AU761304B2 - Use of N-substituted heterocyclylalkylamines as herbicides and novel N-substituted thienylalkylamines - Google Patents

Description

WO 00165916 PCT/EP00/03496 -1- Use of N-substituted heterocyclylalkylamines as herbicides, and novel Nsubstituted thienylalkylamines The invention relates to the use of N-substituted heterocyclylalkylamines as herbicides, and to novel N-substituted thienylalkylamines and to processes for their preparation.

It is known that certain N-substituted heterocyclylalkylamines have insecticidal properties (cf. EP-A-364844, EP-A-418199, JP-A-08231524 cited in Chem.

Abstracts 125:300813). However, herbicidal properties of such compounds have hitherto not been disclosed.

It is furthermore known that certain substituted arylalkyl guanidines can influence the growth of plants (cf. DE-A-3345281, US-A-4639268).

It has now been found that the N-substituted heterocyclylalkylamines of the general formula (I) R R 2 Z.A N N H Y in which A represents a single bond or represents alkanediyl, R' represents optionally substituted alkyl,

R

2 represents hydrogen, amino or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, Y represents cyano or nitro and WO 00165916 PCT/EP00/03496 -2- Z represents optionally substituted heterocyclyl, have strong herbicidal activity.

Saturated or unsaturated hydrocarbon radicals, such as alkyl or alkenyl, are in each case straight-chain or branched as far as this is possible including in combination with heteroatoms, such as in alkoxy.

Optionally substituted radicals can be mono- or polysubstituted, where in the case of polysubstitution, the substituents can be identical or different.

The compounds of the general formula according to the invention contain at least one carbon-nitrogen double bond and can therefore be present in different E- and Zconfigured isomeric forms. The invention relates both to the use of the individual Eand Z-configured isomeric forms of the compounds of the general formula and of the mixtures of these isomeric compounds.

The compounds of the general formula according to the invention contain at least one asymmetrically substituted carbon atom and can therefore be present in different enantiomeric and S-configured forms) or diastereomeric forms. The invention relates both to the use of the different possible individual enantiomeric or stereoisomeric forms of the compounds of the general formula and of the mixtures of these isomeric compounds.

Preferred substituents or ranges of the radicals present in the formulae listed above and below are described below.

A preferably represents a single bond or represents alkanediyl having 1 to 4 carbon atoms.

WO 00165916 WO 0065916PCT/EPOO/03496 -3- R1 preferably represents optionally cyano-, halogen-, or C 1

-C

4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms.

R 2 preferably represents hydrogen, amino or represents in each case optionally cyano-, halogen-, C 1

-C

4 -alkoxy-, C 1

-C

4 -alkylthio-, C 1

-C

4 -alkylsulfinyl- or C 1

C

4 -alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups.

Z preferably represents an optionally substituted monocyclic or bicyclic heterocyclic grouping from the group consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, i sobenzofuryl, thienyl, tetrahydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolyl, isoindolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl.

where the preferred substituents are selected from the group consisting of nitro, cyano, carboxyl, carbamoyl, thiocarbamnoyl, sulfamoyl, halogen, C 1

-C

4 alkyl, C 1

-C

4 -halogenoalkyl, C 1

-C

4 -alkoxy, C 1

-C

4 -halogenoalkoxy, C 1

-C

4 alkylthio, C 1

-C

4 -halogenoalkylthio, C 1

-C

4 -alkylsulfinyl, C 1

-C

4 -halogenoalkylsulfinyl, C 1

-C

4 -alkylsulfonyl, C 1

-C

4 -halogenoalkylsulfonyl, C 1

-C

4 -alkylcarbonyl, C 1

-C

4 -alkoxy-carbonyl, C 1

-C

4 -alkylamino-carbonyl, di-(C 1

-C

4 alkyl)-amino-carbonyl, C 1

-C

4 -alkylamino-sulfonyl, di-(C 1

-C

4 -alkyl)aminosulfonyl, phenyl.

A particularly preferably represents a single bond, represents methylene (-CH 2 dimethylene (ethane- I ,2-diyl, -CH 2

CH

2 ethylidene (ethane- 1, 1 -diyl,

-CH(CH

3 trimethylene (propane- 1,3-diyl, -CH 2

CH

2

CH

2 or propane-1,2di'yl (-CH 2

CH(CH

3 WO 00165916 PCT/EPOO/03496 -4- R' particularly preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, i-, s- or t-butyl.

R

2 particularly preferably represents hydrogen, amino, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonylsubstituted methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, 1-, s- or t-butylamino, dimethylamino, diethylamino or dipropylamino.

Z particularly preferably represents an optionally substituted monocyclic or bicyclic heterocyclic grouping from the group consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, isobenzofuryl, thienyl, tetrahydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolyl, isoindolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl, where the particularly preferred substituents are selected from the group consisting of nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, s- or tbutyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or ipropoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or propylthio, 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- WO 00165916 PCT/EPOO/03496 propoxy-carbonyl, methylaminocarbonyl, ethylami nocarbonyl, n- or i-propylamino-carbonyl, dimethylaminocarbonyl, diethylamino-carbonyl, methylaminosulfonyl, ethylaminosulfonyl, n- or i-propylamino-sulfonyl, dimethylaminosulfonyl, diethylamino-sulfonyl, phenyl.

A very particularly preferably represents a single bond or represents dimethylene

(-CH

2

CH

2 R very particularly preferably represents methyl, ethyl, n- or -propyl.

R very particularly preferably represents hydrogen, amino, methyl, ethyl, n- or ipropyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or ipropylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino.

Z very particularly preferably represents in each case optionally substituted thienyl or benzothienyl.

where the very particularly preferred substituents are selected from the group consisting of nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, chlorodifluoromethyl, fiuorodichloromethyl, 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, trifluoromethylsulfonyl, acetyl, propionyl, n- or i- butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl.

WO 00165916 PCT/EP00/03496 -6- The abovementioned general or preferred radical definitions apply both to the end products of the formula and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, i.e. including combinations between the given preferred ranges.

Preference according to the invention is given to the herbicidal use of compounds of the formula which contain a combination of the meanings listed above as being preferred.

Particular preference according to the invention is given to the herbicidal use of compounds of the formula which contain a combination of the meanings listed above as being particularly preferred.

Very particular preference according to the invention is given to the herbicidal use of compounds of the formula which contain a combination of the meanings listed above as being very particularly preferred.

A small number of the compounds of the general formula is already known (cf.

EP-A-364844, EP-A-418199, EP-A-483062, JP-A-08231524 cited in Chem.

Abstracts 125:300813) or as part of an earlier, but not prior-published application (cf.

DE-A-19 832 447).

A relatively large number of the compounds of the general formula has hitherto not been disclosed in the literature. Among these, emphasis is given, in particular, to the novel compounds of the general formula in which Z represents in each case optionally substituted thienyl or benzothienyl excluding the compounds N'-cyano- N-[l-methyl-3-(3-thienyl)-propyl]-ethaneimidamide, N'-cyano-N-[ 1-ethyl-3-(3thienyl)-propyl]-ethaneimidamide, N'-cyano-N-[l-methyl-3-(2-thienyl)-propyl]ethaneimidamide, N'-cyano-N-[1-(2-thienyl)-ethyl]-ethaneimidamide and N'-cyano- WO 00165916 PCT/EPOO/03496 -7- N-[1 -(3-thienyl)-ethyl]-ethaneimidamide (cf. DE-A-19 832 447) mentioned as examples in earlier applications.

Accordingly, the novel substances according to the invention that are claimed are all those compounds of the general formula in which A represents a single bond or represents alkanediyl having 1 to 4 carbon atoms, R' represents optionally cyano-, halogen- or C 1

-C

4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms, R2 represents hydrogen, amino or represents in each case optionally cyano-, halogen-, C 1

-C

4 -alkoxy-, C 1

-C

4 -alkylthio-, C 1

-C

4 -alkylsulfinyl- or C 1

-C

4 alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups, Y represents cyano or nitro, and Z represents in each case optionally substituted thienyl or benzothienyl, where the possible substitutents are selected from the group consisting of nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, CI-C 4 alkyl, C 1

-C

4 -halogenoalkyl, C 1

-C

4 -alkoxy, C -C 4 -halogenoalkoxy, C 1

-C

4 alkylthio, C 1

-C

4 -halogenoalkylthio, Cl-C 4 -alkylsulfinyl, C-C 4 -halogenoalkylsulfinyl, C -C 4 -alkylsulfonyl, C 1

-C

4 -halogenoalkylsulfonyl, C 1

I-C

4 -alkylcarbonyl, C 1

-C

4 -alkoxy-carbonyl, CI-C 4 -alkylamino-carbonyl, di-(C 1

-C

4 alkyl)-amino-carbonyl, C -C 4 -alkylamino-sulfonyl, di-(C -C 4 -alkyl)-aminosulfonyl, phenyl, WO 00165916 PCT/EP00/03496 -8except for the compounds N'-cyano-N-[1-methyl-3-(3-thienyl)-propyl]-ethaneimidamide, N'-cyano-N-[l-ethyl-3-(3-thienyl)-propyl]-ethaneimidamide, N'-cyano-N-[1methyl-3-(2-thienyl)-propyl]-ethaneimidamide, N'-cyano-N-[ -(2-thienyl)-ethyl]ethaneimidamide and N'-cyano-N-[l-(3-thienyl)-ethyl]-ethaneimidamide (cf. DE-A- 19 832 447).

A, R 1

R

2 and the substituents listed for Z preferably have the meanings given above as being preferred.

Examples of the compounds of the general formula according to the invention are listed in the groups below. Independently of the individual formulae shown, the compounds represented by these formulae are in each case the possible E and Z isomers and mixtures thereof.

WO 00165916 WO 0065916PCT/EPOO/03496 -9- Group 1 a R1 R2 I I H Y Here, A, R 1, R 2and Y have, for example, the meanings listed in the table below.

A R' R 2 Y A RI R2Y

CH

3 H CN CH 3 H NO 2

CH

3

CH

3 CN CH 3

CH

3

NO

2

CH

3

C

2

H

5 CN CH 3

C

2

H

5

NO

2

CH

3

C

3 CN CH 3

C

3

NO

2

CH

3

C

3 CN CH 3

C

3

NO

2

CH

3

OCH

3 CN CH 3

OCH

3

NO

2

CH

3 0C 2

H

5 CN CH 3 0C 2

H

5

NO

2

CH

3 0C 3

H

7 -n CN CH 3

OC

3

NO

2

CH

3

OC

3 H-1 CN CH 3 0C 3

H

7 -i NO 2

CH

3

SCH

3 CN CH 3

SCH

3

NO

2

CH

3

SC

2

H

5 CN CH 3

SC

2

H

5

NO

2

CH

3

SC

3

H

7 -n CN CH 3

SC

3

NO

2

CH

3

SC

3

H

7 -i CN CH 3

SC

3

H

7 -i NO 2

CH

3

NH

2 CN CH 3

NH

2

NO

2

CH

3

NHCH

3 CN CH 3

NHCH

3

NO

2

CH

3

NHC

2

H

5 CN CH 3

NHC

2

H

5

NO

2

CH

3

NHC

3

H

7 -n CN CU 3

NHC

3

NO

2

CU

3

NHC

3

H

7 -i CN CU 3

NHC

3

U

7 -i NO 2

CH

3

N(CH

3 2 CN CH 3

N(CH

3 2

NO

2

CU

3

N(C

2

H

5 2 CN CU 3

N(C

2

H

5 2

NO

2

C

2

H

5 H CN C 2

U

5 H NO 2 WO 00165916 W00015916PCT/EPOO/03496 10 RI R 2 Y A R R 2

Y

C

2

H

5

CH

3 CN C 2

H

5

CH

3

NO

2

C

2

H

5

C

2

H

5 CN C 2

H

5

C

2

H

5 N0 2

C

2

H

5

C

3

H

7 -n CN C 2

H

5

C

3

H

7 -n NO 2

C

2

H

5

C

3

H

7 -i CN C 2

H

5

C

3

H

7 -i N0 2

C

2

H

5

OCH

3 CN C 2

H

5

OCH

3

NO

2

C

2

H

5

OC

2

H

5 CN C 2

H

5 0C 2

H

5

NO

2

C

2

H

5

OC

3 CN C 2

H

5

OC

3 H7-n NO 2

C

2

H

5 0C 3

H

7 -i CN C 2

H

5 0C 3

H

7 -i NO 2

C

2

H

5

SCH

3 CN C 2

H

5

SCH

3

NO

2

C

2

H

5

SC

2

H

5 CN C 2

H

5

SC

2

H

5

NO

2

C

2

H

5

SC

3

H

7 -n CN C 2

H

5

SC

3

H

7 -n NO 2

C

2

H

5

SC

3

H

7 -i CN C 2

H

5

SC

3

H

7 -i NO 2

C

2

H

5

NH

2 CN C 2

H

5

NH

2

NO

2

C

2

H

5

NHCH

3 CN -C 2

H

5

NHCH

3

NO

2

C

2

H

5

NHC

2

H

5 CN -C 2

H

5

NHC

2

H

5

NO

2

C

2

H

5

NHC

3 CN -C 2

H

5

NHC

3

NO

2

C

2

H

5

NHC

3

H

7 -i CN -C 2

H

5

NHC

3

H

7 -i NO 2

C

2

H

5

N(CH

3 2 CN -C 2

H

5

N(CH

3 2

NO

2

C

2

H

5

N(C

2

H

5 2 CN -C 2

H

5

N(C

2

H

5 2

NO

2

-CH

2

CH

2

ICH

3

-CH

2

CH

2

CH

3

NO

2

-CH

2

CH

2

CH

3

CH

3 CN -CH 2

CH

2

CH

3

CH

3

NO

2

-CH

2

CH

2

CH

3

C

2

H

5 CN -CH 2

CH

2

CH

3

C

2

H

5

NO

2

-CH

2

CH

2

CH

3

C

3

H

7 -n CN -CH 2

CH

2

CH

3

C

3

H

7 -n NO 2

-CH

2

CH

2

CH

3

C

3 CN -CH 2

CH

2

CH

3

C

3

H

7 -i NO 2

-CH

2

CH

2

CH

3

OCH

3 CN -CH 2

CH

2

CH

3

OCH

3

NO

2

-CH

2

CH

2

CH

3 0C 2

H

5 CN -CH 2

CH

2

CH

3 0C 2

H

5

NO

2

-CH

2

CH

2

CH

3

OC

3 CN -CH 2

CH

2

CH

3 0C 3

H

7 -n NO 2

-CH

2

CH

2

CH

3 0C 3

H

7 -i CN -CH 2

CH

2

CH

3 0C 3

H

7 -i NO 2 WO 00165916 WO 0065916PCT/EPOO/03496 I1I- A R R 2 y A R R2

-CH

2

CH

2

CH

3

SCH

3 CN -CH 2

CH

2

CH

3

SCH

3 N0 2

-CH

2

CH

2

CH

3

SC

2

H

5 CN -CH 2

CH

2

CH

3

SC

2

H

5

NO

2

-CH

2

CH

2

CH

3

SC

3

H

7 -n CN -CH 2

CH

2

CH

3

SC

3

NO

2

-CH

2

CH

2

CH

3

SC

3

H

7 -i CN -CH 2

CH

2

CH

3

SC

3

H

7 -i NO 2

-CH

2

CH

2

CH

3

NH

2 CN -CH 2

CH

2

CH

3

NH

2

NO

2

-CH

2

CH

2

CH

3

NHCH

3 CN -CH 2

CH

2

CH

3

NHCH

3

NO

2 -C H 2 H 2 H 3 H C 2 H C N-C H 2 H 2 H 3 H C 2 H N O

-CH

2

CH

2

CH

3 NHC2H5- CN -CH 2

CH

2

CH

3 NHC2H5- NO 2

-CH

2

CH

2

CH

3

NHC

3

H

7 -i CN -CH 2

CH

2

CH

3

NHC

3

H

7 -i NO 2

-CH

2

CH

2

CH

3 N(CH7) 2 CN -CH 2

CH

2

CH

3 N(CH7) 2 N0 2

-CH

2

CH

2

CH

3

N(C

2 H3) 2 CN -CH 2

CH

2

CH

3

N(C

2 H3) 2

NO

2

-CH

2

CH

2

C

2 H3 NH5 CN -CH 2

CH

2

C

2 H3 NH5 NO 2

-CH

2

CH

2

C

2

H

5 H CN -CH 2

CH

2

C

2

H

5 H N0 2

-CH

2

CH

2

C

2

H

5

C

2 H3 CN -CH 2

CH

2

C

2

H

5

C

2 H3 NO 2

-CH

2

CH

2

C

2

H

5 C2H-,- CN -CH 2

CH

2

C

2

H

5 C2H5- NO 2

-CH

2

CH

2

C

2

H

5

C

3

H

7 -i CN -CH 2

CH

2

C

2

H

5

C

3 H-n NO 2

-CH

2

CH

2

C

2

H

5 CH7 CN -CH 2

CH

2

C

2

H

5 CH7- NO 2

-CH

2

CH

2

C

2

H

5 0C 2 H3 CN -CH 2

CH

2

C

2

H

5 0C 2 H3 NO 2

-CH

2

CH

2

C

2

H

5 OC2H-,- CN -CH 2

CH

2

C

2

H

5 0C2H5- NO 2

-CH

2

CH

2

C

2

H

5 0C 3

H

7 -i CN -CH 2

CH

2

C

2

H

5 0C 3

H

7 -i NO 2

-CH

2

CH

2

C

2

H

5 SC3H7- CN -CH 2

CH

2

C

2

H

5 SC3H7- NO 2

-CH

2

CH

2

C

2

H

5

SC

2 H3 CN -CH 2

CH

2

C

2

H

5

SC

2 H3 NO 2

-CH

2

CH

2

C

2

H

5 SC2H-,- CN -CH 2

CH

2

C

2

H

5 SC2H-,- NO 2

-CH

2

CH

2

C

2

H

5

SC

3

H

7 -i CN -CH 2

CH

2

C

2

H

5

SC

3

H

7 -i NO 2

-CH

2

CH

2

C

2

H

5 NCH- CN -CH 2

CH

2

C

2

H

5 NcH- NO 2

-CH

2

CH

2

C

2

H

5 NHCH CN -CH 2

CH

2

C

2

H

5 NHCH NO 2

-CH

2

CH

2

C

2

H

5

NHC

2 H3 CN -CH 2

CH

2

C

2

H

5

NHC

2 H3 NO 2

-CH

2

CH

2

C

2

H

5 NHC2H5- CN -CH 2

CH

2

C

2

H

5 NHC2H5- NO 2 WO 00165916 WO 0065916PCT/EPOO/03496 12 A R' R2Y A R' R2Y

-CH

2

CH

2

C

2

H

5

NHC

3 CN -CH 2

CH

2

C

2

H

5

NHC

3

H

7 -1 NO 2

-CH

2

CH

2

C

2

H

5

N(CH

3 2 CN -CH 2

CH

2

C

2

H

5

N(CH

3 2

NO

2

-CH

2

CH

2

C

2

H

5

N(C

2

H

5 2 CN -CH 2

CH

2

C

2

H

5

N(C

2

H

5 2

NO

2

C

3 H CN -C 3 H NO 2

C

3

H

7 -i CH 3 CN C 3

H

7 -i CH 3

NO

2

C

3

C

2

H

5 CN

C

3

C

2

H

5

NO

2

C

3

H

7 -i C 3

H

7 -n CN C 3

C

3

H

7 -n NO 2

C

3

H

7 -i C 3

H

7 -i CN C 3

C

3

H

7 -i NO 2

C

3

H

7 -i OCH 3 CN

C

3

OCH

3

NO

2

C

3

H

7 -i 0C 2

H

5 CN C 3

H

7 -i 0C 2

H

5

NO

2

C

3

H

7 -i OC 3 CN C 3 0C 3

H

7 -n NO 2

C

3

H

7 -i OC 3 CN

C

3

OC

3

NO

2

C

3

H

7 -i SCH 3 CN

C

3

H

7 -i SCH 3

NO

2

C

3

SC

2

H

5 CN C 3

H

7 -i SC 2

H

5

NO

2

C

3

SC

3

H

7 -n CN C 3

SC

3

H

7 -n NO 2

C

3

SC

3

H

7 -i CN C 3

SC

3

H

7 -i NO 2

C

3

H

7 -i NH 2 CN C 3

H

7 -i NH 2

NO

2

C

3

H

7 -i NHCH 3 CN C 3

NHCH

3

NO

2

C

3

H

7 -i NHC 2

H

5 CN C 3

H

7 -i NHC 2

H

5

NO

2

C

3

H

7 -i NHC 3

H

7 -n CN C 3

NHC

3

H

7 -n NO 2

C

3

NHC

3 CN C 3

H

7 -i NHC 3

H

7 -i NO 2

C

3

H

7 -i N(CH 3 2 CN C 3 H-1 N(CH 3 2

NO

2

C

3

H

7 -i N(C 2

H

5 2 .CN C 3

H

7 -i N(C 2

H

5 2

NO

2

-CH

2

CH

2

C

3

H

7 -i H CN -CH 2

CH

2

C

3

H

7 -i H NO 2

-CH

2

CH

2

C

3

H

7 -i CH 3 CN -CH 2

CH

2

C

3

H

7 -i CH 3

NO

2

-CH

2

CH

2

C

3

H

7 -i C 2

H

5 CN -CH 2

CH

2

C

3

H

7 -i C 2

H

5

NO

2

-CH

2

CH

2

C

3

C

3

H

7 -n CN -CH 2

CH

2

C

3

C

3

NO

2

-CH

2

CH

2

C

3

H

7 -i C 3 H-1 CN -CH 2

CH

2

C

3

H

7 -i C 3

H

7 -i NO 2 WO 00165916 WO 0065916PCT/EPOO/03496 13 A R1 R2Y A RI R2Y

-CH

2

CH

2

C

3

H

7 -i OCH 3 CN -CH 2

CH

2

C

3

H

7 -i OCH 3

NO

2

-CH

2

CH

2

C

3 H7,-i OC 2

H

5 CN -CH 2

CH

2

C

3 H-1 0C 2

H

5

NO

2

-CH

2

CH

2

C

3

OC

3 CN -CH 2

CH

2

C

3

H

7 -i OC 3

NO

2

-CH

2

CH

2

C

3

H

7 -i OC 3 CN -CH 2

CH

2

C

3

H

7 -i OC 3

NO

2

-CH

2

CH

2

C

3

SCH

3 CN -CH 2

CH

2

C

3

SCH

3

NO

2

-CH

2

CH

2

C

3

H

7 -i SC 2

H

5 CN -CH 2

CH

2

C

3

SC

2

H

5

NO

2

-CH

2

CH

2

C

3

SC

3

H

7 -n CN -CH 2

CH

2

C

3

H

7 -i SC 3

NO

2

-CH

2

CH

2

C

3

H

7 -i SC 3

H

7 -i CN -CH 2

CH

2

C

3

H

7 -i SC 3

H

7 -i NO 2

-CH

2

CH

2

C

3

NH

2 CN -CH 2

CH

2

C

3

H

7 -i NH 2

NO

2

-CH

2

CH

2

C

3

H

7 -i NHCH 3 CN -CH 2

CH

2

C

3

H

7 -i NHCH 3

NO

2

-CH

2

CH

2

C

3

NHC

2

H

5 CN -CH 2

CH

2

C

3

H

7 -i NHC 2

H

5

NO

2

-CH

2

CH

2

C

3

H

7 -i NHC 3

H

7 -n CN -CH 2

CH

2

C

3

H

7 -i NHC 3

NO

2

-CH

2

CH

2

C

3

NHC

3

H

7 -i CN -CH 2

CH

2

C

3

NHC

3

H

7 -i NO 2

-CH

2

CH

2

C

3

H

7 -i N(CH 3 2 CN -CH 2

CH

2

C

3

H

7 -i N(CH 3 2

NO

2 Group 2 R1 R2 I I H Y Here, A, R1, R 2and Y have, for example, the meanings listed above in the table for Group 1.

Group 3

OH

3 1 2 I I H Y WO 00165916 PCT/EP00/03496 14- Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 4 1 2 I R H Y Here, A, R R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group R1 2 R R2 S A,'NkN I I H Y Here, A, R R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 6 Br S 1 R2 I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

WO 00165916 PCT/EP00/03496 Group 7 Br I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 8

CH

3 H3C A NN I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 9

R

1 R 2 S A N N I I H Y Here, A, R R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group

SR

1

R

2 I I In H Y WO 00165916 PCT/EP00/03496 -16- Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 11

H

3

C

HaSl R 1

R

2 H3C S A N

N

I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 12

CH

3 S A N N I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 13 SR 1 2 I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

WO 00165916 PCT/EPOO/03496 -17- Group 14

H

3

C

n

R

1

R

2 C A N" N I I H Y Here, A, R R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group

F

sRF

R

1

R

2 I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 16 C2 RH I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

WO 00165916 PCT/EP00/03496 -18- Group 17

H

3

C

I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 18

SR

1

R

2 I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 19

CH

CH

3

R

1

R

2

H

3 C I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

WO 00165916 PCT/EP00/03496 -19- Group

C

2

H

5

R

1

R

2 Cl- A N I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 21

CI

H

5

C

2 A N

N

S f R 1

R

2 I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 22

R

1

R

2 CI-< A N

N

I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

WO 00165916 PCTEPOO/03496 Group 23

CI

S C

R

1

R

2 CI A N" N I I H Y Here, A, R R 2 and Y have, for example, the meanings listed above in the table for Group 1.

Group 24

CH,

SOH

3

R

2 H3C S I IR 3 A N N I I H Y Here, A, R 2 and Y have, for example, the meanings listed above in the table for Group 1.

The compounds of the general formula are obtained when heterocyclylamines of the general formula (II) Z A N ,.H in which A, R' and Z are as defined above are reacted with imino compounds of the general formula (HI) WO 00165916 PCT/EPOO/03496 -21-

R

2 X N m

I),

Y

in which

R

2 and Y are as defined above and X represents alkoxy or alkylthio, if appropriate in the presence of a diluent.

Using, for example, 1-(5-fluoro-2-thienyl)-ethylamine and (dimethoxymethyleneamino)-(nitrilo)-methane as starting materials, the course of the reaction in the process according to the invention can be illustrated by the formula scheme below: 0CH

C

H

3 OH H3 3 0

CH

3 FNH O N F SC

OH

3 HN H The formula (II) provides a general definition of the heterocyclylalkylamines to be used as starting materials in the process according to the invention for preparing compounds of the general formula In the general formula A, R' and Z preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula as being preferred, particularly preferred or very particularly preferred for A, R' and Z.

The heterocyclylalkylamines of the general formula (II) are known and/or can be prepared by processes known per se (cf. DE-A-19744232 LeA 32589, DE-A- 19816055).

WO 00165916 PCT/EP00/03496 -22- The formula (1I) provides a general definition of the imino compounds further to be used as starting materials in the process according to the invention for preparing compounds of the general formula In the general formula (Ill), R 2 and Y preferably have those meanings which have already been mentioned above, in connection with the description of the compounds of the general formula (I) according to the invention, as being preferred, particularly preferred or very particularly preferred for R 2 and Y; X represents in particular CI-C 4 -alkoxy or CI-C 4 alkylthio, in particular methoxy, ethoxy, methylthio or ethylthio.

The imino compounds of the general formula (lII) are known and/or can be prepared by processes known per se (cf. Chem. Ber. 100 (1967), 2604-2615; J. Am. Chem.

Soc. 76 (1954), 1877-1879; J. Org. Chem. 26 (1961), 3347-3350; loc. cit. 28 (1963), 1816-1821; loc. cit. 35 (1970), 2067-2069; Synthesis 1975, 332-334; Tetrahedron Lett. 1968, 5523-5526; US-A-3910928).

The process according to the invention for preparing the compounds of the general formula is preferably carried out using a diluent. Suitable diluents for carrying out the process according to the invention are, in addition to water, especially inert organic solvents. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethylether, diisopropylether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol 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-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, WO 00165916 PCT/EP00/03496 -23diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water.

When carrying out the process according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the process is carried out at temperatures between 0°C and 150 0 C, preferably between 10 0 C and 120 0

C.

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

To carry out the process according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to use one of the components in a larger excess. In general, the reaction is carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred for several hours at the temperature required.

Working-up is by customary methods (cf. the preparation examples).

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. By weeds, in the broadest sense, are to be understood all plants which grow in locations where they are undesired. 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 be used, for example, in connection with the following plants: Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, WO 00165916 PCT/EP00/03496 -24- Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.

Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.

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

Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.

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

Depending on the concentration, the compounds according to the invention are suitable for total weed control, for example on industrial terrain and rail tracks, and on paths and areas with or without tree stands. Equally, the compounds according to the invention can be employed for controlling weeds in perennial crops, for example forests, ornamental tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, in lawns, turf and pastures, and for selective weed control in annual crops.

WO 00165916 PCT/EP00/03496 The compounds of the formula according to the invention show a potent herbicidal activity and a broad spectrum of action when applied to the soil and to aerial parts of plants. To some extent, they are also suitable for the selective control of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both by the pre- and the post-emergence method.

To a certain extent, the compounds of the general formula according to the invention also have strong activity against animal pests, in particlar against nematodes.

According to the invention, it is possible to treat all plants and parts of plants. Plants are to be understood here as meaning all plants and plant populations such as desired and undesired wild plants or crop plants (including naturally occurring crop plants).

Crop 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 plant cultivars which can or cannot be protected by plant breeders' certificates. Parts of plants are to be understood as meaning all above-ground and below-ground parts and organs of plants, such as shoot, leaf, flower and root, examples which may be mentioned being leaves, needles, stems, trunks, flowers, fruit-bodies, fruits and seeds and also roots, tubers and rhizomes. Parts of plants also include harvested plants and vegetative and generative propagation material, for example seedlings, tubers, rhizomes, cuttings and seeds.

The treatment of the plants and parts of plants according to the invention with the active compounds is carried out directly or by action on their environment, habitat or storage area according to customary treatment methods, for example by dipping, spraying, evaporating, atomizing, broadcasting, brushing-on and, in the case of propagation material, in particular in the case of seeds, furthermore by one- or multilayer coating.

WO 00165916 PCT/EP00/03496 -26- The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspoemulsion concentrates, natural and synthetic materials impregnated with active compound, and microencapsulations in polymeric substances.

These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersants and/or foam-formers.

If the extender used is water, it is also possible to use organic solvents, for example, as auxiliary solvents. Liquid solvents which are mainly suitable are: aromatics such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylenes 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 also 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.

Suitable solid carriers are: for example ammonium salts 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; suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, or else synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; suitable emulsifiers and/or foam formers are: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for WO 00165916 PCT/EP00/03496 -27example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolyzates; suitable dispersants are: for example lignin-sulfite waste liquors and methylcellulose.

Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices such as gum arabic, polyvinyl alcohol and polyvinyl acetate, or else natural phospholipids such as cephalins and lecithins, and synthetic phospholipids can be used in the formulations. Further additives can be mineral and vegetable oils.

It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyestuffs such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dyestuffs, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.

The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and For controlling weeds, the active compounds according to the invention, as such or in the formulations, can also be used as mixtures with known herbicides and/or substances which improve the compatiblity with crop plants ("safeners"), finished formulation or tank mixes being possible. Also possible are mixtures with weed killers comprising one or more known herbicides and a safener.

Possible components for the mixtures are known herbicides, such as, for example, acetochlor, acifluorfen(-sodium), aclonifen, alachlor, alloxydim(-sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, BAS-662H, benazolin(-ethyl), benfuresate, bensulfuron(-methyl), bentazone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac WO 00165916 WO 0065916PCT/EPOO/03496 28 (-sodium), bromobuti de, bromofenoxim, bromoxyni 1, butachlor, butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chiomethoxyfen, chioramben, chioridazon, ch Ioimuron (-ethyl), chiomitrofen, chiorsulfuron, chiortoluron, 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, 2,4-DP, desmedipham, diallate, dicamba, diclofop(-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, diflufenican, diflufenzopyr, dimefuron, dimepiperate, dimethachior, dimethametryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfiural in, ethametsulfuron(-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop(-P-ethyl), fentrazamide, fi amprop(-i sopropyl), flamprop(-i sopropyl-L), flamprop(-methyl), flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fi uometuron, fl uorochloni done, fluoroglycofen(-ethyl), fi upoxam, flupropaci I, flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr (methyl), flurpri midol, fi urtamone, fi uthi acet(-methyl), fluthiami de, fomesafen, glufosinate (-ammoniurn), glyphosate(-i sopropyl ammoniurn), halosafen, haloxyfop(ethoxyethyl), haloxyfop(-P-methyl), hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl, sodium), ioxyni 1, isopropalin, isoproturon, isouron, isoxaben, isoxachiortole, isoxaflutole, isoxapyrifop, lactofen, lenaci I, linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachior, methabenzthi azuron, metobenzuron, metobromuron, (alpha-)metol achior, metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norfiurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, picolinafon, piperophos, pretilachior, primisulfuron(-methyl), prometryn, propachior, propani WO 00165916 PCT/EP00/03496 29 -29propaquizafop, propisochlor, propyzamide, prosulfocarb, prosulfuron, pyraflufen(ethyl), pyrazolate, pyrazosulfuron(-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac(-methyl), pyrithiobac(-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(-P-ethyl), quizalofop(-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) and tritosulfuron.

Mixtures with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil conditioners, are 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 customary manner, for example by pouring, spraying, atomizing or spreading.

The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.

The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the application rates are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between 5 g and 5 kg per ha.

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

WO 00165916 PCT/EP00/03496 Preparation Examples: Example 1

CH

3

CH

N N S H CN g (20 mmol) of methyl N-cyano-thiolimido acetate are added to a mixture of 2.0 g mmol) of 1-(3-thienyl)-ethylamine (racemic) and 60 ml of methanol, and the reaction mixture is stirred at room temperature (approximately 20°C) for 15 hours.

The solvent is then carefully distilled off under reduced pressure.

This gives 3.9 g (100% of theory) of N'-cyano-N-[l-(3-thienyl)-ethyl]-ethaneimidamide (racemate) as an amorphous residue having a refractive index nD 1.5572.

Example 2 CH3 NH N N H NO2 A mixture of 2.0 g (20 mmol) of 1-(3-thienyl)-ethylamine (racemic), 2.7 g (20 mmol) of S-methyl-N-nitro-isothiourea and 80 ml of ethanol is heated at reflux for 8 hours.

After cooling, the resulting crystalline product is isolated by filtration with suction.

This gives 3.1 g (72% of theory) of N'-nitro-N-[l-(3-thienyl)-ethyl]-guanidine (racemate) of melting point 167°C.

WO 00165916 PCT/EP00/03496 -31 Example 3 C CH I I H CN A mixture of 3.4 g (20 mmol) of S-[l-ethyl-3-(2-thienyl)-propyl]-amine, 2.9 g (20 mmol) of dimethyl N-cyano-dithiocarbonimidate and 50 ml of acetonitrile is heated at reflux for 2 hours. After cooling, the mixture is diluted with 80 ml of water and then shaken with methylene chloride. The organic phase is separated off, dried with sodium sulfate and filtered. The filtrate is concentrated under water pump vacuum, the residue is digested with ligroin and the resulting crystalline product is isolated by filtration with suction.

This gives 4.2 g (78% of theory) of [(cyanoimino)-(methylsulfanyl)methyl]-amino}-pentyl)-thiophene of melting point 104°C.

Example 4 ,0CH3 S N N I I I H CN A mixture of 1.7 g (10 mmol) of 1-ethyl-3-(2-thienyl)-propyl-amine (racemic), 1.2 g mmol) of (dimethoxymethylenamino)-(nitrilo)-methane and 60 ml of methanol is stirred at room temperature (approximately 20 0 C) for 18 hours. The solvent is then carefully distilled off under reduced pressure.

WO 00165916 PCT/EP00/03496 -32- This gives 2.4 g (96% of theory) of [(cyanoimino)-(methoxy)-methyl]-amino}pentyl)-thiophene (racemate) as an amorphous residue having a refractive index nD 1.5400.

Similarly to Examples 1 to 4, and in accordance with the general description of the preparation process according to the invention, it is also possible to prepare, for example, the compounds of the general formula listed in Table 1 below.

R

1

R

2 Z'A

N

I I H Y Table 1: Examples of the compounds of the formula (I) Ex. Physical.

No. A RI R 2 Y Z Data

CH

3

CH

3 CN (amorphous) S (racemate) 6 CH 3

CH

3 CN 2 0 =-294 S

(S

enantiomer) 7 CH 3

CH

3 CN logP 1.49 a) S (R enantiomer) 8 -CH 2

CH

2

CH

3

CH

3 CN 92°C S (racemate) 9 -CH 2

CH

2

C

2

H

5

CH

3 CN S (S enantiomer) WO 00165916 WO 0065916PCT/EPOO/03496 33 Ex. Physical.

No. A R' R 2Y Z Data

-CH

2

CH

2

C

2

H

5 Gil 3 CN enantiomer) 11 -C 2

H

5

CIA

3 CN IogP 1.79 a) S (racemate) 12 -CH 2

CH

2

C

2

H

5

CH

3 CN 61 0

C

s (racemate) 13 -CH 2

CH

2

CIA

3

CIA

3 CN 72'C (racemate)

S

14 -C 2 11 5 Gil 3

CN

(racemate)

S

-CH

2

CH

2

C

2

H

5

CH

3 CN (amorphous) (racemate)

S

16 -CH 3

CH

3 CN 64'C CI (racemate) 17 -CH 2

CH

2

CH

3

CH

3 CN CI s (racemate) 18 -C 2

H

5

CH

3 CN 104'C CI s (racemate) 19 -CH 2

CH

2

C

2 11 5

CIA

3

CN/\

CI (racemate)

-CH

3

CIA

3 CN Bt 3- 108TC Br (racemate) WO 00165916 WO 0065916PCT/EPOO/03496 34 Ex. Physical.

No. A R R2Y Z Data 21 -CH 2

CH

2

OH

3

CH

3 CN rcmae Br S (racemate) 23 -CH 2

CH

2

C

2

H

5

CH

3

CN

Brz, (racemate) 24 -CH 3

CH

3 CN H J- H3 S (racemate)

-CH

2

CH

2

CH

3

CH

3 CN (amorphous) H3CJ s\ (racemate) 26 -C 2

H

5

CH

3 ON 7- H3C--S (racemate) 27 -CH 2

CH

2

C

2

H

5

OH

3 ON (amorphous) H3C 't S(racemate) 28 H 3

OH

3 ON OH 3 (racemate) 29 -CH 2

CH

2

OH

3

OH

3 ON OH 3 78'C (racemate)

-C

2

H

5

OH

3 ON CH 3 d/ -,(racemate)

S

31 -CH 2

OH

2 0 2

H

5

CH

3 CN OH 3 91'C C (racemate)

S

WO 00165916 WO 0065916PCT/EPOO/03496 35 Ex. Physical.

No. A RI R2Y Z Data 32 -CH 3

SCH

3 CN 20 S, (racemate) 33 -CH 3

SCH

3 CN logP =1.83 a) s (R enantiomer) 34 -CH 3

SCH

3 CN [E20 =-56 S

(S

-C 2 H C 3 SCH 3 CN s(racemate) 36 -C 2

H

5

SCH

3 CN 84'C s (racemate) 37 -CH 2

CH

2

C

2

H

5

SCH

3 CN 102'C s (racemate) 38 -CH 3

SCH

3

CN

(racemate)

S

39 -CH 2

CH

2

CH

3

SCH

3 CN (racemate)

S

-C

2

H

5

SCH

3

CN

(racemate)

S

41 -CH 2

CH

2 CAH SCH 3 CN 128'C (racemate)

S

WO 00165916 WO 0065916PCT/EPOO/03496 -36- Ex. Physical.

No. A RI R2Y Z Data 42 -CH 3

SCH

3 CN 68'C CI- (racemate) 43 -CH 2

CH

2

CH

3

SCH

3

CN

C1 s (racemate) 44 -C 2

H

5

SCH

3 CN I1I1VC s (racemate)

-CH

2

CH

2

C

2

H

5

SCH

3

CN

CI s (racemate) 46 -CH 3

SCH

3 CN I14WC B rts (racemate) 47 -CH 2

CH

2

CH

3

SCH

3 CN 7 Br s (racemate) 48 -C 2

H

5

SCH

3

CN

Br s (racemate) 49 -CH 2

CH

2

C

2

H

5

SCH

3

CN

Br J-s (racemate)

-CH

3

SCH

3

CN

H3 s (racemate) 51 -CH 2

CH

2

CH

3

SCH

3 CN 47m.P.: 108'C H3C- S (racemate) 52 -C 2

H

5

SCH

3

CN

H3 (racemate) 53 -CH 2

CH

2

C

2

H

5

SCH

3 CN HCW H3 s (racemate) WO 00165916 WO 0065916PCT/EPOO/03496 37 Ex. Physical.

No. A R I R 2 Y Z Data 54 -CH 3

SCH

3 CN OH 3 C (racemate)

S

-CH

2

CH

2

CH

3

SCH

3 CN OH 3 107 0

C

C (racemate)

S

56 -C 2

H

5

SCH

3 CN CH 3 C (racemate)

S

57 -CH 2

CH

2

C

2

H

5

SCH

3 CN OH 3 88'C I (racemate) 58 -CH 3

OCH

3 CN 63'C s (racemate) 59 -CH 2

CH

2

CH

3

OCH

3

CN

S, (racemate)

-C

2

H

5

OCH

3 CN 113'C s (racemate) 61 -CH 3

OCH

3

CN

(racemate)

S

62 -CH 2

CH

2

CH

3

OCH

3 CN 20= .53 (racemate)

S

63 -C 2

H

5

OCH

3

CN

(racemate)

S

WO 00165916 PCT/EPOO/03496 38 Ex. Physical.

No. A R R 2Y Z Data 64 -CH 2

CH

2

C

2

H

5

OCH

3

CN

(racemate)

S

-C

2 11 5

OCH

3 CN 112'C C1 s (racemate) 66 -CH 2

CH

2

CH

3

NH

2

NO

2 S (racemate) 67 -CH 2

CH

2

CH

3

NH

2

NO

2

(R

S enantiomer) 68 -CH 2

CH

2

CH

3

NH

2

NO

2 s

(S

enantiomer) 69 -CH 3

NH

2

NO

2 141'C S (racemate)

-CH

3 NH1 2

NO

2 20=82' CS(S 82.80( 71 CH 3 enantiomer) 71C3 NH 2

NO

2 155 0

C

s (R-Enantiomer) 72 -C 2

H

5 NH1 2

NO

2 153'C CS (racemate) 73 -CH 2

CH

2

C

2

H

5

NH

2

NO

2 S (racemate) 74 -CH 3

NH

2

NO

2 (racemate)

S

WO 00165916 WO 0065916PCT/EPOO/03496 39 Ex. Physical.

No. A RI R2 Y Z Data

-CH

2

CH

2

CH

3

NH

2

NO

2 138'C (racemate)

S

76 -C 2

H

5

NH

2

NO

2 (racemate)

S

77 -CH 2

CH

2

C

2

H

5

NH

2

NO

2 (racemate)

S

78 -CH 3

NH

2

NO

2 145'C CIS (racemate) 79 -CH 2

CH

2

CH

3

NH

2

NO

2 CI S (racem ate)

-C

2

H

5

NH

2

NO

2 106'C s (racemate) 81 -CH 2

CH

2

C

2

H

5

NH

2

NO

2 CI s (racemate) 82 -CH 3

NI-

2

NO

2 125'C Brs (racemate) 83

-CH

2

CH

2

CH

3 NH 2 NO 2 7 Br-ts (racem ate) 84

-C

2

H

5 NH 2 NO 2 /7 Br -s (racemate)

-CH

2

CH

2

C

2

H

5

NH

2

NO

2 Br s (racemate) WO 00165916 PCT/EPOO/03496 WO 00165916 W00015916PCT/EPOO/03496 -41- Ex. Physical.

No. A R R 2 Y Z Data 97 -CH 3 Nib N0 2 134'C CI s (S enantiomer) 98 -CH 3

CH

3 CN 1ogP =2.0 1b) S (R enantiomer) 99 -CH 3

NH

2

NO

2 132'C Cl s (R enantiomer) 100 C 2

H

5

CH

3 CN 68'C

(S

enantiomer) 101 C 2

H

5

SCH

3 CN 131VC s

(S

enantiomer) 102 C 2

H

5

NH

2

NO

2 ~4 63'C s (S enantiomer) 103 C 2

H

5

OCH

3 CN 48'C CI-<S

(S

enantiomer) 104 CH 3

SCH

3 CN H3C 142'C /i (racemate) 105 CH 3

NH

2

NO

2

H

3 C 143'C Il (racemate) WO 00165916 WO 0065916PCT/EPOO/03496 -42 Ex. Physical.

No. A R R2Y Z Data 106 CH 3

CH

3 CN H 3 C 82'C /i (racemate) 107 CH 3

OCH

3 CN H 3 C 140'C C (racemate) 108 C 2

H

5

CH

3 CN 108'C Cl- S (R en an tiomer) 109 C 2

H

5

SCH

3 CN 122'C ,S

(R

enantiomer) 110 C 2

H

5

NH

2 N0 2 162'C s (R enantiomer) 11 C 2

H

5

OCH

3 CN 43'C CI' s (R en an tiomer) 112 CH 3

OCH

3 CN s (S enantiomer) 113

C

3

H

7 -i CH 3 CN \logP =2.07 a) S (racemate) 114

C

3

H

7 -i SCH 3 CN \logP 2.39 a) S (racemate) 115 C 3

H

7 -i NH 2

NO

2 127'C S (racemate) WO 00165916 WO 9065916PCT/EPOO/03496 43 Ex. Physical.

No. A R I R 2Y Z Data 116 -CH 2

CH

2

C

2

H

5 H CN 58'C

S

117 CH 3

CH

3 CN l ogP =2.20a

H

5

C

2 s (racemate) 118 CH 3 NH1 2

NO

2 logp =1.91 a) 2 S (racemate) 119 C 2

H

5

CH

3 CN H 3 C I110 0

C

/ii (racemate) 120 C 2

H

5

SCH

3 CN H 3 C 145'C I (racemate)

CI

121 C 2 11 5

NH

2

NO

2

H

3 C 133'C (racemate)

CI

122 C 2

H

5

OCH

3 CN H 3 C 124'C cI (racemate)

CI

123 C 2

H

5

NHC

3

H

7 -i CN CI- s

(S

en anti omer) 124 C 2

H

5

NHC

3

H

7 -i CN Cl- s (R en anti omer) 125 -CH 2

CH

2

C

2

H

5

SCH

3 CN 118'C H3 S (S enantiomer) WO 00165916 PCT/EP00/03496 -44- Ex. Physical.

No. A R' R 2 Y Z Data 126 -CH 2

CH

2

C

2

H

5

CH

3

CN

H3C S"

(S

enantiomer) 127 -CH 2

CH

2

C

2

H

5

NH

2

NO

2 97°C H3aC S" (S enantiomer) 128 CH 3

CH

3 CN 159°C cI C2H (racemate) Ci S CH 129 CH 3

SCH

3 CN 133°C Sc (racemate) 130 CH 3

NH

2

NO

2 162°C C

C

2

H

s (racemate) 131 CH 3

CH

3 CN 112°C cl I (racemate) 132 CH 3

NH

2

NO

2 114°C c 1 (racemate) The logP values given in Table 1 were determined in accordance with EEC directive 79/831 Annex V.A8 by HPLC (High Performance Liquid Chromatography) using a reversed-phase column (C 18). Temperature: 43°C.

Mobile phases for the determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to acetonitrile corresponding measurement results are marked a) in Table 1.

WO 00165916 PCT/EP00/03496 Mobile phases for the determination in the neutral range: 0.01 molar aqueous phosphate buffer solution, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile corresponding measurement results are marked b) in Table 1.

Calibration was carried out using unbranched alkan-2-ones (having 3 to 16 carbon atoms) with known logP values (determination of the logP values by the retention times using linear interpolation between two successive alkanones).

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

WO 00165916 PCT/EP00/03496 -46- Starting materials of the formula (II): Example (11-1)

H

3

C

H'N

H

Step I

H

At from 140°C to 160 0 C, 150 ml of formic acid are added dropwise with stirring to a mixture of 100 g (079 mol) of 2-acetyl-thiophene and 300 ml of formamide, and the reaction mixture is stirred at 160 0 C for 2 hours. After cooling to room temperature, the mixture is diluted with toluene to about twice its original volume, washed twice with water, dried with sodium sulfate and filtered. From the filtrate, the solvent is carefully distilled off under water pump vacuum.

This gives 78 g (64% of theory) of N-(1-thien-2-yl-ethyl)-formamide (racemate) as an amorphous residue.

Step 2

H

3

C

HNs

H

A mixture of 75 g (0.48 mol) of N-(l-thien-2-yl-ethyl)-formamide, 120 ml of conc.

hydrochloric acid and 50 ml of water is heated at reflux for 3 hours and then concentrated under water pump vacuum. The residue is shaken with water/methylene WO 00165916 PCT/EP00/03496 -47chloride, the aqueous phase is made alkaline using 2 N aqueous sodium hydroxide solution and shaken with toluene. The toluene phase is dried over sodium sulfate and filtered. The filtrate is worked up by distillation under reduced pressure.

This gives 24.8g (41% of theory) of 1-(thien-2-yl)-ethylamine (racemate) of boiling point 40 0 C at 0.8 mbar.

Example (11-2)

H

3 C

H

3 0 S S H

H

A mixture of 160 g (1.25 mol) of 1-(thien-2-yl)-ethylamine (racemate), 140 g of methyl methoxy acetate, 15 g of Novenzym-435 and 1 liter of methyl-tert-butyl ether is stirred for 24 hours and, after addition of a further 5 g of Novenzym-435, for a further 24 hours at 60°C. The mixture is then filtered, the filtrate is concentrated under water pump vacuum, and the residue is taken up in 500 ml of dichloromethane and shaken with 1 liter of 10% strength aqueous hydrochloric acid. The organic phase is separated off and worked up as described below. The aqueous phase is made alkaline by addition of conc. aqueous sodium hydroxide solution and extracted with dichloromethane. The organic extract solution is dried with sodium sulfate and filtered. From the filtrate, the desired product is isolated by distillation under reduced pressure.

This gives 35.5 g (44% of theory) of S-l-(2-thienyl)-ethylamine of boiling point 0 C (at 0.8 mbar).

The organic phase separated off during work-up after the reaction described above is dried with sodium sulfate and filtered. From the filtrate, the solvent is carefully distilled off under reduced pressure. This gives 100 g (84% of theory) of R-(N- WO 00165916 PCT/EP00/03496 -48methoxyacetyl)-l-(2-thienyl)-ethylamine as a solid residue which melts at about 0

C.

g (0.30 mol) of R-(N-methoxyacetyl)-1-(2-thienyl)-ethylamine are heated under reflux with 200 ml of water and 200 ml of cone. hydrochloric acid for 8 hours. After cooling, the mixture is extracted with diethyl ether and the organic phase is worked up by distillation under reduced pressure.

This gives 28.5 g (75% of theory) of R-l-(2-thienyl)-ethylamine of boiling point 55°C (at 2 mbar).

Example (11-3) H x HCl

H

2 8S A mixture of 9.8 g (50 mmol) of N-(l-methyl-4-(thien-2-yl)-butyl)-formamide, 100 ml of conc. hydrochloric acid and 40 ml of water is heated at reflux for minutes. The mixture is then substantially concentrated under water pump vacuum and the residue is stirred with diethyl ether. The ether phase is decanted off, and the solvent is carefully distilled off from the residue under water pump vacuum.

This gives 8.5 g (83% of theory) of 2-amino-5-(thien-2-yl)-pentane hydrochloride as a dark oil.

Similarly to Examples 1-1 to 11-3, it is also possible to prepare, for example, the compounds of the general formula (II) listed in Table 2 below.

WO 00165916 W00015916PCTIEPOO/03496 -49 Z A N H (11),

H

Table 2: Examples of the compounds of the formula (1 Ex.-No. Physical. Data A RIZ 111-4 C 2

H

5 52'C S (at 0.7 mbar) (racemate) 11-5 -CH 2

CH

2

CH

3 53'C s (at 1 mbar) (racemate) 11-6 -CH 2

CH

2

CH

3 (at 0.7 mbar) S (racemate) 11-7 -CH 2

CH

2

CH

3 78'C

H

3 C SZ (at 0.8 mbar) (racemate) 11-8 -CH 2

CH

2

C

2

H

5 s (at 0.7 mbar) (S enantiomer) H1-9 -CH 2

CH

2

C

2

H

5 83'C \J (at 1.6 mbar) S (racemate) 11-10 -CH 2

CH

2

C

2

H

5 85 0

C

H

3 C sA (at 0.6 mbar) (racemate) WO 00165916 WO 0065916PCT/EPOO/03496 50 Ex.-No. Physical. Data A R' Z 11-11 -CH 2

CH

2

C

2

H

5

CH

3 C L\ (at 1.5 mbar) S (racemate) 111-12 CH 3 58'C CI s (at 1.8 mbar) (racemate) 11-13 CH 3 69'C S (at 1.4 mbar) (racemate) 111-14 C 2

H

5 73'C S (at 1.4 mbar) (racemate) 11-15 -CH 2

CH

2

C

2

H

5 H \J C (at 1.5 mbar) S 3 (racemate) 11-16 -CH 2

CH

2

C

2

H

5 Br I I10 0

C

(at 2 mbar) S (racemate) 11-17 -CH 2

CH

2

C

2

H

5 1 10 0

C

/1 Au\ (at 2 mbar) S (racemate) 11-18 Cl- 3 \J (at 3 mbar) S (racemate) 11-19 -C H 2 C H 2 C 2 H 5 B r s( a e a e WO 00165916 WO 0065916PCT/EPOO/03496 -51 Ex.-No. Physical. Data A R'Z 11-20 -CH 2

CH

2

C

2

H

5 Br (racemate) 111-21

C

2

H

(racemate) 11-22

CH

3 /3 CH (racemate) 111-23 C 2

H

H Ct CH (racemate) 11-24

C

2

H

CI S (S enantiomer) 11-25 C 2

H

5 CI S (at I mbar) (R enantiomer) 11-26 CH 3 56'C CI S (at 2 mbar) (S enantiomer) 11-27 CH 3 C S (at 2 mbar) (R enantiomer) 11-28 -CH 2

CH

2

CH

3 62'C CS (at 0.5 mbar) (S enantiomer) WO 00165916 PCT/EPOO/03496 52 WO 00165916 PCT/EP00/03496 -53- Use Examples: Example A Pre-emergence test Solvent: Emulsifier: 5 parts by weight of acetone 1 part 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 concentrated is diluted with water to the desired concentration.

Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of active compound such that the particular amount of active compound desired is applied per unit area. The concentration of the spray liquor is chosen such that the particular amount of active compound desired 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.

The figures denote: 0% 100% no effect (like untreated control) total destruction WO 00165916 PCTEPOO/03496 -54- In this test, for example, the compounds of Preparation Examples 5 and 18 show strong activity against weeds, and they are tolerated well by some crop plants, such as, for example, corn, soybean and wheat.

Example B Post-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.

Test plants of a height of 5 15 cm are sprayed with the preparation of active compound such that the particular amounts of active compound desired are applied per unit area. The concentration of the spray liquor is chosen such that the particular amounts of active compound desired are applied in 1000 1 of water/ha.

After three weeks, the degree of damage to the plants is rated in damage in comparison to the development of the untreated control.

The figures denote: 0% no effect (like untreated control) 100% total destruction WO 00165916 PCT/EPOO/03496 55 In this test, for example, the compounds of Preparation Examples 5 and 44 show strong activity against weeds, and they are tolerated well by some crop plants, such as, for example, barley, corn and wheat.

Throughout this specification and the claims which follow, unless the context requires otherwise, the word "comprise", and variations such as "comprises" or "comprising", will be understood to imply the inclusion of a stated integer or step or group of integers or steps but not the exclusion of any other integer or step or group of integers or steps.

The reference to any prior art in this specification is not, and should not be taken as, an acknowledgment or any form of suggestion that that prior art forms part of the common general knowledge in Australia.

NOTE: Amendments have been made to the claims which appear hereafter in order to further define the invention. These amendments are based on preferments described herein. For integrity of the text and of the specification as filed, corresponding amendments have not been made to the statements of invention which appear on pages 1-2 and 7-8, and the description generally on pages 23-24.

oo 0 0 *00 oS *5oS

S

Claims (7)

1. A method of controlling plants from the group consisting of Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemnis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium,- Convolvulus, Ipomnoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanium, Rorippa, Rotala, Lindemnia, Lamnium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacumn Dicotyledonous crops of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum., Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleumn, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalumn, Ischaemnum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops and Phalaris Monocotyledonous crops of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium. comprising applying a N-substituted heterocyclylalkylamine of the formula (I) P:\WPDOCS\CAB\SPECI\7644430.doo- 57 1 2 R R ZINA I' N I H Y wherein A represents a single bond or represents alkanediyl having 1 to 4 carbon atoms, R1 represents optionally cyano-, halogen-, or C 1 -C 4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms, R 2 represents hydrogen, amino or represents in each case optionally cyano-, halogen-, C 1 -C 4 -alkoxy-, C 1 -C 4 -alkylthio-, Cl-C 4 -alkylsulfinyl- or C,-C,-alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups and Y represents cyano or nitro, and represents an optionally substituted monocyclic or bicyclic heterocyclic grouping from the group consisting of furyl, tetrahydrofliryl, benzofuryl, dihydrobenzofuryl, isobenzofuiryl, thienyl, tetrahydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolyl, isoindolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl, where the substituents are selected from the group consisting of nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, C,- C 4 -alkyl, C 1 -C,-halogenoalkyl, C 1 -C 4 -alkoxy, C 1 -C 4 -halogenoalkoxy, C 1 -C 4 -alkylthio, Cl-C 4 -halogenoalkylthio, C 1 -C 4 -alkylsulfinyl, CI-C 4 halogenoalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 -halogenoalkyl- P:\\PDOCS\CAB\SPECI\7644430.doe- 58 sulfonyl, C 1 -C 4 -alkyl-carbonyl, C 1 -C 4 -alkoxy-carbonyl, C 1 4 -alkyl- amino-carbonyl, di-(C 1 -C 4 -alkyl)-amino-carbonyl, C 1 -C 4 -alkylamino- sulfonyl, di-(C 1 -C 4 -alkyl)amino-sulfonyl, phenyl, to said undesirable plants and/or their habitat.

2. The method according to claim 1, wherein A represents a single bond, represents methylene (-CH 2 dimethylene (ethane- 1 ,2-diyl, -CH 2 CH 2 ethylidene (ethane- 1, 1 -diyl, -CH(CH 3 trimethylene (propane-i ,3-diyl, -CH 2 CH 2 CH 2 or propane-i ,2-diyl (-CH 2 CH(CH 3 *R1 represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, s- or t-butyl, R 2 represents hydrogen, amino, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonyl- substituted methyl, ethyl, n- or i-propyl, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, s- or t-butoxy, methylthio, ethylthio, n- *:or i-propylthio, s- or t-butylthio, methylamino, ethylamino, n- or. i-propylamino, s- or t-butylamino, dimethylamnino, diethylamnino or dipropylamnino and Z represents an optionally substituted monocyclic or bicyclic heterocyclic grouping from the group consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, isobenzofuryl, thienyl, P:%WPDOCS\CABMSPECI\764443.dcM- -59- tetrahydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolyl, isoindolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl, where the substituents are selected from the group consisting of nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, sulfamnoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, s- or t- butyl, difluoromethyl, dichioromethyl, trifluoromethyl, trichioro- methyl, chiorodifluoromethyl, fluorodichioromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methyl- thio, ethylthio, n- or i-propylthio, s- or t-butylthio, difluoro- methylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or 1- propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycar- bonyl, methylamninocarbonyl, ethylaminocarbonyl, n- or i-propyl- aminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, methylaminosulfonyl, ethylaminosulfonyl, n- or i-propylamnino- sulfonyl, dimethylaminosulfonyl, diethylaminosulfonyl, phenyl.

3. The method according to claim 1 wherein A represents a single bond or represents dimnethylene (-CI- 2 CH 2 R 1 represents methyl, ethyl, n- or i-propyl, R2 represents hydrogen, amino, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, P:\WPDOCS\CAB\SPECI\7644430.doc- 60 methylamino, ethylamino, n- or i-propylamino, dimethylamino or di- ethylamino and Z represents in each case optionally substituted thienyl or benzothienyl, where the substituents are selected from the group consisting of nitro, cyano, carbamoyl, thiocarbamnoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, dichloromethyl, trifluo romethyl, trichloromethyl, chiorodifluoromethyl, Fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoro- methylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, tri- fluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propyl- sulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.

4. An N-substituted heterocyclylalkylamine of the formnula (I) R 1 R 2 H Y wherein A represents a single bond or represents alkanediyl having 1 to 4 carbon ****atoms, represents optionally cyano-, halogen- or C 1 -C 4 -alkoxy-substituted alkyl having I to 6 carbon atoms, P:\WPDOCS\CAB\SPEC\764443.do.- 61 R' represents amino, represents in each case cyano-, halogen, CI-C 4 alkoxy-, CX- 4 -alkylthio-, C 1 -C 4 -alkylsulfinyl- or C 1 -C 4 -alkylsulfonyl- substituted alkyl, or represents in each case optionally cyano-, halogen-, CX- 4 -alkoxy-, CX- 4 -alkylthio-, C 1 -C 4 -alkylsulfinyl- or C 1 C 4 -alkylsulfonyl-substituted alkoxy, alkylthio, alkylamino or dialkyl- amino having in each case 1 to 6 carbon atoms in the alkyl groups, Y represents cyano or nitro, and Z represents in each case optionally substituted thienyl or benzothienyl, where the possible substitutents are selected from the group consisting of nitro, cyano, carboxyl, carbamoyl, thiocarbamnoyl, sulfamoyl, halogen, Cl-C 4 -alkyl, C 1 -C 4 -halogenoalkyl, C 1 4 -alkoxy, C 1 -C 4 halogenoalkoxy, C 1 4 -alkylthio, Cl-C 4 -halogenoalkylthio, C 1 -C 4 490 0 alkylsulfinyl, Cl-C 4 -halogenoalkylsulfinyl, C 1 -C 4 -alkylsulfonyl, C 1 -C 4 0 halogenoalkylsulfonyl, CX- 4 -alkyl-carbonyl, C 1 -C 4 -alkoxy-carbonyl, tos C 1 -C 4 -alkylamino-carbonyl, di-(C 1 -C 4 -alkyl)-amnino-carbonyl, C 1 -C 4 alkylamino-sulfonyl, di-(C 1 -C 4 -alkyl)-amino-sulfonyl, phenyl. The compound as claimed in claim 4, characterized in that A, RI and the substituents listed for Z are as defined in claim 2 or 3. A process for preparing compounds as claimed in claim 4 or 5, characterized :in that heterocyclyl amnines of the general formula (11) 0& 00 Z 'A lN II) H in which P:\WPDOCS\CAB\SPEC\7644430.doc -62- A, R' and Z are as defined in claim 4 or are reacted with imino compounds of the general formula (III) Y (III), in which R 2 and Y are as defined in claim 4 and 0000 000 0000 00 0 0 000 0000 0000 0000 000 X represents alkoxy or alkylthio, if appropriate in the presence of a diluent.

7. A herbicidal composition, characterized by the content of at least one compound according to claim 4 or 5 and customary extenders.

8. Methods for controlling plants according to anyone of claims 1-3, substantially as hereinbefore described with reference to the Examples.

9. Compounds of the formula according to either claim 4 or claim 5, processes for their preparation or herbicidal compositions involving/containing same, substantially as hereinbefore described with reference to the Examples. DATED this 31st day of January, 2003 BAYER AKTIENGESELLSCHAFI By its Patent Attorneys DAVIES COLLISON CAVE 00 00 0 0 o 0005 0 0 0000 00 5 ooeo oooo 05 0 00 0000 0 0 0000 oooo 0 00 *o