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(11) Patent Number: KE 334 (45) Date of grant: 18/08/2009
(12) PATENT
(51) Int.CI.A: 0 IN 25/00, 43/38, 47/06
(21)    Application    KE/P/200700614    (84) WO No. WO 2006/077071 A2
Number:    27/07/2006
(22)    Filing Date:    05/07/2007
(31)Priority Number: 102005003076.9    (32) Date: 17/01/2006 (33) Country: DE
(73) Owner(s): Bayer Cropscience Aktiengesellschaft of Alfred-Nobel-Str. 50, 40789 Monheim., Germany
(72) Inventor(s)
(74)Agent/addres; for correspandeince: -
•    FISCHER, Reiner; HUNGENBERG, Heike; THIELERT, Wolfgang; BRUCK, Ernst and NAUEN, Ralf
Kaplan & Stratton Advocates, P.O. Box 40111-00100, Nairobi

(54) Title:    USE OF TETRAMIC ACID DERIVATIVES FOR THE CONTROL OF INSECTS
OF THE. PLANT LOUSE SPECIES (STERNORRHYNCHA)
(57) Abstract: The invention relates to the use of tetramic acid derivatives of formula (I), where A, B, G, W, X, Y and 2 have the meanings given before for the control of insects of the plant louse sub-order (Sternorrhyncha).
 
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Use of tetramic acid derivatives for controlling insects from the genus of the plant lice (Sternorrhyncha)
The present invention relates to the use of tetramic acid derivatives for controlling insects from the suborder of the plant lice (Sternorrhyncha).
5 The tetramic acid derivatives are known from 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-0 668 267, 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,
10 WO 01/74770, WO 03/013249, WO 2004/007 448, WO 2004/024 688, 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, WO 05/066 125.
The insecticidal action of some of these compounds against the species Myzus persicae and
Aphis gossypii from the family of the aphids (Aphididae) in vegetable crops such as, for example,
15 brassica vegetables and cotton, is known. The action against the whitefly Bemisia tabaci (Aleyrodidae) on cotton has also been described.
Surprisingly, it has now been found that tetramic acid derivatives are also particularly suitable for
controlling further animal pests from the suborder of the plant lice, especially from the families of
the gall-making aphids (Pemphigidae), phylloxerans (Phylloxeridae), jumping plant lice (Psyllidae),
20 soft scales (Coccidae), armoured scales (Diaspididae), ensign coccids (Ortheziidae) and mealy bugs (Pseudococcidae).
Furthermore, it has been found that tetramic acid derivatives are also highly active against
whiteflies (Aleyrodidae) in further annual crops, such as vegetables, cotton, melons, potatoes,
tobacco and, surprisingly, also in perennial crops, such as, for example, citrus fruit, soft fruit., but
25 also ornamental plants and spices.
Moreover, it has been found that tetramic acid derivatives are also very active against aphids
(Aphididae) in further annual crops, such as potatoes, tobacco, melons, beet, oilseed rape,
cereals, fruit vegetables, tuber vegetables, leafy vegetables, brassica vegetables, root vegetables,
 
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stem vegetables, bulb crops, flower-heads/curds as vegetables and, surprisingly, also in perennial crops, such as, for example, citrus fruit, pomme fruit and stone fruit, nuts, almonds, soft fruit, grapevines and hops, and also in tropical crops, ornamental plants and spices.
Accordingly, the present invention relates to the use of tetramic acid derivatives for controlling
5 insects from the families a) of the gall-making aphids (Pemphigidae), phylloxerans (Phylloxeridae), jumping plant lice (Psyllidae), soft scales (Coccidae), armoured scales (Diaspididae), ensign coccids (Ortheziidae) and mealy bugs (Pseudococcidae) in annual and perennial and also tropical crops, and also b) for controlling pests from the family of the whiteflies (Aleyrodidae) in further annual crops, such as vegetables, potatoes, tobacco, melons, cotton and, surprisingly, also in
10 perennial crops, such as, for example, citrus fruit, soft fruit, but also ornamental plants and spices and in tropical crops, and c) for controlling insects from the family of the aphids (Aphididae) in further annual crops, such as potatoes, tobacco, melons, beet, oilseed rape, cereal, fruit vegetables, tuber vegetables, leafy vegetables, brassica vegetables, root vegetables, stem vegetables, bulb crops, flower-heads/curds as vegetables and, surprisingly, also in perennial
15 crops, such as, for example, citrus fruit, pomme fruit and stone fruit, nuts, almonds, soft fruit, grapevines and hops, and also tropical crops, ornamental plants and spices.
The crops to be protected, which have only been described in a general manner, are described in
a more differentiated and more specific manner below. Thus, with respect to the use, vegetable is
to be understood as meaning, for example, fruit vegetable and flower-heads/curds as vegetables,
20 for example bell peppers, chilli peppers, tomatoes, aubergines, cucumbers, cucurbits, courgettes, broad beans, runner beans, bush beans, peas, artichokes, maize;
but also leafy vegetables, for example lettuce, chicory, endives, cress, rocket salad, field salad, iceberg lettuce, leek, spinach, Swiss chard;
furthermore tuber vegetables, root vegetables and stem vegetables, for example celeriac, 25 beetroot, carrots, garden radish, horseradish, scorzonera, asparagus, table beet, palm shoots, bamboo shoots, moreover bulb vegetables, for example onions, leek, fennel, garlic;
furthermore brassica vegetables, such as cauliflowers, broccoli, kohlrabi, red cabbage, white cabbage, green cabbage, Savoy cabbage, Brussels sprouts, Chinese cabbage.
 
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Thus, with respect to the use in cereal crops, cereal is to be understood as meaning, for example, wheat, barley, rye, oats, triticale but also maize, millet and rice;
with respect to the use, perennial crops are to be understood as meaning citrus fruit, such as, for
example, oranges, grapefruit, mandarins, lemons, limes, bitter oranges, cumquats, satsumas;
5 but also pomme fruit, such as, for example, apples, pears and quince, and stone fruit, such as, for example, peaches, nectarines, cherries, plums, common plums, apricots;
furthermore grapevine, hops, olives, tea, and tropical crops, such as, for example, mangoes, papayas, figs, pineapples, dates, bananas, &rims, kakis, coconuts, cacao, coffee, avocados, litchis, maracujas, guavas,
10 moreover almonds and nuts, such as, for example, hazelnuts, walnuts, pistachios, cashew nuts, brazil nuts, pecan nuts, butter nuts, chestnuts, hickory nuts, macadamia nuts, peanuts,
additionally also soft fruit, such as, for example, blackcurrants, gooseberries, raspberries, blackberries, blueberries, strawberries, red bilberries, kiwis, cranberries.
With respect to the use, ornamental plants are to be understood as meaning annual and perennial
15 plants, for example cut flowers, such as, for example, roses, carnations, gerbera, lilies, marguerites, chrysanthemums, tulips, daffodils, anemones, poppies, amaryllis, chhlias, azaleas, malves,
but also, for example, bedding plants, potted plants and shrubs, such as, for example, roses, tagetes, pansies, geraniums, fuchsias, hibiscus, chrysanthemums, busy lizzies, cyclamen, African 20 violets, sunflowers, begonias,
furthermore, for example, bushes and conifers, such as, for example, fig trees, rhododendron, spruce trees, fir trees, pine trees, yew trees, juniper trees, stone pines, rose bays.
With respect to the use, spices are to be understood as meaning annual and perennial plants, such as, for example, aniseed, chilli pepper, bell pepper, pepper, vanilla, marjoram, thyme, cloves, 25 juniper berries, cinnamon, estragon, coriander, saffron, ginger.
The tetramic acid derivatives are compounds of the formula (I)
 
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in which
X    represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
W, Y and Z independently of one another represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, 5    haloalkoxy or cyano,
A    represents hydrogen, in each case optionally halogen- substituted alkyl, alkoxyalkyl,
saturated, optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom,
B    represents hydrogen or alkyl,
10    or
A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle which optionally contains at least one heteroatom,
G    represents hydrogen (a) or represents one of the groups
O
R1 (b),    R4
2SO2-- R3    - P
KirR (c),    SO(d),R5(e),

15    R6
E (f) or    N
L
(g),

in which
E    represents a metal ion or an ammonium ion,
 
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L    represents oxygen or sulphur,
M    represents oxygen or sulphur,
RI    represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl,
alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl- or alkoxy- substituted
5 cycloalkyl which may be interrupted by at least one heteroatom, represents in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R2    represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl,
polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, 10    phenyl or benzyl,
R3    represents optionally halogen-substituted alkyl or optionally substituted phenyl,
R4 and R5 independently of one another represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, diallcylamino, alkylthio, alkenylthio, cyclo¬alkylthio or represent in each case optionally substituted phenyl, benzyl, phenoxy
15    or phenylthio and
R6 and le independently of one another represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent optionally substituted phenyl, represent optionally substituted benzyl or together with the nitrogen atom to which they are attached represent an optionally
20    substituted ring which is optionally interrupted by oxygen or sulphur
in the form of their isomer mixtures or pure isomers.
Preference is given to using tetramic acid derivatives of the formula (I) mentioned above in which the radicals are as defined below:
W    preferably represents hydrogen, C -C4- alkyl, C 1-C4- alkoxy, chlorine, bromine or
25    fluorine,
 
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    X    preferably represents C1-Ca-alkyl, C1-C4-alkoxy, C1-Ca-haloallcyl, fluorine, chlorine or
bromine,
Y and Z independently of one another preferably represent hydrogen, C1-C4-alkyl, halogen, C1-Ca-alkoxy or C i-Ca-haloalkA
    5 A    preferably represents hydrogen or in each case optionally halogen-substituted Q-C6-
alkyl or C3-C8-cycloalkyl,
    B    preferably represents hydrogen, methyl or ethyl,
A, B and the carbon atom to which they are attached preferably represent saturated C3-C6- cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur and
10        which is optionally mono- or disubstituted by G-Ca-alkyl, triftuoromethyl or C1-C4-
alkoxy,
    G    preferably represents hydrogen (a) or represents one of the groups
 

 
R6
E (f)    or    N    t„,.\    in particular (a), (b), (c) or (g),
in which
15    E    represents a metal ion or an ammonium ion,
L    represents oxygen or sulphur and
M    represents oxygen or sulphur,
R'    preferably represents in each case optionally halogen-substituted CI-Cm-alkyl, C2-C10-
alkenyl, C1-C4-alkoxy-C1-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl or optionally fluorine-, 20    chlorine-, C1-C4-alkyl- or Ci-C2-alkoxy-substituted C3-C6-cycloalkyl,
 
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represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-alkyl-, C1-C4- alkoxy-, trifluoromethyl- or trifluoromethoxy- substituted phenyl,
represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,
    R2    preferably represents in each case optionally fluorine- or chlorine-substituted Q-C10-
5    alkyl, C2-C10-alkenyl, C1-C4-alkoxy-C2-C4-alkyl,
represents optionally methyl- or methoxy-substituted C5-C6-cycloalkyl or
represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-
 alkyl-, C1-C4-alkoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl or benzA
    R3    preferably represents optionally fluorine-substituted Ci-C4-alkyl or represents optionally
10        fluorine-, chlorine-, bromine-, Ci-C4-alkyl-, C1-C4-alkoxy-, trifluoromethyl-,
trifluoromethoxy-, cyano- or nitro-substituted phenyl,
    R4    preferably represents in each case optionally fluorine- or chlorine-substituted C1-C4-alkyl,
C1-C4-alkoxy,    G-C4-alkylthio or represents in each case optionally
fluorine-, chlorine-, bromine-, nitro-, cyano-, C1-C4-alkoxy-, trifluoromethoxy-,
15        alkylthio-, C1-C4-haloalkylthio-, C1-C4-alkyl- or trifluoromethyl-substituted phenyl,
phenoxy or phenylthio,
    R5    preferably represents C1-C4-alkoxy or C1-C4-thioalkA
    R6    preferably represents C1-C6-alkyl, Q-C6-cycloalkyl, CI-C6-alkoxy, Q-C6-alkenyl or
C1-C4-alkoxy-C1-C4-alkyl,
    20 R7    preferably represents Ci-C6-alkyl, C3-C6-alkenyl or Ci-C4-alkoxy-Ci-C4-alkyl,
R6 and R7 together preferably represent an optionally methyl- or ethyl-substituted C3-C6-alkylene
radical in which optionally one carbon atom is replaced by oxygen or sulphur
in the form of their isomer mixtures or pure isomers.
 
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Particular preference is given to using tetramic acid derivatives of the formula (I) mentioned above in which the radicals are as defined below:
    W    particularly preferably represents hydrogen, methyl, ethyl, chlorine, bromine or methoxy,
    X    particularly preferably represents chlorine, bromine, methyl, ethyl, propyl, isopropyl,
5    methoxy, ethoxy or trifluoromethyl,
Y and Z independently of one another particularly preferably represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, trifluoromethyl or methoxy,
    A    particularly preferably represents methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-
butyl, tert-butyl, cyclopropyl, cyclopentyl or cyclohexyl,
    10 B    particularly preferably represents hydrogen, methyl or ethyl,
Or
A, B and the carbon atom to which they are attached particularly preferably represent saturated C6-cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, ethyl, trifluoromethyl, methoxy, ethoxy, propoxy or
15    butoxy,
    G    particularly preferably represents hydrogen (a) or represents one of the groups
0    0    R6
Ri (b),    -711- NI "R2 (C) or    0    N
in which
M    represents oxygen or sulphur,
    20 R'    particularly preferably represents Q -C8-alkyl, Q-C4-alkenyl, methoxymethyl, ethoxy-
methyl, ethylthiomethyl, cyclopropyl, cyclopentyl or cyclohexyl,
 
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represents phenyl which is optionally mono- or disubstituted by fluorine, chlorine, bromine, cyan, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluor    emethoxy,
or represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,
R2    particularly preferably represents CI - Cr alkyl, C2- C4-alkenyl, methoxyethyl, ethoxyethyl
5    or represents phenyl or benzyl,
R6 and R7 independently of one another particularly preferably represent methyl, ethyl or together represent a C5-alkylene radical in which the C3-methylene group is replaced by oxygen
in the form of their isomer mixtures or pure isomers.
Very particular preference is given to using tetramic acid derivatives of the formula (I) mentioned 10 above in which the radicals are as defined below:
W    very particularly preferably represents hydrogen or methyl,
X    very particularly preferably represents chlorine, bromine or methyl,
Y and Z independently of one another very particularly preferably represent hydrogen, chlorine, bromine or methyl,
15 A, B and the carbon atom to which they are attached very particularly preferably represent saturated C6- cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy,
G    very particularly preferably represents hydrogen (a) or represents one of the groups
20    0    0    R6
,A _Fe    or
(b),    INA    (c)    0

in which
M    represents oxygen or sulphur,
 
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RI    very particularly preferably represents C1- Cs- alkyl, C2-C4-alkenyl, methoxymethyl,
ethoxymethyl, ethylthiomethyl, cyclopropyl, cyclopentyl, cyclohexyl or
represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
5    represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,
R2    very particularly preferably represents C1-C8-alkyl, C2-C4-alkenyl, methoxyethyl,
ethoxyethyl, phenyl or benzyl,
R6 and lf independently of one another very particularly preferably represent methyl, ethyl or together represent a C5- alkylene radical in which the C3-methylene group is replaced by 10    oxygen
in the form of their isomer mixtures or pure isomers.
Special preference is given to using tetramic acid derivatives of the formula (I) mentioned above in which the radicals are as defined below:    (I)
15         (I)

Example No.    W    X    Y    Z    R    G    m.p.°C
I-1    H    Br    H    CH3    OCH3    CO-i-C3H7    122
1-2    H    Br    H    CH3    OCH3    CO2-C2H5    140 - 142
1-3    H    CH3    H    CH3    OCH3    H    > 220
1-4    H    CH3    H    CH3    OCH3    CO2-C2H5    128
1-5    CH3    CH3    H    Br    OCH3    H    > 220
 

Example No.    W    X    Y    Z    R    G    m.p.°C
1-6    CH3    CH3    H    Cl    OCH3    H    219
1-7    H    Br    CH3    CH3    OCH3    CO-i-C3H7    217
1-8    H    CH3    Cl    CH3    OCH3    CO2C2H5    162
1-9    CH3    CH3    CH3    CH3    OCH3    H    >220
I-10    CH3    CH3    H    Br    0C2H5    CO-i-C3H7    212 - 214
I-11    H    CH3    CH3    CH3    0C2H5    CO-n-C3H7    134
I-12    H    CH3    CH3    CH3    0C2H5    CO-i-C3H7    108
I-13    H    CH3    CH3    CH3    0C2H5    CO-c-C3H5    163

in the form of their cis/trans isomer mixtures or their pure cis isomers.
The compounds of the formula (I) are known compounds whose preparation is described in the patents/patent applications cited on page 1 (see especially WO 97/01 535, WO 97/36 868, 5 WO 98/05 638).
From the family of the gall-making aphids (Phemphigidae), preference is given to: Eriosoma spp., Pemphigus spp., Anuraphis spp., in crops such as, for example, citrus fruit, pomme fruit, stone fruit, vegetables, beet, cereals and ornamental plants.
From the family of the phylloxerans (Phylloxeridae), preference is given to: Phylloxera spp. in 10    grapevines, nuts, citrus fruit.
From the family of the jumping plant lice (Psyllidae), preference is given to: Psylla spp., Paratrioza spp., Tenalaphara spp., Diaphorina spp., Trioza spp., in crops such as, for example, pomme fruit, stone fruit, citrus fruit, vegetables, potatoes, in tropical crops.
From the family of the soft scales (Coccidae), preference is given to: Ceroplastes spp., Drosicha
15 spp., Pulvinaria spp., Protopulminaria spp., Saissetia spp., Coccus spp., in perennial crops such as, for example, citrus fruit, pomme fruit, stone fruit, olives, grapevines, coffee, tea, tropical crops, ornamental plants, vegetables.
 
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From the family of the armoured scales (Diaspididae), preference is given to: Quadraspidiotus spp., Aonidiella 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 fruit, pomme fruit, stone fruit, almonds, nuts, olives, tea, ornamental plants,
5 grapevines, tropical crops.
From the family of the ensign coccids (Ortheziidae), preference is given to: Orffiezia spp. in citrus fruit, pomme fruit, stone fruit.
From the family of the mealy bugs (Pseudococcidae), preference is given to: Pericerga,
Pseudococcus spp., Planococcus spp., Dysmicoccus spp., in crops such as, for example, citrus
10 fruit, stone fruit and pomme fruit, tea, grapevines, vegetables, ornamental plants aid tropical crops.
From the family of the whiteffies (Aleyrodidae), preference is furthermore given to: Bemisia
argentifolii, Trialeurodes vaporariorum, Aleurothrixus floccosus, Aleurodes spp., Dialeurodes
spp., Parabemisia myricae in crops such as, for example, vegetables, melons, potatoes, tobacco,
15 soft fruit, citrus fruit, ornamental plants, cotton and tropical crops, and also Bemisia tabaci in crops such as, for example, vegetables, melons, soft fruit, tobacco, citrus fruit, ornamental plants, potatoes and tropical crops.
From the family of the aphids (Aphidae), preference is furthermore given to:
Myzus spp.    in tobacco, cereals, stone fruit, soft fruit, fruit vegetables, leafy
20    vegetables, tuber and root vegetables, melons, potatoes, beet, oilseed
rape, ornamental plants,
Aphis spp.    in tobacco, citrus fruit, pomme fruit, stone fruit, cereals, melons, beet,
soft fruit, oilseed rape, fruit vegetables, leafy vegetables, brassica vegetables, tuber and root vegetables, ornamental plants, potatoes, 25    cucurbits,
Rhodobium porosum in strawberries,
Nasonovia ribisnigri    in leafy vegetables,
Dysaphis spp.    in pomme fruit,
 
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Macrosiphum spp.    in ornamental plants, cereals, potatoes, leafy vegetables, brassica
vegetables and fruit vegetables, strawberries,
Rhopalosiphum padi, Sitobion avenae, Methopolophium dirhodum, Brachycolus noxius in cereals,
5 Phorodon humuli    in hops,
Brachycaudus helychrisii in stone fruit, such as, for example, plums,
Toxoptera spp.    in citrus fruit, stone fruit, almonds, nuts, cereals, spices,
Anlacorthum spp.    in citrus fruit, potatoes, fruit vegetables and leafy vegetables.
Very particular preference is given to the control of the following species from the family of the
10 gal]-making aphids (Pemphigidae) in the following crops, preferably after foliar application: Eriosoma lanigerum    in pomme fruit and stone fruit such as, for example, apples, pears,
cherries, plums, garden plums,
Eriosoma pyricola    in pomme fruit such as apples and pears,
Pemphigus fuscicomis, Pemphigus bursarius in beet, vegetables, ornamental plants.
15
All plants and plant parts can be treated in accordance with the invention. In this context, plants are understood as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (mcluding naturally occurring crop plants). Crop plants can be plants which can be obtained by traditional breeding and optimization methods or by biotechnological and
20 recombinant methods, or combinations of these methods, including the transgenic plants and including the plant varieties which are capable or not capable of being protected by Plant Breeders' Rights. Plant parts are understood as meaning all aerial and subterranean parts and organs of the plants such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stalks, stems, flowers, fruit bodies, fruits and seeds, but also roots, tubers and
25 rhizomes. The plant parts also include crop material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, slips and seeds.
The treatment according to the invention with the active compound, of the plants and plant parts,
is effected directly or by treating their environment, habitat or store using conventional treatment
methods, for example by dipping, spraying, fumigating, fogging, scattering, brushing on, injecting,
 
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and, in the case of propagation material, in particular seeds, furthermore by coating with one or more coats.
As already mentioned above, all plants and their parts can be treated in accordance with the invention. In a preferred embodiment, plant species and plant varieties which are found in the wild
5 or which are obtained by traditional biological breeding methods, such as hybridization or protoplast fusion, and parts of these species and varieties are treated. In a further preferred embodiment, transgenic plants and plant varieties which have been obtained by recombinant methods, if appropriate hi combination with traditional methods (genetically modified organisms) and their parts are treated. The terms "parts", "parts of plants" or "plant parts" have been
10 described above.
Plants which are especially preferably treated in accordance with the invention are those of the varieties which are in each case commercially available or in use. Plant varieties are understood as meaning plants with novel traits which have been bred both by conventional breeding, by mutagenesis or by recombinant DNA techniques. They may take the form of varieties, biotypes
15 or genotypes.
Depending on the plant species or plant varieties, their location and growth conditions (soils, climate, vegetation period, nutrition), superadditive ("synergistic") effects may also occur as a result of the treatment according to the invention. Effects which exceed the effects actually to be expected are, for example, reduced application rates and/or widened activity spectrum and/or an
20 enhancement of the activity of the substances and compositions which can be used in accordance with the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salinity, increased flowering performance, facilitated harvest, speedier maturation, higher yields, higher quality and/or higher nutritional value of the crop products, better storability and/or processibility of the crop products.
25 The preferred transgenic plants or plant varieties (plants or plant varieties obtained by means of genetic engineering) which are to be treated in accordance with the invention include all plants which, by means of the recombinant modification, have received genetic material which confers particularly advantageous valuable 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
 
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water or soil salinity, increased flowering performance, facilitated harvest, speedier maturation,
higher yields, higher quality and/or higher nutritional value of the crop products, better storability
and/or processibility of the crop products. Other examples of such traits which are particularly
emphasized are an improved defence of the plants against animal and microbial pests such as
5 insects, mites, phytopathogenic fungi, bacteria and/or viruses, and an increased tolerance of the
plants to specific herbicidal active compounds. Examples of transgenic plants which are
mentioned are the important crop plants such as cereals (wheat, rice), maize, soybean, potato,
cotton, tobacco, oilseed rape and fruit plants (with he fruits apples, pears, citrus fruits and
grapes), with particular emphasis on maize, soybean, potatoes, cotton, tobacco and oilseed rape.
10 Traits which are particularly emphasized are the increased defence of the plants against insects,
arachnids, nematodes and slugs and snails as the result of toxins formed in the plants, in particular
toxins which are produced in the plants by the genetic material of Bacillus Thuringiensis (for
example by the genes CryIA(a), CryIA(b), CrylA(c), CryIIA, CryffiA, CrylIB2, Cry9c,
Cry2Ab, Cry3Bb and CryiF and their combinations) (hereinbelow "Bt plants"). Traits which are
15 also particularly emphasized are the increased defence of plants against fungi, bacteria and viruses
by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and
correspondingly expressed proteins and toxins. Traits which are furthermore especially
emphasized are the increased tolerance of the plants to specific herbicidal active compounds, for
example imidazolinones, sulphonylureas, glyphosate or phosphinothricin (for example "PAT"
20 gene). The specific genes which confer the desired traits can also occur in combinations with one
another in the transgenic plants. Examples of "Bt plants" which may be mentioned are maize
varieties, cotton varieties, soybean varieties and potato varieties sold under the trade names
YIELD GARD® (for example maize, cotton, soybean), KnockOut® (for example maize),
StarLink® (for example maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato).
25 Examples of herbicide-tolerant plants which may be mentioned are maize varieties, cotton
varieties and soybean varieties which are sold under the trade names Roundup Ready®
(glyphosate tolerance, for example maize, cotton, soybean), Liberty link® (phosphinothricin
tolerance, for example oilseed rape), IMI® (imidazolinone tolerance) and STS® (sulphonylurea
tolerance, for example maize) Herbicide-resistant plants (bred conventionally for herbicide
30 tolerance) which may also be mentioned are the varieties sold under the name Clearfield® (for
example maize). Naturally, what has been said also applies to plant varieties which will be
 
- 16 -
developed, or marketed, in the future and which have these genetic traits or traits to be developed in the future.
The active compound of the formula (I) can be converted into the customary formulations, such
as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble
5 powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and ultrafine encapsulations in polymeric materials.
These formulations are produced in the known manner, for example by mixing the active compound 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.
10 In the case of the use of water as an extender, organic solvents can, for example, also be used as cosolvents. Liquid solvents which are suitable are mainly: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil fractions, mineral oils and vegetable oils,
15 alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl suiphoxide, and water.
Solid carriers which are suitable are:
for example ammonium salts and ground natural minerals, such as kaolin, clays, talc, chalk,
20 quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, 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, and synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam formers
25 are: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as protein hydrolysates; suitable dispersants are: for example lignosulphite waste liquors and methylcellulose.
 
- 17 -
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils.
5 It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general comprise between 0.1 and 95% by weight of active compound, 10 preferably between 0.5 and 90%, and additionally preferably extenders and/or surfactants.
The active compound content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active compound concentration of the use forms can be in the range of from 0.0000001 up to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.
15 Application is in a customary manner which is appropriate for the use forms.
 
- 18-
Use examples
Gall-making aphids (Pemphigidae)
Very particular preference is given to controlling the following species from the family of the gall-making aphids (Pemphigidae):
5 Eriosoma lanigerum in pomme fruit, such as, for example, apples, pears, and stone fruit, such as, for example, cherries, plums, garden plums,
Eriosoma pyricola in pomme fruit, such as, for example, apples and pears,
Pemphigus bursaries, in ornamental plants, such as, for example, duysanthernums, in vegetables, such as, for example, head lettuce,
10 Pemphigus fuscicomis in beet, leafy vegetables, such as, for example, head lettuce, root vegetables, such as, for example, carrots, ornamental plants, such as, for example, chrysanthemums,
Anuraphis cardui in vegetables, such as, for example, artichokes. Example 1
15 Two about 23-year-old apple trees of the cultivar Idared" infested by Eriosoma lanigerum are, under practical conditions, treated with Example (1-9) (240 SC) and Example (1-4) (240 SC) in comparison to the commercial standard inidacloprid 200 SL at the stated application rates. Application is with a motor-operated knapsack sprayer. The application rate is 1500 1 of water/ha.
20 Evaluation is carried out 15 and 37 days after the application by rating the kill in per cent on the branches.
Active compound    Application rate    Kill (%)
    al. in %    15 d    37 d
imidacloprid    0.01    97    100
Example (1-9)    0.0144    99    100
 
- 19-
Example (1-4)    0.0144    100    99
Example 2
In three replications, in each case 10 109-day-old chrysanthemums of the cultivar 'Camilla" in 2
1-vessels are treated against the lettuce root aphid Pemphigus bursarius. Here, the active
5 compounds Example (1-9) (240 SC) and Example (1-2) (240 SC) are applied with a knapsack sprayer operated by pressurized air at the stated application rates only to the above-ground parts of the plants. The soil is covered with a film. The application rate is 3001 of water/ha. 0.1% a.i. of rapeseed oil methyl ester (500 EW) is added to the spray liquor.
The kill in per cent is determined on the roots. 21 and 29 days after the application, the fallowing 10 results are obtained:
Active compound    Application rate    Kill (%)
    a.i. in %    21 d    29 d
Example (I-9)    144    76.5    94.0
Example (1-2)    96    80.8    91.8

Example 3
In three replications, in each case 10 about 5-month-old chrysanthemums (Camilla) in 21-vessels
are treated against the lettuce root aphid Pemphigus bursarius. Here, the active compound
15 Example (1-4) (240 SC) is applied with a knapsack sprayer operated by pressurized air at the beginning of the infestation at the stated application rates to the above-ground parts of the plants. The soil is covered with a film. The application rate is 6001 of water/ha. 0.1% a.i. of rapeseed oil methyl ester (500 EW) is added to the spray liquor. Omethoate as drip irrigation in a concentration of 0.1% is used for comparison. The application is carried out two days later.
20 The kill in per cent is determined on the roots. After 9 and 17 days, the following kills are obtained:
 
- 20 -
Active
compound    Application rate    Kill (%)
Example (I-4)    96 g of a.i./ha    46.9 (9d)    80.4 (17d)
omethoate    drip irrigation 0.1%    20 (7d)    70.6 (15d)

Phylloxerans (Phylloxeridae)
Very particular preference is given to controlling the following species from the family of the 5 phylloxerans (Phylloxeridae), preferably after foliar application:
10    Phylloxera devastatrix
Phylloxera vastatrix, (? Viteus vitifolii)
Example 4     in grapevines, in nuts, such as, for example, pecan nuts,
in grapevines.

In four replications, three in each case about 12-year-old vines of he cultivar `Auvemaf' are
treated against Viteus vitifolii. As commercial standard, inidacloprid is used at the recommended
application rate by drip irrigation. The application of the active compounds is by spray application
15 to the leaves using a knapsack operated with pressurized air. Here, the active compounds Example (I-4) (240 SC) and Example (I-9) (240 SC) are applied in a tank mix with 0.1% a.i. of rapeseed oil methyl ester (500 EW) at the stated amount. There are three applications on day 1, 2 and 15. The application rate is 17761 of water/ha.
Evaluation is carried out 60 days after the last treatment by rating the kill on the roots in per cent.
Active compound    Application rate a.i.    Kill (%)
imidacloprid    drip irrigation
560 g/ha    26
Example (1-4)    0.0168%    55
 
- 21 -
Example (179)    0.0144%    42
Jumping plant lice (Psyllidae)
Very particular preference is given to controlling the following species from the family of the jumping plant lice (Psyllidae):
Psylla pyricola    in pomme fruit, such as, for example, pears, apples, in stone fruit, such
5    as, for example, cherries, plums, garden plums, peaches, nectarines,
Psylla piri    in pomme fruit, such as, for example, pears,
Psylla PYrisuga    in pomme fruit, such as, for example, pears,
Psylla costalis    in pomme fruit, such as, for example, apples,
Paratrioza cockerelli    in fruit vegetables, such as, for example, tomatoes, bell peppers, chilli
10    peppers, in root vegetables, such as, for example, carrots, in potatoes,
Tenalaphara malayensis in tropical crops, such as, for example, durians,
Diaphorina citri    in citrus fruit, such as, for example, oranges, mandarins, limes,
grapefruits,
Trioza erythrae    in citrus fruits, such as, for example, oranges, grapefruits.
15
Example 5
In three replications, pear trees of the cultivar "Williams Christ" are treated against Psylla piri.
Application is shortly before the eggs hatch. The application is carried out using a barrow-
mounted sprayer operated with pressurized air. Here, the active compound Example (1-4) (240
20 SC) E tested in a lank mix with 0.1% a.i. rapeseed oil methyl ester (500 EW) at the stated amount against the standard amitraz (200 EC) at the stated amount. The application rate is 1000 1 of water/ha.
Evaluation is carried out 7, 14 and 21 days after the treatment by rating the kill of the nymphs on the shoots.
25
 
- 22 -
Active
compound    Application rate
g of al/ha/height of crown in
m    Kill
(%)
        7d    14d    21d
amitraz    266    100    95.2    75
Example (1-4)    72    100    100    100

Example 6
In three replications, in each case 4 about 4year-old pear trees of the cultivar "Williams Christ'
are treated against Psylla piri Two applications are carried out at an interval of 11 days using a
5 motor-operated barrow-mounted sprayer. Here, the active compounds Example (1-9) (240 SC), Example (I-2) (240 SC) and Example (I-1) (240 SC) are tested against the commercial standard Arnitraz (200 EC) at the stated amounts. The application rate is 2000 lof water/ha.
Evaluation is carried out 3, 10 and 20 days after the last treatment by rating the kill of the larvae in per cent on the shoots.
Active
compound    Application rate (%) of al.    Kill (%)
        3d    10d    20d
amitraz    0.05    54.3    56.7    21.4
Example (I-9)    0.096    97.7    100    100
Example (1-2)    0.096    96.7    99    97.9
Example (1-1)    0.096    90.0    96.6    95.0

10
Example 7
In four replications, plots of a size of about 7 nf with bell peppers of the cultivar 'Jupiter" are
treated against Paratrioza cockerelli. The application is carried out with a knapsack sprayer
operated with pressurized air. Here, the active compound Example (I-4) (240 SC) is applied in a
 
- 23 -
tank mix with 0.2% a.i. of rapeseed oil methyl ester (500 EW) and the commercial standards imidacloprid 192 SC and dimethoate (480 EC) are applied in a tank mix with 0.125% Induce at the stated application rates. The application is carried out with an application rate of 467 1 of water/ha.
5 Evaluation is carried out 7 and 15 days after the treatment by rating the kill of the animals (nymphs) on the leaves.
Active compound    Application rate g of a.i./ha    Kill (%)
        7d    15d
Imidacloprid    52.6    90    0
Example (I-4)    72    90    100
dimethoate    561    63    0

Example 8
In three replications, about 2.year-old orange trees are treated against Trioza erythreae. The
10 application is carried out using a knapsack sprayer operated with pressurized air. Here, the active compound Example (I-4) (240 SC) is tested in a tank mix with 0.2% a.i. of rapeseed oil methyl ester (500 EW) against the commercial standard imidacloprid (100 SL) at the stated application rates. The application rate is 540 1 of water/ha. Two treatments are carried out, at an interval of 7 days.
15 Evaluation is carried out 7, 14 and 20 days after the first treatment by rating the kill of the nymphs on the branches.
Active
compound    Application rate (%)    Kill (%)
        7d    14d    20d
imidacloprid    0.004    98.4    99.2    98.6
Example (1-4)    0.0144    97.9    98.9    98.3
 
- 24 -
Example 9
In three replications, plots of a size of 10 mz with tomatoes are treated against Paratrioza cockerelli. Application is carried out using a knapsack sprayer operated with pressurized air.
5 Here, the active compound Example (1-4) (240 SC) in a tank mix with 0.2% a.i. of rapeseed oil methyl ester (500 EW) and the commercial standard Leverage (324 SE) are tested at the stated application rates. There are two applications at an interval of 7 days. The application rate is 345 1 of water/ha.
Evaluation is carried out 7, 14 and 21 days after the first treatment by rating the kill of the animals 10 (nymphs) on the leaves.
Active
compound    Application rate g of ailha    Kill (%)
        7d    14d    21d
Levarage    81    75.4    81.1    92.1
Example (1-4)    48    71.3    90.3    95.5

Soft scales (Coccidae)
Very particular preference is given to controlling the following species from the family of the soft scales (Coccidae) in the following crops, preferably after foliar application:
Ceroplastes ceriferus    in citrus fruit, such as, for example, oranges, grapefruits, mandarins,
Ceroplastes floridensis    lemons, limes, satsumas
Ceroplastes rubens
Ceroplastes rusci
Drosicha mangiferae    in tropical crops, for example mangoes
Drosicha stebbengii
 
- 25 -
Pulvinaria aurantii    in citrus fruit, such as, for example, oranges, grapefruits, mandarins,
Pulvinaria aethiopicus    lemons, limes, satsumas, in grapevines
Pulvinaria vitis
Protopulminaria pyriformis in pomme fruit and stone fruit
Saissetia oleae    in citrus fruit, such as, for example, oranges, grapefruits, mandarins,
limes
Saissetia nigra    in citrus fruit, such as, for example, lemons, satsumas, in olives, in
tropical crops, for example bananas
Coccus viridis
Coccus hesperdium
Example 10    in citrus fruit, such as, for example, oranges, mandarins, grapefruits, limes, lemons, satsumas, in tropical crops, for example pineapples
in pomme fruit, such as, for example, apples, pears, in stone fruit, such as, for example, peaches, nectarines, plums, apricots, cherries, in coffee, in olives, in tea, in vegetables, such as, for example, beans, in grapevines

In three replications, about 6-year-old mandarin trees of the cultivar "Naartje" are treated against
Pulvinaria aethiopicus. Two applications are carried out at an interval of 32 days as irradication
treatment using a knapsack operated with pressurized air. Here, the active compounds Example
5 (I-9) (240 SC) and Example (1-2) (240SC) are tested against a commercial tank mix of a mineral oil (835 EC) which is commercially available in South Africa and customarily used in this country and pyriproxifen (100 EC) at the stated amounts. The application rate is 8.31 of water/tree.
Evaluation is carried out 45 days after the last treatment by rating the kill in per cent on the fruits.
 
- 26 -
Active compound    Application rate (%) of
a.i.    Kill (%)
Mineral oil    0.251    90
+ pyriproxifen    0.003   
Example (1-9)    0.0096    91
Example (1-2)    0.0144    72

Example 11
In three replications, in each case one about 4-year-old satsuma tree of the cultivar "Nankan 20"
is treated against Pulvinaria aurantii. Here, the active compound Example (I-4) (240 SC) in a tank
5 mix with 0.2% of rapeseed oil methyl ester (500 EW) at the stated application rate is tested against the commercial standard buprofezin at the stated application rate. The application is carried out using a motor-operated knapsack sprayer. Here, each plant is treated with 400 ml of spray liquor.
Evaluation is carried out before and 41 days after the treatment by counting the live animals. The 10 efficacy in per cent is then calculated according to Henderson and Tilton.
Active compound    Application rate (%) of a.i.    Effect (%)
buprofezin    0.025    68
Example (1-4)    0.0144    100

Example 12
In three replications, in each case one about 4-year-old satsuma tree of the cultivar "Nankan 20"
is treated against Ceroplastes rubens. Here, the active compound Example (1-4) (240 SC) in a
15 tank mix with 0.1% of rapeseed oil methyl ester (500 EW) at the stated application rate is tested against the commercial standard buprofezin (25 WP) at the stated application rate. The application is carried out using a motor-operated knapsack sprayer. Here, treatment is carried out using an application rate of 4001 of water/ha.
 
- 27 -
Evaluation is carried out before and 41 days after the treatment by counting the live animals. The efficacy in per cent is then calculated according to Henderson and Tilton.
Active compound    Application rate (%) of a.i.    Effect (%)
buprofezin    0.025    50
Example (1-4)    0.0072    .    98

Example 13
5 In three replications, in each case two about 8-year-old orange trees are treated against Saissetia oleae. Here, the active compounds Example (1-4) (240 SC) and Example (1-8) (250 SC) in a tank mix with 0.2% a.i. of rapeseed oil methyl ester (500 EW) at the stated application rate are tested against the commercial standard buprofezin in a tank mix with 0.4% a.i. of Oliocin (800 EW) at the stated application rate. The application is carried out using a motor-operated
10 knapsack sprayer. The application rate is 3000 1 of water/ha. Two treatments are carried out, at an interval of 29 days.
Evaluation is carried out 24 and 44 days after the last treatment by rating the kill of the nymphs on the leaves.
Active compound    Application rate g of a.i./ha/height of crown in m    Kill (%)   
        24 d    44 d
buprofezin    500    33.5    50.5
Example (I-4)    72    53.5    56.1
Example (1-8)    30    66.5    56.1

15 Example 14
In three replications, orange trees of the cultivar Navelina" are treated against Saissetia oleae. Here, the active compounds Example (1-4) (240 SC) and Example (I-9) (240 SC) in a tank mix with 0.1% of rapeseed oil methyl ester (500 EW) at the stated application rate are tested against the commercial standards Dursban (480 EC) and pyriproxyfen (100 EC) at the stated application
 
- 28 -
rate. The application is carried out using a motor-operated knapsack sprayer. The application rate is 3200 1 of water/ha.
Evaluation is carried out 120 days after the treatment by rating the kill of the animals on the branches.
Active compound    Application rate (%) of a.i.    Effect (%)
        120 d
Dursban    0.096    0
Example (1-4)    0.012    98
Example (I-9)    0.0054    79
pyriproxyfen    0.005    100

Armoured scales (Diaspididae)
Very particular preference is given to controlling the following species from the family of the armoured scales (Diaspididae) in the following crops, preferably after foliar application:
Quadraspidiotus    in citrus fruit, such as, for example, oranges, mandarins, limes,
pemiciosus    grapefruits, in pomme fruit, such as, for example, apples, pears, quince,
Quadraspidiotus    in stone fruit, such as, for example, peaches, nectarines, apricots, plums,
juglansregiae    cherries, in nuts, such as, for example, almonds, pistachios, walnuts,
hazelnuts, in ornamental plants, such as, for example, shrubs, conifers, potted plants, in tropical crops, for example litchis,
Aonidiella aurantii    in citrus fruit, such as, for example, uanges, mandarins, grapefruits,
Aonidiella citrina    limes, lemons, satsumas,
Lepidosaphes ulmi    in citrus fruit, such as, for example, oranges, nandarins, grapefruits,
Lepidosaphes beckii limes, lemons, satsumas, in pomme fruit, such as, for example, apples and pears, in stone fruit, such as, for example, peaches, nectarines, plums, apricots, cherries,
 
- 29 -
Aspidiotus destructor in citrus fruit, such as, for example, (ranges, mandarins, grapefruits,
Aspidiotus hederae    limes, lemons, satsumas, in ornamental plants, such as, for example,
Aspidiotus nerii    shrubs, potted plants, in olives, in tropical crops, for example mangoes,
Aspidiotus ficus    limes,
Pseudaulacaspis    in pomme fruit, such as, for example, apples, pears, in stone fruit, such
pentagona    as, for example, peaches, apricots, nectarines, cherries, plums, garden
plums, in tea,
Unaspis yanonensis    in citrus fruit, such as, for example, oranges, mandarins, limes,
Unaspis citri    grapefruits, lemons, satsumas, in tropical crops, for example pineapples,
mangoes,
Pinnaspis aspidistrae
Parlatoria ziziphus    in citrus fruit, such as, for example, cranges, mandarins, limes, lemons,
Parlatoria pergandei    satsumas, grapefruits, in olives,
Parlatoria oleae
Selenaspidus    in citrus fruit, such as, for example, oranges, mandarins, limes,
articulatus    grapefruits, lemons, satsumas
Example 15
In three replications, 3-year-old orange trees of the cultivar 'Midnight Valenzia" are treated
against Aonidiella aurantii. Two applications are carried out at an interval of 72 days, using a
5 motor-operated knapsack sprayer. Here, the active compounds Example (1-9) (240 SC) and Example (1-2) (240 SC) in a tank mix with 0.1% a.i. of rapeseed oil methyl ester (500 EW) at the stated application rate are tested against the Sandard Tokuthion (960 EC) at the stated amounts. applied once. The application rate is 41 of water per tree.
Evaluation is carried out 130 and 176 days after the treatment by rating the kill on the fruits.
 
- 30 -
Active
compound    Application rate (%) of a.i.    Kill (%)
        130d    176d
Tokuthion    0.048    12    0
Example (I-9)    0.0096    86    100
Example (I-2)    0.0096    52    76

Example 16
In four replications, an about 10-year-old grapefruit tree of the cultivar 'Rio Red" is treated
against Aonidiella aurantii. The application is carried out using a motor-operated barrow-mounted
5 sprayer. Here, the active compound Example (I-4) (240 SC) and the commercial standard Dursban (480 EC) are tested at the stated application rates. The amount of spray liquor is 5.8 gallons per tree.
Evaluation is carried out 28, 59 and 90 days after the treatment by rating the kill of the animals on the fruits.
Active compound    Application rate per metre of crown height
a.i.    Kill (%)   
        28d    59d    90d
Dursban    6.01 pounds/acre    100    100    100
Example (I-4)    72 g/ha    92.7    100    100

10
Example 17
In three replications, four about 18-year-old apple trees of the cultivar 'Red Chief' are treated
against the San Jose scale louse Quadraspidiotus perniciasus. Two applications are carried out at
an interval of 15 days using a motor-operated barrow-mounted sprayer. Here, the active
15 compound Example (I-4) (240 SC) is applied in a tank mix with 0.2% a.i. of rapeseed oil methyl
 
- 31 -
ester (500 EW) at the stated application rate and the commercial standard Dursban (446 EC) is applied at the stated application rate. The application rate is 1500 1 of water/ha.
Evaluation is carried out 43 days after the last treatment by rating the kill on the shoots.
Active
compound    Application rate
g of ailha/crown height in m    Kill (%)
Dursban    223    68.3
Example (1-4)    72    90.4

5 Example 18
In three replications, in plots of a size of about 20 m2, citrus trees of the cultivar "Oro Nules" are treated against Lepidosaphes beckii. The application is carried out using a high-pressure sprayer. Here, the active compound Example (I-4) (240 SC) in a tank mix with 0.1% a.i_ of rapeseed oil methyl ester (500 EW) is tested against the commercial standard pyriproxyfen (100 EC), at the
10 stated application rates. The application rate is 2500 1 of water/ha.
Evaluation is carried out 140 days after the treatment by rating the kill of the larvae on the fruits.
Active
compound    Application rate
g of al/ha/crown height in m    Kill (%)
140 days
pyriproxyfen    50    100
Example (I-4)    48    100

Example 18a
The evaluation for Example 18a against Parlatoria pergandei is carried out as part of the test as 15 described in Example 27 and is listed separately in Example 27.
Example 19
 
- 32 -
In three replications, 3-year-old orange trees of the cultivar Tem natar' are treated against Selenaspidius articulatus. The application is carried out using a motor-operated knapsack sprayer. Here, the active compounds Example (I-9) (240 SC) and Example (1-4) (240 SC) at the stated application rate are tested against the standard methidathion (400 EC) in the stated
5 amounts, applied once. The application rate is 3.31 of water per tree.
Evaluation is carried out 100 days after the treatment by rating the kill on the leaves.
Active
compound    Application rate (%) of a.i.    Kill (%)
        100d
methidathion    0.05    77
Example (1-9)    0.0288    77
Example (1-4)    0.0144    70

Example 20
In four replications, about 5-year-old lime trees of the cultivar "Fino" are treated against
10 Aspidiotus neri. The application is carried out using a knapsack sprayer. Here, the active compound Example (1-4) (240 SC) in a tank mix with 0.1% a.i. of rapeseed oil methyl ester (500 EW) at the stated application rate is tested against the standards Dursban (480 EC) and Juvinal (100 EC) at the stated amounts, applied once. The application rate is 3000 1 of water/ha per tree.
15 Evaluation is carried out 167 days after the treatment by rating the kill on the fruits.
Active
compound    Application rate (%) of a.i.    Kil (%)
        167d
Dursban    0.096    76.9
Juvinal    0.005    86.5
Example (1-4)    0.0072    96.2
 
- 33 -
Example 21
In four replications, an about 20-year-old almond tree of the cultivar 'Non-Parer is treated
against Quadraspidiotus pemiciosus. The application is carried out using a high-pressure sprayer.
5 Here, the active compound Example (1-4) (240 SC) in a tank mix with 0.125% a.i. of methylated seed oil (1000 EC) and the commercial standard Lorsban (480 EC) are tested at the stated application rates. The amount of spray liquor is 935 I/ha.
Evaluation is canied out 21, 42 and 63 days after the treatment by rating the kill of the animals on the branches.
Active
compound    Application rate per metre of
crown height al.    Kill (%)
        21d    42d    63d
Dursban    2240 g/ha    82.2    73.3    78.4
Example (I-4)    110 g/ha    84.9    90    94.6

10
Example 22
In ten replications, on about 46 rri, peach trees are treated against Pseudaulacaspis pentagons. Two applications are carried out at an interval of 57 days using a sprayer operated with pressurized air. Here, the active compound Example (1-4) (240 SC) in a tank mix with 0.2% of
15 Dynamic (910 XL) is applied at the stated application rate and the commercial standard Esteem
(35 WP) is applied at the stated application rate. The application rate is 935 lof water/ha.
Evaluation is carried out 35 and 79 days after the last treatment by rating the kill of the crawlers on the shoots.
 
- 34 -
Active
compound    Application rate
g of a.i./ha/height of crown
in m    Kill (%)
        35d    79d
Esteem    98    98    94
Example (1-4)    120    90    87

Example 23
In six replications, about 16-year-old Japanese apricot trees of the cultivar "Shirokag" are treated
against Psewlaulacaspis prunicola. The application is carried out using a sprayer. Here, the active
5 compound Example (1-4) (200 SC) is tested against the commercial standard Supracide EC (400 EC), at the stated application rates. The application rate is 1500 lof water/ha.
Evaluation is carried out 58 days after the treatment by rating the kill of the nymphs on the shoots.
Active
compound    Application rate (%) of al.    Kill (%)
58 days
Supracide EC    0.04    91.6
Example (1-4)    0.0075    92.3

Example 24
10 In nine replications, about 7-week-old tea plants of the cultivar "Yakubita" are treated against Pseudaulacaspis pentagons. Here, the active compound Example (1-4) (200 SC) is tested against the commercial standard Supracide EC (400 EC) at the stated application rates. The application is carried out using a sprayer operated with pressurized air. Evaluation is carried out 16 and 35 days after the treatment by rating the kill of the crawlers on the plants.
Active
compound    Application rate (%) of a.i.    Kill (%)
 
- 35 -
        16d    35d
Supracide EC    0.04    60.3    100
Example (1-4)    0.01    81.8    75

Ensign coccids (Ortheziidae)
Very particular preference is given to controlling the following species from the family of the ensign coccids (Ortheziidae) in the following crops, preferably after foliar application
Orthezia praelonga    in citrus fruit, such as, for example, oranges, mandarins, limes,
grapefruits, lemons, satsumas
5
Example 25
In two replications, two about 7-year-old orange trees of the cultivar `Pena Rio" are treated
against Orthezia praelonga. Here, the active compounds Example (I-4) (240 SC) and Example
(1-9) (240 SC), in a tank mix with 0.1% a.i. of Renex, are tested against the commercial standard
10 Methidathion (400 EC), at the stated application rates. The application is carried out using a knapsack sprayer operated with pressurized air. Evaluation is carried out 6 and 16 days after the treatment by rating the kill of the population on the leaves.
Active
compound    Application rate (%) of a.i.    Kill (%)
        6d    16d
methidathion    0.05    91    61
Example (1-4)    0.0144    94    76
Example (I-9)    0.0144    89    63

Mealy bugs (Pseudococcidae)
 
- 36 -
Very particular preference is given to controlling the following species from the family of the mealy bugs (Pseudococcidae) in the following crops:
Pseudococcus citri    in citrus fruit, such as, for example, oranges, mandarins, grapefruits,
Pseudococcus comstocki limes, lemons, satsumas, in pomme fruit, such as, for example,
Pseudococcus maritimus    apples and pears, in grapevines, in ornamental plants, in tropical
crops, such as, for example, pineapple
Dysmicoccus boninsis    in pomme fruit, such as, for example, apples, pears, in tea, in
Dysmicoccus cryptus    tropical crops, such as, for example, pineapples, guyabano
Dysmicoccus brevipes
Planococcus lilacinus    in citrus fruit, such as, for example, oranges, mandarins, grapefruits,
Planococcus citri    limes, lemons, satsumas, in grapevines
Pericerga purchasi    in citrus fruit, such as, for example, oranges, mandarins, grapefruits,
limes, lemons, satsumas
Example 26
5 In three replications, in plots of a size of about 20 m2, citrus trees of the cultivar "Oro Nules" are treated against Pseudococcus citri The application is carried out using a high-pressure sprayer. Here, the active compound Example (I-4) (240SC), in a tank mix with 0.1% a.i. of rapeseed oil methyl ester (500 EW), is tested against the commercial standard Dursban (480 EC), at the stated application rates. The application rate is 2500 1 of water/ha.
10 Evaluation is carried out 62 days after the treatment by rating the kill of the larvae on the fruits.
Active compound    Application rate
g of al/ha/crown height in m    Kill (%)
62 days
Dursban    960    100
Example (I-4)    72    99
 
- 37 -
Example 27
In three replications, orange trees of the cultivar "Navelina" are treated against Parlatoria
pergandei and Pseudococcus citri. Two applications are carried out at an interval of 77 days
using a motor-operated knapsack sprayer. Here, the active compound Example (1-9) (240 SC),
5 in a tank mix with 0.1% a.i. of rapeseed oil methyl ester (500 EW), at the stated amount, is tested against the commercial standard pyriproxyfen (100 EC), at the stated amounts. The application rate is 3000 I of water/ha.
Evaluation is carried out 56 days or 73 days after the last treatment by rating the kill in per cent on the fruits.
10 Parlatoria pergandei (Example 18a)
Active
compound    Application rate (%) of a.i.    Kill (%)
73d
pyriproxyfen    0.005    97.5
Example (1-9)    0.0096    98.7

Pseudococcus citri
Active
compound    Application rate (%) of a.i.    Kill (%)
56d
pyriproxyfen    0.005    28.8
Example (I-9)    0.0096    94.6

15 Example 28
In four replications, three in each case about 12-year-old vines of the cultivar "Auvemaf' are treated against Pseudococcus spp. The commercial standard used is an application with imidacloprid at the recommended application rate, by drip irrigation. The active compounds are applied by spraying using a knapsack sprayer operated with pressurized air. Here, the active
 
- 38 -
compounds Example (I-4) (240 SC) and Example (I-9) (240 SC) are applied in a tank mix with 0.1% a.i. of rapeseed oil methyl ester (500 EW), at the stated amount. Two applications are carried out at an interval of 15 days. The application rate is 1776 1 of water/ha. Evaluation is carried out 28 days after the last treatment by rating the kill on grapes in per cent.
5
Active compound    Application rate of a.i.    Kill (%)
imidacloprid    drip irrigation 560 g/ha    100
Example (1-4)    0.0168 %    99
Example (1-9)    0.0144 %    100

Example 29
In three replications, in plots of a size of 54 m2, about 10-year-old vines of the cultivar
"Napoleon" are treated against Planococcus spp. The application is carried out using a knapsack
10 sprayer. Here, the active compound Example (I-4) (240 SC), in a tank mix with 0.1% a.i. of rapeseed oil methyl ester (500 EW), is tested against the commercial standard Dursban (480 EC), at the stated application rates. The application rate is 864 1 of water/ha. Two treatments are carried out, at an interval of 19 days.
Evaluation is carried out 16 and 38 days after the second treatment by rating the kill of the larvae 15 on the grapes.
Active
compound    Application rate % /    1        Kill (%)
            16d        38d
Dursban    0.096        72.2        64
Example (1-4)    0.0096        94.4        91.9

Example 30
 
- 39 -
In five replications, pineapple plants of the cultivar 'IVID2" of a height of about 35 cm are treated against Dysmicoccus brevipes. The application is carried out using a motor-operated knapsack sprayer. Here, the active compound Example (1-4) (150 OD) is tested against the commercial standard Confidor OD (240 OD), at the stated application rates. The application rate is 4000 lof
5 water/ha. Both active compounds are sprayed as a tank mix with 500 g of a.i./ha of adjuvant NP-7 and 41 of a.i./ha of mineral oil.
Evaluation is carried out 9, 23 and 37 days after the treatment by rating the kill of the nymphs on the plants.
Active
compound    Application rate
g of a.i./ha    Kill (%)
        9 days    23 days    37 days
Confidor OD    140    93.9    98.6    76.8
Example (1-4)    75    80.9    84.0    91.3

10 Example 30a
In three replications, in each case one wyabano tree is treated against Dysmicoceus brevipes. Here, the active compound Example (1-4) (240 SC), in a tank mix with 0.1% of rapeseed oil methyl ester (500 EW), is, at the stated application rate, tested against the commercial standard Lorsban (500 EC), at the stated application rate. The application is carried out using a motor-
15 operated knapsack sprayer. Here, each plant is treated with spray liquor.
Evaluation is carried out 3, 7 and 14 days after the treatment by rating the kill in per cent on the fruits.
Active
compound    Application rate
(g) of a.i./crown height in m    Kill (%)
        3 days    7 days    14 days
Lorsban    180    78.3    94.7    100
 
- 40 -
Example (1-4)    48    89.8    100    100
Whiteflies (Aleyrodidae)
Very particular preference is furthermore given to controlling the following species from the family of the whiteflies (Aleyrodidae), in the following crops:
Bemisia tabaci
Bemisia argentifolii    in vegetables, such as bell peppers, tomatoes, cucumbers, cabbage, for example broccoli, beans, lettuce, aubergines, courgettes, cucurbits, in soft fruits, in melons, for example watermelons, net melons, cantaloupe melons, in ornamental plants, such as roses, hibiscus, in citrus fruit, such as oranges, mandarins, grapefruits, and also in potatoes, in tobacco and in tropical crops, such as, for example, papayas, bananas,
in cotton, in vegetables, such as bell peppers, tomatoes, cucumbers, beans, cucurbits, aubergines, es, courgettes, cabbage, in soft fruit, in melons, for example watermelons, net melons, cantaloupe melons, n ornamental plants, such as, for example, roses, hibiscus, in tropical crops, such as, for example, papayas, bananas,

Trialeurodes vaporariorum in vegetables, such as bmatoes, bell peppers, beans, cucumbers, cucurbits, aubergines, in soft fruit, in melons and also in ornamental plants, such as, for example roses, hibiscus,
Aleurothrixus floccosus    in citrus fruit, such as, for example, oranges, mandarins, lemons
Aleurodes citri    in citrus fruit, such as oranges, mandarins, lemons, grapefruits,
limes, cumquats
Aleurodes fragriae    in soft fruit, such as, for example, strawberries
 
-41-
Aleurodes azaleae    in ornamental plants, such as, for example, azalea
Example 31
In four replications, in each case one orange tree of the cultivar 'Newhall" is treated against
Aleurodes citri. Here, the active compound Example (I-4) (240 SC) is, at the stated application
5 rate, tested against the commercial standard imidacloprid. The active compounds are applied in a tank mix with 0.5% al of Oliocin (700 EW), at an application rate of 1500 1 of water/ha. The application is carried out using a motor-operated knapsack sprayer.
Evaluation is carried out 7, 14 and 21 days after the treatment by rating the kill of the animals on the leaves.
Active
compound    Application rate
g of al./ha/crown height in m    Kill (%)
        7d    14d    21d
imidacloprid    75    98.4    99.6    99.4
Example (I-4)    72    90.9    99.5    99.9

10
Example 32
In three replications, plots of a size of 10 m2 with bell peppers of the cultivar Italiano" are treated
against Bemisia tabaci. The application is carried out using a motor-operated knapsack sprayer.
Here, the active compounds Example (I-9) (240 SC), Example (I-2) (60 SC) and Example (I-
15 11) (60 SC) and the commercial standard imidacloprid (200 SL) are applied at the stated application rates. Three applications at an interval of 14 or 15 days are carried out, at an application rate of 1000 or 1100 1 of water/ha.
Evaluation is carried out 7, 14 and 22 days after the second treatment by rating the kill of the animals (larvae) on the leaves.
20
 
- 42 -
Active
compound    Application rate % of a.i.    Kill (%)
        7d    14d    22d
imidacloprid    0.02    75.8    67.2    69.4
Example (1-9)    0.0144    90.4    95.1    92.6
Example (I-2)    0.0144    84.7    92.6    85.6
Example (I-11)    0.0144    85.4    93.3    91.3

Example 33
In four replications, plots of a size of 26 m2 with cucumbers of the cultivar 'Beta alpha" are
treated against Bemisia tabaci The application is carried out using a knapsack sprayer operated
5 with pressurized air. Here, the active compound Example (1-4) (240 SC), in a tank mix with 0.1% a.i. of rapeseed oil methyl ester (500 EW), and the commercial standard imidacloprid (200 SC) are tested at the stated application rates. Two applications are carried out, at an interval of 10 days. The application rate is 1000 1 of water/ha.
Evaluation is carried out 7, 11 and 21 days after the first treatment by rating the kill of the animals 10 (nymphs) on leaves.
Active
compound    Application rate % of a.i.    Kill (%)
        7d     1 1 d    21d
imidacloprid    0.144    89    96    96
Example (1-4)    0.084    75    87    90

Example 34
In three replications, plots of a size of 5 m2 with tomatoes of the cultivar "Rio Grande" are treated
against Trialeurodes vaporariorum. The application is carried out using a motor-operated
15 knapsack apparatus. Here, the active compounds Example (I-9) (240 SC) and Example (I-4)
 
- 43 -
(240 SC) and the commercial standard imidacloprid (200 SL) are tested at the stated application rates. The application rate is 1000 1 of water/ha. Three applications are carried out, at an interval of 11 or 10 days.
Evaluation is in each case carried out 7 or 10 days after each treatment, by rating the kill of the 5 larvae on the leaves.
Active
compound    Application rate % of ad.    Kill (%)
        10d
after the 1st
treatment    7d
after the 2nd
treatment    10d
after the 3rd
treatment
imidacloprid    0.015    53.5    88.4    67.5
Example (I-9)    0.0144    63.3    99.6    94.3
Example (1-4)    0.0144    81.9    100    94.3

Example 35
In three replications, plots of a size of 10 m2 with aubergines of the cultivar `F 100" are treated
against Bemisia argentifolii. The application is carried out using a knapsack sprayer operated with
10 pressurized air. Here, the active compounds Example (1-9) (60 SC), Example (1-2) (60 SC) and Example (1-11) (60 SC) and the commercial standard inidacloprid (70 WG) are tested at the stated application rates. Three applications are carried out, at an interval or 7 or 8 days. The application rate is 1000 1 of water/ha.
Evaluation is carried out 7 days after the last treatment by rating the kill of the nymphs on the 15    leaves.
Active
compound    Application rate % of al    Kill (%)
        7d
imidacloprid    0.014    100
 
- 44 -
Example (I-9)    0.0144    98
Example (I-2)    0.0144    100
Example (I-11)    0.0144    94

Example 36
In three replications, in each case four aubergine plants of the cultivar "Ityoma" are treated against
Bemisia argentifolii The application is carried out using a motor-operated knapsack sprayer.
5 Here, the active compounds Example (1-4) and Example (I-8), in a tank mix with 0.2% a.i of rapeseed oil methyl ester (500 EW), and the commercial standard pymetrozine (25 WP) are tested at the stated application rates. The application rate is 32001 of water/ha.
Evaluation is carried out 13, 20 and 27 days after the treatment by rating the kill of the nymphs on the leaves.
Active
compound    Application rate % of ad.    Kill (%)
        13d    20d    27d
pymetrozine    0.0125    79    74    75
Example (1-4)    0.072    99.6    100    97
Example (1-8)    0.06    99.5    99.9    97

10
Example 37
In four replications, plots of a size of about 39 m2 with cantaloupe melons of the cultivar 'Western
Shipper" are treated against Bemisia argentifolii. The application is carried out using a knapsack
sprayer operated with pressurized air. Here, the active compound Example (I-4) (240 SC), in a
15 tank mix with 0.2 a.i. of rapeseed oil methyl ester (500 EW), and the commercial standard endosulfan (360 EC) are tested at the stated application rates. Two applications are carried out at an interval of 16 days. The application rate is 187 1 of water/ha.
 
- 45 -
Evaluation is carried out 5, 13, 21 and 29 days after the first treatment by rating the kill of the animals (nymphs) on the leaves.
Active
compound    Application rate g of
a.i./ha    Kill (%)
        5d    13d    21d    29d
endosulfan    1120    0    100    80.8    66.7
Example (1-4)    48    100    100    98.1    90.5

Example 38
5 In three replications, plots of a size of about 7.5 m2 with melons of the cultivar Tiel DE Sapo" are treated against Bemisia tabaci The application is carried out with a motor-operated knapsack sprayer. Here, the active compound Example (1-4) (240 SC), in a tank mix with 0.1% of a.i. of rapeseed oil methyl ester (500 EW), and the commercial standard Confidor (200 SL) are applied at the stated application rates. Two applications are carried out, at an interval of 7 days and at an
10 application rate of 233 1 of water/ha.
Evaluation is carried out 7 and 15 days after the second treatment by rating the kill of the animals (nymphs) on the leaves.
Active
compound    Application rate g of a.i./ha    Kill (%)
        7d    15d
Confidor    100    98.8    75.7
Example (I-4)    72    85.3    95.5

Example 39
15 In three replications, about 55-year-old orange trees of the cultivar "Amargo" are treated against Aleurothrixus floccosus. The application is carried out using a motor-operated knapsack sprayer. Here, the active compound Example (1-4) (240 SC), in a tank mix with 0.1% a.i. of rapeseed oil
 
- 46 -
methyl ester (500 EW), is tested at the stated application rate against the standard Juvinal (100 EC) at the stated application rates, applied once. The application rate is 2630 1 of water/ha.
Evaluation is carried out 36, 51, 62 and 76 days after the treatment by rating the kill on the branches.
Active
compound    Application rate
% of a.i.    Ki11 (%)
        36d    51d    62d    76d
Juvinal    0.005    57.8    60.7    73.1    74.0
Example (I-4)    0.0072    81.1    81.5    92.1    92.9

Aphids (Aphididae)
Moreover, very particular preference is given to controlling the following species from the family of the aphids, in the following crops:
Myzus persicae    in tobacco, in beet, in fruit vegetables and leafy vegetables, such as, for example, bell peppers, tomatoes, aubergines, head lettuce, potatoes, in stone fruit, such as, for example, peaches, nectarines, plums, cherries, strawberries, melons, in ornamental plants, such as, for example, roses

Myzus nicotianae    in tobacco
Myzus cerasi    in stone fruit, such as, for example, cherries
Aphis gossypii    in cereals, such as, for example, wheat, in pomme fruit, such as, for
example, apples, pears, in stone fruit, such as, for example, peaches,
nectarines, cherries, plums, garden plums, apricots, in citrus fruit,
such as, for example, oranges, mandarins, grapefruits, cucurbits,
 
- 47 -
melons, strawberries, oilseed rape, potatoes, beet, in ornamental plants, such as, for example, roses
Aphis pomi    in pomme fruit, such as, for example, apples, pears
Dysaphis plantaginea    in pomme fruit, such as, for example, apples, pears
Dysaphis pin    in pomme fruit, such as, for example, apples, pears
Aphis fabae    in beet and beans
Rhodobium porosum    in strawberries
Nasonovia ribisnigri    in leafy vegetables, such as, for example, head lettuce
Macrosiphum rosae    in ornamental plants, such as, for example, roses
Macrosiphum    in leafy vegetables, fruit vegetables and brassica vegetables, such as,
euphorbiae    for example, aubergines, lettuce, bell peppers, white cabbage,
strawberries
Phorodon humuli    in hops
Brachycaudus helycrisii    in stone fruit, such as, for example, in plums, garden plums
AuLacorthum solani    in citrus fruit, such as, for example, oranges, mandarins, grapefruits,
limes, in fruit vegetables and leafy vegetables, such as, for example, head lettuce, tomatoes, bell peppers, aubergines
Toxoptera citricola    in citrus fruit, such as, for example, oranges, mandarins, limes,
grapefruits, in stone fruit, such as, for example, peaches, apricots
Toxoptera citricida    in citrus fruit, such as, for example, oranges, mandarins, limes,
grapefruits, in stone fruit, such as, for example, peaches, apricots
Toxoptera aurantii    in citrus fruit, such as, for example, oranges, mandarins, grapefruits,
limes, in spices, such as, for example, pepper, in nuts, such as, for
 
- 48 -
example, cashew nuts
Toxoptera odinae    in citrus fruit, such as, for example, oranges, mandarins, grapefruits,
limes, in spices, such as, for example, pepper, in nuts, such as, for example, cashew nuts
Toxoptera graminum    in cereals, such as, for example, wheat, triticale, sorghum
Example 40
In three replications, three about 22-year-old apple trees of the cultivar 'Golden Delicious" are
treated eradicatively against Dysaphis plantaginea and Aphis pomi. The application is carried out
5 using a motor-operated barrow-mounted sprayer. Here, the active compounds Example (1-9) (240 SC) and Example (1-4) (240 SC) in the stated amount are tested against the commercial standard imidacloprid (200 SL), at the stated application rate. The application rate is 1200 1 of water/ha.
Evaluation is carried out 14 d and 21 d after the treatment by rating the kill of the population on 10 the shoots.
Dysaphis plantaginea
Active
compound    Application rate (%) of a.i.    Kill (%)
        14d    21d
imidacloprid    0.007    97.6    99.8
Example (1-9)    0.0144    99.8    100
Example (1-4)    0.0144    99.3    100

Aphis pomi
Active    Application rate (%) of a.i.    Kill (%)
 
- 49 -
compound       
        14d    21d
imidacloprid    0.007    93.6    92.5
Example (1-9)    0.0144    98.5    97.3
Example (1-4)    0.0144    96.9    98.8

Example 41
In three replications, three about 8-year-old apple trees of the cultivar "Golden Delicious" are
treated eradicatively against Dysaphis plantaginea and Aphis pomi. The application is carried out
using a motor-operated barrow-mounted sprayer. Here, the active compounds Example (1-9)
5 (240 SC) and Example (1-2) (240 SC) in the stated amount are tested against the commercial standard imidacloprid (200 SL), at the stated application rate. The application rate is 1200 1 of water/ha.
Evaluation is carried out before and also 7 d and 14 d after the treatment by counting the live animals on the shoots. The efficacy is then calculated by calculating the effect on the population in 10 per cent according to Henderson and Tilton
Dysaphis plantaginea
Active
compound    Application rate (%) of a.i.    Effect (%)
        7d    14d
imidacloprid    0.007    99.6    99.5
Example (1-9)    0.0144    92.1    99.4
Example (1-2)    0.0144    92.3    99.2

Aphis pomi
Active
compound    Application rate (%) of a.i.    Effect (%)
        7d    14d
 
- 50 -
imidacloprid    0.007    99    83.5
Example (I-9)    0.0144    93    93.5
Example (1-2)    0.0144    99.1    97.1

Example 42
In four replications, plots of a size of 5 m2 with head lettuce are, two weeks after transplantation,
treated against Nasonovia ribisnigri. The application is carried out using a knapsack sprayer
5 operated with pressurized air. Here, the active compounds Example (I-4) (240SC) and Example (I-8) (240 SC) are, in a tank mix with 0.2% al. of rapeseed oil methyl ester (500 EW), tested against the commercial standard Pirimor, at the stated application rates. The application rate is 500 1 of water/ha.
Evaluation is carried out 7, 14 and 26 days after the treatment by rating the kill of the animals on 10    the plants.
Active
compound    Application rate g of a.i./ha    Kill (%)
        7d    14d    26d
Pirimor    150    69.2    53.2    46.3
Example (1-4)    48    92.3    95.7    95.1
Example (1-8)    42    80.8    93.6    92.7
 
- 51 -
Example 43
In three replications, plots of a size of 10 m2 with aubergines of the cultivar `F 100" are treated
against Macrosiphum euphorbiae. The application is carried out using a knapsack sprayer
operated with pressurized air. Here, the active compounds Example (I-9) (60 SC), Example (I-
5 2) (60 SC) and Example (I-11) (60 SC) and the commercial standard imidacloprid (70 WG) are tested at the stated application rates. Three applications are carried out, at an interval of 7 or 8 days. The application rate is 10001 of water/ha.
Evaluation is carried out 7 and 14 days after the second treatment by rating the kill of the nymphs on the leaves.
Active
compound    Application rate (%) of a.i.    Kill (%)
        7d    14d
imidacloprid    0.014    100    100
Example (I-9)    0.0144    99    98
Example (I-2)    0.0144    99    91
Example (I-11)    0.0144    98    99

10
Very particular preference is given to controlling Phorodon humuli in hops. Example 44
In two replications, about 4-year-old hop plants of the cultivar `Spalter" are treated against the
hop aphid Phorodon tumuli The application is carried out using a knapsack sprayer operated
15 with pressurized air. Here, the active compounds Example (I-9) (240SC) and Example (I-4)
(240 SC), in a tank mix with 0.1% a.i. of rapeseed oil methyl ester (500 EW), and the standard
imidacloprid are applied at the stated application rates. The application rate is 1200 1 of water/ha.
The first evaluation is carried out 6 days and the last evaluation 46 days after the treatment by rating the kill of the animals on the leaves.
 
- 52 -
Active
compound    Application rate (%) of a.i.    Kill (%)
        6d    46d
imidacloprid    0.0053    99    97.6
Example (1-9)    0.0036    95    85.2
Example (1-4)    0.0084    95    98.7

Example 45
In three replications, in each case one about 8-year-old orange tree of the cultivar Navel" is
treated against Toxoptera citricida. Here, the active compounds Example (1-9) (240 SC) and
5 Example (1-4) (240 SC), in a tank mix with 0.1% a.i. of Marlipal, are tested against the commercial standard inidacloprid (350 SC), at the stated application rates. The application is carried out using a motor-operated knapsack sprayer, the application rate being 6.7 1 of water/plant.
Evaluation is carried out 6 and 20 days after the treatment by rating the kill of the animals on the 10    leaves.
Active
compound    Application rate (%) of a.i.    Kill (%)
        6d    20d
imidacloprid    0.0125    99    94
Example (1-9)    0.0144    96    97
Example (1-4)    0.0144    97    97

Example 46
In four replications, plots of a size of about 33 m2 with head lettuce of the cultivar "PIC 714" are 15 treated against Aulacorthum solani, Macrosiphum euphorbiae and Myzus persicae. The
 
-53-
application is carried out using a tractor sprayer. Here, the active compound Example (I-4) (240 SC), in a tank mix with 0.2% a.i. of rapeseed oil methyl ester (500 EW), is tested against the commercial standard endosulfan (360 EC), at the stated application rates. The application rate is 187 lof water/ha. Two treatments are carried out, at an interval of 22 days.
5 Evaluation is carried out 8, 22, 30 and 40 days after the first treatment by rating the kill of the nymphs on the plants.
Aulaeorthum solani
Active
compound    Application rate g of
a.i✓ha    Kill (%)
        8d    22d    30d    40d
endosulfan    1120    96    88    98    53
Example (I-4)    48    100    99    79    87

Macrosiphum euphorbiae
Active
compound    Application rate g of
a.i./ha    Kill (%)
        8d    22d    30d    40d
endosulfan    1120    100    100    99    96
Example (I-4)    48    95    100    100    96

10
Myzus persicae
Active
compound    Application rate g of
al./ha    Kill (%)
        8d    22d    30d    40d
endosulfan    1120    95    61    100    - *
Example (I-4)    48    95    100    88    - *

* no animals in the control
 
- 54 -
Example 47
In three replications, under practical conditions, about 18-year-old peach trees of the cultivar
"Viviati' infested with Myzus persicae are treated with Example (1-4) (240 SC) in a tank mix with
0.2% a.i. of rapeseed oil methyl ester (500 EW) in comparison to the commercial standard
5 imidacloprid 200 SL, at the stated application rates. The application is carried out using a motor-operated knapsack sprayer. The application rate is 1000 1 of water/ha.
Evaluation is carried out 7, 14 and 21 days after the application by counting the live animals on the shoots. The efficacy is then calculated by calculating the effect on the population in per cent according to Henderson and Tilten
10
Active
compound    Application rate of a.i. in g/ha/crown height in m    Effect (%)
        7d    14d    21d
imidacloprid    25    97.6    95.8    78.1
Example (I-4)    24    94.0    98.9    93.3

Example 48
In three replications, four aubergine plants (age about 7 months) of the cultivar liayabusa" are
treated against Myzus persicae. The application is carried out using a motor-operated knapsack
15 sprayer. Here, the active compound Example (I-4) (240 SC), in a tank mix with 0.1% a.i. of rapeseed oil methyl ester (500 EW), and the commercial standard pymethrozine (25 WP) are tested at the stated application rates. The application rate is 3000 1 of water/ha.
Evaluation is carried out 7, 14, 21 and 29 days after the treatment by rating the kill of the animals on the leaves.
 
- 55 -
        7d    14d    21d    29d
pymethrozine    0.0125    99.9    99    95    73
Example (1-4)    0.024    99.7    99.7    98    97

Example 49
In four replications, plots of a size of about 7.5 m2 with potatoes of the cultivar 'BP 1" are treated
against Myzus persicae. The application is carried out using a knapsack sprayer operated with
5 pressurized air. Here, the active compound Example (1-4) (240 SC), in a tank mix with 0.2% a.i. of rapeseed oil methyl ester (500 EW), and the commercial standard Tamaron (585 SL) are tested at the stated application rates. Two applications are carried out, at an interval of 7 days. The application rate is 500 1 of water/ha.
Evaluation is carried out 7 and 13 days after the first treatment by counting the live animals 10 (nymphs) on the leaves. The efficacy is then calculated by calculating the effect on the population in per cent according to Henderson and Tilten.
Active
compound    Application rate g of a.i./ha    Effect (%)
        7d    13d
Tamaron    585    100    100
Example (1-4)    48    67    100

15 Example 50
In two replications, plots of a size of about 43 m2 with tomatoes of the cultivar 'Yaqui" are
treated against Myzus persicae. The application is carried out using a motor-operated knapsack
sprayer. Here, the active compounds Example (1-9) (240 SC) and Example (1-4) (240 SC), in a
 
- 56 -
tank mix with 0.1% a.i. of rapeseed oil methyl ester (500 EW), and the standard acetamiprid (20 WP) are applied at the stated application rates. The application rate is 2081 of water/ha.
Evaluation is carried out 3 and 10 days after the treatment by rating the kill of the nymphs on the leaves.
Active
compound    Application rate g of a.i./ha    Kill (%)
        3d    10d
acetamiprid    50    78.7    73.5
Example (1-9)    36    87.5    95.9
Example (1-4)    48    92.6    95.9

5 Example 51
In three replications, plots of a size of 10 m2 with broad beans of the cultivar Trite Weisskeirnige" are treated against Aphis fabae. The application is carried out using a knapsack sprayer operated with pressurized air. Here, the active compounds Example (1-9) (240 SC), Example (1-2) (240 SC) and Example (1-4) (240 SC), in a tank mix with 0.2% of rapeseed oil
10 methyl ester (500 EW), and the commercial standard Pirimor (50 WG) are tested at the stated
application rates. Application is carried out once. The application rate is 500 1 of water/ha.
Evaluation is carried out 7 and 15 days after the treatment by rating the kill of the nymphs on the leaves.
Active
compound    Application rate g of
a.i./ha    Kill (%)
        7d    15d
Pirimor    250    100    100
Example (1-9)    36    99.7    100
Example (I-2)    36    98.6    100
Example (1-4)    42    100    100
 
- 57 -
Example 52
In three replications, plots of a size of 15 m2 with melons are treated against Aphis gossypii. The
application is carried out using a knapsack sprayer operated with pressurized air. Here, the active
compound Example (I-4) (240 SC), in a tank mix with 0.1% a.i. of rapeseed oil methyl ester
5 (500 EW), and the standard imidacloprid (200 SL) are applied at the stated application rates. The application rate is 500 1 of water/ha.
Evaluation is carried out 3 days and 7 days after the treatment by rating the kill of the animals on the shoots.
Active
compound    Application rate g of a.i./ha    Kill (%)
        3d    7d
imidacloprid    100    98.2    100
Example (I-4)    48    94.7    100

10 Example 53
In four replications, plum trees of the cultivar "Angeleno" of a height of about 2.8 m are treated against Myzus persicae. The application is carved out using a high-pressure sprayer. Here, the active compound Example (I-4) (100 OD), in the stated amount, is tested against the commercial standard Actara (25 WG), at the stated application rate. The application rate is 500 1 of
15 water/ha/crown height in m.
Evaluation is carried out 6, 9, 12, 20 days after the treatment by rating the kill of the population on the shoots.
Active
compound    Application rate
g of a.i./ha/crown height
in m            Kill (%)       
        6d    9d    12d    20d    27d
 
- 58 -
Actara    33.5    96.7    96.6    86.9    88.4    89.2
Example (1-4)    48    96.4    99.7    99.8    99.9    99.9

Example 54
In four replications, plots of a size of about 8.4 m2 with 36 11-week-old bell pepper plants of the
cultivar `Casea dura ikeda" are treated against Myzus persicae. The application is carried out
5 using a knapsack sprayer operated with pressurized air. Here, the active compound Example (I¬4) (240SC), in a tank mix with 0.2% a.i. of rapeseed oil methyl ester (500 EW), is tested against the commercial standard Provado (200 SC), at the stated application rates. The application rate is 600 1 of water/ha. There are three applications, in each case at an interval of 7 d.
Evaluation is carried out 1, 7, and 14 days after the last treatment by rating the kill of the animals 10 on the leaves.
Active
compound    Application rate g of a.i./ha    Kill (%)
        ld    7d    14d
Provado    50    99.7    100    98.7
Example (I-4)    48    99.1    98.5    100

Example 55
In four replications, plots of a size of about 3 m2 with 3-week-old strawberry plants are treated
against Macrosiphum euphorbiae and Rhodobium porosum. The application is carried out using a
15 knapsack sprayer operated with pressurized air. Here, the active compound Example (1-4) (150 OD) and the commercial standard Calypso (480 SC) are tested at the stated application rates. Here, the standard is sprayed as a tank mix with 0.03% of Motto (adjuvant). The application rate is 500 1 of water/ha.
Evaluation is carried out 7 and 14 days after the second treatment by rating the kill of the nymphs 20 on the plants.
 
-59-
Active
compound    Application rate
g of a.i./ha    Rhodobium
porosum
Kill (%)    Macrosiphum
euphorbiae
Kill (%)
        7d    14d    7d    14d
Calypso    120    99    98    67.7    96
Example (1-4)    75    97    96    62.2    94
 
- 60 -
Patent claims
1.    Use of the compounds of the formula (I)
 

 
in which
5    X    represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
W, Y aid Z independently of one another represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
A    represents hydrogen, in each case optionally halogen-substituted alkyl,
alkoxyalkyl, saturated, optionally substituted cycloalkyl in which optionally at least 10    one ring atom is replaced by a heteroatom,
B    represents hydrogen or alkyl,
A and B together with the carbon atom to which they are attached represent a saturated or unsaturated, unsubstituted or substituted cycle which optionally contains at least one heteroatom,
15    G    represents hydrogen (a) or represents one of the groups
0
Ri (b),
E (f) or    R4
 • R2 (C),    (d), L// R5 (e),
R6
N    (g)
)R7

in which
 
- 61 -
E    represents a metal ion or an ammonium ion,
L    represents oxygen or sulphur,
M    represents oxygen or sulphur,
RI    represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl,
5    alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl- or alkoxy-substituted
cycloalkyl which may be interrupted by at least one heteroatom, represents in each case optionally substituted phenyl, phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R2    represents in each case optionally halogen-substituted alkyl, alkenyl, alkoxyalkyl,
10    polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl,
phenyl or benzyl,
R3    represents optionally halogen-substituted alkyl or optionally substituted phenyl,
R4 and R5 independently of one another represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cyclo-
15        alkylthio or represent in each case optionally substituted phenyl, benzyl, phenoxy
or phenylthio and
R6 and R7 independently of one another represent hydrogen, in each case optionally
halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent
optionally substituted phenyl, represent optionally substituted benzyl or together 20    with the nitrogen atom to which they are attached represent an optionally
substituted ring which is optionally interrupted by oxygen or sulphur
in the form of their isomer mixtures or pure isomers for controlling insects from the suborder of the plant lice (Stemorrhyncha).
2.    Use of compounds of the formula (1) according to Claim 1, where
25    W    represents hydrogen, CI-Ca-alkyl, C1-C4-alkoxy, chlorine, bromine or fluorine,
 
- 62 -
X    represents C1-C4-alkyl, C 1-C4- alkoxy, CI-C4-haloalkyl, fluorine, chlorine or
bromine,
Y and Z independently of one another represent hydrogen, C1-C4-alkyl, halogen, Ci-C4- alkoxy or C1-C4-haloalkA
5    A    represents hydrogen or in each case optionally halogen-substituted CI-Cs-alkyl or
C3-C8-cycloalkyl,
B    represents hydrogen, methyl or ethyl,
A, B and the carbon atom to which they are attached represent saturated Q-C6- cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur 10    and which is optionally mono- or disubstituted by C1-C4-alkyl, trifluoromethyl or
C 1- C4- alkoxy,
G    represents hydrogen (a) or represents one of the groups
15         R4
R2 (c),    SOk- R3 (d),    , R5 (e),
M
R6
R7 (g)

in which
E    represents a metal ion or an ammonium ion,
L    represents oxygen or sulphur and
M    represents oxygen or sulphur,
 
- 63 -
RI    represents in each case optionally halogen-substituted Ci-C10-alkyl, C2-C10-
alkenyl, C1-C4-alkoxy-C1-C4-alkyl, C 1-Cralkylthio-C1-Cralkyl or optionally fluorine-, chlorine-, C1-C4-alkyl- or C1-C2-alkoxy-substituted C 3- C6-cycloalkyl,
represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4alkyl, 5    C1-C4-alkoxy-, trifluommethyl- or trifluoromethoxy-substituted phenyl,
represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,
R2    represents in each case optionally fluorine- or chlorine-substituted CI-Cm-alkyl,
C2-Cio-alkenyl, C1-C4-alkoxy-C2-C4-alkyl,
10    represents optionally methyl- or methoxy-substituted C5-C6-cycloalkyl or
represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, C1-C4-alkoxy-, trifluoromethyl- or trifluommethoxy-substituted phenyl or benzyl,
R3    represents optionally fluorine-substituted C1-C4-alkyl or represents optionally
15    fluorine-, chlorine-, bromine-, CI-C4ralkyl, C1-C4-alkoxy-, trifluoromethyl-,
trifhioromethoxy-, cyano- or nitro-substituted phenyl,
R4    represents in each case optionally fluorine- or chlorine-substituted C1-C4-alkA
C1-C4-alkoxy, C1-C4-alkylamino, C1-C4-alkylthio or represents in each case
optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C1-C4-alkoxy-,
20        triftuoromethoxy- , C1- C4- alkylthio-, C1- C4-haloalkylthio- , C - Cr alkyl- or
trifluoromethyl-substituted phenyl, phenoxy or phenylthio,
R5    represents C1-C4-alkoxy or C1-C4thioalkyl,
R6    represents C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-alkenyl or
CI-Cralkoxy-C1-C4-alkY15
25    R7    represents CI-C6-alkyl, C3-C6-alkenyl or C1-C4-alkoxy-C1-C4-alkyl,
 
- 64 -
R6 and le together lepiesent an optionally methyl- or ethyl-substituted C3- C6-alkylene
radical in which optionally one carbon atom is replaced by oxygen or sulphur
in the form of their isomer mixtures or pure isomers.
3.    Use of compounds of the formula (I) according to Claim 1, where
5    W    represents hydrogen, methyl, ethyl, chlorine, bromine or methoxy,
X    represents chlorine, bromine, methyl, ethyl, propyl, isopiupyl, methoxy, ethoxy or
triftuoromethyl,
Y and Z independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, trifluoromethyl or methoxy,
10    A    represents methyl, ethyl, propyl, Eopropyl, butyl, Eobutyl, sec-butyl, tert-butyl,
cyclopropyl, cyclopentyl or cyclohexyl,
B    represents hydrogen, methyl or ethyl,
or
A, B and the carbon atom to which they are attached represent saturated C6-cycloalkyl in
15 which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, ethyl, triftuoromethyl, methoxy, ethoxy, icropoxy cx butoxy,
G    represents hydrogen (a) or represents one of the groups
 

 
20    in which
M    represents oxygen or sulphur,
 
- 65 -
RI    represents C1- C8- alkyl, C2- C4- alkenyl, methoxymethyl, ethoxymethyl,
ethylthiomethyl, cyclopropyl, cyclopentyl or cyclohexyl,
represents phenyl which is optionally mono- or disubstituted by fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,
5    or represents in each case optionally chlorine- or methyl-substituted pyridyl or
thienyl,
R2    represents CI-Cr alkyl, Q-C4-alkenyl, methoxyethyl, ethoxyethyl or represents
phenyl or benzyl,
R6 and R.7. independently of one another represent methyl, ethyl or together represent a 10    C5-allcylene radical in which the C3-methylene group is replaced by oxygen
in the form of their isomer mixtures or pure isomers.
4.    Use of compounds of the formula (1) according to Claim 1, where
W    represents hydrogen or methyl,
X    represents chlorine, bromine or methyl,
15    Y and Z independently of one another represent hydrogen, chlorine, bromine or methyl,
A, B and the carbon atom to which they are attached represent saturated C6-cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy,
G    represents hydrogen (a) or represents one of the groups
20    0    0    R6
7-1(
R1)-L NA _R2 (c) or    N    (9)1
(b),

in which
M    represents oxygen or sulphur,
 
- 66 -
R'    represents CI-Ca-alkyl, C2-C4-alkenyl, methoxymethyl, ethoxymethyl,
ethylthiomethyl, cyclopropyl, cyclopentyl, cyclohexyl or
represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
5    represents in each case optionally chlorine- or methyl-substituted pyridyl or
thienyl,
R2    represents C,-Cg-alkyl, C2-C4-alkenyl, methoxyethyl, ethoxyethyl, phenyl or
benzyl,
R6 and le independently of one another represent methyl, ethyl or together represent a 10    C5-alkylene radical in which the C3-methylene group is replaced by oxygen
in the form of their isomer mixtures or pure isomers. 5.    Use of compounds of the formula (I)
 

 
according to Claim 1, where the substituents W, X, Y, Z, R and G are as defined in the 15    table:
W    X    Y    Z    R    G
H    Br    H    CH3    OCH3    CO-i-C3H7
H    Br    H    CH3    OCH3    CO2-C2H5
H    CH3    H    CH3    OCH3    H
H    CH3    H    CH3    OCH3    CO2- C2H5
CH3    CH3    H    Br    OCH3    H
CH3    CH3    H    Cl    OCH3    H
 
- 67 -
W    X    Y    Z    R    G
H    Br    CH3    CH3    OCH3    CO-i-C3H7
H    CH3    Cl    CH3    OCH3    CO2C2H5
CH3    CH3    CH3    CH3    OCH3    H
CH3    CH3    H    Br    0C2115    CO-i-C3H7
H    CH3    CH3    CH3    0C2H5    CO-n-C3H7
H    CH3    CH3    CH3    0C2H5    CO-i-C3H7
H    CH3    CH3    CH3    0C2H5    CO-c-C3H5

6.    Use of compounds of the formula (I) according to Claim 1 for controlling insects from the family of the gall-making aphids (Pemphigidae).
7.    Use of compounds of the formula (I) according to Claim 1 for controlling insects from the
5    family of the phylloxerans (Phylloxeridae).
8.    Use of compounds of the formula (I) according to Claim 1 for controlling insects from the family of the jumping plant lice (Psyllidae).
9.    Use of compounds of the formula (I) according to Claim 1 for controlling insects from the family of the soft scales (Coccidae).
10 10.    Use of compounds of the formula (I) according to Claim 1 for controlling insects from the
family of the armoured scales (Diaspididae).
11.    Use of compounds of the formula (I) according to Claim 1 for controlling insects from the family of the ensign coccids (Ortheziidae).
12.    Use of compounds of the formula (I) according to Claim 1 for controlling insects from the
15    family of the mealy bugs (Pseudococcidae).
13.    Use of compounds of the formula (I) according to Claim 1 for controlling insects from the family of the whiteflies (Aleyrodidae), except for the use of the compounds of the formula (I) according to Claim 1 for controlling the whiteflies Bemisia tabaci (Aleyrodidae) on cotton.
 
- 68 -
14.    Use of compounds of the formula (I) according to Claim 1 for controlling Myzus spp. in tobacco, cereals, stone fruit, soft fruit, fruit vegetables, leafy vegetables, tuber and root vegetables, melons, potatoes, beet, oilseed rape, ornamental plants.
15.    Use of the compounds of the formula (I) according to Claim 1 for controlling Aphis spp.
5    in tobacco, citrus fruit, porn= fruit, stone fruit, cereals, melons, beet, soft fruit, oilseed
rape, fruit vegetables, leafy vegetables, brassica vegetables, tuber and root vegetables, ornamental plants, potatoes, cucurbits.
16.    Use of compounds of the formula (I) according to Claim 1 for controlling Rhodobium porosum in strawberries.
    10 17.    Use of compounds of the formula (1) according to Claim 1 for controlling Nasonovia
ribisnigri in leafy vegetables.
18.    Use of compounds of the formula (1) according to Claim 1 for controlling Dysaphis spp. in pomme fruit.
19.    Use of compounds of the formula (1) according to Claim 1 for controlling Macrosiphum
15    spp. in ornamental plants, cereals, potatoes, leafy vegetables, brassica vegetables and fruit
vegetables, strawberries.
20.    Use of compounds of the formula (1) according to Claim 1 for controlling Rhopalosiphum padi„ Sitobion avenae, Methopolophium dirhodum, Brachycolus noxius in cereals.
21.    Use of compounds of the formula (I) according to Claim 1 for controlling Phorodon
20    hvmuli in hops.
22.    Use of compounds of the formula (I) according to Claim 1 for controlling Brachycaudus helychrisii in stone fruit.
23.    Use of compounds of the formula (I) according to Claim 1 for controlling Toxoptera spp. in citrus fruit, stone fruit, almonds, nuts, cereals, spices.
    25 24.    Use of compounds of the formula (I) according to Claim 1 for controlling Aulacorthum
spp. in citrus fruit, potatoes, fruit vegetables and leafy vegetables.
 
- 69 -
Use of tetramic acid derivatives for controlling insects from the genus of the plant lice (Sternorrhyncha)
Abstract
The present invention relates to the use of tetramic acid derivatives of the formula (1)

 
in which
A, B, G, W, X, Y and Z are as defined above
for controlling insects from the suborder of the plant lice (Sternorrhyncha).
 

W    X    V    Z    R    G    •
H    Br    H    CH3    OCH3    C 0-i-C3H7
H    Br    H    CH3    OCH3    C 02-C2H5
H    CH3    H    CH3    OCH3    H
H    CH3    H    CH3    OCH3    C 02-C2115
CH3    CH3    H    Br    0C113    H
                   
H    Br    CH3    CH3    OCH3    C 0-i-C3117
H    CH3    Cl    CH3    OCH3    C 02C2H5
CH3    CH3    C113    CH3    OCH3    H
CH3    CH3    H    Br    0C21-I5    CO-1-C3117
H    CH3    CH3    CH3    0C2H5    C 0-n-C31-17
H    CH3    CH3    CH3    0C2115    C 0-i -C3H7
H    CH3    CH3    CH3    0C2H5    CO-c-C3H5
for controlling insects from the suborder of the plant lice (stemorrhyncha).
Use of compounds of the formula (I) according to Claim 1 for controlling insects from the Family of the gall-making aphids (Pemphigidae).
Use of compounds of the formula (I) accordinfrto Claim 1 for controlling insects from
the family of the phylloxerans (Phylloxeridae).
 
60
1.    Use of compounds of the formula (D according to Claim 1 for controlling insects from the family of the jumping plant lice (Psyllidae).
5.    Use of compounds of the formula (I) according to Claim 1 for controlling insects from
the family of the soft scales (Coccidae).
Use of compounds of the formula (f)-according to Claim 1 for controlling insects from the family of the armoured scales (Diaspididae).
7.    Use of compounds of the formula (D according to Claim 1 for controlling insects from
the family of the ensign coccids (Ortheziidae).
A.     Use of compounds of the formula (I) according to  Claim 1 for controlling insects from
the family of the mealy bugs (Pseudococcidae).
2.    Use of compounds of the formula (D accordin&to Claim 1 for controlling insects from , the family of the whiteflies (Aleyrodidae), except for the use of the compounds of the formula (I) according to Claim 1 for controlling the whiteflies Bemisia tabaci (Aleyrodidae) on cotton.
JO.    Use of compounds of the formula (D according. to Claim 1 for controlling M_yzus spp._
in tobacco, cereals, stone fruit, soft fruit, fruit vegetables, leafy vegetables, tuber and root vegetables, melons, potatoes, beet, oilseed rape, ornamental plants.
11.    Use of the compounds of the formula  (I) according to Claim 1 for controllin_g_ Aphis
spp. in tobacco, citrus fruit, pomme fruit, stone fruit, cereals, melons, beet, soft fruit, oilseed rape, fruit vegetables, leafy vegetables, brassica Vegetables, tuber and root vegetables, ornamental plants, potatoes, cucurbits.
2.    Use of compounds of the formula CI) accordin& to Claim 1 for controllin& Rhodobium
porosum in strawberries.
Use of compounds of the formula (I) according to Claim 1 for controlling Nasonovia ribisnigri in leafy vegetables.
Use of compounds of the formula (D according to Claim 1 for controlling Dysaphis spp. in pomme fruit.
 
kl
5.    Use of compounds of the formula  (.4  according to Claim 1 for controlling Macrosiphum spp. in ornamental plants, cereals, potatoes, leafy vegetables, brassica vegetables and fruit vegetables, strawberries.
6.    Use of compounds of the formula  (11  according to Claim 1 for controlling_ - Rhopalosiphum padi„ Sitobion avenae, Methopolophium dirhodum, Brachycolus noxius in cereals.
7.    Use of compounds of the formula (I) according to Claim 1 for controlling Phorodon_ humuli in hops.
8.    Use of compounds of the formula  (II  according to Claim 1 for controlling - Brachycaudus helychrisii in stone fruit.
9.    Use of compounds of the formula according to Claim 1 for controlling Toxoptera_, spp. in citrus fruit, stone fruit, almonds, nuts, cereals, spices.
0.    Use of compounds of the formula  (1)  according to Claim 1 for controlling ,
kulacorthum spp. in citrus fruit, potatoes, fruit vegetables and leafy vegetables.,    
 
Page 59: [1] Deleted    LMO    4/29/2009 11:31 AM
1.    Use of the compounds of the formula (I)
 

 
in which
X    represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or
W, Y and Z independently of one another represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
A    represents hydrogen, in each case optionally halogen-substituted alkyl,
alkoxyalkyl, saturated, optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom,
B    represents hydrogen or alkyl,
A and B together with the carbon atom to which they are attached represent a
saturated or unsaturated, unsubstituted or substituted cycle which optionally contains at least one heteroatom,
G    represents hydrogen (a) or represents one of the groups
0
Ri
R6
E (f)    or    N.., 7 (g),
in which
E    represents a metal ion or an ammonium ion,
L    represents oxygen or sulphur,
M    represents oxygen or sulphur,
RI    represents in each case optionally halogen-substituted alkyl, alkenyl,
alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl-or alkoxy-substituted cycloalkyl which may be interrupted by at least one
 
heteroatom, represents in each case optionally substituted p phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,
R2    represents in each case optionally halogen-substituted alkyl, alk, ,
alkoxyalkyl, polyalkoxyalkyl or represents in each case optionally substituted cycloalkyl, phenyl or benzyl,
R3    represents optionally halogen-substituted alkyl or optionally substituted
phenyl,
R4 and R5 independently of one another represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio, cycloalkylthio or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio and
R6 and R7 independently of one another represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent optionally substituted phenyl, represent optionally substituted benzyl or together with the nitrogen atom to which they are attached represent an optionally substituted ring which is optionally interrupted by oxygen or sulphur
in the form of their isomer mixtures or pure isomers for controlling insects from the suborder of the plant lice (Sternorrhyncha).
2.    Use of compounds of the formula (I) according to Claim 1, where
W    represents hydrogen, C_I-Ca-alkyl, C1-C4-alkoxy, chlorine, bromine or
fluorine,
X    represents C1-Ca-alkyl, C1-Ca-alkoxy, C1-C4-haloalkyl, fluorine, chlorine
or bromine,
Y and Z independently of one another represent hydrogen, C1-C4-alkyl, halogen, C1-C4-alkoxy or C -Ca-haloalkyl,
A    represents hydrogen or in each case optionally halogen-substituted C1-C6-
alkyl or C3-C8-cycloalkyl,
B    represents hydrogen, methyl or ethyl,
A, B and the carbon atom to which they are attached represent saturated C3-C6-cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur and which is optionally mono- or disubstituted by C1-Ca-alkyl, trifluoromethyl or CI-Ca-alkoxy,
G    represents hydrogen (a) or represents one of the groups
 
0    R4
(b),-    R2 (c),SO-4
— R3 (4    R5 (e),
R6
E (1)    or    t7 (g),
in which
E    represents a metal ion or an ammonium ion,
L    represents oxygen or sulphur and
M    represents oxygen or sulphur,
RI    represents in each case optionally halogen-substituted CI-Cm-alkyl, C2-
C10-alkenyl, Ci-C4-alkoxy-Ci-C4-alkyl, C1-C4-alkylthio-C1-C4-alkyl or optionally fluorine-, chlorine-, Ci-C4-alkyl- or Ci-C2-alkoxy-substituted C3-C6-cycloalkyl,
represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4-
alkyl-, Ci-C4-alkoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl,    - -
represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,
R2    represents in each case optionally fluorine- or chlorine-substituted C1-Cio-
alkyl, C2-Cio-alkenyl, Ci-C4-alkoxy-C2-C4-alkyl,
represents optionally methyl- or methoxy-substituted C5-C6-cycloalkyl or
represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, Ci-C4-alkyl-, Ci-C4-alkoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl or benzyl,
R3    represents optionally fluorine-substituted C1-C4-alkyl or represents
optionally fluorine-, chlorine-, bromine-, C1-C4-alkyl-, C1-C4-alkoxy-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl,
R4    represents in each case optionally fluorine- or chlorine-substituted C1-C4-
alkyl, C1-C4-alkoxy,    Ci-C4-alkylthio or represents in
each case optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C1-C4-
 
alkoxy-, trifluoromethoxy-, C1-C4-alkylthio-, C1-C4-haloalkylthio-, C1-C4-alkyl- or trifluoromethyl-substituted phenyl, phenoxy or phenylthio.
R5    represents Ci-C4-alkoxy or Ci-C4-thioalkyl,
R6    represents Ci-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C -alltEenyl
C1-C4-alkoxy-C1-C4-alkyl,
R7    represents Ci-C6-alkyl, C3-C6-alkenyl or Ci-C4-alkoxy-Ci-C4-ak1,
R6 and R7 together represent an optionally methyl- or ethyl-substituted C3-C67,::• alkylene radical in which optionally one carbon atom is replaced by oxygen or sulphur
in the form of their isomer mixtures or pure isomers.
3.    Use of compounds of the formula (I) according to Claim 1, where
W    represents hydrogen, methyl, ethyl, chlorine, bromine or methoxy,
X    represents chlorine, bromine, methyl, ethyl, propyl, isopropyl, methoxy,
ethoxy or trifluoromethyl,
Y and Z independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, trifluoromethyl or methoxy,
A    represents methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-
butyl, cyclopropyl, cyclopentyl or cyclohexyl,
B    represents hydrogen, methyl or ethyl,
or
A, B and the carbon atom to which they are attached represent saturated C6- cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, ethyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy,
G    represents hydrogen (a) or represents one of the groups
 
R6
N.„ R7 (n) 0
 
R1    represents C1-Cs-alkyl, C2-C4-alkenyl, methoxymethyl, ethoxymethyl,
ethylthiomethyl, cyclopropyl, cyclopentyl or cyclohexyl,
represents phenyl which is optionally mono- or disubstituted by fluorine, chlorine, bromine, cyan, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,
or represents in each case optionally chlorine- or methyl-subst pyridyl or thienyl,
R2    represents C1-C8-alkyl, C2-C4-alkenyl, methoxyethyl, ethoxyetk1,4r
represents phenyl or benzyl,
R6 and R7 independently of one another represent methyl, ethyl or together represent a C5-alkylene radical in which the C3-methylene group is replaced by oxygen
in the form of their isomer mixtures or pure isomers.
4.    Use of compounds of the formula (1) according to Claim 1, where
W    represents hydrogen or methyl,
X    represents chlorine, bromine or methyl,
Y and Z independently of one another represent hydrogen, chlorine, bromine or methyl,
A, B and the carbon atom to which they are attached represent saturated C6- cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy,
G    represents hydrogen (a) or represents one of the groups
 

 
in which
M    represents oxygen or sulphur,
R'    represents C1-Cg-alkyl, C2-C4-alkenyl, methoxymethyl, ethoxymethyl,
ethylthiomethyl, cyclopropyl, cyclopentyl, cyclohexyl or
 
represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,
R2    represents C1-Cralkyl, C2-C4-alkenyl, methoxyethyl, ethoxyethyl, phenyl
or benzyl,
R6 and R7 independently of one another represent methyl, ethyl or together represent a C5-alkylene radical in which the C3-methylene group is replaced by oxygen
in the form of their isomer mixtures or pure isomers.
 
,',/here the substituents W, X, Y, Z, R and G are  as defined in the table:
W    X    Y    Z    R    G
H    Br    H    CH3    OCH3    CO-i-C3H7
H    Br    H    CH3    OCH3    CO2-C2H5
H    CH3    H    CH3    OCH3    H
H    CH3    H    CH3    OCH3    CO2-C21-15
CH3    CH3    H    Br    OCH3    H
                   
H    Br    CH3    CH3    OCH3    CO-i-C3H7
H    CH3    Cl    CH3    OCH3    CO2C2115
CH3    CH3    CH3    CH3    OCH3    H
CH3    CH3    H    Br    0C2H5    CO-i-C3H7
H    CH3    CH3    CH3    0C2H5    CO-n-C3H7
H    CH3    CH3    CH3    0C2H5    .CO-i-C3H7.
H    CH3    CH3    CH3    0C2H5    CO-c-C3H5

For controlling insects from the suborder of the plant lice (sternorrhyncha).
Use of compounds of the formula (I) according to Claim 1 for controlling insects from the family of the gall-making aphids (Pemphigidae).
3.    Use of compounds of the formula (I) according to Claim 1 for controlling insects from
the family of the phylloxerans (Phylloxeridae).
 
4.    Use of compounds of the formula (I) according to Claim 1 for controlling insects fropi
the family of the jumping plant lice (Psyllidae).
Use of compounds of the formula (I) according to Claim 1 for controlling insect4from the family of the soft scales (Coccidae).
Use of compounds of the formula (I) accordin&to Claim 1 for controlling insects frorr the family of the armoured scales (Diaspididae).
7.    Use of compounds of the formula (I) according to Claim 1 for controlling insects frorr
the family of the ensign coccids (Ortheziidae).
Use of compounds of the formula (I) accordingto Claim 1 for controlling insects fron the family of the mealy bugs (Pseudococcidae).
Use of compounds of the formula (D accordin&to Claim 1 for controlling insects fron the family of the whiteflies (Aleyrodidae), except for the use of the compounds of thi formula (I) according to Claim 1 for controlling the whiteflies Bemisia tabac (Aleyrodidae) on cotton.
10.    Use of compounds of the formula (I) according to Claim 1 for controlling Myzus spc
in tobacco, cereals, stone fruit, soft fruit, fruit vegetables, leafy vegetables, tuber an root vegetables, melons, potatoes, beet, oilseed rape, ornamental plants.
H.    Use of the compounds of the formula  (I) according to Claim 1 for controlling. Aphi
spp. in tobacco, citrus fruit, pomme fruit, stone fruit, cereals, melons, beet, soft frui oilseed rape, fruit vegetables, leafy vegetables, brassica vegetables, tuber and roc vegetables, ornamental plants, potatoes, cucurbits.
/..    Use of compounds of the formula (I) according to Claim 1 for controlling_Rhodobiur
porosum in strawberries.
.    Use of compounds of the formula (I) according to Claim 1 for controlling Nasonovi
ribisnigri in leafy vegetables.
Use of compounds of the formula (D according_ to Claim 1 for controlling Dysaph spp. in pomme fruit.
 
61
i.    Use of compounds of the formula  @  according to Claim 1 for controlling
Macrosiphum spp. in ornamental plants, cereals, potatoes, leafy vegetables, brassica vegetables and fruit vegetables, strawberries.
i.    Use of compounds of the formula _@  according to Claim 1 for controlling
Rhopalosiphum padi„ Sitobion avenae, Methopolophium dirhodum, Brachycolus noxius in cereals.
7.    Use of compounds of the formula (I) accordinj to Claim 1 for  controlling Phorodon
humuli in hops.
S.    Use of compounds of the formula  (11  according to Claim 1 for controlling
Brachycaudus helychrisii in stone fruit.
9. Use of compounds of the formula @  according to Claim 1 for controlling Toxoptera • spp. in citrus fruit, stone fruit, almonds, nuts, cereals, spices.
O.    Use of compounds of the formula  (I)  according to Claim 1 for controlling
Lulacorthum spp. in citrus fruit, potatoes, fruit vegetables and leafy vegetables,       
 
Page 59: [1] Deleted    LMO    4/29/2009 11:31 AM
1.    Use of the compounds of the formula (I)
 

 
in which
X    represents halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyan.),
W, Y and Z independently of one another represent hydrogen, halogen, alkyl, alkoxy, haloalkyl, haloalkoxy or cyano,
A    represents hydrogen, in each case optionally halogen-substituted alkyl,
alkoxyalkyl, saturated, optionally substituted cycloalkyl in which optionally at least one ring atom is replaced by a heteroatom,
B    represents hydrogen or alkyl,
A and B together with the carbon atom to which they are attached represent a
saturated or unsaturated, unsubstituted or substituted cycle which optionally contains at least one heteroatom,
G    represents hydrogen (a) or represents one of the groups
O    R4
R1 (b),     R2 (c),    SOT— R3 (d),    8 P R5 (e),
R6
E (f)    or    N    (g),
in which
E    represents a metal ion or an ammonium ion,
L    represents oxygen or sulphur,
M    represents oxygen or sulphur,
R1    represents in each case optionally halogen-substituted alkyl, alkenyl,
alkoxyalkyl, alkylthioalkyl, polyalkoxyalkyl or optionally halogen-, alkyl-or alkoxy-substituted cycloalkyl which may be interrupted by at least one
 
heteroatom, represents in each case optionally substit    phenyl
'
phenylalkyl, hetaryl, phenoxyalkyl or hetaryloxyalkyl,!k
R2    represents in each case optionally halogen-substituted a .Nalkenyl,
alkoxyalkyl, polyalkoxyalkyl or represents in each case o onally substituted cycloalkyl, phenyl or benzyl,
R3    represents optionally halogen-substituted alkyl or optionally substiltiii--,
phenyl,
R4 and R5 independently of one another represent in each case optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio; cycloalkylthio or represent in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio and
R6 and R7 independently of one another represent hydrogen, in each case optionally halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, represent optionally substituted phenyl, represent optionally substituted benzyl or together with the nitrogen atom to which they are attached represent an optionally substituted ring which is optionally interrupted by oxygen or sulphur
in the form of their isomer mixtures or pure isomers for controlling insects from the suborder of the plant lice (Sternorrhyncha).
2.    Use of compounds of the formula (I) according to Claim 1, where
 W    represents hydrogen, Ci-C4-alkyl, C1-Ca-alkoxy, chlorine, bromine or
fluorine,
X    represents C1-C4-alkyl, C1-Ca-alkoxy, C1-Ca-haloalkyl, fluorine, chlorine
or bromine,
Y and Z independently of one another represent hydrogen, C1-C4-alkyl, halogen, C1-C4-alkoxy or C1-Ca-haloalkyl,
A    represents hydrogen or in each case optionally halogen-substituted C1-C6-
alkyl or C3-C8-cycloalkyl,
B    represents hydrogen, methyl or ethyl,
A, B and the carbon atom to which they are attached represent saturated C3-C6-cycloalkyl in which optionally one ring member is replaced by oxygen or sulphur and which is optionally mono- or disubstituted by CI-Ca-alkyl, trifluoromethyl or C1-Ca-alkoxy,
G    represents hydrogen (a) or represents one of the groups
 
R6
E (f) or    N    (g)
in which
E    represents a metal ion or an ammonium ion,
L    represents oxygen or sulphur and
M    represents oxygen or sulphur,
R1    represents in each case optionally halogen-substituted C1-Cio-alkyl, C2-
C10-alkenyl, C1-Ca-alko xy-C -Ca-alkyl, Ci-C4-alkylthio-C1-C4-alkyl or optionally fluorine-, chlorine-, C1-Ca-alkyl- or Ci-C2-alkoxy-substituted C3-C6-cycloalkyl,
represents optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, C1-C4- alkyl-, Ci-C4-alkoxy-, trifluoromethyl- or trifluoromethoxy-substituted phenyl,
represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,
R2    represents in each case optionally fluorine- or chlorine-substituted C1-C10-
alkyl, C2-C10-alkenyl, C1-C4-alkoxy-C2-C4-alkyl,
represents optionally methyl- or methoxy-substituted C5-C6-cycloalkyl or
represents in each case optionally fluorine-, chlorine-, bromine-, cyano-, nitro-, CI-Ca-alkyl-, C1-Ca-alkoxy-, trifluoromethyl- or trifluoromethoxy¬substituted phenyl or benzyl,
R3    represents optionally fluorine-substituted C1-C4-alkyl or represents
optionally fluorine-, chlorine-, bromine-, Ci-C4-alkyl-, C1-C4-alkoxY-, trifluoromethyl-, trifluoromethoxy-, cyano- or nitro-substituted phenyl,
R4    represents in each case optionally fluorine- or chlorine-substituted C1-C4-
alkyl, Ci-C4-alkoxy, C1-Ca-alkylamino, C1-Ca-alkylthio or represents in each case optionally fluorine-, chlorine-, bromine-, nitro-, cyano-, C1-C4-
 
alkoxy-, trifluoromethoxy-, Ci-C4-alkylthio-, Ci-C4-haloalkylthio-, alkyl- or trifluoromethyl-substituted phenyl, phenoxy or phenylthiAcr
R5    represents CLL-C4-alkoxy or Ci-C4-thioalkyl,
R6    represents Ci-C6-alkyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, C3-C6-a    104.
C1-C4-alkoxy-C1-C4-alkyl,
R7    represents Ci-C6-alkyl, C3-C6-alkenyl or C1-C4-alkoxy-C1-C4-alkyl,
R6 and R7 together represent an optionally methyl- or ethyl-substituted C3-C6- alkylene radical in which optionally one carbon atom is replaced by oxygen or sulphur
in the form of their isomer mixtures or pure isomers.
3.    Use of compounds of the formula (I) according to Claim 1, where
W    represents hydrogen, methyl, ethyl, chlorine, bromine or methoxy,
X    represents chlorine, bromine, methyl, ethyl, propyl, isopropyl, methoxy,
ethoxy or trifluoromethyl,
Y and Z independently of one another represent hydrogen, fluorine, chlorine, bromine, methyl, ethyl, propyl, isopropyl, trifluoromethyl or methoxy,
A    represents methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, tert-
butyl, cyclopropyl, cyclopentyl or cyclohexyl,
B    represents hydrogen, methyl or ethyl,
Or
A, B and the carbon atom to which they are attached represent saturated C6- cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, ethyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy,
G    represents hydrogen (a) or represents one of the groups
)0
Fe (b),         (c)    or    R6
N    (g),

in which
M    represents oxygen or sulphur,
 
RI    represents C1-C8-alkyl, C2-C4-alkenyl, methoxymethyl, ethox)kqlethyl,
ethylthiomethyl, cyclopropyl, cyclopentyl or cyclohexyl,
represents phenyl which is optionally mono- or disubstituted by flitonThe,- chlorine, bromine, cyano, nitro, methyl, ethyl, methoxy, trifluoromethyl or trifluoromethoxy,
or represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,
R2    represents C1-C8-alkyl, C2-C4-alkenyl, methoxyethyl, ethoxyethyl or
represents phenyl or benzyl,
R6 and R7 independently of one another represent methyl, ethyl or together represent a C5-alkylene radical in which the C3-methylene group is replaced by oxygen
in the form of their- isomer mixtures or pure isomers.
4.    Use of compounds of the formula (I) according to Claim 1, where
W    represents hydrogen or methyl,
X    represents chlorine, bromine or methyl,
Y and Z independently of one another represent hydrogen, chlorine, bromine or methyl,
A, B and the carbon atom to which they are attached represent saturated C6- cycloalkyl in which optionally one ring member is replaced by oxygen and which is optionally monosubstituted by methyl, trifluoromethyl, methoxy, ethoxy, propoxy or butoxy,
G    represents hydrogen (a) or represents one of the groups
 

 
M    represents oxygen or sulphur,
R1    represents C1-C8-alkyl, C2-C4-alkenyl, methoxymethyl, ethoxymethyl,
ethylthiomethyl, cyclopropyl, cyclopentyl, cyclohexyl or
 
represents phenyl which is optionally monosubstituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
represents in each case optionally chlorine- or methyl-substituted pyridyl or thienyl,
R2    represents C1-C8-alkyl, C2-C4-alkenyl, methoxyethyl, ethoxyethyl, phenyl
. or benzyl,
R6 and R7 independently of one another represent methyl, ethyl or together represent a C5-alkylene radical in which the C3-methylene group is replaced, by oxygen
in the form of their isomer mixtures or pure isomers.
 
indexation.Ist QCOK tags.Ist

 

 

 

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