Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
  • C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
  • C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
  • C07D207/34—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
  • C07D207/36—Oxygen or sulfur atoms
• • A—HUMAN NECESSITIES
  • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
  • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
  • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
  • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
  • A01N43/36—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom five-membered rings

Definitions

• the present invention relates to novel alkoxyalkyl-substituted cyclic ketoenols, to a plurality of processes for their preparation and to their use as pesticides and / or herbicides and / or microbicides.
• the invention also provides selective herbicidal compositions which contain alkoxyalkyl-substituted cyclic ketoenols on the one hand and a crop plant compatibility-improving compound on the other hand.
• EP-A-0 262 399 and GB-A-2 266 888 disclose similarly structured compounds (3-arylpyrrolidine-2,4-diones), of which, however, no herbicidal, insecticidal or acaricidal action has become known.
• Unsubstituted, bicyclic 3-arylpyrrolidine-2,4-dione derivatives (EP-A-355 599, EP-A-415 211 and JP-A-12-053 670 are known to have herbicidal, insecticidal or acaricidal activity ) and substituted monocyclic 3-aryl-pyrrolidine-2,4-dione derivatives (EP-A-377 893 and EP-A-442 077).
• EP-A-442 073 polycyclic 3-arylpyrrolidine-2,4-dione derivatives
• EP-A-456 063 EP-A-521 334, EP-A- 596 298, EP-A-613 884, EP-A-613 885, WO 94/01 997, WO 95/26 954, WO 95/20 572, EP-A-0 668 267, WO 96/25 395, WO 96 / 35,664, WO 97/01 535, WO 97/02 243, WO 97/36868, WO 97/43275, WO 98/05638, WO 98/06721, WO 98/25928, WO 99/24437, WO 99/43649 , WO 99/48869 and WO 99/55673, WO 01/17972, WO 01/23354, WO 01/74770, WO 03/013249,
• W is hydrogen, alkyl, alkenyl, alkynyl, halogen, alkoxy, alkenyloxy, haloalkyl, haloalkoxy or cyano,
• X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkoxy, haloalkenyloxy, nitro or cyano,
• Y is hydrogen, alkyl, alkenyl, alkynyl, alkoxy, halogen, haloalkyl, haloalkoxy, cyano or nitro,
• A is a C 1 -C 6 -alkylidenediyl radical
• B is hydrogen, alkyl or alkoxyalkyl
• D is in each case optionally substituted alkoxy, alkenyloxy, alkynyloxy, alkoxyalkoxy, phenoxy, hetaryloxy, phenylalkoxy, hetarylalkoxyl and optionally substituted, saturated or unsaturated, interrupted by one or two oxygen atoms cycloalkyl
• B is hydrogen or alkyl
• D is optionally substituted, saturated or unsaturated, interrupted by oxygen C 5 -C 6 -cycloalkyl
• G is hydrogen (a) or one of the groups
• E is a metal ion or an ammonium ion
• L is oxygen or sulfur
• M is oxygen or sulfur
• R * is in each case optionally halogen or cyano-substituted alkyl, alkenyl,
• R 1 is in each case optionally halogen or cyano-substituted alkyl, alkenyl, alkoxyalkyl or polyalkoxyalkyl or in each case optionally substituted cycloalkyl, phenyl or benzyl,
• R 3, R 4 and R 4 independently of one another are each optionally halogen-substituted alkyl, alkoxy, alkylamino, dialkylamino, alkylthio, alkenylthio or cycloalkylthio or in each case optionally substituted phenyl, benzyl, phenoxy or phenylthio,
• R6 and R4 independently of one another represent hydrogen, in each case optionally halogen or cyano-substituted alkyl, cycloalkyl, alkenyl, alkoxy, alkoxyalkyl, in each case optionally substituted phenyl or benzyl, or together with the N-atom to which they are attached, form an optionally oxygen or sulfur containing and optionally substituted cycle.
• the compounds of the formula (I) can also be present in different compositions as optical isomers or mixtures of isomers, which can optionally be separated in a customary manner. Both the pure isomers and the mixtures of isomers, their preparation and use and agents containing them are the subject of the present invention. In the following, however, for the sake of simplicity, reference is always made to compounds of the formula (I), although both the pure compounds and, if appropriate, mixtures with different proportions of isomeric compounds are meant.
• R 8 is alkyl (preferably C i -Cg -alkyl),
• R.1 has the meaning given above and
• Hal is halogen (especially chlorine or bromine)
• R 1 has the meaning given above
• R3 has the meaning given above
• Hal is halogen (especially chlorine or bromine),
• Me is a mono- or divalent metal (preferably an alkali metal or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium),
• R 10, R 9, R 12 independently of one another represent hydrogen or alkyl (preferably C 1 -C 6 -alkyl),
• EP-A 835243 (I-1-A-38)
• EP-A-837847 (I-1-A-19)
• the novel compounds of the formula (I) have good activity as pesticides, preferably as insecticides and / or acaricides and / or fungicides and / or herbicides and, moreover, are often very well tolerated by plants, in particular with respect to crop plants.
• n is a number 0, 1, 2, 3, 4 or 5
• A is one of the divalent heterocyclic groupings outlined below,
• n is a number 0, 1, 2, 3, 4 or 5
• a 2 is optionally substituted by Ci-C 4 alkyl and / or C] -C 4 -alkoxy-carbonyl and / or Ci-C 4 - alkenyloxy-carbonyl-substituted alkanediyl having 1 or 2 carbon atoms,
• R 14 represents hydroxyl, mercapto, amino, C r C 6 alkoxy, CpC ö alkylthio, Ci-C 6 -alkylamino or di- (Ci-C 4 -alkyl) -amino,
• R 15 represents hydroxyl, mercapto, amino, Ci-C 7 -alkoxy, Ci-C 6 alkylthio, C r C 6 alkenyloxy, C r C 6 - alkenyloxy-C r C6-alkoxy, Ci-C ⁇ alkylamino or di - (C r C 4 -alkyl) -amino, R 16 is optionally C 1 -C 4 -alkyl which is substituted by fluorine, chlorine and / or bromine,
• R 17 is hydrogen, in each case optionally substituted by fluorine, chlorine and / or bromine-substituted Q- C 6 alkyl, C 2 -C 6 alkenyl or C 2 -C 6 alkynyl, Ci-C 4 alkoxy-Ci-C 4 alkyl, dioxolanyl-Ci-C 4 - alkyl, furyl, furyl-Ci-C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine and / or bromine, or Ci-Gj-alkyl substituted phenyl,
• R 18 represents hydrogen, in each case optionally fluorine, chlorine and / or bromine-substituted Cp C 6 -alkyl, C 2 -C 6 -alkenyl or C 2 -C 6 -alkynyl, C r C 4 -alkoxy-C r C 4 - alkyl, dioxolanyl-Ci-C 4 - alkyl, furyl, furyl-Ci-C 4 -alkyl, thienyl, thiazolyl, piperidinyl, or optionally fluorine-, chlorine and / or bromine, or CpC 4 alkyl-substituted phenyl, R 17 and R 18 also together in each case optionally by Ci-C 4 alkyl, phenyl, furyl, an anneli Being
• Benzene ring or by two substituents which together with the C-atom to which they are attached form a 5- or 6-membered carboxycycle is substituted C 3 -C 6 -alkanediyl or C 2 -C 5 -oxaalkanediyl,
• R 19 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 20 is hydrogen, in each case optionally by hydroxy, cyano, halogen or C 1 -C 4 -
• R 21 is hydrogen, cyano, halogen, or is in each case optionally substituted by fluorine, chlorine and / or bromine-substituted C 1 -C 4 -alkyl, C 3 -C 6 -cycloalkyl or phenyl,
• X 1 represents nitro, cyano, halogen, C r C 4 alkyl, C, -C 4 haloalkyl, C r C 4 alkoxy or C 1 -C 4 - haloalkoxy,
• X 2 represents hydrogen, cyano, nitro, halogen, C, -C 4 alkyl, C r C 4 haloalkyl, C r C 4 alkoxy or Ci-C is 4 haloalkoxy,
• X 3 represents hydrogen, cyano, nitro, halogen, C r C 4 alkyl, C, -C 4 haloalkyl, C r C 4 alkoxy or Ci-C is 4 haloalkoxy,
• R is hydrogen or C 1 -C 4 -alkyl
• R li 4 -alkyl hydrogen or C r C
• R 24 is hydrogen, in each case optionally substituted by Cyario, halogen or Ci-C 4 alkoxy-substituted Ci-C 6 alkyl, dQ-alkoxy, C r C 6 alkylthio, C r C 6 alkylamino or di (Ci-C 4- alkyl) - amino, or in each case optionally substituted by cyano, halogen or Ci-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 25 represents hydrogen, optionally cyano-, hydroxyl-, halogen or Ci-C4 alkoxy-substituted Ci-C 6 -alkyl, in each case optionally cyano- or halogen-substituted C 3 -Ce- alkenyl or C 3 -C 6 alkynyl, or optionally substituted by cyano, halogen or C r C 4 -alkyl-substituted C 3 -C 6 cycloalkyl,
• R 26 represents hydrogen, optionally cyano-, hydroxyl-, halogen or C r C 4 alkoxy-substituted Ci-C 6 -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 CRQ alkyl substituted C 3 -C 6 cycloalkyl, or optionally substituted by nitro, cyano, halogen, C r C 4 alkyl, Ci-C 4 haloalkyl, Ci-C 4 -alkoxy or C r C 4 -haloalkoxy-substituted phenyl, or together with R 25 is optionally substituted by Ci-C 4 alkyl in each case C 2 -C 6 - alkanediyl or C 2 -C 5 -oxaalkanediyl,
• X 4 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halo, Q- C4 alkyl, C] -C 4 haloalkyl, Ci-C4-alkoxy or Ci-C4-haloalkoxy , and
• X 5 represents nitro, cyano, carboxy, carbamoyl, formyl, sulfamoyl, hydroxy, amino, halo, Q- C4 alkyl, Ci-C 4 haloalkyl, C) -C 4 alkoxy or C r C 4 haloalkoxy ,
• W preferably represents hydrogen, C j -CG alkyl, C2-C6-alkenyl, C 2 -Cg- alkynyl, halogen, Cj-Cg-alkoxy, Ci-C 4 haloalkyl, C] -C4 haloalkoxy or cyano .
• X is preferably halogen, C 1 -C 6 -alkyl, C 2 -C 6 -alkenyl, C 2 -C 6 -alkyl, C 1 -C 9 -halogenoalkyl, C 1 -C 6 -alkoxy, C 3 -C 6 -alkenyloxy, C 1 -C 6 -alkylthio, Cg-alkylsulfinyl, Cj-Cg alkylsulfonyl, Cj -CG-haloalkoxy, C3-Cg-halogenoalkenyloxy, nitro or cyano,
• Y is preferably hydrogen, halogen, C j -Cg -alkyl, C 2 -Cg -alkenyl, C 1 -Cg -alkoxy, C j -Cg -haloalkyl, C j -Cg -haloalkoxyl, cyano, C 2 -Cg- Alkenyl or C 2 -Cg alkynyl,
• A preferably represents a Ci-C ö -Alkylidendiylrest
• B is preferably hydrogen, C 1 -C 6 -alkyl or C 1 -C 4 -alkoxyC r C 4 -alkyl,
• D preferably represents in each case mono- or polysubstituted by halogen or cyano, Ci-C 6 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C r C 4 -alkoxy-C 2 -C 4 alkoxy , in each case optionally mono- to trisubstituted by halogen, Ci-C 6 alkyl, C r C 6 alkoxy,
• A is preferably a bond
• B is preferably hydrogen or Ci-Gj-alkyl
• D preferably represents optionally mono- to trisubstituted by Ci-C 2 alkyl or Ci-C 2 - alkoxy-substituted saturated or unsaturated, interrupted by one or two oxygen atoms C 3 -C 8 -Cycloalky,
• G is preferably hydrogen (a) or one of the groups
• E is a metal ion or an ammonium ion
• M is oxygen or sulfur
• R.1 preferably represents in each case optionally substituted by halogen or cyano, C ⁇ - C 2 o alkyl, C2-C2o-alkenyl, Ci-Cg-alkoxy-Ci-Cg-alkyl, Cj-Cg-alkylthio-CJ Cg-alkyl or poly-Ci-Cs-alkoxy-C j is not optionally one or -CG-alkyl or is optionally substituted by halogen, Ci-Cg-alkyl or Ci-Cg-alkoxy-substituted C3-Cg-cycloalkyl in which two directly adjacent methylene groups are replaced by oxygen and / or sulfur, phenyl which is unsubstituted or substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 6 -alkoxy, C 1 -C 6 -halogenoalkyl, C 1 -C 6 -halogen
• R 1 is preferably C 1 -C 20 -alkyl which is optionally substituted by halogen or cyano, C 2 -C 2 () -alkenyl, C 1 -C 8 -alkoxy-C 1 -C 4 -alkyl or poly-C 1 -C 4 -alkoxy-C 6 -C 8 -cycloalkyl; alkyl,
• C3-C8-cycloalkyl optionally substituted by halogen, Cj-Cg-alkyl or Cj-Cg-alkoxy or
• R ⁇ preferably represents optionally halogen-substituted C j -CG alkyl or in each case optionally substituted by halogen, C j -CG alkyl, C j -CG-alkoxy, Cj-C4 haloalkyl, C1-C4 haloalkoxy, cyano or nitro substituted phenyl or benzyl,
• R 1 and R 2 are each independently of the other preferably C 1 -C -alkyl which is optionally substituted by halogen, C 1 -C 6 -alkoxy, C 1 -C 6 -alkylamino, di- (C 1 -C 8 -alkyl) amino, C 1 -C 8 -alkyl, Alkylthio or C3-Cg-alkenylthio or in each case optionally by halogen,
• R6 and R? independently of one another preferably represent hydrogen, in each case optionally halogen- or cyano-substituted C j -Cg-alkyl, C 3 -C 9 -cycloalkyl, C 1 -C -alkoxy, CSS-Cg-alkenyl or Ci-Cg-alkoxy-C2-Cg-alkyl, represents in each case optionally substituted by halogen, Cj-Cg alkyl, Cj-Cg haloalkyl or C j -CG-alkoxy, phenyl or benzyl or together are a optionally substituted by Cj-Cg-AUcyl C3-C6-alkylene radical, in which optionally a methylene group is replaced by oxygen or sulfur.
• halogen is fluorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine.
• W is particularly preferably hydrogen, chlorine, bromine, iodine, Ci-C4-alkyl, C2-C4 alkenyl, C2-C4-alkynyl, Ci-C4-alkoxy, Ci-C 2 haloalkyl, or C r C 2 -haloalkoxy .
• X particularly preferably represents chlorine, bromine, iodine, C j ⁇ alkyl, C2-C4-alkenyl, C2-C4 alkynyl, Ci-C4-alkoxy, Ci-C4-haloalkyl, C] -C4 haloalkoxy or cyano,
• Y particularly preferably represents hydrogen, fluorine, chlorine, bromine, Ci-C4-alkyl, C2-C4 alkenyl, C2-C4 alkynyl, Cj-Cg-alkoxy, C [C4 haloalkyl, Ci-C4-haloalkoxy, Cyano, C 2 -C 4 -alkenyl or C 2 -C 4 -alkynyl,
• X is C 2 -C 4 alkyl, chloro, bromo, iodo or C r C 4 alkoxy, when
• Y is halogen
• A is particularly preferably a C 1 -C 4 -alkylidenediyl radical
• B is hydrogen, C r C 4 alkyl or Ci-C4-alkoxy-Ci-C 2 alkyl,
• D particularly preferably represents in each case optionally mono- to trisubstituted by fluorine, chlorine or cyano substituted C r C 4 alkoxy, C 3 -C 6 alkenyloxy, C 3 -C 6 alkynyloxy, C r
• A is particularly preferably a bond
• B is particularly preferably hydrogen or C 1 -C 2 -alkyl
• D particularly preferably represents saturated or unsaturated C 5 -C 6 -cycloalkyl which is optionally monosubstituted or disubstituted by methyl or ethyl and which is interrupted by one or two oxygen atoms
• G is particularly preferably hydrogen (a) or one of the groups
• E is a metal ion or an ammonium ion
• M is oxygen or sulfur
• R.1 particularly preferably represents in each case optionally monosubstituted to trisubstituted by fluorine or chlorine, Ci-Cig-alkyl, C2-Ci6-alkenyl, Ci-Cg-alkoxy-Ci-C ⁇ alkyl, Ci-Cg-alkylthio-Ci-C4 -alkyl or poly-C i -Cg-alkoxy-Ci-C ⁇ alkyl or optionally mono- to disubstituted by fluorine, chlorine, Ci-C5-alkyl or Cj-Cs-alkoxy-substituted C3-C7-cycloalkyl, in which optionally one or two not directly adjacent methylene groups are replaced by oxygen and / or sulfur,
• phenyl optionally mono- to disubstituted by fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C 1 -C 4 -alkoxy, C 1 -C 6 -haloalkyl or C 1 -C 3 -haloalkoxy, phenyl-C 1 -C 4 -alkyl,
• R 1 particularly preferably represents in each case optionally monosubstituted to trisubstituted by fluorine or chlorine, C 1 -C 18 -alkyl, C 2 -C 16 -alkenyl, C 1 -C 6 -alkoxy-C 1 -C 4 -alkyl or poly-C 1 -C 8 -alkoxy-Cg -alky 1,
• R 1 particularly preferably represents C 1 -C -alkyl which is optionally monosubstituted to trisubstituted by fluorine or chlorine, or in each case optionally mono- or disubstituted by fluorine,
• R ⁇ and R ⁇ independently of one another particularly preferably represent in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted Cj-Cg-alkyl, C j -CG -alkoxy, Cj-Cg alkylamino, di- (C j -CG-alky ⁇ amino, C 1 -C 6 -alkylthio or C 3 -C 4 -alkenylthio or in each case optionally mono- to disubstituted by fluorine, chlorine, bromine, nitro, cyano, C 1 -C 3 -alkoxy, C 1 -C 3 -haloalkoxy, C 1 -C 3 -alkylthio, C 1 -C 3 -haloalkylthio, C 1 -C 3 -alkyl or C 1 -C 3 -haloalkyl-substituted phenyl, phenoxy or phenylthio,
• C3-C6-cycloalkyl Ci-Cg-alkoxy, C3-C 6 alkenyl, or Ci-Cg-alkoxy ⁇ -Cö-alkyl, in each case optionally mono- to trisubstituted by fluorine, chlorine, bromine, Ci-C5-halo- genalkyl , Ci-C5-alkyl or Ci-C5-alkoxy-substituted phenyl or benzyl, or together represent an optionally substituted by C j-C4 alkyl C3-C6-alkylene radical in which optionally one methylene group by oxygen or sulfur is replaced.
• halogen is fluorine, chlorine and bromine, in particular fluorine and chlorine.
• W is very particularly preferably hydrogen, chlorine, bromine, methyl, ethyl, vinyl, ethynyl, propynyl, methoxy, ethoxy or trifluoromethyl,
• X is very particularly preferably chlorine, bromine, methyl, ethyl, propyl, isopropyl, vinyl, ethynyl, propynyl, methoxy, ethoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy or cyano,
• Y very particularly preferably independently of one another represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, vinyl, ethynyl, propynyl, methoxy, trifluoromethyl, trifluoromethoxy or cyano,
• A is most preferably for
• B very particularly preferably represents hydrogen, methyl or ethyl
• D is most preferably methoxy, ethoxy, propoxy, isopropoxy, butoxy, iso-butoxy, allyloxy, methallyloxy, isoprenyloxy, propargyloxy, butinyloxy, methoxyethoxy, ethoxyethoxy, optionally optionally substituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or Trifluoromethoxy substituted phenoxy, or for each optionally mono- to disubstituted by methyl substituted tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl or dioxanyl
• A is most preferably a bond
• B very particularly preferably represents hydrogen, methyl or ethyl
• D very particularly preferably represents tetrahydrofuranyl, tetrahydropyranyl, dioxolanyl or dioxanyl,
• G is very particularly preferably hydrogen (a) or one of the groups SO 2 - R 0
• E is a metal ion or an ammonium ion
• M is oxygen or sulfur
• R.1 very particularly preferably represents in each case optionally monosubstituted to trisubstituted by fluorine or chlorine C 1 -C 10 -alkyl, C 2 -C 6 -alkenyl, C 1 -C 4 -alkoxy-C 1 -C 4 -alkyl, C 1 -C 4 -alkylthio-C 1 -C 2 C3-C6-cycloalkyl, or optionally monosubstituted by fluorine, chlorine, methyl, ethyl or methoxy,
• R.2 is very particularly preferably represents in each case optionally mono- to trisubstituted by fluorine or chlorine-substituted Cj-Cio-alkyl, C2-C ⁇ Q alkenyl, or C j-C4-alkoxy-C2-C4 alkyl,
• R.3 particularly preferably represents in each case optionally mono- to trisubstituted by fluorine or chlorine, methyl, ethyl, propyl or iso-propyl, or in each case if appropriate simply phenyl substituted by fluorine, chlorine, bromine, methyl, ethyl, isopropyl, tert-butyl, methoxy, ethoxy, isopropoxy, trifluoromethyl, trifluoromethoxy, cyano or nitro,
• R.4 and Ry independently of one another very particularly preferably represent C j -C 4 -alkoxy or C ⁇ - C4-alkylthio, or represents in each case optionally monosubstituted by fluorine, chlorine, bromine, nitro,
• R6 and R ⁇ are, independently of one another very particularly preferably represent hydrogen, C1-C4 alkyl, C3-C6-cycloalkyl, C j -C ⁇ alkoxy, C3-C4-alkenyl or C 1 -C 4 alkoxy-C2-C4 alkyl, in each case optionally once or twice by fluorine, chlorine, bromine, methyl,
• Saturated or unsaturated hydrocarbon radicals such as alkyl, alkanediyl or alkenyl can also be straight-chain or branched, as far as possible, also in combination with heteroatoms, for example in alkoxy.
• optionally substituted radicals may be monosubstituted or polysubstituted, with multiple substituents the substituents being the same or different.
• Table 2 W, X and Y as indicated in Table 1
• Table 3 W, X and Y as indicated in Table 1
• Table 4 W, X and Y as indicated in Table 1
• Table 5 W, X and Y as indicated in Table 1
• A bond; B Preferred meanings of the groups listed above in connection with the crop plant compatibility-improving compounds (“herbicide safeners") of the formulas (Da), (Hb), (IIc), (Ud) and (He) are defined below.
• m is preferably 0, 1, 2, 3 or 4.
• a 1 preferably represents one of the divalent heterocyclic groupings 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 or allyloxycarbonyl-substituted methylene or ethylene.
• R 14 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 15 is preferably hydroxyl, mercapto, amino, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, 1-methylhexyloxy, AlIy loxy, 1-allyloxymethyl-ethoxy, 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 16 is preferably in each case optionally substituted by fluorine, chlorine and / or bromine substituted methyl, ethyl, n- or i-propyl.
• R 17 is preferably hydrogen, in each case optionally 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 substituted by fluorine, chlorine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl-substituted phenyl , R 18 is preferably hydrogen, in each case optionally fluorine- and / or chlorine-substituted methyl, ethyl, n- or i-
• R 19 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 20 is preferably hydrogen, optionally substituted by hydroxyl, cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t- butyl.
• R 21 preferably represents hydrogen, cyano, fluorine, chlorine, bromine, or represents in each case optionally fluorine, chlorine and / or bromine-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or 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.
• t preferably stands for the numbers 0, 1, 2, 3 or 4.
• v preferably represents the numbers 0, 1, 2 or 3.
• R 22 is preferably hydrogen, methyl, ethyl, n- or i-propyl.
• R 23 is preferably hydrogen, methyl, ethyl, n- or i-propyl.
• R 24 is preferably 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 .
• R 25 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, each optionally substituted by cyano, fluorine, chlorine or bromine substituted propenyl,
• R 26 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, each optionally substituted by cyano, fluorine, chlorine or bromine substituted propenyl,
• Cyclohexyl or optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i- Propoxy, di-fluoromethoxy or trifluoromethoxy-substituted phenyl, or together with R 25 for each optionally substituted by methyl or ethyl butane-1,4-diyl (trimethylene), pentane
• 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,
• 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.
• herbicidal safeners particularly preferred compounds of formula (Ub) according to the invention 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 (He) are listed in the table below.
• AIs the crop plant compatibility-improving compound [component (b 1 )] are cloquintocet-mexyl, fenchlorazole-ethyl, isoxadifen-ethyl, mefenpyr-diethyl, furilazoles, fenclorim, cumyluron, dymron, dimepiperate and the compounds Ile-5 and 11 is most preferred, with cloquintocet-mexyl and mefenpyr-diethyl being particularly emphasized.
• the compounds of general formula (Ha) to be used according to the invention as safeners are known and / or can be prepared by processes known per se (cf., WO-A-91/07874, WO-A-95/07897).
• reaction course can be represented by the following reaction scheme:
• A, B, D, W, X, Y and R ⁇ have the meanings given above,
• acylamino acid esters of the formula (II) are obtained, for example, if amino acid derivatives of the formula (XIII) are obtained.
• W, X and Y have the meanings given above, and
• U is a leaving group introduced by carboxylic acid activating reagents such as carbonyldiimidazole, carbonyldiimides (such as dicyclohexylcarbondiimide), phosphorylating reagents (such as POCl 3 , BOP-Cl), halogenating agents such as thionyl chloride, oxalyl chloride, phosgene or chloroformic acid esters,
• carboxylic acid activating reagents such as carbonyldiimidazole, carbonyldiimides (such as dicyclohexylcarbondiimide), phosphorylating reagents (such as POCl 3 , BOP-Cl), halogenating agents such as thionyl chloride, oxalyl chloride, phosgene or chloroformic acid esters,
• A, B, D, W, X, Y and Z have the meanings given above,
• the compounds of the formula (XV) are obtained, for example, by reacting 1-amino-cyclohexane-carboxylic acids of the formula (XVI)
• the compounds of the formula (XIV) are known and / or can be prepared by the known processes in the cited Offenlegungsschriften.
• the compounds of the formula (XU!) And (XVI) are novel in part and can be prepared by known processes (see, for example, Compagnon, Ann. Chim. (Paris) [14] 5, pp. 11-22, 23-27 (1970 ), L. Munday, J. Chem. Soc., 4372 (1961); JT Eward, C. Jitrangeri, Can. J. Chem. 53, 3339 (1975).
• A, B, D, W, X, Y and R ⁇ have the meanings given above,
• the compounds of formula (XVIII) are also new.
• the compounds of formula (XVII) are partially novel and can be e.g. as described in EP-A-595 130.
• acid halides of the formula (IH), carboxylic anhydrides of the formula (FV ), Chloroformates or chloroformic thioesters of the formula (V), chloromonothioformic acid esters or chlorodithioic acid esters of the formula (VI), sulfonyl chlorides of the formula (VII), phosphorus compounds of the formula (VIII) and metal hydroxides, metal alkoxides or amines of the formula (DC) and ( X) and isocyanates of the formula (XI) and carbamic acid chlorides of the formula (XII) are generally known compounds of organic or inorganic chemistry.
• Process (A) is characterized in that compounds of the formula (II) in which A, B, D, W, X, Y and R 1 have the abovementioned meanings, in the presence of a diluent and in the presence of a base of a subjected to intramolecular condensation.
• Suitable diluents in process (A) according to the invention are all organic solvents which are inert to the reactants.
• hydrocarbons such as toluene and xylene
• furthermore ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether
• furthermore polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone
• alcohols such as methanol, ethanol, Propanol, iso-propanol, butanol, iso-butanol and tert-butanol.
• AIs base (deprotonating) can be used in carrying out the process (A) according to the invention all conventional proton acceptors.
• alkali metals such as sodium or potassium can be used.
• alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydride and calcium hydride, and also alkali metal alkoxides, such as sodium methoxide, sodium ethylate and potassium tert-butoxide.
• the reaction temperature can be varied within a relatively wide range. In general, temperatures between -75 0 C and 200 ° C, preferably between -5O 0 C and 15O 0 C.
• the process (A) according to the invention is generally carried out under atmospheric pressure.
• reaction component of the formula (II) and the deprotonating base are generally employed in equimolar to about twice the equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 mol).
• the process (B ⁇ ) is characterized in that compounds of the formula (Ia) are each reacted with carboxylic acid halides of the formula (III), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
• Suitable diluents for the process (B 0) according to the invention are all solvents which are inert to the acid halides, preferably hydrocarbons, such as benzine, benzene, toluene, xylene and tetralin, and also halohydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and the like.
• hydrocarbons such as benzine, benzene, toluene, xylene and tetralin
• halohydrocarbons such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and the like.
• ketones such as acetone and methyl isopropyl ketone
• ethers such as diethyl ether, tetrahydrofuran and dioxane
• carboxylic esters such as ethyl acetate
• strongly polar solvents such as dimethylformamide, dimethyl sulphoxide and sulpholane.
• Suitable acid binders in the reaction by the process (B ⁇ ) according to the invention are all customary acid acceptors.
• tertiary amines such as Triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclo-nonene (DBN), Hünig base and N, N-dimethyl-aniline, furthermore alkaline earth metal oxides, such as magnesium and calcium oxide, in addition alkali metal and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate, and alkali hydroxides such as sodium hydroxide and potassium hydroxide.
• DABCO diazabicyclooctane
• DBU diazabicycloundecene
• DBN diazabicyclo-nonene
• Hünig base and N N-dimethyl-aniline
• alkaline earth metal oxides such as magnesium and calcium oxide
• the reaction temperature can be varied within a relatively wide range in the process (B 0 ) according to the invention. In general, one works at temperatures between -20 0 C and + 15O 0 C, preferably between 0 0 C and 100 0 C.
• the starting materials of the formula (Ia) and the carboxylic acid halide of the formula (III) are generally each used in approximately equivalent amounts. However, it is also possible to use the carboxylic acid halide in a larger excess (up to 5 moles). The workup is carried out by conventional methods.
• the process (B ⁇ ) is characterized in that compounds of the formula (I-a) are each reacted with carboxylic anhydrides of the formula (IV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
• Diluents which may be used in the process (B ⁇ ) according to the invention are preferably those diluents which are also preferably used when acid halides are used. Incidentally, an excess carboxylic acid anhydride may also function as a diluent at the same time.
• Suitable acid binders which may be added in the process (B ⁇ ) are preferably those acid binders which are also preferably used when acid halides are used.
• the reaction temperature can be varied within a relatively wide range in the process (B ⁇ ) according to the invention. In general, one works at temperatures between -20 0 C and +150 0 C, preferably between 0 0 C and 100 0 C.
• the starting materials of the formula (Ia) and the carboxylic anhydride of the formula (IV) are generally used in approximately equivalent amounts. However, it is also possible to use the carboxylic acid anhydride in a larger excess (up to 5 moles).
• the workup is carried out by conventional methods. In general, diluent and excess carboxylic anhydride and the resulting carboxylic acid are removed by distillation or by washing with an organic solvent or with water.
• the process (C) is characterized in that compounds of the formula (I-a) are reacted in each case with chloroformates or chloroformic thioesters of the formula (V), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
• Suitable acid binders in the process (C) according to the invention are all customary acid acceptors. Preference is given to using tertiary amines, such as triethylamine, pyridine, DABCO, DBU, DBN, Hünig base and N, N-dimethylaniline, furthermore alkaline earth metal oxides, such as magnesium and calcium oxide, and also alkali metal and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate and alkali hydroxides such as sodium hydroxide and potassium hydroxide.
• tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBN, Hünig base and N, N-dimethylaniline
• alkaline earth metal oxides such as magnesium and calcium oxide
• alkali metal and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate and calcium carbonate and alkali hydroxides such as sodium hydroxide and potassium hydroxide.
• Suitable diluents for the process (C) according to the invention are all solvents which are inert to the chloroformic esters or chloroformic thioesters.
• hydrocarbons such as benzene, benzene, toluene, xylene and tetralin, furthermore halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, chlorobenzene and o-dichlorobenzene, furthermore ketones, such as acetone and methyl isopropyl ether, furthermore ethers, such as diethyl ether, tetrahydrofuran and Dioxane, in addition to carboxylic acid esters, such as ethyl acetate, and also nitriles, such as acetonitrile, and also strongly polar solvents, such as dimethylformamide, dimethyl sulfoxide and sulfolane.
• the reaction temperature can be varied within a relatively wide range.
• the reaction temperature is generally between -20 ° C and +100 0 C, preferably between 0 0 C and 50 0 C.
• the process (C) according to the invention is generally carried out under atmospheric pressure.
• the starting materials of the formula (Ia) and the corresponding chloroformic acid ester or chloroformic thioester of the formula (V) are generally each used in approximately equivalent amounts. However, it is also possible to use one or the other component in a larger excess (up to 2 mol).
• the workup is carried out by conventional methods. In general, the procedure is to remove precipitated salts and to narrow the remaining reaction mixture by stripping off the diluent.
• the process (D) according to the invention is characterized in that compounds of the formula (Ia) are each reacted with compounds of the formula (VI) in the presence of a diluent and, if appropriate, in the presence of an acid binder.
• Suitable optionally added diluents are all inert polar organic solvents, such as ethers, amides, sulfones, sulfoxides, but also haloalkanes.
• the addition of strong deprotonating agents e.g. Sodium hydride or potassium tert-butylate is the enolate salt of the compounds (I-a), can be dispensed with the further addition of acid binders.
• the bases used in process (D) are all customary proton acceptors. Preference is given to using alkali metal hydrides, alkali metal alcoholates, alkali metal or alkaline earth metal carbonates or bicarbonates or nitrogen bases. Examples which may be mentioned are sodium hydride, sodium methoxide, sodium hydroxide, calcium hydroxide, potassium carbonate, sodium bicarbonate, triethylamine, dibenzylamine, diisopropylamine, pyridine, quinoline, diazabicyclooctane (DABCO), diazabicyclononene (DBN) and diazabicycloundecene (DBU).
• DABCO diazabicyclooctane
• DBN diazabicyclononene
• DBU diazabicycloundecene
• the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably is carried out at atmospheric pressure.
• the workup is done by conventional methods.
• the process (E) according to the invention is characterized in that compounds of the formula (I-a) are each reacted with sulfonyl chlorides of the formula (VII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
• the process (E) is preferably carried out in the presence of a diluent.
• Suitable diluents are all inert polar organic solvents such as ethers, amides, ketones, carboxylic acid esters, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride. Preference is given to using dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, ethyl acetate, methylene chloride.
• the addition of strong deprotonating agents represents the enolate salt of the compounds (I-a)
• the further addition of acid binders can be dispensed with.
• acid binders are used, conventional inorganic or organic bases are suitable; sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine may be mentioned by way of example.
• the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
• the workup is done by conventional methods.
• the process (F) according to the invention is characterized in that compounds of the formula (I-a) are reacted in each case with phosphorus compounds of the formula (VIII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
• the process (F) is preferably carried out in the presence of a diluent.
• Suitable diluents are all inert, polar organic solvents such as ethers, carboxylic esters, halogenated hydrocarbons, ketones, amides, nitriles, sulfones, sulfoxides, etc.
• acetonitrile dimethyl sulfoxide, tetrahydrofuran, dimethylformamide, methylene chloride are used.
• Suitable acid binders which may be added are customary inorganic or organic bases such as hydroxides, carbonates or amines. Exemplary sodium hydroxide, sodium carbonate, potassium carbonate, pyridine and triethylamine are listed.
• the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably is carried out at atmospheric pressure.
• the workup is done by conventional methods of organic chemistry.
• the end products are preferably obtained by crystallization, chromato- graphic cleaning or by so-called “distilling", ie removal of the volatile constituents in vacuo.
• the process (G) is characterized in that compounds of the formula (I-a) are reacted with metal hydroxides or metal alkoxides of the formula (EX) or amines of the formula (X), if appropriate in the presence of a diluent.
• Suitable diluents for the process (G) according to the invention are preferably ethers, such as tetrahydrofuran, dioxane, diethyl ether or else alcohols, such as methanol, ethanol, isopropanol, but also water.
• the process (G) according to the invention is generally carried out under atmospheric pressure.
• the reaction temperature is generally between -20 0 C and 100 0 C, preferably between 0 0 C and 5O 0 C.
• the process (H) according to the invention is characterized in that compounds of the formula (Ia) are each reacted with (Ha) compounds of the formula (XI), if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or (H ⁇ ) with compounds of the formula (XII ) if appropriate in the presence of a diluent and, if appropriate, in the presence of an acid binder.
• the process (Ha) is preferably carried out in the presence of a diluent.
• Suitable diluents are all inert organic solvents, such as aromatic hydrocarbons, halogenated hydrocarbons, ethers, amides, nitriles, sulfones or sulfoxides.
• catalysts can be added to accelerate the reaction.
• organotin compounds e.g. Dibutyltin dilaurate can be used.
• Possible diluents which are added are all inert polar organic solvents, such as ethers, carboxylic esters, nitriles, ketones, amides, sulfones, sulfoxides or halogenated hydrocarbons. Preference is given to using dimethyl sulfoxide, tetrahydrofuran, dimethylformamide or methylene chloride.
• the addition of strong deprotonating agents represents the enolate salt of the compound (I-a)
• the further addition of acid binders can be dispensed with.
• customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, triethylamine or pyridine.
• the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
• the workup is done by conventional methods.
• the active compounds / active substance combinations according to 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, forests, gardens and recreational facilities, in supplies 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:
• Anoplura e.g. Damalinia spp., Haematopinus spp., Linognathus spp., Pediculus spp., Trichodectes spp.
• arachnids e.g. Acarus siro, Aceria sheldoni, Aculops spp., Aculus spp., Amblyomma spp., Argas spp., Boophilus spp., Brevipalpus spp., Bryobia praetiosa, Chorioptes spp., Dermanyssus gallinae, Eotetranychus spp., Epitrimerus pyri, Eutetranychus spp.
• Eriophyes spp. Hemitarsonemus spp., Hyalomma spp., Ixodes spp., Latrodectus mactans, Metatetranychus spp., Oligonychus spp., Ornithodoros spp., Panonychus spp., Phyllocoptruta oleivora, Polyphagotarsonemus latus, Psoroptes spp., Rhipicephalus spp. Rhizoglyphus spp., Sarcoptes spp., Scorpio maurus, Stenotarsonemus spp., Tarsonemus spp., Tetranychus spp., Vasates lycopersici.
• Gastropoda e.g. Arion spp., Biomphalaria spp., Bulinus spp., Deroceras spp., Galba spp., Lymnaea spp., Oncomelania spp., Succinea spp.
• helminths from the class of helminths, for example, Ancylostoma duodenale, Ancylostoma ceylanicum, Acylostoma braziliensis, Ancylostoma spp., Ascaris lubricoides, Ascaris spp., Brugia malayi, Brugia timori, Bunostomum spp., Chabertia spp., Clonorchis spp., Cooperia spp., Dicrocoelium spp , Dictyocaulus filaria, Diphyllobothrium latum, Dracunculus medinensis, Echinococcus granulosus, Echinococcus multilocularis, Enterobius vermicularis, Faciola spp., Haemonchus spp., Heterakis spp., Hymenolepis nana, Hyostrongulus spp., Lo
• protozoa such as Eimeria
• Eimeria protozoa
• Heliopeltis spp. Horcias nobilellus, Leptocorisa spp., Leptoglossus phyllopus, Lygus spp., Macropes excavatus, Miridae, Nezara spp., Oebalus spp., Pentomidae, Piesma quadrata, Piezodorus spp., Psallus seriatus, Pseudacysta persea, Rhodnius spp. Sahlbergella singularis, Scotinophora spp., Stephanitis nashi, Tibraca spp., Triatoma spp.
• Empoasca spp. Eriosoma spp., Erythroneura spp., Euscelis bilobatus, Geococcus coffeae, Homalodisca coagulata, Hyalopterus arundinis, Icerya spp., Idiocerus spp., Idioscopus spp., Laodelphax striatellus, Lecanium Spp., Lepidosaphes spp., Lipaphis erysimi, Macrosiphum spp., Mahanarva fbrbriolata, Melanaphis sacchari, Metcalfiella spp., Metopolophium dirhodum, Monellia costalis, Monelliopsis pecanis, Myzus spp., Nasonovia ribisnigri, Nephotettix spp., Nilaparvata lugens, Oncometopia spp.
• Pseudoplusia includens, Pyrausta nubilalis, Spodoptera spp., Thermesia gemmatalis, Tinea pellionella, Tineola bisselliella, Tortrix viridana, Trichoplusia spp.
• Orthoptera e.g. Acheta domesticus, Blatta orientalis, Blattella germanica, Gryllotalpa spp., Leucophaea maderae, Locusta spp., Melanoplus spp., Periplaneta americana, Schistocerca gregaria.
• siphonaptera e.g. Ceratophyllus spp., Xenopsylla cheopis.
• Symphyla e.g. Scutigerella immaculata.
• Thysanoptera e.g. Basothrips biformis, Enneothrips flavens, Frankliniella spp., Heliothrips spp., Hercinothrips femoralis, Rhipiphorothrips cruentarus, Scirtothrips spp., Taeniothrips cardamoni, Thrips spp.
• Thysanura e.g. Lepisma saccharina.
• the plant parasitic nematodes include, for example, Aphelenchoides spp., Bursaphelenchus spp., Ditylenchus dipsaci, Globodera spp., Heterodera spp., Longidorus spp., Meloidogyne spp., Pratylenchus spp., Radopholus similis, Trichodorus spp., Tylenchulus semipenetrans, Xiphinema spp.
• the compounds / active substance combinations according to the invention may optionally also be used in certain concentrations or application rates as herbicides, safeners, growth regulators or agents for improving plant properties, or as microbicides, for example as fungicides, antimycotics, bactericides, viricides (including anti-viral agents) or as agents MLO (Mycoplasma-like-organism) and RLO (Rickettsia-like-organism) are used. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
• plants and parts of plants can be treated.
• 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 that can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the protected by plant breeders' rights or non-protectable plant varieties.
• Plant parts are to be understood as meaning all aboveground and subterranean 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.
• the plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.
• the treatment according to the invention of the plants and plant parts with the active compounds / active agent combinations 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, atomizing, spreading, spreading, injecting and propagating material, in particular in seeds, further by single or multilayer coating.
• the active compounds / active substance combinations can be converted into the customary formulations, such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, Active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances.
• customary formulations such as solutions, emulsions, wettable powders, water- and oil-based suspensions, powders, dusts, pastes, soluble powders, soluble granules, scattering granules, suspension-emulsion concentrates, active substance-impregnated natural products, Active substance-impregnated synthetic substances, fertilizers and ultrafine encapsulations in polymeric substances.
• formulations are prepared in a known manner, for example by mixing the active compounds / active substance combinations with extenders, ie liquid solvents and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam-forming agents.
• extenders ie liquid solvents and / or solid carriers
• surface-active agents ie emulsifiers and / or dispersants and / or foam-forming agents.
• organic solvents can also be used as auxiliary solvents.
• Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, mineral and vegetable oils , Alcohols such as butanol or glycol and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethyl sulfoxide, and water.
• aromatics such as xylene, toluene or alkylnaphthalenes
• chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
• aliphatic hydrocarbons such as
• Ais solid carriers are suitable:
• Ammonium salts and ground natural minerals such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided 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, alkyl sulfates, arylsulfonates and protein hydrolysates; suitable dispersants are: e.g. Lignin-Sulf ⁇ tablaugen and methylcellulose.
• Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids may be used in the formulations.
• Other additives may be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
• the active substance / active substance combinations according to the invention can be present in its commercial formulations as well as in the formulations prepared from these formulations in admixture with other active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.
• active ingredients such as insecticides, attractants, sterilants, bactericides, acaricides, nematicides, fungicides, growth-regulating substances, herbicides, safeners, fertilizers or semiochemicals.
• Particularly favorable mixing partners are e.g. the following:
• 2-phenylphenol 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin;
• Buthiobate butylamine; Calcium polysulfides; capsimycin; captafol; captan; carbendazim;
• carboxin carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb;
• chlorothalonil chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil; Cyproconazoles; cyprodinil; cyprofuram; Dagger G; debacarb; dichlofluanid; dichlone; dichlorophen;
• dimethomorph dimoxystrobin; diniconazole; Diniconazole-M; dinocap; diphenylamines;
• fenpropimorph ferbam; fluazinam; Flubenzimine; fludioxonil; flumetover; flumorph;
• fluoromides fluoxastrobin; fluquinconazole; flurprimidol; flusilazole; flusulfamide; flutolanil;
• flutriafol flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr; Furcarbanil;
• iprobenfos iprodione; iprovalicarb; Irumamycin; isoprothiolane; Isovaledione; kasugamycin;
• Metalaxyl-M metconazole; methasulfocarb; Methfuroxam; metiram; metominostrobin;
• phosdiphen phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz;
• procymidone propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid;
• prothioconazole pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur; Pyrrolnitrine; Quinconazole; quinoxyfen; quintozene; Simeconazole; spiroxamine; Sulfur;
• tebuconazole tecloftalam; Tecnazene; Tetcyclacis; tetraconazole; thiabendazole; Thicyofen;
• Thifluzamide Thiophanate-methyl; thiram; Tioxymid; Tolclofos-methyl; tolylfluanid; Triadimefon; triadimenol; Triazbutil; triazoxide; Tricyclamide; Tricyclazole; tridemorph;
• trifloxystrobin triflumizole; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin; Zineb; ziram; zoxamide; (2S) -N- [2- [4 - [[3- (4-chlorophenyl) -2-propynyl] oxy] -3-methoxyphenyl] ethyl] -3-methyl-2 - [(methylsulfonyl) amino] - butanamide; l- (l-naphthalenyl) -lH-pyrrole-2,5-dione;
• Carbamates for example alanycarb, aldicarb, aldoxycarb, allyxycarb, aminocarb, bendiocarb, benzuracarb, bufencarb, butacarb, butocarboxime, butoxycarboxim, carbaryl, carbofuran, carbosulfan, cloethocarb, dimetilane, ethiofencarb, fenobucarb, fenothiocarb, formetanate, furathiocarb, isoprocarb , Metam-sodium, Methiocarb, Methomyl, Metolcarb, Oxamyl, Pirimicarb, Promecarb, Propoxur, Thiodicarb, Thiofanox,
• Organophosphates for example acephates, azamethiphos, azinphos (-methyl, -ethyl), bromophos-ethyl, bromfenvinfos (-methyl), butathiofos, cadusafos, carbophenothion, chloroethoxyfos, chlorfenvinphos, chloroforms, chlorpyrifos (-methylethyl), coumaphos,
• Pyrethroids for example acrinathrin, allethrin (d-cis-trans, d-trans), beta-cyfluthrin, bifenthrin, bioallethrin, bioallethrin S-cyclopentyl isomer, bioethanomethrin, biopermethrin, bioresmethrin, chlovaporthrin, cis-cypermethrin, cis Resmethrin, cis-permethrin,
• Metaflumizone (BAS 3201)
• Acetylcholine receptor modulators are Acetylcholine receptor modulators
• GABA-driven chloride channel antagonists 5.1
• Organochlorines for example, camphechlor, chlordane, endosulfan, gamma-HCH, HCH, heptachlor, lindane, methoxychlor
• Fiproles for example acetoprole, ethiprole, fipronil, pyrafluprole, pyriprole, vaniliprole
• Mectins for example avermectin, emamectin, emamectin benzoate, ivermectin, milbemycin
• Juvenile hormone mimetics for example, diofenolan, epofenonans, fenoxycarb, hydroprene, kinoprene,
• Diacylhydrazines for example chromafenozides, halofenozides, methoxyfenozides, tebufenozide inhibitors of chitin biosynthesis
• Benzoylureas for example bistrifluron, chlorofluazuron, diflubenzuron, fluazuron, flucycloxuron, fenphenoxuron, hexaflumuron, lufenuron, novaluron, noviflumuron, penfluron, teflubenzuron, triflumuron
• Organotin compounds for example azocyclotin, cyhexatin, fenbutatin oxides
• METI's for example Fenazaquin, Fenpyroximate, Pyrimidifen, Pyridaben, Tebufenpyrad, Tolfenpyrad as well
• Tetronic acids for example spirodiclofen, spiromesifen
• Carboxamides for example flonicamide Octopaminergic agonists, for example, amitraz
• Nereistoxin analogs for example thiocyclam hydrogen oxalate, thiosultap-sodium
• fumigants for example aluminum phosphides, methyl bromides, sulfuryl fluorides
• feed inhibitors for example cryolites, flonicamide, pymetrozines
• mite growth inhibitors for example clofentezine, etoxazole, hexythiazox
• the active compounds / active substance combinations according to the invention can furthermore be present when used as insecticides in their commercial formulations and in the forms of use prepared from these formulations in admixture with synergists.
• Synergists are compounds that increase the effect of the active ingredients without the added synergist itself having to be active.
• the active compounds / active substance combinations according to the invention can also be present in insecticides in their commercial formulations and in the formulations prepared from these formulations in mixtures with inhibitors, the degradation of the active ingredient after application in the environment of the plant, on the surface of plant parts or in plant Reduce tissue.
• the active substance content of the application forms prepared from the commercial formulations can vary within wide ranges.
• the active ingredient concentration of the use forms may be from 0.00000001 up to 95% by weight of active compound, preferably between 0.00001 and 1% by weight.
• the application is done in a custom forms adapted to the application forms.
• plants and their parts can be treated.
• wild species or plant species obtained by conventional biological breeding methods such as crossing or protoplast fusion
• plant 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 parts thereof are treated.
• the terms "parts” or “parts of plants” or “plant parts” have been explained above.
• Plant varieties are understood as meaning plants having new traits which have been bred by conventional breeding, by mutagenesis or by recombinant DNA techniques. These can be varieties, biotypes and genotypes.
• the preferred plants or plant varieties to be treated according to the invention to be treated include all plants which, as a result of the genetic engineering modification, obtained genetic material which gives these plants particularly advantageous valuable properties ("traits").
• traits are better plant growth, increased tolerance to high or low temperatures, increased tolerance to dryness or to bottoms salt, increased flowering, easier harvesting, acceleration of ripeness, higher crop yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or workability of the harvested products.
• Further and particularly emphasized examples of such properties are an increased defense of the plants against animal and microbial pests, as against insects, mites, phytopathogenic fungi, bacteria and / or viruses as well as an increased tolerance of the plants against certain herbicidal active substances.
• transgenic plants are the important crops such as cereals (wheat, rice), corn, soybeans, potatoes, sugar beets, tomatoes, peas and other vegetables, cotton, tobacco, oilseed rape and fruit plants (with the fruits apples, pears, citrus fruits and Grapes), with special emphasis on maize, soya, potato, cotton, tobacco and oilseed rape.
• Traits that are particularly emphasized are the increased defense of the plants against insects, arachnids, nematodes and snails by toxins produced in the plants, in particular those which are produced by the genetic material from Bacillus thuringiensis (eg by the genes Cry ⁇ A (a) , Cry ⁇ A (b), Cry ⁇ A (c), CryllA, CrylüA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CrylF and combinations thereof) in the plants (hereinafter "Bt plants”). Traits also highlight the increased resistance of plants to fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins.
• SAR systemic acquired resistance
• Traits 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).
• the genes which confer the desired properties (“traits”) can also be combined with one another in combinations with one another transgenic plants occur.
• “Bt plants” are maize varieties, cotton varieties, soybean varieties and potato varieties which are sold under the trade names YIELD GARD® (eg corn, cotton, soya), KnockOut® (eg maize), StarLink® (eg maize), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato).
• 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 against 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® tolerance against imidazolinone
• STS® tolerance to sulfonylureas eg corn
• Clearf ⁇ eld® varieties eg corn
• the listed plants can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active substance mixtures according to the invention.
• the preferred ranges given above for the active compounds or mixtures also apply to the treatment of these plants.
• Particularly emphasized is the plant treatment with the compounds or mixtures specifically mentioned in the present text.
• the active compounds / drug combinations according to the invention not only act against plant, hygiene and storage pests, but also in the veterinary sector against animal parasites (ecto- and endoparasites) such as ticks, leather ticks, mange mites, running mites, flies (stinging and licking), parasitic fly larvae , Lice, hair pieces, feathers and fleas.
• animal parasites ecto- and endoparasites
• Anoplurida e.g. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp.
• Trimenopon spp. Menopon spp., Trinoton spp., Bovicola spp., Werneckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp.
• Nematocerina and Brachycerina eg Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp.
• Atylotus spp. Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp.
• siphonaptrida e.g. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp.
• heteropterid e.g. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp.
• Actinedida Prostigmata
• Acaridida e.g. Acarapis spp., Cheyletiella spp., Ornitrocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp., Pterolichus spp , Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp.
• the active compounds / active substance combinations of the formula (I) according to the invention are also suitable for controlling arthropods which are farm animals, such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
• farm animals such as e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, caged birds, aquarium fish and so-called experimental animals, such. Hamsters, guinea pigs, rats and mice.
• the application of the active compounds / active substance combinations according to the invention takes place in the veterinary sector and animal husbandry in a known manner by enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feedthrough method, suppositories, by parenteral Administration, for example by injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, dipping or bathing (dipping), spraying, pouring (pour-on and spot-on), washing, powdering as well as with the aid of active ingredient-containing shaped bodies, such as collars, ear tags, tail tags, limb bands, holsters, marking devices, etc.
• enteral administration in the form of, for example, tablets, capsules, infusions, drenches, granules, pastes, boilies, the feedthrough method, suppositories
• parenteral Administration for
• the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active ingredients in an amount of from 1 to 80% by weight, directly or apply after 100 to 10,000 times dilution or use as a chemical bath.
• formulations for example powders, emulsions, flowable agents
• the compounds / active substance combinations according to the invention have a high insecticidal activity against insects which destroy industrial materials.
• insects By way of example and preferably without limiting however, the following insects are mentioned:
• Hymenoptera such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
• Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
• Non-living materials such as preferably plastics, adhesives, glues, papers and cardboard, leather, wood, wood processing products and paints.
• the material to be protected from insect attack is wood and woodworking products.
• the active compounds can be used as such, in the form of concentrates or generally customary formulations such as powders, granules, solutions, suspensions, emulsions or pastes.
• the formulations mentioned can be prepared in a manner known per se, e.g. by mixing the active compounds with at least one solvent or diluent, emulsifier, dispersing and / or binding or fixing agent, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments, and further processing aids.
• the insecticidal agents or concentrates used for the protection of wood and wood-based materials contain the active ingredient according to the invention in a concentration of 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.
• the amount of agents or concentrates used depends on the nature and occurrence of the insects and on the medium.
• the optimal amount used can be determined in each case by test series. In general, however, it is sufficient to use 0.0001 to 20% by weight, preferably 0.001 to 10% by weight, of the active ingredient, based on the material to be protected.
• the solvent and / or diluent used is an organic-chemical solvent or solvent mixture and / or an oily or oily high-volatile organic-chemical solvent or solvent mixture and / or a polar organic-chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.
• Organic chemical solvents which are preferably oily or oil-type solvents with an evaporation number of above 35 and a flashpoint above 3O 0 C, preferably above 45 ° C, are used.
• water-insoluble, oily and oily solvents corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene are used.
• Mineral oils having a boiling range of 170 to 220 0 C, white spirit having a boiling range of 170 to 22O 0 C, spindle oil with a boiling range of 250 to 350 0 C, petroleum and aromatics with a boiling range of 160 to 280 0 C, oil of turpentine and Like.
• liquid aliphatic hydrocarbons having a boiling range of 180 to 21O 0 C or high-boiling mixtures of aromatic and aliphatic hydrocarbons having a boiling range of 180 to 22O 0 C and / or spindle oil and / or monochloronaphthalene, preferably ⁇ -monochloronaphthalene used.
• the organic semi-volatile oily or oily solvents having an evaporation number above 35 and a flash point above 30 0 C, preferably above 45 ° C, can be partially replaced by light or medium volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flashpoint above 3O 0 C, preferably above 45 0 C, and in that the insecticide fungicide mixture is soluble or emulsifiable in this solvent mixture is.
• a portion of the organic chemical solvent or solvent mixture or an aliphatic polar organic chemical solvent or solvent mixture is replaced.
• aliphatic organic chemical solvents containing hydroxyl and / or ester and / or ether groups are used, for example glycol ethers, esters or the like.
• organic-chemical binders are the water-dilutable and / or soluble or dispersible or emulsifiable synthetic resins and / or binding drying oils used in the organic-chemical solvents used, in particular binders consisting of or containing an acrylate resin, a vinyl resin, eg Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene Cumaronharz, silicone resin, drying vegetable and / or drying oils and / or physically drying binder based on a natural and / or synthetic resin used.
• binders consisting of or containing an acrylate resin, a vinyl resin, eg Polyvinyl acetate, polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene Cumaronharz, silicone
• the synthetic resin used as the binder may be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water repellents, odor correctors and inhibitors or corrosion inhibitors and the like can be used.
• At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably present as the organic-chemical binder in the middle or in the concentrate.
• Alkyd resins with an oil content of more than 45% by weight, preferably 50 to 68% by weight, are preferably used according to the invention.
• the mentioned binder can be completely or partially replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or precipitation. Preferably, they replace 0.01 to 30% of the binder (based on 100% of the binder used).
• the plasticizers are derived from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric esters such as tributyl phosphate, adipic acid esters such as di (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ethers or higher molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid ester.
• phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate
• phosphoric esters such as tributyl phosphate
• adipic acid esters such as di (2-ethylhexyl) adipate
• stearates such as butyl
• Fixing agents are chemically based on polyvinyl alkyl ethers such as e.g. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.
• Particularly suitable solvents or diluents are also water, optionally in admixture with one or more of the abovementioned organochemical solvents or diluents, emulsifiers and dispersants.
• wood protection is provided by large scale impregnation methods, e.g. Vacuum, double vacuum or printing process achieved.
• the ready-to-use agents may optionally contain further insecticides and optionally one or more fungicides.
• Particularly preferred admixing partners may be insecticides such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyphenoxide, triflumuron, chlothianidine, spinosad, tefluthrin,
• insecticides such as chlorpyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, deltamethrin, permethrin, imidacloprid, NI-25, flufenoxuron, hexaflumuron, transfluthrin, thiacloprid, methoxyphenoxide, triflumuron, chlothianidine,
• fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, tebuconazole, cyproconazole, metconazole, imazalil, dichlorofluid, tolylfluanid, 3-iodo-2-propynyl-butylcarbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro N-octylisothiazolin-3-one.
• the compounds according to the invention can be used to protect against fouling of objects, in particular hulls, sieves, nets, structures, quay systems and signal systems, which come into contact with seawater or brackish water.
• Growth by sessile Oligochaeten, like Kalkröhrenwmer as well as by shells and kinds of the group Ledamorpha (barnacles), like different Lepas and Scalpellum kinds, or by kinds of the group Balanomorpha (barnacles), like Baianus or Pollicipes species increases the frictional resistance of As a result of increased energy consumption and, moreover, frequent drydocking periods, the operating costs are significantly increased.
• the ready-to-use antifouling paints may optionally contain other active substances, preferably algicides, fungicides, herbicides, molluscicides or other antifouling active ingredients.
• Suitable combination partners for the antifouling agents according to the invention are preferably:
• the antifouling agents used contain the active ingredient of the compounds of the invention in a concentration of 0.001 to 50 wt .-%, in particular from 0.01 to 20 wt .-%.
• the antifouling agents of the invention further contain the usual ingredients, e.g. in Ungerer, Chem. Ind. 1985, 37, 730-732 and Williams, Antifouling Marine Coatings, Noyes, Park Ridge, 1973.
• antifouling paints contain in particular binders.
• Examples of recognized binders are polyvinyl chloride in a solvent system, chlorinated rubber in a solvent system, acrylic resins in a solvent system, especially in an aqueous system, vinyl chloride / vinyl acetate copolymer systems in the form of aqueous dispersions or in the form of organic solvent systems, butadiene / styrene / acrylonitrile Rubbers, drying oils, such as linseed oil, rosin esters or modified hard resins in combination with tar or bitumens, asphalt and epoxy compounds, small amounts of chlorinated rubber, chlorinated polypropylene and vinyl resins.
• paints also contain inorganic pigments, organic pigments or
• the paints may further plasticizers, the Theological properties contain modifying modifiers as well as other conventional ingredients.
• the compounds according to the invention or the abovementioned mixtures can also be incorporated in self-polishing antifbuling systems.
• the active compounds are also suitable for controlling animal pests, in particular insects, arachnids and mites, which are used in enclosed spaces such as, for example, apartments, factory halls, offices, vehicle cabins and the like. occurrence. They can be used to control these pests, alone or in combination with other active ingredients and adjuvants in household insecticide products. They are effective against sensitive and resistant species and against all stages of development. These pests include:
• Acarina e.g. Argas persicus, Argas reflexus, Bryobia ssp., Dermanyssus gallinae, Glyciphagus domesticus, Ornithodorus moubat, Rhipicephalus sanguineus, Trombicula alfreddugesi, Neutrombicula autumnalis, Dermatophagoides pteronissimus, Dermatophagoides forinae.
• Opiliones e.g. Pseudoscorpiones chelifer, Pseudoscorpiones cheiridium, Opiliones phalangium.
• Zygentoma e.g. Ctenolepisma spp., Lepisma saccharina, Lepismodes inquilinus.
• Diptera e.g. Aedes aegypti, Aedes albopictus, Aedes taeniorhynchus, Anopheles spp., Calliphora erythrocephala, Chrysozona pluvialis, Culex quinquefasciatus, Culex pipiens, Culex tarsalis, Drosophila spp., Fannia canicularis, Musca domestica, Phlebotomus spp., Sarcophaga carnaria, Simulium spp., Stomoxys Calcitrans, Tipula paludosa.
• Lepidoptera e.g. Achroia grisella, Galleria mellonella, Plodia interpunctella, Tinea cloacella, Tinea pellionella, Tineola bisselliella.
• Ctenocephalides canis Ctenocephalides felis, Pulex irritans, Tunga penetrans, Xenopsylla cheopis.
• Hymenoptera e.g. Camponotus herculeanus, Lasius fuliginosus, Lasius niger, Lasius umbratus, Monomorium pharaonis, Paravespula spp., Tetramorium caespitum.
• Heteroptera e.g. Cimex hemipterus, Cimex lectularius, Rhodinus prolixus, Triatoma infestans.
• Application is 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, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
• Pump and atomizer sprays 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, energyless or passive evaporation systems, moth papers, moth cakes and moth gels, as granules or dusts, in litter or bait stations.
• the active compounds / active substance combinations according to the invention can also be used as defoliants,
• Desiccants herbicides and in particular be used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are found in places. grow where they are unwanted. Whether the substances according to the invention act as total or selective herbicides essentially depends on the amount used.
• the active compounds / active ingredient combinations according to the invention may be e.g. used in the following plants:
• the active compounds / active substance combinations according to the invention are suitable, depending on the concentration, for total weed control, for example on industrial and track systems and on paths and squares with and without tree cover.
• the active compounds according to the invention for weed control in permanent crops such as forest, ornamental, fruit, wine, citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants , on ornamental and sports lawns and grazing areas as well as for selective weed control in annual crops.
• the compounds of the formula (I) / active compound combinations according to the invention show strong herbicidal activity and a broad spectrum of activity when applied to the soil and above-ground parts of plants. They also lend themselves, to some extent, to the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both preemergence and postemergence.
• the active compounds / active substance combinations according to the invention can also be used in certain concentrations or application rates for controlling animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active ingredients.
• the active compounds / active substance 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 substance-impregnated natural and synthetic substances and ultrafine encapsulations in polymers substances.
• formulations are prepared in a known manner, e.g. by mixing the active substances with extenders, ie liquid solvents and / or solid carriers, optionally with the use of surface-active agents, ie 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: for example, ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates, as solid carriers for granules: eg broken 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: for example nonionic and anionic emulsifiers, such as polyoxyethylene Fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and
• Adhesives such as carboxymethylcellulose, natural and synthetic powdery, granular or latex-like polymers can be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids.
• Other additives may be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• the formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
• the active compounds / active substance combinations according to the invention can also be used in admixture with known herbicides and / or with substances which improve the crop plant compatibility ("safeners") for weed control, whereby ready-to-use formulations or tank mixes are possible Also possible are mixtures with weedkillers containing one or more known herbicides and a safener.
• safeners substances which improve the crop plant compatibility
• a mixture with other known active ingredients such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and soil conditioners is also possible.
• the active compounds / active substance 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, sprinkling.
• the active compounds / active substance combinations according to the invention can be applied both before and after emergence of the plants. They can also be incorporated into the soil before sowing.
• the amount of active ingredient used can vary within a substantial range. It depends essentially on the type of effect desired. In general, the application rates are between 1 g and 10 kg of active ingredient per hectare of soil, preferably between 5 g and 5 kg per ha.
• the substances / active substance combinations according to the invention have a strong microbicidal action and can be used for controlling unwanted microorganisms, such as fungi and bacteria, in crop protection and in the protection of materials.
• Fungicides can be used for the control of Plasmodiophoromycetes, Oomycetes, Chytridiomycetes, Zygomycetes, Ascomycetes, Basidiomycetes and Deuteromycetes.
• Bactericides can be used in crop protection for controlling Pseudomonadaceae, Rhizobiaceae, Enterobacteriaceae, Corynebacteriaceae and Streptomycetaceae.
• Xanthomonas species such as Xanthomonas campestris pv. Oryzae
• Pseudomonas species such as Pseudomonas syringae pv. Lachrymans
• Erwinia species such as Erwinia amylovora
• Pythium species such as Pythium ultimum
• Phytophthora species such as Phytophthora infestans
• Pseudoperonospora species such as Pseudoperonospora humuli or
• Plasmopara species such as Plasmopara viticola
• Bremia species such as Bremia lactucae
• Peronospora species such as Peronospora pisi or P. brassicae;
• Erysiphe species such as Erysiphe graminis
• Sphaerotheca species such as Sphaerotheca fuliginea
• Podosphaera species such as Podosphaera leucotricha
• Venturia species such as Venruria inaequalis
• Pyrenophora species such as, for example, Pyrenophora teres or P. graminea
• Cochliobolus species such as Cochliobolus sativus
• Uromyces species such as Uromyces appendiculatus
• Puccinia species such as Puccinia recondita
• Sclerotinia species such as Sclerotinia sclerotiorum
• Tilletia species such as Tilletia caries
• Ustilago species such as Ustilago nuda or Ustilago avenae;
• Pellicularia species such as, for example, Pellicularia sasakii; Pyricularia species, such as Pyricularia oryzae;
• Fusarium species such as Fusarium culmorum
• Botrytis species such as Botrytis cinerea
• Septoria species such as Septoria nodorum
• Leptosphaeria species such as Leptosphaeria nodorum
• Cercospora species such as Cercospora canescens
• Altemaria species such as Alternaria brassicae
• Pseudocercosporella species such as Pseudocercosporella herpotrichoides.
• the active compounds / active substance combinations according to the invention also have a strong tonic effect in plants. They are therefore suitable for mobilizing plant-own defenses against attack by unwanted microorganisms.
• plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of plants in such a way that the treated plants exhibit extensive resistance to these microorganisms on subsequent inoculation with undesired microorganisms.
• Undesirable microorganisms in the present case are phytopathogenic fungi, bacteria and viruses.
• the substances according to the invention can therefore be used to protect plants within a certain period of time after the treatment against the infestation by the said pathogens.
• the period within which protection is provided generally extends from 1 to 10 days, preferably 1 to 7 days after the treatment of the plants with the active ingredients.
• the good plant tolerance of the active compounds / active ingredient combinations in the necessary concentrations for controlling plant diseases allows treatment of aboveground plant parts, of plant and seed, and the soil.
• the active compounds / active substance combinations according to the invention are also suitable for increasing crop yield. They are also low toxicity and have good plant tolerance.
• the active compounds / active substance combinations according to the invention may optionally also be used in certain concentrations and application rates as herbicides, for influencing the plant growth, and to control animal pests. If appropriate, they can also be used as intermediates and precursors for the synthesis of other active ingredients.
• the substances of the invention can be used for the protection of industrial materials against infestation and destruction by unwanted microorganisms.
• Technical materials as used herein mean non-living materials that have been prepared for use in the art.
• engineering materials to be protected from microbial alteration or destruction by actives of the invention may be adhesives, glues, paper and board, textiles, leather, wood, paints and plastics, coolants, and other materials that infiltrate or degrade microorganisms can be.
• materials to be protected are also parts of production plants, such as cooling water circuits, called, which can be affected by the proliferation of microorganisms.
• technical materials which may be mentioned are preferably adhesives, glues, papers and cartons, leather, wood, paints, cooling lubricants and heat transfer fluids, particularly preferably wood.
• microorganisms that can cause degradation or a change in the technical materials, for example, bacteria, fungi, yeasts, algae and mucus organisms may be mentioned.
• the active compounds according to the invention preferably act against fungi, in particular molds, wood-discolouring and wood-destroying fungi (Basidiomycetes) and against slime organisms and algae.
• microorganisms of the following genera There may be mentioned, for example, microorganisms of the following genera:
• Alternaria such as Alternaria tenuis
• Aspergillus such as Aspergillus niger
• Chaetomium such as Chaetomium globosum
• Coniophora like Coniophora puetana,
• Lentinus like Lentinus tigrinus
• Penicillium such as Penicillium glaucum
• Polyporus such as Polyporus versicolor
• Aureobasidium such as Aureobasidium pullulans
• Sclerophoma such as Sclerophoma pityophila
• Trichoderma like Trichoderma viride
• Escherichia like Escherichia coli
• Pseudomonas such as Pseudomonas aeruginosa
• Staphylococcus such as Staphylococcus aureus.
• the active compounds / active substance combinations can be converted into the customary formulations, such as solutions, emulsions, suspensions, powders, foams, pastes, granules, aerosols, very fine encapsulations in polymeric substances and in encapsulants for Seeds, as well as ULV-KaIt and warm mist formulations.
• formulations are prepared in a known manner, for example by mixing the active compounds / active substance combinations with extenders, ie liquid solvents, liquefied gases under pressure and / or solid carriers, optionally with the use of surface-active agents, ie emulsifiers and / or dispersants and / or foam generators - funds.
• extenders ie liquid solvents, liquefied gases under pressure and / or solid carriers
• surface-active agents ie emulsifiers and / or dispersants and / or foam generators - funds.
• organic solvents can also be used as auxiliary solvents.
• Suitable liquid solvents are essentially: aromatics such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, eg petroleum fractions, 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 also water.
• aromatics such as xylene, toluene or alkylnaphthalenes
• chlorinated aromatic or chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes or methylene chloride
• aliphatic hydrocarbons such as
• liquefied gaseous diluents or carriers liquids which are gaseous at normal temperature and under normal pressure, for example aerosol propellants, such as halogenated hydrocarbons as well as butane, propane, nitrogen and carbon dioxide.
• Suitable solid carriers are: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates.
• solid carriers for granules are: for example, broken 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 stems.
• Suitable emulsifiers and / or foam-formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohols, holether, for example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolyzates.
• Suitable dispersants are: for example lignin-sulphite liquors and methylcellulose.
• Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex polymers may be used in the formulations, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholipids.
• Other additives may be mineral and vegetable oils.
• Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• inorganic pigments e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
• the formulations generally contain between 0.1 and 95% by weight of active ingredient, preferably between 0.5 and 90%.
• the active compounds / active substance combinations according to the invention can be used as such or in their formulations also in admixture with known fungicides, bactericides, acaricides, nematicides or insecticides, so as to obtain e.g. to broaden the spectrum of action or to prevent development of resistance.
• synergistic effects i. E. the effectiveness of the mixture is greater than the effectiveness of the individual components.
• Suitable mixing partners are, for example, the following compounds:
• 2-phenylphenol 8-hydroxyquinoline sulfate; Acibenzolar-S-methyl; aldimorph; amidoflumet; Ampropylfos; Ampropylfos-potassium; andoprim; anilazine; azaconazole; azoxystrobin;
• bilanafos binapacryl; biphenyl; bitertanol; Blasticidin-S; bromuconazole; Bupirimate;
• Buthiobate butylamine; Calcium polysulfides; capsimycin; captafol; captan; carbendazim;
• carboxin carpropamid; carvones; chinomethionat; Chlobenthiazone; Chlorfenazole; chloroneb; chlorothalonil; chlozolinate; Clozylacon; cyazofamid; cyflufenamid; cymoxanil;
• dichlorophen diclocymet; Diclomezine; dicloran; diethofencarb; Difenoconazole;
• fenpropidin fenpropimorph
• ferbam fluazinam
• Flubenzimine fludioxonil
• flumetover flumorph
• fluoromides fluoxastrobin
• fluquinconazole flurprimidol
• flusilazole flusulfamide
• flutolanil flutriafol; folpet; Fosetyl-Al; Fosetyl-sodium; fuberidazole; furalaxyl; furametpyr;
• Furcarbanil Furmecyclox; guazatine; Hexachlorobenzene; hexaconazole; hymexazol; imazalil;
• Imibenconazole Iminoctadine triacetate; Iminoctadine tris (albesil; iodocarb; ipconazole; iproposite; iprodione; iprovalicarb; irumamycin; isoprothiolane; isovaledione; kasugamycin;
• Metalaxyl-M metconazole; methasulfocarb; Meth tartroxam; metiram; metominostrobin;
• phosdiphen phthalides; picoxystrobin; piperalin; Polyoxins; Polyoxorim; Probenazole; prochloraz;
• procymidone propamocarb; Propanosine-sodium; propiconazole; propineb; proquinazid;
• prothioconazole pyraclostrobin; Pyrazohos; pyrifenox; pyrimethanil; pyroquilon; Pyroxyfur;
• trifloxystrobin triflumizole; triforine; triticonazole; Uniconazole; Validamycin A; vinclozolin;
• DDT deltamethrin, demeton-S-methyl, demeton-S-methylsulphon, diafenthiuron, dialifos, diacinone, dichlofenthione, dichlorvos, dicofol, dicrotophos, dicyclanil, diflubenzuron, dimethoates, dimethylvinphos, dinobutone, dinocap, dinotefuran, diofenolane, disulfone, Docusate-sodium, Dofenapine, DOWCO-439, Eflusilanate, Emamectin, Emamectin benzoate, Empenthrin (IR isomer), Endosulfan, Entomopthora spp., EPN, Esfenvalerate, Ethiofencarb, Ethiprole, Ethion, Ethoprophos, Etofenprox, Etoxazole, Etrimfos,
• Halofenozide HCH, HCN-801, Heptenophos, Hexaflumuron, Hexythiazox, Hydra-methylnone, Hydroprene,
• IKA-2002 Imidacloprid, Imiprothrin, Indoxacarb, Iodofenphos, Iprobenfos, Isazofos, Isofenphos, Isoprocarb, Isoxathion, Ivermectin,
• NC-104 NC-170, NC-184, NC-194, NC-196, Niclosamide, Nicotine, Nitenpyram, Nithiazines, NNI-0001, NNI-0101, NNI-0250, NNI-9768, Novaluron, Noviflumuron,
• Paecilomyces fumosoroseus parathion-methyl, parathion (-ethyl), permethrin (cis-, trans-), petroleum, PH-6045, phenothrin (IR trans isomer), phenthoates, phorates, phosalones, phosmet, phosphamidone, phosphocarb, phoxim, Piperonyl butoxides, Pirimicarb, Pirimiphos-methyl, Pirimiphos-ethyl, Prallethrin, Profenofos, Promecarb, Propaphos, Propargites, Propetamphos, Propoxur, Prothiofos, prothoates, protrifenebutene, pymetrozines, pyraclofos, pyresmethrin, pyrethrum, pyridaben, pyralidyl, pyridapenthione, pyridathione, pyrimid
• the compounds of the formula (I) / active compound combinations according to the invention also have very good antifungal effects. They have a very broad antifungal activity spectrum, especially against dermatophytes and yeasts, mold and diphasic fungi (eg, against Candida species such as Candida albicans, Candida glabrata) and Epidermophyton floccosum, Aspergillus species such as Aspergillus niger and Aspergillus fumigatus, Trichophyton species such as Trichophyton mentagrophytes,
• Microsporon species such as Microsporon canis and audouinii.
• the list of these fungi is by no means a limitation of the detectable mycotic spectrum, but has only an explanatory character.
• the active compounds / active substance combinations can be used as such, in the form of their formulations or the use forms prepared therefrom, such as ready-to-use solutions, suspensions, wettable powders, pastes, soluble powders, dusts and granules.
• the application is done in the usual way, e.g. by pouring, spraying, spraying, scattering, dusting, foaming, brushing, 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. It can also be the seed of the plants to be treated.
• the application rates can be varied within a relatively wide range, depending on the mode of administration.
• Application rates of active ingredient generally between 0.001 and 50 g per kilogram of seed, preferably between 0.01 and 10 g per kilogram of seed. In the treatment of the soil, the application rates of active ingredient are generally between 0.1 and 10,000 g / ha, preferably between 1 and 5,000 g / ha.
• Example XIII-1 Rotate to about 25% of the volume; at 0 - 1O 0 C with concentrated HCl sour, singe and dry.
• the white powder is further reacted directly to prepare Example XIII-1.
• Ammonium carbonate (134.5 g) and sodium cyanide (16.17 g) are placed in 560 ml of water under argon protective gas. Beginning at room temperature, the methoxyacetone (26.4 g) is added dropwise and the reaction mixture stirred for four hours at 55 ° C to 6O 0 C, then stirred at 0 0 C to 5 ° C for two hours.
• the solid is filtered off with suction and dried.
• WP wettable powders
• Seeds of monocotyledonous or dicotyledonous crops are laid out in sandy loam soil in wood fiber pots, covered with soil and grown in the greenhouse under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the single leaf stage.
• the wettable powders (WP) formulated test compounds are sprayed onto the green plant parts in various dosages with a water application rate of 600 l / ha with the addition of 0.2% wetting agent.
• the following compounds show an effect of> 80% in the wake with 320 g / ha ai against Echinocloa crus-galli, Lolium multiflorum and Setaria viridis: Ia-1, Ia-2, Ia-6, Ia-8, Ia-9, Ia-10, Ia-12, Ia-13, Ia-15, Ib-1, Ib-2, Ib-3, Ib-4, Ib-5, Ib-6, 1-b-7, 1-b-9, 1-b-10, 1-b-12, 1-b-13, 1-b-14, 1 c-1, 1-c-2, 1-c-4, 1-c-4, 1-c-5, 1-c-7, 1-c-10.
• Test plants are laid out in sandy loam soil in wood fiber pots or in plastic pots, covered with soil and grown in the greenhouse, during the growing season outside in the greenhouse, under good growth conditions. 2 to 3 weeks after sowing, the test plants are treated in the one to three leaf stage.
• the test compounds formulated as wettable powders (WP) or liquid (EC) are then sprayed onto the plants and the soil surface in various dosages with a water application rate of 300 l / ha with the addition of wetting agent (0.2 to 0.3%).
• WP wettable powders
• EC wettable powders
• Seeds of the crop plants are stained with the safener substance before sowing (indication of the amount of safener in percent relative to the seed weight)
• Crop plants are sprayed before use of the test substances with the safener at a certain hectare application rate (usually 1 day before application of the test substances)
• the safener is applied together with the test substance as a tank mixture (indication of the amount of safener in g / ha or as a ratio to the herbicide).
• Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
• Chinese cabbage leaf discs (Brassica pekinensis) infested with all stages of the green peach aphid ⁇ Myzus persicae) are sprayed with an active compound preparation of the desired concentration.
• the effect is determined in%. 100% means that all aphids have been killed; 0% means that no aphids have been killed.
• Emulsifier 0.5 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the indicated amounts of solvent and emulsifier, and the concentrate is diluted with emulsifier-containing water to the desired concentration.
• Chinese cabbage leaf discs (Brassica pekinensis) are sprayed with a preparation of active compound of the desired concentration and, after drying, are populated with larvae of the horseradish leaf beetle (Phaedon cochleariae).

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