AU2013200344B2 - Use of tetramic acid derivatives for controlling pests by drenching, drip application, dip application or soil injection - Google Patents

Abstract

Abstract Compounds of the formula (I) in which A, B, G, W, X, Y and Z can have the meanings given in the description are highly suitable for controlling animal pests such as insects and/or spider mites and/or nematodes by treating the soil/growth substrate by drenching or drip application or dipping or soil injection. Document2 - 21/1/13

Description

H:Vc\Intrwovn\NRPortbl\DCC\REC\6824532_I.DOC-25/09/2014 Use of tetramic acid derivatives for controlling pests by drenching, drip application, dip application or soil infection The present invention relates to the use of tetramic acid derivatives for controlling insects and/or spider mites and/or nematodes by drenching, drip application, dip application or soil injection. The insecticidal and acaricidal activity of tetramic acid derivatives following spray application is disclosed in EP-A-456 063, EP-A-521 334, EP-A-596 298, EP-A-613 884, WO 95/01 997, WO 95/26 954, WO 95/20 572, EP-A-O 668 267, WO 96/25 395, WO 96/35 664, WO 97/01 535, WO 97/02 243, WO 97/36 868, WO 97/43 275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/16748, WO 99/24437, WO 99/43649, WO 99/48869 and WO 99/55673, WO 01/09092, WO 01/17972, WO 01/23354, WO 01/74770, WO 03/013249, WO 04/007 448, WO 04/024 688, WO 04/065 366, WO 04/080 962, WO 04/111 042, WO 05/044 791, WO 05/044 796, WO 05/048 710, WO 05/049 596 and WO 05/066 125, WO 05/092897, WO 06/000355, WO 06/029799, WO 06/056281, WO 06/056282, WO 06/077071, WO 06/089633 and DE-A-05051325. Surprisingly, it has now been found that tetramic acid derivatives are also highly suitable for controlling insects and/or spider mites and/or nematodes by what is known in expert circles as drenching the soil, by what is known in expert circles as drip application onto the soil, by dipping roots, tubers or bulbs (referred to in expert circles as dip application), by hydroponic systems or by what is known in expert circles as soil injection. In a first aspect, the present invention provides use of the compound: HN 0 CH3 H3CO_ OC2H5 CH3 H:Vc\Intrwovn\NRPortbl\DCC\REC\6824532_I.DOC-25/09/2014 - la in the form of an isomer mixture or a pure isomer for controlling pests selected from Phemphigidae, Tetranychidae, Tarsonemidae, Thripidae, Aleyrodidae, Coccidae, Pseudococcidae, Agromyzidae, Aphelenchoididae and Aphididae on a plant, said plant being located in soil or an artificial growth substrate, and wherein the compound is applied by drip application onto the soil or the artificial growth substrate. In another aspect, the present invention provides a method for controlling pests selected from Phemphigidae, Tetranychidae, Tarsonemidae, Thripidae, Aleyrodidae, Coccidae, Pseudococcidae, Agromyzidae, Aphelenchoididae or Aphididae on a plant, said plant being located in soil or an artificial growth substrate, the method comprising drip application of the compound: HN CH3 H3CO_ OC2H5 CH3 in the form of an isomer mixture or a pure isomer onto the soil or the artificial growth substrate. Also described herein is the use of tetramic acid derivatives for controlling insects and/or spider mites and/or nematodes by drenching the soil, as drip application onto the soil in irrigations systems, as dip application in the case of roots, tubers or bulbs or by soil injection. Furthermore, the present invention relates to these use forms on natural substrates (soil) or artificial substrates (for example rock wool, glass wool, quartz sand, gravel, expanded clay, vermiculite) in the open or in closed systems (for example greenhouses or under film mulch) and in annual crops (for example vegetables, spices, ornamentals) or perennial crops (for example citrus plants, fruits, tropical crops, spices, nuts, grapevines, conifers and ornamentals).

H:Vc\Intrwovn\NRPortbl\DCC\REC\6824532_I.DOC-25/09/2014 - lb 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, climbing and dwarf beans, peas, artichokes, maize; WO 2007/126691 PCT/US2007/007195 -2 but also leafy vegetables, head-forming lettuce, chicory, endives, various types of cress, of rocket, lamb's lettuce, iceberg lettuce, leeks, spinach, Swiss chard; furthermore tuber vegetables, root vegetables and stem vegetables, for example celeriac/celery, beetroot, carrots, radish, horseradish, scorzonera, asparagus, beet for human consumption, palm 5 hearts, bamboo shoots, furthermore bulb vegetables, for example onions, leeks, Florence fennel, garlic; furthermore Brassica vegetables such as cauliflower, broccoli, kohlrabi, red cabbage, white cabbage, curly kale, Savoy cabbage, Brussels sprouts, Chinese cabbage. Regarding .the use, perennial crops are understood as meaning citrus, such as, for example, 10 oranges, grapefruits, tangerines, lemons, limes, Seville oranges, cumquats, 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 15 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, currants, gooseberries, raspberries, blackberries, blueberries, strawberries, cranberries, kiwi fruit, American cranberries. 20 As regards the use, ornamentals are understood as meaning annual and perennial plants, for example cut flowers such as, for example, roses, carnations, gerbera, lilies, marguerites, chrysanthemums, tulips, narcissus, anemones, poppies, amaryllis, dahlias, azaleas, hibiscus, but also for example border plants, pot plants and perennials such as, for example, roses, Tagetes, violas, geraniums, fuchsias, hibiscus, chrysanthemum, busy lizzie, cyclamen, African violet, 25 sunflowers, begonias, furthermore for example bushes and conifers such as, for example, ficus, rhododendron, firs, spruces, pines, yews, juniper, umbrella pines, oleander.

WO 2007/126691 PCT/US2007/007195 -3 As regards the use, spices are understood as meaning annual and perennial plants such as, for example, aniseed, chilli pepper, paprika, pepper, vanilla, marjoram, thyme, cloves, juniper berries, cinnamon, tarragon, coriander, saffron, ginger. The tetramic acid derivatives are compounds of the formula (1) G-O X B N H OW Z 5 H 0 in which X represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano, W, Y and Z independently of each other represent hydrogen, halogen, alkyl, alkoxy, haloalkenyl, haloalkoxy or cyano, 10 A represents hydrogen, or represents in each case optionally halogen-substituted alkyl, alkoxyalkyl, saturated, optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a hetero atom, B represents hydrogen or alkyl, or 15 A and B together with the carbon atom to which they are bonded represent a saturated or unsaturated, unsubstituted or substituted cycle which optionally contains at least one hetero atom, G represents hydrogen (a) or one of the groups O L R 4 R (b), M , R 2 (C), /- SO- R d) -PR' (e), L

R

6 E (f) or L N R 20 WO 2007/126691 PCT/US2007/007195 -4 in which E represent a metal ion or an ammonium ion, L represents oxygen or sulphur, M represents oxygen or sulphur, 5 R' represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl- or alkoxy-substituted cycloalkyl which can be interrupted by at least one hetero atom, in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl, 10 R 2 represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl, polyalkoxyalkyl or in each case optionally substituted cycloalkyl, phenyl or benzyl,

R

3 represents optionally halogen-substituted alkyl or optionally substituted phenyl,

R

4 and R 5 independently of one another represent in each case optionally halogen 15 substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio, or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio, and R' and R 7 independently of one another represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, optionally 20 substituted phenyl, optionally substituted benzyl or, together with the N atom to which they are bonded, represent an optionally substituted ring which is optionally interrupted by oxygen or sulphur, in the form of their isomer mixtures or their pure isomers. Tetramic acid derivatives of the abovementioned formula (1) which can preferably be employed are 25 those in which the radicals have the following meanings: W preferably represents hydrogen, Ci-C 4 -alkyl, CI-C 4 -alkoxy, chlorine, bromine or fluorine, X preferably represents CI-C 4 -alkyl, C 1

-C

4 -alkoxy, Ci-C 4 -haloalkyl, fluorine, chlorine or bromine, WO 2007/126691 PCT/US2007/007195 -5 Y and Z independently of one another preferably represent hydrogen, C-C 4 -alkyl, halogen, C-C 4 alkoxy or C-C 4 -haloallcyl, A preferably represents hydrogen or in each case optionally halogen-substituted C1-C 6 -alkyl or C 3 -Cs-cycloalkyl, 5 B preferably represents hydrogen, methyl or ethyl, A,B and the carbon atom to which they are bonded preferably represent saturated C 3

-C

6 cycloalkyl in which one ring member is optionally replaced by oxygen or sulphur and which is optionally monosubstituted or disubstituted by C-C 4 -alkyl, trifluoromethyl or

C-C

4 -alkoxy, 10 G preferably represents hydrogen (a) or one of the groups 0 L R ~R (b), M ,R ), R SO-g R R, (e), R' (b),R 5 L

R

6 E () o L N (g) in particular (a), (b), (c) or (g) in which E represents a metal ion or an ammonium ion, L represents oxygen or sulphur and 15 M represents.oxygen or sulphur, R preferably represents in each case optionally halogen-substituted C-C 1 o-alkyl, C 2 -Ci alkenyl, C-C 4 -alkoxy-C-C 4 -alkyl, C-C 4 -alkylthio-C-C 4 -alkyl, or represents C 3

-C

6 cycloalkyl which is optionally substituted by fluorine, chlorine, C-C 4 -alkyl or C-C 2 alkoxy, 20 or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C-C 4 -alkyl, C-C 4 -alkoxy, trifluoromethyl or trifluoromethoxy, or represents pyridyl or thienyl, each of which is optionally substituted by chlorine or methyl, WO 2007/126691 PCT/US2007/007195 -6 R2 preferably represents in each case fluorine- or chlorine-substituted C-Cl-alkyl,

C

2 -CIO-alkenyl, C-C 4 -alkoxy-C 2

-C

4 -alkyl, or represents optionally methyl- or methoxy-substituted C 5

-C

6 -cycloalkyl, or represents phenyl or benzyl, each of which is optionally substituted by fluorine, chlorine, 5 bromine, cyano, nitro, C-C 4 -alkyl, C-C 4 -alkoxy, trifluoromethyl or trifluoromethoxy,

R

3 preferably represents optionally fluorine-substituted C-C 4 -alkyl, or represents phenyl which is optionally substituted by fluorine, chlorine, bromine, C-C 4 -alkyl, C-C 4 -alkoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, R! preferably represents in each case optionally fluorine- or chlorine-substituted C-C 4 -alkyl, 10 C-C 4 -alkoxy, C-C 4 -alkylamino, C-C 4 -alkylthio or represents phenyl, phenoxy or phenylthio, each of which is optionally substituted by fluorine, chlorine, bromine, nitro, cyano, C-C 4 -alkoxy, trifluoromethoxy, C-C 4 -alkylthio, Cl-C 4 -haloalkylthio, C-C 4 -alkyl or trifluoromethyl, R preferably represents C-C 4 -alkoxy or C-C 4 -thioalkyl, 15 R preferably represents C-C 6 -alkyl, C 3

-C

6 -cycloalkyl, C-C 6 -alkoxy, C 3

-C

6 -alkenyl or C 1

-C

4 alkoxy-C-C 4 -alkyl, R7 preferably represents C-C 6 -alkyl, C 3

-C

6 -alkenyl or C-C 4 -alkoxy-C-C 4 -alkyl,

R

6 and R! together preferably represent an optionally methyl- or ethyl-substituted C 3

-C

6 -alkylene radical in which one carbon atom is optionally replaced by oxygen or sulphur, 20 in the form of their isomer mixtures or their pure isomers. Tetramic acid derivatives of the abovementioned formula (1) which can especially preferably be employed are those in which the radicals have the following meanings: W especially preferably represents hydrogen, methyl, ethyl, chlorine, bromine or methoxy, X especially preferably represents chlorine, bromine, methyl, ethyl, propyl, i-propyl, 25 methoxy, ethoxy or trifluoromethyl, Y and Z especially preferably independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, i-propyl, trifluoromethyl or methoxy, WO 2007/126691 PCT/US2007/007195 -7 A especially preferably represents methyl, ethyl, propyl, i-propyl, butyl, i-butyl, sec-butyl, tert-butyl, cyclopropyl, cyclopentyl or cyclohexyl, B especially preferably represents hydrogen, methyl or ethyl, or 5 A,B and the carbon atom to which they are bonded especially preferably represent saturated

C

6 -cycloalkyl in which one ring member is optionally replaced by oxygen and which is optionally monosubstituted by methyl, ethyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy, G especially preferably represents hydrogen (a) or one of the groups 0 0 R 6 OAR1 or (g) 10 R (b), M ( oN( in which M represents oxygen or sulphur, R1 especially preferably represents CI-Cs-alkyl, C 2

-C

4 -alkenyl, methoxymethyl, ethoxymethyl, ethylthiomethyl, cyclopropyl, cyclopentyl or cyclohexyl, 15 or represents phenyl which is optionally monosubstituted to disubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy, or represents pyridyl or thienyl, each of which is optionally substituted by chlorine or methyl, 20 R2 especially preferably represents CI-C 8 -alkyl, C 2

-C

4 -alkenyl, methoxyethyl, ethoxyethyl, or represents phenyl or benzyl, R and R! independently of one another especially preferably represent methyl or ethyl or together represent a C 5 -alkylene radical in which the C 3 -methylene group is replaced by oxygen, in the form of their isomer mixtures or their pure isomers.

WO 2007/126691 PCT/US2007/007195 -8 Tetramic acid derivatives of the abovementioned formula (I) which can very especially preferably be employed are those in which the radicals have the following meanings: W very especially preferably represents hydrogen or methyl, X very especially preferably represents chlorine, bromine or methyl, 5 Y and Z independently of one another very especially preferably represent hydrogen, chlorine, bromine or methyl, A, B and the carbon atom to which they are bonded very especially preferably represent saturated

C

6 -cycloalkyl in which one ring member is optionally replaced by oxygen and which is optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy or 10 butoxy, G very especially preferably represents hydrogen (a) or one of the groups 0 o R 6 1 R 2 or N (g), R4(b), M , 2(c), or O NR in which M represents oxygen or sulphur, 15 R 1 very especially preferably represents C-Cs-alkyl, C 2

-C

4 -alkenyl, methoxymethyl, ethoxy methyl, ethylthiomethyl, cyclopropyl, cyclopentyl, cyclohexyl or represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro, or represents pyridyl or thienyl, each of which is optionally substituted by chlorine or 20 methyl, R2 very especially preferably represents C-C 8 -alkyl, C 2

-C

4 -alkenyl, methoxyethyl, ethoxy ethyl, phenyl or benzyl, R6 and R7 independently of one another very especially preferably represent methyl or ethyl or together represent a C 5 -alkylene radical in which the C 3 -methylene group is replaced by 25 oxygen WO 2007/126691 PCT/US2007/007195 -9 in the form of their isomer mixtures or their pure isomers. Tetramic acid derivatives of the abovementioned formula (I) which can especially preferably be employed are those in which the radicals have the following meanings: G-O X R N H OW Z H 0 Example W X Y Z R G M.p.*C No. I-I H Br H CH 3

OCH

3 CO-i-C 3

H

7 122 1-2 H Br H CH 3

OCH

3 C0 2

-C

2

H

5 140-142 1-3 H CH 3 H CH 3

OCH

3 H >220 1-4 H CH 3 H CH3- OCH 3 C0 2

-C

2

H

5 128 1-5 CH 3

CH

3 H Br OCH 3 H > 220 1-6 CH 3 CH3 H Cl OCH 3 H 219 1-7 H Br CH 3

CH

3

OCH

3 CO-i-C 3

H

7 217 1-8 H CH 3 Cl CH 3

OCH

3 C0 2

C

2

H

5 162 1-9 CH 3

CH

3

CH

3

CH

3

OCH

3 H >220 I-10 CH 3

CH

3 H Br OC 2

H

5 CO-i-C 3

H

7 212-214 I-11 H CH 3

CH

3 CH3 OC 2

H

5 CO-n-C 3

H

7 134 1-12 H CH 3

CH

3

CH

3

OC

2

H

5 CO-i-C 3

H

7 108 1-13 H CH 3

CH

3

CH

3

OC

2

H

5 CO-c-C 3

H

5 163 5 in the form of their cis/trans isomer mixtures or their pure cis isomers. The compounds of the formula (1) are known compounds whose preparation has been described in the patents/patent applications which have been cited at the outset (see especially WO 97/01535, WO 97/36868 and WO 98/05 638).

WO 2007/126691 PCT/US2007/007195 - 10 Compounds whose use must be emphasized are the compounds 1-3 and 1-4 as the pure cis isomers (WO 04/007448). O H O H CH N CHa ~~~H3CO HC H3OOH 0==0 CHa OC2H5 CH3 1-3 1-4 5 The tetramic acid derivatives can be applied in accordance with the invention on their own, but also in combination with other insecticidal and/or acaricidal active substances. The use according to the invention of the tetramic acid derivatives extends to a wide range of different animal pests. These include: From the order of the Anoplura (Phthiraptera), for example Damalinia spp., Haematopinus spp., 10 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., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, 15 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.. 20 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 25 zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes WO 2007/126691 PCT/US2007/007195 - 11 bajulus, Hypera postica, Hypothenemus spp., Lachnostema 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, 5 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. 10 From the order of the Dermaptera, 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., 15 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.. 20 From the class of the Helminthes, 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 vermicularis, Faciola spp., Haemonchus spp., 25 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 sodium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, 30 Wuchereria bancrofti. Protozoans such as Eimeria can also be controlled.

WO 2007/126691 PCT/US2007/007195 -12 From the order of the Heteroptera, for example Anasa tristis, Antestiopsis spp., Blissus spp., Calocoris spp., Canpylomma 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., 5 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, 10 Aonidiella spp., Aphanostigma piri, 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 15 spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp., Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffee, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis 20 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., Phlocomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, 25 Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii. 30 From the order of the Hymenoptera, for example Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.. From the order of the Isopoda, for example Armadillidium vulgare, Oniscus asellus, Porcellio scaber.

WO 2007/126691 PCT/US2007/007195 - 13 From the order of the Isoptera, for example Reticulitermes spp., 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, Cheimatobia brumata, 5 Chilo spp., Choristoneura fumiferana, Clysia ambiguella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa 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, 10 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., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.. From the order of the Orthoptera, for example Acheta domesticus, Blatta orientalis, Blattella 15 germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria. From the order of the Siphonaptera, for example Ceratophyllus spp., Xenopsylla cheopis. From the order of the Symphyla, for example Scutigerella immaculata. From the order of the Thysanoptera, for example Baliothrips biformis, Enneothrips flavens, 20 Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakotbrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.. From the order of the Thysanura, for example Lepisma saccharina. The plant-parasitic nematodes include, for example, Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heliocotylenchus 25 spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp., Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema 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, 30 Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, WO 2007/126691 PCT/US2007/007195 -14 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. 5 Among the family of the Pemphigidae, the following are preferred: Eriosoma spp., Pemphigus spp., Anuraphis spp., Brachycaudus spp., in crops such as, for example, pome fruit, conifers, vegetables and ornamentals. From the psyllid family (Psyllidae), the following are preferred: Psylla spp., Paratrioza spp., Trioza spp., in crops such as, for example, citrus, vegetables, potatoes, pome fruit. 10 From the scale insect family (Coccidae), the following are preferred: Ceroplastes spp., Drosicha spp. Pulvinaria spp., Protopulminaria spp., Saissetia spp., Coccus spp., in perennial crops such as, for example, citrus, grapevines, tea, pome and stone fruit, tropical crops, ornamentals, conifers, but also vegetables. From the family of the Diaspididae, the following are preferred: Quadraspidiotus spp., Aonidiella 15 spp., Lepidosaphes spp., Aspidiotus spp., Aspis spp., Diaspis spp., Parlatoria spp., Pseudaulacaspis spp., Unaspis spp., Pinnaspis spp., Selenaspidus spp., in crops such as, for example, citrus, tea, ornamentals, conifers, pome and stone fruit, grapevines, tropical crops. From the family of the Pseudococcidae, the following are preferred: Pericerga, Pseudococcus spp., Planococcus spp., Phenacoccus spp., Dysmicoccus spp., in crops such as, for example, citrus, 20 pome and stone fruit, tea, grapevines, vegetables, ornamentals, conifers, spices and tropical crops. Furthermore preferred are the following from the family of the Aleyrodidae: Bemisia argentifolii, Bemisia tabaci, Trialeurodes vaporariorum, Aleurothrixus floccosus, Aleurodes spp., Dialeurodes spp., Parabemisia myricae in crops such as, for example, vegetables, melons, potatoes, tobacco, soft fruit, citrus, ornamentals, conifers, cotton, potatoes and tropical crops. 25 Furthermore preferred are the following from the family of the Aphidae: Myzus spp. in tobacco, stone fruit, pome fruit, soft fruit, Brassica vegetables, fruiting vegetables, leafy vegetables, tuber and root vegetables, melons, potatoes, spices, ornamentals and conifers. Aphis spp. in cotton, tobacco, citrus, melons, beet, soft fruit, oilseed rape, fruiting 30 vegetables, leafy vegetables, Brassica vegetables, tuber and root vegetables, ornamentals, potatoes, pumpkins, spices. Rhodobium porosum in strawberries, WO 2007/126691 PCT/US2007/007195 - 15 Nasonovia ribisnigri in leafy vegetables, Macrosiphum spp. in ornamentals, cereals, potatoes, leafy vegetables, Brassica vegetables and fruiting vegetables, strawberries, Phorodon humuli in hops, 5 Toxoptera spp. in citrus, stone fruit, almonds, nuts, cereals, spices, Aulacorthum spp. in citrus, potatoes, fruiting vegetables and leafy vegetables. Preferred are furthermore the following from the family of the Tetranychidae: Tetranychus spp., Brevipalpus spp., Panonychus spp., Oligonychus spp., Eotetranychus spp., Bryobia spp. in crops such as, for example, vegetables, ornamentals, spices, conifers, citrus, stone 10 and pome fruit, grapevines, cotton, soft fruit, melons, potatoes. The following are preferred from the family of the Tarsonemidae: Hermitarsonemus batus, Stenotarsonemus spp., Polyphagotarsonemus spp., Stenotarsonemus spinky in crops such as, for example, vegetables, ornamentals, spices, conifers, tea, citrus, melons. Furthermore preferred are the following from the thrips family (Thripidae): Anaphothrips spp., 15 Baliothrips spp., Caliothrips spp., Frankliniella spp., Heliothrips spp., Hercinothrips spp., Rhipiphorothrips spp., Scirtothrips spp., Selenothrips spp. and Thrips spp., in crops such as, for example, fruit, cotton, grapevines, soft fruit, vegetables, melons, ornamentals, spices, conifers, tropical crops, tea. Also preferred are the following from the whitefly family (Agromyzidae): Liriomyza spp., 20 Pegomya spp. in crops such as, for example, vegetables, melons, potatoes and ornamentals. Also preferred are the following from the foliar nematode family (Aphelenchoididae), for example Aphelenchoides ritzemabosi, A. fragariae, A. besseyi, A. blastophthorus in crops such as soft fruits and ornamentals. 25 The invention is illustrated by the examples which follow. These are not to be construed in any way as limiting.

WO 2007/126691 PCT/US2007/007195 -16 Use examples Aphididae and Pemphigidae Very especially preferred is the control of the following species from the family of the Aphididae and the Penphigidae in the following crops: Myzus persicae in fruiting and leafy vegetables such as, for example, bell peppers, beans, aubergine, tomatoes, melons, head-forming lettuce; potatoes, strawberries, in ornamentals such as, for example, roses, in Brassica vegetables such as, for example, broccoli and white cabbage; conifers, spices such as, for example, chilli pepper; tobacco, pome fruit, stone fruit Aphis gossypii in citrus such as, for example, oranges, tangerines, grapefruits, in fruiting vegetables such as, for example, cucumbers, pumpkins, aubergine, melons; strawberries, spices, potatoes, beet, in ornamentals such as, for example, roses; conifers, cotton Aphis craccivora in ornamentals such as, for example, violets; fruiting vegetables such as, for example, peas Aphis fabae in fruiting vegetables such as, for example, beans, peas; in tuber, root and stem vegetables such as, for example, celery/celeriac Rhodobium porosum in strawberries Nasonovia ribisnigri in leafy vegetables such as, for example, head-forming lettuce Macrosiphum rosae in ornamentals such as, for example, roses Macrosiphum euphorbiae in leafy vegetables, fruiting vegetables and Brassica vegetables such as, for example, aubergines, lettuce, bell peppers, white cabbage, tomatoes; potatoes, strawberries Phorodon humuli in hops WO 2007/126691 PCT/US2007/007195 -17 Aulacorthum solani in citrus such as, for example, oranges, tangerines, grapefruits, limes; in fruiting vegetables and leafy vegetables such as, for example, head-forming lettuce, tomatoes, bell peppers, aubergines; potatoes Toxoptera citricola in citrus such as, for example, oranges, tangerines, limes, grapefruits Toxoptera citricida in citrus such as, for example, oranges, tangerines, limes, grapefruits Toxoptera aurantii in citrus such as, for example, oranges, tangerines, grapefruits, limes; in spices such as, for example, pepper; in nuts such as, for example, cashew nuts Toxoptera odinae in citrus such as, for example, oranges, tangerines, grapefruits, limes; in spices such as, for example, pepper; in nuts such as, for example, cashew nuts Pemphigus bursarius, in ornamentals such as, for example, chrysanthemums; in vegetables such as, for example, head-forming lettuce Pemphigus fuscicornis in beet, leaf vegetables such as, for example, head-forming lettuce, root vegetables such as, for example, carrots, ornamentals such as, for example, chrysanthemums Anuraphis cardui in vegetables such as, for example, artichokes Brachycaudus helycrisii in sunflowers WO 2007/126691 PCT/US2007/007195 - 18 Example 1 In an irrigation experiment carried out in 0.5-1-pots, Chinese cabbage, Savoy cabbage, bell peppers and broad beans which had been potted three days earlier are watered, in two replications, with 50 ml of active substance solution containing the active substance 1-4 (cis isomer) at the 5 application rates stated. The greenhouse temperature is 20*C. Infection with MYZUPE is accomplished seven and fourteen days after the application of the active substance. The test is evaluated in each case seven days after each infection by determining the activity with the aid of Abbott's formula. 10 Active substance 1-4 (cis isomer) Application rate Abbott efficacy (%) against MYZUPE (mg active substance/plant) Chinese cabbage Savoy cabbage Bell pepper Broad bean 7d 14d 7d 14d 7d 14d 7d 14d 20 100 99 100 99 100 100 100 99 10 100 99 100 99 100 100 83 23 WO 2007/126691 PCT/US2007/007195 - 19 Example 2 Cucumber plants cv. "Delikatess" which have been grown on rock wool are drenched, in six replications, one week after transplanting with in each case 100 ml active substance solution 5 containing the active substance 1-4 (cis isomer, formulation: 240 SC) at the application rate stated. The greenhouse temperature is 20 0 C. Infection with APHIGO is accomplished in each case seven and fourteen days after the application of the active substance. The test is evaluated in each case seven days after each infection by determining the activity with the aid of Abbott's formula. 10 Active substance 1-4 (cis isomer) Application rate Abbott efficacy (%) (mg active against APHIGO substance/plant) 7d 14d 40 100 99 20 100 96 10 100 91 WO 2007/126691 PCT/US2007/007195 -20 Example 3 Violet plants cv. "Ladies delight" (approximate height 15 cm) in 4-inch pots which had been infected with Aphis craccivora two weeks before the treatment are drenched, in four replications, with an active substance solution containing the active substance 1-4 (cis isomer, formulation: 5 240 SC) and, by way of comparison, with the commercial standard imidacloprid (240 SC) at the application rate stated. The greenhouse temperature is 27-33"C. The test is evaluated 7, 14, 22 and 35 days after the treatment by determining the activity against nymphs on the leaves with the aid of the Henderson-Tilton method. 10 Active substance 1-4 (cis-isomer) Application rate Henderson-Tilton efficacy (%) against (mg active Aphis craccivora substance/i potting compost) 7d 14d 22d 35d Imidacloprid 100 94 100 100 12 1-4 100 84 100 100 12 WO 2007/126691 PCT/US2007/007195 -21 Tetranychidae and Tarsonemidae Furthermore very especially preferred is the control of the following species from the families Tetranychidae and Tarsonemidae in the following crops: Tetranychus urticae in vegetables such as, for example, bell peppers, tomatoes, Tetranychus pacificus cucumbers, cabbage, for example broccoli, beans, lettuce, Tetranychus canadensis aubergines, courgettes, pumpkins, in soft fruit, for example Tetranychus kanzawai strawberries, in melons, for example water melons, musk melons, Tetranychus cinnabarinus Canteloupe melons in ornamentals such as, for example, roses, hibiscus, chrysanthemums, and in potatoes and in cotton, conifers Eotetranychus carpini in cotton, in vegetables such as, for example, bell peppers, Eotetranychus willametti tomatoes, cucumbers, beans, cucurbits, aubergines, courgettes, Eotetranychus banski cabbage, leeks, onions, in soft fruit, in melons, for example water Eotetranychus hicoriae melons, musk melons, Canteloupe melons, in ornamentals such as, Eotetranychus yumensis for example, roses, hibiscus, potatoes, grapevines, cotton, conifers Oligonychus mexicanus in vegetables such as, for example, tomatoes, bell peppers, beans, Oligonychus ilicis cucumbers, pumpkins, aubergines, in melons, and in ornamentals Oligonychus persea such as, for example, roses, hibiscus, azaleas, conifers Oligonychus unungis Hemitarsonemus latus in citrus such as, for example, oranges, lemons, grapefruits, Stenotarsonemus laticeps tangerines, ornamentals, vegetables such as, for example, Polyphagotarsonemus latus cucumbers, tomatoes, beans, aubergines, pumpkins; melons such as water melons, Canteloupe melons, spices such as chilli; tea, conifers WO 2007/126691 PCT/US2007/007195 -22 Example 4 Aubergine plants (25 days after sowing) in 0.5-1-pots are drenched, in three replications, with 50 ml of active substance solution containing the active substance 1-4 (cis isomer, formulation: 240 SC) at the application rate stated. The greenhouse temperature is 20*C. Infection with Aphis 5 gossypii (APHIGO), Myzus persicae (MYZUPE) and Tetranychus urticae (TETRUR) is accomplished in each case seven and fourteen days after the application of the active substance. The test is evaluated in each case seven days after each infection by determining the activity with the aid of Abbott's formula. 10 Active substance 1-4 (cis isomer) Application rate Abbott efficacy (%) (mg active substance/plant) against APIGO MYZUPE TETRUR 7d 14d 7d 14d 7d 14d 20 100 no 100 100 100 77 infection 10 99 no 100 100 96 73 infection WO 2007/126691 PCT/US2007/007195 -23 Example 5 Gardenia plants cv. "Cape jasmine" in 6-inch pots which had been infected with Tetranychus urticae (TETRUR) two weeks before the beginning of the experiment are drenched, in three 5 replications, with in each case 100 ml of active substance solution containing the active substance 1-4 (cis isomer, formulation: 240 SC) and, by way of comparison, with the commercial standard imidacloprid (240 SC) at the application rate stated. The greenhouse temperature is 25-30 0 C. The test is evaluated 3, 15 and 22 days after the treatment by determining the activity against nymphs on the leaves with the aid of the Henderson-Tilton method. 10 Active substance 1-4 (cis isomer) Application rate Henderson-Tilton efficacy (%) against (mg active TETRUR substance/ 1 potting compost) 3d 15d 22d Imidacloprid 72.7 82.2 0 38.4 1-4 39.0 89.1 100 77 WO 2007/126691 PCT/US2007/007195 -24 Thrips (Thripidae) Furthermore very especially preferred is the control of the following species from the thrips family (Thripidae) in the following crops: Frankliniella occidentalis in vegetables such as, for example, bell peppers, tomatoes, Frankliniella schultzei cucumbers, cabbage, for example broccoli, beans, lettuce, Frankliniella fusca aubergines, courgettes, pumpkins, in soft fruit, for example strawberries, in melons, for example water melons, musk melons, Canteloupe melons, in ornamentals such as roses, hibiscus, chrysanthemums and in potatoes and in tropical crops such as, for example, papayas, avocado, cotton, conifers Thrips palmi in cotton, in vegetables such as, for example, bell peppers, Thrips tabaci tomatoes, cucumbers, beans, cucurbits, aubergines, courgettes, Thrips hawaiiensis cabbage, leeks, onions, in soft fruit, in melons, for example water melons, musk melons, Canteloupe melons, in ornamentals such as, for example, roses, hibiscus, in tropical crops such as, for example, papayas, pineapples, bananas, potatoes, grape vines, cotton, rice, nuts, conifers Heliothrips in vegetables such as, for example, tomatoes, bell peppers, beans, haemorrhoidalis cucumbers, pumpkins, aubergines, in melons and in ornamentals such as, for example, roses, hibiscus, azaleas, tropical crops such as guavas, citrus such as, for example, lemons, oranges, grape vines, conifers Hercinothrips femoralis ornamentals, vegetables such as, for example, beans Hercinothrips bicinctus Hercinothrips phaseoli Caliothrips phaseoli in vegetables such as, for example, beans, courgettes Anaphothrips obscurus Brassica vegetables such as, for example, white cabbage Scirthothrips aurantii in citrus such as, for example, oranges, lemons, grapefruits, Scirthothrips dorsalis tangerines, ornamentals, vegetables such as, for example, Scirthothrips citri cucumbers, tomatoes, beans, aubergines, pumpkins; melons such as water melons, Canteloupe melons, spices such as chilli; tea WO 2007/126691 PCT/US2007/007195 -25 Example 6 Verbena plants (approximate height 13 cm) in 6-inch-pots which are infected with Franidiniella occidentalis (FRANOC) are drenched, in four replications, with an active substance solution 5 containing the active substance 1-4 (cis isomer, formulation: 240 SC) and, by way of comparison, with the commercial standard imidacloprid (240 SC) at the application rate stated. The greenhouse temperature is 27-33*C. The test is evaluated 7, 14, 21 and 28 days after the treatment by determining the activity against nymphs on the leaves with the aid of the Henderson-Tilton method. 10 Active substance 1-4 (cis isomer) Application rate Henderson-Tilton efficacy (%) (mg active substance/ 1 against FRANOC potting compost) 7 d 14 d 21 d 28 d Imidacloprid 100 100 49 100 12 1-4 100 100 90 100 12 WO 2007/126691 PCT/US2007/007195 -26 Example 7 Plots approximately 5 m 2 in size and containing cucumber plants are drenched, in three replications, against Thrips palmi with an active substance solution containing the active substance 5 1-4 (cis isomer, formulation: 240 SC) and, by way of comparison, with the standard imidacloprid (100 SL) at the application rate stated, corresponding to an approximate water application rate of 300 1/ha. Two applications are effected at a 10-day interval. The test is evaluated in each case 9 days after the first treatment and 7 and 13 days after the second treatment by determining the efficacy with the aid of Abbott's formula. 10 Active substance 1-4 (cis isomer) Application rate Abbott efficacy (%) (mg active substance/plant) against THRIPL 9d 7d 13d after 1st after 2nd after 2nd treaty. treaty. treatm. Imidacloprid 73.7 68.8 44.0 20 1-4 66.3 64.1 80.0 20 WO 2007/126691 PCT/US2007/007195 -27 Whitefly (Aleyrodidae) Furthermore very especially preferred is the control of the following species from the whitefly family (Aleyrodidae) in the following crops: Bemisia tabaci in vegetables such as bell peppers, tomatoes, cucumbers, cabbage, for example broccoli, beans, lettuce, aubergines, courgettes, pumpkins, in soft fruits, in melons, for example water melons, musk melons, Canteloupe melons, in ornamentals such as roses, hibiscus, tropical sage, in cotton and in potatoes, in tobacco and in tropical crops such as, for example, papayas, bananas, Bemisia argentifolii in cotton, in vegetables such as bell peppers, tomatoes, cucumbers, beans, cucurbits, aubergines, courgettes, cabbage, in soft fruit, in melons, for example water melons, musk melons, Canteloupe melons, in ornamentals such as, for example, roses, hibiscus, tropical sage, in tropical crops such as, for example, papayas, bananas, Trialeurodes vaporariorum in vegetables such as tomato, bell pepper, beans, cucumbers, pumpkins, aubergines, courgettes, in soft fruit, in melons and in ornamentals such as, for example, roses, hibiscus, in conifers Aleurothrixus floccosus in citrus such as oranges, tangerines, lemons Aleurodes citri in citrus such as oranges, tangerines, lemons, grapefruits, limes, kumquats, Aleurodes fragriae in soft fruit such as,.for example, strawberries Aleurodes azaleae in ornamentals such as, for example, azaleas WO 2007/126691 PCT/US2007/007195 -28 Example 8 Tropical sage plants cv. "scarlet sage" (approximate height 29 cm) in 6-inch pots and infested with Bemisia argentifolii (BEMIAR) are drenched, in three replications, with an active substance 5 solution containing the active substance 1-4 (cis isomer, formulation: 240 SC) and, by way of comparison, with the commercial standard imidacloprid (240 SC) at the application rate stated. The greenhouse temperature is 27-33*C. The test is evaluated 9, 13, 20, 34 and 41 days after the treatment by determining the activity against nymphs on the leaves with the aid of the Henderson Tilton method. 10 Active substance 1-4 (cis isomer) Application rate Henderson-Tilton efficacy (%) (mg active substance/ 1 against Bemisia argentifolii potting compost) 9d 13d 20d 34d 41d Imidacloprid 94 100 95 94 100 12 1-4 99 100 98 100 100 12 WO 2007/126691 PCT/US2007/007195 - 29 Example 9 Plots approximately 12 m 2 in size and containing courgette plants (47 days after sowing) are drenched, in three replications, against Trialeurodes vaporarium (TRIAVA) with 100 ml of an 5 active substance solution per plant, containing the active substance 1-4 (cis isomer, formulation: 240 SC) and, by way of comparison, with the standard imidacloprid (200 SL) at the application rate stated. Four applications are effected at 10-day intervals. The test is evaluated 21, 31, 38 and 45 days after the 1st treatment by determining the efficacy with the aid of Abbott's formula. 10 Active substance 1-4 (cis isomer) Application rate Abbott efficacy (%) (mg active substance/plant) against TRIAVA 21d 31d 38d 45d Imidacloprid 88.1 74.0 77.2 63.7 1st treaty. 10 2nd treatm. 10 3rd treaty. 10 4th treaty. 10 1-4 57.5 85.9 88.5 85.7 1st treatm. 10 2nd treatm. 10 3rd treatm. 10 4th treaty. 10 WO 2007/126691 PCT/US2007/007195 -30 Example 10 In each case 12 tomato plants cv. "Briljant" on rock wool are treated, in four replications, with a drip application against Trialeurodes vaporarium (TRIAVA) with an active substance solution 5 containing the active substance 1-4 (cis isomer, formulation: 100 OD) in comparison with the commercial standard imidacloprid (70 WG) at the application rate stated. The greenhouse temperature is 20*C. Three treatments are carried out at intervals of seven and fourteen days. The test is evaluated 14, 21, 28, 36 and 43 days after the 1st treatment by determining the efficacy with the aid of Abbott's formula. 10 Active substance I-4 (cis isomer) Application rate Abbott efficacy (%) (mg active substance/plant) against TRIAVA 14 d 21 d 28 d 36'd 43 d Imidacloprid 28.4 55.3 89.1 92.0 89.8 9.8 1-4 26.8 66.3 90.4 95.6 97.9 20 WO 2007/126691 PCT/US2007/007195 -31 Scale insects (Coccidae) Very especially preferred is the control of the following species from the scale insect family (Coccidae) in the following crops, preferably by foliar application: Ceroplastes ceriferus in citrus such as, for example, oranges, grapefruits, tangerines, Ceroplastes floridensis lemons, limes, satsumas; tropical fruits such as, for example, Ceroplastes rubens mangos, guava Ceroplastes rusci Coccus viridis in citrus such as, for example, oranges, tangerines, grapefruits, limes, lemons, satsumas, in tropical crops, for example pineapples; ornamentals, conifers Coccus hesperdium in tea, in vegetables such as, for example, beans, in grape vines; ornamentals WO 2007/126691 PCT/US2007/007195 -32 Example 11 Gardenia plants cv. "Cape jasmine" (seedlings, 28 cm) in 6-inch pots which are infected with Coccus viridis are drenched, in three replications, with 150 ml of active substance solution 5 containing the active substance 1-4 (cis isomer, formulation: 240 SC) and, by way of comparison, with the commercial standard imidacloprid (240 SC) and dinotefuran (20 G) at the application rate stated. The greenhouse temperature is 27*C. The test is evaluated 7, 15, 21 and 35 days after the treatment by determining the activity against nymphs on the leaves with the aid of the Henderson Tilton method. 10 Active substance 1-4 (cis isomer) Application rate Henderson-Tilton efficacy (%) (mg active substance/ 1 against Coccus viridis potting compost) 7d 15d 21d 35d Imidacloprid 45 55 66 100 12 1-4 35 45 69 100 24 Dinotefuran 0 57 85 91 48 WO 2007/126691 PCT/US2007/007195 - 33 Mealybugs and woollybugs (Pseudococcidae) Very especially preferred is the control of the following species from the mealybug and woollybug family (Pseudococcidae) in the following crops: Pseudococcus citri in citrus such as, for example, oranges, tangerines, grapefruits, Pseudococcus comstocki limes, lemons, satsumas, in grape vines, in ornamentals, in tropical Pseudococcus maritimus crops such as, for example, pineapples, spices such as, for example, chillis, conifers, vegetables such as, for example, bell peppers Dysmicoccus boninsis in tea, in tropical crops such as, for example, pineapples, guyabano, Dysmicoccus cryptus ornamentals, conifers Dysmicoccus brevipes Planococcus lilacinus in citrus such as, for example, oranges, tangerines, grapefruits, Planococcus citri limes, lemons, satsumas, in grape vines, vegetables Phenacoccus maderensis in ornamentals such as, for example, Coleus WO 2007/126691 PCT/US2007/007195 -34 Example 12 Coleus plants (approximate height 29 cm) in 6-inch pots which have been infected approximately 4 weeks before the treatment with citrus mealybug Pseudococcus citri (PSECCI) are drenched, in 5 three replications, with an active substance solution containing the active substance 1-4 (cis isomer, formulation: 240 SC) and, by way of comparison, with the commercial standard imidacloprid (240 SC) at the application rate stated. The greenhouse temperature is 29*C. The test is evaluated 7, 14, 21 and 28 days after the treatment by determining the efficacy with the aid of Abbott's formula. 10 Active substance 1-4 (cis isomer) Application rate Abbott efficacy (%) (mg active substance/i against PSECCI potting compost) 7d 14d 21d 28d Imidacloprid 30 35 19 16 12 1-4 63 91 94 93 24 WO 2007/126691 PCT/US2007/007195 - 35 Example 13 Coleus plants (approximate height 29 cm) in 6-inch pots which have been infected approximately 4 weeks before the beginning of the experiment with Madeira mealybug (Phenacoccus 5 madeirensis) are drenched, in three replications, with an active substance solution containing the active substance 1-4 (cis isomer, formulation: 240 SC) and, by way of.comparison, with the commercial standard imidacloprid (240 SC) at- the application rate stated. The greenhouse temperature is 29*C. The test is evaluated 7, 14, 21 and 28 days after the treatment by determining the efficacy with the aid of Abbott's formula. 10 Active substance 1-4 (cis isomer) Application Abbott efficacy (%) rate (mg active substance/I against Phenacoccus madeirensis potting compost) 7d 14d 21d 28d Imidacloprid 92 83 30 44 12 1-4 84 89 99 98 12 WO 2007/126691 PCT/US2007/007195 -36 Leaf-mining flies (Agromyzidae) Furthermore very especially preferred is the control of the following species from the family of the leaf-mining flies (Agromyzidae) in the following crops: Liriomyza brassicae in vegetables such as bell peppers, tomatoes, cucumbers, cabbage, Liriomyza bryoniae beans, lettuce, aubergines, courgettes, pumpkins, in melons, for Liriomyza cepae example water melons, musk melons, Canteloupe melons, in Liriomyza chilensis ornamentals such as roses, hibiscus, and in potatoes Liriomyza hunidobrensis Liriomyza sativae Liriomyza trifolie Liriomyza quadrata Pegomya hyoscyami in beet, in vegetables and ornamentals Pegomya spinaciae WO 2007/126691 PCT/US2007/007195 -37 Example 14 Plots approximately 2 x 5 m in size which contain bell pepper plants are treated, in three replications, against Liriomyza sp.. The active substance example (1-4) cis isomer (240 SC) is 5 drenched in an active substance solution at the application rate stated. The water application rate is 700 1/ha. Three treatments are carried out at intervals of 7 and 14 days. The test is evaluated in each case 7 days after the 2nd and 3rd treatment and 14 days after the 3rd treatment by scoring the kill rate of the larvae in the leaves. 10 Active Application rate Efficacy (% Abbott) substance (mg/plant) against Liriomyza sp. 7 d after - 7 d after 14 d after 2nd treatment 3rd treatment 3rd treatment Example (I-4) 40+10+10 66.7 100 81.8 WO 2007/126691 PCT/US2007/007195 -38 Example 15 Plots approximately 2 x 5 m in size which contain bell pepper plants are treated, in three replications, against Ben-isia sp.. The active substance example (1-4) cis isomer (240 SC) is 5 drenched in an active substance solution at the application rate stated. The water application rate is 700 1/ha. Three treatments are carried out at intervals of 7 and 14 days. The test is evaluated in each case 7, 14, 21 and 28 days after the 3rd treatment by scoring the kill rate of the larvae on the leaves. 10 Active Application rate Efficacy (% Abbott) substance (mg/plant) against Bemisia sp. 7 d after 14 d after 21 d after 28 d after 3rd treatm. 3rd treaty. 3rd treatm. 3rd treatm. Imidacloprid 10.5 96.6 80.6 84.6 85.7 Example (1-4) 40+5 + 5 86.2 94.4 94.9 90.5 WO 2007/126691 PCT/US2007/007195 -39 Foliar nematodes (Aphelenchoididae) Furthermore very especially preferred is the control of the following species from the family of foliar nematodes (Aphelenchoididae) in the following crops: Aphelenchoides ritzemabosi in ornamentals and strawberries 5 Aphylenchoides fragariae Aphylenchoides besseyi Aphylenchoides blastophthorus Example 16 10 The bulbs of 15 lily plants cv. "L.A. Glow" (growth stage 14/16) are dipped, in four replications, into an active substance solution containing the active substance 1-4 (cis isomer, formulation: 240 SC) at the concentrations stated and subsequently planted into boxes 40 x 60 cm in size. The bulbs came from a field which was homogeneously infested with the foliar nematode 15 Aphelenchoides fragariae. The number of infested plants is determined by examining leaves under the microscope for foliar nematodes 92 days after the dip treatment,. Active substance Infested plants concentration a.i. (%) 0 (control) 8 1-4 0.15 0 1-4 0.075 0 Comparison: foliar 6 treatment with 150 g/ha 1-4 H: \grs\lnterwoven\NRPortbl\DCC\GRS\6152587_1doc-5/06/2014 - 39a Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" or "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps. The reference in this specification to any prior publication (or information derived from it), or to any matter which is known, is not, and should not be taken as an acknowledgment or admission or any form of suggestion that that prior publication (or information derived from it) or known matter forms part of the common general knowledge in the field of endeavour to which this specification relates.

Claims (9)

1. Use of the compound: HN 0 CH3 H3CO OC2H5 CH3 in the form of an isomer mixture or a pure isomer for controlling pests selected from Phemphigidae, Tetranychidae, Tarsonemidae, Thripidae, Aleyrodidae, Coccidae, Pseudococcidae, Agromyzidae, Aphelenchoididae and Aphididae on a plant, said plant being located in soil or an artificial growth substrate, and wherein the compound is applied by drip application onto the soil or the artificial growth substrate.

2. Use according to Claim 1, wherein the compound has the following structure: H 0 N CH3 H3CO Zz 0 OC2HG CH3

3. Use according to Claim 1 or 2, wherein the plant is located in an artificial growth substrate.

4. Use according to Claim 3, wherein the artificial growth substrate is selected from the group consisting of: rock wool, glass wool, quartz sand, gravel, expanded clay and vermiculite. H:Vc\Intrwovn\NRPortbl\DCC\REC\6824532_I.DOC-25/09/2014 - 41

5. Use according to any one of Claims 1 to 4, wherein the plant is located in a closed system.

6. Use according to any one of Claims 1 to 5, wherein the plant is selected from the group consisting of: vegetables, spices, ornamentals, conifers, cotton, citrus plants, fruit, tropical crops, nuts and grape vines.

7. Use according to Claim 1 or 2, wherein the plant is located in soil.

8. A method for controlling pests selected from one or more of Phemphigidae, Tetranychidae, Tarsonemidae, Thripidae, Aleyrodidae, Coccidae, Pseudococcidae, Agromyzidae, Aphelenchoididae or Aphididae on a plant, said plant being located in soil or an artificial growth substrate, the method comprising drip application of the compound: HN 0 CH3 H3CO_ OC2H5 CH3 in the form of an isomer mixture or a pure isomer onto the soil or the artificial growth substrate.

9. Use according to Claim 1, substantially as herein described with reference to the examples.