WO2003043994A1

WO2003043994A1 - Substituted acylaminophenyluracils

Info

Publication number: WO2003043994A1
Application number: PCT/EP2002/012501
Authority: WO
Inventors: Roland Andree; Mark Wilhelm Drewes; Peter Dahmen; Dieter Feucht; Rolf Pontzen; Peter Lösel
Original assignee: Bayer Cropscience Aktiengesellschaft
Priority date: 2001-11-21
Filing date: 2002-11-08
Publication date: 2003-05-30
Also published as: DE10157063A1; AU2002358003A1

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

Substituted acylammophenyluracile

The invention relates to new substituted acylammophenyluracils, ner processes for their preparation 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 so far not gained any particular importance.

New substituted acylammophenyluracils 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 stands} for cyano, carbamoyl, thiocarbamoyl, halogen, or for 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, heterocyclyllycyllyl, carbonyl

found.

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

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

The compounds of the general formula (I) according to the invention can each be present in geometrically isomeric forms: they can be E- or Z-configured with respect to the substitution on the C-C double bond (cf. definition of A). The invention relates in each case to the pure E and Z isomers and to 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,

the respective possible substituents can preferably be found in the following list:

Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, -C-C4-alkyl, Cι-C4-haloalkyl, Cι-C4-Al oxy, Cι-C4-haloalkoxy, Cι-C4-alkylthio, Cι-C4-haloalkylthio , -C-C4-Alkylsulfmyl, Cι-C4-Halogenälkyl- sulfmyl, Cι-C4-Alkylsulfonyl, Cι-C4-Haloalkylsulfonyl, Cι-C4-alkylamino. Di- (-C-C4-alkyl) -amino, C1-C4-alkylcarbonyl, C1-C4- alkoxycarbonyl, Cι-C4-alkylaminocarbonyL Di- (Cι-C4-alkyl) -aminocarbonyl, di- (Cι-C4-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, forms a bicyclic group together with Ar in which the carbon atom adjacent to the adjacent carbonyl group forms A 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, C1-C4-alkoxy or C1-C4-alkoxycarbonyl.

R ² preferably represents carboxy, cyano, carbamoyl, thiocarbamoyl or alkyl or alkoxycarbonyl, each of which is optionally substituted by cyano, halogen or C1-C4alkoxy, 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 optionally substituted by cyano, halogen or C1-C4alkoxy, each having 1 to 6 carbon atoms in the alkyl groups,

for alkylsulfonyl optionally substituted by halogen with 1 to 6

Carbon atoms,

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, C1-C4-alkyl, C1 -

C4-haloalkyl, C1-C4-alkoxy, Cι-C4-haloalkoxy, Cι-C4-alkylthio, C 1 -C4-haloalkylthio, C \ -C4-alkylsulfinyl, C 1 -C4-haloalkylsulfmyl, C 1 -C4-alkylsulfonyl, C \ -C4-Haloalkylsulfonyl, C \ -C4- alkylcarbonyl, C1-C4- alkoxycarbonyl or di- (-C-C4-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, C1-C4-alkyl, -CC-haloalkyl, C1-C4-alkoxy, -C-C4-haloalkoxy, -C-C4-alkyl ~ thio, -C-C4-haloalkylthio, Cι -C4-AlkylsulfLnyl, -C-C4-haloalkylsulfinyl, Cι-C4-alkylsulfonyl, Cι-C4-haloalkylsulfonyl, C1-C4- alkylcarbonyl, Cι-C4-alkoxycarbonyl or di- (Cι-C4-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 furyl series. Tetrahydrofuryl, thienyl, tetrahydrothienyl, benzoniryl, di-hy <-lxobenzofuryl, benzothienyl, pyrrolyl, pyrazolyl, pyranyl, benzopyranyl, Dihydrobenzopyranyl, tetrahydrobenzopyranyl, pyridinyl, quinolinyl, 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, nylamino, n i-, s- or t-butylamino, dimethylamino, diethylamino, 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.

particularly preferably represents hydrogen, amino or 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, meth- or i-propyl, methoxy, ethoxy, n- or i-propoxy, each 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 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 in each case optionally substituted by fluorine, chlorine and / or bromine, ethenyl, propenyl, butenyl, ethenylcarbonyl, propenylcarbonyl, butenylcarbonyl, ethynyl, propynyl or butynyl, for in each case optionally substituted by fluorine, chlorine and / or bromine, cyclopropylcarbonyl, cyclopropylmethylcarbonyl, cyclobutylcarbonyl, cyclobutylmethylcarbonyl, cyclopentylcarbonyl, cyclopentylmethylcarbonyl, cyclohexylcarbonyl, cyclohexylmethylcarbonyl, cyclopropylsulfonyl, cyclopropylmethylsulfonyl, cyclylutylsulfonyl, cyclobutylsulfonyl, cyclobutylsulfonyl, cyclobutylsulfonyl, cyclobutylsulfonyl, cyclobutyl, 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-propylsulfmyl, trifluoromethylsulfyl, ethylsulfyl , n- or i-Propylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl substituted benzoyl, phenylsulfonyl, phenylprosulfonyl, phenylsulfonyl, phenylsulfonyl, phenylpropylyl, Phenylethylsulfonyl, or

each for 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, di- or methylamine aminosulfonyl substituted heterocyclylcarbonyl or heterocyclylsulfonyl from the series furylcarbonyl, furyl sulfonyl, thienylcarbonyl, thienylsulfonyl, pyrazolylcarbonyl, pyrazolylsulfonyl, pyridinylcarbonyl, pyridinylsulfonyl, quinolinylcarbonyl, quinolinylsulfonyl, pyriininylcarbonyl, pyrimidinylsulfonyl.

A very particularly preferably represents in each case optionally by cyano,

Fluorine, chlorine and / or bromine substituted ethene-1,2-diyl, propene-1,2-diyl or propene-2,3-diyl.

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, di-fluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylcarbonyl, trifluoromethylcarbonyl or i-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 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, tri - fluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, methylsulfonyl, Ethoxycarbonyl, n- or i-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 is} hydrogen, in each case optionally substituted by fluorine and / or chlorine, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, n-, i-, s- or t-butylsulfonyl, or for optionally by fluorine and / or chlorine substituted cyclopropylsulfonyl.

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

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-dimethylphenyl, 2,6-dimethylphenyl, 3,4-dimethylphenyl, 3,5-dimethylphenyl, 2-trifluoromethylphenyl, 3-trifluoromethylphenyl, 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-methylphenyl, 4-chloro-2-methylphenyl, 2-fluoro-4-chlorophenyl, 2-chloro-4-fluorophenyl; 2-chloro-4-bromophenyl, 2-bromo-4-chlorophenyl, 2-fluoro-4-bromophenyl, 2-bromo-4-fluorophenyl, 4-fluoro-2-methylphenyl, 4-bromo-2-methyl-phenyl.

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

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

in which

Rl, R ^, R3 R4 ₅ R5 ₅ _an d R 6 _{e eu} _he d above-stated meanings,

with acylating agents of the general formula (III)

^{^} Ar

X (HI) in which

A and Ar have one of the meanings given above and

X represents halogen,

optionally in the presence of a reaction auxiliary and optionally in

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 *: H -> NH ₂ or CH ₃ ) or by reaction with dicyan or hydrogen sulfide, (for example R ^: Br → CN or CN → CSNH ₂ ).

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

The aminophenyluracils to be used as starting materials in the process according to the invention for the preparation of compounds of the formula (I) are characterized by

Formula (II) generally defined. In the formula (II) Rl, R ^. R3, R4 _and ι R5 _before . preferably those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for R, R ^, 3 _S R4 and R5 ^ n-.

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

Formula (III) provides a general definition of the acylating agents further to be used as starting materials in the process according to the invention. In the formula (III) A and Ar preferably have those meanings which have already been given above in connection with the description of the compounds of the formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for A and Ar. X preferably represents fluorine, chlorine or bromine, particularly preferably chlorine.

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

The process according to the invention for the preparation of the compounds of the general

Formula (I) is preferably carried out using a reaction auxiliary. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention. These preferably include alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates and hydrides. hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate , Lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or potassium methoxide, ethanolate, -n- or -i-propanolate, -n-, - i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, N, N-dimethyl benzylamine ₅ 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 according to the invention for the preparation of the compounds of general

Formula (I) is preferably carried out using a diluent. leads. Inert organic solvents are particularly suitable as diluents for carrying out the process according to the invention. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

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

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

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

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers.

Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

The active compounds according to the invention can e.g. can be used in the following plants:

Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura. Desmodium, Emex, Erysimum,

Euphorbia, Galeopsis, Galinsoga, Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippex, Rotal Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

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

However, the use of the active compounds according to the invention is by no means limited to these

Limited genera, but extends in the same way to other plants.

Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems xmd

Because of and places with and without tree cover. The active compounds according to the invention can also be used to combat roughening in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture areas as well for selective weed control in annual crops.

The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for selective use

Control of monocot and dicot weeds in monocot and dicotyledon crops, both pre- and post-emergence.

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

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

Plants are understood to mean all plants and plant populations, such as xmd wished for unwanted wild plants or crops (including naturally occurring crops). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, fruits and seeds as well as roots, tubers and rhizomes. To the

Plant parts also include crops and vegetative and generative propagation material, such as cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and plant parts according to the invention with the active substances takes place directly or by acting on their environment, habitat or

Storage room according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, spreading and, in the case of nutritional material, in particular in the case of seeds, furthermore by wrapping in one or more layers.

The active compounds can be converted into the customary formulations, such as

Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated natural and synthetic substances as well as ultra-fine capsule quantities in polymeric substances.

These formulations are prepared in a known manner, for example by mixing the active ingredients with extenders, that is to say liquid solvents and / or solid carriers, optionally using surface-active agents, that is to say emulsifiers and / or dispersants and / or foam-generating agents. If water is used as an extender, organic solvents can, for example, also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils , Alcohols, such as butanol or glycol, and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

As solid carriers there are suitable: for example Ammom ^'umsalze and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and silicates, as solid carriers for granules come into question: eg broken and fractionated natural rocks such as calcite,

Marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stems; as emulsifying and / or foam-generating agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g.

Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite liquor and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural and synthetic powdery, granular or latex-shaped polymers, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospholipids, such as cephalins and lecithins and synthetic phospholipids, can be used in the formulations. Other additives can be mineral and vegetable oils. Dyes such as inorganic pigments, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes, such as alizarin, azo and metal phthalocyanine dyes, and spherical nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight of active compound, preferably between 0.5 and 90%.

The active compounds according to the invention, as such or in their formulations, can also be mixed with known herbicides and / or with substances which

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

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

(-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl), butroxydim, butylates, cafenstrole, caloxydim, carbetamides, carfentrazone (-ethyl), chloromethoxyid, chloronbenzene , Chlorimuron (-ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cinidone (-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, clodinafop (- propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron (-methyl) (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl), 2,4-D, 2,4-DB, Desmedipham, Diallate, Dicamba, Dichlorprop (-P), Diclofop (- methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefxxron, dimepiperate, dimethachlor, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamide, diquat, dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (- methyl), Ethofumesate, Ethoxyfen, Ethoxysulfuron, Etobenzanid, Fenoxaprop (-P-ethyl), Fentrazamide, Flamprop (-isopropyl, -isopropyl-L, -methyl) Flazasulfuron, Florasulam, Fluazifop (-P-butyl), Fluazolate, Flucarbazone (-sodium), Flufenacet, Flufenpyr, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumet-sulam, Fluometuron, Fluorochloridone (Fluorochloridone) Flupoxam, fluprop-acil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (- butoxypropyl, -meptyl), flurprimidol, flurtamone, fluthiacet (-methyl), fluthiamide, fomesafen, glufosulfinonate, foramsulfinonate -ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop (-ethoxyethyl, -P-methyl), hexazinones, imazamethabenz (-methyl), imazamethapyr, hnazamox, imazapic, imazapyr, imazaquine, imazethapyr, imazosulfuron, (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben , Isoxachlortole, Isoxaflutole, Isoxapyrifop, Ketospirox, Lactofen, Lenacil, Linuron, MCPA, Mecoprop, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuron, (alpha-)

Metolachlor, metosulam, metoxuron. Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxy- fluorfen, Paralquulin, Pendol, Pentacl, Pendulum, Paraquat, Pentacl oxazone, pethoxamide, phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron (-methyl), profluazole, profoxydim, prometryn, propachlor, propanil, propaquizafop, propisochlor, propoxycarbazone (-sodium), propyzamide, prosulfuroncarb, prosulfuron -ethyl), pyrazogyl, pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridate, pyridatol, pyriftalid, pyriminobac (- methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop

(-P-ethyl, -P-tefuryl), Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulfxxron, Tebutam, Tebuthiron, Tepraloxydim, Terbuthylazine, Terbutriafluide, Then Thiazo-pyr, thidiazimin, thifensulfuron (-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate, triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin, trifloxysulfuron, triflusulfuron (-methyl). Known safeners are also suitable for the mixtures, for example AD-67, BAS-145138, Benoxacor, Cloquintocet (-mexyl), Cyometrinil, 2,4-D, DKA-24, dichlormid, Dymron, Fenclorim, Fenchlorazol (-ethyl) , Flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), MCPA, mecoprop (-P), mefenpyr (-diethyl), MG-

191, Oxabetrinil, PPG-1292, R-29148.

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

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

Spray, sprinkle.

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

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

As already mentioned above, all plants and their parts can be treated according to the invention. In a preferred embodiment, plant species and plant cultivars which occur wildly or are obtained by conventional organic breeding methods, such as crossbreeding or protoplast fusion, and their varieties

Parts treated. In a further preferred embodiment, transgenes are Plants and plant varieties obtained by genetic engineering methods, possibly in combination with conventional methods (Genetically Modified Organisms) and their parts treated. The term "parts" or "parts of plants" or "plant parts" was explained above.

Plants of the plant varieties which are in each case commercially available or in use are particularly preferably treated according to the invention. Plant cultivars are understood to mean plants with certain properties (“traits”) which have been obtained by conventional breeding, by mutagenesis, or else by recombinant DNA techniques. These can be varieties, bio and genotypes.

Depending on the plant species or plant cultivars, their location and growth conditions (soils, climate, growing season, nutrition), the treatment according to the invention can also cause superadditive ("synergistic") effects. For example, reduced application rates and / or extensions of the

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

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

Tolerance to high or low temperatures, increased tolerance to Dryness or against water or soil salt content, increased flowering performance, easier harvesting, acceleration of ripeness, higher harvest yields, higher quality and / or higher nutritional value of the harvested products, higher 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 herbicidal active ingredients. Examples of transgenic plants are the important cultivated plants, such as cereals (wheat, rice), corn, soybeans, potatoes, cotton, rapeseed and fruit plants (with the fruits of apples, pears, citrus fruits and grapes), with corn, soybeans, potatoes and cotton xmd rapeseed are particularly highlighted. The traits that are particularly emphasized are the increased defense of the plants against insects by toxins arising in the plants, in particular those which are caused by the genetic material from Bacillus thuringiensis (for example by the genes CryΙA (a), CryIA (b), CryΙA (c), CryllA,

CrylllA, CryIIIB2, Cry9c, Cry2Ab, Cry3Bb and CrylF and their combinations) are produced in the plants (hereinafter referred to as "Bt plants"). The properties ("traits") also particularly emphasize the increased defense of plants against fungi, bacteria and viruses by systemic acquired resistance (SAR), systemin, phytoalexins, elicitors and resistance genes and correspondingly expressed proteins and toxins. The traits are also particularly emphasized by the plants' increased tolerance to certain herbicidal active compounds, for example imidazolinones, sulfonylureas, glyphosate or phosphinothricin (for example the "PAT" gene). The genes imparting the desired properties (“traits”) can also occur in combinations with one another in the transgenic plants. Examples of "Bt plants" are corn varieties, cotton varieties, soy varieties and potato varieties that are sold under the trade names YTELD GARD® (e.g. corn, cotton, soy), KnockOut® (e.g. corn), StarLink® (e.g. corn), Bollgard® ( Cotton), Nucotn® (cotton) and NewLeaf® (potato). As examples of

Herbicide-tolerant plants are maize, cotton and soybeans named under the trade names Roundup Ready® (tolerance to glyphosate e.g. corn, cotton, soy), Liberty Link® (tolerance to phosphinothricin, e.g. rapeseed), DVII® (tolerance to imidazolinones) and STS® (tolerance to sulfonylureas e.g. corn) to be expelled. The herbicide-resistant plants (conventionally bred to herbicide tolerance) include the varieties sold under the name Clearfield® (for example maize). Of course, these statements also apply to plant varieties developed in the future or coming onto the market in the future with these or future-developed genetic properties ("traits").

The plants listed can be treated particularly advantageously according to the invention with the compounds of the general formula I or the active compound mixtures according to the invention, the synergistic effects mentioned above occurring with the transgenic plants or plant cultivars in addition to the good control of the weed plants. The preferred ranges given above for the active substances or mixtures also apply to the treatment of these plants. Plant treatment with the compounds or mixtures specifically listed in the present text should be particularly emphasized.

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

When used as insecticides, the active compounds according to the invention can also be present in their commercially available formulations and in the use forms prepared from these formulations in a mixture with synergists. Synergists are compounds that increase the effectiveness of the active ingredients without the added synergist itself having to be active. The active substance content of the use forms prepared from the commercially available formulations can vary within wide ranges. The active substance concentration of the use forms can be between 0.0000001 and 95% by weight of active substance, preferably between 0.0001 and 1% by weight.

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

The active compounds of the formula (I) according to the invention are also suitable for combating arthropods which are used in agricultural animals, e.g. Cattle, sheep, goats, horses, pigs, donkeys, camels, buffalo, rabbits, chickens, turkeys, ducks, geese, bees, other pets such as e.g. Dogs, cats, house birds, aquarium fish and so-called experimental animals, such as Infest hamsters, guinea pigs, rats and mice. By fighting these arthropods, deaths and

Reductions in performance (for meat, milk, wool, skins, eggs, honey, etc.) are reduced, so that the use of the active compounds according to the invention enables more economical and simple animal husbandry.

The active ingredients according to the invention are used in the veterinary sector in a known manner by enteral administration in the form of, for example, tablets, capsules, drinkers, drenches, granules, pastes, boluses, the feed-through method, suppositories, by parenteral administration, for example by Injections (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.), implants, by nasal application, by dermal application in the form of, for example, diving or

Bathing (dipping), spraying (spray), pouring on (pour-on and spot-on), washing, powdering and with the help of shaped articles containing active ingredients, such as necklaces, ear tags, tail tags, limb tapes, holsters, marking devices, etc. When used for cattle, poultry, pets, etc., the active compounds of the formula (I) can be used as formulations (for example powders, emulsions, flowable agents) which contain the active compounds in an amount of 1 to 80% by weight, directly or apply after 100 to 10,000-fold dilution or use it as a chemical bath.

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

They are used in aerosols, non-pressurized sprays, e.g. Pump and

Atomizer sprays, fog machines, foggers, foams, gels, vaporizer products with cellulose or plastic vaporizer platelets, liquid vaporizers, gel and membrane vaporizers, propeller-driven vaporizers, energy-free or passive evaporation systems, moth papers, moth bags and moth gels, as granules or dusts or baits, in litter stations. ,

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

Manufacturing examples

example 1

A mixture of 2.00 g (4.76 mmol) of 1- (4-cyano-5-ethylsulfonylamino-2-fluorophenyl) -3-methyl-4-trifluoromethyl-3,6-dihydro-2,6-dioxo -l (2H) -pyrimidm, 1.46 g (6.20 mmol) (2E / Z) -3- (3,4-dichlorophenyl) -2-propenyl chloride, 0.63 g (6.20 mmol) Triethylamine and 50 ml of acetonitrile are stirred for 18 hours at room temperature (approx. 20 ° C) and then concentrated under reduced pressure. The residue is taken up in methylene chloride, shaken with aqueous IN hydrochloric acid, washed with water, dried with sodium sulfate and filtered. The mother liquor is washed with IN hydrochloric acid xmd then with water, dried with sodium sulfate and filtered. The filtrate is concentrated under reduced pressure, the residue is digested with diethyl ether / petroleum ether and the crystalline product is isolated by suction.

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

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

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

application examples

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

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

After three weeks, the degree of damage to the plants is rated in% damage in comparison 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 Preparation Example 1, 2, 3, 4, 6, 7, 8, 9, 10, 11 and 12 show with largely good tolerance to cultivated plants, such as e.g. Corn, soybeans and wheat, very powerful against

Weeds. Example B

Post-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

Test plants with a height of 5 to 15 cm are sprayed with the active substance preparation in such a way that the desired amounts of active substance are applied per unit area. The concentration of the spray liquor is chosen so that in

1000 1 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 destruction

In this test, for example, the compounds according to Preparation Example 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11 and 12 show, with largely good tolerance to crop plants, such as, for example, soybean and wheat, very strong activity 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 produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amounts of solvent and emulsifier, and the concentrate is diluted to the desired amount with water containing emulsifier

Concentration.

Seedlings of the broad bean (Viciafaba minor), which are infested with the green peach aphid (Myzus persicae), are immersed in a preparation of active compound of the desired concentration 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 will be killed.

In this test, e.g. the compound according to preparation example 10 at an active ingredient concentration of 100 ppm kills 100%.

Claims

claims

Compounds of formula (I)

in which

A represents optionally substituted, straight-chain or branched alkenediyl,

where A and Ar can also be combined in bicyclic groups,

Rl 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 optionally substituted alkyl or alkoxy, xmd

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

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

A represents alkenediyl with 2 to 10 carbon atoms optionally substituted by cyano or halogen,

Ar for optionally substituted, monocyclic or bicyclic

Aryl with up to 10 carbon atoms, or

represents optionally substituted, monocyclic or bicyclic heterocyclyl having up to 9 carbon atoms xmd 1 to 4 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms,

the respective possible substituents can be found in the following list:

Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C1-C4- alkyl, Cj-C4-haloalkyl, C1-C4- alkoxy, Cι-C4-haloalkoxy, Cι-C4-alkylthio, Cι -C4-haloalkylthio, Cι - C4-alkylsulfmyl, Ci-C4-haloalkylsulfinyl, C1-C4-alkylsulfonyl, Cτ -C4-haloalkylsulfonyl, Cι ^ C4-alkylamino, di- (Cι-C4-alkyl) -amino, C1-C4- Alkylcarbonyl, C 1 -C 4 alkoxycarbonyl, C 1 -C 4 alkylaminocarbonyl, di (C 1 -C 4 alkyl) aminocarbonyl, di (C 4 -C 4 alkyl) aminosulfonyl,

and where A and Ar can also be combined in bicyclic groups such that A, if it stands for ethen-1,2-diyl, together with Ar forms a bicyclic group in which the carbononi from A adjacent to the adjacent carbonyl group is via a Alkylengruppierxmg, in particular methylene or ethylene, or is linked via O (oxygen) or S (sulfur) with an ortho position of Ar,

R 1 represents hydrogen, amino or alkyl which has 1 to 6 carbon atoms and is optionally substituted by cyano, carboxy, halogen, C1-C4-alkoxy or C1-C4-alkoxycarbonyl,

R ^{2 stands} for carboxy, cyano, carbamoyl, thiocarbamoyl or for alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C - [- C4-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 for hydrogen, for alkyl, alkylcarbonyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C1-C4alkoxy, 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, C1-C4-alkyl, C] ^ C4-haloalkyl, C1-C4-alkoxy, Cι-C4-haloalkoxy, Cι-C4-alkylthio, Cι-C4-haloalkylthio, Cι-C4 -Alkylsulfinyl, Ci- C4-haloalkylsulfinyl, C1-C4- alkylsulfonyl, Cτ -C4-haloalkylsulfonyl, C _j -C4- alkylcarbonyl, C1-C4- alkoxycarbonyl or di- (Cι-

C4-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, C1-C4-alkyl, -C-C4-haloalkyl, Cι-C4-alkoxy, Cι-C4-haloalkoxy, Cι-C4-alkylthio, Cι-C4-haloalkylthio, Cι-C4 -Alkylsulfmyl, Ci- C4-haloalkylsulfmyl, C1-C4- alkylsulfonyl, Cι-C4-haloalkyl-sulfonyl, C1-C4- alkylcarbonyl, C1-C4- alkoxycarbonyl or di- (Cι-

C4-alkylamino) -sulfonyl-substituted heterocyclylcarbonyl or Heterocyclylsulfonyl with 1 to 5 carbon atoms and 1 to 3 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms.

3. Verbindungsxmgen 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 for each optionally substituted phenyl or naphthyl, or for each optionally substituted heterocyclyl from the series furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, benzofuryl, dihydrobenzofuryl, benzothienyl, pyrrolyl, pyrazolyl, pyranyl, benzopyranyl, pyridylzyrylopyridylzyrylopyridyl, pyridylzyrylopyridyl, pyridylzyrylopyridyl, dihydrozylyridyl, pyridylzyridyl, pyridylzyridyl Pyrimidinyl stands,

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-propylsulfmyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonamino, trifluoromethylsulfonyl, trifluoromethyl , n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, 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 which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy,

R ^{2 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 represents} hydrogen, fluorine, chlorine, bromine or 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 for cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or for each optionally substituted by fluorine and / or chlorine Is methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, and

for 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 each optionally substituted by fluorine, chlorine and / or bromine, ethenyl, propenyl, butenyl, ethenylcarbonyl, propenylcarbonyl, butenylcarbonyl, ethynyl, propynyl or butynyl,

for in each case optionally substituted by fluorine, chlorine and / or bromine, cyclopropylcarbonyl, cyclopropylmethylcarbonyl, cyclobutylcarbonyl, cyclobutylmethylcarbonyl, cyclopentylcarbonyl, cyclopentylmethylcarbonyl, cyclohexylcarbonyl, cyclohexylmethylcarbonyl, cyclopropylsulfonyl, cyclopropylmethylsulfonyl, cyclyl butyl, cyclyl butyl, cyclyl butyl, cyclyl, 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, difluoro methoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, ethylsulfonyl - or i-propylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-

Butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl substituted benzoyl, phenylsulfonyl, phenylacetyl, phenylpropionyl, benzylsulfonyl or phenylethylsulfonyl, or

each for 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, carbonyl or carbonyl Dimethylaminosulfonyl or diethylamino sulfonyl-substituted heterocyclylcarbonyl or heterocyclylsulfonyl from the series furylcarbonyl, furylsulfonyl, thienylcarbonyl, thienylsulfonyl, pyrazolylcarbonyl, pyrazolylsulfonyl, pyridinylcarbonyl, pyridinylsulfonyl, pyrolinylmethyllaminolylylpyrinylylylvinyl, quinolinylmethyllaminolylyl, quinolinylvinyl, quinolinylmethyllaminolylyl, quinolinylvinyl,

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 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 or i-propoxycarbonyl,

Rl 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-propyl- each optionally substituted by fluorine and / or chlorine sulfonyl, n-, i-, s- or t-butylsulfonyl, or cyclopropylsulfonyl optionally substituted by fluorine and / or chlorine.

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

A and Ar together for grouping

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, trifluoromoxycarbonyl propoxycarbonyl,

Rl 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, xmd

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

Rl, R ^, R3 ₅ R4 ₃ R5 and RÖ 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,

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

8. Insecticidal agents, characterized by the content of at least one compound according to one of claims 1 to 5 and conventional extenders.

9. Use of at least one compound according to one of claims 1 to 5 or an agent according to claim 7 for controlling unwanted plants.

10. Use of at least one compound according to one of claims 1 to 5 or an agent according to claim 8 for controlling unwanted insects.

11. A method for controlling desired plants, characterized in that at least one compound according to one of Claims 1 to 5 or an agent according to Claim 7 is allowed to act on the desired plants or their habitat.