EP1771065A2 - Agents insecticides a base d'insecticides et de phytoprotecteurs selectionnes - Google Patents

Agents insecticides a base d'insecticides et de phytoprotecteurs selectionnes

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Publication number
EP1771065A2
EP1771065A2 EP05772342A EP05772342A EP1771065A2 EP 1771065 A2 EP1771065 A2 EP 1771065A2 EP 05772342 A EP05772342 A EP 05772342A EP 05772342 A EP05772342 A EP 05772342A EP 1771065 A2 EP1771065 A2 EP 1771065A2
Authority
EP
European Patent Office
Prior art keywords
alkyl
phenyl
ethyl
substituted
methyl
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP05772342A
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German (de)
English (en)
Inventor
Reiner Fischer
Wolfram Andersch
Heike Hungenberg
Wolfgang Thielert
Lothar Willms
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Bayer CropScience AG
Original Assignee
Bayer CropScience AG
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Filing date
Publication date
Application filed by Bayer CropScience AG filed Critical Bayer CropScience AG
Publication of EP1771065A2 publication Critical patent/EP1771065A2/fr
Withdrawn legal-status Critical Current

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Classifications

    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
    • A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests

Definitions

  • the invention relates to insecticidally active ingredient combinations which contain one or more compounds selected from the group of acetylcholinesterase inhibitors, sodium channel modulators, inhibitors of chitin biosynthesis, juvenile hormone mimetics, chloride channel activators, ecdysone agonists, GABA -controlled chloride channel antagonists and selected acaricides, on the one hand, and at least one compound that improves crop plant compatibility, on the other hand, and their use for controlling insects and arachnids (acarids) in various crops and for treating seed.
  • the subject of the invention is therefore insecticidal agents comprising
  • H 3 CNC-CH-S- - 9P-OCH, H OCK is known from US 2 494 283 A.1.5 Disulfone
  • n is a number between 0 and 5
  • a 1 represents one of the divalent heterocyclic groupings outlined below,
  • n is a number between 0 and 5
  • a 2 is optionally substituted by Ci-C 4 alkyl, C r C 4 -alkoxy-carbonyl or C r and C is 4 alkenyloxy carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,
  • R 8 is hydroxy, mercapto, amino, Ci-C 6 alkoxy, C r C 6 alkylthio, Ci-C 6 -alkylamino or di- (Ci-C 4 -alkyl) -amino,
  • R 9 is hydroxy, mercapto, amino, C 1 -C 7 -alkoxy, C 1 -C 6 -alkenyloxy, C 1 -C 6 -alkenyloxyC r C 6 -alkoxy, C 1 -C 6 -alkylthio, C 1 -C 6 -alkylamino or di- (C C 4 alkyl) amino,
  • R 10 is in each case optionally fluorine, chlorine and / or bromine-substituted C 1 -C 4 -alkyl
  • R 11 represents hydrogen, in each case optionally substituted by fluorine, chlorine and / or bromine-substituted C 1 - C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, Ci-C 4 -alkoxy-C 4- alkyl, dioxolanyl-C r C 4 - alkyl, furyl, furyl-C r C 4 alkyl, thienyl, thiazolyl, piperidinyl, or optionally substituted by fluorine, chlorine and / or bromine or C] -C 4 alkyl-substituted phenyl stands,
  • R 12 represents hydrogen, in each case optionally substituted by fluorine, chlorine and / or bromine-substituted C 1 - C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, C r C 4 alkoxy-CrC 4 - alkyl, dioxolanyl-Ci-C 4 - alkyl, furyl, furyl-C r C 4 alkyl, 4 alkyl substituted phenyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine and / or bromine or C, and R 11 and R 12 are also taken together in each case optionally by C 1 -C 4 -alkyl, phenyl, furyl, an annel ⁇ nated benzene ring or by two substituents which together with the carbon atom to which they are attached, a 5- or Form a 6-membered carboxy ring, substituted C 3 -
  • R 13 represents hydrogen, cyano, halogen, or represents in each case optionally fluorine, chlorine and / or bromine-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl,
  • R 14 is hydrogen, optionally substituted by hydroxy, cyano, halogen or C 1 -C 4 -alkoxy-substituted CrQ-alkyl, C 3 -C 6 -cycloalkyl or tri- (C 1 -C 4 -alkyl) -silyl,
  • R 15 represents hydrogen, cyano, halogen, or optionally substituted by fluorine, chlorine and / or bromine-substituted C r C 4 alkyl, C 3 -C 6 cycloalkyl or phenyl,
  • X 1 represents nitro, cyano, halogen, C, -C 4 alkyl, dQ-haloalkyl, C, -C 4 alkoxy or C 1 -C 4 - haloalkoxy is,
  • X 2 represents hydrogen, cyano, nitro, halogen, C r C 4 alkyl, Ci-C 4 haloalkyl, C 1 -C
  • X 3 represents hydrogen, cyano, nitro, halogen, Ci-C 4 alkyl, C r C 4 haloalkyl, C 1 -C 4 -alkoxy or C 1 -C 4 haloalkoxy,
  • r and s are a number between 0 and 5
  • R 16 is hydrogen or C 4 -alkyl r C
  • R 17 is hydrogen or C 4 -alkyl r C
  • R 18 represents hydrogen, in each case optionally cyano-, halogen or Ci-C 4 alkoxy substitu ⁇ jewes C r C 6 alkyl, C r C 6 alkoxy, QQ alkylthio, C r C 6 -alkylamino or di- (C R C 4 alkyl) - amino, or in each case optionally substituted by cyano, halogen or C 1 -C 4 -alkyl-substituted C 3 -C 6 -cycloalkyl, C 3 -C 6 -cycloalkyloxy, C 3 -C 6 -cycloalkylthio or C 3 -C 6 -cycloalkylamino,
  • R 19 represents hydrogen, optionally cyano-, hydroxyl-, halogen or Ci-C 4 alkoxy substitu ⁇ jewes Ci-C 6 -alkyl, in each case optionally substituted by cyano or halogen, C 3 -C 6 - alkenyl or C 3 -C 6 - alkynyl, or optionally cyano-, halogen or C r C 4 -alkyl-substituted C 3 -C 6 cycloalkyl,
  • R 20 represents hydrogen, optionally cyano-, hydroxyl-, halogen or C r C 4 alkoxy substitu ⁇ jewes Ci-C ⁇ -alkyl, in each case optionally cyano- or halogen-substituted C 3 -C 6 - alkenyl or C 3 -C 6 - alkynyl optionally substituted by cyano, halogen or C) -C 4 alkyl substi ⁇ tutechnischs C 3 -C 6 cycloalkyl, or optionally substituted by nitro, cyano, halogen, Ci-C4-alkyl, Ci-C 4 haloalkyl, C r C 4 alkoxy or C r C 4 haloalkoxy-substituted phenyl, or together with R 19 represents C 2 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl optionally substituted by C 1 -C 4 -alky
  • X 4 is nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halogen, Q-C 4 alkyl, dC 4 haloalkyl, C 1 -C 4 alkoxy or Ci-C 4 haloalkoxy, and
  • X 5 is nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halo, C r G t alkyl, C r C 4 haloalkyl, C 1 -C 4 alkoxy or C r C 4 haloalkoxy .
  • hydrocarbon chains such as in alkyl, alkenyl or alkanediyl - also in combination with heteroatoms, such as in alkoxy - are in each case straight-chain or branched.
  • optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
  • the compounds of the formula (FV-a), (IV-b), (IV-c), (IV-d) and (FV-e) can also be used as geometric and / or as a function of the nature of the substituents. or optical isomers or mixtures of isomers, in different compositions, which may optionally be separated in a conventional manner. Both the pure isomers and the mixtures of isomers can be used in the compositions according to the invention and can be added to the use according to the invention. For the sake of simplicity, however, the following is always spoken of compounds of the formula (FV-a), (IV-b), (IV-c), (IV-d) and (rV-e), although both the pure compounds if appropriate, mixtures with different proportions of isomeric compounds are meant.
  • a 1 preferably represents one of the divalent heterocyclic groups outlined below
  • n preferably represents the numbers 0, 1, 2, 3 or 4.
  • a 2 preferably represents in each case optionally methyl, ethyl, methoxycarbonyl or ethoxycarbonyl-substituted methylene or ethylene.
  • R 8 is preferably hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i -, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino.
  • R 9 is preferably hydroxy, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methylhexyloxy, allyloxy, 1-allyloxymethyl-ethoxy, methylthio, ethyl ⁇ thio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or diethylamino ,
  • R 10 preferably represents in each case optionally fluorine, chlorine and / or bromine-substituted methyl, ethyl, n- or i-propyl.
  • R 1 ' is preferably hydrogen, in each case optionally substituted by fluorine and / or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl , Methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl substituted phenyl.
  • R 12 is preferably hydrogen, in each case optionally substituted by fluorine and / or chlorine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propynyl or butynyl, Methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, dioxolanylmethyl, furyl, furylmethyl, thienyl, thiazolyl, piperidinyl, or optionally by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t butyl substituted phenyl, or together with R 1 1 represents one of the radicals -CH 2 -O-CH 2 -CH 2 - and -CH 2 -CH 2 -O-CH 2 -CH 2
  • R 13 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally substituted by fluorine, chlorine and / or bromine substituted methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl ,
  • R 14 preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl.
  • R 15 is preferably hydrogen, cyano, fluorine, chlorine, bromine, or in each case optionally substituted by fluorine, chlorine and / or bromine substituted methyl, ethyl, n- or i-propyl, n-, i-, s- o- t-butyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or phenyl.
  • X 1 is preferably nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 2 is preferably hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 3 is preferably hydrogen, nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl , Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • r is preferably one of the numbers 0, 1, 2, 3 or 4.
  • s preferably represents one of the numbers 0, 1, 2, 3 or 4.
  • R 16 is preferably hydrogen, methyl, ethyl, n- or i-propyl.
  • R 17 is preferably hydrogen, methyl, ethyl, n- or i-propyl.
  • R 18 preferably represents hydrogen, in each case optionally cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino , Ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino or die
  • R 19 is preferably hydrogen, in each case optionally cyano, hydroxyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, in each case optionally substituted by cyano, fluorine, chlorine or bromine substituted propenyl, butenyl, propynyl or butynyl, or in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.
  • R 20 is preferably hydrogen, in each case optionally cyano, hydroxyl, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, in each case optionally substituted by cyano, fluorine, chlorine or bromine substituted propenyl, butenyl, propynyl or butynyl, in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, or optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-
  • X 4 is preferably nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • X 5 is preferably nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy.
  • herbicidal safeners particularly preferred compounds of the formula (Ha) according to the invention are listed in the table below. Table Examples of the compounds of the formula (Ha)
  • herbicidal safeners most preferred according to the invention compounds of formula (Eb) are listed in the table below.
  • herbicidal safeners according to the invention very particularly preferred compounds of formula (He) are listed in the table below.
  • herbicidal safeners according to the invention very particularly preferred compounds of formula (Hd) are listed in the table below.
  • herbicidal safeners according to the invention very particularly preferred compounds of formula (Ile) are listed in the table below.
  • crop plant compatibility-improving compound [component (b)] are cloquinetcet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazoles, fenclorim, cumyl uron, dymron, dimepiperate and the compounds IIe-5 and He-11 is most preferred, with cloquintocet-mexyl and mefenpyr-diethyl being particularly emphasized.
  • Preferred combinations include the crop plant compatibility-improving compound cloquintocet-mexyl and an active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or I).
  • these combinations are e.g. Mixtures comprising cloquintocet-mexyl and pirimicarb, indoxacarb, cyromazine, abamectin, tebufenozide, fipronil, 2- (acetyloxy) -3-dodecyl-l, 4-naphthalenedione, diafenthiuron, chlorfenapyr, spinosad, thuringiensin or pymetrocenes.
  • Preferred combinations include the crop plant compatibility-improving compound fenchlorazol-ethyl and an active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or I). Examples of these combinations are e.g.
  • Mixtures comprising fenchlorazole-ethyl and pirimicarb, indoxacarb, cyromazine, abamectin, tebufenozide, fipronil, 2- (acetyloxy) -3-dodecyl-l, 4-naphthalenedione, diafenthiuron, Chlorfenapyr, spinosad, thuringiensin or pymetrocenes.
  • Preferred combinations include the crop plant compatibility-improving compound isoxadifen-ethyl and an active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or I).
  • these combinations are e.g. Mixtures comprising isoxadifen-ethyl and pirimicarb, indoxacarb, cyromazine, abamectin, tebufenozide, fipronil, 2- (acetyloxy) -3-dodecyl-1, 4-naphthalenedione, diafenthiuron, chlorfenapyr, spinosad, thuringiensin or pymetrozine.
  • Preferred combinations contain the crop-plant compatibility-improving compound mefenpyr-diethyl and an active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or I).
  • these combinations are e.g. Mixtures comprising mefenpyr-diethyl and pirimicarb, indoxacarb, cyromazine, abamectin, tebufenozide, fipronil, 2- (acetyloxy) -3-dodecyl-l, 4-naphthalenedione, diafenthiuron, Chlorfenapyr, spinosad, thuringiensin or Pymetrozi ⁇ ne.
  • Preferred combinations include the crop plant compatibility-improving compound flurilazole and an active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or (I).
  • active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or (I).
  • these combinations are, for example, mixtures comprising flurilazoles and pirimicarb, indoxacarb, cyromazine, abamectin, tebufenozide, fipronil, 2- (acetyloxy) -3-dodecyl-1,4-naphthalenedione, diafenthiuron, chlorfenapyr, spinosad, thuringiensin or pymetrozine.
  • Preferred combinations include the crop plant compatibility-improving compound fenclorim and an active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or ( I).
  • these combinations are e.g. Mixtures comprising fenclorim and pirimicarb, indoxacarb, cyromazine, abamectin, tebufenozide, fipronil, 2- (acetyloxy) -3-dodecyl-l, 4-naphthalenedione, diafenthiuron, chlorfenapyr, spinosad, thuringiensin or pymetrozine.
  • Preferred combinations include the crop plant compatibility-improving compound cumyluron and an active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or ( T).
  • Examples of these combinations are e.g. Mixtures comprising cumyluron and pirimicarb, indoxacarb, cyromazine, abamectin, tebufenozide, fipronil, 2- (acetyloxy) -3-dodecyl-l, 4-naphthalenedione, diafenthiuron, chlorfenapyr, spinosad, thuringiensin or pymetrozine.
  • Preferred combinations include the crop plant compatibility-improving compound Dymron and an active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or ( I).
  • these combinations are e.g. Mixtures comprising dymron and pirimicarb, indoxakarb, cyromazine, abamectin, tebufenozide, fipronil, 2- (acetyloxy) -3-dodecyl-l, 4-naphthalenedione, diafenthiuron, chlorfenapyr, spinosad, thuringiensin or pymetrozine.
  • Preferred combinations contain the crop plant compatibility-improving compound dimepiperate and an active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or ( I).
  • Examples of these combinations are e.g. Mixtures comprising dimepiperate and pimaricarb, indoxacarb, cyromazine, abamectin, tebufenozide, fipronil, 2- (acetyloxy) -3-dodecyl-l, 4-naphthalenedione, diafenthiuron, Chlorfenapyr, spinosad, thuringiensin or pymetrozine.
  • Preferred combinations include the crop plant compatibility-improving compound ⁇ e-11 and an active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or I).
  • these combinations are e.g. Mixtures comprising the compound IIe-11 and Piri ⁇ micarb, indoxacarb, cyromazine, abamectin, tebufenozide, fipronil, 2- (acetyloxy) -3-dodecyl-l, 4-naphthalenedione, diafenthiuron, Chlorfenapyr, spinosad, thuringiensin or pymetrozines.
  • Preferred combinations include the crop plant compatibility-improving compound ⁇ e-5 and an active ingredient selected from the group (A), (B), (C), (D), (E), (F), (G), (H) or I).
  • these combinations are, for example, mixtures comprising IIe-5 and pirimicarb, indoxa- carb, cyromazine, abamectin, tebufenozide, fipronil, 2- (acetyloxy) -3-dodecyl-l, 4-naphthalenedione, diafenthiuron, chlorfenapyr, spinosad, thuringiensin or pymetrozine.
  • the compounds of general formula (Ha) to be used as safeners are known and / or can be prepared by processes known per se (cf., WO-A-91/07874, WO-A-95/07897).
  • the compounds of the general formula (IV) to be used as safeners are known and / or can be prepared by processes known per se (cf EP-A-191736).
  • the compounds of general formula (He) to be used as safeners are known and / or can be prepared by processes known per se (cf., DE-A-2218097, DE-A-2350547).
  • the combinations can also be used to protect vegetables. These include artichokes, aubergines, cauliflower, broccoli, green beans, peas, fennel, chicory, cucumbers, kohlrabi, lettuce, cress, leek, chard, carrots, peppers, rhubarb, beetroot, red cabbage, Brussels sprouts, celery, Beets, tomatoes, savoy cabbage, chestnuts, green beans, salsify, corn, asparagus, turnips, spinach, cabbage, savoy cabbage, onions, zucchini,
  • the active ingredient combinations can generally be used in the following plants:
  • the advantageous effect of the crop plant compatibility of the active substance combinations is particularly pronounced in certain concentration ratios.
  • the weight ratios of the active substances in the active substance combinations can be varied in relatively large ranges.
  • 1 part by weight of active substance of group (A) to (I) or its salts accounts for 0.001 to 1000 parts by weight, preferably 0.01 to 100 parts by weight, more preferably 0.05 to 10 parts by weight and most preferably 0.07 to 1.5 parts by weight of one of the above under (b), the crop-compatibility-improving compounds (antidotes / safeners).
  • the combinations according to the invention of the active compounds of groups (A) to (I) and the Sa fenern of group (b) can be used, for example, in the preferred and particularly preferred mixing ratios shown in the table below.
  • the mixing ratios are based on weight ratios.
  • the ratio is to be understood as the active ingredient from one of the groups (A) to (I): Mischpartner the group (b).
  • the ratio is to be understood as the active ingredient of groups (A) to (I) ("mixed partner") and in each case one of the active compounds cloquinetcet-mexyl, fenchlorazol-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazoles, fenclorim, cumyl uron, dymron, dimepiperate, compound IIe-5 or compound He-11. table
  • the mixtures according to the invention are also suitable for the treatment of seed.
  • This phase is particularly critical, as the roots and shoots of the growing plant are particularly sensitive and even minor damage can lead to the death of the entire plant.
  • suitable agents for protecting the seed and the germinating plant by the use of suitable agents
  • 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 agent according to the invention.
  • the invention also relates to the use of the agents according to the invention for the treatment of seed for the protection of the seed and the germinating plant from pests.
  • the invention relates to seed which has been treated with an agent according to the invention for protection against pests.
  • One of the advantages of the present invention is that because of the special properties of the agents according to the invention, the treatment of the seeds with these agents protects not only the seed itself, but also the plants resulting therefrom after emergence from pests. In this way, the immediate treatment of the culture at the time of sowing or shortly afterwards can be omitted.
  • a further advantage consists in the synergistic increase of the insecticidal activity of the agents according to the invention over the respective individual active ingredients. This makes it possible to optimize the amount of active ingredient used. It is to be regarded as particularly advantageous that the damage which may be caused by the insecticidal active ingredients used can be restricted or completely avoided in the surprisingly good manner in the growing plants by the presence of the mixing partners of group (b).
  • the mixtures according to the invention can also be used in particular in the case of transgenic seed, wherein the plants emerging from this seed are capable of expressing a protein directed against pests.
  • certain pests can already be detected by the expression of e.g. insecticidally controlled protein, and it surprisingly also comes to a synergistic effect supplement with the inventive compositions, which again improves the effectiveness of the protection against pest infestation.
  • compositions according to the invention are suitable for the protection of seed of any plant variety used in agriculture, in the greenhouse, in forests, in horticulture or in viticulture.
  • these are corn, peanut, canola, rapeseed, poppy seed, olive, coconut, cocoa, soya, cotton, beet (eg sugarbeet and fodder beet), rice, millet, Wheat, barley, oats, rye, sunflower, sugar cane or tobacco.
  • the compositions according to the invention are likewise suitable for treating the seed of various types of vegetables, such as, for example, broccoli, cauliflower, cabbage, tomato, paprika, melon, zucchini and cucumbers, or various pome fruit plants, such as, for example, apple or pear. Of particular importance is the treatment of the seeds of maize, soya, cotton, wheat and canola or rapeseed.
  • transgenic seed with an agent according to the invention is of particular importance.
  • the heterologous genes in transge ⁇ nem seeds can come from microorganisms such as Bacillus, Rhizobium, Pseudomonas, Serratia, Trichoderma, Clavibacter, Glomus or Gliocladium.
  • the present invention is particularly useful for the treatment of transgenic seed containing at least one heterologous gene derived from Bacillus sp. and whose gene product shows activity against corn borer and / or corn rootworm. Most preferably, this is a heterologous gene derived from Bacillus thuringiensis.
  • the agent according to the invention is applied to the seed alone or in a suitable formulation.
  • the seed is treated in a condition that is so stable that no damage occurs during the treatment.
  • the treatment of the seed can be carried out at any time between the harvest and the sowing.
  • seed is used which has been separated from the plant and freed from flasks, shells, stems, skin, wool or pulp.
  • 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, for example, 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 A1, WO 2002/080675 A1, WO 2002 / 028186 A2.
  • the active compounds or active compound combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension-emulsion concentrates, active ingredient-impregnated natural and synthetic thetic Substances and fine encapsulation in polymeric substances.
  • formulations are prepared in a known manner, for. Example, by mixing the active compounds with extenders, that is liquid solvents and / or solid carriers, optionally with the use of surfactants, emulsifiers and / or dispersants and / or foam-forming agents.
  • Suitable liquid solvents are essentially: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, 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 solid carriers are:
  • Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as fumed silica, alumina and silicates, as solid carriers for granules are suitable: e.g. crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules of inorganic and organic flours and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and / or foam formers are: e.g.
  • nonionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkylsulfonates, alkylsulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Lignin-sulphite liquors and methylcellulose.
  • adhesives such as carboxymethylcellulose, natural and synthetic synthetic powdery, granular or latexformige polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
  • Other additives may be mineral and vegetable oils.
  • Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.
  • the formulations will generally contain between 0.1 and 95% by weight of active ingredients including safener agents, preferably between 0.5 and 90%.
  • the active ingredient combinations are generally applied in the form of ready-to-use formulations.
  • the active substances contained in the active ingredient combinations can also be mixed in individual formulations in the application, i. in the form of tank mixes.
  • the active ingredient combinations can continue to be used as such or in their formulations in admixture with other known herbicides, which in turn Fertig ⁇ formulations or tank mixes are possible.
  • a mixture with other known active substances such as fungicides, insecticides, acaricides, nematicides, attractants, sterilants, bactericides, protective agents against avian, growth substances, plant nutrients and soil structure improvers is also possible.
  • plant-compatible mineral or vegetable oils for example the commercial product "Rako Binol”
  • ammonium salts such as e.g. Ammonium sulfate or ammonium thiocyanate.
  • the active compound combinations can be used as such, in the form of their formulations or the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules.
  • the application is done in the usual way, e.g. by pouring, spraying, spraying, dusts or spreading.
  • the application rates of the active compound combinations can be varied within a certain range; they hang u.a. weather and soil factors. In general, the application rates are between 0.005 and 5 kg per ha, preferably between 0.01 and 2 kg per ha, more preferably between 0.05 and 1.0 kg per ha.
  • the active ingredient combinations can be applied before and after emergence of the plants, ie in the pre-emergence and Nachetzlauf- method.
  • the safeners to be used can be used for pretreatment of the seed of the crop (dressing of the seeds) or introduced into the seed furrow before sowing or applied together with the herbicide before or after the plants have run off.
  • the active ingredient combinations are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which occur in agriculture. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.
  • the above mentioned pests include:
  • Isopoda for example, Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
  • Diplopoda eg Blaniulus guttulatus.
  • Chilopoda for example, Geophelus carpophagus
  • Scutigera spp From the order of the Symphyla, for example Scutigerella immaculata.
  • Thysanura eg Lepisma saccharina.
  • Collembola eg Onychiurus armatus.
  • Phthiraptera for example, Pediculus humanus corporis, Haematopinus spp., Linognathus spp., Trichodectes spp., Damalinia spp.
  • Thysanoptera for example, Hercinothrips femoralis, Thrips tabaci, Thrips palmi, Frankliniella occidentalis.
  • Heteroptera eg Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Ciprollectularus, Rhodnius prolixus, Triatoma spp.
  • From the order of the Homoptera for example, Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloera vastatrix, Pemphigus spp., Macrosiphum avenae, Myzus spp ., Phorodon humuli, Rhapa- losiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saisse tia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiorus hederae, Pse
  • Diprion spp. Hoplocampa spp., Lasius spp., Monorium pharaonis, Vespa spp. From the order of Diptera e.g. Aedes spp., Anopheles spp., Cullex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp , Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula pal
  • arachnids e.g. Scorpio maurus, Latrodectus mactans, Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp.
  • Choriopsis spp. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp., Hemitarsonemus spp., Brevipalpus spp.
  • the plant parasitic nematodes include e.g. Pratylenchus spp., Radopholus similis, Ditylenus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Bursaphelenchus spp.
  • active ingredient combinations may be present in mixtures with other synergists when used as insecticides in their commercial formulations and in the forms of use prepared from these formulations.
  • Synergists are compounds that increase the effect of the active ingredients without the added synergist itself having to be active.
  • the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
  • the active ingredient concentration of the use forms may be from 0.0000001 to 95% by weight of active ingredient, preferably between 0.0001 and 1% by weight.
  • the application is done in a custom forms adapted to the application forms.
  • plants are understood as meaning all plants and plant populations, such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).
  • Crop plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and a finally, plant varieties that can be protected or not protected by plant variety rights.
  • Plant parts are to be understood as meaning all aboveground and underground parts and organs of the plants, such as shoot, leaf, flower and root, examples of which include leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds, and roots, tubers and rhizomes be led.
  • the plant parts also include crops as well as vegetative and generative growth material, for example cuttings, tubers, rhizomes and offshoots.
  • the erfindungsge ⁇ MAESSEN combinations are particularly suitable for the treatment of the seeds of the above crops
  • the treatment according to the invention of the plants and plant parts or of the seed with the active substances takes place directly or by acting on their environment, habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, evaporating, misting Ver ⁇ , spreading, brushing and in propagating material, especially in seeds, further by single or multi-layer wrapping.
  • all plants and their parts can be treated according to the invention.
  • wild-type or plant species obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and plant cultivars and their parts are treated.
  • transgenic plants and plant cultivars which have been obtained by genetic engineering methods, if appropriate in combination with conventional methods (Genetically Modified Organisms), and their parts are treated.
  • the term "parts” or “parts of plants” or “plant parts” has been explained above.
  • plants of the respective commercially available or in use custom plant cultivars are particularly preferably treated.
  • the treatment according to the invention may also give rise to superadditive ("synergistic") effects.
  • superadditive for example, reduced amounts of effort and / or extensions of the spectrum of action and / or an increase in the effect of the substances and agents that can be used according to the invention, better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or Soil salt content, increased flowering efficiency, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or machinability of the harvested products possible, which go beyond the actual expected effects.
  • the preferred plants or plant cultivars to be treated according to the invention which are to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits"). Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to water or soil salt content, increased flowering power, easier harvesting, acceleration of maturity, higher crop yields, higher quality and / or higher nutritional value of the Ern ⁇ te economic, higher shelf life and / or workability of the harvested products.
  • transgenic plants include the important crops such as cereals (wheat, rice), corn, soy, potato, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soy, potato, cotton and rapeseed should be highlighted.
  • Traits which are particularly emphasized are the increased defense of the plants against insects by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thurin giensis (for example by the genes Cry ⁇ A (a), CryIA (b), Cry ⁇ A (c), CryllA, CrylEA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) are produced in the plants (in the following "Bt plants”).
  • trasits which are furthermore particularly emphasized are the increased tolerance of the plants to certain herbicidally active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
  • herbicidally active compounds for example imidazolinones, sulfonylureas, glyphosate or phosphinotricin (eg "PAT" gene).
  • the genes which each confer the desired properties can also occur in combinations with one another in the transgenic plants.
  • Bt plants are maize varieties, cotton varieties, soybean varieties and potato varieties which are listed under the trade names YIELD GARD® (eg maize, cotton, soya), KnockOut® (eg maize), StarLink® (eg maize), Bollgard ® (cotton), Nucotn® (cotton) and NewLeaf® (potato) are vertrie ⁇ ben.
  • YIELD GARD® eg maize, cotton, soya
  • KnockOut® eg maize
  • StarLink® eg maize
  • Bollgard ® cotton
  • Nucotn® cotton
  • NewLeaf® potato
  • herbicide-tolerant plants are maize varieties, cotton varieties and soybean varieties, which are sold under the trade names Roundup Ready® (tolerance to glyphosate eg corn, cotton, soy), Liberty Link® (tolerance to phosphinotricin, eg rapeseed), IMI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas eg corn).
  • Roundup Ready® tolerance to glyphosate eg corn, cotton, soy
  • Liberty Link® tolerance to phosphinotricin, eg rapeseed
  • IMI® to Imidazolinone
  • STS® tolerance to sulfonylureas eg corn.
  • Clearfield® eg corn
  • the listed plants and / or their seeds can be treated particularly advantageously according to the invention with the active ingredient mixtures.
  • the preferred ranges given for the mixtures also apply to the treatment of these plants or their seed. Particularly emphasized is the treatment of plants and seeds with the mixtures specially mentioned in the present text.
  • Active ingredient A and B in amounts of m and n ppm means
  • the combination is over-additive in its kill, i. there is a synergistic effect.
  • the actually observed kill rate must be greater than the expected kill rate (E) value calculated from the above formula.
  • Adjuvant 0.1% rapeseed oil methyl ester
  • Cotton plants (Gossypium hirsutum) are sprayed dripping wet with the desired application concentration and are populated with caterpillars of the cotton budworm ⁇ Heliothis armigera) while the leaves are still moist. See Table A.
  • Maize plants (Zea corn) are sprayed dripping wet with the desired application concentration and are populated with caterpillars of the armyworm ⁇ Spodoptera frugiperda) while the leaves are still moist.
  • Cabbage plants ⁇ Brassica pekinesis) are sprayed dripping wet with the desired application concentration and are populated with larvae of the cabbage moth ⁇ Plutella xylostella) while the leaves are still moist.
  • Cotton plants which are heavily infested by the cotton aphid ⁇ Aphis gossypii) are sprayed with the desired concentration of the application solution to dripping wet.
  • Paprika plants (Capsicum sativum), which are heavily infested with the green peach aphid ⁇ Myzus persicae), are sprayed to drip point with the desired concentration of the application solution. After the desired time each kill is determined in%. 100% means that all larvae have been killed; O% means that no larvae have been killed. The determined kill values are calculated according to the Colby formula described above.

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  • Life Sciences & Earth Sciences (AREA)
  • General Health & Medical Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Toxicology (AREA)
  • Pest Control & Pesticides (AREA)
  • Plant Pathology (AREA)
  • Agronomy & Crop Science (AREA)
  • Engineering & Computer Science (AREA)
  • Dentistry (AREA)
  • Wood Science & Technology (AREA)
  • Zoology (AREA)
  • Environmental Sciences (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Pretreatment Of Seeds And Plants (AREA)
  • Catching Or Destruction (AREA)

Abstract

L'invention concerne des agents insecticides caractérisés en ce qu'ils renferment une quantité efficace d'une association de substances actives comprenant : (a) un ou plusieurs composés sélectionnés dans le groupe rassemblant des inhibiteurs de l'acétylcholinestérase, des modulateurs des canaux sodiques, des inhibiteurs de la biosynthèse de la chitine, des mimétiques de l'hormone juvénile, des activateurs des canaux chlorure, des agonistes de l'ecdysone, des antagonistes des canaux chlorure régulés par GABA ou des acaricides, et ; (b) au moins un composé qui améliore la tolérabilité des plantes cultivées, ce composé étant issu du groupe de composés mentionné dans la description. Les agents insecticides selon l'invention servent à lutter contre des arthropodes. La présente invention se rapporte également à un procédé pour lutter contre des arthropodes, par traitement de plantes et de leurs semences au moyen desdits agents.
EP05772342A 2004-07-20 2005-07-18 Agents insecticides a base d'insecticides et de phytoprotecteurs selectionnes Withdrawn EP1771065A2 (fr)

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DE102004035132A DE102004035132A1 (de) 2004-07-20 2004-07-20 Insektizide Mittel auf Basis von ausgewählten Insektiziden und Safenern
PCT/EP2005/007792 WO2006008109A2 (fr) 2004-07-20 2005-07-18 Agents insecticides a base d'insecticides et de phytoprotecteurs selectionnes

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US20080293676A1 (en) 2008-11-27
WO2006008109A3 (fr) 2006-04-20
AU2005263568A1 (en) 2006-01-26
DE102004035132A1 (de) 2006-02-16
CA2574207A1 (fr) 2006-01-26
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