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WO2008092851A2 - Compositions actives sur le plan pesticide comprenant des composés 3-acétyl-1-phénylpyrazole - Google Patents

Compositions actives sur le plan pesticide comprenant des composés 3-acétyl-1-phénylpyrazole Download PDF

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Publication number
WO2008092851A2
WO2008092851A2 PCT/EP2008/051026 EP2008051026W WO2008092851A2 WO 2008092851 A2 WO2008092851 A2 WO 2008092851A2 EP 2008051026 W EP2008051026 W EP 2008051026W WO 2008092851 A2 WO2008092851 A2 WO 2008092851A2
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composition according
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WO2008092851A3 (fr
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Christopher Koradin
Jürgen LANGEWALD
Douglas D. Anspaugh
Henry Van Tuyl Cotter
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BASF SE
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BASF SE
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
    • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom

Definitions

  • Pesticidally active compositions comprising 3-acetyl-i-phenylpyrazole compounds
  • the present invention relates to pesticidal compositions comprising as active components at least one 3-acetyl-1-phenylpyrazole compound of the formula I or a salt thereof:
  • X is N or C-R 5 ;
  • R 1 is Ci-C 4 -alkyl or Ci-C 4 -haloalkyl
  • R 2 is NR 6 R 7 or S(O) n R 8 ;
  • R 3 is halogen, Ci-C 4 -haloalkyl, Ci-C 4 -haloalkoxy, SF 5 or S(O) P R 9 ;
  • R 4 is hydrogen or halogen
  • R 5 is halogen
  • R 6 is hydrogen, Ci-C 4 -alkyl, Ci-C 4 -haloalkyl, C(O)R 10 , S(O) q CF 3 ;
  • R 7 is hydrogen or Ci-C 4 -alkyl, or R 6 and R 7 are joined so as together form a C 4 - C ⁇ -alkylene moiety, wherein one Chb-group may be replaced by oxygen or a radical N-R 11 ;
  • R 8 , R 9 , R 10 , R 11 are each independently hydrogen, Ci-C 4 -alkyl or Ci-C 4 -haloalkyl; m, n, p and q are each independently 0, 1 or 2;
  • Another problem encountered concerns the need to have available pest control agents which are effective against a broad spectrum of pests.
  • WO 98/28277 does not disclose pesticidal compositions comprising a compound I according to the present invention and at least one further compound Il having in- creased activity in terms of a synergistic effect, enhancing the spectrum of activity, combining knock-down activity with prolonged control or being useful for resistance management.
  • this object is in part or in whole achieved by the combination at least one compound of the formula I with at least one pesticidally active compound II, selected from the group A as defined hereinafter. Moreover, we have found that simultaneous, that is joint or separate, application of a compound I and one or more compounds Il of the group A or successive application of a compound I and one or more compounds Il of the group A allows enhanced control of pests compared to the control rates that are possible with the individual compounds.
  • the group A of pesticidally active compounds consists of:
  • A.1 GABA-gated chloride channel antagonists selected from A.1.a N-ethyl-2,2-dimethylpropionamide-2-(2,6-dichloro- ⁇ . ⁇ . ⁇ -trifluoro-p-tolyl) hy- drazon, N-ethyl-2,2-dichloro-1-methylcyclopropane-carboxamide-2-(2,6-dichloro- ⁇ . ⁇ . ⁇ -trifluoro-p-tolyl) hydrazon and
  • A.1.b the class of phenylpyrazoles consisting of ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole and the phenylpyrazole compound II.A 2 1 :
  • Nicotinic acetylcholine receptor agonists/antagonists selected from nicotin, thiocyclam, from the class of neonicotinoids consisting of acetamiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid, thiamethoxam and AKD-1022; and the allosteric nicotinic acetylcholine receptor agonist spino- sad;
  • A.3 Juvenile hormone mimics selected from hydroprene, kinoprene, fenoxycarb and pyriproxyfen;
  • A.4 Compounds affecting the oxidative phosphorylation selected from diafenthiuron, fenbutatin oxide, propargite and chlorfenapyr;
  • A.5 Inhibitors of the chitin biosynthesis selected from buprofezin and from the class of benzylureas consisting of bistrifluron, diflubenzuron, flufenoxuron, hexaflumuron, lufenuron and novaluron;
  • A.6 Moulting disruptors selected from cyromazine and from the class of ecdysone agonists consisting of methoxyfenozide and tebufenozide;
  • A.7 Mitochondrial electron transport inhibitors selected from pyridaben, tolfenpyrad and flufenerim;
  • A.9 Inhibitors of the lipid synthesis selected from spirodiclofen, spiromesifen and spi- rotetramat;
  • the present invention relates to pesticidal compositions comprising as active components at least one 3-acetyl-1-phenylpyrazole compound of the formula I or a salt thereof and at least one pesticidally active compound of the group A as defined herein.
  • the present invention also provides methods for the control of insects, acarids or nematodes comprising contacting the insect, acarid or nematode or their food supply, habitat, breeding grounds or their locus with a pesticidally effective amount of a composition as defined herein.
  • the present invention also relates to a method of protecting plants from attack or infestation by insects, acarids or nematodes comprising contacting the plant, or the soil or water in which the plant is growing, with a pesticidally effective amount of a composition as defined herein.
  • the invention also provides a method for the protection of seeds from soil insects and of the seedlings' roots and shoots from soil and foliar insects which comprises contacting the seeds before sowing and/or after pregermination with a pesticidally effective amount o of a composition as defined herein.
  • the invention also relates to the use of a composition as defined herein for combating arthropod pests such as insects or arachnids, or nematodes.
  • the compounds of the group A are commercially available compounds and may be found in The Pesticide Manual, 13 th Edition, British Crop Protection Council (2003) among other publications.
  • Thioamides derivatives in analogy of formula II.A 2 1 and their preparation have been described in WO 98/28279. Metaflumizone and its preparation have been described in EP-A1 462 456. Flupyrazofos has been described in Pesticide Science 54, 1988, p.237-243 and in US 4,822,779. Pyrafluprole and its preparation have been described in JP-A 2002-193709 and in WO 01/00614. Pyriprole and its preparation have been described in WO 98/45274 and in US 6,335,357. Amidoflumet and its preparation have been described in US 6,221 ,890 and in JP-A 21010907.
  • Flufenerim and its preparation have been described in WO 03/007717 and in WO 03/007718. Cyflumetofen and its preparation have been described in WO 04/080180. Preparation methods for neonico- tionids similar to AKD-1022 have been desscribed by Zhang, A. et al. in J.Neurochemistry, 75(3), 2000.
  • Ci-C 4 -alkyl or “Ci-C 2 -alkyl” as used herein refer to a branched or non- branched (linear) saturated hydrocarbon group having 1 to 4 or 1 or 2 carbon atoms, respectively, for example methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2- methylpropyl, 1 ,1-dimethylethyl.
  • Ci-C 4 -haloalkyl or "Ci-C 2 -haloalkyl” as used herein refers to a straight- chained or branched alkyl group having 1 to 4 or 1 or 2 carbon atoms (as mentioned above), wherein some or all of the hydrogen atoms in these groups are replaced by halogen atoms, in particular fluorine or chlorine atoms, as mentioned above, for example chloromethyl, bromomethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoro- methyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 1-chloroethyl, 1-bromoethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl,
  • 2,2,2-trifluoroethyl 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro- 2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, CH 2 -C 2 F 5 , CF 2 -C 2 F 5 , CF(CFs) 2 , 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl,
  • Ci-C 2 -fluoroalkyl relates to methyl or ethyl, wherein 1 , 2, 3, 4, or 5 hydrogen atoms have been replaced by fluorine such as in fluoromethyl, difluoromethyl and trifluoromethyl.
  • Ci-C 4 -alkoxy refers to straight-chain or branched alkyl groups having 1 to 4 carbon atoms (as mentioned above) bonded through oxygen linkages, at any bond in the alkyl group.
  • Examples include Ci-C 4 -alkoxy such as methoxy, ethoxy, propoxy, isopropoxy, butoxy, sec-butoxy, isobutoxy and tert-butoxy.
  • Ci-C 4 -haloalkoxy refers to straight-chain or branched alkyl groups having 1 to 4 carbon atoms (as mentioned above) bonded through an oxygen atom at any bond in the alkyl group, where some or all of the hydrogen atoms in these groups are replaced by halogen atoms, in particular fluorine or chlorine atoms, as mentioned above, for example Ci-C 2 -haloalkoxy, such as chloromethoxy, bromomethoxy, dichlorometh- oxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoro- methoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 1-chloroethoxy, 1- bromoethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoro
  • the compounds I may be present in the neutral form or as their salts. Suitable salts are especially the acid addition salts of those acids whose anions do not have any adverse effect on the action of the compounds according to the present invention and which are agriculturally acceptable.
  • Anions of useful acid addition salts are primarily chloride, bro- mide, fluoride, hydrogen sulphate, sulphate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of Ci-C 4 -alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formula I with an acid of the corresponding anion, preferably of hydro- chloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
  • X is N or preferably C-R 5 ; m is O or i ; R 1 is methyl;
  • R 2 is NR 6 R 7 ; wherein R 6 and R 7 are as defined above and wherein R 6 is in particular selected from the group consisting of hydrogen, Ci-C2-alkyl, Ci-C2-haloalkyl,
  • R 7 is in particular selected from hydrogen or Ci-C2-alkyl, more preferably hydrogen, or the radical NR 6 R 7 is 4-morpholinyl, 1-pyrrolidinyl, 1-piperidinyl, 1-piperazinyl or 4- methylpiperazin-1 -yl; R 3 is halogen or Ci-C2-haloalkyl, more preferably Ci-C2-fluoroalkyl, in particular trifluoromethyl;
  • R 4 is halogen, in particular chlorine
  • R 5 is halogen, in particular chlorine.
  • R 1 is methyl;
  • R 2 is NH 2 ;
  • R 3 is halogen or Ci-C2-fluoroalkyl
  • R 4 is halogen, in particular chlorine
  • R 5 is halogen, in particular chlorine.
  • the compound of the formula I is acetoprole,which corresponds to a compound of the formula I, wherein X is C-R 5 ; m is 1 ; R 1 is methyl; R 2 is Nhb; R 3 is trifluoromethyl; R 4 is chlorine; and R 5 is chlorine.
  • X is C-R 5 ; m is 1 ; R 1 is methyl; R 2 is Nhb; R 3 is trifluoromethyl; R 4 is chlorine; and R 5 is chlorine.
  • a first embodiment of the present invention relates to pesticidal compositions, wherein the compound Il comprises at least one compound of the group A.1 as defined above and in particular is selected from the group of compounds A.1.
  • the compound A.1 is selected from N- Ethyl-2,2-dimethylpropionamide-2-(2,6-dichloro- ⁇ . ⁇ . ⁇ -trifluoro-p-tolyl) hydrazon, N- Ethyl-2,2-dichloro-1 -methylcyclopropane-carboxamide-2-(2,6-dichloro- ⁇ . ⁇ . ⁇ -trifluoro-p- tolyl) hydrazon, acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole and the phenylpyrazole compound II.A 2 1 .
  • compositions wherein the compound A1 is selected from N-ethyl-2,2-dimethylpropionamide-2-(2,6- dichloro- ⁇ . ⁇ . ⁇ -trifluoro-p-tolyl) hydrazon and N-ethyl-2,2-dichloro-1-methyl- cyclopropane-carboxamide-2-(2,6-dichloro- ⁇ . ⁇ . ⁇ -trifluoro-p-tolyl) hydrazon. More preference is also given to those compositions, wherein the compound A1 is selected from fipronil and ethiprole.
  • a second embodiment of the present invention relates to pesticidal compositions, wherein the compound Il comprises at least one compound of the group A.2 as defined above and in particular is selected from the group of compounds A.2.
  • the compound A.2 is selected from thiocyclam, acetamiprid, chlothianidin, dinotefuran, imidacloprid, nitenpyram, thiaclo- prid, thiamethoxam, AKD-1022 and spinosad, in particular from clothianidin, imidaclo- prid, thiamethoxam, especially from imidacloprid and thiamethoxam
  • a third embodiment of the present invention relates to pesticidal compositions, wherein the compound Il comprises at least one compound of the group A.4 as defined above and in particular is selected from the group of compounds A.4. Amongst these, prefer- ence is given to those compositions, wherein the compound A.4 is diafenthiuron.
  • a fourth embodiment of the present invention relates to pesticidal compositions, wherein the compound Il comprises at least one compound of the group A.5 as defined above and in particular is selected from the group of compounds A.5. Amongst these, preference is given to those compositions, wherein the compound A.5 is buprofezin.
  • a fifth embodiment of the present invention relates to pesticidal compositions, wherein the compound Il comprises at least one compound of the group A.7 as defined above and in particular is selected from the group of compounds A.7. Amongst these, prefer- ence is given to those compositions, wherein the compound A.7 is pyridaben or flufen- erim.
  • a sixth embodiment of the present invention relates to pesticidal compositions, wherein the compound Il comprises at least one compound of the group A.8 as defined above and in particular is selected from the group of compounds A.8. Amongst these, preference is given to those compositions, wherein the compound A.8 is indoxacarb or meta- flumizone, in particular metaflumizone.
  • a seventh embodiment of the present invention relates to pesticidal compositions, wherein the compound Il comprises at least one compound of the group A.9 as defined above and in particular is selected from the group of compounds A.9. Amongst these, preference is given to those compositions, wherein the compound A.9 is selected from spirodiclofen, spiromesifen and spirotetramat, in particular from spiromesifen and spiro- tetramat.
  • An eigth embodiment of the present invention relates to pesticidal compositions, wherein the compound Il comprises at least one compound of the group A.10 as defined above and in particular is selected from the group of compounds A.10. Amongst these, preference is given to those compositions, wherein the compound A.10 is selected from amitraz, flubendiamide, pymetrozine, pyridalyl and pyrifluquinazon. Amongst these, preference is given to those compositions wherein the compound A.10 is pymetrozine or pyrifluquinazon.
  • pesticidal compositions containing N-ethyl-2,2- dimethylpropionamide-2-(2,6-dichloro- ⁇ . ⁇ . ⁇ -trifluoro-p-tolyl) hydrazon as compound II.
  • pesticidal compositions containing N-ethyl-2,2-dichloro-1- methylcyclopropane-carboxamide-2-(2,6-dichloro- ⁇ . ⁇ . ⁇ -trifluoro-p-tolyl) hydrazon as compound II.
  • compositions containing fipronil as compound II are especially preferred.
  • compositions containing ethiprole as compound II are especially preferred.
  • pesticidal compositions containing clothianidin as compound II.
  • compositions containing thiamethoxam as compound II are especially preferred.
  • pesticidal compositions containing acetamiprid as compound II Especially preferred are pesticidal compositions containing diafenthiuron as compound II.
  • compositions containing buprofezin as compound II are especially preferred.
  • pesticidal compositions containing pyridaben as compound II are especially preferred.
  • pesticidal compositions containing flufenerim as compound II are especially preferred.
  • pesticidal compositions containing metaflumizone as compound II are especially preferred.
  • pesticidal compositions containing pymetrozine as compound II are especially preferred.
  • compositions containing spiromesifen as compound II are especially preferred.
  • pesticidal compositions containing pyrifluquinazon as compound II are especially preferred.
  • compositions wherein the compound Il is fipronil and the compound of formula I is acetoprole.
  • compositions wherein the compound Il is ethiprole and the compound of formula I is acetoprole.
  • pesticidal compositions wherein the compound Il is N-ethyl- 2,2-dimethylpropionamide-2-(2,6-dichloro- ⁇ . ⁇ . ⁇ -trifluoro-p-tolyl) hydrazon and the compound of formula I is acetoprole.
  • pesticidal compositions wherein the compound Il is N-ethyl- 2,2-dichloro-1-methylcyclopropane-carboxamide-2-(2,6-dichloro- ⁇ . ⁇ . ⁇ -trifluoro-p-tolyl) hydrazon and the compound of formula I is acetoprole.
  • pesticidal compositions wherein the compound Il is clothianidin and the compound of formula I is acetoprole.
  • compositions wherein the compound Il is thiameth- oxam and the compound of formula I is acetoprole.
  • compositions wherein the compound Il is pymetro- zine and the compound of formula I is acetoprole.
  • compositions wherein the compound Il is diafenthi- uron and the compound of formula I is acetoprole.
  • compositions wherein the compound Il is buprofezin and the compound of formula I is acetoprole.
  • pesticidal compositions wherein the compound Il is pyridaben and the compound of formula I is acetoprole.
  • compositions wherein the compound Il is flufenerim and the compound of formula I is acetoprole.
  • pesticidal compositions wherein the compound Il is meta- flumizone and the compound of formula I is acetoprole.
  • compositions wherein the compound Il is spirome- sifen and the compound of formula I is acetoprole.
  • compositions wherein the compound Il is spiro- tetramat and the compound of formula I is acetoprole.
  • compositions wherein the compound Il is pyriflu- quinazon and the compound of formula I is acetoprole.
  • compositions it is pre- ferred to employ the pure active compounds I and II, to which further active compounds, e.g. against harmful fungi or having herbicidal activity, or growth-regulating agents or fertilizers can be added.
  • compositions of the present invention may contain both compounds I and II, or the compounds I and Il can be applied simultaneously, that is jointly or separately, in order to exhibit outstanding action against pests.
  • the compositions are particularly useful for combating pests from the following orders: Insects from the order of the lepidopterans (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argillacea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheima- tobia brumata, Choristoneura fumiferana, Choristoneura occidentalis, Cirphis unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandi- osella, Earias insulana, Elasmopalpus lignosell
  • beetles Coldoptera
  • Agrilus sinuatus for example Agrilus sinuatus, Agriotes lineatus, Agriotes obscu- rus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Aphthona euphoridae, Athous haemorrhoidalis, Atomaria linearis, Blasto- phagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruchus pisorum, Bruchus lentis, Byctiscus betulae, Cassida nebulosa, Cerotoma trifurcata, Cetonia aurata,
  • Leptinotarsa decemlineata Limonius californicus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolontha hippocastani, Melolontha melolontha, Oulema oryzae, Ortiorrhynchus sulcatus, Otiorrhynchus ovatus, Phaedon cochleariae, Phyllobius pyri, Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha horticola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sito- philus granaria,
  • mosquitoes e.g. Aedes aegypti, Aedes albopictus, Aedes vexans, An- astrepha ludens, Anopheles maculipennis, Anopheles crucians, Anopheles albimanus, Anopheles gambiae, Anopheles freeborni, Anopheles leucosphyrus, Anopheles minimus, Anopheles quadrimaculatus, Calliphora vicina, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macellaria, Chrysops discalis, Chrysops silacea, Chrysops atlanticus, Cochliomyia hominivorax, Contarinia sorghicola Cordylobia anthropophaga, Culicoides furens, Culex pipiens, Culex nigripal
  • thrips (Thysanoptera), e.g. Dichromothrips corbetti, Dichromothrips ssp , Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,
  • Isoptera e.g. Calotermes flavicollis, Leucotermes flavipes, Heterotermes aureus, Reticulitermes flavipes, Reticulitermes virginicus, Reticulitermes lucifugus, Termes natalensis, and Coptotermes formosanus,
  • cockroaches e.g. Blattella germanica, Blattella asahinae, Peri- planeta americana, Periplaneta japonica, Periplaneta brunnea, Periplaneta fuligginosa, Periplaneta australasiae, and Blatta orientalis,
  • Hemiptera true bugs
  • Hoplocampa minuta Hoplocampa testudinea, Monomorium pha- raonis, Solenopsis geminata, Solen
  • Vespula squamosa Paravespula vulgaris, Paraves- pula pennsylvanica, Paravespula germanica, Dolichovespula maculata, Vespa crabro, Polistes rubiginosa, Camponotus floridanus, and Linepithema humile,
  • crickets grasshoppers, locusts (Orthoptera), e.g. Acheta domestica, Gryllotalpa gryllo- talpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femurrubrum, Melanoplus mexicanus, Melanoplus sanguinipes, Melanoplus spretus, Nomadacris septemfasciata, Schistocerca americana, Schistocerca gregaria, Dociostaurus maroccanus, Tachycines asynamorus, Oedaleus senegalensis, Zonozerus variegatus, Hieroglyphus daganensis, Kraussaria angulifera, Calliptamus italicus, Chortoicetes terminifera, and Locustana pardalina,
  • Arachnoidea such as arachnids (Acarina), e.g. of the families Argasidae, Ixodidae and Sarcoptidae, such as Amblyomma americanum, Amblyomma variegatum, Ambryomma maculatum, Argas persicus, Boophilus annulatus, Boophilus decoloratus, Boophilus microplus, Dermacentor silvarum, Dermacentor andersoni, Dermacentor variabilis, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Ixodes pacificus, Ornithodorus moubata, Ornithodorus hermsi, Ornithodo- rus turicata, Ornithonyssus bacoti, Otobius megnini, Dermanyss
  • Triggerychus pratensis such as Aculus Westendali, Phyllocoptrata oleivora and Eriophyes sheldoni; Tarsonemidae spp. such as Phytonemus pallidus and Polyphagotarsonemus latus; Tenuipalpidae spp. such as Brevipalpus phoenicis; Tetra- nychidae spp. such as Tetranychus cinnabarinus, Tetranychus kanzawai, Tetranychus pacificus, Tetranychus telarius and Tetranychus urticae, Panonychus ulmi, Panony- chus citri, and Oligonychus pratensis; Araneida, e.g.
  • silverfish, firebrat e.g. Lepisma saccharina and Thermobia domestica
  • centipedes Chilopoda
  • Scutigera coleoptrata centipedes
  • Earwigs e.g. forficula auricularia
  • Pediculus humanus capitis e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pthi- rus pubis, Haematopinus eurysternus, Haematopinus suis, Linognathus vituli, Bovicola bovis, Menopon gallinae, Menacanthus stramineus and Solenopotes capillatus.
  • Plant parasitic nematodes such as root-knot nematodes, Meloidogyne arenaria, Meloi- dogyne chitwoodi, Meloidogyne exigua, Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica and other Meloidogyne species; cyst nematodes, Globodera rostochiensis, Globodera pallida, Globodera tabacum and other Globodera species, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, and other Heterodera species; seed gall nematodes, Anguina funesta, Anguina tritici and other Anguina species; stem and foliar nematodes, Aphelenchoides besseyi, Aphelen- choides fragariae, Aphelen
  • the pesticide compositions according to the present invention are especially useful for the control of Lepidoptera, Coleoptera, Diptera, Thysanoptera and Hymenop- tera.
  • the pesticide compositions according to the present invention are useful for the control of Thysanoptera and Hymenoptera, especially Hymenoptera.
  • the pesticide compositions according to the present invention can be converted into the customary formulations, for example solutions, emulsions, suspensions, dusts, powders, pastes and granules.
  • the use form depends on the particular intended pur- pose; in each case, it should ensure a fine and even distribution of the compounds used according to the invention.
  • the formulations are prepared in a known manner (see e.g. for review US 3,060,084, EP-A 707 445 (for liquid concentrates), Browning, "Agglomeration”, Chemical Engi- neering, Dec. 4, 1967, 147-48, Perry's Chemical Engineer's Handbook, 4th Ed.,
  • auxiliaries suitable for the formulation of agrochemicals such as solvents and/or carriers, if desired emulsifiers, surfactants and dispersants, preservatives, anti- foaming agents, anti-freezing agents, for seed treatment formulation also optionally gelling agents.
  • the pesticidal or parasiticidal formulations comprise besides at least one compound of formula I and one or more compounds Il a liquid or solid carrier and optionally further auxilaries such as emulsifiers, surfactants and dispersants, preservatives, antifoaming agents, anti-freezing agents, for seed treatment formulation also optionally gelling agents.
  • Liquid carriers include conventional solvents.
  • solvents examples include water, aromatic solvents (for example Solvesso products, xylene), paraffins (for example mineral oil fractions), alcohols (for example methanol, butanol, pentanol, benzyl alcohol), ketones (for example cyclohexanone, gamma-butyrolactone), pyrrolidones (NMP(N-methyl-pyrrolidone)), NOP (N-octyl- pyrrolidone)), acetates (glycol diacetate), glycols, fatty acid dimethylamides, fatty acids and fatty acid esters. In principle, solvent mixtures may also be used.
  • aromatic solvents for example Solvesso products, xylene
  • paraffins for example mineral oil fractions
  • alcohols for example methanol, butanol, pentanol, benzyl alcohol
  • ketones for example cyclohexanone, gamma-butyrolactone
  • Suitable emulsifiers are nonionic and anionic emulsifiers (for example polyoxyethylene fatty alcohol ethers, alkylsulfonates and arylsulfonates).
  • dispersants examples include lignin-sulfite waste liquors and methylcellulose.
  • Suitable surfactants used are alkali metal, alkaline earth metal and ammonium salts of lignosulfonic acid, naphthalenesulfonic acid, phenolsulfonic acid, dibutylnaphthalene- sulfonic acid, alkylarylsulfonates, alkyl sulfates, alkylsulfonates, fatty alcohol sulfates, fatty acids and sulfated fatty alcohol glycol ethers, furthermore condensates of sulfonated naphthalene and naphthalene derivatives with formaldehyde, condensates of naphthalene or of naphthalenesulfonic acid with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctylphenol, octylphenol, nonylphenol, alkylphenol polyglycol ethers, tributylphenyl
  • Substances which are suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions are mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, etha- nol, propanol, butanol, cyclohexanol, cyclohexanone, isophorone, highly polar solvents, for example dimethyl sulfoxide, N-methylpyrrolidone or water.
  • mineral oil fractions of medium to high boiling point such as kerosene or diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example toluene, x
  • anti-freezing agents such as glycerin, ethylene glycol, propylene glycol and bactericides can be added to the formulation.
  • Suitable antifoaming agents are for example antifoaming agents based on silicon or magnesium stearate.
  • a suitable preservative is e.g. dichlorophen.
  • gelling agent is carrageen (Satiagel®)
  • Powders, materials for spreading and dustable products can be prepared by mixing or concomitantly grinding the active substances with a solid carrier.
  • Granules for example coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers.
  • solid carriers examples include mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders and other solid carriers.
  • mineral earths such as silica gels, silicates, talc, kaolin, attaclay, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers, such as, for example, ammonium sulfate, ammonium phosphate
  • the formulations comprise from 0.01 to 95% by weight, preferably from 0.1 to 90% by weight, of the active compounds.
  • the active compounds are employed in a purity of from 90% to 100% by weight, preferably 95% to 100% by weight (according to NMR spectrum).
  • respective formulations can be diluted 2-10 fold leading to concentrations in the ready to use preparations of 0.01 to 60% by weight active compounds by weight, preferably 0.1 to 40% by weight.
  • the mixtures of the present invention can be used as such, in the form of their formulations or the use forms prepared therefrom, for example in the form of directly sprayable solutions, powders, suspensions or dispersions, emulsions, oil dispersions, pastes, dustable products, materials for spreading, or granules, by means of spraying, atomiz- ing, dusting, spreading or pouring.
  • the use forms depend entirely on the intended purposes; they are intended to ensure in each case the finest possible distribution of the active compounds according to the invention.
  • Aqueous use forms can be prepared from emulsion concentrates, pastes or wettable powders (sprayable powders, oil dispersions) by adding water.
  • emulsions, pastes or oil dispersions the substances, as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetter, tackifier, dispersant or emulsifier.
  • concentrates composed of active substance, wetter, tackifier, dispersant or emulsifier and, if appropriate, solvent or oil and such concentrates are suitable for dilution with water.
  • the active compound concentrations in the ready-to-use preparations can be varied within relatively wide ranges. In general, they are from 0.0001 to 10%, preferably from 0.01 to 1 % per weight.
  • the active compound(s) may also be used successfully in the ultra-low-volume process (ULV), it being possible to apply formulations comprising over 95% by weight of active compound, or even to apply the active compound without additives.
  • UUV ultra-low-volume process
  • Products for dilution with water for foliar applications may be applied to the seed diluted or undiluted.
  • the active compound(s) 10 parts by weight of the active compound(s) are dissolved in 90 parts by weight of water or a water-soluble solvent. As an alternative, wetters or other auxiliaries are added. The active compound(s) dissolve(s) upon dilution with water, whereby a formu- lation with 10 % (w/w) of active compound(s) is obtained.
  • Emulsions EW, EO, ES
  • 25 parts by weight of the active compound(s) are dissolved in 35 parts by weight of xylene with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight).
  • This mixture is introduced into 30 parts by weight of water by means of an emulsifier machine (e.g. Ultraturrax) and made into a homogeneous emulsion. Dilution with water gives an emulsion, whereby a formulation with 25% (w/w) of active compound(s) is obtained.
  • an emulsifier machine e.g. Ultraturrax
  • 50 parts by weight of the active compound(s) are ground finely with addition of 50 parts by weight of dispersants and wetters and made as water-dispersible or water-soluble granules by means of technical appliances (for example extrusion, spray tower, fluid- ized bed). Dilution with water gives a stable dispersion or solution of the active compound ⁇ ), whereby a formulation with 50% (w/w) of active compound(s) is obtained.
  • 75 parts by weight of the active compound(s) are ground in a rotor-stator mill with addition of 25 parts by weight of dispersants, wetters and silica gel. Dilution with water gives a stable dispersion or solution of the active compound(s), whereby a formulation with 75% (w/w) of active compound(s) is obtained.
  • Products to be applied undiluted for foliar applications may be applied to the seed diluted or undiluted.
  • 0.5 parts by weight of the active compound(s) is ground finely and associated with 95.5 parts by weight of carriers, whereby a formulation with 0.5% (w/w) of active com- pound(s) is obtained.
  • Current methods are extrusion, spray-drying or the fluidized bed. This gives granules to be applied undiluted for foliar use.
  • oils, wetters, adjuvants, herbicides, fungicides, other pesticides, or bactericides may be added to the active ingredients, if appropriate just immediately prior to use (tank mix). These agents usually are admixed with the agents according to the invention in a weight ratio of 1 :10 to 10:1.
  • the compounds I and the one or more compound(s) Il can be applied simultaneously, that is jointly or separately, or in succession, the sequence, in the case of separate application, generally not having any effect on the result of the control measures.
  • the compounds I and the one or more compound(s) Il are usually applied in a weight ratio sufficient to achieve the desired synergist action.
  • the wheight ratio of compound I to compound Il is in the range from 1000:1 to 1 :200, preferably from 500:1 to 1 :100.
  • the application rates of the compositions according to the invention are from 1 g/ha to 2000 g/ha, preferably from 5 to 1500 g/ha, in particular from 10 to 750 g/ha, calculated as the applied amount of compound I + compound II.
  • compositions according to the invention are effective through both contact and ingestion.
  • compositions according to the present invention are employed via soil application.
  • Soil application is especially favorable for use against ants, termites, crickets, or cockroaches.
  • compositions according to the present invention are prepared into a bait preparation.
  • the bait can be a liquid, a solid or a semisolid preparation (e.g. a gel).
  • compositions of this invention may further contain other active ingredients than those listed above.
  • active ingredients for example fungicides, herbicides, fertilizers such as ammonium nitrate, urea, potash, and superphosphate, phytotoxicants and plant growth regulators and safeners.
  • additional ingredients may be used sequentially or in combination with the above-described compositions, if appropriate also added only immediately prior to use (tank mix).
  • the plant(s) may be sprayed with a composition of this invention either before or after being treated with other active ingredients.
  • compositions according to the invention can be applied to any and all developmental stages, such as egg, larva, pupa, and adult.
  • the pests may be controlled by contacting the target pest, its food supply, habitat, breeding ground or its locus with a pes- ticidally effective amount of the inventive mixtures or of compositions comprising the mixtures.
  • Locus means a plant, seed, soil, area, material or environment in which a pest is growing or may grow.
  • pesticidally effective amount means the amount of the inventive mixtures or of compositions comprising the mixtures needed to achieve an observable effect on growth, including the effects of necrosis, death, retardation, prevention, and removal, destruction, or otherwise diminishing the occurrence and activity of the target organism.
  • the pesticidally effective amount can vary for the various mixtures / compositions used in the invention.
  • a pesticidally effective amount of the mixtures / compositions will also vary according to the prevailing conditions such as desired pesticidal effect and duration, weather, target species, locus, mode of application, and the like.
  • compositions can also be employed for protecting plants from attack or infestation by insects, acarids or nematodes comprising contacting a plant, or soil or water in which the plant is growing.
  • the term plant refers to an entire plant, a part of the plant or the propagation material of the plant, that is, the seed or the seedling.
  • Plants which can be treated with the inventive mixtures include all genetically modified plants or transgenic plants, e.g. crops which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods, or plants which have modified characteristics in comparison with existing plants, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures.
  • compositions according to the present invention are therefore suitable for the treatment of seeds in order to protect the seed from insect pest, in particular from soil-living insect pests and the resulting plant's roots and shoots against soil pests and foliar insects.
  • the protection of the resulting plant's roots and shoots is preferred. More pre- ferred is the protection of resulting plant's shoots from piercing and sucking insects, wherein the protection from aphids is most preferred.
  • the present invention therefore comprises a method for the protection of seeds from insects, in particular from soil insects and of the seedlings' roots and shoots from in- sects, in particular from soil and foliar insects, said method comprising contacting the seeds before sowing and/or after pregermination with compositions according to the present invention.
  • a method wherein the plant's roots and shoots are protected, more preferably a method, wherein the plants shoots are protected form piercing and sucking insects, most preferably a method, wherein the plants shoots are protected from aphids.
  • seed embraces seeds and plant propagules of all kinds including but not limited to true seeds, seed pieces, suckers, corms, bulbs, fruit, tubers, grains, cuttings, cut shoots and the like and means in a preferred embodiment true seeds.
  • seed treatment comprises all suitable seed treatment techniques known in the art, such as seed dressing, seed coating, seed dusting, seed soaking and seed pelleting.
  • the present invention also comprises seeds coated with or containing the active compound ⁇ ) I and II.
  • coated with and/or containing generally signifies that the active ingredient(s) are for the most part on the surface of the propagation product at the time of application, although a greater or lesser part of the ingredient may penetrate into the propagation product, depending on the method of application. When the said propagation product are (re)planted, it may absorb the active ingredient.
  • Suitable seeds are seeds of cereals, root crops, oil crops, vegetables, spices, ornamentals, for example seed of durum and other wheat, barley, oats, rye, maize (fodder maize and sugar maize / sweet and field corn), soybeans, oil crops, crucifers, cotton, sunflowers, bananas, rice, oilseed rape, turnip rape, sugarbeet, fodder beet, eggplants, potatoes, grass, lawn, turf, fodder grass, tomatoes, leeks, pumpkin/squash, cabbage, iceberg lettuce, pepper, cucumbers, melons, Brassica species, beans, peas, garlic, onions, carrots, tuberous plants such as potatoes, sugar cane, tobacco, grapes, petunias, geranium/pelargoniums, pansies and impatiens.
  • compositions according to the invention may also be used for the treatment of seeds from plants, which tolerate the action of herbicides or fungicides or insecticides owing to breeding, including genetic engineering methods.
  • the active compositions can be employed in treatment of seeds from plants, which are resistant to herbicides from the group consisting of the sulfonylureas, imidazolinones, glufosinate-ammonium or glyphosate-isopropylammonium and analogous active substances (see for example, EP-A-0242236, EP-A-242246) (WO 92/00377) (EP-A-0257993, U.S. Pat. No. 5,013,659) or in transgenic crop plants, for example cotton, with the capability of producing Bacillus thuringiensis toxins (Bt toxins) which make the plants resistant to certain pests (EP-A-0142924, E P-A-0193259),
  • compositions according to the present invention can be used also for the treatment of seeds from plants, which have modified characteristics in comparison with existing plants consist, which can be generated for example by traditional breeding methods and/or the generation of mutants, or by recombinant procedures).
  • a number of cases have been described of recombinant modifications of crop plants for the purpose of modifying the starch synthesized in the plants (e.g. WO 92/11376, WO 92/14827, WO 91/19806) or of transgenic crop plants having a modified fatty acid composition (WO 91/13972).
  • the seed treatment application of the compositions is carried out by spraying or by dusting the seeds before sowing of the plants and before emergence of the plants.
  • the corresponding formulations are applied by treating the seeds with an effective amount of the composition according to the present invention.
  • the application rates of the active compounds I and Il are generally from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 2.5 kg per 100 kg of seed. For specific crops such as lettuce the rate can be higher.
  • compositions which are especially useful for seed treatment may be formulated as e.g.:
  • a Soluble concentrates (SL, LS)
  • Conventional seed treatment formulations include for example flowable concentrates
  • FS solutions LS, powders for dry treatment DS, water dispersible powders for slurry treatment WS, water-soluble powders SS and emulsion ES and EC and gel formulation GF.
  • These formulations can be applied to the seed diluted or undiluted. Application to the seeds is carried out before sowing, either directly on the seeds or after having pre- germinated the latter.
  • a FS formulation is used for seed treatment.
  • a FS formulation may comprise 1-800 g/l of active ingredient(s), 1-200 g/l of surfactant, 0 to 200 g/l of antifreezing agent, 0 to 400 g/l of binder, 0 to 200 g/l of a pigment and up to 1 liter of a solvent, preferably water.
  • Preferred FS formulations of compositions according to the present invention for seed treatment usually comprise from 0.1 to 80% by weight (1 to 800 g/l) of the active ingredients), from 0.1 to 20 % by weight (1 to 200 g/l) of at least one surfactant, e.g. 0.05 to 5 % by weight of a wetter and from 0.5 to 15 % by weight of a dispersing agent, up to 20 % by weight, e.g. from 5 to 20 % of an anti-freeze agent, from 0 to 15 % by weight, e.g. 1 to 15 % by weight of a pigment and/or a dye, from 0 to 40 % by weight, e.g.
  • a binder (sticker /adhesion agent), optionally up to 5 % by weight, e.g. from 0.1 to 5 % by weight of a thickener, optionally from 0.1 to 2 % of an anti-foam agent, and optionally a preservative such as a biocide, antioxidant or the like, e.g. in an amount from 0.01 to 1 % by weight and a filler/vehicle up to 100 % by weight.
  • a binder sticker /adhesion agent
  • a preservative such as a biocide, antioxidant or the like
  • Seed treatment formulations may additionally also comprise binders and optionally colorants.
  • Binders can be added to improve the adhesion of the active materials on the seeds after treatment.
  • Suitable binders are block copolymers EO/PO surfactants but also po- lyvinylalcoholsl, polyvinylpyrrolidones, polyacrylates, polymethacrylates, polybutenes, polyisobutylenes, polystyrene, polyethyleneamines, polyethyleneamides, polyethyle- neimines (Lupasol®, Polymin®), polyethers, polyurethans, polyvinylacetate, tylose and copolymers derived from these polymers.
  • colorants can be included in the formulation. Suitable colorants or dyes for seed treatment formulations are Rhodamin B, C.I. Pigment Red 112, C.I. Solvent Red 1 , pigment blue 15:4, pigment blue 15:3, pigment blue 15:2, pigment blue 15:1 , pigment blue 80, pigment yellow 1 , pigment yellow 13, pigment red 112, pigment red 48:2, pigment red 48:1 , pigment red 57:1 , pigment red 53:1 , pigment orange 43, pigment orange 34, pigment orange 5, pigment green 36, pigment green 7, pigment white 6, pigment brown 25, basic violet 10, basic violet 49, acid red 51 , acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.
  • the invention also relates to seed comprising compositions according to the present invention.
  • the amount of the compounds I + Il or the agriculturally useful salts thereof will in general vary from 0.1 g to 10 kg per 100 kg of seed, preferably from 1 g to 5 kg per 100 kg of seed, in particular from 1 g to 1000 g per 100 kg of seed.
  • compositions are effective through both contact (via soil, glass, wall, bed net, carpet, plant parts or animal parts), and ingestion (bait, or plant part) and through trophallaxis and transfer.
  • Preferred application methods are into water bodies, via soil, cracks and crevices, pastures, manure piles, sewers, into water, on floor, wall, or by perimeter spray application and bait.
  • the inventive mixtures are prepared into a bait preparation.
  • the bait can be a liquid, a solid or a semisolid preparation (e.g. a gel).
  • the bait employed in the composition is a product which is sufficiently attractive to incite insects such as ants, termites, wasps, flies, mosquitoes, crickets etc. or cockroaches to eat it.
  • This attractant may be chosen from feeding stimulants or para and / or sex phero- mones readily known in the art.
  • Methods to control infectious diseases transmitted by insects with the inventive mixtures and their respective compositions also comprise treating surfaces of huts and houses, air spraying and impregnation of curtains, tents, clothing items, bed nets, tsetse-fly trap or the like, lnsecticidal compositions for application to fibers, fabric, knitgoods, non- wovens, netting material or foils and tarpaulins preferably comprise a composition including the inventive compositions, optionally a repellent and at least one binder.
  • inventive compositions can be used for protecting wooden materials such as trees, board fences, sleepers, etc. and buildings such as houses, outhouses, factories, but also construction materials, furniture, leathers, fibers, vinyl articles, electric wires and cables etc. from ants and/or termites, and for controlling ants and termites from doing harm to crops or human being (e.g. when the pests invade into houses and public fa- cilities).
  • the quantity of active compounds I + Il ranges from 0.0001 to 500 g per 100 m 2 , preferably from 0.001 to 20 g per 100 m 2 .
  • Customary application rates in the protection of materials are, for example, from 0.01 g to 1000 g of active compounds I + Il per m 2 treated material, desirably from 0.1 g to 50 g per m 2 .
  • lnsecticidal compositions for use in the impregnation of materials typically contain from 0.001 to 95 weight %, preferably from 0.1 to 45 weight %, and more preferably from 1 to 25 weight % of at least one repellent and / or insecticide.
  • the typical content of active compounds I + Il is from 0.0001 weight % to 15 weight %, desirably from 0.001 weight % to 5% weight % of active compound.
  • the composition used may also comprise other additives such as a solvent of the active material, a flavoring agent, a preserving agent, a dye or a bitter agent. Its attractiveness may also be enhanced by a special color, shape or texture.
  • the content of the mixture of the active ingredients I + 11 is from 0.001 to 80 weight %, preferably from 0.01 to 50 weight % and most preferably from 0.01 to 15 weight %.
  • the rate of application of the mixture of the active ingre- washers I + Il of this invention may be in the range of 0.1 g to 4000 g per hectare, desirably from 25 g to 600 g per hectare, more desirably from 50 g to 500 g per hectare.
  • Synergism can be described as an interaction where the combined effect of two or more compounds is greater than the sum of the individual effects of each of the compounds.
  • the presence of a synergistic effect in terms of percent control, between two mixing partners (X and Y) can be calculated using Limpel's formula (Limpel, L. E.; Schuldt, P. H.; Lamont, D. Proc. N. E. Weed Control. Conf. 1962, 16, 48-53, see also Colby, S. R., 1967, Calculating Synergistic and Antagonistic Responses in Herbicide Combinations, Weeds, 15, 20-22):
  • test unit For evaluating control of vetch aphid (Megoura viciae) through contact or systemic means the test unit consists of 24-well-microtiter plates containing broad bean leaf disks.
  • the compounds or mixtures are formulated using a solution containing 75% water and 25% dimethyl sulfoxide (DMSO). Different concentrations of formulated compounds or mixtures are sprayed onto the leaf disks at 2.5 ⁇ l, using a custom built micro atomizer, at two replications.
  • DMSO dimethyl sulfoxide
  • the leaf disks are air-dried and 5 to 8 adult aphids placed on the leaf disks inside the microtiter plate wells.
  • the aphids are then allowed to suck on the treated leaf disks and incubated at 23 ⁇ 1 0 C, 50 ⁇ 5 % RH (room humidity) for 5 days. Aphid mortality and fecundity is visually assessed. The results are presented in the following table 1 :
  • test unit For evaluating control of boll weevil (Anthonomus grandis) the test unit consists of 24- well-microtiter plates containing an insect diet and 20-30 A. grandis eggs.
  • the compounds or mixtures are formulated using a solution containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures are sprayed onto the insect diet at 20 ⁇ l, using a custom built micro atomizer, at two replications.
  • test unit For evaluating control of Mediterranean fruitfly (Ceratitis capitata) the test unit consists of 96-well-microtiter plates containing an insect diet and 50-80 C. capitata eggs.
  • the compounds or mixtures are formulated using a solution containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures are sprayed onto the insect diet at 5 ⁇ l, using a custom built micro atomizer, at two replications.
  • test unit For evaluating control of tobacco budworm (Heliothis virescens) the test unit consists of 96-well-microtiter plates containing an insect diet and 15-25 H. virescens eggs.
  • the compounds or mixtures are formulated using a solution containing 75% water and 25% DMSO. Different concentrations of formulated compounds or mixtures are sprayed onto the insect diet at 10 ⁇ l, using a custom built micro atomizer, at two replications.
  • Percent mortality observed was greater than the percent mortality expected, which was indicative of synergy, based on Limpel's formula.
  • Percent mortality observed was greater than the percent mortality expected, which was indicative of synergy, based on Limpel's formula.

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Abstract

La présente invention concerne des compositions pesticides comprenant en tant que des composants actifs au moins un composé 3-acétyl-1-phénypyrazol de formule (I) ou un sel de celui-ci : dans laquelle X est N ou C-R5; R1 est un groupe alkyle en C1-C4 ou haloalkyle en C1-C4; R2 est NR6 R7 ou S(O)nR8; R3 est un atome d'halogène, un groupe haloalkyle en C1-C4, haloalkoxy en C1-C4, SF5 ou S(O)pR9; R4 est un atome d'hydrogène ou d'halogène; R5 est un atome d'halogène; R6 est un atome d'hydrogène, un groupe alkyle en C1-C4, un groupe haloalkyle en C1-C4, C(O)R10, S(O)qCF3; R7 est un atome d'hydrogène ou un groupe alkyle en C1-C4, ou R6 et R7 sont joints pour former ensemble une fraction alkylène en C4-C6, un groupe CH2 pouvant être remplacé par un atome d'oxygène ou un radical N-R11; R8, R9, R10, R11 sont indépendamment un atome d'hydrogène, un groupe alkyle en C1-C4 ou haloalkyle en C1-C4; m, n, p et q sont chacun indépendamment 0, 1 ou 2; et au moins un autre composé II actif sur le plan pesticide, choisi parmi A.1 les antagonistes des canaux chlorure à activation GABA; A.2 les agonistes/antagonistes des récepteurs nicotiniques de l'acétylcholine; A.3 les mimétiques de l'hormone juvénile; A.4 les composés affectant la phosphorylation oxydative; A.5 les inhibiteurs de la biosynthèse de la chitine; A.6 les perturbateurs de mue; A.7 les inhibiteurs du transport des électrons mitochondriaux; A.8 les bloquants des canaux sodiques dépendants du voltage; A.9 les inhibiteurs de la synthèse des lipides; et A.10 un groupe de différents composés.
PCT/EP2008/051026 2007-01-30 2008-01-29 Compositions actives sur le plan pesticide comprenant des composés 3-acétyl-1-phénylpyrazole Ceased WO2008092851A2 (fr)

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CN101873800A (zh) * 2007-11-28 2010-10-27 日本农药株式会社 农业和园艺杀虫剂组合物
JPWO2009069676A1 (ja) * 2007-11-28 2011-04-14 日本農薬株式会社 農園芸用殺虫剤組成物
JP2011505394A (ja) * 2007-12-03 2011-02-24 バイエル・クロツプサイエンス・アクチエンゲゼルシヤフト エチプロールおよび特定のカーバメートを含む殺害虫性化合物混合物
CN104222117A (zh) * 2014-09-03 2014-12-24 扬州大学 含有螺虫乙酯的防治斑潜蝇和烟粉虱的农药制剂
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