Classifications

• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D235/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings
  • C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
• • 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
  • A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
  • A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
  • A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
  • A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
• • 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
  • A01N43/38—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 condensed with carbocyclic rings
• • 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
  • A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
  • A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
  • A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
  • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
  • C07C69/74—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring
  • C07C69/757—Esters of carboxylic acids having an esterified carboxyl group bound to a carbon atom of a ring other than a six-membered aromatic ring having any of the groups OH, O—metal, —CHO, keto, ether, acyloxy, groups, groups, or in the acid moiety
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
  • C07D307/94—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom spiro-condensed with carbocyclic rings or ring systems, e.g. griseofulvins

Definitions

• the invention relates to new spirocyclic phenylketoenols, several processes and intermediates for their preparation and their use as pesticides and herbicides
• X represents halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulphinyl, alkylsulphonyl, haloalkyl, haloalkenyl, haloalkoxy, halogenoalkenyloxy, nitro, cyano or in each case optionally substituted phenyl, phenoxy, phenylthio, benzyloxy or benzylthio ,
• Y represents hydrogen, halogen, alkyl, alkenyl, alkynyl, alkoxy, alkenyloxy, alkylthio, alkylsulfinyl, alkylsulfonyl, haloalkyl, haloalkenyl, haloalkoxy, haloalkenyloxy, nitro or cyano,
• n O, 1, 2 or 3
• E represents a metal ion equivalent or an ammonium ion
• L represents oxygen or sulfur
• M oxygen or sulfur
• Rl for alkyl or alkenyl optionally substituted by halogen
• R, R4 and R ⁇ independently of one another for each, if appropriate
• R "and R ⁇ independently of one another represent hydrogen, in each case optionally substituted by halogen-substituted alkyl, cycloalkyl, alkenyl, alkoxy or alkoxyalkyl, optionally substituted phenyl, optionally substituted benzyl, or together with the N atom to which they are attached, stand for a ring which may contain oxygen or sulfur,
• R 9 represents hydrogen, in each case optionally substituted alkyl, cycloalkyl,
• R 10 represents hydrogen or alkyl
• R 1 - represents alkyl or alkenyl
• R 12 represents alkyl or alkenyl
• n 0, 1 or 2
• R 1 'independently of R 1 represents the meanings of R 1 given above and
• R 2 'independently of R 2 represents the meanings of R 2 given above.
• the compounds of the formula (I), depending on the nature of the substituents, can be present as geometric and / or optical isomers or isomer mixtures in different compositions, which may or may not be in the customary manner
• R 8 represents alkyl (preferably C 6 -C 8 alkyl)
• W represents hydrogen, halogen, alkyl (preferably Ci-Cg-alkyl) or alkoxy (preferably Cj-Cg-alkoxy),
• R 1 has the meanings given above and
• R 1 has the meanings given above,
• R 2 and M have the meanings given above,
• R 3 has the meaning given above
• Me for a mono- or divalent metal preferably an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
• an alkali or alkaline earth metal such as lithium, sodium, potassium, magnesium or calcium
• R 13 , R 14 , R 15 independently of one another represent hydrogen or alkyl, (preferably C r C 8 alkyl),
• R 6 and L have the meanings given above,
• the compounds of the formulas (Ila), (I-2-a) and (I-3-a) according to the invention are thus important intermediates for the preparation of the compounds according to the invention bonds of the formulas (II), (1-2) and (1-3), in which G represents one of the groups b), c), d), e), f) or g).
• the new compounds of the formula (I) have very good activity as pesticides, preferably as insecticides and acaricides and as herbicides.
• X preferably represents halogen, Ci-Cg-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, Ci-Cg-alkoxy, C3-C6-alkenyloxy, CI-C ⁇ -alkylthio, Ci-Cö-alkylsulfinyl, Ci-Cß-alkylsulfonyl, Ci-Cß-haloalkyl, C2 ⁇ C6-haloalkenyl, Ci-Cg-haloalkoxy, C3-C6-haloalkenyloxy, nitro, cyano or in each case optionally by halogen, C ⁇ -Cg-alkyl, Ci Cg-alkoxy, -C-C4-haloalkyl, C ⁇ -C4-haloalkoxy, nitro or cyano substituted phenyl, phenoxy, phenylthio, benzyloxy or benzylthio.
• Y preferably represents hydrogen, halogen, C 1 -C 6 -alkyl, C2-C6-alkenyl,
• C2-C6- alkynyl Ci-Cö-alkoxy, Cß-Cö-alkenyloxy, C1 -C6- alkylthio, Ci-Cg-alkylsulfinyl, Ci-Cg- alkylsulfonyl, C ⁇ -C6-haloalkyl, C2-C6- haloalkenyl, Ci Cg-haloalkoxy, C3-C6-haloalkenyloxy, nitro or cyano.
• n is preferably 0, 1, 2 or 3.
• Het preferably represents one of the groups
• G preferably represents hydrogen (a) or one of the groups
• E represents a metal ion equivalent or an ammonium ion
• L represents oxygen or sulfur
• Rl preferably represents in each case optionally substituted by halogen C ⁇ - C20-alkyl, C2-C20 "alkenyl, Ci-Cg-alkoxy-Ci-Cg-alkyl, Ci-Cg-alkylthio-Ci-Cg-alkyl or poly- Ci-Cg-alkoxy-Ci-Cg-alkyl, for C3-Cg-cycloalkyl optionally substituted by halogen, Ci-Cg-alkyl or Ci-Cg-alkoxy, in which one or more (in particular at most two) not directly adjacent methylene groups are replaced by oxygen and / or sulfur,
• phenyl which is optionally substituted by halogen, cyano, nitro, C 1 -C 6 -alkyl, C 1 -C 5 -alkoxy, C 1 -C 6 -haloalkyl, C 1 -C 6 -haloalkoxy, C 1 -C 6 -alkylthio or C 1 -C 6 -alkylsulfonyl,
• phenyl-Ci-C0-alkyl optionally substituted by halogen, nitro, cyano, Ci-Cg-alkyl, Ci-C ⁇ -alkoxy, Ci-Cg-haloalkyl or Ci-Cg-haloalkoxy,
• hetaryl optionally substituted by halogen or C 1 -C 6 -alkyl (for example pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or thienyl,
• phenoxy-Ci-Cg-alkyl which is optionally substituted by halogen or C 1 -C 6 -alkyl or
• R 2 preferably represents in each case optionally substituted by halogen C 1 -C 20 -alkyl, C 2 -C 20 "alkenyl, C 1 -C 6 -alkoxy-C 1 -C 6 -alkyl or poly-C 1 -C 6 -alkoxy-C 2 -C 8 -alkyl, for C3-Cg-cycloalkyl which is optionally substituted by halogen, Ci-Cg-alkyl or Ci-Cg-alkoxy or
• R3 preferably represents Ci-Cg-alkyl optionally substituted by halogen or in each case optionally by halogen, Ci-Cg-alkyl, C ⁇ -Cg-
• R 4 and R5 are preferably independently of one another each optionally substituted by halogen Ci-Cg-alkyl, Ci-Cg-alkoxy, Ci-Cg-alkylamino, di- (-C-Cg-alkyl) amino, Ci -Cg-alkylthio , C2-Cg-alkenylthio, C3-C-cycloalkylthio or for each optionally by halogen, nitro, cyano, C1-C4-alkoxy, C ⁇ -C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C ⁇ -C -Alkyl or -C -C-haloalkyl substituted phenyl, phenoxy or phenylthio.
• R6 and R 7 independently of one another preferably represent hydrogen, in each case optionally substituted by halogen-Ci-Cg-alkyl, C3-Cg-cycloalkyl, Ci-Cg-alkoxy, C3-Cg-alkenyl or Ci-Cg-alkoxy-Ci -Cg-alkyl, for optionally by halogen, C ⁇ -Cg-haloalkyl, Cj-Cg-alkyl or C1 -
• R ⁇ preferably represents hydrogen, represents optionally halogen-substituted C ⁇ -CG alkyl, optionally substituted by halogen, C ⁇ -C4-alkyl or C j-C4-alkoxy-substituted C3-C 8 -cycloalkyl or represents in each case optionally substituted by halogen, C r C 6 alkyl, C r C 4 - alkoxy, C r C 4 haloalkyl, C r C 4 - haloalkoxy, nitro or cyano-substituted phenyl, benzyl or hetaryl
• R 10 preferably represents hydrogen or C 1 -C 6 -alkyl.
• R 11 and R 12 are the same or different and are preferably C j -Cg alkyl or C 3 -C 6 alkenyl.
• m is preferably 0 or 1.
• R 1 ' independently of R 1, preferably has the meanings given above for R 1 as preferred.
• R 2 ' independently of R 2, preferably has the meanings given above for R 2 as preferred.
• X particularly preferably represents fluorine, chlorine, bromine, C1-C4-alkyl, C1-C4-alkoxy, C ⁇ -C4-haloalkyl, -C-C4-haloalkoxy, nitro or cyano.
• Y particularly preferably represents hydrogen, fluorine, chlorine, bromine, C 1 -C 4 -alkyl, CJ-C 4 -alkoxy, C 1 -C 4 -haloalkyl, C 4 -C 4 -haloalkoxy, nitro or cyano.
• Z particularly preferably represents fluorine, chlorine, bromine, C 1 -C 4 -alkyl, C1-C4-
• n particularly preferably represents 0, 1 or 2.
• Het is particularly preferably one of the groups
• G particularly preferably represents hydrogen (a) or one of the groups OLR 4
• E represents a metal ion equivalent or an ammonium ion
• L represents oxygen or sulfur
• M stands for oxygen or sulfur.
• phenyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, -C-C -Al__yl, C ⁇ -C4-Al oxy, C ⁇ -C3-haloalkyl or C ⁇ -C3-haloalkoxy,
• pyrazolyl for pyrazolyl, thiazolyl, pyridyl, pyrimidyl, furanyl or each optionally substituted by fluorine, chlorine, bromine or C1-C4-alkyl
• R 2 particularly preferably represents in each case optionally substituted by fluorine -CC g-alkyl, C2 ⁇ -C g-alkenyl, -C-Cg-alkoxy-C2-Cg-alkyl or poly-C 1 -Cg-alkoxy-C 2 -Cg -alkyl,
• phenyl or benzyl each optionally substituted by fluorine, chlorine, bromine, cyano, nitro, Ci-C4-alkyl, -C-C3 alkoxy, C ⁇ -C3-haloalkyl or C ⁇ -C3-haloalkoxy.
• R ⁇ particularly preferably represents C ⁇ -Cg-alkyl optionally substituted by fluorine or chlorine or in each case optionally by fluorine, chlorine, bromine, Cj-Cs-alkyl, Ci-Cs-alkoxy, Ci ⁇ -haloalkyl, C ⁇ -C3- Halogenoalkoxy, cyano or nitro substituted phenyl or benzyl.
• R 4 and R5 are particularly preferably, independently of one another, in each case optionally substituted by fluorine or chlorine, Cj-Cg-alkyl, Cj-Cg-alkoxy, Ci-Cg-alkylamino, di- (-C-Cg-alkyl) amino, C ⁇ -Cg -Alkylthio, C3-C4-alkenylthio or C3-Cg-cycloalkylthio or for each optionally by fluorine, chlorine, bromine, nitro, cyano, -C-C3-alkoxy, C1-C3-haloalkoxy, -C-C3-alkylthio, C ⁇ -C3 -Halogenalkylthio, -C-C3-alkyl or -C-C3-haloalkyl substituted phenyl, phenoxy or phenylthio.
• R "and R 7 independently of one another particularly preferably represent hydrogen, in each case optionally substituted by halogen (in particular fluorine or chlorine) Ci-Cg-alkyl, C3-Cg-cycloalkyl, Ci-Cg-alkoxy, C3-Cg-alkenyl or Ci -Cg-alkoxy-Ci-Cg-alkyl, for optionally substituted by halogen, -C-C5-haloalkyl, Cj-C5-alkyl or C ⁇ -C5-alkoxy y, phenyl, optionally substituted by halogen, C1 -C5 alkyl, C ⁇ -Cs halogen alkyl or -C ⁇ C5-alkoxy substituted benzyl or together for a C3-Cg-alkylene radical, in which a methylene group which is not directly adjacent to the nitrogen atom is optionally replaced by oxygen or sulfur.
• halogen in particular fluorine or chlorine
• R ⁇ particularly preferably represents hydrogen, optionally substituted by fluorine or chlorine, Ci-Cg-alkyl, C3-C7-cycloalkyl or, in each case optionally by fluorine, chlorine, bromine, -CC5-alkyl, -C ⁇ C 4 - alkoxy, C 1 -C 2 haloalkyl, C 1 -C 2 haloalkoxy, nitro or cyano substituted phenyl or benzyl, pyrimidyl or thiazolyl or for CO-R 1 ', CO 2 R 2 ', SO 2 R r , CONH 2 , CONHR 11 or
• R 10 particularly preferably represents hydrogen or Ci-Cg-alkyl.
• R 11 and R 12 are the same or different and are particularly preferably Cj-C 4 -
• R 1 'independently of R 1 particularly preferably has the meanings given above for R 1 as particularly preferred.
• R 2 'independently of R 2 particularly preferably has the meanings given above for R 2 as particularly preferred.
• X very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, methoxy, ethoxy, n-propoxy, iso-propoxy, trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano.
• Y very particularly preferably represents hydrogen, fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy , Trifluoromethyl, difluoromethoxy, trifluoromethoxy, nitro or cyano.
• Z very particularly preferably represents fluorine, chlorine, bromine, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, tert-butyl, methoxy, ethoxy, n-propoxy, iso-propoxy, difluoromethoxy , Trifluoromethoxy, nitro or cyano.
• n very particularly preferably represents 0, 1 or 2, emphasized 0 or 1.
• G very particularly preferably represents hydrogen (a) or one of the groups
• E represents a metal ion equivalent or an ammonium ion
• L represents oxygen or sulfur
• M stands for oxygen or sulfur.
• R very particularly preferably represents C -C4-alkyl, C2-C14-alkenyl, -C-C4-alkoxy-C ⁇ - each optionally substituted by fluorine or chlorine Cg-alkyl or C1-C4-alkyl thio-Ci-Cg-alkyl or for C3-Cg-cycloalkyl optionally substituted by methyl, ethyl, tert-butyl or methoxy,
• phenyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy,
• benzyl optionally substituted by fluorine, chlorine, bromine, methyl, methoxy, trifluoromethyl or trifluoromethoxy or
• furanyl, thienyl or pyridyl each optionally substituted by fluorine, chlorine, bromine or methyl.
• R 2 very particularly preferably represents C 1 -C 14 -alkyl, C 2 -C 4 -alkenyl or C -C 4 -alkoxy-C2-Cg-alkyl,
• phenyl or benzyl optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl, methoxy, trifluoromethyl or trifluoromethoxy.
• R 3 very particularly preferably represents methyl, ethyl, n-propyl, isopropyl which is optionally substituted by fluorine or chlorine or represents in each case optionally by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, iso-
• R 4 and R5 are very particularly preferably independently of one another each optionally substituted by fluorine or chlorine, C1-C4-alkyl, C1-C4-alkoxy, -C-C4-alkylamino, di- (-C-C4-alkyl) amino or C -C4 alkylthio, or represents in each case optionally substituted by fluorine, chlorine, bromine, nitro, cyano, C2-alkoxy, C ⁇ -C2-fluoroalkoxy, C1-C2 alkylthio, C ⁇ -C 2 fluoroalkyl thio or C-C3 alkyl substituted Phenyl, phenoxy or phenylthio.
• R6 and R 7 independently of one another very particularly preferably represent hydrogen, in each case optionally substituted by fluorine or chlorine, C 4 -C 4 -alkyl, C3-Cg-cycloalkyl, C -C 4 -alkoxy, C3-C4-alkenyl or C1-C4-
• Methylene group is replaced by oxygen or sulfur.
• R ⁇ very particularly preferably represents hydrogen, C1-C4-alkyl, C3-Cg-cycloalkyl or in each case optionally by fluorine, chlorine, bromine, methyl, ethyl, n-propyl, isopropyl, tert-butyl, Methoxy, trifluoromethyl, Trifluoromethoxy, nitro or cyano substituted phenyl or benzyl or for CO-R 1 ', CO 2 R 2 ', SO j R 1 ', CONH 2 , CONHR 11 or R 11 y
• R 10 very particularly preferably represents hydrogen or methyl.
• R 11 and R 12 are the same or different and very particularly preferably represent methyl or ethyl.
• n very particularly preferably stands for 1.
• R 2 'independently of R 2 very particularly preferably has the meanings given above for R 2 as being very particularly preferred.
• Saturated or unsaturated hydrocarbon radicals such as alkyl or alkenyl can also be used in connection with heteroatoms, e.g. in alkoxy, where possible, be straight-chain or branched.
• Optionally substituted radicals can be mono- or polysubstituted, whereby in the case of multiple substitutions the substituents can be the same or different.
• acylamino acid esters of the formula (II) are obtained, for example, if amino acid derivatives of the formula (XV)
• X, Y, Z and n have the meanings given above and
• X, Y, Z and n have the meanings given above and
• reaction scheme shows exemplary synthetic routes to precursors of formula (III) and end products of formula (I).
• benzylthio-carboxylic acid halides of the formula (XXIII) are new. They can be prepared by known processes (J. Antibiotics (1983), 26, 1589, WO 95/26 345).
• Chlorodithio-formic acid esters of the formula (VIII), sulfonic acid chlorides of the formula (IX), phosphorus compounds of the formula (X) and metal hydroxides, metal alkoxides or amines of the formula (XI) and (XII), isocyanates of the formula (XIII) and carbamic acid chlorides of the formula (XIV) are generally known compounds of organic or inorganic chemistry.
• Process (A) is characterized in that compounds of the formula (II) in which Q, X, Y, Z, m, n and R & have the meanings given above are subjected to an intramolecular condensation in the presence of a base
• All inert organic solvents can be used as diluents in process (A) according to the invention.
• Hydrocarbons such as toluene and xylene, preferably ethers such as dibutyl ether, tetrahydrofuran, dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methylpyrrolidone, and alcohols such as methanol, ethanol, propanol, are preferably usable. Iso-propanol, butanol, iso-butanol and tert. Butanol
• Alkali metal and alkaline earth metal oxides, hydroxides and carbonates such as sodium hydroxide, potassium hydroxide, magnesium oxide, calcium oxide, sodium carbonate, potassium carbonate and calcium carbonate, are preferably used
• alkali metals such as sodium or potassium Alkali metal and alkaline earth metal amides and hydrides, such as sodium amide and sodium hydride, are also used and calcium hydride, and also alkali metal alcoholates such as sodium methylate, sodium ethylate and potassium tert
• reaction temperatures can be varied within a substantial range. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.
• Process (A) according to the invention is generally carried out under normal pressure.
• reaction components of the formula (II) and the deprotonating bases are generally employed in approximately equimolar to double equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 moles).
• Process (B) is characterized in that compounds of the formula (III), in which Q, X, Y, Z, m, n and R ⁇ have the meanings given above, in the presence of a diluent and in the presence of a base of an intramolecular one Subject to condensation.
• inert organic solvents can be used as diluents in process (B) according to the invention.
• Hydrocarbons such as toluene and xylene
• ethers such as dibutyl ether, tetrahydrofuran
• Dioxane Dioxane, glycol dimethyl ether and diglycol dimethyl ether, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
• polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N-methyl-pyrrolidone.
• alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol and tert. -Butanol can be used.
• All conventional proton acceptors can be used as the base (deprotonating agent) when carrying out process (B) according to the invention.
• alkali metals such as sodium or potassium can be used.
• alkali metal and alkaline earth metal amides and hydrides such as sodium amide, sodium hydroxide and calcium hydroxide, and also alkali metal alcoholates, such as sodium methyl. lat, Nat ⁇ um ethylate and Ka um tert -butylat usable
• reaction temperatures can be varied within a substantial range when carrying out process (B) according to the invention. In general, temperatures between 0 ° C. and 250 ° C., preferably between 50 ° C. and 150 ° C.
• Process (B) according to the invention is generally carried out under normal pressure
• reaction components of the formula (III) and the deprotonating bases are generally employed in approximately equimolar amounts. However, it is also possible to use one or the other component in a larger excess (up to 3 Mol) to use
• the process (C) is characterized in that compounds of the formula (IV) in which Q, W, X, Y, Z, m, n and R ⁇ have the meaning given above, in the presence of an acid and optionally in the presence of a Diluent cyclized intramolecularly
• All inert organic solvents can be used as diluents in process (C) according to the invention.
• Hydrocarbons such as toluene and xylene can preferably be used, furthermore halogenated hydrocarbons such as dichloromethane, chloroform, ethylene chloride, chlorobenzene, dichlorobenzene, and also polar solvents such as dimethyl sulfoxide, sulfolane, dimethylformamide and N- Methyl pyrrolidone.
• Alcohols such as methanol, ethanol, propanol, isopropanol, butanol, isobutanol, tert-butanol can also be used.
• the acid used can also serve as a diluent.
• All customary inorganic and organic acids such as e.g. Hydrogen halide acids, sulfuric acid, alkyl, aryl and haloalkyl sulfonic acids, especially halogenated alkyl carboxylic acids such as e.g. Trifluoroacetic acid.
• reaction temperatures can be varied within a substantial range when carrying out process (C) according to the invention. In general, temperatures between 0 ° C and 250 ° C, preferably between 50 ° C and 150 ° C.
• Process (C) according to the invention is generally carried out under normal pressure.
• reaction components of the formulas (IV) and the acid for example in equimolar amounts.
• the acid as a solvent or as a catalyst.
• Process (Da) is characterized in that compounds of the formulas (I-l-a) to (1-3 -a) are each reacted with carboxylic acid halides of the formula (V), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
• Diluents which can be used in the process (Da) according to the invention are all solvents which are inert to the acid halides.
• Hydrocarbons such as gasoline, benzene, toluene, xylene and tetralin are preferably usable, furthermore halogenated hydrocarbons such as methylene chloride, chloroform, carbon tetrachloride.
• All customary acid acceptors are suitable as acid binders for the reaction according to the process (Da) according to the invention.
• Tertiary amines such as triethylamine, pyridine, diazabicyclooctane (DABCO), diazabicycloundecene (DBU), diazabicyclonones (DBN), Hunig base and N, N-dimethylaniline, and also alkaline earth metal oxides, such as magnesium and calcium oxide, are also preferably used Alkali and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate and calcium carbonate, and alkali metal hydroxides, such as sodium hydroxide and potassium hydroxide.
• reaction temperatures can be varied within a substantial range in the process (Da) according to the invention. In general, temperatures between -20 ° C and + 150 ° C, preferably between 0 ° C and 100 ° C.
• the starting materials of the formulas (I-l-a) to (I-3-a) and the carboxylic acid halide of the formula (V) are generally in each case used in approximately equivalent amounts. However, it is also possible to use the carboxylic acid halide in a larger excess (up to 5 mol). The processing takes place according to usual methods.
• Process (Dß) is characterized in that compounds of the formulas (I-l-a) to (1-3 -a) are reacted with carboxylic anhydrides of the formula (VI), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
• the diluents used in the process (Dß) according to the invention are preferably those diluents which are also used acid halides are preferred.
• An excess of carboxylic acid anhydride can also act as a diluent
• the acid binders which are optionally added in the process (Dß) are preferably those acid binders which are also preferred when using acid halides
• reaction temperatures can be varied within a substantial range in the process (Dß) according to the invention
• the starting materials of the formulas (I-l-a) to (I-3-a) and the carboxylic anhydride of the formula (VI) are generally used in approximately equivalent amounts in each case. However, it is also possible to use the carboxylic anhydride in a larger excess (up to 5 mol). Working up is carried out by customary methods.
• the general procedure is to remove diluent and excess carboxylic acid anhydride and the resulting carboxylic acid by distillation or by washing with an organic solvent or with water
• Process (E) is characterized in that compounds of the formulas (I-l-a) to (I-3-a) are each reacted with chloroformates or chloroformates of formula (VII), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder
• Suitable acid binders for the reaction according to process (E) according to the invention are all customary acid acceptors.
• Tertiary amines such as triethylamine, pyridine, DABCO, DBU, DBA, humg base and are preferably usable
• N, N-dimethyl-aniline furthermore alkaline earth metal oxides, such as magnesium and calcium oxide, furthermore alkali and alkaline earth metal carbonates, such as sodium carbonate, potassium carbonate nate and calcium carbonate as well as alkali hydroxides such as sodium hydroxide and potassium hydroxide.
• alkaline earth metal oxides such as magnesium and calcium oxide
• alkali and alkaline earth metal carbonates such as sodium carbonate, potassium carbonate nate and calcium carbonate
• alkali hydroxides such as sodium hydroxide and potassium hydroxide.
• Diluents which can be used in process (E) according to the invention are all solvents which are inert to chloroformate or chloroformate, preferably hydrocarbons, such as gasoline, benzene, toluene, xylene and tetralin, and furthermore halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride, Chlorobenzene and o-dichlorobenzene, also ketones such as acetone and methyl isopropyl ketone, nitriles such as acetonitrile, further ethers such as diethyl ether, tetrahydrofuran and dioxane, in addition carboxylic acid esters such as ethyl acetate, and also strongly polar solvents such as dimethyl sulfoxide and Sulfolan
• reaction temperatures can be varied within a substantial range in carrying out process (E) according to the invention
• reaction temperatures are generally between -20 ° C and + 100 ° C, preferably between 0 ° C and 50 ° C
• Process (E) according to the invention is generally carried out under normal pressure
• the starting materials of the formulas (Ila) to (1-3 -a) and the corresponding chloroformate or chloroformate thiol ester of the formula (VII) are generally in each case used in approximately equivalent amounts. However, it is also possible one or the other component to be used in a larger excess (up to 2 mol). Working up is carried out according to customary methods. The general procedure is to remove precipitated salts and to concentrate the remaining reaction mixture by pulling off the diluent
• Process (F) according to the invention is characterized in that compounds of the formulas (Ila) to (I-3-a) in each case with compounds of the formula (VIII) in In the presence of a diluent and optionally in the presence of an acid binder.
• chloromonothio formic acid ester or chlorodithio formic acid ester of the formula (VIII) is set at 0 to 120 ° C., preferably at 20, per mol of starting compound of the form (Ila) to (1-3 -a) up to 60 ° C.
• inert polar organic solvents such as ethers, nitriles, ketones, carboxylic acid esters, amides, are suitable as diluents which may be added.
• Dimethyl sulfoxide, tetrahydrofuran, ethyl acetate, dimethylformamide or methylene chloride are preferably used.
• the addition of strong deprotonating agents such as e.g. Sodium hydride or potassium tert-butylate, the enolate salt of the compounds (I-l-a) to (I-3-a), can be dispensed with the further addition of acid binders.
• customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
• the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
• the processing takes place according to usual methods.
• Process (G) according to the invention is characterized in that compounds of the formulas (I-l-a) to (1-3 -a) are in each case compounded with sulfonyl chlorides of the formula
• any inert polar organic solvents such as ethers, amides, ketones, carboxylic acid esters, nitriles, sulfones, sulfoxides or halogenated hydrocarbons such as methylene chloride can be used as diluents.
• Dimethyl sulfoxide, ethyl acetate, acetonitrile, tetrahydrofuran, dimethylformamide, methylene chloride are preferably used.
• the enolate salt of the compounds (I-1-a) to (I-3-a) is represented by the addition of strong deprotonating agents (such as sodium hydride or potassium tert-butylate), the further addition of acid-binding agents can be dispensed with.
• strong deprotonating agents such as sodium hydride or potassium tert-butylate
• customary inorganic or organic bases are suitable, for example sodium hydroxide, sodium carbonate, potassium carbonate, pyridine, triethylamine.
• the reaction can be carried out at atmospheric pressure or under elevated pressure, preferably at atmospheric pressure.
• the processing takes place according to usual methods.
• Process (H) is characterized in that compounds of the formulas (I-l-a) to (I-3-a) are each reacted with phosphorus compounds of the formula (X), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder.
• the manufacturing process (H) uses compounds of the formulas to obtain compounds
• Acetonitrile, dimethyl sulfoxide, ethyl acetate, tetrahydrofuran, dimethylformamide or methylene chloride are preferably used
• Possible inorganic binders which may be added are customary inorganic or organic bases, such as hydroxides, carbonates or amines
• the reaction can be carried out under atmospheric pressure or under elevated pressure, preferably under atmospheric pressure.
• Working up is carried out by customary methods in organic chemistry.
• the end products obtained are preferably purified by crystallization, chromatographic purification or by so-called “distillation", ie removal of the volatile constituents in vacuo
• Process (I) is characterized in that compounds of the formulas (I-l-a) to (1-3 -a) are reacted with metal hydroxides or metal alkoxides of the formula (XI) or amines of the formula (XII), if appropriate in the presence of a diluent
• Suitable diluents in process (I) according to the invention are preferably ethers such as tetrahydrofuran, dioxane, diethyl ether or alcohols such as methanol, ethanol, isopropanol, but also water.
• Process (I) according to the invention is generally carried out under atmospheric pressure.
• reaction temperatures are in general between -20 ° C and 100 ° C, preferably between 0 ° C and 50 ° C
• Process (J) according to the invention is characterized in that compounds of the formulas (Ila) to (1-3 -a) are each reacted with (Yes) compounds of the formula (XIII), if appropriate in the presence of a diluent and if appropriate in the presence of a catalyst or ( Jß) with compounds of the formula (XIV), if appropriate in the presence of a diluent and if appropriate in the presence of an acid binder
• Possible diluents added are all inert organic solvents, such as ethers, amides, nitriles, ketones, carboxylic acid esters, sulfones, sulfoxides
• catalysts can be added to accelerate the reaction.
• Organotin compounds such as dibutyltin dilaurate, can be used very advantageously as catalysts. It is preferably carried out at normal pressure
• inert polar organic solvents such as ethers, amides, ketones, carboxylic acid esters, sulfones, sulfoxides or halogenated hydrocarbons, are suitable as diluents which may be added
• the enolate salt of the compound (Ila) to (I-3-a) is prepared by adding strong deprotonating agents (such as, for example, sodium hydride or potassium tertiary butylate), the further addition of acid binders can be dispensed with.
• strong deprotonating agents such as, for example, sodium hydride or potassium tertiary butylate
• acid binders are used, customary inorganic or organic bases are possible, examples being 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 processing takes place according to usual methods.
• the active compounds are suitable for controlling animal pests, preferably arthropods and nematodes, in particular insects and arachnids, which are in the
• Isopoda e.g. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.
• Diplopoda e.g. Blaniulus guttulatus.
• Chilopoda e.g. Geophilus carpophagus, Scutigera spec.
• Symphyla e.g. Scutigerella immaculata.
• Thysanura e.g. Lepisma saccharina.
• Collembola e.g. Onychiurus armatus.
• Orthoptera for example Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
• Dermaptera for example, Forficula auricularia.
• Isoptera for example Reticulitermes spp ..
• Thysanoptera e.g. Hercinothrips femoralis, Thrips tabaci.
• Homoptera e.g. Aleurodes brassicae, Bemisia tabaci, Trialeur
• Lepidoptera e.g. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp.
• Hymenoptera e.g. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
• Siphonaptera e.g. Xenopsylla cheopis, Ceratophyllus spp .. From the order of the Arachnida e.g. Scorpio maurus, Latrodectus mactans.
• Acarina e.g. Acarus siro, Argas spp., Ornithodoros spp., Der- manyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipice- phalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psororioptes spp. tes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..
• the active compounds according to the invention are notable for high insecticidal and acaricidal activity.
• insects which damage plants, for example against the larvae of the horseradish leaf beetle (Phedon cochleariae), against the larvae of the green leafhopper (Nephotettix cincticeps), against the peach aphid (Myzus persicae) and also against the fruit tree spider mite (Panonychus ulmi).
• the active compounds according to the invention can furthermore be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
• the active compounds according to the invention can e.g. can be used in the following plants:
• the compounds are suitable for total weed control, for example on industrial and rail tracks, and on paths and squares with and without tree cover.
• the compounds for weed control in permanent crops for example forest, ornamental wood, fruit, wine, Citrus, nut, banana, coffee, tea, gum, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture fields and for selective weed control in annual crops
• the active compounds according to the invention are very well suited for the selective control of monocotyledon weeds in dicotyledon crops in the pre- and post-process. They can be used, for example, in cotton or sugar beets with very good results
• Control of harmful grass can be used
• the active ingredients can be converted into the customary formulations, such as solutions, emulsions, plastic powder, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates and impregnated active ingredients
• formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, if appropriate using surface-active agents, that is
• Aromatic solvents such as xylene, toluene, or alkylnaphthane chlorinated aromatics and chlorinated aphatic hydrocarbons, such as chlorobenzenes, chloroethylene or, are essentially suitable as liquid solvents Methylene chloride, ahphatic 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 dimethylformamide and dimethyl sulfoxide, and water.
• Aromatic solvents such as xylene, toluene, or alkylnaphthane chlorinated aromatics and chlorinated aphatic hydrocarbons, such as chlorobenzenes, chloroethylene or
• Possible solid carriers are: e.g. Ammonium salts and natural rock powders, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders, such as highly disperse silicic acid, aluminum oxide and silicates, are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foaming agents are possible: e.g.
• non-ionic and anionic emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates;
• Possible dispersants are: e.g. Lignin liquor and methyl cellulose.
• Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids such as cephalins and lecithins and synthetic phospholipids can be used in the formulations.
• Other additives can 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 can be used.
• the formulations generally contain between 0.1 and 95% by weight of active compound, preferably between 0.5 and 90%.
• the active substance according to the invention can be present in its commercially available formulations and in the use forms prepared from these formulations in a mixture with other active substances, such as insecticides, attractants, sterilants, acaricides, nematocides, fungicides, growth-regulating substances or herbicides.
• the insecticides include, for example, phosphoric acid esters, carbamates, carboxylic acid esters, chlorinated hydrocarbons, phenylureas, substances produced by microorganisms and others
• Particularly favorable mixing partners are e.g. the following"
• Fenarimol, Fenbuconazole, Fen Inenarimol, Fenbuconazole, Fen Nameam, Fenitropan, Fenpiclonil, Fenpropidin, Fenpropimorph, Fentinacetat, Fentinhydroxyd, Ferbam, Ferimzone, Fluazinam, Fludioxonil, Fluoromide, Fluquinconazole, Flusilazole, Flusulfamide, Flutolanil, Flutriafilil, Flutriafilil
• Nickel dimethyldithiocarbamate Nitrothal-isopropyl, Nuarimol, O requirementsace, Oxadixyl, Oxamocarb, Oxycarboxin,
• Pe Pe
• azoate penconazole, pencycuron, phosdiphen, phthalide, pimaricin, piperalin, polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, propiconazole, propineb, pyrazophos, pyrifenox, pyrimethanil, pyroquilone,
• PCNB Quintozen
• Tebuconazole Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen, thiophanate-methyl, thiram, tolclophos-methyl, tolylfluanid, triadimefon, triadimenol, triazoxide, trichlamid, tricyclazole, tridemorph, triflorolizol, triflorolizol, triflorolizole,
• Bactericides bronopol, dichlorophene, nitrapyrin, nickel-dimethyldithiocarbamate, kasugamycin,
• Insecticides / acaricides / nematicides Abamectin, Acephate, Acetamiprid, Acrinathrin, Alanycarb, Aldicarb, Aldoxycarb,
• Fenamiphos Fenazaquin, Fenbutatin oxide, Fenitrothion, Fenothiocarb, Fenoxacrim, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyrithrin, Fenpyroximate, Fenvalerate, Fipronil, Fluazinam, Fluazuron, Flubrocythrinate, Flucycloxoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxuron, Fluutinoxanone, - fenprox, furathiocarb,
• Halofenozide HCH, Heptenophos, Hexaflumuron, Hexythiazox, Hydroprene, Imidacloprid, Isazofos, Isofenphos, Isoxathion, Ivermectin, Kernpolyederviruses, Lambda-cyhalothrin, Lufenuron,
• Mecarbam Metaldehyde, Methamidophos, Metharhilic anisopliae, Metharhilic flavoviride, Methidathion, Methiocarb, Methomyl, Methoxyfenozide, Metolcarb, Metoxadiazone, Mevinphos, Milbemectin, Monocrotophos, Naled, Nitenpyramo, Oxidomylonomidamyl, Oxitomyl, Oxitomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl, Oxidomyl
• Paecilomyces fuermosoroseus Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalone, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos A, Pirimiphos M, Profenofos, Promecarb, Propoxur, Prothiofos, Prothoat, Pymetclhrumid, Pyromclinophrine, Pymetrozhrin, Pyromethroz , Pyridathione, pyrimidifen, pyriproxyfen,
• Thuringiensine tralocythrin, tralomethrin, triarathenes, triazamates, triazophos, triazurone, trichlophenidines, trichlorfon, triflumuron, trimethacarb,
• Herbicides for example anilides, such as, for example, diflufenican and propanil, arylcarboxylic acids, such as, for example, dichloropicolinic acid, dicamba and picloram, aryloxyalkanoic acids, such as, for example, 2.4 D, 2.4
• Imidazohnones such as, for example, imazethapyr, imazamethabenz, imazapyr and imazaquin, nit ⁇ le, such as, for example, bromoxynil, dichlobenil and ioxynil, oxyacetamides, such as, for example, mefenacet, sulfonylureas, such as, for example, amidosulfuron, bensul matterson-methyl, chloron-chloron, chloro- Cinosul matterson, Metsul matterson-methyl, Nicosul factson, P ⁇ mi- sul closeston, Pyrazosul possiblyon-ethyl, Thifensul rowson-methyl, T ⁇ asulognion and T ⁇ benuron-methyl, Thiolcarbamate, such as Butylate, Cycloate, Diallate, EPTC, Esprocarb, Tohn, Proiulfocarbine, Proobenulfocarb such as Atrazin, Cyanaz
• the active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges.
• the active substance concentration of the use forms can be from 0.0000001 to 95% by weight of active substance, preferably between 0.0001 and 1% by weight
• the application takes place in a customary manner adapted to the application forms
• the active ingredient When used against hygiene and storage pests, the active ingredient is characterized by an excellent residual effect on wood and clay as well as a good alkali treatment on limed substrates
• the active substances according to the invention act not only against plant, hygiene and stored pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, rough mites, running mites, flies (stinging and licking), parasitic larvae, lice, hair - Hangings, featherlings and fleas
• animal parasites ectoparasites
• tick ticks leather ticks
• rough mites rough mites
• running mites running mites
• flies stinging and licking
• parasitic larvae lice, hair - Hangings, featherlings and fleas
• Anoplu ⁇ da for example Haematopinus spp, Lmognathus spp, Pediculus spp, Phtirus spp, Solenopotes spp
• Nematoce ⁇ na and Brachyce ⁇ na e.g. Aedes spp, Anopheles spp, Culex spp, Simuhum spp, Eusimuhum spp, Phle- botomus spp, Lutzomyia spp, Cu coides spp, Chrysops spp, Hybomitra spp, Atyotus spp, Tabanus spp, Haematopota spp, Philipomyia spp, Braula spp, Musca spp, Hydrotaea spp, Stomoxys spp, Haematobia spp, Morellia spp, Fann , Glossina spp, Calliphora spp, Luci a spp, Chrysomyia spp, Wohlfahrtia spp, Sarcophaga spp, Oestrus spp,
• Otodectes spp Sarcoptes spp, Notoedres spp, Knemidocoptes spp, Cytodites spp, Laminosioptes spp
• the active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are used for agricultural purposes, such as, for example, cattle, sheep, goats, Horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as dogs, cats, house birds, aquarium fish and so-called experimental animals such as hamsters, guinea pigs, rats and mice infect with the fight against these arthropods death cases and reduced performance (in meat, milk, wool, skin, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention makes it possible to keep animals more economically and simply
• the active compounds according to the invention are used in the Vetermar sector in a known manner by enteral administration in the form of, for example, tablets,
• Formula (I) as formulations for example powders, emulsions, flowable agents
• formulations for example powders, emulsions, flowable agents
• active compounds in an amount of 1 to 80% by weight, used directly or after 100 to 10,000 times dilution or used as a chemical bath
• insects may be mentioned by way of example and preferably, but without limitation Beetle like
• Hautflieger such as Sirexjuvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur
• Kalotermes flavicolhs Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucihegus, Mastotermes darwiruenisis, Zootermopsis nevadensis, Coptotermes formosanus
• the material to be protected against insect infestation is very particularly preferably wood and wood processing products
• Wood and wood processing products which can be protected by the agent according to the invention or mixtures containing it, are to be understood as examples of construction timber, wooden beams, railway sleepers, bridge parts, jetties, wooden vehicles, boxes, pallets, containers, telephone masts, wooden cladding, wooden windows and doors, plywood , Chipboard, carpentry or wood products that are used in general in house construction or joinery
• the active substances 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 ingredients with at least one solvent or diluent, emulsifier, dispersant and / or binder or fixative, water repellent, optionally siccatives and UV stabilizers and optionally dyes and pigments and further processing aids.
• the insecticidal compositions or concentrates used to protect wood and wood-based materials contain the active compound according to the invention in a concentration of 0.0001 to 95% by weight, in particular 0.001 to 60% by weight.
• the amount of the agents or concentrates used depends on the type and occurrence of the insects and on the medium. The optimal amount 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 compound, based on the material to be protected.
• organic-chemical solvent or solvent mixture and / or an oily or oily or low-volatility 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 agents.
• the organic chemical solvents used are preferably oily or oily solvents with an evaporation number above 35 and a flash point above 30 ° C., preferably above 45 ° C.
• Corresponding mineral oils or their aromatic fractions or mineral oil-containing solvent mixtures preferably white spirit, petroleum and / or alkylbenzene, are used as such low-volatility, water-insoluble, oily and oily solvents.
• Mineral oils with a boiling range of 170 to 220 ° C, white spirit with a boiling range of 170 to 220 ° C, spindle oil with a boiling range of 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 to 280 ° C, turpentine oil and the like are advantageous for use
• the organic slightly volatile oily or oil-like solvents with an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C can be partially replaced by slightly or medium-volatile organic chemical solvents, with the proviso that the solvent mixture also has an evaporation number 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide-fungicide mixture is soluble or emulsifiable in this solvent mixture.
• Solvents or solvent mixtures replaced by an aliphatic polar organic chemical solvent or solvent mixture.
• the known water-thinnable synthetic resins and / or synthetic resins soluble or dispersible or emulsifiable in the organic chemical solvents used and / or binding drying oils, in particular binders consisting of or containing an acrylate resin are used as organic chemical binders
• 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-coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or synthetic resin
• the synthetic resin used as a binder can be used in the form of an emulsion, dispersion or solution. Bitumen or bituminous substances of up to 10% by weight can also be used as binders. In addition, known dyes, pigments, water-repellants, odor correctors and inhibitors or anticorrosive agents and the like can also be used
• At least one alkyd resin or modified alkyd resin and / or a drying vegetable oil is preferably contained in the agent or in the concentrate as organic-chemical binder.
• binder mentioned can be replaced by a fixing agent (mixture) or a plasticizer (mixture). These additives are intended to prevent volatilization of the active ingredients and crystallization or failure. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).
• the plasticizers come from the chemical classes of phthalic acid esters such as dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid 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 ether or higher molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid ester are examples of oleates such as butyl oleate, glycerol ether or higher molecular weight glycol ethers, glycerol esters and p-toluenesulfonic acid ester.
• Fixing agents are chemically based on polyvinyl alkyl ethers such as polyvinyl methyl ether or ketones such as benzophenone and ethylene benzophenone Water is also particularly suitable as a solvent or diluent, if appropriate in a mixture with one or more of the above-mentioned organic chemical solvents or diluents, emulsifiers and dispersants.
• a particularly effective wood protection is achieved through industrial impregnation processes, e.g. Vacuum, double vacuum or pressure process.
• the ready-to-use compositions can optionally contain further insecticides and, if appropriate, one or more fungicides.
• insecticides and fungicides mentioned in WO 94/29 268 are preferably suitable as additional admixing partners.
• the compounds mentioned in this document are an integral part of the present application.
• Insecticides such as chlorpyriphos are particularly preferred mixing partners.
• Phoxim Silafluofin, Alphamethrin, Cyfluthrin, Cypermethrin, Deltamethrin, Permethrin, Imidacloprid, NI-25, Flufenoxuron, Hexaflumuron and Triflumuron as well as Fungicides such as Epoxyconazole, Hexaconazole, Cipermazazole, Propicon 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octyl-isothiazolin-3-one called.
• Fungicides such as Epoxyconazole, Hexaconazole, Cipermazazole, Propicon 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N-octyl-isothiazolin-3
• Example I-2-b-1 Analogously to Example I-2-b-1, if isopropyl chloroformate is used instead of pivaloyl chloride, the compound shown above is obtained in a yield of 46% of the theory, mp 140-141 ° C.
• Example II-B-1 Analogously to Example II-B-1, from 69 g of the compound according to Example XX-B-1, 11.7 g (15% of theory) of the compound shown above are obtained. Mp 118-120 ° C.
• Example II-C-1 Analogously to Example II-B-1, from 69 g of the compound according to Example XX-B-1, 11.7 g (15% of theory) of the compound shown above are obtained. Mp 118-120 ° C.
• Example II-C-1 Example II-C-1
• Example XX-C-1 70 g of the compound according to Example XX-A-1 are oxidized analogously to Example XXV-1. Yield 69.0 g (99% of theory), mp 76-78 ° C.
• Example XX-C-1 70 g of the compound according to Example XX-A-1 are oxidized analogously to Example XXV-1. Yield 69.0 g (99% of theory), mp 76-78 ° C.
• Example XXX-1 A solution of 70.5 g of the compound according to Example XXV-1 in 1600 ml of ethanol is added to 446.4 g of ammonium carbonate and 98.0 g of sodium cyanide in 1600 ml of water and the mixture is stirred for 10 hours at 60 ° C. Then the mixture is cooled to 5 ° C and sucks the precipitate from yield 156.7 g (74% of theory), mp> 250 ° C.
• Example XXX-1 A solution of 70.5 g of the compound according to Example XXV-1 in 1600 ml of ethanol is added to 446.4 g of ammonium carbonate and 98.0 g of sodium cyanide in 1600 ml of water and the mixture is stirred for 10 hours at 60 ° C. Then the mixture is cooled to 5 ° C and sucks the precipitate from yield 156.7 g (74% of theory), mp> 250 ° C.
• hydrocyanic acid 249.5 g are added dropwise to 1004.4 g of 4-hydroxycyclohexanone and 3.70 ml of triethylamine at room temperature in about 45 minutes and the mixture is stirred for about 1
• Cabbage leaves (Brassica oleracea), which are heavily infested with peach aphids (Myzus persicae), are treated by being dipped into the preparation of active compound of the desired concentration
• the death rate is determined in percent. 100% means that all aphids have been killed, 0% means that no aphids have been killed
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
• Rice seedlings (Oryza sativa) are treated by dipping into the active ingredient preparation of the desired concentration and populated with larvae of the green rice leafhopper (Nephotettix cincticeps) while the seedlings are still moist.
• the death rate is determined in%. 100% means that all cicadas have been killed; 0% means that no cicadas have been killed.
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier and the concentrate is diluted with water containing emulsifier to the desired concentrations.
• the effect is determined in%. 100% means that all spider mites have been killed; 0% means that no spider mites have been killed
• the compound according to preparation example I-2-b-2 had an activity of 100% after 7 days at an exemplary active ingredient concentration of 0.02%.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• active compound 1 part by weight of active compound is mixed with the stated amount of solvent and the stated amount of emulsifier, and the concentrate is diluted with water to the desired concentration.
• Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active compound of the desired concentration and populated with larvae of the horseradish leaf beetle (Phaedon cochleariae) while the leaves are still moist.
• the death rate is determined in%. 100% means that all beetle larvae have been killed; 0% means that no beetle larvae have been killed.
• the compounds according to the preparation examples I-2-b-2, I-2-b-3, I-2-C-2, I-2-C-6, Ila-1 and Ilb-1 contributed an exemplary drug concentration of 0.1%, a death rate of 100% after 7 days.
• Emulsifier 1 part by weight of alkylaryl polyglycol ether
• Cabbage leaves (Brassica oleracea) are treated by being dipped into the preparation of active ingredient of the desired concentration and populated with caterpillars of the owl butterfly (Spodoptera frugiperda) while the leaves are still moist.
• the effect is determined in%. 100% means that all spider mites have been killed, 0% means that none of the spider mites have been killed
• the compounds according to the preparation examples I-2-b-2, I-2-a-2, I-2-b-3, I-2-b-4, I-2-b-5 caused , I-2-C-2, I-2-C-3, I-2-C-5, I-2-b-9, I-2-C-6, I-2-b-10, I. -2-bl l and Ilb-1 with an exemplary active ingredient concentration of 0.01% each have an effect of 100% after 7 days
• the test is carried out in 5-fold determination. 1 ⁇ l of the solutions is injected into the abdomen, the animals are transferred into dishes and kept in an air-conditioned room. The effectiveness is checked after 7 days for inhibition of egg laying. A 100% effect means that no tick has laid eggs
• Test animals Lucilia cuprina larvae
• test tube containing approx. 1 cm 3 horse meat and 0.5 ml of the active ingredient preparation to be tested. The effectiveness of the active substance preparation is determined after 24 and 48 hours.
• the test tubes are transferred to beakers with a sand-covered bottom. After a further 2 days, the test tubes are removed and the dolls are counted.
• the effectiveness of the active ingredient preparation is assessed according to the number of joints hatched after 1.5 times the development time of an untreated control. 100% means that no flies hatched; 0% means that all flies hatched normally.

Landscapes

• Life Sciences & Earth Sciences (AREA)
• Organic Chemistry (AREA)
• Chemical & Material Sciences (AREA)
• Environmental Sciences (AREA)
• Agronomy & Crop Science (AREA)
• Engineering & Computer Science (AREA)
• Dentistry (AREA)
• General Health & Medical Sciences (AREA)
• Wood Science & Technology (AREA)
• Zoology (AREA)
• Plant Pathology (AREA)
• Pest Control & Pesticides (AREA)
• Health & Medical Sciences (AREA)
• Agricultural Chemicals And Associated Chemicals (AREA)
• Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
• Plural Heterocyclic Compounds (AREA)
• Furan Compounds (AREA)
• Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
• Indole Compounds (AREA)
• Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
• Pyrrole Compounds (AREA)

Priority Applications (7)

Applications Claiming Priority (2)

Publications (1)

Family

ID=7843694

Family Applications (1)

Country Status (14)

Cited By (74)

Families Citing this family (26)

Citations (7)

Family Cites Families (16)

• 1997
  • 1997-09-26 DE DE19742492A patent/DE19742492A1/de not_active Withdrawn
• 1998
  • 1998-09-12 ES ES98951386T patent/ES2320394T3/es not_active Expired - Lifetime
  • 1998-09-12 TR TR2000/00749T patent/TR200000749T2/xx unknown
  • 1998-09-12 JP JP2000513834A patent/JP4422891B2/ja not_active Expired - Fee Related
  • 1998-09-12 BR BRPI9812535-4A patent/BR9812535B1/pt not_active IP Right Cessation
  • 1998-09-12 WO PCT/EP1998/005809 patent/WO1999016748A1/de not_active Ceased
  • 1998-09-12 KR KR1020007002590A patent/KR100547508B1/ko not_active Expired - Fee Related
  • 1998-09-12 CN CN988095572A patent/CN1217931C/zh not_active Expired - Fee Related
  • 1998-09-12 EP EP98951386A patent/EP1017674B1/de not_active Expired - Lifetime
  • 1998-09-12 AU AU97431/98A patent/AU9743198A/en not_active Abandoned
  • 1998-09-12 AT AT98951386T patent/ATE423097T1/de active
  • 1998-09-12 US US09/509,288 patent/US6589976B1/en not_active Expired - Lifetime
  • 1998-09-12 DE DE59814345T patent/DE59814345D1/de not_active Expired - Lifetime
  • 1998-09-22 TW TW087115725A patent/TW568904B/zh not_active IP Right Cessation
  • 1998-09-25 ZA ZA988784A patent/ZA988784B/xx unknown

Patent Citations (7)

Also Published As

Similar Documents

Legal Events