Classifications

• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
  • A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/713—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with four or more nitrogen atoms as the only ring hetero atoms
• • A—HUMAN NECESSITIES
  • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
  • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
  • A61P33/00—Antiparasitic agents
  • A61P33/14—Ectoparasiticides, e.g. scabicides
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
  • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
  • C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
  • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
  • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings

Definitions

• the present invention relates to novel anthranilic acid diamide derivatives, their use as insecticides and acaricides for combating animal pests and to several processes for their preparation.
• New anthranilic acid derivatives have now been found which have advantages over the already known compounds, e.g. are better biological or ecological properties, broader application methods, a better insecticidal, acaricidal effect, as well as a good tolerance to crops exemplified.
• the Anthranilklarederivate 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 anthranilamides of the formula (I)
• A is N (R 6 ) R 7
• G represents fluoromethyl, difluoromethyl, chlorodifluoromethyl, C 2 -C 6 haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C ⁇ - haloalkynyl, C3-C6-halocycloalkyl, Ci-Ce-alkoxy, fluoromethoxy, fluoroethoxy, difluoroethoxy, tetrafluoroethoxy, Chlordifluorethoxy, Dichlorfluorethoxy, C3-C 6 haloalkoxy, Ci-Ce-haloalkoxy-Ci C 4 alkyl, C 2 -C 4 haloalkylthio, C 2 -C 4 haloalkylsulfinyl, C 2 -C 4 haloalkylsulfonyl or for - W- Q stands if
• A is N (R 8 ) -N (R 9 ) (R 10 ),
• G is Ci-Ce-haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 6 - alkoxy, G-Ce-haloalkoxy, Ci-C 6 - Haloalkoxy-Ci-C-alkyl, Ci-C 4 -Haloalkylthio, GC 4 -Halo- alkylsulfinyl, Ci-C 4 -Haloalkylsulfonyl, halogen or -WQ, if
• A is N (R 6 ) - L
• G is Ci-Ce-haloalkyl, C 2 -C 6 haloalkenyl, C 2 -C 6 haloalkynyl, C 3 -C 6 halocycloalkyl, C 6 - alkoxy, Ci-Ce-haloalkoxy, Ci-C 6 - haloalkoxy-Ci-C4-alkyl, Ci-C4-haloalkylthio, Ci-C 4 -Halo- alkylsulfinyl, Ci-C4-haloalkylsulfonyl, halogen or represents -WQ,
• R 1 is hydrogen or in each case optionally mono- or polysubstituted by identical or different substituents C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl or C 3 -C 6 -cycloalkyl, where the substituents are selected independently of one another may be selected from halogen, cyano, nitro, hydroxy, C 1 -C 4 -alkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, (C 1 -C 4 -alkoxy) carbonyl, C 1 -C 4 -alkyl 4- alkylamino, di- (C 1 -C 4 -alkyl) amino, C 3 -C 6 -cycloalkylamino or (C 1 -C 4 -alkyl) C 3
• R 2 represents Ci-Ce-alkyl, C 3 -C 6 cycloalkyl, Ci-Ce-haloalkyl, Ci-Ce-halocycloalkyl, C 2 -C 6 alkenyl (C 2 - Ce-haloalkenyl, C 2 -C 6 alkynyl, C 2 -C 6 haloalkynyl, Ci-C 4 alkoxy, Ci-C -haloalkoxy, C1-C4 alkylthio, Ci-C4-alkylsulfinyl, Ci-C 4 alkylsulfonyl, Ci-C4-haloalkylthio, Ci- C 4 haloalkylsulfinyl, C 1 -C 4 haloalkylsulfonyl, halogen, cyano, nitro or C 3 -C 6 -trialkylsilyl,
• R 3 independently of one another represent hydrogen, C 1 -C 6 -alkyl, C 3 -C 6 -cycloalkyl, C 1 -C 6 -haloalkyl, halogen, cyano, nitro, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 Alkylthio or C 1 -C 4 haloalkylthio, m is 0 to 2,
• R 4 represents in each case optionally mono- or polysubstituted by identical or different C1-C6 alkyl, Cs-Ce-cycloalkyl, C 2 -C 6 alkenyl, C 2 -C 6 -Aikinyl, Ci-C6 alkylsulfonyl, C1- C4 Alkoxycarbonyl, Ci-Cö-alkylcarbonyl, aminocarbonyl, Ci-C6-alkylaminocarbonyl or GC ⁇ - dialkylaminocarbonyl, where the substituents can be independently selected from halogen, cyano, nitro, hydroxy, Ci-Cö-alkyl, Ci-Cö-haloalkyl , C 3 -C 6 -cycloalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfiny
• Ci-C 4 alkylsulfonyl Ci-C 4 -Alkylsulfimino, C 2 -C 6 alkoxycarbonyl, C 2 -C 6 alkylcarbonyl or C 3 COE trialkylsilyl, or
• R 8 , R 9 independently of one another are a phenyl ring or a 5- or 6-membered unsaturated, partially saturated or saturated heterocycle, where the phenyl ring or heterocycle is optionally mono- or polysubstituted by identical or different substituents, and wherein the
• R 8 and R 9 may be connected to each other via two to six carbon atoms and form a ring which optionally additionally contains a further nitrogen, sulfur or oxygen atom and optionally monosubstituted to fourfold with C 1 -C 2 -alkyl, C 1 -C 2 - Haloalkyl, halogen, cyano, amino, C 1 -C 2 -alkoxy or C 1 -C 2 -haloalkoxy may be substituted,
• R 19 independently of one another represent hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, halogen, cyano, nitro, hydroxyl, COOH, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -haloalkylthio, C 1 -C 4 -haloalkylsulfinyl or C 1 -C 4 -haloalkylsulfonyl, R 20 , R 21 , R 22 independently of one another are C 1 -C 6 -alkyl,
• W is a radical from the group -CH 2 -, -CH 2 O-, -OCH 2 -, -CH 2 OCH 2 -, -CH 2 S-, -CH 2 SCH 2 -, - CH (CN) -, -CH (F) -, -CH (C1) -, -CH (Ci-Cs-alkyl) -, -C (di-Ci-C 6 -alkyl) -, -CH 2 CH 2 - stands,
• Q is an optionally mono- or polysubstituted 5- or 6-membered aromatic heterocyclic ring of the series Ql to Q-61, where the substituents can be independently selected from Ci-C 3 alkyl, Ci-C 3 haloalkyl, Ci C 2 alkoxy, halogen, cyano, hydroxy, nitro or C 1 -C 2 haloalkoxy
• the compounds of the formula (I) according to the invention have very good insecticidal properties and can be used both in crop protection and in the protection of materials for controlling unwanted pests, such as insects.
• the compounds of the invention may optionally be used as mixtures of various possible isomeric forms, in particular of stereoisomers, such as. B. E and Z, threo and erythro, and optical isomers, but optionally also of tautomers. Both the E and the Z isomers, as well as the threo and erythro, and the optical isomers, any mixtures of these isomers, as well as the possible tautomeric forms claimed.
• the anthranilamides according to the invention are generally defined by the formula (I). Preferred radical definitions of the above and below formulas are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates.
• G is preferably fluoromethyl, difluoromethyl, chlorodifluoromethyl, C 2 -C 4 -haloalkyl, C 2 -C 4 -haloalkenyl, C 2 -C 4 -haloalkynyl, C 3 -C 4 -halocycloalkyl, C 1 -C 4 -alkoxy, fluoromethoxy, fluoroethoxy, difluoroethoxy, tetrafluoroethoxy, chlorodifluoroethoxy, dichlorofluoroethoxy , C3-C4-haloalkoxy, Ci-C4-haloalkoxy-Ci-C 4 alkyl, C 2 -C 4 haloalkylthio, C 2 -C 4 haloalkylsulfinyl, C 2 -C 4 - haloalkylsulfonyl or -WQ,
• G particularly preferred for fluoromethyl, difluoromethyl, chlorodifluoromethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 1, 2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, methoxy, ethoxy, n-propoxy, iso-propoxy, fluoromethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-difluoropropoxy, 3-chloro-1, l, 2-trifluoropropoxy, difluoromethoxymethyl, trifluoromethoxymethyl, trifluoroethoxymethyl or for -WQ,
• G is very particularly preferably fluoromethyl, difluoromethyl, methoxy, ethoxy, n-propoxy, isopropoxy, 2,2-difluoroethoxy, or -W-Q,
• A is likewise preferably, more preferably or very particularly preferably N (R 6 ) -L,
• G preferably represents Ci-Gt-haloalkyl, C 2 -C 4 haloalkenyl, Ci-C 4 alkoxy, C 4 haloalkoxy, C 1 -C4- haloalkoxy-Ci-C4-alkyl, Ci-C 4 - Haloalkylthio, C 1 -C 4 -haloalkylsulfinyl, C 1 -C 4 -haloalkylsulfonyl, halogen or for -WQ,
• G is particularly preferably halogen, fluoromethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, 1,1-difluoroethyl, 2,2-difluoroethyl, 1, 2,2-trifluoroethyl, 1,1,2,2-tetrafluoroethyl, pentafluoroethyl, methoxy, ethoxy, n-propoxy, iso -propoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, fluoroethoxy, difluoroethoxy, trifluoroethoxy, 2-chloro-2,2-difluoromethoxy, 2,2-difluoropropoxy, 3-chloro-1, l, 2-trifluoropropoxy, difluoromethoxymethyl, Trifluoromethoxymethyl, trifluoroethoxymethyl, difluoromethylthio, trifluoromethylthio, difluoromethylsulf
• R 1 is preferably hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -alkenyl, C 1 -C 6 -alkynyl, C 1 -C 6 -cycloalkyl, cyano (C 1 -C 6 -alkyl), C 1 -C 6 -haloalkyl, C 2 -C 6- Haloalkenyl, C 2 -C 6 -haloalkynyl, C 1 -C 4 -alkoxy-ci-
• Ci-C4-alkylthio-Ci-C4-alkyl Ci-C alkylsulfinyl-Ci-C alkyl, or Ci-C 4 alkylsulfonyl Ci-C 4 alkyl,
• R 1 particularly preferably represents hydrogen, methyl, cyclopropyl, cyanomethyl, methoxymethyl, methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl, R 1 very particularly preferably represents hydrogen,
• R 2 is preferably hydrogen, C 1 -C 4 -alkyl, halogen, cyano, C 1 -C 4 -alkoxy,
• R 2 particularly preferably represents methyl, ethyl, methoxy, ethoxy, F, Cl or Br,
• R 2 very particularly preferably represents methyl, Br, Cl,
• R 2 is particularly preferably methyl
• R 3 is preferably hydrogen, C 1 -C 6 -alkyl, C 1 -C 4 -alkoxy, halogen, cyano or nitro
• R 3 particularly preferably represents hydrogen, methyl, methoxy, F, Cl or Br,
• R 3 is very particularly preferably hydrogen, m is preferably 0 to 2, m is particularly preferably 0 to 1, m is very particularly preferably 0,
• R 4 is preferably in each case optionally monosubstituted or polysubstituted, identically or differently, C 1 -C -alkyl, C 1 -C -cycloalkyl, C 2 -C 4 -alkenyl, C 2 -C -alkynyl, C 1 -C -alkylsulfonyl, C 1 -C 4 -alkyl 4 alkoxycarbonyl, Ci-C4-alkylcarbonyl, aminocarbonyl, Ci-C4-alkylaminocarbonyl, where the substituents may be independently selected from halogen, cyano, Ci-C 4 - alkyl, Ci-C alkoxy, C - Alkylthio, Ci-C 4 alkylsulfinyl or Ci-C alkylsulfonyl, particularly preferably represents methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-
• R 5 independently of one another preferably represents hydrogen, halogen, cyano, C 1 -C -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 1 -C 4 -haloafkoxy,
• R 5 independently of one another particularly preferably represents hydrogen, halogen or C 1 -C 4 -haloalkyl
• R 5 very particularly preferably represents fluorine, chlorine or bromine
• R 5 particularly preferably represents 3-chloro, if n is 1, n is preferably 1, 2 or 3, n is more preferably 1 or 2, n is very particularly preferably 1,
• X is preferably N, CH, CF or CC1,
• X is particularly preferably N, CH or CF
• X is very particularly preferably N
• R 6 is preferably hydrogen or C 1 -C 6 -alkyl
• R 6 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, n-butyl, R 6 very particularly preferably represents hydrogen or methyl,
• R 7 is preferably hydrogen or in each case optionally mono- or polysubstituted, identically or differently substituted C 1 -C 6 -alkyl, C 1 -C 8 -alkenyl, C 3 -C 6 -alkynyl, where the substituents can be selected independently of one another from halogen, cyano, nitro , Ci-COE-alkyl, C1-C4 alkoxy, Ci-C 4 alkylthio, Ci-C4-alkylsulfinyl, Ci-C 4 alkylsulfonyl, Ci-C 6 alkoxycarbonyl, Ci- C6-alkylcarbonyl,
• R 7 also preferably further represents optionally substituted phenylmethyl, pyridylmethyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-Ci-C 4 -alkyl or C 4 -Cs-bicycloalkyl, wherein the substituents may be independently selected from halogen , cyano, nitro, hydroxy, amino, Ci-C 4 alkyl, Ci-C 4 alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C 4 alkyl sulfinyl, Ci-C 4 Alkylsulfonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl,
• R 7 also preferably represents optionally mono- or polysubstituted by identical or different substituents phenyl, pyridyl, pyrimidinyl, thiazolyl, oxazolyl, pyrazolyl, thienyl, or furanyl, where the substituents independently of one another can be selected from halogen, cyano, nitro, hydroxy, amino, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -alkyl 4- alkylsulfinyl or C 1 -C 4 -alkylsulfonyl, C 2 -C 6 -alkoxycarbonyl, C 2 -C 6 -alkylcarbonyl, R 7 particularly preferably represents hydrogen, in each case optionally monosubstituted or polysubstituted by identical or different
• R 8, R 9 are each independently preferably represents hydrogen or represents in each case optionally monosubstituted or polysubstituted by identical or different substituents, Ci-C 4 alkyl, C 2 -C 4 alkenyl, C 3 -C 4 alkynyl,
• R 8 independently of one another are particularly preferably hydrogen, methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl or tert-butyl, cyclopropyl, prop-2-enyl, prop-2-yl
• R 8 , R 9 independently of one another very particularly preferably represent hydrogen, methyl, ethyl, methylcarbonyl, methylsulfonyl,
• R 8 , R 9 independently of one another are particularly preferably hydrogen and methyl
• R 11 , R 12 , R 13 , R 1 'independently of one another are preferably each optionally mono- or polysubstituted by identical or different substituents C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 Cycloalkyl, C 3 -C 6 -cycloalkyl-C 1 -C 4 -alkyl or aryl, where the substituents can be selected independently of one another from halogen, cyano, nitro, hydroxy, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, ci C 4
• R 11 , R 12 , R 13 , R 16 are each independently particularly preferably each optionally mono- or polysubstituted, identically or differently substituted methyl, ethyl, n-propyl, iso-propyl, n-, iso-, sec-, tert. Butyl, propenyl, butenyl, propynyl, butynyl or phenyl wherein the substituents can be independently selected from halogen, cyano, methoxy, ethoxy, methylthio, Mylsulfinyl, methylsulfonyl, methoxycarbonyl, or methylcarbonyl
• R 11 , R 12 , R 13 , R 16 independently of one another very particularly preferably represent methyl, ethyl, n-
• R 12 particularly preferably represents methyl
• R 14 , R 15 , R 17 ; R 18 independently of one another are preferably hydrogen or R 11 ,
• R 14 , R 15 , R 17 ; R 18 independently of one another particularly preferably represents hydrogen, methyl,
• R 14 , R 15 , R 17 , R 18 independently of one another very particularly preferably represent hydrogen or methyl
• L is preferred, especially preferred and most preferred for
• U is preferably O, S, SO or SO 2
• U is particularly preferably O, S, SO or SO 2 ,
• U is very particularly preferably O, S, SO or SO 2
• R 19 is preferably hydrogen or C 1 -C 4 -alkyl
• R 19 particularly preferably represents hydrogen, methyl, ethyl, n-propyl, isopropyl,
• R 19 very particularly preferably represents hydrogen or methyl
• P is preferably 0, 1, 2, p is particularly preferably 0, 1, 2, p is very particularly preferably 0 or 1,
• W is preferably -CH 2 -, -CH 2 O-, -OCH 2 -, -CH 2 OCH 2 -, -CH 2 S-, -CH 2 SCH 2 -, -CH (CN) -, - CH ( C 1 -C 6 -alkyl) -, - C (di-C 1 -C 6 -alkyl) -, -CH 2 CH 2 -, W is particularly preferably -CH 2 -, -OCH 2 -, -CH (CH 3 ), C (CH 3 ) 2 or CH 2 CH 2 ,
• W is very particularly preferably CH 2 , or -OCH 2 -,
• W is particularly preferably -OCH 2 if Q is Q-42.
• W is furthermore particularly preferably CH 2 , if Q is Q-58.
• Q preferably represents an optionally mono- or polysubstituted 5- or 6-membered aromatic heterocyclic ring of the series Q-15, Q-16, Q-24, Q-25, Q-34, Q-37, Q-38, Q -39,
• Q is particularly preferably an optionally mono- or polysubstituted 5- or 6-membered aromatic heterocyclic ring of the series Q-37, Q-38, Q-39, Q-40, Q-41, Q-42,
• R 1 , R 2 , R 3 , R 4 , R 5 , G, X, m and n have the abovementioned meanings obtained by the synthesis of anthranilamides of the formula (I) in which R 1 represents Is hydrogen, benzoxazinones of the formula (II)
• R 1 , R 2 , R 3 , R 4 , R 5 , R 8 , R 9 , G, X, m and n have the meanings given above, with a building block YR 10 , wherein R 10 has the meaning given above and Y represents a suitable leaving group such as halogen;
• the active compounds according to the invention are suitable for good plant compatibility, favorable warm-blooded toxicity and good environmental compatibility for protecting plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, nematodes and molluscs which are found in agriculture, horticulture, livestock, forests, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. 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 Arthropoda, especially from the class of arachnids, e.g. Acarus spp., Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssius , Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Epitrimeras pyri, Eutetranychus spp., Eriophyes spp., Halotydeus destructor, Hemitarsonemus spp., Hyalomma spp., Ix
• Nuphersa spp. Oligonychus spp., Ornithodorus spp., Ornithonyssus spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vaejovis spp., Vasates lycopersici.
• Anoplura e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Ptirus pubis, Trichodectes spp.
• Curculio spp. Curculio spp., Cryptorhynchus lapathi, Cylindrocoprurus spp., Dermestes spp., Diabrotica spp., Dichocrocis spp., Diloboderus spp., Epilachna spp., Epitrix spp., Faustinus spp., Gibbium psylloides, Hellula and alis, Heteronychus arator, Heteronyx spp , Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Lema spp., Leptinotarsa decemlineata, Leucoptera spp., Lissorhoptrus oryzophilus, Lixus spp., Luperodes spp., Lyctus spp., Megascelis
• Stegobium paniceum Starchus spp., Symphyletes spp., Tanymecus spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.
• Lucilla spp. Lutzomia spp., Mansonia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia spp., Phlebotomus spp., Phorbia spp., Phormia spp., Prodiplosis spp., Psila rosae, Rhagoletis spp., Sarcophaga spp., Simulium spp, Stomoxys spp., Tabanus spp. , Tannia spp., Tetanops spp., Tipula spp.
• Idioscopus spp. Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva spp., Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Qrthezia praelonga, Parabemisia myricae, Paratrioza spp.
• Parlatoria spp. Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Protopulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp.
• Hymenoptera e.g. Acromyrmex spp., Athalia spp., Atta spp., Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Solenopsis invicta, Tapinoma spp., Vespa spp.
• Lepidoptera From the order of Lepidoptera, for example, Acronicta major, Adoxophyes spp., Aedia leucomelas, Agrotis spp., Alabama spp., Amyelois transitella, Anarsia spp., Anticarsia spp., Argyroploce spp., Barathra brassicae, Borbo cinnara, Bucculatrix thurberiella, Bupalus piniarius , Busseola spp., Cacoecia spp., Caloptilia theivora, Capua reticulana, Carpocapsa pomonella, Carposina niponensis, Cheimatobia brumata, Chilo spp., Choristoneura spp., Clysia ambiguella, Cnaphalocerus spp., Cnephasia spp., Conopomorph
• Copitarsia spp. Cydia spp., Dalaca noctuides, Diaphania spp., Diatraea saccharalis, Earias spp., Ecdytolopha aurantium, Elasmopalpus lignosellus, Eidana saccharina, Ephestia spp., Epinotia spp., Epiphyas postvittana, Etiella spp., Eulia spp.
• Eupoecilia ambiguella Euproctis spp., Euxoa spp., Feltia spp., Galleria mellonella, Gracillaria spp., Grapholitha spp., Hedylepta spp., Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homoeosoma spp., Homona spp.
• Orthoptera for example, Acheta domesticus, Blatta orientalis, Blattella germanica, Dichroplus spp., Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta spp., Pulex irritans, Schistocerca gregaria, Supella longipalpa.
• siphonaptera e.g. Ceratophyllus spp., Ctenocephalides spp., Tunga penetrans, Xenopsylla cheopis.
• Pests from the strain Mollusca, especially from the bivalve class, e.g. Dreissena spp.
• Gastropoda e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp.
• Animal parasites from the strains Plathelminthes and Nematoda, especially from the Helminths eg Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp, Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp.
• plant parasitic nematodes in particular Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.
• Protozoa can be controlled.
• the compounds according to the invention may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as anti-MLO agents ( Mycoplasma-like-organism) and RLO (Rickettsia-like-organism). 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 crop protection agents and / or pesticides such.
• B. drench, drip and spray comprising at least one of the active compounds according to the invention.
• the use forms contain other crop protection agents and / or pesticides and / or the effect of improving adjuvants such as penetration enhancers, eg.
• vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g.
• organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
• 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 active compounds according to the invention, further agrochemical active substances.
• auxiliaries such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example adjuvants.
• 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.
• formulations are prepared in a known manner, for example by mixing the active ingredients with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surface-active substances.
• 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.
• excipients there may be used those substances which are suitable for conferring special properties, such as certain physical, technical and / or biological properties, to the formulation of the active substance or to the forms of use prepared from these formulations (for example usable plant protection agents such as spray or seed dressing).
• polar and non-polar organic chemical liquids e.g. from the classes of 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) and (poly) ethers, simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as dimethylsulfoxide).
• 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
• 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, e.g.
• Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.
• suitable solvents are, for example, aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, e.g. Chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, e.g.
• Cyclohexane paraffins, petroleum fractions, mineral and vegetable oils, alcohols, e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents, such as dimethyl sulfoxide, and water.
• alcohols e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters
• ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
• strong polar solvents such as dimethyl sulfoxide, and water.
• Suitable carriers are in particular: for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and ground synthetic minerals, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and / or solid Fertilizer. Mixtures of such carriers can also be used.
• Suitable carriers for granules are: eg broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
• liquefied gaseous diluents or solvents can be used.
• Particularly suitable are those extenders or carriers which are gaseous at normal temperature and under atmospheric pressure, for example aerosol propellants, such as halogenated hydrocarbons, as well as 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 lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic 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 sulphosuccinic acid esters, taurine derivatives (preferably alkyltaurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols, and derivatives of the compounds containing sulphates, sulphonates and phosphates, for example alkylarylpolyglycol ethers, alkylsulphonates, Alkyl sulfates, arylsulfonates, protein hydro
• dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes, and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• 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 applications derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex 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 active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
• retention promoters are all those substances which 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 material mobility (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 Kokosiettethoxylat (10) or Isotridecylethoxylat (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
• the formulations generally contain between 0.01 and 98% by weight of active ingredient, preferably between 0.5 and 90%.
• the active compounds according to the invention can also be used in admixture with one or more suitable fungicides, bactericides, acaricides, nematicides, insecticides, microbiologicals, fertilizers, attractants, phytotonics, sterilants, synergists, safeners, semiochemicals and / or plant growth regulators. for example to broaden the spectrum of action, to extend the duration of action, to increase the speed of action, to prevent re-prominence or to prevent the development of resistance. Furthermore, such combinations can improve plant growth, tolerance to abiotic factors such. As high or low temperatures, against dryness or increased water or Bodensalzgehalt.
• flowering and fruiting behavior can be improved, germination and rooting optimized to facilitate cropping and harvest yields, affect ripeness, increase the quality and / or nutritional value of the harvested products, extend shelf life and / or improve crop workability.
• synergistic effects are obtained by combining the active compounds according to the invention and the mixing partners. the effectiveness of each mixture is greater than the effectiveness of the individual components.
• the combinations can be used both in pre-mix, tank or finished mixes and in seed applications.
• Pesticide Manual The Pesticide Manual 14th Ed., British Crop Protection Council 2006
• searchable on the Internet e.g., http://www.alanwood.net/pesticides
• Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC and xylylcarb; or
• AChE Acetylcholinesterase
• Organophosphates e.g. Acephate, Azamethiphos, Azinophos-ethyl, Azinophos-methyl, Cadusafos, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinone, Dichlorvos / DDVP, Dicrotophos, Dimethoates, Dimethylvinphos, Disulfone, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O- (methoxyaminothio-phosphoryl) salicylate, Isoxathione, Malathion, Mecarbam, Methamidophos, Methida
• GABA-controlled chloride channel antagonists such as cyclodiene organochlorines, e.g. Chlordane and endosulfan; or
• Phenylpyrazoles e.g. Ethiprole and fipronil.
• Pyrethroids e.g. Acrinathrin, AUethrin, d-cis-trans AUethrin, d-trans AUethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin, alpha Cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) trans isomers], deltamethrin, empenthrin [(EZ) (lR) isomers], esfenvalerates, etof
• nicotinergic acetylcholine receptor (nAChR) agonists such as Neonicotinoids, eg acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or
• nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
• Avermectins / milbemycins e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
• Juvenile hormone mimics such as juvenile hormone analogs, e.g. Hydroprene, kinoprene and methoprene; or fenoxycarb; or pyriproxyfen.
• agents with unknown or nonspecific modes of action such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or
• mite growth inhibitors e.g. Clofentezine, hexythiazox and diflovidazine; or Etoxazole.
• Insect intestinal membrane microbial disruptors e.g. Bacillus thuringiensis subspecies israelensis, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and B.t. Plant proteins: CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34 From 1/35 Abi; or
• Bacillus sphaericus Bacillus sphaericus.
• inhibitors of oxidative phosphorylation, ATP disraptors such as diafenthiuron; or organotin compounds, eg azocyclotin, cyhexatin and fenbutatin oxide; or propargite; or tetradifon.
• Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
• Type 0 inhibitors of chitin biosynthesis such as bistrilluron, chloraluazuron, dillubenzuron, flucycloxuron, flufenoxuron, hexallumuron, lufenuron, novaluron, noviflumuron, tellubenzuron and triflumuron.
• inhibitors of chitin biosynthesis type 1, such as buprofezin.
• Moulting agents dipteran, such as cyromazine.
• ecdysone receptor agonists such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
• Octopaminergic agonists such as amitraz.
• complex III electron transport inhibitors such as hydramethylnone; or acequinocyl; or fluacrypyrim.
• METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad and Tolfenpyrad; or
• Rotenone (Derris). (22) voltage dependent sodium channel blockers, e.g. indoxacarb; or metaflumizone.
• Tetronic and tetramic acid derivatives e.g. Spirodiclofen, spiromesifen and spirotetramat.
• Phosphines e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanide.
• Diamides e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide.
• drugs with unknown mechanism of action such as amidoflumet, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, quinomethionate, cryolites, dicofol, diflovidazine, fluensulfones, flufenerim, flufiprole, fluopyram, fufenozide, imidaclothiz, iprodione, meperfluthrin, pyralidyl, pyrifluquinazone, tetramethylfluthrin and iodomethane; furthermore preparations based on Bacillus firmus (in particular strain CNCM 1-1582, for example VOTiVO TM, BioNem) and the following known active compounds:
• Fungicides (1) inhibitors of ergosterol biosynthesis, such as Aldm ph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, DodenKM-ph, DodenK ⁇ h acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, Fenhexamid, fenpropidin, fenpropimo ⁇ h, fluquinconazole, ⁇ , flusilazole, flutriafol, furconazole, furconazole cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoc
• inhibitors of respiration on the complex I and II of the respiratory chain, such as bixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, furmecyclox, isopyrazam mixture of syn-epimeric racemate 1RS, 4SR, 9RS and the anti-empleric racemate 1RS, 4SR, 9SR, isopyrazam (anti-epimeric racemate), isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS), isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS), isopyrazam (syn-epimeric racemate 1RS, 4SR,
• inhibitors of respiration at the complex III of the respiratory chain, such as ametoctradine, amisulbrom, azoxystrobin, cyazofamide, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enoxastrobin, famoxadone, fenamidone, flufenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, qrysastrobin , Picoxystrobin, Pyraclostrobin, Pyrametostrobin, Pyraoxystrobin, Pyribencarb, Triclopyricarb, Trifloxystrobin, (2E) -2- (2- ⁇ [6- (3-chloro-2-methylphenoxy) -5-fluoropyrimidin-4-yl] oxy ⁇ phenyl) -2- (methoxyimino) -N-methylacetamide, (2E) -2- (methoxyimino) -N-
• Mitosis and cell division inhibitors such as benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fluopicolide, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl,
• Compounds with multisite activity such as Bordeaux mixture, captafol, captan, chlorothalonil, copper preparations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate, dichlofluanid, dithianon, dodine, dodine free base, Ferbam, Fluorofolpet, Folpet, Guazatin, Guazatin acetate , Iminoctadine, iminoctadinal besylate, iminoctadine triacetate, Mancopper, mancozeb, maneb, metiram, zinc metiram, copper oxine, propamidine, propineb, sulfur and sulfur preparations such as calcium polysulfide, thiram, tolylfluanid, zineb, ziram and anilazine.
• copper preparations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate, dich
• resistance inducers such as acibenzolar-S-methyl, isotianil, probenazole, tiadinil and laminarin.
• inhibitors of amino acid and protein biosynthesis such as andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil, 3- (5-fluoro-3,3,4,4-tetramethyl-3 , 4-dihydroisoquinolin-1-yl) quinolines, oxytetracyclines and streptomycin.
• inhibitors of ATP production such as fentin acetate, fentin chloride, fentin hydroxide and silthiofam.
• inhibitors of cell wall synthesis such as benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamide, polyoxins, polyoxorim, validamycin A, valifenate and polyoxin B.
• inhibitors of lipid and membrane synthesis such as biphenyl, chloroneb, dicloran, edifenphos, etridiazole, iodocarb, Iprobenfos, isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb, pyrazophos, quintozene, tecnazene and tolclofos-methyl.
• Inhibitors of melanin biosynthesis such as carpropamide, diclocymet, fenoxanil, fthalide, pyroquilone, tricyclazole, and 2,2,2-trifluoroethyl ⁇ 3-methyl-1 - [(4-methylbenzoyl) amino] butane-2 - yl carbamate.
• Inhibitors of nucleic acid synthesis such as benalaxyl, benalaxyl-M (kiralaxyl), bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M
• Signal transduction inhibitors such as chlozolinate, fenpiclonil, fludioxonil, iprodione, procymidone, quinoxyfen, vinclozoline and proquinazide
• Decouplers such as binapacryl, dinocap, ferimzone, fluazinam and meptyldinocap.
• Other compounds such as benthiazole, bethoxazine, capsimycin, carvone, quinomethionate, pyriofenone (Chlazafenone), Cufraneb, cyflufenamid, cymoxanil, cyprosulfamide, dazomet, debacarb, dichlorophen, diclomethine, difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomat, fenpyrazamine, Flumetover, fluoromide, flusulfamide, flutianil, fosetyl-aluminum, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, irumamycin, methasulfocarb, methylisothiocyanate, me
• a mixture with other known active ingredients, such as herbicides, fertilizers, growth regulators, safeners, semiochemicals, or with agents for improving the plant properties is possible.
• the active compounds according to the invention can furthermore be present in the form of insecticides in their commercial formulations and in the formulations prepared from these formulations in admixture with synergists.
• Synergists are compounds which increase the effect of the active ingredients without the added synergist itself having to be active.
• the active compounds according to the invention may furthermore, when used as insecticides in their commercial formulations and in the forms of use prepared from these formulations, be present in mixtures with inhibitors which reduce degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant tissues ,
• the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
• the active ingredient concentration of the use forms may be from 0.00000001 up to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.
• the application is done in a custom forms adapted to the application.
• plants and parts of plants can be treated.
• plants are understood as meaning all plants and plant populations, such as desired and undesired ones Wild plants or crops (including naturally occurring crops).
• 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.
• Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, by way of example leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and roots, tubers and rhizomes.
• the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
• the treatment according to the invention of the plants and plant parts with the active ingredients is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in propagating material, in particular in seeds, further by single or multi-layered wrapping.
• plants and their parts can be treated.
• wild-type or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
• plant cultivars 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 terms "parts” or “parts of plants” or “plant parts” have been explained above.
• Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
• the treatment according to the invention may also give rise to superadditive ("synergistic") effects.
• superadditive for example, reduced application rates and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents usable in the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering power facilitated harvest, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability of the harvested products, which exceed the actual expected effects.
• 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 defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.
• transgenic plants are the important crops such as cereals (wheat, rice), corn, soybeans, potatoes, sugar beets, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and Grapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape.
• Traits which are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those which are 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 combinations thereof) in the plants (hereinafter "Bt plants”). Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
• SAR systemic acquired resistance
• Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
• the genes which confer the desired properties (“traits") can also occur in combinations with one another in the transgenic plants.
• Examples of “Bt plants” are maize varieties, cotton varieties, soybean varieties and potato varieties which are sold under the trade names YIELD GARD® (eg corn, cotton, soya), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
• herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
• Roundup Ready® tolerance to glyphosate eg corn, cotton, soy
• Liberty Link® tolerance to phosphinotricin, eg rapeseed
• IMI® tolerance against imidazolinone
• STS® tolerance to sulfonylureas eg corn
• Clearfield® varieties eg corn
• the listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active substance mixtures according to the invention.
• the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants.
• Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
• the active compounds of the present invention may be used to control a variety of pests including, for example, noxious sucking insects, biting insects and other plant parasitic pests, storage pests, pests that destroy industrial materials, and use and control pests, including animal health parasites, such as their extinction and eradication.
• the present invention thus also includes a method of controlling pests.
• the active substances according to the present invention act against animal parasites, in particular ectoparasites or endoparasites.
• the term endoparasites includes in particular helminths such as cestodes, nematodes or trematodes, and protozoa such as kozzidia.
• Ectoparasites are typically and preferably arthropods, especially insects such as flies (stinging and licking), parasitic fly larvae, lice, hair-pieces, feathers, fleas and the like; or acarids such as ticks, for example ticks or leather ticks, or mites such as mange mites, mites, feather mites and the like.
• These parasites include: From the order of Anoplurida eg Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; specific examples are: Linognathus setosus, Linognathus vituli, Linognathus ovillus, Linognathus oviformis, Linognathus pedalis, Linognathus stenopsis, Haematopinus asini macrocephalus, Haematopinus eurysternus, Haematopinus suis, Pediculus humanus capitis, Pediculus humanus corporis, Phylloera vastatrix, Phthirus pubis, Solenopotes capillatus; From the order of Mallophagida and the suborders Amblycerina and Ischnocerina eg Trimenopon spp., Menopon
• heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
• Ornithonyssus spp. Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp .; specific examples are: Argas persicus, Argas reflexus, Ornithodorus moubata, Otobius megnini, Rhipicephalus (Boophilus) microplus, Rhipicephalus (Boophilus) decoloratus, Rhipicephalus (Boophilus) annulatus, Rhipicephalus (Boophilus) calceratus, Hyalomma anatolicum, Hyalomma aegypticum, Hyalomma marginatum, Hyalomma transiens, Rhipicephalus evertsi, Ixodes ricinus, Ixodes hexagonus, Ixodes
• Actinedida Prostigmata
• Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp , Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp .; special examples are: Cheyletiella yasguri, Cheyletiella yasguri,
• the active compounds according to the invention are also suitable for controlling arthropods, helminths and protozoa which infect animals.
• the animals include farm animals such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, farmed fish, honey bees.
• farm animals such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, farmed fish, honey bees.
• the animals also include domestic animals - also referred to as pets - such as pets. Dogs, cats, caged birds, aquarium fish and so-called experimental animals such. Hamsters, guinea pigs, rats and mice.
• control of the parasites can also help to prevent the transmission of infectious substances.
• control means that the active ingredients act by reducing the incidence of the parasite in question in an animal affected by such parasites to harmless levels. More specifically, as used herein, “control” means that the agent kills the subject parasite, inhibits its growth, or inhibits its proliferation.
• the active compounds of the invention when used for the treatment of animals, can be used directly.
• they are used as pharmaceutical compositions which may contain pharmaceutically acceptable excipients and / or adjuvants known in the art.
• the active ingredients in
• the active compounds according to the invention can be used as formulations (for example powders, wettable powders, WP), emulsions, emulsifiable concentrates (EC), flowable agents, homogeneous solutions and Suspension concentrates [suspension concentrates, "SC"]) containing the active ingredients in an amount of 1 to 80% by weight, directly or after dilution (eg 100 to 10 000 times dilution) or use them as a chemical bath.
• formulations for example powders, wettable powders, WP), emulsions, emulsifiable concentrates (EC), flowable agents, homogeneous solutions and Suspension concentrates [suspension concentrates, "SC”]
• SC Suspension concentrates
• the compounds according to the invention have a high insecticidal activity against insects which destroy industrial materials.
• insects such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Ernobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollis, Lyctus linearis, Lyctus pubescens, Trogoxylon aequale, Minthes rugicollis, Xyleborus spec. Tryptodendron spec.
• Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
• Bristle tails like Lepisma saccharina.
• Technical materials in the present context are non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
• the ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
• the compounds according to the invention can be used alone or in combinations with other active substances as antifouling agents.
• the active compounds are also suitable for controlling animal pests in household, hygiene and storage protection, in particular of insects, arachnids and mites, in closed rooms, such as apartments, factories, offices, vehicle cabins, etc. occurrence. They can be used to control these pests, alone or in combination with other active ingredients and adjuvants in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
• Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
• Araneae e.g. Aviculariidae, Araneidae.
• Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
• Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
• Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys Calcitrans, Tipula paludosa.
• Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
• siphonaptera e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
• Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
• Heteroptera e.g. Cimex hemipterus, Cimex lectulanus, Rhodinus prolixus, Triatoma infestans.
• the benzoxazinones required as starting materials in carrying out the process (A) are generally defined by the formula (II).
• R 2 , R, R 4 , R 5 , G, X, m and n are as defined above.
• Benzoxazinones of the formula (II) are new. They are obtained, for example, by reacting pyrazolecarboxylic acid derivatives of the formula (VI)
• R 2 , R 3 , R 4 and m have the meanings given above, in the presence of a base (eg triethylamine or pyridine) and in the presence of a sulfonyl chloride (eg methanesulfonyl chloride) and optionally in the presence of a diluent (eg acetonitrile).
• a base eg triethylamine or pyridine
• a sulfonyl chloride eg methanesulfonyl chloride
• a diluent eg acetonitrile
• Aldehydes of the formula (IX) are known in some cases (WO 2013/024005). In analogy to known processes, they can be prepared from anthranilic acids of the formula (XI)
• Anthranilic acids of the formula (XI) are commercially available, known in the literature or can be synthesized in analogy to known methods.
• G, X, n and R 5 have the abovementioned meaning are novel, known from the literature or can be prepared analogously to processes known from the literature.
• aminobenzamides required as starting materials in carrying out the process (B) are generally defined by the formula (IV)
• the process (B) is carried out in the presence of an acid binder.
• an acid binder Suitable for this purpose are all customary for such coupling reactions inorganic or organic bases.
• polymer-supported acid binders for example polymer-bound diisopropylamine and polymer-bound dimethylaminopyridine.
• the process (B) may optionally be carried out in the presence of an inert organic diluent customary for such reactions.
• aliphatic, alicyclic or aromatic hydrocarbons such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane, 1, 2-diethoxyethane or anisole; Ketones such as acetone, butanone, methyl isobutyl ketone or cyclohexanone; Nitriles,
• R 2 , R 3 , R 4 and m have the abovementioned meaning, according to a generally known reaction with compounds R : -Y, where Y is a leaving group, such as halogen, in the presence of a base.
• G, X, n and R 5 have the abovementioned meaning
• a chlorinating agent eg thionyl chloride or oxalyl chloride
• an inert diluent eg toluene or dichloromethane
• process (B) The pyrazolecarboxylic acids which are furthermore required as starting materials for carrying out process (B) have already been described by process (A).
• process (C) is carried out in the presence of a condensing agent. All agents customary for such coupling reactions are suitable for this purpose.
• acid halide formers such as phosgene, phosphorus tribromide, phosphorus trichloride, phosphorus pentachloride, phosphorus oxychloride or thionyl chloride;
• Anhydride formers such as ethyl chloroformate, methyl chloroformate, isopropyl chloroformate, isobutyl chloroformate or methanesulfonyl chloride;
• Carbodiimides such as ⁇ , ⁇ '-dicyclohexylcarbodiimide (DCC) or other conventional condensing agents, such as phosphorus pentoxide, polyphosphoric acid, ⁇ , ⁇ -carbonyldiimidazole, 2-ethoxy-N-ethoxycarbonyl-l, 2-dihydroquinoline (EEDQ), triphenylphosphine / carbon tetrachloride, bromine -tripyrrolidinophosphonium hexafluoride
• the process (C) is optionally carried out in the presence of a catalyst.
• a catalyst examples which may be mentioned are 4-dimethylaminopyridine, 1-hydroxybenzotriazole or dimethylformamide.
• the process (C) may optionally be carried out in the presence of an inert organic diluent customary for such reactions.
• organic diluent customary for such reactions.
• these include, preferably, aliphatic, alicyclic or aromatic hydrocarbons, such as, for example, petroleum ether, hexane, heptane, cyclohexane, methylcyclohexane, benzene, toluene, xylene or decalin; halogenated hydrocarbons, such as chlorobenzene, dichlorobenzene, dichloromethane, chloroform, carbon tetrachloride, dichloroethane or trichloroethane; Ethers, such as diethyl ether, diisopropyl ether, methyl t-butyl ether, methyl t-amyl ether, dioxane, tetrahydrofuran, 1,2-dimethoxyethane,
• the hydrazides required as starting materials in carrying out the process (D) are generally defined by the formula (VII).
• R 1 , R 2 , R 3 , R 4 , R 5 , R 8 , R 9 , G, X, m and n have the abovementioned meaning.
• the process (D) is carried out in the presence of an acid binder as described in connection with process (B).
• Step 1 Ethyl 1- (3-chloropyridin-2-yl) -3- (2,2-difluoroethoxy) -1H-pyrazole-5-carboxylate 1.00 g (3.73 mmol) of ethyl 1- (3 -chloropyridin-2-yl) -3-ydroxy-lH-pyrazole-5-carboxylate (Li: WO 2004046129) were initially charged in 6 ml of pyridine and washed successively with 1.08 g (5.60 mmol) of 2-iodo-1, 1-difluoroethane and 1.03 g (7.47 mmol) of potassium carbonate. It was then heated to 100 ° C for 18 hours.
• Step 2 1- (3-Chloropyridin-2-yl) -3- (2,2-difluoroethoxy) -1H-pyrazole-5-carboxylic acid
• the compounds of the formula (I) can be obtained, for example the following compounds of the formula (I):
• Step 2 2-Amino-5 - [(E) - (methoxyimino) methyl] -3-methylbenzoic acid (VIII-1)
• Step 3 2- [1- (3-Chibridinyl-2-yl) -3- (2,2-difluoroethoxy) -1 H -pyrazol-5-yl] -8-methyl-4-oxo-4H- 3, 1 - benzoxazine-6-carbaldehyde O-methyloxime
• Step 4 Methyl 2- ⁇ 2 - ( ⁇ [1- (3-chloropyridin-2-yl) -3- (2,2-difluoroethoxy) -1H-pyrazol-5-yl] carbonyl ⁇ amino) -5- [(E) - ( ⁇ - 1-methylhydrazinecarboxylate
• Step 1 2- [1- (3-Chloropyridin-2-yl) -3- (difluoromethoxy) -1-H-pyrazol-5-yl] -8-methyl-4-oxo-4H-3,1-benzoxazine 6-carbaldehyde O-methyloxime
• Step 2 1- (3-Chloro-2-yl) -3- (difluoromethoxy) -N- ⁇ 2- (hydrazinocarbonyl) -4 - [(E) - (methoxyimino) methyl] -6-methylp-carboxamide
• Step 3 Methyl 2- ⁇ 2 - ( ⁇ [1- (3-chloropyridin-2-yl) -3- (difluoromethoxy) -1H-pyrazol-5-yl] carbonyl ⁇ 5 - [(E) - (methoxyimino ) methyl] -3-methylbenzoyl ⁇ hydrazinecarboxylate
• R 1 and (R 3 ) m are H, R 2 and R 4 are CH 3 , X is N and (R 5 ) "is 3-Cl and G, R 8 , R 9 and R 10 are as shown in Table A have indicated meaning.
• A-36 H ⁇ N F F H H -C (O) OMe 661, 1 2.87
• R ⁇ R 6 and (R 3 ) m are H, R 2 and R 4 are CH 3 , X is N, and (R 5 ) n is 3-Cl and G, U and (R 19 ) p are those in Table B given meaning.
• R 1 , and (R 3 ) m is H
• R 2 is CH 3
• X is N
• (R 5 ) n is 3-Cl
• R 4 , R 6 , R 7 and G are those given in Table C. Have meaning.
• Me methyl
• Et ethyl
• iPr iso-propyl
• cPr cyclo-propyl
• tBu tertiary-butyl
• the alkoximino compounds listed in Tables A, B and C are generally present as mixtures of the E and Z isomers on the Alkoximinofunktion.
• the E isomer is the main component (> 90%) and the Z isomer is the minor component ( ⁇ 10%). Unless stated otherwise, the data given refer to the E isomer.
• a) The determination of M + with the LC-MS in the acidic range is carried out at pH 2.7 acetonitrile (contains 0.1% formic acid) and water as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile Device: Agilent 1100 LC system, Agilent MSD system, HTS PAL.
• ⁇ -NMR data is performed with a Bruker Avance 400 equipped with a 60 ⁇ volume flow-through head, with tetramethylsilane as reference (0.0) and the solvents CD 3 CN, CDC1 3 , De-DMSO.
• 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 peak list of an example therefore has the form: ⁇ (intensityi); ⁇ 2 (intensity 2); ; ⁇
• Boophilus microplus injection test (BOOPMI Inj)
• ⁇ of the drug solution is injected into the abdomen of 5 wet, adult, female bovine ticks (Boophilus microplus). The animals are transferred to trays and kept in an air-conditioned room.
• the effect control takes place after the desired time on storage of fertile eggs. Eggs whose fertility is not visible from the outside are stored in the climatic cabinet for about 42 days until larval hatching. An effect of 100% means that none of the ticks have laid fertile eggs, 0% means that all eggs are fertile.
• Lucilla cuprina - test (LUCICU)
• 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.
• the kill is determined in%. 100% means that all flies have been killed; 0% means that none of the flies have been killed. In this test, e.g. the following compounds of the preparation examples an effect of 100% at a rate of lOOppm: C-24
• Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
• 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. After the desired time, the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
• Phaedon cochleariae - Spray Test (PHAECO) Solvent 78.0 parts by weight acetone
• Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
• Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).
• the effect is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
• SPODFR Spodoptera frugiperda - spray test
• Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
• a suitable preparation of active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
• Corn leaf disks ⁇ Zea mays) are sprayed with an active compound preparation of the desired concentration and, after drying, are populated with caterpillars of the armyworm (Spodoptera frugiperda).
• the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.
• Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
• Bean leaf discs Phaseolus vulgaris
• etranychus urticae Bean leaf discs infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active substance preparation of the desired concentration.
• the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.

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