AU4749000A - Use of n-substituted heterocyclylalkylamines as herbicides and novel n-substituted thienylalkylamines - Google Patents

Description

-1 Use of N-substituted heterocyclylalkylamines as herbicides, and novel N substituted thienylalkylamines The invention relates to the use of N-substituted heterocyclylalkylamines as 5 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. 10 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). 15 It has now been found that the N-substituted heterocyclylalkylamines of the general formula (I) R1 R2 R R2 A N N '(), I I H Y in which 20 A represents a single bond or represents alkanediyl, R' represents optionally substituted alkyl, 25 R2 represents hydrogen, amino or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, Y represents cyano or nitro and -2 Z represents optionally substituted heterocyclyl, have strong herbicidal activity. 5 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 10 polysubstitution, the substituents can be identical or different. The compounds of the general formula (I) according to the invention contain at least one carbon-nitrogen double bond and can therefore be present in different E- and Z configured isomeric forms. The invention relates both to the use of the individual E 15 and Z-configured isomeric forms of the compounds of the general formula (I) and of the mixtures of these isomeric compounds. The compounds of the general formula (I) according to the invention contain at least one asymmetrically substituted carbon atom and can therefore be present in different 20 enantiomeric (R- 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 (I) and of the mixtures of these isomeric compounds. 25 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. 30 A AI Jul VV2I UU.Yt7u -3 R preferably represents optionally cyano-, halogen-, or Ci-C 4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms. R2 preferably represents hydrogen, amino or represents in each case optionally 5 cyano-, halogen-, Ci-C 4 -alkoxy-, C 1

-C

4 -alkylthio-, Ci-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 10 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, 15 quinazolinyl. where the preferred substituents are selected from the group consisting of nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, CI-C 4 alkyl, Ci-C 4 -halogenoalkyl, Ci-C 4 -alkoxy, Ci-C 4 -halogenoalkoxy, C 1

-C

4 20 alkylthio, C 1

-C

4 -halogenoalkylthio, Ci-C 4 -alkylsulfinyl, Ci-C 4 -halogenoalkyl sulfinyl, C 1

-C

4 -alkylsulfonyl, C 1

-C

4 -halogenoalkylsulfonyl, CI-C 4 -alkyl carbonyl, C 1

-C

4 -alkoxy-carbonyl, C 1

-C

4 -alkylamino-carbonyl, di-(Ci-C 4 alkyl)-amino-carbonyl, C 1

-C

4 -alkylamino-sulfonyl, di-(CI-C 4 -alkyl)amino sulfonyl, phenyl. 25 A particularly preferably 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-1,3-diyl, -CH 2

CH

2

CH

2 -) or propane-1,2 diyl (-CH 2

CH(CH

3

)-).

-4 R' particularly preferably represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl. 5 R2 particularly preferably represents hydrogen, amino, represents in each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, methylthio-, ethyl thio-, methylsulfinyl-, ethylsulfinyl-, methylsulfonyl- or ethylsulfonyl substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, 10 n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, 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, 15 tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, isobenzofuryl, thienyl, tetra hydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolyl, isoindolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl, 20 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, n-, i-, s- or t butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloromethyl, 25 chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i propoxy, 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, 30 acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i- -5 propoxy-carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl amino-carbonyl, dimethylaminocarbonyl, diethylamino-carbonyl, methyl aminosulfonyl, ethylaminosulfonyl, n- or i-propylamino-sulfonyl, dimethyl aminosulfonyl, diethylamino-sulfonyl, phenyl. 5 A very particularly preferably represents a single bond or represents dimethylene

(-CH

2

CH

2 -). R I very particularly preferably represents methyl, ethyl, n- or i-propyl. 10 R2 very particularly preferably represents hydrogen, amino, methyl, ethyl, n- or i propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i propylthio, methylamino, ethylamino, n- or 1-propylamino, dimethylamino or diethylamino. 15 Z very particularly preferably represents in each case optionally substituted thienyl or benzothienyl. where the very particularly preferred substituents are selected from the group 20 consisting of nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, dichloromethyl, tri fluoromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethyl 25 thio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethyl sulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethyl sulfonyl, acetyl, propionyl, n- or i- butyroyl, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxy-carbonyl.

- - -~- = =.~= ~ ~J- 6 -' -6 The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) 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 5 given preferred ranges. Preference according to the invention is given to the herbicidal use of compounds of the formula (I) which contain a combination of the meanings listed above as being preferred. 10 Particular preference according to the invention is given to the herbicidal use of compounds of the formula (I) which contain a combination of the meanings listed above as being particularly preferred. 15 Very particular preference according to the invention is given to the herbicidal use of compounds of the formula (I) which contain a combination of the meanings listed above as being very particularly preferred. A small number of the compounds of the general formula (I) is already known (cf. 20 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 (I) has hitherto 25 not been disclosed in the literature. Among these, emphasis is given, in particular, to the novel compounds of the general formula (I) in which Z represents in each case optionally substituted thienyl or benzothienyl - excluding the compounds N'-cyano N-[1-methyl-3-(3-thienyl)-propyl]-ethaneimidamide, N'-cyano-N-[1 -ethyl-3-(3 thienyl)-propyl]-ethaneimidamide, N'-cyano-N-[1-methyl-3-(2-thienyl)-propyl] 30 ethaneimidamide, N'-cyano-N-[I-(2-thienyl)-ethyl]-ethaneimidamide and N'-cyano- -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 5 those compounds of the general formula (I) in which A represents a single bond or represents alkanediyl having I to 4 carbon atoms, R' represents optionally cyano-, halogen- or Ci-C 4 -alkoxy-substituted alkyl 10 having 1 to 6 carbon atoms, R2 represents hydrogen, amino or represents in each case optionally cyano-, halogen-, CI-C 4 -alkoxy-, C 1

-C

4 -alkylthio-, CI-C 4 -alkylsulfinyl- or C 1

-C

4 alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino 15 having in each case I to 6 carbon atoms in the alkyl groups, Y represents cyano or nitro, and Z represents in each case optionally substituted thienyl or benzothienyl, 20 where the possible substitutents are selected from the group consisting of nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, Ci-C 4 alkyl, Ci-C 4 -halogenoalkyl, Ci-C 4 -alkoxy, C 1

-C

4 -halogenoalkoxy, Ci-C 4 alkylthio, Cl-C 4 -halogenoalkylthio, Ci-C 4 -alkylsulfinyl, Ci-C 4 -halogenoalkyl 25 sulfinyl, CI-C 4 -alkylsulfonyl, Cl-C 4 -halogenoalkylsulfonyl, CI-C 4 -alkyl carbonyl, C 1

-C

4 -alkoxy-carbonyl,

C

1

-C

4 -alkylamino-carbonyl, di-(CI-C 4 alkyl)-amino-carbonyl, Ci-C 4 -alkylamino-sulfonyl, di-(CI-C 4 -alkyl)-amino sulfonyl, phenyl, A A I A A Ulu/l U.71,U -8 except for the compounds N'-cyano-N- [1 -methyl-3-(3-thienyl)-propyl]-ethaneimid amide, N'-cyano-N-[1-ethyl-3-(3-thienyl)-propyl]-ethaneimidamide, N'-cyano-N-[1 methyl-3-(2-thienyl)-propyl]-ethaneimidamide, N'-cyano-N-[1-(2-thienyl)-ethyl] ethaneimidamide and N'-cyano-N-[1-(3-thienyl)-ethyl]-ethaneimidamide (cf. DE-A 5 19832447). A, R 1 , R 2 and the substituents listed for Z preferably have the meanings given above as being preferred. 10 Examples of the compounds of the general formula (I) 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.

-9 Group 1 SIA N N I I H Y Here, A, R , R2 and Y have, for example, the meanings listed in the table below. 5 A RI R2 Y A R1 R2 y - 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

H

7 -n CN - CH 3

C

3

H

7 -n NO 2 - CH 3

C

3

H

7 -i CN - CH 3

C

3

H

7 -i NO 2 - CH 3

OCH

3 CN - CH 3

OCH

3

NO

2 - CH 3

OC

2

H

5 CN - CH 3

OC

2

H

5

NO

2 - CH 3

OC

3

H

7 -n CN - CH 3

OC

3

H

7 -n NO 2 - CH 3

OC

3

H

7 -i CN - CH 3

OC

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

H

7 -n 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 - CH 3

NHC

3

H

7 -n NO 2 - CH 3

NHC

3

H

7 -i CN - CH 3

NHC

3

H

7 -i NO 2 - CH 3

N(CH

3

)

2 CN - CH 3

N(CH

3

)

2

NO

2 - CH 3

N(C

2

H

5

)

2 CN - CH 3

N(C

2

H

5

)

2

NO

2 - C 2

H

5 H CN - C 2

H

5 H NO 2 -10 A RI R2 Y A Rl R2 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

NO

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 NO 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

OC

2

H

5

NO

2 - C 2

H

5

OC

3

H

7 -n CN - C 2

H

5

OC

3

H

7 -n NO 2 - C 2

H

5

OC

3

H

7 -i CN - C 2

H

5

OC

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 H7-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

H

7 -n CN - C 2

H

5

NHC

3

H

7 -n 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 - CH 3 H CN -CH 2

CH

2 - CH 3 H 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

H

7 -i 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

OC

2

H

5 CN -CH 2

CH

2 - CH 3

OC

2

H

5

NO

2

-CH

2

CH

2 - CH 3

OC

3

H

7 -n CN -CH 2

CH

2 - CH 3

OC

3

H

7 -n NO 2

-CH

2

CH

2 - CH 3

OC

3

H

7 -i CN -CH 2

CH

2 - CH 3

OC

3

H

7 -i NO 2 -11 A RI R2 Y A R R2

-CH

2

CH

2 - CH 3

SCH

3 CN -CH 2

CH

2 - CH 3

SCH

3

NO

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

H

7 -n 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

-CH

2

CH

2 - CH 3

NHC

2

H

5 CN -CH 2

CH

2 - CH 3

NHC

2 Hs NO 2

-CH

2

CH

2 - CH 3

NHC

3

H

7 -n CN -CH 2

CH

2 - CH 3

NHC

3

H

7 -n 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(CH

3

)

2 CN -CH 2

CH

2 - CH 3

N(CH

3

)

2

NO

2

-CH

2

CH

2 - CH 3

N(C

2

H

5

)

2 CN -CH 2

CH

2 - CH 3

N(C

2

H

5

)

2

NO

2

-CH

2

CH

2 - C 2

H

5 H CN -CH 2

CH

2 - C 2

H

5 H NO 2

-CH

2

CH

2 - C 2

H

5

CH

3 CN -CH 2

CH

2 - C 2

H

5

CH

3

NO

2

-CH

2

CH

2 - C 2

H

5

C

2

H

5 CN -CH 2

CH

2 - C 2

H

5

C

2

H

5

NO

2

-CH

2

CH

2 - C 2

H

5

C

3

H

7 -n CN -CH 2

CH

2 - C 2

H

5

C

3 H7-n 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

7 -i NO 2

-CH

2

CH

2 - C 2

H

5

OCH

3 CN -CH 2

CH

2 - C 2

H

5

OCH

3

NO

2

-CH

2

CH

2 - C 2

H

5

OC

2

H

5 CN -CH 2

CH

2 - C 2

H

5

OC

2

H

5

NO

2

-CH

2

CH

2 - C 2

H

5

OC

3

H

7 -n CN -CH 2

CH

2 - C 2

H

5

OC

3

H

7 -n NO 2

-CH

2

CH

2 - C 2

H

5

OC

3

H

7 -i CN -CH 2

CH

2 - C 2

H

5

OC

3

H

7 -i NO 2

-CH

2

CH

2 - C 2

H

5

SCH

3 CN -CH 2

CH

2 - C 2

H

5

SCH

3

NO

2

-CH

2

CH

2 - C 2

H

5

SC

2

H

5 CN -CH 2

CH

2 - C 2

H

5

SC

2

H

5

NO

2

-CH

2

CH

2 - C 2

H

5

SC

3

H

7 -n CN -CH 2

CH

2 - C 2

H

5

SC

3

H

7 -n 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

NH

2 CN -CH 2

CH

2 - C 2

H

5

NH

2

NO

2

-CH

2

CH

2 - C 2

H

5

NHCH

3 CN -CH 2

CH

2 - C 2

H

5

NHCH

3

NO

2

-CH

2

CH

2 - C 2

H

5

NHC

2

H

5 CN -CH 2

CH

2 - C 2

H

5

NHC

2

H

5

NO

2

-CH

2

CH

2 - C 2

H

5

NHC

3 H7-n CN -CH 2

CH

2 - C 2

H

5

NHC

3 H7-n NO 2 -12 A RY R2 Y A RI R 2Y

-CH

2

CH

2 - C 2

H

5

NHC

3 H7-i CN -CH 2

CH

2 - C 2

H

5

NHC

3

H

7 -i 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

7 -i H CN - C 3

H

7 -i H NO 2 - C 3 H7-i CH 3 CN - C 3

H

7 -i CH 3

NO

2 - C 3 H7-i C 2

H

5 CN - C 3

H

7 -i C 2

H

5

NO

2 - C 3

H

7 -i C 3

H

7 -n CN - C 3

H

7 -i C 3

H

7 -n NO 2 - C 3 H7-i C 3

H

7 -i CN - C 3

H

7 -i C 3

H

7 -i NO 2 - C 3

H

7 -i OCH 3 CN - C 3

H

7 -i OCH 3

NO

2 - C 3

H

7 -i OC 2

H

5 CN - C 3

H

7 -i OC 2

H

5

NO

2 - C 3

H

7 -i OC 3

H

7 -n CN - C 3

H

7 -i OC 3

H

7 -n NO 2 - C 3

H

7 -i OC 3

H

7 -i CN - C 3 Hy-i OC 3

H

7 -i NO 2 - C 3

H

7 -i SCH 3 CN - C 3

H

7 -i SCH 3

NO

2 - C 3

H

7 -i SC 2

H

5 CN - C 3

H

7 -i SC 2

H

5

NO

2 - C 3

H

7 -i SC 3

H

7 -n CN - C 3 H7-i SC 3

H

7 -n NO 2 - C 3

H

7 -i SC 3

H

7 -i CN - C 3 H7-i 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 H7-i NHCH 3

NO

2 - C 3 H7-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

H

7 -i NHC 3

H

7 -n NO 2 - C 3

H

7 -i NHC 3 H7-i CN - C 3

H

7 -i NHC 3

H

7 -i NO 2 - C 3 H7-i N(CH 3

)

2 CN - C 3

H

7 -i 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

H

7 -i C 3

H

7 -n CN -CH 2

CH

2 - C 3

H

7 -i C 3

H

7 -n NO 2

-CH

2

CH

2 - C 3

H

7 -i C 3

H

7 -i CN -CH 2

CH

2 - C 3

H

7 -i C 3 H7-i NO 2 -13 A RI R2 Y A RY R2

-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

H

7 -i OC 2

H

5 CN -CH 2

CH

2 - C 3

H

7 -i OC 2

H

5

NO

2

-CH

2

CH

2 - C 3

H

7 -i OC 3

H

7 -n CN -CH 2

CH

2 - C 3

H

7 -i OC 3 H7-n NO 2

-CH

2

CH

2 - C 3 H7-i OC 3

H

7 -i CN -CH 2

CH

2 - C 3

H

7 -i OC 3

H

7 -i NO 2

-CH

2

CH

2 - C 3

H

7 -i SCH 3 CN -CH 2

CH

2 - C 3

H

7 -i SCH 3

NO

2

-CH

2

CH

2 - C 3

H

7 -i SC 2

H

5 CN -CH 2

CH

2 - C 3 H7-i SC 2

H

5

NO

2

-CH

2

CH

2 - C 3

H

7 -i SC 3

H

7 -n CN -CH 2

CH

2 - C 3 H7-i SC 3

H

7 -n 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

H

7 -i 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

H

7 -i 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

H

7 -n NO 2

-CH

2

CH

2 - C 3 H7-i NHC 3

H

7 -i CN -CH 2

CH

2 - C 3

H

7 -i 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

R

1 R 2 C A NkN I I H Y 5 Here, A, R], R2 and Y have, for example, the meanings listed above in the table for Group 1. Group 3

CH

3 1 2 S A N 'N I I 10 H Y AI II~ Uflfu .YI7u - 14 Here, A, R', R2 and Y have, for example, the meanings listed above in the table for Group 1. Group 4 R1 R2

H

3 S AY N N I 1 5 H Y Here, A, R1, R 2 and Y have, for example, the meanings listed above in the table for Group 1. 10 Group 5 R R2 qS A N N~k I I H Y Here, A, R', R 2 and Y have, for example, the meanings listed above in the table for Group 1. 15 Group 6 Br R1 R2 S A N" N I I H Y Here, A, R', R2 and Y have, for example, the meanings listed above in the table for 20 Group 1.

- 15 Group 7 Br 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 5 Group 1. Group 8 CH

HOH

3 HO S A N N I I H Y 10 Here, A, R , R2 and Y have, for example, the meanings listed above in the table for Group 1. Group 9 O2N 1 A N 'N I 2 H Y 15 Here, A, R', R 2 and Y have, for example, the meanings listed above in the table for Group 1. Group 10 R1 R2 Br R R / I IIN" I I 20 H Y - 16 Here, A, R , R2 and Y have, for example, the meanings listed above in the table for Group 1. Group 11

H

3 A R1 R 2

H

3 0 'S A N N 1 1 5 H Y Here, A, R1, R2 and Y have, for example, the meanings listed above in the table for Group 1. 10 Group 12

CH

3 1 2 Cl 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. 15 Group 13 I I H Y Here, A, R1, R2 and Y have, for example, the meanings listed above in the table for 20 Group 1.

- -------- %- AIZCIA VVU/ V.Y.7U - 17 Group 14

H

3

R

1

R

2 S A N 'kN I I H Y Here, A, R', R 2 and Y have, for example, the meanings listed above in the table for 5 Group 1. Group 15 F A N kN I I H Y 10 Here, A, R', R 2 and Y have, for example, the meanings listed above in the table for Group 1. Group 16 COH R5 R2 A N"'N I I H Y 15 Here, A, R', R 2 and Y have, for example, the meanings listed above in the table for Group 1.

- 18 Group 17

H

3 0 CIA N"'N I I H Y Here, A, R', R 2 and Y have, for example, the meanings listed above in the table for 5 Group 1. Group 18 alA N" N I I H Y 10 Here, A, R', R 2 and Y have, for example, the meanings listed above in the table for Group 1. Group 19 S- CH H C \ H -\C f A N N I I H Y 15 Here, A, R', R 2 and Y have, for example, the meanings listed above in the table for Group 1.

- 19 Group 20

C

2

H

5 S Rl R 2 CIA NI N N I I H Y Here, A, R', R 2 and Y have, for example, the meanings listed above in the table for 5 Group 1. Group 21 C1

HC

2 A N N I I H Y 10 Here, A, R', R 2 and Y have, for example, the meanings listed above in the table for Group 1. Group 22 ClA N -'N I I H Y 15 Here, A, R', R 2 and Y have, for example, the meanings listed above in the table for Group 1.

- 20 Group 23 Cl S R' R C1A N kN I I H Y Here, A, R , R2 and Y have, for example, the meanings listed above in the table for 5 Group 1. Group 24 OH S 3 R' R 2

H

3 C A N N I I H Y 10 Here, A, R1, R2 and Y have, for example, the meanings listed above in the table for Group 1. The compounds of the general formula (I) are obtained when heterocyclylamines of the general formula (II) 15 Z A NH (II), H in which A, R' and Z are as defined above 20 are reacted with imino compounds of the general formula (III) -21 R 2 X"YN (Ill), Y in which R2 and Y are as defined above and 5 X represents alkoxy or alkylthio, if appropriate in the presence of a diluent. 10 Using, for example, 1-(5-fluoro-2-thienyl)-ethylamine and (dimethoxymethylene amino)-(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: CH3 F HNH2 H N >~ F H3 C3 3 ONH 15 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 (I). In the general formula (II), A, R' and Z preferably have those meanings which have already been mentioned above, in 20 connection with the description of the compounds of the general formula (I), 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 25 19816055).

- 22 The formula (III) 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 (I). In the general formula (III), R 2 and Y preferably have those meanings which have already been mentioned above, in 5 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 R2 and Y; X represents in particular C-C 4 -alkoxy or CI-C 4 alkylthio, in particular methoxy, ethoxy, methylthio or ethylthio. 10 The imino compounds of the general formula (UT) 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). 15 The process according to the invention for preparing the compounds of the general formula (I) 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, 20 optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclo hexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropylether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether; ketones, such as acetone, butanone or methyl isobutyl 25 ketone; nitriles, such as acetonitrile, propionitrile or butyronitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formanilide, N-methyl pyrrolidone or hexamethylphosphoric triamide; esters such as methyl acetate or ethyl acetate, sulfoxides, such as dimethyl sulfoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, -23 diethylene 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 5 can be varied within a relatively wide range. In general, the process is carried out at temperatures between 0 0 C and 150'C, preferably between 10 0 C and 120'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 10 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 15 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, 20 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. 25 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, 30 Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, -24 Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum. 5 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, 10 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. 15 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. 20 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 25 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.

-25 The compounds of the formula (I) 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 5 dicotyledonous crops, both by the pre- and the post-emergence method. To a certain extent, the compounds of the general formula (I) according to the invention also have strong activity against animal pests, in particlar against nematodes. 10 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 15 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 20 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. 25 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 multi 30 layer coating.

-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 5 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 10 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 15 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 20 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, 25 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, 30 such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for -27 example alkylaryl polyglycol ethers, alkylsulfonates, alkyl sulfates, arylsulfonates and protein hydrolyzates; suitable dispersants are: for example lignin-sulfite waste liquors and methylcellulose. 5 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. 10 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. 15 The formulations generally comprise between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%. For controlling weeds, the active compounds according to the invention, as such or in 20 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. 25 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, 30 benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac -28 (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, butylate, cafenstrole, caloxydim, carbetamide, carfentrazone(-ethyl), chlomethoxyfen, chloramben, chloridazon, chlorimuron(-ethyl), chlornitrofen, chlorsulfuron, chlortoluron, cinidon(-ethyl), cinmethylin, cinosulfuron, clefoxydim, clethodim, 5 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, dimethachlor, dimethametryn, 10 dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithiopyr, diuron, dymron, epoprodan, EPTC, esprocarb, ethalfluralin, ethametsulfuron(-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanid, fenoxaprop(-P-ethyl), fentrazamide, flamprop(-isopropyl), flamprop(-isopropyl-L), flamprop(-methyl), flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate, flucarbazone, flufenacet, 15 flumetsulam, flumiclorac(-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen(-ethyl), flupoxam, flupropacil, flurpyrsulfuron(-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr (methyl), flurprimidol, flurtamone, fluthiacet(-methyl), fluthiamide, fomesafen, glufosinate (-ammonium), glyphosate(-isopropylammonium), halosafen, haloxyfop( 20 ethoxyethyl), haloxyfop(-P-methyl), hexazinone, imazamethabenz(-methyl), imazamethapyr, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron(-methyl, sodium), ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole, isoxaflutole, isoxapyrifop, lactofen, lenacil, linuron, MCPA, MCPP, mefenacet, mesotrione, metamitron, metazachlor, 25 methabenzthiazuron, metobenzuron, metobromuron, (alpha-)metolachlor, metosulam, metoxuron, metribuzin, metsulfuron(-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendimethalin, pendralin, pentoxazone, phenmedipham, picolinafon, 30 piperophos, pretilachlor, primisulfuron(-methyl), prometryn, propachlor, propanil, -29 propaquizafop, 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, 5 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 10 tritosulfuron. Mixtures with other known active compounds such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and soil conditioners, are also possible. 15 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. 20 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 25 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 30 seen from the examples which follow.

%-~,A I 12IX Ul/ vor - 30 Preparation Examples: Example 1 CH3 CH N N H CN 5 2.0 g (20 mmol) of methyl N-cyano-thiolimido acetate are added to a mixture of 2.0 g (20 mmol) of 1-(3-thienyl)-ethylamine (racemic) and 60 ml of methanol, and the reaction mixture is stirred at room temperature (approximately 20 0 C) for 15 hours. The solvent is then carefully distilled off under reduced pressure. 10 This gives 3.9 g (100% of theory) of N'-cyano-N-[1-(3-thienyl)-ethyl]-ethaneimid 20 amide (racemate) as an amorphous residue having a refractive index nD = 1.5572. Example 2 CH3 NH N N 15 H NO 2 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. 20 This gives 3.1 g (72% of theory) of N'-nitro-N-[1-(3-thienyl)-ethyl]-guanidine (racemate) of melting point 167 0

C.

-31 Example 3

C

2 H S- 3 X II I H UN A mixture of 3.4 g (20 mmol) of S-[1-ethyl-3-(2-thienyl)-propyl]-amine, 2.9 g 5 (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 10 isolated by filtration with suction. This gives 4.2 g (78% of theory) of 2-((3S)-3-{ [(cyanoimino)-(methylsulfanyl) methyl]-amino}-pentyl)-thiophene of melting point 104'C. 15 Example 4

C

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

-32 This gives 2.4 g (96% of theory) of 2-(3-{ [(cyanoimino)-(methoxy)-methyl]-amino} 20 pentyl)-thiophene (racemate) as an amorphous residue having a refractive index nD = 1.5400. 5 Similarly to Examples I 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 (I) listed in Table 1 below. R1 R2 R R2 ZNJ A N N I I H Y 10 Table 1: Examples of the compounds of the formula (I) Ex. Physical. No. A Ri R2 Y Z Data 5 - CH 3

CH

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

CH

3 CN 20 (S] = -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 m.p.: 92'C S (racemate) 9 -CH 2

CH

2 - C 2

H

5

CH

3 CN m.p.: 50'C S (S enantiomer) -33 Ex. Physical. No. A RI R2 Y Z Data 10 -CH 2

CH

2 - C 2

H

5

CH

3 CN enantiomer) 11 - C 2

H

5

CH

3 CN logP = 1.79) S (racemate) 12 -CH 2

CH

2 - C 2

H

5

CH

3 CN m.p.: 61'C S (racemate) 13 -CH 2

CH

2 - CH 3

CH

3 CN m.p.: 72'C d-\ (racemate) S 14 - C 2

H

5

CH

3 CN / \ (racemate) S 15 -CH 2

CH

2 - C 2

H

5

CH

3 CN (amorphous) / \ (racemate) S 16 - CH 3

CH

3 CN m.p.: 64'C Cl (racemate) 17 -CH 2

CH

2 - CH 3

CH

3 CN S (racemate) 18 - C 2

H

5

CH

3 CN C m.p.: 104 0 C C1 s (racemate) 19 -CH 2

CH

2 - C 2

H

5

CH

3 CN / \ CIs (racemate) 20 - CH 3

CH

3 CN m.p.: 108'C Br- (racemate) -34 Ex. Physical. No. A RI R2 Y Z Data 21 -CH 2

CH

2 - CH 3

CH

3 CN Br (racemate) 22 - C 2

H

5

CH

3 CN Br S (racemate) 23 -CH 2

CH

2 - C 2

H

5

CH

3 CN Br S (racemate) 24 - CH 3

CH

3 CN H3C s (racemate) 25 -CH 2

CH

2 - CH 3

CH

3 CN (amorphous)

H

3 CA1S (racemate) 26 - C 2

H

5

CH

3 CN

H

3 C S (racemate) 27 -CH 2

CH

2 - C 2

H

5

CH

3 CN H C (amorphous) 3 S (racemate) 28 - CH 3

CH

3 CN CH 3 C \ (racemate) S 29 -CH 2

CH

2 - CH 3

CH

3 CN CH 3 m.p.: 78'C / \ (racemate) 30 - C 2

H

5

CH

3 CN CH 3 \ (racemate) S 31 -CH 2

CH

2 - C 2

H

5

CH

3 CN CH 3 m.p.: 91'C C \ (racemate)

S

-35 Ex. Physical. No. A RI R2 Y Z Data 32 - CH 3

SCH

3 CN n2 = 1.5956 S (racemate) 33 - CH 3

SCH

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

CH

3

SCH

3 CN [a]20 85.6 S(S enantiomer) 35 -CH2CH2- CH3

SCH

3 CN racematee) 36 - C 2

H

5

SCH

3 CN m.p.: 84'C S (racemate) 37 -CH 2

CH

2 - C 2

H

5

SCH

3 CN m.p.: 102 0 C S (racemate) 38 - CH 3

SCH

3 CN (racemate) S 39 -CH 2

CH

2 - CH 3

SCH

3 CN m.p.: 45'C / \ (racemate) S 40 - C 2

H

5

SCH

3 CN d-\ (racemate) S 41 -CH 2

CH

2 - C 2

H

5

SCH

3 CN m.p.: 128'C / \ (racemate)

S

-36 Ex. Physical. No. A RI R2 Y Z Data 42 - CH 3

SCH

3 CN m.p.: 68'C CI (racemate) 43 -CH 2

CH

2 - CH 3

SCH

3 CN S (racemate) 44 - C 2

H

5

SCH

3 CN m.p.: 111 C CI S (racemate) 45 -CH 2

CH

2 - C 2 H SCH 3 CN CI (racemate) 46 - CH 3

SCH

3 CN m.p.: 114'C Br s (racemate) 47

-CH

2

CH

2

-

CH

3 SCH 3 CN B ( Brs (racemate) 48 - C 2 H SCH 3 CN Br s (racemate) 49 -CH 2

CH

2 - C 2 H SCH 3 CN Br (racemate) 50 - CH 3

SCH

3 CN H3 S (racemate) 51 -CH 2

CH

2 - CH 3

SCH

3 CN m.p.: 108'C H s (racemate) 52 - C 2 H SCH 3 CN 3 S (racemate) 53 -CH 2

CH

2 - C 2

H

5

SCH

3 CN H3 s (racemate) -37 Ex. Physical. No. A RI R2 Y Z Data 54 - CH 3

SCH

3 CN CH 3 / \ (racemate) S 55 -CH 2

CH

2 - CH 3

SCH

3 CN CH 3 m.p.: 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 CH 3 m.p.: 88*C C \ (racemate) S 58 - CH 3

OCH

3 CN m.p.: 63'C S (racemate) 59 -CH 2

CH

2 - CH 3

OCH

3 CN S (racemate) 60 - C 2

H

5

OCH

3 CN m.p.: 113'C S (racemate) 61 - CH 3

OCH

3 CN (racemate) S 62 -CH 2

CH

2 - CH 3

OCH

3 CN 20 nD 1.5434 d-\ (racemate) S 63 - C 2

H

5

OCH

3 CN d-\ (racemate)

S

v, v~ v oval TU 1/15rUU/U3'4Y0 -38 Ex. Physical. No. A RI R2 Y Z Data 64 -CH 2

CH

2 - C 2

H

5

OCH

3 CN / \ (racemate) S 65 - C 2

H

5

OCH

3 CN m.p.: 112 0 C Cl I (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 m.p.: 141'C S (racemate) 70 - CH 3

NH

2

NO

2 [a =82.80 S (S enantiomer) 71 - CH 3

NH

2

NO

2 m.p.: 155 0 C S (R-Enantio mer) 72 - C 2

H

5

NH

2

NO

2 m.p.: 153'C S (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

-39 Ex. Physical. No. A RI R 2 Y Z Data 75 -CH 2

CH

2 - CH 3

NH

2

NO

2 m.p.: 138C / \ (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 m.p.: 145'C CI s (racemate) 79 -CH 2

CH

2 - CH 3

NH

2

NO

2 C1 s (racemate) 80 - C 2

H

5

NH

2

NO

2 m.p.: 106'C CI s (racemate) 81 -CH 2

CH

2 - C 2

H

5

NH

2

NO

2 s (racemate) 82 - CH 3

NH

2

NO

2 m.p.: 125'C Br (racemate) 83 -CH 2

CH

2 - CH 3

NH

2

NO

2 Br (racemate) 84 - C 2

H

5

NH

2

NO

2 Br s (racemate) 85 -CH 2

CH

2 - C 2

H

5

NH

2

NO

2 Br s (racemate) v v VU J UJl..A %U 1 I'JLs1 UUIU)t7U -40 Ex. Physical. No. A R' R2 Y Z Data 86 - CH 3

NH

2

NO

2 H3C s (racemate) 87 -CH 2

CH

2 - CH 3

NH

2

NO

2 m.p.: 130'C 3 S (racemate) 88 - C 2

H

5

NH

2

NO

2 H3C S (racemate) 89 -CH 2

CH

2 - C 2

H

5

NH

2

NO

2 m.p.: 135*C H3C S (racemate) 90 - CH 3

NH

2

NO

2

CH

3 C/ \ (racemate) 91 -CH 2

CH

2 - CH 3

NH

2

NO

2

CH

3 m.p.: 142'C (racemate) S 92 - C 2

H

5

NH

2

NO

2

CH

3 (racemate) S 93 -CH 2

CH

2 - C 2

H

5

NH

2

NO

2

CH

3 m.p.: 134'C (racemate) S 94 -CH 2

CH

2 - C 2

H

5

NH

2 NO2 (S S enantiomer) 95 - CH 3

CH

3 CN logP 2.00b) Cl s (S enantlomer) 96 - CH 3

SCH

3 CN logP 2.31b) CI S (S enantiomer) VV UU1010 rl Io -41 Ex. Physical. No. A R' R2 Y Z Data 97 - CH 3

NH

2

NO

2 m.p.: 134'C C s (S enantiomer) 98 - CH 3

CH

3 CN logP = 2.01b> C1 s (R enantiomer) 99 - CH 3

NH

2

NO

2 m.p.: 132'C C I (R enantiomer) 100 - C 2

H

5

CH

3 CN m.p.: 68*C C S (S enantiomer) 101 - C 2

H

5

SCH

3 CN m.p.: 131 C C s (S enantiomer) 102 - C 2

H

5

NH

2

NO

2 m.p.: 63'C s (S enantiomer) 103 - C 2

H

5

OCH

3 CN m.p.: 48'C C1 s (S enantiomer) 104 - CH 3

SCH

3 CN H 3 C m.p.: 142'C C \ (racemate) 105 - CH 3

NH

2

NO

2

H

3 C m.p.: 143'C C \ (racemate) VVU UU103Y10 r- I r vvu U-7u -42 Ex. Physical. No. A RI R2 Y Z Data 106 - CH 3

CH

3 CN H3C m.p.: 82'C C \ (racemate) 107 - CH 3

OCH

3 CN H 3 C m.p.: 140'C cl (racemate) 108 - C 2

H

5

CH

3 CN m.p.: 108,C S (R enantiomer) 109 - C 2

H

5

SCH

3 CN m.p.: 122'C C s (R enantiomer) 110 - C 2

H

5

NH

2

NO

2 Cl m.p.: 162'C s (R enantiomer) 111 - C 2

H

5

OCH

3 CN Clm.p.: 43*C s (R enantiomer) 112 - CH 3

OCH

3 CN m.p.: 55'C S (S enantiomer) 113 - C 3

H

7 -i CH 3 CN logP =2.07 a) (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 m.p.: 127'C s (racemate) -43 Ex. Physical. No. A R' R 2 Y Z Data 116 -CH 2

CH

2 - C 2

H

5 H CN m.p.: 58'C S 117 - CH 3

CH

3 CN logP = 2.20 a) 5 2 S (racemate) 118 - CH 3

NH

2

NO

2 logP = 1.91 a)

H

5

C

2 S (racemate) 119 - C 2

H

5

CH

3 CN H3 m.p.: 110 0 C C I (racemate) 120 - C 2

H

5

SCH

3 CN H3C m.p.: 145'C Cl \ (racemate) 121 - C 2

H

5

NH

2

NO

2

H

3 C m.p.: 133'C C \ (racemate) 122 - C 2

H

5

OCH

3 CN H 3 C m.p.: 124*C C / (racemate) 123 - C 2

H

5

NHC

3

H

7 -i CN Cl (S enantiomer) 124 - C 2

H

5

NHC

3

H

7 -i CN C s (R enantiomer) 125 -CH 2

CH

2 - C 2

H

5

SCH

3 CN m.p.: 118'C H3 C (S enantiomer) -44 Ex. Physical. No. A RI R2 Y Z Data 126 -CH 2

CH

2 - C 2

H

5

CH

3 CN 3 S (S enantiomer) 127 -CH 2

CH

2 - C 2

H

5

NH

2

NO

2 m.p.: 97'C

H

3 s (S enantiomer) 128 - CH 3

CH

3 CN m.p.: 159'C ClIg C2H (racemate) 129 - CH 3

SCH

3 CN m.p.: 133'C Cl \ C 2

H

5 (racemate) 130 - CH 3

NH

2

NO

2 m.p.: 162'C CI g C 2

H

5 (racemate) 131 - CH 3

CH

3 CN m.p.: 112'C C \ (racemate) 132 - CH 3

NH

2

NO

2 m.p.: 114'C C I\ (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. 5 (a) Mobile phases for the determination in the acidic range: 0.1% aqueous phosphoric acid, acetonitrile; linear gradient from 10% acetonitrile to 90% acetonitrile - corresponding measurement results are marked a) in Table 1.

WO UUIO_16916 r. I /EYUUU.VO -45 (b) 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. 5 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). 10 The lambda max values were determined in the maxima of the chromatographic signals using the UV spectra from 200 to 400 nm.

- ------- A I A A WW'.I U.J*V' W -46 Starting materials of the formula (II): Example (II-1)

H

3 C S H H 5 Step 1 0H C H C H At from 140'C to 160'C, 150 ml of formic acid are added dropwise with stirring to a 10 mixture of 100 g (079 mol) of 2-acetyl-thiophene and 300 ml of formamide, and the reaction mixture is stirred at 160'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. 15 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 S H 20 A mixture of 75 g (0.48 mol) of N-(1-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 -47 chloride, 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. 5 This gives 24.8g (41% of theory) of 1-(thien-2-yl)-ethylamine (racemate) of boiling point 40*C at 0.8 mbar. Example (11-2)

H

3 C HO H H,,-\0 H H 10 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 15 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 20 filtered. From the filtrate, the desired product is isolated by distillation under reduced pressure. This gives 35.5 g (44% of theory) of S-1-(2-thienyl)-ethylamine of boiling point 50'C (at 0.8 mbar). 25 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- -48 methoxyacetyl)-1-(2-thienyl)-ethylamine as a solid residue which melts at about 30 0 C. 60 g (0.30 mol) of R-(N-methoxyacetyl)-1-(2-thienyl)-ethylamine are heated under 5 reflux with 200 ml of water and 200 ml of conc. 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-1-(2-thienyl)-ethylamine of boiling point 10 55'C (at 2 mbar). Example (11-3) H 3 x HCI 15 A mixture of 9.8 g (50 mmol) of N-(1-methyl-4-(thien-2-yl)-butyl)-formamide, 100 ml of conc. hydrochloric acid and 40 ml of water is heated at reflux for 90 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. 20 This gives 8.5 g (83% of theory) of 2-amino-5-(thien-2-yl)-pentane hydrochloride as a dark oil. Similarly to Examples 11-1 to 11-3, it is also possible to prepare, for example, the 25 compounds of the general formula (II) listed in Table 2 below.

,,',A % I IE vu I*~'7v -49 R Z A" NH () H Table 2: Examples of the compounds of the formula (11) Ex.-No. Physical. Data A R' Z H-4 - C 2

H

5 b.p.: 52'C S (at 0.7 mbar) (racemate) H-5 -CH 2

CH

2 - CH 3 b.p.: 53'C S (at I mbar) (racemate) 11-6 -CH 2

CH

2 - CH 3 b.p.: 60'C / \ (at 0.7 mbar) S (racemate) 1-7 -CH 2

CH

2 - CH 3 b.p.: 78'C

H

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

CH

2 - C 2

H

5 b.p.: 65'C S (at 0.7 mbar) (S enantiomer) 11-9 -CH 2

CH

2 - C 2

H

5 b.p.: 83'C / \J (at 1.6 mbar) S (racemate) 11-10 -CH 2

CH

2 - C 2

H

5 b.p.: 85'C H3C_ S (at 0.6 mbar) (racemate) - 50 Ex.-No. Physical. Data A R Z 11-11 -CH 2

CH

2 - C 2

H

5

CH

3 b.p.: 85'C C \ (at 1.5 mbar) S (racemate) 11-12 - CH 3 b.p.: 58'C CI S (at 1.8 mbar) (racemate) 11-13 - C H 3 B.p.: 69 aC Br__ _Is(at 1.4 mbar) (racemate) 1-14 - C 2

H

5 b.p.: 73'C (at 1.4 mbar) (racemate) 1-15 -CH 2

CH

2 - C 2

H

5 b.p.: 90*C H \ C (at 1.5 mbar) 3 S C3 (racemate) 1-16 -CH 2

CH

2 - C 2

H

5 Br b.p.: 1 10 C C/S (at 2 mbar) (racemate) 1-17 -CH 2

CH

2 - C 2

H

5 b.p.: I 10*C /\ C (at 2 mbar) I 0 (racemate) 1-18 - CH 3 b.p.: 50'C / \ (at 3 mbar) S (racemate) 11-19 -CH 2

CH

2 - C 2

H

5 Br S (racemate) -51 Ex.-No. Physical. Data A R Z 11-20 -CH 2

CH

2 - C 2

H

5 Br / \ (racemate) 1-21 -

C

2

H

5 /" \ (racemate) H-22 -

CH

3 / S\ (racemate)

H

3 C s CH 3 11-23 -

C

2

H

5 / S\ (racemate)

H

3 C C H 3 11-24 -

C

2

H

5 CI S(S enantiomer) 11-25 - C 2

H

5 b.p.: 75'C CI S (at 1 mbar) (R enantiomer) 11-26 - CH 3 b.p.: 56'C CI S (at 2 mbar) (S enantiomer) 11-27 - CH 3 b.p.: 60'C CI S (at 2 mbar) (R enantiomer) 1-28 -CH 2

CH

2 - CH 3 b.p.: 62'C S (at 0.5 mbar) (S enantiomer) -52- -53 Use Examples: Example A 5 Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part weight of alkylaryl polyglycol ether 10 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. 15 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. 20 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: 25 0% = no effect (like untreated control) 100% = total destruction -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. 5 Example B Post-emergence test Solvent: 5 parts by weight of acetone 10 Emulsifier: I 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 15 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 20 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. 25 The figures denote: 0% = no effect (like untreated control) 100% = total destruction WO 00165916 i /hrUU/Us3yo -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.

Claims (8)

1. The use of N-substituted heterocyclylalkylamines of the general formula (I) R1 R

2 Z A (), I I H Y 5 in which A represents a single bond or represents alkanediyl, R Represents optionally substituted alkyl, 10 R2 represents hydrogen, amino or represents in each case optionally substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino, Y represents cyano or nitro and 15 Z represents optionally substituted heterocyclyl, for controlling undesirable plants. 20 2. The use as claimed in claim 1, characterized in that A represents a single bond or represents alkanediyl having 1 to 4 carbon atoms, 25 R represents optionally cyano-, halogen-, or C-C 4 -alkoxy-substituted alkyl having 1 to 6 carbon atoms, -57 R2 represents hydrogen, amino or represents in each case optionally cyano-, halogen-, CI-C 4 -alkoxy-, Ci-C 4 -alkylthio-, CI-C 4 alkylsulfinyl- or Ci-C 4 -alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 6 5 carbon atoms in the alkyl groups and Z represents an optionally substituted monocyclic or bicyclic heterocyclic grouping from the group consisting of furyl, tetrahydrofuryl, benzofuryl, dihydrobenzofuryl, isobenzofuryl, thienyl, 10 tetrahydrothienyl, benzothienyl, dihydrobenzothienyl, pyrrolyl, indolyl, isoindolyl, pyrazolyl, indazolyl, imidazolyl, benzimidazolyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzthiazolyl, pyridinyl, quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl, 15 where the substituents are selected from the group consisting of nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, sulfamoyl, halogen, C 1 C 4 -alkyl, Ci-C 4 -halogenoalkyl, CI-C 4 -alkoxy, Ci-C 4 -halogenoalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -halogenoalkylthio, C 1 -C 4 -alkylsulfinyl, CI-C 4 halogenoalkylsulfinyl, CI-C 4 -alkylsulfonyl, C-C 4 -halogenoalkyl 20 sulfonyl, Ci-C 4 -alkyl-carbonyl, Ci-C 4 -alkoxy-carbonyl, CI-C 4 -alkyl amino-carbonyl, di-(CI-C 4 -alkyl)-amino-carbonyl, Ci -C 4 -alkylamino sulfonyl, di-(Ci-C 4 -alkyl)amino-sulfonyl, phenyl.

3. The use as claimed in claim I or 2, characterized in that 25 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-1,3-diyl, -CH 2 CH 2 CH 2 -) or propane-1,2-diyl (-CH 2 CH(CH 3 )-), 30 -58 R' represents in each case optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s or t-butyl, 5 R2 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, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n 10 or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino or dipropylamino and Z represents an optionally substituted monocyclic or bicyclic 15 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, 20 quinolinyl, isoquinolinyl, pyrimidinyl, quinazolinyl, where the substituents are selected from the group consisting of nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, sulfamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t 25 butyl, difluoromethyl, dichloromethyl, trifluoromethyl, trichloro methyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethyl thio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, tri fluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, 30 trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propyl- VvfUU1U071U I U"1/1)7 UUIU.TJU - 59 sulfonyl, trifluoromethylsulfonyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl, methyl aminocarbonyl, ethylaminocarbonyl, n- or i-propylamino-carbonyl, di methylaminocarbonyl, diethylamino-carbonyl, methylaminosulfonyl, 5 ethyl aminosulfonyl, n- or i-propylamino-sulfonyl, dimethylamino sulfonyl, diethylamino-sulfonyl, phenyl.

4. The use as claimed in any of claims I to 3, characterized in that 10 A represents a single bond or represents dimethylene (-CH 2 CH 2 -), R I represents methyl, ethyl, n- or i-propyl, R2 represents hydrogen, amino, methyl, ethyl, n- or i-propyl, methoxy, 15 ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or di ethylamino and Z represents in each case optionally substituted thienyl or benzothienyl, 20 where the 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, Fluorodichloromethyl, 25 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, 30 methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy-carbonyl. - 60

5. An N-substituted heterocyclylalkylamine of the general formula (I) R1 R2 R R2 A N N '(), I I H Y in which 5 A represents a single bond or represents alkanediyl having 1 to 4 carbon atoms, R' represents optionally cyano-, halogen- or Ci-C 4 -alkoxy-substituted 10 alkyl having 1 to 6 carbon atoms, R2 represents hydrogen, amino or represents in each case optionally cyano-, halogen-, CI-C 4 -alkoxy-, Ci-C 4 -alkylthio-, CI-C 4 -alkyl sulfinyl- or CI-C 4 -alkylsulfonyl-substituted alkyl, alkoxy, alkylthio, 15 alkylamino or dialkylamino having in each case 1 to 6 carbon atoms in the alkyl groups, Y represents cyano or nitro, and 20 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, Ci-C 4 -halogenoalkyl, Ci-C 4 -alkoxy, Ci-C 4 25 halogenoalkoxy, Ci-C 4 -alkylthio, Ci-C 4 -halogenoalkylthio, Ci-C 4 alkylsulfinyl, Ci-C 4 -halogenoalkylsulfinyl, Ci-C 4 -alkylsulfonyl, Ci C 4 -halogenoalkylsulfonyl, C I-C 4 -alkyl-carbonyl, CI-C 4 -alkoxy carbonyl, C 1 -C 4 -alkylamino-carbonyl, di-(Ci -C 4 -alkyl)-amino- -61 carbonyl, Ci-C 4 -alkylamino-sulfonyl, di-(Ci-C 4 -alkyl)-amino-sulfonyl, phenyl, except for the compounds N'-cyano-N-[1-methyl-3-(3-thienyl)-propyl] 5 ethaneimidamide, N'-cyano-N-[1-ethyl-3-(3-thienyl)-propyl]-ethaneimid amide, N'-cyano-N-[1-methyl-3-(2-thienyl)-propyl]-ethaneimidamide, N' cyano-N-[1-(2-thienyl)-ethyl]-ethaneimidamide and N'-cyano-N-[1-(3 thienyl)-ethyl]-ethaneimidamide (cf. DE-A-19 832 447). 10

.6. The compound as claimed in claim 5, characterized in that A, RI, R 2 and the substituents listed for Z are as defined in claim 3 or 4.

7. A process for preparing compounds as claimed in claim 5 or 6, characterized in that heterocyclyl amines of the general formula (II) 15 R Z A N (), I H in which A, R' and Z are as defined in claim 5 or 6 20 are reacted with imino compounds of the general formula (IHI) R 2 X N '11) Y in which 25 - 62 262 R2 and Y are as defined in claim 5 or 6 and X represents alkoxy or alkylthio, 5 if appropriate in the presence of a diluent.

8. A herbicidal composition, characterized by the content of at least one compound as claimed in claim 5 or 6 and customary extenders.