WO2010078906A2 - Hydrazides method for production and use thereof as herbicide and insecticide - Google Patents

Hydrazides method for production and use thereof as herbicide and insecticide Download PDF

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WO2010078906A2
WO2010078906A2 PCT/EP2009/008813 EP2009008813W WO2010078906A2 WO 2010078906 A2 WO2010078906 A2 WO 2010078906A2 EP 2009008813 W EP2009008813 W EP 2009008813W WO 2010078906 A2 WO2010078906 A2 WO 2010078906A2
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group
substituted
alkoxy
alkyl
crc
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PCT/EP2009/008813
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German (de)
French (fr)
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WO2010078906A3 (en
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Hartmut Ahrens
Hansjörg Dietrich
Dieter Feucht
Heinz Kehne
Arnim Köhn
Stefan Lehr
Christian Paulitz
Christopher Hugh Rosinger
Jörg Tiebes
Angela Becker
Ulrich Görgens
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Bayer Cropscience Ag
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/86—Hydrazides; Thio or imino analogues thereof
    • C07D213/87—Hydrazides; Thio or imino analogues thereof in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C243/00—Compounds containing chains of nitrogen atoms singly-bound to each other, e.g. hydrazines, triazanes
    • C07C243/24—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids
    • C07C243/38—Hydrazines having nitrogen atoms of hydrazine groups acylated by carboxylic acids with acylating carboxyl groups bound to carbon atoms of six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D253/00—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00
    • C07D253/02—Heterocyclic compounds containing six-membered rings having three nitrogen atoms as the only ring hetero atoms, not provided for by group C07D251/00 not condensed with other rings
    • C07D253/06—1,2,4-Triazines
    • C07D253/065—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members
    • C07D253/07—1,2,4-Triazines having three double bonds between ring members or between ring members and non-ring members with hetero atoms, or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D401/12—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 chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links

Definitions

  • the invention relates to the technical field of herbicides and insecticides, in particular the hydrazides and processes for their preparation and formulations containing hydrazides, for the selective control of weeds and weeds in crops and for controlling animal pests.
  • J is pyridine, pyridinium, pyrazole or isothiazole, each substituted, and
  • R 1 is H or (C r C 4 ) alkyl
  • R 2 is H, (CrC-O-alkyl, (C r C4) -haloalkyl, (C 3 -C 6) cycloalkyl, (C 2 -C 3) alkenyl, (C 2 - C 3) alkynyl, (C 2 -C 4 ) alkoxymethyl, cyano, (C r C 4 ) alkoxy or (C 2 -C 4 ) alkoxycarbonyl.
  • the known heterocyclic substituted compounds have various drawbacks with respect to the control of harmful plants.
  • the disadvantages are in addition to a too low activity too little spectrum of combated harmful plants and too low selectivity in crops.
  • the object of the present invention is to provide specially substituted hydrazides having improved herbicidal and insecticidal activity and improved herbicidal selectivity.
  • Q is an aryl or heteroaryl group, each unsubstituted or substituted by one or more substituents each independently selected from the group consisting of halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl , Alkenyl, haloalkenyl, alkynyl, haloalkynyl, hydroxy, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkenylthio, haloalkenylthio, alken
  • R 1 is hydrogen, alkyl, cycloalkyl or means
  • R 3 is a fragment of general formula (IIa), (IIb), (Hc), (Hd), (Me), (Hf), (Hg), (Hh) 1 (IIi), (Hj) 1 (IIk) 1 (IIm), (Hn), (Ho) or (Hp)
  • R 4 , R 5 , R 6 , R 7 and R 8 independently of one another are hydrogen, halogen, cyano, nitro, alkyl, cycloalkylalkyl, arylalkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, cycloalkoxy, alkenyloxy, cycloalkenyloxy, alkynyloxy, alkylthio, Cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynyl
  • R 9 and R 10 independently of one another are hydrogen, alkyl, cycloalkyl, alkenyl or alkynyl.
  • (C 3 -C 7) -cycloalkyl where the cycloalkyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (Ci-C 4) -alkyl, (dC 4) -alkoxy or (C r C 4 ) -Alkylthio existing group, (C 3 -C 7 ) -cycloalkyl- (Ci-C 6 ) alkyl, wherein the cycloalkylalkyl is unsubstituted, or substituted only the cycloalkyl radical, or only the
  • Alkyl radical is substituted, or substituted both the cycloalkyl radical and the alkyl radical, wherein the cycloalkyl radical by one or more substituents selected from among halogen, cyano, (C r C 4 ) alkyl, (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) -alkylthio group, and the alkyl radical is substituted by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio, Aryl- (CrC 6 ) alkyl, wherein the arylalkyl is unsubstituted, or only the aryl radical is substituted, or only the alkyl radical is substituted, or both the aryl radical and the alkyl radical are substituted, wherein the aryl radical by one or more substituents selected is substituted from the group consisting
  • Alkenylcarbonyl wherein the alkenyl group is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C r C 4 ⁇ -alkoxy or (C r C 4) -alkylthio group consisting of, (C 2 - C ⁇ J- Alkynylcarbonyl, wherein the alkynyl radical is unsubstituted or by one or more substituents selected from the group consisting of halogen, cyano, (Cr
  • R 4 , R 5 , R 6 , R 7 and R 8 independently of one another are hydrogen, halogen, cyano, nitro, (C 1 -C 6 ) -alkyl, where the alkyl radical is unsubstituted or by one or more substituents selected from halogen, cyano , (CrC 4) - alkoxy or (Ci -C 4 J-AI alkylthio group existing is substituted, (C 3 -C 7) - cycloalkyl (CrC 6) alkyl, wherein the cycloalkylalkyl group is unsubstituted, or only the cycloalkyl is substituted or only the alkyl radical is substituted, or both the cycloalkyl radical and the alkyl radical are substituted, wherein the cycloalkyl radical by one or more substituents selected from among halogen, cyano, (CrC 4 ) alkyl, (Ci-C 4 ) Alk
  • Cycloalkyl group is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4) alkyl, (dC 4) alkoxy or (CrC 4) alkylthio existing group is substituted, (C 2 -C 6 ) -alkenyl, where the alkenyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C r C4) alkoxy or (C r C 4) -
  • Alkylthio existing group (C 3 -C 7 ) -Cycloalkenyl, wherein the cycloalkenyl radical is unsubstituted or by one or more Is substituent selected from the group consisting of halogen, cyano, (CrC 4) alkyl, (d- C / O-alkoxy or (CrC 4) -alkylthio group consisting of substituted, (C 2 - C ⁇ J-alkynyl, where the Alkynyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4 ) - alkoxy or (dC 4 ) -Alkylthio, (C 1 -C 6 ) -
  • alkoxy radical is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4 J -oxyoxy or (C 1 -C 4 ) -alkylthio, (C 3 -C 7 ) cycloalkoxy wherein the cycloalkoxy group is unsubstituted or substituted (by one or more substituents selected from the group consisting of halogen, cyano, (C r C4) alkyl C r
  • Alkylsulfinylrest is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4 -j-alkoxy or (C 1 -C 4 ) -alkylthio, (C 2 -C 6 ) - Alkenylsulfinyl, wherein the alkenylsulfinyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or
  • (C 1 -C 4 ) -alkylthio group (C 2 -C 6 ) -alkynylsulfinyl, where the alkynylsulfinyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C 1 -C 4 -alkoxy or C 1 -C 4 ) -alkylthio group, (C 1 -C 6 ) -alkylsulfonyl wherein the alkylsulfonyl radical is unsubstituted or substituted by one or more
  • R 2 is hydrogen, (C r C 5) alkyl, dihaloalkyl, trihaloalkyl, (C r C 3) alkoxy (C- ⁇ -C 5) alkyl, (C 2 -C 5) alkenyl, Dihalogenalkenyl, Trihalogenalkenyl , (C r C 3 ) alkoxy- (C 2 -C 5 ) -alkenyl, (C 2 -C 5 ) -alkynyl, dihaloalkynyl, trihaloalkynyl or (dC 3 ) -alkoxy- (C 2 -C 5 ) -alkynyl means, and R 4, R 5, R 6, R 7 and R 8 are independently hydrogen, halogen, cyano, nitro, (C r C 5) alkyl, dihaloalkyl, trihaloalkyl, (CrC 3) alkoxy (CrC 5) alkyl , (Ci-Cs)
  • R 2 is hydrogen, (C r C 5 ) alkyl, (C r C 3 ) alkoxy (CrC 5 ) alkyl or (C 2 -C 5 ) alkynyl, and R 4 , R 5 , R 6 , R 7 and R 8 independently of one another hydrogen, fluorine, chlorine, bromine,
  • Trifluoromethylthio (C r C 2 ) alkylsulfinyl, (C r C 2 ) alkylsulfonyl or (C r C 2 ) dialkylamino.
  • R 9 and R 10 independently of one another are hydrogen, (C 1 -C 6) -alkyl, where the alkyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) - alkylthio existing group is substituted, (C 3 -C 7) -cycloalkyl, where the cycloalkyl is unsubstituted or substituted (by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4) alkyl -C 4) is group alkoxy or (dC 4) alkylthio existing substituted, (C 2 -C 6) -alkenyl, where the alkenyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4 J- AIkOXy or (C
  • Alkynyl radical is unsubstituted or substituted by one or more substituents, selected from the group consisting of halogen, cyano, (CrC 4) -alkoxy or (C r C 4) -, substituted alkylthio existing group mean.
  • R 11 is unsubstituted or substituted by one or more substituents selected from the group consisting of R 11 , R 12 , R 13 , R 14 or R 11a , wherein
  • R 11 , R 12 , R 13 , R 14 independently of one another are hydrogen, halogen, cyano, nitro, alkyl, cycloalkylalkyl, arylalkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, cycloalkoxy, alkenyloxy, cycloalkenyloxy, alkynyloxy, alkylthio, cycloalkylthio, alkenylthio , Cycloalkenylthio, alkynylthio, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, each radical other than the first four radicals mentioned being optionally substituted by one or more substituents selected from among halogen, cyano, (C 1
  • R 11a is hydrogen, halogen, cyano, nitro, alkyl, cycloalkylalkyl, arylalkyl,
  • T is hydrogen, (C 1 -C 6 -alkyl, benzyl or phenyl, each of the last three radicals optionally being substituted by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio existing group, is substituted.
  • Particular preference is furthermore given to hydrazides of the general formula (1) in which, in the case where Q is phenyl, phenoxy or a 5- to 6-membered heteroaromatic ring, these are monosubstituted, disubstituted or trisubstituted by R 15 ,
  • R 15 is halogen, cyano, nitro, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) halocycloalkyl, (C 2 - C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) -alkynyl, (C 2 -C 4) haloalkynyl, (C r C4) alkoxy, (C r C 4 ) haloalkoxy, (C r C4) alkylthio, (C 1 - C 4) haloalkylthio, (C r C4) alkylsulfinyl, (C r C4) -alkylsulfonyl, (C 1 -C 4) - alkylamino , (C 2 -C 8) dialkylamino,
  • Alkylaminocarbonyl, (C 2 -C 8 ) -dialkylaminocarbonyl or (Cs-C ⁇ J-trialkylsilyl means.
  • hydrazides of the general formula (I) in which the radicals R 4 , R 5 , R 6 , R 7 and R 8 are each substituted by one or more of the radicals R 16 , wherein R 16 is selected from the group consisting of Halogen, cyano, nitro, (C 1 -C 4 ) -alkyl, except in the event that the corresponding radical R 4 , R 5 , R 6 , R 7 or R 8 is an alkyl radical, (C r C 4) alkoxy, (C r C 4) -haloalkoxy, (C 1 -C 4) - alkylthio, (C r C4) haloalkylthio, (C r C4) alkylsulfinyl, (C r C4) - Alkylsulfonyl, (C 1 -C 4 ) -alkylamino, (C 2 -C 8 ) -dialkylamino, (C 3 -C 6
  • the present invention includes all isomers, atropisomers, geometric and optical isomers, and in the case of the nitrogen-containing heterocycles also the N-oxides and the salts of these compounds.
  • the terms used above and below are explained. These are familiar to the person skilled in the art and in particular have the meanings explained below:
  • halogen means, for example, fluorine, chlorine, bromine or iodine.
  • halogen means, for example, a fluorine, chlorine, bromine or iodine atom.
  • Alkyl is a straight-chain or branched open-chain hydrocarbon radical.
  • the expression means a short notation for alkyl having one to 4 carbon atoms corresponding to the range for C atoms, ie, the radicals comprises methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl.
  • General alkyl radicals having a larger specified range of carbon atoms eg. B. "(Ci-C 6 ) alkyr, accordingly also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, ie according to Example, the alkyl radicals having 5 and 6 carbon atoms.
  • hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are the lower carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred.
  • Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or triple bond.
  • alkenyl also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1, 4-pentadienyl, but also allenyl or Kumulenyl residues with one or more cumulative double bonds, such as allenyl (1, 2-propadienyl), 1, 2-butadienyl and 1, 2,3-pentatrienyl.
  • alkynyl also includes straight-chain or branched open-chain
  • Hydrocarbon radicals having more than one triple bond or having one or more triple bonds and one or more double bonds such as 1, 3-butatrienyl or 3-penten-1-yn-1-yl.
  • Alkenyl means e.g. Vinyl, which is optionally substituted by further alkyl radicals, e.g. Prop-1-en-i-yl, but-1-en-1-yl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, But-2-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl, 2-methylprop-1 -ene-1-yl, 1-methylprop-1 -ene-1-yl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, butyrene 3-en-1-yl, 1-methyl-but-3-en-1-yl or 1-methyl-but-2-en-1-yl, pentenyl, 2-methylpentenyl or hexenyl.
  • alkyl radicals e.g. Prop-1-en-i-yl, but-1-en-1-yl, allyl,
  • (C 2 -C 6 ) -alkynyl is, for example, ethinyl, propargyl, 1-methyl-prop-2-yn-1-yl, 2-butynyl, 2-pentynyl or 2-hexynyl, preferably propargyl, but-2-yn 1-yl, but-3-yn-1-yl or 1-methyl-but-3-yn-1-yl.
  • Cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • substituents wherein substituents having a double bond on the cycloalkyl, z.
  • alkylidene group such as methylidene, are included.
  • polycyclic aliphatic systems are also included, such as bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl , Bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.2.1] hept-2-yl (norbornyl), adamantan-1-yl and adamantan-2 yl.
  • spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl.
  • Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein also substituents with a Double bond on Cycloalkenylrest, z.
  • an alkylidene group such as methylidene, are included.
  • the explanations for substituted cycloalkyl apply correspondingly.
  • Aryl is a mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
  • optionally substituted aryl also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the binding site is on the aromatic system.
  • aryl is also encompassed by the term "optionally substituted phenyl".
  • Alkoxy is an alkyl radical bonded via an oxygen atom
  • alkenyloxy is an alkynyl radical bonded via an oxygen atom
  • alkynyloxy is an alkynyl radical bound via an oxygen atom
  • cycloalkyloxy is a cycloalkyl radical bonded via an oxygen atom
  • cycloalkenyloxy is a cycloalkenyl radical bonded via an oxygen atom.
  • Alkylthio means an alkyl radical bonded via a sulfur atom
  • alkenylthio means an alkenyl radical bonded via a sulfur atom
  • alkynylthio an alkynyl radical bound via a sulfur atom
  • cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom
  • cycloalkenylthio means a cycloalkenyl radical bonded via a sulfur atom.
  • Haloalkyl, alkenyl and alkynyl mean the same or different
  • monohaloalkyl such as CH 2 CH 2 Cl, CH 2 CH 2 F, CHCICH 3 , CHFCH 3 , CH 2 Cl, CH 2 F; Per
  • substituted by one or more radicals means, independently of one another, one or more identical or different radicals, it being possible for two or more radicals to form one or more rings on one cycle as main body.
  • Substituted radicals such as a substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, are, for example, a substituted radical derived from the unsubstituted radical, where the substituents are, for example, a or more, preferably 1, 2 or 3 radicals selected from the group consisting of halogen, alkoxy, alkylthio, hydroxy, amino, nitro, carboxy or a carboxy group equivalent group, cyano, isocyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and Dialkylaminocarbonyl, substituted amino such as acylamino, mono- and dialkylamino, trialkylsilyl and optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heterocycl
  • substituted radicals such as substituted alkyl, etc.
  • substituents in addition to the saturated hydrocarbon radicals mentioned corresponding unsaturated aliphatic and aromatic radicals, such as unsubstituted or substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenyloxycarbonyl, alkynyloxycarbonyl, alkenylcarbonyl, alkynylcarbonyl, Mono- and dialkenylaminocarbonyl, mono- and dialkynylaminocarbonyl, mono- and dialkenylamino, mono- and dialkynylamino, trialkenylsilyl, trialkynylsilyl, optionally substituted cycloalkenyl, optionally substituted
  • Cycloalkynyl, phenyl, phenoxy, etc. included.
  • substituted cyclic radicals having aliphatic moieties in the ring cyclic systems are also included with those substituents attached to the ring with a double bond, e.g. B. substituted with an alkylidene group such as methylidene or ethylidene or an oxo group, imino group or substituted imino group.
  • radicals form one or more rings, these may be carbocyclic, heterocyclic, saturated, partially saturated, unsaturated, for example also aromatic and optionally further substituted.
  • the fused rings are preferably 5- or 6-membered rings, particularly preferred are benzo-fused rings.
  • first substituent level if they contain hydrocarbon-containing moieties, may optionally be further substituted there (“second substituent plane"), for example by one of the substituents as defined for the first substituent level.
  • second substituent plane corresponds further substituent levels.
  • substituted radical includes only one or two substituent levels.
  • Preferred substituents for the substituent levels are, for example, amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, carboxy, carbonamide, SF 5 , aminosulfonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, Alkynyl, monoalkylamino, dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl, alkenylcarbonyl, alkynylcarbonyl, Arylcarbonyl, alkylthio, cycloalkylthio, alkenylthio, cycloalkenylthio, alkyny
  • Substituents composed of plural substituent levels are preferably alkoxyalkyl, alkylthioalkyl, alkylthioalkoxy, alkoxyalkoxy, phenethyl, benzyloxy, haloalkyl, haloalkoxy, haloalkylthio, haloalkanoyl, haloalkylcarbonyl, haloalkoxycarbonyl, haloalkoxyalkoxy, haloalkoxyalkylthio, haloalkoxyalkanoyl, haloalkoxyalkyl.
  • Collections of compounds of formula I and / or their salts, which may be synthesized following the above reactions, may also be prepared in a parallelized manner, which may be done in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34.
  • the listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed.
  • This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots.
  • Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
  • the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods.
  • solid-phase assisted synthesis methods are well described in the literature, eg Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley, 1999.
  • Use Solid-phase assisted synthesis methods allow a series of protocols known from the literature, which in turn can be performed manually or automatically can be.
  • the reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
  • the preparation according to the processes described herein yields compounds of formula I and their salts in the form of substance collections called "libraries.”
  • the present invention also provides libraries containing at least two compounds of formula I and their salts.
  • Hydrazides of the general formula I may have one or more centers of chirality, which is why they may be present as a racemate, as a mixture of enantiomers, as one of the two enantiomers, as a mixture of diastereomers or as one of several diastereomers.
  • the enantiomers are separated by methods known to those skilled in the art, for example by chromatography on chiral sorbents. Diastereomers can also be separated by methods known to a person skilled in the art, such as crystallization or chromatography.
  • the chromatographic separation can be used both on an analytical scale to determine the enantiomeric excess and the
  • the “ee” can be determined by various physical methods, such as previously mentioned, by chromatography on chiral sorbents in the liquid as well as the gas phase, NMR measurements with chiral derivatives, or by determination of the specific rotation, which, however, requires the specific rotation of the pure enantiomer is known.
  • optical yield P optical purity multiplied by 100
  • ee optical purity multiplied by 100
  • the activation of the carboxylic acid is carried out using common condensation reagents, such as carbonyldiimidazole (CDI), N-hydroxy-1,2,3-benzotriazole (HOBt), 1,3-dicyclohexylcarbidiimide (DCC) or 1- [3- (dimethylamino) propyl] - 3-ethylcarbodiimide (EDC).
  • CDI carbonyldiimidazole
  • HOBt N-hydroxy-1,2,3-benzotriazole
  • DCC 1,3-dicyclohexylcarbidiimide
  • EDC 1- [3- (dimethylamino) propyl] - 3-ethylcarbodiimide
  • polymer-bound reagents such as polystyrene-bound cyclohexylcarbodiimide (DCC polystyrene) can be used.
  • the condensation reagents are used equimolar or up to 3-fold excess, preferably equimolar or up to 1.5-fold excess.
  • the carboxylic acids can also be converted to the corresponding carboxylic acid halides, which can then be reacted in the presence of a base with the hydrazine (IV).
  • the carboxylic acids (III) are preferably converted into the relevant carbonyl chlorides or carbonyl bromides (V) and then reacted with the hydrazine (IV) in the presence of a base.
  • the preparation of the carbonyl halides (V) from the carboxylic acids (III) is carried out using common halogenating reagents such as oxalyl chloride, thionyl chloride, phosphorus oxychloride, oxalyl bromide, thionyl bromide or phosphorus oxybromide.
  • common halogenating reagents such as oxalyl chloride, thionyl chloride, phosphorus oxychloride, oxalyl bromide, thionyl bromide or phosphorus oxybromide.
  • organic bases such as triethylamine, pyridine, N-methylmorpholine but also inorganic bases such as sodium carbonate, potassium carbonate or potassium hydroxide are used, but preferably triethylamine and pyridine.
  • Polymer-bound bases such as DMAP polystyrene can also be used.
  • the bases are used equimolar or up to a 4-fold excess.
  • ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, tetrahydrofuran, 1, 4-dioxane or dimethoxyethane, chlorinated hydrocarbons such as dichloromethane, 1, 2-dichloroethane or chloroform, aromatic hydrocarbons such as toluene, xylene or chlorobenzene , tertiary amides such as N, N-dimethylformamide, N, N-dimethylacetamide or N-methylpyrrolidone, or nitriles such as acetonitrile.
  • chlorinated hydrocarbons such as dichloromethane, 1, 2-dichloroethane or chloroform
  • aromatic hydrocarbons such as toluene, xylene or chlorobenzene
  • tertiary amides such as N, N-dimethylformamide, N, N-dimethylacetamide or N-
  • the carboxylic acids of formula (III) are commercially available in a wide variety. Specially substituted nicotinic acids (IIIa) as well as specifically substituted pyrazolecarboxylic acids (MIb) and 1,2-thiazolecarboxylic acids (IMc) can be prepared according to the procedures published in documents WO 93/11117, WO2005 / 070889 and WO 2008/029370.
  • Hydrazines (IV), as well as the carboxylic acids (III), and with a variety of substitution patterns are commercially available.
  • a common reducing agent for such purposes tin (II) chloride in hydrochloric acid solution (Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag Stuttgart / New York, Vol. E 16a / Part 1, Extension and follow-up volumes to the fourth edition 1990, P. 656 ff.).
  • the radical R 2 can optionally subsequently be introduced via reaction of the hydrazine with an electrophile R 2 -LG (VII), where LG is a suitable leaving group (for example halogen, sulfonates).
  • LG is a suitable leaving group (for example halogen, sulfonates).
  • compounds of formula (I) may form salts.
  • Salt formation can be effected by the action of a base on those compounds of the formula (I) which carry an acidic hydrogen atom.
  • Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate.
  • These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular
  • Alkali metal salts or alkaline earth metal salts especially sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts, for example with cations of the formula [NRR ' R " R '" ] + , wherein R to R '"are each independently from each other represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • R to R '" are each independently from each other represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.
  • Suitable are also alkylsulfonium and alkylsulfoxonium salts, such as (CrC 4 ) -Trialkylsulfonium- and (C r CO-Trialkylsulfoxoniumsalze.
  • the compounds of formula (I) may be prepared by addition of a suitable inorganic or organic acid, such as mineral acids, such as HCl, HBr, H 2 SO 4 , H 3 PO 4, HNO 3 , or organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid, form salts with the basic group. These salts then contain the conjugate base of the acid as anion.
  • mineral acids such as HCl, HBr, H 2 SO 4 , H 3 PO 4, HNO 3
  • organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid
  • Suitable substituents which are in deprotonated form e.g. Sulfonic acids or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups.
  • the compounds of the invention have excellent insecticidal activity.
  • An effective amount of one or more of the compounds of formula (I) or one of their ⁇ / oxides or one of its salts may be in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or
  • Granules are used in the usual preparations. It is envisaged that the composition may contain at least one of the customary in plant protection formulation auxiliaries.
  • the invention also relates to plant growth-regulating agents which contain the compounds according to the invention.
  • the compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as Oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes.
  • WP wettable powder
  • SP water-soluble powders
  • EC emulsifiable concentrates
  • EW
  • Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain ionic and / or nonionic surfactants (wetting agents, dispersants) other than a diluent or inert substance, for example polyoxyethylated alkylphenols.
  • the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
  • Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers).
  • organic solvent e.g. Butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents.
  • alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers
  • fatty acid polyglycol esters alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g. Polyoxyethylene.
  • Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • finely divided solids e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
  • Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
  • Emulsions for example oil-in-water emulsions (EW)
  • EW oil-in-water emulsions
  • Granules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
  • Active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • adhesives e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils
  • carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
  • Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
  • the agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
  • the active ingredient concentration is for example about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components.
  • the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%.
  • Contain dusty formulations 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% active ingredient.
  • the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used.
  • the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
  • the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
  • the present invention therefore also provides a method for controlling undesirable plants or for regulating the growth of plants, preferably in plant crops, wherein one or more compounds of the invention are applied to the plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds) or the area on which the plants grow (eg the acreage) are applied.
  • the compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufmaschinene.
  • some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
  • Monocotyledonous weeds include the genera Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata , Ishaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
  • the compounds according to the invention are applied to the surface of the earth before germination, then either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die off completely after a lapse of three to four weeks.
  • the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, eg dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, depending on the structure of the respective compound of the invention and their application rate only insignificantly or not at all damaged.
  • the present compounds are very well suited for the selective control of undesired plant growth in crops such as agricultural crops or ornamental plants
  • the compounds according to the invention (depending on their respective structure and the applied application rate) have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented.
  • the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known.
  • Preferred with respect to transgenic crops is the use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice and corn or even crops of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
  • the compounds according to the invention can preferably be employed as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
  • the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants.
  • the transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses.
  • Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients.
  • the compounds of formula I can be used as herbicides in crops that are resistant to the phytotoxic Effects of the herbicides are resistant or have been made genetically resistant.
  • EP-A-0193259 transgenic crops with modified fatty acid composition (WO 91/13972), genetically modified crops with new content or secondary substances z.
  • nucleic acid molecules can be used in any genetic manipulations.
  • nucleic acid molecules can be used in any genetic manipulations.
  • Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added.
  • adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. CoId Spring Harbor Laboratory Press, ColD Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996.
  • Gene product can be obtained, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
  • DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences that have a high degree of homology to the coding sequences of a gene product but are not completely identical.
  • the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z.
  • the coding region can be linked to DNA sequences that ensure localization in a particular compartment.
  • sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).
  • the expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
  • the transgenic plant cells can be regenerated to whole plants by known techniques.
  • the transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
  • the compounds (I) according to the invention can be used in transgenic cultures which are resistant to growth substances, such as. B. Dicamba or against herbicides, the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydoxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, are resistant.
  • the active compounds according to the invention in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled
  • the invention therefore also relates to the use of the compounds of the formula I according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
  • Mixture formulations or in the tank mix are, for example, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase , Photosystem I, photosystem II, protoporphyrinogen oxidase are based, can be used, such as from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 13th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and cited therein.
  • Examples of known herbicides which can be combined with the compounds according to the invention are the following active substances (note: the compounds are either with the "common name” according to the International Organization for Standardization (ISO) or with a common code number together with the chemical Names) and always include all forms of use such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • active substances note: the compounds are either with the "common name” according to the International Organization for Standardization (ISO) or with a common code number together with the chemical Names) and always include all forms of use such as acids, salts, esters and isomers such as stereoisomers and optical isomers.
  • Fluorochloridones fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl-sodium, fluridone, fluroxypyr, fluroxypyr-butoxypropyl, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, glufosinate, glufosinate-ammonium, glyphosate, halosulfuron-methyl, Haloxyfop, haloxyfopethoxyethyl, haloxyfopmethyl, haloxyfop-P-methyl, hexazinone, HOK-201 (ie N- (2,4-difluorophenyl) -N- (1-methylethyl) -5-oxo-1 - (tetrahydroxy) 2H-pyran-2-ylmethyl) -1, 5-dihydro-4H-1, 2,4-
  • Aminocyclopyrachlor saflufenacil, indaziflam, methiozoline, iepcarbazone, fenoxasulfone, bicyclopyrone, propyrisulfuron and metazosulfuron.
  • Mixture formulations of compounds of the general formula (I) according to the invention may also contain fungicides and / or insecticides.
  • the safeners used with an antidote effective content reduce the phytotoxic side effects of the herbicides or herbicide / pesticide combinations used, e.g. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, oilseed rape, cotton and soybeans, preferably cereals.
  • the mixing ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the particular safener and can vary within wide limits.
  • the ratio is in the range from 200: 1 to 1: 200, preferably in the range from 100: 1 to 1: 100, in particular in the range from 20: 1 to 1:20.
  • the safeners can be formulated analogously to the compounds of general formula I or mixtures thereof with further herbicides or pesticides and as Ready-made formulation or tank mix with the herbicides are provided and used.
  • the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-form preparations, soil and spreading granulates and sprayable solutions are usually no longer diluted with further inert substances before use.
  • the type of herbicide u. a. varies the required application rate of the compounds of formula I. It can therefore vary within wide limits, z. Between 0.001 and 10,000 kg / ha or more of active substance, but is preferably between 0.005 and 5.000 kg / ha.
  • the invention furthermore relates to a method for controlling animal pests, in particular insects, using the compounds according to the invention and compositions.
  • Animal pests include:
  • Anoplura e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
  • Epitrimerus pyri Eutetranychus spp., Eriophyes spp., Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp , Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
  • helminths From the genus of helminths, eg, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, 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., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp, Strongyloides fuellebomi, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.
  • protozoa such as Eimeria
  • Eimeria protozoa
  • Calocoris spp. Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., Heliopeltis spp., Horcias nobilellus, Leptocorisa spp.
  • Empoasca spp. Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp , Nilaparvata lugens, Oncometopia spp., Orthezi
  • 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 e.g. Scutigerella immaculata.
  • Thysanoptera e.g. Basothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips 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., Ditylenchus 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., Ditylenchus dipsaci, Globodera
  • plants and plant parts are generally treated with the compounds according to the invention, i. Active ingredients and compositions directly or by affecting their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, (spraying), (spraying), sprinkling, evaporating, atomizing, misting, (ver) spreading, foaming, brushing, spreading, pouring
  • active ingredients and compositions directly or by affecting their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, (spraying), (spraying), sprinkling, evaporating, atomizing, misting, (ver) spreading, foaming, brushing, spreading, pouring
  • Drenchen drip irrigation and propagating material, especially in seeds, further treated by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer wrapping, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil.
  • a preferred direct treatment of the plants is foliar application, ie active compounds according to the invention, combinations of active substances or compositions are applied to the foliage, the frequency of treatment and the rate of application is adapted to the infestation pressure of the respective pathogen, insect, weed.
  • the treatment of the plants is then carried out by the action of the active compounds according to the invention, active ingredient combinations or compositions on the habitat of the plant.
  • This may be, for example, Drenchen, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the active compounds, drug combinations, or compositions of the invention, or by the soil application, i. the active compounds, active ingredient combinations or compositions according to the invention are introduced in solid form (for example in the form of granules) into the location of the plants. In water rice crops this may also be by metering the invention in a solid application form (e.g., as granules) into a flooded paddy field.
  • plants are meant all plant species, plant varieties and plant populations, such as desirable and undesirable wild plants or crop plants.
  • Crop plants to be treated according to the invention are plants which occur naturally or those which have been obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or by combinations of the abovementioned methods.
  • the term crop also includes transgenic plants.
  • Plant varieties are understood as meaning plants having new properties, so-called traits, which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques or a combination thereof. These may be varieties, breeds, biotypes and genotypes.
  • Plant parts are understood to mean all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, in particular leaves, Needles, stems, stems, flowers, fruiting bodies, fruits, seeds, roots, tubers and rhizomes.
  • plant parts further includes crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds or seeds.
  • naturally occurring or plant species and plant cultivars obtained by conventional breeding and optimization methods e.g., crossing or protoplast fusion
  • plant parts thereof are treated.
  • transgenic plants which have been obtained by genetic engineering, if appropriate in combination with conventional methods, and their parts are treated.
  • the present invention further relates to a method of protecting seeds and germinating plants from attack by pests by treating the seeds with compounds or compositions of the invention.
  • the invention also relates to the use of the compounds or compositions according to the invention for the treatment of seed for the protection of the seed and the resulting plant from pests. Furthermore, the invention relates to seed which has been treated for protection against pests with compounds or compositions according to the invention.
  • One of the advantages of the present invention is that because of the particular systemic properties of the compounds or compositions of the present invention, treatment of the seed with these compounds or compositions protects not only the seed itself but also the resulting plants from pests after emergence. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • the compounds or compositions according to the invention can also be used in particular in the case of transgenic seed, wherein the plants resulting from this seed are capable of expressing a protein directed against pests.
  • certain pests can already be controlled by the expression of the insecticidal protein, for example, and additionally protected against damage by the active compound combinations according to the invention.
  • the compounds or compositions according to the invention are suitable for the protection of seed of any plant variety as mentioned above, which is used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are corn, peanut, canola, rapeseed, poppy, soybean, cotton, turnip (eg sugarbeet and fodder beet), rice, millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables ( eg tomatoes, cabbage).
  • the compounds or compositions according to the invention are likewise suitable for the treatment of the seed of fruit plants and vegetables as already mentioned above. Of particular importance is the treatment of the seeds of maize, soya, cotton, wheat and canola or rapeseed.
  • transgenic seed with compounds or compositions according to the invention is of particular importance.
  • the heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. and its gene product activity against European corn borer and / or corn rootworm shows. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have obtained genetic material by the genetic engineering modification which gives these plants particularly advantageous valuable properties ("traits”) .
  • traits are better plant growth, increased tolerance to high or lower temperatures, increased tolerance to dryness or to bottoms salt, increased flowering efficiency, 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
  • Particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses and increased tolerance the plants against certain herbicidal active ingredients.
  • transgenic plants include the important crops such as cereals (wheat, rice), corn, soybean, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybean, 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 formed in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CrylA (a) , CrylA (b), CrylA (c), CryllA, CrylllA, CrylllB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) in the plants (hereinafter "Bt plants”). Traits also highlight the increased defense of plants against 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
  • the increased tolerance of the plants to certain herbicidally active compounds for example imidazolinones, are particularly emphasized.
  • Sulfonylureas, glyphosate or phosphinotricin eg "PAT” gene.
  • the genes conferring the desired properties can also be present in combinations with one another in the transgenic plants.
  • “Bt plants” are maize varieties, cotton varieties, soybean varieties and potato varieties sold under the trade names YIELD GARD® (eg maize , Cotton, soybean), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® (cotton), Nucoton® (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), IMICB ) (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Herbicide-resistant plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned.
  • the compounds or compositions according to the invention can, in particular because of their strong insecticidal action in the protection of materials for the protection of industrial materials against attack and destruction by insects, such as As termites, are used. Accordingly, the invention relates to the use of the active ingredients or compositions for the protection of technical materials against attack or destruction by insects.
  • insects include, for example, beetles 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.
  • the compounds or compositions according to the invention are suitable for protection against fouling of objects, in particular of hulls, screens, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.
  • compositions can be used alone or in combination with other active ingredients as anti-fouling agents.
  • the compounds or compositions are preferably used in household, hygiene and storage.
  • the active compounds or compositions are used alone or in combination with other active ingredients and / or adjuvants. They are preferred in
  • the active compounds according to the invention are active against sensitive and resistant species as well as against all stages of development.
  • pests include, for example:
  • Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp.
  • Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
  • isopods e.g. Oniscus asellus, Porcellio scaber.
  • Lepismodes inquilinus From the order of the Blattaria e.g. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa,
  • Saltatoria e.g. Acheta domesticus.
  • Dermaptera e.g. Forficula auricularia.
  • 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.
  • Anoplura e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix, Phthirus pubis.
  • Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
  • the application of the invention as a household insecticide is carried out alone or in combination with other suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, neo-nicotinoids, growth regulators or agents from other known insecticide classes.
  • Application is for example in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • Pump and atomizer sprays misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
  • 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 like 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:
  • Anoplurida e.g. 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 submissions Amblycerina and Ischnocerina, for example.
  • Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; specific examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; From the order of the Diptera and the suborders Nematocerina and Brachycerina, e.g.
  • siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp .
  • specific examples are: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; From the order of the heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp .;
  • Hyalomma spp. Dermanyssus spp., Rhipicephalus spp. (the original genus of the multiple ticks), 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,
  • the active compounds according to the invention are also suitable for controlling
  • the animals include farm animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, farmed fish, honey bees.
  • farm animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, farmed fish, honey bees.
  • the animals also include pets - which are also referred to as pets - such as dogs, cats, caged birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice.
  • 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.
  • enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, BoIi, the feed-through process, suppositories
  • parenteral administration for
  • the active ingredients can be used as shampoo or as appropriate, in aerosols or non-pressurized sprays, eg pump sprays and Nebulizer sprays, applicable, formulated formulations.
  • 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, apply directly or after dilution (eg 100-10,000 times dilution) or use them as a chemical bath.
  • the active compounds according to the invention can be used in combination with suitable synergists or other active substances such as, for example, acaricides, insecticides, anthelmintics, antiprotozoal agents.
  • insecticidal mixing partner is a variety of drugs in question. It is known that insecticides often have an acaricidal and / or nematicidal action.
  • Acetylcholinesterase (AChE) inhibitors such as
  • Carbamates for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendivarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilane, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb , Metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, and xylylcarb; or Organophosphates, eg acephates, azamethiphos, azinphos (-methyl, -ethy
  • GABA-controlled chloride channel antagonists such as organochlorines, eg, camphechlor, chlordane, endosulfan, gamma-HCH, HCH 1 heptachlor, lindane, and methoxychlor; or fiproles (phenylpyrazoles), for example, acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, and vaniliprole.
  • organochlorines eg, camphechlor, chlordane, endosulfan, gamma-HCH, HCH 1 heptachlor, lindane, and methoxychlor
  • fiproles phenylpyrazoles
  • Sodium channel modulators / voltage-dependent sodium channel blockers such as pyrethroids, eg acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, biphenol, bioallethrin, bioallethrin-S cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin , Deltamethrin, empenthrin (1R isomer), esfenvalerate, etofenprox
  • nicotinergic acetylcholine receptor agonists / antagonists such as chloronicotinyls, eg acetamipride, clothianidin, dinotefuran, imidacloprid, imidactliziz, nitenpyram, nithiazines, thiacloprid, thiamethoxam, AKD-1022, nicotine, bensultap, cartap, thiosultap sodium, and thiocylam.
  • chloronicotinyls eg acetamipride, clothianidin, dinotefuran, imidacloprid, imidactliziz, nitenpyram, nithiazines, thiacloprid, thiamethoxam, AKD-1022, nicotine, bensultap, cartap, thiosultap sodium, and thiocylam.
  • Allosteric acetylcholine receptor modulators such as spinosyns, e.g. Spinosad and Spinetoram.
  • Mectins / macrolides e.g. Abamectin, Emamectin, Emamectin benzoate, Ivermectin, Lepimectin, and Milbemectin; or
  • Juvenile hormone analogues e.g. Hydroprene, Kinoprene, Methoprene, Epofenonane, Triprene, Fenoxycarb, Pyriproxifen, and Diofenolan.
  • agents with unknown or non-specific mechanisms of action such as
  • Fumigant e.g. Methyl bromides, chloropicrin and sulfuryl fluorides
  • Selective feeding inhibitors e.g. Cryolites, Pymetrozines, Pyrifluquinazone and Flonicamid; or
  • Mite growth inhibitors e.g. Clofentezine, hexythiazox, etoxazole.
  • inhibitors of oxidative phosphorylation, ATP disruptors such as diafenthiuron
  • Organotin compounds e.g. Azocyclotine, cyhexatin and fenbutatin oxides; or propargite, tetradifon.
  • Microwave disruptors of insect intestinal membrane such as Bacillus thuringiensis strains.
  • inhibitors of chitin biosynthesis for example benzoylureas, for example bistrifluron, chlorofluorazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, Hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron or triflumuron.
  • benzoylureas for example bistrifluron, chlorofluorazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, Hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron or triflumuron.
  • Moulting agents such as cyromazines.
  • ecdysone agonists / disruptors such as
  • Diacylhydrazines e.g. Chromafenozide, halofenozide, methoxyfenozide, tebfenozide, and fufenozide (JS118); or Azadirachtin.
  • Octopaminergic agonists such as amitraz.
  • side-III electron transport inhibitors / side II electron transport inhibitors such as, for example, hydramethylnone; acequinocyl; fluacrypyrim; or Cyflumetofen and Cyenopyrafen.
  • Electron transport inhibitors such as side-I electron transport inhibitors, from the group of METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad, and Rotenone; or voltage dependent sodium channel blockers, e.g. Indoxacarb and Metaflumizone.
  • METI acaricides e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad, and Rotenone
  • voltage dependent sodium channel blockers e.g. Indoxacarb and Metaflumizone.
  • inhibitors of fatty acid biosynthesis such as tetronic acid derivatives, e.g. Spirodiclofen and spiromesifen; or tetramic acid derivatives, e.g. Spirotetramat.
  • Neuronal inhibitors of unknown mechanism of action e.g. Bifenazate.
  • ryanodine receptor effectors such as diamides, eg flubendiamide, (R) -, (S) -3-chloro-N 1 - ⁇ 2-methyl-4- [1, 2,2,2-tetrafluoro-1 - (trifluoromethyl) ethyl] phenyl ⁇ -N 2 - (1-methyl-2-methylsulfonylethyl) phthalamide, chlorantraniliprole (Rynaxypyr), or cyantraniliprole (Cyazypyr).
  • Example 1 2,4-dichloro-6-methylpyridine-3-carboxylic acid (N-3 ', 5' -dichlorphenyl-N '- prop-2 "-in-1" -yl) hydrazide (No. 1a. 718)
  • N '-3,5-dichlorophenyl-N' -prop-2 '-in-1' -ylhydrazin is analogous to the procedure for the synthesis of the compound a-1 7231 (Step 1) via a propargylation of 3,5- dichlorophenylhydrazine.
  • N '-3,4-difluorophenyl-N' -prop-2 '-in-1' -ylhydrazin is analogous to the procedure for the synthesis of compound 1a-7231 (Step 1) via a propargylation of 3,4-difluorophenylhydrazine ,
  • Step 2 Synthesis of 2-bromo-6-methyl-4-isopropyloxypyridine-3-carboxylic acid (N ' - 3 ' , 4 ' -dichlorophenyl-N ' -prop-2 " -in- 1 " -yl) -hydrazide ( No. 1a-7231):
  • Example 4 6-chloro-5-methyl-pyridine-3-carboxylic acid (N '-4' -chlorophenyl-N '-prop-2 "- in-1" -yl) hydrazide (No. 3a-644).
  • Residue was purified by chromatography. 116 mg of product were obtained.
  • nPr is 1-propyl iPr is 2-propyl cPr is cyclopropyl
  • a dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuted in a hammer mill.
  • a wettable powder readily dispersible in water is obtained by reacting 25 parts by weight of a compound of formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium lignosulfonate and 1 part by weight Mix oleoylmethyl tauric acid sodium as wetting and dispersing agent and mill in a pin mill.
  • a dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether ( ⁇ Triton X 207), 3
  • isotridecanol polyglycol ether 8 EO
  • paraffinic mineral oil oil range, for example, about 255 to more than 277 C
  • An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
  • a water-dispersible granule is also obtained by adding 25 parts by weight of a compound of formula (I) and / or salts thereof, 5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid 2 wt Parts of oleoylmethyl tauric acid sodium,
  • Seeds of monocotyledonous or dicotyledonous weed plants are placed in sandy loam soil in wood fiber pots and covered with soil.
  • the compounds of the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent applied.
  • Seeds of monocotyledonous or dicotyledonous weed plants are placed in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage.
  • the compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
  • dimethylformamide emulsifier 1.5 parts by weight of dimethylformamide emulsifier: 0.5 part by weight of alkylaryl polyglycol ether
  • Part by weight of active compound 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.
  • Boophilus microplus test (BOOPMI injection)
  • the drug solution is injected into the abdomen (Boophilus microplus), the animals are transferred to trays and stored in an air-conditioned room. The effect control takes place on storage of fertile eggs.
  • the effect is determined in%. 100% means that no ticks have laid fertile eggs.
  • Vessels containing horsemeat treated with the preparation of active compound of the desired concentration are infested with Lucilia cuprina larvae.
  • the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed.

Abstract

Hydrazide compounds of formula (I), where Q and R3 = an aryl or heteroaryl group either unsubstituted or substituted by one or more substituents, R1 = H, C1-C4 alkyl, C3-C4 cycloalkyl or formula (I') and R2 = H, alkyl, cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclylalkyl, cycloalkoxyalkyl, aryloxyalkyl, heterocyclyloxyalkyl, alkenyl, cycloakenyl, cycloalkylalkenyl, arylalkenyl, heterocyclylalkenyl, cycloalkoxyalkenyl, aryloxyalkenyl, heterocyclyloxyalkenyl, alkinyl, cycloalkylalkinyl, arylalkinyl, heterocyclylalkinyl, cycloalkoxyalkinyl, aryloxyalkinyl, heterocyclyloxyalkinyl, alkylcarbonyl, alkenylcarbonyl, alkinylcarbonyl, arylcarbonyl, heterocyclylcarbonyl, aryl or heterocyclyl, where all groups apart from H are optionally substituted. The invention further relates to a method for combatting undesired plant growth and insects and use of compounds of general formula (I) as herbicide and insecticide.

Description

Hydrazide, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Insektizide Hydrazides, process for their preparation and their use as herbicides and insecticides
Beschreibungdescription
Die Erfindung betrifft das technische Gebiet der Herbizide und der Insektizide, insbesondere der Hydrazide und Verfahren zu deren Herstellung sowie Formulierungen, die Hydrazide enthalten, zur selektiven Bekämpfung von Unkräutern und Ungräsem in Nutzpflanzenkulturen sowie zur Bekämpfung von tierischen Schädlingen.The invention relates to the technical field of herbicides and insecticides, in particular the hydrazides and processes for their preparation and formulations containing hydrazides, for the selective control of weeds and weeds in crops and for controlling animal pests.
Es ist bekannt, dass Amide, die heterocyclisch substituiert sind, herbizideIt is known that amides substituted heterocyclic are herbicidal
Eigenschaften besitzen. Aus dem Dokument WO2005/070889 sind als herbizide wirksame Amide Verbindungen der allgemeinen Formel (A) bekannt,Own properties. From document WO2005 / 070889 compounds of the general formula (A) are known as herbicidally active amides,
Figure imgf000003_0001
worin,
Figure imgf000003_0001
wherein,
J für Pyridin, Pyridinium, Pyrazol oder Isothiazol, das jeweils substituiert ist, stehen, undJ is pyridine, pyridinium, pyrazole or isothiazole, each substituted, and
R1 H oder (CrC4)-Alkyl, undR 1 is H or (C r C 4 ) alkyl, and
R2 H, (CrC-O-Alkyl, (CrC4)-Haloalkyl, (C3-C6)-Cycloalkyl, (C2-C3)-alkenyl, (C2- C3)-alkynyl, (C2-C4)-alkoxymethyl, cyano, (CrC4)-Alkoxy oder (C2-C4)- alkoxycarbonyl bedeuten.R 2 is H, (CrC-O-alkyl, (C r C4) -haloalkyl, (C 3 -C 6) cycloalkyl, (C 2 -C 3) alkenyl, (C 2 - C 3) alkynyl, (C 2 -C 4 ) alkoxymethyl, cyano, (C r C 4 ) alkoxy or (C 2 -C 4 ) alkoxycarbonyl.
Jedoch weisen die bekannten heterocyclisch substituierten Verbindungen im Hinblick auf die Bekämpfung von Schadpflanzen verschiedene Nachteile auf. Zu den Nachteilen gehören neben einer zu geringen Aktivität ein zu geringes Spektrum der bekämpften Schadpflanzen sowie eine zu geringe Selektivität in Nutzpflanzenkulturen.However, the known heterocyclic substituted compounds have various drawbacks with respect to the control of harmful plants. Among the disadvantages are in addition to a too low activity too little spectrum of combated harmful plants and too low selectivity in crops.
Die Aufgabe der vorliegenden Erfindung besteht in der Bereitstellung speziell substituierter Hydrazide mit verbesserter herbizider und insektizider Wirksamkeit sowie verbesserter herbizider Selektivität.The object of the present invention is to provide specially substituted hydrazides having improved herbicidal and insecticidal activity and improved herbicidal selectivity.
Gelöst wird die Aufgabe durch Verbindungen der allgemeinen Formel (I):The problem is solved by compounds of general formula (I):
worin
Figure imgf000004_0001
wherein
Figure imgf000004_0001
Q ein Aryl- oder Heteroarylrest bedeutet, der jeweils unsubstituiert ist oder substituiert ist durch einen oder mehrere Substituenten, jeweils unabhängig voneinander, ausgewählt aus der Gruppe bestehend aus Halogen, Cyano, Nitro, Alkyl, Haloalkyl, Cycloalkyl, Halocycloalkyl, Hydroxyalkyl, Alkoxyalkyl, Haloalkoxyalkyl, Alkenyl, Haloalkenyl, Alkinyl, Haloalkinyl, Hydroxy, Alkoxy, Haloalkoxy, Alkenyloxy, Haloalkenyloxy, Alkinyloxy, Haloalkinyloxy, Alkylthio, Haloalkylthio, Alkylsulfinyl, Haloalkylsulfinyl, Alkylsulfonyl, Haloalkylsulfonyl, Alkenylthio, Haloalkenylthio, Alkenylsulfinyl, Haloalkenylsulfinyl, Alkenylsulfonyl, Haloalkenylsulfonyl, Alkinylthio, Haloalkinylthio, Alkinylsulfinyl, Haloalkinylsulfinyl, Alkinylsulfonyl, Haloalkinylsulfonyl, Amino, Alkylamino, Dialkylamino, Cycloalkylamino, N-Alkyl-N-cycloalkylamino, Formyl, Alkylcarbonyl, (C=O)OH, (C=O)NH2, Alkoxycarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Alkylcarbonyloxy, Alkylcarbonylamino, Cycloalkylcarbonylamino,Q is an aryl or heteroaryl group, each unsubstituted or substituted by one or more substituents each independently selected from the group consisting of halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl , Alkenyl, haloalkenyl, alkynyl, haloalkynyl, hydroxy, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkenylthio, haloalkenylthio, alkenylsulfinyl, haloalkenylsulfinyl, alkenylsulfonyl, haloalkenylsulfonyl, alkynylthio, haloalkynylthio , Alkynylsulfinyl, haloalkynylsulfinyl, alkynylsulfonyl, haloalkynylsulfonyl, amino, alkylamino, dialkylamino, cycloalkylamino, N-alkyl-N-cycloalkylamino, formyl, alkylcarbonyl, (C =O) OH, (C =O) NH 2 , alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, Alkylcarbonyloxy, alkylcarbonylamino, cycloalkylcarbonylamino,
Phenylcarbonylamino, Trialkylsilyl, Phenyl, Phenoxy und einem 5- bis 6-gliedrigen heteroaromatischen Ring,Phenylcarbonylamino, trialkylsilyl, phenyl, phenoxy and a 5- to 6-membered heteroaromatic ring,
R1 Wasserstoff, Alkyl, Cycloalkyl oder
Figure imgf000005_0001
bedeutet,R 1 is hydrogen, alkyl, cycloalkyl or
Figure imgf000005_0001
means
Wasserstoff, Alkyl, Cycloalkyl, Cycloalkylalkyl, Arylalkyl, Heterocyclylalkyl, Alkoxyalkyl, Cycloalkoxyalkyl, Aryloxyalkyl, Heterocyclyloxyalkyl, Alkenyl, Cycloakenyl, Cycloalkylalkenyl, Arylalkenyl, Heterocyclylalkenyl, Cycloalkoxyalkenyl, Aryloxyalkenyl, Heterocyclyloxyalkenyl, Alkinyl, Cycloalkylalkinyl, Arylalkinyl, Heterocyclylalkinyl, Cycloalkoxyalkinyl, Aryloxyalkinyl, Heterocyclyloxyalkinyl, Alkylcarbonyl, Alkenylcarbonyl,Is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclylalkyl, alkoxyalkyl, cycloalkoxyalkyl, aryloxyalkyl, heterocyclyloxyalkyl, alkenyl, cycloalkyl, cycloalkylalkenyl, arylalkenyl, heterocyclylalkenyl, cycloalkoxyalkenyl, aryloxyalkenyl, heterocyclyloxyalkenyl, alkynyl, cycloalkylalkynyl, arylalkynyl, heterocyclylalkynyl, cycloalkoxyalkynyl, aryloxyalkynyl, heterocyclyloxyalkynyl, Alkylcarbonyl, alkenylcarbonyl,
Alkinylcarbonyl, Arylcarbonyl, Heterocyclylcarbonyl, Aryl oder Heterocyclyl bedeutet, wobei alle Reste außer Wasserstoff gegebenenfalls substituiert sind, Alkynylcarbonyl, arylcarbonyl, heterocyclylcarbonyl, aryl or heterocyclyl, all radicals other than hydrogen being optionally substituted,
R3 ein Fragment der allgemeinen Formel (IIa), (IIb), (Hc), (Hd), (Me), (Hf), (Hg), (Hh)1 (IIi), (Hj)1 (IIk)1 (IIm), (Hn), (Ho) oder (Hp)R 3 is a fragment of general formula (IIa), (IIb), (Hc), (Hd), (Me), (Hf), (Hg), (Hh) 1 (IIi), (Hj) 1 (IIk) 1 (IIm), (Hn), (Ho) or (Hp)
Figure imgf000006_0001
(He) (Hf) (Hg) (Hh)
Figure imgf000006_0002
(Hi) OU) (Hk) (Hm)
Figure imgf000006_0003
(Hn) (Ho) (Hp) bedeutet, R4, R5, R6, R7 und R8 unabhängig voneinander Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Cycloalkylalkyl, Arylalkyl, Cycloalkyl, Alkenyl, Cycloalkenyl, Alkinyl, Alkoxy, Cycloalkoxy, Alkenyloxy, Cycloalkenyloxy, Alkinyloxy, Alkylthio, Cycloalkylthio, Alkenylthio, Cycloalkenylthio, Alkinylthio, Alkylsulfinyl, Alkenylsulfinyl, Alkinylsulfinyl, Alkylsulfonyl, Alkenylsulfonyl, Alkinylsulfonyl, wobei jeder der vorgenannten Reste, mit Ausnahme von Wasserstoff, Halogen, Cyano und Nitro, gegebenenfalls substituiert ist, R9CONR10 oder R9R10NSO2, sowie
Figure imgf000006_0001
(He) (Hf) (Hg) (Hh)
Figure imgf000006_0002
(Hi) OU ) (Hk) (Hm)
Figure imgf000006_0003
(Hn) (Ho) (Hp) means R 4 , R 5 , R 6 , R 7 and R 8 independently of one another are hydrogen, halogen, cyano, nitro, alkyl, cycloalkylalkyl, arylalkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, cycloalkoxy, alkenyloxy, cycloalkenyloxy, alkynyloxy, alkylthio, Cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl wherein each of the foregoing radicals except hydrogen, halogen, cyano and nitro is optionally substituted, R 9 CONR 10 or R 9 R 10 NSO 2 , as well
R9 und R10 unabhängig voneinander Wasserstoff, Alkyl, Cycloalkyl, Alkenyl oder Alkinyl bedeuten.R 9 and R 10 independently of one another are hydrogen, alkyl, cycloalkyl, alkenyl or alkynyl.
Bevorzugt sind Hydrazide der allgemeinen Formel (I), in der Q ein Aryl- oder Heteroarylrest bedeutet, der jeweils unsubstituiert ist oder substituiert ist durch einen oder mehrere Substituenten, jeweils unabhängig voneinander, ausgewählt aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (CrC6)-Alkyl, (CrC6)-Haloalkyl, (C3- C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (CrC6)-Hydroxyalkyl, (C2-C6)-Alkoxyalkyl, (C2-C6)-Haloalkoxyalkyl, (C2-C6)-Alkenyl, (C2-C6)-Haloalkenyl, (C2-C6)-Alkinyl, (C2- C6)-Haloalkinyl, Hydroxy, (CrC6)-Alkoxy, (CrC6)-Haloalkoxy, (C2-C6)-Alkenyloxy, (C2-C6)-Haloalkenyloxy, (C2-C6)-Alkinyloxy, (C2-C6)-Haloalkinyloxy, (CrC6)-Alkylthio, (CrC6)-Haloalkylthio, (CrC6)-Alkylsulfinyl, (CrC6)-Haloalkylsulfinyl, (CrC6)- Alkylsulfonyl, (CrC6)-Haloalkylsulfonyl, (C2-C6)-Alkenylthio, (C2-C6)-Haloalkenylthio, (C2-C6)-Alkenylsulfinyl, (C2-C6)-Haloalkenylsulfinyl, (C2-C6)-Alkenylsulfonyl, (C2-C6)- Haloalkenylsulfonyl, (C2-C6)-Alkinylthio, (C2-C6)-Haloalkinylthio, (C2-C6)- Alkinylsulfinyl, (C2-C6)-Haloalkinylsulfinyl, (C2-C6)-Alkinylsulfonyl, (C2-C6)-Preferred are hydrazides of the general formula (I) in which Q is an aryl or heteroaryl radical which is in each case unsubstituted or substituted by one or more substituents, each independently of one another, selected from the group consisting of halogen, cyano, nitro, ( CrC 6) alkyl, (CrC 6) -haloalkyl, (C 3 - C 6) cycloalkyl, (C 3 -C 6) halocycloalkyl, (CrC 6) hydroxyalkyl, (C 2 -C 6) alkoxyalkyl, (C 2 -C 6) -Haloalkoxyalkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) haloalkenyl, (C 2 -C 6) -alkynyl, (C 2 - C 6) haloalkynyl, hydroxy, (C r C6) alkoxy, (CrC 6) -haloalkoxy, (C 2 -C 6) alkenyloxy, (C 2 -C 6) -Haloalkenyloxy, (C 2 -C 6) alkynyloxy, (C 2 -C 6) -Haloalkinyloxy, (C r C6) alkylthio, (C r C6) haloalkylthio, (C r C6) alkylsulfinyl, (C r C6) haloalkylsulfinyl, (C r C 6) - alkylsulfonyl, (C r C6) haloalkylsulfonyl, (C 2 -C 6) -alkenylthio, (C 2 -C 6) -Haloalkenylthio, (C 2 -C 6) alkenylsulfinyl, (C 2 -C 6) - Haloalkenylsulfinyl, (C 2 -C 6 ) alkenyl sulfonyl, (C 2 -C 6 ) haloalkenylsulfonyl, (C 2 -C 6 ) -alkynylthio, (C 2 -C 6 ) -haloalkynylthio, (C 2 -C 6 ) -alkynylsulfinyl, (C 2 -C 6 ) - Haloalkynylsulfinyl, (C 2 -C 6 ) -alkynylsulfonyl, (C 2 -C 6 ) -
Haloalkinylsulfonyl, Amino, (Ci-C6)-Alkylamino, (C2-C8)-Dialkylamino, (C3-C6)- Cycloalkylamino, (C4-C6)-N-Alkyl-N-cycloalkylamino, Formyl, (CrC6)-Alkylcarbonyl, (C=O)OH, (C=O)NH2, (d-CeJ-Alkoxycarbonyl, (CrCeJ-Alkylaminocarbonyl, (C2-C8)- Dialkylaminocarbonyl, (CrC6)-Alkylcarbonyloxy, (CrC^-Alkylcarbonylamino, (C3- C6)-Cycloalkylcarbonylamino, Phenylcarbonylamino, (C3-C6)-Trialkylsilyl, Phenyl, Phenoxy und einem 5- bis 6-gliedrigen heteroaromatischen Ring. Bevorzugt sind weiterhin Hydrazide der allgemeinen Formel (I), in der R1 Wasserstoff, (CrC4)-Alkyl oder (C-3-C4)-Cycloalkyl oderHaloalkynylsulfonyl, amino, (C 1 -C 6 ) -alkylamino, (C 2 -C 8 ) -dialkylamino, (C 3 -C 6 ) -cycloalkylamino, (C 4 -C 6 ) -N-alkyl-N-cycloalkylamino, formyl , (C 1 -C 6 ) -alkylcarbonyl, (C =O) OH, (C =O) NH 2 , (C 1 -C 6 -alkoxycarbonyl, (C 1 -C 6 -alkylaminocarbonyl, (C 2 -C 8 ) -dialkylaminocarbonyl, (C 1 -C 6 ) - alkylcarbonyloxy, (CrC ^ alkylcarbonylamino, (C 3 - C 6) -Cycloalkylcarbonylamino, phenylcarbonylamino, (C 3 -C 6) trialkylsilyl, phenyl, phenoxy and a 5- to 6-membered heteroaromatic ring. Also preferred are hydrazides of the general formula (I) in which R 1 is hydrogen, (C r C4) alkyl or (C 3 -C 4) -cycloalkyl or
Figure imgf000008_0001
bedeutet, wobei Q die in Anspruch 1 oder Anspruch 2 genannte Bedeutung hat.
Figure imgf000008_0001
where Q has the meaning given in claim 1 or claim 2.
Bevorzugt sind weiterhin Hydrazide der allgemeinen Formel (I), in der R2 Wasserstoff, (Ci-C6)-Alkyl, wobei der Alkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (Ci -C4J-AIkOXy oder (Ci-C4)-Alkylthio bestehenden Gruppe, substituiert ist,Preference is furthermore given to hydrazides of the general formula (I) in which R 2 is hydrogen, (C 1 -C 6 ) -alkyl, where the alkyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C 1 -C 6 ) 4 J-AIkOXy or (Ci-C 4 ) -alkylthio existing group, is substituted,
(C-3-C7)-Cycloalkyl, wobei der Cycloalkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (Ci-C4)-Alkyl, (d-C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkyl-(Ci-C6)-alkyl, wobei der Cycloalkylalkylrest unsubstituiert ist, oder nur der Cycloalkylrest substituiert ist, oder nur der(C 3 -C 7) -cycloalkyl, where the cycloalkyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (Ci-C 4) -alkyl, (dC 4) -alkoxy or (C r C 4 ) -Alkylthio existing group, (C 3 -C 7 ) -cycloalkyl- (Ci-C 6 ) alkyl, wherein the cycloalkylalkyl is unsubstituted, or substituted only the cycloalkyl radical, or only the
Alkylrest substituiert ist, oder sowohl der Cycloalkylrest als auch der Alkylrest substituiert sind, wobei der Cycloalkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (d- C4)-Alkoxy oder (Ci-C4)-Alkylthio bestehenden Gruppe, substituiert ist, und der Alkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, Aryl-(CrC6)-alkyl, wobei der Arylalkylrest unsubstituiert ist, oder nur der Arylrest substituiert ist, oder nur der Alkylrest substituiert ist, oder sowohl der Arylrest als auch der Alkylrest substituiert sind, wobei der Arylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C-ι-C4)-Alkyl, (d-C4)-Alkoxy oder (d-C4)-Alkylthio bestehenden Gruppe, substituiert ist, und der Alkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)- Alkoxy oder (Ci-C4)-Alkylthio bestehenden Gruppe, substituiert ist, Heterocyclyl-(Ci-C6)-alkyl, wobei der Heterocyclylalkylrest unsubstituiert ist, oder nur der Heterocyclylrest substituiert ist, oder nur der Alkylrest substituiert ist, oder sowohl der Heterocyclylrest als auch der Alkylrest substituiert sind, wobei der Heterocyclylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (d-C4)-Alkoxy oder (C-ι-C4)-Alkylthio bestehenden Gruppe, substituiert ist, und der Alkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano,Alkyl radical is substituted, or substituted both the cycloalkyl radical and the alkyl radical, wherein the cycloalkyl radical by one or more substituents selected from among halogen, cyano, (C r C 4 ) alkyl, (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) -alkylthio group, and the alkyl radical is substituted by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio, Aryl- (CrC 6 ) alkyl, wherein the arylalkyl is unsubstituted, or only the aryl radical is substituted, or only the alkyl radical is substituted, or both the aryl radical and the alkyl radical are substituted, wherein the aryl radical by one or more substituents selected is substituted from the group consisting of halogen, cyano, (C-ι-C 4) -alkyl, (dC 4) alkoxy group or (dC 4) alkylthio existing, and the alkyl moiety by one or more substituents selected from the Halogen, cyano, (CrC 4 ) alkox y or (Ci-C 4 ) -Alkylthio existing group, heterocyclyl (Ci-C 6 ) alkyl, wherein the heterocyclylalkyl is unsubstituted, or only the heterocyclyl is substituted, or substituted only the alkyl radical is, or both the heterocyclyl and the alkyl radical are substituted, wherein the heterocyclyl radical by one or more substituents selected from among halogen, cyano, (CrC 4 ) alkyl, (dC 4 ) alkoxy or (C-ι-C 4 ) alkylthio group, and the alkyl radical is substituted by one or more substituents selected from halogen, cyano,
(CrC4)-Alkoxy oder (Ci-C4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkenyl, wobei der Alkenylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)- Alkoxy oder (C-ι-C4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)- Alkinyl, wobei der Alkinylrest unsubstituiert ist oder durch einen oder mehrere(C 1 -C 4 ) -Alkoxy or (C 1 -C 4 ) -alkylthio group, (C 2 -C 6 ) -alkenyl, wherein the alkenyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano , (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) -alkylthio group, (C 2 -C 6 ) -alkynyl, where the alkynyl radical is unsubstituted or substituted by one or more
Substituenten, ausgewählt aus der aus Halogen, Cyano, (d-C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (CrC6)-Alkylcarbonyl, wobei der Alkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-CO)-Substituent selected from the group consisting of halogen, cyano, (dC 4 ) alkoxy or (C 1 -C 4 ) alkylthio, (C 1 -C 6 ) alkylcarbonyl wherein the alkyl group is unsubstituted or substituted by one or more substituents selected from which is substituted by halogen, cyano, (C r C 4 ) alkoxy or (C r C 4 ) alkylthio, (C 2 -CO) -
Alkenylcarbonyl, wobei der Alkenylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (Cr C4^AIkOXy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2- CβJ-Alkinylcarbonyl, wobei der Alkinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrAlkenylcarbonyl, wherein the alkenyl group is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C r C 4 ^ -alkoxy or (C r C 4) -alkylthio group consisting of, (C 2 - CβJ- Alkynylcarbonyl, wherein the alkynyl radical is unsubstituted or by one or more substituents selected from the group consisting of halogen, cyano, (Cr
C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, Arylcarbonyl, wobei der Arylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)- Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, Heterocyclylcarbonyl, wobei der Heterocyclylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, Aryl, wobei der Arylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, Heterocyclyl, wobei derC 4 ) alkoxy or (C 1 -C 4 ) alkylthio group, arylcarbonyl wherein the aryl group is unsubstituted or substituted by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) alkoxy or (C r C 4 ) -Alkylthio existing substituted heterocyclylcarbonyl, wherein the heterocyclyl unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4 ) alkoxy or (CrC 4 ) alkylthio is, aryl, wherein the aryl radical is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4 ) alkoxy or (C r C 4 ) alkylthio, heterocyclyl, wherein the
Heterocyclylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (d-C4)-Alkylthio bestehenden Gruppe, substituiert ist, bedeutet.Heterocyclyl unsubstituted or by one or more Substituents selected from the group consisting of halogen, cyano, (CrC 4 ) alkoxy or (dC 4 ) alkylthio group is substituted means.
Besonders bevorzugt sind Hydrazide der allgemeinen Formel (I), in derParticular preference is given to hydrazides of the general formula (I) in which
R4, R5, R6, R7 und R8 unabhängig voneinander Wasserstoff, Halogen, Cyano, Nitro, (CrC6)-Alkyl, wobei der Alkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)- Alkoxy oder (Ci -C4J-AI kylthio bestehenden Gruppe, substituiert ist, (C3-C7)- Cycloalkyl-(CrC6)-alkyl, wobei der Cycloalkylalkylrest unsubstituiert ist, oder nur der Cycloalkylrest substituiert ist, oder nur der Alkylrest substituiert ist, oder sowohl der Cycloalkylrest als auch der Alkylrest substituiert sind, wobei der Cycloalkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (Ci-C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, und der Alkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)- Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, Aryl-(Cr C6)-alkyl, wobei der Arylalkylrest unsubstituiert ist, oder nur der Arylrest substituiert ist, oder nur der Alkylrest substituiert ist, oder sowohl der Arylrest als auch der Alkylrest substituiert sind, wobei der Arylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)- Alkyl, (CrC4)-Alkoxy oder (d-C4)-Alkylthio bestehenden Gruppe, substituiert ist, und der Alkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkyl, wobei derR 4 , R 5 , R 6 , R 7 and R 8 independently of one another are hydrogen, halogen, cyano, nitro, (C 1 -C 6 ) -alkyl, where the alkyl radical is unsubstituted or by one or more substituents selected from halogen, cyano , (CrC 4) - alkoxy or (Ci -C 4 J-AI alkylthio group existing is substituted, (C 3 -C 7) - cycloalkyl (CrC 6) alkyl, wherein the cycloalkylalkyl group is unsubstituted, or only the cycloalkyl is substituted or only the alkyl radical is substituted, or both the cycloalkyl radical and the alkyl radical are substituted, wherein the cycloalkyl radical by one or more substituents selected from among halogen, cyano, (CrC 4 ) alkyl, (Ci-C 4 ) Alkoxy or (C r C 4 ) alkylthio group, and the alkyl group is substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4 ) alkoxy or (C 1 -C 4 ) alkylthio is substituted, aryl (C r C 6 ) alkyl, wherein the arylalkyl unsubstituie rt is, or only the aryl radical is substituted, or only the alkyl radical is substituted, or both the aryl radical and the alkyl radical are substituted, wherein the aryl radical is replaced by one or more substituents selected from among halogen, cyano, (CrC 4 ) - Alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio group, and the alkyl radical is substituted by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) - Alkylthio existing group, (C 3 -C 7 ) -cycloalkyl, wherein the
Cycloalkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (d-C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkenyl, wobei der Alkenylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Cycloalkyl group is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4) alkyl, (dC 4) alkoxy or (CrC 4) alkylthio existing group is substituted, (C 2 -C 6 ) -alkenyl, where the alkenyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C r C4) alkoxy or (C r C 4) -
Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkenyl, wobei der Cycloalkenylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (d- C/O-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2- CδJ-Alkinyl, wobei der Alkinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C1-C4)- Alkoxy oder (d-C4)-Alkylthio bestehenden Gruppe, substituiert ist, (C1-C6)-Alkylthio existing group, (C 3 -C 7 ) -Cycloalkenyl, wherein the cycloalkenyl radical is unsubstituted or by one or more Is substituent selected from the group consisting of halogen, cyano, (CrC 4) alkyl, (d- C / O-alkoxy or (CrC 4) -alkylthio group consisting of substituted, (C 2 - C δ J-alkynyl, where the Alkynyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4 ) - alkoxy or (dC 4 ) -Alkylthio, (C 1 -C 6 ) -
Alkoxy, wobei der Alkoxyrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4J-AIkOXy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkoxy, wobei der Cycloalkoxyrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (Cr Alkoxy, wherein the alkoxy radical is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4 J -oxyoxy or (C 1 -C 4 ) -alkylthio, (C 3 -C 7 ) cycloalkoxy wherein the cycloalkoxy group is unsubstituted or substituted (by one or more substituents selected from the group consisting of halogen, cyano, (C r C4) alkyl C r
C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2- C6)-Alkenyloxy, wobei der Alkenyloxyrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (Cr C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3- C7)-Cycloalkenyloxy, wobei der Cycloalkenyloxyrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (d-C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkinyloxy, wobei der Alkinyloxyrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (CrCβJ-Alkylthio, wobei der Alkylthiorest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkylthio, wobei der Cycloalkylthiorest unsubstituiert ist oder durch einen oder mehrereC 4 ) alkoxy or (C 1 -C 4 ) alkylthio group, (C 2 -C 6 ) alkenyloxy, wherein the alkenyloxy group is unsubstituted or substituted by one or more substituents selected from among halogen, cyano, (Cr C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio group, (C 3 -C 7 ) -cycloalkenyloxy wherein the cycloalkenyloxy group is unsubstituted or substituted by one or more substituents selected from among halogen, cyano, (CrC 4) -alkyl, (dC 4) -alkoxy or (C r C 4) -alkylthio group consisting of substituted, (C 2 -C 6) alkynyloxy, wherein the alkynyloxy group is unsubstituted or substituted by one or more substituents selected is the group consisting of halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio, (C 1 -C 6 -alkylthio wherein the alkylthio radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C r C 4 ) alkoxy or (C r C 4 ) alkylthio existing Group, (C 3 -C 7 ) -Cycloalkylthio, wherein the cycloalkylthio is unsubstituted or by one or more
Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (Cr C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2- C6)-Alkenylthio, wobei der Alkenylthiorest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (Cr C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3-Substituent selected from the group consisting of halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio, (C 2 -C 6 ) -alkenylthio, wherein the alkenylthio radical is unsubstituted or is substituted by one or more substituents selected from the group consisting of halogen, cyano, (C r C4) alkoxy or (CrC 4) -alkylthio group consisting of, (C 3 -
C7)-Cycloalkenylthio, wobei der Cycloalkenylthiorest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkinylthio, wobei der Alkinylthiorest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (CrC6)-Alkylsulfinyl, wobei derC 7 ) -cycloalkenylthio, wherein the cycloalkenylthio radical is unsubstituted or by one or more substituents selected from halogen, Cyano, (C r C 4 ) alkyl, (C r C 4 ) alkoxy or (C r C 4 ) alkylthio group substituted, (C 2 -C 6 ) alkynylthio, wherein the alkynylthio radical is unsubstituted or is substituted by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) alkylthio, (C 1 -C 6 ) alkylsulfinyl, wherein the
Alkylsulfinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C1 -C4J-AIkOXy oder (C-ι-C4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkenylsulfinyl, wobei der Alkenylsulfinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oderAlkylsulfinylrest is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4 -j-alkoxy or (C 1 -C 4 ) -alkylthio, (C 2 -C 6 ) - Alkenylsulfinyl, wherein the alkenylsulfinyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or
(CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkinylsulfinyl, wobei der Alkinylsulfinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4J-AIkOXy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (CrC6)-Alkylsulfonyl wobei der Alkylsulfonylrest unsubstituiert ist oder durch einen oder mehrere(C 1 -C 4 ) -alkylthio group, (C 2 -C 6 ) -alkynylsulfinyl, where the alkynylsulfinyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C 1 -C 4 -alkoxy or C 1 -C 4 ) -alkylthio group, (C 1 -C 6 ) -alkylsulfonyl wherein the alkylsulfonyl radical is unsubstituted or substituted by one or more
Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (C-ι-C4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkenylsulfonyl wobei der Alkenylsulfonylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C-ι-C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkinylsulfonyl wobei der Alkinylsulfonylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, NR9R10, R9CONR10 oder R9R10NSO2 bedeuten.Substituents selected from the group consisting of halogen, cyano, (CrC 4 ) alkoxy or (C-ι-C 4 ) -Alkylthio substituted, (C 2 -C 6 ) alkenylsulfonyl wherein the Alkenylsulfonylrest is unsubstituted or by a or more substituents selected from the group consisting of halogen, cyano, (C-ι-C 4) alkoxy or (CrC 4) alkylthio existing group is substituted, (C 2 -C 6) alkynylsulfonyl wherein the Alkinylsulfonylrest is unsubstituted or is substituted by one or more substituents selected from the group consisting of halogen, cyano, (C r C4) alkoxy or (C r C 4) alkylthio existing group, NR 9 R 10, CONR 9 R 10 or R 9 R 10 NSO 2 mean.
Ganz besonders bevorzugt sind Verbindungen der allgemeinen Formel (I), in derVery particular preference is given to compounds of the general formula (I) in which
R2 Wasserstoff, (CrC5)-Alkyl, Dihalogenalkyl, Trihalogenalkyl, (CrC3)-Alkoxy- (C-ι-C5)-alkyl, (C2-C5)-Alkenyl, Dihalogenalkenyl, Trihalogenalkenyl, (CrC3)- Alkoxy-(C2-C5)-alkenyl, (C2-C5)-Alkinyl, Dihalogenalkinyl, Trihalogenalkinyl oder (d-C3)-Alkoxy-(C2-C5)-alkinyl bedeutet, und R4, R5, R6, R7 und R8 unabhängig voneinander Wasserstoff, Halogen, Cyano, Nitro, (CrC5)-Alkyl, Dihalogenalkyl, Trihalogenalkyl, (CrC3)-Alkoxy-(CrC5)-alkyl, (Ci-Cs)-AIkOXy, Dihalogenalkoxy, Trihalogenalkoxy, (CrC3)-Alkoxy-(CrC5)- alkoxy, (CrC3)-Alkenyloxy, (CrC3)-Alkinyloxy, (CrC5)-Alkylthio, Dihalogenalkylthio, Trihalogenalkylthio, (CrC5)-Alkylsulfιnyl, (CrC5)-R 2 is hydrogen, (C r C 5) alkyl, dihaloalkyl, trihaloalkyl, (C r C 3) alkoxy (C-ι-C 5) alkyl, (C 2 -C 5) alkenyl, Dihalogenalkenyl, Trihalogenalkenyl , (C r C 3 ) alkoxy- (C 2 -C 5 ) -alkenyl, (C 2 -C 5 ) -alkynyl, dihaloalkynyl, trihaloalkynyl or (dC 3 ) -alkoxy- (C 2 -C 5 ) -alkynyl means, and R 4, R 5, R 6, R 7 and R 8 are independently hydrogen, halogen, cyano, nitro, (C r C 5) alkyl, dihaloalkyl, trihaloalkyl, (CrC 3) alkoxy (CrC 5) alkyl , (Ci-Cs) -alkoxy, Dihalogenalkoxy, trihaloalkoxy, (CrC 3) alkoxy (CrC 5) - alkoxy, (C r C 3) alkenyloxy, (C r C 3) alkynyloxy, (C r C 5 ) -Alkylthio, dihaloalkylthio, trihaloalkylthio, (CrC 5 ) -alkylsulfinyl, (CrC 5 ) -
Alkylsulfonyl, (CrC5)-Dialkylamino, (CrCsJ-Alkylcarbonylamino oder (C3-C7)- Cycloalkylcarbonylamino bedeuten.Alkylsulfonyl, (CrC 5 ) -dialkylamino, (CrCsJ-alkylcarbonylamino or (C 3 -C 7 ) -cycloalkylcarbonylamino.
Am meisten bevorzugt sind Verbindungen der allgemeinen Formel (I), in derMost preferred are compounds of general formula (I) in which
R2 Wasserstoff, (CrC5)-Alkyl, (CrC3)-Alkoxy-(CrC5)-alkyl oder (C2-C5)-Alkinyl, und R4, R5, R6, R7 und R8 unabhängig voneinander Wasserstoff, Fluor, Chlor, Brom,R 2 is hydrogen, (C r C 5 ) alkyl, (C r C 3 ) alkoxy (CrC 5 ) alkyl or (C 2 -C 5 ) alkynyl, and R 4 , R 5 , R 6 , R 7 and R 8 independently of one another hydrogen, fluorine, chlorine, bromine,
Cyano, Nitro, (CrC4)-Alkyl, Difluormethyl und Trifluormethyl, (CrC4)-Alkoxy, Difluormethoxy und Trifluormethoxy, (CrC4)-Alkylthio, Difluormethylthio,Cyano, nitro, (C r C4) alkyl, difluoromethyl and trifluoromethyl, (C r C 4) -alkoxy, difluoromethoxy and trifluoromethoxy, (CrC 4) alkylthio, difluoromethylthio,
Trifluormethylthio, (CrC2)-Alkylsulfinyl, (CrC2)-Alkylsulfonyl oder (CrC2)- Dialkylamino bedeuten.Trifluoromethylthio, (C r C 2 ) alkylsulfinyl, (C r C 2 ) alkylsulfonyl or (C r C 2 ) dialkylamino.
Ebenfalls bevorzugt sind Hydrazide der allgemeinen Formel (I), in derAlso preferred are hydrazides of the general formula (I) in which
R9 und R10 unabhängig voneinander Wasserstoff, (CrCβ)-Alkyl bedeuten, wobei der Alkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C-ι-C4)-Alkoxy oder (CrC4)- Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkyl, wobei der Cycloalkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (CrC4)-Alkoxy oder (d-C4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkenyl, wobei der Alkenylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4J-AIkOXy oder (CrC4)- Alkylthio bestehenden Gruppe, substituiert ist, (C2-Ce)-Alkinyl, wobei derR 9 and R 10 independently of one another are hydrogen, (C 1 -C 6) -alkyl, where the alkyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) - alkylthio existing group is substituted, (C 3 -C 7) -cycloalkyl, where the cycloalkyl is unsubstituted or substituted (by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4) alkyl -C 4) is group alkoxy or (dC 4) alkylthio existing substituted, (C 2 -C 6) -alkenyl, where the alkenyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4 J- AIkOXy or (CrC 4 ) - alkylthio existing group, (C 2 -Ce) alkynyl, wherein the
Alkinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)- Alkylthio bestehenden Gruppe, substituiert ist, bedeuten.Alkynyl radical is unsubstituted or substituted by one or more substituents, selected from the group consisting of halogen, cyano, (CrC 4) -alkoxy or (C r C 4) -, substituted alkylthio existing group mean.
Besonders bevorzugt sind Hydrazide der allgemeinen Formel (I), in der Q ein Rest ist, der ausgewählt ist aus der aus Q1-Q17 bestehenden GruppeParticularly preferred are hydrazides of general formula (I) wherein Q is a radical selected from the group consisting of Q1-Q17
Figure imgf000014_0001
und unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus R11, R12, R13, R14 oder R11a bestehenden Gruppe, substituiert ist, wobei
Figure imgf000014_0001
and is unsubstituted or substituted by one or more substituents selected from the group consisting of R 11 , R 12 , R 13 , R 14 or R 11a , wherein
R11, R12, R13, R14 unabhängig voneinander Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Cycloalkylalkyl, Arylalkyl, Cycloalkyl, Alkenyl, Cycloalkenyl, Alkinyl, Alkoxy, Cycloalkoxy, Alkenyloxy, Cycloalkenyloxy, Alkinyloxy, Alkylthio, Cycloalkylthio, Alkenylthio, Cycloalkenylthio, Alkinylthio, Alkylsulfinyl, Alkenylsulfinyl, Alkinylsulfinyl, Alkylsulfonyl, Alkenylsulfonyl, Alkinylsulfonyl, wobei jeder Rest außer der vier erstgenannten Reste gegebenenfalls durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)- Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, NR9R10, R9CONR10 oder R9R10NSO2 und R9 oder R10 unabhängig voneinander, die oben genannte Bedeutung haben,R 11 , R 12 , R 13 , R 14 independently of one another are hydrogen, halogen, cyano, nitro, alkyl, cycloalkylalkyl, arylalkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, cycloalkoxy, alkenyloxy, cycloalkenyloxy, alkynyloxy, alkylthio, cycloalkylthio, alkenylthio , Cycloalkenylthio, alkynylthio, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, each radical other than the first four radicals mentioned being optionally substituted by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) Alkylthio group, NR 9 R 10 , R 9 CONR 10 or R 9 R 10 NSO 2 and R 9 or R 10 independently of one another, have the abovementioned meaning,
R11a Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Cycloalkylalkyl, Arylalkyl,R 11a is hydrogen, halogen, cyano, nitro, alkyl, cycloalkylalkyl, arylalkyl,
Cycloalkyl, Alkenyl, Cycloalkenyl, Alkinyl, Alkoxy, Cycloalkoxy, Alkenyloxy, Cycloalkenyloxy, Alkinyloxy, Alkylthio, Cycloalkylthio, Alkenylthio, Cycloalkenylthio, Alkinylthio, Alkylsulfinyl, Alkenylsulfinyl, Alkinylsulfinyl, Alkylsulfonyl, Alkenylsulfonyl, Alkinylsulfonyl, wobei jeder Rest außer der vier erstgenannten Reste gegebenenfalls durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4J-AIkOXy oder (CrC4)- Alkylthio bestehenden Gruppe, substituiert ist, oder R9R10NSO2 bedeutet, undCycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, cycloalkoxy, alkenyloxy, cycloalkenyloxy, alkynyloxy, alkylthio, cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, wherein each of the radicals other than the four first mentioned radicals is optionally substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4 J -oxyoxy or (C 1 -C 4 ) -alkylthio, or R 9 R 10 is NSO 2 , and
T Wasserstoff, (d-CβJ-Alkyl, Benzyl oder Phenyl bedeutet, wobei jeder der drei letzt genannten Reste gegebenenfalls durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist. Besonders bevorzugt sind weiterhin Hydrazide der allgemeinen Formel (1 ) in der für den Fall, dass Q Phenyl, Phenoxy oder ein 5- bis 6-gliedriger heteroaromatischer Ring ist, diese einfach, zweifach oder dreifach mit R15 substituiert sind, wobeiT is hydrogen, (C 1 -C 6 -alkyl, benzyl or phenyl, each of the last three radicals optionally being substituted by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio existing group, is substituted. Particular preference is furthermore given to hydrazides of the general formula (1) in which, in the case where Q is phenyl, phenoxy or a 5- to 6-membered heteroaromatic ring, these are monosubstituted, disubstituted or trisubstituted by R 15 ,
R15 Halogen, Cyano, Nitro, (Ci-C4)-Alkyl, (Ci-C4)-Haloalkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Haloalkenyl, (C2-C4)-Alkinyl, (C2-C4)-Haloalkinyl, (CrC4)-Alkoxy, (CrC4)-Haloalkoxy, (CrC4)-Alkylthio, (C1- C4)-Haloalkylthio, (CrC4)-Alkylsulfinyl, (CrC4)-Alkylsulfonyl, (C1-C4)- Alkylamino, (C2-C8)-Dialkylamino, (C3-C6)-Cycloalkylamino, (C4-C6)-N-Alkyl-N- cycloalkylamino, (CrC4)-Alkylcarbonyl, (CrC6)-Alkoxycarbonyl, (CrCe)-R 15 is halogen, cyano, nitro, (Ci-C 4) alkyl, (Ci-C 4) -haloalkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) halocycloalkyl, (C 2 - C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) -alkynyl, (C 2 -C 4) haloalkynyl, (C r C4) alkoxy, (C r C 4 ) haloalkoxy, (C r C4) alkylthio, (C 1 - C 4) haloalkylthio, (C r C4) alkylsulfinyl, (C r C4) -alkylsulfonyl, (C 1 -C 4) - alkylamino , (C 2 -C 8) dialkylamino, (C 3 -C 6) cycloalkylamino, (C 4 -C 6), -N-alkyl-N- cycloalkylamino, (CrC 4) alkylcarbonyl, (CrC 6) alkoxycarbonyl , (CrCe) -
Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl oder (Cs-CβJ-Trialkylsilyl bedeutet.Alkylaminocarbonyl, (C 2 -C 8 ) -dialkylaminocarbonyl or (Cs-CβJ-trialkylsilyl means.
Ganz besonders bevorzugt sind Hydrazide der allgemeinen Formel (I) in der für den Fall, dass Q Phenyl, Phenoxy oder ein 5- bis 6-gliedriger heteroaromatischer Ring ist zwei benachbarte Reste an Q zusammen einen difunktionellen Rest -OCH2O-, -O(CH2)2O-, -CH2CH2O-, -OCH(CH3)O-, -OC(CH3)2O-, -CH2CH2CH2O-, -OCF2O-, -CF2CF2O-, -OCF2CF2O- oder -CH=CH-CH=CH- bilden.Very particular preference is given to hydrazides of the general formula (I) in which, in the case where Q is phenyl, phenoxy or a 5- to 6-membered heteroaromatic ring, two adjacent radicals on Q together form a difunctional radical -OCH 2 O-, -O (CH 2 ) 2 O-, -CH 2 CH 2 O-, -OCH (CH 3 ) O-, -OC (CH 3 ) 2 O-, -CH 2 CH 2 CH 2 O-, -OCF 2 O- -CF 2 CF 2 O-, -OCF 2 CF 2 O- or -CH = CH-CH = CH- form.
Bevorzugt sind weiterhin Hydrazide der allgemeinen Formel (I) in der die Reste R4, R5, R6, R7 und R8 jeweils mit einem oder mehreren der Reste R16 substituiert sind, wobei R16 ausgewählt ist aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (C1- C4)-Alkyl, außer für den Fall, dass es sich bei dem entsprechenden Rest R4, R5, R6, R7 oder R8 um einen Alkylrest handelt, (CrC4)-Alkoxy, (CrC4)-Haloalkoxy, (C1-C4)- Alkylthio, (CrC4)-Haloalkylthio, (CrC4)-Alkylsulfinyl, (CrC4)-Alkylsulfonyl, (C1-C4)- Alkylamino, (C2-C8)-Dialkylamino, (C3-C6)-Cycloalkylamino, (C4-C6)-N-Alkyl-N- cycloalkylamino, (CrC4)-Alkylcarbonyl, (CrCδJ-Alkoxycarbonyl, (C1-C6)- Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl oder (C3-C6)-Trialkylsilyl.Also preferred are hydrazides of the general formula (I) in which the radicals R 4 , R 5 , R 6 , R 7 and R 8 are each substituted by one or more of the radicals R 16 , wherein R 16 is selected from the group consisting of Halogen, cyano, nitro, (C 1 -C 4 ) -alkyl, except in the event that the corresponding radical R 4 , R 5 , R 6 , R 7 or R 8 is an alkyl radical, (C r C 4) alkoxy, (C r C 4) -haloalkoxy, (C 1 -C 4) - alkylthio, (C r C4) haloalkylthio, (C r C4) alkylsulfinyl, (C r C4) - Alkylsulfonyl, (C 1 -C 4 ) -alkylamino, (C 2 -C 8 ) -dialkylamino, (C 3 -C 6 ) -cycloalkylamino, (C 4 -C 6 ) -N-alkyl-N-cycloalkylamino, (CrC 4 ) -alkylcarbonyl, (CrC δ J -alkoxycarbonyl, (C 1 -C 6 ) -alkylaminocarbonyl, (C 2 -C 8 ) -dialkylaminocarbonyl or (C 3 -C 6 ) -trialkylsilyl.
Die vorliegende Erfindung umfasst alle Isomere, Atropisomere, geometrische sowie optische Isomere und im Fall der Stickstoff enthaltenden Heterocyclen auch die N- Oxide sowie die Salze dieser Verbindungen. Im Hinblick auf die erfindungsgemäßen Verbindungen werden die vorstehend und weiter unten verwendeten Bezeichnungen erläutert. Diese sind dem Fachmann geläufig und haben insbesondere die im Folgenden erläuterten Bedeutungen:The present invention includes all isomers, atropisomers, geometric and optical isomers, and in the case of the nitrogen-containing heterocycles also the N-oxides and the salts of these compounds. With regard to the compounds according to the invention, the terms used above and below are explained. These are familiar to the person skilled in the art and in particular have the meanings explained below:
Die Bezeichnung "Halogen" bedeutet beispielsweise Fluor, Chlor, Brom oder lod. Wird die Bezeichnung für einen Rest verwendet, dann bedeutet "Halogen" beispielsweise ein Fluor-, Chlor-, Brom- oder lodatom.The term "halogen" means, for example, fluorine, chlorine, bromine or iodine. When the term for a group is used, "halogen" means, for example, a fluorine, chlorine, bromine or iodine atom.
Alkyl bedeutet einen geradkettigen oder verzweigten offenkettigen Kohlenwasserstoff rest.Alkyl is a straight-chain or branched open-chain hydrocarbon radical.
Der Ausdruck
Figure imgf000017_0001
bedeutet eine Kurzschreibweise für Alkyl mit einem bis 4 Kohlenstoffatomen entsprechend der Bereichsangabe für C-Atome, d. h. umfasst die Reste Methyl, Ethyl, 1-Propyl, 2-Propyl, 1-Butyl, 2-Butyl, 2-Methylpropyl oder tert- Butyl. Allgemeine Alkylreste mit einem größeren angegebenen Bereich von C- Atomen, z. B. "(Ci-C6)Alkyr, umfassen entsprechend auch gradkettige oder verzweigte Alkylreste mit einer größeren Zahl von C-Atomen, d. h. gemäß Beispiel auch die Alkylreste mit 5 und 6 C-Atomen.The expression
Figure imgf000017_0001
means a short notation for alkyl having one to 4 carbon atoms corresponding to the range for C atoms, ie, the radicals comprises methyl, ethyl, 1-propyl, 2-propyl, 1-butyl, 2-butyl, 2-methylpropyl or tert-butyl. General alkyl radicals having a larger specified range of carbon atoms, eg. B. "(Ci-C 6 ) alkyr, accordingly also include straight-chain or branched alkyl radicals having a larger number of carbon atoms, ie according to Example, the alkyl radicals having 5 and 6 carbon atoms.
Wenn nicht speziell angegeben, sind bei den Kohlenwasserstoffresten wie Alkyl-, Alkenyl- und Alkinylresten, auch in zusammengesetzten Resten, die niederen Kohlenstoffgerüste, z.B. mit 1 bis 6 C-Atomen bzw. bei ungesättigten Gruppen mit 2 bis 6 C-Atomen, bevorzugt. Alkylreste, auch in den zusammengesetzten Resten wie Alkoxy, Haloalkyl usw., bedeuten z.B. Methyl, Ethyl, n- oder i-Propyl, n-, i-, t- oder 2-Butyl, Pentyle, Hexyle, wie n-Hexyl, i-Hexyl und 1 ,3-Dimethylbutyl, Heptyle, wie n-Heptyl, 1-Methylhexyl und 1 ,4-Dimethylpentyl; Alkenyl- und Alkinylreste haben die Bedeutung der den Alkylresten entsprechenden möglichen ungesättigten Reste, wobei mindestens eine Doppelbindung bzw. Dreifachbindung enthalten ist. Bevorzugt sind Reste mit einer Doppelbindung bzw. Dreifachbindung.Unless specifically stated, the hydrocarbon radicals such as alkyl, alkenyl and alkynyl radicals, even in assembled radicals, are the lower carbon skeletons, e.g. with 1 to 6 C atoms or with unsaturated groups having 2 to 6 C atoms, preferred. Alkyl radicals, also in the assembled radicals such as alkoxy, haloalkyl, etc., mean e.g. Methyl, ethyl, n- or i-propyl, n-, i-, t- or 2-butyl, pentyls, hexyls, such as n-hexyl, i-hexyl and 1,3-dimethylbutyl, heptyls, such as n-heptyl, 1-methylhexyl and 1, 4-dimethylpentyl; Alkenyl and alkynyl radicals have the meaning of the possible unsaturated radicals corresponding to the alkyl radicals, wherein at least one double bond or triple bond is contained. Preference is given to radicals having a double bond or triple bond.
Alkenyl schließt insbesondere auch geradkettige oder verzweigte offenkettige Kohlenwasserstoffreste mit mehr als einer Doppelbindung ein, wie 1 ,3-Butadienyl und 1 ,4-Pentadienyl, aber auch Allenyl- oder Kumulenyl-reste mit einer bzw. mehreren kumulierten Doppelbindungen, wie beispielsweise Allenyl (1 ,2- Propadienyl), 1 ,2-Butadienyl und 1 ,2,3-Pentatrienyl.In particular, alkenyl also includes straight-chain or branched open-chain hydrocarbon radicals having more than one double bond, such as 1,3-butadienyl and 1, 4-pentadienyl, but also allenyl or Kumulenyl residues with one or more cumulative double bonds, such as allenyl (1, 2-propadienyl), 1, 2-butadienyl and 1, 2,3-pentatrienyl.
Alkinyl schließt insbesondere auch geradkettige oder verzweigte offenkettigeIn particular, alkynyl also includes straight-chain or branched open-chain
Kohlenwasserstoffreste mit mehr als einer Dreifachbindung oder auch mit einer oder mehreren Dreifachbindungen und einer oder mehreren Doppelbindungen ein, wie beispielsweise 1 ,3-Butatrienyl bzw. 3-Penten-1-in-1-yl.Hydrocarbon radicals having more than one triple bond or having one or more triple bonds and one or more double bonds, such as 1, 3-butatrienyl or 3-penten-1-yn-1-yl.
Alkenyl bedeutet z.B. Vinyl, welches ggf. durch weitere Alkylreste substituiert ist, z.B. Prop-1-en-i-yl, But-1-en-1-yl, AIIyI, 1-Methyl-prop-2-en-1-yl, 2-Methyl-prop-2-en-1-yl, But-2-en-1-yl, 1-Methyl-but-3-en-1-yl und 1-Methyl-but-2-en-1-yl, 2-Methylprop-1 -en-1 -yl, 1 -Methylprop-1 -en-1 -yl, 1 -Methylprop-2-en-1 -yl, 2-Methyl-prop-2-en-1-yl, But-2-en-1-yl, But-3-en-1-yl, 1-Methyl-but-3-en-1-yl oder 1-Methyl-but-2-en-1-yl, Pentenyl, 2-Methylpentenyl oder Hexenyl.Alkenyl means e.g. Vinyl, which is optionally substituted by further alkyl radicals, e.g. Prop-1-en-i-yl, but-1-en-1-yl, allyl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, But-2-en-1-yl, 1-methylbut-3-en-1-yl and 1-methylbut-2-en-1-yl, 2-methylprop-1 -ene-1-yl, 1-methylprop-1 -ene-1-yl, 1-methylprop-2-en-1-yl, 2-methyl-prop-2-en-1-yl, but-2-en-1-yl, butyrene 3-en-1-yl, 1-methyl-but-3-en-1-yl or 1-methyl-but-2-en-1-yl, pentenyl, 2-methylpentenyl or hexenyl.
(C2-C6)-Alkynyl bedeutet beispielsweise Ethinyl, Propargyl, 1-Methyl-prop-2-in-1-yl, 2-Butinyl, 2-Pentinyl oder 2-Hexinyl, vorzugsweise Propargyl, But-2-in-1-yl, But-3-in-1-yl oder 1-Methyl-but-3-in-1-yl.(C 2 -C 6 ) -alkynyl is, for example, ethinyl, propargyl, 1-methyl-prop-2-yn-1-yl, 2-butynyl, 2-pentynyl or 2-hexynyl, preferably propargyl, but-2-yn 1-yl, but-3-yn-1-yl or 1-methyl-but-3-yn-1-yl.
Cycloalkyl bedeutet ein carbocyclisches, gesättigtes Ringsystem mit vorzugsweise 3-8 Ring-C-Atomen, z.B. Cyclopropyl, Cyclobutyl, Cyclopentyl oder Cyclohexyl. Im Falle von gegebenenfalls substituiertem Cycloalkyl werden cyclische Systeme mit Substituenten umfasst, wobei auch Substituenten mit einer Doppelbindung am Cycloalkylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind.Cycloalkyl means a carbocyclic saturated ring system preferably having 3-8 ring C atoms, e.g. Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl. In the case of optionally substituted cycloalkyl cyclic systems are included with substituents, wherein substituents having a double bond on the cycloalkyl, z. As an alkylidene group such as methylidene, are included.
Im Falle von gegebenenfalls substituiertem Cycloalkyl werden auch mehrcyclische aliphatische Systeme umfaßt, wie beispielsweise Bicyclo[1.1.0]butan-1-yl, Bicyclo[1.1.0]butan-2-yl, Bicyclo[2.1.0]pentan-1-yl, Bicyclo[2.1.0]pentan-2-yl, Bicyclo[2.1.0]pentan-5-yl, Bicyclo[2.2.1]hept-2-yl (Norbornyl), Adamantan-1-yl und Adamantan-2-yl. Im Falle von substituiertem Cycloalkyl werden auch spirocyclische aliphatische Systeme umfaßt, wie beispielsweise Spiro[2.2]pent-1-yl, Spiro[2.3]hex-1-yl, Spiro[2.3]hex-4-yl, 3-Spiro[2.3]hex-5-yl.In the case of optionally substituted cycloalkyl, polycyclic aliphatic systems are also included, such as bicyclo [1.1.0] butan-1-yl, bicyclo [1.1.0] butan-2-yl, bicyclo [2.1.0] pentan-1-yl , Bicyclo [2.1.0] pentan-2-yl, bicyclo [2.1.0] pentan-5-yl, bicyclo [2.2.1] hept-2-yl (norbornyl), adamantan-1-yl and adamantan-2 yl. In the case of substituted cycloalkyl, spirocyclic aliphatic systems are also included, such as spiro [2.2] pent-1-yl, spiro [2.3] hex-1-yl, spiro [2.3] hex-4-yl, 3-spiro [2.3] hex-5-yl.
Cycloalkenyl bedeutet ein carbocyclisches, nicht aromatisches, partiell ungesättigtes Ringsystem mit vorzugsweise 4-8 C-Atomen, z.B. 1-Cyclobutenyl, 2-Cyclobutenyl, 1- Cyclopentenyl, 2-Cyclopentenyl, 3-Cyclopentenyl, oder 1-Cyclohexenyl, 2- Cyclohexenyl, 3-Cyclohexenyl, 1 ,3-Cyclohexadienyl oder 1 ,4-Cyclohexadienyl, wobei auch Substituenten mit einer Doppelbindung am Cycloalkenylrest, z. B. eine Alkylidengruppe wie Methyliden, umfasst sind. Im Falle von gegebenenfalls substituiertem Cycloalkenyl gelten die Erläuterungen für substituiertes Cycloalkyl entsprechend.Cycloalkenyl means a carbocyclic, non-aromatic, partially unsaturated ring system preferably having 4-8 C atoms, e.g. 1-cyclobutenyl, 2-cyclobutenyl, 1-cyclopentenyl, 2-cyclopentenyl, 3-cyclopentenyl, or 1-cyclohexenyl, 2-cyclohexenyl, 3-cyclohexenyl, 1, 3-cyclohexadienyl or 1, 4-cyclohexadienyl, wherein also substituents with a Double bond on Cycloalkenylrest, z. As an alkylidene group such as methylidene, are included. In the case of optionally substituted cycloalkenyl, the explanations for substituted cycloalkyl apply correspondingly.
Aryl bedeutet ein mono-, bi- oder polycyclisches aromatisches System mit vorzugsweise 6 bis 14, insbesondere 6 bis 10 Ring-C-Atomen, beispielsweise Phenyl, Naphthyl, Anthryl, Phenanthrenyl, und ähnliches, vorzugsweise Phenyl.Aryl is a mono-, bi- or polycyclic aromatic system having preferably 6 to 14, in particular 6 to 10 ring C atoms, for example phenyl, naphthyl, anthryl, phenanthrenyl, and the like, preferably phenyl.
Vom Begriff „gegebenenfalls substituiertes Aryl" sind auch mehrcyclische Systeme, wie Tetrahydronaphtyl, Indenyl, Indanyl, Fluorenyl, Biphenylyl, umfasst, wobei die Bindungsstelle am aromatischen System ist.The term "optionally substituted aryl" also includes polycyclic systems, such as tetrahydronaphthyl, indenyl, indanyl, fluorenyl, biphenylyl, where the binding site is on the aromatic system.
Von der Systematik her ist Aryl in der Regel auch von dem Begriff „gegebenenfalls substituiertes Phenyl"umfasst.As a rule, aryl is also encompassed by the term "optionally substituted phenyl".
Alkoxy bedeutet ein über ein Sauerstoffatom gebundenen Alkylrest, Alkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkenylrest, Alkinyloxy bedeutet ein über ein Sauerstoffatom gebundenen Alkinylrest, Cycloalkyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkylrest und Cycloalkenyloxy bedeutet ein über ein Sauerstoffatom gebundenen Cycloalkenylrest.Alkoxy is an alkyl radical bonded via an oxygen atom, alkenyloxy is an alkynyl radical bonded via an oxygen atom, alkynyloxy is an alkynyl radical bound via an oxygen atom, cycloalkyloxy is a cycloalkyl radical bonded via an oxygen atom, and cycloalkenyloxy is a cycloalkenyl radical bonded via an oxygen atom.
Alkylthio bedeutet ein über ein Schwefelatom gebundenen Alkylrest, Alkenylthio bedeutet ein über ein Schwefelatom gebundenen Alkenylrest, Alkinylthio bedeutet ein über ein Schwefelatom gebundenen Alkinylrest, Cycloalkylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkylrest und Cycloalkenylthio bedeutet ein über ein Schwefelatom gebundenen Cycloalkenylrest.Alkylthio means an alkyl radical bonded via a sulfur atom, alkenylthio means an alkenyl radical bonded via a sulfur atom, alkynylthio an alkynyl radical bound via a sulfur atom, cycloalkylthio means a cycloalkyl radical bonded via a sulfur atom, and cycloalkenylthio means a cycloalkenyl radical bonded via a sulfur atom.
Haloalkyl, -alkenyl und -alkinyl bedeuten durch gleiche oder verschiedeneHaloalkyl, alkenyl and alkynyl mean the same or different
Halogenatome, teilweise oder vollständig substituiertes Alkyl, Alkenyl bzw. Alkinyl, z.B. Monohaloalkyl (= Monohalogenalkyl) wie CH2CH2CI, CH2CH2F, CHCICH3, CHFCH3, CH2CI, CH2F; Perhaloalkyl wie CCI3 oder CF3 oder CF2CF3; Polyhaloalkyl wie CHF2, CH2F, CH2CHFCI, CHCI2, CF2CF2H, CH2CF3,; Haloalkoxy ist z.B. OCF3, OCHF2, OCH2F, OCF2CF3, OCH2CF3 und OCH2CH2CI; entsprechendes gilt für Haloalkenyl und andere durch Halogen substituierten Reste.Halogen atoms, partially or fully substituted alkyl, alkenyl or alkynyl, for example monohaloalkyl (= monohaloalkyl) such as CH 2 CH 2 Cl, CH 2 CH 2 F, CHCICH 3 , CHFCH 3 , CH 2 Cl, CH 2 F; Perhaloalkyl such as CCI 3 or CF 3 or CF 2 CF 3 ; Polyhaloalkyl such as CHF 2, CH 2 F, CH 2 CHFCI, CHCI 2, CF 2 CF 2 H, CH 2 CF 3; Haloalkoxy is, for example, OCF 3 , OCHF 2 , OCH 2 F, OCF 2 CF 3 , OCH 2 CF 3 and OCH 2 CH 2 Cl; the same applies to haloalkenyl and other halogen-substituted radicals.
Mit der Definition „mit einem oder mehreren Resten substituiert ist" sind, wenn nicht anders definiert, unabhängig voneinander ein oder mehrere gleiche oder verschiedene Reste gemeint, wobei zwei oder mehrere Reste an einem Cyclus als Grundkörper einen oder mehrere Ringe bilden können.Unless defined otherwise, the definition "substituted by one or more radicals" means, independently of one another, one or more identical or different radicals, it being possible for two or more radicals to form one or more rings on one cycle as main body.
Substituierte Reste, wie ein substituierter Alkyl-, Alkenyl-, Alkinyl-, Cycloalkyl-, Cycloalkenyl-, Aryl-, Phenyl-, Benzyl-, Heterocyclyl- und Heteroarylrest, bedeuten beispielsweise einen vom unsubstituierten Grundkörper abgeleiteten substituierten Rest, wobei die Substituenten beispielsweise einen oder mehrere, vorzugsweise 1 , 2 oder 3 Reste aus der Gruppe Halogen, Alkoxy, Alkylthio, Hydroxy, Amino, Nitro, Carboxy oder eine der Carboxygruppe äquivalente Gruppe, Cyano, Isocyano, Azido, Alkoxycarbonyl, Alkylcarbonyl, Formyl, Carbamoyl, Mono- und Dialkylaminocarbonyl, substituiertes Amino, wie Acylamino, Mono- und Dialkylamino, Trialkylsilyl und gegebenenfalls substituiertes Cycloalkyl, gegebenenfalls substituiertes Aryl, gegebenenfalls substituiertes Heterocyclyl, wobei jeder der letztgenannten cyclischen Gruppen auch über Heteroatome oder divalente funktionelle Gruppen wie bei den genannten Alkylresten gebunden ist, und Alkylsulfinyl, wobei beide Enantiomere der Alkylsulfinylgruppe umfasst sind, Alkylsulfonyl, Alkylphosphinyl, Alkylphosphonyl und, im Falle cyclischer Reste (= "cyclischer Grundkörper"), auch Alkyl, Haloalkyl, Alkylthioalkyl, Alkoxyalkyl, gegebenfalls substituiertes Mono- und Dialkylaminoalkyl und Hydroxyalkyl bedeuten.Substituted radicals, such as a substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, aryl, phenyl, benzyl, heterocyclyl and heteroaryl radical, are, for example, a substituted radical derived from the unsubstituted radical, where the substituents are, for example, a or more, preferably 1, 2 or 3 radicals selected from the group consisting of halogen, alkoxy, alkylthio, hydroxy, amino, nitro, carboxy or a carboxy group equivalent group, cyano, isocyano, azido, alkoxycarbonyl, alkylcarbonyl, formyl, carbamoyl, mono- and Dialkylaminocarbonyl, substituted amino such as acylamino, mono- and dialkylamino, trialkylsilyl and optionally substituted cycloalkyl, optionally substituted aryl, optionally substituted heterocyclyl, each of the latter cyclic groups also being bonded via heteroatoms or divalent functional groups as in said alkyl radicals, and alkylsulfinyl where both enantiomers of the alkylsulfinyl group e, alkylsulfonyl, alkylphosphinyl, alkylphosphonyl and, in the case of cyclic radicals (= "cyclic parent"), also alkyl, haloalkyl, alkylthioalkyl, alkoxyalkyl, optionally substituted mono- and Dialkylaminoalkyl and hydroxyalkyl mean.
Im Begriff "substituierte Reste" wie substituiertes Alkyl etc. sind als Substituenten neben den genannten gesättigten kohlenwasserstoffhaltigen Resten entsprechende ungesättigte aliphatische und aromatische Reste, wie gegebenenfalls substituiertes Alkenyl, Alkinyl, Alkenyloxy, Alkinyloxy, Alkenylthio, Alkinylthio, Alkenyloxycarbonyl, Alkinyloxycarbonyl, Alkenylcarbonyl, Alkinylcarbonyl, Mono- und Dialkenylaminocarbonyl, Mono- und Dialkinylaminocarbonyl, Mono- und Dialkenylamino, Mono- und Dialkinylamino, Trialkenylsilyl, Trialkinylsilyl, gegebenenfalls substituiertes Cycloalkenyl, gegebenenfalls substituiertesIn the term "substituted radicals" such as substituted alkyl, etc., as substituents in addition to the saturated hydrocarbon radicals mentioned, corresponding unsaturated aliphatic and aromatic radicals, such as unsubstituted or substituted alkenyl, alkynyl, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenyloxycarbonyl, alkynyloxycarbonyl, alkenylcarbonyl, alkynylcarbonyl, Mono- and dialkenylaminocarbonyl, mono- and dialkynylaminocarbonyl, mono- and dialkenylamino, mono- and dialkynylamino, trialkenylsilyl, trialkynylsilyl, optionally substituted cycloalkenyl, optionally substituted
Cycloalkinyl, Phenyl, Phenoxy etc. eingeschlossen. Im Falle von substituierten cyclischen Resten mit aliphatischen Anteilen im Ring sind auch cyclische Systeme mit jenen Substituenten umfaßt, die mit einer Doppelbindung am Ring gebunden sind, z. B. mit einer Alkylidengruppe wie Methyliden oder Ethyliden oder einer Oxogruppe, Iminogruppe oder substituierten Iminogruppe substituiert sind.Cycloalkynyl, phenyl, phenoxy, etc. included. In the case of substituted cyclic radicals having aliphatic moieties in the ring, cyclic systems are also included with those substituents attached to the ring with a double bond, e.g. B. substituted with an alkylidene group such as methylidene or ethylidene or an oxo group, imino group or substituted imino group.
Wenn zwei oder mehrere Reste einen oder mehrere Ringe bilden, so können diese carbocyclisch, heterocyclisch, gesättigt, teilgesättigt, ungesättigt, beispielsweise auch aromatisch und gegebenenfalls weiter substituiert sein. Die annellierten Ringe sind vorzugsweise 5- oder 6-Ringe, besonders bevorzugt sind benzokondensierte Cyclen.If two or more radicals form one or more rings, these may be carbocyclic, heterocyclic, saturated, partially saturated, unsaturated, for example also aromatic and optionally further substituted. The fused rings are preferably 5- or 6-membered rings, particularly preferred are benzo-fused rings.
Die beispielhaft genannten Substituenten ("erste Substituentenebene") können, sofern sie kohlenwasserstoffhaltige Anteile enthalten, dort gegebenenfalls weiter substituiert sein ("zweite Substitutentenebene"), beispielsweise durch einen der Substituenten, wie er für die erste Substituentenebene definiert ist. Entsprechende weitere Substituentenebenen sind möglich. Vorzugsweise werden vom Begriff "substituierter Rest" nur ein oder zwei Substitutentenebenen umfasst.The exemplified substituents ("first substituent level"), if they contain hydrocarbon-containing moieties, may optionally be further substituted there ("second substituent plane"), for example by one of the substituents as defined for the first substituent level. Corresponding further substituent levels are possible. Preferably, the term "substituted radical" includes only one or two substituent levels.
Bevorzugte Substituenten für die Substituentenebenen sind beispielsweise Amino, Hydroxy, Halogen, Nitro, Cyano, Isocyano, Mercapto, Isothiocyanato, Carboxy, Carbonamid, SF5, Aminosulfonyl, Alkyl, Cycloalkyl, Alkenyl, Cycloalkenyl, Alkinyl, Monoalkyl-amino, Dialkyl-amino, N-Alkanoyl-amino, Alkoxy, Alkenyloxy, Alkinyloxy, Cycloalkoxy, Cycloalkenyloxy, Alkoxy-carbonyl, Alkenyloxy-carbonyl, Alkinyloxy-carbonyl, Aryloxycarbonyl, Alkanoyl, Alkenyl-carbonyl, Alkinyl-carbonyl, Aryl-carbonyl, Alkylthio, Cycloalkylthio, Alkenylthio, Cycloalkenylthio, Alkinylthio, Alkylsulfenyl, Alkylsulfinyl, wobei beide Enantiomere der Alkylsulfinylgruppe umfasst sind, Alkylsulfonyl, Monoalkyl-aminosulfonyl, Dialkyl-aminosulfonyl, Alkylphosphinyl, Alkylphosphonyl, wobei für Alkylphosphinyl bzw. Alkylphosphonyl beide Enantiomere umfasst sind, N-Alkyl-aminocarbonyl, N,N-Dialkyl-aminocarbonyl, N-Alkanoyl-amino- carbonyl, N-Alkanoyl-N-alkyl-aminocarbonyl, Aryl, Aryloxy, Benzyl, Benzyloxy, Benzylthio, Arylthio, Arylamino, Benzylamino, Heterocyclyl und Trialkylsilyl.Preferred substituents for the substituent levels are, for example, amino, hydroxyl, halogen, nitro, cyano, isocyano, mercapto, isothiocyanato, carboxy, carbonamide, SF 5 , aminosulfonyl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, Alkynyl, monoalkylamino, dialkylamino, N-alkanoylamino, alkoxy, alkenyloxy, alkynyloxy, cycloalkoxy, cycloalkenyloxy, alkoxycarbonyl, alkenyloxycarbonyl, alkynyloxycarbonyl, aryloxycarbonyl, alkanoyl, alkenylcarbonyl, alkynylcarbonyl, Arylcarbonyl, alkylthio, cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfenyl, alkylsulfinyl wherein both enantiomers of the alkylsulfinyl group are included, alkylsulfonyl, monoalkylaminosulfonyl, dialkylaminosulfonyl, alkylphosphinyl, alkylphosphonyl, wherein for alkylphosphinyl and alkylphosphonyl both enantiomers are included , N-alkylaminocarbonyl, N, N-dialkylaminocarbonyl, N-alkanoylaminocarbonyl, N-alkanoyl-N-alkylaminocarbonyl, aryl, aryloxy, benzyl, benzyloxy, benzylthio, arylthio, arylamino, benzylamino, heterocyclyl and trialkylsilyl.
Substituenten, die aus mehreren Substituentenebenen zusammengesetzt sind, sind bevorzugt Alkoxyalkyl, Alkylthioalkyl, Alkylthioalkoxy, Alkoxyalkoxy, Phenethyl, Benzyloxy, Haloalkyl, Haloalkoxy, Haloalkylthio, Haloalkanoyl, Haloalkylcarbonyl, Haloalkoxycarbonyl, Haloalkoxyalkoxy, Haloalkoxyalkylthio, Haloalkoxyalkanoyl, Haloalkoxyalkyl.Substituents composed of plural substituent levels are preferably alkoxyalkyl, alkylthioalkyl, alkylthioalkoxy, alkoxyalkoxy, phenethyl, benzyloxy, haloalkyl, haloalkoxy, haloalkylthio, haloalkanoyl, haloalkylcarbonyl, haloalkoxycarbonyl, haloalkoxyalkoxy, haloalkoxyalkylthio, haloalkoxyalkanoyl, haloalkoxyalkyl.
Kollektionen aus Verbindungen der Formel I und/oder deren Salzen, die nach den oben genannten Reaktionen synthetisiert werden können, können auch in parallelisierter Weise hergestellt werden, wobei dies in manueller, teilweise automatisierter oder vollständig automatisierter Weise geschehen kann. Dabei ist es beispielsweise möglich, die Reaktionsdurchführung, die Aufarbeitung oder die Reinigung der Produkte bzw. Zwischenstufen zu automatisieren. Insgesamt wird hierunter eine Vorgehensweise verstanden, wie sie beispielsweise durch D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley 1999, auf den Seiten 1 bis 34 beschrieben ist.Collections of compounds of formula I and / or their salts, which may be synthesized following the above reactions, may also be prepared in a parallelized manner, which may be done in a manual, partially automated or fully automated manner. It is possible, for example, to automate the reaction procedure, the work-up or the purification of the products or intermediates. Overall, this is understood to mean a procedure as described, for example, by D. Tiebes in Combinatorial Chemistry - Synthesis, Analysis, Screening (publisher Günther Jung), Verlag Wiley 1999, on pages 1 to 34.
Zur parallelisierten Reaktionsdurchführung und Aufarbeitung können eine Reihe von im Handel erhältlichen Geräten verwendet werden, beispielsweise Calpyso- Reaktionsblöcke (Caylpso reaction blocks) der Firma Barnstead International,For the parallelized reaction procedure and workup, a number of commercially available devices can be used, for example Calypyso reaction blocks (Caylpso reaction blocks) from Barnstead International,
Dubuque, Iowa 52004-0797, USA oder Reaktionsstationen (reaction stations) der Firma Radleys, Shirehill, Saffron Waiden, Essex, CB 11 3AZ, England oder MultiPROBE Automated Workstations der Firma Perkin Elmar, Waltham, Massachusetts 02451 , USA. Für die parallelisierte Aufreinigung von Verbindungen der allgemeinen Formel (I) und deren Salzen beziehungsweise von bei der Herstellung anfallenden Zwischenprodukten stehen unter anderem Chromatographieapparaturen zur Verfügung, beispielsweise der Firma ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.Dubuque, Iowa 52004-0797, USA or reaction stations from Radleys, Shirehill, Saffron Waiden, Essex, CB 11 3AZ, England or MultiPROBE Automated Workstations from Perkin Elmar, Waltham, Massachusetts 02451, USA. For the parallelized purification of compounds of the general formula (I) and their salts or of intermediates obtained during the preparation, among others, chromatography apparatuses are available, for example the company ISCO, Inc., 4700 Superior Street, Lincoln, NE 68504, USA.
Die aufgeführten Apparaturen führen zu einer modularen Vorgehensweise, bei der die einzelnen Arbeitsschritte automatisiert sind, zwischen den Arbeitsschritten jedoch manuelle Operationen durchgeführt werden müssen. Dies kann durch den Einsatz von teilweise oder vollständig integrierten Automationssystemen umgangen werden, bei denen die jeweiligen Automationsmodule beispielsweise durch Roboter bedient werden. Derartige Automationssysteme können zum Beispiel von der Firma Caliper, Hopkinton, MA 01748, USA bezogen werden.The listed equipment leads to a modular procedure, in which the individual work steps are automated, but between the work steps, manual operations must be performed. This can be circumvented by the use of partially or fully integrated automation systems in which the respective automation modules are operated, for example, by robots. Such automation systems can be obtained, for example, from Caliper, Hopkinton, MA 01748, USA.
Die Durchführung einzelner oder mehrerer Syntheseschritte kann durch den Einsatz von Polymer-supported reagents/Scavanger-Harzen unterstützt werden. In der Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in ChemFiles, Vol. 4, No. 1 , Polymer-Supported Scavengers and Reagents for Solution-Phase Synthesis (Sigma-Aldrich).The implementation of single or multiple synthetic steps can be supported by the use of polymer-supported reagents / scavanger resins. A number of experimental protocols are described in the literature, for example in ChemFiles, Vol. 1, Polymer-Supported Scavengers and Reagents for Solution Phase Synthesis (Sigma-Aldrich).
Neben den hier beschriebenen Methoden kann die Herstellung von Verbindungen der allgemeinen Formel (I) und deren Salzen vollständig oder partiell durch Festphasen unterstützte Methoden erfolgen. Zu diesem Zweck werden einzelne Zwischenstufen oder alle Zwischenstufen der Synthese oder einer für die entsprechende Vorgehensweise angepassten Synthese an ein Syntheseharz gebunden. Festphasen- unterstützte Synthesemethoden sind in der Fachliteratur hinreichend beschrieben, z.B. Barry A. Bunin in "The Combinatorial Index", Verlag Academic Press, 1998 und Combinatorial Chemistry - Synthesis, Analysis, Screening (Herausgeber Günther Jung), Verlag Wiley, 1999. Die Verwendung von Festphasen- unterstützten Synthesemethoden erlaubt eine Reihe von literaturbekannten Protokollen, die wiederum manuell oder automatisiert ausgeführt werden können. Die Reaktionen können beispielsweise mittels IRORI-Technologie in Mikroreaktoren (microreactors) der Firma Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA durchgeführt werden.In addition to the methods described herein, the preparation of compounds of general formula (I) and their salts can be carried out fully or partially by solid-phase assisted methods. For this purpose, individual intermediates or all intermediates of the synthesis or adapted for the appropriate approach synthesis are bound to a synthetic resin. Solid-phase assisted synthesis methods are well described in the literature, eg Barry A. Bunin in "The Combinatorial Index", Academic Press, 1998 and Combinatorial Chemistry - Synthesis, Analysis, Screening (published by Günther Jung), published by Wiley, 1999. Use Solid-phase assisted synthesis methods allow a series of protocols known from the literature, which in turn can be performed manually or automatically can be. The reactions can be carried out, for example, by means of IRORI technology in microreactors (microreactors) from Nexus Biosystems, 12140 Community Road, Poway, CA92064, USA.
Sowohl an fester als auch in flüssiger Phase kann die Durchführung einzelner oder mehrerer Syntheseschritte durch den Einsatz der Mikrowellen-Technologie unterstützt werden. In der Fachliteratur sind eine Reihe von Versuchsprotokollen beschrieben, beispielsweise in Microwaves in Organic and Medicinal Chemistry (Herausgeber C. O. Kappe und A. Stadler), Verlag Wiley, 2005.Both solid and liquid phases can be supported by the implementation of single or multiple synthetic steps through the use of microwave technology. A number of experimental protocols are described in the specialist literature, for example in Microwaves in Organic and Medicinal Chemistry (publishers C. O. Kappe and A. Stadler), Verlag Wiley, 2005.
Die Herstellung gemäß der hier beschriebenen Verfahren liefert Verbindungen der Formel I und deren Salze in Form von Substanzkollektionen, die „Bibliotheken" genannt werden. Gegenstand der vorliegenden Erfindung sind auch Bibliotheken, die mindestens zwei Verbindungen der Formel I und deren Salzen enthalten.The preparation according to the processes described herein yields compounds of formula I and their salts in the form of substance collections called "libraries." The present invention also provides libraries containing at least two compounds of formula I and their salts.
Hydrazide der allgemeinen Formel I können ein oder mehrere Chiraltätszentren aufweisen, weshalb sie als Racemat, als Enantiomerengemisch, als eines der beiden Enantiomere, als Diastereomerengemisch oder als eines von mehreren Diastereomeren vorliegen können.Hydrazides of the general formula I may have one or more centers of chirality, which is why they may be present as a racemate, as a mixture of enantiomers, as one of the two enantiomers, as a mixture of diastereomers or as one of several diastereomers.
Die Trennung der Enantiomeren erfolgt durch dem Fachmann bekannte Methoden, wie zum Beispiel durch Chromatograhie an chiralen Sorbentien. Auch Diasteromere lassen sich durch dem Fachmannn bekannte Methoden wie Kristallisation oder Chromatographie trennen.The enantiomers are separated by methods known to those skilled in the art, for example by chromatography on chiral sorbents. Diastereomers can also be separated by methods known to a person skilled in the art, such as crystallization or chromatography.
Die chromatographische Trennung kann sowohl im analytischen Maßstab zur Feststellung des Enantiomerenüberschusses bzw. desThe chromatographic separation can be used both on an analytical scale to determine the enantiomeric excess and the
Diastereomerenüberschusses, wie auch im präparativen Maßstab zur Herstellung von Prüfmustern für die biologische Ausprüfung erfolgen. Handelt es sich um ein Enantiomerengemisch und ist ein Enantiomer im Überschuß vorhanden, so wird dieser Überschuß als Enantiomerenüberschuß oder „enantiomeric excess", abgekürzt „ee" bezeichnet, der wie folgt definiert ist:Diastereomerenüberschusses, as well as on a preparative scale for the production of test samples for biological testing done. If the mixture of enantiomers is in excess and one enantiomer is present in excess, this excess is referred to as the enantiomeric excess, abbreviated "ee", which is defined as follows:
ee = (2X-1 ) x 100%ee = (2X-1) x 100%
X steht für die Molfraktion (=Molanteile) des im Überschuß vorhandenen Enantiomers in der Mischung. So bedeuten z. B. 40% ee ein Enantiomerenverhältnis von 70:30.X represents the mole fraction (= mole fractions) of the excess enantiomer in the mixture. So z. B. 40% ee an enantiomeric ratio of 70:30.
Der „ee" kann durch verschiedene physikalische Methoden bestimmt werden, wie zum Beispiel vorher erwähnt, durch Chromatographie an chiralen Sorbentien in der flüssigen wie auch in der Gasphase, NMR-Messungen mit chiralen Derivaten oder durch Bestimmung des spezifischen Drehwerts, was allerdings voraussetzt, dass der spezifische Drehwert des reinen Enantiomeren bekannt ist. Die so bestimmbare optische Reinheit p,The "ee" can be determined by various physical methods, such as previously mentioned, by chromatography on chiral sorbents in the liquid as well as the gas phase, NMR measurements with chiral derivatives, or by determination of the specific rotation, which, however, requires the specific rotation of the pure enantiomer is known.
P = N/N maxP = N / N max
wird in der Praxis oft zur Charakterisierung von Enantiomerengemischen verwendet, wobei [α] der gemessene, spezifische Drehwert von polarisiertem Licht einer bestimmten Frequenz und [α]max der spezifische Drehwert des reinen Enantiomeren ist.is often used in practice for the characterization of enantiomeric mixtures, where [α] is the measured specific rotation of polarized light of a given frequency and [α] max is the specific rotation of the pure enantiomer.
Die mit 100 multiplizierte optische Reinheit wird als optische Ausbeute P bezeichnet und ist dem Enantiomerenüberschuß oder „enantiomeric excess", kurz „ee" äquivalent:The optical purity multiplied by 100 is referred to as optical yield P and is equivalent to the enantiomeric excess, "ee" for short:
P = p x 100%P = p × 100%
Entsprechendes gilt für die Charakterisierung von Diastereomerengemischen, mit dem Unterschied, dass die Messung des spezifischen Drehwerts nicht zur Charakterisierung des Diastereomerengemischs ausreicht. In diesem Fall können physikalische Methoden, wie zum Beispiel Chromatographie an chiralen Sorbentien in der flüssigen wie auch in der Gasphase, angewandt werden.The same applies to the characterization of diastereomer mixtures, with the difference that the measurement of the specific rotation value is not sufficient to characterize the mixture of diastereomers. In this case, you can physical methods, such as chromatography on chiral sorbents in the liquid as well as in the gas phase.
Die Herstellung von Verbindungen der allgemeinen Formel (I) kann auf den nachfolgend beschriebenen Verfahren basieren.The preparation of compounds of general formula (I) may be based on the methods described below.
Die Synthese der erfindungsgemäßen Verbindungen erfolgt am zweckmäßigsten aus der betreffenden Carbonsäure (III) und dem jeweiligen Hydrazin (IV):The synthesis of the compounds according to the invention is most conveniently carried out from the relevant carboxylic acid (III) and the respective hydrazine (IV):
Figure imgf000026_0001
Figure imgf000026_0001
(Hi) (IV) (i)(Hi) (IV) (i)
Eine generelle Beschreibung der Durchführung der Synthese ergibt sich aus der Fachliteratur (Houben-Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag Stuttgart / New York, Bd. E 5, Erweiterungs- und Folgebände zur vierten Auflage 1985, S. 1154 ff. sowie Houben-Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag Stuttgart / New York, Bd. E 16a/Teil 1 , Erweiterungs- und Folgebände zur vierten Auflage 1990, S. 799 ff.)A general description of the implementation of the synthesis results from the specialist literature (Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag Stuttgart / New York, Vol. E 5, extension and follow-up volumes to the fourth edition in 1985, p 1154 et seq Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag Stuttgart / New York, Vol. E 16a / Part 1, Extensions and follow-up volumes to the fourth edition 1990, p. 799 ff.)
Die Aktivierung der Carbonsäure erfolgt mit gängigen Kondensationsreagenzien, wie Carbonyldiimidazol (CDI), N-Hydroxy-1 ,2,3-benzotriazol (HOBt), 1 ,3- Dicyclohexylcarbidiimid (DCC) oder 1-[3-(Dimethylamino)propyl]-3-ethylcarbodiimid (EDC).The activation of the carboxylic acid is carried out using common condensation reagents, such as carbonyldiimidazole (CDI), N-hydroxy-1,2,3-benzotriazole (HOBt), 1,3-dicyclohexylcarbidiimide (DCC) or 1- [3- (dimethylamino) propyl] - 3-ethylcarbodiimide (EDC).
Vorteilhaft können auch polymergebundene Reagenzien wie an Polystyrol gebundenes Cyclohexylcarbodiimid (DCC-Polystyrol) eingesetzt werden.Advantageously, polymer-bound reagents such as polystyrene-bound cyclohexylcarbodiimide (DCC polystyrene) can be used.
Die Kondensationsreagenzien werden äquimolar oder bis zum 3-fachen Überschuß eingesetzt, vorzugsweise äquimolar oder bis zum 1.5-fachen Überschuß. Die Carbonsäuren können auch in die entsprechenden Carbonsäurehalogenide umgewandelt werden, die dann in Gegenwart einer Base mit dem Hydrazin (IV) umgesetzt werden können. Bevorzugt werden die Carbonsäuren (III) in die betreffenden Carbonylchloride oder Carbonylbromide (V) überführt und dann in Gegenwart einer Base mit dem Hydrazin (IV) umgesetzt.The condensation reagents are used equimolar or up to 3-fold excess, preferably equimolar or up to 1.5-fold excess. The carboxylic acids can also be converted to the corresponding carboxylic acid halides, which can then be reacted in the presence of a base with the hydrazine (IV). The carboxylic acids (III) are preferably converted into the relevant carbonyl chlorides or carbonyl bromides (V) and then reacted with the hydrazine (IV) in the presence of a base.
Die Herstellung der Carbonylhalogenide (V) aus den Carbonsäuren (III) erfolgt mit gängigen Halogenierungsreagenzien wie Oxalylchlorid, Thionylchlorid, Phosphoroxychlorid, Oxalylbromid, Thionylbromid oder Phosphoroxybromid.The preparation of the carbonyl halides (V) from the carboxylic acids (III) is carried out using common halogenating reagents such as oxalyl chloride, thionyl chloride, phosphorus oxychloride, oxalyl bromide, thionyl bromide or phosphorus oxybromide.
Zum Binden der entstehenden Säure dienen organische Basen, wieTriethylamin, Pyridin, N-Methylmorpholin aber auch anorganische Basen wie Natriumcarbonat, Kaliumcarbonat oder Kaliumhydroxid, bevorzugt jedoch Triethylamin und Pyridin.For binding the resulting acid, organic bases such as triethylamine, pyridine, N-methylmorpholine but also inorganic bases such as sodium carbonate, potassium carbonate or potassium hydroxide are used, but preferably triethylamine and pyridine.
Figure imgf000027_0001
Figure imgf000027_0001
(V) (IV) (I)(V) (IV) (I)
Auch polymergebundene Basen wie DMAP-Polystyrol können zum Einsatz kommen.Polymer-bound bases such as DMAP polystyrene can also be used.
Die Basen werden äquimolar oder bis zum 4-fachen Überschuß eingesetzt.The bases are used equimolar or up to a 4-fold excess.
Als Lösungsmittel für alle Reaktionen können Ether, wie Diethylether, Diisopropylether, tert-Butyl-methylether, Tetrahydrofuran, 1 ,4-Dioxan oder Dimethoxyethan, chlorierte Kohlenwasserstoffe wie Dichlormethan, 1 ,2-Dichlorethan oder Chloroform, aromatische Kohlenwasserstoffe wie Toluol, XyIoI oder Chlorbenzol, tertiäre Amide, wie N,N-Dimethylformamid, N,N-Dimethylacetamid oder N-Methylpyrrolidon, oder Nitrile wie Acetonitril verwendet werden. Die Carbonsäuren der Formeln (III) sind in großer Auswahl kommerziell erhältlich. Speziell substituierte Nicotinsäuren (lila) können ebenso wie speziell substiuierte Pyrazolcarbonsäuren (MIb) und 1 ,2-Thiazolcarbonsäuren (IMc) nach den in den Dokumenten WO 93/11117, WO2005/070889 sowie WO 2008/029370 publizierten Vorschriften hergestellt werden.As solvents for all reactions ethers, such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, tetrahydrofuran, 1, 4-dioxane or dimethoxyethane, chlorinated hydrocarbons such as dichloromethane, 1, 2-dichloroethane or chloroform, aromatic hydrocarbons such as toluene, xylene or chlorobenzene , tertiary amides such as N, N-dimethylformamide, N, N-dimethylacetamide or N-methylpyrrolidone, or nitriles such as acetonitrile. The carboxylic acids of formula (III) are commercially available in a wide variety. Specially substituted nicotinic acids (IIIa) as well as specifically substituted pyrazolecarboxylic acids (MIb) and 1,2-thiazolecarboxylic acids (IMc) can be prepared according to the procedures published in documents WO 93/11117, WO2005 / 070889 and WO 2008/029370.
Figure imgf000028_0001
Figure imgf000028_0001
Ia) (MIb) Ic)Ia) (MIb) Ic)
Hydrazine (IV) sind, ebenso wie die Carbonsäuren (III), und mit den verschiedensten Substitutionsmustern kommerziell erhältlich.Hydrazines (IV), as well as the carboxylic acids (III), and with a variety of substitution patterns are commercially available.
Aryl- oder Heteroarylhydrazine mit R1 = R2 = Wasserstoff, deren aromatische bzw. heteroaromatische Reste R3 spezielle Substitutionsmuster tragen, werden beispielsweise aus den entsprechenden Anilinen bzw. Aminoheteroaromaten (VI) über eine Diazotierung mit anschließender Reduktion zum Hydrazin hergestellt. Ein übliches Reduktionsmittel ist für solche Zwecke Zinn(ll)chlorid in salzsaurer Lösung (Houben-Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag Stuttgart / New York, Bd. E 16a/Teil 1 , Erweiterungs- und Folgebände zur vierten Auflage 1990, S. 656 ff.).Aryl or heteroarylhydrazines with R 1 = R 2 = hydrogen whose aromatic or heteroaromatic radicals R 3 carry special substitution patterns are prepared, for example, from the corresponding anilines or aminoheteroaromatics (VI) via a diazotization with subsequent reduction to the hydrazine. A common reducing agent for such purposes tin (II) chloride in hydrochloric acid solution (Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag Stuttgart / New York, Vol. E 16a / Part 1, Extension and follow-up volumes to the fourth edition 1990, P. 656 ff.).
Figure imgf000028_0002
Figure imgf000028_0002
(VI) (IV) mit Ri = R2 = H(VI) (IV) with R i = R 2 = H
Der Rest R2 kann gegebenenfalls anschließend über eine Umsetzung des Hydrazins mit einem Elektrophil R2-LG (VII) eingeführt werden, wobei es sich bei LG um eine geeignete Abgangsgruppe (beispielsweise Halogen, Sulfonate) handelt. Solche Reaktionen sind beispielsweise in Houben-Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag Stuttgart / New York, Bd. E 16a/Teil 1 , Erweiterungsund Folgebände zur vierten Auflage 1990, S. 588 ff. beschrieben.The radical R 2 can optionally subsequently be introduced via reaction of the hydrazine with an electrophile R 2 -LG (VII), where LG is a suitable leaving group (for example halogen, sulfonates). Such Reactions are described for example in Houben-Weyl, Methods of Organic Chemistry, Georg Thieme Verlag Stuttgart / New York, Vol. E 16a / Part 1, Extension and follow-up volumes to the fourth edition 1990, p 588 ff.
FTFT
HH
,N, ^Nk 3 , N, ^ Nk 3
H2N' ^R0 + R— LG H2N RH 2 N '^ R 0 + R LG H 2 NR
(IV) mit R1 = R2 = H (VII) (IV) mit R1 = H(IV) where R 1 = R 2 = H (VII) (IV) where R 1 = H
Abhängig vom Substituentenmuster können Verbindungen der Formel (I) Salze bilden. Salzbildung kann durch Einwirkung einer Base auf solche Verbindungen der Formel (I) erfolgen, die ein acides Wasserstoffatom tragen. Geeignete Basen sind beispielsweise organische Amine, wie Trialkylamine, Morpholin, Piperidin oder Pyridin sowie Ammonium-, Alkali- oder Erdalkalimetallhydroxide, -carbonate und -hydrogencarbonate, insbesondere Natrium- und Kaliumhydroxid, Natrium- und Kaliumcarbonat und Natrium- und Kaliumhydrogencarbonat. Diese Salze sind Verbindungen, in denen der acide Wasserstoff durch ein für die Landwirtschaft geeignetes Kation ersetzt wird, beispielsweise Metallsalze, insbesondereDepending on the substituent pattern, compounds of formula (I) may form salts. Salt formation can be effected by the action of a base on those compounds of the formula (I) which carry an acidic hydrogen atom. Suitable bases are, for example, organic amines, such as trialkylamines, morpholine, piperidine or pyridine, and ammonium, alkali metal or alkaline earth metal hydroxides, carbonates and bicarbonates, in particular sodium and potassium hydroxide, sodium and potassium carbonate and sodium and potassium bicarbonate. These salts are compounds in which the acidic hydrogen is replaced by a cation suitable for agriculture, for example metal salts, in particular
Alkalimetallsalze oder Erdalkalimetallsalze, insbesondere Natrium- und Kaliumsalze, oder auch Ammoniumsalze, Salze mit organischen Aminen oder quartäre (quaternäre) Ammoniumsalze, zum Beispiel mit Kationen der Formel [NRR'R"R'"]+, worin R bis R'" jeweils unabhängig voneinander einen organischen Rest, insbesondere Alkyl, Aryl, Aralkyl oder Alkylaryl darstellen. Infrage kommen auch Alkylsulfonium- und Alkylsulfoxoniumsalze, wie (CrC4)-Trialkylsulfonium- und (Cr C-O-Trialkylsulfoxoniumsalze.Alkali metal salts or alkaline earth metal salts, especially sodium and potassium salts, or ammonium salts, salts with organic amines or quaternary (quaternary) ammonium salts, for example with cations of the formula [NRR ' R " R '" ] + , wherein R to R '"are each independently from each other represent an organic radical, in particular alkyl, aryl, aralkyl or alkylaryl.Suitable are also alkylsulfonium and alkylsulfoxonium salts, such as (CrC 4 ) -Trialkylsulfonium- and (C r CO-Trialkylsulfoxoniumsalze.
Besitzen die Verbindungen der Formel (I) ein basisches Zentrum, so können sie durch Anlagerung einer geeigneten anorganischen oder organischen Säure, wie Mineralsäuren, wie zum Beispiel HCl, HBr, H2SO4, H3Pθ4θder HNO3, oder organischen Säuren, wie zum Beispiel Ameisensäure, Essigsäure, Propionsäure, Oxalsäure, Milchsäure oder Salicylsäure oder Sulfonsäuren, wie zum Beispiel p- Toluolsulfonsäure, an die basische Gruppe Salze bilden. Diese Salze enthalten dann die konjugierte Base der Säure als Anion.If the compounds of formula (I) have a basic center, they may be prepared by addition of a suitable inorganic or organic acid, such as mineral acids, such as HCl, HBr, H 2 SO 4 , H 3 PO 4, HNO 3 , or organic acids such as formic acid, acetic acid, propionic acid, oxalic acid, lactic acid or salicylic acid or sulfonic acids such as p-toluenesulfonic acid, form salts with the basic group. These salts then contain the conjugate base of the acid as anion.
Geeignete Substituenten, die in deprotonierter Form, wie z.B. Sulfonsäuren oder Carbonsäuren, vorliegen, können innere Salze mit ihrerseits protonierbaren Gruppen, wie Aminogruppen bilden.Suitable substituents which are in deprotonated form, e.g. Sulfonic acids or carboxylic acids, may form internal salts with their turn protonatable groups, such as amino groups.
Die erfindungsgemäßen Verbindungen der Formel (I) und/oder deren Salze, im folgenden zusammen als „erfindungsgemäße Verbindungen" bezeichnet, weisen eine ausgezeichnete herbizide Wirksamkeit gegen ein breites Spektrum wirtschaftlich wichtiger mono- und dikotyler annueller Schadpflanzen auf. Auch schwer bekämpfbare perennierende Schad pflanzen, die aus Rhizomen, Wurzelstöcken oder anderen Dauerorganen austreiben, werden durch die Wirkstoffe gut erfaßt.The compounds of the formula (I) according to the invention and / or their salts, together referred to as "compounds according to the invention", have excellent herbicidal activity against a broad spectrum of economically important monocotyledonous and dicotyledonous harmful plants. which expel from rhizomes, rhizomes or other permanent organs are well detected by the active ingredients.
Außerdem weisen die erfindungsgemäßen Verbindungen eine ausgezeichnete insektizide Wirksamkeit auf.In addition, the compounds of the invention have excellent insecticidal activity.
Eine wirksame Menge einer oder mehrerer der Verbindungen der Formel (I) oder eines ihrer Λ/-Oxide oder eines ihrer Salze können in Form von Spritzpulvern, emulgierbaren Konzentraten, versprühbaren Lösungen, Stäubemitteln oderAn effective amount of one or more of the compounds of formula (I) or one of their Λ / oxides or one of its salts may be in the form of wettable powders, emulsifiable concentrates, sprayable solutions, dusts or
Granulaten in den üblichen Zubereitungen angewendet werden. Es ist vorgesehen, dass die Zusammensetzung mindestens eines der im Pflanzenschutz üblichen Formulierungshilfsmittels enthalten kann.Granules are used in the usual preparations. It is envisaged that the composition may contain at least one of the customary in plant protection formulation auxiliaries.
Gegenstand der Erfindung sind auch pflanzenwachstumsregulierende Mittel, welche die erfindungsgemäßen Verbindungen enthalten.The invention also relates to plant growth-regulating agents which contain the compounds according to the invention.
Die erfindungsgemäßen Verbindungen können auf verschiedene Art formuliert werden, je nachdem welche biologischen und/oder chemisch-physikalischen Parameter vorgegeben sind. Als Formulierungsmöglichkeiten kommen beispielsweise in Frage: Spritzpulver (WP), wasserlösliche Pulver (SP), wasserlösliche Konzentrate, emulgierbare Konzentrate (EC), Emulsionen (EW), wie Öl-in-Wasser- und Wasser-in-ÖI-Emulsionen, versprühbare Lösungen, Suspensionskonzentrate (SC), Dispersionen auf Öl- oder Wasserbasis, ölmischbare Lösungen, Kapselsuspensionen (CS), Stäubemittel (DP), Beizmittel, Granulate für die Streu- und Bodenapplikation, Granulate (GR) in Form von Mikro-, Sprüh-, Aufzugs- und Adsorptionsgranulaten, wasserdispergierbare Granulate (WG), wasserlösliche Granulate (SG), ULV-Formulierungen, Mikrokapseln und Wachse. Diese einzelnen Formulierungstypen sind im Prinzip bekannt und werden beispielsweise beschrieben in: Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, N.Y., 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.The compounds according to the invention can be formulated in various ways, depending on which biological and / or chemical-physical parameters are predetermined. Possible formulation options are, for example: wettable powder (WP), water-soluble powders (SP), water-soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as Oil-in-water and water-in-oil emulsions, sprayable solutions, suspension concentrates (SC), oil- or water-based dispersions, oil-miscible solutions, capsule suspensions (CS), dusts (DP), mordants, granules for spreading and soil application, granules (GR) in the form of micro, spray, elevator and adsorption granules, water-dispersible granules (WG), water-soluble granules (SG), ULV formulations, microcapsules and waxes. These individual formulation types are known in principle and are described, for example, in: Winnacker-Kuchler, "Chemische Technologie", Volume 7, C. Hanser Verlag, Munich, 4th edition, 1986; Wade van Valkenburg, "Pesticide Formulations", Marcel Dekker, NY, 1973; K. Martens, "Spray Drying" Handbook, 3rd ed. 1979, G. Goodwin Ltd. London.
Die notwendigen Formulierungshilfsmittel wie Inertmaterialien, Tenside, Lösungsmittel und weitere Zusatzstoffe sind ebenfalls bekannt und werden beispielsweise beschrieben in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y.; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J.; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schönfeldt,The necessary formulation auxiliaries such as inert materials, surfactants, solvents and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticides Dust Diluents and Carriers", 2nd ed., Darland Books, Caldwell N.J., H.v. Olphen, "Introduction to Clay Colloid Chemistry"; 2nd Ed., J. Wiley & Sons, N.Y .; C. Marsden, "Solvents Guide"; 2nd Ed., Interscience, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Active Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt,
"Grenzflächenaktive Äthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Band 7, C. Hanser Verlag München, 4. Aufl. 1986."Surface-active ethylene oxide adducts", Wiss. Publishing company, Stuttgart 1976; Winnacker-Kuchler, "Chemical Technology", Volume 7, C. Hanser Verlag Munich, 4th ed. 1986.
Auf der Basis dieser Formulierungen lassen sich auch Kombinationen mit anderen Pestizid wirksamen Stoffen, wie z.B. Insektiziden, Akariziden, Herbiziden, Fungiziden, sowie mit Safenern, Düngemitteln und/oder Wachstumsregulatoren herstellen, z.B. in Form einer Fertigformulierung oder als Tankmix.On the basis of these formulations, combinations with other pesticidally active substances, such as e.g. Insecticides, acaricides, herbicides, fungicides, as well as with safeners, fertilizers and / or growth regulators, e.g. in the form of a ready-made formulation or as a tank mix.
Spritzpulver sind in Wasser gleichmäßig dispergierbare Präparate, die neben dem Wirkstoff außer einem Verdünnungs- oder Inertstoff noch Tenside ionischer und/oder nichtionischer Art (Netzmittel, Dispergiermittel), z.B. polyoxyethylierte Alkylphenole, polyoxethylierte Fettalkohole, polyoxethylierte Fettamine, Fettalkoholpolyglykolethersulfate, Alkansulfonate, Alkylbenzolsulfonate, ligninsulfonsaures Natrium, 2I2'-dinaphthylmethan-6,61-disulfonsaures Natrium, dibutylnaphthalin-sulfonsaures Natrium oder auch oleoylmethyltaurinsaures Natrium enthalten. Zur Herstellung der Spritzpulver werden die herbiziden Wirkstoffe beispielsweise in üblichen Apparaturen wie Hammermühlen, Gebläsemühlen und Luftstrahlmühlen feingemahlen und gleichzeitig oder anschließend mit den Formulierungshilfsmitteln vermischt.Injectable powders are preparations which are uniformly dispersible in water and, in addition to the active substance, also contain ionic and / or nonionic surfactants (wetting agents, dispersants) other than a diluent or inert substance, for example polyoxyethylated alkylphenols. polyoxethylated fatty alcohols, polyoxethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkanesulfonates, alkylbenzenesulfonates, sodium lignosulfonate, 2 I 2'-dinaphthylmethane-6,6 1 -disulfonate sodium, dibutylnaphthalenesulfonate sodium or sodium oleoylmethyltaurine. To prepare the wettable powders, the herbicidal active compounds are finely ground, for example, in customary apparatus such as hammer mills, blower mills and air-jet mills and mixed simultaneously or subsequently with the formulation auxiliaries.
Emulgierbare Konzentrate werden durch Auflösen des Wirkstoffes in einem organischen Lösungsmittel z.B. Butanol, Cyclohexanon, Dimethylformamid, XyIoI oder auch höhersiedenden Aromaten oder Kohlenwasserstoffen oder Mischungen der organischen Lösungsmittel unter Zusatz von einem oder mehreren Tensiden ionischer und/oder nichtionischer Art (Emulgatoren) hergestellt. Als Emulgatoren können beispielsweise verwendet werden: Alkylarylsulfonsaure Calzium-Salze wie Ca-Dodecylbenzolsulfonat oder nichtionische Emulgatoren wie Fettsäurepolyglykolester, Alkylarylpolyglykolether, Fettalkoholpolyglykolether, Propylenoxid-Ethylenoxid-Kondensationsprodukte, Alkylpolyether, Sorbitanester wie z.B. Sorbitanfettsäureester oder Polyoxethylensorbitanester wie z.B. Polyoxyethylensorbitanfettsäureester.Emulsifiable concentrates are prepared by dissolving the active ingredient in an organic solvent, e.g. Butanol, cyclohexanone, dimethylformamide, xylene or else higher-boiling aromatics or hydrocarbons or mixtures of the organic solvents with the addition of one or more ionic and / or nonionic surfactants (emulsifiers). Examples of emulsifiers which can be used are: alkylarylsulfonic acid calcium salts such as calcium dodecylbenzenesulfonate or nonionic emulsifiers such as fatty acid polyglycol esters, alkylaryl polyglycol ethers, fatty alcohol polyglycol ethers, propylene oxide-ethylene oxide condensation products, alkyl polyethers, sorbitan esters such as e.g. Sorbitan fatty acid esters or polyoxethylenesorbitan esters such as e.g. Polyoxyethylene.
Stäubemittel erhält man durch Vermählen des Wirkstoffes mit fein verteilten festen Stoffen, z.B. Talkum, natürlichen Tonen, wie Kaolin, Bentonit und Pyrophyllit, oder Diatomeenerde.Dusts are obtained by milling the active ingredient with finely divided solids, e.g. Talc, natural clays such as kaolin, bentonite and pyrophyllite, or diatomaceous earth.
Suspensionskonzentrate können auf Wasser- oder Ölbasis sein. Sie können beispielsweise durch Naß-Vermahlung mittels handelsüblicher Perlmühlen und gegebenenfalls Zusatz von Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, hergestellt werden.Suspension concentrates may be water or oil based. They can be prepared, for example, by wet grinding using commercially available bead mills and, if appropriate, addition of surfactants, as described, for example, in US Pat. are already listed above for the other formulation types.
Emulsionen, z.B. ÖI-in-Wasser-Emulsionen (EW), lassen sich beispielsweise mittels Rührern, Kolloidmühlen und/oder statischen Mischern unter Verwendung von wäßrigen organischen Lösungsmitteln und gegebenenfalls Tensiden, wie sie z.B. oben bei den anderen Formulierungstypen bereits aufgeführt sind, herstellen.Emulsions, for example oil-in-water emulsions (EW), can be prepared, for example, by means of stirrers, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants, as they are already listed above, for example, in the other types of formulation produce.
Granulate können entweder durch Verdüsen des Wirkstoffes auf adsorptionsfähiges, granuliertes Inertmaterial hergestellt werden oder durch Aufbringen vonGranules can be prepared either by spraying the active ingredient on adsorptive, granulated inert material or by applying
Wirkstoffkonzentraten mittels Klebemitteln, z.B. Polyvinylalkohol, polyacrylsaurem Natrium oder auch Mineralölen, auf die Oberfläche von Trägerstoffen wie Sand, Kaolinite oder von granuliertem Inertmaterial. Auch können geeignete Wirkstoffe in der für die Herstellung von Düngemittelgranulaten üblichen Weise - gewünschtenfalls in Mischung mit Düngemitteln - granuliert werden.Active substance concentrates by means of adhesives, e.g. Polyvinyl alcohol, polyacrylic acid sodium or mineral oils, on the surface of carriers such as sand, kaolinites or granulated inert material. It is also possible to granulate suitable active ingredients in the manner customary for the production of fertilizer granules, if desired in admixture with fertilizers.
Wasserdispergierbare Granulate werden in der Regel nach den üblichen Verfahren wie Sprühtrocknung, Wirbelbett-Granulierung, Teller-Granulierung, Mischung mit Hochgeschwindigkeitsmischern und Extrusion ohne festes Inertmaterial hergestellt.Water-dispersible granules are generally prepared by the usual methods such as spray drying, fluidized bed granulation, plate granulation, mixing with high-speed mixers and extrusion without solid inert material.
Zur Herstellung von Teller-, Fließbett-, Extruder- und Sprühgranulate siehe z.B. Verfahren in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, Seiten 147 ff; "Perry's Chemical Engineer's Handbook", 5th Ed., McGraw-Hill, New York 1973, S. 8-57.For the preparation of plate, fluid bed, extruder and spray granules, see e.g. Process in "Spray-Drying Handbook" 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browning, "Agglomeration", Chemical and Engineering 1967, pages 147 ff; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-Hill, New York 1973, pp. 8-57.
Für weitere Einzelheiten zur Formulierung von Pflanzenschutzmitteln siehe z.B. G. C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961 , Seiten 81-96 und J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, Seiten 101-103.For further details on the formulation of crop protection agents see, e.g. G.C. Klingman, "Weed Control as a Science", John Wiley and Sons, Inc., New York, 1961, pp. 81-96 and J.D. Freyer, S.A. Evans, "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pp. 101-103.
Die agrochemischen Zubereitungen enthalten in der Regel 0.1 bis 99 Gew.-%, insbesondere 0.1 bis 95 Gew.-%, erfindungsgemäße Verbindungen.The agrochemical preparations generally contain from 0.1 to 99% by weight, in particular from 0.1 to 95% by weight, of compounds according to the invention.
In Spritzpulvern beträgt die Wirkstoffkonzentration z.B. etwa 10 bis 90 Gew.-%, der Rest zu 100 Gew.-% besteht aus üblichen Formulierungsbestandteilen. Bei emulgierbaren Konzentraten kann die Wirkstoffkonzentration etwa 1 bis 90, vorzugsweise 5 bis 80 Gew.-% betragen. Staubförmige Formulierungen enthalten 1 bis 30 Gew.-% Wirkstoff, vorzugsweise meistens 5 bis 20 Gew.-% an Wirkstoff, versprühbare Lösungen enthalten etwa 0.05 bis 80, vorzugsweise 2 bis 50 Gew.-% Wirkstoff. Bei wasserdispergierbaren Granulaten hängt der Wirkstoffgehalt zum Teil davon ab, ob die wirksame Verbindung flüssig oder fest vorliegt und welche Granulierhilfsmittel, Füllstoffe usw. verwendet werden. Bei den in Wasser dispergierbaren Granulaten liegt der Gehalt an Wirkstoff beispielsweise zwischen 1 und 95 Gew.-%, vorzugsweise zwischen 10 und 80 Gew.-%.In wettable powders, the active ingredient concentration is for example about 10 to 90 wt .-%, the remainder to 100 wt .-% consists of conventional formulation components. For emulsifiable concentrates, the active ingredient concentration may be about 1 to 90, preferably 5 to 80 wt .-%. Contain dusty formulations 1 to 30 wt .-% of active ingredient, preferably usually 5 to 20 wt .-% of active ingredient sprayable solutions contain about 0.05 to 80, preferably 2 to 50 wt .-% active ingredient. In the case of water-dispersible granules, the active ingredient content depends, in part, on whether the active compound is liquid or solid and which granulating aids, fillers, etc. are used. In the case of the water-dispersible granules, the content of active ingredient is, for example, between 1 and 95% by weight, preferably between 10 and 80% by weight.
Daneben enthalten die genannten Wirkstofformulierungen gegebenenfalls die jeweils üblichen Haft-, Netz-, Dispergier-, Emulgier-, Penetrations-, Konservierungs-, Frostschutz- und Lösungsmittel, Füll-, Träger- und Farbstoffe, Entschäumer, Verdunstungshemmer und den pH-Wert und die Viskosität beeinflussende Mittel.In addition, the active substance formulations mentioned optionally contain the customary adhesion, wetting, dispersing, emulsifying, penetrating, preserving, antifreeze and solvent, fillers, carriers and dyes, antifoams, evaporation inhibitors and the pH and the Viscosity-influencing agent.
Gegenstand der vorliegenden Erfindung ist daher auch ein Verfahren zur Bekämpfung von unerwünschten Pflanzen oder zur Wachstumsregulierung von Pflanzen, vorzugsweise in Pflanzenkulturen, worin eine oder mehrere erfindungsgemäße Verbindung(en) auf die Pflanzen (z.B. Schadpflanzen wie mono- oder dikotyle Unkräuter oder unerwünschte Kulturpflanzen), das Saatgut (z.B. Körner, Samen oder vegetative Vermehrungsorgane wie Knollen oder Sprossteile mit Knospen) oder die Fläche, auf der die Pflanzen wachsen (z.B. die Anbaufläche), ausgebracht werden. Dabei können die erfindungsgemäßen Verbindungen z.B. im Vorsaat- (ggf. auch durch Einarbeitung in den Boden), Vorauflauf- oder Nachauflaufverfahren ausgebracht werden. Im einzelnen seien beispielhaft einige Vertreter der mono- und dikotylen Unkrautflora genannt, die durch die erfindungsgemäßen Verbindungen kontrolliert werden können, ohne dass durch die Nennung eine Beschränkung auf bestimmte Arten erfolgen soll.The present invention therefore also provides a method for controlling undesirable plants or for regulating the growth of plants, preferably in plant crops, wherein one or more compounds of the invention are applied to the plants (eg harmful plants such as monocotyledonous or dicotyledonous weeds or undesired crop plants), the seeds (eg grains, seeds or vegetative propagules such as tubers or sprout parts with buds) or the area on which the plants grow (eg the acreage) are applied. The compounds of the invention may be e.g. in pre-sowing (possibly also by incorporation into the soil), pre-emergence or Nachauflaufverfahren be applied. Specifically, by way of example, some representatives of the monocotyledonous and dicotyledonous weed flora can be mentioned, which can be controlled by the compounds according to the invention, without the intention of limiting them to certain species.
Monokotyle Schadpflanzen umfassen die Gattungen Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.Monocotyledonous weeds include the genera Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata , Ishaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.
Dikotyle Unkräuter der Gattungen Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.Dicotyledonous weeds of the genera Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Artemisia, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga Galium Hibiscus Ipomoea Kochia Lamium Lepidium Lindernia Matricaria Mentha Mercurialis Mullugo Myosotis Papaver Pharbitis Plantago Polygonum Portulaca Ranunculus Raphanus Rorippa Rotala Rumex Salsola Senecio Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.
Werden die erfindungsgemäßen Verbindungen vor dem Keimen auf die Erdoberfläche appliziert, so wird entweder das Auflaufen der Unkrautkeimlinge vollständig verhindert oder die Unkräuter wachsen bis zum Keimblattstadium heran, stellen jedoch dann ihr Wachstum ein und sterben schließlich nach Ablauf von drei bis vier Wochen vollkommen ab.If the compounds according to the invention are applied to the surface of the earth before germination, then either the emergence of the weed seedlings is completely prevented or the weeds grow up to the cotyledon stage, but then cease their growth and finally die off completely after a lapse of three to four weeks.
Bei Applikation der Wirkstoffe auf die grünen Pflanzenteile im Nachauflaufverfahren tritt nach der Behandlung Wachstumsstop ein und die Schadpflanzen bleiben in dem zum Applikationszeitpunkt vorhandenen Wachstumsstadium stehen oder sterben nach einer gewissen Zeit ganz ab, so dass auf diese Weise eine für die Kulturpflanzen schädliche Unkrautkonkurrenz sehr früh und nachhaltig beseitigt wird.When the active ingredients are applied to the green parts of the plants postemergence, growth stops after the treatment and the harmful plants remain in the growth stage existing at the time of application or die completely after a certain time, so that a weed competition harmful to the crop plants takes place very early and sustainably eliminated.
Obgleich die erfindungsgemäßen Verbindungen eine ausgezeichnete herbizide Aktivität gegenüber mono- und dikotylen Unkräutern aufweisen, werden Kulturpflanzen wirtschaftlich bedeutender Kulturen z.B. dikotyler Kulturen der Gattungen Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, oder monokotyler Kulturen der Gattungen Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, insbesondere Zea und Triticum, abhängig von der Struktur der jeweiligen erfindungsgemäßen Verbindung und deren Aufwandmenge nur unwesentlich oder gar nicht geschädigt. Die vorliegenden Verbindungen eignen sich aus diesen Gründen sehr gut zur selektiven Bekämpfung von unerwünschtem Pflanzenwuchs in Pflanzenkulturen wie landwirtschaftlichen Nutzpflanzungen oder Zierpflanzungen.Although the compounds according to the invention have excellent herbicidal activity against monocotyledonous and dicotyledonous weeds, crops of economically important crops, eg dicotyledonous crops of the genera Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia, or monocotyledonous crops of the genera Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea, in particular Zea and Triticum, depending on the structure of the respective compound of the invention and their application rate only insignificantly or not at all damaged. For these reasons, the present compounds are very well suited for the selective control of undesired plant growth in crops such as agricultural crops or ornamental plants.
Darüberhinaus weisen die erfindungsgemäßen Verbindungen (abhängig von ihrer jeweiligen Struktur und der ausgebrachten Aufwandmenge) hervorragende wachstumsregulatorische Eigenschaften bei Kulturpflanzen auf. Sie greifen regulierend in den pflanzeneigenen Stoffwechsel ein und können damit zur gezielten Beeinflussung von Pflanzeninhaltsstoffen und zur Ernteerleichterung wie z.B. durch Auslösen von Desikkation und Wuchsstauchung eingesetzt werden. Desweiteren eignen sie sich auch zur generellen Steuerung und Hemmung von unerwünschtem vegetativen Wachstum, ohne dabei die Pflanzen abzutöten. Eine Hemmung des vegetativen Wachstums spielt bei vielen mono- und dikotylen Kulturen eine große Rolle, da beispielsweise die Lagerbildung hierdurch verringert oder völlig verhindert werden kann.In addition, the compounds according to the invention (depending on their respective structure and the applied application rate) have excellent growth-regulatory properties in crop plants. They regulate the plant's metabolism and can thus be used to specifically influence plant constituents and facilitate harvesting, such as be used by triggering desiccation and stunted growth. Furthermore, they are also suitable for the general control and inhibition of undesirable vegetative growth, without killing the plants. Inhibition of vegetative growth plays an important role in many monocotyledonous and dicotyledonous crops, since, for example, storage formation can thereby be reduced or completely prevented.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von gentechnisch oder durch konventionelle Mutagenese veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z. B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekannt. Bevorzugt bezüglich transgener Kulturen ist die Anwendung der erfindungsgemäßen Verbindungen in wirtschaftlich bedeutenden transgenen Kulturen von Nutz- und Zierpflanzen, z. B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten.Because of their herbicidal and plant growth regulatory properties, the active compounds can also be used to control harmful plants in crops of genetically engineered or conventional mutagenized plants. The transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known. Preferred with respect to transgenic crops is the use of the compounds of the invention in economically important transgenic crops of useful and ornamental plants, eg. As cereals such as wheat, barley, rye, oats, millet, rice and corn or even crops of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
Vorzugsweise können die erfindungsgemäßen Verbindungen als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind.The compounds according to the invention can preferably be employed as herbicides in crops which are resistant to the phytotoxic effects of the herbicides or have been made genetically resistant.
Aufgrund ihrer herbiziden und pflanzenwachstumsregulatorischen Eigenschaften können die Wirkstoffe auch zur Bekämpfung von Schadpflanzen in Kulturen von bekannten oder noch zu entwickelnden gentechnisch veränderten Pflanzen eingesetzt werden. Die transgenen Pflanzen zeichnen sich in der Regel durch besondere vorteilhafte Eigenschaften aus, beispielsweise durch Resistenzen gegenüber bestimmten Pestiziden, vor allem bestimmten Herbiziden, Resistenzen gegenüber Pflanzenkrankheiten oder Erregern von Pflanzenkrankheiten wie bestimmten Insekten oder Mikroorganismen wie Pilzen, Bakterien oder Viren. Andere besondere Eigenschaften betreffen z. B. das Erntegut hinsichtlich Menge, Qualität, Lagerfähigkeit, Zusammensetzung und spezieller Inhaltsstoffe. So sind transgene Pflanzen mit erhöhtem Stärkegehalt oder veränderter Qualität der Stärke oder solche mit anderer Fettsäurezusammensetzung des Ernteguts bekanntDue to their herbicidal and plant growth regulatory properties, the active compounds can also be used for controlling harmful plants in crops of known or yet to be developed genetically modified plants. The transgenic plants are usually characterized by particular advantageous properties, for example by resistance to certain pesticides, especially certain herbicides, resistance to plant diseases or pathogens of plant diseases such as certain insects or microorganisms such as fungi, bacteria or viruses. Other special properties relate to z. B. the crop in terms of quantity, quality, shelf life, composition and special ingredients. Thus, transgenic plants with increased starch content or altered quality of the starch or those with other fatty acid composition of the crop are known
Bevorzugt ist die Anwendung der erfindungsgemäßen Verbindungen der Formel I oder deren Salze in wirtschaftlich bedeutenden transgenen Kulturen von Nutz-und Zierpflanzen, z. B. von Getreide wie Weizen, Gerste, Roggen, Hafer, Hirse, Reis, Maniok und Mais oder auch Kulturen von Zuckerrübe, Baumwolle, Soja, Raps, Kartoffel, Tomate, Erbse und anderen Gemüsesorten.Preference is given to the use of the compounds of the formula I or their salts according to the invention in economically important transgenic crops of useful and ornamental plants, for. As cereals such as wheat, barley, rye, oats, millet, rice, cassava and corn or cultures of sugar beet, cotton, soy, rape, potato, tomato, pea and other vegetables.
Vorzugsweise können die Verbindungen der Formel I als Herbizide in Nutzpflanzenkulturen eingesetzt werden, welche gegenüber den phytotoxischen Wirkungen der Herbizide resistent sind bzw. gentechnisch resistent gemacht worden sind.Preferably, the compounds of formula I can be used as herbicides in crops that are resistant to the phytotoxic Effects of the herbicides are resistant or have been made genetically resistant.
Herkömmliche Wege zur Herstellung neuer Pflanzen, die im Vergleich zu bisher vorkommenden Pflanzen modifizierte Eigenschaften aufweisen, bestehen beispielsweise in klassischen Züchtungsverfahren und der Erzeugung von Mutanten. Alternativ können neue Pflanzen mit veränderten Eigenschaften mit Hilfe gentechnischer Verfahren erzeugt werden (siehe z. B. EP-A-0221044, EP-A- 0131624). Beschrieben wurden beispielsweise in mehreren FällenConventional ways of producing new plants which have modified properties in comparison to previously occurring plants consist, for example, in classical breeding methods and the production of mutants. Alternatively, new plants with altered properties can be generated by means of genetic engineering methods (see, for example, EP-A-0221044, EP-A-0131624). For example, several cases have been described
gentechnische Veränderungen von Kulturpflanzen zwecks Modifikation der in den Pflanzen synthetisierten Stärke (z. B. WO 92/11376, WO 92/14827, WO 91/19806), transgene Kulturpflanzen, welche gegen bestimmte Herbizide vom Typ Glufosinate (vgl. z. B. EP-A-0242236, EP-A-242246) oder Glyphosategenetic modifications of crop plants for the purpose of modifying the starch synthesized in the plants (for example WO 92/11376, WO 92/14827, WO 91/19806), transgenic crop plants which are resistant to certain glufosinate-type herbicides (cf. EP-A-0242236, EP-A-242246) or glyphosate
(WO 92/00377) oder der Sulfonylharnstoffe (EP-A-0257993, US-A-5013659) resistent sind, transgene Kulturpflanzen, beispielsweise Baumwolle, mit der Fähigkeit Bacillus thuringiensis-Toxine (Bt-Toxine) zu produzieren, welche die Pflanzen gegen bestimmte Schädlinge resistent machen (EP-A-0142924,(WO 92/00377) or the sulfonylureas (EP-A-0257993, US-A-5013659) are resistant to produce transgenic crops, for example cotton, with the ability Bacillus thuringiensis toxins (Bt toxins), the plants against make certain pests resistant (EP-A-0142924,
EP-A-0193259), transgene Kulturpflanzen mit modifizierter Fettsäurezusammensetzung (WO 91/13972), gentechnisch veränderte Kulturpflanzen mit neuen Inhalts- oder Sekundärstoffen z. B. neuen Phytoalexinen, die eine erhöhteEP-A-0193259), transgenic crops with modified fatty acid composition (WO 91/13972), genetically modified crops with new content or secondary substances z. B. new phytoalexins, which increased one
Krankheitsresistenz verursachen (EPA 309862, EPA0464461 ), gentechnisch veränderte Pflanzen mit reduzierter Photorespiration, die höhere Erträge und höhere Stresstoleranz aufweisen (EPA 0305398), Transgene Kulturpflanzen, die pharmazeutisch oder diagnostisch wichtige Proteine produzieren („molecular pharming"), transgene Kulturpflanzen, die sich durch höhere Erträge oder bessere Qualität auszeichnen, transgene Kulturpflanzen die sich durch eine Kombinationen z. B. der o. g. neuen Eigenschaften auszeichnen („gene stacking").Disease resistance (EPA 309862, EPA0464461), genetically modified plants with reduced photorespiration, which have higher yields and higher stress tolerance (EPA 0305398), transgenic crops that produce pharmaceutically or diagnostically important proteins ("molecular pharming"), transgenic crops that are characterized by higher yields or better quality, transgenic crops characterized by a combination z. B. the above-mentioned new properties ("gene stacking").
Zahlreiche molekularbiologische Techniken, mit denen neue transgene Pflanzen mit veränderten Eigenschaften hergestellt werden können, sind dem Prinzip nach bekannt; siehe z. B. I. Potrykus und G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, oder Christou, "Trends in Plant Science" 1 (1996) 423-431).Numerous molecular biological techniques that can be used to produce new transgenic plants with altered properties are known in principle; see, for. B. I. Potrykus and G. Spangenberg (eds.) Gene Transfer to Plants, Springer Lab Manual (1995), Springer Verlag Berlin, Heidelberg, or Christou, "Trends in Plant Science" 1 (1996) 423-431).
Für derartige gentechnische Manipulationen können Nucleinsäuremoleküle inFor such genetic manipulations, nucleic acid molecules can be used in
Plasmide eingebracht werden, die eine Mutagenese oder eine Sequenzveränderung durch Rekombination von DNA-Sequenzen erlauben. Mit Hilfe von Standardverfahren können z. B. Basenaustausche vorgenommen, Teilsequenzen entfernt oder natürliche oder synthetische Sequenzen hinzugefügt werden. Für die Verbindung der DNA-Fragmente untereinander können an die Fragmente Adaptoren oder Linker angesetzt werden, siehe z. B. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2. Aufl. CoId Spring Harbor Laboratory Press, CoId Spring Harbor, NY; oder Winnacker "Gene und Klone", VCH Weinheim 2. Auflage 1996.Plasmids are introduced which allow mutagenesis or a sequence change by recombination of DNA sequences. With the help of standard methods z. For example, base substitutions are made, partial sequences are removed, or natural or synthetic sequences are added. For the connection of the DNA fragments with one another adapters or linkers can be attached to the fragments, see, for example, US Pat. Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd ed. CoId Spring Harbor Laboratory Press, ColD Spring Harbor, NY; or Winnacker "Genes and Clones", VCH Weinheim 2nd edition 1996.
Die Herstellung von Pflanzenzellen mit einer verringerten Aktivität einesThe production of plant cells with a reduced activity of a
Genprodukts kann beispielsweise erzielt werden durch die Expression mindestens einer entsprechenden antisense-RNA, einer sense-RNA zur Erzielung eines Cosuppressionseffektes oder die Expression mindestens eines entsprechend konstruierten Ribozyms, das spezifisch Transkripte des obengenannten Genprodukts spaltet.Gene product can be obtained, for example, by the expression of at least one corresponding antisense RNA, a sense RNA to obtain a cosuppression effect or the expression of at least one appropriately engineered ribozyme which specifically cleaves transcripts of the above gene product.
Hierzu können zum einen DNA-Moleküle verwendet werden, die die gesamte codierende Sequenz eines Genprodukts einschließlich eventuell vorhandener flankierender Sequenzen umfassen, als auch DNA-Moleküle, die nur Teile der codierenden Sequenz umfassen, wobei diese Teile lang genug sein müssen, um in den Zellen einen antisense-Effekt zu bewirken. Möglich ist auch die Verwendung von DNA-Sequenzen, die einen hohen Grad an Homologie zu den codiereden Sequenzen eines Genprodukts aufweisen, aber nicht vollkommen identisch sind.For this purpose, DNA molecules may be used which comprise the entire coding sequence of a gene product, including any flanking sequences that may be present, as well as DNA molecules which comprise only parts of the coding sequence, which parts must be long enough to be present in the cells to cause an antisense effect. It is also possible to use DNA sequences that have a high degree of homology to the coding sequences of a gene product but are not completely identical.
Bei der Expression von Nucleinsäuremolekülen in Pflanzen kann das synthetisierte Protein in jedem beliebigen Kompartiment der pflanzlichen Zelle lokalisiert sein. Um aber die Lokalisation in einem bestimmten Kompartiment zu erreichen, kann z. B. die codierende Region mit DNA-Sequenzen verknüpft werden, die die Lokalisierung in einem bestimmten Kompartiment gewährleisten. Derartige Sequenzen sind dem Fachmann bekannt (siehe beispielsweise Braun et al., EMBO J. 11 (1992), 3219- 3227; Wolter et al., Proc. Natl. Acad. Sei. USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991 ), 95-106). Die Expression der Nukleinsäuremoleküle kann auch in den Organellen der Pflanzenzellen stattfinden.In the expression of nucleic acid molecules in plants, the synthesized protein may be located in any compartment of the plant cell. But to achieve the localization in a particular compartment, z. For example, the coding region can be linked to DNA sequences that ensure localization in a particular compartment. Such sequences are known to those skilled in the art (see, for example, Braun et al., EMBO J. 11 (1992), 3219-3227; Wolter et al., Proc. Natl. Acad., U.S.A. 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106). The expression of the nucleic acid molecules can also take place in the organelles of the plant cells.
Die transgenen Pflanzenzellen können nach bekannten Techniken zu ganzen Pflanzen regeneriert werden. Bei den transgenen Pflanzen kann es sich prinzipiell um Pflanzen jeder beliebigen Pflanzenspezies handeln, d.h., sowohl monokotyle als auch dikotyle Pflanzen.The transgenic plant cells can be regenerated to whole plants by known techniques. The transgenic plants may, in principle, be plants of any plant species, that is, both monocotyledonous and dicotyledonous plants.
So sind transgene Pflanzen erhältlich, die veränderte Eigenschaften durch Überexpression, Suppression oder Inhibierung homologer (= natürlicher) Gene oder Gensequenzen oder Expression heterologer (= fremder) Gene oder Gensequenzen aufweisen.Thus, transgenic plants are available which have altered properties by overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or expression of heterologous (= foreign) genes or gene sequences.
Vorzugsweise können die erfindungsgemäßen Verbindungen (I) in transgenen Kulturen eingesetzt werden, welche gegen Wuchsstoffe, wie z. B. Dicamba oder gegen Herbizide, die essentielle Pflanzenenzyme, z. B. Acetolactatsynthasen (ALS), EPSP Synthasen, Glutaminsynthasen (GS) oder Hydoxyphenylpyruvat Dioxygenasen (HPPD) hemmen, respektive gegen Herbizide aus der Gruppe der Sulfonylharnstoffe, der Glyphosate, Glufosinate oder Benzoylisoxazole und analogen Wirkstoffe, resistent sind. Bei der Anwendung der erfindungsgemäßen Wirkstoffe in transgenen Kulturen treten neben den in anderen Kulturen zu beobachtenden Wirkungen gegenüber Schadpflanzen oftmals Wirkungen auf, die für die Applikation in der jeweiligen transgenen Kultur spezifisch sind, beispielsweise ein verändertes oder speziell erweitertes Unkrautspektrum, das bekämpft werden kann, verändertePreferably, the compounds (I) according to the invention can be used in transgenic cultures which are resistant to growth substances, such as. B. Dicamba or against herbicides, the essential plant enzymes, eg. As acetolactate synthases (ALS), EPSP synthases, glutamine synthases (GS) or Hydoxyphenylpyruvat dioxygenases (HPPD) inhibit or herbicides from the group of sulfonylureas, the glyphosate, glufosinate or benzoylisoxazole and analogues, are resistant. In the application of the active compounds according to the invention in transgenic crops, in addition to the effects observed in other crops on harmful plants, effects which are specific for the application in the respective transgenic crop often occur, for example a modified or specially extended weed spectrum which can be controlled
Aufwandmengen, die für die Applikation eingesetzt werden können, vorzugsweise gute Kombinierbarkeit mit den Herbiziden, gegenüber denen die transgene Kultur resistent ist, sowie Beeinflussung von Wuchs und Ertrag der transgenen Kulturpflanzen.Application rates that can be used for the application, preferably good combinability with the herbicides to which the transgenic culture is resistant, and influencing growth and yield of the transgenic crops.
Gegenstand der Erfindung ist deshalb auch die Verwendung der erfindungsgemäßen Verbindungen der Formel I als Herbizide zur Bekämpfung von Schadpflanzen in transgenen Kulturpflanzen.The invention therefore also relates to the use of the compounds of the formula I according to the invention as herbicides for controlling harmful plants in transgenic crop plants.
Als Kombinationspartner für die erfindungsgemäßen Verbindungen inAs a combination partner for the compounds of the invention in
Mischungsformulierungen oder im Tank-Mix sind beispielsweise bekannte Wirkstoffe, die auf einer Inhibition von beispielsweise Acetolactat-Synthase, Acetyl-CoA- Carboxylase, Cellulose-Synthase, Enolpyruvylshikimat-3-phosphat-Synthase, Glutamin-Synthetase, p-Hydroxyphenylpyruvat-Dioxygenase, Phytoendesaturase, Photosystem I, Photosystem II, Protoporphyrinogen-Oxidase beruhen, einsetzbar, wie sie z.B. aus Weed Research 26 (1986) 441-445 oder "The Pesticide Manual", 13th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 und dort zitierter Literatur beschrieben sind.Mixture formulations or in the tank mix are, for example, known active ingredients which are based on an inhibition of, for example, acetolactate synthase, acetyl-CoA carboxylase, cellulose synthase, enolpyruvylshikimate-3-phosphate synthase, glutamine synthetase, p-hydroxyphenylpyruvate dioxygenase, phytoene desaturase , Photosystem I, photosystem II, protoporphyrinogen oxidase are based, can be used, such as from Weed Research 26 (1986) 441-445 or "The Pesticide Manual", 13th edition, The British Crop Protection Council and the Royal Soc. of Chemistry, 2003 and cited therein.
Als bekannte Herbizide, die mit den erfindungsgemäßen Verbindungen kombiniert werden können, sind z.B. folgende Wirkstoffe zu nennen (Anmerkung: Die Verbindungen sind entweder mit dem "common name" nach der International Organization for Standardization (ISO) oder mit einer üblichen Codenummer zusammen mit dem chemischen Namen bezeichnet) und umfassen stets sämtliche Anwendungsformen wie Säuren, Salze, Ester und Isomere wie Stereoisomere und optische Isomere. Dabei sind eine und zum Teil auch mehrere Anwendungsformen genannt: 2,4-D, Acetochlor, Acifluorfen, Acifluorfen-sodium, Aclonifen, Alachlor, Alloxydim, Alloxydim-sodium, Ametryn, Amicarbazone, Amidosulfuron, Aminopyralid, Amitrole, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, Beflubutamid, Benazolin, Benazolin-ethyl, Bencarbazone, Benfuresate, Bensulfuron-methyl, Bentazone, Benzfendizone, Benzobicyclon, Benzofenap, Bifenox, Bilanafos, Bispyribac-natrium, Bromacil, Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butafenacil, Butenachlor, Butralin, Butroxydim, Butylate, Cafenstrole, Carbetamide, Carfentrazone-ethyl, Chlomethoxyfen, Chloridazon, Chlorimuron-ethyl, Chlornitrofen, Chlorotoluron, Chlorsulfuron, Cinidon-ethyl, Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop-propargyl, Clomazone, Clomeprop, Clopyralid, Cloransulam- methyl, Cumyluron, Cyanazine, Cyclosulfamuron, Cycloxydim, Cyhalofop-butyl, Desmedipham, Dicamba, Dichlobenil, Dichlorprop, Dichlorprop-P, Diclofop-methyl, Diclosulam, Difenzoquat, Diflufenican, Diflufenzopyr, Dikegulac-sodium, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Triaziflam, Diquat- dibromide, Dithiopyr, Diuron, Dymron, EPTC, Esprocarb, Ethalfluralin,Examples of known herbicides which can be combined with the compounds according to the invention are the following active substances (note: the compounds are either with the "common name" according to the International Organization for Standardization (ISO) or with a common code number together with the chemical Names) and always include all forms of use such as acids, salts, esters and isomers such as stereoisomers and optical isomers. One and in part also several application forms are mentioned: 2,4-D, acetochlor, acifluorfen, acifluorfen-sodium, aclonifen, alachlor, alloxydim, alloxydim-sodium, ametryn, amicarbazone, amidosulfuron, aminopyralid, amitrole, anilofos, asulam, atrazine, azafenidine, azimsulfuron, beflubutamide, benazoline, benazoline ethyl, bencarbazone, benfuresate, bensulfuron-methyl, bentazone, benzfendizone, benzobicyclone, benzofenap, bifenox, bilanafos, bispyribac sodium, bromacil, bromobutide, bromofenoxime, bromoxynil, butachlor, butafenacil, butenachlor, butraline, butroxydim, butylates, cafenstrole, carbetamides, Carfentrazone-ethyl, chlomethoxyfen, chloridazon, chlorimuron-ethyl, chlornitrofen, chlorotoluron, chlorsulfuron, cinidon-ethyl, cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop-propargyl, clomazone, clomeprop, clopyralid, cloransulam-methyl, cumyluron, cyanazine, cyclosulfamuron, Cycloxydim, cyhalofop-butyl, desmedipham, dicamba, dichlobenil, dichlorprop, dichlorprop-P, diclofop-methyl, diclosulam, difenzoquat, diflufenican, diflufenzopyr , Dikegulac-sodium, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Triaziflam, Diquatdibromide, Dithiopyr, Diuron, Dymron, EPTC, Esprocarb, Ethalfluralin,
Ethametsulfuron-methyl, Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop-ethyl, Fenoxaprop-P-ethyl, Fentrazamide, Flamprop-M-isopropyl, Flamprop-M-methyl, Flazasulfuron, Florasulam, Fluazifop, Fluazifop-butyl, Fluazifop- P-butyl, Fluazolate, Flucarbazone-sodium, Flucetosulfuron, Fluchloralin, Flufenacet, Flufenpyr, Flumetsulam, Flumiclorac-pentyl, Flumioxazin, Fluometuron,Ethametsulfuron-methyl, ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop-ethyl, fenoxaprop-P-ethyl, fentrazamide, flamprop-M-isopropyl, flamprop-M-methyl, flazasulfuron, florasulam, fluazifop, fluazifop-butyl, fluazifop- butyl, fluazolate, flucarbazone-sodium, flucetosulfuron, fluchloralin, flufenacet, flufenpyr, flumetsulam, flumiclorac-pentyl, flumioxazine, fluometuron,
Fluorochloridone, Fluoroglycofen-ethyl, Flupoxam, Flupyrsulfuron-methyl-sodium, Fluridone, Fluroxypyr, Fluroxypyr-butoxypropyl, Fluroxypyr-meptyl, Flurprimidol, Flurtamone, Fluthiacet-methyl, Fomesafen, Foramsulfuron, Glufosinate, Glufosinate- ammonium, Glyphosate, Halosulfuron-methyl, Haloxyfop, Haloxyfop-ethoxyethyl, Haloxyfop-methyl, Haloxyfop-P-methyl, Hexazinone, HOK-201 (d.h. N-(2,4- Difluorphenyl)-N-(1 -methylethyl)-5-oxo-1 -(tetrahydro-2H-pyran-2-ylmethyl)-1 ,5- dihydro-4H-1 ,2,4-triazol-4-carboxamid), IDH-100 (d.h. (5-Hydroxy-1-methyl-1 H- pyrazol-4-yl)(3,3,4-trimethyl-1 ,1-dioxido-2>3-dihydro-1-benzothiophen-5-yl)methanon), Imazamethabenz-methyl, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Indanofan, lodosulfuron-methyl-natrium, loxynil, Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Ketospiradox, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mecoprop-P, Mefenacet, Mesosulfuron-methyl, Mesotrione, Metamifop, Metamitron, Metazachlor, Methabenzthiazuron, Methyldymron, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron-methyl, Molinate, Monolinuron, MonosulfuronNaproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Pelargonie acid, Pendimethalin, Pendralin, Penoxsulam, Pentoxazone, Pethoxamid, Phenmedipham, Picloram, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron-methyl, Profluazol, Profoxydim, Prohexadione-calcium, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone-sodium, Propyzamide, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolate, Pyrazosulfuron-ethyl, Pyrazoxyfen, Pyribambenz-isopropyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridate, Pyriftalid, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac-sodium, Pyroxasulfone, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamine, Quizalofop-ethyl, Quizalofop-P- ethyl, Quizalofop-P-tefuryl, Rimsulfuron, Sethoxydim, Simazine, Simetryn, S- Metolachlor, Sulcotrione, Sulfentrazone, Sulfometuron-methyl, Sulfosate, Sulfosulfuron, SYN-523 (d.h. Ethyl-[(3-{2-chlor-4-fluor-5-[3-methyl-2,6-dioxo-4- (trifluormethyl)-3,6-dihydropyrimidin-1(2H)-yl]phenoxy}pyridin-2-yl)oxy]acetate), SYP- 249 (d.h. 1 -(Ethoxycarbonyl)2-methylprop-2-en-1 -yl-5-[2-chlor-4- (trifluormethyl)phenoxy]-2-nitrobenzolcarboxylat), Tebuthiuron, Tembotrione, Tepraloxydim, Terbuthylazine, Terbutryn, Terfuryltrione, Thenylchlor, Thiazopyr, Thiencarbazone-methyl, Thifensulfuron-methyl, Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron-methyl, Triclopyr, Tridiphane, Trifloxysulfuron, Trifluralin, Triflusulfuron-methyl und Tritosulfuron sowie die VerbindungenFluorochloridones, fluoroglycofen-ethyl, flupoxam, flupyrsulfuron-methyl-sodium, fluridone, fluroxypyr, fluroxypyr-butoxypropyl, fluroxypyr-meptyl, flurprimidol, flurtamone, fluthiacet-methyl, fomesafen, foramsulfuron, glufosinate, glufosinate-ammonium, glyphosate, halosulfuron-methyl, Haloxyfop, haloxyfopethoxyethyl, haloxyfopmethyl, haloxyfop-P-methyl, hexazinone, HOK-201 (ie N- (2,4-difluorophenyl) -N- (1-methylethyl) -5-oxo-1 - (tetrahydroxy) 2H-pyran-2-ylmethyl) -1, 5-dihydro-4H-1, 2,4-triazole-4-carboxamide), IDH-100 (ie, (5-hydroxy-1-methyl-1H-pyrazole-4 -yl) (3,3,4-trimethyl-1,1-dioxo-2 > 3-dihydro-1-benzothiophen-5-yl) -methanone), imazamethabenz-methyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron , Indanofan, lodosulfuron-methyl-sodium, loxynil, isoproturon, isouron, isoxaben, isoxachlorotole, isoxaflutole, ketospiradox, lactofen, lenacil, linuron, MCPA, mecoprop, mecoprop-P, mefenacet, mesosulfuron-methyl, mesotrione, Metamifop, Metamitron, Metazachlor, Methabenzothiazuron, Methyldymrone, Metobromuron, Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron-methyl, Molinate, Monolinuron, MonosulfuronNaproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazone, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Pelargonium acid, Pendimethalin, Pendralin, Penoxsulam, Pentoxazone, Pethoxamide, Phenmedipham, Picloram, Picolinafen, Pinoxaden, Piperophos, Pretilachlor, Primisulfuron-methyl, Profluazole, Profoxydim, Prohexadione-calcium, Prometry, Propachlor, Propanil, Propaquizafop, Propisochlor , Propoxycarbazone-sodium, Propyzamide, Prosulfocarb, Prosulfuron, Pyraclonil, Pyraflufen-ethyl, Pyrasulfotole, Pyrazolate, Pyrazosulfuron-ethyl, pyrazoxyfen, Pyribambenz-isopropyl, Pyribenzoxim, Pyributicarb, Pyridafol, Pyridate, Pyriftalid, Pyriminobac-methyl, Pyrimisulfan, Pyrithiobac-sodium , Pyroxasulfones, Pyroxsulam, Quinclorac, Quinmerac, Quinoclamine, Quizalofop-e ethyl, quizalofop-P-ethyl, quizalofop-P-tefuryl, rimsulfuron, sethoxydim, simazine, simetryn, S-metolachlor, sulcotrione, sulfentrazone, sulfometuron-methyl, sulfosate, sulfosulfuron, SYN-523 (ie ethyl - [(3- { 2-chloro-4-fluoro-5- [3-methyl-2,6-dioxo-4- (trifluoromethyl) -3,6-dihydropyrimidin-1 (2H) -yl] phenoxy} pyridin-2-yl) oxy] acetate), SYP-249 (ie 1 - (ethoxycarbonyl) 2-methylprop-2-en-1-yl-5- [2-chloro-4- (trifluoromethyl) phenoxy] -2-nitrobenzenecarboxylate), tebuthiuron, tembotrione, tepraloxydim , Terbuthylazine, terbutryn, terfuryltrione, thenylchloro, thiazopyr, thiencarbazone-methyl, thifensulfuron-methyl, thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron-methyl, triclopyr, tridiphane, trifloxysulfuron, trifluralin, triflusulfuron-methyl and tritosulfuron and the compounds
Figure imgf000043_0001
Aminocyclopyrachlor, Saflufenacil, Indaziflam, Methiozolin, Ipfencarbazone, Fenoxasulfone, Bicyclopyrone, Propyrisulfuron und Metazosulfuron.
Figure imgf000043_0001
Aminocyclopyrachlor, saflufenacil, indaziflam, methiozoline, iepcarbazone, fenoxasulfone, bicyclopyrone, propyrisulfuron and metazosulfuron.
Mischungsformulierungen erfindungsgemäßer Verbindungen der allgemeinen Formel (I) können auch Fungizide und/oder Insektizide enthalten.Mixture formulations of compounds of the general formula (I) according to the invention may also contain fungicides and / or insecticides.
Von besonderem Interesse ist die selektive Bekämpfung von Schadpflanzen in Kulturen von Nutz- und Zierpflanzen. Obwohl die erfindungsgemäßen Verbindungen der allgemeinen Formel (I) bereits in vielen Kulturen sehr gute bis ausreichende Selektivität aufweisen, können prinzipiell in einigen Kulturen und vor allem auch im Falle von Mischungen mit anderen Herbiziden, die weniger selektiv sind, Phytotoxizitäten an den Kulturpflanzen auftreten.Of particular interest is the selective control of harmful plants in crops of commercial and ornamental plants. Although the compounds of the general formula (I) according to the invention already have very good to sufficient selectivity in many cultures, phytotoxicities can in principle occur in the crop plants in some crops and, above all, in the case of mixtures with other herbicides which are less selective.
Diesbezüglich sind Kombinationen erfindungsgemäßer Verbindungen der allgemeinen Formel (I) von besonderem Interesse, welche Verbindungen der allgemeinen Formel (I) bzw. deren Kombinationen mit anderen Herbiziden oder Pestiziden und Safenern enthalten.In this connection, combinations of compounds of the general formula (I) according to the invention which contain compounds of the general formula (I) or their combinations with other herbicides or pesticides and safeners are of particular interest.
Die Safener, welche mit einem antidotisch wirksamen Gehalt eingesetzt werden, reduzieren die phytotoxischen Nebenwirkungen der eingesetzten Herbizide bzw. Herbizid-Pestizid-Kombinationen, z.B. in wirtschaftlich bedeutenden Kulturen wie Getreide ( Weizen, Gerste, Roggen, Mais, Reis, Hirse), Zuckerrübe, Zuckerrohr, Raps, Baumwolle und Soja, vorzugsweise Getreide.The safeners used with an antidote effective content reduce the phytotoxic side effects of the herbicides or herbicide / pesticide combinations used, e.g. in economically important crops such as cereals (wheat, barley, rye, corn, rice, millet), sugar beet, sugar cane, oilseed rape, cotton and soybeans, preferably cereals.
Das Mischungsverhältnis von Herbizid(mischung) zu Safener hängt im allgemeinen von der Aufwandmenge an Herbizid und der Wirksamkeit des jeweiligen Safeners ab und kann innerhalb weiter Grenzen variieren.The mixing ratio of herbicide (mixture) to safener generally depends on the application rate of herbicide and the effectiveness of the particular safener and can vary within wide limits.
So liegt das Verhältnis bespielsweise im Bereich von 200:1 bis 1 :200, vorzugsweise im Bereich von 100:1 bis 1 :100, insbesondere im Bereich von 20:1 bis 1 :20. Die Safener können analog zu den Verbindungen der allgemeinen Formel I oder deren Mischungen mit weiteren Herbiziden bzw. Pestiziden formuliert werden und als Fertigformulierung oder Tankmischung mit den Herbiziden bereitgestellt und angewendet werden.For example, the ratio is in the range from 200: 1 to 1: 200, preferably in the range from 100: 1 to 1: 100, in particular in the range from 20: 1 to 1:20. The safeners can be formulated analogously to the compounds of general formula I or mixtures thereof with further herbicides or pesticides and as Ready-made formulation or tank mix with the herbicides are provided and used.
Zur Anwendung werden die in handelsüblicher Form vorliegenden Formulierungen gegebenenfalls in üblicher Weise verdünnt z.B. bei Spritzpulvern, emulgierbaren Konzentraten, Dispersionen und wasserdispergierbaren Granulaten mittels Wasser. Staubförmige Zubereitungen, Boden- und Streugranulate sowie versprühbare Lösungen werden vor der Anwendung üblicherweise nicht mehr mit weiteren, inerten Stoffen verdünnt.For use, the formulations present in commercial form are optionally diluted in a customary manner, e.g. for wettable powders, emulsifiable concentrates, dispersions and water-dispersible granules by means of water. Dust-form preparations, soil and spreading granulates and sprayable solutions are usually no longer diluted with further inert substances before use.
Mit den äußeren Bedingungen wie Temperatur, Feutigkeit, der Art des verwendeten Herbizids u. a. variiert die erforderliche Aufwandmenge der Verbindungen der Formel I. Sie kann deshalb innerhalb weiter Grenzen schwanken, z. B. zwischen 0,001 und 10,000 kg/ha oder mehr Aktivsubstanz, vorzugsweise liegt sie jedoch zwischen 0,005 und 5,000 kg/ha.With the external conditions such as temperature, solubility, the type of herbicide u. a. varies the required application rate of the compounds of formula I. It can therefore vary within wide limits, z. Between 0.001 and 10,000 kg / ha or more of active substance, but is preferably between 0.005 and 5.000 kg / ha.
Gegenstand der Erfindung ist außerdem ein Verfahren zur Bekämpfung von tierischen Schädlingen, insbesondere von Insekten unter Verwendung der erfindungsgemäßen Verbindungen und Zusammensetzungen.The invention furthermore relates to a method for controlling animal pests, in particular insects, using the compounds according to the invention and compositions.
Zu den tierischen Schädlingen gehören:Animal pests include:
Aus der Ordnung der Anoplura (Phthiraptera), z.B. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp..From the order of the Anoplura (Phthiraptera), e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
Aus der Klasse der Arachnida z.B. 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., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici. Aus der Klasse der Bivalva z.B. Dreissena spp.. Aus der Ordnung der Chilopoda z.B. Geophilus spp., Scutigera spp.. Aus der Ordnung der Coleoptera z.B. Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptino- tarsa decemlineata, Lissorhoptrus oryzophilus, Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Sternechus spp., Symphyletes spp., Tenebrio molitor, Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp.. Aus der Ordnung der Collembola z.B. Onychiurus armatus. Aus der Ordnung der Dermaptera z.B. Forficula auricularia. Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus. Aus der Ordnung der Diptera z.B. 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., Hyppo- bosca spp., Hypoderma spp., Liriomyza spp.. Lucilia spp., Musca spp., Nezara spp., Oestrus spp., Oscinella frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp.. Aus der Klasse der Gastropoda z.B. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.. Aus der Klasse der Helminthen z.B. Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, 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., Hymeno- lepis nana, Hyostrongulus spp., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp, Strongyloides fuellebomi, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.From the class of the Arachnida eg 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., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp , Rhipicephalus spp., Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici. From the class of the Bivalva eg Dreissena spp .. From the order of the Chilopoda eg Geophilus spp., Scutigera spp .. From the order of the Coleoptera eg Acanthoscelides obtectus, Adoretus spp., Agelastica alni, Agriotes spp., Amphimallon solstitialis, Anobium punctatum, Anoplophora spp., Anthonomus spp., Anthrenus spp., Apogonia spp., Atomaria spp., Attagenus spp., Bruchidius obtectus, Bruchus spp., Ceuthorhynchus spp., Cleonus mendicus, Conoderus spp., Cosmopolites spp., Costelytra zealandica, Curculio Spp., Cryptorhynchus lapathi, Dermestes spp., Diabrotica spp., Epilachna spp., Faustinus cubae, Gibbium psylloides, Heteronychus arator, Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypothenemus spp., Lachnosterna consanguinea, Leptino-tarsa decemlineata, Lissorhoptrus oryzophilus , Lixus spp., Lyctus spp., Meligethes aeneus, Melolontha melolontha, Migdolus spp., Monochamus spp., Naupactus xanthographus, Niptus hololeucus, Oryctes rhinoceros, Oryzaephilus surinamensis, Otiorrhynchus sulcatus, Oxycetonia jucunda, Phaedon cochleariae, Phyllophaga spp., Popillia japonica, Premnotrypes spp., Psylliodes chrysocephala, Ptinus spp., Rhizobius ventralis, Rhizopertha dominica, Sitophilus spp., Sphenophorus spp., Starchus spp., Symphyletes spp., Tenebrio molitor , Tribolium spp., Trogoderma spp., Tychius spp., Xylotrechus spp., Zabrus spp. From the order of Collembola eg Onychiurus armatus. From the order of the Dermaptera eg Forficula auricularia. From the order of Diplopoda eg Blaniulus guttulatus. From the order of Diptera eg 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 frit, Pegomyia hyoscyami, Phorbia spp., Stomoxys spp., Tabanus spp., Tannia spp., Tipula paludosa, Wohlfahrtia spp .. From the class of Gastropoda eg Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp. From the genus of helminths, eg, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, 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., Loa Loa, Nematodirus spp., Oesophagostomum spp., Opisthorchis spp., Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosomen spp, Strongyloides fuellebomi, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis, Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti.
Weiterhin lassen sich Protozoen, wie Eimeria, bekämpfen.Furthermore, protozoa, such as Eimeria, can be combated.
Aus der Ordnung der Heteroptera z.B. Anasa tristis, Antestiopsis spp., Blissus spp.,From the order of Heteroptera, e.g. Anasa tristis, Antestiopsis spp., Blissus spp.,
Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., 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..Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Euschistus spp., Eurygaster spp., 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.
Aus der Ordnung der Homoptera z.B. Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp., Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp.,From the order of Homoptera e.g. Acyrthosipon spp., Aeneolamia spp., Agonoscena spp., Aleurodes spp., Aleurolobus barodensis, Aleurothrixus spp., Amrasca spp., Anuraphis cardui, Aonidiella spp., Aphanostigma piri, Aphis spp., Arboridia apicalis, Aspidiella spp., Aspidiotus spp , Atanus spp., Aulacorthum solani, Bemisia spp., Brachycaudus helichrysii, Brachycolus spp., Brevicoryne brassicae, Calligypona marginata, Carneocephala fulgida, Ceratovacuna lanigera, Cercopidae, Ceroplastes spp., Chaetosiphon fragaefolii, Chionaspis tegalensis, Chlorita onukii, Chromaphis juglandicola, Chrysomphalus ficus, Cicadulina mbila, Coccomytilus halli, Coccus spp., Cryptomyzus ribis, Dalbulus spp., Dialeurodes spp., Diaphorina spp., Diaspis spp., Doralis spp., Drosicha spp., Dysaphis spp., Dysmicoccus spp.
Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp., Proto- pulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Sticto- cephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii.. Aus der Ordnung der Hymenoptera z.B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp..Empoasca spp., Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fimbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp , Nilaparvata lugens, Oncometopia spp., Orthezia praelonga, Parabemisia myricae, Paratrioza spp., Parlatoria spp., Pemphigus spp., Peregrinus maidis, Phenacoccus spp., Phloeomyzus passerinii, Phorodon humuli, Phylloxera spp., Pinnaspis aspidistrae, Planococcus spp. , Protulvinaria pyriformis, Pseudaulacaspis pentagona, Pseudococcus spp., Psylla spp., Pteromalus spp., Pyrilla spp., Quadraspidiotus spp., Quesada gigas, Rastrococcus spp., Rhopalosiphum spp., Saissetia spp., Scaphoides titanus, Schizaphis graminum, Selenaspidus articulatus, Sogata spp., Sogatella furcifera, Sogatodes spp., Stictocephala festina, Tenalaphara malayensis, Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurod es vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii .. From the order of Hymenoptera eg Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
Aus der Ordnung der Isopoda z.B. Armadillidium vulgäre, Oniscus asellus, Porcellio scaber. Aus der Ordnung der Isoptera z.B. Reticulitermes spp., Odontotermes spp.. Aus der Ordnung der Lepidoptera z.B. Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thur- beriella, Bupalus piniarius, Cacoecia podana, Capua reticulana, Carpocapsa pomo- nella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambi- guella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp., Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma spp., Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae, Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylo- stella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp..From the order of the Isopoda eg Armadillidium vulgare, Oniscus asellus, Porcellio scaber. From the order of the Isoptera eg Reticulitermes spp., Odontotermes spp. From the order of the Lepidoptera eg Acronicta major, Aedia leucomelas, Agrotis spp., Alabama argillacea, Anticarsia spp., Barathra brassicae, Bucculatrix thurberiella, Bupalus piniarius, Cacoecia podana , Capua reticulana, Carpocapsa pomo- nella, Cheimatobia brumata, Chilo spp., Choristoneura fumiferana, Clysia ambigella, Cnaphalocerus spp., Earias insulana, Ephestia kuehniella, Euproctis chrysorrhoea, Euxoa spp., Feltia spp., Galleria mellonella, Helicoverpa spp , Heliothis spp., Hofmannophila pseudospretella, Homona magnanima, Hyponomeuta padella, Laphygma spp., Lithocolletis blancardella, Lithophane antennata, Loxagrotis albicosta, Lymantria spp., Malacosoma neustria, Mamestra brassicae, Mocis repanda, Mythimna separata, Oria spp., Oulema oryzae , Panolis flammea, Pectinophora gossypiella, Phyllocnistis citrella, Pieris spp., Plutella xylostella, Prodenia spp., Pseudaletia spp., Pseudoplusia includens, Pyra sta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.
Aus der Ordnung der Orthoptera z.B. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.From the order of Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
Aus der Ordnung der Siphonaptera z.B. Ceratophyllus spp., Xenopsylla cheopis. Aus der Ordnung der Symphyla z.B. Scutigerella immaculata. Aus der Ordnung der Thysanoptera z.B. Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.. Aus der Ordnung der Thysanura z.B. Lepisma saccharina.From the order of siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis. From the order of Symphyla e.g. Scutigerella immaculata. From the order of Thysanoptera e.g. Baliothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Kakothrips spp., Rhipiphorothrips cruentatus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp. From the order of Thysanura e.g. Lepisma saccharina.
Zu den pflanzenparasitären Nematoden gehören z.B. Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus 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..The plant parasitic nematodes include e.g. Anguina spp., Aphelenchoides spp., Belonoaimus spp., Bursaphelenchus spp., Ditylenchus 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.
Um die gewünschte Wirkung im Pflanzenschutz zu erzielen, werden im Allgemeinen Pflanzen und Pflanzenteile mit den erfindungsgemäßen Verbindungen, d.h. Wirkstoffen und Zusammensetzungen direkt oder durch Einwirkung auf deren Umgebung, Lebensraum oder Lagerraum nach den üblichen Behandlungsmethoden, z.B. durch Tauchen, (Ver-)Spritzen, (Ver-)Sprühen, Berieseln, Verdampfen, Zerstäuben, Vernebeln, (Ver-)Streuen, Verschäumen, Bestreichen, Verstreichen, GießenIn order to achieve the desired effect in crop protection, plants and plant parts are generally treated with the compounds according to the invention, i. Active ingredients and compositions directly or by affecting their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, (spraying), (spraying), sprinkling, evaporating, atomizing, misting, (ver) spreading, foaming, brushing, spreading, pouring
(drenchen), Tröpfchenbewässerung und bei Vermehrungsmaterial, insbesondere bei Saatgut, weiterhin durch Trockenbeizen, Nassbeizen, Schlämmbeizen, Inkrustieren, ein- oder mehrschichtiges Umhüllen usw. behandelt. Es ist ferner möglich, die Wirkstoffe nach dem Ultra-Low-Volume-Verfahren auszubringen oder die Wirkstoff- Zubereitung oder den Wirkstoff selbst in den Boden zu injizieren.(Drenchen), drip irrigation and propagating material, especially in seeds, further treated by dry pickling, wet pickling, slurry pickling, encrusting, single or multi-layer wrapping, etc. It is also possible to apply the active ingredients by the ultra-low-volume method or to inject the active ingredient preparation or the active ingredient itself into the soil.
Eine bevorzugte direkte Behandlung der Pflanzen ist die Blattapplikation, d.h. erfindungsgemäße Wirkstoffe, Wirkstoffkombinationen bzw. Zusammensetzungen werden auf das Blattwerk aufgebracht, wobei die Behandlungsfrequenz und die Aufwandmenge auf den Befallsdruck des jeweiligen Pathogens, Insekts, Unkrauts abgestimmt ist.A preferred direct treatment of the plants is foliar application, ie active compounds according to the invention, combinations of active substances or compositions are applied to the foliage, the frequency of treatment and the rate of application is adapted to the infestation pressure of the respective pathogen, insect, weed.
Bei systemisch wirksamen Verbindungen gelangen die erfindungsgemäßenIn the case of systemically active compounds, the inventive compounds
Wirkstoffe, Wirkstoffkombinationen bzw. Zusammensetzungen über das Wurzelwerk in die Pflanzen. Die Behandlung der Pflanzen erfolgt dann durch Einwirkung der erfindungsgemäßen Wirkstoffe, Wirkstoffkombinationen bzw. Zusammensetzungen auf den Lebensraum der Pflanze. Das kann beispielsweise durch Drenchen sein, d.h. der Standort der Pflanze (z.B. Boden oder hydroponische Systeme) wird mit einer flüssigen Form der erfindungsgemäßen Wirkstoffe, Wirkstoffkombinationen bzw. Zusammensetzungen getränkt, oder durch die Bodenapplikation, d.h. die erfindungsgemäßen Wirkstoffe, Wirkstoffkombinationen bzw. Zusammensetzungen werden in fester Form, (z.B. in Form eines Granulats) in den Standort der Pflanzen eingebracht. Bei Wasserreiskulturen kann das auch durch Zudosieren der Erfindung in einer festen Anwendungsform (z.B. als Granulat) in ein überflutetes Reisfeld sein.Active ingredients, active ingredient combinations or compositions via the root system in the plants. The treatment of the plants is then carried out by the action of the active compounds according to the invention, active ingredient combinations or compositions on the habitat of the plant. This may be, for example, Drenchen, i. the location of the plant (e.g., soil or hydroponic systems) is soaked in a liquid form of the active compounds, drug combinations, or compositions of the invention, or by the soil application, i. the active compounds, active ingredient combinations or compositions according to the invention are introduced in solid form (for example in the form of granules) into the location of the plants. In water rice crops this may also be by metering the invention in a solid application form (e.g., as granules) into a flooded paddy field.
Unter Pflanzen werden alle Pflanzenarten, Pflanzensorten und Pflanzenpopulationen, wie erwünschte und unerwünschte Wildpflanzen oder Kulturpflanzen verstanden. Erfindungsgemäß zu behandelnde Kulturpflanzen sind Pflanzen, die natürlich vorkommen, oder solche, die durch konventionelle Züchtungs- und Optimierungsmethoden oder durch biotechnologische und gentechnologische Methoden oder durch Kombinationen der vorgenannten Methoden erhalten wurden. Der Begriff Kulturpflanze umfasst selbstverständlich auch transgene Pflanzen.By plants are meant all plant species, plant varieties and plant populations, such as desirable and undesirable wild plants or crop plants. Crop plants to be treated according to the invention are plants which occur naturally or those which have been obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or by combinations of the abovementioned methods. Of course, the term crop also includes transgenic plants.
Unter Pflanzensorten versteht man Pflanzen mit neuen Eigenschaften, sogenannten Traits, die sowohl durch konventionelle Züchtung, durch Mutagenese oder durch rekombinante DNA-Techniken oder einer Kombination hieraus gezüchtet worden sind. Dies können Sorten, Rassen, Bio- und Genotypen sein.Plant varieties are understood as meaning plants having new properties, so-called traits, which have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques or a combination thereof. These may be varieties, breeds, biotypes and genotypes.
Unter Pflanzenteile werden alle oberirdischen und unterirdischen Teile und Organe der Pflanzen, wie Spross, Blatt, Blüte und Wurzel verstanden, insbesondere Blätter, Nadeln, Stängel, Stämme, Blüten, Fruchtkörper, Früchte, Samen, Wurzeln, Knollen und Rhizome. Der Begriff Pflanzenteile umfasst weiterhin Erntegut sowie vegetatives und generatives Vermehrungsmaterial, wie z.B. Stecklinge, Knollen, Rhizome, Ableger und Samen bzw. Saatgut.Plant parts are understood to mean all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, in particular leaves, Needles, stems, stems, flowers, fruiting bodies, fruits, seeds, roots, tubers and rhizomes. The term plant parts further includes crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds or seeds.
In einer erfindungsgemäßen Ausführungsform werden natürlich vorkommende oder durch konventionelle Züchtungs- und Optimierungsmethoden (z.B. Kreuzung oder Protoplastenfusion) erhaltene Pflanzenarten und Pflanzensorten sowie deren Pflanzenteile behandelt.In one embodiment of the invention, naturally occurring or plant species and plant cultivars obtained by conventional breeding and optimization methods (e.g., crossing or protoplast fusion) and plant parts thereof are treated.
In einer weiteren erfindungsgemäßen Ausführungsform werden transgene Pflanzen, die durch gentechnologische Methoden gegebenenfalls in Kombination mit konventionellen Methoden erhalten wurden und deren Teile behandelt.In a further embodiment according to the invention, transgenic plants which have been obtained by genetic engineering, if appropriate in combination with conventional methods, and their parts are treated.
Die vorliegende Erfindung bezieht sich weiterhin auf ein Verfahren zum Schutz von Saatgut und keimenden Pflanzen vor dem Befall von Schädlingen, indem das Saatgut mit erfindungsgemäßen Verbindungen oder Zusammensetzungen behandelt wird.The present invention further relates to a method of protecting seeds and germinating plants from attack by pests by treating the seeds with compounds or compositions of the invention.
Die Erfindung bezieht sich ebenfalls auf die Verwendung der erfindungsgemäßen Verbindungen oder Zusammensetzungen zur Behandlung von Saatgut zum Schutz des Saatguts und der daraus entstehenden Pflanze vor Schädlingen. Weiterhin bezieht sich die Erfindung auf Saatgut, welches zum Schutz vor Schädlingen mit erfindungsgemäßen Verbindungen oder Zusammensetzungen behandelt wurde. Einer der Vorteile der vorliegenden Erfindung ist es, dass aufgrund der besonderen systemischen Eigenschaften der erfindungsgemäßen Verbindungen oder Zusammensetzungen die Behandlung des Saatguts mit diesen Verbindungen oder Zusammensetzungen nicht nur das Saatgut selbst, sondern auch die daraus hervorgehenden Pflanzen nach dem Auflaufen vor Schädlingen schützt. Auf diese Weise kann die unmittelbare Behandlung der Kultur zum Zeitpunkt der Aussaat oder kurz danach entfallen. Ebenso ist es als vorteilhaft anzusehen, dass die erfindungsgemäßen Verbindungen oder Zusammensetzungen insbesondere auch bei transgenem Saatgut eingesetzt werden können, wobei die aus diesem Saatgut hervorgehenden Pflanzen zur Expression eines gegen Schädlinge gerichteten Proteins befähigt sind. Durch die Behandlung solchen Saatguts mit den erfindungsgemäßen Verbindungen oder Zusammensetzungen können bestimmte Schädlinge bereits durch die Expression des z.B. insektiziden Proteins kontrolliert werden, und zusätzlich durch die erfindungsgemäßen Wirkstoffkombinationen vor Schäden bewahrt werden.The invention also relates to the use of the compounds or compositions according to the invention for the treatment of seed for the protection of the seed and the resulting plant from pests. Furthermore, the invention relates to seed which has been treated for protection against pests with compounds or compositions according to the invention. One of the advantages of the present invention is that because of the particular systemic properties of the compounds or compositions of the present invention, treatment of the seed with these compounds or compositions protects not only the seed itself but also the resulting plants from pests after emergence. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted. Likewise, it is to be regarded as advantageous that the compounds or compositions according to the invention can also be used in particular in the case of transgenic seed, wherein the plants resulting from this seed are capable of expressing a protein directed against pests. By treating such seeds with the compounds or compositions according to the invention, certain pests can already be controlled by the expression of the insecticidal protein, for example, and additionally protected against damage by the active compound combinations according to the invention.
Die erfindungsgemäßen Verbindungen oder Zusammensetzungen eignen sich zum Schutz von Saatgut jeglicher Pflanzensorte wie bereits vorstehend genannt, die in der Landwirtschaft, im Gewächshaus, in Forsten oder im Gartenbau eingesetzt wird. Insbesondere handelt es sich dabei um Saatgut von Mais, Erdnuss, Canola, Raps, Mohn, Soja, Baumwolle, Rübe (z.B. Zuckerrübe und Futterrübe), Reis, Hirse, Weizen, Gerste, Hafer, Roggen, Sonnenblume, Tabak, Kartoffeln oder Gemüse (z.B. Tomaten, Kohlgewächs). Die erfindungsgemäßen Verbindungen oder Zusammensetzungen eignen sich ebenfalls zur Behandlung des Saatguts von Obstpflanzen und Gemüse wie vorstehend bereits genannt. Besondere Bedeutung kommt der Behandlung des Saatguts von Mais, Soja, Baumwolle, Weizen und Canola oder Raps zu.The compounds or compositions according to the invention are suitable for the protection of seed of any plant variety as mentioned above, which is used in agriculture, in the greenhouse, in forests or in horticulture. In particular, these are corn, peanut, canola, rapeseed, poppy, soybean, cotton, turnip (eg sugarbeet and fodder beet), rice, millet, wheat, barley, oats, rye, sunflower, tobacco, potatoes or vegetables ( eg tomatoes, cabbage). The compounds or compositions according to the invention are likewise suitable for the treatment of the seed of fruit plants and vegetables as already mentioned above. Of particular importance is the treatment of the seeds of maize, soya, cotton, wheat and canola or rapeseed.
Wie vorstehend bereits erwähnt, kommt auch der Behandlung von transgenem Saatgut mit erfindungsgemäßen Verbindungen oder Zusammensetzungen eine besondere Bedeutung zu. Dabei handelt es sich um das Saatgut von Pflanzen, die in der Regel zumindest ein heterologes Gen enthalten, das die Expression eines Polypeptids mit insbesondere insektiziden Eigenschaften steuert. Die heterologen Gene in transgenem Saatgut können dabei aus Mikroorganismen wie Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus oder Gliocladium stammen. Die vorliegende Erfindung eignet sich besonders für die Behandlung von transgenem Saatgut, das zumindest ein heterologes Gen enthält, das aus Bacillus sp. stammt und dessen Genprodukt Wirksamkeit gegen Maiszünsler und/oder Maiswurzel-Bohrer zeigt. Besonders bevorzugt handelt es sich dabei um ein heterologes Gen, das aus Bacillus thuringiensis stammt.As already mentioned above, the treatment of transgenic seed with compounds or compositions according to the invention is of particular importance. These are the seeds of plants, which as a rule contain at least one heterologous gene which controls the expression of a polypeptide with in particular insecticidal properties. The heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium. The present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. and its gene product activity against European corn borer and / or corn rootworm shows. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
Zu den bevorzugten erfindungsgemäß zu behandelnden transgenen Pflanzen bzw. Pflanzensorten gehören alle Pflanzen, die durch die gentechnologische Modifikation genetisches Material erhielten, welches diesen Pflanzen besondere vorteilhafte wertvolle Eigenschaften („Traits") verleiht. Beispiele für solche Eigenschaften sind besseres Pflanzenwachstum, erhöhte Toleranz gegenüber hohen oder niedrigen Temperaturen, erhöhte Toleranz gegen Trockenheit oder gegen Wasser- bzw. Bodensalzgehalt, erhöhte Blühleistung, erleichterte Ernte, Beschleunigung der Reife, höhere Ernteerträge, höhere Qualität und/oder höherer Ernährungswert der Ernteprodukte, höhere Lagerfähigkeit und/oder Bearbeitbarkeit der Ernteprodukte. Weitere und besonders hervorgehobene Beispiele für solche Eigenschaften sind eine erhöhte Abwehr der Pflanzen gegen tierische und mikrobielle Schädlinge, wie gegenüber Insekten, Milben, pflanzenpathogenen Pilzen, Bakterien und/oder Viren sowie eine erhöhte Toleranz der Pflanzen gegen bestimmte herbizide Wirkstoffe. Als Beispiele transgener Pflanzen werden die wichtigen Kulturpflanzen, wie Getreide (Weizen, Reis), Mais, Soja, Kartoffel, Baumwolle, Tabak, Raps sowie Obstpflanzen (mit den Früchten Äpfel, Birnen, Zitrusfrüchten und Weintrauben) erwähnt, wobei Mais, Soja, Kartoffel, Baumwolle, Tabak und Raps besonders hervorgehoben werden. Als Eigenschaften („Traits") werden besonders hervorgehoben die erhöhte Abwehr der Pflanzen gegen Insekten, Spinnentiere, Nematoden und Schnecken durch in den Pflanzen entstehende Toxine, insbesondere solche, die durch das genetische Material aus Bacillus thuringiensis (z.B. durch die Gene CrylA(a), CrylA(b), CrylA(c), CryllA, CrylllA, CrylllB2, Cry9c Cry2Ab, Cry3Bb und CrylF sowie deren Kombinationen) in den Pflanzen erzeugt werden (im Folgenden „Bt Pflanzen"). Als Eigenschaften („Traits") werden auch besonders hervorgehoben die erhöhte Abwehr von Pflanzen gegen Pilze, Bakterien und Viren durch Systemische Akquirierte Resistenz (SAR), Systemin, Phytoalexine, Elicitoren sowie Resistenzgene und entsprechend exprimierte Proteine und Toxine. Als Eigenschaften („Traits") werden weiterhin besonders hervorgehoben die erhöhte Toleranz der Pflanzen gegenüber bestimmten herbiziden Wirkstoffen, z.B. Imidazolinonen, Sulfonylharnstoffen, Glyphosate oder Phosphinotricin (z.B. "PAT"-Gen). Die jeweils die gewünschten Eigenschaften („Traits") verleihenden Gene können auch in Kombinationen miteinander in den transgenen Pflanzen vorkommen. Als Beispiele für „Bt Pflanzen" seien Maissorten, Baumwollsorten, Sojasorten und Kartoffelsorten genannt, die unter den Handelsbezeichnungen YIELD GARD® (z.B. Mais, Baumwolle, Soja), KnockOut® (z.B. Mais), StarLink® (z.B. Mais), Bollgard® (Baumwolle), Nucoton® (Baumwolle) und NewLeaf® (Kartoffel) vertrieben werden. Als Beispiele für Herbizid tolerante Pflanzen seien Maissorten, Baumwollsorten und Sojasorten genannt, die unter den Handelsbezeichnungen Roundup Ready® (Toleranz gegen Glyphosate z.B. Mais, Baumwolle, Soja), Liberty Link® (Toleranz gegen Phosphinotricin, z.B. Raps), IMICB) (Toleranz gegen Imidazolinone) und STS® (Toleranz gegen Sulfonylharnstoffe z.B. Mais) vertrieben werden. Als Herbizid resistente (konventionell auf Herbizid-Toleranz gezüchtete) Pflanzen seien auch die unter der Bezeichnung Clearfield® vertriebenen Sorten (z.B. Mais) erwähnt. Selbst- verständlich gelten diese Aussagen auch für in der Zukunft entwickelte bzw. zukünftig auf den Markt kommende Pflanzensorten mit diesen oder zukünftig entwickelten genetischen Eigenschaften („Traits"). Neben der Verwendung der erfindungsgemäßen Verbindungen oder Zusammensetzungen im Pflanzenschutz, insbesondere zur Bekämpfung einer Vielzahl verschiedener Schädlinge einschließlich beispielsweise schädlicher saugender Insekten, beißender Insekten und anderen an Pflanzen parasitierenden Schädlingen, können die erfindungsgemäßen Verbindungen oder Zusammensetzungen, wie oben erwähnt, zur Bekämpfung von Vorratsschädlingen, Schädlingen, die industrielle Materialien zerstören und Hygieneschädlingen, einschließlich Parasiten im Bereich Tiergesundheit verwendet werden und zu ihrer Bekämpfung, wie zum Beispiel ihrer Auslöschung und Ausmerzung eingesetzt werden. Die vorliegende Erfindung schließt somit auch ein Verfahren zur Bekämpfung von Schädlingen ein.The preferred transgenic plants or plant cultivars to be treated according to the invention include all plants which have obtained genetic material by the genetic engineering modification which gives these plants particularly advantageous valuable properties ("traits") .Examples of such properties are better plant growth, increased tolerance to high or lower temperatures, increased tolerance to dryness or to bottoms salt, increased flowering efficiency, 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 Particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses and increased tolerance the plants against certain herbicidal active ingredients. Examples of transgenic plants include the important crops such as cereals (wheat, rice), corn, soybean, potato, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybean, 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 formed in the plants, in particular those produced by the genetic material from Bacillus thuringiensis (eg by the genes CrylA (a) , CrylA (b), CrylA (c), CryllA, CrylllA, CrylllB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) in the plants (hereinafter "Bt plants"). Traits also highlight the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. ), the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, are particularly emphasized. Sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene). The genes conferring the desired properties ("traits") can also be present in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soybean varieties and potato varieties sold under the trade names YIELD GARD® (eg maize , Cotton, soybean), KnockOut® (eg corn), StarLink® (eg corn), Bollgard® (cotton), Nucoton® (cotton) and NewLeaf® (potato). Examples of 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), IMICB ) (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas eg corn). Herbicide-resistant (conventionally grown on herbicide tolerance) plants are also the varieties marketed under the name Clearfield® (eg corn) mentioned. Of course, these statements also apply to plant varieties developed or to be marketed in the future with these or future-developed genetic traits In addition to the use of the compounds or compositions according to the invention in crop protection, in particular for controlling a large number of different Pests, including, for example, noxious sucking insects, biting insects, and other plant parasitic pests, may be used to combat stock pests, pests which destroy industrial materials, and sanitary pests, including parasites in the animal health field, and compounds of the present invention their control, such as their extinction and eradication.The present invention thus also includes a method of controlling pests.
Die erfindungsgemäßen Verbindungen oder Zusammensetzungen können insbesondere aufgrund ihrer starken insektiziden Wirkung im Materialschutz zum Schutz von technischen Materialien gegen Befall und Zerstörung durch Insekten, wie z.B. Termiten, eingesetzt werden. Demgemäß bezieht sich die Erfindung auf die Verwendung der Wirkstoffe bzw. Zusammensetzungen zum Schutz von technischen Materialien gegen Befall oder Zerstörung durch Insekten. Zu diesen Insekten gehören z.B. Käfer wie 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. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus; Hautflügler wie Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;The compounds or compositions according to the invention can, in particular because of their strong insecticidal action in the protection of materials for the protection of industrial materials against attack and destruction by insects, such as As termites, are used. Accordingly, the invention relates to the use of the active ingredients or compositions for the protection of technical materials against attack or destruction by insects. These insects include, for example, beetles 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. Apate monachus, Bostrychus capucins, Heterobostrychus brunneus, Sinoxylon spec. Dinoderus minutus; Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
Termiten wie Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Masto- termes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus; Borstenschwänze wie Lepisma saccharina.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.
Unter technischen Materialien sind im vorliegenden Zusammenhang nichtlebende Materialien zu verstehen, wie vorzugsweise Kunststoffe, Klebstoffe, Leime, Papiere und Kartone, Leder, Holz, Holzverarbeitungsprodukte und Anstrichmittel. Die Anwendung der Erfindung zum Schutz von Holz ist besonders bevorzugt.Technical materials in the present context are to be understood as meaning non-living materials, such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints. The application of the invention for the protection of wood is particularly preferred.
Gleichfalls eignen sich die erfindungsgemäßen Verbindungen oder Zusammensetzungen zum Schutz vor Bewuchs von Gegenständen, insbesondere von Schiffskörpern, Sieben, Netzen, Bauwerken, Kaianlagen und Signalanlagen, welche mit See- oder Brackwasser in Verbindung kommen, verwendet werden können. Gleichfalls können die erfindungsgemäßen Wirkstoffe undLikewise, the compounds or compositions according to the invention are suitable for protection against fouling of objects, in particular of hulls, screens, nets, structures, quays and signal systems, which come into contact with seawater or brackish water. Likewise, the active compounds of the invention and
Zusammensetzungen allein oder in Kombinationen mit anderen Wirkstoffen als Anti- fouling-Mittel eingesetzt werden.Compositions can be used alone or in combination with other active ingredients as anti-fouling agents.
Im Hygienebereich, d.h. zur Bekämpfung von Hygieneschädlingen, werden die Verbindungen oder Zusammensetzungen bevorzugt im Haushalts-, Hygiene- und Vorratsschutz verwendet. Insbesondere zur Bekämpfung von Insekten, Spinnentieren und Milben, die in geschlossenen Räumen, wie beispielsweise Wohnungen, Fabrikhallen, Büros, Fahrzeugkabinen vorkommen. Zur Bekämpfung werden die Wirkstoffe oder Zusammensetzungen allein oder in Kombination mit anderen Wirk- und/oder Hilfsstoffen verwendet. Bevorzugt werden sie inIn the hygiene sector, ie to combat hygiene pests, the compounds or compositions are preferably used in household, hygiene and storage. In particular, for the control of insects, arachnids and mites, in enclosed spaces, such as Apartments, factories, offices, vehicle cabs happen. For control, the active compounds or compositions are used alone or in combination with other active ingredients and / or adjuvants. They are preferred in
Haushaltsinsektizid-Produkten verwendet. Die erfindungsgemäßen Wirkstoffe sind gegen sensible und resistente Arten sowie gegen alle Entwicklungsstadien wirksam.Household insecticide products used. The active compounds according to the invention are active against sensitive and resistant species as well as against all stages of development.
Zu diesen Schädlingen gehören beispielsweise:These pests include, for example:
Aus der Ordnung der Scorpionidea z.B. Buthus occitanus.From the order of Scorpionidea e.g. Buthus occitanus.
Aus der Ordnung der Acarina z.B. Argas persicus, Argas reflexus, Bryobia ssp.,From the order of Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp.,
Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis,Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis,
Dermatophagoides pteronissimus, Dermatophagoides forinae.Dermatophagoides pteronissimus, Dermatophagoides forinae.
Aus der Ordnung der Araneae z.B. Aviculariidae, Araneidae.From the order of the Araneae e.g. Aviculariidae, Araneidae.
Aus der Ordnung der Opiliones z.B. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium. Aus der Ordnung der Isopoda z.B. Oniscus asellus, Porcellio scaber.From the order of Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium. From the order of isopods e.g. Oniscus asellus, Porcellio scaber.
Aus der Ordnung der Diplopoda z.B. Blaniulus guttulatus, Polydesmus spp..From the order of diplopoda e.g. Blaniulus guttulatus, Polydesmus spp ..
Aus der Ordnung der Chilopoda z.B. Geophilus spp..From the order of Chilopoda e.g. Geophilus spp ..
Aus der Ordnung der Zygentoma z.B. Ctenolepisma spp., Lepisma saccharina,From the order of Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina,
Lepismodes inquilinus. Aus der Ordnung der Blattaria z.B. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa,Lepismodes inquilinus. From the order of the Blattaria e.g. Blatta orientalies, Blattella germanica, Blattella asahinai, Leucophaea maderae, Panchlora spp., Parcoblatta spp., Periplaneta australasiae, Periplaneta americana, Periplaneta brunnea, Periplaneta fuliginosa,
Supella longipalpa.Supple longipalpa.
Aus der Ordnung der Saltatoria z.B. Acheta domesticus. Aus der Ordnung der Dermaptera z.B. Forficula auricularia.From the order of Saltatoria e.g. Acheta domesticus. From the order of the Dermaptera e.g. Forficula auricularia.
Aus der Ordnung der Isoptera z.B. Kalotermes spp., Reticulitermes spp.From the order of Isoptera e.g. Kalotermes spp., Reticulitermes spp.
Aus der Ordnung der Psocoptera z.B. Lepinatus spp., Liposcelis spp.From the order of Psocoptera e.g. Lepinatus spp., Liposcelis spp.
Aus der Ordnung der Coleoptera z.B. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.From the order of Coleoptera e.g. Anthrenus spp., Attagenus spp., Dermestes spp., Latheticus oryzae, Necrobia spp., Ptinus spp., Rhizopertha dominica, Sitophilus granarius, Sitophilus oryzae, Sitophilus zeamais, Stegobium paniceum.
Aus der Ordnung der Diptera z.B. 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.From the order of the Diptera eg 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.
Aus der Ordnung der Lepidoptera z.B. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.From the order of Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
Aus der Ordnung der Siphonaptera z.B. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis. Aus der Ordnung der Hymenoptera z.B. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.From the order of siphonaptera e.g. Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis. From the order of Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
Aus der Ordnung der Anoplura z.B. Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix, Phthirus pubis. Aus der Ordnung der Heteroptera z.B. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.From the order of the Anoplura e.g. Pediculus humanus capitis, Pediculus humanus corporis, Pemphigus spp., Phylloera vastatrix, Phthirus pubis. From the order of Heteroptera, e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
Die Anwendung der Erfindung als Haushaltsinsektizid erfolgt allein oder in Kombination mit anderen geeigneten Wirkstoffen wie Phosphorsäureestern, Carbamaten, Pyrethroiden, Neo-nicotinoiden, Wachstumsregulatoren oder Wirkstoffen aus anderen bekannten Insektizidklassen.The application of the invention as a household insecticide is carried out alone or in combination with other suitable active ingredients such as phosphoric acid esters, carbamates, pyrethroids, neo-nicotinoids, growth regulators or agents from other known insecticide classes.
Die Anwendung erfolgt beispielsweise in Aerosolen, drucklosen Sprühmitteln, z.B. Pump- und Zerstäubersprays, Nebelautomaten, Foggern, Schäumen, Gelen, Verdampferprodukten mit Verdampferplättchen aus Cellulose oder Kunststoff, Flüssigverdampfern, Gel- und Membranverdampfern, propellergetriebenen Verdampfern, energielosen bzw. passiven Verdampfungssystemen, Mottenpapieren, Mottensäckchen und Mottengelen, als Granulate oder Stäube, in Streuködern oder Köderstationen.Application is for example in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, misting machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller driven evaporators, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
Im Bereich Tiergesundheit, d.h. auf dem veterinärmedizinischen Gebiet, wirken die Wirkstoffe gemäß der vorliegenden Erfindung gegen tierische Parasiten, insbesondere Ektoparasiten oder Endoparasiten. Der Begriff Endoparasiten schließt insbesondere Helminthen wie Cestoden, Nematoden oder Trematoden, und Protozoen wie Kozzidien ein. Ektoparasiten sind typischerweise und vorzugsweise Arthropoden, insbesondere Insekten wie Fliegen (stechend und leckend), parasitische Fliegenlarven, Läuse, Haarlinge, Federlinge, Flöhe und dergleichen; oder Akariden wie Zecken, zum Beispiel Schildzecken oder Lederzecken, oder Milben wie Räudemilben, Laufmilben, Federmilben und dergleichen. Zu diesen Parasiten gehören:In the field of animal health, ie in the veterinary field, 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 like 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:
Aus der Ordnung der Anoplurida z.B. Haematopinus spp., Linognathus spp., Pedi- culus spp., Phtirus spp., Solenopotes spp.; spezielle Beispiele sind: 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; Aus der Ordnung der Mallophagida und den Unterordnungen Amblycerina und Ischnocerina z.B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.; spezielle Beispiele sind: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; Aus der Ordnung der Diptera und den Unterordnungen Nematocerina und Brachy- cerina z.B. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia 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., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp.,From the order of the Anoplurida e.g. 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 submissions Amblycerina and Ischnocerina, for example. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; specific examples are: Bovicola bovis, Bovicola ovis, Bovicola limbata, Damalina bovis, Trichodectes canis, Felicola subrostratus, Bovicola caprae, Lepikentron ovis, Werneckiella equi; From the order of the Diptera and the suborders Nematocerina and Brachycerina, e.g. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Odagmia spp., Wilhelmia 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. Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp.,
Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp.; spezielle Beispiele sind: Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis, Haematopota italica, Musca autumnalis, Musca domestica, Haematobia irritans irritans, Haematobia irritans exigua, Haematobia Stimulans, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chloropyga, Chrysomya bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobia hominis, Melophagus ovinus, Lipoptena capreoli, Lipoptena cervi, Hippobosca variegata, Hippobosca equina, Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis, Gasterophilus nigricomis, Gasterophilus pecorum, Braula coeca;Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp., Rhinoestrus spp., Tipula spp .; specific examples are: Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles gambiae, Anopheles maculipennis, Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Fannia canicularis, Sarcophaga carnaria, Stomoxys calcitrans, Tipula paludosa, Lucilia cuprina, Lucilia sericata, Simulium reptans, Phlebotomus papatasi, Phlebotomus longipalpis, Odagmia ornata, Wilhelmia equina, Boophthora erythrocephala, Tabanus bromius, Tabanus spodopterus, Tabanus atratus, Tabanus sudeticus, Hybomitra ciurea, Chrysops caecutiens, Chrysops relictus, Haematopota pluvialis, Haematopota italica, Musca autumnalis, Musca domestica, Haematobia irritans irritans, Haematobia irritans exigua, Haematobia stimulant, Hydrotaea irritans, Hydrotaea albipuncta, Chrysomya chloropyga, Chrysomia bezziana, Oestrus ovis, Hypoderma bovis, Hypoderma lineatum, Przhevalskiana silenus, Dermatobia hominis, Melophagus ovinus, Lipoptena capreoli, Lipoptena cervi, Hippobosca variegata, Hippobosca equina, Gasterophilus intestinalis, Gasterophilus haemorroidalis, Gasterophilus inermis, Gasterophilus nasalis , Gasterophilus nigricomis, Gasterophilus pecorum, Braula coeca;
Aus der Ordnung der Siphonapterida z.B. Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp.; spezielle Beispiele sind: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; Aus der Ordnung der Heteropterida z.B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.;From the order of siphonapterida e.g. Pulex spp., Ctenocephalides spp., Tunga spp., Xenopsylla spp., Ceratophyllus spp .; specific examples are: Ctenocephalides canis, Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis; From the order of the heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp .;
Aus der Ordnung der Blattarida z.B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp. (z.B. Suppella longipalpa);From the order of Blattarida e.g. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp. (e.g., suppella longipalpa);
Aus der Unterklasse der Acari (Acarina) und den Ordnungen der Meta- und Meso- stigmata z.B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp., Haemophysalis spp.,From the subclass of Acari (Acarina) and the orders of meta- and mesostigmata, e.g. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp., Dermacentor spp., Haemophysalis spp.,
Hyalomma spp., Dermanyssus spp., Rhipicephalus spp. (der ursprünglichen Gattung der Mehrwirtszecken), Ornithonyssus spp., Pneumonyssus spp., Raillietia spp., Pneumonyssus spp., Sternostoma spp., Varroa spp., Acarapis spp.; spezielle Beispiele sind: 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 canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa, Ornithonyssus sylviarum, Varroa jacobsoni; Aus der Ordnung der Actinedida (Prostigmata) und Acaridida (Astigmata) z.B. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp., Psoroptes spp.,Hyalomma spp., Dermanyssus spp., Rhipicephalus spp. (the original genus of the multiple ticks), 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 canisuga, Ixodes pilosus, Ixodes rubicundus, Ixodes scapularis, Ixodes holocyclus, Haemaphysalis concinna, Haemaphysalis punctata, Haemaphysalis cinnabarina, Haemaphysalis otophila, Haemaphysalis leachi, Haemaphysalis longicorni, Dermacentor marginatus, Dermacentor reticulatus, Dermacentor pictus, Dermacentor albipictus, Dermacentor andersoni, Dermacentor variabilis, Hyalomma mauritanicum, Rhipicephalus sanguineus, Rhipicephalus bursa, Rhipicephalus appendiculatus, Rhipicephalus capensis, Rhipicephalus turanicus, Rhipicephalus zambeziensis, Amblyomma americanum, Amblyomma variegatum, Amblyomma maculatum, Amblyomma hebraeum, Amblyomma cajennense, Dermanyssus gallinae, Ornithonyssus bursa Ornithonyssus sylviarum, Varroa jacobsoni; From the order of Actinedida (Prostigmata) and Acaridida (Astigmata) eg Acarapis spp., Cheyletiella spp., Ornithocheyletia 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.; spezielle Beispiele sind: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri, Neoschöngastia xerothermobia, Trombicula akamushi, Otodectes cynotis, Notoedres cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae (=S. caprae), Sarcoptes equi, Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange, Pneumonyssoides caninum, Acarapis woodi. Die erfindungsgemäßen Wirkstoffe eignen sich auch zur Bekämpfung vonChorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp .; special examples are: Cheyletiella yasguri, Cheyletiella blakei, Demodex canis, Demodex bovis, Demodex ovis, Demodex caprae, Demodex equi, Demodex caballi, Demodex suis, Neotrombicula autumnalis, Neotrombicula desaleri, Neoschöngastia xerothermobia, Trombicula akamushi, Otodectes cynotis, Notoedres cati, Sarcoptis canis, Sarcoptes bovis, Sarcoptes ovis, Sarcoptes rupicaprae (= S. caprae), Sarcoptes equi, Sarcoptes suis, Psoroptes ovis, Psoroptes cuniculi, Psoroptes equi, Chorioptes bovis, Psoergates ovis, Pneumonyssoidic mange, Pneumonyssoides caninum, Acarapis woodi. The active compounds according to the invention are also suitable for controlling
Arthropoden, Helminthen und Protozoen, die Tiere befallen. Zu den Tieren zählen landwirtschaftliche Nutztiere wie z.B. Rinder, Schafe, Ziegen, Pferde, Schweine, Esel, Kamele, Büffel, Kaninchen, Hühner, Puten, Enten, Gänse, Zuchtfische, Honigbienen. Zu den Tieren zählen außerdem Haustiere - die auch als Heimtiere bezeichnet werden - wie z.B. Hunde, Katzen, Stubenvögel, Aquarienfische sowie sogenannte Versuchstiere wie z.B. Hamster, Meerschweinchen, Ratten und Mäuse. Durch die Bekämpfung dieser Arthropoden, Helminthen und/oder Protozoen sollen Todesfälle vermindert und die Leistung (bei Fleisch, Milch, Wolle, Häuten, Eiern, Honig usw.) und die Gesundheit des Wirtstieres verbessert werden, so dass durch den Einsatz der erfindungsgemäßen Wirkstoffe eine wirtschaftlichere und einfachere Tierhaltung möglich ist. So ist es beispielsweise wünschenswert, die Aufnahme von Blut des Wirts durch die Parasiten (falls zutreffend) zu verhindern oder zu unterbrechen. Eine Bekämpfung der Parasiten kann außerdem dazu beitragen, die Übertragung infektiöser Substanzen zu verhindern.Arthropods, helminths and protozoa that infest animals. The animals include farm animals such as cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, farmed fish, honey bees. The animals also include pets - which are also referred to as pets - such as dogs, cats, caged birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice. By controlling these arthropods, helminths and / or protozoa deaths should be reduced and the performance (in meat, milk, wool, hides, eggs, honey, etc.) and the health of the host animal to be improved, so that by using the active compounds of the invention more economical and easier animal husbandry is possible. For example, it is desirable to prevent or interrupt the ingestion of the host's blood by the parasites (if applicable). Control of the parasites can also help to prevent the transmission of infectious substances.
Der Begriff "Bekämpfung", so wie er hier bezogen auf den Bereich Tiergesundheit verwendet wird, bedeutet, dass die Wirkstoffe wirken, indem sie das Vorkommen des betreffenden Parasiten in einem mit solchen Parasiten befallenen Tier auf unschädliche Niveaus reduzieren. Genauer gesagt bedeutet "Bekämpfung", wie hier verwendet, dass der Wirkstoff den betreffenden Parasiten tötet, sein Wachstum hemmt oder seine Proliferation inhibiert.The term "control", as used herein in relation to animal health, 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.
Im allgemeinen können die erfindungsgemäßen Wirkstoffe, wenn sie für die Behandlung von Tieren eingesetzt werden, direkt angewendet werden. Vorzugsweise werden sie als pharmazeutische Zusammensetzungen angewendet, die im Stand der Technik bekannte pharmazeutisch unbedenkliche Exzipienten und/oder Hilfsstoffe enthalten können.In general, the active compounds of the invention, when used for the treatment of animals, can be used directly. Preferably, they are used as pharmaceutical compositions which may contain pharmaceutically acceptable excipients and / or adjuvants known in the art.
Die Anwendung (= Verabreichung) der Wirkstoffe im Bereich Tiergesundheit und in der Tierhaltung erfolgt in bekannter Weise durch enterale Verabreichung in Form von beispielsweise Tabletten, Kapseln, Tränken, Drenchen, Granulaten, Pasten, BoIi, des feed-through-Verfahrens, von Zäpfchen, durch parenterale Verabreichung, wie zum Beispiel durch Injektionen (intramuskulär, subkutan, intravenös, intraperitoneal u.a.), Implantate, durch nasale Applikation, durch dermale Applikation in Form beispielsweise des Tauchens oder Badens (Dippen), Sprühens (Spray), Aufgießens (Pour-on und Spot-on), des Waschens, des Einpudems sowie mit Hilfe von wirkstoffhaltigen Formkörpern, wie Halsbändern, Ohrmarken, Schwanzmarken, Gliedmaßenbändern, Halftern, Markierungsvorrichtungen usw. Die Wirkstoffe können als Shampoo oder als geeignete, in Aerosolen oder drucklosen Sprays, z.B. Pumpsprays und Zerstäubersprays, anwendbare, Formulierungen formuliert werden. Bei der Anwendung für Nutztiere, Geflügel, Haustiere etc. kann man die erfindungsgemäßen Wirkstoffe als Formulierungen (beispielsweise Pulver, Spritzpulver [wettable powders, "WP"], Emulsionen, Emulsionskonzentrate [emulsifiable concentrates ,"EC"], fließfähige Mittel, homogene Lösungen und Suspensionskonzentrate [Suspension concentrates, "SC"]), die die Wirkstoffe in einer Menge von 1 bis 80 Gew.-% enthalten, direkt oder nach Verdünnung (z.B. 100- bis 10 OOOfacher Verdünnung) anwenden oder sie als chemisches Bad verwenden.The application (= administration) of the active ingredients in the field of animal health and animal husbandry is carried out in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, BoIi, the feed-through process, suppositories, by parenteral administration, for example by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal administration, by dermal application in the form of, for example, dipping or bathing (dipping), spraying, pouring (pour-on and spot-on), washing, Einpudems and with the help of active substance-containing moldings, such as collars, ear tags, tail marks, limb bands, halters, marking devices, etc. The active ingredients can be used as shampoo or as appropriate, in aerosols or non-pressurized sprays, eg pump sprays and Nebulizer sprays, applicable, formulated formulations. In the application for livestock, poultry, pets, etc., 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, apply directly or after dilution (eg 100-10,000 times dilution) or use them as a chemical bath.
Beim Einsatz im Bereich Tiergesundheit können die erfindungsgemäßen Wirkstoffe in Kombination mit geeigneten Synergisten oder anderen Wirkstoffen wie beispielsweise Akariziden, Insektiziden, Anthelmintika, Mittel gegen Protozoen, verwendet werden.When used in the animal health field, the active compounds according to the invention can be used in combination with suitable synergists or other active substances such as, for example, acaricides, insecticides, anthelmintics, antiprotozoal agents.
Als insektizide Mischungspartner kommt eine Vielzahl von Wirkstoffen in Frage. Dabei ist bekannt, dass Insektizide häufig auch eine akarizide und/oder nematizide Wirkung haben.As insecticidal mixing partner is a variety of drugs in question. It is known that insecticides often have an acaricidal and / or nematicidal action.
Die in dieser Beschreibung mit ihrem „common name" nachfolgend ihrem Wirkmechanismus (mode of action) entsprechend in 21 Gruppe eingeteilte Wirkstoffe sind beispielsweise aus „The Pesticide Manual" 13th Ed., British Crop Protection Council 2003, und der Webseite http://www.alanwood.net/pesticides bekannt und kommen als insektizide Mischpartner für Zusammensetzungen, welche mindestens eine der Verbindungen der Formel (I) enthalten, in Frage.The active ingredients classified in this description with their "common name" following their mode of action according to 21 group, for example, from "The Pesticide Manual" 13th Ed., British Crop Protection Council 2003, and the website http: // www .alanwood.net / pesticides and come as insecticidal Mischpartner for compositions containing at least one of the compounds of formula (I) in question.
(1 ) Acetylcholinesterase (AChE) Inhibitoren, wie beispielsweise(1) Acetylcholinesterase (AChE) inhibitors, such as
Carbamate, z.B. Alanycarb, Aldicarb, Aldoxycarb, Allyxycarb, Aminocarb, Bendio- carb, Benfuracarb, Bufencarb, Butacarb, Butocarboxim, Butoxycarboxim, Carbaryl, Carbofuran, Carbosulfan, Cloethocarb, Dimetilan, Ethiofencarb, Fenobucarb, Feno- thiocarb, Formetanate, Furathiocarb, Isoprocarb, Metam-sodium, Methiocarb, Metho- myl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox, Trimethacarb, XMC, und Xylylcarb; oder Organophosphate, z.B. Acephate, Azamethiphos, Azinphos (-methyl, -ethyl), Bromo- phos-ethyl, Bromfenvinfos (-methyl), Butathiofos, Cadusafos, Carbophenothion, Chlorethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos (-methyl/-ethyl), Coumaphos, Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphon, Dialifos, Diazinon, Dichlofenthion, Dichlorvos/DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos, Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilan, Fosthiazate, Heptenophos, lodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl, O-salicylate, Isoxathion, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos,Carbamates, for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendivarb, benfuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxime, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilane, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb , Metam-sodium, methiocarb, methomyl, metolcarb, oxamyl, pirimicarb, promecarb, propoxur, thiodicarb, thiofanox, trimethacarb, XMC, and xylylcarb; or Organophosphates, eg acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophosphethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chloroethoxyfos, chlorfenvinphos, chlormephos, chlorpyrifos (-methyl / -ethyl), coumaphos , Cyanofenphos, Cyanophos, Chlorfenvinphos, Demeton-S-methyl, Demeton-S-methylsulphone, Dialifos, Diazinon, Dichlofenthione, Dichlorvos / DDVP, Dicrotophos, Dimethoate, Dimethylvinphos, Dioxabenzofos, Disulfoton, EPN, Ethion, Ethoprophos, Etrimfos, Famphur, Fenamiphos , Fenitrothion, Fensulfothion, Fenthion, Flupyrazofos, Fonofos, Formothion, Fosmethilane, Fosthiazate, Heptenophos, iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isopropyl, O-Salicylate, Isoxathione, Malathion, Mecarbam, Methacrifos, Methamidophos, Methidathion, Mevinphos,
Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl/-ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methyl/-ethyl), Profenofos, Propaphos, Propetamphos, Prothiofos, Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon, Vamidothion, und Imicyafos.Monocrotophos, Naled, Omethoate, Oxydemeton-methyl, Parathion (-methyl / -ethyl), Phenthoate, Phorate, Phosalone, Phosmet, Phosphamidon, Phosphocarb, Phoxim, Pirimiphos (-methyl / -ethyl), Profenofos, Propaphos, Propetamphos, Prothiofos, Prothoate, Pyraclofos, Pyridaphenthion, Pyridathion, Quinalphos, Sebufos, Sulfotep, Sulprofos, Tebupirimfos, Temephos, Terbufos, Tetrachlorvinphos, Thiometon, Triazophos, Triclorfon, Vamidothion, and Imicyafos.
(2) GABA-gesteuerte Chlorid-Kanal-Antagonisten, wie beispielsweise Organochlorine, z.B. Camphechlor, Chlordane, Endosulfan, Gamma-HCH, HCH1 Heptachlor, Lindane, und Methoxychlor; oder Fiprole (Phenylpyrazole), z.B. Acetoprole, Ethiprole, Fipronil, Pyrafluprole, Pyriprole, und Vaniliprole.(2) GABA-controlled chloride channel antagonists, such as organochlorines, eg, camphechlor, chlordane, endosulfan, gamma-HCH, HCH 1 heptachlor, lindane, and methoxychlor; or fiproles (phenylpyrazoles), for example, acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, and vaniliprole.
(3) Natrium-Kanal-Modulatoren / Spannungsabhängige Natrium-Kanal-Blocker, wie beispielsweise Pyrethroide, z.B. Acrinathrin, Allethrin (d-cis-trans, d-trans), Beta-Cyfluthrin, Bifen- thrin, Bioallethrin, Bioallethrin-S-cyclopentyl-isomer, Bioethanomethrin, Bio- permethrin, Bioresmethrin, Chlovaporthrin, Cis-Cypermethrin, Cis-Resmethrin, Cis- Permethrin, Clocythrin, Cycloprothrin, Cyfluthrin, Cyhalothrin, Cypermethrin (alpha-, beta-, theta-, zeta-), Cyphenothrin, Deltamethrin, Empenthrin (1 R-isomer), Esfenvalerate, Etofenprox, Fenfluthrin, Fenpropathrin, Fenpyrithrin, Fenvalerate, FIu- brocythrinate, Flucythrinate, Flufenprox, Flumethrin, Fluvalinate, Fubfenprox, Gamma-Cyhalothrin, Imiprothrin, Kadethrin, Lambda-Cyhalothrin, Metofluthrin, Permethrin (eis-, trans-), Phenothrin (1 R-trans isomer), Prallethrin, Profluthrin, Protrifenbute, Pyresmethrin, Rθsmethrin, RU 15525, Silafluofen, Tau-Fluvalinate, Tefluthrin, Terallethrin, Tetramethrin (-1 R- isomer), Tralomethrin, Transfluthrin, ZXI 8901 , Pyrethrin (pyrethrum), Eflusilanat; DDT; oder Methoxychlor. (4) Nikotinerge Acetylcholin-Rezeptor-Agonisten/-Antagonisten, wie beispielsweise Chloronicotinyle, z.B. Acetamiprid, Clothianidin, Dinotefuran, Imidacloprid, Imidaclothiz, Nitenpyram, Nithiazine, Thiacloprid, Thiamethoxam, AKD-1022, Nicotin, Bensultap, Cartap, Thiosultap-Natrium, und Thiocylam.(3) Sodium channel modulators / voltage-dependent sodium channel blockers, such as pyrethroids, eg acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, biphenol, bioallethrin, bioallethrin-S cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis-resmethrin, cis-permethrin, clocthrin, cycloprothrin, cyfluthrin, cyhalothrin, cypermethrin (alpha-, beta-, theta-, zeta-), cyphenothrin , Deltamethrin, empenthrin (1R isomer), esfenvalerate, etofenprox, fenfluthrin, fenpropathrin, fenpyrithrine, fenvalerate, flucothritates, flucythrinates, flufenprox, flumethrin, fluvalinate, fubfenprox, gamma-cyhalothrin, imiprothrine, kadethrin, lambda-cyhalothrin, metofluthrin , Permethrin (cis-, trans-), phenothrin (1 R-trans isomer), prallethrin, profuthrin, Protrifenebutene, pyresmethrin, Rθsmethrin, RU 15525, silafluofen, tau-fluvalinate, tefluthrin, terallethrin, tetramethrin (-1R isomer), tralomethrin, transfluthrin, ZXI 8901, pyrethrin (pyrethrum), eflusilanate; DDT; or methoxychlor. (4) nicotinergic acetylcholine receptor agonists / antagonists, such as chloronicotinyls, eg acetamipride, clothianidin, dinotefuran, imidacloprid, imidactliziz, nitenpyram, nithiazines, thiacloprid, thiamethoxam, AKD-1022, nicotine, bensultap, cartap, thiosultap sodium, and thiocylam.
(5) Allosterische Acetylcholin-Rezeptor-Modulatoren (Agonisten), wie beispielsweise Spinosyne, z.B. Spinosad und Spinetoram.(5) Allosteric acetylcholine receptor modulators (agonists), such as spinosyns, e.g. Spinosad and Spinetoram.
(6) Chlorid-Kanal-Aktivatoren, wie beispielsweise(6) chloride channel activators, such as
Mectine / Macrolide, z.B. Abamectin, Emamectin, Emamectin-benzoate, Ivermectin, Lepimectin, und Milbemectin; oderMectins / macrolides, e.g. Abamectin, Emamectin, Emamectin benzoate, Ivermectin, Lepimectin, and Milbemectin; or
Juvenilhormon Analoge, z.B. Hydroprene, Kinoprene, Methoprene, Epofenonane, Triprene, Fenoxycarb, Pyriproxifen, und Diofenolan.Juvenile hormone analogues, e.g. Hydroprene, Kinoprene, Methoprene, Epofenonane, Triprene, Fenoxycarb, Pyriproxifen, and Diofenolan.
(7) Wirkstoffe mit unbekannten oder nicht spezifischen Wirkmechanismen, wie beispielsweise(7) agents with unknown or non-specific mechanisms of action, such as
Begasungsmittel, z.B. Methyl bromide, Chloropicrin und Sulfuryl fluoride; Selektive Fraßhemmer, z.B. Cryolite, Pymetrozine, Pyrifluquinazon und Flonicamid; oderFumigant, e.g. Methyl bromides, chloropicrin and sulfuryl fluorides; Selective feeding inhibitors, e.g. Cryolites, Pymetrozines, Pyrifluquinazone and Flonicamid; or
Milbenwachstumsinhibitoren, z.B. Clofentezine, Hexythiazox, Etoxazole.Mite growth inhibitors, e.g. Clofentezine, hexythiazox, etoxazole.
(8) Inhibitoren der oxidativen Phosphorylierung, ATP-Disruptoren, wie beispielsweise Diafenthiuron;(8) inhibitors of oxidative phosphorylation, ATP disruptors such as diafenthiuron;
Organozinnverbindungen, z.B. Azocyclotin, Cyhexatin und Fenbutatin-oxide; oder Propargite, Tetradifon.Organotin compounds, e.g. Azocyclotine, cyhexatin and fenbutatin oxides; or propargite, tetradifon.
(9) Entkoppler der oxidativen Phoshorylierung durch Unterbrechung des H-Proton- gradienten, wie beispielsweise Chlorfenapyr, Binapacyrl, Dinobuton, Dinocap und DNOC.(9) Decoupling of the oxidative phosphorylation by interruption of the H proton gradient, such as, for example, chlorfenapyr, binapacyrl, dinobutone, dinocap and DNOC.
(10) Mikrowelle Disruptoren der Insektendarmmembran, wie beispielsweise Bacillus thuringiensis-Stämme.(10) Microwave disruptors of insect intestinal membrane, such as Bacillus thuringiensis strains.
(11 ) Inhibitoren der Chitinbiosynthese, wie beispielsweise Benzoylharnstoffe, z.B. Bistrifluron, Chlorfluazuron, Diflubenzuron, Fluazuron, Flucycloxuron, Flufenoxuron, Hexaflumuron, Lufenuron, Novaluron, Noviflumuron, Penfluron, Teflubenzuron oder Triflumuron.(11) inhibitors of chitin biosynthesis, for example benzoylureas, for example bistrifluron, chlorofluorazuron, diflubenzuron, fluazuron, flucycloxuron, flufenoxuron, Hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron or triflumuron.
(12) Buprofezin.(12) Buprofezin.
(13) Häutungsstörende Wirkstoffe, wie beispielsweise Cyromazine. (14) Ecdysonagonisten/disruptoren, wie beispielsweise(13) Moulting agents, such as cyromazines. (14) ecdysone agonists / disruptors, such as
Diacylhydrazine, z.B. Chromafenozide, Halofenozide, Methoxyfenozide, Tebu- fenozide, und Fufenozide (JS118); oder Azadirachtin.Diacylhydrazines, e.g. Chromafenozide, halofenozide, methoxyfenozide, tebfenozide, and fufenozide (JS118); or Azadirachtin.
(15) Oktopaminerge Agonisten, wie beispielsweise Amitraz. (16) Seite-Ill-Elektronentransportinhibitoren/Seite-Il-Elektronentransportinhibitoren, wie beispielsweise Hydramethylnon; Acequinocyl; Fluacrypyrim; oder Cyflumetofen und Cyenopyrafen.(15) Octopaminergic agonists, such as amitraz. (16) side-III electron transport inhibitors / side II electron transport inhibitors such as, for example, hydramethylnone; acequinocyl; fluacrypyrim; or Cyflumetofen and Cyenopyrafen.
(17) Elektronentransportinhibitoren, wie beispielsweise Seite-I-Elektronentransportinhibitoren, aus der Gruppe der METI-Akarizide, z.B. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad, und Rotenone; oder Spannungsabhängige Natriumkanal-Blocker, z.B. Indoxacarb und Metaflumizone.(17) Electron transport inhibitors, such as side-I electron transport inhibitors, from the group of METI acaricides, e.g. Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad, and Rotenone; or voltage dependent sodium channel blockers, e.g. Indoxacarb and Metaflumizone.
(18) Inhibitoren der Fettsäurebiosynthese, wie beispielsweise Tetronsäure-Derivate, z.B. Spirodiclofen und Spiromesifen; oder Tetramsäure-Derivate, z.B. Spirotetramat.(18) inhibitors of fatty acid biosynthesis, such as tetronic acid derivatives, e.g. Spirodiclofen and spiromesifen; or tetramic acid derivatives, e.g. Spirotetramat.
(19) Neuronale Inhibitoren mit unbekannten Wirkmechanismus, z.B. Bifenazate.(19) Neuronal inhibitors of unknown mechanism of action, e.g. Bifenazate.
(20) Ryanodinrezeptor-Effektoren, wie beispielsweise Diamide, z.B. Flubendiamide, (R)-, (S)-3-Chlor-N1-{2-methyl-4-[1 ,2,2,2-tetrafluor-1 -(trifluormethyl)ethyl]phenyl}-N2- (1-methyl-2-methylsulfonylethyl)phthalamid, Chlorantraniliprole (Rynaxypyr), oder Cyantraniliprole (Cyazypyr).(20) ryanodine receptor effectors, such as diamides, eg flubendiamide, (R) -, (S) -3-chloro-N 1 - {2-methyl-4- [1, 2,2,2-tetrafluoro-1 - (trifluoromethyl) ethyl] phenyl} -N 2 - (1-methyl-2-methylsulfonylethyl) phthalamide, chlorantraniliprole (Rynaxypyr), or cyantraniliprole (Cyazypyr).
(21 ) Weitere Wirkstoffe mit unbekanntem Wirkmechanismus, wie beispielsweise Amidoflumet, Benclothiaz, Benzoximate, Bromopropylate, Buprofezin, Chino- methionat, Chlordimeform, Chlorobenzilate, Clothiazoben, Cycloprene, Dicofol, Di- cyclanil, Fenoxacrim, Fentrifanil, Flubenzimine, Flufenerim, Flutenzin, Gossyplure, Japonilure, Metoxadiazone, Petroleum, Potassium oleate, Pyridalyl, Sulfluramid, Tetrasul, Triarathene, oder Verbutin; oder folgende bekannte wirksame Verbindungen 4-{[(6-Brompyrid-3-yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/115644), 4-{[(6-Fluorpyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/115644), 4-{[(2-Chlor-1 ,3-thiazol-5-yl)methyl](2- fluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/115644), 4-{[(6-Chlorpyrid-3- yl)methyl](2-fluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/ 115644), 4- {[(6-Chlorpyrid-3-yl)methyl](2,2-difluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/115644), 4-{[(6-Chlor-5-fluorpyrid-3-yl)methyl](methyl)amino}furan-2(5H)-on (bekannt aus WO 2007/115643), 4-{[(5,6-Dichlorpyrid-3-yl)methyl](2- fluorethyl)amino}furan-2(5H)-on (bekannt aus WO 2007/115646), 4-{[(6-Chlor-5- fluorpyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (bekannt aus WO 2007/115643), 4-{[(6-Chlorpyrid-3-yl)methyl](cyclopropyl)amino}furan-2(5H)-on (bekannt aus EP-A-O 539 588), 4-{[(6-Chlorpyrid-3-yl)methyl](methyl)amino}furan- 2(5H)-on (bekannt aus EP-A-O 539 588), [(6-Chlorpyridin-3-yl)methyl](methyl)oxido- λ4-sulfanylidencyanamid (bekannt aus WO 2007/149134), [1-(6-Chlorpyridin-3- yl)ethyl](methyl)oxido-λ4-sulfanylidencyanamid (bekannt aus WO 2007/149134) und seine Diastereomere (A) und (B)(21) Other agents with unknown mechanism of action, such as amidoflumet, benclothiaz, benzoximate, bromopropylate, buprofezin, quinomethionate, chlordimeform, chlorobenzilate, clothiazoben, cycloprene, dicofol, dicyanil, fenoxacrim, fentrifanil, flubenzimines, flufenerim, flutenzin, gossyplasty , Japonilure, Metoxadiazone, Petroleum, Potassium oleate, Pyralidyl, Sulfluramid, Tetrasul, Triarathene, or Verbutin; or the following known effective compounds 4 - {[(6-bromopyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/115644), 4 - {[(6-fluoropyrid-3-ol) yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/115644), 4 - {[(2-chloro-1, 3-thiazol-5-yl) methyl ] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/115644), 4 - {[(6-chloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/115644), 4- {[(6-chloropyrid-3-yl) methyl] (2,2-difluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/115644), 4 - {[(6-chloro-5-fluoropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one (known from WO 2007/115643), 4 - {[ (5,6-dichloropyrid-3-yl) methyl] (2-fluoroethyl) amino} furan-2 (5H) -one (known from WO 2007/115646), 4 - {[(6-chloro-5-fluoropyridine) 3-yl) methyl] (cyclopropyl) amino} furan-2 (5H) -one (known from WO 2007/115643), 4 - {[(6-chloropyrid-3-yl) methyl] (cyclopropyl) amino} furan 2 (5H) -one (known from EP-A-0 539 588), 4 - {[(6-chloropyrid-3-yl) methyl] (methyl) amino} furan-2 (5H) -one (known from EP-AO 539 588), [(6-chloropyridin-3-yl) me ethyl] (methyl) oxido-λ 4 -sulfanylidenecyanoanamide (known from WO 2007/149134), [1- (6-chloropyridin-3-yl) ethyl] (methyl) oxido-λ 4 -sulfanylidenecyanoanamide (known from WO 2007/149134 ) and its diastereomers (A) and (B)
Figure imgf000066_0001
Figure imgf000066_0001
(A) (B)(A) (B)
(ebenfalls bekannt aus WO 2007/149134), [(6-Trifluormethylpyridin-3- yl)methyl](methyl)oxido-λ4-sulfanylidencyanamid (bekannt aus WO 2007/095229), oder [1-(6-Trifluoπnethylpyridin-3-yl)ethyl](methyl)oxido-λ4-sulfanylidencyanamid (bekannt aus WO 2007/149134) und seine Diastereomere (C) und (D), nämlich Sulfoxaflor
Figure imgf000067_0001
(also known from WO 2007/149134), [(6-trifluoromethylpyridin-3-yl) methyl] (methyl) oxido-λ 4 -sulfanylidenecyanoanamide (known from WO 2007/095229), or [1- (6-trifluoromethylpyridine-3 -yl) ethyl] (methyl) oxido-λ 4 -sulfanylidenecyanoanamide (known from WO 2007/149134) and its diastereomers (C) and (D), namely sulfoxaflor
Figure imgf000067_0001
(C) (D).(C) (D).
(ebenfalls bekannt aus WO 2007/149134). (also known from WO 2007/149134).
In den folgenden Synthesebeispielen beziehen sich die Mengenangaben (auch Prozentangaben) auf das Gewicht, sofern nichts anderes speziell angegeben ist.In the following Synthesis Examples, the amounts (even percentages) are by weight unless otherwise specified.
A. SynthesebeispieleA. Synthesis Examples
Beispiel 1 : 2,4-Dichlor-6-methylpyridin-3-carbonsäure-(N'-3',5'-dichlorphenyl-N'- prop-2"-in-1 "-yl)hydrazid (Nr. 1a-718)Example 1: 2,4-dichloro-6-methylpyridine-3-carboxylic acid (N-3 ', 5' -dichlorphenyl-N '- prop-2 "-in-1" -yl) hydrazide (No. 1a. 718)
Die Synthese von 2,4-Dichlor-6-methylpyridin-3-carbonsäure ist bereits aus der Literatur bekannt und beispielsweise beschrieben in WO 2005/070889 oder von E. C. Kooyman und J. P. Wibaut in Recueil des Travaux Chimiques des Pays-Bas et de Ia Belgique (1946), 65, 10.The synthesis of 2,4-dichloro-6-methylpyridine-3-carboxylic acid is already known from the literature and described, for example, in WO 2005/070889 or by EC Kooyman and JP Wibaut in Recueil des Travaux Chimiques des Pays-Bas et de Ia Belgique (1946), 65, 10.
Die Synthese von N'-3,5-Dichlorphenyl-N'-prop-2'-in-1 '-ylhydrazin erfolgt analog der Vorschrift zur Synthese der Verbindung 1 a-7231 (Schritt 1 ) über eine Propargylierung von 3,5-Dichlorphenylhydrazin.The synthesis of N '-3,5-dichlorophenyl-N' -prop-2 '-in-1' -ylhydrazin is analogous to the procedure for the synthesis of the compound a-1 7231 (Step 1) via a propargylation of 3,5- dichlorophenylhydrazine.
Synthese von 2,4-Dichlor-6-methylpyridin-3-carbonsäure-(N'-3',5'-dichlorphenyl-N'- prop-2"-in-1 "-yl)hydrazid (Nr. 1a-718):Synthesis of 2,4-dichloro-6-methylpyridine-3-carboxylic acid (N ' -3 ' , 5 ' -dichlorophenyl-N ' - prop-2 " -in- 1 " -yl) -hydrazide (No. 1a-718 ):
137 mg (0.66 mmol) 2,4-Dichlor-6-methylpyridin-3-carbonsäure wurden mit 1 ml Dichlormethan und 95 mg (0.80 mmol) Thionylchlorid versetzt und 4 h lang auf Rückfluss erhitzt. Das Reaktionsgemisch wurde anschließend am Rotationsverdampfer eingeengt. Der Rückstand wurde in 15 ml Tetrahydrofuran aufgenommen, anschließend wurden 150 mg (70 mmol) N'-3,5-Dichlorphenyl-N'- prop-2'-in-1 '-ylhydrazin sowie 87 mg (0.86 mmol) Triethylamin zugegeben, und das Gemisch wurde vier Tage bei Raumtemperatur gerührt. Schließlich wurde das Reaktionsgemisch am Rotationsverdampfer vom Lösungsmittel befreit und der Rückstand wurde chromatographisch gereinigt. Es wurden 156 mg sauberes Produkt erhalten. Beispiel 2: 2-Chlor-6-methyl-4-n-propyloxypyridin-3-carbonsäure-(N'-3',4'- difluorphenyl-N'-prop-2"-in-1 "-yl)hydrazid (Nr. 1a-2075)137 mg (0.66 mmol) of 2,4-dichloro-6-methylpyridine-3-carboxylic acid were admixed with 1 ml of dichloromethane and 95 mg (0.80 mmol) of thionyl chloride and heated at reflux for 4 h. The reaction mixture was then concentrated on a rotary evaporator. The residue was taken up in 15 ml of tetrahydrofuran, followed by adding 150 mg (70 mmol) of N '-3,5-dichlorophenyl-N' - prop-2 '-in-1' -ylhydrazin and 87 mg (0.86 mmol) of triethylamine, and the mixture was stirred at room temperature for four days. Finally, the reaction mixture was freed from the solvent on a rotary evaporator and the residue was purified by chromatography. There was obtained 156 mg of clean product. Example 2: 2-Chloro-6-methyl-4-n-propyloxypyridin-3-carboxylic acid (N '-3', 4 '- difluoro-phenyl-N' -prop-2 "-in-1" -yl) hydrazide ( No. 1a-2075)
Die Synthese von 2-Chlor-6-methyl-4-n-propyloxypyridin-3-carbonsäure ist bereits aus der Literatur bekannt und beispielsweise beschrieben in WO 2005/070889.The synthesis of 2-chloro-6-methyl-4-n-propyloxypyridine-3-carboxylic acid is already known from the literature and described, for example, in WO 2005/070889.
Die Synthese von N'-3,4-Difluorphenyl-N'-prop-2'-in-1 '-ylhydrazin erfolgt analog der Vorschrift zur Synthese der Verbindung 1a-7231 (Schritt 1 ) über eine Propargylierung von 3,4-Difluorphenylhydrazin.The synthesis of N '-3,4-difluorophenyl-N' -prop-2 '-in-1' -ylhydrazin is analogous to the procedure for the synthesis of compound 1a-7231 (Step 1) via a propargylation of 3,4-difluorophenylhydrazine ,
Synthese von 2-Chlor-6-methyl-4-n-propyloxypyridin-3-carbonsäure-(N'-3',4'- difluorphenyl-N'-prop-2"-in-1 "-yl)hydrazid (Nr. 1a-2075):Synthesis of 2-chloro-6-methyl-4-n-propyloxypyridin-3-carboxylic acid (N '-3', 4 '- difluoro-phenyl-N' -prop-2 "-in-1" -yl) hydrazide (No. 1a-2075):
250 mg (1.09 mmol) 2-Chlor-6-methyl-4-n-propyloxypyridin-3-carbonsäure wurden mit 1 ml Dichlormethan und 155 mg (1.31 mmol) Thionylchlorid versetzt und 4 h lang auf Rückfluss erhitzt. Das Reaktionsgemisch wurde anschließend am Rotationsverdampfer eingeengt. Der Rückstand wurde in 15 ml Tetrahydrofuran aufgenommen, anschließend wurden 208 mg (1.14 mmol) N'-3,4-Difluorphenyl-N'- prop-2'-in-1 '-ylhydrazin sowie 143 mg (1.42 mmol) Triethylamin zugegeben, und das Gemisch wurde mehrere Tage bei Raumtemperatur gerührt, bis eine LC/MS-Analyse eine weitgehende Umsetzung der Edukte anzeigte. Schließlich wurde das Reaktionsgemisch am Rotationsverdampfer vom Lösungsmittel befreit und der Rückstand wurde chromatographisch gereinigt. Es wurden 228 mg sauberes Produkt erhalten.250 mg (1.09 mmol) of 2-chloro-6-methyl-4-n-propyloxypyridine-3-carboxylic acid were treated with 1 ml of dichloromethane and 155 mg (1.31 mmol) of thionyl chloride and heated to reflux for 4 h. The reaction mixture was then concentrated on a rotary evaporator. The residue was taken up in 15 ml of tetrahydrofuran, followed by adding 208 mg (1.14 mmol) N '-3,4-difluorophenyl-N' - prop-2 '-in-1' -ylhydrazin and 143 mg (1:42 mmol) of triethylamine, and the mixture was stirred for several days at room temperature until LC / MS analysis indicated substantial reaction of the starting materials. Finally, the reaction mixture was freed from the solvent on a rotary evaporator and the residue was purified by chromatography. 228 mg of clean product were obtained.
Beispiel 3: 2-Brom-6-methyl-4-isopropyloxypyridin-3-carbonsäure-(N'-3',4'- dichlorphenyl-N'-prop-2"-in-1 "-yl)hydrazid (Nr. 1a-7231)Example 3: 2-bromo-6-methyl-4-isopropyloxypyridin-3-carboxylic acid (N '-3', 4 '- dichlorophenyl-N' -prop-2 "-in-1" -yl) hydrazide (no. 1a-7231)
Die Synthese von 2-Brom-6-methyl-4-isopropyloxypyridin-3-carbonsäure ist bereits aus der Literatur bekannt und beispielsweise beschrieben in WO 2005/070889. Schritt 1 : Synthese von N'-3\4-Dichlorphenyl-N'-prop-2'-in-1 '-ylhydrazin:The synthesis of 2-bromo-6-methyl-4-isopropyloxypyridine-3-carboxylic acid is already known from the literature and described, for example, in WO 2005/070889. Step 1: Synthesis of N '-3 \ 4-dichlorophenyl-N' -prop-2 '-in-1' -ylhydrazin:
54.3 g (1.35 mol) Natriumhydroxid wurden in 52 ml Wasser aufgenommen und mit 788 mg (2.83 mmol) Tetrabutylammoniumchloridmonohydrat versetzt. 20.8 g (94.5 mmol; 97 Gew.-% Reinheit) 3,4-Dichlorphenylhydrazinhydrochlorid sowie 60 ml Dichlormethan wurden zugegeben, und das Reaktionsgemisch wurde 10 min. bei Raumtemperatur gerührt. Anschließend wurden 21.1 g (141.8 mmol; 80 Gew.-% Reinheit) Propargylbromid tropfenweise zugegeben, danach wurde das Gemisch 16 h bei Raumtemperatur gerührt. Zur Vervollständigung der Reaktion wurden nochmals 3 ml (32.0 mmol; 80 Gew.-% Reinheit) Propargylbromid tropfenwesie zugegeben, und das Gemisch wurde erneut 16 h bei Raumtemperatur gerührt. Zur Aufarbeitung wurde das Reaktionsgemisch mit Wasser und Dichlormethan versetzt. Nach der Phasentrennung wurde die wässrige Phase zweimal mit Dichlormethan extrahiert, und die vereinigten organischen Phasen wurden getrocknet und am Rotationsverdampfer vom Lösungsmittel befreit. Der Rückstand wurde chromatographisch gereinigt, wobei 17.8 g sauberes Produkt gewonnen wurden.54.3 g (1.35 mol) of sodium hydroxide were taken up in 52 ml of water and admixed with 788 mg (2.83 mmol) of tetrabutylammonium chloride monohydrate. 20.8 g (94.5 mmol, 97% by weight purity) of 3,4-dichlorophenylhydrazine hydrochloride and 60 ml of dichloromethane were added and the reaction mixture was stirred for 10 min. stirred at room temperature. Subsequently, 21.1 g (141.8 mmol, 80 wt.% Purity) of propargyl bromide were added dropwise, after which the mixture was stirred at room temperature for 16 h. To complete the reaction, a further 3 ml (32.0 mmol, 80 wt.% Purity) of propargyl bromide were added dropwise, and the mixture was stirred again at room temperature for 16 h. For workup, the reaction mixture was treated with water and dichloromethane. After phase separation, the aqueous phase was extracted twice with dichloromethane, and the combined organic phases were dried and freed from the solvent on a rotary evaporator. The residue was purified by chromatography to yield 17.8 g of clean product.
Schritt 2: Synthese von 2-Brom-6-methyl-4-isopropyloxypyridin-3-carbonsäure-(N'- 3',4'-dichlorphenyl-N'-prop-2"-in-1 "-yl)hydrazid (Nr. 1a-7231):Step 2: Synthesis of 2-bromo-6-methyl-4-isopropyloxypyridine-3-carboxylic acid (N ' - 3 ' , 4 ' -dichlorophenyl-N ' -prop-2 " -in- 1 " -yl) -hydrazide ( No. 1a-7231):
800 mg (2.92 mmol) 2-Brom-6-methyl-4-isopropyloxypyridin-3-carbonsäure wurden mit 11.4 g (96.0 mmol) Thionylchlorid versetzt und 2 h bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde anschließend am Rotationsverdampfer eingeengt, danach wurde zur Entfernung restlicher Mengen Thionylchlorid zweimal Dichlormethan zum Rückstand gegeben und nochmals am Rotationsverdampfer eingeengt. Von dem so erhaltenen rohen Säurechlorid wurden 143 mg (0.49 mmol) in 15 ml Tetrahydrofuran aufgenommen, anschließend wurden 100 mg (0.47 mmol) N'-3,4-Dichlorphenyl-N'-prop-2'-in-1 '-ylhydrazin sowie 54 mg (0.54 mmol) Triethylamin zugegeben, und das Gemisch wurde 6 h bei 60 0C gerührt. Schließlich wurde das Reaktionsgemisch am Rotationsverdampfer vom Lösungsmittel befreit und der Rückstand wurde chromatographisch gereinigt. Es wurden 109 mg Produkt erhalten. Beispiel 4: 6-Chlor-5-methyl-pyridin-3-carbonsäure-(N'-4'-chlorphenyl-N'-prop-2"- in-1 "-yl)hydrazid (Nr. 3a-644)800 mg (2.92 mmol) of 2-bromo-6-methyl-4-isopropyloxypyridine-3-carboxylic acid were admixed with 11.4 g (96.0 mmol) of thionyl chloride and stirred at room temperature for 2 h. The reaction mixture was then concentrated on a rotary evaporator, then to remove remaining amounts of thionyl chloride twice dichloromethane was added to the residue and concentrated again on a rotary evaporator. From the thus-obtained crude acid chloride 143 mg was added (0:49 mmol) in 15 ml of tetrahydrofuran, then 100 mg (0:47 mmol) of N '-3,4-dichlorophenyl-N' -prop-2 '-in-1' -ylhydrazin and 54 mg (0:54 mmol) of triethylamine, and the mixture was stirred for 6 h at 60 0 C. Finally, the reaction mixture was freed from the solvent on a rotary evaporator and the residue was purified by chromatography. There were obtained 109 mg of product. Example 4: 6-chloro-5-methyl-pyridine-3-carboxylic acid (N '-4' -chlorophenyl-N '-prop-2 "- in-1" -yl) hydrazide (No. 3a-644).
Die Synthese von δ-Chlor-δ-methyl-pyridin-S-carbonsäure ist bereits aus der Literatur bekannt und beispielsweise beschrieben in WO 2008/029370.The synthesis of δ-chloro-δ-methyl-pyridine-S-carboxylic acid is already known from the literature and described, for example, in WO 2008/029370.
Die Synthese von N'-4-Chlorphenyl-N'-prop-2'-in-1 '-ylhydrazin erfolgt analog der Vorschrift zur Synthese der Verbindung 1a-7231 (Schritt 1 ) über eine Propargylierung von 4-Chlorphenylhydrazin.The synthesis of N '-4-chlorophenyl-N' -prop-2 '-in-1' takes place -ylhydrazin the procedure for the synthesis of compound 1a-7231 analog (Step 1) via a propargylation of 4-chlorophenylhydrazine.
Synthese von θ-Chlor-δ-methyl-pyridin-S-carbonsäure^N'^'-chlorphenyl-N'-prop- 2"-in-1 "-yl)hydrazid (Nr. 3a-644):Synthesis of θ-chloro-δ-methyl-pyridin-S-carboxylic acid ^ N '^' -chlorophenyl-N '-prop-2 "-in-1" -yl) hydrazide (No. 3a-644).:
320 mg (1.87 mmol) β-Chlor-δ-methyl-pyridin-S-carbonsäure wurden mit 3.26 g (27.4 mmol) Thionylchlorid versetzt und 2 h bei Raumtemperatur gerührt. Das Reaktionsgemisch wurde anschließend am Rotationsverdampfer eingeengt, danach wurde zur Entfernung restlicher Mengen Thionylchlorid zweimal Dichlormethan zum Rückstand gegeben und nochmals am Rotationsverdampfer eingeengt. Von dem so erhaltenen rohen Säurechlorid wurden 89 mg (0.47 mmol) in 15 ml Tetrahydrofuran aufgenommen, anschließend wurden 80 mg (0.44 mmol) N'-4-Chlorphenyl-N'-prop- 2'-in-1 '-ylhydrazin sowie 52 mg (0.51 mmol) Triethylamin zugegeben, und das Gemisch wurde mehrere Tage bei Raumtemperatur gerührt, bis eine LC/MS-Analyse eine weitgehende Umsetzung der Edukte anzeigte. Schließlich wurde das Reaktionsgemisch am Rotationsverdampfer vom Lösungsmittel befreit und der320 mg (1.87 mmol) of β-chloro-δ-methyl-pyridine-S-carboxylic acid were admixed with 3.26 g (27.4 mmol) of thionyl chloride and stirred at room temperature for 2 h. The reaction mixture was then concentrated on a rotary evaporator, then to remove remaining amounts of thionyl chloride twice dichloromethane was added to the residue and concentrated again on a rotary evaporator. From the thus-obtained crude acid chloride 89 mg were taken (0:47 mmol) in 15 ml tetrahydrofuran, then 80 mg (0:44 mmol) of N '-4-chlorophenyl-N' -prop-2 '-in-1' and 52 -ylhydrazin mg (0.51 mmol) of triethylamine, and the mixture was stirred for several days at room temperature until LC / MS analysis indicated substantial reaction of the starting materials. Finally, the reaction mixture was freed from the solvent on a rotary evaporator and the
Rückstand wurde chromatographisch gereinigt. Es wurden 116 mg Produkt erhalten.Residue was purified by chromatography. 116 mg of product were obtained.
Beispiel 5: 1-Methyl-3-trifluormethylpyrazol-4-carbonsäure-(N'-4'-chlorphenyl-N'- prop-2"-in-1 "-yl)hydrazid (Nr. 6a-2990)Example 5: 1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid (N '-4' -chlorophenyl-N '- prop-2 "-in-1" -yl) hydrazide (No. 6a-2990th)
Die Synthese von 1-Methyl-3-trifluormethylpyrazol-4-carbonsäurechlorid ist bereits aus der Literatur bekannt und beispielsweise beschrieben in WO 93/11117. Die Synthese von N'-4-Chlorphenyl-N'-prop-2'-in-1 '-ylhydrazin erfolgt analog der Vorschrift zur Synthese der Verbindung 1a-7231 (Schritt 1 ) über eine Propargylierung von 4-Chlorphenylhydrazin.The synthesis of 1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid chloride is already known from the literature and described, for example, in WO 93/11117. The synthesis of N '-4-chlorophenyl-N' -prop-2 '-in-1' takes place -ylhydrazin the procedure for the synthesis of compound 1a-7231 analog (Step 1) via a propargylation of 4-chlorophenylhydrazine.
Synthese von 1-Methyl-3-trifluormethylpyrazol-4-carbonsäure-(N'-4'-chlorphenyl-N'- prop-2"-in-1 "-yl)hydrazid (Nr. 6a-2990):Synthesis of 1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid (N '-4' -chlorophenyl-N '- prop-2 "-in-1" -yl) hydrazide (No. 6a-2990th):
124 mg (0.58 mmol) i-Methyl-S-trifluormethylpyrazoM-carbonsäurechlorid wurden in 15 ml Tetrahydrofuran aufgenommen, anschließend wurden 100 mg (0.55 mmol) N'- 4-Chlorphenyl-N'-prop-2'-in-1 '-ylhydrazin sowie 65 mg (0.64 mmol) Triethylamin zugegeben, und das Gemisch wurde mehrere Tage bei Raumtemperatur gerührt, bis eine LC/MS-Analyse eine weitgehende Umsetzung der Edukte anzeigte. Schließlich wurde das Reaktionsgemisch am Rotationsverdampfer vom Lösungsmittel befreit und der Rückstand wurde chromatographisch gereinigt. Es wurden 158 mg sauberes Produkt erhalten.124 mg (0:58 mmol) of i-methyl-S-trifluormethylpyrazoM-carboxylic acid chloride were added to 15 ml of tetrahydrofuran, then 100 mg (0:55 mmol) of N '- 4-chlorophenyl-N' -prop-2 '-in-1' - ylhydrazine and 65 mg (0.64 mmol) of triethylamine were added, and the mixture was stirred for several days at room temperature until LC / MS analysis indicated substantial reaction of the reactants. Finally, the reaction mixture was freed from the solvent on a rotary evaporator and the residue was purified by chromatography. 158 mg of clean product were obtained.
Die in den nachfolgenden Tabellen aufgeführten Beispiele wurden analog zu den oben genannten Methoden hergestellt, beziehungsweise sind analog oben genannten Methoden erhältlich. The examples listed in the following tables were prepared analogously to the abovementioned methods, or are obtainable analogously to the abovementioned methods.
In den nachfolgenden Tabellen werden folgende Abkürzungen mit der jeweils angegebenen Bedeutung verwendet, wobei in den Strukturformeln die gestrichelte gezeichnete Bindung die Bindung des Rests R2 an den Hydrazid-Stickstoff gemäß Formel (I) bedeutet:In the following tables, the following abbreviations are used with the meanings given in each case, wherein in the structural formulas the dashed bond denotes the binding of the radical R 2 to the hydrazide nitrogen according to formula (I):
nPr bedeutet 1-Propyl iPr bedeutet 2-Propyl cPr bedeutet CyclopropylnPr is 1-propyl iPr is 2-propyl cPr is cyclopropyl
AIIyI bedeutet
Figure imgf000073_0001
AIIyI means
Figure imgf000073_0001
Me2-AIIyI bedeutetMe 2 -AIIyI means
Propargyl bedeutet
Figure imgf000073_0002
Propargyl means
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But-2-inyl bedeutet
Figure imgf000073_0003
But-2-inyl means
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Isoxazol bedeutet
Figure imgf000073_0004
Isoxazole means
Figure imgf000073_0004
CH2-lsoxazol bedeutet
Figure imgf000073_0005
Tabelle 1 a: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2 mit R12 = Wasserstoff und R13 = Methyl, R1 für Wasserstoff sowie R3 für IIa mit R8 = Wasserstoff stehen.CH 2 -lsoxazole means
Figure imgf000073_0005
Table 1 a: Compounds of the general formula (I) according to the invention in which Q is Q 2 where R 12 = hydrogen and R 13 = methyl, R 1 is hydrogen and R 3 is IIa where R 8 = hydrogen.
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Figure imgf000166_0001
Figure imgf000167_0001
Figure imgf000168_0001
Figure imgf000169_0001
Figure imgf000170_0001
Figure imgf000171_0001
Figure imgf000172_0001
Figure imgf000173_0001
Figure imgf000174_0001
Figure imgf000175_0001
Figure imgf000176_0001
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Figure imgf000187_0001
Figure imgf000188_0001
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Figure imgf000190_0001
Figure imgf000191_0001
Figure imgf000192_0001
Figure imgf000193_0001
Figure imgf000194_0001
Figure imgf000195_0001
Figure imgf000196_0001
Figure imgf000197_0001
Figure imgf000198_0001
Figure imgf000199_0001
Figure imgf000200_0001
Figure imgf000201_0001
Figure imgf000202_0001
Figure imgf000203_0001
Figure imgf000204_0001
Figure imgf000205_0001
Figure imgf000206_0001
Figure imgf000207_0001
Figure imgf000208_0001
Figure imgf000209_0001
Figure imgf000210_0001
Figure imgf000211_0001
Figure imgf000212_0001
Figure imgf000213_0001
Figure imgf000214_0001
Figure imgf000215_0001
Figure imgf000216_0001
Figure imgf000217_0001
Figure imgf000218_0001
Figure imgf000219_0001
Figure imgf000220_0001
Figure imgf000221_0001
Figure imgf000222_0001
Figure imgf000223_0001
Figure imgf000224_0001
Figure imgf000225_0001
Figure imgf000226_0001
Figure imgf000227_0001
Figure imgf000228_0001
Figure imgf000229_0001
Figure imgf000230_0001
Figure imgf000231_0001
Figure imgf000232_0001
Figure imgf000233_0001
Figure imgf000234_0001
Figure imgf000235_0001
Figure imgf000236_0001
Figure imgf000237_0001
Figure imgf000238_0001
Figure imgf000239_0001
Figure imgf000240_0001
Figure imgf000241_0001
Figure imgf000242_0001
Figure imgf000243_0001
Figure imgf000244_0001
Figure imgf000245_0001
Figure imgf000246_0001
Figure imgf000247_0001
Figure imgf000248_0001
Figure imgf000249_0001
Figure imgf000250_0001
Figure imgf000251_0001
Figure imgf000252_0001
Figure imgf000253_0001
Figure imgf000255_0001
Figure imgf000256_0001
Figure imgf000257_0001
Tabelle 1 b: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2 mit R12 = Wasserstoff und R13 = Methyl, R1 für Wasserstoff sowie R3 für Mc mit R8 = Wasserstoff stehen.
Figure imgf000210_0001
Figure imgf000211_0001
Figure imgf000212_0001
Figure imgf000213_0001
Figure imgf000214_0001
Figure imgf000215_0001
Figure imgf000216_0001
Figure imgf000217_0001
Figure imgf000218_0001
Figure imgf000219_0001
Figure imgf000220_0001
Figure imgf000221_0001
Figure imgf000222_0001
Figure imgf000223_0001
Figure imgf000224_0001
Figure imgf000225_0001
Figure imgf000226_0001
Figure imgf000227_0001
Figure imgf000228_0001
Figure imgf000229_0001
Figure imgf000230_0001
Figure imgf000231_0001
Figure imgf000232_0001
Figure imgf000233_0001
Figure imgf000234_0001
Figure imgf000235_0001
Figure imgf000236_0001
Figure imgf000237_0001
Figure imgf000238_0001
Figure imgf000239_0001
Figure imgf000240_0001
Figure imgf000241_0001
Figure imgf000242_0001
Figure imgf000243_0001
Figure imgf000244_0001
Figure imgf000245_0001
Figure imgf000246_0001
Figure imgf000247_0001
Figure imgf000248_0001
Figure imgf000249_0001
Figure imgf000250_0001
Figure imgf000251_0001
Figure imgf000252_0001
Figure imgf000253_0001
Figure imgf000255_0001
Figure imgf000256_0001
Figure imgf000257_0001
Table 1 b: Compounds of the invention of the general formula (I) wherein Q is Q 2 with R 12 = hydrogen and R 13 = methyl, R 1 is hydrogen and R 3 is Mc with R 8 = hydrogen.
Figure imgf000258_0001
Figure imgf000258_0001
Figure imgf000258_0002
Figure imgf000259_0001
Figure imgf000260_0001
Figure imgf000261_0001
Figure imgf000262_0001
Figure imgf000263_0001
Figure imgf000264_0001
Figure imgf000265_0001
Figure imgf000266_0001
Figure imgf000267_0001
Figure imgf000268_0001
Figure imgf000269_0001
Figure imgf000270_0001
Figure imgf000271_0001
Figure imgf000272_0001
Figure imgf000273_0001
Figure imgf000258_0002
Figure imgf000259_0001
Figure imgf000260_0001
Figure imgf000261_0001
Figure imgf000262_0001
Figure imgf000263_0001
Figure imgf000264_0001
Figure imgf000265_0001
Figure imgf000266_0001
Figure imgf000267_0001
Figure imgf000268_0001
Figure imgf000269_0001
Figure imgf000270_0001
Figure imgf000271_0001
Figure imgf000272_0001
Figure imgf000273_0001
Tabelle 2a: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2 mit R11 = R12 = Wasserstoff, R13 = Methyl und R14 = Chlor, R1 für Wasserstoff sowie R3 für IIa mit R8 = Wasserstoff stehen.Compounds of the invention of the general formula (I) wherein Q = Q2 R 11 = R 12 is hydrogen, R 13 = methyl and R 14 = chlorine, R 1 is hydrogen and R 3 represent IIa with R 8 = hydrogen: Table 2a ,
Figure imgf000274_0001
Figure imgf000274_0001
Figure imgf000274_0002
Figure imgf000275_0001
Figure imgf000276_0001
Figure imgf000277_0001
Figure imgf000278_0001
Figure imgf000279_0001
Figure imgf000280_0001
Figure imgf000281_0001
Figure imgf000282_0001
Figure imgf000283_0001
Figure imgf000284_0001
Figure imgf000285_0001
Figure imgf000286_0001
Figure imgf000287_0001
Figure imgf000288_0001
Figure imgf000289_0001
Figure imgf000290_0001
Figure imgf000291_0001
Figure imgf000292_0001
Figure imgf000293_0001
Figure imgf000294_0001
Figure imgf000295_0001
Figure imgf000296_0001
Figure imgf000297_0001
Figure imgf000298_0001
Figure imgf000299_0001
Figure imgf000300_0001
Tabelle 2b: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2 mit R11 = R12 = Wasserstoff, R13 = Methyl und R14 = Chlor, R1 für Wasserstoff sowie R3 für Mc mit R8 = Wasserstoff stehen.
Figure imgf000274_0002
Figure imgf000275_0001
Figure imgf000276_0001
Figure imgf000277_0001
Figure imgf000278_0001
Figure imgf000279_0001
Figure imgf000280_0001
Figure imgf000281_0001
Figure imgf000282_0001
Figure imgf000283_0001
Figure imgf000284_0001
Figure imgf000285_0001
Figure imgf000286_0001
Figure imgf000287_0001
Figure imgf000288_0001
Figure imgf000289_0001
Figure imgf000290_0001
Figure imgf000291_0001
Figure imgf000292_0001
Figure imgf000293_0001
Figure imgf000294_0001
Figure imgf000295_0001
Figure imgf000296_0001
Figure imgf000297_0001
Figure imgf000298_0001
Figure imgf000299_0001
Figure imgf000300_0001
Compounds of the invention of the general formula (I) wherein Q = Q2 R 11 = R 12 is hydrogen, R 13 = methyl and R 14 = chlorine, R 1 is hydrogen and R 3 are Mc with R 8 = hydrogen: Table 2b ,
Figure imgf000301_0001
Figure imgf000301_0001
Figure imgf000301_0002
Figure imgf000302_0001
Figure imgf000303_0001
Figure imgf000301_0002
Figure imgf000302_0001
Figure imgf000303_0001
Tabelle 3a: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2 mit R11 = R14 = Wasserstoff, R12 = Methyl und R13 = Chlor, R1 für Wasserstoff sowie R3 für IIa mit R8 = Wasserstoff stehen.Table 3a: Compounds of the invention of the general formula (I) wherein Q = Q2 R 11 = R 14 is hydrogen, R 12 = methyl and R 13 = chlorine, R 1 is hydrogen and R 3 represent IIa with R 8 = hydrogen ,
Figure imgf000304_0001
Figure imgf000304_0001
Figure imgf000304_0002
Figure imgf000305_0001
Figure imgf000306_0001
Figure imgf000307_0001
Figure imgf000308_0001
Figure imgf000309_0001
Figure imgf000310_0001
Figure imgf000311_0001
Figure imgf000312_0001
Figure imgf000313_0001
Figure imgf000314_0001
Figure imgf000315_0001
Figure imgf000304_0002
Figure imgf000305_0001
Figure imgf000306_0001
Figure imgf000307_0001
Figure imgf000308_0001
Figure imgf000309_0001
Figure imgf000310_0001
Figure imgf000311_0001
Figure imgf000312_0001
Figure imgf000313_0001
Figure imgf000314_0001
Figure imgf000315_0001
Figure imgf000316_0001
Figure imgf000317_0001
Figure imgf000318_0001
Figure imgf000319_0001
Figure imgf000320_0001
Figure imgf000321_0001
Figure imgf000322_0001
Figure imgf000323_0001
Figure imgf000324_0001
Figure imgf000325_0001
Figure imgf000326_0001
Figure imgf000327_0001
Figure imgf000328_0001
Figure imgf000329_0001
Figure imgf000330_0001
Figure imgf000331_0001
Figure imgf000316_0001
Figure imgf000317_0001
Figure imgf000318_0001
Figure imgf000319_0001
Figure imgf000320_0001
Figure imgf000321_0001
Figure imgf000322_0001
Figure imgf000323_0001
Figure imgf000324_0001
Figure imgf000325_0001
Figure imgf000326_0001
Figure imgf000327_0001
Figure imgf000328_0001
Figure imgf000329_0001
Figure imgf000330_0001
Figure imgf000331_0001
Tabelle 3b: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q2 mit R11 = R14 = Wasserstoff, R12 = Methyl und R13 = Chlor, R1 für Wasserstoff sowie R3 für Hc mit R8 = Wasserstoff stehen.Compounds of the invention of the general formula (I) wherein Q = Q2 R 11 = R 14 is hydrogen, R 12 = methyl and R 13 = chlorine, R 1 is hydrogen and R 3 represent Hc with R 8 = hydrogen: Table 3b ,
Figure imgf000332_0001
Figure imgf000332_0001
Figure imgf000332_0002
Figure imgf000333_0001
Figure imgf000334_0001
Figure imgf000332_0002
Figure imgf000333_0001
Figure imgf000334_0001
Tabelle 4a: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q14 mit R12 = Methyl, R1 für Wasserstoff sowie R3 für IIa mit R8 = Wasserstoff stehen.Table 4a: Compounds of the general formula (I) according to the invention, in which Q is Q14 with R 12 = methyl, R 1 is hydrogen and R 3 is IIa where R 8 = hydrogen.
Figure imgf000335_0001
Figure imgf000335_0001
Figure imgf000335_0002
Figure imgf000336_0001
Figure imgf000337_0001
Figure imgf000338_0001
Figure imgf000339_0001
Figure imgf000340_0001
Figure imgf000341_0001
Figure imgf000342_0001
Figure imgf000343_0001
Figure imgf000344_0001
Figure imgf000345_0001
Figure imgf000346_0001
Figure imgf000347_0001
Figure imgf000348_0001
Figure imgf000349_0001
Figure imgf000350_0001
Figure imgf000351_0001
Figure imgf000352_0001
Figure imgf000353_0001
Figure imgf000354_0001
Figure imgf000355_0001
Figure imgf000356_0001
Figure imgf000357_0001
Figure imgf000358_0001
Figure imgf000359_0001
Figure imgf000360_0001
Figure imgf000362_0001
Figure imgf000363_0001
Figure imgf000364_0001
Figure imgf000365_0001
Figure imgf000366_0001
Figure imgf000367_0001
Figure imgf000368_0001
Figure imgf000369_0001
Figure imgf000370_0001
Figure imgf000371_0001
Figure imgf000372_0001
Figure imgf000373_0001
Figure imgf000374_0001
Figure imgf000375_0001
Figure imgf000376_0001
Figure imgf000335_0002
Figure imgf000336_0001
Figure imgf000337_0001
Figure imgf000338_0001
Figure imgf000339_0001
Figure imgf000340_0001
Figure imgf000341_0001
Figure imgf000342_0001
Figure imgf000343_0001
Figure imgf000344_0001
Figure imgf000345_0001
Figure imgf000346_0001
Figure imgf000347_0001
Figure imgf000348_0001
Figure imgf000349_0001
Figure imgf000350_0001
Figure imgf000351_0001
Figure imgf000352_0001
Figure imgf000353_0001
Figure imgf000354_0001
Figure imgf000355_0001
Figure imgf000356_0001
Figure imgf000357_0001
Figure imgf000358_0001
Figure imgf000359_0001
Figure imgf000360_0001
Figure imgf000362_0001
Figure imgf000363_0001
Figure imgf000364_0001
Figure imgf000365_0001
Figure imgf000366_0001
Figure imgf000367_0001
Figure imgf000368_0001
Figure imgf000369_0001
Figure imgf000370_0001
Figure imgf000371_0001
Figure imgf000372_0001
Figure imgf000373_0001
Figure imgf000374_0001
Figure imgf000375_0001
Figure imgf000376_0001
Tabelle 4b: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q14 mit R12 = Methyl, R1 für Wasserstoff sowie R3 für Mc mit R8 = Wasserstoff stehen.Table 4b: Compounds of the invention of the general formula (I) wherein Q is Q14 with R 12 = methyl, R 1 is hydrogen and R 3 is Mc with R 8 = hydrogen.
Figure imgf000377_0001
Figure imgf000377_0001
Figure imgf000377_0002
Figure imgf000378_0001
Figure imgf000379_0001
Figure imgf000380_0001
Figure imgf000377_0002
Figure imgf000378_0001
Figure imgf000379_0001
Figure imgf000380_0001
Tabelle 5a: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q17 mit R11a = Chlor, R12 = Wasserstoff und R13 = Fluor, R1 für Wasserstoff sowie R3 für IIa mit R8 = Wasserstoff stehen.Table 5a: Compounds of the invention of the general formula (I) wherein Q is Q17 with R 11a = chlorine, R 12 = hydrogen and R 13 = fluorine, R 1 is hydrogen and R 3 is IIa with R 8 = hydrogen.
Figure imgf000381_0001
Figure imgf000381_0001
Figure imgf000381_0002
Figure imgf000382_0001
Figure imgf000383_0001
Figure imgf000384_0001
Figure imgf000385_0001
Figure imgf000386_0001
Figure imgf000387_0001
Figure imgf000388_0001
Figure imgf000389_0001
Figure imgf000390_0001
Figure imgf000391_0001
Figure imgf000392_0001
Figure imgf000393_0001
Figure imgf000394_0001
Figure imgf000395_0001
Figure imgf000396_0001
Figure imgf000397_0001
Figure imgf000398_0001
Figure imgf000399_0001
Figure imgf000400_0001
Figure imgf000401_0001
Figure imgf000402_0001
Figure imgf000403_0001
Figure imgf000404_0001
Figure imgf000405_0001
Figure imgf000406_0001
Figure imgf000407_0001
Figure imgf000408_0001
Figure imgf000409_0001
Figure imgf000410_0001
Figure imgf000411_0001
Figure imgf000412_0001
Figure imgf000413_0001
Figure imgf000414_0001
Figure imgf000415_0001
Figure imgf000416_0001
Figure imgf000417_0001
Figure imgf000418_0001
Figure imgf000419_0001
Figure imgf000420_0001
Figure imgf000421_0001
Figure imgf000422_0001
Figure imgf000381_0002
Figure imgf000382_0001
Figure imgf000383_0001
Figure imgf000384_0001
Figure imgf000385_0001
Figure imgf000386_0001
Figure imgf000387_0001
Figure imgf000388_0001
Figure imgf000389_0001
Figure imgf000390_0001
Figure imgf000391_0001
Figure imgf000392_0001
Figure imgf000393_0001
Figure imgf000394_0001
Figure imgf000395_0001
Figure imgf000396_0001
Figure imgf000397_0001
Figure imgf000398_0001
Figure imgf000399_0001
Figure imgf000400_0001
Figure imgf000401_0001
Figure imgf000402_0001
Figure imgf000403_0001
Figure imgf000404_0001
Figure imgf000405_0001
Figure imgf000406_0001
Figure imgf000407_0001
Figure imgf000408_0001
Figure imgf000409_0001
Figure imgf000410_0001
Figure imgf000411_0001
Figure imgf000412_0001
Figure imgf000413_0001
Figure imgf000414_0001
Figure imgf000415_0001
Figure imgf000416_0001
Figure imgf000417_0001
Figure imgf000418_0001
Figure imgf000419_0001
Figure imgf000420_0001
Figure imgf000421_0001
Figure imgf000422_0001
Tabelle 5b: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q17 mit R11a = Chlor, R12 = Wasserstoff und R13 = Fluor, R1 für Wasserstoff sowie R3 für Hc mit R8 = Wasserstoff stehen.Table 5b: Compounds of the invention of the general formula (I) wherein Q is Q17 with R 11a = chlorine, R 12 = hydrogen and R 13 = fluorine, R 1 is hydrogen and R 3 is Hc with R 8 = hydrogen.
Figure imgf000423_0001
Figure imgf000423_0001
Figure imgf000423_0002
Figure imgf000424_0001
Figure imgf000425_0001
Figure imgf000426_0001
Figure imgf000423_0002
Figure imgf000424_0001
Figure imgf000425_0001
Figure imgf000426_0001
Tabelle 6a: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q8 mit R12 = Wasserstoff und T = Methyl, R1 für Wasserstoff sowie R3 für IIa mit R8 = Wasserstoff stehen.Table 6a: Compounds of the invention of the general formula (I) wherein Q is Q8 with R 12 = hydrogen and T = methyl, R 1 is hydrogen and R 3 is IIa with R 8 = hydrogen.
Figure imgf000427_0001
Figure imgf000427_0001
Figure imgf000427_0002
Figure imgf000428_0001
Figure imgf000429_0001
Figure imgf000430_0001
Figure imgf000431_0001
Figure imgf000432_0001
Figure imgf000433_0001
Figure imgf000434_0001
Figure imgf000435_0001
Figure imgf000436_0001
Figure imgf000437_0001
Figure imgf000438_0001
Figure imgf000439_0001
Figure imgf000427_0002
Figure imgf000428_0001
Figure imgf000429_0001
Figure imgf000430_0001
Figure imgf000431_0001
Figure imgf000432_0001
Figure imgf000433_0001
Figure imgf000434_0001
Figure imgf000435_0001
Figure imgf000436_0001
Figure imgf000437_0001
Figure imgf000438_0001
Figure imgf000439_0001
Figure imgf000440_0001
Figure imgf000441_0001
Figure imgf000442_0001
Figure imgf000443_0001
Figure imgf000444_0001
Figure imgf000445_0001
Figure imgf000446_0001
Figure imgf000447_0001
Figure imgf000448_0001
Figure imgf000449_0001
Figure imgf000450_0001
Figure imgf000451_0001
Figure imgf000452_0001
Figure imgf000453_0001
Figure imgf000454_0001
Figure imgf000455_0001
Figure imgf000456_0001
Figure imgf000457_0001
Figure imgf000458_0001
Figure imgf000459_0001
Figure imgf000460_0001
Figure imgf000461_0001
Figure imgf000440_0001
Figure imgf000441_0001
Figure imgf000442_0001
Figure imgf000443_0001
Figure imgf000444_0001
Figure imgf000445_0001
Figure imgf000446_0001
Figure imgf000447_0001
Figure imgf000448_0001
Figure imgf000449_0001
Figure imgf000450_0001
Figure imgf000451_0001
Figure imgf000452_0001
Figure imgf000453_0001
Figure imgf000454_0001
Figure imgf000455_0001
Figure imgf000456_0001
Figure imgf000457_0001
Figure imgf000458_0001
Figure imgf000459_0001
Figure imgf000460_0001
Figure imgf000461_0001
Figure imgf000463_0001
Figure imgf000464_0001
Figure imgf000465_0001
Figure imgf000466_0001
Figure imgf000467_0001
Figure imgf000468_0001
Figure imgf000469_0001
Figure imgf000470_0001
Figure imgf000471_0001
Figure imgf000463_0001
Figure imgf000464_0001
Figure imgf000465_0001
Figure imgf000466_0001
Figure imgf000467_0001
Figure imgf000468_0001
Figure imgf000469_0001
Figure imgf000470_0001
Figure imgf000471_0001
Figure imgf000472_0001
Figure imgf000472_0001
Figure imgf000473_0001
Figure imgf000473_0001
Figure imgf000474_0001
Figure imgf000475_0001
Figure imgf000476_0001
Figure imgf000477_0001
Figure imgf000478_0001
Figure imgf000479_0001
Figure imgf000480_0001
Figure imgf000481_0001
Figure imgf000482_0001
Figure imgf000483_0001
Figure imgf000474_0001
Figure imgf000475_0001
Figure imgf000476_0001
Figure imgf000477_0001
Figure imgf000478_0001
Figure imgf000479_0001
Figure imgf000480_0001
Figure imgf000481_0001
Figure imgf000482_0001
Figure imgf000483_0001
Figure imgf000484_0001
Figure imgf000484_0001
Figure imgf000485_0001
Figure imgf000485_0001
Figure imgf000486_0001
Figure imgf000487_0001
Figure imgf000488_0001
Figure imgf000489_0001
Figure imgf000490_0001
Figure imgf000486_0001
Figure imgf000487_0001
Figure imgf000488_0001
Figure imgf000489_0001
Figure imgf000490_0001
Figure imgf000491_0001
Figure imgf000492_0001
Figure imgf000493_0001
Tabelle 6b: Erfindungsgemäße Verbindungen der allgemeinen Formel (I), worin Q für Q8 mit R12 = Wasserstoff und T = Methyl, R1 für Wasserstoff sowie R3 für Mc mit R8 = Wasserstoff stehen.
Figure imgf000491_0001
Figure imgf000492_0001
Figure imgf000493_0001
Table 6b: Compounds of the invention of the general formula (I) wherein Q is Q8 with R 12 = hydrogen and T = methyl, R 1 is hydrogen and R 3 is Mc with R 8 = hydrogen.
Figure imgf000494_0001
Figure imgf000494_0001
Figure imgf000494_0002
Figure imgf000495_0001
Figure imgf000496_0001
Figure imgf000497_0001
Figure imgf000498_0001
Figure imgf000499_0001
Figure imgf000494_0002
Figure imgf000495_0001
Figure imgf000496_0001
Figure imgf000497_0001
Figure imgf000498_0001
Figure imgf000499_0001
B. FormulierungsbeispieleB. Formulation Examples
a) Ein Stäubemittel wird erhalten, indem man 10 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze und 90 Gew.-Teile Talkum als Inertstoff mischt und in einer Schlagmühle zerkleinert.a) A dust is obtained by mixing 10 parts by weight of a compound of formula (I) and / or salts thereof and 90 parts by weight of talc as an inert material and comminuted in a hammer mill.
b) Ein in Wasser leicht dispergierbares, benetzbares Pulver wird erhalten, indem man 25 Gewichtsteile einer Verbindung der Formel (I) und/oder deren Salze, 64 Gew.-Teile kaolinhaltigen Quarz als Inertstoff, 10 Gewichtsteile ligninsulfonsaures Kalium und 1 Gew.-Teil oleoylmethyltaurinsaures Natrium als Netz- und Dispergiermittel mischt und in einer Stiftmühle mahlt.b) A wettable powder readily dispersible in water is obtained by reacting 25 parts by weight of a compound of formula (I) and / or its salts, 64 parts by weight of kaolin-containing quartz as inert material, 10 parts by weight of potassium lignosulfonate and 1 part by weight Mix oleoylmethyl tauric acid sodium as wetting and dispersing agent and mill in a pin mill.
c) Ein in Wasser leicht dispergierbares Dispersionskonzentrat wird erhalten, indem man 20 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze mit 6 Gew.-Teilen Alkylphenolpolyglykolether (©Triton X 207), 3c) A dispersion concentrate readily dispersible in water is obtained by reacting 20 parts by weight of a compound of the formula (I) and / or salts thereof with 6 parts by weight of alkylphenol polyglycol ether (© Triton X 207), 3
Gew.-Teilen Isotridecanolpolyglykolether (8 EO) und 71 Gew.-Teilen paraffinischem Mineralöl (Siedebereich z.B. ca. 255 bis über 277 C) mischt und in einer Reibkugelmühle auf eine Feinheit von unter 5 Mikron vermahlt.Parts by weight of isotridecanol polyglycol ether (8 EO) and 71 parts by weight of paraffinic mineral oil (boiling range, for example, about 255 to more than 277 C) and ground in a ball mill to a fineness of less than 5 microns.
d) Ein emulgierbares Konzentrat wird erhalten aus 15 Gew.-Teilen einer Verbindung der Formel (I) und/oder deren Salze, 75 Gew.-Teilen Cyclohexanon als Lösungsmittel und 10 Gew.-Teilen oxethyliertes Nonylphenol als Emulgator.d) An emulsifiable concentrate is obtained from 15 parts by weight of a compound of the formula (I) and / or salts thereof, 75 parts by weight of cyclohexanone as solvent and 10 parts by weight of ethoxylated nonylphenol as emulsifier.
e) Ein in Wasser dispergierbares Granulat wird erhalten indem mane) A water-dispersible granules are obtained by
75 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze, 10 Gew.-Teile ligninsulfonsaures Calcium, 5 Gew.-Teile Natriumlaurylsulfat, 3 Gew.-Teile Polyvinylalkohol und 7 Gew.-Teile Kaolin mischt, auf einer Stiftmühle mahlt und das Pulver in einem Wirbelbett durch Aufsprühen von Wasser als Granulierflüssigkeit granuliert. Ein in Wasser dispergierbares Granulat wird auch erhalten, indem man 25 Gew.-Teile einer Verbindung der Formel (I) und/oder deren Salze, 5 Gew.-Teile 2,2'-dinaphthylmethan-6,6'-disulfonsaures Natrium 2 Gew.-Teile oleoylmethyltaurinsaures Natrium,75 parts by weight of a compound of formula (I) and / or salts thereof, 10 parts by weight of calcium lignosulfonate, 5 parts by weight of sodium lauryl sulfate, 3 parts by weight of polyvinyl alcohol and 7 parts by weight of kaolin mixed on one Grinds pin mill and the powder granulated in a fluidized bed by spraying water as Granulierflüssigkeit. A water-dispersible granule is also obtained by adding 25 parts by weight of a compound of formula (I) and / or salts thereof, 5 parts by weight of 2,2'-dinaphthylmethane-6,6'-disulfonic acid 2 wt Parts of oleoylmethyl tauric acid sodium,
1 Gew.-Teil Polyvinylalkohol, 17 Gew.-Teile Calciumcarbonat und 50 Gew.-Teile Wasser auf einer Kolloidmühle homogenisiert und vorzerkleinert, anschließend auf einer Perlmühle mahlt und die so erhaltene Suspension in einem Sprühturm mittels einer Einstoffdüse zerstäubt und trocknet. 1 part by weight of polyvinyl alcohol, 17 parts by weight of calcium carbonate and 50 parts by weight of water homogenized on a colloid mill and pre-crushed, then grinded on a bead mill and the resulting suspension in a spray tower by means of a Einstoffdüse atomized and dried.
C. Biologische BeispieleC. Biological examples
I. Herbizide Wirkung im Vorauflauf (PE)I. Pre-emergence herbicidal action (PE)
Samen von mono- bzw. dikotylen Unkrautpflanzen werden in Holzfasertöpfen in sandiger Lehmerde ausgelegt und mit Erde abgedeckt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw. Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha unter Zusatz von 0,2% Netzmittel auf die Oberfläche der Abdeckerde appliziert.Seeds of monocotyledonous or dicotyledonous weed plants are placed in sandy loam soil in wood fiber pots and covered with soil. The compounds of the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then applied to the surface of the cover soil as an aqueous suspension or emulsion having a water application rate of 600 to 800 l / ha with the addition of 0.2% wetting agent applied.
Nach der Behandlung werden die Töpfe im Gewächshaus aufgestellt und unter guten Wachstumsbedingungen für die Testpflanzen gehalten. Die visuelle Bonitur der Schäden an den Versuchspflanzen erfolgt nach einer Versuchszeit von 3 Wochen im Vergleich zu unbehandelten Kontrollen (herbizide Wirkung in Prozent (%): 100% Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontrollpflanzen).After the treatment, the pots are placed in the greenhouse and kept under good growth conditions for the test plants. The visual assessment of the damage to the test plants is carried out after a test period of 3 weeks in comparison to untreated controls (herbicidal action in percent (%): 100% effect = plants are dead, 0% effect = like control plants).
Figure imgf000502_0001
Figure imgf000503_0001
Figure imgf000504_0001
Figure imgf000505_0001
Figure imgf000502_0001
Figure imgf000503_0001
Figure imgf000504_0001
Figure imgf000505_0001
II. Herbizide Wirkung im Nachauflauf (PO)II. Post-emergence herbicidal action (PO)
Samen von mono- bzw. dikotylen Unkrautpflanzen werden in Holzfasertöpfen in sandigem Lehmboden ausgelegt, mit Erde abgedeckt und im Gewächshaus unter guten Wachstumsbedingungen angezogen. 2 bis 3 Wochen nach der Aussaat werden die Versuchspflanzen im Einblattstadium behandelt. Die in Form von benetzbaren Pulvern (WP) oder als Emulsionskonzentrate (EC) formulierten erfindungsgemäßen Verbindungen werden dann als wäßrige Suspension bzw.Seeds of monocotyledonous or dicotyledonous weed plants are placed in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage. The compounds according to the invention formulated in the form of wettable powders (WP) or as emulsion concentrates (EC) are then used as aqueous suspension or
Emulsion mit einer Wasseraufwandmenge von umgerechnet 600 bis 800 l/ha unter Zusatz von 0,2% Netzmittel auf die grünen Pflanzenteile gesprüht. Nach ca. 3 Wochen Standzeit der Versuchspflanzen im Gewächshaus unter optimalen Wachstumsbedingungen wird die Wirkung der Präparate visuell im Vergleich zu unbehandelten Kontrollen bonitiert (herbizide Wirkung in Prozent (%): 100% Wirkung = Pflanzen sind abgestorben, 0 % Wirkung = wie Kontrollpflanzen).Emulsion sprayed with an amount of water equivalent of 600 to 800 l / ha with the addition of 0.2% wetting agent on the green plant parts. After about 3 weeks of life of the test plants in the greenhouse under optimal growth conditions, the effect of the preparations is scored visually compared to untreated controls (herbicidal activity in percent (%): 100% effect = plants are dead, 0% effect = like control plants).
Figure imgf000505_0002
Figure imgf000506_0001
Figure imgf000507_0001
Figure imgf000505_0002
Figure imgf000506_0001
Figure imgf000507_0001
I. Insektizide WirkungI. Insecticidal activity
Beispiel AExample A
Tetranychus-Test, OP-resistent (TETRUR Spritzbehandlung)Tetranychus test, surgical-resistant (TETRUR spray treatment)
Lösungsmittel: 78,0 Gewichtsteile AcetonSolvent: 78.0 parts by weight of acetone
1 ,5 Gewichtsteile Dimethylformamid Emulgator: 0,5 Gewichtsteile Alkylarylpolyglykolether1.5 parts by weight of dimethylformamide emulsifier: 0.5 part by weight of alkylaryl polyglycol ether
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1To prepare a suitable preparation of active compound, 1
Gewichtsteil Wirkstoff mit den angegebenen Mengen Lösungsmittel und Emulgator und verdünnt das Konzentrat mit emulgatorhaltigem Wasser auf die gewünschte Konzentration.Part by weight of active compound with the stated amounts of solvent and emulsifier and the concentrate is diluted with emulsifier-containing water to the desired concentration.
Bohnenblattscheiben (Phaseolus vulgaris), die von allen Stadien der Gemeinen Spinnmilbe (Tetranychus urticae) befallen sind, werden mit einer Wirkstoffzubereitung der gewünschten Konzentration gespritzt.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.
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100 %, dass alle Spinnmilben abgetötet wurden; 0 % bedeutet, dass keine Spinnmilben abgetötet wurden.After the desired time, the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed.
Bei diesem Test zeigen z. B. die in der Tabelle zusammengefassten Verbindungen eine Wirkung von > 80 % bei einer Aufwandmenge von 500 g/ha.In this test, z. B. the compounds summarized in the table an effect of> 80% at a rate of 500 g / ha.
Figure imgf000508_0001
Beispiel B
Figure imgf000508_0001
Example B
Boophilus microplus -Test (BOOPMI Injektion)Boophilus microplus test (BOOPMI injection)
Lösungsmittel: DimethylsulfoxidSolvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.
Die Wirkstofflösung wird in das Abdomen (Boophilus microplus) injiziert, die Tiere werden in Schalen überführt und in einem klimatisierten Raum aufbewahrt. Die Wirkungskontrolle erfolgt auf Ablage fertiler Eier.The drug solution is injected into the abdomen (Boophilus microplus), the animals are transferred to trays and stored in an air-conditioned room. The effect control takes place on storage of fertile eggs.
Nach der gewünschten Zeit wird die Wirkung in % bestimmt. Dabei bedeutet 100%, dass keine Zecke fertile Eier gelegt hat.After the desired time, the effect is determined in%. 100% means that no ticks have laid fertile eggs.
Bei diesem Test zeigen z.B. die in der Tabelle zusammengefassten Verbindungen eine Wirksamkeit ≥ 80 % bei einer Aufwandmenge von 20 μg / TierIn this test, e.g. the compounds summarized in the table have an activity ≥ 80% at an application rate of 20 μg / animal
Figure imgf000509_0001
Figure imgf000509_0001
Beispiel CExample C
Lucilia cuprina-Test (LUCICU)Lucilia cuprina test (LUCICU)
Lösungsmittel: DimethylsulfoxidSolvent: dimethyl sulfoxide
Zur Herstellung einer zweckmäßigen Wirkstoffzubereitung vermischt man 1 Gewichtsteil Wirkstoff mit der angegebenen Menge Lösungsmittel und verdünnt das Konzentrat mit Wasser auf die gewünschte Konzentration.To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent and the concentrate is diluted with water to the desired concentration.
Gefäße, die Pferdefleisch enthalten, das mit der Wirkstoffzubereitung der gewünschten Konzentration behandelt wurde, werden mit Lucilia cuprina Larven besetzt.Vessels containing horsemeat treated with the preparation of active compound of the desired concentration are infested with Lucilia cuprina larvae.
Nach der gewünschten Zeit wird die Abtötung in % bestimmt. Dabei bedeutet 100 %, dass alle Larven abgetötet wurden; 0 % bedeutet, dass keine Larven abgetötet wurden.After the desired time the kill is determined in%. 100% means that all larvae have been killed; 0% means that no larvae have been killed.
Bei diesem Test zeigt z. B. die in der Tabelle zusammengefassten Verbindung eine Wirkung von > 80 % bei einer Aufwandmenge von 100 ppm.In this test, z. B. the compound summarized in the table an effect of> 80% at a rate of 100 ppm.
Figure imgf000510_0001
Figure imgf000510_0001

Claims

Patentansprüche claims
1. Verbindungen der allgemeinen Formel (I) und deren N-Oxide oder Salze1. Compounds of general formula (I) and their N-oxides or salts
worin
Figure imgf000511_0001
wherein
Figure imgf000511_0001
Q ein Aryl- oder Heteroarylrest bedeutet, der jeweils unsubstituiert ist oder substituiert ist durch einen oder mehrere Substituenten, jeweils unabhängig voneinander, ausgewählt aus der Gruppe bestehend aus Halogen, Cyano, Nitro, Alkyl, Haloalkyl, Cycloalkyl, Halocycloalkyl, Hydroxyalkyl, Alkoxyalkyl, Haloalkoxyalkyl, Alkenyl, Haloalkenyl, Alkinyl, Haloalkinyl, Hydroxy, Alkoxy, Haloalkoxy, Alkenyloxy, Haloalkenyloxy, Alkinyloxy, Haloalkinyloxy, Alkylthio, Haloalkylthio, Alkylsulfinyl, Haloalkylsulfinyl, Alkylsulfonyl, Haloalkylsulfonyl, Alkenylthio, Haloalkenylthio, Alkenylsulfinyl, Haloalkenylsulfinyl, Alkenylsulfonyl, Haloalkenylsulfonyl, Alkinylthio, Haloalkinylthio, Alkinylsulfinyl, Haloalkinylsulfinyl, Alkinylsulfonyl, Haloalkinylsulfonyl, Amino, Alkylamino, Dialkylamino, Cycloalkylamino, N-Alkyl-N-cycloalkylamino, Formyl, Alkylcarbonyl, (C=O)OH, (C=O)NH2, Alkoxycarbonyl, Alkylaminocarbonyl, Dialkylaminocarbonyl, Alkylcarbonyloxy, Alkylcarbonylamino, Cycloalkylcarbonylamino,Q is an aryl or heteroaryl group, each unsubstituted or substituted by one or more substituents each independently selected from the group consisting of halogen, cyano, nitro, alkyl, haloalkyl, cycloalkyl, halocycloalkyl, hydroxyalkyl, alkoxyalkyl, haloalkoxyalkyl , Alkenyl, haloalkenyl, alkynyl, haloalkynyl, hydroxy, alkoxy, haloalkoxy, alkenyloxy, haloalkenyloxy, alkynyloxy, haloalkynyloxy, alkylthio, haloalkylthio, alkylsulfinyl, haloalkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkenylthio, haloalkenylthio, alkenylsulfinyl, haloalkenylsulfinyl, alkenylsulfonyl, haloalkenylsulfonyl, alkynylthio, haloalkynylthio , Alkynylsulfinyl, haloalkynylsulfinyl, alkynylsulfonyl, haloalkynylsulfonyl, amino, alkylamino, dialkylamino, cycloalkylamino, N-alkyl-N-cycloalkylamino, formyl, alkylcarbonyl, (C =O) OH, (C =O) NH 2 , alkoxycarbonyl, alkylaminocarbonyl, dialkylaminocarbonyl, Alkylcarbonyloxy, alkylcarbonylamino, cycloalkylcarbonylamino,
Phenylcarbonylamino, Trialkylsilyl, Phenyl, Phenoxy und einem 5- bis 6-gliedrigen heteroaromatischen Ring,Phenylcarbonylamino, trialkylsilyl, phenyl, phenoxy and a 5- to 6-membered heteroaromatic ring,
R1 Wasserstoff, Alkyl, Cycloalkyl oderR 1 is hydrogen, alkyl, cycloalkyl or
Figure imgf000511_0002
bedeutet, Wasserstoff, Alkyl, Cycloalkyl, Cycloalkylalkyl, Arylalkyl, Heterocyclylalkyl, Alkoxyalkyl, Cycloalkoxyalkyl, Aryloxyalkyl, Heterocyclyloxyalkyl, Alkenyl, Cycloakenyl, Cycloalkylalkenyl, Arylalkenyl, Heterocyclylalkenyl, Cycloalkoxyalkenyl, Aryloxyalkenyl, Heterocyclyloxyalkenyl, Alkinyl, Cycloalkylalkinyl, Arylalkinyl, Heterocyclylalkinyl, Cycloalkoxyalkinyl, Aryloxyalkinyl, Heterocyclyloxyalkinyl, Alkylcarbonyl, Alkenylcarbonyl, Alkinylcarbonyl, Arylcarbonyl, Heterocyclylcarbonyl, Aryl oder Heterocyclyl bedeutet, wobei alle Reste außer Wasserstoff gegebenenfalls substituiert sind,
Figure imgf000511_0002
means Is hydrogen, alkyl, cycloalkyl, cycloalkylalkyl, arylalkyl, heterocyclylalkyl, alkoxyalkyl, cycloalkoxyalkyl, aryloxyalkyl, heterocyclyloxyalkyl, alkenyl, cycloalkyl, cycloalkylalkenyl, arylalkenyl, heterocyclylalkenyl, cycloalkoxyalkenyl, aryloxyalkenyl, heterocyclyloxyalkenyl, alkynyl, cycloalkylalkynyl, arylalkynyl, heterocyclylalkynyl, cycloalkoxyalkynyl, aryloxyalkynyl, heterocyclyloxyalkynyl, Alkylcarbonyl, alkenylcarbonyl, alkynylcarbonyl, arylcarbonyl, heterocyclylcarbonyl, aryl or heterocyclyl, all radicals other than hydrogen being optionally substituted,
R3 ein Fragment der allgemeinen Formel (IIa), (IIb), (Mc)1 (Hd), (Me), (Mf)1 (Mg), (Mh)1 (Mi), (Hj), (Mk), (Mm), (Hn), (Mo) oder (Mp)
Figure imgf000513_0001
R 3 is a fragment of general formula (IIa), (IIb), (Mc) 1 (Hd), (Me), (Mf) 1 (Mg), (Mh) 1 (Mi), (Hj), (Mk) , (Mm), (Hn), (Mo) or (Mp)
Figure imgf000513_0001
bedeutet,means
R4, R5, R6, R7 und R8 unabhängig voneinander Wasserstoff, Halogen, Cyano, Nitro,R 4 , R 5 , R 6 , R 7 and R 8 independently of one another are hydrogen, halogen, cyano, nitro,
Alkyl, Cycloalkylalkyl, Arylalkyl, Cycloalkyl, Alkenyl, Cycloalkenyl, Alkinyl, Alkoxy, Cycloalkoxy, Alkenyloxy, Cycloalkenyloxy, Alkinyloxy, Alkylthio, Cycloalkylthio, Alkenylthio, Cycloalkenylthio, Alkinylthio, Alkylsulfinyl, Alkenylsulfinyl, Alkinylsulfinyl, Alkylsulfonyl, Alkenylsulfonyl, Alkinylsulfonyl, wobei jeder der vorgenannten Reste, mit Ausnahme von Wasserstoff, Halogen, Cyano und Nitro, gegebenenfalls substituiert ist, R9CONR10 oder R9R10NSO2, sowieAlkyl, cycloalkylalkyl, arylalkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, cycloalkoxy, alkenyloxy, cycloalkenyloxy, alkynyloxy, alkylthio, Cycloalkylthio, alkenylthio, cycloalkenylthio, alkynylthio, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl wherein each of the foregoing radicals except hydrogen, halogen, cyano and nitro is optionally substituted, R 9 CONR 10 or R 9 R 10 NSO 2 , as well
R9 und R10 unabhängig voneinander Wasserstoff, Alkyl, Cycloalkyl, Alkenyl oderR 9 and R 10 are independently hydrogen, alkyl, cycloalkyl, alkenyl or
Alkinyl bedeuten.Alkynyl mean.
2. Verbindungen nach Anspruch 1 , dadruch gekennzeichnet, dass Q ein Aryl- oder Heteroarylrest bedeutet, der jeweils unsubstituiert ist oder substituiert ist durch einen oder mehrere Substituenten, jeweils unabhängig voneinander, ausgewählt aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (CrC6)-Alkyl, (CrC6)-Haloalkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C1-C6)- Hydroxyalkyl, (C2-C6)-Alkoxyalkyl, (C2-C6)-Haloalkoxyalkyl, (C2-C6)-Alkenyl, (C2-C6)- Haloalkenyl, (C2-C6)-Alkinyl, (C2-C6)-Haloalkinyl, Hydroxy, (CrC6)-Alkoxy, (C1-C6)- Haloalkoxy, (C2-C6)-Alkenyloxy, (C2-C6)-Haloalkenyloxy, (C2-C6)-Alkinyloxy, (C2-C6)- Haloalkinyloxy, (CrC6)-Alkylthio, (CrC6)-Haloalkylthio, (CrC6)-Alkylsulfinyl, (C1-C6)- Haloalkylsulfinyl, (CrC6)-Alkylsulfonyl, (CrC6)-Haloalkylsulfonyl, (C2-C6)-Alkenylthio, (C2-C6)-Haloalkenylthio, (C2-C6)-Alkenylsulfinyl, (C2-C6)-Haloalkenylsulfinyl, (C2-C6)- Alkenylsulfonyl, (C2-C6)-Haloalkenylsulfonyl, (C2-C6)-Alkinylthio, (C2-C6)- Haloalkinylthio, (C2-C6)-Alkinylsulfinyl, (C2-C6)-Haloalkinylsulfinyl, (C2-C6)- Alkinylsulfonyl, (C2-C6)-Haloalkinylsulfonyl, Amino, (Ci-C6)-Alkylamino, (C2-Cs)- Dialkylamino, (C3-C6)-Cycloalkylamino, (C4-C6)-N-Alkyl-N-cycloalkylamino, Formyl, (CrCe)-Alkylcarbonyl, (C=O)OH, (C=O)NH2, (CrC6)-Alkoxycarbonyl, (C1-C6)- Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl, (C-i-C^-Alkylcarbonyloxy, (C1- C6)-Alkylcarbonylamino, (C3-C6)-Cycloalkylcarbonylamino, Phenylcarbonylamino, (C3-C6)-Trialkylsilyl, Phenyl, Phenoxy und einem 5- bis 6-gliedrigen heteroaromatischen Ring. 2. Compounds according to claim 1, characterized dadruch characterized in that Q is an aryl or heteroaryl radical which is in each case unsubstituted or substituted by one or more substituents, each independently selected from the group consisting of halogen, cyano, nitro, (C r C 6 ) -alkyl, (C r C 6 ) -haloalkyl, (C 3 -C 6 ) -cycloalkyl, (C 3 -C 6 ) -halocycloalkyl, (C 1 -C 6 ) -hydroxyalkyl, (C 2 - C 6 ) -alkoxyalkyl, (C 2 -C 6 ) -haloalkoxyalkyl, (C 2 -C 6 ) -alkenyl, (C 2 -C 6 ) -haloalkenyl, (C 2 -C 6 ) -alkynyl, (C 2 - C 6) haloalkynyl, hydroxy, (C r C6) alkoxy, (C 1 -C 6) - haloalkoxy, (C 2 -C 6) alkenyloxy, (C 2 -C 6) -Haloalkenyloxy, (C 2 -C 6) alkynyloxy, (C 2 -C 6) - Haloalkinyloxy, (CrC 6) alkylthio, (C r C6) haloalkylthio, (C r C6) alkylsulfinyl, (C 1 -C 6) - haloalkylsulfinyl, (C r C6) alkylsulfonyl, (C r C6) haloalkylsulfonyl, (C 2 -C 6) -alkenylthio, (C 2 -C 6) -Haloalkenylthio, (C 2 -C 6) alkenylsulfinyl, (C 2 -C 6 ) haloalkenylsulfinyl, (C 2 -C 6 ) - alkenylsulfonyl, (C 2 -C 6 ) -haloalkenylsulfonyl, (C 2 -C 6 ) -alkynylthio, (C 2 -C 6 ) -haloalkynylthio, (C 2 -C 6 ) -alkynylsulfinyl, (C 2 -C 6 ) -haloalkynylsulfinyl, (C 2 -C 6 ) -alkynylsulfonyl, (C 2 -C 6 ) -haloalkynylsulfonyl, amino, (C 1 -C 6 ) -alkylamino, (C 2 -Cs) -dialkylamino, (C 3 -C 6 ) -cycloalkylamino, (C 4 -C 6 ) -N-alkyl-N-cycloalkylamino, formyl, (C 1 -C 6 ) -alkylcarbonyl, (C =O) OH, (C =O) NH 2 , (CrC 6 ) alkoxycarbonyl, (C1-C6) - alkylaminocarbonyl, (C 2 -C 8) dialkylaminocarbonyl, (CiC ^ alkylcarbonyloxy, (C 1 - C 6) alkylcarbonylamino, (C 3 -C 6) -Cycloalkylcarbonylamino, phenylcarbonylamino , (C 3 -C 6 ) -trialkylsilyl, phenyl, phenoxy and a 5- to 6-membered heteroaromatic ring.
3. Verbindungen nach einem der Ansprüche 1 und 2, dadurch gekennzeichnet, dass3. Compounds according to one of claims 1 and 2, characterized in that
R1 Wasserstoff (CrC4)-Alkyl, (C3-C4)-Cycloalkyl oderR 1 is hydrogen (CrC 4) alkyl, (C 3 -C 4) -cycloalkyl or
Figure imgf000515_0001
bedeutet, wobei Q die in Anspruch 1 oder Anspruch 2 genannte Bedeutung hat.
Figure imgf000515_0001
where Q has the meaning given in claim 1 or claim 2.
4. Verbindungen nach einem der Ansprüche 1 bis 3, dadurch gekennzeichnet, dass4. Compounds according to one of claims 1 to 3, characterized in that
R2 Wasserstoff, (CrC6)-Alkyl, wobei der Alkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkyl, wobei der Cycloalkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (CrC4J-AIkOXy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkyl-(Ci-Ce)-alkyl, wobei der Cycloalkylalkylrest unsubstituiert ist, oder nur der Cycloalkylrest substituiert ist, oder nur der Alkylrest substituiert ist, oder sowohl der Cycloalkylrest als auch der Alkylrest substituiert sind, wobei der Cycloalkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (Ci-C-4)-Alkyl, (Cr C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, und der Alkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehendenR 2 is hydrogen, (CrC 6) alkyl, wherein the alkyl group is unsubstituted or existing by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4) -alkoxy or (C r C 4) -alkylthio group substituted, is (C 3 -C 7) -cycloalkyl, where the cycloalkyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4) alkyl, (CrC 4 J -alkoxy or (CrC 4) Alkylthio group, (C 3 -C 7 ) -cycloalkyl- (C 1 -C 6 ) -alkyl wherein the cycloalkylalkyl group is unsubstituted or substituted only the cycloalkyl group, or only the alkyl group is substituted, or both the cycloalkyl group and the alkyl radical are substituted, wherein the cycloalkyl radical is represented by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio , is substituted, and the alkyl radical by one or more substituents, selected It consists of halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio
Gruppe, substituiert ist, Aryl-(CrC6)-alkyl, wobei der Arylalkylrest unsubstituiert ist, oder nur der Arylrest substituiert ist, oder nur der Alkylrest substituiert ist, oder sowohl der Arylrest als auch der Alkylrest substituiert sind, wobei der Arylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (CrC4)-Alkoxy oder (d-C4)-Alkylthio bestehenden Gruppe, substituiert ist, und der Alkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)- Alkoxy oder (Ci -C4)-AI kylthio bestehenden Gruppe, substituiert ist, Heterocyclyl-(Ci-C6)-alkyl, wobei der Heterocyclylalkylrest unsubstituiert ist, oder nur der Heterocyclylrest substituiert ist, oder nur der Alkylrest substituiert ist, oder sowohl der Heterocyclylrest als auch der Alkylrest substituiert sind, wobei der Heterocyclylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC-O-Alkyl, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, und der Alkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C-ι-C4)-Alkoxy oder (C-ι-C4)-Alkylthio bestehenden Gruppe, substituiert ist,Group is substituted, aryl- (CrC 6 ) alkyl, wherein the arylalkyl is unsubstituted, or only the aryl radical is substituted, or only the alkyl radical is substituted, or both the aryl radical and the alkyl radical are substituted, wherein the aryl radical by a or a plurality of substituents selected from the group consisting of halogen, cyano, (C r C 4 ) alkyl, (CrC 4 ) alkoxy or (dC 4 ) alkylthio group, and the alkyl group by one or is substituted alkoxy, or (Ci-C4) alkylthio -AI existing group, heterocyclyl (Ci-C 6) alkyl, wherein the heterocyclylalkyl group is unsubstituted, - more substituents selected from the group consisting of halogen, cyano, (CrC 4) or only the heterocyclyl radical is substituted, or only the alkyl radical is substituted, or both the heterocyclyl radical and the alkyl radical are substituted, where the heterocyclyl radical is represented by one or more substituents selected from among halogen, cyano, (C 1 -C -O-alkyl, ( -C 4) -alkoxy or (C r C 4) alkylthio existing group is substituted, and the alkyl moiety by one or more substituents selected from the group consisting of halogen, cyano, (C-ι-C 4) alkoxy or (C -ι-C 4 ) -Alkylthio existing group, is substituted,
(02-CO)-AI kenyl, wobei der Alkenylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)- Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-Ce)- Alkinyl, wobei der Alkinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder(O 2-CO) -Alkenyl, wherein the alkenyl radical is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) alkylthio, (C 2- Ce) - alkynyl, wherein the alkynyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C r C 4 ) alkoxy or
(CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (CrC6)-Alkylcarbonyl, wobei der Alkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-Ce)- Alkenylcarbonyl, wobei der Alkenylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (Cr C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2- CβJ-Alkinylcarbonyl, wobei der Alkinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (Cr C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist,Is substituted (C r C 4) -alkylthio group consisting of (CrC 6) alkylcarbonyl, wherein the alkyl group is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4) alkoxy or (CrC 4 ) -Alkylthio existing group, (C 2 -Ce) - alkenylcarbonyl, wherein the alkenyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C r C 4 ) alkoxy or (CrC 4 ) -alkylthio group, (C 2 -C 6) -alkynylcarbonyl wherein the alkynyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) Alkylthio group, is substituted,
Arylcarbonyl, wobei der Arylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)- Alkoxy oder (CrC4)-AI kylthio bestehenden Gruppe, substituiert ist, Heterocyclylcarbonyl, wobei der Heterocyclylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano,Arylcarbonyl wherein the aryl radical is unsubstituted or substituted by one or more substituents selected from the group consisting of halo, cyano, (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) alkylthio, heterocyclylcarbonyl wherein the heterocyclyl radical is unsubstituted or by one or more substituents selected from halogen, cyano,
(CrC4)-Alkoxy oder (d-C4)-Alkylthio bestehenden Gruppe, substituiert ist, Aryl, wobei der Arylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, Heterocyclyl, wobei der Heterocyclylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, bedeutet.(C 1 -C 4 ) -Alkoxy or (C 1 -C 4 ) -Alkylthio group, aryl, wherein the aryl radical is unsubstituted or substituted by one or more Substituent selected from the group consisting of halogen, cyano, (C 1 -C 4 ) alkoxy or (C 1 -C 4 ) alkylthio, heterocyclyl wherein the heterocyclyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano , (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio existing group, is substituted.
5. Verbindungen nach einem der Ansprüche 1 bis 4, dadurch gekennzeichnet, dass R4, R5, R6, R7 und R8 unabhängig voneinander Wasserstoff, Halogen, Cyano, Nitro, (C-i-CβJ-Alkyl, wobei der Alkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C1-C4)- Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)- Cycloalkyl-(Ci-C6)-alkyl, wobei der Cycloalkylalkylrest unsubstituiert ist, oder nur der Cycloalkylrest substituiert ist, oder nur der Alkylrest substituiert ist, oder sowohl der Cycloalkylrest als auch der Alkylrest substituiert sind, wobei der Cycloalkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC-4)-Alkyl, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, und der Alkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-5. Compounds according to one of claims 1 to 4, characterized in that R 4 , R 5 , R 6 , R 7 and R 8 independently of one another hydrogen, halogen, cyano, nitro, (Ci-CβJ-alkyl, wherein the alkyl radical unsubstituted or by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4) -, substituted existing alkoxy or (CrC 4) alkylthio group, (C 3 -C 7) - cycloalkyl- (C C 6 ) alkyl, wherein the cycloalkylalkyl is unsubstituted, or only the cycloalkyl radical is substituted, or only the alkyl radical is substituted, or both the cycloalkyl radical and the alkyl radical are substituted, wherein the cycloalkyl radical by one or more substituents selected from is substituted from halogen, cyano, (CrC 4) alkyl, (CrC 4) -alkoxy or (C r C 4) alkylthio existing group and the alkyl moiety by one or more substituents selected from the group consisting of halogen, cyano , (CrC 4 ) -
Alkoxy oder (Ci-C4)-Alkylthio bestehenden Gruppe, substituiert ist, Aryl-(Cr C6)-alkyl, wobei der Arylalkylrest unsubstituiert ist, oder nur der Arylrest substituiert ist, oder nur der Alkylrest substituiert ist, oder sowohl der Arylrest als auch der Alkylrest substituiert sind, wobei der Arylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy or (Ci-C 4 ) -Alkylthio existing group, aryl (C r C 6 ) alkyl, wherein the arylalkyl is unsubstituted, or only the aryl radical is substituted, or only the alkyl radical is substituted, or both the Aryl radical and the alkyl radical are substituted, wherein the aryl radical by one or more substituents selected from among halogen, cyano, (CrC 4 ) -
Alkyl, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, und der Alkylrest durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkyl, wobei der Cycloalkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkenyl, wobei der Alkenylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)- Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkenyl, wobei der Cycloalkenylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (Cr Alkyl, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio group, and the alkyl radical is substituted by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) - Alkylthio existing group, (C 3 -C 7 ) -cycloalkyl, wherein the cycloalkyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (CrC 4 ) alkyl, (CrC 4 ) alkoxy or (C 1 -C 4 ) -alkylthio group, (C 2 -C 6 ) -alkenyl, wherein is existing alkylthio group, substituted (C 3 -C 7) cycloalkenyl, - the alkenyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C r C4) alkoxy or (CrC 4) wherein the cycloalkenyl radical is unsubstituted or substituted (by one or more substituents selected from the group consisting of halogen, cyano, (C r C4) alkyl C r
C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2- C6)-Alkinyl, wobei der Alkinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)- Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (CrCβ)- Alkoxy, wobei der Alkoxyrest unsubstituiert ist oder durch einen oder mehrereC 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio group, (C 2 -C 6 ) -alkynyl, wherein the alkynyl radical is unsubstituted or substituted by one or more substituents selected from among halogen, cyano, (CrC 4 ) alkoxy or (C 1 -C 4 ) -alkylthio group, (C 1 -C 6) -alkoxy, wherein the alkoxy radical is unsubstituted or substituted by one or more
Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkoxy, wobei der Cycloalkoxyrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (Cr C4J-AIkOXy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-Substituents selected from the group consisting of halogen, cyano, (CrC 4 ) alkoxy or (CrC 4 ) alkylthio substituted, (C 3 -C 7 ) -Cycloalkoxy, wherein the cycloalkoxy is unsubstituted or by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4 ) -alkyl, (C 1 -C 4 -alkoxy or (C 1 -C 4 ) -alkylthio), (C 2 -
C6)-Alkenyloxy, wobei der Alkenyloxyrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (Cr C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3- C7)-Cycloalkenyloxy, wobei der Cycloalkenyloxyrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen,C 6) alkenyloxy, wherein the alkenyloxy group is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C r C4) alkoxy or (CrC 4) alkylthio existing group, (C 3 C 7 ) cycloalkenyloxy, where the cycloalkenyloxy radical is unsubstituted or by one or more substituents selected from halogen,
Cyano, (CrC4)-Alkyl, (d-C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkinyloxy, wobei der Alkinyloxyrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4J-AIkOXy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (CrCβJ-Alkylthio, wobei der Alkylthiorest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkylthio, wobei der Cycloalkylthiorest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (C1-Is cyano, (CrC 4) alkyl, (dC 4) alkoxy or (CrC 4) -alkylthio group consisting of substituted, (C 2 -C 6) alkynyloxy, wherein the alkynyloxy group is unsubstituted or substituted by one or more substituents is selected from the group consisting of halogen, cyano, (CrC 4 J -alkoxy or (CrC 4) -alkylthio group consisting of substituted, (CrCβJ alkylthio wherein the alkylthio group is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen Cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio group, (C 3 -C 7 ) -cycloalkylthio, wherein the cycloalkylthio radical is unsubstituted or by one or more substituents selected from among halogen, cyano , (C 1 -C 4 ) -alkyl, (C 1 -
C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2- CβJ-Alkenylthio, wobei der Alkenylthiorest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (Cr C4)-Alkoxy oder (C-i-C-O-Alkylthio bestehenden Gruppe, substituiert ist, (C3- C7)-Cycloalkenylthio, wobei der Cycloalkenylthiorest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehendenC 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio group, (C 2 -CβJ-alkenylthio wherein the alkenylthio radical is unsubstituted or substituted by a or a plurality of substituents selected from the group consisting of halogen, cyano, (C 1 -C 4 ) alkoxy or (C 1 -C 4 -alkylthio), (C 3 -C 7 ) -cycloalkenylthio, wherein the cycloalkenylthio radical is unsubstituted or substituted by one or more Substituents selected from those consisting of halogen, cyano, (CrC 4 ) alkyl, (C r C 4 ) alkoxy or (C r C 4 ) alkylthio
Gruppe, substituiert ist, (C2-C6)-Alkinylthio, wobei der Alkinylthiorest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (Ci-C4)-Alkylthio bestehenden Gruppe, substituiert ist, (CrCβJ-Alkylsulfinyl, wobei der Alkylsulfinylrest unsubstituiert ist oder durch einen oder mehrereSubstituted group, (C 2 -C 6 ) -alkynylthio, wherein the alkynylthio radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or (C 1 -C 4 ) -alkylthio existing group, (CrCβJ-alkylsulfinyl, wherein the alkylsulfinyl is unsubstituted or by one or more
Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkenylsulfinyl, wobei der Alkenylsulfinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (Ci -C4J-AIkOXy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkinylsulfinyl, wobei der Alkinylsulfinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C-ι-C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (CrC6)-Alkylsulfonyl wobei der Alkylsulfonylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C-ι-C4)-Alkoxy oderSubstituents selected from the group consisting of halogen, cyano, (CrC 4 ) alkoxy or (CrC 4 ) -Alkylthio substituted, (C 2 -C 6 ) alkenylsulfinyl, wherein the Alkenylsulfinylrest is unsubstituted or by one or more substituents is selected from the group consisting of halogen, cyano, (Ci -C 4 J -alkoxy or (CrC 4) -alkylthio group consisting of substituted, (C 2 -C 6) alkynylsulfinyl, wherein the Alkinylsulfinylrest is unsubstituted or substituted by one or more is substituted substituent selected from the group consisting of halogen, cyano, (C-ι-C 4) alkoxy or (CrC 4) -alkylthio group consisting of, (C r C6) alkylsulfonyl wherein the alkylsulfonyl group is unsubstituted or substituted by one or a plurality of substituents selected from among halogen, cyano, (C 1 -C 4 ) -alkoxy or
(CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkenylsulfonyl wobei der Alkenylsulfonylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C-ι-C4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkinylsulfonyl wobei der Alkinylsulfonylrest unsubstituiert ist oder durch einen oder mehrere(C 1 -C 4 ) -alkylthio group, (C 2 -C 6 ) -alkenylsulfonyl wherein the alkenylsulfonyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (C 1 -C 4 ) - Alkoxy or (C 1 -C 4 ) -alkylthio group, (C 2 -C 6 ) -alkynylsulfonyl wherein the alkynylsulfonyl radical is unsubstituted or substituted by one or more
Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, NR9R10, R9CONR10 oder R9R10NSO2 bedeuten.Substituents selected from the group consisting of halogen, cyano, (C r C 4 ) alkoxy or (CrC 4 ) -Alkylthio substituted, NR 9 R 10 , R 9 CONR 10 or R 9 R 10 NSO 2 mean.
6. Verbindungen nach einem der Ansprüche 1 bis 5, dadurch gekennzeichnet, dass R2 Wasserstoff, (Ci-C5)-Alkyl, Dihalogenalkyl, Trihalogenalkyl, (CrC3)-Alkoxy- (CrCδJ-alkyl, (C2-C5)-Alkenyl, Dihalogenalkenyl, Trihalogenalkenyl, (CrC3)- Alkoxy-(C2-C5)-alkenyl, (C2-C5)-Alkinyl, Dihalogenalkinyl, Trihalogenalkinyl oder (C-ι-C3)-Alkoxy-(C2-C5)-alkinyl bedeutet, und6. Compounds according to one of claims 1 to 5, characterized in that R 2 is hydrogen, (Ci-C 5) alkyl, dihaloalkyl, trihaloalkyl, (C r C 3) alkoxy (CrC δ J-alkyl, (C 2 -C 5) alkenyl, Dihalogenalkenyl, Trihalogenalkenyl, (CrC 3 ) - alkoxy- (C 2 -C 5 ) -alkenyl, (C 2 -C 5 ) -alkynyl, dihaloalkynyl, trihaloalkynyl or (C 1 -C 3 ) -alkoxy- (C 2 -C 5 ) -alkynyl, and
R4, R5, R6, R7 und R8 unabhängig voneinander Wasserstoff, Halogen, Cyano, Nitro, (CrC5)-Alkyl, Dihalogenalkyl, Trihalogenalkyl, (CrC3)-Alkoxy-(CrC5)-alkyl, (CrC5)-Alkoxy, Dihalogenalkoxy, Trihalogenalkoxy, (CrC3)-Alkoxy-(CrC5)- alkoxy, (CrC3)-Alkenyloxy, (CrC3)-Alkinyloxy, (CrC5)-Alkylthio, Dihalogenalkylthio, Trihalogenalkylthio, (CrC5)-Alkylsulfinyl, (CrC5)-R 4, R 5, R 6, R 7 and R 8 are independently hydrogen, halogen, cyano, nitro, (C r C 5) alkyl, dihaloalkyl, trihaloalkyl, (CrC 3) alkoxy (CrC 5) alkyl , (CrC 5 ) -alkoxy, dihaloalkoxy, trihaloalkoxy, (CrC 3 ) -alkoxy- (CrC 5 ) -alkoxy, (C r C 3 ) -alkenyloxy, (C r C 3 ) -alkynyloxy, (C r C 5 ) Alkylthio, dihaloalkylthio, trihaloalkylthio, (C r C 5 ) -alkylsulfinyl, (C r C 5 ) -
Alkylsulfonyl, (CrC5)-Dialkylamino, (CrCsJ-Alkylcarbonylamino oder (C3-C7)- Cycloalkylcarbonylamino bedeuten.Alkylsulfonyl, (CrC 5 ) -dialkylamino, (CrCsJ-alkylcarbonylamino or (C 3 -C 7 ) -cycloalkylcarbonylamino.
7. Verbindungen nach einem der Ansprüche 1 bis 6, dadurch gekennzeichnet, dass R2 Wasserstoff, (CrC5)-Alkyl, (CrC3)-Alkoxy-(CrC5)-alkyl oder (C2-C5)-Alkinyl, und7. A compound according to any one of claims 1 to 6, characterized in that R 2 is hydrogen, (C r C 5 ) alkyl, (CrC 3 ) alkoxy (CrC 5 ) alkyl or (C 2 -C 5 ) - Alkynyl, and
R4, R5, R6, R7 und R8 unabhängig voneinander Wasserstoff, Fluor, Chlor, Brom, Cyano, Nitro, (CrC4)-Alkyl, Difluormethyl und Trifluormethyl, (CrC4)-Alkoxy,R 4, R 5, R 6, R 7 and R 8 are independently hydrogen, fluorine, chlorine, bromine, cyano, nitro, (C r C4) alkyl, difluoromethyl and trifluoromethyl, (C r C4) alkoxy,
Difluormethoxy und Trifluormethoxy, (CrC4)-Alkylthio, Difluormethylthio, Trifluormethylthio, (CrC2)-Alkylsulfinyl, (CrC2)-Alkylsulfonyl oder (CrC2)- Dialkylamino bedeuten.Difluoromethoxy and trifluoromethoxy, (CrC 4 ) -Alkylthio, difluoromethylthio, trifluoromethylthio, (CrC 2 ) alkylsulfinyl, (C r C 2 ) alkylsulfonyl or (C r C 2 ) - dialkylamino mean.
8. Verbindungen nach einem der Ansprüche 1 bis 7, dadurch gekennzeichnet, dass8. Compounds according to one of claims 1 to 7, characterized in that
R9 und R10 unabhängig voneinander Wasserstoff, (CrC6)-Alkyl bedeuten, wobei derR 9 and R 10 independently of one another denote hydrogen, (C 1 -C 6 ) -alkyl, where the
Alkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4J-AIkOXy oder (CrC4)-Alkyl radical is unsubstituted or by one or more substituents selected from among halogen, cyano, (CrC 4 J -alkoxy or (CrC 4 ) -
Alkylthio bestehenden Gruppe, substituiert ist, (C3-C7)-Cycloalkyl, wobei der Cycloalkylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkyl, (C-ι-C4)-Alkoxy oder (C-i-C4)-Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkenyl, wobei der Alkenylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C-ι-C4)-Alkoxy oder (CrC4)- Alkylthio bestehenden Gruppe, substituiert ist, (C2-C6)-Alkinyl, wobei derAlkylthio group, (C 3 -C 7 ) -cycloalkyl, where the cycloalkyl radical is unsubstituted or substituted by one or more substituents, is selected from the group consisting of halogen, cyano, (CrC 4) alkyl, (C-ι-C 4) -alkoxy or (CiC 4) alkylthio existing substituted, (C 2 -C 6) -alkenyl, wherein the Alkenyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (C-ι-C 4 ) alkoxy or (CrC 4 ) - alkylthio, (C 2 -C 6 ) alkynyl , where the
Alkinylrest unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (C1-C4)- Alkylthio bestehenden Gruppe, substituiert ist, bedeuten.Alkynyl is unsubstituted or substituted by one or more substituents selected from the group consisting of halogen, cyano, (CrC 4 ) alkoxy or (C 1 -C 4 ) - alkylthio group.
9. Verbindungen nach einem der Ansprüche 1 bis 8, dadurch gekennzeichnet, dass Q ein Rest ist, der ausgewählt ist aus der aus Q1-Q17 bestehenden Gruppe 9. Compounds according to one of claims 1 to 8, characterized in that Q is a radical which is selected from the group consisting of Q1-Q17
Figure imgf000522_0001
Figure imgf000522_0001
und unsubstituiert ist oder durch einen oder mehrere Substituenten, ausgewählt aus der aus R11, R12, R13, R14 oder R11a bestehenden Gruppe, substituiert ist, wobeiand is unsubstituted or substituted by one or more substituents selected from the group consisting of R 11 , R 12 , R 13 , R 14 or R 11a , wherein
R11, R12, R13, R14 unabhängig voneinander Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Cycloalkylalkyl, Arylalkyl, Cycloalkyl, Alkenyl, Cycloalkenyl, Alkinyl, Alkoxy, Cycloalkoxy, Alkenyloxy, Cycloalkenyloxy, Alkinyloxy, Alkylthio, Cycloalkylthio, Alkenylthio, Cycloalkenylthio, Alkinylthio, Alkylsulfinyl, Alkenylsulfinyl, Alkinylsulfinyl, Alkylsulfonyl, Alkenylsulfonyl, Alkinylsulfonyl, wobei jeder Rest außer der vier erstgenannten Reste gegebenenfalls durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (C1-C4)- Alkoxy oder (CrC4)-Alkylthio bestehenden Gruppe, substituiert ist, NR9R10, R9CONR10 oder R9R10NSO2 und R9 oder R10 unabhängig voneinander, die in einem der Ansprüche 1 oder 8 angegebene Bedeutung haben,R 11 , R 12 , R 13 , R 14 independently of one another are hydrogen, halogen, cyano, nitro, alkyl, cycloalkylalkyl, arylalkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, cycloalkoxy, alkenyloxy, cycloalkenyloxy, alkynyloxy, alkylthio, cycloalkylthio, alkenylthio , Cycloalkenylthio, alkynylthio, alkylsulfinyl, alkenylsulfinyl, Alkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, each being other than the first four radicals are optionally substituted by one or more substituents selected from the group consisting of halogen, cyano, (C 1 -C 4) - alkoxy or existing (CrC 4) -alkylthio group, NR 9 R 10 , R 9 CONR 10 or R 9 R 10 NSO 2 and R 9 or R 10 independently of one another have the meaning given in one of claims 1 or 8,
R11a Wasserstoff, Halogen, Cyano, Nitro, Alkyl, Cycloalkylalkyl, Arylalkyl,R 11a is hydrogen, halogen, cyano, nitro, alkyl, cycloalkylalkyl, arylalkyl,
Cycloalkyl, Alkenyl, Cycloalkenyl, Alkinyl, Alkoxy, Cycloalkoxy, Alkenyloxy, Cycloalkenyloxy, Alkinyloxy, Alkylthio, Cycloalkylthio, Alkenylthio,Cycloalkyl, alkenyl, cycloalkenyl, alkynyl, alkoxy, cycloalkoxy, alkenyloxy, cycloalkenyloxy, alkynyloxy, alkylthio, cycloalkylthio, alkenylthio,
Cycloalkenylthio, Alkinylthio, Alkylsulfinyl, Alkenylsulfinyl, Alkinylsulfinyl, Alkylsulfonyl, Alkenylsulfonyl, Alkinylsulfonyl, wobei jeder Rest außer der vier erstgenannten Reste gegebenenfalls durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oder (C1-C4)- Alkylthio bestehenden Gruppe, substituiert ist, oder R9R10NSO2 bedeutet, undCycloalkenylthio, alkynylthio, alkylsulfinyl, alkenylsulfinyl, alkynylsulfinyl, alkylsulfonyl, alkenylsulfonyl, alkynylsulfonyl, each being other than the first four radicals are optionally substituted by one or more substituents selected from the group consisting of halogen, cyano, (C r C4) alkoxy or (C 1 -C 4 ) - alkylthio group, or R 9 R 10 is NSO 2 , and
T Wasserstoff, (d-CβJ-Alkyl, Benzyl oder Phenyl bedeutet, wobei jeder der drei letzt genannten Reste gegebenenfalls durch einen oder mehrere Substituenten, ausgewählt aus der aus Halogen, Cyano, (CrC4)-Alkoxy oderT is hydrogen, (C 1 -C 6 -alkyl, benzyl or phenyl, wherein each of the last three radicals optionally substituted by one or more substituents selected from among halogen, cyano, (C r C 4 ) alkoxy or
(CrC4)-Alkylthio bestehenden Gruppe, substituiert ist.(CrC 4 ) -Alkylthio existing group is substituted.
10. Verbindungen nach einem der Ansprüche 1 bis 9, dadurch gekennzeichnet, dass falls Q Phenyl, Phenoxy oder ein 5- bis 6-gliedriger heteroaromatischer Ring ist, diese einfach, zweifach oder dreifach mit R15 substituiert sind, wobei10. Compounds according to one of claims 1 to 9, characterized in that if Q is phenyl, phenoxy or a 5- to 6-membered heteroaromatic ring, these are mono-, di- or trisubstituted by R 15 , wherein
R15 Halogen, Cyano, Nitro, (CrC4)-Alkyl, (CrC4)-Haloalkyl, (C3-C6)-Cycloalkyl, (C3-C6)-Halocycloalkyl, (C2-C4)-Alkenyl, (C2-C4)-Haloalkenyl, (C2-C4)-Alkinyl, (C2-C4)-Haloalkinyl, (CrC4)-Alkoxy, (CrC4)-Haloalkoxy, (CrC4)-Alkylthio, (C1- C4)-Haloalkylthio, (CrC4)-Alkylsulfinyl, (CrC4)-Alkylsulfonyl, (C1-C4)-R 15 is halogen, cyano, nitro, (CrC 4) alkyl, (CrC 4) -haloalkyl, (C 3 -C 6) -cycloalkyl, (C 3 -C 6) halocycloalkyl, (C 2 -C 4) - alkenyl, (C 2 -C 4) haloalkenyl, (C 2 -C 4) -alkynyl, (C 2 -C 4) haloalkynyl, (C r C4) alkoxy, (CrC 4) haloalkoxy, (C r C 4) -alkylthio, (C 1 - C 4) haloalkylthio, (C r C4) alkylsulfinyl, (C r C4) -alkylsulfonyl, (C 1 -C 4) -
Alkylamino, (C2-C8)-Dialkylamino, (C3-C6)-Cycloalkylamino, (C4-C6)-N-Alkyl-N- cycloalkylamino, (CrC4)-Alkylcarbonyl, (CrC6)-Alkoxycarbonyl, (C-i-Cβ)- Alkylaminocarbonyl, (C2-C8)-Dialkylaminocarbonyl oder (C3-C6)-Trialkylsilyl bedeutet.Alkylamino, (C 2 -C 8 ) -dialkylamino, (C 3 -C 6 ) -cycloalkylamino, (C 4 -C 6 ) -N-alkyl-N- cycloalkylamino, (CrC 4) alkylcarbonyl, (CrC 6) alkoxycarbonyl, (Ci-Cβ) - alkylaminocarbonyl, (C 2 -C 8) means dialkylaminocarbonyl or (C 3 -C 6) trialkylsilyl.
11. Verbindung nach einem der Ansprüche 1 bis 10, dadurch gekennzeichnet, dass falls Q Phenyl, Phenoxy oder ein 5- bis 6-gliedriger heteroaromatischer Ring ist zwei benachbarte Reste an Q zusammen einen difunktionellen Rest -OCH2O-, -0(CH2J2O-, -CH2CH2O-, -OCH(CH3)O-, -OC(CHg)2O-, -CH2CH2CH2O-, -OCF2O-, -CF2CF2O-, -OCF2CF2O- oder -CH=CH-CH=CH- bilden.11. A compound according to any one of claims 1 to 10, characterized in that if Q is phenyl, phenoxy or a 5- to 6-membered heteroaromatic ring is two adjacent residues of Q together a difunctional radical -OCH 2 O-, -0 (CH 2 J 2 O-, -CH 2 CH 2 O-, -OCH (CH 3 ) O-, -OC (CHg) 2 O-, -CH 2 CH 2 CH 2 O-, -OCF 2 O-, -CF 2 CF 2 O, -OCF 2 CF 2 O- or -CH = CH-CH = CH- form.
12. Verbindung nach einem der Ansprüche 1 bis 11 , dadurch gekennzeichnet, dass die Reste R4, R5, R6, R7 und R8 jeweils mit einem oder mehreren der Reste R16 substituiert sind, wobei12. A compound according to any one of claims 1 to 11, characterized in that the radicals R 4 , R 5 , R 6 , R 7 and R 8 are each substituted with one or more of the radicals R 16 , wherein
R16 ausgewählt ist aus der Gruppe bestehend aus Halogen, Cyano, Nitro, (CrC4)- Alkyl außer für den Fall, dass es sich bei dem entsprechenden Rest R4, R5, R6, R7 oder R8 jeweils um einen Alkylrest handelt, (CrC4)-Alkoxy, (CrC4)- Haloalkoxy, (CrC4)-Alkylthio, (CrC4)-Haloalkylthio, (CrC4)-Alkylsulfinyl, (C1- C4)-Alkylsulfonyl, (CrC4)-Alkylamino, (C2-C8)-Dialkylamino, (C3-C6)- Cycloalkylamino, (C4-C6)-N-Alkyl-N-cycloalkylamino, (C-pCO-Alkylcarbonyl,R 16 is selected from the group consisting of halogen, cyano, nitro, (C 1 -C 4 ) -alkyl except in the event that the corresponding radical R 4 , R 5 , R 6 , R 7 or R 8 is in each case a Alkyl radical, (C r C 4 ) alkoxy, (C r C 4 ) haloalkoxy, (C r C 4 ) alkylthio, (C r C 4 ) haloalkylthio, (C r C 4 ) alkylsulfinyl, (C 1 - C 4) alkylsulfonyl, (C r C4) alkylamino, (C 2 -C 8) dialkylamino, (C 3 -C 6) - cycloalkylamino, (C 4 -C 6), -N-alkyl-N cycloalkylamino, (C-pCO-alkylcarbonyl,
(Ci-C6)-Alkoxycarbonyl, (CrC^-Alkylaminocarbonyl, (C2-Cs)- Dialkylaminocarbonyl oder (C3-C6)-Trialkylsilyl. (Ci-C 6) -alkoxycarbonyl, (CrC ^ alkylaminocarbonyl, (C 2 -Cs) - dialkylaminocarbonyl or (C 3 -C 6) trialkylsilyl.
13. Verfahren zur Herstellung einer Verbindung der Formel (I) nach einem der Ansprüche 1 bis 12, dadurch gekennzeichnet, dass eine Carbonsäure (III)13. A process for preparing a compound of formula (I) according to any one of claims 1 to 12, characterized in that a carboxylic acid (III)
Figure imgf000525_0001
(III)
Figure imgf000525_0001
(III)
mit einem Hydrazin (IV)with a hydrazine (IV)
Figure imgf000525_0002
(IV)
Figure imgf000525_0002
(IV)
umgesetzt wird, wobei die Aktivierung der Carbonsäure (III) mit einem Kondensationsreagenz erfolgt.is reacted, wherein the activation of the carboxylic acid (III) is carried out with a condensation reagent.
14. Verfahren zur Herstellung einer Verbindung der Formel (I) nach einem der Ansprüche 1 bis 12, dadurch gekennzeichnet, dass eine Carbonsäure (IM)14. Process for the preparation of a compound of the formula (I) according to one of claims 1 to 12, characterized in that a carboxylic acid (IM)
Figure imgf000525_0003
Figure imgf000525_0003
(III)(III)
mit einem Halogenierungsreagenz in ein Carbonylhalogenid (V)with a halogenating reagent in a carbonyl halide (V)
Figure imgf000525_0004
Figure imgf000525_0004
Y = Cl, Br (V) umgewandelt wird, welches dann in Gegenwart einer Base mit einem Hydrazin (IV)Y = Cl, Br (V) which is then converted in the presence of a base with a hydrazine (IV)
Figure imgf000526_0001
(IV)
Figure imgf000526_0001
(IV)
umgesetzt wird.is implemented.
15. Herbizides oder pflanzenwachstumsregulierendes Mittel, dadurch gekennzeichnet, dass es eine wirksame Menge einer oder mehrerer derA herbicidal or plant growth regulating agent, characterized in that it contains an effective amount of one or more of
Verbindungen der Formel (I) oder eines ihrer Λ/-Oxide oder eines ihrer Salze nach einem der Ansprüche 1 bis 12 und mindestens eines der im Pflanzenschutz üblichen Formulierungshilfsmittel enthält.Compounds of formula (I) or one of their Λ / oxides or one of its salts according to one of claims 1 to 12 and at least one customary in plant protection formulation auxiliaries.
16. Insektizides Mittel, dadurch gekennzeichnet, dass es eine wirksame Menge einer oder mehrerer der Verbindungen der Formel (I) oder eines ihrer Λ/-Oxide oder eines ihrer Salze nach einem der Ansprüche 1 bis 12 und mindestens eines der im Pflanzenschutz üblichen Formulierungshilfsmittel enthält.16. Insecticidal agent, characterized in that it contains an effective amount of one or more of the compounds of formula (I) or one of their Λ / oxides or one of its salts according to any one of claims 1 to 12 and at least one customary in plant protection formulation auxiliaries ,
17. Verfahren zur Bekämpfung von Schadpflanzen und zur17. Method for controlling harmful plants and for
Wachstumsregulierung von Pflanzen, dadurch gekennzeichent, dass man eine wirksame Menge einer oder mehrerer der Verbindungen der Formel (I) oder eines ihrer Λ/-Oxide oder eines ihrer Salze nach einem der Ansprüche 1 bis 12 auf Schadpflanzen, bzw. Pflanzen, Pflanzensamen oder die Fläche auf der die Pflanzen wachsen, appliziert.Growth regulation of plants, characterized in that an effective amount of one or more of the compounds of formula (I) or one of their Λ / oxides or one of its salts according to one of claims 1 to 12 on harmful plants, or plants, plant seeds or Area on which the plants grow, applied.
18. Verfahren zur Bekämpfung von Insekten, dadurch gekennzeichnet, dass man eine wirksame Menge einer oder mehrerer der Verbindungen der Formel (I) oder eines ihrer N-Oxide oder eines ihrer Salze nach einem der Ansprüche 1 bis 12 mit Insekten in Kontakt bringt oder auf deren Lebensraum appliziert. 18. A method for controlling insects, characterized in that bringing an effective amount of one or more of the compounds of formula (I) or one of its N-oxides or one of its salts according to one of claims 1 to 12 in contact with insects or on their habitat applied.
19. Verwendung von Verbindungen der allgemeinen Formel (I) oder eines ihrer N- Oxide oder eines ihrer Salze nach einem der Ansprüche 1 bis 12 zur Bekämpfung von unerwünschtem Pflanzenwachstum.19. Use of compounds of general formula (I) or one of their N-oxides or one of their salts according to one of claims 1 to 12 for controlling unwanted plant growth.
20. Verwendung von Verbindungen der allgemeinen Formel (I) oder eines ihrer ZV- Oxide oder eines ihrer Salze nach einem der Ansprüche 1 bis 12 zur Bekämpfung von tierischen Schädlingen, insbesondere von Insekten. 20. Use of compounds of the general formula (I) or one of their ZV oxides or one of their salts according to one of claims 1 to 12 for controlling animal pests, in particular insects.
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