DE19547475A1 - Substituted cyanophenyluracile - Google Patents

Abstract

The invention concerns novel substituted cyanophenyl uracils of general formula (I), in which R<1>, R<2>, R<3>, R<4>, R<5> and Q have the meanings indicated in the description. Also disclosed are processes for producing these compounds, novel intermediate products and their use as herbicides and insecticides.

Description

The invention relates to new substituted cyanophenyluracils, processes for their Production and their use as plant treatment agents, in particular as herbicides and insecticides.

It is known that certain substituted phenyluracils have herbicidal properties (see EP-408 382 / US-5 084 084 / US-5 127 935 / US-5 154 755, EP- 563,384, EP-648,749, WO 91/00278, US-4,979,982, US-5,169,430). This ver However, bonds have so far had no significant significance.

There were now the new substituted cyanophenyluracils of the general Formula (I) found

in which
Q represents O, S, SO or SO₂,
R¹ represents hydrogen, cyano or halogen,
R² represents hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
R³ represents hydrogen, halogen or an optionally substituted radical from the alkyl or alkoxy series,
R⁴ represents optionally substituted alkyl and
R⁵ represents hydrogen or an optionally substituted radical from the series alkyl, alkoxy, alkenyl or alkynyl, the known compounds 1- (4-cyano-2-fluoro-5-methylthio-phenyl) -3,6-dihydro-2 , 6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine, 1- (4-cyano-2-fluoro-5-methoxycarbonylmethylthio-phenyl) -3,6-dihydro-2,6-dioxo- 3-methyl-4-t-rifluoromethyl-1 (2H) pyrimidine and 1- [4-cyano-2-fluoro-5- (1-ethoxycarbonyl-ethylthio) phenyl] -3,6-dihydro-2 , 6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine- (cf. EP-408 382, p. 85 and US-5 084 084, col. 76) are excluded by disclaimers.

The new substituted cyanophenyluracils of the general formula (I) are obtained if
(a) substituted halophenyluracils of the general formula (II)

in which
R¹, R³, R⁴ and R⁵ have the meanings given above and
X represents halogen,
with nucleophilic compounds of the general formula (III)

M-Q-R² (III)

in which
Q and R² have the meanings given above and
M represents hydrogen or an alkali metal,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or if you
(b) substituted cyanophenyluracils of the general formula (Ia)

in which
Q, R¹, R², R³ and R⁴ have the meanings given above,
with an alkylating agent, if appropriate in the presence of a reaction auxiliary, and if appropriate in the presence of a diluent.

Draw the new substituted cyanophenyluracils of the general formula (I) are characterized by strong herbicidal and insecticidal activity.

In the definitions are the saturated or unsaturated hydrocarbon chains, such as alkyl, alkenyl or alkynyl, in each case straight-chain or branched.

Halogen generally represents fluorine, chlorine, bromine or iodine, preferably Fluorine, chlorine or bromine, especially for fluorine or chlorine.

The invention preferably relates to compounds of the formula (I)
in which
Q represents O, S, SO or SO₂,
R¹ represents hydrogen, cyano, fluorine or chlorine,
R² for hydrogen, each optionally by cyano, carboxy, fluorine, chlorine, bromine, C₁-C₄-alkoxy, C₁-C₄-alkylcarbonyl, C₁-C₄-alkoxy-carbonyl, di- (C₁-C₄-alkyl) -amino-carbonyl or N-C₁-C₄-alkyl-N-phenylamino carbonyl (where the phenyl group is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl or methoxy) substituted alkyl, alkenyl or alkynyl each with up to 10 carbon atoms, each optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkyl-carbonyl or C₁-C₄-alkoxy-carbonyl-substituted cycloalkyl or cycloalkylalkyl 3 to 8 carbon atoms in the cycloalkyl part and optionally up to 4 carbon atoms in the alkyl part, for each optionally by cyano, carboxy, nitro, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, by C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁ -C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄- alkyl-c arbonyl or C₁-C₄-alkoxy-carbonyl (which are optionally given by fluorine and / or chlorine), by phenyl, phenoxy or phenylthio (which in each case by fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and / or trifluoromethoxy are substituted) substituted aryl or arylalkyl having 6 or 10 carbon atoms in the aryl part and optionally up to 4 carbon atoms in the alkyl part,
R² further for each optionally by cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, by C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkylsulfonyl , C₁-C₄-alkyl carbonyl or C₁-C₄-alkoxy-carbonyl (which are each optionally by fluorine and / or chlorine), by phenyl, phenoxy or phenylthio (which are each optionally by fluorine, chlorine, bromine, cyano, methyl, methoxy , Trifluoromethyl and / or trifluoromethoxy are substituted) sub-substituted substituted furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxetanyl, thietanyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thia diazolyl, pyrazolyl, pyridolylinylazylidyl, pyridolylinyl, pyridinyl, pyridinyl, pyridolylinyl, pyridinyl, pyridyl, pyridylalyl, pyridinyl, pyridinyl, pyridyl, pyridylalyl, pyridolylyl, pyridyl, pyridyl, pyridyl, vinyl,
R³ represents hydrogen, fluorine, chlorine, bromine or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms,
R⁴ represents optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms and
R⁵ represents hydrogen or alkyl, alkoxy, alkenyl or alkynyl, each optionally substituted by fluorine, chlorine or C₁-C-alkoxy, each having up to 6 carbon atoms,
where the known compounds 1- (4-cyano-2-fluoro-5-methylthio-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine, 1 - (4-Cyano-2-fluoro-5-methoxycarbonylmethylthio-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4 - trifluoromethyl-1 (2H) -pyrimidine and 1- [4 -Cyano-2-fluoro-5- (1-ethoxycarbonyl-ethylthio) -phenyl] -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine- (cf. EP-408 382, p. 85 and US-5 084 084, Col. 76) are excluded by disclaimers.

The invention relates in particular to compounds of the formula (I)
in which
Q represents O, S, SO or SO₂,
R¹ represents hydrogen, fluorine or chlorine,
R² for hydrogen, for methyl optionally substituted by cyano, carboxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or diethylaminocarbonyl, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl,
R² further for each optionally by cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-prop oxy, acetyl or propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,
R² further for each optionally by cyano, carboxy, nitro, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy , Ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethyl sulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, benzyl or phenylethyl, or
R² further for each optionally by cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl , methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl oxy, by phenyl, Phen or phenylthio-substituted substituted furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxetanyl, thietanyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, Thiadiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, triazinyl, indolyl, quinolinyl or quinoxalinyl,
R³ represents hydrogen, fluorine, chlorine, bromine or methyl,
R⁴ is methyl, ethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, chloroethyl, fluoroethyl, dichloroethyl, dichloroethyl, chlorofluoroethyl, chlorodifluoroethyl, fluorodichloroethyl, trifluoroethyl, tetrafluoroethyl, and chlorotrifluoroethyl
R⁵ represents hydrogen or methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-, each substituted by fluorine, chlorine, meth oxy or ethoxy Propoxy, n-, i- or s-butoxy, propenyl, butenyl, propynyl or butynyl,
where the known compounds 1- (4-cyano-2-fluoro-5-methylthio-phenyl) -3,6-di hydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) pyrimidine, 1 - (4-cyano-2-fluoro-5-methoxycarbonylmethylthio-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-t-rifluoromethyl-1 (2H) -pyrimidine and 1- [4-cyano-2-fluoro-5- (1-ethoxycarbonyl-ethylthio) -phenyl] -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine- (cf. EP-408 382, p. 85 or US-5 084 084, col. 76) are excluded by disclaimers.

The radicals listed above or listed in preferred areas definitions apply both to the end products of the formula (I) and to the corresponding chend for the respective starting materials or intermediates required for production Products. These residual definitions can be among themselves, that is, between the specified preferred ranges can be combined as desired.

Examples of the compounds of formula (I) according to the invention are in the groups listed below.

Group 1

R² has, for example, the meanings given in the list below:

Hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, fluorodichloromethyl, Fluoroethyl, chloroethyl, chlorofluoroethyl, difluoroethyl, dichloroethyl, trifluoroethyl, Trichloroethyl, chlorodifluoroethyl, tetrafluoroethyl, chlorotrifluoroethyl, pentafluoroethyl, Fluoropropyl, chloropropyl, difluoropropyl, dichloropropyl, trifluoropropyl, trifluor propyl, cyanomethyl, cyanoethyl, cyanopropyl, cyanobutyl, carboxymethyl, Carboxyethyl, carboxypropyl, carboxybutyl, methoxymethyl, ethoxymethyl, Propoxymethyl, methoxyethyl, ethoxyethyl, propoxyethyl, methoxypropyl, Ethoxypropyl, propoxypropyl, methoxycarbonylmethyl, ethoxycarbonylmethyl, Propoxycarbonylmethyl, methoxycarbonylethyl, ethoxycarbonylethyl, propoxy carbonylethyl, methoxycarbonylpropyl, ethoxycarbonylpropyl, propoxycarbonyl propyl, 1-propen-3-yl (allyl), 3-methyl-1-propen-3-yl, 2-buten-4-yl (crotonyl), 1-  Propin-3-yl (propargyl), 3-methyl-1-propin-3-yl, 2-butyn-4-yl, cyclopropyl, Cyanocyclopropyl, carboxycyclopropyl, difluorocyclopropyl, dichlorocyclopropyl, Methylcyclopropyl, methoxycarbonylcyclopropyl, ethoxycarbonylcyclopropyl, Cyclobutyl, cyanocyclobutyl, carboxycyclobutyl, difluorocyclopropyl, trifluor cyclobutyl, tetrafluorocyclobutyl, chlorotrifluorocyclobutyl, methylcyclobutyl, cyclo pentyl, cyanocyclopentyl, carboxycyclopentyl, fluorocyclopentyl, chlorocyclo pentyl, difluorocyclopentyl, dichlorocyclopentyl, methylcyclopentyl, methoxy carbonylcyclopentyl, ethoxycarbonylcyclopentyl, cyclohexyl, cyanocyclohexyl, Carboxycyclohexyl, fluorocyclohexyl, chlorocyclohexyl, difluorocyclohexyl, dichloro cyclohexyl, methylcyclohexyl, trifluoromethylcyclohexyl, methoxycarbonylcyclo hexyl, ethoxycarbonylcyclohexyl, cyclopropylmethyl, difluorocyclopropylmethyl, Dichlorocyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexyl methyl, cyanocyclohexylmethyl, carboxycyclohexylmethyl, fluorocyclohexyl methyl, chlorocyclohexylmethyl, methylcyclohexylmethyl, trifluoromethylcyclo hexylmethyl, phenyl, cyanophenyl, carboxyphenyl, nitrophenyl, fluorophenyl, Chlorophenyl, bromophenyl, methylphenyl, trifluoromethylphenyl, methoxyphenyl, Difluoromethoxyphenyl, trifluoromethoxyphenyl, methoxycarbonylphenyl, ethoxy carbonylphenyl, benzyl, cyanobenzyl, carboxybenzyl, fluorobenzyl, chlorobenzyl, Methylbenzyl, trifluoromethylbenzyl, methoxybenzyl, difluoromethoxybenzyl, Trifluoromethoxybenzyl, methoxycarbonylbenzyl, ethoxycarbonylbenzyl, phenyl ethyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxetanyl, oxazolyl, Isoxazolyl.

Group 2

R² has, for example, the meanings listed above in Group 1.

Group 3

R² has, for example, the meanings listed above in Group 1.

Group 4

R² has, for example, the meanings listed above in Group 1.

Group 5

R² has, for example, the meanings listed above in Group 1.  

Group 6

R² has, for example, the meanings listed above in Group 1.

Group 7

R² has, for example, the meanings listed above in Group 1.

Group 8

R² has, for example, the meanings listed above in Group 1.  

Group 9

R² has, for example, the meanings listed above in Group 1.

Group 10

R² has, for example, the meanings listed above in Group 1.

Group 11

R² has, for example, the meanings listed above in Group 1.  

Group 12

R² has, for example, the meanings listed above in Group 1.

Group 13

R² has, for example, the meanings listed above in Group 1.

Group 14

R² has, for example, the meanings listed above in Group 1.  

Group 15

R² has, for example, the meanings listed above in Group 1.

Group 16

R² has, for example, the meanings listed above in Group 1.

Group 17

R² has, for example, the meanings listed above in Group 1.  

Group 18

R² has, for example, the meanings listed above in Group 1.

Group 19

R² has, for example, the meanings listed above in Group 1.

Group 20

R² has, for example, the meanings listed above in Group 1.  

If, for example, 1- (4-cyano-2,5-difluorophenyl) -3,6-dihydro-2,6-di is used oxo-5-chloro-4-difluoromethyl-3-methyl-1 (2H) -pyrimidine and potassium ethylate as out materials, the course of the reaction in process (a) according to the invention can be outlined by the following formula:

For example, 1- (2-chloro-4-cyano-5-methylthio-phenyl) -3,6-dihy is used dro-2,6-dioxo-4-chlorodifluoromethyl-5-methyl-1 (2H) -pyrimidine and bromomethane as Starting materials, so the course of the reaction in the process according to the invention (b) are outlined by the following formula scheme:

The process according to the invention for the preparation of the compounds of Formula (I) substituted halophenyl to be used as starting materials uracile are generally defined by the formula (II). In formula (II), R¹, R³, R⁴ and R⁵ preferably or in particular that meaning that already above in the description of the compounds to be produced according to the invention Formula (I) preferably or as particularly preferred for R¹, R³, R⁴ and R⁵ was specified; X preferably represents fluorine, chlorine or bromine, in particular for fluorine.

The starting materials of formula (II) are known and / or can be per se known processes can be produced (cf. EP 648749, production examples).  

The process according to the invention for the preparation of the compounds of Formula (I) further used as starting materials nucleophilic compounds are generally defined by the formula (III). In formula (III), Q and R² preferably or in particular that meaning already above in the Description of the compounds of the formula (I) to be prepared according to the invention preferably or as particularly preferred for Q and R²; M preferably represents hydrogen, lithium, sodium or potassium, in particular for hydrogen, sodium or potassium.

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

Process (a) according to the invention for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a suitable reaction auxiliary guided. The usual inorganic auxiliaries generally come or organic bases or acid acceptors. This includes preferably alkali metal or alkaline earth metal acetates, amides, carbonates, hy drug carbonates, hydrides, hydroxides or alkanolates, such as Na trium, 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 trimethylamine, triethyl amine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclo hexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, 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), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), and 1.8 diazabicyclo [5,4,0] undec-7-en (DBU).

Process (a) according to the invention for the preparation of the compounds of the formula (I) is preferably carried out in the presence of a diluent. As Diluents generally come with the usual organic solutions medium into consideration. These preferably include aliphatic, alicyclic and aro Matic, optionally halogenated hydrocarbons, such as pen tan, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, chlorine  benzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (methylene chloride), trichloromethane (chloroform) or carbon tetrachloride, dialkyl ether, such as for example diethyl ether, diisopropyl ether, methyl t-butyl ether (MTBE), ethyl t-butyl ether, methyl t-pentyl ether (TAME), ethyl t-pentyl ether, tetrahydrofuran (THF), 1,4-dioxane, ethylene glycol dimethyl ether or diethyl ether, diethylene glycol dimethyl ether or diethyl ether; Dialkyl ketones, such as acetone, Butanone (methyl ethyl ketone), methyl i-propyl ketone or methyl i-butyl ketone, Ni triles such as acetonitrile, propionitrile, butyronitrile or benzonitrile; Amides, such as N, N-dimethylformamide (DMF), N, N-dimethyl-acet amide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl-phosphoric acid triamid; Esters, such as, for example, methyl acetate, ethyl ester, n or i propyl ester, -n-, -i- or -s-butyl ester; Sulfoxides such as dimethyl sulfoxide; Alkanols, such as methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether or monoethyl ether, Di ethylene glycol monomethyl ether or monoethyl ether; their mixtures with water or pure water.

The reaction temperatures can be carried out when carrying out the process according to the invention Process (a) can be varied over a wide range. Generally works one at temperatures between 0 ° C and 200 ° C, preferably between 10 ° C and 150 ° C.

Process (a) according to the invention is generally carried out under atmospheric pressure carried out. However, it is also possible to use the method according to the invention increased or reduced pressure - generally between 0.1 bar and 10 bar - to be carried out.

To carry out process (a) according to the invention, the starting substances 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 for several hours at the required temperature. The processing is carried out according to customary methods (cf. the manufacturer examples).  

The process (b) according to the invention for the preparation of the compounds of Formula (I) substituted cyanophenyluracils to be used as starting materials are generally defined by the formula (Ia). In formula (Ia) Q, R¹, R², R³ and R⁴ preferably or in particular that meaning already above in the description of the compounds of For mel (I) preferably or as particularly preferred for Q, R¹, R², R³ and R⁴ was specified.

The starting materials of the formula (Ia) are new compounds according to the invention; they can be prepared by process (a) according to the invention.

Process (b) according to the invention is carried out using an alkylation carried out by means. Among alkylating agents are in this context preferably optionally substituted by fluorine, chlorine or C₁-C₄ alkoxy Alkyl, alkenyl or alkynyl halides (especially chlorides, bromides or Iodides) each with up to 6 carbon atoms or dialkyl sulfates with up to 6 Understand carbon atoms in the alkyl groups. It is about known synthetic chemicals.

Process (b) according to the invention for the preparation of the compounds of For mel (I) is preferably in the presence of a suitable reaction auxiliary carried out. The usual reaction aids generally arrive organic or organic bases or acid acceptors. For this ge preferably hear alkali metal or alkaline earth metal acetates, amides, carbo nates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as, for example Sodium, potassium or calcium acetate, lithium, sodium, potassium or cal cium 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 methanolate, ethanolate, n- or i-propanolate, n-, i-, s- or t-butanolate; Farther also basic organic nitrogen compounds, such as trimethyl amine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-Di methyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N-dime thyl-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), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), and 1.8 diaza bicyclo [5,4,0] -undec-7-ene (DBU).

Process (b) according to the invention for the preparation of the compounds of For mel (I) is preferably carried out in the presence of a diluent. The usual organic solvents are generally used as diluents means. These preferably include aliphatic, alicyclic and aromatic, optionally halogenated hydrocarbons, such as white pentane, hexane, heptane, petroleum ether, ligroin, gasoline, benzene, toluene, xylene, Chlorobenzene, dichlorobenzene, cyclohexane, methylcyclohexane, dichloromethane (Me ethylene chloride), trichloromethane (chloroform) or carbon tetrachloride, dialkyl ether, such as, for example, diethyl ether, diisopropyl ether, methyl t-butyl ether (MTBE), Ethyl t-butyl ether, methyl t-pentyl ether (TAME), ethyl t-pentyl ether, tetrahydro furan (THF), 1,4-dioxane, ethylene glycol dimethyl ether or diethyl ether, Di ethylene glycol dimethyl ether or diethyl ether; Dialkyl ketones, such as Acetone, butanone (methyl ethyl ketone), methyl i-propyl ketone or methyl i-butyl ketone, nitriles such as acetonitrile, propionitrile, butyronitrile or benzo nitrile; Amides such as N, N-dimethylformamide (DMF), N, N-dimethyl acetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethyl-phosphorus acid triamide; Esters, such as, for example, methyl acetate, ethyl ester, n- or -i-propyl ester, -n-, -i- or -s-butyl ester; Sulfoxides such as dimethyl sulfoxide; Alkanols, such as methanol, ethanol, n- or i-propanol, n-, i-, s- or t-butanol, ethylene glycol monomethyl ether or monoethyl ether, Di ethylene glycol monomethyl ether or monoethyl ether; their mixtures with water or pure water.

The reaction temperatures can be carried out when carrying out the process according to the invention Process (b) can be varied over a wide range. Generally working tet at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C. and 120 ° C.

Process (b) according to the invention is generally carried out under normal pressure carried out. However, it is also possible to use the method according to the invention increased or reduced pressure - generally between 0.1 bar and 10 bar - to be carried out.  

The starting materials are used to carry out the process according to the invention generally used in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. The The reaction is generally carried out in a suitable diluent In the presence of a reaction auxiliary and the reaction mixture is generally stirred for several hours at the required temperature. The processing is carried out according to customary methods (cf. the manufacturer examples). The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are in places grow up where they are undesirable. Whether the substances according to the invention as total or selective herbicides act essentially depends on the applied Amount off.

The active compounds according to the invention can, for. B. ver used in the following plants:
Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matri caria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Sonuum, Carduus Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranun culus, Taraxacum.

Dicot cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, lactuca, cucumis, cucurbita.

Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecu rus, apera.  

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, sorghum, panicum, saccharum, pineapple, asparagus, allium.

However, the use of the active compounds according to the invention is by no means limited to limited to these genera, but also extends in the same way other plants.

Depending on the concentration, the compounds are suitable for the total weed control z. B. on industrial and track systems and on paths and Places with and without tree cover. Likewise, the connections to Weed control in permanent crops, e.g. B. forest, ornamental trees, fruit, wine, Citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hops, on ornamental and sports turf and pastures and for selective Weed control can be used in annual crops.

The compounds of formula (I) according to the invention are particularly suitable for selective control of monocot and dicot weeds in mono cotyledonous and dicotyledon cultures both in the pre- and post-emergence Method.

Furthermore, the compounds of the formula (I) according to the invention also show strong ones insecticidal activity, especially against beetle larvae, such as B. Phaedon coch leariae, and against caterpillars, e.g. B. Plutella xylostella.

To a certain extent, the compounds of formula (I) also show fungicides Effect, for example against Pyricularia oryzae on rice.

With good plant tolerance and favorable warm-blood toxicity, the active substances are suitable for combating animal pests, in particular insects, arachnids and nematodes, which occur in agriculture, in forests, in the protection of stored products 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. The pests mentioned above include:
From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Por cellio scaber.
From the order of the Diplopoda z. B. Blaniulus guttulatus.
From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spec.
From the order of the Symphyla z. B. Scutigerella immaculata.
From the order of the Thysanura z. B. Lepisma saccharina.
From the order of the Collembola z. B. Onychiurus armatus.
From the order of Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leucophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria.
From the order of the Dermaptera z. B. Auricular Forficula.
From the order of the Isoptera z. B. Reticulitermes spp. .
From the order of the Anoplura z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.
From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp.
From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.
From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.
From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeurodes vaporariorum, Aphis gossypii, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Phylloxera vastatrix, Pemphigus sppe, Phrosiphumumonpp., Macrosiphumum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantii, Aspidiotus hederae, Pseudococcus spp., Psylla spp.
From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosomaneustria, Euproctischrysorrhoea, Lymantria spp., Bucculatrix thurberiisisppiasppia, Phyllella. Phyllocnella, Phylloc spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Spodoptera litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonelliellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaellaella , Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magnanima, Tortrix viridana.
From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Bruchidius obtectus, Acanthoscelides obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chrysocephppis, Orphusus spp. , Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assimilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Giptusibbium psol. Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.
From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.
From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomox ., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.
From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp. .
From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.
From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Choroptes spp.,. Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp. .
The plant parasitic nematodes include z. B. Pratylenchus spp., Radopho lus similis, Ditylenchus dipsaci, Tylenchulus semipenetrans, Heterodera spp., Glo bodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp. .
Mixing partners suitable for use are e.g. B. the following:

Fungicides

2-aminobutane; 2-anilino-4-methyl-6-cyclopropyl-pyrimidine; 2 ′, 6′-dibromo-2-me thyl-4'-trifluoromethoxy-4'-trifluoromethyl-1,3-thiazole-5-carboxani-lid; 2,6-Tue chloro-N- (4-trifluoromethylbenzyl) benzamide; (E) -2-methoxyimino-N-methyl-2- (2- phenoxyphenyl) acetamide; 8-hydroxyquinoline sulfate; Methyl- (E) -2- {2- [6- (2-cyano phenoxy) pyrimidin-4-yloxy] phenyl} -3-methoxyacrylate; Methyl- (E) -methoximino- [alpha- (o-tolyloxy) -o-tolyl] acetate; 2-phenylphenol (OPP), aldimorph, ainpropylfos, Anilazine, azaconazole, Benalaxyl, Benodanil, Benomyl, Binapacryl, Biphenyl, Bitertanol, Blasticidin-S, Bromuconazole, Bupirimate, Buthiobate, Calcium polysulfide, captafol, captan, carbendazim, carboxin, quinomethionate (Quinomethionate), chloroneb, chloropicrin, chlorothalonil, chlozolinate, cufraneb, Cymoxanil, cyproconazole, cyprofuram, Dichlorophen, diclobutrazole, diclofluanide, diclomezin, dicloran, diethofencarb, Difenoconazole, dimethirimol, dimethomorph, diniconazole, dinocap, diphenyl amine, dipyrithione, ditalimfos, dithianon, dodine, drazoxolone, Edifenphos, epoxyconazole, ethirimol, etridiazole, Fenarimol, Fenbuconazole, Fenfuram, Fenitropan, Fenpiclonil, Fenpropidin, Fen propimorph, fentin acetate, fentin hydroxide, ferbam, ferimzone, fluazinam, fludi  oxonil, fluoromide, fluquinconazole, flusilazole, flusulfamide, flutolanil, flu triafol, folpet, fosetyl aluminum, fthalides, fuberidazole, furalaxyl, furmecyclox, Guazatine, Hexachlorobenzene, hexaconazole, hymexazole, Imazalil, Imibenconazol, Iminoctadin, Iprobefos (IBP), Iprodione, Isoprothiolan, Kasugamycin, copper preparations such as: copper hydroxide, copper naphthenate, Copper oxychloride, copper sulfate, copper oxide, oxine copper and Bordeaux-Mi shung, Mancopper, Mancozeb, Maneb, Mepanipyrim, Mepronil, Metalaxyl, Metconazol, Methasulfocarb, methfuroxam, metiram, metsulfovax, myclobutanil, Nickel dimethyldithiocarbamate, nitrothal isopropyl, Nuarimol, Ofurace, oxadixyl, oxamocarb, oxycarboxin, Pefurazoate, penconazole, pencycuron, phosdiphene, phthalide, pimaricin, piperalin, Polycarbamate, polyoxin, probenazole, prochloraz, procymidon, propamocarb, pro piconazole, Propineb, Pyrazophos, Pyrifenox, Pyrimethanil, Pyroquilon, Quintozen (PCNB), Sulfur and sulfur preparations, Tebuconazole, tecloftalam, tecnazen, tetraconazole, thiabendazole, thicyofen, Thiophanat-methyl, Thiram, Tolclophos-methyl, Tolylfluanid, Triadimefon, Triadi menol, triazoxide, trichlamide, tricyclazole, tridemorph, triflumizole, triforin, tri ticonazole, Validamycin A, vinclozolin, Zineb, ziram.  

Bactericides

Bronopol, dichlorophene, nitrapyrin, nickel dimethyldithiocarbamate, Kasugamy cin, octhilinone, furan carboxylic acid, oxytetracycline, probenazole, streptomycin, Tecloftalam, copper sulfate and other copper preparations.

Insecticides / acaricides / nematicides

Abamectin, AC 303 630, acephate, acrinathrin, alanycarb, aldicarb, alpha methrin, Amitraz, Avermectin, AZ 60541, Azadirachtin, Azinphos A, Azinphos M, Azocyclotin, Bacillus thuringiensis, Bendiocarb, Benfuracarb, Bensultap, Betacyfluthrin, Bi fenthrin, BPMC, Brofenprox, Bromophos A, Bufencarb, Buprofezin, Butocarboxin, Butyl pyridaben, Cadusafos, Carbaryl, Carbofuran, Carbophenothion, Carbosulfan, Cartap, CGA 157 419, CGA 184699, chloethocarb, chlorethoxyfos, chlorfenvinphos, chlorine fluazuron, Chlormephos, Chlorpyrifos, Chlorpyrifos M, Cis-Resmethrin, Clocy thrin, clofentezin, cyanophos, cycloprothrin, cyfluthrin, cyhalothrin, cyhexatin, Cypermethrin, cyromazine, Deltamethrin, Demeton M, Demeton S, Demeton-S-methyl, Diafenthiuron, Di azinon, dichlofenthion, dichlorvos, dicliphos, dicrotophos, diethion, diflu benzuron, dimethoate, dimethylvinphos, dioxathione, disulfoton, Edifenphos, Emamectin, Esfenvalerat, Ethiofencarb, Ethion, Ethofenprox, Etho prophos, etrimphos, Fenamiphos, fenazaquin, fenbutatin oxide, fenitrothion, fenobucarb, fenothiocarb, Fenoxycarb, Fenpropathrin, Fenpyrad, Fenpyroximat, Fenthion, Fenvalerate, Fipro nil, fluazinam, flucycloxuron, flucythrinate, flufenoxuron, flufenprox, fluvalinate, Fonophos, Formothion, Fosthiazat, Fubfenprox, Furathiocarb, HCH, heptenophos, hexaflumuron, hexythiazox, Imidacloprid, Iprobefos, Isazophos, Isofenphos, Isoprocarb, Isoxathion, Iver mectin, lambda-cyhalothrin, lufenuron,  Malathion, Mecarbam, Mervinphos, Mesulfenphos, Metaldehyde, Methacrifos, Methamidophos, methidathione, methiocarb, methomyl, metolcarb, milbemectin, Monocrotophos, moxidectin, Naled, NC 184, M 25, Nitenpyram, Omethoate, Oxamyl, Oxydemethon M, Oxydeprofos, Parathion A, Parathion M, Permethrin, Phenthoat, Phorat, Phosalon, Phosmet, Phosphamidon, Phoxim, Pirimicarb, Pirimiphos M, Pirimiphos A, Profenofos, Promecarb, Propaphos, Propoxur, Prothiofos, Prothoat, Pymetrozin, Pyrachlophos, Pyradaphenthion, Pyresmethrin, Pyrethrum, Pyridaben, Pyrimidifen, Pyriproxifen, Quinalphos, RH 5992, Salithion, Sebufos, Silafluofen, Sulfotep, Sulprofos, Tebufenozid, Tebufenpyrad, Tebupirimphos, Teflubenzuron, Tefluthrin, Temephos, Terbam, Terbufos, Tetrachlorvinphos, Thiafenox, Thiodicarb, Thiofanox, Thiome thon, thionazin, thuringiensin, tralomethrin, triarathen, triazophos, triazuron, Trichlorfon, triflumuron, trimethacarb, Vamidothione, XMC, xylylcarb, YI 5301/5302, zetamethrin.

A mixture with other known active ingredients, such as herbicides or with Fertilizers and growth regulators are possible.

The active compounds according to the invention can also be used in their commercially available form formulations and in the application forms prepared from these formulations in a mixture with synergists. Synergists are connections through which the effect of the active ingredients is increased without the added synergist must be actively active itself.

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

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

When used against hygiene and storage pests, the stands out Active ingredient through an excellent residual effect on wood and clay as well due to good stability to alkali on limed substrates.

The active compounds according to the invention act not only against plant, hygiene and stored-product pests, but also in the veterinary sector against animal parasites (ectoparasites) such as tick ticks, leather ticks, mites, running mites, flies (stinging and licking), parasitic fly larvae, lice, hair lice, Featherlings and fleas. These parasites include:
From the order of the Anoplurida z. B. Haematopinus spp., Linognathus spp., Pediculus spp., Phtirus spp., Solenopotes spp. .
From the order of the Mallophagida and the subordinates Amblycerina and Ischnocerina z. B. Trimenopon spp., Menopon spp., Trinoton spp., Bovicola spp., Wemeckiella spp., Lepikentron spp., Damalina spp., Trichodectes spp., Felicola spp. .
From the order Diptera and the subordinates Nematocerina and Brachycerina z. B. Aedes spp., Anopheles spp., Culex spp., Simulium spp., Eusimulium spp., Phlebotomus spp., Lutzomyia spp., Culicoides spp., Chrysops spp., Hybomitra spp., Atylotus spp., Tabanus spp., Haematopota spp., Philipomyia spp., Braula spp., Musca spp., Hydrotaea spp., Stomoxys spp., Haematobia spp., Morellia spp., Fannia spp., Glossina spp., Calliphora spp., Lucilia spp., Chrysomyia spp ., Wohlfahrtia spp., Sarcophaga spp., Oestrus spp., Hypoderma spp., Gasterophilus spp., Hippobosca spp., Lipoptena spp., Melophagus spp. .
From the order of the Siphonapterida z. B. Pulex spp., Ctenocephalides spp., Xenopsylla spp., Ceratophyllus spp. .
From the order of the Heteropterida z. B. Cimex spp., Triatoma spp., Rhodnius spp., Panstrongylus spp. .
From the order of the Blattarida z. B. Blatta orientalis, Periplaneta americana, Blattela germanica, Supella spp. .
From the subclass of Acaria (Acarida) and the orders of the Meta and Mesostigmata z. B. Argas spp., Ornithodorus spp., Otobius spp., Ixodes spp., Amblyomma spp., Boophilus spp., Dermacentor spp., Haemophysalis spp., Hyalomma spp., Rhipicephalus spp., Dermanyssus spp., Raillietia spp. Pneumonyssus spp., Sternostoma spp., Vairoa spp. .
From the order of the Actinedida (Prostigmata) and Acaridida (Astigmata) z. B. Acarapis spp., Cheyletiella spp., Ornithocheyletia spp., Myobia spp., Psorergates spp., Demodex spp., Trombicula spp., Listrophorus spp., Acarus spp., Tyrophagus spp., Caloglyphus spp., Hypodectes spp. Pterolichus spp., Psoroptes spp., Chorioptes spp., Otodectes spp., Sarcoptes spp., Notoedres spp., Knemidocoptes spp., Cytodites spp., Laminosioptes spp. .
The active compounds of the formula (I) according to the invention are also suitable for controlling arthropods which are agricultural animals, such as, for. B. cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as. B. dogs, cats, house birds, aquarium fish and so-called experimental animals, such as. B. hamsters, sea pigs, rats and mice infested. By fighting these arthro pods death cases and reduced performance (for meat, milk, wool, skins, eggs, honey, etc.) are to be reduced, so that more economical and simple animal husbandry is possible through the use of the active compounds according to the invention.

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, Tab Latvian, capsules, watering, drenching, granules, pastes, boluses, feed-through Method, of suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), Implan tate, by nasal application, by dermal application in the form, for example of diving or bathing (dipping), spraying (spray), pouring on (pour-on and  Spot-on), washing, powdering and with the help of active ingredients Shaped bodies, such as collars, ear tags, tail tags, limb straps, Halters, marking devices etc.

When used for cattle, poultry, pets etc. you can use the active ingredients of the formula (I) as formulations (for example powders, emulsions, flowable Agents), which contain the active ingredients in an amount of 1 to 80 wt .-%, directly or after 100 to 10,000-fold dilution, or as a chemical Use bath.

It has also been found that the compounds of the formula (I) show a high insecticidal activity against insects, the technical materia destroy lien.

The following insects may be mentioned by way of example and preferably, but without limitation:
Beetles such as Hylotrupes bajulus, Chlorophorus pilosis, Anobium punctatum, Xestobium rufovillosum, Ptilinus pecticornis, Dendrobium pertinex, Emobius mollis, Priobium carpini, Lyctus brunneus, Lyctus africanus, Lyctus planicollicesis, Lyctusollisisisis, Lyctusollisoxis, Lyctus pubxisis Xyle borus spec. Tryptodendron spec. Apate monachus, Bostrychus capucins, Hetero bostrychus brunneus, Sinoxylon spec. Dinoderus minutus;
Common wing such as Sirex juvencus, Urocerus gigas, Urocerus gigas taignus, Urocerus augur;
Termites such as Kalotermes flavicollis, Cryptotermes brevis, Heterotermes indicola, Reticulitermes flavipes, Reticulitermes santonensis, Reticulitermes lucifugus, Mastotermes darwiniensis, Zootermopsis nevadensis, Coptotermes formosanus;
Bristle tail like Lepisma saccarina.

In the present context, technical materials include non-living ones To understand materials, such as preferably plastics, adhesives, glues, Pa paper and cardboard, leather, wood and wood processing products and paints.  

It is very particularly preferred to prevent insect attack protective material around wood and wood processing products.

Among wood and wood processing products, which by the inventive Agents or mixtures containing them can be protected is exemplary to understand: timber, wooden beams, railway sleepers, bridge parts, jetties, Wooden vehicles, boxes, pallets, containers, telephone poles, wooden panels, Wooden windows and doors, plywood, chipboard, carpentry or wood products that are used in general in house construction or in joinery Find.

The active ingredients can be used as such, in the form of concentrates or in general usual formulations such as powders, granules, solutions, suspensions, emul sions or pastes.

The formulations mentioned can be prepared in a known manner, for. B. by mixing the active ingredients with at least one solution or diluent agents, emulsifiers, dispersants and / or binders or fixatives, water Repellants, optionally desiccants and UV stabilizers and if necessary Dyes and pigments as well as other processing aids.

The insecticidal agents used to protect wood and wood-based materials or concentrates contain the active ingredient according to the invention in a concentra tration from 0.0001 to 95 wt .-%, in particular 0.001 to 60 wt .-%.

The amount of agents or concentrates used depends on the type and type come from insects and depending on the medium. The optimal amount to use can be determined by test series in the application. Generally in my opinion, however, it is sufficient 0.0001 to 20% by weight, preferably 0.001 to 10 wt .-%, of the active ingredient, based on the material to be protected.

An organic chemical solvent serves as the solvent and / or diluent solvent or solvent mixture and / or an oily or oily heavy volatile organic chemical solvent or solvent mixture and / which is a polar organic chemical solvent or solvent mixture and / or water and optionally an emulsifier and / or wetting agent.  

The organic chemical solvents used are preferably oily or oily ones Solvents with an evaporation number above 35 and a flash point above half 30 ° C, preferably above 45 ° C, used. As such volatile, Water-insoluble, oily and oily solvents become corresponding minerals oils or their aromatic fractions or mineral oil-containing solvent mixtures, preferably white spirit, petroleum and / or alkylbenzene used. Mineral oils with a boiling range of 170 to 220 ° C are advantageous, test petrol with a boiling range of 170 to 220 ° C, spindle oil with a boil range from 250 to 350 ° C, petroleum or aromatics with a boiling range of 160 up to 280 ° C, turpentine oil and the like.

In a preferred embodiment, liquid aliphatic hydrocarbons substances with a boiling range of 180 to 210 ° C or high-boiling mixtures of aromatic and aliphatic hydrocarbons with a boiling range from 180 to 220 ° C and / or locker oil and / or monochloronaphthalene, preferably two se α-monochloronaphthalene used.

The organic non-volatile oily or oily solvents with a Evaporation rate above 35 and a flash point above 30 ° C, preferably above 45 ° C, can be partly due to slightly or medium volatile organic Mix solvent to be replaced, provided that the solvent mix also an evaporation number above 35 and a flash point above 30 ° C, preferably above 45 ° C, and that the insecticide fungicide Mixture is soluble or emulsifiable in this solvent mixture.

According to a preferred embodiment, part of the organic chemical Solvent or solvent mixture or an aliphatic polar orga niche chemical solvent or solvent mixture replaced. Preferably come alipha containing hydroxyl and / or ester and / or ether groups organic chemical solvents such as glycol ether, esters or the like for use.

As an organic chemical binder in the present Er finding the known water-dilutable and / or in the used organic chemical solvents soluble or dispersing or emul gable synthetic resins and / or binding drying oils, especially binders  consisting of or containing an acrylic resin, a vinyl resin, e.g. B. polyvinyl acetate, Polyester resin, polycondensation or polyaddition resin, polyurethane resin, alkyd resin or modified alkyd resin, phenolic resin, hydrocarbon resin such as indene Coumarone resin, silicone resin, drying vegetable and / or drying oils and / or physically drying binders based on a natural and / or Resin used.

The synthetic resin used as a binder can be in the form of an emulsion, disper sion or solution. Bitumen or bituminous substances up to 10 wt .-%, are used. In addition, you can known dyes, pigments, water repellants, odor correctors and Inhibitors or anticorrosive agents and the like are used.

According to the invention, preference is given to organic chemical binders least an alkyd resin or modified alkyd resin and / or a drying one vegetable oil contained in the medium or in the concentrate. According to the invention alkyd resins with an oil content of more than 45 wt .-%, preferably as 50 to 68 wt .-%, used.

The binder mentioned can be wholly or partly by means of a fixing agent tel (mixture) or by a plasticiser (mixture). This too sentences should volatilize the active ingredients and crystallize or Prevent failures. They preferably replace 0.01 to 30% of the binder (based on 100% of the binder used).

The plasticizers come from the chemical classes of phthalic acid esters such as Dibutyl, dioctyl or benzyl butyl phthalate, phosphoric acid esters such as tributyl phosphate, adipic acid esters such as di- (2-ethylhexyl) adipate, stearates such as butyl stearate or amyl stearate, oleates such as butyl oleate, glycerol ether or higher molecular weight Gly kolether, glycerol ester and p-toluenesulfonic acid ester.

Fixing agents are chemically based on polyvinyl alkyl ethers such as. B. Polyvinyl methyl ether or ketones such as benzophenone, ethylene benzophenone.

Water is also particularly suitable as a solvent or diluent, optionally in a mixture with one or more of the above or  ganic-chemical solvents or diluents, emulsifiers and dispersers gators.

A particularly effective wood protection is provided by industrial impregnation drive, e.g. B. vacuum, double vacuum or printing process.

The ready-to-use agents can optionally also be other insecticides and optionally contain one or more fungicides.

The additional mixing partners are preferably those in WO 94/29 268 Insecticides and fungicides mentioned in question. The ones mentioned in this document Connections are an integral part of this application.

Insecticides such as chlorine can be used as very particularly preferred mixing partners pyriphos, phoxim, silafluofin, alphamethrin, cyfluthrin, cypermethrin, delta methrin, permethrin, imidacloprid, M-25, flufenoxuron, hexaflumuron and tri flumuron, as well as fungicides such as epoxyconazole, hexaconazole, azaconazole, propiconazole, Tebuconazole, cyproconazole, metconazole, imazalil, dichlorofiuanide, tolylfluanid, 3-iodo-2-propynyl butyl carbamate, N-octyl-isothiazolin-3-one and 4,5-dichloro-N- octylisothiazolin-3-one.

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 nated natural and synthetic substances as well as very fine encapsulation in polymers Fabrics.

These formulations are prepared in a known manner, e.g. B. by Ver mixing the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surface-active agents Agents, that is emulsifiers and / or dispersants and / or foam generators resources.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl  naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylene or methylene chloride, aliphatic coal water serstoffe, such as cyclohexane or paraffins, e.g. B. 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.

As solid carriers come into question: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks like Calcite, marble, pumice, sepiolite, dolomite and synthetic granules from an organic and organic flours and granules made from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as an emulsifier and / or foam-generating agents are possible: z. B. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fat alcohol ether, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. Lignin sulfite liquor and methyl cellulose.

In the formulations, adhesives such as carboxymethyl cellulose, ver natural and synthetic polymers in powder, granular or latex form be used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, as well natural phospholipids such as cephalins and lecithins and synthetic phos pholipid. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, Ferrocyan blue and organic dyes such as alizarin, azo and metal phthalalo cyanine 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 weight percent active ingredient, preferably between 0.5 and 90%.  

The active compounds according to the invention can be used as such or in their form in mixtures with known herbicides for weed control Ver find application, whereby finished formulations or tank mixes are possible.

Known herbicides are suitable for the mixtures, for example anilides, such as B. Diflufenican and Propanil; Arylcarboxylic acids, such as. B. dichloropicolin acid, dicamba and picloram; Aryloxyalkanoic acids, such as. B. 2.4 D, 2.4 DB, 2.4 DP, fluroxypyr, MCPA, MCPP and triclopyr; Aryloxy-phenoxy-alkanoic acid esters, such as B. Diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; Azinones, such as B. Chloridazon and Norflurazon; Carbamates, such as B. Chlorpropham, Desmedipham, Phenmedipham and Propham; Chloroacet anili4e, such as B. alachlor, acetochlor, butachlor, metazachlor, metolachlor, Pretilachlor and propachlor; Dinitroanilines such as e.g. B. Oryzalin, Pendimethalin and Trifluralin; Diphenyl ether, such as. B. acifluorfen, bifenox, fluoroglycofen, Fomesafen, halosafen, lactofen and oxyfluorfen; Ureas, such as B. chlorine toluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; Hy droxylamines, such as. B. Alloxydim, Clethodim, Cycloxydim, Sethoxydim and Tralkoxydim; Imidazolinones, e.g. B. Imazethapyr, Imazamethabenz, Imazapyr and imazaquin; Nitriles such as B. bromoxynil, dichlobenil and ioxynil; Oxyacet amides such as B. Mefenacet; Sulfonylureas, such as. B. Amidosulfuron, Ben sulfuron-methyl, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, metsulfuron methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, Triasulfuron and tribenuron-methyl; Thiol carbamates such as e.g. B. butylates, cycloates, Dialallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; Triazines, e.g. B. Atrazin, Cyanazin, Simazin, Simetryne, Terbutryne and Ter butylazine; Triazinones such as e.g. B. hexazinone, metamitron and metribuzin; Other, such as B. Aininotriazole, Benfuresate, Bentazone, Cinmethylin, Clomazone, Clo pyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufosinate, Glyphosate, Isoxaben, Pyridate, Quinchlorac, Quinmerac, Sulphosate and Tri diphane.

Also a mixture with other known active ingredients, such as fungicides secticides, acaricides, nematicides, bird repellants, plant nutrients substances and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use  Solutions, suspensions, emulsions, powders, pastes and granules are used will. The application is done in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after run of the plants can be applied. You can also sow in the soil before sowing be incorporated.

The amount of active ingredient used can vary over a wide range. she depends essentially on the type of effect desired. In general the application rates are between 1 g and 10 kg of active ingredient per hectare of soil area, preferably between 5 g and 5 kg per ha.

The manufacture and use of the active compounds according to the invention start out the following examples.

Manufacturing examples example 1 (Method (a))

A mixture of 3.8 g (12 mmol) of 1- (4-cyano-2,5-difluorophenyl) -3,6-dihydro- 2,6-dioxo-4-trifluoromethyl-1 (2H) pyrimidine, 1.5 g (21 mmol) sodium methylate and 50 ml of N-methyl-pyrrolidone is stirred at 130 ° C for 36 hours. After cooling Mix and dilute approximately three times with ethyl acetate Volume is washed with water and by chromatography over a Silica gel column (cyclohexane / ethyl acetate, vol .: 1/1) the product isolated.

1.6 g (41% of theory) of 1- (4-cyano-2-fluoro-5-methoxyphenyl) -3,6- dihydro-2,6-dioxo-4-trifluoromethyl-1 (2H) pyrimidine, melting point 114 ° C.  

Example 2 (Method (b))

A mixture of 1.5 g (4 mmol) of 1- (4-cyano-2-fluoro-5-methoxy-phenyl) -3,6- dihydro-2,6-dioxo4-trifluoromethyl-1 (2H) pyrimidine, 0.6 g (5 mmol) dimethyl sulfate, 0.7 g (5 mmol) of potassium carbonate and 100 ml of acetonitrile is used for 18 hours heated under reflux and then concentrated in a water jet vacuum. The residue is shaken with water / ethyl acetate, the organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is in a water jet vacuum concentrated, the residue digested with ethyl acetate / diisopropyl ether and the crystalline product is isolated by suction.

1.0 g (73% of theory) of 1- (4-cyano-2-fluoro-5-methoxyphenyl) -3,6- dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) pyrimidine, melting point 155 ° C.  

Analogous to Examples 1 and 2 and in accordance with the general description Exercise of the manufacturing method according to the invention can also, for example Compounds of formula (I) listed in Table 1 below be put.

Table I

Examples of the compounds of the formula (I)

Examples of use Example A Pre-emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

Seeds of the test plants are sown in normal soil. The bottom will poured or sprayed with the active ingredient preparation after 24 hours. It stops the amount of water per unit area is expediently constant. The effect Concentration of substances in the preparation does not matter, only the decisive factor Application rate of the active ingredient per unit area.

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 annihilation.

In this test, for example, show application rates between 8 and 125 g / ha as the compounds according to Preparation Examples 2 and 4 with a good contract sensitivity to crops, such as. B. wheat (0%), very strong effect against weeds such as Digitaria (90-100%), Setaria (95-100%), Abutilon (100%), Chenopodium (100%) and Matricaria (100%).  

Example B Post emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the information the same amount of emulsifier and dilute the concentrate with water to the wanted concentration.

The active ingredient preparation is used to inject test plants which are 5 - 15 cm so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 2000 l water / ha the desired amounts of active ingredient are applied. After three weeks, the degree of damage to the plants is rated in% pest compared to the development of the untreated control.

It means:
0% = no effect (like untreated control)
100% = total annihilation.

In this test, for example, the compounds according to the manufacturing example show games 2 and 4 at application rates between 30 and 500 g / ha strong effect ge against weeds such as panicum (95-100%), setaria (90-100%), sorghum (80-95%), Abutilon (100%), Chenopodium (100%) and Matricaria (100%).  

Example C Phaedon larval test

Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with horseradish leaf beetle larvae (Phaedon cochleariae) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. Here means 100% that all beetle larvae have been killed; 0% means that no beetles Larvae were killed.

In this test, e.g. B. the connection of preparation example 4 in a exemplary drug concentration of 0.1%, a kill of 100% after 7 Days.  

Example D Plutella test

Solvent: 7 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent and the specified amount of emulsifier and dilute the concentrate with water to the wanted concentration.

Cabbage leaves (Brassica oleracea) are dipped into the active ingredient preparation the desired concentration and treated with caterpillars (Plutel la maculipennis) occupied while the leaves are still moist.

After the desired time, the kill is determined in%. Here means 100% that all caterpillars have been killed; 0% means that no caterpillars are removed were killed.

In this test, e.g. B. the connection of preparation example 4 in a exemplary drug concentration of 0.1%, a kill of 100% after 7 Days.

Claims (9)

1. Cyanophenyluracils of the general formula (I) in which
Q represents O, S, SO or SO₂,
R¹ represents hydrogen, cyano or halogen,
R² represents hydrogen or an optionally substituted radical from the series alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkyl alkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl,
R³ represents hydrogen, halogen or an optionally substituted radical of the alkyl or alkoxy series,
R⁴ represents optionally substituted alkyl and
R⁵ represents hydrogen or an optionally substituted radical from the series alkyl, alkoxy, alkenyl or alkynyl,
except the compounds 1- (4-cyano-2-fluoro-5-methylthio-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine, 1- (4-Cya no-2-fluoro-5-methoxycarbonylmethylthio-phenyl) -3,6-dihydro-2,6-dioxo - 3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine and 1- [4- Cyano-2-fluoro-5- (1-eth oxycarbonyl-ethylthio) phenyl] -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) pyrimidine. 2. Cyanophenyluracile of the general formula (I) according to claim 1, characterized in that
Q represents O, S, SO or SO₂,
R¹ represents hydrogen, cyano, fluorine or chlorine,
R² for hydrogen, for each optionally by cyano, carboxy, fluorine, chlorine, bromine, C₁-C₄alkoxy, C₁-C₄alkylcarbonyl, C₁-C₄alkoxycarbonyl, di- (C₁-C₄alkyl) - amino-carbonyl or N-C₁-C₄-alkyl-N-phenyl-amino-carbonyl (where the phenyl group is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, methyl or methoxy) substituted alkyl, alkenyl or alkynyl with each up to 10 carbon atoms, each optionally substituted by cyano, carboxy, fluorine, chlorine, bromine, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkyl-carbonyl or C₁-C₄-alkoxy-carbonyl-substituted cycloalkyl or Cycloalkylalkyl with 3 to 8 carbon atoms in the cycloalkyl part and optionally up to 4 carbon atoms in the alkyl part, for each optionally by cyano, carboxy, nitro, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, by C₁-C₄-alkyl, C₁-C₄ -Alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkyl sulfinyl, C₁-C₄-alkylsulfonyl, C₁-C₄-alk yl-carbonyl or C₁-C₄- alkoxy-carbonyl (which are each optionally through fluorine and / or chlorine), through phenyl, phenoxy or phenylthio (which are each optionally through fluorine, chlorine, bromine, cyano, methyl, methoxy, trifluoromethyl and / or trifluoromethoxy are substituted) substituted aryl or arylalkyl having 6 or 10 carbon atoms in the aryl part and optionally up to 4 carbon atoms in the alkyl part,
R² further for each optionally by cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, by C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl, C₁-C₄-alkyl sulfonyl, C₁-C₄-alkyl-carbonyl or C₁-C Alk-alkoxy-carbonyl (which are in each case optionally by fluorine and / or chlorine), by phenyl, phenoxy or phenylthio (which are each optionally by fluorine, chlorine, bromine, cyano, Methyl, methoxy, trifluoromethyl and / or trifluoromethoxy are substituted) substituted substituted furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, oxetanyl, thietanyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadazolyl, tri-pyridylylylylylyl, pyrazolylylylylylylylinyl, pyrazolylylylylylylylylyl, pyrazolylylylylyl, pyrrazolylylyl, pyrazolylyl, pyrid or quinoxalinyl,
R³ represents hydrogen, fluorine, chlorine, bromine or alkyl or alkoxy, each optionally substituted by fluorine and / or chlorine, each having 1 to 4 carbon atoms,
R⁴ represents optionally substituted by fluorine and / or chlorine alkyl having 1 to 4 carbon atoms and
R⁵ represents hydrogen or alkyl, alkoxy, alkenyl or alkynyl, each optionally substituted by fluorine, chlorine or C₁-C₄alkoxy, each having up to 6 carbon atoms,
except the compounds 1- (4-cyano-2-fluoro-5-methylthio-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine, 1- (4-Cy ano-2-fluoro-5-methoxycarbonylmethylthio-phenyl) -3,6-dihydro-2,6-diox-o-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine and 1- [4 -Cyano-2-fluoro-5- (1-eth oxycarbonyl-ethylthio) phenyl] -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) pyrimidine . 3. Cyanophenyluracile of the general formula (I) according to claim 1, characterized in that
Q represents O, S, SO or SO₂,
R¹ represents hydrogen, fluorine or chlorine,
R² for hydrogen, for each optionally substituted by cyano, carboxy, fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or diethylaminocarbonyl substituted methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, propenyl, butenyl, pentenyl, propynyl, butynyl or pentynyl,
R² for each optionally by cyano, carboxy, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, acetyl or propionyl, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl,
R² further for each optionally by cyano, carboxy, nitro, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, Ethoxy, n- or i-propoxy, methylthio, ethylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl substituted phenyl, benzyl or phenylethyl, or
R² further for each optionally by cyano, carboxy, carb amoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethyl thio, methylsulfinyl, ethylsulfinyl, methylsulfonyl, ethylsulfonyl, Acßtyl, propionyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, substitu iertes by phenyl, phenoxy or phenylthio substituted furyl, tetrahydrofuryl, thienyl, tetrahydro thienyl, oxetanyl, thietanyl, oxazolyl, isoxazolyl, thiazolyl, oxa diazolyl, thiadiazolyl, pyrazolyl, pyridinyl, pyrimidinyl, triazinyl, indolyl, quinolinyl or quinoxalinyl,
R³ represents hydrogen, fluorine, chlorine, bromine or methyl,
R⁴ is methyl, ethyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, chloroethyl, fluoroethyl, dichloroethyl, dichloroethyl, chlorofluoromethyl, chlorodifluoroethyl, fluorodichloroethyl, trifluoroethyl, tetrafluorethyl or pentafluoromethyl or pentafluoromethyl, and chlorotrifluoromethyl
R⁵ for hydrogen or for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, each substituted by fluorine, chlorine <methoxy or ethoxy , n-, i- or s-butoxy, propenyl, butenyl, propynyl or butynyl,
except the compounds 1- (4-cyano-2-fluoro-5-methylthio-phenyl) -3,6-dihydro-2,6-dioxo-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine, 1- (4-Cy ano-2-fluoro-5-methoxycarbonylmethylthio-phenyl) -3,6-dihydro-2,6-diox-o-3-methyl-4-trifluoromethyl-1 (2H) -pyrimidine and 1- [4 -Cyano-2-fluoro-5- (1-eth oxycarbonyl-ethylthio) phenyl] -3,6-dihydro-2,6-dioxo-3-methyl-4-trif-luoromethyl-1 (2H) -pyrimidine . 4. Cyanophenyluracils of the general formula (Ia) characterized in that
Q, R¹, R², R³ and R⁴ have the meanings given in Claim 1. 5. Process for the preparation of cyanophenyluracils of the general formula (I) in which
R¹, R², R³, R⁴, R⁵ and Q have the meanings given in Claim 1,
characterized in that one
(a) substituted halophenyluracils of the general formula (II) in which
R¹, R³, R⁴ and R⁵ have the meanings given above and
X represents halogen,
with nucleophilic compounds of the general formula (III) MQ-R² (III) in which
Q and R² have the meanings given above and
M represents hydrogen or an alkali metal,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
or that one
(b) substituted cyanophenyluracils of the general formula (Ia) in which
Q, R¹, R², R³ and R⁴ have the meanings given above, optionally with an alkylating agent in the presence of a reaction and optionally in the presence of a diluent. 6. Herbicides and / or insecticidal agents, characterized by a content on at least one cyanophenyluracil of the general formula (I) according to claims 1 to 3 and 5. 7. methods for controlling unwanted plants and / or insects, characterized in that cyanophenyluracils of the general For mel (I) according to claims 1 to 3 and 5 on undesirable plants and / or insects and / or their habitats. 8. Use of cyanophenyluracils of the general formula (I) according to of claims 1 to 3 and 5 for controlling undesirable plants and / or insects. 9. Process for the preparation of herbicidal and / or insecticidal agents, characterized in that cyanophenyluracils of the general For mel (I) according to claims 1 to 3 and 5 with extenders and / or surface-active substances mixed.