EP1511383A1

EP1511383A1 - Substituted phenyluracils

Info

Publication number: EP1511383A1
Application number: EP03730057A
Authority: EP
Inventors: Hans-Georg Schwarz; Roland Andree; Dorothee Hoischen; Karl-Heinz Linker; Mark Wilhelm Drewes; Peter Dahmen; Dieter Feucht; Rolf Pontzen
Original assignee: Bayer CropScience AG
Current assignee: Bayer CropScience AG
Priority date: 2002-05-29
Filing date: 2003-05-16
Publication date: 2005-03-09
Also published as: AU2003240662A1; WO2003099009A1; US20050288185A1; DE10223914A1; BR0311567A; AR040114A1; MXPA04011823A; CA2487781A1

Abstract

The invention relates to novel substituted phenyluracils of general formula (I) wherein A, Q, R<1>, R<2>, R<3>, R<4>, R<5> and R<6> have the designation cited in the description, to a method for producing said phenyluracils, and to the use of the same as plant treating agents.

Description

Substituted phenyluracile

The invention relates to new substituted phenyluracils, ner processes for their preparation and their use as plant treatment agents, in particular as herbicides.

Certain substituted phenyluracils which have a structure similar to the compounds of the present invention are already known (e.g. EP-A-255 047, EP-A-831 091, EP-A-1 061 075, US-6,207,830). However, these compounds have so far had no particular significance because they have various disadvantages.

New substituted phenyluracils of the general formula (I)

in which

A represents alkanediyl having 1 to 6 carbon atoms, alkenediyl having 2 to 6 carbon atoms or alkindiyl having 2 to 6 carbon atoms,

represents O (oxygen), S (sulfur), SO or SO ₂ ,

R ^{1 represents} hydrogen, amino or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C _r C ₄ alkoxy, R ² for carboxy, cyano ,. Carbamoyl, thiocarbamoyl or in each case optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy-substituted alkyl or alkoxycarbonyl, each having 1 to 6 carbon atoms in the alkyl groups,

R ^{3 represents} hydrogen, halogen or optionally substituted by halogen

Alkyl having 1 to 6 carbon atoms,

R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,

R ^{5 represents} nitro, cyano, carbamoyl, thiocarbamoyl, halogen or in each case optionally substituted by halogen substituted alkyl or alkoxy each having 1 to 6 carbon atoms, and

R ⁶ for a bonded to A via a carbon atom, by cyano, carboxy, carbamoyl or thiocarbamoyl, or by Ci-Cö-alkoxy-carbonyl, C ₃ -C ₆ -

Cycloalkyloxy-carbonyl or -CC ₆ -alkylamino-carbonyl (which are each optionally substituted by cyano, carboxy, halogen or -CC ₆ -alkoxy-carbonyl), or by di- (C ₁ -C ₄ -alkyl) -amino -carbonyl or N- (- C ₄ alkoxy) -C ₁ -C ₄ alkylamino carbonyl, or by C ₂ -C ₆ alkenyloxy carbonyl or C ₂ -C ₆ alkynyloxy carbonyl (which in each case optionally are substituted by halogen), or by cyano-CrC ₆ -alkyl, carboxy-Ci- C ₆ -alkyl, C ₁ -C ₄ -alkoxy-carbonyl-C ₁ -C ₆ -alkyl, cyano-C ₂ -C ₆ - alkenyl, carboxy-C ₂ -C ₆ -alkenyl or C ₁ -C ₄ -alkoxy-carbonyl-C ₂ -C ₆ -alkenyl (which are each optionally substituted by halogen), and optionally additionally by nitro, halogen or by -Gr Alkyl, CrC -alkoxy, -

C ₄ alkylthio, CrC ₄ alkylsulfmyl or C ₁ -C ₄ alkylsulfonyl (which are each optionally substituted by halogen) substituted, monocyclic or bicyclic heterocyclyl having up to 9 carbon atoms and up to 5 heteroatoms, selected from up to 5 Nitrogen atoms and / or up to 2 oxygen atoms and / or up to 2 sulfur atoms as well optionally with up to 2 -SO groups, up to 2 -SO ₂ groups, up to 2 -CO groups or up to 2 -CS groups,

including the possible stereoisomeric forms

found.

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:

A preferably represents alkanediyl having 1 to 5 carbon atoms, alkenediyl having 2 to 5 carbon atoms or alkindiyl having 2 to 5 carbon atoms.

Q preferably represents O (oxygen), S (sulfur) or SO ₂ .

R ¹ preferably represents hydrogen, amino or alkyl having 1 to 4 carbon atoms which is optionally substituted by cyano, halogen or C 1 -C 4 -alkoxy.

R ² preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally by cyano, halogen or Cι _. -C ₄ -alkoxy-substituted alkyl or alkoxycarbonyl, each with 1 to 4 carbon atoms in the alkyl groups. R ³ preferably represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 4 carbon atoms.

R ⁴ preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine,

Chlorine, bromine or iodine.

R ⁵ preferably represents nitro, cyano, carbamoyl, thiocarbamoyl, halogen or in each case optionally substituted by halogen substituted alkyl or alkoxy each having 1 to 4 carbon atoms.

R ⁶ preferably represents a bonded to A via a carbon atom, by cyano, carboxy, carbamoyl or thiocarbamoyl, or by C Cs-alkoxycarbonyl, C ₅ -C ₆ -cycloalkyloxy-carbonyl or CrCs-alkylamino-carbonyl (which in each case optionally by Cyano, carboxy, halogen or CrC ₄ -

Alkoxy-carbonyl are substituted), or by di- (C ₁ -C ₄ -alkyl) -amino-carbonyl or N- (C ₁ -C ₄ -alkoxy) -C ₁ -C ₄ -alkyl-amino-carbonyl, or by C ₂ - C ₅ alkenyloxy-carbonyl or C ₂ -C ₅ -alkynyloxy-carbonyl (which are each optionally substituted by halogen), or by cyano-G-Cs-alkyl, carboxy-CrCs-alkyl, -C ^ alkoxy -carbonyl-CrCs-alkyl, cyano-C ₂ -C5-alkenyl, carboxy-C ₂ -C ₅ -alkenyl or C ₁ -C ₄ -alkoxycarbonyl-C2-C5-alkenyl (which are each optionally substituted by halogen), and optionally additionally by nitro, halogen or by C ₁ -C ₄ alkyl, -CC alkoxy, C ₁ -C ₄ alkylthio, C _ϊ ^' -C ^ alkylsulfinyl or C ₁ -C ₄ alkylsulfonyl (which in each case optionally by Halogen substituted) substituted, monocyclic or bicyclic heterocyclyl with up to 9 carbon atoms and up to 5 heteroatoms selected from up to 3 nitrogen atoms and / or an oxygen atom and / or a sulfur atom, and optionally with an additional -SO group, an -SO ₂ group, a -CO group or a -CS group. A particularly preferably represents alkanediyl having 1 to 4 carbon atoms, alkenediyl having 2 to 4 carbon atoms or alkindiyl having 2 to 4 carbon atoms.

Q particularly preferably represents O (oxygen) or S (sulfur).

R ¹ particularly preferably represents hydrogen, amino or methyl, ethyl or n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.

R ² particularly preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted alkyl or alkoxycarbonyl each having 1 to 3 carbon atoms in the alkyl groups.

R ³ particularly preferably represents hydrogen, fluorine, chlorine, bromine or methyl, ethyl or n- or i-propyl optionally substituted by fluorine and / or chlorine.

R ⁴ particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine.

R ⁵ particularly preferably represents nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 to 3 carbon atoms.

R ⁶ particularly preferably represents a bonded to A via a carbon atom, by cyano, carboxy, carbamoyl or thiocarbamoyl, or by C 1 -C ₄ -

Alkoxy-carbonyl, C ₅ -C ₆ -cycloalkyloxy-carbonyl or C ₁ -C ₄ -alkylamino-carbonyl (which are each optionally substituted by cyano, carboxy, halogen or C ₁ -C ₄ -alkoxy-carbonyl), or by di - (C ₁ -C ₃ alkyl) - amino-carbonyl or N- (C ₁ -C -alkoxy) -C-C -alkyl-amino-carbonyl, or by C ₃ -C ₄ -alkenyloxy-carbonyl or C ₃ -C -alkynyloxy-carbonyl (which in each case optionally by Halogen are substituted), or by cyano -CC ₃ alkyl, carboxy -CC _. -C ₃ -alkyl, C ₁ -C ₄ -alkoxy-carbonyl-C ₁ -C ₃ -alkyl, cyano-C ₂ -C ₃ -alkenyl, carboxy-C ₂ -C ₃ -alkenyl or C ₁ -C ₄ - alkoxy-carbonyl

C ₂ -C ₃ alkenyl (each of which is optionally substituted by halogen), and optionally additionally by nitro, halogen or by Ci-C ₄ - alkyl, -C ₄ alkoxy, C ₁ -C ₄ alkylthio, Cι-C ₄ -Alkylsulfmyl or CrC ₄ - alkylsulfonyl (which are each optionally substituted by halogen) substituted heterocyclyl from the series furyl, benzofuryl, tetrahydrofuryl, thienyl, benzothienyl, pyrrolyl, benzopyrrolyl, pyrrolinyl, pyrazolyl, benzopyrazolyl, pyrazolylimide, imazrazolinyl, im , Oxazolyl, benzoxazolyl, oxazolinyl, isoxazolyl, isoxazolinyl, thiazolyl, benzthiazolyl, thiazolinyl, thiadiazolyl, triazolyl, pyridinyl, pyrimidinyl, triazinyl.

A very particularly preferably represents methylene, ethane-l, l-diyl, ethane-l, 2-diyl (dimethylene), propane-l, l-diyl, propane-l, 2-diyl, propane-l, 3-diyl , Ethene-1,1-diyl, ethene-1,2-diyl, propene-1,1-diyl, propene-1,2-diyl, propene-1,3-diyl, ethyne-1,2-diyl or propyne - 1,3-diyl.

Q very particularly preferably represents O (oxygen).

R ¹ very particularly preferably represents hydrogen, amino or in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy

Methyl or ethyl.

R ² very particularly preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or in each case methyl, ethyl, methoxycarbonyl or ethoxycarbonyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy. R ³ very particularly preferably represents hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine.

R ⁴ very particularly preferably represents hydrogen, cyano, fluorine or chlorine.

R ⁵ very particularly preferably represents nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or in each case methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine.

R ⁶ very particularly preferably represents a bonded to A via a carbon atom, by cyano, carboxy, carbamoyl or thiocarbamoyl, or by methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl (which are each optionally substituted by cyano, carboxy, fluorine, chlorine, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl), or by dimethylamino-carbonyl, diethylaminocarbonyl or N-methoxy-methylaminocarbonyl, or by propenyloxycarbonyl, butenyloxycarbonyl, propynyloxycarbonyl or

Butinyloxy-carbonyl (which are each optionally substituted by fluorine or chlorine), or by cyanomethyl, cyanoethyl, cyanopropyl, carboxymethyl, carboxyethyl, carboxypropyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n- or i-propoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n- or i -Propoxycarbonylethyl, cyanoethenyl,

Cyanopropenyl, carboxyethenyl, carboxypropenyl, methoxycarbonylethenyl, ethoxycarbonylethenyl, n- or i-propoxycarbonylethenyl, methoxycarbonylpropenyl, ethoxycarbonylpropenyl, n- or i-propoxycarbonyl-propenyl (which are each optionally substituted by fluorine and / or chlorine) and optionally additionally by nitro, fluorine, chlorine, bromine,

Methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl (which are each optionally substituted by fluorine and / or chlorine) substituted heterocyclyl from the series furyl, thienyl, pyrrolyl, pyrrolinyl, pyrazolyl , Pyrazolinyl, fmidazolyl, imidazolinyl, oxazolyl, oxazolinyl, isoxazolyl, isoxazolinyl,

Thiazolyl, thiazolinyl, pyridinyl, pyrimidinyl.

A most preferably represents methylene.

R ¹ most preferably represents hydrogen, methyl or amino.

R ² most preferably represents trifluoromethyl.

R ³ most preferably represents hydrogen.

R ⁴ most preferably represents fluorine.

R ⁵ most preferably represents chlorine, bromine or cyano.

R ⁶ most preferably represents one of the following groupings (A) to (L)

(A) (B) (C) (°) ( ^E )

(F) (G) (H) (J)

() (L) where

R ^{7 represents} carboxy, carbamoyl, methoxycarbonyl, ethoxycarbonyl or n- or i-propoxycarbonyl.

R ⁷ preferably represents methoxycarbonyl or ethoxycarbonyl.

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.

Most preferred according to the invention are the compounds of formula (I) in which there is a combination of the meanings listed as most preferred above.

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

A represents methylene, Q stands for O (oxygen),

R ^{1 represents} hydrogen, amino or methyl,

R ^{2 represents} cyano or trifluoromethyl,

R ^{3 represents} hydrogen, chlorine, bromine or methyl,

R ^{4 represents} hydrogen, fluorine or chlorine,

R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

R ⁶ for through cyano, carboxy, carbamoyl, thiocarbamoyl, through methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and optionally additionally through nitro, fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy,

Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl is substituted furyl.

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

A represents methylene,

Q stands for O (oxygen),

R ^{1 represents} hydrogen, amino or methyl,

R ^{2 represents} cyano or trifluoromethyl,

R ^{3 represents} hydrogen, chlorine, bromine or methyl, R ^{4 represents} hydrogen, fluorine or chlorine,

R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

R ^{6 represents} by cyano, carboxy, carbamoyl, thiocarbamoyl, by methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and optionally additionally by nitro, fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, Ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted oxazolyl.

A represents methylene,

Q stands for O (oxygen),

R ^{1 represents} hydrogen, amino or methyl,

R ^{2 represents} cyano or trifluoromethyl,

R ^{3 represents} hydrogen, chlorine, bromine or methyl,

R ^{4 represents} hydrogen, fluorine or chlorine,

R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

R ⁶ for through cyano, carboxy, carbamoyl, thiocarbamoyl, through methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and optionally additionally through nitro, fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted isoxazolyl.

A represents methylene,

Q stands for O (oxygen),

R ^{1 represents} hydrogen, amino or methyl,

R ^{2 represents} cyano or trifluoromethyl,

R ^{3 represents} hydrogen, chlorine, bromine or methyl,

R ^{4 represents} hydrogen, fluorine or chlorine,

R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

R ^{6 represents} by cyano, carboxy, carbamoyl, thiocarbamoyl, by methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and optionally additionally by nitro, fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, Ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted thiazolyl.

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

A represents methylene, Q stands for O (oxygen),

R ^{1 represents} hydrogen, amino or methyl,

R ^{2 represents} cyano or trifluoromethyl,

R ^{3 represents} hydrogen, chlorine, bromine or methyl,

R ^{4 represents} hydrogen, fluorine or chlorine,

R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

Methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted pyridinyl.

A represents methylene,

Q stands for O (oxygen),

R ^{1 represents} hydrogen, amino or methyl,

R ^{2 represents} cyano or trifluoromethyl,

R ^{5 represents} cyano, thiocarbamoyl, chlorine, bromine or trifluoromethyl,

R ^{6 represents} by cyano, carboxy, carbamoyl, thiocarbamoyl, by methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and optionally additionally by nitro, fluorine, chlorine, bromine, methyl, ethyl, methoxy, ethoxy, methylthio, ethylthio, methylsulfinyl, Ethylsulfinyl, methylsulfonyl or ethylsulfonyl substituted thienyl.

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 residual definitions can be combined with one another as desired, that is to say also between the specified preferred ranges.

The new substituted phenyluracils of the general formula (I) are notable for strong and selective herbicidal activity.

The new substituted phenyluracils of the general formula (I) are obtained if hydroxyphenyl- or mercaptophenyluracils of the general formula (II)

in which

Q, R, R, R, R and R have the meanings given above, with substituted heterocycles of the general formula (HI)

in which

A and R ^{6 have} the meanings given above and

X represents halogen or optionally substituted alkylsulfonyloxy or arylsulfonyloxy,

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

and optionally the compounds of the formula (I) thus obtained are converted into other compounds of the formula (I) by customary methods.

If, for example, 3- (2,4-dichloro-5-mercapto-phenyl) -l-methyl-6-trifluoromethyl-1H-pyrimidine-2,4-dione and 2-bromomethyl-furan-4-carboxylic acid-methyl are used ester as starting materials, the course of the reaction in the ner driving according to the invention can be outlined by the following formula:

Formula (II) provides a general definition of the hydroxyphenyl- and mercapto-phenyluracils to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I). In the formula (II), Q, R ¹ , R ² , R ³ , R ⁴ and R ⁵ preferably have those meanings which are particularly preferred, particularly preferred, in connection with the description of the compounds of the formula (I) according to the invention particularly preferred or most preferred for Q, R ¹ , R ² , R ³ , R ⁴ and R ^{5 have been} given.

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. WO 97/01541, WO 98/54155).

Formula (ITI) provides a general definition of the substituted heterocycles to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I). In the formula (TU), A and R ⁶ preferably have those meanings which have been given above as preferred, particularly preferred, very particularly preferred or most preferred for A and R ⁶ in connection with the description of the compounds of the formula (I) according to the invention have been; X preferably represents fluorine, chlorine, bromine, iodine, C ₁ -C ₄ -alkylsulfonyloxy optionally substituted by fluorine and / or chlorine or phenylsulfonyloxy, optionally substituted by fluorine, chlorine or methyl, in particular for chlorine, bromine, methylsulfonyloxy, phenylsulfonyloxy or tolylsulfonyloxy.

The starting materials of the general formula (III) are known and / or can be prepared by processes known per se (cf. J. Chem. Soc, Chem. Commun. 19 (1996), 2251-2252; J. Med. Chem. 38 (1995), .4806-4820; Tetrahedron 54 (1998), 7525-7538; Dokl. Akad. Nauk. Arm. SSR 17 (1953), 97-103; Organic Process Research & Development 5 (2001), 37-44 ).

The substituted heterocycles of the general formula (III) are obtained if, for example, alkyl heterocycles of the general formula (IV)

in which

A and R have the meanings given above,

with halogenating agents, e.g. N-bromosuccinimide or N-chlorosuccinimide, preferably in the presence of a reaction auxiliary, e.g. 2,2'-azo bis-2-methyl-propanenitrile, and preferably in the presence of a diluent such as e.g. Tetrachloromethane, at temperatures between 0 ° C and 100 ° C (see. The manufacturing examples).

The substituted heterocycles of the general formula (IN) are known organic synthetic chemicals. The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using a reaction auxiliary. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as 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, s or t butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, 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), 1,5-diazabicyclo [4.3.0] non-5-ene (DBN), or 1,8-diazabicyclo [5.4 .0] -undec-7-en (DBU).

The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using a diluent. Inert organic solvents are particularly suitable as diluents for carrying out the process according to the invention. These include in particular ahphatic, alicyclic or aromatic, optionally halogenated

Hydrocarbons such as gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetxahydrofuran 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-methyl-pyrrolidone or hexamethylphosphoric 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, diethylene glycol mononomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be carried out. of the procedure according to the invention can be varied within a substantial range. In general, temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

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

To carry out the process 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 processing is carried out according to customary methods (cf. the manufacturing examples). ^' *,

The compounds of the general formula (I) can be converted by conventional methods into other compounds of the general formula (I) as defined above, for example compounds in which R ^{1 is} hydrogen, in corresponding compounds in which R ^{1 is} amino, by reaction with suitable amimerizing agents, such as, for example, l-aminooxy-2,4-dinitro-benzene (cf. Preparation example) or in corresponding compounds in which R ^{1 is} methyl stands, by reaction with dimethyl sulfate or methyl bromide (see. Preparation example).

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 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 substances according to the invention can e.g. can be used in 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,

Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercuriahs, MuUugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rorippa, Rorippa Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, 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 ^' , Nicia.

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Fistula, Eriochaimis, Antherocho, Eriocha, Antherocho , Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,

Scirpus, Setaria, Sorghum. Monocot cultures of the genera: Allium, 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 limited to these

Limited 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

Because of and places 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 areas as well for selective weed control 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 selective use

Control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in pre-emergence and in post-emergence ner driving.

The active compounds according to the invention can also be used in certain concentrations or application rates for controlling animal pests and fungal or bacterial plant diseases. If appropriate, they can also be used as intermediates or precursors for the synthesis of further active compounds.

According to the invention, all plants and parts of plants can be treated. Under

Plants are understood to mean all plants and plant populations, such as wanted and unwanted wild plants or crops (including naturally occurring crops). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including those by

Plant variety rights of protectable or non-protectable plant varieties. 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 as well as roots, tubers and rhizomes. 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 plant parts according to the invention with the active substances takes place directly or by acting on their environment, habitat or

Storage room according to the usual 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 usual formulations, such as

Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as very fine encapsulations in polymeric substances. ^'» _T

These 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, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated ahphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, ahphatic 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 and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; 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. Ligmn 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 mixed with known herbicides and / or with substances which

Improving crop compatibility ("safeners") can be used for weed control, ready-to-use formulations or tank mixes being possible. Mixtures with weed control compositions which contain one or more known herbicides and a safener are also possible.

Known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amicarbazone, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin (beflubutamide, 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, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop (-pro-pargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron ( - Sulam (-methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, desmedipham, dialallate, dicamba, dichloroprop (-P), diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamide, diquat, dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl), Fentrazamide, Flamprop (-isopropyl, -isopropyl-L, -methyl) Flazasulfuron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufenacet, Flufenpyr, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumet-sulam, Fluometuron, Fluorochloridone (Fluorochloridone) Flupoxam, Fluprop-acil, Flurpyrsulfuron (-methyl, -sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-butoxypropyl, -meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthi- a ide, Fomesafen, Foramsafen , Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl, -P-methyl), Hexazinone,

Imazamethabenz (-methyl), Imazamethapyr, Lmazamox, Lmazapic, Imazapyr, Imaza- quin, Imazethapyr, Imazosulfuron, Iodosulfüron (-methyl, -sodium), Ioxynil, Iso-propalin, Isoproturon, Isouron, Isoxabeno, Isoxabeno, Oxox , 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, Primisulfuron (-methyl), Profluazol, Profoxydim, Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propoxycarbazone (-sodium), Propyzamide, Prosulfocarb, Prosulfuron, Pyraflufen (-e thyl), pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, ^' pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine-quizalofac -ethyl, -P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn, sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutrynopyridium, thenchloride , Thifensulfuron (-methyl), Thiobencarb, Tio-carbazil, Tralkoxydi, 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 soil conditioner improvers, 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,

Spray, sprinkle.

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 amounts used are between ^'are 1 g and 10 kg of active compound per hectare of soil surface, 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 organic breeding methods, such as crossbreeding or protoplast fusion, and their varieties

Parts treated. In a further preferred embodiment, transgenes are Plants and plant varieties obtained by genetic engineering methods, possibly in combination with conventional methods (Genetically Modified Organisms) and their parts treated. The term "parts" or "parts of plants" or "plant parts" 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 have been obtained by conventional breeding, by mutagenesis, or else by recombinant DNA techniques. 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 cause superadditive ("synergistic") effects. For example, reduced application rates and / or extensions of the

Spectrum of activity and / or an enhancement of the effect of the substances and agents which can be used according to the invention - also in combination with other agrochemical active substances, better growth of the crop plants, increased tolerance of the crop plants to high or low temperatures, increased tolerance of the crop plants to drought or to water or Soil salinity, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher shelf life and / or workability of the harvested products, which go beyond the effects that are actually to be expected.

The preferred transgenic 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 against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher storage life and / or workability of the harvested products. Further and particularly highlighted examples of such properties are an increased defense of the plants against animal and microbial

Pests, such as insects, mites, phytopathogenic fungi, bacteria and / or niren, as well as an increased tolerance of the plants to certain herbicidal active ingredients. Examples of transgenic plants include the important crop plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes , Cotton and rapeseed are highlighted. 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), CryΙA (c), CryLIA, CrylllA, CryιLIB2, Cry9c Cry2Ab,

Cry3Bb and CrylF and their combinations) are generated in the plants (hereinafter referred to as "Bt plants"). The increased defense of plants against fungi, bacteria and niren by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins are also particularly emphasized as properties ("traits").

The traits are also particularly emphasized by the plants' increased tolerance to certain herbicidal active compounds, for example lmidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example the "PAT" gene). The genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are corn varieties, cotton varieties, soy varieties and potato varieties that are marketed under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Νucotn® (cotton) and ΝewLeaf® (potato). Examples of herbicide-tolerant plants are maize varieties,

Sorts of cotton and soy called under the trade names Roundup Ready® (tolerance against glyphosate eg corn, cotton, soy), Liberty Link® (tolerance against phosphinothricin, eg rape), IMI® (tolerance against imidazolinone) and STS® (tolerance against sulfonylureas eg maize). The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (e.g.

Corn) mentioned. 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").

According to the invention, the plants listed can be used particularly advantageously with the

Compounds of the general formula I or the active compound mixtures according to the invention are treated, the synergistic effects mentioned above occurring with the transgenic plants or plant cultivars in addition to the good control of the weed plants. 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.

The active compounds 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, the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with 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 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

Wise.

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, buffaloes, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as 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, watering, drenching, granules, pastes, boluses, the feed-through method, of suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal Application in the form of, for example, diving or bathing (dipping), spraying (spray), ¹ pouring on (pour-on and spot-on), des

Washing, powdering and with the aid 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 platelets 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, as granules or dust, 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

A mixture of 7.50 g (20.3 mmol) of 3- (4-bromo-2-fluoro-5-hydroxy-phenyl) -6-trifluoromethyl-1H-pyrimidine-2,4-dione, 4.45 g (20.3 mmol) of methyl 3-bromomethyl-furan-2-carboxylate, 5.6 g (40.6 mmol) of potassium carbonate and 120 ml of acetonitrile are heated under reflux for 6 hours. After cooling to room temperature, the mixture is poured into approximately the same volume of 2N hydrochloric acid and shaken with ethyl acetate. The organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is concentrated under reduced pressure and the residue is worked up by column chromatography (silica gel, methylene chloride / ethyl acetate, vol .: 95/5).

5.80 g (55% of theory) of 3- [2-bromo-5- (2,6-dioxo-4-trifluoromethyl-3,6-dmydro-2H-pyrirmdin-l-yl) -4-fluorine are obtained -phenoxymemyl] furan-2-carboxylic acid methyl ester. Example 2

(Subsequent reaction)

A mixture of 2.50 g (4.93 mmol) of 3- [2-bromo-5- (2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimidm-l-yl) -4- fluorophenoxymethyl] furan-2-carboxylic acid methyl ester, 0.82 g (5.92 mmol) of potassium carbonate and 65 ml of acetonitrile is stirred at room temperature (approx. 20 ° C.) for 10 minutes and then with a solution of 0.75 g (5.92 mmol) of dimethyl sulfate in 5 ml of acetonitrile are added dropwise with stirring. The reaction mixture is then stirred at 45 ° C. for 2 hours, then poured into about twice the amount of water and shaken with methylene chloride. The organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, the residue is stirred with hexane and the crystalline product is isolated by suction.

2.2 g (79% of theory) of 3- [2-bromo-5- (2,6-dioxo-3-methyl-4-trifluoromethyl-3, 6-dihydro-2H-pyrimidine-1 - yl) ^ 4-fluoro-phenoxymemyl] furan-2-carboxylic acid methyl ester.

LogP (pH 2.3) = 3.34. Example 3

(Subsequent reaction)

A mixture of 2.50 g (4.93 mmol) of 2- [2-bromo-5- (2,6-dioxo-4-trifluoromethyl-3,6-dihy (o-2H-pyrimidm-l-yl) - Methyl 4-fluorophenoxymemyl] furan-3-carboxylate, 0.50 g (5.92 mmol) sodium hydrogen carbonate and 50 ml N, N-dimethylformamide is at room temperature (approx. 20 ° C) for 10 minutes stirred and then with 1.18 g (5.92 mmol) of l-aminooxy-2,4-dinitro-benzene within 6 hours

- divided into small portions - offset. The reaction mixture is stirred for 15 hours at room temperature. Then another 0.60 g of l-aminooxy-2,4-dinitrobenzene are added and the mixture is stirred for a further 15 hours at room temperature. It is then poured into about twice the volume of water and then shaken with ethyl acetate. The organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is concentrated under reduced pressure and the residue purified by column chromatography (silica gel, hexane / ethyl acetate, Vol .: 2/1) worked up ^'.

1.0 g (39% of theory) of 2- [2-bromo-5- (3-amino-2,6-dioxo-4-trifluoromethyl-3,6-dihydro-2H-pyrimimn-1- yl) -4-fluoro-phenoxymethyl] furan-3-carboxylic acid methyl ester.

LogP (pH 2.3) = 3.00. Analogously to Examples 1 to 3 and in accordance with the general description of the production process according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Table 1 below.

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

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 ^D ).

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 using the

Retention times by linear interpolation between two consecutive alkanones).

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

Starting materials of formula (III):

Example Iil-l

A mixture of 26.0 g (185.5 mmol) of 3-methyl-furan-2-carboxylic acid methyl ester, 33.0 g (185.5 mmol) of N-bromosuccinimide (NBS), a spatula tip 2.2 ' -Azobis-2-methyl-propanenitrile and 150 ml of carbon tetrachloride is heated under reflux for 15 hours and then filtered. The filtrate is worked up by distillation under reduced pressure. 24.7 g (50% of theory) of 3-bromomethyl-furan-2-carboxylic acid methyl ester are obtained.

Boiling range: 62-64 ° C (0.1 Torr).

Application examples:

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

- To produce a suitable preparation of active compound, mix L parts by weight of active compound with the stated amount of solvent, add the stated amount of emulsifier and dilute the concentrate 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 active ingredient concentration in the spray liquor is selected 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 2, 3, 5, 6, 14, 17, 18, 19, 28, 29, 30, 31, 34, 35 and 36 show, in some cases, good tolerance to crop plants, such as, for example, maize, Soy and wheat, very strong against weeds. Example B

Post-emergence test

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 quantities of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 water / ha the desired amounts of active ingredient are applied.

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

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

2, 3, 4, 5, 6, 7, 8, 14, 16, 17, 18, 19, 20, 21, 22, 28, 29, 30, 31, 32, 33, 34, 35 and 36 in part good tolerance to crops, such as Wheat and sugar beet, very effective against weeds.

Claims

claims

1. Compounds of formula (I)

in which

represents O (oxygen), S (sulfur), SO or SO ₂ ,

R ^{1 represents} hydrogen, amino or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, halogen or C ₁ -C alkoxy,

R ^{2 represents} carboxy, cyano, carbamoyl, thiocarbamoyl or in each case alkyl or alkoxycarbonyl, each substituted by cyanp, halogen or C ₁ -C ₄ -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups,

R ^{3 represents} hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 6 carbon atoms, R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,

R ^{6 is} connected to A via a carbon atom, by cyano, carboxy, carbamoyl or thiocarbamoyl, or by Ci-C ₆ -alkoxycarbonyl, C ₃ -C ₆ -cycloalkyloxy-carbonyl or CrC ₆ -alkylamino-carbonyl (each of which, if appropriate are substituted by cyano, carboxy, halogen or CrCe-alkoxy-carbonyl), or by di- (C ₁ -C -alkyl) -amino-carbonyl or N- (C ₁ -C -alkoxy) -C ₁ -C ₄ - alkyl- amino-carbonyl, or C ₂ -C ₆ -alkenyloxy-carbonyl or C ₂ -C ₆ - alkynyloxy-carbonyl (which are in each case optionally substituted by halogen), or cyano-CrC _ö alkyl, carboxy-Ci- Ce-alkyl, Cr -AJJtoxy-carbonyl-CrCö-alkyl, cyano-C ₂ -C ₆ -alkenyl, carboxy-C ₂ -C ₆ -alkenyl or C ₁ -C ₄ -alkoxy-carbonyl-C ₂ -C ₆ - alkenyl (which are each optionally substituted by halogen), and optionally additionally by nitro, halogen or by C ₁ -C -

Alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or CC alkylsulfonyl (which are each optionally substituted by halogen) substituted, monocyclic or bicyclic heterocyclicl with up to 9 Carbon atoms and up to 5 heteroatoms, selected from up to 5 nitrogen atoms and / or up to 2 oxygen atoms and / or up to 2 sulfur atoms and optionally with up to 2 -SO groups, up to 2 -SO ₂ groups, up to 2 -CO groups or up to 2 -CS groups,

including the possible stereoisomeric forms. Compounds of formula (I) according to claim 1, characterized in that

A represents alkanediyl having 1 to 5 carbon atoms, alkenediyl having 2 to 5 carbon atoms or alkindiyl having 2 to 5 carbon atoms,

Q represents O (oxygen), S (sulfur) or SO ₂ ,

R ^{1 represents} hydrogen, amino or alkyl having 1 to 4 carbon atoms which is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy,

R ² for carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy

Alkyl or alkoxycarbonyl each having 1 to 4 carbon atoms in the alkyl groups,

R ^{3 represents} hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 4 carbon atoms,

R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or iodine,

R ^{5 represents} nitro, cyano, carbamoyl, thiocarbamoyl, halogen or in each case optionally substituted by halogen substituted alkyl or alkoxy each having 1 to 4 carbon atoms, and

R ⁶ for a bonded to A via a carbon atom, by cyano, carboxy, carbamoyl or thiocarbamoyl, or by Ci-Cs-alkoxycarbonyl, C ₅ -C ₆ -cycloalkyloxy-carbonyl or Ci-Cs-alkylamino- carbonyl (which are each optionally substituted by cyano, carboxy, halogen or C 1 -C ₄ -alkoxy-carbonyl), or by di- (C 1 -C 4 -alkyl) amino-carbonyl or N- (C 1 -C 4 -alkoxy) - C ₁ -C ₄ alkylamino carbonyl, or by C ₂ -C ₅ alkenyloxy carbonyl or C ₂ -C ₅ alkynyloxy carbonyl (which are each optionally substituted by halogen), or by cyano-Ci-Cs -alkyl, carboxy-d-Cs- alkyl, -C-C ₄ alkoxy-carbonyl-C ₁ -C ₅ alkyl ,. Cyano-C ₂ -C ₅ -alkenyl, carboxy-C ₂ -C ₅ -alkenyl or C ₁ -C -alkoxycarbonyl-C ₂ -C ₅ -alkenyl (which are each optionally substituted by halogen), and optionally additionally by nitro, Halogen or by -Gr

Alkyl, C ₁ -C ₄ -alkoxy, C ₁ -C ₄ -alkylthio, C ₁ -C ₄ -alkylsulfmyl or C ₁ -C ₄ -alkylsulfonyl (which are each optionally substituted by halogen) substituted, monocyclic or bicyclic heterocyclyl with up to 9 carbon atoms and up to to 5 heteroatoms selected from up to 3 nitrogen atoms and / or an oxygen atom and / or a sulfur atom, and optionally with an additional -SO group, an -SO ₂ group, a -CO group or a -CS group.

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

A represents alkanediyl having 1 to 4 carbon atoms, alkenediyl having 2 to 4 carbon atoms or AMndiyl having 2 to 4 carbon atoms,

Q represents O (oxygen) or S (sulfur),

R ^{1 represents} hydrogen, amino or methyl, ethyl or n- or i-propyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, R ^{2 represents} carboxy, cyano, carbamoyl, thiocarbamoyl or in each case optionally substituted by cyano, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy-substituted alkyl or alkoxycarbonyl each having 1 to 3 carbon atoms in the alkyl groups,

R ^{3 represents} hydrogen, fluorine, chlorine, bromine or methyl, ethyl or n- or i-propyl optionally substituted by fluorine and or chlorine,

R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine,

R ⁵ for nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or in each case optionally substituted by fluorine and / or chlorine

Is alkyl or alkoxy each having 1 to 3 carbon atoms, and

R ⁶ for a bonded to A via a carbon atom, by cyano, carboxy, carbamoyl or thiocarbamoyl, or by C ₁ -C ₄ alkoxycarbonyl, C ₅ -C ₆ cycloalkyloxycarbonyl or - alkylaminocarbonyl (which in each case, if appropriate are substituted by cyano, carboxy, halogen or C ₁ -C ₄ -alkoxy-carbonyl), or by di- (C ₁ -C ₃ -alkyl) -amino-carbonyl or N- (C ₁ -C ₃ -alkoxy) - C ₁ -C ₃ alkylamino-carbonyl, or by C ₃ -C ₄ alkenyloxy-carbonyl or C ₃ -C ₃ -alkynyloxy-carbonyl (which are each optionally substituted by halogen), or by cyano-Ci-cralkyl, Carboxy-C Cs-alkyl, Cr -alkoxy-carbonyl-Ci-Cs-alkyl, cyano-C ₂ -C ₃ -alkenyl, carboxy-C ₂ -C ₃ -alkenyl or C ₁ -C ₄ -alkoxy-carbonyl-C ₂ -C ₃ -alkenyl (which are each optionally substituted by halogen), and optionally additionally by nitro, halogen or by Cχ-C -

Alkyl, C ₁ -C alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ alkylsulfinyl or Ci C ₄ alkylsulfonyl (which are each optionally substituted by halogen) substituted heterocyclyl from the series furyl, benzofuryl, tetrahydrofuryl, thienyl, benzothienyl, pyrrolyl, benzopyrrolyl, pyrrolinyl, pyrazolyl, benzopyrazolyl, pyrazolinyl, imidazolyl, benzimidazolyl, benzimidazolyl, benzimidazolyl, benzimidazolyl, Oxazolyl, benzoxazolyl,

Oxazolinyl, isoxazolyl, isoxazolinyl, thiazolyl, benzthiazolyl, thiazolinyl, thiadiazolyl, triazolyl, pyridinyl, pyrimidinyl, triazinyl.

Compounds of formula (I) according to any one of claims 1 to 3, characterized in that

A for methylene, ethane-l, l-diyl, ethane-1,2-diyl (dimethylene), propane

1,1-diyl, propane-1,2-diyl, propane-l, 3-diyl, ethene-l, l-diyl, ethene-1,2-diyl, propene-1,1-diyl, propene-1, 2-diyl, propene-1,3-diyl, ethyne-1,2-diyl or propyne-1,3-diyl,

Q stands for O (oxygen),

R ^{1 represents} hydrogen, amino or in each case optionally by cyano,

Fluorine, chlorine, methoxy or ethoxy substituted methyl or ethyl,

R ^{2 represents} carboxy, cyano, carbamoyl, thiocarbamoyl or methyl, ethyl, methoxycarbonyl or ethoxycarbonyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ^{3 represents} hydrogen, fluorine, chlorine, bromine or methyl or ethyl which is in each case optionally substituted by fluorine and / or chlorine,

R ^{4 represents} hydrogen, cyano, fluorine or chlorine, R ^{5 represents} nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine or methyl, ethyl, methoxy or ethoxy which is optionally substituted by fluorine and / or chlorine, and

R ⁶ for a bonded to A via a carbon atom, by cyano, carboxy, carbamoyl or thiocarbamoyl ,. or by methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, cyclopentyloxycarbonyl, cyclohexyloxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl (which are each optionally replaced by cyano, carboxy, fluorine, chlorine, methoxycarbonyl, ethoxycarbonyl, n- or i-Propoxy-carbonyl are substituted), or by dimethylaminocarbonyl, diethylaminocarbonyl or N-methoxy-methylaminocarbonyl, or by propenyloxycarbonyl, butenyloxy-carbonyl, propynyloxycarbonyl or butynyloxy-carbonyl

(which are each optionally substituted by fluorine or chlorine), or by cyanomethyl, cyanoethyl, cyanopropyl, carboxyethyl, carboxyethyl, carboxypropyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, n- or i-propoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, n- or i- propoxycarbonylethyl,

Cyanoethenyl, cyanopropenyl, carboxyethenyl, carboxypropenyl, methoxycarbonylethenyl, ethoxycarbonylethenyl, n- or i-propoxycarbonylethenyl, methoxycarbonylpropenyl, ethoxycarbonylpropenyl, n- or i-propoxycarbόnylpropenyl (which are each optionally substituted by fluorine and / or chlorine) , Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i -Propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl (which are each optionally substituted by fluorine and / or chlorine)

Heterocyclyl from the series furyl, thienyl, pyrrolyl, pyrrolinyl, pyra- zolyl, pyrazolinyl, hnidazolyl, imidazolinyl, oxazolyl, oxazolinyl, isoxazolyl, isoxazolinyl, thiazolyl, thiazolinyl, pyridinyl, pyrimidinyl.

Compounds of formula (I) according to any one of claims 1 to 4, characterized in that

A represents methylene,

R ^{1 represents} hydrogen, methyl or amino,

R ^{2 represents} trifluoromethyl,

R ^{3 represents} hydrogen,

R ^{4 represents} fluorine,

R ^{5 represents} chlorine, bromine or cyano, and

R ^{6 represents} one of the following groupings (A) to (L)

(A) (B) (C)

(D) (E)

(F) (G)

wherein

Process for the preparation of compounds of the formula (I) according to one of Claims 1 to 5, characterized in that compounds of the formula (II)

in which

Q, R ¹ , R ² , R ³ , R ⁴ and R ^{5 have} the meanings given in one of Claims 1 to 5,

with substituted heterocycles of the general formula (III)

in which

A and R ^{6 have} the meanings given in one of claims 1 to 5 and

7. Agent, characterized by the content of at least one compound according to one of claims 1 to 5 and conventional extenders.

8. Use of compounds of formula (I) according to one of claims 1 to 5 or an agent according to claim 7 for controlling unwanted plants and / or arthropods.

Process for controlling unwanted plants and / or arthropods, characterized in that at least one compound of the formula (I) according to one of Claims 1 to 5 _. or an agent according to claim 7