EP1504005A2

EP1504005A2 - Substituted pyrazolo-pyrimidine-4-ones

Info

Publication number: EP1504005A2
Application number: EP03720510A
Authority: EP
Inventors: Karl-Heinz Linker; Roland Andree; Dorothee Hoischen; Hans-Georg Schwarz; Mark Wilhelm Drewes; Peter Dahmen; Dieter Feucht; Rolf Pontzen; Peter Lösel
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2002-05-02
Filing date: 2003-04-22
Publication date: 2005-02-09
Also published as: WO2003093269A2; WO2003093269A3; CA2484997A1; AU2003224111A1; US20050209251A1; DE10219435A1; BR0309873A; AR039468A1; JP2005531549A

Abstract

The invention relates to compounds of formula (I), in which Q, R1, and R2 have the meaning indicated in the description, methods for the production thereof, and the use thereof as herbicides and/or nematicides.

Description

Substituted pyrazolo-pyrimidin-4-ones

The invention relates to new substituted pyrazolo-pyrimidin-4-ones, to their preparation and their use as plant treatment agents, in particular as herbicides and as nematicides.

Certain substituted pyrazolo-pyrimidin-4-ones, e.g. the compound 1,5-di-hydro-6-methyl-l- (2,4,6-trichlorophenyl) -4H-pyrazolo- [3,4-d] pyrimidin-4-one are already known ( see WO 94/13677, US 6,218,397). However, these compounds have gained no importance as plant treatment agents.

There have now been new substituted pyrazolo-pyrimidin-4-ones of the general formula (I)

in which

for in each case by at least two identical or different substituents from the series nitro, cyano, halogen and in each case optionally substituted by halogen Cr-alkyl, -C _ö alkoxy, Cj-C _ö alkylthio, CrC ₆ - alkylsulfinyl or Cι-C ₆ - Alkylsulfonyl-substituted aryl or heteroaryl each having up to 10 carbon atoms and optionally up to 5 nitrogen atoms and / or optionally an oxygen or sulfur atom, R ¹ for hydrogen, for each -Ce-alkyl or -Cβ-alkoxycarbonyl optionally substituted by cyano, halogen or Cr C ₄ -alkoxy, for each optionally substituted by halogen C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -alkynyl , for C ₃ -C ₆ cycloalkyl or C ₃ -C ₆ cycloalkyl-C ₁ -C ₄ alkyl optionally substituted by cyano, halogen or - alkyl, for each optionally substituted by nitro, cyano, halogen, C ₁ - C ₄ alkyl, C ₁ -C ₄ haloalkyl, dC ₄ alkoxy or C ₁ -C ₄ haloalkoxy substituted aryl or arylalkyl, each with up to 10 carbon atoms in the aryl group and optionally up to 4 carbon atoms in the alkyl part, or for counter - also by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl,

C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy substituted heterocyclyl having up to 10 carbon atoms, up to 5 nitrogen atoms and / or an oxygen or sulfur atom, and

R ² represents hydrogen, represents optionally cyano-, halogen, Cj-C ₄ -alkoxy or C ₁ -C ₄ -alkoxy-carbonyl-substituted alkyl, or -C _ö each case optionally halogen-substituted C ₂ -C ₆ alkenyl or C -C ₆ alkyl,

found,

where the previously known compound 1,5-dihydro-6-methyl-1- (2,4,6-trichlorophenyl) -4H-pyrazolo- [3,4-d] pyrirnidin-4-one (cf. WO 94 / 13677) is excluded by disclaimer.

The pyrazolopyrimidines of the general formula (Ia) which are isomerically substituted to the substituted pyrazolo-pyrimidin-4-ones of the general formula (I)

in which

Q, R ¹ and R ^{2 have} the meanings given above,

are also the subject of the present invention.

In the definitions, the hydrocarbon chains, such as alkyl or alkenyl - also in combination with heteroatoms, such as in alkoxy - are each straight-chain or branched.

Optionally substituted radicals can be mono- or polysubstituted; in the case of multiple substitution, the substituents can be the same or different.

Preferred substituents or ranges of the radicals present in the formulas listed above and below are defined as follows:

preferably represents in each case at least two identical or different substituents from the series nitro, cyano, fluorine, chlorine, bromine, each optionally substituted by 1 to 3 fluorine and / or chlorine atoms Ci-C ₄ - alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, - -alkylsulfinyl or - - alkylsulfonyl-substituted aryl having 6 or 10 carbon atoms or heteroaryl having up to 5 carbon atoms, up to 3 nitrogen atoms and / or optionally an oxygen or sulfur atom. R ¹ preferably represents hydrogen, in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, d-Cs-alkyl or -Cs-alkoxycarbonyl, in each case optionally by fluorine, chlorine and / or bromine substituted C ₂ -C ₅ alkenyl or C -C ₅ alkynyl, each substituted by cyano, fluorine, chlorine, methyl or ethyl

C ₃ -C ₆ -cycloalkyl or CrC _δ -cycloalkyl-CrCs-alkyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,

Fluoroethoxy, chloroethoxy, difluoroethoxy, Dϊchlorethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl group and optionally up to 3 carbon atoms in the alkyl part, or for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl , Ethyl, n- or i-propyl, n-, i-, s- or t-

Butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, dichloroethoxy, dichloro Chlorofluoroethoxy, chlorofluoroethoxy or trifluoroethoxy substituted heterocyclyl with up to 10

Carbon atoms, up to 4 nitrogen atoms and / or an oxygen or sulfur atom.

R preferably represents hydrogen, optionally by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,

Ethoxycarbonyl, n- or i-propoxy-carbonyl substituted CrCs-alkyl or for each optionally substituted by fluorine, chlorine and / or bromine

C ₂ -C ₅ alkenyl or C ₂ -C ₅ alkynyl.

Q particularly preferably represents in each case by at least two identical or different substituents from the series nitro, cyano, fluorine, chlorine, bromine, Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, bromoethyl, difluoroethyl, dichloroethyl, Chlorfluorethyl, trifluoroethyl, tri- chloroethyl, Chlordifluorethyl, Fluordichlorethyl, tetrafluoroethyl, pentafluoro ethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, Fluordichlormethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, Chlorfluorethoxy , Trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, methylsulfmyl,

Ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted phenyl, pyridinyl, pyrimidinyl, pyrazolyl, furyl or thienyl.

is particularly preferably hydrogen, each optionally by

Cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl, ethoxycarbonyl, n- or i- Propoxycarbonyl, n-, i-, s- or t-butoxycarbonyl, for ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or optionally substituted in each case by fluorine, chlorine and / or bromine

Pentinyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy substituted phenyl, benzyl or phenylethyl, or for each optionally substituted by nitro, bromo, methyl, fluorine, chlorine Ethyl, n- or i- Propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy , Trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy substituted

Pyridinyl, pyrimidinyl, furyl, tetrahydrofuryl or thienyl.

R ² particularly preferably represents hydrogen, in each case methyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,

Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or for ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, each optionally substituted by fluorine, chlorine and or bromine.

Q very particularly preferably represents in each case by at least two identical or different substituents from the series nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, difluoromethoxy , Trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy,

Trifluoroethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, methylsulfmyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl-substituted phenyl or pyridylphenyl-substituted phenyl.

R ¹ very particularly preferably represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl , Chlorofluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, methoxymethyl, ethoxymethyl, methoxyethyl,

Ethoxyethyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for ethenyl, propenyl, butenyl, pentenyl, fluoropropenyl, chloropropenyl, difluoropropenyl, dichloropropenyl, chlorofluoropropenyl, fluorobutenyl, chlorobutenyl, difluorobutenyl, dichlorobutenyl, chlorofluorobutenyl, ethynyl, propynyl, butmyl or pentynyl, for each optionally by fluorine, chlorine substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl , Dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, dichloroethoxy, dichloroethoxy, dichloroethoxy or trifluoroethoxy substituted phenyl, benzyl or phenylethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-

Propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy substituted pyridinyl, pyrimidinyl, furyl, tetrahydrofuryl or thienyl.

R ² very particularly preferably represents hydrogen, in each case methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, or for each propenyl, butenyl, pentenyl, propynyl, butmyl or pentynyl optionally substituted by fluorine and / or chlorine.

According to the invention, preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as preferred. According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

According to the invention, very particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

Those compounds of the formula (I) in which Q is substituted by two radicals are also preferred. A very particularly preferred group are also those

Compounds of formula (I) in which

Q for in each case by at least two identical or different substituents from the series nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl,

Fluorodichloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, fluoroethoxy, chloroethoxy, difluorethoxy, dichloroethoxy, chlorofluorethoxy, trifluorethoxy, methylthio, ethylthio, difluoromethylthio, methylifio, chlorofluoromethylthio, methylifio, methylifio

Methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted phenyl or pyridinyl.

A very particularly preferred group are those compounds of the formula

(I) in which

Q represents phenyl which contains at least two identical or different substituents in the 2- and 4-position and optionally a further substituent in the 6-position, the substituents from the series nitro,

Cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, dichloromethyl, Trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, Fluordichlormethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, Chlorfluorethoxy, trifluoroethoxy, methylthio, ethylthio, difluoro- methylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, Methylsulfmyl, ethylsulfinyl, Trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl and trifluoromethylsulfonyl are selected,

for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, chlorofluoroethyl , Trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for ethenyl, propenyl, butenyl, pentenyl, fluoropropenyl, chloropropenyl, difluoropropenyl, chlorofluoropropenyl, dichloropropenyl , Chlorobutenyl, difluorobutenyl, dichlorobutenyl, chlorofluorobutenyl, ethynyl, propynyl, butynyl or pentynyl, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by fluorine, chlorine or methyl, each in each case optionally by nitro, cyano, fluorine, chlorine, bromine , Methyl, ethyl, n- or i-

Propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy , Trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy substituted

Phenyl, benzyl or phenylethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl , Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoro- ethoxy substituted pyridinyl, pyrimidinyl, furyl, tetrahydrofuryl or thienyl, and

R ² for hydrogen, for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or for each optionally by fluorine and / or chlorine-substituted propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl.

Particularly noteworthy here are those compounds in which Q is 2,4-dichlorophenyl, 2,4,6-trichlorophenyl, 2-chloro-4-trifluoromethylphenyl or 2,6-dichloro-4-trifluoromethyl phenyl stands.

Another very particularly preferred group are those compounds of the formula (I) in which

Q represents pyridin-2-yl, which contains at least two identical or different substituents in the 3- and 5-position and optionally a further substituent in the 6-position, the substituents from the series nitro, cyano, fluorine, chlorine, bromine, Methyl, ethyl, difluoromethyl, dichloromethyl,

Trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, Fluordichlormethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, Chlorfluorethoxy, trifluoroethoxy, methylthio, ethylthio, difluoro- methylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, Methylsulfmyl, ethylsulfinyl, Trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl are selected,

R ¹ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloro- ethyl, chlorofluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for ethenyl, propenyl, butenyl, pentenyl, fluoropropenyl, chloropropenyl, difluoropropenyl, difluoropropenyl Chlorofluoropropenyl, fluorobutenyl, chlorobutenyl, difluorobutenyl,

Dichlorobutenyl, chlorofluorobutenyl, ethynyl, propynyl, butynyl or pentynyl, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted with fluorine, chlorine or methyl, for each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n - or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl,

Chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluorethoxy, chlorodifluorethoxy, chlorodifluorethoxy, chlorodifluoromethoxy, chlorodifluoromethoxy, chlorodifluoromethoxy, chlorodifluoromethoxy, chlorodifluoromethyl Benzyl or phenylethyl, or for each optionally by nitro,

Cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i -Propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy substituted pyridinyl, pyrimidinyl, furyl, tetrahydrofuryl and thienyl

Particularly noteworthy are those compounds in which Q is 3,5-dichloropyridm-2-yl or 3-chloro-5-trifluoromethyl-pyridin-2-yl. Another very particularly preferred group are those compounds of the formula (I) in which

Q represents pyrazol-3-yl, which is at least two identical or different

Contains substituents in the 1- and 5-position and optionally a further substituent in the 4-position, the substituents from the series nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl , Methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy,

Fluordichlormethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, Chlorfluorethoxy, trifluoroethoxy, methylthio, ethylthio, difluoro- methylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, Methylsulfmyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl are selected,

R ¹ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, chlorofluoroethyl , Trifluoroethyl, tetrafluoroethyl, pentafluoroethyl,

Methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for ethenyl, propenyl, butenyl, pentenyl, fluopropenyl, chloropropenyl, difluoropropenyl, dichloropropenyl, chlorofluorophenyl, dichlorobutyl, fluorobutyl, fluorobutyl, fluorobutyl, fluorobutyl, fluorobutyl, fluorobutyl, Chlorofluorobutenyl, ethynyl, propynyl, butynyl or pentynyl, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally substituted by fluorine, chlorine or methyl, for each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i - Propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-

Propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodi- fluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy substituted phenyl, benzyl or phenylethyl, or for each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n- , i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl,

Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, Chlorfluorethoxy, Chlordifluorethoxy trifluoroethoxy or substituted pyridinyl, pyrimidinyl, furyl, tetrahydrofuryl or thienyl, and

R ² for hydrogen, for each optionally by cyano, fluorine, chlorine,

Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl-substituted methyl, ethyl, n- or i-propyl, or for propenyl, butenyl which is optionally substituted by fluorine and / or chlorine,

Pentenyl, propynyl, butynyl or pentynyl.

Particular mention should be made of those compounds in which Q represents 5-difluoromethoxy-1-methyl-pyrazol-3-yl or 5-difluoromethoxy-1, 4-dimethyl-pyrazol-3-yl.

The general or preferred radical definitions listed above apply both to the end products of the formula (I) and correspondingly to the starting or intermediate products required in each case for the preparation. These radical definitions can be combined with one another, that is to say also between the specified preferred ranges.

The new substituted pyrazolo-pyrimidin-4-ones of the general formula (I) are notable for strong and selective herbicidal and nematicidal activity. The new substituted pyrazolo-pyrimidin-4-ones of the general formula (I) are obtained if

(a) 5-amino-l-aryl-pyrazole-4-carboxamides of the general formula (II)

in which

Q has the meaning given above,

with carboxylic acid orthoesters of the general formula (III)

R ^] - (OR ') 3 (III)

in which

R ^{1 has} the meaning given above and

R 'represents alkyl,

if appropriate in the presence of one or more reaction auxiliaries and, if appropriate, in the presence of one or more diluents, or if

(b) 5-amino-1-aryl-pyrazole-4-carbonitriles of the general formula (IV)

in which

Q has the meaning given above,

with carboxylic anhydrides of the general formula (V)

in which

R has the meaning given above,

if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents,

or if (c) 5-amino-l-aryl-pyrazole-4-carboxamides of the general formula (II)

in which

Q has the meaning given above, with carboxylic anhydrides of the general formula (V)

° γ ^Rl

° γ ° (V)

R ¹ in which

R ^{1 has} the meaning given above,

or if you

(d) 5-Acylamino-l-aryl-pyrazole-4-carboxamides of the general formula

(VI)

in which

Q and R ^{1 have} the meanings given above,

if appropriate in the presence of one or more condensation auxiliaries and, if appropriate, in the presence of one or more diluents, or if (e) substituted pyrazolo-pyrimidin-4-ones of the general formula (Ib)

in which

Q and R ^{1 have} the meaning given above,

with alkylating, alkenyling or alkynylating agents of the general formula (VII)

XR ² (VII)

or the general formula (VIII)

R ² -O-SO ₂ -OR ² (VIII) wherein each

R ^{2 has} the meaning given above and

X represents halogen,

if appropriate in the presence of one or more reaction auxiliaries and, if appropriate, in the presence of one or more diluents. If, for example, 5-amino-1- (3,5-dichloropyridin-2-yl) pyrazole-4-carboxamide and orthoformic acid trimethyl ester are used as starting materials, the course of the reaction in process (a) according to the invention can be outlined by the following formula become:

If, for example, 5-amino-1- (3-chloro-5-trifluoromethyl-pyridin-2-yl) pyrazole-4-carbonitrile and acetic anhydride are used as starting materials, the course of the reaction in process (b) according to the invention can be outlined by the following formula become:

If, for example, 5-amino-1- (2,4-dichlorophenyl) pyrazole-4-carboxamide and propionic anhydride are used as starting materials, the reaction can proceed in method (c) according to the invention are outlined by the following formula:

If, for example, 1- (2-chloro-4-trifluoromethyl-phenyl) -5-trifluoroacetylamino-pyrazole-4-carboxamide is used as the starting material, the course of the reaction in process (d) according to the invention can be outlined using the following formula:

If, for example, 1- (2,6-dichloro-4-trifluoromethyl-phenyl) -6-methyl-1,5-dihydro-pyrazolo [3,4-d] pyrimidin-4-one and methyl bromide are used as starting materials, the The course of the reaction in process (e) according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the 5-amino-l-aryl-pyrazole-4-carboxamides to be used as starting materials in processes (a) and (c) for the preparation of compounds of the formula (I). In formula (II), Q preferably has the meaning which has already been given as preferred, particularly preferred or as very particularly preferred for Q in connection with the description of the compounds of the formula (I) according to the invention.

With the exception of the compound 5-amino-1- (2,4,6-trichlorophenyl) pyrazole-4-carboxamide (cf. WO 94/13677), the starting materials of the general formula (II) are not yet from the literature known; With the exception of the compound 5-amino-1- (2,4,6-trichlorophenyl) pyrazole-4-carboxamide, they are also the subject of the present application as new substances.

The 5-amino-l-aryl-pyrazole-4-carboxamides of the general formula (II) are obtained if 5-amino-l-aryl-pyrazole-4-carbonitriles of the general formula (IV)

in which Q has the meaning given above,

hydrolyzed in the usual way, for example by reaction with sulfuric acid, at temperatures between 0 ° C. and 100 ° C. (cf. the preparation examples).

Formula (III) provides a general definition of the carboxylic acid orthoesters to be used as starting materials in process (a) according to the invention for the preparation of compounds of formula (I). In the formula (III), R ¹ preferably has the meaning which has already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or as very particularly preferred for R; R 'preferably represents alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.

The starting materials of the general formula (III) are known organic synthetic chemicals.

Formula (IV) provides a general definition of the 5-amino-l-aryl-pyrazole-4-carbonitriles to be used as starting materials in process (b) according to the invention for the preparation of compounds of the formula (I). In formula (IV), Q preferably has the meaning which has already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or as very particularly preferred for Q.

The starting materials of the general formula (IV) are known and / or can be prepared by processes known per se (cf. DE 34 08 727, DE 34 20 985, DE 35 20 327, DE 35 20 331, DE 35 40 839, DE 36 25 686, DE 195 30 606, DE 196 23 892, DE 196 31 865, EP 542 388, GB 21 23 420, US 5,167,691, US 5,198,014, US 5,250,504, WO 83/00331, WO 94/08999). Formula (V) provides a general definition of the carboxylic anhydrides which are further to be used as starting materials in processes (b) and (c) according to the invention for the preparation of compounds of the formula (I). In formula (V), R ¹ preferably has the meaning which has already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or as very particularly preferred for R ¹ .

The starting materials of the general formula (V) are known organic synthetic chemicals.

Formula (VI) provides a general definition of the 5-acylamino-1-aryl-pyrazole-4-carboxamides to be used as starting materials in process (d) according to the invention for the preparation of compounds of the formula (I). In formula (VI), Q and R ¹ preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the invention

Formula (I) has been given as preferred, particularly preferred or as very particularly preferred for Q and R ¹ .

The starting materials of the general formula (VI) are, with the exception of the compound 1- (2,6-dichloro-4-trifluoromethylthio-phenyl) -5-propionylamino-pyrazole-4-carboxamide

(cf. DE 3420 985) not yet known from the literature; with the exception of compound 1 - (2,6-dichloro-4-trifluoromethylthio-ρhenyl) -5-propionylamino-pyrazole-4-carboxamide as new substances, they are also the subject of the present application.

The new 5-acylamino-l-aryl-pyrazole-4-carboxamides of the formula (VI) are obtained if 5-Ammo-l-aryl-pyrazole-4-carboxamides of the general formula (II) in which

has the meaning given above,

with acylating agents of the general formula (IX)

X'-R ¹ (IX) in which

R ^{1 has} the meaning given above and

X ^{1 represents} halogen, in particular fluorine, chlorine or bromine,

optionally in the presence of a reaction auxiliary, e.g. Sodium hydride, potassium carbonate or pyridine, and optionally in the presence of a diluent, e.g. Acetonitrile, at temperatures between 0 ° C and 100 ° C (see. The preparation examples).

The compounds of formula (IX) used in the process are known synthetic chemicals.

Formula (Ib) provides a general definition of the substituted pyrazolo-pyrimidin-4-one to be used as starting materials in process (e) according to the invention for the preparation of compounds of the formula (I). In formula (Ib), Q and R ¹ preferably have those meanings which have already been mentioned above in connection with the description of the compounds of the formula (I) according to the invention. moves, particularly preferred or have been specified as very particularly preferred for Q and R ¹ .

The starting materials of the general formula (Ib) are the subject of the present application as new substances; they can according to the inventive method (a) to

(d) are made.

The formulas (VII) and (VIII) generally define the alkylating, alkenyling or alkynylating agents which are further to be used as starting materials in process (e) according to the invention for the preparation of compounds of the formula (I). In the formulas (VII) and (VIII), R ² preferably has the meaning which has already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or as very particularly preferred for R; X in formula (VII) preferably represents fluorine, chlorine, bromine or iodine, in particular chlorine or

Bromine.

The starting materials of formulas (VII) and (VIII) are known organic synthetic chemicals.

Process (d) according to the invention is carried out using a condensation aid. Basic compounds are particularly suitable as condensation aids. These include in particular ammonia or amines, such as methylamine, ethylamine, n- or i-propylamine, n-, i-, s- or t-butylamine, dimethylamine, diethylamine, dipropylamine or dibutylamine, trimethylamine, triethylamine, tripropylamine or tributylamine , and also alkali metal or alkaline earth metal hydroxides, such as sodium, potassium, magnesium or calcium hydroxide, or alcoholates, such as sodium or potassium methylate, ethylate, n- or i-propylate, n-, i-, s - or t-butylate. Processes (a), (b), (c) and (e) according to the invention for the preparation of the compounds of the general formula (I) are preferably carried out using one or more reaction auxiliaries. Reaction aids for processes (a), (b), (c) and (e) according to the invention are generally the customary inorganic or organic bases or acid acceptors.

These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example, sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride,

Lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, i or t butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-

Dimethyl aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl, 3-methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino-pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2.2.2] octane (DABCO), l, 5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1,8-diazabicyclo [5.4.0] undec-7-ene (DBU).

Processes (a) to (e) according to the invention for the preparation of the compounds of the general formula (I) are preferably carried out using one or more diluents. Inert organic solvents are particularly suitable as diluents for carrying out the processes according to the invention

Consideration. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether;

Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, Propionitrile or butyronitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate; Sulfoxides such as dimethyl sulfoxide; Alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether; Ethylene glycol monoethyl ether, diefhylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be varied within a substantial range when carrying out the processes according to the invention. In general, temperatures between -30 ° C and + 150 ° C, preferably between 0 ° C and 120 ° C.

The processes according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

To carry out the processes according to the invention, the starting materials are generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary and the reaction mixture is generally stirred at the required temperature for several hours. The work-up is carried out using customary methods (cf. the manufacturing examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are understood to mean all plants that grow in places grow 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 for the following plants:

Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Gupopsisia, Euphorbia , Galium, Hibiscus, Ipomoea, Kochia, Lamiurn,

Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenus Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Dicotyledon cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea, Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus,

Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaaemum, Lumochloemum, Lolochochumem, Lolochochumem, Lolochochumum, Lolochochumum, Lolochochumem, Lolochochumum, Lolochochumum, Lolochochumum, Lolochochumum, Lolochochumum, Lolochochumum, Lolochochumum Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Sciφus, Setaria, Sorghum.

Monocot cultures of the genera: AUium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea. However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to other plants.

Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, e.g. 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, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective purposes Weed control can be used in annual crops.

The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.

The active compounds according to the invention can be used in certain concentrations or

Application rates can also be used to control animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or products for the synthesis of further active ingredients.

According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and undesirable wild plants or cultivated plants (including naturally occurring cultivated plants). Cultivated plants can be plants 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 plant varieties that can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds and

Roots, tubers and rhizomes are listed. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space according to the customary treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.

The active ingredients can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.

These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and or dispersants and / or foam-producing agents

Means.

If water is used as an extender, e.g. also organic

Solvents are used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example 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.

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 silica, 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 as well as granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-generating 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 sulfite 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, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used. The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance (“safeners”) for weed control, finished formulations or tank mixes being possible. Mixtures are therefore also possible possible with weed control agents which contain one or more known herbicides and a safener.

Known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asula, atrazine, azafenidin, azimsulfuron, beflubutamide, benazubutamide, ethyl), benfuresate, bensulfuron (methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop

(-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butafenacil (-allyl), Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyidazon, Chlorambenben , Chlorimuron (-ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cinidone (-ethyl), cinmethylin, cinosulfüron, clefoxydim, clethodim, clodinafop

(-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl), Clor-ansulam (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2 , 4-DB, Desmedipham, Diallate, Dicamba, Dichloφrop (-P), Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethamamydyn, Dimefyamide , Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralm, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl), Fentrazamide, Flentrazamide, Flentrazamide -isopropyl-L, -methyl), flazasulfüron, florasulam, fluazifop (-P-butyl), fluazolates, flucarbazone (-sodium), flufenacet,

Flufenpyr, flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumet- sulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, fluprop-acil, fluorophyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl), fluφrimidol, fluretamone, fluretamone -methyl), fluthimides, fomesafen, foramsulfuron, glufosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl, -P-methyl), hexazinones,

Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imaza- quin, Imazethapyr, Imazosulfuron, Iodosulfuron (-methyl, -sodium), Ioxynil, Iso-propalin, Isoproturon, Isouron, Isoxaben, Isoxaflotirpole, Isoxaflopyrutolole , Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Mesotione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-) Metolachlor, Metosulam, Metoxuron, Metribuzin, Metsulfuron (-methylolin, -methylolin, -methylolin, -methylolin, -methyl) -methyl- , Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Pelargonic Acid, Pendimethalin, Pendralin, Penoxysmedam, Pipoxoxamine, Pentoxazone, Pentoxazoline , Preilachlor, Primisulfüron (-methyl), Profluazol, Profoxydim, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-et hyl), pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine-quizalofop ethyl, -P-tefuryl), rimsulfüron, sethoxydim, Simazine, Simetryn, Sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutriafl, thiazidiaziazidium, thiazidine, thenyl chloride, Thifensulfüron (-methyl), Thiobencarb, Tio-carbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridipiphane, Trifluralin, Trifloxysulfuron, Triflusulfuron (-methyl), Tritosulfuron.

Known safeners are also suitable for the mixtures, for example AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-24, dichlormid, Dymron, Fenclorim, Fenchlorazol (-ethyl) , Flurazole, fluxofenim, Furilazole, Isoxadifen (-ethyl), MCPA, Mecoprop (-P), Mefenpyr (-diethyl), MG-191, Oxabetrinil, PPG-1292, R-29148.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the usual way, e.g. by pouring, spraying, spraying, sprinkling.

The active compounds according to the invention can be applied both before and after emergence of the plants. They can also be worked into the soil before sowing.

The amount of active ingredient used can vary over a wide range. It essentially depends 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.

As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, plant species and plant cultivars which occur wildly or are obtained by conventional biological breeding methods, such as crossing or protoplast fusion, and parts thereof are treated. In a further preferred embodiment, transgenic plants and plant cultivars which have been obtained by genetic engineering methods, optionally in combination with conventional methods (genetically modified organisms) and their parts are treated. The term "parts" or "parts of

Plants "or" parts of plants "was explained above. Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with certain properties (“traits”) which are produced by conventional breeding, by mutagenesis, or also by recombinant DNA

Techniques have been obtained. These can be varieties, bio and genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also give rise to superadditive ("synergistic") effects.

For example, reduced application rates and / or widening of the spectrum of action and / or an increase in the action of the substances and agents which can be used according to the invention - also in combination with other agrochemical active compounds, better growth of the crop plants, increased tolerance of the crop plants to high or low temperatures, increased tolerance of

Cultivated plants against drought or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storability and / or workability of the harvested products, which are beyond those actually to be expected Effects go beyond.

The preferred transgenic (genetically engineered) plants or plant cultivars to be treated according to the invention include all plants which have received genetic material through the genetic engineering modification, which gives these plants particularly advantageous, valuable properties (“traits”).

Examples of such properties are better plant growth, increased tolerance to high or low temperatures, increased tolerance to drought or to water or soil salt content, increased flowering performance, easier harvesting, accelerated ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products , higher shelf life and / or

Machinability of crop products. Further and particularly highlighted examples for such properties are an increased defense of the plants against animal and microbial pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses, and an increased tolerance of the plants against certain herbicidal active ingredients. The important cultivated plants such as cereals (wheat, rice), corn, soybeans, potatoes, cotton,

Rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes) are mentioned, whereby maize, soybeans, potatoes, cotton and rapeseed are particularly emphasized. The traits that are particularly emphasized are the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryΙA (a), CryIA (b), CrylA (c), CryllA, CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants (hereinafter referred to as "Bt plants"). The properties ("traits") also particularly emphasize the increased defense of plants against fungi, bacteria and viruses through systemic acquired resistance (SAR),

Systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. The properties (“traits”) which are particularly emphasized are the increased tolerance of the plants to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example “PAT” gene). The one you want

Genes conferring traits can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are maize varieties, cotton varieties, soy varieties and potato varieties which are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples of herbicide-tolerant plants are corn varieties, cotton varieties and soy varieties that are sold under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinothricin, e.g. rapeseed), IMI® (tolerance against imidazolinones) and STS® (tolerance to sulfonylureas such as corn). As a herbicide-resistant (conventional on Plants cultivated with herbicide tolerance may also be mentioned the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").

The plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active compound mixtures according to the invention, in addition to the good control of the weed plants, the above-mentioned synergistic effects with the transgenic

Plants or plant varieties occur. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.

Active substances according to the invention are also suitable for controlling animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored goods and materials and in the hygiene sector. They can preferably be used as pesticides. They are effective against normally sensitive and resistant species as well as against all or individual stages of development.

When used as insecticides, acaricides or nematicides, the active compounds according to the invention can also be used in their commercially available formulations and in the use forms prepared from these formulations in a mixture with

There are synergists. Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active.

The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The drug concentration of the Application forms can be from 0.0000001 to 95% by weight of active compound, preferably between 0.0001 and 1% by weight.

The application takes place in a customary manner adapted to the application forms.

The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice. By combating these arthropods, deaths and reduced performance (in the case of meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.

The active compounds according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by injections

(intramuscular, subcutaneous, intravenous, intraperitonal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the help of shaped articles containing active ingredients, such as collars, ear tags, tail tags, limb tapes, holsters, marking devices, etc.

When used for cattle, poultry, pets etc., you can use the active ingredients in

Formula (I) as formulations (for example powders, emulsions, flowable agents), which contain the active compounds in an amount of 1 to 80% by weight, directly or after 100 to 10,000-fold dilution or use it as a chemical bath.

The active substances are also suitable for combating animal pests, in particular insects, arachnids and mites, which live in closed spaces such as, for example, apartments, factories, offices, vehicle cabins and the like. occurrence. To control these pests, they can be used alone or in combination with other active ingredients and auxiliaries in household insecticide products. They are effective against sensitive and resistant species and against all stages of development.

They are used in aerosols, non-pressurized sprays, e.g. Pump and atomizer sprays, automatic foggers, foggers, foams, gels, vaporizer products with vaporizer plates made of cellulose or plastic, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, energy-free or passive evaporation systems, moth papers, moth bags and moth gels, in granules or dust or bait stations.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

Preparation Examples

example 1

(Expire (a))

A mixture of 0.70 g (2.29 mmol) of 5-amino-1- (3-chloro-5-trifluoromethyl-pyridin-2-yl) pyrazole-4-carboxamide, 0.27 g (2.52 mmol ) Trymethyl orthoformate, 0.10 g of p-toluenesulfonic acid and 80 ml of toluene are stirred under reflux for 12 hours. Then this mixture is mixed with a further 0.14 g of trimethyl orthoformate and stirred under reflux for a further 12 hours. After cooling, the mixture is filtered and the filtrate is concentrated under reduced pressure. The residue is stirred with isopropanol and the crystalline product isolated by suction.

0.32 g (44% of theory) of l- (3-chloro-5-trifluoromethyl-ρyridin-2-yl) -l, 5-dihydro-pyrazolo [3,4-d] pyrimidin-4-one of Melting point 331 ° C. LogP (pH 2): 1.54

Example 2

(Method (s))

A mixture of 0.21 g (0.665 mmol) of 1- (3-chloro-5-trifluoromethyl-pyridm-2-yl) - 1,5-dihydro-pyrazolo [3,4-d] pyrimidin-4-one, 0 , 11 g (0.80 mmol) potassium carbonate,

0.10 g (0.73 mmol) of methyl iodide and 40 ml of acetonitrile is stored at 20 ° C for 12 hours Stirred at 25 ° C and then concentrated under reduced pressure. The residue is then stirred with water, with conc. Acidified hydrochloric acid and the crystalline product isolated by suction.

0.12 g (55% of theory) of 1- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -5-methyl-1,5-dihydro-pyrazolo [3,4-d] pyrimidine is obtained. 4-one with a melting point of 253 ° C. LogP (pH 2): 1.76

Example 3

(Method (c))

A mixture of 1.36 g (4.0 mmol) of 5-amino-1- (2,6-dichloro-4-trifluoromethylphenyl) pyrazole-4-carboxamide, 0.61 g (6 mmol) of acetic anhydride and 50 ml of xylene is stirred at reflux temperature for 8 hours and then concentrated under reduced pressure. The oily residue is stirred with n-propanol and the crystalline product obtained is isolated by suction.

0.48 g (30% of theory) of 1- (2,6-dichloro-4-trifluoromethyl-phenyl) -6-methyl-1,5-dihydro-pyrazolo [3,4-d] pyrimidin-4-one is obtained from the melting point 300 ° C.

LogP (pH 2): 2.25

Example 4

(Method (s)) A mixture of 0.38 g (1.04 mmol) of 1- (2,6-dichloro-4-trifluoromethyl-phenyl) -6-methyl-1,5-dihydro-pyrazolo [3,4-d] pyrimidine-4 -on, 0.22 g (1.56 mmol) of methyl iodide, 0.22 g (1.56 mmol) of potassium carbonate and 30 ml of dimethylformamide is stirred at 20 ° C. to 25 ° C. for 6 hours and then under reduced pressure - narrowed. The residue is stirred with water and concentrated. Acidified hydrochloric acid.

The product obtained in crystalline form is isolated by suction.

0.30 g (75.5% of theory) of 1- (2,6-dichloro-4-trifluoromethylphenyl) -5,6-dimethyl-1,5-dihydro-pyrazolo [3,4-d] are obtained. pyrimidin-4-one with a melting point of 195 ° C. LogP (pH 2): 2.69

Example 5

(Method (b))

A mixture of 2.88 g (10 mmol) of 5-amino-1- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -pyrazole-4-carbonitrile, 2.0 g (13 mmol) of cyclopropanecarboxylic acid anhydride, 4 Drops conc. Sulfuric acid and 80 ml of toluene are stirred under reflux for 3 hours and then concentrated under reduced pressure. The residue is stirred with i-propanol and the crystalline product isolated by suction.

1.4 g (38% of theory) of 1- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -6-cyclopropyl-1,5-dihydro-pyrazolo [3,4-d] pyrimidine are obtained. 4-one with a melting point of 239 ° C. LogP (pH 2): 2.19 Example 6

(Method (d))

A mixture of 0.29 g (0.74 mmol) of 5- (l-fluoro-cyclopropylcarbonylamino) -l- (3-chloro-5-trifluoromethyl-pyridin-2-yl) pyrazole-4-carboxamide, 20 ml conc. Ammonia water and 30 ml of ethanol are heated under reflux for 6 hours. After cooling to room temperature (approx. 20 ° C.), the mixture is extracted with ethyl acetate, the organic phase is dried over sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate under reduced pressure.

38 mg (12.5% of theory) of 6- (l-fluoro-cyclopropyl) -l- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -1,5-dihydro-pyrazolo [ 3,4-d] pyrimidin-4-one from the melting point

211 ° C.

LogP (pH 2): 2.29

Analogously to Examples 1 to 6 and in accordance with the general description of the production processes according to the invention, it is also possible, for example, to prepare the compounds of the general formulas (I) and (Ia) listed in Table 1 below.

(I) (Ia) Table 1: Examples of the compounds of the formula (I) and (Ia)

The logP values specified in the table were determined in accordance with EEC Directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) on a phase reversal column (C 18). Temperature: 43 ° C.

(a) Eluents for determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with ^a ). (b) eluents for determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked in Table 1 with b).

The calibration was carried out with unbranched alkan-2-ones (with 3 to 16 carbon atoms) whose logP values are known (determination of the logP values on the basis of the retention times by linear interpolation between two successive alkanones).

The lambda max values were determined using the UV spectra from 200 nm to 400 nm in the maxima of the chromatographic signals.

The compounds listed as examples 109 and 110 in Table 1 above can be prepared, for example, as follows:

A mixture of 0.80 g (2.25 mmol) of 1- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -6-cyclopropyl-1,5-dihydro-pyrazolo [3,4-d] pyrimidine -4-one (cf. Example 5), 0.31 g (2.47 mmol) of dimethyl sulfate, 0.37 g (2.7 mmol) of potassium carbonate and 40 ml of N, N-dimethylformamide are added for 12 hours Room temperature (about 20 ° C) stirred and then concentrated under reduced pressure. The residue is stirred with water, with conc. Acidified hydrochloric acid, extracted with ethyl acetate, dried over sodium sulfate and filtered. The filtrate is concentrated under reduced pressure. For purification, 0.90 g of the crude product obtained as a residue is chromatographed on a silica gel column (toluene / ethyl acetate, vol .: 1: 1). 0.22 g (26% of theory) of 1- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -4-methoxy-6-cyclopropyl-pyrazolo-pyrimidin-4-one with a melting point of 142 ° C. is obtained (LogP (pH 2): 3.97) and 0.56 g (63% of theory) 1- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -5-methyl-6-cyclopropyl-l, 5-dihydro-pyrazolo [3,4-d] pyrimidin-4-one, melting point 121 ° C (LogP (pH 2): 2.61).

Starting materials of formula (II): Example (II- 1)

15 g (52 mmol) of 5-amino-1- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -pyrazole-4-carbonitrile are stirred in 150 ml of 98% sulfuric acid at 60 ° C. for 4 hours , The solution, cooled to 20 ° C., is then stirred with 800 ml of ice water. The solution is then extracted three times with ethyl acetate and three times with methylene chloride. The combined organic phases are dried over sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate under reduced pressure.

14.8 g (94% of theory) of 5-amino-1- (3-chloro-5-trifluoromethyl-pyridine-

2-yl) -pyrazole-4-carboxamide, melting point 196 ° C (LogP (pH 2): 1.46).

Analogously to Example (II-1), the compounds of the formula (II) listed in Table 2 below can also be prepared, for example.

Table 2: Examples of the compounds of the formula (II)

Starting materials of the formula (VI): Example (VI- 1)

4.86 g (15.9 mmol) of 5-amino-1- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -pyrazole-4-carboxamide are dissolved in 50 ml of acetonitrile at room temperature (approx. 20 ° C) in portions with 0.80 g (31.8 mmol) of sodium hydride (80% in paraffin), stirred for 10 minutes, mixed with 3.9 g (31.8 mmol) of 1-fluoro-cyclopropanecarboxylic acid chloride and then for 12 hours Room temperature stirred. After concentration under reduced pressure, the residue is mixed with water and concentrated. Acidified hydrochloric acid. The product obtained in crystalline form is isolated by suction.

3.1 g (46% of theory) of 5- (l-fluoro-cyclopropylcarbonylamino) -l- (3-chloro-5-trifluoromethyl-pyridin-2-yl) -pyrazole-4-carboxamide, of melting point, are obtained

204 ° C (LogP (pH 2): 2.02).

Analogously to Example (VI-1), for example, the compounds of the formula (VI) listed in Table 3 below can also be prepared.

Table 3: Examples of the compounds of the formula (VI)

Application examples:

Example A

Pre-emergence test (herbicidal activity)

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After 24 hours, the soil is sprayed with the active ingredient preparation in such a way that the desired amount of active ingredient is applied per unit area. The concentration of active ingredient in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.

After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control. It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to Preparation Example 8, 16, 18, 24, 27, 32, 33, 57, 59, 60, 64, 66, 67, 80, 92 and 109 show with good tolerance to cultivated plants, such as Corn, wheat and sugar beet, strong weed control. Example B

Post emergence test (herbicidal activity)

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired level

Concentration.

Test plants with a height of 5-15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 1000 l of water / ha.

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to the preparation example show

6, 16, 18, 24, 27, 31, 32, 33, 39, 57, 59, 60, 64, 66, 61, 69, 80, 85, 92, 109 and 110 with partially good tolerance to cultivated plants, such as Wheat, effective against weeds. Example C

Meloidogyne test (nematicidal activity)

Solvent: 7 parts by weight of dimethylformnamide

Emulsifier: 2 parts by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted with water to the desired concentration.

Vessels are filled with sand, active ingredient solution, Meloidogyne incognita egg larva suspension and lettuce seeds. The lettuce seeds germinate and the plantlets develop. The galls develop at the roots.

After the desired time, the nematicidal effect is determined in% using the formation of bile. 100% means that no galls were found; 0% means that the number of galls on the treated plants corresponds to that of the untreated control.

In this test, e.g. B. the following compounds of the preparation examples good activity: 16 and 80.

Claims

claims

1. Compounds of formula (I)

in which

Q represents in each case by at least two identical or different substituents from the series comprising nitro, cyano, halogen, and in each case optionally halogen-substituted -C _Ö - alkyl, CrCβ-alkoxy, dC ₆ -

Alkylthio, alkylsulfinyl or Cr -C _ö alkylsulfonyl substituted aryl or heteroaryl having up to 10 carbon atoms and optionally up to 5 nitrogen atoms and / or optionally an oxygen or sulfur atom respectively,

R ¹ for hydrogen, for each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy Ci-C ₆ alkyl or d- alkoxycarbonyl, for each optionally substituted by halogen C - C ₆ alkenyl or C ₂ -C ₆ -alkynyl, each for C ₃ -C ₆ -cycloalkyl or C ₃ -C ₆ -cycloalkyl-C ₁ -C ₄ -alkyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl, for each optionally substituted by Nitro, cyano, halogen, C ₁ -C ₄ -alkyl, Ci-G _t -haloalkyl, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy-substituted aryl or arylalkyl, each with up to 10 carbon atoms in the aryl group and against - appropriate, up to 4 carbon atoms in the alkyl moiety, or represents optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ halo-alkyl, C ₁ -C ₄ alkoxy or - haloalkoxy substituted heterocyclo - cyclyl with up to 10 carbon atoms, up to 5 nitrogen atoms and / or an oxygen or sulfur atom, and

R ² for hydrogen, for CrCβ-alkyl optionally substituted by cyano, halogen, CrC ₄ -alkoxy or C ₁ -C ₄ -alkoxy-carbonyl or for in each case optionally substituted by halogen C ₂ -C ₆ -alkenyl or C ₂ -C ₆ -Alkynyl stands,

with the exception of 1,5-dihydro-6-methyl-l- (2,4,6-trichlorophenyl) -4H- ρyrazolo- [3,4-d] pyrimidin-4-one.

2. Compounds of the formula (Ia)

in which

Q, R ¹ and R ^{2 have} the meanings given in Claim 1.

3. Compounds of formula (I) and (Ia) according to claim 1 or 2, characterized in that

Q represents - alkyl, C ₁ -C ₄ - each substituted by at least two identical or different substituents from the series nitro, cyano, fluorine, chlorine, bromine, each optionally substituted by 1 to 3 fluorine and / or chlorine atoms Alkoxy, - -alkylthio, - -alkylsulfmyl or C ₁ -C ₄ -alkylsulfonyl-substituted aryl with 6 or 10 carbons - atoms or heteroaryl with up to 5 carbon atoms, up to 3 nitrogen atoms and / or optionally an oxygen or sulfur atom,

R ¹ for hydrogen, each optionally by cyano, fluorine, chlorine,

Methoxy, ethoxy, n- or i-propoxy substituted d-Cs-alkyl or -Cs-alkoxycarbonyl, for in each case optionally substituted by fluorine, chlorine and / or bromine, C -C ₅ -alkenyl or C ₂ -C ₅ -alkynyl, for in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, C ₃ -C ₆ -cycloalkyl or C ₃ -C ₆ -cycloalkyl-C ₁ -C ₃ -alkyl, each in each case optionally by nitro, cyano, fluorine, chlorine, bromine , Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i -, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy,

Chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluroethoxy substituted aryl or arylalkyl, each with 6 or 10 carbon atoms in the aryl group and optionally up to 3 carbon atoms in the alkyl part, or, if appropriate, by nitro, cyano, fluorine, chlorine, bromine, methyl , Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluroethoxy substituted heterocyclyl with up to 10 carbon atoms, up to 4 nitrogen atoms and / or is a sulfur atom and / or,

R ² for hydrogen, for optionally by cyano, fluorine, chlorine, bromine,

Methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxy-carbonyl-substituted Cι-C ₅ alkyl or C ₂ -C ₅ alkenyl or C ₂ -C ₅ alkynyl represents in each case optionally substituted by fluorine, chlorine and / or bromine, C.

Compounds of formulas (I) and (Ia) according to claim 1 or 2, characterized in that

Q represents phenyl, pyridinyl, pyrimidinyl, pyrazolyl, furyl or thienyl, each of which has at least two identical or different substituents from the series nitro, cyano, fluorine, chlorine, bromine,

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, chloromethyl, bromomethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, bromethyl, difluorethyl, Dichloroethyl, chlorofluoroethyl, trifluoroethyl, trichloroethyl, chlorodifluoroethyl, fluorodichloroethyl, tetrafluoroethyl, pentafluoroethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, fluoroethoxychloroethoxy, chloroethoxychloroethoxy, chloro , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, methylsulfmyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl and trifluoromethylsulfon

R ¹ for hydrogen, each optionally by cyano, fluorine, chlorine,

Methoxy, ethoxy, n- or i-propoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, n-, i -, S- or t-butoxycarbonyl, for ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, optionally substituted by fluorine, chlorine and / or bromine, for each optionally substituted by cyano, fluorine, chlorine, Methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, Chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy, or phenyl, benzyl or phenylethyl substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n- , i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy , Fluoroethoxy,

Chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy substituted pyridinyl, pyrimidinyl, furyl, tetrahydrofuryl or thienyl, and

for hydrogen, for each optionally by cyano, fluorine, chlorine,

Bromine, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally substituted by fluorine, chlorine and / or bromine ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl. Compounds of formulas (I) and (Ia) according to claim 1 or 2, characterized in that

Q represents phenyl which has at least two identical or different substituents in the 2- and 4-position and optionally another

Contains substituents in the 6-position, the substituents from the series nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethyl , Fluorodichloromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluorethoxy, trifluoroethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethyl, trifluoromethylsulfonyl, ethylsulfonylsulfonylsulfylethylsulfonylsulfylethylsulfonylsulfylethylsulfonylsulfylethylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfonylsulfylethylsulfonylsulfylethylsulfonylsulfonyl

R ¹ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, di-fluoroethyl, dichloroethyl, chlorofluoroethyl , Trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for ethenyl, propenyl, butenyl, pentenyl, fluoropropenyl, chloropropenyl, difluorofluorophenyl, difluorofluoropropenyl , Chlorobutenyl, difluorobutenyl, dichlorobutenyl,

Chlorofluorobutenyl, ethynyl, propynyl, butynyl or pentynyl, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally substituted by fluorine, chlorine or methyl, for each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy or substituted phenyl, benzyl or for each optionally by nitro, cyano,

Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy , Difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy substituted pyridinyl, pyrimidinyl, furyl, tetrahydrofuryl or thienyl, and

R ² for hydrogen, for each optionally by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxy-carbonyl substituted methyl, ethyl, n- or i-propyl, or for propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl which is optionally substituted by fluorine and / or chlorine.

Q stands for pyridin-2-yl which contains at least two identical or different substituents in the 3- and 5-position and optionally a further substituent in the 6-position, the substituents from the series nitro, cyano, fluorine, chlorine, bromine, Methyl, ethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, fluoroethoxy, chloroethoxy, difluorooxy, chloro

Trifluoroethoxy, methylthio, ethylthio, difluoromethylthio, trifluoro methylthio, chlorodifluoromethylthio, fluorodichloromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl are selected,

for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i- or s-

Butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, di-fluoroethyl, dichloroethyl, chlorofluoromethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, methoxymethyl, ethoxymethyl, methoxyethyl, methoxyethyl, ethoxyethyl, ethoxyethyl, ethoxyethyl, ethoxyethyl, ethoxyethyl, ethoxyethyl - carbonyl, for ethenyl, propenyl, butenyl, pentenyl, fluopropenyl, chloropropenyl, difluoropropenyl, dichloropropenyl, chlorofluoropropenyl, fluorobutenyl, chlorobutenyl, difluorobutenyl, dichlorobutenyl, chlorofluorobutenyl, optionally or because pentyl, for vinyl, for chlorine Methyl substituted

Cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each optionally with nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, Trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluorifluoroxy or chlorofluorifluoroxy, chlorofluorifluoroxy or chlorofluorifluorethoxy, chlorofluorifluoroxy or chlorofluorifluoroxy or chlorofluoromethoxy or chlorofluoromethoxy or chlorofluoromethoxy or chlorofluoromethoxy or chlorofluoromethyl Phenyl, benzyl or phenylethyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-

Butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, Chlorfluorethoxy, chlorine difluoroethoxy or trifluoroethoxy-substituted pyridinyl, pyridine midinyl , Furyl, tetrahydrofuryl or thienyl, and R ² for hydrogen, for each methyl, ethyl, n- or i-propyl optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, or for each optionally by fluorine and / or chlorine-substituted propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl.

Compounds of formulas (I) or (Ia) according to claim 1 or 2, characterized in that

Q represents pyrazol-3-yl, which contains at least two identical or different substituents in the 1- and 5-position and optionally a further substituent in the 4-position, the substituents from the series nitro, cyano, fluorine, chlorine, bromine, Methyl, ethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluorodichloromethoxy, fluoroethoxy, chloroethoxy, difluoromethoxy, dichloroethoxy, dichloroethioifluorethioifluorethioifluorethioifluorethioifluorethioifluorethioifluorethioifluorethioifluorethioifluorethioifluoroethioifluoroethioifluoroethioifluoroethioifluorethioifluorethioifluorethioifluorethioifluorethioifluorethioifluorethioifluoromethyl, methylthio, chlorodifluoromethylthio, fluorodichloromethylthio, methylsulfmyl, ethylsulfmyl, trifluoromethylsulfmyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl are selected,

R ¹ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl,

Chlorodifluoromethyl, fluorodichloromethyl, fluoroethyl, chloroethyl, di-fluoroethyl, dichloroethyl, chlorofluoroethyl, trifluoroethyl, tetrafluoroethyl, pentafluoroethyl, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, for ethenyl, propenyl, for ethenyl, benzenes Pentenyl, fluopropenyl,

Chloφropenyl, Difluoφropenyl, Dichloφropenyl, Chlorfluor- propenyl, fluorobutenyl, chlorobutenyl, difluorobutenyl, dichlorobutenyl, chlorofluorobutenyl, ethynyl, propynyl, butynyl or pentynyl, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by fluorine, chlorine or methyl, each optionally substituted by nitro, cyano, fluorine, chlorine Bromine, methyl,

Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s - or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy substituted phenyl, benzyl or phenylethyl, or for each optionally substituted by nitro, cyano, methyl, fluorine, fluorine , Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, dichloromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, Chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, chlorodifluoroethoxy or trifluoroethoxy substituted pyridinyl, pyrimidinyl, furyl, tetrahydrofuryl or thienyl, and

R> 2 for hydrogen, for each optionally by cyano, fluorine, chlorine,

Methoxy, ethoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxy-carbonyl substituted methyl, ethyl, n- or i-propyl, or for propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl which is optionally substituted by fluorine and / or chlorine. A process for the preparation of compounds of formulas (I) and (Ia) according to claim 1 or 2, characterized in that

a) compounds of the formula (II)

in which

Q has the meaning given in claim 1,

with compounds of the formula (III)

R ¹ - (OR ') ₃ (HI)

in which

R ^{1 has} the meaning given in claim 1 and

R 'represents alkyl,

or that one (b) compounds of the formula (IV)

in which

Q has the meaning given in claim 1,

with compounds of formula (V)

in which

R ^{1 has} the meaning given in claim 1,

or that one

(c) compounds of the formula (II)

in which

Q has the meaning given in claim 1,

with compounds of formula (V)

° γ ^Rl

° γ ° (V)

R ¹ in which

R ^{1 has} the meaning given in claim 1,

or that one

(d) compounds of the formula (VI)

in which

Q and R ^{1 have} the meanings given in Claim 1, if appropriate in the presence of one or more condensation auxiliaries and if appropriate in the presence of one or more diluents,

or that one

(e) compounds of the formula (Ib)

in which

Q and R have the meaning given in claim 1,

with alkylating, alkenyling or alkynylating agents of the formula (VII)

XR ^l (VII)

or of the formula (VIII)

R ² -O-SO ₂ -OR ² (VIII)

where each

R ^{2 has} the meaning given in claim 1 and

X represents halogen, if appropriate in the presence of one or more reaction auxiliaries and if appropriate in the presence of one or more diluents.

9. Compounds of formula (II)

in which

Q has the meaning given in claim 1.

10. Compounds of the formula (VI)

in which

Q and R ^{1 have} the meanings given in claim 1.

11. Compounds of the formula (Ib)

in which

Q and R ^{1 have} the meaning given in claim 1.

12. Plant treatment agent, characterized by a content of at least one compound according to one of claims 1 to 7 and conventional extenders and / or surface-active substances.

13. Use of at least one compound according to one of claims 1 to 7 or an agent according to claim 12 for combating undesirable plants and / or nematodes.

14. Method for controlling undesirable plants and / or

Nematodes, characterized in that at least one compound according to one of claims 1 to 7 or an agent according to claim 12 is allowed to act on the plants and / or nematodes and / or their habitat.