EP1814874A1 - Diamides d'acide n-heterocyclylphtalique utilises comme insecticide - Google Patents

Diamides d'acide n-heterocyclylphtalique utilises comme insecticide

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Publication number
EP1814874A1
EP1814874A1 EP05811673A EP05811673A EP1814874A1 EP 1814874 A1 EP1814874 A1 EP 1814874A1 EP 05811673 A EP05811673 A EP 05811673A EP 05811673 A EP05811673 A EP 05811673A EP 1814874 A1 EP1814874 A1 EP 1814874A1
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EP
European Patent Office
Prior art keywords
spp
alkyl
formula
carbonyl
cyano
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05811673A
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German (de)
English (en)
Inventor
Rüdiger Fischer
Christian Funke
Olga Malsam
Tetsuya Murata
Katsuaki Wada
Yasushi Yoneta
Katsuhiko Shibuya
Eiichi Shimojo
Christian Arnold
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Bayer CropScience AG
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Bayer CropScience AG
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Publication of EP1814874A1 publication Critical patent/EP1814874A1/fr
Withdrawn legal-status Critical Current

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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
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • 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
    • A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
    • A01N43/647—Triazoles; Hydrogenated triazoles
    • A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • 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
    • C07D401/06—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 linked by a carbon chain containing only aliphatic carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/06—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
    • 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
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Definitions

  • the present application of an invention relates to novel N-heterocyclylphthalic diamides, processes for their preparation and their use as pesticides and pesticides, in particular as insecticides.
  • N-arylphthalic diamides have insecticidal properties (compare US Pat. Nos. 6,362,369, 6,003,044, WO 01/02354, WO 01/21576, WO 01/46124, WO 02/48137, WO 02/94765 , WO 04/018415).
  • n stands for the numbers 0, 1, 2, 3 or 4,
  • A represents O (oxygen), S (sulfur), SO or SO 2 , NH or N (alkyl), or represents straight-chain or branched, optionally substituted and optionally by O (oxygen), S (sulfur), SO or SO 2 , NH or N (alkyl) is interrupted alkanediyl (alkylene),
  • Q 1 represents an optionally substituted heterocyclic grouping
  • Q 2 is an optionally substituted heterocyclic grouping
  • R 1 is hydrogen, cyano or the grouping A 1 -X 1 , wherein A 1 is a single bond, for O (oxygen), S (sulfur), SO, SO 2 , NH, CO, COO, or straight-chain or branched alkanediyl (Alkylene) and X 1 is in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl or heterocyclyl, and X is nitro, cyano, halogen or the grouping A 2 -X 2 , where A 2 is a single bond, O (oxygen), S (sulfur), SO, SO 2 , OSO 2 , NHSO 2 , CO, OCO, NHCO or alkanediyl (alkylene) and X 2 is in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl or aryl.
  • the compounds of formula (T) may be "optionally also in the form of addition compounds with acidic or basic substances and, if appropriate, also as adducts with oxygen in the form of N-oxides.
  • the compounds of formula (T) may also be optionally substituted as stereoisomers, i.e., depending on the nature of the substituents. as geometric and / or as optical isomers or as mixtures of isomers in different compositions. Both the pure stereoisomers and any desired mixtures of these isomers form the subject of the invention, even though in general only the compounds of the formula (T) are mentioned here.
  • Halogen substituted radicals e.g. HaloalkyL
  • Halogen substituted radicals are halogenated once or several times up to the maximum possible substituent number.
  • the halogen atoms may be the same or different.
  • Halogen is fluorine, chlorine, bromine or iodine, in particular fluorine, chlorine or bromine.
  • N-heterocyclylphthalamides of the formula (I) are obtained when 3-imino-2-benzofuran-1 (3H) -ones of the formula (H)
  • the compounds of the formula (I) according to the invention have very interesting biological properties and for controlling animal pests, such as arthropods and nematodes, in particular insects, in crop protection, material protection and Vorrats ⁇ protection, as well as in the areas of household / hygiene and Animal health are suitable.
  • animal pests such as arthropods and nematodes, in particular insects, in crop protection, material protection and Vorrats ⁇ protection, as well as in the areas of household / hygiene and Animal health are suitable.
  • N-heterocyclylphthalic diamides according to the invention are generally defined by the formula (T).
  • Preferred definitions of the radicals of the formulas listed above and below are given below. These definitions apply equally to the end products of formula (I) as well as to all intermediates.
  • n is preferably the numbers 1, 2 or 3.
  • n is particularly preferably the numbers 1 or 2.
  • A is preferably O (oxygen), S (sulfur), SO or SO 2 , NH or N (C 1 -C 4 -alkyl), or straight-chain or branched, optionally substituted by cyano, halogen or C 1 -C 6 -alkoxy and optionally O (oxygen), S (sulfur), SO or SO 2 , NH or
  • Q 1 is preferably an optionally substituted heterocyclic moiety having up to 10 carbon atoms and at least one heteroatom from the series O (oxygen), S
  • Q 1 is particularly preferably an optionally substituted monocyclic heterocyclic grouping having up to 5 carbon atoms and 1 to 4 N atoms and / or an O atom and / or an S atom and / or an SO 2 or SO 2 - Grouping as -A -
  • Q 1 most preferably represents an optionally substituted pyridine moiety, pyrimidine moiety, pyrazole moiety, pyridazine moiety, triazole moiety, oxadiazole moiety, thiadiazole moiety, pyrazole moiety, imidazole moiety,
  • Q 2 is preferably an optionally substituted heterocyclic moiety having up to 10 carbon atoms and at least one heteroatom from the series O (oxygen), S
  • Q 2 is particularly preferably an optionally substituted monocyclic or bicyclic heterocyclic grouping having up to 9 carbon atoms and 1 to 5 N atoms and / or an O atom and / or an S atom and / or an SO or SO 2 -
  • Q 2 very particularly preferably represents an optionally substituted pyrrole group
  • R 1 is preferably hydrogen or the group A 1 -X 1 , where A 1 is a single bond, for O (oxygen), S (sulfur), SO, SO 2 , NH, CO or COO, or for straight-chain -chain or branched alkanediyl (alkylene) having 1 to 10 carbon atoms, and X 1 is optionally substituted by hydroxyl, cyano, carbamoyl, hydroxyimino, halogen, Ci-C 6 - alkoxy, Ci-C ⁇ alkylthio, Ci-C 6 -Alkylsulfmyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -alkyl-amino-sulfonyl, C 1 -C 6 -alkyl-carbonyl, C 1 -C 6 -alkyl-carbonyl-amino, C 1 -C 6 -alkyl-amino, C 1 -C 6
  • a 1 is a single bond, O (oxygen), S (sulfur), SO, SO 2 , NH, CO or COO, or straight-chain or branched alkanediyl ( Alkylene) having 1 to 6 carbon atoms
  • X 1 is optionally substituted by hydroxy, cyano, carbamoyl, hydroxyimino, halogen, C 1 -C 5 - alkoxy, Q-Cs-alkylthio, Ci-Cs-alkylsulfinyl, C r C 5 - alkylsulfonyl, Cs-Q-alkyl-sulfonyl am ⁇ no-, C r C 5 alkyl-carbonyl, CRQ-alkyl-carbonyl-amino, CRCS-alkyl-amino-carbonyl-oxy, di-fQ-Cs-alkyty-ainmo-carbonyl
  • a 1 is a single bond, for O (oxygen), S (sulfur), SO, SO 2 , NH, CO or COO, or for methylene, Ethane-1, l-diyl (ethylidene), ethane-l, 2-diyl (dimethylene), propane-l, l-diyl (propylidene), propane-l, 2-diyl or propane-l, 3-diyl (trimethylene ), and X 1 is in each case optionally substituted by hydroxy, cyano, carbamoyl, hydroximino, fluorine, chlorine, bromine or iodine, methoxy,
  • Phenyl or in each case optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Fluoromethyl, chloromethyl, difluoromethyl, Dichlo ⁇ nethyl, trifluoromethyl, trichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, trifluoroethyl, trichloroethyl, chlorofluoroethyl, chlorodifluoroethyl, fluoro-dichloroethyl, tetrafluoroethyl, pentafluoroethyl, methoxy, ethoxy, n- or i-
  • a 2 is preferably nitro, cyano, halogen or the group A 2 -X 2 , where A 2 is a single bond, for O (oxygen), S (sulfur), SO, SO 2 , OSO 2 , NHSO 2 , CO, OCO or NHCO, or atoms is straight-chain or branched alkanediyl (alkylene) having 1 to 10 Kohlen ⁇ and X 2 is optionally substituted by hydroxy, cyano, halogen, C r C 6 alkoxy, C r C 6 alkylthio, C r C 6 - alkoxyimino atoms or Ci-C 6 alkoxy-carbonyl-substituted alkyl having 1 to 10 Kohlenstoff ⁇ , represents in each case optionally cyano-, halogen and / - alkylsulphinyl, C r C 6 alkylsulfonyl, C r C 5 alkyl-carbonyl, QC 6 or C r C
  • X particularly preferably represents nitro, cyano, halogen or the group A 2 -X 2 , where A 2 is a single bond, for O (oxygen), S (sulfur), SO, SO 2 , OSO 2 , NHSO 2 , CO, OCO or NHCO, or represents straight-chain or branched alkanediyl atoms of (alkylene) having 1 to 6 carbon atoms and X 2 is optionally substituted by hydroxy, cyano, halogen, Ci-C 5 alkoxy, C 5 - alkylthio, C 1 - C 5 -AlkYlSuIfUIyI, Q-Cs-alkylsulfonyl, Ci-Cs-alkyl-carbonyl, Ci-C 5 -alkoximino or Q-Cs-alkoxycarbonyl-substituted alkyl having 1 to 6 carbon atoms, in each case if appropriate by cyano, halogen and / or C
  • X very particularly preferably represents nitro, cyano, fluorine, chlorine, bromine, iodine or the grouping A 2 -X 2 , where A 2 is a single bond, for O (oxygen), S (sulfur), SO, SO 2 , OSO 2 , NHSO 2 , CO, OCO or NHCO, or for methylene, ethane-1, l-diyl (ethylidene),
  • A is methylene
  • Q 1 represents one of the heterocyclic groupings below
  • these groups each optionally represent one or optionally two substituents from the series nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, etbyl, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl,
  • Q 2 is one of the heterocyclic groupings below,
  • these groups each optionally substituents from the series cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, difluoromethyl, trifluoromethyl , Chlorodifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl,
  • R 1 is the grouping A 1 -X 1 , wherein A 1 is a single bond and X 1 is in each case optionally substituted by hydroxy, cyano, carbamoyl, hydroximino, fluorine, chlorine, bromine or iodine, methoxy, ethoxy, n- or i -Propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulfinyl, ethylsulfinyl, propylsulfinyl, methylsulfonyl, ethylsulfonyl, Methylaminosulfonyl, ethylaminosulfonyl, n- or i-propylaminosulfonyl, n-
  • X 3 represents chlorine, bromine, iodine, methylsulfonyloxy or ethylsulfonyloxy.
  • A is methylene
  • Q 1 represents one of the heterocyclic groupings below
  • these groups each optionally having substituents from the series nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, methylthio, ethyl thio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, most preferably methyl,
  • Q 1 further represents the heterocyclic grouping below,
  • this group optionally contains substituents from the series nitro, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, methylthio, ethylthio,
  • Q 2 is one of the heterocyclic groupings below,
  • substituents for Q 2 are fluorine, iodine, difluoromethyl, pentafluoroethyl, heptafluoropropyl and methylsulfonyl, and
  • R 1 is 1 -methyl-2-memylthio-ethyl, 1-methyl-2-ethylthio-e% l, 1-methyl-2-methylsulfinyl-ethyl, 1-methyl-2-ethylsulfinyl-ethyl, 1-methyl-2 -methylsulfonyl-ethyl, 1-methyl-2-ethylsulfonyl-ethyl - very particularly preferably for (S) -l-methyl-2-methylthio-ethyl, (S) -l-methyl-
  • X 3 represents chlorine, bromine, iodine or methylsulfonyloxy.
  • A is methylene
  • Q 1 represents one of the heterocyclic groupings below
  • these groups each optionally contain substituents from the series fluorine, chlorine, bromine, iodine, methyl, very particularly preferably methyl,
  • Q 1 further represents the heterocyclic grouping below,
  • this grouping optionally contains substituents from the series fluorine, chlorine, bromine, iodine, methyl, very particularly preferably methyl,
  • Q 2 is one of the heterocyclic groupings below,
  • these groups each being optionally substituents from the series fluorine, iodine, methyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, chlorofluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoroethyl, fluoro-dichloroethyl, tetrafluoroethyl, pentafluoroethyl, hexafluoropropyl, heptafluoropropyl , Methylsulfonyl - most preferably trifluoromethyl -, further particularly preferred substituents for Q 2 are fluorine, iodine, difluoromethyl, pentafluoroethyl, heptafluoropropyl and methylsulf
  • R 1 represents 1 -methyl-2-methylthio-ethyl, 1-methyl-2-methylsulfinyl-ethyl, 1-methyl-2-methylsulfonyl-ethyl - very particularly preferably (S) -l-methyl-2-methylthio -ethyl, (S) -l-methyl-2-methylsulfinyl-ethyl, (S) -l-methyl-2-me% islsulfonyl-ethyl -, and
  • X 3 is chlorine, bromine, iodine.
  • hydrocarbon radicals such as alkyl
  • alkyl are in each case straight-chain or branched as far as possible, including in combination with heteroatoms, such as in alkoxy.
  • the compounds of the formula (I) have acidic or basic properties and can form salts. If the compounds of the formula (T) bear hydroxyl, carboxy or other acid-inducing groups, these compounds can be reacted with bases to form salts.
  • bases are, for example, hydroxides, carbonates, bicarbonates of the alkali and alkaline earth metals, in particular those of sodium, potassium, magnesium and calcium, furthermore ammonia, primary, secondary and tertiary amines having (QG ⁇ -Alkvlresten and mono-, di- and trialkanolamines of (Ci-C 4) alkanols.
  • acids are for example mineral acids, such as hydrochloric, sulfuric and phosphoric acid, organic acids such as acetic acid or oxalic acid, and acid salts such as NaHSO 4 and KHSO 4 .
  • the salts thus obtainable also have fungicidal, insecticidal, acaricidal and miticidal properties.
  • the invention also provides the salt-like derivatives formed from compounds of the formula (T) by reaction with basic or acidic compounds and the N-oxides which can be prepared by customary oxygenation methods.
  • reaction sequence in the inventive method can be outlined by the following equation:
  • n, R 1 and X preferably or in particular have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) as being preferred or particularly preferred for n, R 1 and X have been specified.
  • the starting materials of the formula (IT) are known and / or can be prepared by processes known per se (cf .. EP-A 0 919 542, EP-A 1 006 102, EP-A 1 006 107, US 6,559,341, WO 01 / 21576, WO 02/88075, WO 02/94765, WO 03/093228); in part, they are also the subject of a prior application (see European Patent Application No. 04020618.7 dated 31.08.2004, see the preparation examples).
  • Starting materials to be substituted heterocyclylamines are generally defined by the formula (TD).
  • formula (HT) A, Q 1 and Q 2 preferably or in particular have those meanings which have already been mentioned above in connection with the description of US Pat compounds of the formula (T) according to the invention have been indicated as being preferred or particularly preferred for A, Q 1 and Q 2 .
  • the starting materials of the formula (EU) are known and / or can be prepared by processes known per se (compare J. Heterocycl Chem 20 (1983), 807-809, J. Med. Chem., 21 (1978), 331 -337, J. Org Chem.42 (1977), 1523-1527, loc.cit 43 (1978), 736-737, WO 00/61572, WO 02/070494).
  • Q 3 , Q 4 , Q 5 , Q 6 and Q 7 are each CH or N (nitrogen), wherein in the two heterocyclic moieties, the H atoms in the CH positions are each also replaced by one of the substituents X listed above can.
  • reducing agents such as tin (IT) chloride / hydrochloric acid
  • diluents such as ethanol
  • R is alkyl, especially methyl or ethyl
  • R 2 is alkyl, preferably C 1 -C 4 -alkyl, in particular t-butyl,
  • the Azolylmethylnitroazine of the formula (TV) required for the synthesis variant (a) are not yet known from the literature.
  • the novel azolylmethylnitroazines of the formula (JV) are obtained when halomethylnitroazines of the formula (VH)
  • X 4 is halogen, in particular chlorine or bromine
  • a basic reaction auxiliary such as potassium carbonate
  • a diluent such as N, N-dimethyl-formamide
  • N-Azolylmethylpyrimidinyl-carbamates of the formula (VI) as intermediates are not yet known from the literature.
  • the N-Azolylmemylpyrimidinyl-carbamates of the formula (VI) are the subject of the present application as new substances.
  • Azolylacetamidines of the formula (IX) are known or can be prepared in a manner known per se.
  • azoles of the formula (VID) can be reacted with ethyl bromoacetate to give an azolylacetic acid ester (Abdul-Ghani et al., Journal of Fluorine Chemistry 1990, 48 (1), 149-52), which is then further converted into the aimidine of the formula (II. TX) (Gielen et al., Tetrahedron Lett. 2002, 43, 419-422).
  • Q 8 is O (oxygen) or S (sulfur) and
  • Q 9 is N (nitrogen) or CH, but in each case the H atoms in the CH positions of the heterocyclic groupings can also be replaced by one of the substituents X listed above.
  • reducing agents such as tin (IT) chloride / hydrochloric acid
  • diluents such as ethanol
  • nitro compounds of the formula (X) are not yet known from the literature. They can be prepared in a manner known per se from corresponding precursors of the formula (XI)
  • X 5 is halogen, in particular chlorine or bromine, or represents alkylsulfonyloxy, in particular methylsulfonyloxy or ethylsulfonyloxy,
  • nitro compounds of the formula (XI) are known or can be prepared in a known manner.
  • the alcohols can be brominated in a known manner.
  • Q 6 , Q 7 and Q 8 have the abovementioned meaning
  • Q 10 is N (nitrogen) or CH, but in each case the H atoms in the CH positions of the heterocyclic groupings can also be replaced by one of the abovementioned substituents X.
  • reducing agents such as tin (II) chloride / hydrochloric acid
  • diluents such as ethanol
  • nitro compounds of the formula (XH) are not yet known from the literature. They can be prepared in a manner known per se from corresponding precursors of the formula (XIH)
  • X 5 represents halogen, in particular chlorine or bromine, or represents alkylsulfonyloxy, in particular methylsulfonyloxy or ethylsulfonyloxy,
  • Q 6 and Q 7 have the abovementioned meaning, optionally in the presence of a basic reaction auxiliary, such as potassium carbonate, and optionally in the presence of a diluent such as acetonitrile, at temperatures between 0 ° C and 120 0 C are obtained (see, the preparation examples).
  • a basic reaction auxiliary such as potassium carbonate
  • a diluent such as acetonitrile
  • nitro compounds of the formula (XIII) are known or can be prepared in a known manner.
  • the alcohols can be brominated in a known manner.
  • reaction auxiliaries include, for example, hydrogen chloride or hydrochloric acid, hydrogen bromide, sulfuric acid, phosphoric acid, acetic acid, trifluoroacetic acid, methanesulfonic acid, benzenesulfonic acid and p-toluenesulfonic acid.
  • Suitable diluents for carrying out the process according to the invention are all inert solvents.
  • halogenated hydrocarbons especially chlorinated hydrocarbons such as tetrachlorethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1,2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene ; Alcohols such as methanol, ethanol, isopropanol, butanol; Ethers, such as ethyl propyl ether, methyl tert-
  • reaction temperatures can be varied within a substantial range when carrying out the process according to the invention. In general, one works at temperatures between -3O 0 C and +150 0 C, preferably between -10 0 C and + 100 0 C.
  • the process according to the invention is generally carried out under normal pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure-generally between 0.1 bar and 15 bar.
  • the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess.
  • the reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, if appropriate also under an inert gas atmosphere (for example under nitrogen, argon or helium) and the reaction mixture is generally stirred for several hours at the required temperature.
  • a reaction auxiliary for example under nitrogen, argon or helium
  • the work-up is carried out by customary methods (cf., the preparation examples).
  • the active compounds according to the invention are suitable for plant protection, good warm-blood toxicity and good environmental compatibility for the protection of plants and plant organs
  • Mollusks used in agriculture horticulture, animal husbandry, forests, gardens and
  • arachnids e.g. Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp.
  • Eriophyes spp. Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptrufa oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp. Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
  • Ceuthorhynchus spp. Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Derniestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptinotarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Mono
  • Diptera e.g. Aedes spp., Anopheles spp., Bibio hortulanus, Calliphora erythrocephala, Ceratitis capitata, Chrysomyia spp., Cochliomyia spp., Cordylobia anthropophaga, Culex spp., Cuterebra spp., Dacus oleae, Dermatobia hominis, Drosophila spp., Fannia spp.
  • Gastrophilus spp. Hylemyia spp., Hyppobosca spp., Hypoderma spp., Liriomyza spp. Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella firit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spp., Taimia spp., Tipulapaludosa, Wohlfahrtiaspp.
  • Gastropoda e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
  • helminths e.g. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris brericoides, 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., HeteraMs spp., Hymenolepis nana, Hyostrongulus spp., Loa Loa,
  • protozoa such as Eimeria
  • Eimeria protozoa
  • Heliopeltis spp. Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp. Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.
  • Stictocephala festina Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii.
  • Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
  • Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
  • siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
  • Symphyla eg Scutigerella immaculata.
  • Thysanoptera eg Basothrips biformis, Enneothrips flavens, Frarikliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., RMpiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
  • Thysanura e.g. Lepisma saccharina.
  • the plant parasitic nematodes include e.g. Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Dixtylenchus dipsaci, Globodera spp., Heliocotylenchus spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Rotylenchus spp. Trichodorus spp., Tylenchorhynchus spp., Tylenchulus spp., Tylenchulus semipenetrans, Xiphinema spp.
  • Anguina spp. Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Dixtylenchus dipsaci
  • the compounds of formula (I) according to the invention are distinguished by potent action against aphids (for example Aphis gossypii and Myzus persicae), beetle larvae (for example Phaedon cochleariae), butterfly caterpillars (for example Plutella xylostella, Spodoptera exigua and Spodoptera frugiperda).
  • aphids for example Aphis gossypii and Myzus persicae
  • beetle larvae for example Phaedon cochleariae
  • butterfly caterpillars for example Plutella xylostella, Spodoptera exigua and Spodoptera frugiperda.
  • the compounds according to the invention may 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.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • 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 variety protection 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, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, as well as roots, tubers and rhizomes.
  • the plant parts also include harvested material and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.
  • the treatment according to the invention of the plants and plant parts with the active ingredients takes place directly or by acting on their environment, habitat or storage space according to the usual treatment methods, for example by dipping, spraying, evaporating, atomizing, spreading, brushing, injecting and in the case of propagation material, in particular Seeds, still by single or multi-layer coating.
  • the active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural substances, Active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances.
  • customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural substances, Active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances.
  • formulations are prepared in a known manner, e.g. by mixing the active compounds with extenders, ie liquid solvents and / or solid carriers, if appropriate using surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
  • extenders ie liquid solvents and / or solid carriers
  • surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
  • auxiliaries it is possible to use those substances which are suitable for imparting special properties to the composition itself and / or preparations derived therefrom (for example spray liquors, seed dressing), such as certain technical properties and / or special biological properties.
  • Typical auxiliaries are: extenders, solvents and carriers.
  • 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 dimethyl sulfoxide).
  • 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
  • organic solvents can also be used as auxiliary solvents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, eg 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 dimethyl sulfoxide, and water.
  • Ais solid carriers are suitable:
  • Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed 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 paper, sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolysates;
  • Suitable dispersants are nonionic and / or ionic substances, e.g.
  • POE and / or POP ethers from the classes of alcohol POE and / or POP ethers, acid and / or POP-POE esters, alkyl-aryl and / or POP-POE ethers, fatty and / or POP-POE adducts, POE and / or POP polyol derivatives, POE and / or POP sorbitol or sugar adducts, alkyl or aryl sulfates, sulfonates and phosphates or the corresponding PO ether adducts.
  • suitable oligo- or polymers e.g. starting from vinylic monomers, from acrylic acid, from EO and / or PO alone or in combination with e.g.
  • Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids.
  • 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 trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • additives may be fragrances, mineral or vegetable optionally modified oils, waxes and nutrients (also 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.
  • the formulations generally contain between 0.01 and 98% by weight of active compound, preferably between 0.5 and 90%.
  • the active ingredient according to the invention may be present in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.
  • active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth regulators, herbicides, safeners, fertilizers or semiochemicals.
  • Particularly favorable mixing partners are e.g. the following:
  • Azoxystrobin Cyazofamide, Dimoxystrobin, Enestrobin, Famoxadone, Fenamidon, Fluoxastrobin, Kresoximmethyl, Metominostrobin, Orysastrobin, Pyraclostrobin, Picoxystrobin decoupler
  • Metconazole myclobutanil, paclobutrazol, penconazole, propiconazole, prothioconazole, simeconazole, tebuconazole, tetraconazole, triadimefon, triadimenol, triticonazole, Uniconazole, voriconazole, imazalil, imazalil sulfate, oxpoconazole, fenarimol, flurprimidol, nuarimol, pyrifenox, triforin, pefurazoate, prochloraz, triflumizole, viniconazole,
  • Carbamates for example Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Bendiocarb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran,
  • Organophosphates for example acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothione, chloroethoxyfos, chlorfenvinphos, chlormephos, chlo ⁇ yrifos (-methyl / -ethyl), coumaphos, Cyanofenphos, cyanophos, chlorfenvinphos, demeton-S-methyl, demeton-S-methylsulphone, dialifos, diacinone, dichlofenthione, dichlorvos / DDVP, dicrotophos, dimethoates, dimethylvinphos, dioxabenzofos, disulfoton, EPN, ethion, ethoprophos, etrimfos, Famphur, Fenamiphos
  • Pyrethroids for example, acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin-S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resithrn , Cis-permethrin,
  • Oxadiazines for example Indoxacarb
  • Chloronicotinyls for example acetamipride, clothianidin, dinotefuran, imidacloprid, nitenpyram, nithiazines, thiacloprid, thiamethoxam
  • Acetylcholine receptor modulators are Acetylcholine receptor modulators
  • Organochlorines for example, camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
  • Fiproles for example, acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole
  • Mectins for example avermectin, emamectin, emamectin benzoate, ivermectin, milbemycin
  • Juvenile hormone mimetics for example, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprenes, methoprenes, pyriproxifen, triprene Ecdysone agonists / disruptors
  • Diacylhydrazines for example chromafenozide, Halofenozide, Methoxyfenozide, Tebufenozide
  • Benzoylureas for example bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, fenphenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
  • Organotin compounds for example azocyclotin, cyhexatin, fenbutatin oxides
  • Dinitrophenols for example binapacyrl, dinobutone, dinocap, DNOC
  • METI's for example fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad,
  • spirotetramat for example, spirotetramat (CAS Reg. No .: 203313-25-1) and 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-ene-4 -yl ethyl carbonate (also known as: Carbonic acid, 3- (2,5-dimethylphenyl) -8-methoxy-2-oxo-1-azaspiro [4.5] dec-3-en-4-yl ethyl ester, CAS Reg. No .: 382608-10-8)
  • thiocyclam hydrogen oxalate for example, thiocyclam hydrogen oxalate, thiosultap-sodium Biologics, hormones or pheromones
  • Begasimgsmittel for example aluminum phosphides, methyl bromides, sulfuryl fluorides
  • Food inhibitors for example Cryolite, Flonicamid, Pymetrozine
  • Mite growth inhibitors for example clofentezine, etoxazole, hexythiazox
  • a mixture with other known active substances, such as herbicides, fertilizers, growth regulators, safeners, semi-seminicals, or with agents for improving the plant properties is possible.
  • the active compounds according to the invention can furthermore be present when used as insecticides in their commercial formulations as well as 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 also be present in insecticides in their commercially available formulations and in the formulations prepared from these formulations in mixtures with inhibitors, the degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant Reduce tissue.
  • 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 their parts can be treated.
  • wild species or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
  • plant varieties and their parts are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, 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 erf ⁇ ndungshiel usable substances and agents, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or 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 storage stability and / or machinability of Ernte ⁇ 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 and increased tolerance of the plants against certain herbicidal active ingredients.
  • 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 which are formed in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (for example by the genes CryIA (a) , CryIA (b), CryIA (c), CryDA, CrylllA, Cryi ⁇ B2, 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. Traits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example hidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "P AT” gene). The genes which confer the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants.
  • SAR systemic acquired resistance
  • P AT phosphinotricin
  • 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).
  • YIELD GARD® eg corn, cotton, soya
  • KnockOut® eg maize
  • StarLink® eg maize
  • Bollgard® Cotton
  • Nucotn® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants maize varieties, cotton varieties and Sqjasorten be called, under the trade names Roundup Ready® (tolerance to glyphosate such as corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rape), Evfl® (tolerance against imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Roundup Ready® tolerance to glyphosate such as corn, cotton, soy
  • Liberty Link® tolerance to phosphinotricin, eg rape
  • Evfl® 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 invention not only against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ecto- and endoparasites) such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae, lice , Hair pieces, featherlings and fleas.
  • animal parasites ecto- and endoparasites
  • Anoplurida e.g. Haematopinus spp., Linognatfaus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
  • Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
  • Nematocerina and Brachycerina e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp , Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Glossina spp., Chrysomyia spppp
  • siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
  • heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
  • Actinedida Prostigmata
  • Acaridida e.g. Acarapis spp.
  • Pterolichus spp. Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
  • the active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
  • arthropods are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
  • the application of the active compounds according to the invention takes place in the veterinary sector and in animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feed-through process, suppositories, by parenteral administration, as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying, pouring (pour-on and spot-on ), washing, powdering and with the aid of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, holsters, Mark réellesvor ⁇ directions, etc.
  • enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feed-through process, suppositories
  • parenteral administration as by
  • the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of from 1 to 80% by weight, directly or apply after 100 to 10,000 times dilution or use as a chemical bath.
  • formulations for example powders, emulsions, flowable agents
  • the compounds according to the invention show a high insecticidal activity against insects which destroy industrial materials.
  • insects By way of example and preferably without limiting however, the following insects are mentioned:
  • Hymenoptera such as Sirex juvencus, Urocera's gigas, Urocerus gigas taignus, Urocerus augur;
  • Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
  • 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 for protection against the growth of objects, in particular hulls, sieves, nets, structures, wharfage installations and signaling installations, which come into contact with seawater or brackish water.
  • 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, which are used in closed rooms, such as apartments, factory buildings, offices, vehicle cabins u.a. 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 moübat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
  • 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.
  • Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
  • Hymenoptera for example, Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
  • a ⁇ oplura for example, Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix, Phthirus pubis.
  • Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • the reaction mixture is added with stirring at 50 0 C with 5 ml of a 10% sodium bisulfite solution (Bisulf ⁇ t), stirred for 10 minutes and quenched with 10 ml of a 10% sodium bicarbonate solution.
  • the organic phase is separated, the aqueous phase extracted twice with dichloromethane and the combined organic phases dried over sodium sulfate. After distilling off the solvent by means of reduced pressure, the product is obtained in the form of a white solid.
  • the determination is carried out in the acidic range at pH 2.3 with 0.1% aqueous phosphoric acid and acetonitrile as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile.
  • the determination with the LC-MS in the acidic range is carried out at pH 2.7 with 0.1% aqueous formic acid and acetonitrile (containing 0.1% formic acid) as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile
  • the determination with the LC-MS in the neutral range is carried out at pH 7.8 with 0.001 molar aqueous ammonium bicarbonate solution and acetonitrile as eluent; linear gradient from 10% acetonitrile to 95% acetonitrile.
  • the calibration is carried out with unbranched 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 lambda-max values were determined on the basis of the UV spectra from 200 to 400 nm in the maxima of the chromatographic signals.
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • 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.
  • the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have 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.
  • 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.
  • 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.
  • 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 frugiperdd).
  • the effect is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillar has been killed.
  • Emulsifier 2 parts 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.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are populated with caterpillars of the cabbage (Plutella xylostella) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.
  • Emulsifier 2 'parts 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.
  • Cotton leaves which are heavily infested with the cotton aphid (Aphis gossypii) are treated by being dipped into the preparation of active compound of the desired concentration.
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Emulsifier 2 parts 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.
  • Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and are infested with caterpillars of the armyworm (Spodoptera exigu ⁇ ) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have 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 stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • 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.
  • the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
  • Emulsifier 2 parts 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 water to the desired concentration.
  • the preparation of active compound is mixed with water.
  • the treated water is filled into peas with a pea plant (Piswn sativum) and then infected with the green peach aphid ⁇ Myzus persicae).
  • the kill is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
  • Emulsifier 2 parts 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.
  • Soybean leaves (Glycine max.) Are treated by being dipped into the preparation of active compound of the desired concentration and are populated with caterpillars of the cotton bollworm (Heliothis armigera) while the leaves are still moist.
  • the kill is determined in%. 100% means that all caterpillars have been killed; 0% means that no caterpillars have been killed.

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  • Organic Chemistry (AREA)
  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Environmental Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Plant Pathology (AREA)
  • Pest Control & Pesticides (AREA)
  • Agronomy & Crop Science (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Indole Compounds (AREA)

Abstract

L'invention concerne de nouveaux diamides d'acide N-heterocyclylphthalique de formule (I), dans laquelle n, A, Q<SUP>1</SUP>, Q<SUP>2</SUP>, R<SUP>1</SUP> et X ont la signification indiquée dans la description. Elle concerne également plusieurs procédés pour produire ces substances et l'utilisation de ces dernières pour lutter contre les parasites, ainsi que de nouveaux produits intermédiaires et procédés pour leur production.
EP05811673A 2004-11-18 2005-11-05 Diamides d'acide n-heterocyclylphtalique utilises comme insecticide Withdrawn EP1814874A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102004055582A DE102004055582A1 (de) 2004-11-18 2004-11-18 N-Heterocyclyl-phthalsäurediamide
PCT/EP2005/011846 WO2006053643A1 (fr) 2004-11-18 2005-11-05 Diamides d'acide n-heterocyclylphtalique utilises comme insecticide

Publications (1)

Publication Number Publication Date
EP1814874A1 true EP1814874A1 (fr) 2007-08-08

Family

ID=35759148

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EP05811673A Withdrawn EP1814874A1 (fr) 2004-11-18 2005-11-05 Diamides d'acide n-heterocyclylphtalique utilises comme insecticide

Country Status (16)

Country Link
US (1) US7884242B2 (fr)
EP (1) EP1814874A1 (fr)
JP (1) JP4918042B2 (fr)
KR (1) KR20070085530A (fr)
CN (1) CN101103014A (fr)
AR (1) AR051953A1 (fr)
AU (1) AU2005306072B2 (fr)
BR (1) BRPI0517735A (fr)
CA (1) CA2587482A1 (fr)
DE (1) DE102004055582A1 (fr)
MA (1) MA29036B1 (fr)
MX (1) MX2007005874A (fr)
RU (1) RU2007122281A (fr)
TW (1) TW200630357A (fr)
WO (1) WO2006053643A1 (fr)
ZA (1) ZA200703983B (fr)

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JP2006347936A (ja) * 2005-06-15 2006-12-28 Bayer Cropscience Ag 殺虫性ベンズアニリド類
JP2007031395A (ja) * 2005-07-29 2007-02-08 Bayer Cropscience Ag 殺虫性３−アシルアミノベンズアニリド類
WO2008013622A2 (fr) * 2006-07-27 2008-01-31 E. I. Du Pont De Nemours And Company Amides azocycliques fongicides
JP2010030970A (ja) * 2008-07-31 2010-02-12 Bayer Cropscience Ag 殺虫性ベンゼンジカルボキサミド誘導体
WO2010128003A2 (fr) * 2009-05-06 2010-11-11 Basf Se Procédé pour augmenter la vigueur et/ou le rendement de culture de plantes agricoles sous une pression pathogène essentiellement non existante
JP2015027951A (ja) * 2011-11-02 2015-02-12 日本農薬株式会社 フタルアミド誘導体及び該誘導体を含有する農園芸用殺虫剤並びにその使用方法

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Also Published As

Publication number Publication date
US20090023752A1 (en) 2009-01-22
AU2005306072A1 (en) 2006-05-26
BRPI0517735A (pt) 2008-10-21
DE102004055582A1 (de) 2006-05-24
JP2008520599A (ja) 2008-06-19
RU2007122281A (ru) 2008-12-27
MA29036B1 (fr) 2007-11-01
AR051953A1 (es) 2007-02-21
WO2006053643A1 (fr) 2006-05-26
KR20070085530A (ko) 2007-08-27
JP4918042B2 (ja) 2012-04-18
AU2005306072B2 (en) 2012-01-19
ZA200703983B (en) 2008-08-27
CA2587482A1 (fr) 2006-05-26
MX2007005874A (es) 2007-06-19
TW200630357A (en) 2006-09-01
CN101103014A (zh) 2008-01-09
US7884242B2 (en) 2011-02-08

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