WO2012000922A2 - Nouvelle utilisation - Google Patents

Nouvelle utilisation Download PDF

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Publication number
WO2012000922A2
WO2012000922A2 PCT/EP2011/060685 EP2011060685W WO2012000922A2 WO 2012000922 A2 WO2012000922 A2 WO 2012000922A2 EP 2011060685 W EP2011060685 W EP 2011060685W WO 2012000922 A2 WO2012000922 A2 WO 2012000922A2
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WO
WIPO (PCT)
Prior art keywords
crc
alkyl
spp
halogen
alkoxy
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Ceased
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PCT/EP2011/060685
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English (en)
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WO2012000922A3 (fr
Inventor
Pierre Ducray
François PAUTRAT
Jacques Bouvier
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Novartis AG
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Novartis AG
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Publication of WO2012000922A3 publication Critical patent/WO2012000922A3/fr
Anticipated expiration legal-status Critical
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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
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • 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
    • A01N43/60—1,4-Diazines; Hydrogenated 1,4-diazines
    • 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
    • A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
    • A01N43/84—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms six-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,4

Definitions

  • the present invention relates to the use of certain 2,4,6-trisubstituted 5-aminopyrimidine compounds, especially insects and acari, in agriculture, processes in the control of agricultural or botanical pests, and furthermore agricultural compositions containing one or more of these compounds.
  • the present invention therefore in one aspect relates to a the use of a compound of formula
  • (Ri )i -5 is 1 to 5 same or different substituents selected from the group consisting of CrC 4 -alkyl, halogen-CrC 4 -alkyl, hydroxy-CrC 4 -alkyl, Ci-C 4 -alkoxy-Ci-C 4 -alkyl, R2R 3 N-C1-C4- alkyl, halogen, cyano, hydroxy, CrC 4 -alkoxy, halogen-CrC 4 -alkoxy, thiol, CrC 4 -alkylthio, halogen-CrC 4 -alkylthio, CrC 4 -alkanoyl, halogen-CrC 4 -alkanoyl, Ci-C 4 -alkanoylamino, PAT054251 -WO-PCT
  • Alkyl - as a group per se and as structural element of other groups and compounds such as halogen-alkyl, hydroxyl-alkyl, alkoxy-alkyl, R 2 R 3 N-alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl or alkylsulfonyloxy alkylsulfonylamino - is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question, either straight-chained, i.e.
  • alkyl methyl, ethyl, propyl, butyl, pentyl, hexyl, heptyl or octyl, or branched, e.g. isopropyl, isobutyl, sec. -butyl, tert. -butyl, isopentyl, neopentyl or isohexyl.
  • Preferred meanings of alkyl are methyl, ethyl or n- or isopropyl, in particular Ci-C 2 -alkyl and especially methyl or ethyl.
  • Alkoxy - as a group per se and as structural element of other groups - is for example methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec.-butoxy or tert.-butoxy; preferably CrC 2 -alkoxy, and especially methoxy or ethoxy.
  • PAT054251 -WO-PCT is for example methoxy, ethoxy, propoxy, isopropoxy, n-butoxy, isobutoxy, sec.-butoxy or tert.-butoxy; preferably CrC 2 -alkoxy, and especially methoxy or ethoxy.
  • Halogen - as a group per se and as structural element of other groups - preferably means, for example, iodine, bromine, chlorine or fluorine, preferably chlorine or fluorine.
  • Halogen-substituted carbon-containing groups and compounds such as halogen-alkyl, halogen-CrC 4 -alkoxy, halogen-Ci-C 4 -alkylthio, halogen -Ci-C 4 -alkanoyl, halogen-Ci-C 4 - alkanoylamino, halogen-Ci-C 4 -alkylsulfonyloxy or halogen-CrC 4 -alkylsulfonyl, may be partially halogenated or perhalogenated, whereby in the case of multiple halogenation, the halogen substituents may be identical or different.
  • halogen-alkyl - as a group per se and as structural element of other groups and compounds such as halogen- alkoxy or halogen-alkylthio, - are methyl which is mono- to trisubstituted by fluorine, chlorine and/or bromine, such as CHF 2 or CF 3 ; ethyl which is mono- to pentasubstituted by fluorine, chlorine and/or bromine, such as CH 2 CF 3 , CF 2 CF 3 , CF 2 CCI 3 , CF 2 CHCI 2 , CF 2 CHF 2 ,
  • heterocyclic radicals or heterocyclic rings are thienyl, furanyl, pyrryl, pyrrolidinyl, dioxolanyl, oxazolyl, thiadiazolyl, oxadiazolyl, pyrazolyl, pirazinyl, piperazinyl, piperidinyl, morpholinyl, pyridyl, pyrimidyl, s-triazinyl, 1 ,2,4-triazinyl, imidazolyl, thiazolyl, triazolyl, tetrazolyl, benzothienyl, benzofuranyl, benzothiazolyl, benzoxazolyl,
  • benzimidazolyl, benztriazolyl, indolyl or indazolyl which may each be further substituted, for example, by Ci-C 2 -alkyl or halogen.
  • X 2 are different or preferably identical and are each most preferably chlorine or fluorine, in particular fluorine.
  • R 2 and R 3 are hydrogen or Ci-C 2 -alkyl, which is unsubstituted or substituted by chlorine hydroxyl, methoxy, ethoxy, thiol, methylthio or ethylthio. Most preferred meanings of R 2 and R 3 are hydrogen, methyl, ethyl or hydroxyethyl.
  • Preferred radicals NR2R 3 are amino, methylamino, ethylamino, N.N-dimethylamino, N,N- diethylamino and N-2-hydroxyethylamino, in particular amino or ⁇ , ⁇ -dimethyl- or diethylamino.
  • R 2 R 3 N-Ci-C 4 -alkyl examples include R 2 R 3 N-ethyl or, in particular R 2 R 3 N-methyl, wherein the above-given meaning and preferences apply for R 2 and R 3 .
  • Preferred R 2 R 3 N-CrC 4 -alkyl radicals are aminomethyl, N-methylaminomethyl, ⁇ , ⁇ -dimethylaminomethyl and N,N- diethylaminomethyl.
  • Ri as a C 3 -C 5 -heterocyclic radical may be, for example, any one of the above mentioned heterocyclic radicals having 3 to 5 C-atoms in its basic structure.
  • Examples of preferred heterocyclic radicals Ri are 1 ,3-dioxolan-2-yl, 2-methyl-1 ,3-dioxolan-2-yl, N-pyrrolidinyl or a radical of the formula N Y (4) wherein Y is NH, NCi-C 2 -alkyl, O or S, preferably NH, NCH 3 or O, and in particular O.
  • Preferred radicals Ri are unsubstituted or halogeno-, thiol-, Ci-C 2 -alkoxy- or hydroxyl- substituted CrC 4 -alkyl, hydroxyl, unsubstituted or halogeno-substituted CrC 4 -alkoxy, thiol, CrC 4 -alkylthio, halogen, Ci-C 2 -alkylsulfinyl, CrC 2 -alkylsulfonyl, Ci-C 2 -alkylsulfonylamino, acetyl, acetylamino, a radical N R 2 R 3 or R 2 R 3 N-Ci-C 2 -alkyl wherein each the above-given meanings and preferences for R 2 and R 3 apply, and a radical of formula N Y (4) wherein Y is NH, NCi-C 2 -alkyl, O or S, preferably NH, NCH 3 or O,
  • radicals Ri include unsubstituted or Ci-C 2 -alkoxy- or hydroxyl- substituted CrC 4 -alkyl, hydroxyl, unsubstituted or halogen-substituted Ci-C 2 -alkoxy, Ci-C 2 - PAT054251 -WO-PCT
  • Particular preferred radicals Ri include methyl, ethyl, isopropyl, 1 - or 2-hydroxyethyl, hydroxyl, methoxy, ethoxy, trifluoromethoxy, methylthio, chlorine, fluorine, amino, N-mono- or N,N-dimethylamino, N-mono- or N,N-diethylamino, N-2-hydroxyethylamino, N,N- dimethylaminomethyl, ⁇ , ⁇ -diethylaminomethyl and morpholinyl.
  • a preferred phenyl radical A is a radical of formula
  • R 1a the meanings and preferences given above for R-i apply
  • Ri b is H or has independently one the meanings given above for R-i .
  • a particularly preferred embodiment of the present invention concerns a radical of the above-given formula (2a) wherein R 1 b is H, halogen, CrC 2 -alkoxy, CrC 2 -alkyl, halo-Ci-C 2 -alkyl or halo-Ci-C 2 -alkoxy, in particular H, and for R 1a the meanings and preferences given above for R-i apply.
  • R 1 b is H, chlorine, fluorine, methyl, trifluoromethyl, methoxy or trifluoromethoxy, in particular H, and for R 1a the meanings and preferences given above for R- ⁇ apply.
  • the ring (a) denotes, for example, an annulated phenyl, cyclopentyl or cyclohexyl ring which may be further substituted , for example by a substituent as given before for Ri .
  • the annulated ring (a) is a 6-membered or, in particular, a 5-membered heterocyclic ring having one or two heteroatoms selected from the group consisting of N, O and S and being unsubstituted or further substituted by CrC 2 -alkyl.
  • annulated rings (a) are a 5-membered heterocyclic ring having 1 or 2 N-or O-atoms.
  • Y is -NH-, -N(Ci-C 2 -alkyl)-, -O- or -S- and Z is CH or N, or most preferably, Y is -NH- or -N(CrC 2 -alkyl)- and Z is CH; and Yi is -0-.
  • A denotes a heterocyclic radical
  • said radical A is preferably a 5- or 6-membered ring having 1 or 2 same or different heteroatoms selected from the group consisting of N, O and S, which radical may be further substituted, for example, by CrC 2 -alkyl, CrC 2 -alkoxy or halogen, and/or may carry an annulated benzo ring.
  • suitable heterocyclic radicals are mentioned before.
  • Preferred heterocyclic radicals A are heteroaromatic radicals.
  • heterocyclic radicals A are thienyl; furanyl; pyrrolyl; benzothienyl; benzofuranyl; pyrazolyl, pyridinyl; or pyrimidinyl; each of which unsubstituted or substituted, for example, by halogen or Ci-C 2 -alkyl.
  • the heterocyclic radical may be bonded via the C- atom in o- or m-position, in case of a 6-membered ring also in p-position, relative to the heteroatom.
  • heterocyclic radicals A are thien-2- or -3-yl, which is unsubstituted or substituted by methyl or chlorine; benzothien-3-yl; furan-2- or -3-yl; pyrazol- 3- or -4-yl; N-methyl-pyrazol-3- or -4-yl or pyridine-3- or -4-yl.
  • One preferred embodiment of the compounds as used in the present invention concerns a compound of the above-given formula (1 ), wherein X-i and X 2 are each fluorine or chlorine; and A is
  • (i) a radical of the above-given formula (2), wherein (Ri)i -5 is 1 to 4, preferably 1 or 2, same or different substituents selected from the group consisting of unsubstituted or halogeno-, thiol-, Ci-C 2 -alkoxy- or hydroxyl-substituted CrC 4 -alkyl; hydroxyl; unsubstituted or halogeno- substituted Ci-C 4 -alkoxy; thiol; Ci-C 4 -alkylthio; halogen; Ci-C 2 -alkylsulfinyl; Ci-C 2 - PAT054251 -WO-PCT
  • annulated ring (a) is a 6-membered or, in particular, a 5-membered heterocyclic ring having one or two heteroatoms selected from the group consisting of N, O and S; or is
  • (iii) is a 5- or 6-membered heterocyclic radical having 1 or 2 same or different heteroatoms selected from the group consisting of N, O and S, which radical may be further substituted, for example, by CrC 2 -alkyl, CrC 2 -alkoxy or halogen, and/or may carry an annulated benzo ring.
  • a further preferred embodiment of the compounds as used in the present invention concerns a compound of the above-given formula (1 ), wherein X-i and X 2 are each fluorine; and A is
  • R 1a is unsubstituted or Ci-C 2 -alkoxy- or hydroxyl-substituted CrC 4 -alkyl hydroxyl; unsubstituted or halogen-substituted Ci-C 2 - alkoxy; Ci-C 2 -alkylthio; halogen; a radical NR 2 R 3 or R 2 R 3 N-methyl, wherein R 2 and R 3 are each independently hydrogen or Ci-C 2 -alkyl, which is unsubstituted or substituted by chlorine hydroxyl, methoxy, ethoxy, thiol, methylthio or ethylthio; or morpholinyl; and Ri b is H, halogen, Ci-C 2 -alkoxy, Ci-C 2 -alkyl, halo-Ci-C 2 -alkyl or halo-Ci-C 2 -alkoxy; or
  • (ii) is a radical of the above-given formula (3a) or (3b),wherein Y is -NH-, -N(Ci-C 2 -alkyl)-, - O- or -S- and Z is CH or N; and Yi is -0-; or is
  • a particularly preferred embodiment of the compounds as used in the present invention concerns a compound of the above-given formula (1 ), wherein X-i and X 2 are each fluorine; and A is a radical of the above-given formula (2a), wherein R 1a is methyl, ethyl, isopropyl, 1 - or 2-hydroxyethyl, hydroxy, methoxy, ethoxy, trifluoromethoxy, methylthio, chlorine, fluorine, amino, N-mono- or N,N-dimethylamino, N-mono- or ⁇ , ⁇ -diethylamino, N-2- hydroxyethylamino, N,N-dimethylaminomethyl, ⁇ , ⁇ -diethylaminomethyl or morpholinyl; and R-ib is H, chlorine, fluorine, methyl, trifluoromethyl, methoxy or trifluoromethoxy, in particular PAT054251 -WO-PCT
  • the compounds according to the present invention have potent insecticidal and acaricidal activity in the agricultural field. Therefore, the compounds represented by formula (I) or formula (la) of the present invention can be used as insecticides and acaricides.
  • the compounds according to the present invention also exert an appropriate controlling effect against harmful insects without phytotoxicity against cultured plants.
  • the compounds of the present invention can be used for controlling a wide variety of pests including, for example, harmful sucking insects, biting insects and other plant-parasitic pests and stored grain pests and can be applied for their control, in particular eradication and extermination. Therefore, the present invention also encompasses a method for combating harmful pests.
  • the compounds according to the invention in combination with good plant tolerance and being tolerated well by the environment, are suitable for protecting plants and plant organs, for increasing the harvest yields, for improving the quality of the harvested material and for controlling pests, in particular insects, arachnids, helminths, nematodes and molluscs, which are encountered in agriculture, in horticulture, in animal husbandry, in forests, in gardens and leisure facilities, in the protection of stored products and of materials. They may be preferably employed as plant protection agents. They are active against normally sensitive and resistant species and against all or some stages of development.
  • the agricultural invertebrate pests which can be combated by using the compounds and compositions according to the invention include inter alia: PAT054251 -WO-PCT
  • Anoplura for example, Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
  • Acarus siro Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus lat
  • Lissorhoptrus oryzophilus Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha PAT054251 -WO-PCT
  • Premnotrypes spp. Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Stemechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogo- derma spp., Tychius spp., Xylotrechus spp., Zabrus spp.; as well as Callosobruchus Chinensis, Sitophilus zeamais, Tribolium Castaneum, Epilachna vigintioctomaculata, Agriotes fuscicollis, Anomala rufocuprea, Leptinotarsa decemlineata, Diabrotica spp., Monochamus alternatus, Lissorhoptrus oryz
  • Thysanoptera From the order of the Thysanoptera, for example, Basothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp.,
  • burning devices include, for example, fumigation and smoking cartridges, cans and coils
  • UVL cold mist, warm mist
  • the concentration of the active compound according to the present invention for application may be in the range of from 0.0000001 to 100% by weight, preferably in the range of from 0.00001 to 1 % by weight.
  • the compounds according to the present invention may be used in ordinary manners suitable for their application forms. It is understood that the compounds according to the invention can also be present in compositions containing further ingredients, such as auxiliaries or active ingredients. The skilled person will choose a suitable ingredient among those named herein and known in the art and which are supposed to enhance a property which is considered being favorable in view of the intended application and use.
  • customary treatment methods for example by immersion, spraying, evaporation, fogging, scattering, painting on, injecting and, in the case of propagation material, in particular in the case of seed, also by applying one or more coats.
  • plants of the plant cultivars which are in each case commercially available or in use are treated according to the invention.
  • Plant cultivars are understood as meaning plants having novel properties ("traits") which have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be cultivars, bio- or genotypes. Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, vegetation period, diet), the treatment according to the invention may also result in superadditive "synergistic") effects.
  • cereals wheat, rice
  • maize soya beans, potatoes, sugar beet, tomatoes, peas and other vegetable varieties, cotton, tobacco, oilseed rape and also fruit plants (with the fruits apples, pears, citrus fruits and grapes), and particular emphasis is given to maize, soya beans, potatoes, cotton, tobacco and oilseed rape.
  • the compounds according to the invention also have a strong insecticidal action against insects which destroy industrial materials.
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
  • Bristletails such as Lepisma saccharina.
  • Industrial materials in the present connection are to be understood as meaning non-living materials, such as, preferably, plastics, adhesives, sizes, papers and cardboards, leather, wood and processed wood products and coating compositions.
  • the compounds according to the invention can likewise be employed for protecting objects which come into contact with saltwater or brackish water, in particular hulls, screens, nets, buildings, moorings and signalling systems, against fouling.
  • the active compounds are also suitable for controlling insects, arachnids and mites, which are found in enclosed spaces such as, for example, dwellings, factory halls, offices, vehicle cabins and the like. They can be employed alone or in combination with other active compounds and auxiliaries in domestic insecticide products for controlling these pests. They are active against sensitive and resistant species and against all developmental stages. These pests include:
  • Diplopoda for example, Blaniulus guttulatus, Polydesmus spp.
  • Chilopoda for example, Geophilus spp.
  • Anthrenus spp. From the order of the Coleoptera, for example, Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
  • Lepidoptera From the order of the Lepidoptera, for example, Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
  • Hymenoptera From the order of the Hymenoptera, for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • the compounds or compositions according to the invention can be used in aerosols, pressure-free spray products, for example pump and atomizer sprays, automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller- driven evaporators, energy-free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for scattering or in bait stations.
  • pump and atomizer sprays automatic fogging systems, foggers, foams, gels, evaporator products with evaporator tablets made of cellulose or polymer, liquid evaporators, gel and membrane evaporators, propeller- driven evaporators, energy-free, or passive, evaporation systems, moth papers, moth bags and moth gels, as granules or dusts, in baits for scattering or in bait stations.
  • the compounds or compositions according to the invention are particularly suitable for treating seed.
  • a large part of the damage to crop plants which is caused by pests occurs as early as when the seed is attacked during storage and after the seed is introduced into the soil, during and immediately after germination of the plants. This phase is particularly critical since the roots and shoots of the growing plant are particularly sensitive and even minor damage can lead to the death of the whole plant. Protecting the seed and the germinating plant by the use of suitable compositions is therefore of particularly great interest.
  • the present invention therefore in particular also relates to a method for the protection of seed and germinating plants from attack by pests, by treating the seed with a composition according to the invention.
  • the invention likewise relates to the use of the compositions according to the invention for the treatment of seed for protecting the seed and the resulting plant from pests.
  • the invention relates to seed which has been treated with a composition according to the invention so as to afford protection from pests.
  • One of the advantages of the present invention is that the particular systemic properties of the compositions according to the invention mean that treatment of the seed with these compositions not only protects the seed itself, but also the resulting plants after emergence, from pests. In this manner, the immediate treatment of the crop at the time of sowing or shortly thereafter can be dispensed with.
  • the compounds or compositions according to the invention are suitable for protecting seed of any plant variety as already mentioned above which is employed in agriculture, in the greenhouse, in forests or in horticulture.
  • this takes the form of seed of maize, peanut, canola, oilseed rape, poppy, soya beans, cotton, beet (for example sugar beet and fodder beet), rice, sorghum and millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables (for example tomatoes, cabbage plants).
  • the compositions according to the invention are likewise suitable for treating the seed of fruit plants and vegetables as already mentioned above. The treatment of the seed of maize, soya beans, cotton, wheat and canola or oilseed rape is of particular importance.
  • the formulation i.e. preparations containing the active ingredient of formula (1 ), or combinations of these active ingredients with other active ingredients, and optionally a solid, semi-solid or liquid adjuvant, are produced in a manner known per se, for example by intimately mixing, kneading or dispersing the active ingredients with compositions of excipients, whereby the physiological compatibility of the formulation excipients must be taken into consideration.
  • polymeric agents with controlled release properties may be applied derivatives made by e.g. polylactic acid, polylactic coglycolic acid, poly orthoester, polyethylene carbonate, poly anhydrids and starch and PVC based matrices.
  • preservatives like sorbic acid, benzyl alcohol and parabenes, and antioxidants as e.g. alpha tocopherol may be added.
  • the active ingredient or combinations of the active ingredient may also applied in capsules, like hard gelatine capsules or soft capsules.
  • the binders for tablets and boli may be chemically modified polymeric natural substances PAT054251 -WO-PCT
  • cellulose or protein derivatives e.g. methyl cellulose, carboxymethyl cellulose, ethylhydroxyethyl cellulose, proteins such as zein, gelatin and the like
  • synthetic polymers such as polyvinyl alcohol, polyvinyl pyrrolidone etc.
  • the tablets also contain fillers (e.g. starch, microcrystalline cellulose, sugar, lactose etc.), lubricants (e.g. magnesium stearate), glidants (e.g. colloidal silicon dioxide) and disintegrants (e.g. cellulose derivatives) and acid resistant coatings, like e.g. acrylic acid esters.
  • the compounds of formula (1 ) according to the invention may be used alone or in combination with other biocides. They may be combined with pesticides having the same sphere of activity e.g. to increase activity, or with substances having another sphere of activity e.g. to broaden the range of activity. It can also be sensible to add so-called repellents. Since the compounds of formula (1 ) are adulticides, i.e. since they are effective in particular against the adult stage of the target parasites, the addition of pesticides which instead attack the juvenile stages of the parasites may be very advantageous. In this way, the greatest part of those parasites that produce great economic damage will be covered. Moreover, this action will contribute substantially to avoiding the formation of resistance. Many combinations may also lead to synergistic effects, i.e. the total amount of active ingredient can be reduced, which is desirable from an ecological point of view. Preferred groups of combination partners and especially preferred combination partners are known to the art-skilled worker.
  • a further aspect of the present invention relates to a combination preparation for the control of agricultural invertebrate pests, characterised in that it contains, in addition to a compound of formula (1 ), at least one further active ingredient having the same or different sphere of activity and at least one physiologically acceptable carrier.
  • the present invention is not restricted to two-fold combinations.
  • the agricultural compositions according to the invention contain 0.1 to 99 % by weight, especially 0.1 to 95 % by weight of one or more active ingredients of formula (1 ), 99.9 to 1 % by weight, especially 99.8 to 5 % by weight of a solid or liquid admixture, including 0 to 25 % by weight, especially 0.1 to 25 % by weight of a surfactant.
  • the active ingredients of formula (1 ) can be PAT054251 -WO-PCT
  • Table 1 a provides 34 compounds of formula
  • Table 1 b provides 34 compounds of formula
  • Table 2 provides 12 compounds of formula
  • Table 2a provides 12 compounds of formula
  • Table 2b provides 12 compounds of formula PAT054251 -WO-PCT
  • Leaf discs (3 cm diameter) were cut fresh from uninfested Chinese cabbage (Brassica napus L var chinensis cv Tip-Top). Leaf discs were placed onto a bed of agar (1 % w/w) contained in 5 cm Petri dishes. Each leaf disc was infested with 20 adult aphids, and then sprayed with the test solution in a Burkhard Potter Tower calibrated to apply a volume of 300 l/ha. The Burkhard Potter Tower was calibrated following the methodology set out in i2LResearch Ltd SOP/231/02, 'Use, Calibration and Maintenance of the Potter Tower'. The Petri dishes were sealed with a ventilated lid, and incubated in a controlled environment room at 20 ⁇ 2 °C, 60-70% relative humidity and a L16:D8 photoperiod.
  • Aphid mortality was assessed at 24h and 72 h after treatment. Aphids were scored as dead if they were unable to walk after stimulation with a seeking needle.
  • Leaf discs (3 cm diameter) were cut fresh from uninfested dwarf French bean plants. Leaf discs were placed onto a bed of agar contained in 5 cm Petri dishes. Each leaf disc was infested with 20-25 adult mites within the circle of insect glue using a fine brush. Leaf discs were then sprayed with the test solution in a Burkhard Potter Tower. The Petri dishes were sealed with a ventilated lid, and incubated at 26 ⁇ 2 °C, 60-70% relative humidity on L16:D8 photoperiod.
  • Mites were scored as dead or alive under a binocular microscope 24 h and 72 h after treatment with the two compounds.

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  • Life Sciences & Earth Sciences (AREA)
  • Agronomy & Crop Science (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

L'invention concerne l'utilisation de composés de pyrimidine spécifiques représentés par la formule (I), dans cette formule, les variables sont telles de définies dans les revendications; sous une forme libre et sous une forme saline; et éventuellement, les énantiomères et les isomères géométriques de ceux-ci, pour lutter contre les nuisibles invertébrés dans l'agriculture.
PCT/EP2011/060685 2010-06-28 2011-06-27 Nouvelle utilisation Ceased WO2012000922A2 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
CH1083/10 2010-06-28
CH10832010 2010-06-28

Publications (2)

Publication Number Publication Date
WO2012000922A2 true WO2012000922A2 (fr) 2012-01-05
WO2012000922A3 WO2012000922A3 (fr) 2012-02-23

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2011/060685 Ceased WO2012000922A2 (fr) 2010-06-28 2011-06-27 Nouvelle utilisation

Country Status (1)

Country Link
WO (1) WO2012000922A2 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111712182A (zh) * 2018-02-09 2020-09-25 爱尔康公司 用于激光扫描系统的系统反相控制器

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005085211A1 (fr) 2004-03-08 2005-09-15 Novartis Ag Utilisation de composes de pyrimidine dans la preparation de d'antiparasitaires
WO2008009691A1 (fr) 2006-07-21 2008-01-24 Novartis Ag Dérivés de pyrimidine et leur utilisation comme pesticides

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
IL106324A (en) * 1992-07-17 1998-09-24 Shell Int Research Transformed pyrimidine compounds, their preparation and use as pesticides

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2005085211A1 (fr) 2004-03-08 2005-09-15 Novartis Ag Utilisation de composes de pyrimidine dans la preparation de d'antiparasitaires
WO2008009691A1 (fr) 2006-07-21 2008-01-24 Novartis Ag Dérivés de pyrimidine et leur utilisation comme pesticides

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111712182A (zh) * 2018-02-09 2020-09-25 爱尔康公司 用于激光扫描系统的系统反相控制器
CN111712182B (zh) * 2018-02-09 2023-07-14 爱尔康公司 用于激光扫描系统的系统反相控制器

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