Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • 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
  • A01N43/88—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 three ring hetero atoms
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
  • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
  • C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

• the object of the present invention is a compound of formula
• Z signifies six- or seven-membered, optionally substituted, aromatic or non- aromatic heterocyclyl
• X is CH or N
• Y is halogen
• n is 1 , 2 or 3
• m is O or l
• the E/Z isomers, E/Z isomeric mixtures and/or tautomers thereof, each in free form or in salt form a method of producing and the use of these compounds, pesticides whose active ingredient is selected from these compounds or from an agrochemically acceptable salt thereof, a method of producing and the use of these compositions, plant propagating material that has been treated with these compositions and a method of controlling pests.
• the compounds of formula (I) and where appropriate their tautomers can form salts, for example acid addition salts. These are formed for example with strong inorganic acids, typically mineral acids, e.g. sulphuric acid, a phosphoric acid or a hydrohalic acid, or with strong organic carboxylic acids, typically acids substituted where appropriate for example by halogen, e.g. acetic acid, such as optionally unsaturated dicarboxylic acids, e.g. oxalic, malonic, maleic, fumaric or phthalic acid, such as hydroxycarboxylic acids, e.g.
• strong inorganic acids typically mineral acids, e.g. sulphuric acid, a phosphoric acid or a hydrohalic acid
• strong organic carboxylic acids typically acids substituted where appropriate for example by halogen, e.g. acetic acid, such as optionally unsaturated dicarboxylic acids, e.g. oxalic, malonic, maleic,
• compounds of formula (I) with at least one acid group can form salts with bases.
• Suitable salts with bases are for example metal salts, such as alkali 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 dimethylpropylamine, or a mono-, di- or trihydroxy-lower alkylamine, e.g. mono-, di- or triethanolamine.
• Corresponding internal salts where appropriate may also be formed. The free form is preferred. Of the salts of compounds of formula (I), the agrochemically beneficial salts are preferred.
• Halogen - as a group perse or as structural element of other groups and compounds such as haloalkyl, halocycloalkyl, haloalkenyl, haloalkinyl and haloalkoxy - is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine, mainly fluorine or chlorine, especially chlorine.
• carbon-containing groups and compounds each contain 1 to 20, inclusively, preferably 1 to 18, in particular 1 to 10, especially 1 to 6, in particular 1 to 4, especially 1 to 3, particularly 1 or 2, carbon atoms, with methyl being preferred in particular.
• Alkyl - as a group per se and as structural element of other groups and compounds such as haloalkyl, alkoxy, alkoxyalkyl, haloalkoxy, alkoxycarbonyl, alkylthio, haloalkylthio, alkylsulphonyl and alkylsulphonyloxy is, in each case with due consideration of the specific number of carbon atoms in the group or compound in question, either straight-chained, e.g.
• Alkenyl and alkinyl - as groups per se and as structural elements of other groups and compounds, such as of haloalkenyl, haloalkinyl, alkenyloxy, haloalkenyloxy, alkinyloxy or haloalkinyloxy - are straight-chained or branched and respectively contain two or preferably one unsaturated carbon-carbon bond(s).
• Vinyl, prop-2-en-1-yl, 2-methylprop-2-en-1-yl, but-2- en-1-yl, but-3-en-1-yl, prop-2-in-1-yl, but-2-in-1-yl and but-3-in-1-yl may be mentioned by way of example.
• Cycloalkyl - as a group per se and as a structural element of other groups and compounds, for example of alkyl - is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl. Cyclopentyl and cyclohexyl are preferred, in particular cyclopropyl.
• Halogen-substituted carbon-containing groups and compounds can be partially halogenated or perhalogenated, in the case of polyhalogenation it being possible for the halogen substituents to be identical or different.
• haloalkyl - as a group perse and as structural element of other groups and compounds such as haloalkoxy, - are methyl which is mono- to trisubstituted by fluorine, chlorine and/or bromine, such as CHF , CF 3 or CH 2 CI; 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 , CF 2 CFCI 2 , CH 2 CH 2 CI, CF 2 CHBr 2 , CF 2 CHCIF, CF 2 CHBrF oder CCIFCHCIF; propyl or isopropyl, mono- to heptasubstituted by fluorine, chlorine and/or bromine, such as CH 2 CHBrCH 2 Br, CF 2 CHFCF 3 , CH 2 CF 2 CF
• di-(C 1 -C -alkyl)amine the two alkyl groups are independent of each other.
• Aryl signifies especially phenyl or naphthyl, preferably phenyl.
• Heterocyclyl signifies a 6- or 7-membered, saturated or unsaturated ring which is bonded to the basic structure by a carbon atom, the ring having preferably two to four hetero atoms selected from the group comprising N, O and S. Preference is given to 6-rings having a nitrogen atom as the hetero atom and two further hetero atoms, preferably nitrogen or oxygen, especially one oxygen and one nitrogen.
• the heterocyclyl radicals may bear one to three, preferably one, substituent selected from the group comprising C ⁇ -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkinyl; halogen, nitro, cyano, -OH, -SH, C 3 -C 8 -cycloalkyl, halogen-C 3 -C 8 -cycloalkyl, C C 6 -alkoxy, halogen-d-C 6 -alkoxy, C 3 -C 6 - alkenyloxy, C ⁇ -C 4 -alkylthio and di-(C 1 -C -alkyl)amine.
• substituent selected from the group comprising C ⁇ -C 6 -alkyl, C 2 -C 6 -alkenyl, C 3 -C 6 -alkinyl; halogen, nitro, cyano, -OH, -SH, C 3 -C 8 -cycl
• Preferred embodiments in terms of the invention are compounds of formula (I) a) wherein Z signifies a ring of formula
• bonds U-A, A-M, M-D, D-E, E-G and G-U are single or double bonds, with the provision that no accumulated double bonds occur
• Ri, R 2 , R 7 and R 10 independently of one another, signify hydrogen, d-C 20 -alkyl, C 3 -C 8 - cycloalkyl, C 2 -C 20 -alkenyl or C 3 -C 20 -alkinyl; or mono- or poly-substituted d-C 2 o-alkyl,
• C 2 -C 20 -alkenyl or C 3 -C 20 -alkinyl aryl which is optionally substituted by one or more substituents selected from the group comprising d-C- 6 -alkyl, halogen-d-C 6 -alkyl, C 2 -C 6 -alkenyI, C 3 -C 6 -alkinyl, halogen, C C 6 - alkoxy, halogen-d-Ce-alkoxy, nitro, cyano, C 3 -C 8 -cycloaIkyl, halogen-C 3 -C 8 -cycloalkyl,
• Rn signifies hydrogen, OH, SH, d-C 6 -alkyl, C 3 -C 8 -cycloalkyl, d-C 6 -alkoxy, d-C 6 -alkylthio,
• C 3 -C 6 -alkinyl or C 3 -C 6 -alkinyloxy which are substituted by one or more substituents selected from the group comprising halogen, nitro, cyano, -OH, -SH, C 3 -C 8 -cycloalkyl, halogen-C 3 -C 8 -cycloalkyl and di-(d-C 4 -alkyl)amine; or aryl, heterocyclyl, aryloxy, benzyloxy or heterocyclyloxy, which are substituted by one to three substituents selected from the group comprising halogen, nitro, cyano, -OH, -SH,
• Z preferably has the following definitions, whereby Ri, R 2 , R 22 and R 7 are defined as described above:
• a further object of the invention is a process for the production of the compounds of formula (la), or a salt thereof, wherein a) a compound of formula
• a compound of formula (la), in which m is 1 , a compound of formula (I) in which m is 0 is reacted with an oxidation agent, for example inorganic peroxides, such as sodium perborate, potassium permanganate or hydrogen peroxide; or with mCPBA or organic per acids, such as perbenzoic acid or peracetic acid, or mixtures of organic acids and hydrogen peroxide, e.g. acetic acid/hydrogen peroxide;
• an oxidation agent for example inorganic peroxides, such as sodium perborate, potassium permanganate or hydrogen peroxide; or with mCPBA or organic per acids, such as perbenzoic acid or peracetic acid, or mixtures of organic acids and hydrogen peroxide, e.g. acetic acid/hydrogen peroxide;
• a compound of formula (I) obtainable according to the method or by other means, present in free form or in the form of a salt, is converted into a different compound of formula (I)
• a mixture of isomers obtainable according to the method is separated and the desired isomer is isolated and/or a free compound of formula (I) obtainable according to the method or by other means is converted into a salt, or a salt of a compound of formula (I) obtainable according to the method or by other means is converted into the free compound of formula (I) or into a different salt.
• the starting materials of formulae (II) and (III), listed hereinbefore and hereinafter, which are used to produce the compounds of formula (I), in free form or in salt form, are known or may be produced by methods known per se.
• the starting materials of formula (IV) are novel and therefore similarly form an object of the invention.
• the reactions described hereinbefore and hereinafter are carried out in a known manner, e.g. in the absence or, where appropriate, in the presence of a suitable solvent or diluent or a mixture thereof, proceeding as required under conditions of cooling, of ambient temperature, or of heating, e.g.
• reaction medium in a temperature range of about -80°C to the boiling temperature of the reaction medium, preferably about -20°C to about +150°C, and where appropriate in a closed vessel, under pressure, in an inert gas atmosphere, and/or under non-aqueous conditions.
• a temperature range of about -80°C to the boiling temperature of the reaction medium preferably about -20°C to about +150°C
• a closed vessel under pressure, in an inert gas atmosphere, and/or under non-aqueous conditions.
• non-aqueous conditions are described in the Examples.
• reaction of process a) is effected in the presence of an acid, for example HCI, sulphuric acid or phosphoric acid.
• an acid for example HCI, sulphuric acid or phosphoric acid.
• the reaction is generally carried out at temperatures of -30°C to +70°C, preferably from -10°C to +50°C.
• the process is conveniently carried out in the presence of an inert solvent or solvent mixture.
• suitable solvents for this purpose are for example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylenes, petroleum ether, hexane; halogenated hydrocarbons, such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, ethylene tetrachloride; ethers and ether-like compounds, such as dialkyl ether (diethyl ether, diisopropyl ether, tert.-butylmethyl ether, etc.), anisole, dioxane, tetrahydrofuran; nitriles such as acetonitrile, propionitrile; esters such as ethyl acetate (acetic
• the reaction is carried out at atmospheric pressure, although it may also be carried out at elevated or reduced pressure.
• the reaction is advantageously carried out in the presence of an inert solvent or solvent mixture at temperatures of -30°C to +70°C, preferably -10°C to +50°C. It is preferably carried out in the presence of a base, for example in the presence of an organic amine such as a trialkylamine (trimethylamine, triethylamine, triisopropylamine or diisopropylethylamine), a pyridine (pyridine itself, 4-dimethylaminopyridine or 4-pyrrolidino- pyridine), a morpholine (N-methylmorpholine) or a N,N-dialkylaniline (N,N-dimethylaniline or N-methyl-N-ethylaniline).
• an organic amine such as a trialkylamine (trimethylamine, triethylamine, triisopropylamine or diisopropylethylamine), a pyridine (pyridine itself, 4-dimethylaminopyridine or 4-
• Suitable solvents for this purpose are for example aliphatic and aromatic hydrocarbons, such as benzene, toluene, xylenes, petroleum ether, hexane; halogenated hydrocarbons, such as chlorobenzene, methylene chloride, ethylene chloride, chloroform, carbon tetrachloride, ethylene tetrachloride; ethers such as dialkyl ether (diethyl ether, diisopropyl ether, tert.-butylmethyl ether, etc.), anisole, dioxane, tetrahydrofuran; nitriles such as acetonitrile, propionitrile; esters such as ethyl acetate (acetic acid ethyl ester), propyl acetate or butyl acetate; and mixtures of such solvents with one another.
• aliphatic and aromatic hydrocarbons such as benzene, toluene, xy
• the reactions are expediently carried out in the presence of an inert solvent or solvent mixture at temperatures of -40°C to +120°C, preferably -20°C to +80°C.
• the solvents in question may be the same as those mentioned for variant b).
• a base for example alkali or alkaline earth metal hydroxides or for example alkali or alkaline earth metal carbonates or hydrogen carbonates, pyridine, 4-dimethylaminopyridine, 4-pyrrolidinopyridine, lutidine, collidine, trialkylamine, N,N- dialkylaniline, or a bicyclic, non-nucleophilic base such as 1 ,4-diazabicyclo[2.2.2]octane (DABCO), 1 ,5-diazabicyclo[4.3.0]non-5-ene (DBN) or 1 ,8-diazabicyclo[5.4.0]undec-7-ene (1 ,5-5) (DBU).
• DABCO 1 ,4-diazabicyclo[2.2.2]octane
• DBN 1 ,5-diazabicyclo[4.3.0]non-5-ene
• DBU 1 ,8-diazabicyclo[5.4.0]und
• Salts of compounds of formula (I) may be prepared in a known manner. For example, it is possible to obtain salts of compounds of formula (I) with bases, by treating the free compounds with an appropriate base or with an appropriate ion exchanger reagent.
• Salts of compounds of formula (I) may be converted in conventional manner into the free compounds of formula (I), e.g. by treatment with a suitable acid or with a suitable ion exchanger reagent.
• Salts of compounds of formula (I) may be transformed in known manner into other salts of a compound of formula (I).
• the compounds of formula (I) in free form or in salt form may exist in the form of one of the possible isomers or as a mixture thereof, e.g. depending on the number, the absolute and relative configuration of asymmetric carbon atoms appearing in the molecule and/or depending on the configuration of non-aromatic double bonds appearing in the molecule, as pure isomers such as antipodes and/or diastereoisomers, or as isomer mixtures such as enantiomer mixtures, e.g. racemates, diastereoisomer mixtures or racemate mixtures.
• the invention relates both to the pure isomers and to all the possible mixtures of isomers, and hereinbefore and hereinafter is to be understood as such accordingly, even if the stereo- chemical details are not specifically mentioned in each case.
• diastereoisomer mixtures, racemate mixtures and mixtures of double bond isomers of compounds of formula (I) in free form or in salt form which are obtainable by the process or in another way, may be separated in known manner, on the basis of the physical-chemical differences in their components, into the pure diastereoisomers or racemates, for example by fractiional crystallisation, distillation and/or chromatography.
• Enantiomer mixtures that are obtainable correspondingly, such as racemates may be broken down by known methods into the optical antipodes, for example by recrystallisation from an optically active solvent, by chromatography on chiral adsorbents, e.g. high pressure liquid chromatography on acetyl cellulose, with the assistance of suitable microorganisms, by cleavage with specific, immobilised enzymes, through the formation of inclusion compounds, e.g. using chiral crown ethers, whereby only one enantiomer is complexed, or by converting into diastereoisomeric salts and separating the diastereoisomer mixture obtained in this way, e.g. on the basis of their different solubilities, by fractional crystallisation, into the diastereoisomers, from which the desired enantiomer can be released upon the action of suitable agents.
• chiral adsorbents e.g. high pressure liquid chromatography on acetyl
• the invention relates to all those forms of the method, according to which one starts from a compound obtainable as a primary material or an intermediate at any stage of the method and carries out all or some of the missing steps, or uses, or - especially under the reaction conditions - produces a starting material in the form of a derivative or a salt and/or its racemate or antipodes.
• the starting materials and intermediates used are preferably those that lead to the compounds of formula (I) or salts thereof described at the beginning as being especially useful.
• the invention relates especially to the method of preparation described in Example P1.
• the compounds of formula (I) according to the invention are active ingredients of preventive and/or curative merit for use in pest control and offer a very favourable spectrum of biocidal activity with favourable tolerability in warm-blooded animals, fish, and plants even at low concentrations.
• the active ingredients according to the invention are active against all or individual development stages of animal pests showing normal sensitivity, as well as those showing resistance, such as insects or members of the order Acarina.
• the insecticidal or acaricidal effect of the active substances of the invention can manifest itself directly, i.e. killing the pests either immediately or after some time has elapsed, for example when moulting occurs, or indirectly, e.g. reducing the number of eggs laid and/or the hatching rate, good efficacy corresponding to a pesticidal rate (mortality) of at least 50 to 60%.
• the said animal pests include, for example, those which are mentioned in the European Patent application EP-A-736'252, page 2, line 55 to page 6, line 55.
• the pests mentioned therein are thus included by reference in the object of the present invention.
• the compounds according to the invention are also active against pests from the class of the nematodes, for example, of the families Filariidae and Setariidae and the genera Haemonchus, Tricho- strongylus, Ostertagia, Nematodirus, Cooperia, Ascaris, Bunostumum, Oesophagostonum, Chabertia, Trichuris, especially Trichuris vulpis, Strongylus, Trichonema, Dictyocaulus, Capillaria, Strongyloides, Heterakis, Toxocara, especially Toxocara canis, Ascaridia, Oxyuris, Ancylostoma, especially Ancylostoma caninum, Uncinaria, Toxascar
• the active ingredients according to the invention are especially suitable for controlling sucking insects, especially of the order Homoptera, preferably for controlling these pests in vegetable, fruit, rice and cotton crops.
• sucking insects especially of the order Homoptera
• One particular advantage of the compounds according to the invention is their systemic action.
• Pests of said type which occur on plants, especially on crops and ornamentals in agriculture, horticulture and forestry, or on parts of such plants, such as fruits, blooms, leaves, stems, tubers or roots, can be controlled, i.e. kept in check or eradicated, using the active ingredients of the invention, this protection remaining for parts of some plants whose growth does not occur until later.
• Target crops include especially cereals, such as wheat, barley, rye, oats, rice, corn or sorghum; beet, such as sugar beet or fodder beet; fruit, e.g. pomes, drupes and soft fruit, such as apples, pears, plums, peaches, almonds, cherries or berries, e.g.
• strawberries, raspberries or blackberries leguminous plants, such as beans, lentils, peas or soybean; oleaginous fruits, such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans or groundnuts; cucumber plants, such as squashes, cucumbers or melons; fibrous plants, such as cotton, flax, hemp or jute; citrus fruits, such as oranges, lemons, grapefruit or mandarins; vegetables, such as spinach, lettuce, asparagus, cabbages, carrots, onions, tomatoes, potatoes or paprika; lauraceae, such as avocado, cinnamon or camphor; and tobacco, nuts, coffee, aubergines, sugar cane, tea, pepper, vines, hops, banana plants, natural rubber plants and ornamentals.
• oleaginous fruits such as rape, mustard, poppy, olives, sunflowers, coconut, castor oil plants, cocoa beans or groundnuts
• cucumber plants such as squashes, cucumbers or melons
• fibrous plants such as cotton
• the invention therefore relates also to pesticides, such as emulsifiable concentrates, suspension concentrates, ready-to-spray or ready-to-dilute solutions, coatable pastes, dilute emulsions, spray powders, soluble powders, dispersible powders, wettable powders, dusts, granulates or encapsulations in polymeric substances, chosen in accordance with the intended objectives and prevailing circumstances, and comprising at least one active ingredient of the invention.
• pesticides such as emulsifiable concentrates, suspension concentrates, ready-to-spray or ready-to-dilute solutions, coatable pastes, dilute emulsions, spray powders, soluble powders, dispersible powders, wettable powders, dusts, granulates or encapsulations in polymeric substances, chosen in accordance with the intended objectives and prevailing circumstances, and comprising at least one active ingredient of the invention.
• the active ingredient is used in these compositions in pure form, a solid active ingredient e.g. in a specific particle size, or preferably together with at least one of the adjuvants conventionally employed in the art of formulation, such as extenders, e.g. solvents or solid carriers, or surface-active compounds (surfactants).
• adjuvants conventionally employed in the art of formulation, such as extenders, e.g. solvents or solid carriers, or surface-active compounds (surfactants).
• the adjuvants which can be used for formulation are, for example, solid carriers, solvents, stabilisers, "slow-release” agents, dyes, and where appropriate surfactants.
• Carriers and adjuvants can be any substance conventionally used in crop protection agents, especially agents for slug and snail control.
• Adjuvants such as solvents, solid carriers, surface-active agents, non-ionic surfactants, cationic surfactants, anionic surfactants, and other adjuvants in the compositions of the invention can, for example, be the same as those described in EP- A-736'252 , and are included by reference in the object of the present invention.
• the compositions comprise 0.1 to 99%, especially 0.1 to 95%, of active ingredient and 1 to 99.9%, especially 5 to 99.9%, of at least one solid or liquid adjuvant, it being possible as a rule for 0 to 25%, especially 0.1 to 20%, of the composition to be surfactants (% in each case meaning percent by weight).
• surfactants % in each case meaning percent by weight.
• Emulsifiable concentrates active ingredient: 1 to 95%, preferably 5 to 20% surfactant: 1 to 30%, preferably 10 to 20 % solvent: 5 to 98%, preferably 70 to 85%
• Dusts active ingredient: 0.1 to 10%, preferably 0.1 to 1% solid carrier: 99.9 to 90%, preferably 99.9 to 99%
• Suspension concentrates active ingredient: 5 to 75%, preferably 10 to 50% water: 94 to 24%, preferably 88 to 30% surfactant: 1 to 40%, preferably 2 to 30%
• Wettable powders active ingredient: 0.5 to 90%, preferably 1 to 80% surfactant: 0.5 to 20%, preferably 1 to 15% solid carrier: 5 to 99%, preferably 15 to 98%
• Granulates active ingredient: 0.5 to 30%, preferably 3 to 15% solid carrier: 99.5 to 70%, preferably 97 to 85%
• compositions of the invention can be substantially broadened and adapted to prevailing circumstances by adding other insecticidal substances.
• Additional active ingredients are, for example, substances from the following classes: organic phosphorus compounds, nitrophenols and their derivatives, formamidines, acylureas, carbamates, pyre- throids, neonicotinoides and their derivatives, pyrroles, thioureas and their derivatives, chlorinated hydrocarbons and Bacillus thuringiensis preparations.
• azamethiphos chlorfenvinphos; cypermethrin, cypermethrin high- cis; cyromazin; diafenthiuron; diazinon; dichlorvos; dicrotophos; dicyclanil; fenoxycarb; fluazuron; furathiocarb; isazofos; iodofenphos; kinoprene; lufenuron; methacriphos; methi- dathion; monocrotophos; phosphamidon; profenofos; diofenolan; a substance obtainable from the Bacillus thuringiensis strain GC91 or from NCTC11821; pymetrozine; bromo- propylate; methoprene; disulfuton; quinalphos; tau-fluvalinate; thiocyclam; thiometon; aldicarb; azinphos-methyl
• compositions of the invention can also contain further solid or liquid adjuvants, such as stabilisers, e.g. vegetable oils, epoxidized where appropriate (e.g. epoxidized coconut oil, rapeseed oil or soya oil), antifoaming agents, e.g. silicone oil, preservatives, viscosity modulators, binders and/or tackifiers, as well as fertilisers or other active ingredients to achieve specific effects, e.g. acaricides, bactericides, fungicides, nematocides, molluscicides or selective herbicides.
• stabilisers e.g. vegetable oils, epoxidized where appropriate (e.g. epoxidized coconut oil, rapeseed oil or soya oil), antifoaming agents, e.g. silicone oil, preservatives, viscosity modulators, binders and/or tackifiers, as well as fertilisers or other active ingredients to achieve specific
• compositions of the invention are prepared in a known manner, in the absence of adjuvants, for example, by grinding, sieving, and/or compressing a solid active ingredient or active ingredient mixture, e.g. to a specific particle size, and in the presence of at least one adjuvant, for example, by intimately mixing and/or grinding the active ingredient or the mixture of active ingredients with the adjuvant(s).
• adjuvants for example, by grinding, sieving, and/or compressing a solid active ingredient or active ingredient mixture, e.g. to a specific particle size
• at least one adjuvant for example, by intimately mixing and/or grinding the active ingredient or the mixture of active ingredients with the adjuvant(s).
• Typical concentrations of active ingredient are between 0.1 and 1000 ppm, preferably between 0.1 and 500 ppm.
• the rates of application are generally 1 to 2000 g of active ingredient per hectare, especially 10 to 1000 g/ha, and preferably 20 to 600 g/ha.
• a preferred method of application for crop protection is to apply the active ingredient to the foliage of the plants (leaf application), the number of applications and the rate of application depending on the intensity of infestation by the pest in question.
• the active ingredients can also penetrate the plant through the roots (systemic action) by impregnating the locus of the plant with a liquid composition, or by applying the active ingredient in solid form to the locus of the plants, e.g. the soil, for example in granular form (soil application). With paddy rice cultures, granules may be metered into the flooded paddy field.
• compositions of the invention are also suitable for protecting plant propagation material, including genetically modified propagation material, e.g. seeds, such as fruits, tubers or grains, or plant seedlings, from animal pests.
• the propagation material can be treated with the composition before the start of cultivation, seeds for example being dressed before they are sown.
• the active ingredients of the invention can also be applied to seeds (coating) by either soaking the seeds in a liquid composition or coating them with a solid composition.
• the composition can also be applied when the propagation material is introduced to the place of cultivation, e.g. when the seeds are sown in the seed furrow.
• the treatment procedures for plant propagation material and the propagation material thus treated are further objects of the invention.
• Example P2 The remaining compounds of Table 1 may be produced analogously to the manner described above.
• Example F1 Emulsion concentrates a) b) c) active ingredient 25% 40% 50% calcium dodecylbenzenesulphonate 5% 8% 6% castor oil polyethylene glycol ether(36 mols EO) 5% - - tributyl phenol polyethylene glycol ether (30 mols EO) - 12% 4% cyclohexanone - 15% 20% xylene mixture 65% 25% 20%
• Example F2 Solutions a) b) c) d) active ingredient 80% 10% 5% 95% ethylene glycol monomethyl ether 20% - - - polyethylene glycol (MW 400) - 70% - -
• N-methylpyrrolid-2-one 20% - - epoxidised coconut oil - - 1% 5% petrol (boiling limits: 160-190°) - - 94% -
• Example F3 Granulates 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 sprayed onto the carrier mixture, and the solvent evaporated off under vacuum.
• Example B1 Effect on Diabrotica balteata larvae
• Corn seedlings are sprayed with an aqueous emulsion spray mixture containing 400 ppm of active ingredient. After drying of the spray deposit, the corn seedlings are colonised with 10 second instar larvae of Diabrotica balteata and placed in a plastic container. Six days later they are evaluated. The percentage reduction of the population (% response) is determined by comparing the number of dead larvae on the treated plants with those on the untreated plants.
• Especially compound 1.2 has an effect of over 80%.
• Example B2 Systemic effect against Myzus persicae
• Pea seedlings are infected with Myzus persicae, then the roots are placed in a spray mixture containing 400 ppm of active ingredient, and incubated at 20°C. 3 and 6 days later, they are evaluated.
• the percentage reduction of the population is determined by comparing the number of dead aphids on the treated plants with those on the untreated plants.
• Especially compound 1.2 has an effect of over 80%.

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