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WO2014060381A1 - Composés hétérocycliques pour la lutte contre les nuisibles - Google Patents

Composés hétérocycliques pour la lutte contre les nuisibles Download PDF

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Publication number
WO2014060381A1
WO2014060381A1 PCT/EP2013/071469 EP2013071469W WO2014060381A1 WO 2014060381 A1 WO2014060381 A1 WO 2014060381A1 EP 2013071469 W EP2013071469 W EP 2013071469W WO 2014060381 A1 WO2014060381 A1 WO 2014060381A1
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alkyl
optionally substituted
group
radical
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English (en)
Inventor
Peter Jeschke
Thomas Bretschneider
Adeline KÖHLER
Reiner Fischer
Martin FÜSSLEIN
Olga Malsam
Kerstin Ilg
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Bayer CropScience AG
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Bayer CropScience AG
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond

Definitions

  • the present application relates to novel heterocyclic compounds, to processes for their preparation and their use for controlling animal pests, which include arthropods and in particular insects, as well as intermediates for the preparation of the heterocyclic compounds.
  • Plant protection products including pesticides, must meet many requirements, for example, in terms of the level, duration and breadth of their effect and possible use. Issues of toxicity, of the ability to be combined with other active substances or formulation auxiliaries play a role, as well as the question of the effort that has to be spent on the synthesis of an active substance. Furthermore, resistances can occur. For all these reasons, the search for new pesticides can not be considered complete and there is a constant need for new compounds with improved properties over the known compounds, at least with respect to individual aspects.
  • the object of the present invention was to provide compounds which broaden the spectrum of pesticides from various aspects.
  • R is a radical from the group consisting of hydrogen, alkyl, haloalkyl, alkenyl, alkynyl, cycloalkyl and halogenocycloalkyl
  • R 1 is a radical from the series halogen, cyano, nitro, alkyl, haloalkyl, alkenyl, haloalkenyl, alkoxy, haloalkoxy, cycloalkyl, Halocycloalkyl, alkylthio, haloalkylthio, alkylsulfinyl, haloalylsulfinyl, alkylsulfonyl, haloalkylsulfonyl,
  • R 2 is a radical selected from the group consisting of hydrogen, alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkenyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylthioalkyl, alkenylthioalkyl, cyanoalkyl, alkoxyalkyl,
  • R 3 is a radical of the formula in which one radical is selected from the group consisting of alkyl, haloalkyl, alkoxy, haloalkoxy, alkoxyalkyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylthio, haloalkylsulfinyl, haloalkylsulfonyl, alkylthioalkyl, alkylsulfinylalkyl, alkylsulfonylalkyl, alkylthioalkyloxy, alkylsulfinylalkyloxy, alkylsulfonylalkyloxy, haloalkylthioalkyl, haloalkylsulfinylalkyl, haloalkylsulfonylalkyl, alkylthioalkenyl , Alkylsulfinylalkenyl,
  • R 5 is a radical from the group consisting of hydrogen (only in the radicals C-33, C-36 and C-42), halogen, cyano, nitro, amino, hydroxyl and in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, Alkoxy, alkenyloxy, alkynyloxy, cycloalkyloxy, alkylcarbonyloxy, alkenylcarbonyloxy, alkynylcarbonyloxy, cycloalkylcarbonyloxy, alkoxycarbonyloxy, alkylsulfonyloxy, alkylamino, alkenylamino, alkynylamino, cycloalkylamino, alkylthio, haloalkylthio, alkenylthio, alkynylthio, cycloalkylthio, alkylsulfinyl, alkylsulf
  • Alkylthiocarbonylamino, bicycloalkyl, aryl, aryloxy, heteroaryl and heteroaryloxy, where the substituents are independently selected from halogen, cyano, nitro, hydroxy and amino, is a radical from the series consisting of hydrogen, alkyl, cycloalkyl, haloalkyl, alkenyl, alkynyl, cycloalkylalkyl, cyanoalkyl, alkylcarbonyl, alkenylcarbonyl, haloalkylcarbonyl, haloalkenylcarbonyl, alkoxyalkyl, alkoxycarbonyl, alkylsulfonyl and haloalkylsulfonyl, or a radical from the series
  • X is oxygen or sulfur
  • n is 1 or 2 .
  • R 8 is a radical from the group consisting of hydrogen, alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, alkenyl, alkoxyalkyl, in each case optionally halogen-substituted alkylcarbonyl and alkylsulfonyl, optionally halogen-substituted alkoxycarbonyl, if appropriate by halogen, alkyl, alkoxy, haloalkyl and cyano substituted cycloalkylcarbonyl, or a cation, such as a mono- or divalent metal ion (for example, alkali metal ions such as Li + , Na + , Cs + and K + and alkaline earth metal ions such as
  • R 15 and R 9 independently of one another from the series each optionally substituted amino, alkyl, alkenyl and alkynyl, each optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings at least one heteroatom selected from the group sulfur, oxygen (oxygen atoms not may be immediately adjacent) and contain nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
  • R 8 and R 15 together with the NS (0) n group to which they are attached, may also form a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing one or more further heteroatoms selected from the group consisting of sulfur, Oxygen (where oxygen atoms are not allowed to be immediately adjacent) and nitrogen and / or at least one carbonyl group,
  • R 17 is a radical from the series in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings are at least one heteroatom from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and each may contain nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
  • R 16 is a radical from the group consisting of hydrogen, in each case optionally substituted alkyl, alkoxy, alkenyl and alkynyl, in each case optionally substituted cycloalkyl, cycloalkylalkyl and cycloalkenyl, in which the rings are at least one heteroatom selected from the group consisting of sulfur, oxygen (oxygen atoms not being directly adjacent may each contain) and nitrogen, each optionally substituted aryl, heteroaryl, arylalkyl and heteroarylalkyl and an optionally substituted amino group,
  • R 8 and R 17 may also together with the NC (X) group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing one or more further heteroatoms selected from sulfur, oxygen (where oxygen atoms not immediately adjacent) and may contain nitrogen and / or at least one carbonyl group,
  • R 10 is hydrogen or alkyl
  • R 8 and R 10 together with the N atoms to which they are attached, may represent a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing at least one further heteroatom selected from the group consisting of sulfur, oxygen (where Sauers toffatome not be immediately adjacent) and may contain nitrogen and / or at least one carbonyl group,
  • R and R in the radical (Dl) together with the NS (0) n group to which they are attached can form a saturated or unsaturated and optionally substituted 4- to 8-membered ring which comprises one or more further heteroatoms the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or at least one carbonyl group,
  • R and R may also together with the NS (0) n group to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing one or more further heteroatoms selected from the group consisting of sulfur, oxygen (where oxygen atoms are not allowed to be immediately adjacent) and may contain nitrogen and / or at least one carbonyl group,
  • R 8 and R 16 may also together with the N-atom to which they are attached form a saturated or unsaturated and optionally substituted 4- to 8-membered ring containing one or more further heteroatoms selected from the group consisting of sulfur and oxygen (where Oxygen atoms may not be immediately adjacent) and may contain nitrogen and / or at least one carbonyl group,
  • L is oxygen or sulfur
  • R and R independently of one another are each an optionally substituted radical from the series alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkynyloxy, cycloalkyl, cycloalkyloxy, cycloalkenyloxy, cycloalkylalkoxy, alkylthio, alkenylthio, phenoxy, phenylthio, benzyloxy, benzylthio, heteroaryloxy, heteroarylthio, Heteroarylalkoxy and heteroarylalkylthio,
  • R and R may also together with the phosphorus atom to which they are attached form a saturated or unsaturated and optionally substituted 5- to 7-membered ring, the or two heteroatoms from the series oxygen (oxygen atoms may not be immediately adjacent) and sulfur may contain and
  • R and R are each independently an optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl
  • R 18 and R 19 are independently hydrogen or each optionally substituted radical from the series alkyl, alkenyl, alkynyl, phenyl and phenylalkyl
  • novel compounds of the formula (I) have a good activity as pest control agents, for example against arthropods and in particular insects, moreover, in general, especially against crop plants are very well plant tolerated and / or favorable toxicological and / or environmental properties feature.
  • B-1 B-2 wherein the dashed line represents the bond to A and the arrow represents the bond to the group NR 2 R 3 .
  • Ci-C6-alkyl stands for a radical from the series halogen, cyano, nitro, Ci-C6-alkyl, Ci-C6-haloalkyl, C 2 - C 6 alkenyl, C 2 -C 6 haloalkenyl, Ci-C6-alkoxy, Ci-C6-halogenoalkoxy , C 3 -C 6 -cycloalkyl, C 3 -C 6 -halocycloalkyl, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 6 -halogenoylsulfinyl, C 1 -C 6 -alkylsulfonyl, C 1 -C 6 -haloalkylsulfonyl.
  • C 1 -C 6 -alkyl is a radical from the group consisting of hydrogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 6 -alkoxy, C 2 - C6-alkenyloxy, C 2 -C 6 alkynyloxy, C 3 -C 6 cycloalkyloxy, Ci-C6 alkylthio-Ci-C 6 alkyl, C 2 -C 6 alkenylthio-Ci-C 6 alkyl, cyano C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl.
  • Ci-C6-alkyl stands for the rest of the formula is a radical from the series Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy, Ci-Ce-haloalkoxy, Ci-C6-alkoxy-Ci-C6-alkyloxy, Ci-C6-alkylthio, Ci C6-alkylsulfinyl, CI-C ⁇ - alkylsulfonyl, Ci-C6-haloalkylthio, Ci-C6 haloalkylsulfinyl, Ci-Ce
  • Ci-Ce-alkylthio-Ci-Ce-alkyl Ci-C 6 alkylsulfinyl-Ci-C 6 alkyl, C 6 - alkylsulphonyl-Ci-Ce-alkyl, Ci-C 6 -alkylthio-C 6 alkyloxy, Ci-C 6 alkylsulfinyl-Ci-C 6 - alkyloxy, Ci-C6-alkylsulfonyl-Ci-C6-alkyloxy, Ci-C6-halogenoalkylthio-Ci-C6-alkyl, Ci-Ce-haloalkylsulfinyl-Ci C6-alkyl, Ci-C6-haloalkylsulfonyl-Ci-C6-alkyl, Ci-C6-alkylthio, C 2 -C 6 alkenyl, Ci-C 6 alkyl
  • Alkylaminocarbonyl di- (C 1 -C 6 -alkyl) aminocarbonyl, aminothiocarbonyl, C 1 -C 5
  • R 5 is a radical from the series hydrogen (only in the radicals C-33, C-36 and C-42), halogen, cyano, nitro, amino, hydroxy, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-Ci-C6-alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-Ci-C 6 alkyl, C 6 alkoxy, Ci-C6-haloalkoxy, C3-C6-alkenyloxy, C 3 -C 6 alkynyloxy, C 3 -C 6 cycloalkyloxy, C ⁇ -
  • Ci-C6-alkoxycarbonyl aminocarbonyl, Ci-C6-alkylaminocarbonyl, di (Ci-C6) alkylaminocarbonyl, aminothiocarbonyl, Ci-C6-alkylaminosulfonyl, Cl-C ⁇ - alkylsulfonylamino, Ci-C6 Alkylcarbonylamino, C 1 -C 6 -alkylthiocarbonylamino, aryl, aryloxy, heteroaryl and heteroaryloxy.
  • R 6 is a radical selected from hydrogen, Ci-C6-alkyl, C3-C6-cycloalkyl, CI-C ⁇ - haloalkyl, C 3 -C 6 alkenyl, C 2 -C 6 alkynyl, C 3 - C 6 -cycloalkyl-C 1 -C 6 -alkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkylcarbonyl, C 2 -C 6 -alkenylcarbonyl, C 1 -C 6 -haloalkylcarbonyl,
  • Haloalkenylcarbonyl C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxycarbonyl,
  • Alkylsulfonyl and Ci-C6-Halogengenalkylsufonyl is synonymous for a rest of the series
  • X is oxygen or sulfur, n is 1 or 2.
  • R 8 is a radical selected from hydrogen, C 1 -C 6 -alkyl, C 1 -C 6 -haloalkyl, cyano-C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy , Ci-C6-haloalkoxy, C 2 -C 6 -alkenyl, Ci-C6-alkoxy-Ci-C6-alkyl, in each case optionally substituted by halogen Ci-C6-alkylcarbonyl and Ci-C6-alkylsulfonyl, optionally substituted by halogen Ci-C6 Alkoxycarbonyl, optionally substituted by halogen, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-haloalky
  • R 9 is a radical from the series in each case optionally substituted by halogen, Ci-C6-alkoxy, Ci-Ce- haloalkoxy, Ci-C6-alkylthio, Ci-C6-haloalkylthio, Ci-C6-alkylsulfinyl, CI-C ⁇ - haloalkylsulfinyl , Ci-C6-alkylsulfonyl, and Ci-C6-haloalkylsulfonyl-substituted CI-C ⁇ - alkyl, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl, each optionally substituted by halogen, Ci-C6-alkyl, Ci-
  • halogen is a radical from the series in each case optionally substituted by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -haloalkylthio, C 1 -C 6 -alkylsulfinyl, C 1 -C 8 -haloalkylsulfinyl, C6-alkylsulfonyl or Ci-C6-haloalkylsulfonyl-substituted CI-C ⁇ - alkyl, Ci-C6 alkoxy, C 2 -C 6 alkenyl and C 2 -C 6 alkynyl, each optionally substituted by halogen, Ci-COE-alkyl, Ci- C6-haloalkyl, Ci-C6-alkoxy or Ci-C6-haloalkoxy-substituted C3-C6
  • R 8 and R 17 can also be used together with the NC (X) group to which they are attached, a saturated or unsaturated and optionally halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, CI-C ⁇ - alkoxy, Ci-C6-haloalkoxy-substituted 5- to 7-membered ring form, which may contain one or two further heteroatoms from the series sulfur, oxygen (oxygen atoms may not be immediately adjacent) and nitrogen and / or a carbonyl group, in particular R 8 and R 17, together with the NC (X) group to which they are attached, are out of line for a remainder
  • R independently of one another represent hydrogen or an optionally substituted radical from the group consisting of C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, phenyl and phenylalkyl.
  • B-1 wherein the dashed line represents the bond to A and the arrow represents the bond to the group NR 2 R 3 .
  • Ci-C4-alkyl stands for a radical from the series halogen, cyano, nitro, Ci-C4-alkyl, Ci-C 4 haloalkyl, C 2 - C 4 alkenyl, C 2 -C 4 haloalkenyl, Ci-C 4 alkoxy, Ci-C 4 haloalkoxy, C 3 -C 6 cycloalkyl, C 3 -C 6 halocycloalkyl, Ci-C 4 alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci- C 4 -Halogenalylsulfinyl, C -C 4 alkylsulfonyl, Ci-C4-haloalkylsulfonyl.
  • C 1 -C 4 -alkyl is a radical from the series consisting of hydrogen, C 1 -C 4 -alkyl, C 2 -C 4 -alkenyl, C 2 -C 4 -alkynyl, C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkenyl, C 1 -C 4 - alkoxy, C 2 -C 4 alkenyloxy, C 2 -C 4 alkynyloxy, C 3 -C 6 cycloalkyloxy, Ci-C4-alkylthio-Ci-C 4 alkyl, C 2 -C 4 alkenylthio-Ci C 4 -alkyl, cyano-C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl.
  • R 3 is a radical of the formula stands for a radical from the group Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-alkylthio-Ci-C4-alkyl, Ci-C4-alkylsulfinyl-Ci-C4-alkyl, Ci-C 4 - alkylsulfonyl-Ci-C4-alkyl, Ci-C 4 haloalkyl thio-Ci-C4-alkyl, Ci-C4-haloalkylsulfinyl-Ci-C4-alkyl, Ci-C4-haloalkylsulfonyl-Ci-C4-alkyl, Ci- C 4 -alkylthio-C 2 -C 4 alkenyl, C 4 alkylsulfinyl-C 2 -C 4 alkenyl, Ci-C 4 alkylsulfonyl C 2 -C 4 alken
  • halogen is also optionally substituted by halogen, cyano, nitro, amino, hydroxy, C 1 -C 6 -alkyl, ce-Ce-haloalkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkynyl, C 3 -C 6 -cycloalkyl , C 1 -C 6 -alkoxy, C 1 -C 6 -haloalkoxy, C 3 -C 6 -alkenyloxy, C 3 -C 6 -alkynyloxy, C 1 -C 6 -alkoxycarbonyloxy, C 1 -C 6 -alkylamino, C 3 -C 6 -alkenylamino, C 3 -C 6 -alkynylamino, C3-C6-cycloalkylamino, CI-C ⁇ - alkylthio, Ci-C 6 haloalkylthio, C 3 -C 6
  • R 3 is also out of line for a rest
  • R 5 is (only in the radical B-36), halogen, cyano, nitro, hydroxy, Ci-C4-alkyl, Ci-C alkyl 4 haloalkyl, cyano-Ci-C 4 is a radical selected from hydrogen, C 2 -C 4 alkenyl, C 2 -C alkynyl, C 3 -C 6 cycloalkyl, C 3 -C 6 cycloalkyl-Ci-C4-alkyl, Ci-C 4 alkoxy, Ci-C 4 - haloalkoxy, C 3 -C 4 - alkenyloxy, C 3 -C alkynyloxy, C 3 -C 6 cycloalkyloxy, Ci-C alkylsulfinyl, Ci-C alkylthio, Ci- C4-haloalkylthio, Ci-C 4 alkylsulfonyl, C 1 -C 4 -alkoxyimino-C 1 -C
  • ⁇ is a radical selected from the group consisting of hydrogen, C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl and C 1 -C 4 -haloalkyl.
  • halogen is a radical from the series in each case optionally substituted by halogen, C 1 -C 4 -alkoxy, C 1 -C 4 -haloalkoxy, C 1 -C 4 -alkylthio, C 1 -C 4 -haloalkylthio, C 1 -C 4 -alkylsulfinyl, C 1 -C 4 - haloalkylsulfinyl, Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl-substituted C 1 -C 4 - alkyl, C 2 -C 4 alkenyl and C 2 -C 4 alkynyl each optionally substituted by halogen, Ci-C 4 alkyl, C - C4-haloalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy-substituted C3-C6-cycloalkyl
  • 4 -alkoxy represents a radical from the series in each case optionally substituted by halogen, Ci-C, C 1 -C 4 - haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, C1-C4 haloalkylsulfinyl , Ci-C4-alkylsulfonyl and Ci-C4-haloalkylsulfonyl-substituted C 1 -C 4 - alkyl, C 2 -C 4 alkenyl and C 2 -C 4 alkynyl each optionally substituted by halogen, Ci-C 4 alkyl , C 4 haloalkyl, C 1 -C 4 alkoxy, C 1 -C 4 haloalkoxy, substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyl-
  • R 2 is hydrogen
  • R 3 represents the remainder of the formula R 4 stands for Ci-C4-alkylthio-Ci-C 4 -alkyl or optionally substituted by one or two radicals from the series halogen, nitro and Ci-C4-haloalkyl substituted phenyl.
  • N-alkyl especially N-Ci-C6-alkyl
  • Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably again from the series fluorine, chlorine and bromine,
  • Aryl also as part of a larger unit, such as arylalkyl selected from the group phenyl, naphthyl, anthryl, phenanthrenyl and in turn preferably represents phenyl, hetaryl (equivalent to heteroaryl, also as part of a larger unit, such as hetarylalkyl) selected from the series furyl, thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1, 2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1, 2,4- Oxadiazolyl, 1,3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, Pyridyl,
  • Halogen selected from the group fluorine, chlorine, bromine and iodine, preferably in turn from the series fluorine, chlorine and bromine,
  • Aryl also as part of a larger unit, such as, for example, arylalkyl selected from among phenyl, naphthyl, anthryl, phenanthrenyl and in turn preferably represents phenyl, hetaryl (also as part of a larger unit, such as, for example, hetarylalkyl) selected from the series furyl, Thienyl, pyrrolyl, pyrazolyl, imidazolyl, 1,2,3-triazolyl, 1, 2,4-triazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-oxadiazolyl, 1, 2,4-oxadiazolyl, 1, 3,4-oxadiazolyl, 1,2,5-oxadiazolyl, 1,2,3-thiadiazolyl, 1, 2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 1,2,5-thiadiazolyl, pyridyl
  • Halogen stands for fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
  • Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl
  • heteroatoms e.g. in alkoxy, as far as possible, in each case straight-chain or branched.
  • Optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents may be the same or different.
  • Suitable metal ions in the radical R 8 are, for example, alkali metal ions such as Li + , Na + , Cs + and K + and alkaline earth metal ions such as Mg ++ and Ca ++ .
  • alkali metal ions such as Li + , Na + , Cs + and K +
  • alkaline earth metal ions such as Mg ++ and Ca ++ .
  • the abovementioned general or preferred radical definitions or explanations apply to the end products (also for the compounds of the formulas (IA) to (IM) listed below) and correspondingly to the starting materials and intermediates. These remainder definitions can be combined with one another as desired, ie also between the respective preferred ranges. Preference according to the invention is given to compounds of the formula (I) which contain a combination of the meanings listed above as being preferred.
  • the invention relates to compounds of the formula (IB)
  • the invention relates to compounds of the formula (IC)
  • the invention relates to compounds of the formula (ID)
  • the invention relates to compounds of the formula (IE)
  • the invention relates to compounds of the formula (IF)
  • the invention relates to compounds of the formula (IG)
  • the invention relates to compounds of the formula (IH)
  • the invention relates to compounds of the formula (I-J)
  • the invention relates to compounds of the formula (I-K)
  • the invention relates to compounds of the formula (I-L)
  • the invention relates to compounds of the formula (III)
  • the compounds of the formula (I) according to the invention and their acid addition salts and metal salt complexes have good activity, in particular for controlling animal pests, which include arthropods and in particular insects.
  • the compounds of formula (I) may also be optionally substituted as stereoisomers, i.e., depending on the nature of the substituents. as geometric and / or as optical isomers or mixtures of isomers are present in different compositions. Both the pure stereoisomers and any mixtures of these isomers are the subject of this invention, although in general only compounds of the formula (I) are mentioned here.
  • the compounds of the formula (I) according to the invention can be present in different polymorphic forms or as a mixture of different polymorphic forms. Both the pure polymorphs and the polymorph mixtures are the subject of the invention and can be used according to the invention.
  • the optically active stereoisomeric forms of the compounds of the formula (I) and salts thereof are used according to the invention.
  • the invention therefore relates to both the pure enantiomers and diastereomers, as well as their mixtures for controlling animal pests, which include arthropods and in particular insects.
  • Suitable salts of the compounds of general formula (I) may be conventional non-toxic salts, i. H. Salts with corresponding bases and salts with added acids.
  • salts with inorganic bases such as alkali metal salts, for example sodium, potassium or cesium salts, alkaline earth metal salts, for example calcium or magnesium salts, ammonium salts, salts with organic bases and with inorganic amines, for example triethylammonium, dicyclohexylammonium, ⁇ , ⁇ '- Dibenzylethylenediammonium, pyridinium, picolinium or ethanolammonium salts, salts with inorganic acids, for example hydrochlorides, hydrobromides, dihydrosulfates, trihydrosulfates, or phosphates, salts with organic carboxylic acids or organic sulfonic acid, for example formates, acetates, trifluoroacetates, maleates, tartrates, methanesul
  • N-pyrazol-1-yl is B
  • LG is an in situ generated nucleofuge leaving group
  • Nitrations can be carried out by customary processes, as described, for example, in Houben-Weyl, Methods of Organic Chemistry, Volume XI / 2 (Georg Thieme Verlag Stuttgart 1958), pages 99-116.
  • Suitable nitrating reagents are fuming or 100% nitric acid, optionally in the presence of sulfuric acid (MJ Middleton et al., / Heterocyclic Chem. 1970, 7, pp. 1045-1049, LW Deady et al., Aust. J. Chem. 10), pp 2025-2034; EP 0192060) or the use of nitric acid esters, acyl nitrate or nitronium tetrafluoroborate.
  • Suitable catalysts for carrying out the catalytic hydrogenation are all customary hydrogenation catalysts, for example platinum catalysts (platinum plate, platinum sponge, platinum black, colloidal platinum, platinum oxide, platinum wire, etc.), palladium catalysts (for example palladium sponge, Palladium black, palladium oxide, palladium-carbon, colloidal palladium, palladium-barium sulfate, palladium-barium carbonate, palladium hydroxide, etc.), ruthenium catalysts, cobalt catalysts (e.g., reduced cobalt, Raney cobalt, etc.), copper catalysts (for example, reduced copper, Raney copper, Ullman copper, etc.).
  • noble metal catalysts for example platinum and palladium or ruthenium catalysts, if appropriate on a suitable support such as carbon or silicon.
  • the hydrogenation catalysts used are preferably palladium or platinum catalysts, in particular palladium-hydroxide-carbon or platinum oxide (cf., Preparation Example 1, Step 3).
  • the heterocyclic compounds of the formula (Al) with 3-substituted pyrazoles of the formula (A-6) according to method B in a first reaction step to compounds of formula (A-7) are reacted, which then either in a second reaction step Removal of the protective group PG to compounds of formula (A-5) or equal to compounds of formula (IA to ID) can be implemented.
  • the compounds of the formula (A1) are known in some cases or can be obtained by production processes known in principle, cf.
  • LG Br
  • LG 4- (4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -isoxazole
  • LG B [-OC (CH 3 ) 2 C (CH 3 ) 2 O-], J. Velcicky et al., Amer. Chem.
  • heterocycle A is, for example, optionally substituted by an R radical substituted pyrazol-4-yl (Aa), isothiazol-4-yl (Ab), isoxazol-4-yl (Ac) or pyrazine -yl (Ah), and the heterocycle B is l, 3-thiazol-2-yl, which is substituted in the 4-position by a radical R 1 , for example, by Method C according to Reaction Scheme II are shown.
  • Hal halogen, preferably bromine or iodine
  • PG tertiarybutyloxacarbonyl
  • halogen-substituted heteroaryl compounds for example halogen-substituted 1,3-thiazoles of the formula (A-8)
  • known methods such as Chem Rev. 1995, 95, 2457-2483, Tetrahedron 2002, 58, 9633-9695, Metal-Catalyzed Cross-Coupling Reactions (Eds .: A. de Meijere , F. Diederich), 2 nd ed., Wiley-VCH, Weinheim, 2004
  • suitable catalysts from the series of transition metal salts to give compounds of formula (A-9).
  • Halogen iodine
  • R 1 ethoxycarbonyl
  • R 2 hydrogen
  • PG tert- Butyloxycarbonyl (Boc)
  • heterocycle A is substituted, for example, by pyrazol-4-yl optionally substituted by one R (see IA), isothiazol-4-yl (see IB), isoxazol-4-yl (cf. IC) or pyrazine-2-yl (see ID), and the heterocycle B is l, 3,4-thiadiazol-2-yl (B-3), for example, by the method C according to Reaction Scheme III.
  • Hal halogen, preferably chlorine, bromine or iodine
  • LG stands for an in-situ generated nucleofuge leaving group
  • Hai stands for halogen (preferably bromine or iodine)
  • PG means protection group.
  • PG tertiarybutyloxacarbonyl
  • halogen-substituted heteroaryl compounds for example halogen-substituted 1,3-thiadiazoles of the formula (A-10), according to the method mentioned in Reaction Scheme III C in the presence of suitable catalysts from the series of transition metal salts to give compounds of formula (A-11).
  • Compounds of the formula (A-1) are known in some cases or can be obtained by the production processes mentioned above.
  • N-alkylation j N-alkylation / N-acylation / N-sulfonation
  • PG ferf-butyloxycarbonyl (Boc) AB-NR 2 NR 3
  • PG means Protection Group.
  • Amides, N-alkylamines, N-arylamines, imine derivatives, enamine derivatives, N-sulfenyl derivatives, N-sulfonyl derivatives or N-diarylphosphinyl derivatives can be used (see Greene TW, Wuts PGW in Protective Croups in Organic Synthesis, John Wiley & Sons, Inc 1999, "Protection for the Amino Group", p. 494).
  • carbamate-type protecting groups are used. _
  • Compounds of formulas (1-2) and (1-4) can be prepared from the compounds of formula (1-1) and (1-3) by deprotection, respectively.
  • acidic or basic reaction auxiliaries can be used according to the literature procedure for the removal of the protective group.
  • carbamate-type protecting groups preference is given to using acidic reaction auxiliaries.
  • the tert-butylcarbamate protecting group (Boc group) is used, for example, mixtures of mineral acids such as hydrochloric, hydrobromic, nitric, sulfuric, phosphoric or organic acids such as benzoic, formic, acetic, trifluoroacetic, methanesulfonic, benzenesulfonic or toluenesulfonic acid in a suitable diluent such as water and / or an organic solvent such as tetrahydrofuran, dioxane, dichloromethane, chloroform, ethyl acetate, ethanol or methanol.
  • a suitable diluent such as water and / or an organic solvent
  • the compounds of the formulas (1-1), (1-2) and (1-4) can be prepared by methods known in principle with suitable reactants and in the presence of diluents and basic reaction auxiliaries to give compounds of the formulas (1-3), (1-4) and (I) N-alkylated, N-acylated or N-sulfonylated (see Preparation Examples, Examples 1 and 2).
  • Diluents are advantageously used in such an amount that the reaction mixture remains easy to stir throughout the process.
  • Suitable diluents for carrying out the process according to the invention are all organic solvents which are inert under the reaction conditions.
  • halogenated hydrocarbons especially chlorinated hydrocarbons such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1, 2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene, trichlorobenzene; Alcohols such as methanol, ethanol, isopropanol, butanol; Ethers such as ethyl propyl ether, methyl tert-butyl ether, n-butyl ether, anisole, phenetole, cyclohexylmethyl ether, dimethyl ether, diethyl ether, dipropl ether, diisopropyl ether
  • Preferred diluents for carrying out the process according to the invention are halogenated hydrocarbons, in particular chlorohydrocarbons, such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluorobenzene, 1, 2-dichloroethane, chlorobenzene, bromobenzene, dichlorobenzene, chlorotoluene and trichlorobenzene.
  • chlorohydrocarbons such as tetraethylene, tetrachloroethane, dichloropropane, methylene chloride, dichlorobutane, chloroform, carbon tetrachloride, trichloroethane, trichlorethylene, pentachloroethane, difluoro
  • Activation reagents which may be used are all reagents which are suitable for the preparation of an amide or hydrazide bond (cf., for example, Houbel-Weyl, Methods of Organic Chemistry, Volume 15/2, Bodansky et al., Peptide Synthesis 2 nd ed. (Wiley & Sons, New York 1976) or Gross, Meienhofer, The Peptides: Analysis, Synthesis, Biology (Academy Press, New York 1979).
  • the coupling with phosphonium reagents such as bis (2-oxo-3-oxazolidinyl) phosphonium chloride ( BOP-Cl), benzotriazole-1-yl-oxy-tris (dimethylamino-phosphonium) hexafluorophosphate (BOP), benzotriazol-l-yl-tris-pyrrolidino-phosphonium hexafluorophosphate (PyBOB ®), bromo-tris- pyrrolidino-phosphonium -hexafluorophospha (PyBroP ®) or Phosphonklarreagenzien such as diethyl cyanophosphonate (DEPC) and diphenylphosphoryl azide (DPPA).
  • BOP-Cl bis (2-oxo-3-oxazolidinyl) phosphonium chloride
  • BOP benzotriazole-1-yl-oxy-tris (dimethylamino-phosphon
  • Preferred activating agents for the (thio) carboxylic acids or sulfonic acids are, for example, phosphonium reagents such as bis (2-oxo-3-oxazolidinyl) phosphonium chloride (BOP-Cl) (compare also Preparation Examples, Example 1, Step 4 and Example 2).
  • reaction auxiliaries for carrying out the process according to the invention in Reaction Scheme IV it is possible to use all suitable acid binders, for example amines, in particular tertiary amines, and also alkali metal and alkaline earth metal compounds.
  • suitable acid binders for example amines, in particular tertiary amines, and also alkali metal and alkaline earth metal compounds.
  • Examples include the hydroxides, hydrides, oxides and carbonates of lithium, sodium, potassium, magnesium, calcium and barium, further basic compounds such as amidine bases or guanidine bases such as 7-methyl-l, 5,7-triaza-bicyclo (4.4.0 ) dec-5-ene (MTBD); Diazabicyclo (4.3.0) nonene (DBN), diazabicyclo (2.2.2) octane (DABCO), 1,8-diazabicyclo (5.4.0) undecene (DBU), cyclohexyltetrabutyl-guanidine (CyTBG), cyclohexyltetramethylguanidine (CyTMG), ⁇ , ⁇ , ⁇ , ⁇ -tetramethyl-l, 8-naphthalenediamine, pentamethylpiperidine, tertiary amines such as triethylamine, trimethylamine, tribenzylamine, triisopropylamine, tributyl
  • hydroxides of lithium potassium or sodium are used.
  • tertiary amines such as N-propyl-diisopropylamine or N-ethyl-diisopropylamine (Hünig's base) are preferably used.
  • R 2 is an acceptor radical such as acyl, sulfonyl, etc.
  • tertiary amines such as N-propyl-diisopropylamine or N, depending on R 2 Ethyl-diisopropylamine (Hünig's base)
  • R 2 is optionally substituted alkyl, alkenyl, alkynyl, etc.
  • the active compounds according to the invention or to be used in accordance with the invention are suitable for plant tolerance, favorable warm-blooded toxicity and good environmental compatibility for protecting plants and plant organs, for increasing crop yields, improving the quality of the crop and for controlling animal pests, in particular insects, arachnids, helminths, Nematodes and molluscs found in agriculture, horticulture, livestock, forestry, gardens and recreational facilities, in the protection of materials and materials and in the hygiene sector. They can preferably be used as crop protection agents. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Pests of the genus Arthropoda in particular of the class Arachnida eg Acarus spp., Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Amphitetranychus viennensis, Argas spp., Boophilus spp., Brevipalpus spp., Bryobia graminum , Bryobia praetiosa, Centruroides spp., Chorioptes spp., Dermanyssus gallinae, Dermatophagoides pteronyssinus, Dermatophagoides farinae, Dermacentor spp., Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp., Eriophyes spp., Glycyphagus domesticus, Halotydeus destructor, Hemitarsonemus spp
  • Curculio spp. Cryptolestes ferruginus, Cryptorhynchus lapathi, Cylindrocopturus spp., Dermestes spp., Diabrotica spp., Dichocrocis spp., Dicladispa armigera, Diloboderus spp., Epilachna spp., Epitrix spp., Faustinus spp., Gibbium psylloides, Gnathocerus cornutus , Hellula and alis, Heteronychus arator, Heteronyx spp., Hylamorpha elegans, Hylotrupes bajulus, Hypera postica, Hypomeces squamosus, Hypothenemus spp., Lachnosterna consanguinea, Lasioderma serricorne, Latheticus oryzae, Lathridius spp., Lema spp., Leptinotarsa decem
  • Phormia spp. Piophila casei, Prodiplosis spp., Psila rosae, Rhagoletis spp., Sarcophaga spp., Simulium spp., Stomoxys spp., Tabanus spp., Tetanops spp., Tipula spp .; from the order of the Heteroptera eg Anasa tristis, Antestiopsis spp., Boisea spp., Blissus spp., Calocoris spp., Campylomma livida, Cavelerius spp., Cimex spp., Collaria spp., Creontiades dilutus, Dasynus piperis, Dichelops furcatus, Diconocoris hewetti, Dysdercus spp., Eushtus spp., Eurygaster spp., Heli
  • Pentomidae Piesma quadrata, Piezodorus spp., Psallus spp., Pseudacysta persea, Rhodnius spp., Sahlbergella singularis, Scaptocoris castanea, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.
  • Tinocallis caryaefoliae Tinocallis caryaefoliae, Tomaspis spp., Toxoptera spp., Trialeurodes vaporariorum, Trioza spp., Typhlocyba spp., Unaspis spp., Viteus vitifolii, Zygina spp .; from the order of Hymenoptera eg Acromyrmex spp., Athalia spp., Atta spp., Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Sirex spp., Solenopsis invicta, Tapinoma spp., Urocerus spp., Vespa spp ., Xeris spp .; from the order of Isopoda, for example, Armadillidium vulgare, Oniscus asellus, Porcellio scaber
  • Protoparce spp. Pseudaletia spp., Pseudaletia unipuncta, Pseudoplusia includens, Pyrausta nubilalis, Rachiplusia nu, Schoenobius spp., Scirpophaga spp., Scirpophaga innotata, Ontario segetum, Sesamia spp., Sesamia inferens, Sparganothis spp. , Spodoptera spp., Spodoptera praefica, Stathmopoda spp., Stomopteryx subsecivella, ""
  • Synanthedon spp. Tecia solanivora, Thermesia gemmatalis, Tinea cloacella, Tinea pellionella, Tineola bisselliella, Tortrix spp., Trichophaga tapetzella, Trichoplusia spp., Tryporyza incertulas, Tuta absolutea, Virachola spp .; from the order of Orthoptera or Saltatoria e.g.
  • Thysanoptera e.g. Anaphothrips obscurus, Baliothrips biformis, Drepanothrips reuteri, Enneothrips hevens
  • Ctenolepisma spp. Lepisma saccharina, Lepismodes inquilinus, Thermobia domestica; from the class of Symphyla e.g. Scutigerella spp .;
  • Pests from the strain of Mollusca in particular from the class of bivalvia, eg Dreissena spp., And from the class of Gastropoda eg Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Pomacea spp., Succinea spp .; Animal parasites from the strains of Plathelminthes and Nematoda, eg Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp.,
  • Opisthorchis spp. Onchocerca volvulus, Ostertagia spp., Paragonimus spp., Schistosome spp., Strongyloides fuelleborni, Strongyloides stercoralis, Stronyloides spp., Taenia saginata, Taenia solium, Trichinella spiralis, Trichinella nativa, Trichinella britovi, Trichinella nelsoni, Trichinella pseudopsiralis , Trichostrongulus spp., Trichuris trichuria, Wuchereria bancrofti; Plant pests from the Nematoda strain, ie plant parasitic nematodes, in particular Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus spp., Globodera spp., Heterodera spp., Longidorus spp., Meloidogy
  • Hemicycliophora spp. Anguina spp., Subanguina spp., Hemicriconemoides spp., Psilenchus spp., Pseudohalenchus spp., Criconemoides spp., Cacopaurus spp.
  • the order of coccidia can be determined, e.g. Eimeria spp. fight.
  • the present invention further relates to formulations and application forms prepared therefrom as crop protection agents and / or pesticides such. B. drench, drip and spray, comprising at least one of the active compounds according to the invention. If appropriate, the use forms contain other crop protection agents and / or pesticides and / or the effect of improving adjuvants such as penetration enhancers, eg.
  • vegetative oils such as rapeseed oil, sunflower oil, mineral oils such as paraffin oils, alkyl esters of vegetal fatty acids such as rapeseed oil or soybean oil methyl ester or alkanol alkoxylates and / or spreading agents such as alkyl siloxanes and / or salts, e.g. organic or inorganic ammonium or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate and / or retention-promoting agents such.
  • Typical formulations are, for example, water-soluble liquids (SL), emulsion concentrates (EC), emulsions in water (EW), suspension concentrates (SC, SE, FS, OD), water-dispersible granules (WG), granules (GR) and capsule concentrates (CS). ;
  • SL water-soluble liquids
  • EC emulsion concentrates
  • EW emulsions in water
  • SC suspension concentrates
  • SC SE, SE, FS, OD
  • WG water-dispersible granules
  • GR granules
  • capsule concentrates CS
  • the formulations contain, in addition to one or more active compounds according to the invention, further agrochemical active substances.
  • auxiliaries such as extenders, solvents, spontaneity promoters, carriers, emulsifiers, dispersants, antifreeze agents, biocides, thickeners and / or further auxiliaries, for example adjuvants.
  • An adjuvant in this context is a component that enhances the biological effect of the formulation without the component itself having a biological effect.
  • Examples of adjuvants are agents which enhance retention, spreading behavior, adherence to the Promote leaf surface or penetration.
  • formulations are prepared in a known manner, e.g. by mixing the active ingredients with excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
  • excipients such as extenders, solvents and / or solid carriers and / or other excipients such as surfactants.
  • the preparation of the formulations is carried out either in suitable systems or before or during use.
  • Excipients which can be used are those which are suitable for imparting special properties, such as physical, technical and / or biological properties, to the formulation of the active substance or to the forms of use prepared from these formulations (for example usable plant protection agents such as spray mixtures or seed dressing).
  • extender e.g. Water, polar and non-polar organic chemical liquids e.g.
  • aromatic and non-aromatic hydrocarbons such as paraffins, alkylbenzenes, alkylnaphthalenes, chlorobenzenes
  • alcohols and polyols which may also be substituted, etherified and / or esterified
  • ketones such as acetone, cyclohexanone
  • Esters including fats and oils
  • poly) ethers simple and substituted amines, amides, lactams (such as N-alkylpyrrolidones) and lactones, sulfones and sulfoxides (such as methyl sulfoxide).
  • Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, e.g.
  • Petroleum fractions mineral and vegetable oils, alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide and water.
  • alcohols such as butanol or glycol and their ethers and esters
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone
  • strongly polar solvents such as dimethylformamide and dimethyl sulfoxide and water.
  • Suitable solvents are, for example, aromatic hydrocarbons, e.g. Xylene, toluene or alkylnaphthalenes, chlorinated aromatic or aliphatic hydrocarbons, e.g. Chlorobenzene, chloroethylene, or methylene chloride, aliphatic hydrocarbons, e.g. Cyclohexane, paraffins, petroleum fractions, mineral and vegetable oils, alcohols such as e.g. Methanol, ethanol, iso-propanol, butanol or glycol and their ethers and esters, ketones such as e.g. Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethyl sulfoxide and water.
  • aromatic hydrocarbons e.g. Xylene, toluene or alkylnaphthalenes
  • chlorinated aromatic or aliphatic hydrocarbons e
  • Suitable carriers are in particular: for example, ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock flour, such as finely divided silica, alumina and natural or synthetic silicates, resins, waxes and ""
  • Suitable carriers for granules are: e.g. Cracked and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, paper, coconut shells, corn cobs and tobacco stems.
  • liquefied gaseous diluents or solvents can be used.
  • Examples of emulsifying and / or foaming agents, dispersants or wetting agents having ionic or non-ionic properties or mixtures of these surfactants are salts of polyacrylic acid, salts of lignosulphonic acid, salts of phenolsulphonic acid or naphthalenesulphonic acid, polycondensates of ethylene oxide with fatty alcohols or with fatty acids or with fatty amines, with substituted phenols (preferably alkylphenols or arylphenols), salts of sulphosuccinic acid esters, taurine derivatives (preferably alkyl taurates), phosphoric acid esters of polyethoxylated alcohols or phenols, fatty acid esters of polyols and derivatives of the compounds containing sulphates, sulphonates and phosphates, eg Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, arylsulfonates, protein hydro
  • dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes, and nutrient and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
  • Stabilizers such as cold stabilizers, preservatives, antioxidants, light stabilizers or other chemical and / or physical stability-improving agents may also be present. It may also contain foam-forming agents or defoamers.
  • formulations and the use forms derived therefrom may also contain, as additional auxiliaries, adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-containing polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • additional auxiliaries may be mineral and vegetable oils.
  • auxiliaries may be present in the formulations and in the use forms derived therefrom.
  • additives are, for example, perfumes, protective "
  • the active ingredients can be combined with any solid or liquid additive commonly used for formulation purposes.
  • retention promoters are all those substances which reduce the dynamic surface tension such as dioctylsulfosuccinate or increase the visco-elasticity such as hydroxypropyl guar polymers.
  • Suitable penetration promoters in the present context are all those substances which are usually used to improve the penetration of agrochemical active substances into plants.
  • Penetration promoters are in this context defined by the fact that they can penetrate from the (usually aqueous) application broth and / or from the spray coating into the cuticle of the plant and thereby increase the material mobility (mobility) of the active ingredients in the cuticle.
  • the method described in the literature can be used to determine this property.
  • Examples include alcohol alkoxylates such as coconut oil ethoxylate (10) or Isotridecylethoxylat (12), fatty acid esters such as rapeseed oil or soybean oil, fatty amine alkoxylates such as Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • alcohol alkoxylates such as coconut oil ethoxylate (10) or Isotridecylethoxylat (12)
  • fatty acid esters such as rapeseed oil or soybean oil
  • fatty amine alkoxylates such as Tallowamine ethoxylate (15) or ammonium and / or phosphonium salts such as ammonium sulfate or diammonium hydrogen phosphate.
  • the formulations preferably contain between 0.00000001 and 98% by weight of active ingredient or, more preferably, between 0.01 and 95% by weight of active compound, more preferably between 0.5 and 90% by weight of active ingredient, based on the weight of the formulation.
  • the active substance content of the application forms (pesticides) prepared from the formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms can usually be between 0.00000001 and 95% by weight of active ingredient, preferably between 0.00001 and 1% by weight, based on the weight of the application form.
  • the application is done in a custom forms adapted to the application.
  • the active substances to be used according to the invention or according to the invention can also be used as such or in their formulations as a mixture with one or more suitable fungicides, bactericides, acaricides, molluscicides, nematicides, insecticides, microbiologicals, beneficials, fertilizers, bird repellents, phytotonics, sterilants, synergists, Safeners, semiochemicals and / or plant growth regulators can be used, for example, to broaden the spectrum of action, to extend the duration of action, to increase the rate of action, to prevent repellence or to prevent the development of resistance. Furthermore, such drug combinations plant growth and / or tolerance to abiotic factors such. B. high or t rn
  • Acetylcholinesterase (AChE) inhibitors such as carbamates, e.g. Alanycarb, Aldicarb, Bendiocarb, Benfuracarb, Butocarboxime, Butoxycarboxime, Carbaryl, Carbofuran, Carbosulfan, Ethiofencarb, Fenobucarb, Formetanate, Furathiocarb, Isoprocarb, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Propoxur, Thiodicarb, Thiofanox, Triazamate, Trimethacarb, XMC and xylylcarb; or
  • AChE Acetylcholinesterase
  • Organophosphates e.g. Acephate, Azamethiphos, Azinophos-ethyl, Azinophos-methyl, Cadusafos, Chloroethoxyfos, Chlorfenvinphos, Chlormephos, Chlorpyrifos, Chlorpyrifos-methyl, Coumaphos, Cyanophos, Demeton-S-methyl, Diazinone, Dichlorvos / DDVP, Dicrotophos, Dimethoates, Dimethylvinphos, Disulfone, EPN, Ethion, Ethoprophos, Famphur, Fenamiphos, Fenitrothion, Fenthion, Fosthiazate, Heptenophos, Imicyafos, Isofenphos, Isopropyl O- (methoxyaminothio-phosphoryl) salicylate, Isoxathione, Malathion, Mecarbam, Methamidophos, Methida
  • GABA-controlled chloride channel antagonists such as cyclodiene organochlorines, e.g. Chlordane and endosulfan; or
  • Phenylpyrazoles e.g. Ethiprole and fipronil.
  • Sodium channel modulators / voltage dependent sodium channel blockers such as Pyrethroids, eg acrinathrin, allethrin, d-cis-trans allethrin, d-trans allethrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentenyl isomer, bioresmethrin, cycloprothrin, cyfluthrin, beta-cyfluthrin, cyhalothrin, lambda-cyhalothrin, gamma-cyhalothrin, cypermethrin alpha-cypermethrin, beta-cypermethrin, theta-cypermethrin, zeta-cypermethrin, cyphenothrin [(lR) trans isomers], deltamethrin, empenthrin [(EZ) (lR) isomers], e
  • nicotinergic acetylcholine receptor (nAChR) agonists such as
  • Neonicotinoids e.g. Acetamiprid, clothianidin, dinotefuran, imidacloprid, nitenpyram, thiacloprid and thiamethoxam; or
  • nicotinergic acetylcholine receptor (nAChR) allosteric activators such as spinosines, e.g. Spinetoram and spinosad.
  • Avermectins / milbemycins e.g. Abamectin, Emamectin benzoate, Lepimectin and Milbemectin.
  • Juvenile hormone mimics such as juvenile hormone analogs, e.g. Hydroprene, kinoprene and methoprene; or fenoxycarb; or pyriproxyfen.
  • agents with unknown or nonspecific modes of action such as alkyl halides, e.g. Methyl bromide and other alkyl halides; or
  • mite growth inhibitors eg clofentezine, hexythiazox and diflovidazine; or Etoxazole.
  • Insect intestinal membrane microbial disruptors e.g. Bacillus thuringiensis subspecies israelensis, Bacillus thuringiensis subspecies aizawai, Bacillus thuringiensis subspecies kurstaki, Bacillus thuringiensis subspecies tenebrionis and B.t.
  • Plural proteins CrylAb, CrylAc, CrylFa, CrylA.105, Cry2Ab, Vip3A, mCry3A, Cry3Ab, Cry3Bb, Cry34 From 1/35 From 1; or
  • Bacillus sphaericus Bacillus sphaericus.
  • inhibitors of oxidative phosphorylation, ATP disruptors such as diafenthiuron; or
  • Organotin Compounds e.g. Azocyclotine, cyhexatin and fenbutatin oxide; or propargite; or tetradifon.
  • Nicotinergic acetylcholine receptor antagonists such as Bensultap, Cartap hydrochloride, thiocyclam and thiosultap sodium.
  • Type 0 inhibitors of chitin biosynthesis such as bistrilluron, chloraluazuron, dillubenzuron, flucycloxuron, flufenoxuron, hexallumuron, lufenuron, novaluron, novillumuron, tellubenzuron, and triilumuron.
  • inhibitors of chitin biosynthesis type 1, such as buprofezin.
  • Moulting agents dipteran, such as cyromazine.
  • ecdysone receptor agonists such as chromafenozides, halofenozides, methoxyfenozides, and tebufenozides.
  • Octopaminergic agonists such as amitraz.
  • complex III electron transport inhibitors such as hydramethylnone; or acequinocyl; or fluacrypyrim.
  • complex I electron transport inhibitors for example
  • METI acaricides eg fenazaquin, fenpyroximate, pyrimidifen, pyridaben, tebufenpyrad and tolfenpyrad; or Rotenone (Derris).
  • Tetronic and tetramic acid derivatives e.g. Spirodiclofen, spiromesifen and spirotetramat.
  • complex IV electron transport inhibitors such as
  • Phosphines e.g. Aluminum phosphide, calcium phosphide, phosphine and zinc phosphide; or cyanide.
  • ryanodine receptor effectors such as diamides, e.g. Chlorantraniliprole, Cyantraniliprole and Flubendiamide.
  • agents such as amidoflumet, azadirachtin, benclothiaz, benzoximate, bifenazate, bromopropylate, quinomethionate, cryolite, dicofol, diflovidazine, fluensulfone, flufenerim, flufiprole, fluopyram, fufenocide, imidaclothiz, iprodione, meperfluthrin, pyralidyl, pyrifluquinazone, tetramethylfluthrin and iodomethane; furthermore preparations based on Bacillus firmus (in particular strain CNCM 1-1582, for example VOTiVO TM, BioNem) and the following compounds:
  • 2-yl ⁇ pyrimidine (known from WO2010 / 006713), 1- (3-chloropyridin-2-yl) -N- [4-cyano-2-methyl-6- (methylcarbamoyl) phenyl] -3 - ⁇ [5-10] (trifluoromethyl) -1 H -tetrazol-1-yl] methyl ⁇ -1 H -pyrazole-5-carboxamide (known from WO2010 / 069502), 1- (3-chloropyridin-2-yl) -N- [4-cyano 2-methyl-6- (methylcarbamoyl) phenyl] -3 - ⁇ [5- (trifluoromethyl) -2H-tetrazol-2-yl] methyl ⁇ -1H-pyrazole-5-carboxamide (known from WO2010 / 069502 ), N- [2- (tert -butylcarbamoyl) -4-cyano-6-methylphenyl] -1-
  • Fungicides suitable as mixing partners are:
  • inhibitors of ergosterol biosynthesis such as aldimorph, azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole, difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorph acetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole, fenhexamide, fenpropidin, fenpropimorph, Fluquinconazole, flurprimidol, flusilazole, flutriafol, furconazole, furconazole cis, hexaconazole, imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole, myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazole, pe
  • inhibitors of respiration such as bixafen, boscalid, carboxin, diflumetorim, fenfuram, fluopyram, flutolanil, fluxapyroxad, furametpyr, furmecyclox, isopyrazam mixture of the syn-epimeric racemate 1RS, 4SR, 9RS and the anti- more reactive racemate 1RS, 4SR, 9SR, isopyrazam (anti-epimeric racemate), isopyrazam (anti-epimeric enantiomer 1R, 4S, 9S), isopyrazam (anti-epimeric enantiomer 1S, 4R, 9R), isopyrazam (syn-epimeric racemate 1RS, 4SR, 9RS), isopyrazam (syn-epimeric enantiomer 1R, 4S, 9R), isopyrazam (syn-epimeric enantiomer 1S, 4S, 9R), iso
  • inhibitors of respiration at the complex III of the respiratory chain, such as ametoctradine, amisulbrom, azoxystrobin, cyazofamide, coumethoxystrobin, coumoxystrobin, dimoxystrobin, enestroburin, famoxadone, fenamidone, fenoxystrobin, fluoxastrobin, kresoxim-methyl, metominostrobin, orysastrobin , Picoxystrobin, Pyraclostrobin, Pyrametostrobin, Pyraoxystrobin, Pyribencarb, Triclopyricarb, Trilloxystrobin, (2E) -2- (2- ⁇ [6- (3-chloro-2-methylphenoxy) -5-fluoro-imidin-4-yl] oxy ⁇ phenyl ) -2- (methoxyimino) -N-methylethaneamide, (2E) -2- (methoxyimino) -N-
  • Mitosis and cell division inhibitors such as benomyl, carbendazim, chlorfenazole, diethofencarb, ethaboxam, fluopicolide, fuberidazole, pencycuron, thiabendazole, thiophanate-methyl, " ⁇
  • Compounds with multisite activity such as Bordeaux mixture, captafol, captan, chlorothalonil, copper preparations such as copper hydroxide, copper naphthenate, copper oxide, copper oxychloride, copper sulfate, dichlofiuanide, dithianone, dodine, dodine free base, Ferbam, Fluorofolpet, Folpet, guazatine, guazatin acetate , Ininoctadine, ininoctadinalesilate, iminoctadine triacetate, mancopper, mancozeb, maneb, metiram, zinc metiram, copper oxine, propamidine, propineb, sulfur and sulfur preparations such as calcium polysulide, thiram, tolylfluanid, zineb and ziram.
  • resistance inducers such as acibenzolar-S-methyl, isotianil, probenazole and tiadinil.
  • Inhibitors of amino acid and protein biosynthesis such as andoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycin hydrochloride hydrate, mepanipyrim, pyrimethanil, and 3- (5-fluoro-3, 3,4,4-tetramethyl-3 , 4-dihydroisoquinolin-1-yl) quinoline.
  • inhibitors of ATP production such as fentin acetate, fentin chloride, fentin hydroxide and silthiofam.
  • inhibitors of cell wall synthesis such as benthiavalicarb, dimethomorph, flumorph, iprovalicarb, mandipropamide, polyoxins, polyoxorim, validamycin A, and valifenalate.
  • inhibitors of lipid and membrane synthesis such as biphenyl, chloroneb, dicloran, edifenphos, etridiazole, iodocarb, Iprobenfos, isoprothiolane, propamocarb, propamocarb hydrochloride, prothiocarb, pyrazophos, quintozene, tecnazene and tolclofos-methyl.
  • Inhibitors of melanin biosynthesis such as carpropamide, diclocymet, fenoxanil, fthalide, pyroquilone, tricyclazole and 2,2,2-trifluoroethyl ⁇ 3-methyl-1 - [(4-methylbenzoyl) amino] butan-2-yl carbamate ,
  • Inhibitors of nucleic acid synthesis such as benalaxyl, benalaxyl-M (kiralaxyl), bupirimate, clozylacon, dimethirimol, ethirimol, furalaxyl, hymexazole, metalaxyl, metalaxyl-M
  • signal transduction inhibitors such as chlozolinate, fenpiclonil, fludioxonil, iprodione, procymidone, quinoxyfen and vinclozolin.
  • Decouplers such as binapacryl, dinocap, ferimzone, fluazinam and meptyldinocap.
  • Other compounds such as benthiazole, bethoxazine, capsimycin, carvone, quinomethionate, pyriofenone (Chlazafenone), Cufraneb, cyilufenamide, cymoxanil, cyprosulfamide, dazomet, debacarb, dichlorophen, diclomethine, difenzoquat, difenzoquat methylsulphate, diphenylamine, ecomat, fenpyrazamine, Flumetover, fluoromide, flusulfamide, flutianil, fosetyl-aluminum, fosetyl-calcium, fosetyl-sodium, hexachlorobenzene, irumamycin, methasulfocarb, methylisothiocyanate, me
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • crops may be plants which may be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering techniques or combinations of these methods, including transgenic plants and including plant varieties that are protectable or unprotectable by plant variety rights.
  • Plant parts are understood to mean all aboveground and subterranean parts and organs of plants such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes.
  • the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
  • crops and vegetative and generative propagation material such as cuttings, tubers, rhizomes, offshoots and seeds.
  • all plants and their parts can be treated.
  • wild plant species or varieties of plants obtained by conventional biological breeding methods such as crossing or protoplast fusion and their parts are treated.
  • transgenic plants and varieties of plants which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and parts thereof are treated.
  • Parts or “parts of plants” or “Pfianzenmaschine” has been explained above.Particular plants according to the invention are treated according to the invention of the respective commercially available or in use plant varieties.Piezian cultivars are understood as meaning plants with new properties (“traits”) have been bred either by conventional breeding, by mutagenesis or by recombinant DNA techniques. These may be varieties, breeds, biotypes and genotypes.
  • the treatment of the plants and plant parts with the active substances or active compound combinations or agents to be used according to the invention or according to the invention is carried out directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, spraying, sprinkling, evaporating, atomising, atomizing, sprinkling, foaming, brushing, spreading, injecting, pouring, drip irrigation and propagating material, in particular in the case of seeds Furthermore, 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, i. the active compounds, active ingredient combinations or agents are applied to the foliage, wherein the treatment frequency and the application rate can be adapted to the infestation pressure of the respective pathogen, pest or weed.
  • the active ingredients, active ingredient combinations or agents reach the plants via the root system.
  • the treatment of the plants is then carried out by the action of Active ingredients, active ingredient combinations or agents on the habitat of the plant.
  • This can be, for example, by drenching, mixing into the soil or the nutrient solution, ie the location of the plant (eg soil or hydroponic systems) is impregnated with a liquid form of the active ingredients, active ingredient combinations or compositions, or by the soil application, ie the active compounds according to the invention , Active ingredient combinations or agents are introduced in solid form, (eg in the form of granules) in the location of the plants. In water rice crops, this may also be by metered addition of the invention in a solid form (eg as granules) into a flooded paddy field.
  • seed treatment methods should also include the intrinsic insecticidal or nematicidal properties of pest-resistant transgenic plants in order to achieve optimum protection of the seed and of the germinating plant with a minimum of pesticide use.
  • the present invention therefore also relates in particular to a method for protecting seed and germinating plants from attack by pests by treating the seed with an active substance according to the invention or to be used according to the invention.
  • the method according to the invention for the protection of seeds and germinating plants from infestation by pests comprises a method in which the seed is treated simultaneously in one operation with an active compound of the formula (I) and mixing partner. It also includes a method in which the seed is treated at different times with an active ingredient of formula (I) and mixing partner.
  • the invention also relates to the use of the active ingredients according to the invention for the treatment of seed for the protection of the seed and the resulting plant from animal pests.
  • the invention relates to seed which has been treated with an active ingredient according to the invention for protection against animal pests.
  • the invention also relates to seed treated at the same time with an active ingredient of formula (I) and mixing partner.
  • the invention further relates to seed which has been treated at different times with an active compound of the formula (I) and mixing partner.
  • the individual active substances of the agent according to the invention may be present in different layers on the seed. In this case, the layers which contain an active ingredient of the formula (I) and mixing partners may optionally be separated by an intermediate layer.
  • the invention also relates to seed in which an active compound of the formula (I) and mixing partner are applied as a constituent of a coating or as a further layer or further layers in addition to a coating. Furthermore, the invention relates to seed, which after the treatment with the active ingredient of the formula (I) or an active ingredient combination containing it has been subjected to a film coating process in order to avoid dust abrasion on the seed.
  • One of the advantages of the present invention is that because of the particular systemic properties of the agents of the invention, the treatment of the seed with these agents not only protects the seed itself, but also the resulting plants after emergence from animal pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • Another advantage is the fact that by the treatment of the seed with active ingredient of the formula (I) or combination of active substances containing germination and emergence of the treated seed can be promoted.
  • active compounds of the formula (I) and the named active substance combinations can be used in particular also in the case of transgenic seed.
  • active compounds of the formula (I) can be used in combination with signal technology agents, by way of example a better colonization with symbionts, such as rhizobia, mycorrhiza and / or endophytic bacteria, taking place and / or optimizing them Nitrogen fixation is coming.
  • compositions according to the invention are suitable for the protection of seeds of any plant variety used in agriculture, in the greenhouse, in forests or in horticulture.
  • these are seeds of cereals (eg wheat, barley, rye, millet and oats), maize, cotton, soy, rice, potatoes, sunflower, coffee, tobacco, canola, rapeseed, turnip (eg Sugar beet and fodder beet), peanut, vegetables (eg tomato, cucumber, bean, cabbage, onions and lettuce), fruit plants, turf and ornamental plants.
  • cereals eg wheat, barley, rye and oats
  • corn, soya, cotton, canola, oilseed rape and rice are examples of seeds of cereals (such as wheat, barley, rye and oats), corn, soya, cotton, canola, oilseed rape and rice.
  • transgenic seed with active ingredients of the formula (I) or a combination of active substances is of particular importance.
  • active ingredients of the formula (I) or a combination of active substances are of particular importance.
  • the heterologous genes in transgenic seed can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. comes.
  • the active ingredient of the formula (I) is applied to the seed alone (or as active ingredient combination) or in a suitable formulation.
  • the seed is treated in a state where it is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be done at any time between harvesting and sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, hull, wool or pulp.
  • seeds may be used which have been harvested, cleaned and dried to a moisture content of less than 15% by weight.
  • seed may also be used which, after drying, e.g. treated with water and then dried again.
  • the agents according to the invention can be applied directly, ie without containing further components and without being diluted.
  • suitable formulations and methods for seed treatment are known to those skilled in the art and are described e.g. in the following documents: US 4,272,417 A, US 4,245,432 A, US 4,808,430 A, US 5,876,739 A, US 2003/0176428 AI, WO 2002/080675 AI, WO 2002/028186 A2.
  • the active compounds / active substance combinations that can be used according to the invention can be converted into the customary seed dressing formulations, such as solutions, emulsions, suspensions, powders, foams, slurries or other seed coating compositions, as well as ULV formulations.
  • formulations are prepared in a known manner by mixing the active ingredients / drug combinations with conventional additives, such as conventional extenders and - 61 -
  • Solvents or diluents dyes, wetting agents, dispersants, emulsifiers, defoamers, preservatives, secondary thickeners, adhesives, gibberellins and also water.
  • Dyes which may be present in the seed dressing formulations which can be used according to the invention are all dyes customary for such purposes. Both water-insoluble pigments and water-soluble dyes are useful in this case. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes.
  • Suitable wetting agents which may be present in the seed dressing formulations which can be used according to the invention are all wetting-promoting substances customary for the formulation of agrochemical active compounds.
  • Preferably used are alkylnaphthalene sulfonates, such as diisopropyl or diisobutyl naphthalene sulfonates.
  • Suitable dispersants and / or emulsifiers which may be present in the seed dressing formulations which can be used according to the invention are all nonionic, anionic and cationic dispersants customary for the formulation of agrochemical active compounds.
  • Preferably usable are nonionic or anionic dispersants or mixtures of nonionic or anionic dispersants.
  • Particularly suitable nonionic dispersants are, in particular, ethylene oxide-propylene oxide block polymers, alkylphenol polyglycol ethers and tristryrylphenol polyglycol ethers and their phosphated or sulfated derivatives.
  • Suitable anionic dispersants are in particular lignosulfonates, polyacrylic acid salts and arylsulfonate-formaldehyde condensates.
  • Defoamers which may be present in the seed dressing formulations which can be used according to the invention are all foam-inhibiting substances customary for the formulation of agrochemical active compounds.
  • Preferably usable are silicone defoamers and magnesium stearate.
  • Preservatives which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Examples include dichlorophen and Benzylalkoholhemiformal.
  • Suitable secondary thickeners which may be present in the seed dressing formulations which can be used according to the invention are all substances which can be used for such purposes in agrochemical compositions. Preference is given to cellulose derivatives, acrylic acid derivatives, xanthan, modified clays and finely divided silica.
  • Suitable adhesives which may be present in the seed dressing formulations which can be used according to the invention are all customary binders which can be used in pickling agents. Preferably mentioned are polyvinylpyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose. n
  • the gibberellins are known (see R. Wegler "Chemie der convinced- und Swdlingsbekungsstoff", Vol. 2, Springer Verlag, 1970, pp. 401-412).
  • the seed dressing formulations which can be used according to the invention can be used either directly or after prior dilution with water for the treatment of seed of various kinds.
  • the concentrates or the preparations obtainable therefrom by dilution with water can be used for dressing the seeds of cereals such as wheat, barley, rye, oats and triticale, as well as the seeds of corn, rice, rape, peas, beans, cotton, sunflowers and beets or even vegetable seeds of various nature.
  • the seed dressing formulations which can be used according to the invention or their diluted preparations can also be used for pickling seeds of transgenic plants. In this case, additional synergistic effects may occur in interaction with the substances formed by expression.
  • the seed dressing formulations which can be used according to the invention or the preparations prepared therefrom by the addition of water
  • all mixing devices customarily usable for the dressing can be considered.
  • the seed is placed in a mixer which adds either desired amount of seed dressing formulations either as such or after prior dilution with water and mixes until evenly distributed the formulation on the seed.
  • a drying process follows.
  • the application rate of the seed dressing formulations which can be used according to the invention can be varied within a relatively wide range. It depends on the respective content $ of the active substance (s) in the formulations and on the seed.
  • the application rates for active compounds / active substance combinations are generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 15 g per kilogram of seed.
  • the active compounds of the formula (I) have an effect against biotic stress factors and / or abiotic stress of plants or with regard to plant growth. It has now been found that the active compounds of the formula (I) according to the invention are suitable for increasing the plant's own defenses (pathogen defense in plants).
  • plants react to natural stress conditions, such as, for example, cold, heat, dryness, wounding, pathogen infestation (viruses, bacteria, fungi), insects, etc., but also to herbicides with specific or nonspecific defense mechanisms (plant biochemistry, - 63 -
  • enzymatic proteins such as chitinases, glucanases, or (d) specific inhibitors of essential proteins, such as protease inhibitors, xylanase inhibitors attack the pathogen directly or impede its proliferation (Dangl and Jones, Nature 411, 826-833, 2001; Kessler and Baldwin, Annual Review of Plant Biology, 53, 299-328, 2003).
  • HR hypersensitive reaction
  • a known synthetic product, which one of the salicylic acid similar function is performed and can provide a protective effect against phytopathogenic fungi, bacteria and viruses, is benzothiadiazole (CGA 245704; Common name: acibenzolar-5-methyl; trade name: Bion ®) (Achuo et al. , Plant Pathology 53 (1), 65-72, 2004, Tamblyn et al., Pesticide Science 55 (6), 676-677, 1999, EP-OS 0 313 512).
  • CGA 245704 Common name: acibenzolar-5-methyl
  • Bion ® Bion ®
  • pathogenesis-related proteins which primarily support plants in the defense against biotic stressors, such as phytopathogens Fungi, Bacteria and Viruses (DE 10 2005 045 174 A; DE 10 2005 022 994 A and WO 2006/122662 A; Thielert Maischutz-Nachzin Bayer, 59 (1), 73-86, 2006; Francis et al., European Journal of Plant Pathology, publ. online 23.1.2009).
  • plants have a number of endogenous reaction mechanisms that can effect effective defense against various harmful organisms (biotic stress) and / or abiotic stress.
  • the cultivation of healthy and uniformly grown seedlings is an essential prerequisite for the large-scale cultivation and economic management of agricultural, horticultural and forestry crops.
  • Styrofoam perforated trays seeded in a special potting soil based on peat culture substrate and then cultivated in containers with suitable nutrient solution until the desired transplant size is reached (Figure 1).
  • the containers are allowed to run on the nutrient solution, from which the name of the growing method is derived (Leal, 2001, supra).
  • Floating processes have been using insecticides from the class of neonicotiniodes (chlornicotinyls) for the control of sucking pests for several years.
  • the plants are sprayed with neonicotinoid (chloronicotinyl) insecticides in the float process shortly before transplanting or are infused with neonicotinoid (chloronicotinyl) insecticides immediately before or during transplantation, which is termed "drenching" (Leal, 2001, supra; and Rogers, 2001, supra) Both methods of application are technically relatively complex.
  • Fungicides and insecticides are used to protect the crops of seed or plant material from fungal pathogens and pests until they are transplanted.
  • the choice of pesticides, the place and time of application and the application rate of the funds depend here mainly on the type of fungal diseases and pests occurring, the specific mode of action and duration of action of the agents and their plant compatibility, and thus directly to the specific requirements of different Adapted to crops and regions.
  • the active compounds of the formula (I) lead, regardless of insect control, to good protection of the plant from damage by fungal, bacterial or viral pathogens.
  • the active compounds of the formula (I) not only increase the pathogen defense in plants, but also improve plant growth and / or increase the resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO (Mycoplasma -like organisms) and / or RLO (Rickettsia-like organisms) are caused, especially against soil-borne fungal diseases, and / or are suitable for increasing the resistance of plants to abiotic stress factors.
  • Abiotic stress conditions may include, for example, drought, cold and heat conditions, osmotic stress, waterlogging, increased soil salinity, increased exposure to minerals, ozone conditions, high light conditions, limited availability of nitrogen nutrients, limited availability of phosphorous nutrients, or avoidance of shade.
  • the present invention therefore relates firstly to the use of at least one active substance of the formula (I) for increasing plant-specific defense forces and / or for improving plant growth and / or for increasing the resistance of plants to plant diseases caused by fungi, bacteria, viruses, MLO (mycoplasma-like organisms) and / or RLO (Rickettsia-like organisms) are caused, in particular against soil-borne fungal diseases, and / or to increase the resistance of plants to abiotic stress factors.
  • the term plant growth is understood to mean various advantages for plants which are not directly related to the known pesticidal activity, preferably to the insecticidal activity of the active compounds of the formula (I).
  • Such advantageous properties are, for example, the following improved plant characteristics: accelerated germination and emergence of the seed and planting material, improved surface and depth root growth, increased runners or stocking, stronger and more productive shoots and tillers, improvement in shoot growth, increased stability, increased shoot base diameter, increased leaf area, greener leaf color, higher yields of nutrients and ingredients, such as carbohydrates, fats, oils, proteins, vitamins, minerals, essential oils, dyes, fibers, better fiber quality, earlier flowering, increased number of flowers, reduced content of toxic products such as Mycotoxins, reduced content of residues or unfavorable components of any kind or better digestibility, improved storage stability of the crop, improved tolerance to unfavorable temperature improved tolerance to drought and dryness as well as oxygen deficiency due to excess water, improved tolerance to increased salt levels in soils and water, increased tolerance to UV radiation, increased tolerance to ozone stress, improved ⁇
  • Soche terms are, for example, the following: phytotonic effect, resistance to stressors, less plant stress, plant health, healthy plants, Plant Fitness, Plant Wellness, Plant Concept, Vigor Effect, Stress Shield "Crop Health Properties”, “Crop Health Products”, “Crop Health Management”, “Crop Health Therapy”, “Plant Health”, “Plant Health Properties”, “Plant Health Products”, “Plant Health Management”, “Plant Health Therapy”, “Greening Effect” or “Re-greening Effect”), “Freshness” or other terms that are well known to a person skilled in the art.
  • Fertilizers which can be used according to the invention together with the above-described active agents or agents are generally organic and inorganic nitrogen-containing compounds such as ureas, urea-formaldehyde condensation products, amino acids, ammonium salts and nitrates, potassium salts (preferably chlorides, sulfates, nitrates ), Phosphoric acid salts and / or salts of phosphorous acid (preferably potassium salts and ammonium salts).
  • NPK fertilizers ie fertilizers containing nitrogen, phosphorus and potassium, calcium ammonium nitrate, ie fertilizers that still contain calcium, ammonium sulfate nitrate (General formula NH4NO3), ammonium phosphate and ammonium sulfate.
  • These fertilizers are well known to those skilled in the art, see also, for example, Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, Vol. A 10, pages 323 to 431, Verlagsgesellschaft, Weinheim, 1987.
  • the fertilizers may also contain salts of micronutrients (preferably calcium, sulfur, boron, manganese, magnesium, iron, boron, copper, zinc, molybdenum and cobalt) and phytohormones (eg, vitamin B1 and indol-3-ylacetic acid (IAA)). or mixtures thereof.
  • Fertilizers used according to the invention may also contain other salts such as monoammonium phosphate (MAP), diammonium phosphate (DAP), potassium sulfate, potassium chloride or magnesium sulfate.
  • Suitable amounts for the secondary nutrients or trace elements are amounts of from 0.5 to 5% by weight, based on the total fertilizer.
  • fertilizers can be used, for example, in the form of powders, granules, prills or compactates. However, the fertilizers can also be used in liquid form dissolved in an aqueous medium. In this case, dilute aqueous ammonia can be used as nitrogen fertilizer. Further possible ingredients for fertilizers are described, for example, in Ullmann's Encyclopedia of Industrial Chemistry, 5th Edition, 1987, Volume A 10, pages 363 to 401, DE-A 41 28 828, DE-A 19 05 834 and DE-A 196 31 764 ,
  • the general composition of the fertilizers which in the context of the present invention may be single nutrient and / or multi-nutrient fertilizers, for example nitrogen, potassium or phosphorus, may vary within a wide range.
  • a content of 1 to 30% by weight of nitrogen preferably 5 to 20% by weight
  • of 1 to 20% by weight of potassium preferably 3 to 15% by weight
  • Phosphorus preferably 3 to 10 parts by weight
  • the content of microelements is usually in the ppm range, preferably in the range of 1 to 1000 ppm.
  • the fertilizer and the active ingredient of the formula (I) at the same time, i. synchronously, administered.
  • the application takes place in a functional context, in particular within a period of generally 24 hours, preferably 18 hours, more preferably 12 hours, especially 6 hours, even more specifically 4 hours, more specifically within 2 hours.
  • the active compounds of the general formula (I) and of the fertilizer according to the invention are used in a time frame of less than 1 hour, preferably less than 30 minutes, more preferably less than 15 minutes.
  • the corresponding constituents can be mixed with one another and optionally extruded or the at least one active compound of the formula (I) to be used according to the invention can be applied to the fertilizer.
  • formulation aids may also be used in the dimensionally stable mixtures, such as extenders or pressure-sensitive adhesives, to achieve dimensional stability of the resulting mixture. Due to the corresponding dimensional stability, corresponding mixtures are suitable, in particular for use in the "Home & Garden" sector, ie for a private user or home gardener, who can use the dimensionally stable mixture or the constituents contained therein with a predetermined, clearly defined amount and without special aids ,
  • the mixtures of at least one of the active ingredients to be used according to the invention and the at least one fertilizer may also be liquid, so that-for example, in the case of a professional user in the field of agriculture-the resulting mixture can be applied as a so-called tank solution.
  • the active compounds to be used according to the invention can, if appropriate in combination with fertilizers, preferably be applied to the following plants, the following listing not being restrictive.
  • the forest stock includes trees for the production of wood, pulp, paper and products made from parts of the trees.
  • crops as used herein refers to crops used as plants for the production of food, feed, fuel or for technical purposes.
  • the crops include, for example, the following plant species: turf, vines, cereals, for example wheat, barley, rye, oats, triticale, rice, corn and millet; Beets, for example sugar beets and fodder beets; Fruits, such as pome fruit, stone fruit and soft fruit, such as apples, pears, plums, peaches, almonds, cherries and berries, eg. Strawberries, raspberries, blackberries; Legumes, such as beans, lentils, peas and soybeans; Oil crops such as rapeseed, mustard, poppy, olive, sunflower, coconut, castor oil, cocoa beans and peanuts; Cucurbits, for example squash, cucumbers and melons; Fiber plants, for example 7Q
  • Vegetables such as spinach, (headj salad, asparagus, cabbage, carrots, onions, tomatoes, potatoes and peppers, laurel family, such as avocado, cinnamomum, camphor, or even plants such as tobacco, nuts, coffee, eggplant, sugarcane, tea, pepper , Vines, hops, bananas, natural rubber plants and ornamental plants, such as flowers, shrubs, deciduous trees and conifers, this list is not limiting.
  • Particularly suitable target crops are the following plants: bamboo wool, eggplant, turf, pome fruit, stone fruit, berry fruit, corn, wheat, barley, cucumber, tobacco, vines, rice, cereals, pear, beans, soybeans, oilseed rape, tomatoes, peppers, melons , Cabbage, potato and apple.
  • trees are: Abies sp., Eucalyptus sp., Picea sp., Pinus sp., Aesculus sp., Platanus sp., Tilia sp., Acer sp., Tsuga sp., Fraxinus sp., Sorbus sp., Betula sp., Crataegus sp., Ulmus sp., Quercus sp., Fagus sp., Salix sp., Populus sp.
  • trees From the tree species Aesculus: A. hippocastanum, A. pariflora, A. carnea; from the tree species Platanus: P. aceriflora, P. occidentalis, P. racemosa; from the tree species Picea: P. abies; from the species Pinus: P. radiate, P. ponderosa, P. contorta, P. sylvestre, P. elliottii, P. montecola, P. albicaulis, P. resinosa, P. palustris, P. taeda, P. flexilis, P jeffregi, P. baksiana, P. strobes; from the tree species Eucalyptus: E. grandis, E. globulus, E. camadentis, E. nitens, E. obliqua, E. regnans, E. pilularus.
  • Particularly preferred trees can be called: horse chestnut, sycamore, linden, maple tree.
  • the present invention may also be practiced on any type of "turigrass", including "cool season turigrasses” and "warm season turigrasses.”
  • cold season lawn species are blue grasses (Poa spp “Kentucky bluegrass” (Poa pratensis L.), “rough bluegrass” (Poa trivialis L.), “Canada bluegrass” (Poa compressa L.), “annual bluegrass” (Poa annua L.), “upland bluegrass” (Poa glaucantha Gaudin), “wood bluegrass” (Poa nemoralis L.) and “bulbous bluegrass” (Poa bulbosa L.); ostrich grasses ("Bentgrass”, Agrostis spp.), such as “creeping bentgrass” (Agrostis palustris Huds.), “ colonial bentgrass “(Agrostis tenuis sib.),” velvet bentgrass “(Agrostis canina L.),” South
  • Examples of other "cool season turfgrasses” are “beachgrass” (Ammophila breviligulata Fern.), “Smooth bromegrass” (Bromus inermis leyss.), Reeds ("cattails") such as “Timothy” (Phleum pratense L.), “sand cattail “(Phleum subulatum L.),” orchardgrass “(Dactylis glomerata L.),” weeping alkaligrass “(Puccinellia distans (L.) Pari.) And” crested dog's-tail “(Cynosurus cristatus L.).
  • Examples of “warm season turfgrasses” are “Bermudagrass” (Cynodon spp., LC Rieh), “zoysiagrass” (Zoysia spp. Willd.), “St. Augustine grass” (Stenotaphrum secundatum Walt Kuntze), “centipedegrass” (Eremochloa ophiuroides Munrohack.), “Carpetgrass” (Axonopus afflnis Chase), “Bahia grass” (Paspalum notatum flügge), “Kikuyugrass” (Pennisetum clandestinum detergent, ex Chiov.), “Buffalo grass” (Buchloe daetyloids (Nutt.) Engelm.) , “Blue gramma” (Bouteloua gracilis (HBK) lag.
  • the active compounds of the formula (I) and their compositions are suitable for controlling animal pests in the hygiene sector.
  • the invention can be used in household, hygiene and storage protection, especially for controlling insects, arachnids and mites, which occur in enclosed spaces, such as apartments, factories, offices, vehicle cabins.
  • the active compounds or compositions are used alone or in combination with other active ingredients and / or adjuvants.
  • they are used in household insecticide products.
  • the active compounds according to the invention are active against sensitive and resistant species as well as against all stages of development.
  • pests of the class Arachnida from the orders Scorpiones, Araneae and Opiliones, from the classes Chilopoda and Diplopoda, from the class Insecta the order Blattodea, from the orders Coleoptera, Dermaptera, Diptera, Heteroptera, Hymenoptera, Isoptera, Lepidoptera, Phthiraptera, Psocoptera, Saltatoria or Orthoptera, Siphonaptera and Zygentoma and from the class Malacostraca the order Isopoda.
  • Application is for example in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cushions and moth gels, as granules or dusts, in litter or bait stations.
  • Pump and atomizer sprays e.g. Pump and atomizer sprays, fog machines, foggers, foams, gels, evaporator products with cellulose or plastic evaporator plates, liquid evaporators, gel and membrane evaporators, propeller-driven evaporators, energy-less or passive evaporation systems, moth papers, moth cushions and moth gels, as granules or dusts, in litter or bait stations.
  • the active ingredients of formula (I) may be used to combat a variety of pests including, for example, noxious sucking insects, biting insects and other plant parasitic pests, storage pests, pests that destroy industrial materials, and use and include sanitary pests including animal health parasites combat such as their extinction and eradication.
  • the present invention thus also includes a method of controlling pests.
  • the active compounds according to the invention are active against animal parasites, in particular ectoparasites or endoparasites.
  • the term endoparasite includes in particular helminths and protozoa such as coccidia.
  • Ectoparasites are typically and preferably arthropods, especially insects and acarids.
  • the compounds of the present invention having favorable toxicity to warm-blooded animals are useful in the control of parasites found in livestock and livestock in livestock, breeding animals, zoo animals, laboratory animals, experimental animals and domestic animals. They are effective against all or individual stages of parasite development.
  • Farm animals include, for example, mammals such as sheep, goats, horses, donkeys, camels, buffaloes, rabbits, reindeer, fallow deer, and especially cattle and pigs; or poultry such as turkeys, ducks, geese and, in particular, chickens; or fish or crustaceans, e.g. in aquaculture; or possibly insects such as bees.
  • the domestic animals include, for example, mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets or, in particular, dogs, cats; Caged birds; reptiles; Amphibians or aquarium fish.
  • mammals such as hamsters, guinea pigs, rats, mice, chinchillas, ferrets or, in particular, dogs, cats; Caged birds; reptiles; Amphibians or aquarium fish.
  • the compounds of the invention are administered to mammals.
  • the compounds according to the invention are administered to birds, namely caged birds or, in particular, poultry.
  • control means that the agents can effectively reduce the incidence of the particular parasite in an animal infected with such parasites to a harmless extent. More specifically, “combat” in the present context means that the active ingredient can kill the respective parasite, prevent its growth or prevent its replication.
  • arthropods include, but are not limited to, the order Anoplurida, for example Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp .; from the order Mallophagida and the suborders Amblycerina and Ischnocerina, for example Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp .; from the order Diptera and the suborders Nematocerina and Brachycerina, for example Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus
  • the following Akari are exemplary, but without limitation, from the subclass Akari (Acarina) and the order Metastigmata, for example, from the family Argasidae, such as Argas spp., Ornithodorus spp., Otobius spp., From the family Ixodidae, such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp.
  • Argasidae such as Argas spp., Ornithodorus spp., Otobius spp.
  • Ixodidae such as Ixodes spp., Amblyomma spp., Rhipicephalus (Boophilus) spp. Dermacentor spp., Haem
  • parasitic protozoa examples include, but are not limited to:
  • Mastigophora such as Trypanosomatidae, for example Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax, Leishmania brasiliensis, L. donovani, L. tropica, such as Trichomonadidae, for example Giardia lamblia, G. canis.
  • Trypanosomatidae for example Trypanosoma b. brucei, T.b. gambiense, T.b. rhodesiense, T. congolense, T. cruzi, T. evansi, T. equinum, T. lewisi, T. percae, T. simiae, T. vivax
  • Sarcomastigophora such as Entamoebidae, for example Entamoeba histolytica, Hartmanellidae, for example Acanthamoeba sp., Harmanella sp.
  • Apicomplexa such as Eimeridae, for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E. brunetti, E canis, E. chinchillae, E. clupearum, E. columbae, E. contorta, E. crandalis, E. debliecki, E. dispersa, E. ellipsoidales, E. falciformis, E. faurei, E. flavescens, E.
  • Eimeridae for example Eimeria acervulina, E. adenoides, E. alabamensis, E. anatis, E. anserina, E. arloingi, E. ashata, E. auburnensis, E. bovis, E.
  • gallopavonis E. hagani, E. intestinalis, E. iroquoina, E. irresidua, E. labbeana, E. leucarti, E. magna, E. maxima, E.media, E. meleagridis, E. meleagrimitis, E. mitis, E necatrix, E. ninakohlyakimovae, E.ovis, E.parva, E.pavonis, E. perforans, E. phasani, E. piriformis, E. praecox, E. residua, E. scabra, E.spec, E. sitesdai E. suis, E. tenella, E.
  • S. suihominis such as Leucozoidae, for example Leucocytozoon simondi, such as Plasmodiidae, for example Plasmodium berghei, P. falciparum, P. malariae, P. ovale, P.vivax, P.spec, such as piroplasmea, for example Babesia argentina, B.bovis, B.canis, B.spec, Theileriaparva, Theileria spec, such as Adeleina, for example Hepatozoon canis, H. spec.
  • pathogenic endoparasites examples include flatworms (e.g., Monogenea, Cestodes, and Trematodes), roundworms, Acanthocephala, and Pentastoma.
  • flatworms e.g., Monogenea, Cestodes, and Trematodes
  • roundworms e.g., Acanthocephala
  • Pentastoma e.g., Pentastoma.
  • Other helminths include, but are not limited to:
  • Monogenea e.g., Gyrodactylus spp., Dactylogyrus spp., Polystoma spp.
  • Cestodes from the order Pseudophyllidea for example: Diphyllobothrium spp., Spirometra spp., Schistocephalus spp., Ligula spp., Bothridium spp., Diplogonoporus spp.
  • Taenia spp. Echinococcus spp., Hydatigera spp., Davainea spp., Raillietina spp., Hymenolepis spp., Echinolepis spp., Echinocotyle spp., Diorchis spp., Dipylidium spp., Joyeuxiella spp., Diplopylidium spp.
  • Trematodes from the genus Digenea, for example: Diplostomum spp., Posthodiplostomum spp., Schistosoma spp., Trichobilharzia spp., Ornithobilharzia spp., Austrobilharzia spp., Gigantobilharzia spp., Leucochloridium spp., Brachylaima spp., Echinostoma spp., Echinoparyphium spp., Echinochasmus spp., Hypoderaeum spp., Fasciola spp., Fasciolides spp., Fasciolopsis spp., Cyclocoelum spp., Typhlocoelum spp., Paramphistomum spp., Calicophoron spp., Cotylophoron spp., Gigantocoty
  • Stephanurus spp. Ancylostoma spp., Uncinaria spp., Bunostomum spp., Globocephalus spp., Syngamus spp., Cyathostoma spp., Metastrongylus spp., Dictyocaulus spp., Muellerius spp., Protostrongylus spp., Neostrongylus spp., Cystocaulus spp., Pneumostrongylus spp., Spicocaulus spp., Elaphostrongylus spp.
  • Parelaphostrongylus spp. Crenosoma spp., Paracrenosoma spp., Angiostrongylus spp., Aelurostrongylus spp., Filaroides spp., Parafilaroides spp., Trichostrongylus spp., Haemonchus spp., Ostertagia spp., Marshallagia spp., Cooperia spp., Nematodirus spp , Hyostrongylus spp., Obeliscoides spp., Amidostomum spp., Ollulanus spp.
  • Acanthocephala from the order Oligacanthorhynchida eg: Macracanthorhynchus spp., Prosthenorchis spp .; from the order Polymorphida for example: Filicollis spp .; from the order Moniliformida for example: Moniliformis spp.,
  • Echinorhynchida for example Acanthocephalus spp.
  • Echinorhynchus spp. Echinorhynchus spp.
  • Pentastoma from the order Porocephalida for example Linguatula spp.
  • the administration of the active compounds according to the invention is carried out by methods well known in the art, such as enteral, parenteral, dermal or nasal in the form of suitable preparations.
  • the administration can be prophylactic or therapeutic.
  • one embodiment of the present invention relates to compounds of the invention for use as a medicament.
  • Another aspect relates to compounds of the invention for use as antiendoparasitic agents, in particular a helminthicide or antiprotozoal agent.
  • compounds of the invention for use as antiendoparasitic agents in particular a helminthicide or antiprotozoal agents, e.g. in animal husbandry, animal husbandry, stables and in the hygiene sector.
  • Another aspect relates to compounds of the invention for use as an antiectica, in particular an arthropodicide such as an insecticide or an acaricide.
  • compounds according to the invention for use as anti-topazarasitic, in particular an arthropodicide such as an insecticide or acaricide for example in animal husbandry, in animal husbandry, in stables, in the hygiene sector.
  • the active compounds of the formula (I) and compositions containing them are suitable for the protection of industrial materials against attack or destruction by insects, e.g. from the order Coleoptera, Hymenoptera, Isoptera, Lepidoptera, Psocoptera and Zygentoma.
  • compositions or compositions according to the invention contain at least one further insecticide and / or at least one fungicide.
  • this composition according to the invention is a ready-to-use composition, that is, it can be applied without further changes to the _
  • the active compounds and compositions according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quays and signal systems, which come into contact with seawater or brackish water.
  • the active compounds and compositions according to the invention can be used alone or in combinations with other active substances as antifouling agents.
  • N-acylation reaction was carried out analogously to the procedure of Example 1 using: 84.0 mg (0.42 mmol) of 2- (3-chloro-4-amino-1H-pyrazol-1-yl) -pyrazine 77.4 mg (0.64 mmol) of 3-methylthio-propionic acid 4.2 ml of dichloromethane
  • reaction mixture was stirred for about 18 hours at room temperature.
  • reaction mixture was concentrated in vacuo and the remaining residue purified by silica gel chromatography (cyclohexane-acetone gradient).
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
  • active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
  • Bean leaf discs Phaseolus vulgaris infected by all stages of the common spider mite (Tetranychus urticae) are sprayed with an active compound preparation of the desired concentration.
  • Emulsifier 0.5 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration. 0 "
  • Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).

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Abstract

La présente invention concerne de nouveaux composés hétérocycliques, des procédés pour les fabriquer et leur utilisation pour lutter contre des animaux nuisibles, parmi lesquels des arthropodes et en particulier des insectes, ainsi que des produits intermédiaires servant à préparer les composés hétérocycliques.
PCT/EP2013/071469 2012-10-18 2013-10-15 Composés hétérocycliques pour la lutte contre les nuisibles Ceased WO2014060381A1 (fr)

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CN104945326A (zh) * 2015-06-24 2015-09-30 安徽农业大学 一种双吡唑酰胺类衍生物及其制备方法及在防治小菜蛾中的应用

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