Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
  • C07D213/53—Nitrogen atoms
• • 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
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
• • 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
  • A01N47/40—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 a double or triple bond to nitrogen, e.g. cyanates, cyanamides
• • 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
  • A01N51/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds having the sequences of atoms O—N—S, X—O—S, N—N—S, O—N—N or O-halogen, regardless of the number of bonds each atom has and with no atom of these sequences forming part of a heterocyclic ring
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
  • C07D213/59—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals with at least one of the bonds being to sulfur
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D213/61—Halogen atoms or nitro radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
  • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
  • C07D213/89—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members with hetero atoms directly attached to the ring nitrogen atom
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/22—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
  • C07D277/30—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
  • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
  • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
  • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
  • C07D307/04—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
  • C07D307/10—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
  • C07D307/16—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Definitions

• the invention relates to compounds of formula
• A is an unsubstituted or substituted heterocyclyl group
• R ⁇ is hydrogen or alkyl
• R 2 is hydrogen or alkyl
• R 3 is hydrogen or alkyl
• R 5 is alkyl, alkoxy, N(R 6 )R or an unsubstituted or substituted aryl, aryloxy or benzyloxy group;
• R 6 is hydrogen, alkyl or unsubstituted or substituted aryl
• R 7 is hydrogen, alkyl or unsubstituted or substituted aryl
• any reference hereinbefore and hereinafter to the compounds I or to tautomers thereof should be understood as including also the corresponding tautomers or compounds I, respectively, as appropriate and expedient, even when the latter are not specifically mentioned in each case.
• Compounds I that have at least one basic centre may, for example, form acid addition salts, for example with strong inorganic acids, such as mineral acids, e.g. perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid, with strong organic carboxyiic acids, such as unsubstituted or substituted, for example halo-substituted, CrC alkanecarboxylic acids, e.g. acetic acid, saturated or unsaturated dicarboxylic acids, e.g. oxalic acid, malonic acid, succinic acid, maleic acid, fumaric acid or phthalic acid, hydroxycarboxylic acids, e.g.
• strong inorganic acids such as mineral acids, e.g. perchloric acid, sulfuric acid, nitric acid, nitrous acid, a phosphoric acid or a hydrohalic acid
• strong organic carboxyiic acids such as unsub
• Compounds I having at least one acid group may, for example, form salts with bases, for example metal salts, such as alkali metal or alkaline earth metal salts, e.g.
• sodium, potassium or magnesium salts or salts with ammonia or an organic amine, such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl-, diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- or tri-hydroxy-lower alkylamine, e.g. mono-, di- or tri-ethanolamine. It may also be possible for corresponding internal salts to be formed.
• an organic amine such as morpholine, piperidine, pyrrolidine, a mono-, di- or tri-lower alkylamine, e.g. ethyl-, diethyl-, triethyl- or dimethyl-propyl-amine, or a mono-, di- or tri-hydroxy-lower alkylamine, e.g. mono-, di- or tri-ethanolamine. It may also be possible for
• any reference hereinbefore and hereinafter to the free compounds I or to salts thereof should be understood as including also the corresponding salts or the free compounds I, respectively, as appropriate and expedient, even when the latter are not specifically mentioned in each case.
• the ring hetero atom(s) in the basic ring structure of the heterocyclyl group A which is, for example, bicyclic or, preferably, monocyclic, may be any element of the Periodic Table that is capable of forming at least two covalent bonds (there being understood by a "ring nitrogen atom” also the N-oxide form thereof), it being possible, when the basic ring structure of A is constructed from more than one ring, for a ring hetero atom or ring hetero atoms to be present either in one ring only or, alternatively, in more than one ring of the basic ring structure of A.
• carbon-containing groups and compounds each contain, for example, from 1 up to and including 10, preferably from 1 up to and including 8, especially from 1 up to and including 5, more especially 1 or 2, carbon atom(s).
• N-oxide form thereof with not more than one ring oxygen atom or one ring sulfur atom being present in the basic ring structure, especially contains at least one ring nitrogen atom (there being understood by "a ring nitrogen atom” also the N-oxide form thereof), especially contains at least one ring nitrogen atom;
• A preferably is unsubstituted or mono- or di-substituted, the substituent(s) being selected from the group consisting of halogen, C C 5 alkyl, halo-CrC 5 alkyl, d-C 5 alkoxy and halo-
• A especially is unsubstituted or mono- or di-substituted, the substituents being selected from the group consisting of halogen,
• a more especially is mono-substituted by halogen
• A preferably is a tetrahydrofur-3-yl, pyrid-3-yl, 2-halopyrid-5-yl, 1 -oxido-3-pyridinio, 2-halo-1- oxido-5-pyridinio, thiazol-5-yl or 2-halothiazol-5-yl group, A especially is a 2-chlorothiazol-5-yl or, more especially, 2-chloropyrid-5-yl group;
• R 3 especially is hydrogen
• R 5 is alkyl, alkoxy, N(R 6 )R or an unsubstituted or substituted aryl, aryloxy or benzyloxy group
• R 6 is hydrogen, alkyl or unsubstituted or substituted aryi
• R 7 is hydrogen, alkyl or unsubstituted or substituted aryl
• R preferably is hydrogen, C ⁇ -C 7 alkyl, C 2 -C 5 alkenyl or C 2 -C 5 alkynyl, R 4 especially is C C 5 alkyl;
• the invention relates also to a process for the preparation of the compounds of formula I or, where applicable, the tautomers thereof, in each case in free form or in salt form, which process comprises, for example, reacting a compound of formula
• the reactions described hereinbefore and hereinafter are carried out in a manner known perse, for example in the absence or usually in the presence of a suitable solvent or diluent or a mixture thereof, the reactions being carried out, as required, with cooling, at room temperature or with heating, for example in a temperature range from approximately -80 C C to the boiling temperature of the reaction mixture, preferably from approximately -20°C to approximately +150°C, and, if required, in a closed vessel, under pressure, in an inert gas atmosphere and/or under anhydrous conditions.
• a suitable solvent or diluent or a mixture thereof for example in the absence or usually in the presence of a suitable solvent or diluent or a mixture thereof, the reactions being carried out, as required, with cooling, at room temperature or with heating, for example in a temperature range from approximately -80 C C to the boiling temperature of the reaction mixture, preferably from approximately -20°C to approximately +150°C, and, if required, in a closed vessel, under pressure, in
• the starting materials mentioned hereinbefore and hereinafter, which are used in the preparation of compounds I or, where applicable, tautomers thereof, in each case in free form or in salt form are known or can be prepared according to methods known per se, for example in accordance with the details given hereinafter.
• the compounds II and tautomers thereof used as starting materials, in each case in free form or in salt form are novel and the invention also relates thereto.
• the invention relates furthermore to a process for the preparation of the compounds of formula II or tautomers thereof, in each case in free form or in salt form.
• a compound I or II can be converted in a manner known perse into a different compound I or II, respectively, by replacing one or more substituents of the starting compound I or II by (an)other substituent(s) according to the invention in customary manner.
• Salts of compounds I and II can be prepared in a manner known perse.
• acid addition salts of compounds I and II are obtained by treatment with a suitable acid or a suitable ion exchange reagent and salts with bases are obtained by treatment with a suitable base or a suitable ion exchange reagent.
• Salts of compounds I and II can be converted in customary manner into the free compounds I and II, respectively; acid addition salts can be converted, for example, by treatment with a suitable basic medium or a suitable ion exchange reagent and salts with bases, for example, by treatment with a suitable acid or a suitable ion exchange reagent.
• Salts of compounds I and II can be converted into different salts of compounds I and II, respectively, in a manner known per se; for example acid addition salts can be converted into different acid addition salts, for example by treatment of a salt of an inorganic acid, such as a hydrochloride, with a suitable metal salt, such as a sodium, barium or silver salt, of an acid, for example with silver acetate, in a suitable solvent in which an inorganic salt being formed, for example silver chloride, is insoluble and is therefore precipitated out from the reaction mixture.
• a salt of an inorganic acid such as a hydrochloride
• a suitable metal salt such as a sodium, barium or silver salt
• the compounds I and II having salt-forming properties can be obtained in free form or in the form of salts.
• the compounds I and II and, in each case, where applicable, the tautomers thereof, in each case in free form or in salt form, may be in the form of one of the possible isomers or in the form of a mixture thereof, for example depending upon the number of asymmetric carbon atoms occurring in the molecule and the absolute and relative configuration thereof and/or depending upon the configuration of non-aromatic double bonds occurring in the molecule, or may be in the form of pure isomers, such as antipodes and/or diastereoisomers, or in the form of mixtures of isomers, such as mixtures of enantiomers, for example racemates, mixtures of diastereoisomers or mixtures of racemates; the invention relates both to the pure isomers and to all possible mixtures of isomers and this is to be understood accordingly hereinbefore and hereinafter, even when stereochemical details are not specifically mentioned in each case.
• Pure diastereoisomers and enantiomers can be obtained not only by separation of corresponding mixtures of isomers but also, according to the invention, by generally known methods of diastereoselective or enantioselective synthesis, for example by carrying out the process according to the invention with starting materials that have appropriate stereochemistry.
• the biologically more active isomer for example enantiomer or diastereoisomer, or mixture of isomers, for example mixture of enantiomers or mixture of diastereoisomers, insofar as the individual components have different biological activity.
• the compounds I and II, in free form or in salt form, may also, where applicable, be obtained in the form of hydrates and/or may include other solvents, for example solvents that may optionally have been used for the crystallisation of compounds that occur in solid form.
• the invention relates to all those embodiments of the process according to which a compound obtainable as starting material or intermediate at any stage of the process is used as starting material and all or some of the remaining steps are carried out, or in which a starting material is used in the form of a derivative and/or a salt and/or its racemates or antipodes, or, especially, is formed under the reaction conditions.
• the invention relates especially to the preparation processes described in Examples P1 to P17.
• the invention relates also to the novel starting materials and intermediates, in each case in free form or in salt form, that are used according to the invention in the preparation of compounds I or salts thereof, to a process for the preparation thereof and to their use as starting materials and intermediates in the preparation of compounds I; that applies especially to the compounds II, but also to the novel starting materials and intermediates, in each case in free form or in salt form, that are used according to the invention in the preparation of compounds II or salts thereof, the variables in the last mentioned starting materials and intermediates preferably having those meanings, which lead to the compounds I according to the invention.
• Preferred processes for the preparation of these starting materials and intermediates are described in the Preparation Examples hereinafter.
• the compounds I according to the invention are valuable preventive and/or curative active ingredients having a very advantageous biocidal spectrum even at low rates of concentration, while being well tolerated by warm-blooded animals, fish and plants.
• the compounds of the invention are effective against all or individual development stages of normally sensitive animal pests, but also of resistant animal pests, such as insects or representatives of the order Acarina.
• the insecticidal or acaricidal action of the compounds of the invention may manifest itself directly, i.e. in the mortality of the pests, which occurs immediately or only after some time, for example during moulting, or indirectly, for example in reduced oviposition and/or hatching rate, good activity corresponding to a mortality of at least 50 to 60 %.
• the mentioned animal pests include, for example: pests of the order Acarina, for example,
• Boophilus spp. Brevipalpus spp., Bryobia praetiosa, Calipitrimerus spp., Chorioptes spp.,
• Haematopinus spp. Linognathus spp., Pediculus spp., Pemphigus spp. and Phylloxera spp.; pests of the order Coleoptera, for example,
• Agriotes spp. Anthonomus spp., Atomaria linearis, Chaetocnema tibialis, Cosmopolites spp., Curculio spp., Dermestes spp., Diabrotica spp., Epilachna spp., Eremnus spp.,
• Otiorhynchus spp. Phlyctinus spp., Popillia spp., Psylliodes spp., Rhizopertha spp.,
• Aedes spp. Antherigona soccata, Bibio hortulanus, Calliphora erythrocephala, Ceratitis spp., Chrysomyia spp., Culex spp., Cuterebra spp., Dacus spp., Drosophila melanogaster,
• Liriomyza spp. Luciiia spp., Melanagromyza spp., Musca spp., Oestrus spp., Orseolia spp.,
• Leptocorisa spp. Leptocorisa spp., Nezara spp., Piesma spp., Rhodnius spp., Sahlbergella singularis,
• Scotinophara spp. and Triatoma spp. pests of the order Homoptera, for example,
• Aleurothrixus floccosus Aleurothrixus floccosus, Aleyrodes brassicae, Aonidiella spp., Aphididae, Aphis spp.,
• Aspidiotus spp. Bemisia tabaci, Ceroplaster spp., Chrysomphalus aonidium,
• Erythroneura spp. Gascardia spp., Laodelphax spp., Lecanium corni, Lepidosaphes spp.,
• Macrosiphus spp. Myzus spp., Nephotettix spp., Nilaparvata spp., Parlatoria spp.,
• Pemphigus spp. Planococcus spp., Pseudaulacaspis spp., Pseudococcus spp., Psylla spp., Pulvinaria aethiopica, Quadraspidiotus spp., Rhopalosiphum spp., Saissetia spp.,
• Vespa spp. pests of the order Isoptera, for example, Reticulitermes spp.; pests of the order Lepidoptera, for example,
• Blatta spp. Blattella spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Periplaneta spp. und Schistocerca spp.; pests of the order Psocoptera, for example, Liposceiis spp.; pests of the order Siphonaptera, for example, Ceratophyllus spp., Ctenocephalides spp. and Xenopsylla cheopis; pests of the order Thysanoptera, for example,
• Thysanura pests of the order Thysanura, for example, Lepisma saccharina.
• Target crops are especially cereals, such as wheat, barley, rye, oats, rice, maize and sorghum; beet, such as sugar beet and fodder beet; fruit, such as pomes, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries, or berries, for example strawberries, raspberries or blackberries; leguminous plants, such as beans, lentils, peas and soybeans; oil plants, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans and groundnuts; cucurbitaceae, such as marrows, cucumber and melons; fibre plants, such as cotton, flax, hemp and jute; citrus fruit, such as oranges, lemons, grapefruit and mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes and paprika; lauraceae, such as avocados, cinnamon and camphor; and tobacco, nuts, coffee
• the compounds according to the invention are suitable especially for controlling Aphis craccivora, Diabrotica balteata, Myzus persicae, Nephotettix cincticeps and Nilaparvata lugens in crops of vegetables, maize and rice.
• the invention therefore relates also to pesticidal compositions, such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, aerosols, coatable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymer substances, comprising - at least - one of the active ingredients of the invention, the type of formulation being chosen in accordance with the intended objectives and prevailing circumstances.
• pesticidal compositions such as emulsifiable concentrates, suspension concentrates, directly sprayable or dilutable solutions, aerosols, coatable pastes, dilute emulsions, soluble powders, dispersible powders, wettable powders, dusts, granules or encapsulations in polymer substances, comprising - at least - one of the active ingredients of the invention, the type of formulation being chosen in accordance with the intended objectives and prevailing circumstances.
• the active ingredient is used in those compositions in pure form, a solid active ingredient, for example, in a specific particle size, or, preferably, together with - at least - one of the adjuvants customary in formulation technology, such as extenders, for example solvents or solid carriers, or surface-active compounds (surfactants).
• extenders for example solvents or solid carriers, or surface-active compounds (surfactants).
• surfactants for example, those described in EP-A-0 736 252, the description of these adjuvants in EP-A-0 736 252 herewith being included by reference in the present description of the invention.
• compositions usually comprise 0.000 000 1 to 99.999 999 9 %, especially 0.1 to 95 %, of active ingredient and 0.000 000 1 to 99.999 999 9 %, especially 5 to 99.9 %, of - at least - one solid or liquid adjuvant, it generally being possible for 0 to 25 %, preferably 0.1 to 20 %, of the composition to be surfactants (in each case percentages are by weight).
• surfactants in each case percentages are by weight.
• the end user will normally employ dilute formulations which have considerably lower active ingredient concentrations.
• compositions according to the invention can be substantially broadened and adapted to prevailing circumstances by the addition of other insecticidal or acaricidal active ingredients.
• suitable additional active ingredients include representatives of the following classes of compounds: organophosphorus compounds, nitrophenol derivatives, thioureas, juvenile hormones, formamidines, ureas, pyrrole derivatives, avermectins and other macrolides, carbamates, pyrethroids, chlorinated hydrocarbons, neonicotinoids, acylureas, pyridylmethyieneamino derivatives and Bacillus thuringiensis preparations.
• compositions may also comprise further solid or liquid adjuvants, such as stabilisers, for example vegetable oils or epoxidised vegetable oils (e.g. epoxidised coconut oil, rape oil or soybean oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, as well as fertilisers or other active ingredients for obtaining special effects, for example bactericides, fungicides, nematocides, plant activators, molluscicides or herbicides.
• stabilisers for example vegetable oils or epoxidised vegetable oils (e.g. epoxidised coconut oil, rape oil or soybean oil), antifoams, for example silicone oil, preservatives, viscosity regulators, binders and/or tackifiers, as well as fertilisers or other active ingredients for obtaining special effects, for example bactericides, fungicides, nematocides, plant activators, mollusc
• compositions according to the invention are prepared in a manner known per se, in the absence of adjuvants, for example, by grinding, sieving and/or compressing a solid active ingredient, and in the presence of at least one adjuvant, for example, by intimately mixing and/or grinding the active ingredient with the adjuvant(s).
• the invention relates also to those processes for the preparation of the compositions and to the use of the compounds I in the preparation of those compositions.
• the invention relates also to the methods of application of the compositions, i.e.
• Typical rates of concentration are from 0.001 to 1 000 ppm, preferably from 0.1 to 500 ppm, of active ingredient.
• the rates of application per hectare are generally from 1 to 2 000 g of active ingredient per hectare, especially from 10 to 1 000 g/ha, preferably from 10 to 600 g/ha.
• a preferred method of application in the area of plant protection is application to the foliage of the plants (foliar application), the number of applications and the rate of application depending on the risk of infestation by the pest in question.
• the active ingredient can also penetrate the plants through the roots (systemic action) if the locus of the plants is impregnated with a liquid formulation or if the active ingredient is incorporated in solid form into the locus of the plants, for example into the soil, e.g. in granular form (soil application). In paddy rice crops, such granules may be applied in metered amounts to the flooded rice field.
• compositions according to the invention are also suitable for protecting plant propagation material, e.g. seed, such as fruit, tubers or grains, or plant cuttings, from animal pests of the mentioned type.
• the propagation material can be treated with the formulation before planting; seed, for example, can be dressed before being sown.
• the formulations can also be applied to grains (coating), either by impregnating the grains with a liquid formulation or by coating them with a solid formulation.
• the formulation can also be applied to the planting site when the propagation material is being planted, for example to the seed furrow during sowing.
• the invention relates also to those methods of treating plant propagation material and to the plant propagation material thus treated.
• Example P2 The other 31 compounds of Table 1 may also be prepared in a manner analogous to that described in Example P1.
• Example P4 The other 31 compounds of Table 2 may also be prepared in a manner analogous to that described in Example P3.
• Example P6 The other 31 compounds of Table 3 may also be prepared in a manner analogous to that described in Example P5.
• Example P8 The other 31 compounds of Table 4 may also be prepared in a manner analogous to that described in Example P7.
• Example P10 The other 127 compounds of Table 5 may also be prepared in a manner analogous to that described in Example P9. Table 5
• Example P12 The other 127 compounds of Table 6 may also be prepared in a manner analogous to that described in Example P11.
• Example P14 The other 127 compounds of Table 7 may also be prepared in a manner analogous to that described in Example P13.
• Example P17 The other 670 compounds of Tables 8 to 10 may also be prepared in a manner analogous to that described in Examples P15 and P16.
• Example F1 Emulsif iable concentrates a) b) c) active ingredient 25 % 40 % 50 % calcium dodecylbenzenesulfonate 5 % 8 % 6 % castor oil polyethylene glycol ether 5 % - - (36 mol of ethylene oxide) tributylphenoxypolyethylene glycol ether - 12 % 4 % (30 mol of ethylene oxide) cyclohexanone - 15 % 20 % xylene mixture 65 % 25 % 20 %
• Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
• Example F2 Solutions a) b) c) d) active ingredient 80% 10% 5% 95% ethylene glycol monomethyl ether 20% - - - polyethylene glycol (mol. wt.400) - 70% - -
• the solutions are suitable for application in the form of micro-drops.
• Example F3 Granules a) b) c) d) active ingredient 5% 10% 8% 21 % kaolin 94% - 79% 54% highly dispersed silicic acid 1 % - 13% 7% attapulgite - 90% - 18%
• the active ingredient is dissolved in dichloromethane, the solution is sprayed onto the carrier, and the solvent is subsequently evaporated off in vacuo.
• Example F4 Dusts a) b) active ingredient 2% 5% highly dispersed silicic acid 1 % 5% talcum 97% . kaolin 90%
• Example F5 Wettable powders a) b) c) active ingredient 25 % 50 % 75 % sodium lignosulfonate 5 % 5 % - sodium lauryl sulfate 3 % - 5 % sodium diisobutylnaphthalenesulfonate - 6 % 10 % octylphenoxypolyethylene glycol ether - 2 % -
• the active ingredient is mixed with the adjuvants and the mixture is thoroughly ground in a suitable mill, affording wettable powders which can be diluted with water to give suspensions of any desired concentration.
• Example F6 Suspension concentrate active ingredient 40 % ethylene glycol 10 % nonylphenoxypolyethylene glycol ether 6 %
• the finely ground active ingredient is intimately mixed with the adjuvants, giving a suspension concentrate from which suspensions of any desired concentration can be obtained by dilution with water.
• Example B1 Action against Aphis craccivora
• Pea seedlings are infested with Aphis craccivora, subsequently sprayed with a spray mixture comprising 400 ppm of active ingredient and then incubated at 20°. Evaluation is made 3 and 6 days later. The percentage reduction in population (% activity) is determined by comparing the number of dead aphids on the treated plants with that on untreated plants.
• Maize seedlings are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient. After the spray-coating has dried, the maize seedlings are populated with 10 Diabrotica balteata larvae in the second stage and then placed in a plastics container. The evaluation is made 6 days later. The percentage reduction in population
• % activity is determined by comparing the number of dead larvae on the treated plants with that on untreated plants.
• Example B4 Action against Heliothis virescens
• Young soybean plants are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient. After the spray-coating has dried, the plants are populated with 10 Heliothis virescens caterpillars in the first stage and then placed in a plastics container. Evaluation is made 6 days later. The percentage reduction in population and the percentage reduction in feeding damage (% activity) are determined by comparing the treated plants and untreated plants for the number of dead caterpillars and the feeding damage.
• Pea seedlings are infested with Myzus persicae, subsequently sprayed with a spray mixture comprising 400 ppm of active ingredient and then incubated at 20°. Evaluation is made 3 and 6 days later. The percentage reduction in population (% activity) is determined by comparing the number of dead aphids on the treated plants with that on untreated plants. Compounds of Tables 8 to 10 exhibit good activity in this test. In particular, compounds 8.2 and 8.15 are more than 80 % effective.
• Example B6 Action against Nephotettix cincticeps
• Pots containing rice plants are placed in an aqueous emulsion solution comprising 400 ppm of active ingredient.
• the plants are then populated with Nephotettix cincticeps larvae in the second and third stages. Evaluation is made 6 days later.
• the percentage reduction in population is determined by comparing the number of surviving cicadas on the treated plants with that on untreated plants.
• Example B7 Action against Nilaparvata lugens
• Rice plants are sprayed with an aqueous emulsion spray mixture comprising 400 ppm of active ingredient. After the spray-coating has dried, the plants are populated with
• Nilaparvata lugens larvae in the second and third stages Evaluation is made 21 days later.
• the percentage reduction in population is determined by comparing the number of surviving cicadas on the treated plants with that on untreated plants.

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• Chemical & Material Sciences (AREA)
• Organic Chemistry (AREA)
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• Agronomy & Crop Science (AREA)
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• 1998
  • 1998-09-07 EP EP98948924A patent/EP1021409A1/de not_active Withdrawn
  • 1998-09-07 AU AU95372/98A patent/AU9537298A/en not_active Abandoned
  • 1998-09-07 JP JP2000510717A patent/JP2001515888A/ja active Pending
  • 1998-09-07 WO PCT/EP1998/005667 patent/WO1999012906A1/en not_active Application Discontinuation

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