Thiazolimine derivatives

Details Thiazolimine derivatives Thiazolimine derivatives

1999-09-21

2000-12-26

Gerstl, Robert

Plant protecting and regulating compositions

Plant growth regulating compositions

Organic active compound containing

548193, 548195, 548196, C07D41704, A01N 4378

Patent

active

061659436

DESCRIPTION:

BRIEF SUMMARY
The present invention relates to novel thiazolimine derivatives having herbicidal activity, to a process for preparing the thiazolimine derivatives, to compositions comprising them and to the use of these derivatives or of the compositions comprising them for controlling weeds.
Herbicidally active thiazolimine derivatives are known from the literature (U.S. Pat. No. 5,244,863; EP 529 482, EP 446 802).
However, the herbicidal properties of the known compounds and their tolerability are not entirely satisfactory.
It is an object of the present invention to provide novel thiazolimine derivatives having improved properties.
We have found that this object is achieved by the novel thiazolimine derivatives of the formula I, ##STR3## where:
X and Y independently of one another are each hydrogen, halogen, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl;
Z is hydrogen; C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -alkynyl, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkylthio, it being possible for these groups to be substituted by one to five halogens or C.sub.1 -C.sub.4 -alkoxy; aryl, hetaryl, benzyl, it being possible for these groups to be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or cyano; or one of the groups below: ##STR4##
R.sup.1 and R.sup.2 are each hydrogen, halogen; C.sub.1 -C.sub.4 -alkyl, C.sub.2 -C.sub.4 -alkenyl, C.sub.2 -C.sub.4 -alkynyl, it being possible for these groups to be substituted by one to five halogens or by C.sub.1 -C.sub.4 -alkoxy;
R.sup.3 is hydrogen; C.sub.1 -C.sub.8 -alkyl, C.sub.2 -C.sub.8 -alkenyl, C.sub.2 -C.sub.8 -alkynyl, C.sub.2 -C.sub.8 -alkylcarbonyl, C.sub.3 -C.sub.8 -alkenylcarbonyl, C.sub.3 -C.sub.8 -alkynylcarbonyl, it being possible for these groups to be substituted by one to eight halogens or by C.sub.1 -C.sub.4 -alkoxy; C.sub.3 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.7 -cycloalkenyl, it being possible for these groups to be substituted by one to eight halogen atoms, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -haloalkyl; aryl, hetaryl, benzyl, it being possible for these groups to be substituted by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, halogen, cyano, or nitro;
R.sup.4 and R.sup.5 are each hydrogen; C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, it being possible for these groups to be substituted by one to four halogens or by C.sub.1 -C.sub.4 -alkoxy; C.sub.3 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.7 -cycloalkenyl, which may be substituted by one to four halogens or by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy; aryl, hetaryl, it being possible for these groups to be substituted by C.sub.l -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or cyano;
R.sup.4 and R.sup.5 together form a 3- to 7-membered heterocycle which may carry a further hetero atom from the group consisting of N, O and S, may contain at least one double bond and may be substituted by C.sub.l -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or cyano;
R.sup.6 is hydrogen; C.sub.1 -C.sub.6 -alkyl, C.sub.2 -C.sub.6 -alkenyl, C.sub.2 -C.sub.6 -alkynyl, it being possible for these groups to be substituted by one to four halogens or by alkoxy; C.sub.3 -C.sub.7 -cycloalkyl, C.sub.3 -C.sub.7 -cycloalkenyl, which may be substituted by one to four halogen atoms or by C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, haloalkoxy; aryl, hetaryl, it being possible for these groups to be substituted by C.sub.1 -C.sub.4 -alkyl C.sub.1 -C.sub.4 -haloalkyl, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.4 -haloalkoxy, halogen, nitro or cyano;
n is 1 or 2;
m is 0, 1 or 2
The thiazolimine derivatives of the formula I are prepared by reacting anilines o

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