Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00

Definitions

• the present invention relates to novel condensed bicyclic heterocyclic derivatives of the formula (I) or the formula ( ⁇ ), their use as acaricides and / or insecticides for combating animal pests, especially arthropods and in particular of insects and arachnids, and methods and intermediates their production.
• condensed bicyclic heterocyclic derivatives which have advantages over the already known compounds, e.g. are better biological or ecological properties, broader application methods, better insecticides, acaricidal activity, as well as a good tolerance to crops exemplified.
• the condensed bicyclic heterocyclic derivatives can be used in combination with other agents for improving the effectiveness in particular against difficult-to-control insects.
• the present invention therefore relates to novel compounds of the formulas (I) or (II)
• Aa is nitrogen or ⁇ (a carbon atom with a double bond to Ab or Ad),
• R 1 alkyl is (Ci-C 6) alkyl, (Ci-C 6) haloalkyl, (Ci-C 6) cyanoalkyl, (Ci-C 6) hydroxyalkyl, (Ci-C6) alkoxy (Ci-C 6) , (Ci-C 6) haloalkoxy (Ci-C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6)
• C8 cycloalkylamino, (Ci-C6) alkylcarbonyl-amino, (Ci-C6) alkylthio (Ci-C6) alkyl, (Ci- C 6) haloalkylthio (Ci-C 6) alkyl, (Ci-C 6) Alkylsulfinyl- (C 1 -C 6 ) -alkyl,
• Hetaryl or heterocyclyl substituted (C 1 -C 6) alkyl, (C 1 -C 6) alkoxy, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, (C 3 -C 8 ) cycloalkyl, wherein aryl, hetaryl or heterocyclyl respectively optionally mono- or polysubstituted, identically or differently, by halogen, cyano, nitro, hydroxyl, amino, carboxy, carbamoyl, aminosulfonyl, (C 1 -C 6 ) -alkyl, (C 3 -C 6 ) -cycloalkyl, (C 1 -C 6 ) -alkoxy, C 6) haloalkyl, (Ci-C 6) haloalkoxy, (Ci-C 6) alkylthio, (Ci-C 6) alkylsulfinyl,
• R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 independently of one another represent hydrogen, cyano, halogen,
• C8 cycloalkylaminocarbonyl (Ci-C6) alkylsulfonylamino, (Ci-C6) alkylamino, di (Ci- C6) alkylamino, aminosulfonyl, (Ci-C6) alkylaminosulfonyl, di (Ci-Ce) alkyl aminosulfonyl, (C -C6) alkylsulfoximino, aminothiocarbonyl, (
• C8 cycloalkylamino or NHCO- (Ci-Ce) alkyl ((Ci-C6) alkylcarbonylamino are) hydrogen, acetyl, (Ci-C 4) alkyl, (Ci-C 4) hydroxyalkyl, (Ci-C 4) haloalkyl, (Ci C 4) cyanoalkyl, (Ci-C 4) alkoxy (Ci-C 4) alkyl, (Ci-C 4) haloalkoxy (Ci-C 4) alkyl, (C 2 - C 4) alkenyl , (C 2 -C 4) alkenyloxy (Ci-C 4) alkyl, (C 2 -C 4) Halogenalkenyloxy- (Ci-C 4) alkyl, (C 2 - C 4) haloalkenyl, (C 2 -C 4 ) cyanoalkenyl, (C 2 -C 4) alky
• C ⁇ ) alkylcarbonylamino), - or wherein the substituents may be independently selected from phenyl or a 5- or 6-membered heteroaromatic ring, wherein phenyl or the ring optionally mono- or polysubstituted by C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl , C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, Ci-C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, halogen, CN , NO 2 , C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, is 0, 1 or 2, stands for 0, 1 or 2,
• the compounds of the formulas (I) or (II) have very good activity as pesticides, preferably as insecticides and / or acaricides, moreover, as a rule, are very well tolerated by plants, in particular with respect to crop plants.
• Aa is preferably nitrogen
• R 1 is preferably (Ci-C 4 ) alkyl, (Ci-C 4 ) hydroxyalkyl, (Ci-C 4 ) haloalkyl, (C 2 -C 4 ) alkenyl, (C 2 -C 4 ) haloalkenyl, (C 2 -C 4 ) alkynyl, (C 2 -C 4 ) haloalkynyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkylthio (C 1 -C 4 ) alkyl, (C 1 -C 4 ) haloalkylthio (Ci -C 4) alkyl, (Ci-C 4) alkylsulfinyl (CI-C 4) alkyl, (Ci-C 4) alkylsulfonyl (Ci-C 4) alkyl, or represents in each case optionally monosubstituted or disubstitute
• R 2 , R 3 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 independently of one another preferably represent hydrogen
• R 7 is preferably hydrogen, acetyl, (Ci-C) alkyl, (Ci-C) haloalkyl, (Ci-C) cyanoalkyl, (Ci-C 4 ) alkoxy (Ci-C 4 ) alkyl, (Ci-C 4 ) haloalkoxy- (C 1 -C 4 ) alkyl, (C 3 -C 6 ) cycloalkyl, (C 1 -C 4 ) alkyl- (C 3 -C 6 ) cycloalkyl, halo (C 3 -C 6 ) cycloalkyl, (Ci -C 4) alkylthio (Ci-C 4) alkyl, or represents in each case optionally mono- or disubstituted by identical or different aryl or heterocyclyl substituted (Ci-C 4) alkyl, wherein aryl or heterocyclyl each optionally monosubstituted or disubstitute
• Q preferably represents a heteroaromatic 9-membered or 12-membered fused bicyclic or tricyclic ring system from the series Q1 to QU, Q14 to Q17 or Q20,
• R 4 is preferably (Ci-C 4) alkyl, (Ci-C 4) haloalkyl, (Ci-C 4) cyanoalkyl, - -
• R 5, R 6 independently of one another preferably represent hydrogen, cyano, halogen, (Ci-C 4) alkyl, (Ci C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) alkynyl, (C 2 - C 4) -haloalkynyl, (C 3 -C 6) cycloalkyl, (C3-C6) cycloalkyl (C3-C6) cycloalkyl (C3-C6) cycloalkyl, (Ci-C 4) alkyl (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy, (C 1 -C 4) alkoxyimino, (C 1 -C 4) -alkylthio,
• Aa is particularly preferably nitrogen
• the following structural units are particularly preferably obtained: A5, A6, A7, A8, A9, A10, Al1, A12, A13, A19, A20,
• R 1 particularly preferably represents (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -haloalkyl or (C 3 -C 6 ) -cycloalkyl,
• R 2 , R 3 , R 8 independently of one another particularly preferably represent hydrogen, cyano, halogen,
• R 7 particularly preferably represents hydrogen, (Ci-C4) alkyl, (Ci-C4) haloalkyl, (CI-C 4) cyanoalkyl or (Ci-C 4) alkoxy (Ci-C 4) alkyl,
• Q particularly preferably represents a 9-membered heteroaromatic bicyclic ring system of the series Q1, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17,
• R 4 particularly preferably represents (C 1 -C 4 ) -alkyl or (C 1 -C 4 ) -alkoxy- (C 1 -C 4 ) -alkyl,
• R 5 is particularly preferably halogen, (C 1 -C 4) haloalkyl, (C 1 -C 4) haloalkoxy or (C 1 -C 4) haloalkylthio,
• R 6 is particularly preferably hydrogen, n is particularly preferably 0, 1 or 2, m is particularly preferably 0.
• Aa is very particularly preferably nitrogen
• Ad is very particularly preferably -S (0) m -, - -O- or -N (R 7 ) -. where very particular preference is given to the following structural units: A6, A10, Al1, A12, A13,
• A12 A13 R 1 very particularly preferably represents ethyl
• R 2 , R 3 independently of one another very particularly preferably represent hydrogen, fluorine, chlorine,
• R 7 very particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl, sec-propyl or tert-butyl, very particularly preferably represents a heteroaromatic 9-membered fused bicyclic ring system from the series Q 2 or Q 3,
• R 4 very particularly preferably represents methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl,
• R 5 very particularly preferably represents fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CFH 2 , CHFCH 3 ), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3 , CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy or trifluoromethylthio,
• R 6 is very particularly preferably hydrogen, n is very particularly preferably 0, 1 or 2, m is very particularly preferably 0.
• Aa stands for nitrogen
• Ad stands for -S (0) m -, the result being the following structural units: Al 1, R 1 stands for ethyl,
• R 2 , R 3 are hydrogen
• R 5 stands for trifluoromethyl
• R 6 stands for hydrogen, n stands for 0 or 2, m stands for 0. Configuration 5-2
• Aa stands for nitrogen
• Ad stands for -S (0) m -, with the following structural units being highlighted: A 11,
• R 1 stands for ethyl
• R 2 is hydrogen
• R 3 is hydrogen or trifluoromethyl
• R 4 is methyl
• R 3 stands for trifluoromethyl
• R 6 is hydrogen, n is 0 or 2, m is highlighted for 0.
• Aa stands for nitrogen in particular
• Ad stands in particular for -C (R 13 ) (R 14 ) -,
• R 1 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and n have the meanings given in embodiment 1.
• Aa stands for nitrogen in particular
• Ad stands in particular for -C (R 1 ) (R 14 ) -,
• R 1 , R 4 , R 5 , R 6 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 and n have the meanings given in embodiment 2.
• Aa stands for nitrogen in particular
• Ad stands in particular for -C (R 13 ) (R 14 ) -,
• R 1 stands for particular (Ci-C 4) alkyl, (Ci-C 4) haloalkyl or (C 3 -C 6) cycloalkyl
• R 9 , R 10 , R 11 , R 12 , R 13 , R 14 are, independently of one another, particularly hydrogen
• Q is especially for a heteroaromatic 9-membered annell investigatings bicyclic ring system from the series Ql, Q2, Q3, Q4, Q5, Q6, Q8, Q9, Q10, Q15, Q17, R 4 is in particular is (Ci-C 4) alkyl or (C 1 -C 4 ) alkoxy- (C 1 -C 4 ) -alkyl,
• R 5 is in particular halogen, (Ci-C 4) haloalkyl, (Ci-C 4) haloalkoxy or (Ci- C4) haloalkylthio,
• R 6 is in particular hydrogen, n is in particular 0, 1 or 2.
• Aa stands for nitrogen in particular
• Ad stands in particular for -C (R 13 ) (R 14 ) -, whereby in particular the following structural units result: AI,
• R 1 is especially ethyl
• R 9 , R 10 , R 11 , R 12 , R 13 , R 14 independently of one another are especially hydrogen, methyl or ethyl
• Q is in particular a heteroaromatic 9-membered fused bicyclic ring system from the series Q2 or Q3,
• R 4 is especially methyl, ethyl, i-propyl, methoxymethyl or methoxyethyl, - -
• R 5 is in particular fluorine, chlorine, bromine, fluoromethyl, difluoromethyl, trifluoromethyl, fluoroethyl (CH 2 CFH 2 , CHFCH 3 ), difluoroethyl (CF 2 CH 3 , CH 2 CHF 2 , CHFCFH 2 ), trifluoroethyl, (CH 2 CF 3 , CHFCHF 2 , CF 2 CFH 2 ), tetrafluoroethyl (CHFCF 3 , CF 2 CHF 2 ), pentafluoroethyl, trifluoromethoxy, difluorochloromethoxy, dichlorofluoromethoxy or trifluoromethylthio, R 6 is in particular hydrogen, n is especially 0, 1 or 2.
• Ab in particular stands for -C (R 9 ) (R 10 ) -
• Ac stands in particular for -C (R U ) (R 12 ) -
• ad stands in particular for -C (R 13 ) (R 14 ) -, wherein in particular the following structural units are obtained: Al, R 1 is in particular ethyl,
• R 9 , R 10 , R 11 , R 12 , R 13 , R 14 are in particular hydrogen
• Q is in particular a heteroaromatic 9-membered fused bicyclic ring system from the series Q3
• R 4 is especially methyl
• R 5 is especially trifluoromethyl
• R 6 is in particular hydrogen, n is insbesosnders for 2.
• the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m have the meanings given in embodiment (1).
• the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m are those in Embodiment (2) or Embodiment (3) or Embodiment (4) or Embodiment (5-1) or Embodiment (5-2) or Embodiment (6-1) or Embodiment (6-2) or Embodiment (6-3) or Embodiment (6-4) - - or embodiment (6-5) have specified meanings.
• the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m have the meanings given in embodiment (1).
• the invention relates to compounds of the formula (I) in which R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , Q, Aa, Ab, Ac, Ad, n and m are those in Embodiment (2) or Embodiment (3) or Embodiment (4) or Embodiment (5-1) or Embodiment (5-2) or design (6-1) or design (6-2) or design (6-3) or design (6-4) or design (6-5) have specified meanings.
• the invention relates to compounds of the formula (I) of the structural unit Al 1
• R 1 , R 2 , R 3 , R 4 , R 5 , R 6 and n are those in embodiment (2) or embodiment (3) or embodiment (4) or embodiment (5-1) or embodiment Have (5-2) indicated meanings.
• the invention relates to compounds of the formula (I) of the structural unit AI
• the invention relates to compounds of the formula (I) of the structural unit AI - -
• Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
• Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
• alkyl either alone or in combination with other terms, such as, for example, haloalkyl, in the context of the present invention means a radical of a saturated, aliphatic hydrocarbon group having 1 to 12 carbon atoms, which may be branched or unbranched Examples of C 1 -C 2 -alkyl radicals are methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, n-pentyl, iso-pentyl, neopentyl, tert-pentyl, 1-methylbutyl, 2-methylbutyl, 1-ethylpropyl, 1,2-dimethylpropyl, hexyl n -heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl and n
• alkenyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 2 -alkenyl radical having at least one double bond, for example vinyl, allyl , 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,3-butadienyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1,3-pentadienyl, 1-hexenyl , understood.
• 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl and 1, 4-hexadienyl thereof are C 2 -C 6 alkenyl groups and particularly preferred are C 2 -C 4 -alkenyl.
• alkynyl either alone or in combination with other terms, according to the invention a linear or branched C 2 -C 2 alkynyl having at least one triple bond, for example ethynyl, 1 Propynyl and propargyl, preferably C3-C6 alkynyl radicals and C 3 -C 4 -alkynyl radicals are particularly preferred.
• the alkynyl radical can also have at least one double bond.
• cycloalkyl either alone or in combination with other terms, according to the invention a C3-C8-cycloalkyl understood, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl and cyclooctyl, understood Preferred of these are C 3 -C 6 -cycloalkyl radicals.
• alkoxy either alone or in combination with other terms, such as, for example, haloalkoxy, is understood herein to mean a radical O-alkyl, the term “alkyl” having the meaning given above.
• Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
• optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
• Very particularly preferably used according to the invention are compounds of the formulas (I) or (II) which contain a combination of the meanings given above as being very particularly preferred.
• the compounds of the formulas (I) or (II) can be used as geometric and / or as optically active isomers or corresponding isomer mixtures in different composition.
• These stereoisomers are, for example, enantiomers, diastereomers, atropisomers or geometric isomers.
• the invention thus comprises pure stereoisomers as well as any mixtures of these isomers.
• the compounds of the formula (I) in which Q is Q1 to Q9 or Q20 can be prepared by known methods, for example analogously to those described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, WO2015 / 000715 and WO2015 / 121136.
• R 1 , R 4 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above, A 2 and A 3 are CH or N (where A 2 and A 3 are not simultaneously N A 4 is O, S or NR 4 and X 1 is halogen. - - Step a)
• the compounds of the formula (IV) can be prepared in analogy to the process described in US Pat. No. 5,573,335 by reacting compounds of the formula (II) with carboxylic acids of the formula (III) in the presence of a condensing agent or a base.
• Compounds of the formula (II) are either commercially available or can be prepared by known methods, for example analogously to US2003 / 69257, WO2006 / 65703, WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928 or WO2015 / 000715 described method.
• Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G.
• reaction of the compounds of the formula (II) with carboxylic acids of the formula (III) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
• ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
• halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene
• Nitriles such as acetonitrile or propionitrile
• aromatic hydrocarbons such as toluene or xylene
• aprotic polar solvents such as N, N-
• Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
• carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
• bases are inorganic bases which are commonly used in such reactions.
• bases are used which are selected by way of example from the group consisting of acetates, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals.
• Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
• the reaction can be carried out in vacuo, under normal pressure or under excess pressure and at temperatures of 0 ° C to 180 ° C, preferably the reaction is carried out at atmospheric pressure and temperatures of 20 to 140 ° C.
• the compounds of the formula (V) can be prepared by condensation of the compounds of the formula (IV), for example analogously to those in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, - -
• the reaction to give compounds of the formula (V) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
• ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
• the reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.
• suitable condensing agents are carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azo diester such as e.g. Diethylazodicarbonklare.
• carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide
• Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachlor
• acids examples include sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
• suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
• nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
• DBU 1,8-diazabicyclo [5.4.0] -7-undecene
• tertiary amines such as triethylamine and N, N
• An example of a suitable chlorinating agent is phosphorus oxychloride.
• the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
• the compounds of the formula (I) wherein n is 0 can be prepared by reacting the compounds of the formula (V) with the compounds of the formula (Via) in the presence of a base.
• Mercaptan derivatives of the formula (IVa) such as, for example, methylmercaptan, ethylmercaptan or isopropylmercaptan, are either commercially available or can be prepared by known methods - be prepared, for example analogously to those in US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329 described method.
• the reaction to give compound of formula (I) wherein n is 0 may be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent selected from conventional solvents inert to the prevailing reaction conditions.
• ethers for example diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, tert-butyl methyl ether; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as ⁇ , ⁇ -dimethylformamide, N-methylpyrrolidone or dimethyl sulfoxide.
• suitable bases are inorganic bases from the group consisting of acetates, phosphates and carbonates of alkali or alkaline earth metals. Cesium carbonate, sodium carbonate and potassium carbonate are preferred. Other suitable bases are alkali metal hydrides, e.g. Sodium hydride.
• the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
• X 1 is preferably a fluorine or chlorine atom.
• the compounds of formula (I) wherein n is 1 may be prepared by oxidation of the compounds of formula (I) wherein n is 0.
• the oxidation is generally carried out in a solvent selected from conventional solvents which are inert under the prevailing reaction conditions. Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
• suitable oxidizing agents are hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
• the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
• Step e) The compounds of formula (I) wherein n is 2 can be prepared by oxidation of the compounds of formula (I) wherein n is 1.
• the oxidation is generally in a solvent - - carried out.
• Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
• Suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
• the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
• the compounds of the formula (I) wherein n is 2 can also be prepared in a one-step process by oxidation of the compounds of the formula (I) where n is 0.
• the oxidation is generally carried out in a solvent.
• Preference is given to halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
• Suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
• the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
• Process A-2 The compounds of the formula (I) in which Q is Ql to Q9, Q17 or Q20 can be prepared by known methods, for example analogously to those described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928, WO2015 / 000715 and WO2015 / 121136.
• R 1 , R 4 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above, A 2 and A 3 are CH or N, A 4 is O, S or NR 4 , M is lithium, sodium or potassium and X 1 - - stands for halogen.
• compounds of formula (I) wherein n is 2 may also be prepared in a one-step process, for example, by analogy to the methods described in Journal of Organic Chemistry 2005, 70, 2696-2700, by a halogen-sulfone substitution a compound of formula (VIb) starting from compounds of formula (V).
• the exchange is generally carried out in a solvent. Preference is given to using polar aprotic solvents, for example dimethyl sulfoxide and ⁇ , ⁇ -dimethylformamide.
• sulfur reagents examples include the lithium, sodium or potassium salts of sulfinic acid.
• the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
• R 1 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above.
• a 2 , A 3 , A 4 and A 5 are CH or N (wherein A 2 , A 3 , A 4 and A 5 are not simultaneously N) and X 1 is halo.
• Carboxylic acids of the formula (III) are converted in analogy to the process described in WO2011 / 75643 or EP2671582 in the presence of ⁇ , ⁇ -dimethylhydroxylamine hydrochloride into Weinreb amides of the formula (VI).
• Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G.
• the compounds of the formula (X) can be prepared by cyclization of the compounds of the formula (VIII) with amines of the formula (IX).
• the cyclization is carried out, for example, in ethanol, acetonitrile or ⁇ , ⁇ -dimethylformamide by known methods analogously to, for example, WO2005 / 66177, WO2012 / 88411, WO2013 / 3298, US2009 / 203705, US2012 / 258951, WO2012 / 168733, WO2014 / 187762 or J. Med. Chem. 31 (1988) 1590-1595.
• the compounds of the formula (I) wherein n is 0 can be prepared by reacting the compounds of the formula (X) with the compounds of the formula (Via) in the presence of a base.
• Mercaptan derivatives of the formula (Via) such as, for example, methylmercaptan, ethylmercaptan or isopropylmercaptan, are either commercially available or can be prepared by known methods, for example analogously to US2006 / 25633, US2006 / 111591, US2820062, Chemical Communications, 13 (2000), 1163-1164 or Journal of the American Chemical Society, 44 (1922), p. 1329 described method.
• the compounds of formula (I) wherein n is 1 may be prepared by oxidation of the compounds of formula (I) wherein n is 0.
• the oxidation is carried out by known methods with a suitable oxidizing agent such recordable as hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
• a suitable oxidizing agent such recordable as hydrogen peroxide, meta-chloroperbenzoic acid or sodium periodate.
• the compounds of formula (I) wherein n is 2 may be prepared by oxidation of the compounds of formula (I) wherein n is 1.
• the oxidation is generally carried out in a solvent.
• halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1,2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
• suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
• the compounds of the formula (I) wherein n is 2 can also be prepared in a one-step process by oxidation of the compounds of the formula (I) where n is 0.
• the oxidation is generally carried out in a solvent.
• halogenated hydrocarbons such as, for example, dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Alcohols such as methanol or ethanol; Formic acid, acetic acid. Propionic acid or water.
• suitable oxidizing agents are hydrogen peroxide and meta-chloroperbenzoic acid.
• the compounds of the formula (I) in which Q is Q10, QU, Q15 and Q16 can be prepared by known methods, for example analogously to those described in US2009 / 203705, US2012 / 258951, WO2013 / 3298 or J. Med. Chem. 31, (1988) 1590-1595.
• R 1 , R 4 , R 5 , R 6 , Aa, Ab, Ac, Ad and n have the meanings described above, A 2 , A 3 , A 4 and A 5 are CH or N, M is lithium , Sodium or potassium and X 1 is halogen.
• compounds of formula (I) wherein n is 2 may also be prepared in a one-step process, for example, by analogy to the methods described in Journal of Organic Chemistry 2005, 70, 2696-2700, by a halogen-sulfone substitution a compound of formula (VIb) starting from compounds of formula (X).
• the exchange is generally carried out in a solvent. Preference is given to using polar aprotic solvents, for example dimethyl sulfoxide and N, N-dimethylformamide.
• Suitable sulfur reagents are the lithium, sodium or potassium salts of sulfinic acid.
• the reaction can be carried out in vacuo, at atmospheric pressure or under excess pressure and at temperatures of -20 ° C ° C to 120 ° C.
• the compounds of the formula (I) in which Q is Q17 can be prepared by known methods, for example analogously to the processes described in WO2014 / 142292.
• R 4 , R 5 , R 6 , Aa, Ab, Ac and Ad have the meanings described above.
• X 1 is halogen.
• the compounds of the formula (XI) can be prepared by reacting, analogously to the process described in US Pat. No. 5,374,446 or Bioorganic and Medicinal Chemistry Letters 2003, 13, 1093-1096
• Compounds of formula (III) can be prepared with an ammonia source in the presence of a condensing agent.
• Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G.
• the reaction of the compounds of the formula (III) with the source of ammonia is preferably carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions. Preference is given to ethers such as, for example, dioxane or tetrahydrofuran.
• a suitable condensing agent is, for example, carbonyldiimidazole.
• the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure. Preferably, the reaction is carried out at atmospheric pressure and temperatures of 20 to 70 ° C.
• the compounds of the formula (XIII) can be prepared in analogy to the process described in WO2014 / 142292 by the reaction of compounds of the formula (XI) with compounds of the formula (XII) in the presence of a palladium catalyst in basic.
• the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure. Preferably, the reaction is carried out at atmospheric pressure and temperatures of 20 to 110 ° C.
• R 4 , R 5 , R 6 , Aa, Ab, Ac and Ad have the meanings described above.
• X 1 is halogen.
• Step a) The compounds of the formula (XV) can be prepared in analogy to the process described in WO2011 / 073149 or US5576335 by reacting compounds of the formula (XIV) with a carboxylic acid of the formula (III) in the presence of a condensing agent or a base become.
• Carboxylic acids of the formula (III) are either commercially available or can be prepared by known methods. Possible preparation routes are described in methods E, F and G.
• the reaction of the compounds of the formula (XIV) with carboxylic acids of the formula (III) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
• ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine. - -
• Suitable condensing agents are, for example, carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
• carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide.
• bases are inorganic bases which are commonly used in such reactions.
• bases are used which are selected by way of example from the group consisting of acetates, phosphates, carbonates and bicarbonates of alkali or alkaline earth metals.
• Particularly preferred are sodium acetate, sodium phosphate, potassium phosphate, cesium carbonate, sodium carbonate, potassium carbonate, sodium bicarbonate, potassium bicarbonate.
• the reaction can be carried out in vacuo, under normal pressure or under excess pressure and at temperatures of 0 ° C to 180 ° C, preferably the reaction is carried out at atmospheric pressure and temperatures of 20 to 140 ° C.
• the compounds of formula (XVI) can be prepared by condensation of the compounds of formula (XV) e.g. analogously to the process described in WO2009 / 131237, WO2010 / 125985, WO2011 / 043404, WO2011 / 040629, WO2012 / 086848, WO2013 / 018928 or WO2015 / 000715.
• the reaction to give compounds of the formula (XVI) can be carried out in bulk or in a solvent, preferably the reaction is carried out in a solvent which is selected from conventional solvents which are inert under the prevailing reaction conditions.
• ethers such as diisopropyl ether, dioxane, tetrahydrofuran, 1, 2-dimethoxyethane, tert-butyl methyl ether; halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene; Nitriles, such as acetonitrile or propionitrile; aromatic hydrocarbons such as toluene or xylene; aprotic polar solvents such as N, N-dimethylformamide or N-methylpyrrolidone or nitrogen-containing compounds such as pyridine.
• halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, 1, 2-dichloroethane or chlorobenzene
• Nitriles such as acetonitrile or propionitrile
• aromatic hydrocarbons such as toluene or xylene
• the reaction can be carried out in the presence of a condensing agent, an acid, a base or a chlorinating agent.
• suitable condensing agents are carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide; Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachloride or a mixture of triphenylphosphine and an azo diester such as e.g. Diethylazodicarbonklare.
• carbodiimides such as 1- (3-dimethylaminopropyl) -3-ethylcarbodiimide hydrochloride (EDCI) or 1,3-dicyclohexylcarbodiimide
• Anhydrides such as acetic anhydride, trifluoroacetic anhydride; a mixture of triphenylphosphine, a base and carbon tetrachlor
• suitable acids that can be used in the reaction described are sulfonic acids such as para-toluenesulfonic acid; Carboxylic acids such as acetic acid or polyphosphoric acids.
• suitable bases are nitrogen-containing heterocycles such as pyridine, picoline, 2,6-lutidine, 1,8-diazabicyclo [5.4.0] -7-undecene (DBU); tertiary amines such as triethylamine and N, N-diisopropylethylamine; inorganic bases such as potassium phosphate, potassium carbonate and sodium hydride.
• An example of a suitable chlorinating agent is phosphorus oxychloride.
• the reaction can be carried out in vacuo, at atmospheric pressure or under overpressure and at temperatures of 0 ° C to 200 ° C.
• Carboxylic acids of the formula (IIIa) with the structural unit AI are either commercially available or can be prepared by known methods, for example from pyrrolidine derivatives analogous to those described in WO2011 / 098904, Chemical Communications, 48 (2012), 3133-3135, Organic Letters , 6 (2004), 3525-3528, Journal of Organic Chemistry, 73 (2008), 312-315, Journal of the American Chemical Society, 131 (2009), 1766-1774, Journal of the American Chemical Society, 135 (2013 ), 9588-9591, Journal of the American Chemical Society, 133 (2011), 12394-12397, Journal of the American Chemical Society, 130, (2008), 1570-1571 and Organic Letters, 8 (2006), 5303-5305 described method. - -
• R 9 , R 10 , R 11 , R 12 , R 13 and R 14 have the meanings described above.
• X 1 is halogen and R 15 is (Ci-C 6 ) alkyl or aryl (Ci-C 2 ) alkyl. Step a), b), c)
• the compounds of the formula (XXII) can be prepared by reacting compounds of the formula (XXI) with a propiolate of the formula (XX) under neutral conditions in analogy to the processes described in Chemical Communications, 48 (2012), 3133-3135 and WO2011 / 098904 Conditions in a Michael addition followed by diazotization at the oc-carbon of the Michael adduct using typical diazotization reagents and subsequent cyclization under basic conditions to the desired 6,7-dihydro-5H-pyrrolo [1,2-a] imidazole getting produced.
• the compounds of formula (XXI) are either commercially available or can be prepared by known methods, for example analogously to those described in Organic Letters, 6 (2004), 3525-3528, Journal of Organic Chemistry, 73 (2008), 312-315, Journal of the American Chemical Society, 131 (2009), 1766-1774, Journal of the American Chemical Society, 135 (2013), 9588-9591, Journal of the American Chemical Society, 133 (2011), 12394-12397, Journal of the American Chemical Society, 130, (2008), 1570-1571 and Organic Letters, 8 (2006), 5303-5305.
• Compounds of formula (XXIII) may be prepared by known methods, for example via direct ortho-lithiation followed by trapping of the carbanion with a suitable electrophilic halogenating reagent or alternatively via a carboxylic acid derivative - -
• Compounds of the formula (IIIa) can be prepared by known methods from compounds of the formula (XXIII) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions.
• Carboxylic acids of the formula (IIIb) having the structural units A2, A3 or A4 are either commercially available or can be prepared by known methods, for example from oxazolidinone, thiazolidinone or imidazolidinone derivatives analogous to those described in Russian Journal of Organic Chemistry, 46 (US Pat.
• R 9 , R 10 , R 11 and R 12 have the meanings described above.
• Ad stands for -S (0) m -, -O- or -N (R 7 ) -.
• X 1 and X 2 are halogen, R 15 is (Ci-C 4 ) alkyl or aryl (Ci-C 2 ) alkyl and R 16 is -CN or -COOR 17 , wherein R 17 is (Ci-C 4 ) Alkyl.
• Step a) The compounds of the formula (XXV) can be prepared in analogy to those described in Russian Journal of Organic Chemistry, 46 (2010), 1461-1465, US2005 / 0256164 and US2002 / 0098443 via an alkylation of oxazolidinone, thiazolidinone or Imidazolidinone derivatives of the formula (XXIV) with the corresponding oc-halo or ⁇ -diazo carboxylic acid esters or nitriles are synthesized under acidic or basic conditions.
• the compounds of formula (XXIV) are either commercially available or can be prepared by known methods, for example analogous to those described in Chemical Biology & Drug Design, 85 (2015), 454-460, Synthetic Communications, 45 (2015), 1183-1189, Journal of the American Chemical Society, 137 (2015), 6440-6443, Journal of Medicinal Chemistry, 58 (2015), 3892-3909, Helvetica Chimica Acta, 33 (1950), 1776-1787 and Journal of the American Chemical Society, 73 (1951), 4199-4204.
• Carboxylic acid ester derivatives of the formula (XXIX) are either commercially available or can be prepared by known methods, for example via halogenation. This can be accomplished, for example, via directed ortho-lithiation, followed by capturing the carbanion with a suitable electrophilic halogenating reagent, or alternatively via a carboxylic acid derivative-directed halogenation analogous to those described in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146 described methods.
• Carboxylic acids of the formula (IIIc) having the structural units A5, A6, A7, A8, A9, A10, Al, A12 or Al 3 are either commercially available or can be prepared by known methods, for example analogously to those described in WO2013 / 163244, Farmaco, Ediette Scientifica, 40 (1985), 190-199, WO2013 / 087792, Journal of Medicinal Chemistry, 46 (2003), 3914-3929, WO2015 / 011082, Journal of Medicinal Chemistry, 58 (2015), 8309- 8313, Advanced Synthesis & Catalysis, 357 (2015), 1065-1069, Bioorganic Chemistry, 59 (2015), 151-167, Journal of the Chemical Society, (1929), 815-816, Organic Syntheses, 19 (1939), 10-11, Journal of the American Chemical Society, 63 (1941), 2946-2948, Helvetica Chimica Acta, 32 (1949), 35-38, Journal of Organic Chemistry, 15 (1950), 1082-1092, Journal of the American Chemical Society
• the compounds of the formula (XXXII) can be prepared, for example, in analogy to those described in WO2013 / 163244, Farmaco, Ediette Scientifica, 40 (1985), 190-199, WO2013 / 087792, Journal of Medicinal Chemistry, 46 (2003), 3914-3929 and WO2015 / 011082 are synthesized via a condensation of 2-amino heteroaryl derivatives of the formula (XXXI) with a oc-Halopyruvat of formula (XXX).
• Step b) Compounds of the formula (XXXIII) can be prepared by known methods, for example via halogenation. This may be, for example, via directed ortho-lithiation, followed by trapping of the carbanion with a suitable electrophilic halogenating reagent or, alternatively, via a carboxylic acid derivative-directed halogenation in analogy to that described in Bioorganic - -
• Compounds of the formula (IIIc) can be prepared by known methods from compounds of the formula (XXIII) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions.
• Carboxylic acids of the formula (IIIa ') having the structural units A15 or A17 are either commercially available or can be prepared by known methods, for example in analogy to the methods described in WO2006 / 130588, Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236- 4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146.
• the compounds of formula (XLVI) are either commercially available or can be prepared via the methods described in Journal of Organic Chemistry, 65 (2000), 2379-2385; Tetrahedron: Asymmetry, 16 (2005), 2973-2979; Chemische Berichte, 111 (1987), 411-414 and Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, 208 (1981), 617-619, via a dibromination of the corresponding olefin compounds.
• Compounds of formula (XLVIII) are either commercially available or can be prepared via halogenation of the compounds of formula (XL VII). This can be accomplished, for example, via directed ortho-lithiation, followed by capturing the carbanion with a suitable electrophilic halogenating reagent, or alternatively via a carboxylic acid derivative-directed halogenation analogous to those described in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146 described methods.
• Compounds of the formula (IIIa ') can be prepared by known methods from compounds of the formula (XLVIII) via ester cleavage under acidic, basic, thermal or hydrogenolytic conditions.
• Carboxylic acids of the formula (IIIb ") having the structural units A14, A16 or A18 are either commercially available or can be prepared by known methods, for example in analogy to those described in Organic Process Research & Development, 10 (2006), 712-716, WO2006 / 130588, WO2010 / 117425, Journal of the American Chemical Society, 71 (1949), 2818-2820, Journal of Biological Chemistry, 198 (1952), 587-597, Bulletin of the Chemical Society of Japan, 36 (1963) , 25-29, Italian Journal of Biochemistry, 28 (1979), 104-110, Chemical & Pharmaceutical Bulletin, 30 (1982), 440-461, Chemistry Letters, 7 (1985), 939-942, Tetrahedron Letters, 24 (1989). 1983), 1067-1070, Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238, Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146.
• R 15 is (Ci-Ce) alkyl or aryl (Ci-C 2 ) alkyl.
• Ab stands for -C (R 9 ) (R 10 ) -, -S (0) m -, -O- or -N (R 7 ) -.
• Ac is -C (R U) (R 12) -, -S (0) m -, -O- or -N (R 7) -.
• X 1 is halogen.
• Nitrosoproline derivatives of the formula (XXXV) are either commercially available or can be prepared by known methods, for example analogously to the methods described in Organic Process Research & Development, 10 (2006), 712-716, WO2006 / 130588 and WO2010 / 117425 Nitrosation of compounds of the formula (XXXIV).
• Mesoionic sydnone derivatives of the formula (XXXVI) are either commercially available or can be prepared by known methods, for example analogously to the method described in Organic Process Research & Development, 10 (2006), 712-716, WO2006 / 130588 and WO2010 / 117425 Compounds of formula (XXXV) by heterocyclization using e.g. B. trifluoroacetic acid anhydride as dehydrating reagent.
• Compounds of the formula (XXXIX) are either commercially available or can be prepared by known methods via halogenation of the compounds of the formula (XXVIII). This can be accomplished, for example, via directed ortho-lithiation, followed by capturing the carbanion with a suitable electrophilic halogenating reagent, or alternatively via a carboxylic acid derivative-directed halogenation analogous to those described in Bioorganic & Medicinal Chemistry Letters, 24 (2014), 4236-4238; Tetrahedron, 58 (2002), 6723-6728 and WO2003 / 010146 described methods.
• Carboxylic acids of the formula (IIIc ') having the structural units A19 or A20 are either commercially available or can be prepared by known methods, for example analogously to those described in Bioorganic & Medicinal Chemistry, 16 (2008), 1890-1902, WO2003 / 093280 WO200001 / 016138, WO2008 / 067257, WO2011 / 079230, WO2008 / 015271, WO2004 / 092140, Russian Chemical Bulletin, 59 (2010), 1631-1638, Journal of Combinatorial Chemistry, 7 (2005), 236-245, Journal of Chemical Society, Perkin Transaction 1: Organic and Organic Biochemistry, 18 (1999), 2639-2644, WO2003 / 035644, WO2013 / 050437, European Journal of Medicinal Chemistry, 84 (2014), 718-730, Chemistry-A European Journal, 18 (2012), 14943-14947 and WO2013 / 036994.
• X 1 and X 3 are halogen and R 21 is (Ci-C 4 ) alkyl or aryl (Ci-C 2 ) alkyl. Step a) - -
• the compounds of formula (XLI) are either commercially available or can be prepared via the methods described in Journal of the American Chemical Society, 132 (2010), 1264-1266, Organic Preparations and Procedures International, 7 (1975), 149-154 and European Journal of Medicinal Chemistry, 16 (1981), 495-501, via ⁇ -halogenation of the corresponding ketones.
• the invention also relates to methods for controlling animal pests, in which compounds of the formula (I) or of the formula ( ⁇ ) are allowed to act on animal pests and / or their habitat. Preference is given to the control of animal pests in agriculture and forestry and in the protection of materials. Excluded therefor are preferably methods for the surgical or therapeutic treatment of the human or animal body and diagnostic methods that are performed on the human or animal body.
• the invention further relates to the use of the compounds of the formula (I) or of the formula (II) as pesticides, in particular pesticides.
• pest control always always includes the term pesticides.
• the compounds of the formula (I) or of the formula (II) are suitable for plant protection, favorable toxicity to warm-blooded animals and good environmental compatibility for protecting plants and plant organs against biotic and abiotic stress factors, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, in particular nematodes, and molluscs, which are found in agriculture, horticulture, animal breeding, aquaculture, forestry, gardens and recreational facilities, in the protection of stored products and in the sanitary sector.
• the term "hygiene” is to be understood as meaning any and all measures, rules and procedures whose purpose is to prevent diseases, in particular infectious diseases, and which serve to protect human health and / or to maintain cleanliness According to the invention, this includes, in particular, measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramics, Plastic or also metal (s) to ensure that they are free of hygiene pests and / or their excretions.
• measures for the cleaning, disinfection and sterilization of, for example, textiles or hard surfaces, in particular surfaces of glass, wood, cement, porcelain, ceramics, Plastic or also metal (s) to ensure that they are free of hygiene pests and / or their excretions Preferably excluded from the scope of the invention in this regard are surgical or therapeutic, to be applied to the human body or the body of animals treatment regulations and diagnostic Regulations that are carried out on the human body or the bodies of animals.
• honeygiene sector covers all areas, technical fields and industrial applications where these hygiene measures, rules and procedures are important, for example in the - -
• the term "hygiene pest” should therefore be understood as referring to one or more animal pests whose presence in the hygiene sector is problematic, in particular for health reasons, and it is therefore a primary objective to determine the presence of and / or exposure to hygiene pests in the hygiene sector This can be achieved, in particular, by the use of a pesticide which can be used both to prevent infestation and to prevent an existing infestation, or to use preparations which prevent exposure to pests
• hygiene pests include the organisms mentioned below.
• the compounds of the formula (I) or the formula (II) can be preferably used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
• the above mentioned pests include:
• Pests from the strain of Arthropoda in particular from the class of Arachnida z. Acarus spp., E.g. Acarus siro, Aceria kuko, Aceria sheldoni, Aculops spp., Aculus spp., E.g. Aculus fockeui, Aculus badendali, Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., E.g. B.
• Oligonychus coffeae Oligonychus coniferarum, Oligonychus ilicis, Oligonychus indicus, Oligonychus mangiferus, Oligonychus pratensis, Oligonychus punicae, Oligonychus yothersi, Ornithodorus spp., Ornithonyssus spp., Panonychus spp., E.g.
• Panonychus citri Metatetranychus citri
• Panonychus ulmi Metatetranychus ulmi
• Phyllocoptruta oleivora Platytetranychus multidigituli
• Polyphagotarsonemus latus Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Steneotarsonemus spp. Steneotarsonemus spinki, Tarsonemus spp. Tarsonemus confusus, Tarsonemus pallidus, Tetranychus spp., E.g.
• Blatta orientalis Blattella asahinai, Blattella germanica, Leucophaea maderae, Loboptera decipiens, Neostylopyga rhombifolia, Panchlora spp., Parcoblatta spp., Periplaneta spp., E.g. Periplaneta americana, Periplaneta australasiae, Pycnoscelus surinamensis, Supella longipalpa; from the order of Coleoptera z.
• Diabrotica balteata Diabrotica barberi, Diabrotica undecimpunctata howardi, Diabrotica undecimpunctata undecimpunctata, Diabrotica virgifera virgifera, Diabrotica virgifera zeae, Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epicaerus spp., Epilachna spp., E.g. Epilachna borealis, Epilachna varivestis, Epitrix spp., E.g.
• Epitrix cucumeris Epitrix fuscula, Epitrix hirtipennis, Epitrix subcrinita, Epitrix tuberis, Faustinus spp., Gibbium psylloides, Gnathocerus cornutus, Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes b Camillus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., z.
• hypothenemus hampei Hypothenemus obscurus, Hypothenemus pubescens, Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decemlineata, Leucoptera spp., E.g. B.
• Melolontha melolontha Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Necrobia spp., Neogalerucella spp., Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Oryzaphagus oryzae, Otiorhynchus spp., E.g.
• Otiorhynchus cribricollis Otiorhynchus ligustici, Otiorhynchus ovatus, Otiorhynchus rugosostriarus, Otiorhynchus sulcatus, Oulema spp., E.g. Oulema melanopus, Oulema oryzae, Oxycetonia jucunda, Phaedon cochleariae, - -
• Phyllophaga spp. Phyllophaga helleri
• Phyllotreta spp. E.g. Phyllotreta armoraciae, Phyllotreta pusilla, Phyllotreta ramosa, Phyllotreta striolata, Popillia japonica, Premnotrypes spp., Prostephanus truncatus, Psylliodes spp., E.g.
• Tanymecus spp. E.g. Tanymecus dilaticollis, Tanymecus indicus, Tanymecus palliatus, Tenebrio molitor, Tenebrioides mauretanicus, Tribolium spp., E.g. Tribolium audax, Tribolium castaneum, Tribolium confusum, Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp., E.g. Zabrus tenebrioides; from the order of Dermaptera z. B.
• Delia antiqua Delia coarctata, Delia llorilega, Delia platura, Delia radicum, Dermatobia hominis, Drosophila spp., E.g. Drosophila melanogaster, Drosophila suzukii, Echinocnemus spp., Euleia heraclei, Fannia spp., Gasterophilus spp., Glossina spp., Haematopota spp., Hydrellia spp., Hydrellia griseola, Hylemya spp., Hippobosca spp., Hypoderma spp. Liriomyza spp., E.g.
• Acyrthosiphon pisum Acrogonia spp., Aeneolamia spp., Agonoscena spp., Aleurocanthus spp., Aleyrodes proletella, Aleurolobus barodensis, Aleurothrixus - - floccosus, Allocaridara malayensis, Amrasca spp. Amrasca bigutulla, Amrasca devastans, Anuraphis cardui, Aonidiella spp.
• Aspidiella spp. Aspidiella spp., Aspidiotus spp., E.g. Aspidiotus nerii, Atanus spp., Aulacorthum solani, Bemisia tabaci, Blastopsylla occidentalis, Boreioglycaspis melaleucae, Brachycaudus helichrysi, Brachycolus spp., Brevicoryne brassicae, Cacopsylla spp., E.g.
• Icerya purchasi Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., E.g.
• B. Lecanium corni ( Parthenolecanium corni), Lepidosaphes spp., Z. Lepidosaphes ulmi, Lipaphis erysimi, Lopholeucaspis japonica, Lycorma americanula, Macrosiphum spp., E.g.
• Macrosiphum euphorbiae Macrosiphum lilii, Macrosiphum rosae, Macrosteies facifrons, Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metealfa pruinosa, Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., E.g.
• Nephotettix spp. E.g. Nephotettix cinetieeps, Nephotettix nigropictus, Nettigoniclla spectra, Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Oxya chinensis, Pachypsylla spp., Parabemisia myricae, Paratrioza spp., E.g.
• Paratrioza cockerelli Parlatoria spp., Pemphigus spp., E.g. B. Pemphigus bursarius, Pemphigus populivenae, Peregrinus maidis, Perkinsiella spp., Phenacoccus spp., Z. Phenacoccus madeirensis, Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., E.g. Phylloxera devastatrix, Phylloxera notabilis, Pinnaspis aspidistrae, Planococcus spp., E.g. B.
• Planococcus citri Prosopidopsylla flava, Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Z. Pseudococcus calceolariae, Pseudococcus comstocki, Pseudococcus longispinus, Pseudococcus maritimus, Pseudococcus viburni, Psyllopsis spp., Psylla spp., E.g.
• Rhopalosiphum spp. E.g. Rhopalosiphum maidis, Rhopalosiphum oxyacanthae, Rhopalosiphum padi, Rhopalosiphum rufiabdominal, Saissetia spp., E.g.
• Trioza spp. E.g. Trioza diospyri, Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the subordination of Heteroptera z.
• Aelia spp. Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., E.g.
• Cimex adjunctus Cimex hemipterus, Cimex lectularius, Cimex pilosellus, Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., E.g.
• Lygus elisus Lygus hesperus, Lygus lineolaris, Macropes excavatus, Megacopta cribraria, Miridae, Monaionion atratum, Nezara spp., Z. Nezara viridula, Nysius spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., E.g.
• Hoplocampa cookei Hoplocampa testudinea, Lasius spp., Linepithema (Iridiomyrmex) humile, Monomorium pharaonis, Paratrechina spp., Paravespula spp., Plagiolepis spp., Sirex spp., Solenopsis invicta, Tapinoma spp., Technomyrmex albipes, Urocerus spp. , Vespa spp., Z. Vespa crabro, Wasmannia auropunctata, Xeris spp .; from the order of Isopoda z.
• Autographa spp. Barathra brassicae, Blastodacna atra, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius, Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., Z.
• Cydia nigricana Cydia pomonella, Dalaca noctuides, Diaphania spp., Diparopsis spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., E.g.
• Grapholita molesta Grapholita prunivora, Hedylepta spp., Helicoverpa spp., Z. Helicoverpa armigera, Helicoverpa zea, Heliothis spp.
• Heliothis virescens Hofmannophila pseudospretella Homoeosoma spp., Homona spp., Hyponomeuta padella, Kakivoria ilavofasciata, Lampides spp., Laphygma spp., Laspeyresia molesta, Leucinodes orbonalis, Leucoptera spp., E.g. B.
• Leucoptera coffeella Lithocolletis spp., Z. B. Lithocolletis blancardella, Lithophane antennata, Lobesia spp., Z. Lobesia botrana, Loxagrotis albicosta, Lymantria spp., E.g. B. Lymantria dispar, Lyonetia spp., Z. B.
• Pieris rapae, Platynota stultana, Plodia interpunctella, Plusia spp., Plutella xylostella ( Plutella maculipennis), Prays spp., Prodenia spp., Protoparce spp., Pseudaletia spp., E.g. B. Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Z. Schoenobius bipunctifer, Scirpophaga spp., E.g.
• Trichoplusia ni Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of Orthoptera or Saltatoria z.
• Lepinotus spp. Liposcelis from the order of Siphonaptera z. Ceratophyllus spp., Ctenocephalides spp., E.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; from the order of Thysanoptera z.
• Anaphothrips obscurus Basothrips biformis, Chaetanaphothrips leeuweni, Drepanothrips reuteri, Enneothrips hevens, Frankliniella spp., Z.
• Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla z. B. Scutigerella spp., Z. B. Scutigerella immaculata;
• Bursaphelenchus cocophilus, Bursaphelenchus eremus, Bursaphelenchus xylophilus, Cacopaurus spp., E.g. Cacopaurus pestis, Criconemella spp., E.g. Criconemella curvata, Criconemella onoensis, Criconemella ornata, Criconemella rusium, Criconemella xenoplax ( Mesocriconema xenoplax), Criconemoides spp., E.g. Criconemoides ferniae, Criconemoides onoense, Criconemoides ornatum, Ditylenchus spp., E.g.
• Meloidogyne spp. Longidorus africanus, Meloidogyne spp., E.g. Meloidogyne chitwoodi, Meloidogyne fallax, Meloidogyne hapla, Meloidogyne incognita, Meloinema spp., Nacobbus spp., Neotylenchus spp., Paralongidorus spp., Paraphelenchus spp., Paratrichodorus spp., E.g. Paratrichodorus minor, Paratylenchus spp., Pratylenchus spp., E.g.
• Pratylenchus penetrans Pseudohalenchus spp., Psilenchus spp., Punctodera spp., Quinisulcius spp., Radopholus spp., E.g. Radopholus citrophilus, Radopholus similis, Rotylenchulus spp., Rotylenchus - - spp., Scutellonema spp., Subanguina spp., Trichodorus spp. Trichodorus obtusus, Trichodorus primitivus, Tylenchorhynchus spp., E.g. Tylenchorhynchus annulatus, Tylenchulus spp., E.g. B. Tylenchulus semipenetrans, Xiphinema spp., Z. B. Xiphinema index.
• the compounds of the formula (I) or of the formula (II) may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, as microbicides or gametocides, for example as fungicides, antimycotics, bactericides, Viricides (including anti-viral agents) or as agents against MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism) can be used. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
• the present invention further relates to formulations and application forms prepared therefrom as pesticides such.
• B. drench, drip and spray comprising at least one compound of formula (I) or formula ( ⁇ ).
• the uses include other pesticides and / or effect-improving adjuvants such as penetration enhancers, e.g. As vegetable oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of fatty acids such as rapeseed oil or soybean oil or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, eg.
• organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
• organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
• dioctyl sulfosuccinate or hydroxypropyl guar polymers and / or humectants such.
• glycerol and / or fertilizers such as ammonium, potassium or phosphorus-containing fertilizer.
• Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
• SL water-soluble liquids
• EC emulsion concentrates
• EW emulsions in water
• SC suspension concentrates
• SC SE, SE, FS, OD
• WG water-dispersible granules
• GR granules
• capsule concentrates CS
• the formulations contain, in addition to one or more compounds of the formula (I) or of the formula (II), further agrochemical active compounds.
• compositions or application forms which contain adjuvants such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries such as - -
• An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
• Examples of adjuvants are agents that promote retention, spreading behavior, adherence to the leaf surface, or penetration.
• These formulations are prepared in a known manner, for. Example by mixing the compounds of formula (I) or the formula ( ⁇ ) with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surface-active substances. The preparation of the formulations is carried out either in suitable systems or before or during use.
• aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
• alcohols and polyols which may also be substituted, etherified and / or esterified
• ketones such as acetone, cyclohexanone
• Esters including fats and oils
• poly ethers simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
• Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg.
• Suitable solvents are, for example, aromatic hydrocarbons such. As xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such. As chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons such. As cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such. Methanol, ethanol, iso-propanol, - -
• Suitable carriers can be used.
• carriers are in particular question: z.
• ammonium salts and natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic minerals such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid fertilizers. Mixtures of such carriers can also be used.
• Suitable carriers for granules are: z.
• liquefied gaseous diluents or solvents can be used.
• extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for.
• aerosol propellants such as halogenated hydrocarbons and butane, propane, nitrogen and carbon dioxide.
• Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulfonic acid, salts of phenolsulfonic acid or naphthalenesulfonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulfosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulfates, sulfonates and phosphates, e.g.
• alkylaryl polyglycol ethers alkylsulfonates, alkyl sulfates, arylsulfonates, protein hydrolysates, lignin-Sulphatablaugen and methylcellulose.
• a surfactant is advantageous when one of the compounds of formula (I) or formula (II) and / or one of the inert carriers is not soluble in water and when applied in water.
• auxiliaries can in the formulations and the applications derived therefrom dyes such as inorganic pigments, eg.
• dyes such as inorganic pigments, eg.
• iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and Metallphthalocyaninfarbstoffe and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc may be present.
• Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers. - -
• formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
• additional auxiliaries may be mineral and vegetable oils.
• auxiliaries may be present in the formulations and in the use forms derived therefrom.
• additives are, for example, fragrances, protective colloids, binders, adhesives, thickeners, thixotropic substances, penetration promoters, retention promoters, stabilizers, sequestrants, complexing agents, humectants, spreading agents.
• the compounds of formula (I) or formula (II) may be combined with any solid or liquid additive commonly used for formulation purposes.
• Retentionsiörderer are all those substances that reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
• Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
• Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the mobility of the active ingredients in the cuticle.
• the method described in the literature can be used to determine this property.
• Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12), fatty acid esters such as rapeseed oil or soybean oil, Fettaminalkoxylate such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
• alcohol alkoxylates such as coconut oil ethoxylate (10) or isotridecyl ethoxylate (12)
• fatty acid esters such as rapeseed oil or soybean oil
• Fettaminalkoxylate such as tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
• the formulations preferably contain between 0.00000001 and 98% by weight of the compound of the formula (I) or of the formula (II), particularly preferably between 0.01 and 95% by weight of the compound of the formula (I) or of the formula (II ), very particularly preferably between 0.5 and 90% by weight of the compound of the formula (I) or of the formula (II), based on the weight of the formulation.
• the content of the compound of the formula (I) or the formula (II) in the forms of application prepared from the formulations (in particular pesticides) can vary within wide ranges.
• the concentration of the compound of the formula (I) or the formula (II) in the use forms may usually be between 0.00000001 and 95% by weight of the compound of the - -
• the application is done in a custom forms adapted to the application.
• the compounds of formula (I) or formula (II) may also be used in admixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, herbicides, fertilizers, avian repellents, phytotonics, sterilants, safeners , Semiochemicals and / or plant growth regulators are used so z. B. to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent development of resistance. Furthermore, such drug combinations, plant growth and / or tolerance to abiotic factors such.
• the compounds of the formula (I) or of the formula (II) may be present in admixture with other active substances or semiochemicals such as attractants and / or avian repellents and / or plant activators and / or growth regulators and / or fertilizers.
• the compounds of formula (I) or formula ( ⁇ ) can be used to improve plant properties such as growth, yield and quality of the crop.
• the compounds of the formula (I) or of the formula (II) are present in formulations or in the formulations prepared from these formulations in admixture with other compounds, preferably those as described below.
• Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, aldicarb, bendiocarb, benfuracarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan,
• GABA-controlled chloride channel B loosened such as cyclodiene organochlorines, e.g. As chlordane and endosulfan or Phenylpyrazole (Fiprole), z. Ethiprol and fipronil.
• sodium channel modulators such as pyrethroids, e.g.
• nAChR nicotinic acetylcholine receptor
• neonicotinoids e.g. Acetaminopride, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam or nicotine or sulfoxaflor or flupyradifurone.
• nAChR nicotinic acetylcholine receptor
• allosteric modulators of the glutamate-dependent chloride channel such as avermectins / milbemycins, e.g. Abamectin, emamectin benzoate, lepimectin and milbemectin.
• juvenile hormone mimetics such as juvenile hormone analogs, e.g. As hydroprene, kinoprene and methoprene or fenoxycarb or pyriproxyfen.
• Various non-specific (multi-site) inhibitors such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or chloropicrin or sulfuryl fluoride or borax or crushing tartar or methyl isocyanate producers, e.g. Diazomet and Metam.
• modulators of chordotonic organs e.g. As pymetrozine or flonicamide.
• mite growth inhibitors such as. Clofentezine, hexythiazox and dillovidazine or etoxazole.
• inhibitors of mitochondrial ATP synthase such as ATP disruptors such as diafenthiuron or organotin compounds, e.g. As azocyclotin, cyhexatin and fenbutatin oxide or
• Blockers of the nicotinic acetylcholine receptor channel such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
• Type 0 inhibitors of chitin biosynthesis such as bistrifluron, chlorofluorazuron, dillubenzuron, flucycloxuron, flufenoxuron, hexallumuron, lufenuron, novaluron, novillumuron, teflubenzuron and triflumuron.
• inhibitors of chitin biosynthesis type 1, such as buprofezin.
• Skinning disruptor especially in dipterans, i.e., two-winged, such as cyromazine.
• ecdysone receptor agonists such as chromafenozide, halofenozide, methoxyfenozide and tebufenozide.
• Electron Transport Inhibitors such as METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidia, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
• METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidia, Pyridaben, Tebufenpyrad and Tolfenpyrad or Rotenone (Derris).
• (22) blocker of the voltage-dependent sodium channel such.
• (23) inhibitors of acetyl-CoA carboxylase such as tetronic and tetramic acid derivatives, e.g. Spirodiclofen, spiromesifen and spirotetramat.
• inhibitors of mitochondrial complex IV electron transport such as phosphines, e.g. As aluminum phosphide, calcium phosphide, phosphine and zinc phosphide or cyanides, calcium cyanide, potassium cyanide and sodium cyanide.
• inhibitors of mitochondrial complex II electron transport such as beta-ketonitrile derivatives, e.g. Cyenopyrafen and Cyilumetofen and carboxanilides, such as Pyllubumid.
• ryanodine receptor modulators such as diamides, e.g. B. chlorantraniliprole, cyanotriliprol and flubendiamide, other active substances such as afidopyropene, afoxolaner, azadirachtin, benclothiaz, benzoximate, bifenazate, broflanilide, bromopropylate, quinomethionate, chloroprallethrin, cryolite, cyclaniliprole, cycloxapride, cyhalodiamide, dicloromezotiaz, dicofol, epsilon-metofluthrin, epsilon- Momfluthrin, Flometoquine, Fluazaindolizine, Fluensulfone, Flufenerim, Flufenoxystrobin, Flufiprol, Fluhexafon, Fluopyram, Fluralaner, Fluxa
• Fungicides The active ingredients specified here by their "common name” are known and described, for example, in the "Pesticide Manual” (16th edition British Crop Protection Council) or searchable on the Internet (for example: http://www.alanwood.net/pesticides) ,
• All of the above-mentioned mixture partners of classes (1) to (15), if they are capable of doing so on the basis of their functional groups, may optionally form salts with suitable bases or acids.
• All of the mentioned fungicidal mixture partners of classes (1) to (15) may optionally include tautomeric forms.
• inhibitors of ergosterol biosynthesis for example, (1,001) cyproconazole, (1,002) difenoconazole, (1,003) epoxiconazole, (1,004) fenhexamide, (1,005) fenpropidin, (1,006) fenpropimorph, (1,007) fenpyrazamine, (1,008) fluquinconazole, ( 1,009) flutriafol, (1,010) imazalil, (1,011) imazalil sulfate, (1,012) ipconazole, (1,013) metconazole, (1,014) myclobutanil, (1,015) paclobutrazole, (1,016) prochlorazole, (1,017) propiconazole, (1,018) prothioconazole, (1.019) pyrisoxazole, (1.020) spiroxamine, (1.021) tebuconazole, (1.022) tetracon
• N-methylimidoformamide (1.076) ⁇ '- ⁇ 5-bromo-6- [(1 R) -1- (3, 5-difluorophenyl) ethoxy] -2-methylpyridin-3-yl ⁇ -N-ethyl-N- methylimidoformamide, (1.077) N '- ⁇ 5-bromo-6- [(1S) -1- (3,5-difluorohexyl) ethoxy] -2-methylpyridin-3-yl ⁇ -N-ethyl-N-methylimidoformamide , (1.078) N '- ⁇ 5-bromo-6- [(cis-4-isopropylcyclohexyl) oxy] -2-methylpyridin-3-yl ⁇ -N-ethyl-N-methylimidoformamide, (1.079) N'- ⁇ 5 - bromo-6- [(trans-4-isopropylcyclo
• inhibitors of the respiratory chain on complex I or II for example (2.001) benzovindiflupyr, (2.002) bixafen, (2.003) boscalid, (2.004) carboxin, (2.005) fluopyram, (2.006) flutolanil, (2.007) fluxapyroxad, (2.008) furametpyr , (2.009) isoietamide, (2.010) isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), (2.011) isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), (2.012) isopyrazam (anti-epimeric racemate 1RS, 4SR , 9SR), (2.013) isopyrazam (mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti-epimeric racemate 1RS, 4SR, 9SR), (2.014) isopyrazam (syn-epimeric enantiomer 1
• 3) respiratory chain inhibitors on complex III for example, (3,001) ametoctradine, (3,002) amisulbrom, (3,003) azoxystrobin, (3,004) coumethoxystrobin, (3,005) coumoxystrobin, (3,006) cyazofamide, (3,007) dimoxystrobin, (3,008) enoxastrobin, (3,009) famoxadone, (3,010) fenamidone, (3,011) flufenoxystrobin, (3,012) fluoxastrobin, (3,013) kresoxime methyl, (3,014) metominostrobin, (3,015) orysastrobin, (3,016) picoxystrobin, (3,017) pyraclostrobin, (3,018) Pyrametostrobin, (3.019) Pyraoxystrobin, (3.020) Trifloxystrobin (3.021) (2E) -2- ⁇ 2 - [( ⁇ [(IE)
• inhibitors of mitosis and cell division for example (4,001) carbendazim, (4,002) diethofencarb, (4,003) ethaboxam, (4,004) fluopicolide, (4,005) pencycuron, (4,006) thiabendazole, (4,007) thiophanate-methyl, (4,008) zoxamide , (4.009) 3- ⁇ 1 ⁇ -4- (2,6 ⁇ ⁇ 1 ⁇ 6 ⁇ 1) -6- ⁇ 6 ⁇ 1 ⁇ 1-5phenylpyridazine, (4.010) 3-chloro-5- (4-chlorophenyl) -4- (2,6- difluorophenyl) -6-methylpyridazine, (4.011) 3-chloro-5- (6-chloropyridin-3-yl) -6-methyl-4- (2,4,6-trifluorophenyl) pyridazine, (4.012) 4- (2 -Brom-4-fluoro-1-yl) -
• Copper naphthenate (5.007) copper oxide, (5.008) copper oxychloride, (5.009) copper (2 +) sulfate, (5.010) dithianon, (5.011) dodin, (5.012) folpet, (5.013) mancozeb, (5.014) maneb, (5.015 ) Metiram, (5.016) Zinc Metiram, (5.017) Copper Oxine, (5.018) Propineb, (5.019) Sulfur and Sulfur Preparations Including Calcium Polysulfide, (5.020) Thiram, (5.021) Zineb, (5.022) Ziram. 6) Compounds capable of inducing host defense, for example, (6.001) acibenzolar-S-methyl, (6.002) isotianil, (6.003) probenazole, (6.004) tiadinil.
• inhibitors of amino acid and / or protein biosynthesis for example (7.001) cyprodinil,
• inhibitors of cell wall synthesis for example, (9.001) benthiavalicarb, (9.002) dimethomorph,
• Inhibitors of lipid and membrane synthesis for example (10,001) propamocarb, (10,002) propamocarb hydrochloride, (10,003) tolclofos-methyl.
• Inhibitors of melanin biosynthesis for example, (11.001) tricyclazole, (11.002) 2,2,2-trifluoroethyl ⁇ 3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl ⁇ carbamate.
• 12) inhibitors of nucleic acid synthesis for example, (12.001) benalaxyl, (12.002) benalaxyl-M (kiralaxyl), (12.003) metalaxyl, (12.004) metalaxyl-M (mefenoxam).
• inhibitors of signal transduction for example (13.001) fludioxonil, (13.002) iprodione, (13.003) procymidone, (13.004) proquinazide, (13.005) quinoxyfen, (13.006) vinclozolin.
• the compounds of the formula (I) or the formula (II) can be combined with biological pesticides.
• Bio pesticides include, in particular, bacteria, fungi, yeasts, plant extracts and those products formed by microorganisms, including proteins and secondary metabolites.
• Biological pesticides include bacteria such as spore-forming bacteria, root-colonizing bacteria and bacteria that act as biological insecticides, fungicides or nematicides.
• Bacillus amyloliquefaciens strain FZB42 (DSM 231179), or Bacillus cereus, in particular B. cereus strain CNCM 1-1562 or Bacillus firmus, strain 1-1582 (Accession number CNCM 1-1582) or Bacillus pumilus, especially strain GB34 (Accession no. ATCC 700814) and strain QST2808 (Accession No. NRRL B-30087), or Bacillus subtilis, especially strain GB03 (Accession No. ATCC SD-1397), or Bacillus subtilis strain QST713 (Accession No. NRRL B-21661) or Bacillus subtilis Strain OST 30002 (Accession No.
• NRRL B-50421 Bacillus thuringiensis, in particular B. thuringiensis subspecies israelensis (serotype H-14), strain AM65-52 (Accession No. ATCC 1276), or B. thuringiensis subsp. aizawai, in particular strain ABTS-1857 (SD-1372), or B. thuringiensis subsp. kurstaki strain HD-1, or B. thuringiensis subsp. tenebrionis strain NB 176 (SD-5428), - -
• fungi and yeasts which can be used as biological pesticides are:
• Beauveria bassiana in particular strain ATCC 74040, coniothyrium minitans, in particular strain CON / M / 91-8 (Accession No. DSM-9660), Lecanicillium spp., In particular strain HRO LEC 12, Lecanicillium lecanii (formerly known as Verticillium lecanii), in particular Strain KV01, Metarhizium anisopliae, in particular strain F52 (DSM3884 / ATCC 90448), Metschnikowia fructicola, in particular strain NRRL Y-30752, Paecilomyces fumosoroseus (new: Isaria fumosorosea), in particular strain IFPC 200613, or strain Apopka 97 (Accesion No.
• Paecilomyces lilacinus in particular P. lilacinus strain 251 (AGAL 89/030550), Talaromyces flavus, in particular strain VI 17b, Trichoderma atroviride, in particular strain SCI (Accession Number CBS 122089), Trichoderma harzianum, in particular T. harzianum rifai T39. (Accession Number CNCM 1-952).
• viruses that can be used or used as biological pesticides are:
• Adoxophyes orana Apple peel winder
• Granulosis virus GV
• Cydia pomonella codling moth
• Granulosis virus GV
• Helicoverpa armigera cotton capsule worm
• Nuclear polyhedrosis virus NPV
• Spodoptera exigua mNPV Spodoptera frugiperda (armyworm) mNPV
• Spodoptera littoralis African cotton worm
• bacteria and fungi which are added as Jnokulant 'plants or plant parts or plant organs and promote by their special properties, plant growth and plant health. Examples are:
• Agrobacterium spp. Azorhizobium caulinodans, Azospirillum spp., Azotobacter spp., Bradyrhizobium spp., Burkholderia spp., In particular Burkholderia cepacia (formerly known as Pseudomonas cepacia), Gigaspora spp., Or Gigaspora monosporum, Glomus spp., Laccaria spp., Lactobacillus buchneri, Paraglomus spp., Pisolithus tinctorus, Pseudomonas spp., Rhizobium spp., Especially Rhizobium trifolii, Rhizopogon spp., Scleroderma spp., Suillus spp., Streptomyces spp.
• plant extracts and products formed by microorganisms including proteins and secondary metabolites, which can be used as biological pest control agents are:
• the compounds of the formula (I) or of the formula (II) can be combined with safeners, for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic anhydrides, oxabetrinil, 2-methoxy-N - ( ⁇ 4-
• safeners for example Benoxacor, Cloquintocet (-mexyl), Cyometrinil, Cyprosulfamide, Dichlormid, Fenchlorazole (-ethyl), Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen (-ethyl), mefenpyr (-diethyl), naphthalic
• Plants and Plant Parts can be treated.
• Plants are understood to mean all plants and plant populations, such as desirable and unwanted wild plants or crops (including naturally occurring crops), for example cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugarcane, tomatoes , Paprika, cucumber, melon, carrot, watermelon, onion, lettuce, spinach, leek, beans, Brassica oleracea (eg cabbage) and other vegetables, cotton, tobacco, rapeseed, as well as fruit plants (with the fruits apples, pears, Citrus fruits and grapes).
• Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant varieties which can or can not be protected by plant breeders' rights.
• Plants are to be understood as meaning all stages of development, such as seeds, cuttings, young (unripe) plants and mature plants.
• Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
• the plant parts also include harvested plants or harvested plant parts as well as vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
• plants and their parts can be treated.
• wild-type or plant species and plant varieties obtained by conventional biological breeding methods such as crossing or protoplast fusion and their parts are treated.
• transgenic plants and plant cultivars obtained by genetic engineering, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
• the term "parts” or “parts of plants” or “parts of plants” has been explained above.
• Propes of the respective commercially available or in use plant varieties are particularly preferably treated according to the invention.
• PV plants are understood as meaning plants with new properties ("traits") have been obtained by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
• the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
• traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
• Further and particularly emphasized examples of such properties are an increased resistance of the plants against animal and microbial pests, such as insects, arachnids, nematodes, mites, snails, causes z.
• toxins produced in the plants in particular those produced by the genetic material from Bacillus thuringiensis (for example by the genes CrylA (a), CrylA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants, further increased resistance of the plants against plant pathogenic fungi, bacteria and / or viruses, causes z.
• systemically acquired resistance SAR
• systemin phytoalexins
• elicitors elicitors
• resistance genes and correspondingly expressed proteins and toxins as well as an increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
• herbicidal active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT "-Gene).
• the genes which confer the desired properties can also occur in combinations with one another in the transgenic plants. Examples of transgenic plants are the important crops, such as cereals (wheat, rice, triticale, barley, rye, oats), corn, soybeans, potatoes, sugar beets, sugar cane, - -
• Tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape, as well as fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, whereby maize, soy, wheat, rice, potato, cotton, sugar cane, tobacco and oilseed rape are particularly emphasized , Traits that are particularly emphasized are the increased resistance of the plants to insects, arachnids, nematodes and snails.
• the treatment of the plants and plant parts with the compounds of the formula (I) or the formula ( ⁇ ) is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, eg. B. by dipping, spraying, spraying, sprinkling, vaporizing, atomizing, atomizing, scattering, foaming, brushing, spreading, injecting, pouring (drenchen), drip irrigation and propagating material, especially in seeds, further by dry pickling, wet pickling, slurry pickling, encrusting It is also possible to apply the compounds of the formula (I) or the formula (II) by the ultra-low-volume method or the use form or the compound of the formula (I) or the Inject formula ( ⁇ ) itself into the soil.
• a preferred direct treatment of the plants is foliar application, i. H. the compounds of the formula (I) or of the formula (II) are applied to the foliage, wherein the treatment frequency and the application rate should be adjusted to the infestation pressure of the respective pest.
• the compounds of the formula (I) or of the formula (II) also enter the plants via the root system.
• the treatment of the plants is then carried out by the action of the compounds of formula (I) or formula ( ⁇ ) on the habitat of the plant.
• This can be, for example, by drenching, mixing into the soil or the nutrient solution, d. H. the location of the plant (e.g., soil or hydroponic systems) is impregnated with a liquid form of the compounds of formula (I) or formula (II), or by the soil application, i. H. the compounds of the formula (I) or the formula (II) according to the invention are introduced into the plant in solid form (for example in the form of granules). In water rice crops, this may also be by metered addition of the compound of formula (I) or formula (II) in a solid form (eg as granules) into a flooded paddy field.
• Seed treatment The control of animal pests by the treatment of seed of plants has long been known and is subject to constant improvement. Nevertheless, there are a number of problems in the treatment of seeds that can not always be satisfactorily resolved. Thus, it is desirable to have methods of protecting the seed and the germinating plant - - which make unnecessary, or at least significantly reduce, the additional application of pesticides during storage, after sowing or after emergence of the plants. It is also desirable to optimize the amount of the active ingredient used in such a way that the seed and the germinating plant are best protected against attack by animal pests, but without damaging the plant itself by the active ingredient used.
• seed treatment methods should also include the intrinsic insecticidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and also of the germinating plant with minimal pest control effort.
• the present invention therefore more particularly relates to a method of protecting seeds and germinating plants from attack by pests by treating the seed with one of the compounds of formula (I) or formula (II).
• the method according to the invention for the protection of seeds and germinating plants from infestation by pests further comprises a method in which the seed is treated simultaneously in one operation or sequentially with a compound of formula (I) or formula (II) and a mixture component. It also further comprises a method in which the seed is treated at different times with a compound of the formula (I) or the formula (II) and a mixture component.
• the invention also relates to the use of the compounds of the formula (I) or of the formula (II) for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
• the invention relates to seed which has been treated for protection against animal pests with a compound of the formula (I) or the formula ( ⁇ ) according to the invention.
• the invention also relates to seed treated at the same time with a compound of formula (I) or formula (II) and a mixture component.
• the invention further relates to seed which has been treated at different times with a compound of the formula (I) or the formula (II) and a mixture component.
• the individual substances may be present in different layers on the seed.
• the layers which comprise a compound of the formula (I) or of the formula (II) and of the mixture components may optionally be separated by an intermediate layer.
• the invention also relates to seed in which a compound of the formula (I) or the formula (II) and a mixture component are applied as a constituent of an envelope or as a further layer or further layers in addition to an envelope. Furthermore, the invention relates to seed which, after treatment with a compound of the formula (I) or the formula (II), is subjected to a film coating process in order to avoid dust abrasion on the seed.
• Another advantage is the fact that by treating the seed with a compound of formula (I) or the formula ( ⁇ ) germination and emergence of the treated seed can be promoted.
• Compounds of formula (I) or formula (II) may also be used in combination with signal technology agents whereby better colonization with symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or occurs an optimized nitrogen fixation comes.
• symbionts such as rhizobia, mycorrhiza and / or endophytic bacteria or fungi takes place and / or occurs an optimized nitrogen fixation comes.
• the compounds of the formula (I) or of the formula (II) are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
• these are seeds of cereals (eg wheat, barley, rye, millet and oats), corn, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rape, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants.
• cereals eg wheat, barley, rye and oats
• corn, soybean, cotton, canola, oilseed rape, vegetables and rice are examples of seeds of cereals (such as wheat, barley, rye and oats), corn, soybean, cotton, canola, oilseed rape, vegetables and rice.
• transgenic seed with a compound of the formula (I) or the formula (II) is also of particular importance.
• the heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
• the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis. - -
• the compound of the formula (I) or the formula (II) is applied to the seed.
• the seed is treated in a state where it is so stable that no damage occurs during the treatment.
• the treatment of the seed can be done at any time between harvesting and sowing.
• seed is used which has been separated from the plant and freed from flasks, shells, stems, hulls, wool or pulp.
• seed may be used that has been harvested, cleaned and dried to a moisture content that is storable.
• seed can be used, which after drying z. B. was treated with water and then dried again, for example, priming.
• the compounds of the formula (I) or of the formula (II) are generally applied to the seed in the form of a suitable formulation. Suitable formulations and methods for seed treatment are known to those skilled in the art.
• the compounds of the formula (I) or of the formula (II) can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
• formulations are prepared in a known manner by mixing the compounds of formula (I) or formula ( ⁇ ) with conventional additives, such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives , secondary thickeners, glues, gibberellins and even water.
• conventional additives such as conventional extenders and solvents or diluents, dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives , secondary thickeners, glues, gibberellins and even water.
• Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned are the dyes known under the names Rhodamine B, CI Pigment Red 112 and CI Solvent Red 1. - -
• Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
• Preferably used are alkylnaphthalenesulfonates such as diisopropyl or diisobutylnaphthalenesulfonates.
• Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds. Preference is given to using nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
• nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tri-stryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
• Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
• Defoamers which may be present in the seed-dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
• Preferably usable are silicone defoamers and magnesium stearate.
• Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal. Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
• Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents.
• Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.
• the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
• the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds - - become.
• the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers , Soy and beets or vegetable seed of various nature.
• the seed dressing formulations which can be used according to the invention or their dilute application forms can also be used for pickling seeds of transgenic plants.
• the seed dressing formulations which can be used according to the invention or the use forms prepared therefrom by the addition of water
• all mixing devices which can usually be used for the dressing can be considered.
• the seed is placed in a batch or continuous mixer, adding either desired amount of seed dressing formulations, either as such or after prior dilution with water, and until the formulation is evenly distributed mix the seed.
• a drying process follows.
• the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the particular content of the compounds of the formula (I) or of the formula (II) in the formulations and according to the seed.
• the application rates in the compound of the formula (I) or of the formula (II) are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
• the compounds of formula (I) or of formula (II) are active against animal parasites, in particular ectoparasites or endoparasites.
• the term endoparasite includes in particular helminths and protozoa such as coccidia.
• Ectoparasites are typically and preferably arthropods, especially insects or acarids.
• the compounds of the formula (I) or of the formula (I), which have a favorable toxicity to warm-blooded animals, are suitable for the control of parasites used in livestock and animal husbandry in livestock, breeding animals, zoo animals, laboratory animals, Experimental animals and pets occur. They are effective against all or individual stages of parasite development.
• Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; or poultry such as turkeys, ducks, geese and, in particular, chickens; or fish or shellfish, e.g. As in aquaculture, or optionally insects such as bees. - -
• the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets, and especially dogs, cats, caged birds; Reptiles, amphibians or aquarium fish.
• the compounds of the formula (I) or the formula (II) are administered to mammals.
• the compounds of the formula (I) or of the formula (II) are administered to birds, namely caged birds or, in particular, poultry.
• controlling means that the compounds of the formula (I) or the formula ( ⁇ ) are effective for the occurrence of the respective parasite in an animal that is infected with such parasites is infected to a harmless extent, is reduced. More specifically, “combat” in the present context means that the compounds of the formula (I) or the formula ( ⁇ ) kill the respective parasite, prevent its growth or prevent its replication.
• the arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Bovicola spp., Damalina spp., Felicola spp .; Lepikentron spp., Menopon spp., Trichodectes spp., Trimenopon spp., Trinoton spp., Werneckiella spp; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Atylotus spp., Braula spp., Calliphora spp., Chrysomy
• Melophagus spp. Melophagus spp., Morellia spp., Musca spp., Odagmia spp., Oestrus spp., Philipomyia spp., Phlebotomus spp., Rhinoestrus spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tipula spp., Wilhelmia spp., Wohlfahrtia spp .; from the order Siphonaptrida, for example Ceratophyllus spp., Ctenocephalides spp., Pulex spp., Tunga spp., Xenopsylla spp .; from the order Heteropterida, for example Cimex spp., Panstrongylus spp., Rhodnius spp., Triatoma spp .; as well as pests
• Metastigmata From the subclass Akari (Acarina) and the order Metastigmata, for example from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephalus (Boophilus) spp., Rhipicephalus spp.
• Argasidae such as Argas spp., Ornithodorus spp., Otobius spp.
• Ixodidae such as Amblyomma spp., Dermacentor spp., Haemaphysalis spp. Hyalomma spp., Ixodes spp., Rhipicephal
• parasitic protozoa examples include, but are not limited to:
• Mastigophora such as: Metamonada: from the order Vaccinonadida, for example Giardia spp., Spironucleus spp.
• Trichomonadida for example Histomonas spp., Pentatrichomonas spp., Tetratrichomonas spp., Trichomonas spp., Tritrichomonas spp.
• Euglenozoa from the order Trypanosomatida for example Leishmania spp., Trypanosoma spp.
• Sarcomastigophora such as Entamoebidae, for example Entamoeba spp., Centramoebidae, for example Acanthamoeba sp., Euamoebidae, e.g. Hartmanella sp.
• Alveolata such as Apicomplexa (Sporozoa): z. Cryptosporidium spp .; from the order Eimeriida for example Besnoitia spp., Cystoisospora spp., Eimeria spp., Hammondia spp., Isospora spp., Neospora spp., Sarcocystis spp., Toxoplasma spp .; from the order Adeleida z. B. Hepatozoon spp., Klossiella spp .; from the order Haemosporida z. B. Leucocytozoon spp., Plasmodium spp .; out of order - -
• Microspora such as Encephalitozoon spp., Enterocytozoon spp., Globidium spp., Nosema spp., And also e.g. B. Myxozoa spp.
• Acute helixes pathogenic to humans or animals include, for example, Acanthocephala, nematodes, pentastoma, and platyhelminthes (e.g., Monogenea, Cestodes, and Trematodes).
• Exemplary helminths include, but are not limited to:
• Monogenea z.
• Cestodes from the order Pseudophyllidea for example: Bothridium spp., Diphyllobothrium spp., Diplogonoporus spp. Ichthyobothrium spp., Ligula spp., Schistocephalus spp., Spirometra spp.
• Echinolepis spp. Hydatigera spp., Hymenolepis spp., Joyeuxiella spp., Mesocestoides spp., Moniezia spp., Paranoplocephala spp., Raillietina spp., Stilesia spp., Taenia spp., Thysaniezia spp., Thysanosoma spp.
• Trematodes from the genus Digenea for example: Austrobilharzia spp., Brachylaima spp., Calicophoron spp., Catatropis spp., Clonorchis spp.
• Collyricum spp. Cotylophoron spp., Cyclocoelum spp., Dicrocoelium spp., Diplostomum spp., Echinochasmus spp., Echinoparyphium spp., Echinostoma spp., Eurytrema spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Fischoederius spp , Gastrothylacus spp., Gigantobilharzia spp., Gigantocotyle spp., Heterophyes spp., Hypoderaeum spp., Leucochloridium spp., Metagonimus spp., Metorchis spp., Nanophyetus spp., Notocotylus spp., Opisthorchis spp., Or
• Nematodes from the order Trichinellida for example: Capillaria spp., Trichinella spp., Trichomosoides spp., Trichuris spp.
• Coperosides spp. Cylicostephanus spp., Cylindropharynx spp., Cystocaulus spp., Dictyocaulus spp., Elaphostrongylus spp., Filaroides spp., Globocephalus spp , Graphidium spp., Gyalocephalus spp., Haemonchus spp., Heligmosomoides spp., Hyostrongylus spp., Marshallagia spp., Metastrongylus spp., Muellerius spp., Necator spp., Nematodirus spp., Neostrongylus spp., Nippostrongylus spp.
• Acanthocephala from the order Oligacanthorhynchida, for example: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Moniliformida for example: Moniliformis spp.,
• Pentastoma from the order Porocephalida for example Linguatula spp.
• the compounds of the formula (I) or of the formula (II) are administered by methods which are generally known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations. Administration may be prophylactic; metaphylactically or therapeutically.
• an embodiment of the present invention relates to the compounds of the formula (I) or the formula ( ⁇ ) for use as a medicament.
• Another aspect relates to the compounds of formula (I) or formula ( ⁇ ) for use as antiendoparasitic. - -
• Another specific aspect of the invention relates to the compounds of the formula (I) or of the formula (II) for use as antihelminthic agents, in particular for use as nematicide, platyhelminthicide, acanthocephalicide or pentastomicide.
• Another specific aspect of the invention relates to the compounds of formula (I) or formula (II) for use as antiprotozoic.
• Another aspect relates to the compounds of the formula (I) or the formula ( ⁇ ) for use as anti-topazarasitic, in particular an arthropodicide, very particularly an insecticide or an acaricide.
• veterinary formulations comprising an effective amount of at least one compound of formula (I) or formula (II) and at least one of the following: a pharmaceutically acceptable excipient (eg solid or liquid diluent), a pharmaceutically acceptable adjuvant (eg surfactants), in particular a pharmaceutically acceptable excipient conventionally used in veterinary formulations and / or a pharmaceutically acceptable excipient conventionally used in veterinary formulations.
• a pharmaceutically acceptable excipient eg solid or liquid diluent
• a pharmaceutically acceptable adjuvant eg surfactants
• a related aspect of the invention is a process for the preparation of a veterinary formulation as described herein, which comprises the step of mixing at least one compound of formula (I) or formula (II) with pharmaceutically acceptable excipients and / or adjuvants, especially conventionally in veterinary medicine
• Formulations used include pharmaceutically acceptable excipients and / or adjuvants conventionally used in veterinary formulations.
• veterinary formulations selected from the group of ectoparasiticidal and endoparasiticidal formulations, in particular selected from the group of anthelmintic, antiprotozoic and arthropodicidal formulations, more particularly selected from the group of nematicidal, platyhelminthicidal, acanthocephalicidal, pentastomicidal, insecticidal and acaricidal formulations the aspects mentioned, as well as methods for their preparation.
• Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, by using an effective amount of a compound of the formula (I) or the formula ( ⁇ ) an animal, especially a nonhuman animal, that needs it.
• Another aspect relates to a method for treating a parasitic infection, in particular infection by a parasite selected from the group of those mentioned here Ectoparasites and endoparasites, by applying a veterinary formulation as defined herein to an animal, especially a non-human animal in need thereof.
• Another aspect relates to the use of the compounds of the formula (I) or of the formula (I) in the treatment of a parasitic infection, in particular an infection by a parasite selected from the group of the ectoparasites and endoparasites mentioned here, in an animal, in particular one nonhuman animal.
• treatment includes prophylactic, metaphylactic and therapeutic treatment.
• mixtures of at least one compound of the formula (I) or of the formula (II) with other active substances, in particular with endo- and ectoparasiticides, are provided hereby for the veterinary field.
• blending not only means that two (or more) different active ingredients are formulated in a single formulation and applied together, but also refers to products comprising separate formulations for each active ingredient. if more than two active substances are to be used, all active substances should be formulated in a common formulation, or all active substances should be formulated in separate formulations, or mixed forms where some of the active substances are formulated together and some of the active substances are formulated separately the separate or sequential use of the active substances in question.
• Exemplary agents from the group of ectoparasiticides as compounding partners include, but are not limited to, the insecticides and accicides detailed above.
• Other useful agents are listed below in accordance with the above mentioned classification based on the current IRAC Mode of Action Classification Scheme: (1) acetylcholinesterase (AChE) inhibitors; (2) GABA-controlled chloride channel blockers; (3) sodium channel modulators; (4) competitive nicotinic acetylcholine receptor (nAChR) modulators; (5) allosteric modulators of the nicotinic acetylcholine receptor (nAChR); (6) allosteric modulators of the glutamate-dependent chloride channel (GluCl); (7) juvenile hormone mimetics; (8) various non-specific (multi-site) inhibitors; (9) modulators of chordotonic organs; (10) mite growth inhibitors; (12) inhibitors of mitochondrial ATP synthase, such as ATP disruptors; (13) decoupling of
• Active substances with unknown or non-specific mechanisms of action eg. Fentrifanil, fenoxacrim, cycloprene, chlorobenzilate, chlordimeform, flubenzimine, dicyclanil, amidoflumet, quinomethionate, triarathene, clothiazoben, tetrasul, potassium oleate, petroleum, metoxadiazone, gossyplur, flotenzin, bromopropylate, cryolite;
• Organochlorine compounds e.g. B. Camphechlor, Lindane, Heptachlor; or phenylpyrazoles, e.g. Acetoprol, pyrafluprol, pyriprole, vaniliprole, sisapronil; or isoxazolines, e.g. Sarolaner, Afoxolaner, Lotilaner, Fluralaner; Pyrethroids, e.g.
• Neonicotinoids e.g. B. Nithiazin Dicloromezotiaz, Triflumezopyrim macrocyclic lactones, eg. Nemadectin, ivermectin, latidectin, moxidectin, selamectin, eprinomectin, doramectin, emamectin benzoate; milbemycin
• Biologicals, hormones or pheromones for example natural products, eg thuringiensin, codlemon or neem components Dinitrophenols, e.g. Dinocap, dinobuton, binapacryl;
• Benzoylureas eg. Fluazuron, penfluron,
• Amidine derivatives e.g. B. Chlormebuform, cymiazole, demiditraz
• Hive varroa acaricides for example organic acids, e.g. Formic acid, oxalic acid.
• agents from the group of endoparasiticides, as a mixture partner include, but are not limited to, anthelmintic agents and antiprotozoal agents.
• the anthelmintic agents include, but are not limited to, the following nematicidal, tremesticidal and / or cestotic agents: from the class of macrocyclic lactones, for example: eprinomectin, abamectin, nemadectin, moxidectin, doramectin, selamectin, lepimectin, latidectin, milbemectin, Ivermectin, emamectin, milbemycin; from the class of benzimidazoles and sample zimidazoles, for example: oxibendazole, mebendazole, triclabendazole, thiophanate, parbendazole, oxfendazole, netobimine, fenbendazole, febantel, thiabendazole, cyclobendazole, cambendazole, albendazole sulfoxide, albendazole, flu
• Antiprotozoal agents including, but not limited to, the following: from the class of triazines, for example: diclazuril, ponazuril, letrazuril, toltrazuril; from the class polyl ether ionophore for example: monensin, salinomycin, maduramicin, narasin; from the class of macrocyclic lactones, for example: milbemycin, erythromycin; from the class of quinolones for example: enrofloxacin, pradofloxacin; from the class of quinines for example: chloroquine; from the class of pyrimidines for example: pyrimethamine; from the class of sulfonamides for example: sulfachinoxalin, trimethoprim, sulfaclozin; from the class of thiamine for example: amprolium; from the class of lincosamides for example: clindamycin; from the class of carbanilides,
• all said mixing partners can optionally form salts with suitable bases or acids.
• a vector in the context of the present invention is an arthropod, in particular an insect or arachnid, which is able to attack pathogens such.
• pathogens such as viruses, worms, protozoa and bacteria from a reservoir (plant, animal, human, etc.) to a host to transfer.
• the pathogens can be transferred to a host either mechanically (eg, trachoma by non-stinging flies) on a host, or after injection (eg, malaria parasites by mosquitoes).
• vectors and their transmitted diseases or pathogens are:
• Anopheles malaria, filariasis
• flies sleeping sickness (trypanosomiasis); Cholera, other bacterial diseases;
• Ticks Borellioses such as Borrelia bungdorferi sensu lato., Borrelia duttoni, tick-borne encephalitis, Q fever (Coxiella burnetii), Babesia (Babesia canis canis), ehrlichiosis.
• vectors for the purposes of the present invention are insects, for example aphids, flies, cicadas or thrips, which can transmit plant viruses to plants.
• Other vectors that can transmit plant viruses are spider mites, lice, beetles and nematodes.
• vectors for the purposes of the present invention are insects and arachnids such as mosquitoes, in particular of the genera Aedes, Anopheles, z. A. gambiae, A. arabiensis, A. funestus, A. dirus (malaria) and Culex, psychodides such as phlebotomus, lutzomyia, lice, fleas, flies, mites and ticks that can transmit pathogens to animals and / or humans.
• Vector control is also possible when the compounds of formula (I) or formula (II) are resistance-disrupting.
• Compounds of formula (I) or formula (II) are suitable for use in the prevention of diseases and / or pathogens transmitted by vectors.
• another aspect of the present invention is the use of compounds of formula (I) or formula ( ⁇ ) for vector control, e.g. As in agriculture, horticulture, forests, gardens and recreational facilities and in the protection of materials and materials.
• the compounds of the formula (I) or the formula (II) are suitable for the protection of industrial materials against attack or destruction by insects, eg. B. from the orders Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
• non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
• the application of the invention for the protection of wood is particularly preferred.
• the compounds of the formula (I) or of the formula (II) are used together with at least one further insecticide and / or at least one fungicide.
• the compounds of the formula (I) or of the formula (II) are present as ready-to-use pesticides, ie they can be applied to the corresponding material without further changes.
• insecticides or fungicides in particular those mentioned above come into question. - -
• the compounds of the formula (I) or of the formula (II) protect against the growth of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water. can be used.
• the compounds of the formula (I) or the formula (II) can be used alone or in combinations with other active substances as antifouling agents.
• the compounds of the formula (I) or of the formula (II) are suitable for controlling animal pests in the hygiene sector.
• the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids, ticks and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins, animal husbandry.
• the compounds of the formula (I) or of the formula (II) are used alone or in combination with other active ingredients and / or adjuvants.
• they are used in household insecticide products.
• the compounds of formula (I) or formula (II) are effective against sensitive and resistant species as well as against all stages of development.
• pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
• the application is carried out for example in aerosols, non-pressurized sprays, z.
• the calibration is carried out with un branched alkan-2-ones (having 3 to 16 carbon atoms) whose logP values are known (determination of the logP values by retention times by linear interpolation between two consecutive alkanones).
• the NMR data of selected examples are listed either in classical form ( ⁇ values, multiplet splitting, number of H atoms) or as NMR peak lists.
• the IH-NMR data of selected examples are recorded in the form of IH-NMR peak lists. For each signal peak, first the ⁇ value in ppm and then the signal intensity in round brackets are listed. The ⁇ -value signal intensity number pairs of different signal peaks are listed separated by semicolons.
• the peak list of an example therefore has the form: ⁇ (intensity ⁇ ; 82 (intensity 2);; 5i (intensity;; ⁇ ⁇ (intensity);
• the intensity of sharp signals correlates with the height of the signals in a printed example of an NMR spectrum in cm and shows the true ratios of the signal intensities. For broad signals, multiple peaks or the center of the signal and their relative intensity can be shown compared to the most intense signal in the spectrum.
• Such stereoisomers and / or impurities may be typical of the particular preparation process. Their peaks can thus help identify the reproduction of our manufacturing process by "by-product fingerprints.”
• the vials are filled with 5-10 adult cat fleas ⁇ Ctenocephalides felis), closed with a perforated plastic lid and incubated lying at room temperature and ambient humidity. After 48 h the efficacy is determined. For this purpose, the jars are placed upright and the fleas are tapped on the bottom of the jar. Fleas that remain immobile on the ground or move in an uncoordinated manner are considered dead or struck.
• a substance shows good activity against Ctenocephalides felis, if in this test at an application rate of 5 ⁇ g / cm 2 at least 80% effect was achieved. It means 100% effect that all fleas were struck or dead. 0% effect means that no fleas were harmed.
• active compound For the preparation of a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide. Dilution with citrated bovine blood gives the desired concentration. Approximately 20 sober adult cat fleas (Ctenocephalides felis) are placed in a chamber sealed with gauze at the top and bottom. A metal cylinder is placed on the chamber, the underside of which is sealed with parafilm. The cylinder contains the blood-drug preparation that can be absorbed by the fleas through the parafilm membrane.
• Solvent dimethylsulfoxide To prepare a suitable preparation of active compound, 10 mg of active compound are mixed with 0.5 ml of dimethyl sulfoxide and the concentrate is diluted with water to the desired concentration.
• Vessels containing a sponge treated with sugar solution and the preparation of active compound of the desired concentration are populated with 10 adult house flies (Musca domestica).
• the kill is determined in%. 100% means that all flies have been killed; 0% means that none of the flies have been killed.
• the active ingredient preparation 50 ⁇ of the active ingredient preparation are transferred into microtiter plates and filled with 150 ⁇ l IPL41 insect medium (33% + 15% sugar) to a final volume of 200 ⁇ . Subsequently, the plates are sealed with parafilm, through which a mixed population of green peach aphid (Myzus persicae), which is located in a second microtiter plate, can pierce and take up the solution.
• IPL41 insect medium 33% + 15% sugar
• Emulsifier alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
• Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid (Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
• Emulsifier alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
• Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with an active compound preparation of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae j.
• Emulsifier alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
• Maize leaf discs (Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are infested with caterpillars of the armyworm (Spodoptera frugiperda).
• Emulsifier alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is dissolved with the stated parts by weight of solvent and filled with water containing an emulsifier concentration of 1000 ppm until reaching the desired concentration. To prepare further test concentrations, dilute with emulsifier-containing water.
• Bean leaf discs Phaseolus vulgaris infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
• Emulsifier alkylaryl polyglycol ether
• Paprika plants Capsicum annuum which are heavily infested with the green peach aphid (Myzus persicae) are treated by spraying with the preparation of active compound in the desired concentration.

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• Nitrogen Condensed Heterocyclic Rings (AREA)
• Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
• Plural Heterocyclic Compounds (AREA)

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• 2017
  • 2017-01-16 WO PCT/EP2017/050773 patent/WO2017125340A1/de not_active Ceased
  • 2017-01-19 TW TW106101784A patent/TW201738248A/zh unknown
  • 2017-01-19 AR ARP170100149A patent/AR107397A1/es unknown
  • 2017-01-20 UY UY0001037081A patent/UY37081A/es not_active Application Discontinuation

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