WO2010078906A2 - Hydrazides, procédé permettant leur préparation et leur utilisation en tant qu'herbicides et insecticides - Google Patents

Hydrazides, procédé permettant leur préparation et leur utilisation en tant qu'herbicides et insecticides 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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WO2010078906A3 (fr
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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.

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Abstract

La présente invention concerne des composés hydrazides de formule générale (I) dans laquelle Q et R3 sont un radical aryle ou hétaryle qui est respectivement non substitué ou substitué par un ou plusieurs substituants, et R1 est hydrogène, alkyle en (C1-C4), cycloalkyle en (C3-C4) ou un composé de formule (I'), et R2 est hydrogène, alkyle, cycloalkyle, cycloalkylalkyle, arylalkyle, hétérocyclylalkyle, cycloalcoxyalkyle, aryloxyalkyle, hétérocyclyloxyalkyle, alcényle, cycloacényle, cycloalkylalcényle, arylalcényle, hétérocyclylalcényle, cycloalcoxyalcényle, aryloxyalcényle, hétérocyclyloxyalcényle, alcynyle, cycloalkylalcynyle, arylalcynyle, hétérocyclylalcynyle, cycloalcoxyalcynyle, aryloxyalcynyle, hétérocyclyloxyalcynyle, alkylcarbonyle, alcénylcarbonyle, alcynylcarbonyle, arylcarbonyle, hétérocyclylcarbonyle, aryle ou hétérocyclyle, tous les radicaux excepté l'hydrogène étant éventuellement substitués. L'invention a également pour objet un procédé pour lutter contre la croissance de végétaux indésirables et contre des insectes indésirables, ainsi que l'utilisation de composés de formule (I) en tant qu'herbicides et insecticides.
PCT/EP2009/008813 2008-12-18 2009-12-10 Hydrazides, procédé permettant leur préparation et leur utilisation en tant qu'herbicides et insecticides WO2010078906A2 (fr)

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