WO1999055156A2 - The use of derivatives of iminotriazole as crop protection agents and novel iminotriazoles - Google Patents

Abstract

The invention relates to the use of iminotriazoles of general formula (I), wherein R1 represents aryl or heteroaryl and these radicals can carry one to five groups independently of each other or the aryl- or heteroaryl radical forms a bicyclic system together with a fused phenyl ring, a fused C¿3?-C6 carbocyclic compound or a 5- or 6-membered heterocyclic compound; A is COOR?3¿ or CONR?3R4, R3 and R4¿ being independently of each other, hydrogen, C¿1?-C6-alkyl, C2-C6-alkenyl, C3-C7-cycloalkyl or C1-C6-alkyl-aryl which can optionally be partially or completely halogenised or can carry one to three substituents chosen from the following: C1-C4 alkoxy, C1-C4-halogenalkoxy, C1-C4-alkylthio, C3-C7-cycloalkyl and C5-C7-cycloalkenyl.

Description

 Use of derivatives of iminotriazole as crop protection agents and new iminotriazoles

5 The present invention relates to the use of derivatives of iminotriazole of the formula I as a crop protection agent

15 The invention further relates to new derivatives of iminotriazole of the general formula I.

The object of the present invention was to provide active compounds as crop protection agents.

20th

This object was achieved by the use according to the invention as claimed in claim 1.

Preferred embodiments of the invention can be found in the subclaims and the detailed description below.

In the iminotriazole derivatives of the formula I to be used according to the invention, the substituents R ¹ and A have the following meanings

30 gen:

R ⁱ aryl or heteroaryl, where these radicals can independently carry one to five of the following groups: hydrogen, halogen, cyano, nitro, hydroxy, mercapto, thio-

35 cyanato, carboxy, amino, Ci-C _ß -alkyl, C ₆ cyanoalkyl, C -Cg- alkenyl, Cι-C ₆ -alkoxy-C ₂ -C ₆ alkenyl, C ₃ -C ₆ alkynyl, Ci-Cg-alkoxy-C ₃ -C ₆ -alkynyl, C ₃ -C ₆ -alkynyl-Cι-C ₆ -alkoxy, C ₃ -C ₇ -cycloal-kyl, Cι-C ₆ -alkyl-C ₃ -C ₇ -cycloalkyl, -C-C ₆ -alkoxy-C ₃ -C ₇ -cycloalkyl-, C ₃ -C ₇ -cycloalkyloxy, C ₃ -C -cyanocycloalkyloxy, Ci-Cg-Al-

40 alkyl-C ₃ -C ₇ cycloalkyloxy, C ₃ -C halocycloalkyl, cyano C ₃ -C cycloalkyl, C ₃ -C -Halogencycloalkyloxy, C ₅ -C ₇ cycloalkenyl, _Cι-C6 alkyl-C ₅ -C ₇ -cycloalkenyl, -C-C ₆ -alkoxy-C ₅ -C ₇ -cycloalkenyl, C ₅ -C -cyanocycloalkenyl, C ₅ -C -halo-cycloalkenyl, -C-C ₆ -alkoxy-Cι-C ₆ - Alkyl, -CC ₆ -haloalkyl, C ₂ -C ₆ -halogenal-

45 -alkenyl, C ₃ -C ₆ haloalkynyl, C ₂ -C ₆ -Cyanoalkenyl, cyano C ₃ -C ₆ alkynyl, Cχ-C ₆ -alkoxy, C ₆ -Cyanoalkoxy, Ci-Cg haloalkoxy, C ₂ -C ₆ alkenyloxy, C -C ₆ cyanoalkenyloxy, C -C ₆ haloalkeny- loxy, C ₂ -Cg alkynyloxy, Ci-Cg-alkylthio, C] _. -Cg-cyanoalkylthio, -C-C ₆ -haloalkylthio, Ci-Cg-alkoxy-Ci-Cg-alkylthio, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylcarbonyl, Ci-Cg-alkylcarboxy-Ci-Cg- alkyl, Cι-Cg-alkylcarbonyl-Cι-Cg-alkyl, Cχ-Cg-alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl-Ci-Cg-alkyl, aryl-Cg-C ₃ -alkenyl, aryl -cg-alkynyl, heteroaryl-Ci-Cg-alkyl, heteroaryl-C ₂ -cg-alkenyl, heteroaryl-C ₃ -C ₆ -alkynyl, aryl-Ci Cς-alkoxy, _aryl-C-C6 alkenyloxy , Aryl-C ₃ -C ₆ -alkynyloxy, heteroaryl-CiCg-alkoxy, heteroaryl-C ₂ -Cg-alkenyloxy, heteroaryl-C ₃ -C ₆ -alkynyloxy, Ci-Cg-alkylsulphinyl, Ci-Cg-alkylsulpho- nyl, C -Cg-alkenylsulphinyl, C ₂ -Cg-alkenylsulphonyl, Cχ-Cg-alkylamino, di-Ci-Cg-alkylamino, HC = NOH, Cι-Cg-alkyl-C = NOH, HC = N-0 -C-Cg-alkyl, HC ^ N-0-Cχ-Cg-alkyl-aryl, Cι-C ₆ -alkyl-C = N- 0-Cχ-Cg-alkyl, HC = N-0-C ₂ -C _6- alkenyl, -CC ₆ -alkyl-C = N-0-C ₂ -Cg-alkenyl, HC = N-0-aryl, -C-Cg-alkyl-C = N-0-aryl, aryl, aryloxy, Heteroar yl, heteroaryloxy, arylthio, heteroarylthio, where the cyclic substituents in turn can independently carry one to five of the following substituents: hydrogen, halogen, cyano, nitro, hydroxy, mercapto, thiocyanato, carboxy, amino, Ci-Cg-alkyl, Ci-Cg-cyanoalk-, C ₂ -Cg-alkenyl, -C-Cg-alkoxy-C ₂ -Cg-alkenyl, C ₃ -C ₆ -alkynyl, Cι-Cg-alkoxy-C ₃ -Cg-alkynyl, C ₃ -Cg-alkynyl-Cι-Cg-alkoxy, C ₃ ~ C ₇ - cycloalkyl, Cι-Cg-alkyl-C -C ₇ cycloalkyl, Cι-C ₆ alkoxy-C ₃ -C ₇ - cycloalkyl, C ₃ -C -Cycloalkyloxy, C ₃ -C -Cyanocycloalkyloxy, Cι-Cg-alkyl-C ₃ -C -Cycloalkyloxy, C ₃ -C ₇ -Halogencycloalkyl, C -C -Cyanocycloalkyl, C ₃ -C -Halogencycloalkyloxy, C ₅ -C -Cy- cloalkenyl, -C-Cg-alkyl-C ₅ -C ₇ -cycloalkenyl, Cι-Cg-alkoxy-C ₅ -C ₇ - cycloalkenyl, C ₅ -C -Cyanocycloalkenyl, C ₅ -C -Halogencycloalken- nyl, Cι -C ₆ -alkoxy-Cι-C ₆ alkyl, Ci-Cg-haloalkyl, C -Cg-haloalkenyl, C ₃ -Cg-haloalkynyl, C -Cg-cyanoalkenyl, C ₃ -Cg-cyanoalkynyl, Ci -Cg-alkoxy, Ci-Cg-cyanoalkoxy, Ci-Cg-haloalkoxy, C ₂ -Cg-alkenyloxy, C -Cg-cyanoalkenyloxy, C ₂ -Cg-haloalkenyloxy, C -Cg-alkynyloxy, Ci-Cg -Alkylthio, Cχ-Cg-Cyano- alkylthio, Cι-C ₆ -Halogenalkylthio, Cι-Cg-Alkoxy-Cι-Cg-Alkylt- hio, Ci-Cg-Alkoxycarbonyl, Ci-Cg-Alkylcarbonyl, Cχ-Cg-Alkyl- carboxy-Ci-Cg-alkyl, Cι-Cg-alkylcarbonyl-Cι-Cg-alkyl, Cι-C ₆ -Al - kylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl-Ci-Cg-alkyl, aryl ₂ -Cg-alkenyl, aryl-C ₃ -Cg-alkynyl, heteroaryl-Ci-Cg-alkyl, heteroaryl-C -Cg-alkenyl, heteroaryl-C ₃ - Cg-alkynyl, aryl-Ci-Cg-alkoxy, Aryl-C ₂ -Cg-alkenyloxy, aryl-C ₃ -Cg-alkynyloxy, heteroaryl-CiCg-alkoxy, heteroaryl-C ₂ -Cg -alkenyloxy, heteroaryl-C ₃ -C ₆ -alkynyloxy, Ci-Cg-alkylsulphinyl , Ci-Cg-alkylsulphonyl, C -C ₆ -alkenylsulphinyl, C -Cg-alkenylsulphonyl, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, HC = NOH, Cι-Cg-alkyl-C = NOH, HC = N-0 -C ₆ alkyl, HC = N-0 -C ₆ -A lkyl- Aryl, _Cι-C6 alkyl-C = N-0-Cι-Cg-alkyl, HC = N-0-C ₂ -C ₆ alkenyl, _Cι-C6 alkyl-C = N-0-C ₂ -Cg-alkenyl, HC = N-0-aryl, -C-C ₆ -alkyl-C = N-0-aryl, aryl, aryloxy, heteroaryl, heteroaryloxy, arylthio, heteroarylthio; or

wherein the aryl or heteroaryl radical with a fused-on phenyl ring, a fused-on C ₃ -Cg carbocycle or a 5- or 6-membered heterocycle forms a bicyclic system, the fused-on ring system optionally being able to carry one to three of the substituents mentioned above for aryl.

A COOR ³ or CONR ³ R ⁴ , where R ³ and R ⁴ independently of one another are hydrogen, Ci-Cg-alkyl, C -Cg-alkenyl, C ₃ -C ₇ -cycloalkyl or Ci-Cg-alkyl-aryl, which may be . may be partially or fully halogenated or one to three substituents selected from Cι-C ₄ -alkoxy, C ₄ haloalkoxy, Cι-C ₄ alkylthio, C ₃ -C cycloalkyl may bear Cs-C cycloalkenyl;

and their agriculturally useful salts.

The iminotriazole derivatives to be used according to the invention can be used with respect to the position of the substituent R ¹ as E or Z isomers or as a mixture of the two isomers.

The iminotriazole derivatives of the formula I to be used according to the invention are new and form a separate subject of the invention:

The organic molecule parts mentioned in the definition of R ¹ and A are collective terms for individual enumeration of the individual meanings. All carbon chains, that is to say all alkyl, haloalkyl, cyanoalkyl, alkoxy, haloalkoxy, cyanoalkoxy, alkylthio -, Alkylsulfinyl, alkylsulfonyl, alkylamino, dialkylamino, alkyloximino, alkyliminooxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy and alkynylthio parts can be straight-chain or branched. Halogenated substituents preferably carry one to five identical or different halogen atoms.

Halogen is fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine. Furthermore, for example:

Ci-Cg-alkyl for: methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1-methylpropyl, 2-methylpropyl or 1, 1-dimethyl - ethyl, n-pentyl, 1-methylbutyl, 2-methylbutyl , 3-methylbutyl, 2, 2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1, 1-dimethylpropyl, 1, 2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1 , 1-dimethylbutyl, 1,2-dimethylbutyl, 1, 3-dimethylbutyl, 2, 2-dimethylbutyl, 2, 3-dimethylbutyl, 3, 3-dimethylbutyl, 1-ethylbutyl,

2-ethylbutyl, 1, 1, 2-trimethylpropyl, 1, 2, 2-trimethylpropyl, 1-ethyl-l-methylpropyl or l-ethyl-2-methylpropyl, especially for methyl, ethyl, n-propyl, 1-methylethyl, n-butyl, 1, 1-dimethylethyl, n-pentyl or n-hexyl;

Ci-Cg-haloalkyl for: Ci-Cg-alkyl as mentioned above, which is partially or completely substituted by fluorine, chlorine, bromine and / or iodine, that is, for example, one of the radicals mentioned under C 1 -C ₄ -haloalkyl or for 5- Fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro l-hexyl, 6-chloro-1-hexyl, 6-bromo-l-hexyl, 6-iodo-l-hexyl, 6, 6, 6-trichloro-l-hexyl or dodecafluorohexyl, in particular for chloromethyl, fluoromethyl, difluoromethyl, Trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;

Ci-Cg-alkylamino for: methylamino, ethylamino, n-propylamino, 1-methylethylamino, n-butylamino, 1-methylpropylamino, 2-methylpropylamino, 1, 1-dimethylethylamino, n-pentylamino, 1-methylbutylamino, 2 -Methylbutylamino, 3-methylbutylamino,

2, 2-dimethylpropylamino, 1-ethylpropylamino, n-hexylamino, 1, 1-dimethylpropylamino, 1, 2-dimethylpropylamino, 1-methylpentylamino, 2-methylpentylamino, 3-methylpentyl ino, 4-methylpentylamino, 1, 1 -Dimethylbutylamino, 1, 2-dimethylbutylamino, 1, 3-dimethylbutylamino, 2, 2-dimethylbutylamino, 2,3-dimethylbutylamino, 3, 3-dimethylbutylamino, 1-ethylbutylamino, 2-ethylbutylamino, 1, 1, 2 Trimethylpropylamino, 1,2,2-trimethylpropylamino, 1-ethyl-l-methylpropylamino or l-ethyl-2-methylpropylamino, especially for methyl ino, ethylamino, n-propylamino, 1-methylethylamino, n-butylamino, 1, 1-dimethylethylamino, n-pentylamino or n-hexylamino;

Cyano-Ci-Cg-alkyl for: e.g. cyanomethyl, 1-cyanoeth-l-yl, 2-cyanoeth-l-yl, 1-cyanoprop-l-yl, 2-cyanoprop-l-yl, 3-cyano-prop- 1-yl, l-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-l-yl, 3-cyanobut-l-yl, 4-cyanobut-l- yl, l-cyanobut-2-yl, 2-cyanobut-2-yl, l-cyanobut-3-yl, 2-cyano but-3-yl, l-cyano-2-methyl-prop-3-yl, 2-cyano-2-methyl-prop-3-yl, 3-cyano-2-methyl-prop-3-yl or 2- Cyanomethyl-prop-2-yl, especially for cyanomethyl or 2-cyanoethyl;

(Ci-Cg-alkyl) carbonyl for: methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1, 1-dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1, 1-dimethylpropylcarbonyl, 1, 2-dimethylpropylcarbonyl, 2, 2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methyl- pentylcarbonyl, 4-methylpentylcarbonyl, 1, 1-dimethylbutylcarbonyl, 1, 2-dimethylbutylcarbonyl, 1, 3-dimethylbutyl - carbonyl, 2, 2-dimethylbutylcarbonyl, 2, 3-dimethylbutyl - carbonyl, 3, 3-dimethylbutylcarbonyl, 1- Ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1, 2-trimethylpropylcarbonyl, 1,2, 2-trimethylpropylcarbonyl, 1-ethyl-l-methylpropylcarbonyl or l-ethyl-2-methylpropylcarbonyl, in particular for methylcarbonyl, ethylcarbonyl or 1-methylethylcarbonyl;

(Ci-Cg-alkyl) carbonyl-Ci-Cg-alkyl for: Ci-Cg-alkyl substituted by (Ci-Cg-alkyl) carbonyl as mentioned above, e.g. for methylcarbonylmethyl;

(Ci-Cg-alkyl) carboxyl for: Ci-Cg-alkyl as defined above, substituted with a carboxyl group, e.g. Methylcarboxyl, ethylcarboxyl, n-propylcarboxyl, 1-methylethylcarboxyl, n-butylcarboxyl, 1-methylpropylcarboxyl, 2-methylpropylcarboxyl or 1, 1-dimethylethylcarboxyl, especially for methylcarboxyl;

(Ci-Cg-alkylcarboxyl) -Ci-Cg-alkyl: for Ci-Cg-alkylcarboxyl as defined above, substituted with a Ci-Cg-alkyl group as defined above;

Ci-Cg-alkoxy for: methoxy, ethoxy, n-propoxy, 1-methylethoxy, n-butoxy, 1-methylpropoxy, 2-methylpropoxy or 1, 1-dimethylethoxy, e.g. n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1, 1-dimethylpropoxy, 1, 2-dimethylpropoxy, 2, 2-dimethylpropoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2- Methylpentoxy, 3-methylpentoxy, 4-methylpentoxy,

1, 1-dimethylbutoxy, 1, 2-dimethylbutoxy, 1, 3-dimethylbutoxy,

2, 2-dimethylbutoxy, 2, 3-dimethylbutoxy, 3, 3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1, 1, 2-trimethylpropoxy,

1, 2, 2-trimethylpropoxy, 1-ethyl-l-methylpropoxy and l-ethyl-2-methylpropoxy, especially for methoxy, ethoxy or 1-methylethoxy;

Ci-Cg-haloalkoxy for: a Ci-Cg-alkoxy radical as mentioned above, partially or completely by fluorine, chlorine,

Bromine and / or iodine is substituted, for example one of the radicals mentioned under C 1 -C ₄ -haloalkoxy or for 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5 -Iodine-1-pentoxy, 5, 5, 5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodine-1 -hexoxy,

6, 6, 6-trichloro-l-hexoxy or dodecafluorohexoxy, in particular for chloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy;

(Ci-Cg-alkoxy) carbonyl for: methoxycarbonyl, ethoxycarbonyl, n-propoxycarbonyl, 1-methylethoxycarbonyl, n-butoxycarbonyl, 1-methylpropoxycarbonyl, 2-methylpropoxycarbonyl or 1, 1-dimethylethoxycarbonyl, n-pentoxycarbonyl, 1-methyl - butoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2, 2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1, 1-dimethylpropoxycarbonyl, 1, 2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl 4-methylpentoxycarbonyl, 1, 1-dimethylbutoxycarbonyl, 1, 2-dimethylbutoxycarbonyl, 1, 3-dimethylbutoxycarbonyl, 2, 2-dimethylbutoxycarbonyl, 2,3-dirnethylbutoxycarbonyl, 3,3-dirnethylbutoxycarbonyl, 1- Ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1, 2-trimethylpropoxycarbonyl, 1,2, 2-trimethylpropoxycarbonyl, 1-ethyl-l-ιuethyl-propoxycarbonyl or l-ethyl-2-methyl-propoxycarbonyl, especially for methoxycarbonyl, ethoxycarbonyl or 1-methylethoxycarbon yl;

Ci-Cg-alkylthio for: methylthio, ethylthio, n-propylthio, 1-methylethylthio, n-butylthio, 1-methylpropylthio, 2-methylpropylthio, 1, 1-dimethylethylthio, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3 -Methylbutylthio, 2, 2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1, 1-dimethylpropylthio, 1, 2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio , 1-dimethylbutylthio, 1, 2-dimethylbutylthio,

1, 3-dimethylbutylthio, 2, 2-dimethylbutylthio, 2, 3-dimethylbutylthio, 3, 3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1, 1, 2-trimethylpropylthio, 1, 2, 2- Trimethylpropyl - thio, 1-ethyl-l-methylpropylthio and l-ethyl-2-methylpropyl - thio, especially for methylthio or ethylthio; Ci-Cg-haloalkylthio for: C -Cg-alkylthio as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example one of the radicals mentioned under -C-C ₄ -haloalkylthio or for 5-fluoro- pentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio or 6-chlorohexylthio, especially for chloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, 2-fluoroethylthio, 2-fluoro-ethylthio 2,2-trifluoroethylthio;

Ci-Cg-alkylsulfinyl for: methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 1, 1-dimethyl-ethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfyl, 2-methylsulfinyl , 3-methylbutylsulfinyl, 1, 1-dimethylpropylsulfinyl, 1, 2-dimethylpropylsulfinyl, 2, 2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methyl-pentylsulfinyl -Methylpentylsulfinyl, 1, 1-dimethylbutylsulfinyl, 1, 2-dimethylbutylsulfinyl, 1, 3-dimethylbutylsulfinyl, 2, 2-dimethylbutylsulfinyl, 2, 3-dimethylbutylsulfinyl, 3, 3-dimethylbutylsulfinyl, 1-ethylbutylsulfinyl -Ethylbutylsulfinyl, 1,1, 2-trimethylpropylsulfinyl, 1,2, 2-trimethylpropylsulfinyl, 1-ethyl-l-methylpropylsulfinyl or l-ethyl-2-methylpropylsulfinyl, especially for methylsulfinyl;

Ci-Cg-alkylsulfonyl for: methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, 1-methylethylsulfonyl, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, 1, 1-dimethyl-ethylsulfonyl, n-pentylsulfonyl, 1-methyl-sulfonyl, 1-methyl-sulfonyl-1, , 3-methylbutylsulfonyl, 1, 1-dimethylpropylsulfonyl, 1, 2-dimethylpropylsulfonyl, 2, 2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 4-methylsulfonyl -Methylpentylsulfonyl, 1, 1-dimethylbutylsulfonyl, 1, 2-dimethylbutylsulfonyl, 1, 3-dimethylbutylsulfonyl, 2, 2-dimethylbutylsulfonyl, 2, 3-dimethylbutylsulfonyl, 3, 3-dimethylbutylsulfonyl, 1-ethylsulfonyl -Ethylbutylsulfonyl, 1, 1, 2-trimethylpropylsulfonyl,

1,2, 2-trimethylpropylsulfonyl, 1-ethyl-l-methylpropylsulfonyl or l-ethyl-2-methylpropylsulfonyl, especially for methylsulfonyl;

C -Cg-alkenyl for: e.g. ethenyl, prop-2-en-l-yl, n-buten-4-yl, l-methyl-prop-2-en-l-yl, 2-methyl-prop-2- en-l-yl, 2-butene-1-yl, n-penten-3-yl, n-penten-4-yl, l-methyl-but-2-en-l-yl, 2-methyl-but-2-en-l-yl, 3-methyl-but-2-en-l-yl, 1-methyl-but-3-en-l-yl, 2-methyl-but-3- en-l-yl, 3-methyl-but-3-en-1-yl, 1, 1-dimethyl-prop-2-en-l-yl, 1, 2-dimethyl-prop-2-en- 1- yl, l-ethyl-prop-2-en-l-yl, n-hex-3-en-l-yl, n-hex-4-en-1-yl, n-hex-5-en-l- yl, 1-methyl-pent-3-en-l-yl, 2-methyl-pent-3-en-l-yl, 3-methyl-pent-3-en-l-yl, 4-methyl-pent 3- en-l-yl, l-methyl-pent-4-en-l-yl, 2-methyl-pent-4-en-l-yl, 3-methyl-pent-4-en-l-yl, 4-methyl-pent-4-en-1-yl, 1, 1-dimethyl-but-2-en-1-yl, 1, 1-dimethyl-but-3-en-1-yl, 1, 2- Dimethyl-but-2-en-l-yl, 1, 2-dimethyl-but-3-en-l-yl, 1, 3-dimethyl-but-2-en-l-yl, 1, 3-dimethyl but-3-en-l-yl, 2, 2-dimethyl-but-3-en-l-yl, 2, 3-dimethyl-but-2-en-l-yl, 2, 3-dimethyl-but- 3-en-l-yl, 3,3-dimethyl-but-2-en-l-yl, l-ethyl-but-2-en-l-yl, l-ethyl-but-3-en-l- yl, 2-ethyl-but-2-en-1-yl, 2-ethyl-but-3-en-1-yl, 1, 1, 2-trimethyl-prop-2-ene

1-yl, l-ethyl-l-methyl-prop-2-en-l-yl or l-ethyl-2-methyl-prop-2-en-l-yl, especially for ethenyl, prop-2 -en l-yl or n-butene -4 -yl;

C ₂ -Cg alkenylsulfinyl for: C -Cg alkenyl as defined above, substituted with a sulfinyl group, for example ethenylsulfinyl, prop-2-en-l-ylsulfinyl, n-buten-4-ylsulfinyl, l-methyl-prop -2-en-l-ylsulfinyl, 2-methyl-prop-2-en-l-ylsulfinyl, 2-buten-l-ylsulfinyl, n-penten-3-ylsulfinyl, n-pentene-4-ylsulfinyl , l-methyl-but-2-en-l-ylsulfinyl, 2-methyl-but-2-en-l-ylsulfinyl, 3-methyl-but-2-en-l-ylsulfinyl, 1-methyl-but -3-en-l-ylsulfinyl, 2-methyl-but-3-en-l-ylsulfinyl, 3-methyl-but-3-en-l-ylsulfinyl, 1, 1-dimethyl-prop-2-en-l -yl-sulfinyl, 1, 2-dimethyl-prop-2-en-l-ylsulfinyl, 1-ethyl-prop-2-en-l-ylsulfinyl, n-hex-3-en-l-ylsulfinyl, n-

Hex-4-en-l-ylsulfinyl, n-hex-5-en-l-ylsulfinyl, 1-methyl-pent-3-en-l-ylsulfinyl, 2-methyl-pent-3-en-l-ylsulfinyl, 3-methyl-pent-3-en-l-ylsulfinyl, 4-methyl-pent-3-en-1-ylsulfinyl, l-methyl-pent-4-en-l-ylsulfinyl, 2-methyl-pent-4- en-l-ylsulfinyl, 3-methyl-pent-4-en-l-ylsulfinyl,

4-methyl-pent-4-en-l-ylsulfinyl, 1, l-dimethyl-but-2-en-l-yl, 1, l-dimethyl-but-3-en-l-ylsulfinyl, 1, 2- Dimethyl-but-2-en-l-ylsulfinyl, 1, 2-dimethyl-but-3-en-l-ylsulfinyl,

1, 3-dimethyl-but-2-en-l-ylsulfinyl, 1, 3-dimethyl-but-3-en-l-ylsulfinyl, 2, 2-dimethyl-but-3-en-l-ylsulfinyl,

2,3-dimethyl-but-2-en-l-ylsulfinyl, 2,3-dimethyl-but-3-en-l-ylsulfinyl, 3,3-dimethyl-but-2-en-l-ylsulfinyl, l- Ethyl-but-2-en-l-ylsulfinyl, l-ethyl-but-3-en-l-ylsulfinyl, 2-ethyl-but-2-, 2-ethyl-but-3-en-l-ylsulfinyl, 1 , 1,2-trimethyl-prop-2-en-, l-ethyl-l-methyl-prop-2-en-l-ylsulfinyl or l-ethyl-2-methyl-prop-2-en-l- ylsulfinyl, in particular for ethenylsulfinyl, prop-2 -en-1-ylsulfinyl or n-buten-4 -ylsulfinyl;

C ₂ -Cg alkenylsulfonyl for: C ₂ -Cg alkenyl as defined above, substituted with a sulfonyl group, for example ethenylsulfonyl, prop-2-en-l-ylsulfonyl, n-buten-4-ylsulfonyl, l-methyl- prop-2-en-l-ylsulfonyl, 2-methyl-prop-2-en-l-ylsul - fonyl, 2-buten-l-ylsulfonyl, n-pentene-3-ylsulfonyl, n-pentene-4- ylsulfonyl, l-methyl-but-2-en-l-ylsulfonyl, 2-methyl-but-2-en-l-ylsulfonyl, 3-methyl-but-2-en-l-ylsulfonyl, 1-methyl- but-3-en-l-ylsulfonyl, 2-methyl-but-3-en-l-ylsulfonyl, 3-methyl-but-3-en-l-ylsulfonyl, 1, l-dimethyl-prop-2-en- l-yl-sulfonyl, 1, 2-dimethyl-prop-2-en-l-ylsulfonyl, 1-ethyl-prop-2-en-l-ylsulfonyl, n-hex-3-en-l-ylsulfonyl, n- Hex-4-en-l-ylsulfonyl, n-hex-5-en-l-ylsulfonyl, 1-methyl-pent-3-en-l-ylsulfonyl, 2-methyl-pent-3-en-l-ylsulfonyl, 3-methyl-pent-3-en-l-ylsulfonyl, 4-methyl-pent-3-en-1-ylsulfonyl, l-methyl-pent-4-en-l-ylsulfonyl, 2-methyl-pent-4- en-l-ylsulfonyl, 3-methyl-pent-4-en-l-ylsulfonyl, 4-methyl-pent-4-en-l-ylsulfonyl, 1, l-dimethyl-but-2-en-l -yl, 1, l-dimethyl-but-3-en-l-ylsulfonyl, 1, 2-dimethyl-but-2-en-l-ylsulfonyl, 1, 2-dimethyl-but-3-en-l-ylsulfonyl , 1, 3-Dimethyl-but-2-en-l-ylsulfonyl, 1, 3-dimethyl-but-3-en-l-ylsulfonyl, 2, 2-dimethyl-but-3-en-l-ylsulfonyl, 2 , 3-Dimethyl-but-2-en-l-ylsulfonyl, 2, 3-dimethyl-but-3-en-l-ylsulfonyl, 3, 3-dimethyl-but-2-en-l-ylsulfonyl, l-ethyl -but-2-en-l-ylsulfonyl, l-ethyl-but-3-en-l-ylsulfonyl, 2-ethyl-but-2-, 2-ethyl-but-3-en-l-ylsulfonyl, 1, 1,2-trimethyl-prop-2-ene, l-ethyl-l-methyl-prop-2-en-l-ylsulfonyl or l-ethyl-2-methyl-prop-2-en-l-ylsulfonyl , especially for ethenylsulfonyl, prop-2-en-1 -ylsulfonyl or n-butene-4 -ylsulfonyl;

C -Cg haloalkenyl for: C ₃ -Cg alkenyl as mentioned above, which is partially or completely substituted by fluorine, chlorine and / or bromine, for example 2-chloroallyl, 3-chloroallyl, 2, 3-dichloroallyl, 3, 3-dichlorallyl, 2,3,3-trichlorallyl, 2, 3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2, 3-dibromoallyl, 3, 3-dibromoallyl, 2, 3, 3- Tribromoallyl or 2,3-dibromobut-2-enyl, in particular for 2-chloroallyl or 3,3-dichlorallyl;

C -Cg alkenyloxy for: ethenyloxy, prop-1-en-l-yloxy, prop-2-en-l-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy , n-buten-3-yloxy, 1-methyl-prop-l-en-l-yloxy,

2-methyl-prop-l-en-l-yloxy, l-methyl-prop-2-en-l-yloxy, 2-methyl-prop-2-en-l-yloxy, n-pentene-1- yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methyl-but-l-en-l-yl-oxy, 2-methyl-but-l-en-l-yloxy, 3-methyl- but-l-en-l-yloxy, l-methyl-but-2-en-l-yloxy, 2-methyl-but-2-en-l-yloxy, 3-methyl-but-2-en-l- yloxy, l-methyl-but-3-en-l-yloxy, 2-methyl-but-3-en-l-yloxy, 3-methyl-but-3-en-l-yloxy,

1, l-dimethyl-prop-2-en-l-yloxy, 1, 2-dimethyl-prop-l-en-l-yl-oxy, 1, 2-dimethyl-prop-2-en-l-yloxy, l-ethyl-prop-l-en-2-yl - oxy, l-ethyl-prop-2-en-l-yloxy, n-hex-1-en-l-yloxy, n-hex-2-en- 1-yloxy, n-hex-3-en-l-yloxy, n-hex-4-en-l-yloxy, n-hex-5-en-1-yloxy, 1-methyl-pent-l-en- l-yloxy, 2-methyl-pent-l-en-

1-yloxy, 3-methyl-pent-l-en-l-yloxy, 4-methyl-pent-1-en-l-yl-oxy, l-methyl-pent-2-en-l-yloxy, 2- Methyl-pent-2-en-l-yloxy, 3-methyl-pent-2-en-l-yloxy, 4-methyl-pent-2-en-l-yloxy, 1-methyl-pent-3-en- 1-yloxy, 2-methyl-pent-3-en-l-yloxy, 3-methyl-pent-3-en-l-yloxy, 4-methyl-pent-3-en-l-yloxy, 1-methyl- pent-4-en-l-yloxy, 2-methyl-pent-4-en-l-yloxy, 3-methyl-pent-4-en-l-yloxy, 4-methyl-pent-4-en-l- yloxy, 1, 1-dimethyl-but-2-en-l-yloxy, 1, l-dimethyl-but-3-en-l-yloxy, 1, 2-dimethyl-but-1-en-l-yloxy, 1, 2-dimethyl-but-2-en-l-yloxy, 1, 2-dimethyl-but-3-en-l-yloxy, 1, 3-dimethyl-but-l-en-l-yloxy, 1, 3-dimethyl-but-2-en-l-yloxy, 1, 3-dimethyl-but-3-en-l-yloxy, 2, 2-dimethyl-but-3-en-l-yloxy, 2, 3- Dimethyl-but-l-en-l-yloxy, 2, 3-dimethyl-but-2-en-l-yloxy, 2, 3-dimethyl-but-3-en-l-yloxy, 3, 3-dimethyl but-l-en-l-yloxy, 3, 3-dimethyl-but-2-en-l-yloxy, 1-ethyl-but-l-en-l-yloxy, l-ethyl-but-2-en- l-yloxy, 1-ethyl-but-3-en-l-yloxy, 2-ethyl-but-l-en-l-yloxy, 2-ethyl-but-2-en-1-yloxy, 2-ethyl bu t-3-en-l-yloxy, 1, 1, 2-trimethyl-prop-2-en-1-yloxy, l-ethyl-l-methyl-prop-2-en-l-yloxy, l-ethyl- 2-methyl-prop-1-en-1-yloxy or 1-ethyl-2-methyl-prop-2-en-1-yloxy, in particular for ethenyloxy or prop-2-en-1-yloxy;

C ₃ -C ₅ alkynyl for: ethynyl, prop-1-in-l-yl, prop-2-in-l-yl, n-but-1-in-l-yl, n-but-l-in -3-yl, n-but-l-in-4-yl, n-but-2-in-l-yl, n-pent-1-in-l-yl, n-pent-l-in-3 -yl, n-pent-1-in-4-yl, n-pent-1-in-5-yl, n-pent-2-in-1-yl, n-pent-2-in-4-yl , n-Pent-2-in-5-yl, 3-methyl-but-l-in-3-yl, 3-methyl-but-l-in-4-yl, n-hex-1-in-l -yl, n-hex-1-in-3-yl, n-hex-1-in-4-yl, n-hex-1-in-5-yl, n-hex-1-in-6-yl , n-Hex-2-in-l-yl, n-Hex-2-in-4-yl, n-Hex-2-in-5-yl, n-Hex-2-in-6-yl, n -Hex-3-in-1-yl, n-hex-3-in-2-yl, 3-methyl-pent-1-in-1-yl, 3-methyl-pent-1-in-3-yl , 3-methylpent-1-in-4-yl, 3-methylpent-1-in-5-yl, 4-methylpent-1-in-1-yl, 4-methylpent-2 -in-4-yl or 4-methyl-pent-2-yn-5-yl, especially for ethynyl or prop-2-yn-l-yl; C -Cg alkynyloxy for: ethynyloxy, prop-1-in-1-yloxy, prop-2-in-1-yloxy, n-but-1-in-1-yloxy, n-but-1-ynoxy -yloxy, n-but-l-in-4-yloxy, n-but-2-in-l-yloxy, n-pent-1-in-l-yloxy, n-pent-l-in-3-yloxy , n-pent-1-in-4-yloxy, n-pent-1-in-5-yloxy, n-pent-2-in-1-yloxy, n-pent-2-in-4-yloxy, n Pent-2-in-5-yl-oxy, 3-methyl-but-l-in-3-yloxy, 3-methyl-but-l-in-4-yloxy, n-hex-1-in-l -yloxy, n-hex-1-in-3-yloxy, n-hex-1-in-4-yloxy, n-hex-1-in-5-yloxy, n-hex-1-in-6-yloxy , n-Hex-2-in-1-yloxy, n-Hex-2-in-4-yloxy, n-Hex-2-in-5-yloxy, n-Hex-2-in-6-yloxy, n - Hex-3-in-1-yloxy, n-Hex-3-in-2-yloxy, 3-methylpent-1-in-1-yloxy, 3-methylpent-1-in-3-yloxy , 3-methyl-pent-l-in-4-yloxy, 3-methyl-pent-l-in-5-yloxy, 4-methyl-pent-l-in-l-yloxy, 4-methyl-pent -2-in-4-yloxy or 4-methylpent-2-in-5-yloxy, especially for ethynyloxy or prop-2-in-l-yloxy;

C ₃ -C cycloalkyl for: cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, in particular for cyclopentyl or cyclohexyl;

- C ₃ -C cycloalkyloxy for: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy or cycloheptyloxy;

C ₅ -C cycloalkenyl for: cyclopent-1-enyl, cyclopent-2-enyl, cyclopent-3-enyl, cyclohex-1-enyl, cyclohex-2-enyl, cyclohex-3-enyl, cyclohept-1-enyl, Cyclohept-2-enyl, cyclohept-3-enyl or cyclohept-4-enyl;

Heteroaryl: aromatic heterocycles with one to three heteroatoms selected from a group consisting of - one to three nitrogen atoms, one or two oxygen and one or two sulfur atoms, e.g.

Furyl such as 2-furyl and 3-furyl, thienyl such as 2-thienyl and 3-thienyl, pyrrolyl such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl such as 2-0xazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl such as 2-thiazolyl, 4-thiazolyl and 5- Thiazolyl, imidazolyl such as 2-imidazolyl and 4-imidazolyl, oxadiazolyl such as 1, 2, 4-oxadiazol-3-yl, 1, 2, 4-oxadiazol-5-yl and 1, 3, 4-oxadiazol-2-yl, Thiadiazolyl such as 1, 2, 4-thiadiazol-3-yl, l, 2,4-thiadiazol-5-yl and 1, 3, 4-thiadiazol-2-yl, triazolyl such as 1,2,4-triazol-l- yl, 1, 2, 4-triazol-3-yl and 1,2,4-triazol-4-yl, pyridinyl such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl such as 3-pyridazinyl and 4- Pyridazinyl, Pyrimidinyl such as 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore 2-pyrazinyl, 1, 3, 5-triazin-2-yl and 1, 2, 4-triazin-3-yl, in particular pyridyl, pyridyl, Furanyl and thienyl;

Aryl is: Cg-Ci ~ ₄ aryl such as phenyl, naphthyl, anthracenyl before ^¬ preferably phenyl.

The iminotriazole derivatives can be obtained by processes known per se to the person skilled in the art and described in the literature, so that further details are unnecessary here. For example, please refer to Houben Weyl Volume 7/1, page 453.

A preferred process variant can be found in Reaction Scheme 1 below. The detailed reaction conditions are known to the person skilled in the art:

"I

The aminotriazoles of formula II are known and can e.g. according to the in J. Liebigs Ann. Chem. 303 (1898), 51 or Bull. Pharm.

Be. Assvit. Univ. 1997, 20, 47 described methods are produced.

Iminotriazole derivatives are preferably used according to the invention in which A for a grouping COOH or COO-Ci-Cg-alkyl and R ^{1 has} the meanings given in Tables A and B below.

The compounds of formula I are particularly preferred in NEN de ^¬ A is COOH, COOCH ₃ or COOC ₂ H ₅ and R ¹ has one of the meanings given in the following tables A and B is aryl or heteroaryl.

Table A: R ¹ = aryl

According to a preferred embodiment, the immotriazoles I and their agriculturally useful salts are used both as isomer mixtures and in the form of the pure isomers as herbicides. The herbicidal compositions containing I control plant growth very well on non-cultivated areas. In crops such as wheat, rice, corn, soybeans and cotton, they act against weeds and grass weeds without significantly damaging the crop plants. This effect occurs especially at low application rates. Depending on the particular application method, the compounds I or herbicidal compositions comprising them can also be used in a further number of crop plants for eliminating undesired plants. For example, the following cultures can be considered:

Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var. napo- brassica, Brassica rapa var. silvestris, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea libericaus), Cucumis sativ Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgäre, Lens humus lupulus, I Linum usitatissimum, Lycopersicon lycopersicum, Malus spec, Manihot esculenta, Medicago sativa, Musa spec, Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec, Pisum sativum, Prunus Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Seeale cereale, Solanum tuberosum, Sorghum bicolor (see vulgar), Theobroma cacao, Tri - folium pratense, Triticum aestivum, Triticum durum, Vicia faba, Vitis vinifera and Zea mays.

In addition, the compounds I can also be used in crops which are tolerant to the action of herbicides by breeding, including genetic engineering methods.

The herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active ingredients are less compatible for certain crop plants, application techniques can be used in which the herbicides are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not struck wherever possible, while the active ingredients grow on the leaves below them unwanted plants or the uncovered floor area (post, directed, lay-by).

Furthermore, the iminotriazoles I are also suitable for the desiccation and / or defoliation of plants. As desiccants, they are particularly suitable for drying out the above-ground parts of crops such as potatoes, rapeseed, sunflower and soybeans. This enables a fully mechanical harvesting of these important crops.

Also of economic interest is the ease of harvesting, which is made possible by the temporally concentrated decrease or decrease in the adhesive strength on the tree in the case of citrus fruits, olives or other types and varieties of pome, stone and nuts. The same mechanism, that is to say the promotion of the formation of separating tissue between the fruit or leaf and shoot part of the plants, is also essential for a well controllable defoliation of useful plants, in particular cotton.

In addition, the shortening of the time interval in which the individual cotton plants ripen leads to increased fiber quality after the harvest.

According to the invention, the compounds of the formula I are also used for combating animal pests from the class of the insects, arachnids and nematodes. They can be used in crop protection as well as in the hygiene, storage protection and veterinary sectors to control animal pests. They are particularly suitable for controlling the following animal pests:

• Insects from the order of the butterflies (Lepidoptera), for example Agrotis ypsilon, Agrotis segetum, Alabama argilla- cea, Anticarsia gemmatalis, Argyresthia conjugella, Autographa gamma, Bupalus piniarius, Cacoecia murinana, Capua reticulana, Cheimatobone brumoneurumuraisumuraisumuraisumanaurumura, chorus unipuncta, Cydia pomonella, Dendrolimus pini, Diaphania nitidalis, Diatraea grandiosella, Earias insulana, Elasmopalpus lignosellus, Eupoecilia ambiguella, Evetria bouliana, Feltia subterranea, Galleria mellonella, Grapholitha funebrana, Helithiothiothiothiella, Helithiothiothiothi, Helithium, Helithiothiothiothiothi, Helithiothiothiothi, Helithiothiothiothi, Helithiothiothiothiothi, Helithiothiothiothi, Helithiothiothi, Helithiothiothiothi, Helithiothiothiothi, Helithiothiothi undalis, Hibernia defoliaria, Hyphantria cunea, Hyponomeuta malinellus, Keiferia lycopersi- cella, Lambdina fiscellaria, Laphygma exigua, Leucoptera cof- feella, Leucoptera scitella, Lithocolletis blancardella, Lobe- sia botrana, Licalisiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaiaa Malacosoma neustria, Mamestr a brassicae, Orgyia pseudotsugata, Ostrinia nubilalis, Panolis flammea, Pectinophora gossypiella, Peridroma saucia, Phalera bucephala, Phthorimaea operculella, Phyllocnistis citrella,

Pieris brassicae, Plathypena scabra, Plutella xylostella, Pseudodusus includens, Rhyacionia frustrana, Scrobipalpula abso- luta, Sitotroga cerealella, Sparganothis pilleriana, Spodoptera frugiperda, Spodoptera littoralis, Spodoptera litura, Thaumato-poea pityocampa, Tortrix viridana, Trichoplusia ni and Zeiraphera canadensis,

Beetles (Coleoptera), e.g. Agrilus sinuatus, Agriotes lineatus, Agriotes obscurus, Amphimallus solstitialis, Anisandrus dispar, Anthonomus grandis, Anthonomus pomorum, Atomaria linearis, Blastophagus piniperda, Blitophaga undata, Bruchus rufimanus, Bruechus pisorum, Bruchus lentisu- losa, Byiscus , Cerotoma trifurcata, Ceuthorrhynchus assi ilis, Ceuthorr- hynchus napi, Chaetocnema tibialis, Conoderus vespertinus, Crioceris asparagi, Diabrotica longicornis, Diabrotica 12-punc- tata, Diabrotica virgiferisisisobirisisutobisisirobisisisobirisisobutisis, Epilachinisisobutisis, Epilachinisis, Epilachinisis, Epilachinisis, Epilachinitris, Epilachinis, varilobis brunneipennis, Hypera postica, Ips typographus, Lema bilineata, Lema melanopus, Leptinotarsa dece lineata, Limonius californi- cus, Lissorhoptrus oryzophilus, Melanotus communis, Meligethes aeneus, Melolonche, melolonthaulolonhychon Phyllotreta chrysocephala, Phyllophaga sp., Phyllopertha hort icola, Phyllotreta nemorum, Phyllotreta striolata, Popillia japonica, Sitona lineatus and Sitophilus granaria,

• Two-winged (Diptera), e.g. Aedes aegypti, Aedes vexans, Anas- trepha ludens, Anopheles maculipennis, Ceratitis capitata, Chrysomya bezziana, Chrysomya hominivorax, Chrysomya macella- ria, Contarinia sorghicola, Cordylobia anthropophaga, Culex pi piens, Dacus cucurbitae, Dacus oleae, Dasineura brassicae, fan- nia canicularis, Gasterophilus intestinalis, Glossina morsitans, Haematobia irritans, Haplodiplosis equestris, Hylemyia platura, Hypoderma lineata, Liriomyza sativae, Liriomyza trifolii, Lucilia caprina, Lucilia cuprina, Lucilia sericata pectoral, Lyco- rica pomica, lyco- rica, lorica- rica, lalica- rorica p , Muscina stabulans, Oestrus ovis, Oscinella frit, Pegomya hysocyami,

Phorbia antiqua, Phorbia brassicae, Phorbia coarctata, Rhagoletis cerasi, Rhagoletis pomonella, Tabanus bovinus, Tipula ole-racea and Tipula paludosa,

Thrips (Thysanoptera), e.g. Frankliniella fusca, Frankliniella occidentalis, Frankliniella tritici, Scirtothrips citri, Thrips oryzae, Thrips palmi and Thrips tabaci,

Cuticle fly (Hymenoptera), for example Athalia rosae, Atta cephalotes, Atta sexdens, Atta texana, Hoplocampa minuta, Hoplocampa testu- dinea, Monomorium pharaonis, Solenopsis geminata and Solenopsis invicta,

Bugs (Heteroptera), e.g. Acrosternum hilare, Blissus leucopterus, Cyrtopeltis notatus, Dysdercus cingulatus, Dysdercus intermedius, Eurygaster integriceps, Euschistus impictiventris, Leptoglossus phyllopus, Lygus lineolaris, Lygus pratensis, Nezara quadrantulais, Pyanma viridula, Pies

Plant suckers (Homoptera), e.g. Acyrthosiphon onobrychis, Adelges laricis, Aphidula nasturtii, Aphis fabae, Aphis pomi, Aphis sambuci, Brachycaudus cardui, Brevicoryne brassicae, Ce-rosipha gossypii, Dreyfusia nordmannianae, Dreyfusia picisacumaumolaisolapiaaciaacolaicausolaapiaolapiaacolaicausolaapiaolabiaapiaaciosaapiaaciaiaabiaapiaaciaapiaaciaapiaaciaapiaaciaapiaaciaiaapiaumapiaapiaapiaapiaumia Macrosiphon rosae, Megoura viciae, Metopolophium dirhodum, Myzodes persicae, Myzus cerasi, Nilaparvata lugens, Pemphigus bursarius, Perkinsiella saccharicida, Phorodon humuli, Psylla mali, Psylla piri, Rhopa- lomyzus papalisisaphapisis, Sapphiphalis, Malaidisosalappa, Rhaidalisisapphicus, Saidalappa, Rhaid graminum, Schizoneura lanuginosa, Tria- leurodes vaporariorum and Viteus vitifolii,

Termites (Isoptera), e.g. Calotermes flavicollis, Leucotermes flavipes, Reticulitermes lucifugus and Termes natalensis,

Straight wing aircraft (Orthoptera), e.g. Acheta domestica, Blatta orien- talis, Blattella germanica, Forficula auricularia, Gryllotalpa gryllotalpa, Locusta migratoria, Melanoplus bivittatus, Melanoplus femur-rubrum, Melanoplus mexicanus, Melanoplus sanguini- pes, Melanoplus spretus, Ameradococentina, Pericocarpeanus, Pericocarpus america, Nomadascacrata ameracerana, Periscus america, Pericocarpus nec , Stauronotus maroccanus and Tachycines asynamorus,

Arachnoid such as arachnids (Acarina), e.g. Amblyomma america- num, Amblyomma variegatum, Argas persicus, Boophilus annulatus,

Boophilus decoloratus, Boophilus microplus, Brevipalpus phoeni- cis, Bryobia praetiosa, Dermacentor silvarum, Eotetranychus carpini, Eriophyes sheldoni, Hyalomma truncatum, Ixodes ricinus, Ixodes rubicundus, Ornithodorus moubatanorausiniusinioginobus, pilini, Otini , Polyphagotarsonemus latus, Psoroptes ovis, Rhipicephalus appendiculatus, Rhipicephalus evertsi, Sarcoptes scabiei, Tetranychus cinnabarinus, Tetranychus kanzawai, Tetra - nychus pacificus, Tetranychus telarius and Tetranychus urticae

Nematodes such as root biliary nematodes, for example Meloidogyne hapla, Meloidogyne incognita, Meloidogyne javanica, cyst-forming Nematodes, for example Globodera rostochiensis, Heterodera avenae, Heterodera glycines, Heterodera schachtii, Heterodera trifolii, stick and leaf aphids, for example Belonolaimus longicaudatus, Dity- lenchus destructor, Ditylenchus dipsaci, Heliocotylenusususus, Rad- longicililinus- Longidilinilus- Longidilinilus- Longidilinilus- Longidilinus chus robustus, Trichodorus primitivus, Tylenchorhynchus claytoni, Tylenchorhynchus dubius, Pratylenchus neglectus, Pratylenelenchus penetrans, Pratylenchus curvitatus and Pratylenchus goodeyi.

The compounds I or the compositions comprising them can be sprayed, for example in the form of directly sprayable aqueous solutions, powders, suspensions, including high-strength aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, sprays or granules. Nebulization, dusting, scattering or pouring can be used. The application forms depend on the purposes; in any case, they should ensure the finest possible distribution of the active compounds according to the invention.

The following are essentially considered as inert auxiliaries: mineral oil fractions of medium to high boiling point such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. Paraffins, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, strongly polar solvents, e.g. Amines such as N-methylpyrrolidone and water.

Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or old dispersions, the immotriazoles as such or dissolved in an oil or solvent can be homogenized in water by means of wetting agents, adhesives, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of an active substance, wetting agent, tackifier, dispersant or emulsifier and possibly solvent or oil, which are suitable for dilution with water.

The surface-active substances are the alkali metal, alkaline earth metal and ammonium salts of aromatic sulfonic acids, for example lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, and salts of sulfated hexa- , Hepta- and octadecanols as well as fatty alcohol glycol ether, condensate tion products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or 5 nonylphenol, alkylphenyl, tributylphenyl polyglycol ether, alkyl - aryl alcohol fatty alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol ether, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol ether, alkyl - aryl alcohol fatty alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol fatty alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol and alcohol - alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol fatty alcohol, alkyl - aryl alcohol alcohol, alkyl - aryl alcohol fatty alcohol, alkyl - aryl alcohol alcohol, and alkyl - aryl alcohol fatty alcohol; -Condensates, ethoxylated castor oil, polyoxyethylene or polyoxypropylene alkyl ether, lauryl alcohol polyglycol ether acetate, sorbitol ester, lignin sulfite waste liquor or methyl cellulose into consideration.

Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.

15

Granules, e.g. Coated, impregnated and homogeneous granules can be produced by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, silica gels, silicates, talc, kaolin, limestone, lime,

20 chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, ureas and vegetable products such as flour, tree bark, wood and nutshell flour, cellulose powder or others

25 solid carriers.

The concentrations of the active ingredients I in the ready-to-use preparations can be varied over a wide range. The formulations generally contain from about 0.001 to 30 98% by weight, preferably 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to the NMR spectrum).

35 The following formulation examples illustrate the preparation of such preparations:

I. 20 parts by weight of a compound of the formula I are dissolved in a mixture which is alkylated from 80 parts by weight of

40 tem benzene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide with 1 mole of oleic acid-N-monoethanol amide, 5 parts by weight of calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide with 1 mole of castor oil. By off -

Pour 45 and finely distribute the solution in 100,000 weight parts of water, an aqueous dispersion is obtained which contains 0.02% by weight of the active ingredient.

II. 20 parts by weight of a compound of the formula I are dissolved in a mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide and 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide on 1 Mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.

III. 20 parts by weight of a compound of the formula I are dissolved in a mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction with a boiling point of 210 to 280 ° C. and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which contains 0.02% by weight of the active ingredient.

IV. 20 parts by weight of a compound of formula I are mixed well with 3 parts by weight of the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of powdered silica gel and ground in a hammer mill. A fine spray mixture containing 0.1% by weight of the active ingredient is obtained by finely distributing the mixture in 20,000 parts by weight of water.

V. 3 parts by weight of a compound of formula I are mixed with 97 parts by weight of finely divided kaolin. In this way, a dusting agent is obtained which contains 3% by weight of the active ingredient.

VI. 20 parts by weight of a compound of formula I are intimately mixed with 2 parts by weight of calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained. VII. 1 part by weight of a compound of formula I is dissolved in a mixture consisting of 70 parts by weight of cyclohexanone,

There are 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtained.

VIII. 1 part by weight of a compound of formula I is dissolved in a mixture consisting of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol ^® EM 31 (= nonionic emulsifier based on ethoxylated castor oil). A stable emulsion concentrate is obtained.

The active ingredients I or the herbicidal compositions can be applied pre- or post-emergence. If the active ingredients are less compatible with certain crop plants, application techniques can be used in which the herbicidal compositions are sprayed with the aid of sprayers in such a way that the leaves of the sensitive crop plants are not hit as far as possible, while the active ingredients are applied to the leaves of undesirable plants growing below them or the uncovered floor area (post-directed, lay-by).

The application rates of active ingredient I are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a.S.) depending on the control target, the season, the target plants and the growth stage.

To broaden the spectrum of activity and to achieve synergistic effects, the immotriazoles I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups and applied together. For example, 1, 2, 4-thiadiazoles, 1, 3, 4-thiadiazoles, amides, aminophosphoric acid and their derivatives, aminotriazoles, anilides, aryloxy- / heteroaryloxyalkanoic acids and their derivatives, benzoic acid and their derivatives, benzothiaediazinones, 2 - (Hetaroyl / Aroyl) - 1, 3 -cyclohexanediones, heteroaryl-aryl-ketones, benzylisoxazolidinones, meta-CF ₃ -phenyl derivatives, carbamates, quinolinecarboxylic acid and their derivatives, chloroacetanilides, cyclohexane-1, 3-dione derivatives, diazione, dichloro-dichloro acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3, 4, 5, 6- tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy and hetero-aryloxyphenoxypropionic acid esters, phenylacetic acid and its derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinca rbonic acid and its derivatives, pyrimidyl ether, sulfonamides, sulfonylureas, Triazines, Triazinones, Triazolinones, Triazolcarboxamides and Uracile.

It may also be useful to apply the compounds I alone or in combination with other herbicides, mixed with other crop protection agents, for example with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used to remedy nutritional and trace element deficiencies. Non-phytotoxic oils and oil concentrates can also be added.

example 1

The herbicidal activity of the iminotriazole of the formula below

1 was shown by greenhouse experiments:

Plastic pots with loamy sand with about 3.0% humus as substrate served as culture vessels. The seeds of the test plants were sown separately according to species.

In pre-emergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing using finely distributing nozzles. The tubes were lightly sprinkled to promote germination and growth, and then covered with clear plastic hoods until the plants had grown. This cover causes the test plants to germinate evenly, provided that this has not been impaired by the active ingredients.

For the purpose of post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the growth habit, and then treated with the active ingredients suspended or emulsified in water. The test plants were either sown directly and grown in the same containers or they were first grown separately as seedlings and transplanted into the test containers a few days before the treatment. The application rate for post-emergence treatment was 1.0 or 0.5 kg / ha a.S.

The plants were kept at temperatures of 10 - 25 ° C or 20 - 35 ° C depending on the species. The trial period spanned

2 to 4 weeks. During this time, the plants were cared for and their response to each treatment was evaluated. Evaluation was carried out on a scale from 0 to 100. 100 means no emergence of the plants or complete destruction of at least the aerial parts and 0 means no damage or normal growth.

The plants used in the greenhouse experiments are composed of the following types:

Table 1:

Post-emergence herbicidal activity in the greenhouse

Connection used:

N-N

Claims

claims 1. Use of imonotriazoles of the general formula I 5

where the substituents have the following meanings: 15 R ¹ aryl or heteroaryl, where these radicals can independently carry one to five of the following groups: Hydrogen, halogen, cyano, nitro, hydroxy, mercapto, 20 thiocyanato, carboxy, amino, Ci-Cg-alkyl, Ci-Cg-cyanoalkyl, C ₂ -Cg-alkenyl, Cι-Cg-alkoxy-C ₂ -Cg-alkenyl, C ₃ -Cg-alkynyl, Cι-Cg- Alkoxy-C ₃ -Cg-alkynyl, C ₃ -Cg-alkynyl-Cι-Cg-alkoxy, C ₃ -C ₇ -cycloalkyl, Cι-C ₆ -alkyl-C ₃ -C ₇ cycloalkyl, Ci-Cg-Al - koxy-C ₃ -C ₇ cycloalkyl, C ₃ -C cycloalkyloxy, C ₃ -C ₇ - 25 cyanocycloalkyloxy, -C-Cg-alkyl-C ₃ -C ₇ -cycloalkyloxy, C ₃ -C -halogenocycloalkyl, C ₃ -C ₇ -cyanocycloalkyl, C ₃ -C ₇ - halocycloalkyloxy, C ₅ -C -cycloalkenyl, Ci-Cg -Alkyl-C ₅ -C ₇ -cycloalkenyl, Cι-Cg-alkoxy-C ₅ -C ₇ -cycloalkenyl, C ₅ -C -cyanocycloalkenyl, C ₅ -C ₇ -halogenocycloalkenyl, Cι ~ Cg- 30 alkoxy-Ci-Cg-alkyl, -C ~ Cg-haloalkyl, C ₂ -Cg-haloalkenyl, C ₃ -Cg-haloalkynyl, C ₂ -Cg-cyanoalkenyl, C ₃ ~ Cg-cyanoalkynyl, Ci-Cg-alkoxy , Ci-Cg-cyanoalkoxy, Ci-Cg-haloalkoxy, C -C ₆ -alkenyloxy, C ₂ -Cg-cyanoalkenyloxy, C ₂ -Cg-haloalkenyloxy, C ₂ -Cg-alkynyloxy, Ci-Cg-alkylthio, - ₅ Ci-Cg-cyanoalkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkoxy-Ci-Cg-alkylthio, C ~ Cg-alkoxycarbonyl, Ci-Cg-alkyl - carbonyl, Cι-Cg-alkylcarboxy-Cι- Cg-alkyl, Ci-Cg-alkylcarbonyl-Ci-Cg-alkyl, Ci-Cg-alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphi - 40 nyl, heteroarylsulphonyl, aryl-Ci-Cg-alkyl, aryl-C ₂ -Cg-alkenyl, aryl-C ₃ -Cg-alkynyl, heteroaryl-Ci-Cg-alkyl, heteroaryl-C -Cg-alkenyl, heteroaryl-C ₃ -Cg-alkynyl, aryl-Ci-Cg-alkoxy, aryl-C ₂ -Cg-alkenyloxy, aryl-C ₃ -Cg-alkynyloxy, heteroaryl-CiCg-alkoxy, heteroaryl-C ₂ -Cg-alkenyloxy, ₄₅ heteroaryl-C ₃ -Cg-alkynyloxy, Ci-Cg-alkylsulphinyl, Cι ~ Cg- Alkylsulphonyl, C ₂ -Cg alkenylsulphinyl, C ₂ -Cg alkenylsulphonyl, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, HC = NOH, -C-Cg-alkyl-C = NOH, HC = N-0-Cι-C ₆ -alkyl, HC = N-0-Cι-C ₆ -alkyl-aryl, Cι-Cg-alkyl-C = N-0- -C-Cg-alkyl, HC = N-0-C ₂ -Cg-alkenyl, Cι-Cg-alkyl-C = N-0-C ₂ -Cg-alkenyl, HC = N-0-aryl, Ci-Cg- Alkyl-C = N-0-aryl, aryl, aryloxy, heteroaryl, heteroaryloxy, arylthio, heteroarylthio, where the cyclic substituents in turn can independently carry one to five of the following substituents: hydrogen, halogen, cyano, nitro, hydroxy, Mercapto, thiocyanato, carboxy, amino, Ci-Cg-alkyl, Ci-Cg-cyanoalkyl, C ₂ -Cg-alkenyl, -C-Cg-alkoxy-C ₂ -Cg-alkenyl, C ₃ -Cg-alkynyl, -C-Cg-alkoxy-C ₃ -Cg-alkynyl, C ₃ -Cg-alkynyl-Cι-Cg-alkoxy, C ₃ -C ₇ -cycloalkyl, Cι-Cg-alkyl-C ₃ -C ₇ -cycloalkyl, Ci- Cg-alkoxy-C ₃ -C cycloalkyl, C ₃ -C cycloalkyloxy, C ₃ -C cyanocycloalkyloxy, C -Cg alkyl-C ₃ -C ₇ cycloalkyloxy, C ₃ -C halo gencycloalkyl, C ₃ -C cyanocycloalkyl, C ₃ -C halocycloalkyloxy, C ₅ -C ₇ cycloalkenyl, C -Cg alkyl-C ₅ -C cycloalkenyl, Cι-Cg-alkoxy-C ₅ - C ₇ -Cycloalkenyl, C ₅ -C cyanocycloal kenyl, C ₅ -C halocycloalkenyl, -C-Cg-alkoxy-Cι-Cg- alkyl, Ci-Cg-haloalkyl, C ₂ -Cg-haloalkenyl, C ₃ ~ Cg Haloalkynyl, C ₂ -Cg-cyanoalkenyl, C ₃ -Cg-cyanoalkynyl, Cι ~ Cg-alkoxy, C -Cg-cyanoalkoxy, Ci-Cg-haloalkoxy, C ₂ -Cg-alkenyloxy, C ₂ -Cg-cyanoalkenyloxy, C ₂ -Cg-haloalkenyloxy, C ₂ -Cg-alkynyloxy, Ci- Cg-alkylthio, Ci-Cg-cyano-alkylthio, Ci-Cg-haloalkylthio, Cι-Cg-alkoxy-Cι-Cg-alkylthio, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkylcarbonyl, -C-Cg-alkylcarboxy-Cι-Cg-alkyl, Cι-Cg-alkylcarbonyl-Cι-Cg-alkyl, Ci-Cg-alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl-aryl-Cg-Cg-Cg C -Cg-alkenyl, aryl-C ₃ -Cg-alkynyl, heteroaryl-Ci-Cg-alkyl, heteroaryl- C ₂ -Cg alkenyl, heteroaryl-C ₃ -Cg alkynyl, aryl-Ci-Cg-Al-koxy, aryl-C ₂ -Cg-alkenyloxy, aryl-C ₃ -Cg-alkynyloxy, heteroaryl-CiCg-alkoxy, Heteroaryl-C ₂ -Cg-alkenyloxy, heteroaryl-C ₃ -Cg-alkynyloxy, Ci-Cg-alkylsulphinyl, Ci-Cg-alkylsulphonyl, C-Cg-alkenylsulphinyl, C ₂ -Cg-alkenylsul-phonyl, Ci-Cg-alkylamino , Di-Ci-Cg-alkylamino, HC = NOH, -C-C ₆ alkyl-C = NOH, HC = N-0 -C-Cg-alkyl, HC = N-0-Cι-Cg-alkyl-aryl, -C-Cg-alkyl-C = N-0-Cι-Cg-alkyl, HC = N-0-C ₂ -Cg-alkenyl, Cι-C ₆ -alkyl-C = N-0-C ₂ -C ₆ - Alkenyl, HC = N-0-aryl, Ci-Cg-alkyl-C = N-0-aryl, aryl, aryloxy, heteroaryl, heteroaryloxy, Arylthio, heteroarylthio; or wherein the aryl or heteroaryl radical with a fused phenyl ring, a fused C -Cg carbocycle or a 5- or 6-membered heterocycle forms a bicyclic system, which fused Ring system can optionally carry one to three of the substituents mentioned above for aryl. A COOR ³ or CONR ³ R ⁴ , where R ³ and R ⁴ independently of one another are 5 hydrogen, -CC ₆ alkyl, C -Cg alkenyl, C ₃ -C ₇ cycloalkyl or Ci-Cg-alkyl-aryl, which optionally partially or fully halogenated or may be one to three substituents selected from Cι ~ C ₄ alkoxy, C ₁ -C ₄ - haloalkoxy, Cι-C ₄ alkylthio, C ₃ -C ₇ cycloalkyl, C ₅ -C Can wear ₇ - 10 cycloalkenyl; and their agriculturally useful salts as crop protection agents. 15 2. Use of iminotriazoles of the formula I according to claim 1 as herbicides. 3. Use of iminotriazoles of the formula I according to claim 1 as insecticides. 20th Immotriazoles of formula I.

30 with the following meanings for R ¹ and A: R ¹ aryl or heteroaryl, where these radicals can independently carry one to five of the following groups: -. Hydrogen, halogen, cyano, nitro, hydroxy, mercapto, Thiocyanato, carboxy, amino, Ci-Cg-alkyl, Ci-Cg-cyanoalkyl, C ₂ -Cg-alkenyl, Cι-Cg-alkoxy-C ₂ -Cg-alkenyl, C ₃ -Cg-alkynyl, Cι-Cg-alkoxy -C ₃ -Cg-alkynyl, C ₃ -Cg -alkynyl-Cι-C ₆ -alkoxy, C ₃ -C ₇ -cycloalkyl, Cι-Cg-alkyl-C ₃ -C ₇ -cycloalkyl, Ci-Cg-Al- _{Λ Q} koxy-C ₃ -C ₇ -cycloalkyl, C ₃ -C -cycloalkyloxy, C ₃ -C -cyano-cycloalkyloxy, -C-Cg-alkyl-C ₃ -C -cycloalkyloxy, C ₃ -C - halocycloalkyl, C ₃ -C -Cyanocycloalkyl, C ₃ -C -halo-cycloalkyloxy, C ₅ -C ₇ -cycloalkenyl, -C-Cg-alkyl-C ₅ -C ₇ - cycloalkenyl, -C-Cg-alkoxy-C ₅ -C -cycloalkenyl, Cs -C - _{Λ C} cyanocycloalkenyl, C ₅ -C halocycloalkenyl, Ci-Cg-alkoxy-Ci-Cg-alkyl, Ci-Cg-haloalkyl, C ₂ -Cg-haloalkenyl, C ₃ -Cg-haloalkynyl, C ₂ - Cg-cyanoalkenyl, C ₃ -Cg- Cyanoalkynyl, Ci-Cg-alkoxy, Ci-Cg-cyanoalkoxy, Ci-Cg-halo ^¬ genalkoxy, C ₂ -Cg-alkenyloxy, C -Cg-cyanoalkenyloxy, C ₂ -Cg-haloalkenyloxy, C ₂ -Cg-alkynyloxy, Ci -Cg-alkylthio, Ci-Cg-cyanoalkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkoxy-Ci-Cg-alkylthio, Ci-Cg-alkoxycarbonyl, Ci-Cg-alkyl - carbonyl, Cι-Cg-alkylcarboxy -C-Cg-alkyl, -C-C ₆ -alkylcarbonyl-Ci-Cg-alkyl, Ci-Cg-alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl, heteroarylsulphonyl, aryl-Ci-Cg-alkyl, aryl-C ₂ -Cg-alkenyl, aryl-C ₃ -Cg-alkynyl, heteroaryl-Ci-Cg-alkyl, heteroaryl- C ₂ -Cg alkenyl, heteroaryl-C ₃ -Cg alkynyl, aryl-Ci-Cg-Al-koxy, aryl-C ₂ -Cg-alkenyloxy, aryl-C ₃ -Cg-alkynyloxy, heteroaryl-CiCg-alkoxy, Heteroaryl-C ₂ -Cg-alkenyloxy, heteroaryl-C ₃ -Cg-alkynyloxy, Ci-Cg-alkylsulphinyl, Cι ~ Cg-alkylsulphonyl, C ₂ -Cg-alkenylsulphinyl, C -Cg-alkenylsul-phonyl, Ci-Cg-alkylamino , Di-Ci-Cg-alkylamino, HC = NOH, -C-Cg-alkyl-C = NOH, HC = N-0-Cι-C ₆ alkyl, HC = N-0-Cι-Cg-alkyl aryl, -C-C ₆ alkyl-C = N-0 -C-Cg-alkyl, HC = N-0-C ₂ -Cg-alkenyl, -C-Cg-alkyl-C = N-0-C ₂ -Cg-alkenyl , HC = N-0-aryl, Ci-Cg-alkyl-C = N-0-aryl, aryl, aryloxy, heteroaryl, heteroaryloxy, Arylthio, heteroarylthio, where the cyclic substituents in turn can independently carry one to five of the following substituents: hydrogen, halogen, cyano, nitro, hydroxy, mercapto, thio-cyanato, carboxy, amino, Ci-Cg-alkyl, Ci-Cg- Cyanoalkyl, C ₂ -Cg-alkenyl, -C-Cg-alkoxy-C ₂ -Cg-alkenyl, C ₃ -Cg-alkynyl, Cι-Cg-alkoxy-C ₃ -Cg-alkynyl, C ₃ -Cg-alkynyl-Cι-Cg -Alkoxy, C ₃ -C ₇ -cycloalkyl, C -Cg-alkyl-C ₃ -C ₇ -cycloalkyl, Ci-Cg- alkoxy-C ₃ -C ₇ -cycloalkyl, C ₃ -C -cycloalkyloxy, C ₃ -C _7- cyano-cycloalkyloxy, -C-Cg-alkyl-C ₃ -C -cycloalkyloxy, C ₃ ~ C - Halogencycloalkyl, C ₃ -C cyanocycloalkyl, C ₃ ~ C halo cycloalkyloxy, C ₅ -C ₇ cycloalkenyl, -C-Cg-alkyl-C ₅ -C ₇ - cycloalkenyl, Cι-Cg-alkoxy-C ₅ -C _7- cycloalkenyl, C ₅ -C ₇ -cyanocycloalkenyl, C ₅ -C ₇ -halogenocycloalkenyl, Ci-Cg-alkoxy-Ci-Cg-alkyl, Ci-Cg-haloalkyl, C ₂ -C ₆ -haloalkenyl, C ₃ -cg haloalkynyl, C -cg-cyanoalkenyl, C ₃ -Cg- cyanoalkynyl, Ci-Cg-alkoxy, Ci-Cg-cyanoalkoxy, Ci-Cg haloalkoxy, C ₂ -C ₆ alkenyloxy, C ₂ -cg-Cyanoalkenyloxy , C -Cg haloalkenyloxy, C ₂ -C _e alkynyloxy, Ci-Cg-alkylthio, Ci-Cg-cyanoalkylthio, Ci-Cg-haloalkylthio, Ci-Cg-alkoxy-Ci-Cg-alkylthio, Ci-Cg -Alkoxycarbonyl, Ci-Cg-alkylcarbonyl, C -Cg-alkylcarboxy-Cι-Cg-alkyl, Ci-Cg-alkylcarbonyl-Ci-Cg-alkyl, Ci-Cg-alkylcarbonylamino, arylcarbonylamino, arylsulphinyl, arylsulphonyl, heteroarylsulphinyl , Heteroarylsulphonyl, aryl-Ci-Cg-alkyl, aryl-C ₂ -Cg-alkenyl, Aryl-C ₃ -Cg-alkynyl, heteroaryl-Ci-Cg-alkyl, heteroaryl-C ₂ -Cg-alkenyl, heteroaryl-C ₃ -Cg-alkynyl, aryl-Ci-Cg-Al - koxy, aryl-C ₂ -Cg-alkenyloxy, aryl-C ₃ -Cg-alkynyloxy, heteroaryl-CiCg-alkoxy, heteroaryl-C-Cg-alkenyloxy, heteroaryl-C ₃ -Cg-alkynyloxy, Ci-Cg -Alkylsulphinyl, Ci-Cg-alkyl-sulphonyl, C ₂ -Cg-alkenylsulphinyl, C ₂ -Cg-alkenylsulphonyl, Ci-Cg-alkylamino, di-Ci-Cg-alkylamino, HC = NOH, Ci-Cg-alkyl -C = NOH, HC = N-0 -C-C ₆ -alkyl, HC = N-0-Cι-C ₆ -alkyl-aryl, Cι-Cg-alkyl-C = N-0-Cι-C ₆ - Alkyl, HC = N-0-C ₂ -Cg-alkenyl, -C-C ₆ -alkyl-C = N-0-C ₂ -C ₆ -alkenyl, HC = N-0-aryl, Ci-Cg-Al- kyl-C = N-0-aryl, aryl, aryloxy, heteroaryl, heteroaryloxy, arylthio, heteroarylthio; or wherein the aryl or heteroaryl radical with a fused-on phenyl ring, a fused-on C ₃ -Cg carbocycle or a 5- or 6-membered heterocycle forms a bicyclic system, which fused on Ring system can optionally carry one to three of the substituents mentioned above for aryl, COOR ³ or C0NR ³ R ⁴ , where R ³ and R ⁴ independently of one another are hydrogen, C ₆ -C ₆ -alkyl, C ₂ -C ₆ alkenyl, C ₃ -C ₇ cycloalkyl or Ci-Cg-alkyl-aryl, which may be partially or completely halogenated or one to three substituents selected from C ₄ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C -C ₄ alkylthio, C ₃ -C cycloalkyl, Cs-C - cycloalkenyl can wear.