         
         
             
             
         
       
     
     known from EP-A 71 279
         and/or       

     
       
         
         
             
             
         
       
     
     known from WO 98/00394
         and/or
 
10. noviflumuron
       

     
       
         
         
             
             
         
       
     
     known from WO 98/19542
         and/or
 
B) macrolides, preferably
 
11. emamectin
       

     known from EP-A-089 202
         and/or
 
C) diacylhydrazines, preferably
 
12. methoxyfenozide
       

     
       
         
         
             
             
         
       
     
     known from EP-A-639 559
         and/or
 
13. tebufenozide
       

     
       
         
         
             
             
         
       
     
     known from EP-A-339 854
         and/or
 
14. halofenozide
       

     
       
         
         
             
             
         
       
     
     known from EP-A 228 564
         and/or       

     15. JS-118 
     
       
         
         
             
             
         
       
     
     known from ZL 01108161.9, trade name Fu-Shen, 
     Modern Agrochemicals, Vol. 4, No. 3, 2005, 1-7
         and/or
 
16. chromafenozide
 
D) halocycloalkanes, preferably
 
17. endosulfan
       

     
       
         
         
             
             
         
       
     
     known from EP-A-496342
         and/or       

     
       
         
         
             
             
         
       
     
     known from DE-A-1 015 797
         and/or       

     18.  Trichogramma  spp. 
     known from The Pesticide Manual, 11th Edition, 1997, p. 1236
         and/or
 
19.  Verticillium lecanii  
       

     known from The Pesticide Manual, 11th Edition, 1997, p. 1266
         and/or
 
20. fipronil
       

     
       
         
         
             
             
         
       
     
     known from EP-A-295 117
         and/or
 
21. ethiprole
       

     
       
         
         
             
             
         
       
     
     known from WO 97/22593
         and/or
 
22. pyrafluprole
       

     
       
         
         
             
             
         
       
     
     known from WO 01/00614
         and/or
 
23. pyriprole
       

     
       
         
         
             
             
         
       
     
     known from WO 02/10153
         and/or
 
24. cyromazine
       

     
       
         
         
             
             
         
       
     
     known from DE-A-2 736 876
         and/or
 
25. azadirachtin
       

     known from The Pesticide Manual, 11th Edition, 1997, p. 59
         and/or
 
26. diofenolan
       

     
       
         
         
             
             
         
       
     
     known from DE-A 2 655 910
         and/or
 
27. indoxacarb
       

     
       
         
         
             
             
         
       
     
     known from WO 92/11249 and also the +-enantiomer DPX-KN 128 known from ACS Symposium Series 800, p. 178
         and/or       

     28. Rynaxapyr 
     
       
         
         
             
             
         
       
     
     known from WO 03/015519
         and/or
 
29. flubendiamide
       

     
       
         
         
             
             
         
       
     
     known from EP-A-01006107
         and/or
 
30. metaflumizone
       

     
       
         
         
             
             
         
       
     
     known from EP-A-00462456 have very good insecticidal and/or acaricidal properties. 
     Surprisingly, the insecticidal and/or acaricidal activity of the active compound combinations according to the invention is substantially higher than the activities of the prior-art mixtures from WO 02/19824, WO 05/004603, WO 05/053405 and DE-A-05008033 consisting of cis/trans isomer mixtures of the formula I-a or II-a and one of the compounds mentioned therein. 
     
       
         
         
             
             
         
       
     
     Preference is given to active compound combinations comprising the compound of the formula (I) and at least one active compound of the compounds 1 to 30. 
     Preference is also given to active compound combinations comprising the compound of the formula (II) and at least one active compound of the compounds 1 to 30. 
     In addition, the active compound combinations may also comprise further fungicidally, acaricidally or insecticidally active additives. 
     The improved activity becomes evident when the active compounds in the active compound combinations according to the invention are present in certain weight ratios. However, the weight ratios of the active compounds in the active compound combinations can be varied within a relatively wide range. In general, the combinations according to the invention comprise active compounds of the formula (I) or (II) and the mixing partner in the preferred and particularly preferred mixing ratios stated in the table below: 
     
       
         
           
               
               
               
               
             
               
                   
                   
               
               
                   
                   
                   
                 Particularly 
               
               
                   
                   
                 Preferred mixing 
                 preferred 
               
               
                   
                 Mixing partner 
                 ratio 
                 mixing ratio 
               
               
                   
                   
               
             
            
               
                   
               
            
           
           
               
               
               
               
            
               
                 1. 
                 chlorfluazuron 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 2. 
                 diflubenzuron 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 3. 
                 lufenuron 
                 20:1 to 1:5 
                 10:1 to 1:2 
               
               
                 4. 
                 teflubenzuron 
                 20:1 to 1:5 
                 10:1 to 1:2 
               
               
                 5. 
                 triflumuron 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 6. 
                 novaluron 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 7. 
                 flufenoxuron 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 8. 
                 hexaflumuron 
                 20:1 to 1:5 
                 5:1 to 1:2 
               
               
                 9. 
                 bistrifluoron 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 10. 
                 noviflumuron 
                 20:1 to 1:10 
                 10:1 to 1:5 
               
               
                 11. 
                 emamectin 
                 50:1 to 1:5 
                 10:1 to 1:1 
               
               
                 12. 
                 methoxyfenozide 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 13. 
                 tebufenozide 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 14. 
                 halofenozide 
                 2:1 to 1:100 
                 1:1 to 1:30 
               
               
                 15. 
                 JS-118 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 16. 
                 chromafenozide 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 17. 
                 endosulfan 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 18. 
                 
                   Trichogramma 
                 
                 1 000 g a.i./ha: 
                 300 g a.i./ha: 
               
               
                   
                 spp. 
                 20 000 wasps/ha to 
                 50 000 wasps/ha to 
               
               
                   
                   
                 10 g a.i./ha: 
                 50 g a.i./ha: 
               
               
                   
                   
                 500 000 wasps/ha 
                 300 000 wasps/ha 
               
               
                 19. 
                 
                   Verticillium 
                 
                 0.05% a.i.:0.05% F ( * )  to 
                 0.03% a.i.:0.1% F ( * )  to 
               
               
                   
                 
                   lecanii 
                 
                 0.001% a.i.:0.5% F ( * )   
                 0.005% a.i.:0.2% F ( * )   
               
               
                 20. 
                 fipronil 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 21. 
                 ethiprole 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 22. 
                 pyrafluprole 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 23. 
                 pyriprole 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 24. 
                 cyromazine 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 25. 
                 azadirachtin 
                 50:1 to 1:5 
                 10:1 to 1:1 
               
               
                 26. 
                 diofenolan 
                 100:1 to 1:2 
                 20:1 to 1:1 
               
               
                 27. 
                 indoxacarb 
                 50:1 to 1:5 
                 25:1 to 1:2 
               
               
                 28. 
                 Rynaxapyr 
                 50:1 to 1:25 
                 10:1 to 1:5 
               
               
                 29. 
                 flubendiamide 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                 30. 
                 metaflumizone 
                 10:1 to 1:10 
                 5:1 to 1:5 
               
               
                   
               
               
                 F ( * )  formulation comprising 10 9  to 10 10  spores/g 
               
               
                 *the mixing ratios are based on weight ratios. The ratio is to be understood as active compound of the formula (I): mixing partner or formula (II): mixing partner 
               
            
           
         
       
     
     The active compound combinations according to the invention are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, encountered in viticulture, in the cultivation of fruit, in the garden, in agriculture, in animal health, in forests, in the protection of stored products and in the protection of materials and also in the hygiene sector. They are effective against normally sensitive and resistant species and against all or individual stages of development. The abovementioned pests include: 
     From the order of the Isopoda, for example,  Oniscus asellus, Armadillidium vulgare, Porcellio scaber.    
     From the order of the Diplopoda, for example,  Blaniulus guttulatus.    
     From the order of the Chilopoda, for example,  Geophilus carpophagus, Scutigera  spp. 
     From the order of the Symphyla, for example,  Scutigerella immaculata.    
     From the order of the Thysanura, for example,  Lepisma saccharina.    
     From the order of the Collembola, for example,  Onychiurus armatus.    
     From the order of the Orthoptera, for example,  Acheta domesticus, Gryllotalpa  spp.,  Locusta migratoria migratorioides, Melanoplus  spp.,  Schistocerca gregaria.    
     From the order of the Blattaria, for example,  Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica.    
     From the order of the Dermaptera, for example,  Forficula auricularia.    
     From the order of the  Isoptera , for example,  Reticulitermes  spp. 
     From the order of the Phthiraptera, for example,  Pediculus humanus corporis, Haematopinus  spp.,  Linognathus  spp.,  Trichodectes  spp.,  Damalinia  spp. 
     From the order of the Thysanoptera, for example,  Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella occidentalis.    
     From the order of the Heteroptera, for example,  Eurygaster  spp.,  Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma  spp. 
     From the order of the  Homoptera , for example,  Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus  spp.,  Macrosiphum avenae, Myzus  spp.,  Phorodon humuli, Rhopalosiphum padi, Empoasca  spp.,  Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus  spp.,  Psylla  spp. 
     From the order of the  Lepidoptera , for example,  Pectinophora gossypiella, Bupalus piniarius, Chematobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella xylostella, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria  spp.,  Bucculatrix thurberiella, Phyllocnistis citrella, Agrotis  spp.,  Euxoa  spp.,  Feltia  spp.,  Earias insulana, Heliothis  spp.,  Mamestra brassicae, Panolis flammea, Spodoptera  spp.,  Trichoplusia ni, Carpocapsa pomonella, Pieris  spp.,  Chilo  spp.,  Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, Tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana, Cnaphalocerus  spp.,  Oulema oryzae.    
     From the order of the Coleoptera, for example,  Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica  spp.,  Psylliodes chrysocephala, Epilachna varivestis, Atomaria  spp.,  Oryzaephilus surinamensis, Anthonomus  spp.,  Sitophilus  spp.,  Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes  spp.,  Trogoderma  spp.,  Anthrenus  spp.,  Attagenus  spp.,  Lyctus  spp.,  Meligethes aeneus, Ptinus  spp.,  Niptus hololeucus, Gibbium psylloides, Tribolium  spp.,  Tenebrio molitor, Agriotes  spp.,  Conoderus  spp.,  Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica, Lissorhoptrus oryzophilus.    
     From the order of the  Hymenoptera , for example,  Diprion  spp.,  Hoplocampa  spp.,  Lasius  spp.,  Monomorium pharaonis, Vespa  spp. 
     From the order of the Diptera, for example,  Aedes  spp.,  Anopheles  spp.,  Culex  spp.,  Drosophila melanogaster, Musca  spp.,  Fannia  spp.,  Calliphora erythrocephala, Lucilia  spp.,  Chrysomyia  spp.,  Cuterebra  spp.,  Gastrophilus  spp.,  Hyppobosca  spp.,  Stomoxys  spp.,  Oestrus  spp.,  Hypoderma  spp.,  Tabanus  spp.,  Tannia  spp.,  Bibio hortulanus, Oscinella frit, Phorbia  spp.,  Pegomyia hyoscyami, Ceratitis capitata, Dacus  oleae, Tipula paludosa,  Hylemyia  spp.,  Liriomyza  spp. 
     From the order of the  Siphonaptera , for example,  Xenopsylla cheopis, Ceratophyllus  spp. 
     From the class of the Arachnida, for example,  Scorpio maurus, Latrodectus mactans, Acarus siro, Argas  spp.,  Ornithodoros  spp.,  Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus  spp.,  Rhipicephalus  spp.,  Amblyomma  spp.,  Hyalomma  spp.,  Ixodes  spp.,  Psoroptes  spp.,  Chorioptes  spp.,  Sarcoptes  spp.,  Tarsonemus  spp.,  Bryobia praetiosa, Panonychus  spp.,  Tetranychus  spp.,  Hemitarsonemus  spp.,  Brevipalpus  spp. 
     The plant-parasitic nematodes include, for example,  Pratylenchus  spp.,  Radopholus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera  spp.,  Globodera  spp.,  Meloidogyne  spp.,  Aphelenchoides  spp.,  Longidorus  spp.,  Xiphinema  spp.,  Trichodorus  spp.,  Bursaphelenchus  spp. 
     The active compound combinations can be converted into the customary formulations such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric materials. 
     These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is, liquid solvents and/or solid carriers, optionally with the use of surfactants, that is, emulsifiers and/or dispersants, and/or foam formers. 
     If the extender used is water, it is also possible, for example, to use organic solvents as cosolvents. The following are essentially suitable as liquid solvents: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as 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 dimethylformamide and dimethyl sulfoxide, or else water. 
     Suitable solid carriers are: 
     for example ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic materials such as highly disperse silica, alumina and silicates; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn 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, alkylsulfonates, alkyl sulfates, arylsulfonates, or else protein hydrolysates; suitable dispersants are: for example lignosulfite waste liquors and methylcellulose. 
     Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations. Other possible additives are mineral and vegetable oils. 
     It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic colorants such as alizarin colorants, azo colorants and metal phthalocyanine colorants, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. 
     The formulations generally comprise between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%. 
     The active compound combinations according to the invention can be present in commercially available formulations and in the use forms, prepared from these formulations, as a mixture with other active compounds, such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances or herbicides. The insecticides include, for example, phosphates, carbamates, carboxylates, chlorinated hydrocarbons, phenylureas and substances produced by microorganisms, inter alia. 
     Mixtures with other known active compounds such as herbicides or with fertilizers and growth regulators are also possible. 
     When used as insecticides, the active compound combinations according to the invention can furthermore be present in their commercially available formulations and in the use forms, prepared from these formulations, as a mixture with 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 active compound content of the use forms prepared from the commercially available formulations can vary within wide limits. The active compound concentration of the use forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight. 
     The compounds are employed in a customary manner appropriate for the use forms. 
     According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants). Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders&#39; certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds. 
     The treatment according to the invention of the plants and parts of plants with the active compound combinations is carried out directly or by action on their environment, habitat or storage area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multi-layer coating. 
     As already mentioned above, it is possible to treat all plants and their parts according to the invention. In a preferred embodiment, wild plant species and plant cultivars, or those obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof, are treated. In a further preferred embodiment, transgenic plants and plant cultivars obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetic Modified Organisms), and parts thereof are treated. The terms “parts”, “parts of plants” and “plant parts” have been explained above. 
     Particularly preferably, plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention. 
     Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive (“synergistic”) effects. Thus, for example, reduced application rates and/or a widening of the activity spectrum and/or an increase in the activity of the substances and compositions which can be used 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 performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products are possible which exceed the effects which were actually to be expected. 
     The transgenic plants or plant cultivars (i.e. those obtained by genetic engineering) which are preferred and to be treated according to the invention include all plants which, in the genetic modification, received genetic material which imparts particularly advantageous useful traits to these plants. Examples of such traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated maturation, higher harvest yields, better quality and/or a higher nutritional value of the harvested products, better storage stability and/or processability of the harvested products. Further and particularly emphasized examples of such properties are a better defence 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, cotton, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton and oilseed rape. Traits that are particularly emphasized are the increased defence of the plants against insects by toxins formed 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 furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulphonylureas, glyphosate or phosphinotricin (for example the “PAT” gene). The genes in question which impart the desired traits can also be present in combination 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 to glyphosate, for example maize, cotton, soya bean), Liberty Link® (tolerance to phosphinotricin, for example oilseed rape), IMI® (tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, 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 or still-to-be-developed genetic traits, which plants will be developed and/or marketed in the future. 
     The plants listed can be treated according to the invention in a particularly advantageous manner with the active compound mixture according to the invention. The preferred ranges stated above for the mixtures also apply to the treatment of these plants. Particular emphasis is given to the treatment of plants with the mixtures specifically mentioned in the present text. 
     The expected action for a given combination of two active compounds can be calculated as follows, according to S. R. Colby, Weeds 15 (1967), 20-22: 
     If 
     
         
         X is the kill rate, expressed as a percentage of the untreated control, when employing active compound A at an application rate of m g/ha or in a concentration of m ppm, 
         Y is the kill rate, expressed as a percentage of the untreated control, when employing active compound B at an application rate of n g/ha or in a concentration of n ppm and 
         E is the kill rate, expressed as a percentage of the untreated control, when employing active compounds A and B at application rates of m and n g/ha or in a concentration of m and n ppm,
 
then
 
       
    
     
       
         
           
             E 
             = 
             
               X 
               + 
               Y 
               - 
               
                 
                   X 
                   · 
                   Y 
                 
                 100 
               
             
           
         
       
     
     If the actual kill rate exceeds the calculated value, the kill of the combination is superadditive, i.e. a synergistic effect is present. In this case, the actually observed kill rate must exceed the value calculated using the above formula for the expected kill rate (E). 
    
    
     EXAMPLE A 
       Aphis gossypii  Test 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 Solvent: 
                 7 parts by weight of dimethylformamide 
               
               
                   
                 Emulsifier: 
                 2 parts 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 emulsifier-containing water to the desired concentration. 
     Cotton leaves ( Gossypium herbaceum ) which are heavily infested by the cotton aphid ( Aphis gossypii ) are treated by being dipped into the active compound preparation of the desired concentration. 
     After the desired period of time, the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed. The kill rates determined are entered into Colby&#39;s formula. 
     In this test, for example, the following active compound combinations in accordance with the present application show a synergistically enhanced activity compared to the active compounds applied individually: 
     
       
         
           
               
             
               
                 TABLE A1 
               
             
            
               
                   
               
               
                 Plant-damaging insects 
               
               
                   Aphis gossypii  test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in ppm 
                 in % after 6 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (II) 
                 0.8 
                 0 
               
               
                 compound (IIa) 
                 0.8 
                 0 
               
               
                 emamectin benzoate 
                 0.8 
                 15 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + emamectin 
                   
                   
                   
               
               
                 benzoate (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 0.8 + 0.8 
                 30 
                 15 
               
               
                 compound (IIa) + emamectin 
               
               
                 benzoate (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 0.8 + 0.8 
                 20 
                 15 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     
       
         
           
               
             
               
                 TABLE A2 
               
             
            
               
                   
               
               
                 Plant-damaging insects 
               
               
                   Aphis gossypii  test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in ppm 
                 in % after 1 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (I) 
                 100 
                 0 
               
               
                 compound (Ia) 
                 100 
                 0 
               
               
                 Rynaxapyr 
                 100 
                 75 
               
            
           
           
               
               
               
               
            
               
                 compound (I) + Rynaxapyr (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 100 + 100 
                 90 
                 75 
               
               
                 compound (Ia) + Rynaxapyr (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 100 + 100 
                 80 
                 75 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     EXAMPLE B 
       Myzus persicae  Test 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 Solvent: 
                  78 parts by weight of acetone 
               
               
                   
                   
                 1.5 parts by weight of dimethylformamide 
               
               
                   
                 Emulsifier: 
                 0.5 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 solvents and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. 
     Cabbage leaves ( Brassica oleracea ) which are heavily infested by the Green peach aphid ( Myzus persicae ), are treated by spraying with the active compound preparation of the desired concentration. 
     After the desired period of time, the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed. The kill rates determined are entered into Colby&#39;s formula. 
     In this test, for example, the following active compound combinations in accordance with the present application show a synergistically enhanced activity compared to the active compounds applied individually: 
     
       
         
           
               
             
               
                 TABLE B1 
               
             
            
               
                   
               
               
                 Plant-damaging insects 
               
               
                   Myzus persicae  test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in g/ha 
                 in % after 1 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (II) 
                 100 
                 10 
               
               
                   
                 20 
                 10 
               
               
                 compound (IIa) 
                 100 
                 0 
               
               
                   
                 20 
                 0 
               
               
                 fipronil 
                 20 
                 20 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + fipronil (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 20 + 20 
                 100 
                 28 
               
               
                 compound (IIa) + fipronil (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 20 + 20 
                 90 
                 20 
               
            
           
           
               
               
               
            
               
                 triflumuron 
                 100 
                 0 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + triflumuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 100 + 100 
                 20 
                 10 
               
               
                 compound (IIa) + triflumuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 100 + 100 
                 0 
                 0 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     EXAMPLE C 
       Myzus persicae  Test 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 Solvent: 
                 7 parts by weight of dimethylformamide 
               
               
                   
                 Emulsifier: 
                 2 parts 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 emulsifier-containing water to the desired concentration. 
     Cabbage leaves ( Brassica oleracea ) which are heavily infested by the green peach aphid ( Myzus persicae ) are treated by spraying with the active compound preparation of the desired concentration. 
     After the desired period of time, the kill in % is determined. 100% means that all aphids have been killed; 0% means that none of the aphids have been killed. The kill rates determined are entered into Colby&#39;s formula. 
     In this test, for example, the following active compound combinations in accordance with the present application show a synergistically enhanced activity compared to the active compounds applied individually: 
     
       
         
           
               
             
               
                 TABLE C1 
               
             
            
               
                   
               
               
                 Plant-damaging insects 
               
               
                   Myzus persicae  test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in ppm 
                 in % after 1 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (I) 
                 20 
                 15 
               
               
                   
                 4 
                 0 
               
               
                 compound (Ia) 
                 20 
                 10 
               
               
                   
                 4 
                 0 
               
               
                 fipronil 
                 20 
                 10 
               
            
           
           
               
               
               
               
            
               
                 compound (I) + fipronil (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 20 + 20 
                 25 
                 23.5 
               
               
                 compound (Ia) + fipronil (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 20 + 20 
                 10 
                 19 
               
            
           
           
               
               
               
            
               
                 Rynaxapyr 
                 4 
                 35 
               
            
           
           
               
               
               
               
            
               
                 compound (I) + Rynaxapyr (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 4 + 4 
                 85 
                 35 
               
               
                 compound (Ia) + Rynaxapyr (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 4 + 4 
                 65 
                 35 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     EXAMPLE D 
       Phaedon cochleariae  Larvae Test 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 Solvent: 
                  78 parts by weight of acetone 
               
               
                   
                   
                 1.5 parts by weight of dimethylformamide 
               
               
                   
                 Emulsifier: 
                 0.5 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 solvents and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. 
     Cabbage leaves ( Brassica oleracea ) are treated by spraying with the active compound preparation of the desired concentration and are populated with larvae of the mustard beetle ( Phaedon cochleariae ) while the leaves are still moist. 
     After the desired period of time, the kill in % is determined. 100% means that all beetle larvae have been killed; 0% means that none of the beetle larvae have been killed. The kill rates determined are entered into Colby&#39;s formula. 
     In this test, the following active compound combinations in accordance with the present application show a synergistically enhanced activity compared to the active compounds applied individually: 
     
       
         
           
               
             
               
                 TABLE D1 
               
             
            
               
                   
               
               
                 Plant-damaging insects 
               
               
                   Phaedon cochleariae  larvae test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in g/ha 
                 in % after 6 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (II) 
                 100 
                 50 
               
               
                   
                 20 
                 17 
               
               
                 compound (IIa) 
                 100 
                 67 
               
               
                   
                 20 
                 0 
               
               
                 flufenoxuron 
                 20 
                 50 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + flufenoxuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 20 + 20 
                 67 
                 58.5 
               
               
                 compound (IIa) + flufenoxuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 20 + 20 
                 50 
                 50 
               
            
           
           
               
               
               
            
               
                 lufenuron 
                 20 
                 83 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + lufenuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 20 + 20 
                 100 
                 85.89 
               
               
                 compound (IIa) + lufenuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 20 + 20 
                 83 
                 83 
               
            
           
           
               
               
               
            
               
                 metaflumizone 
                 100 
                 0 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + metaflumizone (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 100 + 100 
                 100 
                 50 
               
               
                 compound (IIa) + 
               
               
                 metaflumizone (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 100 + 100 
                 83 
                 67 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     EXAMPLE E 
       Plutella xylostella  Test 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 Solvent: 
                 7 parts by weight of dimethylformamide 
               
               
                   
                 Emulsifier: 
                 2 parts 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 emulsifier-containing water to the desired concentration. 
     Cabbage leaves ( Brassica oleracea ) are treated by being dipped into the active compound preparation of the desired concentration and are populated with larvae of the diamondback moth ( Plutella xylostella ) while the leaves are still moist. 
     After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed. The kill rates determined are entered into Colby&#39;s formula. 
     In this test, the following active compound combinations in accordance with the present application show a synergistically enhanced activity compared to the active compounds applied individually: 
     
       
         
           
               
             
               
                 TABLE E1 
               
             
            
               
                   
               
               
                 Plant-damaging insects 
               
               
                   Plutella xylostella  test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in ppm 
                 in % after 6 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (II) 
                 0.8 
                 10 
               
               
                 compound (IIa) 
                 0.8 
                 80 
               
               
                 indoxacarb 
                 0.032 
                 10 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + indoxacarb (25:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 0.8 + 0.032 
                 90 
                 19 
               
               
                 compound (IIa) + indoxacarb (25:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 0.8 + 0.032 
                 80 
                 82 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     EXAMPLE F 
       Spodoptera frugiperda  Larvae Test 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 Solvent: 
                  78 parts by weight of acetone 
               
               
                   
                   
                 1.5 parts by weight of dimethylformamide 
               
               
                   
                 Emulsifier: 
                 0.5 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 solvents and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. 
     Cabbage leaves ( Brassica oleracea ) are treated by spraying with the active compound preparation of the desired concentration and are populated with larvae of the armyworm ( Spodoptera frugiperda ) while the leaves are still moist. 
     After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed. The kill rates determined are entered into Colby&#39;s formula. 
     In this test, the following active compound combinations in accordance with the present application show a synergistically enhanced activity compared to the active compounds applied individually: 
     
       
         
           
               
             
               
                 TABLE F1 
               
             
            
               
                   
               
               
                 Plant-damaging insects 
               
               
                   Spodoptera frugiperda  larvae test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in g/ha 
                 in % after 2 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (II) 
                 20 
                 0 
               
               
                   
                 4 
                 0 
               
               
                 compound (IIa) 
                 20 
                 0 
               
               
                   
                 4 
                 0 
               
               
                 lufenuron 
                 20 
                 50 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + lufenuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 20 + 20 
                 67 
                 50 
               
               
                 compound (IIa) + lufenuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 20 + 20 
                 50 
                 50 
               
            
           
           
               
               
               
            
               
                 Rynaxapyr 
                 0.8 
                 67 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + Rynaxapyr (5:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                   4 + 0.8 
                 83 
                 67 
               
               
                 compound (IIa) + Rynaxapyr (5:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                   4 + 0.8 
                 50 
                 67 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     
       
         
           
               
             
               
                 TABLE F2 
               
             
            
               
                   
               
               
                 Plant-damaging insects 
               
               
                   Spodoptera frugiperda  larvae test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in g/ha 
                 in % after 6 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (II) 
                 20 
                 0 
               
               
                   
                 0.8 
                 0 
               
               
                   
                 0.16 
                 0 
               
               
                 compound (IIa) 
                 20 
                 0 
               
               
                   
                 0.8 
                 0 
               
               
                   
                 0.16 
                 0 
               
               
                 flubendiamide 
                 0.8 
                 50 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + flubendiamide (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 0.8 + 0.8 
                 83 
                 50 
               
               
                 compound (IIa) + 
               
               
                 flubendiamide (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 0.8 + 0.8 
                 33 
                 50 
               
            
           
           
               
               
               
            
               
                 flufenoxuron 
                 0.16 
                 83 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + flufenoxuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 0.16 + 0.16 
                 100 
                 83 
               
               
                 compound (IIa) + flufenoxuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 0.16 + 0.16 
                 67 
                 83 
               
            
           
           
               
               
               
            
               
                 metaflumizone 
                 20 
                 83 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + metaflumizone (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 20 + 20 
                 100 
                 83 
               
               
                 compound (IIa) + 
               
               
                 metaflumizone (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 20 + 20 
                 83 
                 83 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     EXAMPLE G 
       Spodoptera frugiperda  Larvae Test 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 Solvent: 
                 7 parts by weight of dimethylformamide 
               
               
                   
                 Emulsifier: 
                 2 parts 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 emulsifier-containing water to the desired concentration. 
     Cabbage leaves ( Brassica oleracea ) are treated by dipping into the active compound preparation of the desired concentration and are populated with larvae of the armyworm ( Spodoptera frugiperda ) while the leaves are still moist. 
     After the desired period of time, the kill in % is determined. 100% means that all caterpillars have been killed; 0% means that none of the caterpillars have been killed. The kill rates determined are entered into Colby&#39;s formula. 
     In this test, the following active compound combinations in accordance with the present application show a synergistically enhanced activity compared to the active compounds applied individually: 
     
       
         
           
               
             
               
                 TABLE G1 
               
             
            
               
                   
               
               
                 Plant-damaging insects 
               
               
                   Spodoptera frugiperda  test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in ppm 
                 in % after 3 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (II) 
                 4 
                 0 
               
               
                 compound (IIa) 
                 4 
                 0 
               
               
                 indoxacarb 
                 0.16 
                 70 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + indoxacarb (25:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 4 + 0.16 
                 85 
                 70 
               
               
                 compound (IIa) + indoxacarb (25:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 4 + 0.16 
                 70 
                 70 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     
       
         
           
               
             
               
                 TABLE G2 
               
             
            
               
                   
               
               
                 Plant-damaging insects 
               
               
                   Spodoptera frugiperda  larvae test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in ppm 
                 in % after 2 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (I) 
                 100 
                 0 
               
               
                 compound (Ia) 
                 100 
                 0 
               
               
                 lufenuron 
                 100 
                 40 
               
            
           
           
               
               
               
               
            
               
                 compound (I) + lufenuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 100 + 100 
                 100 
                 40 
               
               
                 compound (Ia) + lufenuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 100 + 100 
                 80 
                 40 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     EXAMPLE H 
       Tetranychus  Test 
     OP—Resistant/Spray Treatment 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 Solvent: 
                  78 parts by weight of acetone 
               
               
                   
                   
                 1.5 parts by weight of dimethylformamide 
               
               
                   
                 Emulsifier: 
                 0.5 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 emulsifier-containing water to the desired concentration. 
     Disks of bean leaves ( Phaseolus vulgaris ) which are infested by all stages of the greenhouse red spider mite ( Tetranychus urticae ) are sprayed with an active compound preparation of the desired concentration. 
     After the desired period of time, the activity in % is determined. 100% means that all spider mites have been killed; 0% means that none of the spider mites have been killed. 
     In this test, the following active compound combination in accordance with the present application showed a synergistically enhanced activity compared to the active compounds applied individually: 
     
       
         
           
               
             
               
                 TABLE H1 
               
             
            
               
                   
               
               
                 Plant-damaging mites 
               
               
                   Tetranychus urticae  test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in g/ha 
                 in % after 2 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (II) 
                 100 
                 20 
               
               
                   
                 20 
                 10 
               
               
                 compound (IIa) 
                 100 
                 10 
               
               
                   
                 20 
                 0 
               
               
                 ethiprole 
                 20 
                 20 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + ethiprole (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 20 + 20 
                 40 
                 28 
               
               
                 compound (IIa) + ethiprole (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 20 + 20 
                 10 
                 20 
               
            
           
           
               
               
               
            
               
                 triflumuron 
                 100 
                 0 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + triflumuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 100 + 100 
                 50 
                 20 
               
               
                 compound (IIa) + triflumuron (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 100 + 100 
                 10 
                 10 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     
       
         
           
               
             
               
                 TABLE H2 
               
             
            
               
                   
               
               
                 Plant-damaging mites 
               
               
                   Tetranychus urticae  test 
               
            
           
           
               
               
               
            
               
                   
                 Concentration 
                 Kill 
               
               
                 Active compound 
                 in g/ha 
                 in % after 6 d   
               
               
                   
               
            
           
           
               
               
               
            
               
                 compound (II) 
                 0.8 
                 50 
               
               
                 compound (IIa) 
                 0.8 
                 60 
               
               
                 fipronil 
                 0.8 
                 0 
               
            
           
           
               
               
               
               
            
               
                 compound (II) + fipronil (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 according to the invention 
                 0.8 + 0.8 
                 100 
                 50 
               
               
                 compound (IIa) + fipronil (1:1) 
                   
                 found.* 
                 calc.** 
               
               
                 prior art 
                 0.8 + 0.8 
                 30 
                 60 
               
               
                   
               
               
                 *found. = activity found 
               
               
                 **calc. = activity calculated using Colby&#39;s formula 
               
            
           
         
       
     
     EXAMPLE I 
     Critical Concentration Test/Soil Insects 
     Treatment of Transgenic Plants 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 test insect: 
                   Diabrotica balteata  - larvae in the soil 
               
               
                   
                 solvent: 
                 7 parts by weight of acetone 
               
               
                   
                 emulsifier: 
                 2 parts 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 amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration. 
     The preparation of active compound is poured onto the soil. Here, the concentration of the active compound in the preparation is virtually immaterial, only the amount by weight of active compound per volume unit of soil, which is stated in ppm (mg/l), matters. The soil is filled into 0.25 pots, and these are allowed to stand at 20° C. 
     Immediately after the preparation, 5 pre-germinated maize corns of the cultivar YIELD GUARD (trademark of Monsanto Comp., USA) are placed into each pot. After 2 days, the appropriate test insects are placed into the treated soil. After a further 7 days, the efficacy of the active compound is determined by counting the maize plants that have emerged (all plants emerge=100% activity). 
     EXAMPLE J 
       Heliothis virescens  Test 
     Treatment of Transgenic Plants 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 Solvent: 
                 7 parts by weight of dimethylformamide 
               
               
                   
                 Emulsifier: 
                 2 parts 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 amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration. 
     Soybean shoots ( Glycine max ) of the cultivar Roundup Ready (trademark of Monsanto Comp. USA) are treated by spraying with the preparation of active compound of the desired concentration and are populated with the tobacco budworm  Heliothis virescens  while the leaves are still moist. 
     After the desired period of time, the kill of the insects is determined. 
     EXAMPLE K 
       Myzus persicae  Test 
     Treatment of Transgenic Plants 
       
     
       
         
           
               
               
               
             
               
                   
                   
               
             
            
               
                   
                 solvent: 
                 7 parts by weight of acetone 
               
               
                   
                 emulsifier: 
                 2 parts 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 amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration. 
     Transgenic cabbage plants ( Brassica oleracea ) which are heavily infested by the green peach aphid  Myzus persicae  are treated by spraying with the active compound preparation of the desired concentration. 
     After the desired period of time, the kill of the insects is determined.