DE10157063A1 - Substituted acylaminophenyluracile - Google Patents

Abstract

The invention relates to novel substituted acylaminophenyluracils of general formula (I), in which A = optionally substituted, straight- or branched-chain alkendiyl, Ar = optionally substituted, monocyclic or bicyclic aryl or heterocyclyl, where A and Ar can also be combined in bicyclic groups; R1 = H, amino or optionally substituted alkyl, R2 = carboxy, cyano, carbamoyl, thiocarbamoyl or optionally substituted alkyl or alkoxycarbonyl, R3 = H, halogen or optionally substituted alkyl, R4 = H, cyano, carbamoyl, thiocarbamoyl or halogen, R5 = cyano, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl or alkoxy and R6 = H, or optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkenyl, alkenylcarbonyl, alkenylsulphonyl, alkinyl, cycloalkylcarbonyl, cycloalkylsulphonyl, arylcarbonyl, arylsulphonyl, arylalkylcarbonyl, arylalkylsulphonyl, heterocyclylcarbonyl or heterocyclylsulphonyl and methods for production and use thereof as herbicides or insecticides.

Description

The invention relates to new substituted acylaminophenyluracils, processes for their Production and their use as herbicides.

Certain substituted aryluracils are already known (e.g. EP-A-408 382, US-A-5 084 084, US-A-5 127 935, US-A-5 154 755, EP-A-563 384, US-A-5 356 863, WO-A-95/29168, WO-A-96/35679, WO-A-97/01542, WO-A-97/09319, WO-A-98/06706 and in particular WO-A-00/02867). However, these connections have has so far gained no special significance.

New substituted acylaminophenyluracils of the general formula (I)


in which
A represents optionally substituted, straight-chain or branched alkenediyl,
Ar represents in each case optionally substituted, monocyclic or bicyclic aryl or heterocyclyl,
where A and Ar can also be combined in bicyclic groups,
R ^{1 represents} hydrogen, amino or optionally substituted alkyl,
R ^{2 stands} for carboxy, cyano, carbamoyl, thiocarbamoyl or for optionally substituted alkyl or alkoxycarbonyl,
R ^{3 represents} hydrogen, halogen or optionally substituted alkyl,
R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,
R ^{5 represents} cyano, carbamoyl, thiocarbamoyl, halogen, or in each case optionally substituted alkyl or alkoxy, and
R ^{6 stands} for hydrogen or for optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkenyl, alkenylcarbonyl, alkenylsulfonyl, alkynyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl, arylsulfonyl, arylalkylcarbonyl, arylalkylsulfonyl, heterocycylcyclyllylcarbonyl
found.

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

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

The compounds of general formula (I) according to the invention can each in There are geometrically isomeric forms: they can be substituted the C-C double bond (see definition of A) can be E- or Z-configured. The The invention relates in each case to the pure E and Z isomers and any Mixtures of these.

Preferred substituents or ranges of the radicals present in the formulas listed above and below are defined as follows:
A preferably represents alkenediyl with 2 to 10 carbon atoms optionally substituted by cyano or halogen.
Ar preferably represents optionally substituted, monocyclic or bicyclic aryl having up to 10 carbon atoms, or
for optionally substituted, monocyclic or bicyclic heterocyclyl having up to 9 carbon atoms and 1 to 4 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms,
where the possible substituents are preferably given in the following list:
Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ - Alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylamino, Di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylaminocarbonyl, di (C ₁ -C ₄ alkyl) - aminocarbonyl, di (C ₁ -C ₄ alkyl) aminosulfonyl,
and wherein A and Ar can also be combined in bicyclic groups such that A, when it stands for ethene-1,2-diyl, together with Ar forms a bicyclic group in which the carbon atom from A adjacent to the adjacent carbonyl group is via an alkylene group , in particular methylene or ethylene, or via O (oxygen) or S (sulfur) is linked to an ortho position of Ar.
R ¹ preferably represents hydrogen, amino or alkyl having 1 to 6 carbon atoms which is optionally substituted by cyano, carboxy, halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -alkoxycarbonyl.
R ² preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or alkyl or alkoxycarbonyl, each of which is optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups.
R ³ preferably represents hydrogen, halogen or optionally halogen-substituted alkyl having 1 to 6 carbon atoms.
R ⁴ preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen.
R ⁵ preferably represents cyano, carbamoyl, thiocarbamoyl, halogen, or alkyl or alkoxy, each optionally substituted by halogen, each having 1 to 4 carbon atoms.
R ⁶ preferably represents hydrogen, in each case alkyl, alkylcarbonyl or alkoxycarbonyl, each of which is optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, each having 1 to 6 carbon atoms in the alkyl groups,
for alkylsulfonyl with 1 to 6 carbon atoms optionally substituted by halogen,
for alkenyl, alkenylcarbonyl, alkenylsulfonyl or alkynyl each optionally substituted by halogen, each having up to 6 carbon atoms,
for cycloalkylcarbonyl or cycloalkylsulfonyl, each optionally substituted by halogen, each having 3 to 6 carbon atoms in the cycloalkyl groups,
in each case optionally substituted by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ - C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl or di- (C ₁ -C ₄ alkylamino) sulfonyl substituted arylcarbonyl, arylsulfonyl, arylalkylcarbonyl or arylalkylsulfonyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl part,
or for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio , C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl or di (C ₁ -C ₄ alkylamino) sulfonyl substituted heterocyclylcarbonyl or heterocyclylsulfonyl having 1 to 5 carbon atoms and 1 to 3 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms.
A particularly preferably represents ethene-1,2-diyl, propene-1,2-diyl, propene-2,3-diyl, propene-1,3-diyl, each optionally substituted by cyano, fluorine, chlorine and / or bromine, Butene-1,2-diyl, butene-1,3-diyl, butene-2,3-diyl, butene-3,4-diyl or butene-1,4-diyl.
Ar particularly preferably stands for optionally substituted phenyl or naphthyl, or for optionally substituted heterocyclyl from the series furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, benzofuryl, dihydrobenzofuryl, benzothienyl, pyrrolyl, pyrazolyl, pyranyl, benzopyranyopyrylopyranyl, pyridrozolylyridylzyridylzyrinophenyl, pyridyl, pyridyl, pyridyl, pyridyl, pyridyl, pyridyl, pyrrole , Pyrimidinyl,
where the possible substituents are preferably given in the following list:
Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl trifluoromethyl, methoxy, ethoxy, n- or i- Propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl , n- or i-Propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethyl -amino, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl, diethylaminosulfonyl,
and where A and Ar are also common for grouping


can stand.
R ¹ particularly preferably represents hydrogen, amino or in each case methyl or ethyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.
R ² particularly preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy.
R ³ particularly preferably represents hydrogen, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine.
R ⁴ particularly preferably represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine or chlorine.
R ⁵ particularly preferably represents cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy which is optionally substituted by fluorine and / or chlorine ,
R ⁶ particularly preferably represents hydrogen,
for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, n optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -, i- or sec-valeroyl, pivaloyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
for methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl optionally substituted by fluorine and / or chlorine,
for each optionally substituted by fluorine, chlorine and / or bromine, ethenyl, propenyl, butenyl, ethenylcarbonyl, propenylcarbonyl, butenylcarbonyl, ethynyl, propynyl or butynyl,
in each case optionally substituted by fluorine, chlorine and / or bromine-substituted cyclopropylcarbonyl, Cyclopropylmethylcarbonyl, cyclobutylcarbonyl, Cyclobutylmethylcarbonyl, cyclopentylcarbonyl, Cyclopentylmethylcarbonyl, cyclohexylcarbonyl, cyclohexylmethylcarbonyl, cyclopropylsulfonyl, Cyclopropylmethylsulfonyl, Cyclobutylsulfonyl, Cyclobutylmethylsulfonyl, cyclopentylsulfonyl, Cyclopentylmethylsulfonyl, cyclohexylsulfonyl or cyclohexylmethylsulfonyl,
for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy , n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbononyl or sulfethylamino-methylyl-sulfonylamethyl-sulfonylamethyl-sulfonyl-sulfonylamethyl-sulfonyl Benzoyl, phenylsulfonyl, phenylacetyl, phenylpropionyl, benzylsulfonyl or phenylethylsulfonyl, or
for each optionally nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n - or i-Propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, or dimethylaminosulfonyl substituted heterocyclylcarbonyl or heterocyclylsulfonyl from the series furylcarbonyl, furylsulfonyl, thienylcarbonyl, thienylsulfonyl, pyrazolylcarbonyl, pyrazolylsulfonyl, pyridinylcarbonyl, pyridinylsulfonyl, quinolinylcarbonyl, quinolinylsulfonyl, pyrimidinylcarbonyl.
A very particularly preferably represents ethene-1,2-diyl, propene-1,2-diyl or propene-2,3-diyl, each of which is optionally substituted by cyano, fluorine, chlorine and / or bromine.
Ar very particularly preferably represents optionally substituted phenyl or naphthyl,
the possible substituents in particular can be found in the following list:
Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylcarbonyl, trifluoromethylcarbonyl propoxycarbonyl.

The substituents from the following list are particularly preferred:
Fluorine, chlorine, bromine, methyl, ethyl, methoxy or ethoxy.
R ¹ very particularly preferably represents hydrogen, amino or methyl.
R ² very particularly preferably represents trifluoromethyl.
R ³ very particularly preferably represents hydrogen, chlorine or methyl.
R ⁴ very particularly preferably represents hydrogen, fluorine or chlorine.
R ⁵ very particularly preferably represents cyano, chlorine or bromine,
R ⁶ very particularly preferably represents hydrogen, in each case methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl optionally substituted by fluorine and / or chlorine, or optionally by fluorine and / or or chlorine substituted cyclopropylsulfonyl.

A further preferred group of compounds are those compounds of the formula (I) in which
A and Ar together for grouping


stand,
the possible substituents can be found in particular in the following list:
Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylcarbonyl, trifluoromethylcarbonyl propoxycarbonyl,
R ^{1 represents} hydrogen, amino or methyl,
R ^{2 represents} trifluoromethyl,
R ^{3 represents} hydrogen, chlorine or methyl,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} cyano, chlorine or bromine, and
R ⁶ for hydrogen, for methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl, which are optionally substituted by fluorine and / or chlorine, or for cyclopropylsulfonyl which is optionally substituted by fluorine and / or chlorine stands.

The general or preferred areas listed above Residual definitions apply both to the end products of the formula (I) and accordingly for the starting or intermediate products required for the production. This Residual definitions can be among themselves, that is, between the specified ones preferred areas can be combined as desired.

Examples of the compounds of the general formula (I) according to the invention are listed in the groups below. Group 1

Ar has one of the meanings given below:
2-cyano-phenyl, 3-cyano-phenyl, 4-cyano-phenyl, 2-fluorophenyl, 3-fluorophenyl, 4-fluorophenyl, 2,3-difluorophenyl, 2,4-difluoro- phenyl, 2,5-difluorophenyl, 2,6-difluorophenyl, 3,4-difluorophenyl, 3,5-difluorophenyl, 2-chlorophenyl, 3-chlorophenyl, 4-chloro phenyl, 2,3-dichlorophenyl, 2,4-dichlorophenyl, 2,5-dichlorophenyl, 2,6-dichlorophenyl, 3,4-dichlorophenyl, 3,5-dichlorophenyl, 2-bromophenyl, 3-bromophenyl, 4-bromophenyl, 2-methylphenyl, 3-methylphenyl, 4-methylphenyl, 2,3-dimethylphenyl, 2,4-dimethyl phenyl, 2,5-dimethyl-phenyl, 2,6-dimethyl-phenyl, 3,4-dimethyl-phenyl, 3,5-dimethyl-phenyl, 2-trifluoromethyl-phenyl, 3-trifluoromethyl-phenyl, 4-trifluoromethyl- phenyl, 2-methoxyphenyl, 3-methoxyphenyl, 4-methoxyphenyl, 2,4-dimethoxyphenyl, 2,5-dimethoxyphenyl, 2,6-dimethoxyphenyl, 3,4-dimethoxy phenyl, 2-difluoromethoxy-phenyl, 4-difluoromethoxy-phenyl, 2-trifluoromethoxy-phenyl, 4-trifluoromethoxy-phenyl, 2-chloro-4-methyl-phenyl, 4-chloro-2-methyl-phenyl, 2-fluoro- 4-chloro-p henyl, 2-chloro-4-fluorophenyl, 2-chloro-4-bromophenyl, 2-bromo-4-chlorophenyl, 2-fluoro-4-bromophenyl, 2-bromo-4-fluoro- phenyl, 4-fluoro-2-methylphenyl, 4-bromo-2-methylphenyl. Group 2

Ar has one of the meanings given above for group 1. Group 3

Ar has one of the meanings given above for group 1. Group 4

Ar has one of the meanings given above for group 1. Group 5

Ar has one of the meanings given above for group 1. Group 6

Ar has one of the meanings given above for group 1. Group 7

Ar has one of the meanings given above for group 1. Group 8

Ar has one of the meanings given above for group 1. Group 9

Ar has one of the meanings given above for group 1. Group 10

Ar has one of the meanings given above for group 1. Group 11

Ar has one of the meanings given above for group 1. Group 12

Ar has one of the meanings given above for group 1. Group 13

Ar has one of the meanings given above for group 1. Group 14

Ar has one of the meanings given above for group 1. Group 15

Ar has one of the meanings given above for group 1. Group 16

Ar has one of the meanings given above for group 1. Group 17

Ar has one of the meanings given above for group 1. Group 18

Ar has one of the meanings given above for group 1. Group 19

Ar has one of the meanings given above for group 1. Group 20

Ar has one of the meanings given above for group 1. Group 21

Ar has one of the meanings given above for group 1. Group 22

Ar has one of the meanings given above for group 1. Group 23

Ar has one of the meanings given above for group 1. Group 24

Ar has one of the meanings given above for group 1.

The new substituted acylaminophenyluracils of the general formula (I) have interesting biological properties. They are particularly characterized by a strong herbicidal activity.

The new substituted acylaminophenyluracils of the general formula (I) are obtained if aminophenyluracils of the general formula (II)


in which
R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^{6 have} one of the meanings given above,
with acylating agents of the general formula (III)


in which
A and Ar have one of the meanings given above and
X represents halogen,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, subsequently carries out electrophilic or nucleophilic or oxidation or reduction reactions as part of the definition of substituents.

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 by amination or alkylation (for example R ¹ : H → NH ₂ or CH ₃ ) or by Reaction with dicyan or hydrogen sulfide, (e.g. R ⁵ : Br → CN or CN → CSNH ₂ ).

For example, if 1- (2,4-dichloro-5-methylsulfonylamino-phenyl) -4-difluoromethyl-3,6-dihydro-2,6-dioxo-1 (2H) -pyrimidine and (2E) -3- (2nd , 4-dichlorophenyl) -2-propenyl chloride as starting materials, the course of the reaction in the process according to the invention can be outlined by the following formula:

Formula (II) provides a general definition of the aminophenyluracils to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I). In formula (II), R ¹ , R ² , R ³ , R ⁴ and R ⁵ preferably have those meanings which are preferred, particularly preferred or very particularly preferred in connection with the description of the compounds of the formula (I) according to the invention for R ¹ , R ² , R ³ , R ⁴ and R ⁵ .

The starting materials of the general formula (II) are known and / or can be according to processes known per se (cf. EP-A-408 382, EP-A-648 749 or WO-A-97/01542).

Those to be used further as starting materials in the process according to the invention Acylating agents are generally defined by the formula (III). In the formula (III) A and Ar preferably have those meanings which have already been mentioned above in Connection with the description of the compounds of the invention Formula (I) as preferred, particularly preferred or very particularly preferred for A. and Ar were given. X preferably represents fluorine, chlorine or bromine, particularly preferred for chlorine.

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

The process of the invention for the preparation of the compounds of general Formula (I) is preferably carried out using a reaction auxiliary carried out. As reaction aids for the inventive method come in Generally the usual inorganic or organic bases or Acid acceptors into consideration. These preferably include alkali metal or Alkaline earth metal acetate, amide, carbonate, bicarbonate, hydride, hydroxide 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 methanolate, ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t- butoxide; also basic organic nitrogen compounds, such as for example trimethylamine, triethylamine, tripropylamine, tributylamine, Ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, 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), or 1,8- Diazabicyclo [5,4,0] -undec-7-ene (DBU).

The process of the invention for the preparation of the compounds of general Formula (I) is preferably made using a diluent carried out. As a diluent for carrying out the method according to the invention inert organic solvents are particularly suitable. This includes in particular aliphatic, 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, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or Methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methyl-formanilide, N- Methyl pyrrolidone or hexamethyl phosphoric acid triamide; Esters like 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 monomethyl ether, Diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be carried out when carrying out the inventive Process can be varied over a wide range. Generally you work at 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 carried out. However, it is also possible to increase the process according to the invention or reduced pressure - generally between 0.1 bar and 10 bar - perform.

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 The reaction is generally carried out in a suitable diluent In the presence of a reaction auxiliary and the reaction mixture is in generally stirred for several hours at the required temperature. The Refurbishment is carried out according to customary methods (cf. the Preparation Examples).

The active compounds according to the invention can be used as defoliants, desiccants, Herbicides and especially as weed killers. 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 amount used.

The active compounds according to the invention can, for. B. 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, Gupopsis, Euphorbia , Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsesb, Senania, , 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, Vicia.
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, Secale, Sorghum, Triticale, Triticum, Zea.

However, the use of the active compounds according to the invention is by no means limited to them Limited genres, but extends in the same way to others Plants.

The active compounds according to the invention are suitable depending on the Total weed control concentration, e.g. B. on industrial and track systems and on Because of and places with and without tree cover. Likewise, the Active compounds according to the invention for weed control in permanent crops, for. B. Forst, 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 and used for selective weed control in annual crops become.

The compounds of formula (I) according to the invention show strong herbicides Efficacy and a wide range of effects when used on the floor and on aerial parts of plants. To a certain extent, they are also suitable for selective use Control of monocot and dicot weeds in monocotyledon and dicotyledon cultures, both pre-emergence and post-emergence.

The active compounds according to the invention can be used in certain concentrations or Application rates also to control animal pests and fungal or bacterial plant diseases can be used. You let yourself be optionally also as intermediates or precursors for the synthesis of further active ingredients deploy.

According to the invention, all plants and parts of plants can be treated. Under Plants are understood here as all plants and plant populations desired and undesirable wild plants or crops (including naturally occurring crops). Cultivated plants can be plants that by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these Methods can be obtained, including transgenic plants and including those that can or cannot be protected by plant variety rights Plant varieties. Under plant parts, all above-ground and underground Parts and organs of plants, such as sprout, leaf, flower and root understood leaves, needles, stems, stems, flowers, fruiting bodies, Fruits and seeds as well as roots, tubers and rhizomes are listed. To the Plant parts also include crops as well as vegetative and generative Propagation material, for example cuttings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and plant parts according to the invention with the Active substances take place directly or by influencing their environment, habitat or Storage room according to the usual treatment methods, e.g. B. by diving, spraying, Evaporation, atomization, scattering, spreading and in the case of propagation material, especially in the case of seeds, further 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 encapsulation in polymers Substances.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, optionally using surface-active agents, So emulsifiers and / or dispersants and / or foam-generating Means.

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 Alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, 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.

Possible solid carriers are: B. ammonium salts and natural Rock flours, such as kaolins, clays, talc, chalk, quartz, attapulgite, Montmorillonite 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 such as calcite, Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust, Coconut shells, corn cobs and tobacco stems; as emulsifying and / or Foaming agents are possible: z. B. non-ionic and anionic Emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants come into question: z. B. lignin sulfite and Methylcellulose.

In the formulations, adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural Phospholipids such as cephalins and lecithins and synthetic phospholipids. Further 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 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 Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known herbicides and / or with substances which Improve crop tolerance ("safeners") for weed control can be used, whereby ready formulations or tank mixes are possible. It So mixtures with weed control agents are also possible, which a or contain several known herbicides and a safener.

Known herbicides are suitable for the mixtures, for example Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), Ametryne, Amicarbazone, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, azimsulfuron, beflubutamide, benazolin (-ethyl), benfuresate, Bensulfuron (-methyl), bentazone, benzfendizone, benzobicyclone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxime, Bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylates, cafenstrole, Caloxydim, carbetamides, carfentrazone (-ethyl), chloromethoxyfen, chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulfuron, Clefoxydim, Clethodim, Clodinafop (- propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron (-methyl), Cloransulam (methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichloroprop (-P), diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (- methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop (-P- ethyl), fentrazamide, flamprop (-isopropyl, -isopropyl-L, -methyl), flazasulfron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufenacet, Flufenpyr, flumetsulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, Flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, Flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (- butoxypropyl, -meptyl), flurprimidol, flurtamone, fluthiacet (-methyl), fluthiamide, Fomesafen, foramsuliron, glufosinate (ammonium), Glyphosate (-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl, -P-methyl), hexazinones, Imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, Imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, Isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, Ketospiradox, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Mesotrione, Metamitron, metazachlor, methabenzthiazuron, metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin, metsulfuron (-methyl), molinates, Monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, penoxysulam, Pentoxazone, pethoxamide, phenmedipham, picolinafen, piperophos, pretilachlor, Primisulfuron (-methyl), profluazole, profoxydim, prometryn, propachlor, propanil, Propaquizafop, propisochlor, propoxycarbazone (sodium), propyzamide, prosulfocarb, Prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), Pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac (- methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop (-Pethyl, -P-tefuryl), rimsulfuron, sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, Tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, thiafluamide, Thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, 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, fenchlorazole (-ethyl), flurazole, fluxofenim, Furilazoles, isoxadifene (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG- 191, Oxabetrinil, PPG-1292, R-29148.

A mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellants, Plant nutrients 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 become. The application happens 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 emergence of the plants are 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 Soil area, preferably between 5 g and 5 kg per ha.

As already mentioned above, according to the invention all plants and their parts can be treated. In a preferred embodiment, go wild existing or by conventional organic breeding methods, such as crossing or protoplast fusion obtained plant species and plant varieties and their Parts treated. In a further preferred embodiment, transgenes are Plants and plant varieties by genetic engineering methods, if necessary in combination with conventional methods (Genetically Modified Organisms) and their parts. The term "parts" or "parts of." Plants "or" parts of plants "was explained above.

Plants of the commercially available in each case are particularly preferred according to the invention or plant varieties in use. Among plant varieties is understood to mean plants with certain properties ("traits") that are caused by conventional breeding, by mutagenesis, or also by recombinant DNA Techniques have been obtained. These can be varieties, bio and genotypes.

Depending on the plant species or plant varieties, their location and Growth conditions (soils, climate, growing season, nutrition) can be determined by the Treatment according to the invention also results in 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 invention usable substances and agents - also in combination with other agrochemicals Active ingredients, better growth of crops, increased tolerance of Crops against high or low temperatures, increased tolerance of the Crops against drought or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripening, higher Crop yields, higher quality and / or higher nutritional value of the crop products, higher Shelf life and / or workability of the harvested products possible via the effects that are actually to be expected.

Among the preferred transgenic (genetic engineering received) plants or plant varieties include all plants by the genetic engineering modification received genetic material, which these plants gives special advantageous valuable properties ("traits"). examples for such properties are better plant growth, increased tolerance towards high or low temperatures, increased tolerance to drought or to Water or soil salt content, increased flowering performance, easier harvesting, Acceleration of ripeness, higher crop yields, higher quality and / or higher Nutritional value of the harvested products, higher shelf life and / or workability of the Harvested products. Further and particularly highlighted examples of such Properties are an increased defense of the plants against animal and microbial Pests, such as against insects, mites, phytopathogenic fungi, bacteria and / or viruses and an increased tolerance of the plants to certain herbicides Agents. The important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and Fruit plants (with the fruits apples, pears, citrus fruits and grapes) mentioned, corn, soybeans, potatoes, cotton and rapeseed are particularly emphasized. The increased defense is particularly emphasized as traits of plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (e.g. by the Gene CryIA (a), CryIA (b), CryIA (c), CryIIA, CryIIIA, CryIIIB2, Cry9c Cry2Ab, Cry3Bb and CryIF and their combinations) are generated in the plants (in Hereinafter referred to as "Bt plants"). As traits, too particularly emphasized the increased defense of plants against fungi, bacteria and Viruses through Systemic Acquired Resistance (SAR), Systemin, Phytoalexins, Elicitors and resistance genes and correspondingly expressed proteins and toxins. The traits that are particularly emphasized are the increased ones Plant tolerance to certain herbicidal active ingredients, for example Imidazolinones, sulfonylureas, glyphosate or phosphinothricin (e.g. "PAT" gene). Those which confer the desired properties ("traits") Genes can also be used in combinations with each other in the transgenic plants occurrence. Examples of "Bt plants" are corn varieties, cotton varieties, Soybeans and potatoes are sold under the trade names YIELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. Maize), Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato) to be expelled. Examples of herbicide-tolerant plants are maize varieties, Sorts of cotton and soy called under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinothricin, e.g. rapeseed), IMI® (tolerance to Imidazolinone) and STS® (tolerance to sulfonylureas e.g. maize) become. As herbicide-resistant (conventionally bred to herbicide tolerance) Plants are also the varieties sold under the name Clearfield® (e.g. Corn) mentioned. Of course, these statements also apply to the future developed or future plant varieties with these or future developed genetic traits.

The plants listed can be particularly advantageous according to the invention with the Compounds of general formula I or those of the invention Active ingredient mixtures are treated, in addition to the good control of Weed plants have the above-mentioned synergistic effects with the transgenic Plants or plant varieties occur. The active ingredients or mixtures Preferred ranges given above also apply to the treatment of these plants. Plant treatment with those in the present text should be particularly emphasized Specially listed compounds or mixtures.

Active ingredients are also suitable for controlling animal pests, especially insects, arachnids and nematodes, which are used in agriculture, in Forest, in the protection of stocks and materials and in the hygiene sector. she can preferably be used as pesticides. You are against normally sensitive and resistant species as well as against all or some Stages of development effective.

When used as insecticides, the active compounds according to the invention can also be used in their commercial formulations and in those formulations prepared application forms in a mixture with synergists. synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself must be active.

The active substance content of those prepared from the commercially available formulations Application forms can vary widely. The drug concentration of the Use forms can be from 0.0000001 to 95% by weight of active compound, preferably are 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 combating of arthropods, the farm animals, such as. B. cattle, sheep, goats, Horses, pigs, donkeys, camels, buffaloes, rabbits, chickens, turkeys, ducks, geese, Bees, other pets such as B. dogs, cats, house birds, aquarium fish as well as so-called experimental animals, such as. B. hamsters, guinea pigs, rats and Infest mice. By fighting these arthropods, deaths and Reductions in performance (for meat, milk, wool, skins, eggs, honey, etc.) can be reduced, so that by using the active compounds according to the invention more economical and easier animal husbandry is possible.

The active compounds according to the invention are used in the veterinary sector in in a known manner by enteral administration in the form of, for example, tablets, Capsules, watering, drenching, granules, pastes, boluses, the feed-through process, suppositories, by parenteral administration, such as by injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, through nasal Application, by dermal application in the form of, for example, diving or Bathing (dipping), spraying (spray), pouring (pour-on and spot-on), des Washing, powdering and with the help of shaped articles containing active ingredients, such as Collars, ear tags, tail tags, limb straps, 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 ingredients in an amount of 1 to 80 wt .-%, directly or after 100 to 10,000-fold dilution or use it as a chemical bath use.

The active ingredients are also suitable for controlling animal pests, especially of insects, arachnids and mites that live in enclosed spaces, such as for example apartments, factory buildings, offices, vehicle cabins and the like. occur. You can fight these pests alone or in combination with other active ingredients and adjuvants can be used in household insecticide products. They are against sensitive and resistant species as well as against all stages of development effective.

The application takes place in aerosols, unpressurized sprays, e.g. B. Pump and Atomizer sprays, automatic fog machines, foggers, foams, gels, Vaporizer products with vaporizer platelets made of cellulose or plastic, liquid vaporizers, Gel and membrane evaporators, propeller-driven evaporators, energy-free or passive evaporation systems, moth papers, moth bags and Moth angels, as granules or dusts, in lures or bait stations.

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

Preparation Examples example 1

A mixture of 2.00 g (4.76 mmol) of 1- (4-cyano-5-ethylsulfonylamino-2-fluoro- phenyl) -3-methyl-4-trifluoromethyl-3,6-dihydro-2,6-dioxo-1 (2H) pyrimidine, 1.46 g (6.20 mmol) (2E / Z) -3- (3,4-dichlorophenyl) -2-propenyl chloride, 0.63 g (6.20 mmol) of triethylamine and 50 ml of acetonitrile is added for 18 hours Room temperature (about 20 ° C) stirred and then concentrated under reduced pressure. The residue is taken up in methylene chloride, with aqueous 1N hydrochloric acid shaken, washed with water, dried with sodium sulfate and filtered. The Mother liquor is washed with 1N hydrochloric acid and then with water, with Dried sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, the residue was digested with diethyl ether / petroleum ether and the crystalline product Product isolated by suction.

2.1 g (71% of theory) (E / Z) -1- [4-cyano-5- (N-ethylsulfonyl-N- (3- (3,4- dichloro-phenyl) -2-propenoyl-amino) -2-fluoro-phenyl] -3-methyl-4-trifluoromethyl-3,6- dihydro-2,6-dioxo-1 (2H) pyrimidine, melting point 243 ° C.

Analogously to Preparation Example 1 and in accordance with the general description of the preparation process according to the invention, it is also possible, for example, to prepare the compounds of the formula (I) listed in Table 1 below.

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

These are E / Z mixtures

applications 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, mix 1 Part by weight of active ingredient with the specified amount of solvent gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

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

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, the compounds according to the preparation example show 1, 2, 3, 4, 6, 7, 8, 9, 10, 11 and 12 with largely good tolerance to Cultivated plants, such as. B. corn, soybeans and wheat, very strong action against Weeds.

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, mix 1 Part by weight of active ingredient with the specified amount of solvent gives the specified amount of emulsifier and dilute the concentrate with water to the desired concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5 to 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 1000 l water / ha the desired amounts of active ingredient are applied.

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, the compounds according to the preparation example show 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 12 with largely good tolerance to Cultivated plants, such as. B. soybeans and wheat, very strong action against weeds.

Example C Myzus test / field beans

Solvent: 31 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To prepare a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the stated amounts of solvent and emulsifier and dilute the concentrate to the desired level with water containing emulsifier Concentration.

Seedlings of the broad bean (Vicia faba minor), which with the green Peach aphids (Myzus persicae) are infested in a drug preparation desired concentration dipped and placed in a plastic can.

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

In this test, e.g. B. the compound according to Production Example 10 in a Active ingredient concentration of 100 ppm kills 100%.

Claims (11)

1. Compounds of formula (I)


in which
A represents optionally substituted, straight-chain or branched alkenediyl,
Ar represents in each case optionally substituted, monocyclic or bicyclic aryl or heterocyclyl,
where A and Ar can also be combined in bicyclic groups,
R ^{1 represents} hydrogen, amino or optionally substituted alkyl,
R ^{2 stands} for carboxy, cyano, carbamoyl, thiocarbamoyl or for optionally substituted alkyl or alkoxycarbonyl,
R ^{3 represents} hydrogen, halogen or optionally substituted alkyl,
R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl or halogen,
R ^{5 represents} cyano, carbamoyl, thiocarbamoyl, halogen, or in each case optionally substituted alkyl or alkoxy, and
R ^{6 stands} for hydrogen or for optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulfonyl, alkenyl, alkenylcarbonyl, alkenylsulfonyl, alkynyl, cycloalkylcarbonyl, cycloalkylsulfonyl, arylcarbonyl, arylsulfonyl, arylalkylcarbonyl, arylalkylsulfonyl, heterocycylcyclyllylcarbonyl or 2. Compounds of formula (I) according to claim 1, characterized in that
A represents alkenediyl having 2 to 10 carbon atoms optionally substituted by cyano or halogen,
Ar for optionally substituted, monocyclic or bicyclic aryl having up to 10 carbon atoms, or
represents optionally substituted, monocyclic or bicyclic heterocyclyl having up to 9 carbon atoms and 1 to 4 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms,
where the respective possible substituents can be found in the following list:
Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ - Alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ - C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylamino, Di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylaminocarbonyl, di (C ₁ -C ₄ alkyl) - aminocarbonyl, di (C ₁ -C ₄ alkyl) aminosulfonyl,
and where A and Ar can also be combined in bicyclic groups such that A, if it stands for ethene-1,2-diyl, together with Ar forms a bicyclic group in which the carbon atom from A adjacent to the adjacent carbonyl group is via a Alkylene group, in particular methylene or ethylene, or linked to an ortho position of Ar via O (oxygen) or S (sulfur),
R ^{1 represents} hydrogen, amino or alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, carboxy, halogen, C ₁ -C ₄ alkoxy or C ₁ -C ₄ alkoxycarbonyl,
R ^{2 stands} for carboxy, cyano, carbamoyl, thiocarbamoyl or for alkyl or alkoxycarbonyl, each optionally substituted by cyano, 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 ^{5 stands} for cyano, carbamoyl, thiocarbamoyl, halogen, or for alkyl or alkoxy each optionally substituted by halogen, each having 1 to 4 carbon atoms, and
R ^{6 represents} hydrogen, each alkyl, alkylcarbonyl or alkoxycarbonyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having 1 to 6 carbon atoms in the alkyl groups,
for alkylsulfonyl with 1 to 6 carbon atoms optionally substituted by halogen,
for alkenyl, alkenylcarbonyl, alkenylsulfonyl or alkynyl each optionally substituted by halogen, each having up to 6 carbon atoms,
for cycloalkylcarbonyl or cycloalkylsulfonyl, each optionally substituted by halogen, each having 3 to 6 carbon atoms in the cycloalkyl groups,
for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ -alkoxycarbonyl or di- (C ₁ - C ₄ alkylamino) sulfonyl-substituted arylcarbonyl, arylsulphonyl, arylalkylcarbonyl or arylalkylsulphonyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl moiety,
or for each optionally by nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio , C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ - C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylcarbonyl, C ₁ -C ₄ -alkoxycarbonyl or di- (C ₁ - C ₄ alkylamino) sulfonyl-substituted heterocyclylcarbonyl or heterocyclylsulphonyl having 1 to 5 carbon atoms and 1 to 3 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms. 3. Compounds of formula (I) according to claim 1 or 2, characterized in that
A for ethene-1,2-diyl, propene-1,2-diyl, propene-2,3-diyl, propene-1,3-diyl, butene-1, each optionally substituted by cyano, fluorine, chlorine and / or bromine , 2-diyl, butene-1,3-diyl, butene-2,3-diyl, butene-3,4-diyl or butene-1,4-diyl,
Ar represents in each case optionally substituted phenyl or naphthyl, or for in each case substituted or unsubstituted heterocyclyl from the series furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, benzofuryl, dihydrobenzofuryl, benzothienyl, pyrrolyl, pyrazolyl, pyranyl, benzopyranyl, dihydrozidylyryl, pyridlyl benzyryl, pyridine, pyridine, pyridine, pyridine, pyridine, pyridine, pyridine, pyridine, benzyl pyridine .
where the respective possible substituents can be found in the following list:
Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl trifluoromethyl, methoxy, ethoxy, n- or i- Propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl , n- or i-Propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethyl , Acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl,
and where A and Ar are also common for grouping


can stand
R ^{1 represents} hydrogen, amino or in each case methyl or ethyl substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
R ^{2 stands} for carboxy, cyano, carbamoyl, thiocarbamoyl or for methyl, ethyl, n- or i-propyl, methoxycarbonyl or ethoxycarbonyl optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,
R ^{3 represents} hydrogen, fluorine, chlorine, bromine or in each case methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine and / or chlorine,
R ^{4 represents} hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine or chlorine,
R ^{5 stands} for cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for methyl, ethyl, n- or i-propyl, meth- or i-propyl, methoxy, ethoxy, n- or i-propoxy which is optionally substituted by fluorine and / or chlorine, and
R ⁶ for hydrogen,
for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, n which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -, i- or sec-valeroyl, pivaloyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,
for methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl optionally substituted by fluorine and / or chlorine,
for each optionally substituted by fluorine, chlorine and / or bromine, ethenyl, propenyl, butenyl, ethenylcarbonyl, propenylcarbonyl, butenylcarbonyl, ethynyl, propynyl or butynyl,
in each case optionally substituted by fluorine, chlorine and / or bromine-substituted cyclopropylcarbonyl, Cyclopropylmethylcarbonyl, cyclobutylcarbonyl, Cyclobutylmethylcarbonyl, cyclopentylcarbonyl, Cyclopentylmethylcarbonyl, cyclohexylcarbonyl, cyclohexylmethylcarbonyl, cyclopropylsulfonyl, Cyclopropylmethylsulfonyl, Cyclobutylsulfonyl, Cyclobutylmethylsulfonyl, cyclopentylsulfonyl, Cyclopentylmethylsulfonyl, cyclohexylsulfonyl or cyclohexylmethylsulfonyl,
for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy , n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbononyl or sulfethylamino-methylyl-sulfonylamethyl-sulfonyl-sulfonylamethyl-sulfonyl Benzoyl, phenylsulfonyl, phenylacetyl, phenylpropionyl, benzylsulfonyl or phenylethylsulfonyl, or
for each optionally nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n - or i-Propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, or dimethylaminosulfonyl substituted heterocyclylcarbonyl or heterocyclylsulfonyl from the series furylcarbonyl, furylsulfonyl, thienylcarbonyl, thienylsulfonyl, pyrazolylcarbonyl, pyrazolylsulfonyl, pyridinylcarbonyl, pyridinylsulfonyl, quinolinylcarbonyl, quinolinylsulfonyl, pyrimidinylcarbonyl. 4. Compounds of formula (I) according to any one of claims 1 to 3, characterized in that
A represents ethene-1,2-diyl, propene-1,2-diyl or propene-2,3-diyl which is optionally substituted by cyano, fluorine, chlorine and / or bromine,
Ar represents in each case optionally substituted phenyl or naphthyl,
where the respective possible substituents can be found in the following list:
Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylcarbonyl, trifluoromethylcarbonyl propoxycarbonyl,
R ^{1 represents} hydrogen, amino or methyl,
R ^{2 represents} trifluoromethyl,
R ^{3 represents} hydrogen, chlorine or methyl,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} cyano, chlorine or bromine, and
R ⁶ for hydrogen, for methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl, which are optionally substituted by fluorine and / or chlorine, or for cyclopropylsulfonyl which is optionally substituted by fluorine and / or chlorine stands. 5. Compounds of formula (I) according to any one of claims 1 to 4, characterized in that
A and Ar together for grouping


stand,
the possible substituents can be found in the following list:
Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylcarbonyl, trifluoromethylcarbonyl propoxycarbonyl,
R ^{1 represents} hydrogen, amino or methyl,
R ^{2 represents} trifluoromethyl,
R ^{3 represents} hydrogen, chlorine or methyl,
R ^{4 represents} hydrogen, fluorine or chlorine,
R ^{5 represents} cyano, chlorine or bromine, and
R ⁶ for hydrogen, for methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl, which are optionally substituted by fluorine and / or chlorine, or for cyclopropylsulfonyl which is optionally substituted by fluorine and / or chlorine stands. 6. A process for the preparation of compounds of the formula (I) according to any one of claims 1 to 5, characterized in that compounds of the general formula (II)


in which
R ¹ , R ² , R ³ , R ⁴ , R ⁵ and R ^{6 have} one of the meanings given in one of Claims 1 to 5,
with acylating agents of the general formula (III)


in which
A and Ar have one of the meanings given in one of claims 1 to 5 and
X represents halogen,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, subsequently carries out electrophilic or nucleophilic or oxidation or reduction reactions as part of the definition of substituents. 7. Herbicidal agents, characterized by the content of at least one Connection according to one of claims 1 to 5 and conventional extenders. 8. Insecticidal agents, characterized by the content of at least one Connection according to one of claims 1 to 5 and conventional extenders. 9. Use of at least one compound according to one of the claims 1 to 5 or an agent according to claim 7 for combating unwanted plants. 10. Use of at least one compound according to one of the claims 1 to 5 or an agent according to claim 8 for combating unwanted insects. 11. A method of controlling undesirable plants, thereby characterized in that at least one compound according to one of the claims 1 to 5 or an agent according to claim 7 on the undesirable plants or let their living space take effect.