WO2000042032A1

WO2000042032A1 - Substituted 2-imino thiazolines

Info

Publication number: WO2000042032A1
Application number: PCT/EP2000/000045
Authority: WO
Inventors: Klaus-Helmut Müller; Mark Wilhelm Drewes; Dieter Feucht; Rolf Pontzen; Ingo Wetcholowsky
Original assignee: Bayer Aktiengesellschaft
Priority date: 1999-01-12
Filing date: 2000-01-05
Publication date: 2000-07-20
Also published as: AU2435300A; DE19900824A1

Abstract

The invention relates to novel substituted 2-imino thiazolines of general formula (I) in which Q, R<1>, R<2>, R<3> and R<4> have the meanings cited in the description. The invention also relates to methods for producing the inventive substituted 2-imino thiazolines and to their use as herbicides.

Description

Substituted 2-imino-thiazoIine

The invention relates to new substituted 2-imino-thiazolines, processes for their preparation and their use as herbicides.

It is known that certain substituted 2-imino-thiazolines have herbicidal properties (cf. EP-A-446802, EP-A-529481, EP-A-529482, EP-A-531970, WO-A-98/42703) . However, these connections have so far not been particularly important.

New substituted 2-imino-thiazolines of the general formula (I)

in which

Q represents oxygen or sulfur,

R ^! for optionally substituted by cyano, halogen or C, -C-alkoxy alkyl with 1 to 6 carbon atoms, for each optionally substituted by cyano or halogen alkenyl or alkynyl each having 2 to 6 carbon atoms, for each optionally substituted by cyano, halogen or - - alkyl Substituted cycloalkyl or cycloalkylalkyl each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C _r C ₄ alkyl, C, -C ₄ -

Haloalkyl, C, -C ₄ -alkoxy, C, -C ₄ -haloalkoxy, C, -C ₄ -alkylthio, C, -C ₄ - haloalkylthio, C, -C ₄ -alkylsulfinyl, C, -C ₄ -haloalkylsulfinyl, C, -C ₄ - Alkylsulfonyl, C, -C ₄ haloalkylsulfonyl, C, -C ₄ alkylamino, di (C, -C ₄ alkyl) amino, C, -C ₄ alkoxycarbonyl, C _r C ₄ alkylamino carbonyl , Di- (C, -C ₄ -alkyl) -amino-carbonyl or di- (C, -C ₄ -alkyl) -aminosulfonyl-substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 Carbon atoms in the alkyl part, or for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C, -C ₄ alkyl, C, -C ₄ haloalkyl, C, -C ₄ alkoxy, C, -C ₄ -Halogenalkoxy, C, -C ₄ alkylthio, C, -C ₄ -haloalkylthio, C, -C ₄ - alkylsulfinyl, C, -C ₄ -haloalkylsulfonyl, C, -C ₄ -alkylsulfonyl, C, -C ₄ - haloalkylsulfonyl , C, -C ₄ alkylamino, di- (C, -C ₄ alkyl) amino, C _r C ₄ -

Alkoxy-carbonyl, Cj- alkylamino-carbonyl, di- (C, -C ₄ -alkyl) -amino-carbonyl or di- (C [-C ₄ -alkyl) -aminosulfonyl-substituted, monocyclic or bicylic heterocyclyl or heterocyclylalkyl where the heterocyclic group contains up to 10 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 or 2 oxygen atoms or sulfur atoms,

R ^{2 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C, -C ₄ -alkoxy, each having up to 6 carbon atoms,

R ^{3 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or represents alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C, -C ₄ -alkoxy, each having up to 6 carbon atoms, and

R ⁴ for cycloalkyl or cycloalkylalkyl, each of which is optionally substituted by cyano, halogen or C, -C ₄ -alkyl and each has 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, for in each case optionally by nitro, cyano, carboxy,

Carbamoyl, thiocarbamoyl, halogen, C, -C ₄ alkyl, C, -C ₄ haloalkyl, C, -C ₄ alkoxy, C, -C ₄ haloalkoxy, C, -C ₄ alkylthio, C, -C ₄ haloalkylthio, C, -C ₄ alkylsulfinyl, C, -C ₄ haloalkylsulfinyl, C, -C ₄ -alkylsulfonyl, C, -C ₄ -haloalkylsulfonyl, C, -C ₄ -alkylamino, di- (C, -C ₄ -alkyl) -amino, C, -C ₄ -alkoxy-carbonyl, C, -C ₄ -alkylamino-carbonyl, di- (C, -C ₄ -alkyl) - amino-carbonyl or di- (C, -C ₄ -alkyl) -aminosulfonyl-substituted aryl or

Arylalkyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C _r C ₄ alkyl, C, -C ₄ haloalkyl , C, -C ₄ -alkoxy, C, -C ₄ -haloalkoxy, C, -C ₄ -alkylthio, C, -C ₄ -haloalkylthio, C, -C ₄ -alkylsulfinyl, C, -C ₄ -

Haloalkylsulfinyl, C, -C ₄ -alkylsulfonyl, C, -C ₄ -haloalkylsulfonyl, C, -C ₄ -alkylamino, di- (C, -C ₄ -alkyl) -amino, C _r C ₄ -alkoxy-carbonyl, C , -C ₄ - alkylamino-carbonyl, di- (C, -C ₄ -alkyl) -amino-carbonyl or di- (C, -C ₄ -alkyl) -aminosulfonyl-substituted, monocyclic or bicyclic heterocyclyl or heterocyclylalkyl, where the heterocyclyl group contains up to 10 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 or 2 oxygen atoms or sulfur atoms,

including the possible E and Z isomers of the compounds of formula (I) found.

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

R ¹ preferably represents in each case optionally by cyano, fluorine, chlorine,

Methoxy or ethoxy substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl for each optionally by cyano, fluorine, chlorine or Bromine-substituted ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl optionally substituted by cyano, fluorine, chlorine, methyl, ethyl, n- or i-propyl , Cyclobutyl methyl, cyclopentylmethyl or cyclohexylmethyl, each optionally with nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmylsulfonyl, trifluoromethyl , Ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminoc ,

Dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl, benzyl or phenylethyl, or for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, sulfyl Methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl,

Ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or Dimetir, laminosulfonyl substituted monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, benzofuryl, furyl methyl, thienyl, benzothienyl, thienylmethyl, oxazolyl, oxazolylmethyl, isoxazolyl, isoxazolylmethyl, thiazolyl, thiazolylmethyl , Oxadiazolyl, oxadiazoylmethyl, thiadiazolyl, thiadiazolylmethyl, pyridinyl, quinolinyl, isoquinolinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl.

preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or in each case optionally by fluorine or chlorine substituted methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.

R ¹ preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or in each case optionally by cyano,

Fluorine, chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-

Propyl, n-, i-, s- or t-butyl, methoxycarbonyl, ethoxycarbonyl, n- or i-

Propoxycarbonyl.

R ⁴ preferably represents in each case optionally by cyano, fluorine, chlorine, bromine,

Methyl, ethyl, n- or i-propyl substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally with nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl , Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy,

Ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, nylsulfonyl, ethylsulfonyl i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminosulfonyl or dimethylaminosulfonyl , Benzyl or phenylethyl, or for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfmyl, trif luormethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl,

Methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxy- carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl-substituted, monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, benzofienyl, methyl-furyl, furyl-, methyl-furyl Oxazolyl, oxazolylmethyl,

Isoxazolyl, isoxazolylmethyl, thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazoylmethyl, thiadiazolyl, thiadiazolylmethyl, pyridinyl, quinolinyl, isoquinolinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl.

particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, each optionally substituted by fluorine or chlorine, propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine or chlorine, for each cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by fluorine, chlorine or methyl, for each optionally by

Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio , Trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl,

Trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or od; Dimethylaminosulfonyl substituted phenyl or benzyl, or for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfmyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylcarbonyl, trifluoromethylcarbonyl n- or i-Propoxycarbonyl, Dimethylaminocarbonyl or Dimethylaminosulfonyl substituted, monocyclic or bicylic heterocyclyl or Heterocyclylalkyl from the series furyl, benzofuryl, furylmethyl, thienyl, benzothienyl, thienylmethyl, pyridinyl, quinolinyl, pyridinylmethyl.

R ² particularly preferably represents chlorine or bromine, or methyl, ethyl, n- or i-propyl which may be substituted by fluorine or chlorine.

R ³ particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine or methyl which is optionally substituted by fluorine or chlorine.

R ⁴ particularly preferably represents in each case optionally by fluorine, chlorine or

Methyl substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally with nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy , Ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, ethylsulfonyl, methylsulfonyl - Propylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl or benzyl, or for each optionally substituted by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, methyl, ethyl, chlorine, bromine , n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n - or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-

Propylsulphinyl, trifluoromethylsulphinyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, trifluoromethylsulphonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulphylyl, cyclocylylcyclyl or cyclocylyl, cyclocylyl, cyclocylyl, cyclocylyl, cyclocyclic or monocyclic, cyclocylyl, cyclocyclic or monocyclic, cyclocyclic or monocyclic, cyclocyclic or monocyclic, cyclocyclic or monocyclic, cyclocyclic or monocyclic, cyclocyclic or monocyclic, cyclocyclic from monocyclic or cyclocyclic, cyclocyclic or monocyclic, cyclocyclic or cyclocyclic, monocyclic or cyclocyclic, methyl, thienyl, benzothienyl, thienylmethyl, pyridinyl, quinolinyl, isoquinolinyl, pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl.

R ¹ very particularly preferably represents methyl, ethyl, n- or i-propyl, which is optionally substituted by fluorine or chlorine, n-, i- or s-butyl represents propenyl, butenyl, propynyl or butynyl which is optionally substituted by fluorine or chlorine, for each cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by fluorine, chlorine or methyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-

Propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfonyl, tryl , n- or i-propylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl,

Ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl or benzyl, or for each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted pyridinylmethyl.

R ² very particularly preferably represents chlorine or bromine, or methyl or ethyl which is in each case optionally substituted by fluorine or chlorine.

R ³ very particularly preferably represents hydrogen, chlorine, bromine or methyl which is optionally substituted by fluorine or chlorine.

R ⁴ very particularly preferably represents in each case optionally by nitro,

Cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy,

Difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propyl thio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxy, carbonyl, methyloxy, nyloxy, methyloxy, nyloxy, methyloxy, nyloxy, methyloxy, nyloxy, methyloxy, nyloxy, methyloxy, nyloxy, carbonyl, carbonyl, carbonyl, carbonyl, carbonyl, carbonyl substituted phenyl, or for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, Trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylifoxy, methylylmethylcarbonyl, , n- or i-Propoxycarbonyl, Dimethylaminocarbonyl or Dimethylaminosulfonyl substituted heterocyclyl from the Oxa series zolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl.

R ⁴ most preferably represents phenyl which contains a substituent from the series fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy in the 3- or meta position and, if appropriate, a further substituent from the series Contains fluorine, chlorine, trifluoromethyl, the grouping 3-trifluoromethylphenyl being particularly emphasized for R ⁴ .

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

According to the invention, particular preference is given to the compounds of the formula (I) in which there is a combination of the meanings listed above as being particularly preferred.

According to the invention, very particular preference is given to the compounds of the formula (I) in which a combination of those listed above as being particularly preferred

Meanings exist.

The new substituted 2-imino-thiazolines of the general formula (I) have interesting biological properties. They are particularly characterized by strong herbicidal - and to a certain extent also by insecticidal - effectiveness.

The new substituted 2-imino-thiazolines of the general formula (I) are obtained if

(a) 2-imino-thiazolines of the general formula (II)

in which

R ² , R ³ and R ^{4 have} the meaning given above,

- or acid adducts of compounds of the general formula (II) with halogen (di) thioformic acid esters of the general formula (III)

^(III) in which

Q and R ^{1 have} the meaning given above and

X represents halogen,

- or with corresponding pyro (di) thioesters -

if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,

or if you

(b) 2-Imino-thiazolines of the general formula (II) - above - in a first stage with carbon oxide sulfide (COS) or carbon disulfide (CS ₂ ) if appropriate in

Presence of a metal compound and optionally in the presence of a

Reacts diluent and the resulting compounds of the general formula (IV)

in which

Q, R ² , R and R ^{4 have} the meaning given above and M stands for a metal equivalent,

in a second stage with compounds of the general formula (V)

YR ¹ (V) in which

R ^{1 has} the meaning given above and

Y represents halogen or alkylsulfonyl,

if appropriate in the presence of a diluent,

and, if appropriate, subsequently carries out substitution reactions in the customary manner as part of the definition of substituents.

In principle, the compounds of the general formula (I) can also be synthesized as shown schematically below:

Isomerization of 5-alkylidene-2-imino-thiazolidines of the general formula (VI) - where Q, R ¹ , R ³ and R ^{4 have} the meaning given above and R ^{2 "1 is} hydrogen or alkyl - at elevated temperature:

(VI) (Ia)

If, for example, 5-ethyl-2-imino-3- (3-trifluoromethyl-phenyl) thiazoline and chlorothio formic acid methyl ester are used as starting materials, the reaction sequence in process (a) according to the invention can be outlined by the following formula:

If, for example, 5-chloromethyl-2-imino-3- (3-cyano-phenyl) thiazoline and carbon disulfide (CS2) are used as starting materials in the first stage and allyl bromide in the second stage, the course of the reaction in process (b) according to the invention can be can be outlined by the following formula:

Formula (II) provides a general definition of the 2-iminothiazolines to be used as starting materials in processes (a) and (b) according to the invention for the preparation of compounds of the general formula (I). In the general formula (II), R ² , R ³ and R ⁴ preferably have those meanings which are already preferred, particularly preferred, very particularly preferred or most preferred in connection with the description of the compounds of the general formula (I) according to the invention for R ² , R ³ and R ^{4 have been} specified. The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. US-A-5459277, EP-A-545431).

Formula (III) provides a general definition of the halogeno- (di) thioformic acid esters to be used further as starting materials in process (a) according to the invention. In the general formula (III), Q and R ^{1 have} the meaning which have already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for Q and R '; X preferably represents fluorine, chlorine or bromine.

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

Formula (V) provides a general definition of the compounds to be used as starting materials in process (b) according to the invention for the preparation of compounds of the general formula (I). In the general formula (V), R ¹ preferably has the meaning which has already been given above in connection with the description of the compounds of the general formula (I) according to the invention as preferred, particularly preferred or very particularly preferred for R ¹ ; Y preferably represents fluorine, chlorine, bromine, methylsulfonyl or ethylsulfonyl, in particular chlorine.

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

Process (a) according to the invention for the preparation of compounds of the general formula (I) is optionally carried out using a reaction auxiliary. The usual inorganic or organic bases or are generally used as reaction aids for the process according to the invention

Acid acceptors into consideration. These preferably include alkali metal or earth alkali metal acetates, amides, carbonates, hydrogen carbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or calcium amide, sodium , Potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride, lithium, sodium, potassium or calcium hydroxide,

Sodium or potassium methoxide, ethanolate, n or i propanolate, n, i, s or t butanolate; also basic organic nitrogen compounds, such as trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine. Ethyl-dicyclo-hexylamine, N, N-dimethyl-aniline, N, N-dimethyl-benzylamine, pyridine, 2-methyl-, 3-

Methyl, 4-methyl, 2,4-dimethyl, 2,6-dimethyl, 3,4-dimethyl and 3,5-dimethyl-pyridine, 5-ethyl-2-methyl-pyridine, 4-dimethylamino -pyridine, N-methyl-piperidine, 1,4-diazabicyclo [2,2,2] octane (DABCO), 1,5-diazabicyclo [4,3,0] non-5-ene (DBN), or 1,8-diazabicyclo [5,4,0] -undec-7-ene (DBU).

Phase transfer catalysts are also suitable as further reaction aids for process (a) according to the invention. Examples of such catalysts are:

Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, hexadecyl trimethylammonium chloride, hexadecyl trimethylammonium bromide, benzylchloride, benzylchloride, benzyl methylammonium hydroxide, benzyl triethylammonium hydroxide, benzyl tributyl ammonium chloride, benzyl tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributyl hexadecylphosphonium bromide, butyl triphenyl Tetraphenylphosphonium bromide.

Process (b) according to the invention for the preparation of compounds of the general formula (I) is carried out in the presence of a metal compound. It come here preferably alkali metal or alkaline earth metal acetates, amides, carbonates, bicarbonates, hydrides, hydroxides or alkanolates, such as sodium, potassium or calcium acetate, lithium, sodium, potassium or Calcium amide, sodium, potassium or calcium carbonate, sodium, potassium or calcium hydrogen carbonate, lithium, sodium, potassium or calcium hydride,

Lithium, sodium, potassium or calcium hydroxide, sodium or potassium methanolate, ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate into consideration .

Processes (a) and (b) according to the invention for the preparation of the compounds of the general formula (I) are preferably carried out using diluents. In addition to water, suitable diluents for carrying out the processes according to the invention are, above all, inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene,

Toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles such as acetonitrile, propionitrile or butyronitrile; Amides, such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

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

10 ° C and 120 ° C. Processes (a) and (b) according to the invention are generally carried out under normal pressure. However, it is also possible to carry out the processes according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

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

The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and in particular as weed killers. Weeds in the broadest sense are all plants that grow in places where they are undesirable. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.

According to the invention, all plants and parts of plants can be treated. Plants are understood here to mean all plants and plant populations, such as desired and unwanted wild plants or crop plants (including naturally occurring crop plants). Cultivated plants can be plants which can be obtained by conventional breeding and optimization methods or by biotechnological and genetic engineering methods or combinations of these methods, including the transgenic plants and including the plant cultivars which can or cannot be protected by plant breeders' rights. Plant parts are to be understood to mean all above-ground and underground parts and organs of plants, such as shoots, leaves, flowers and roots, examples being leaves, needles, stems, stems, flowers, fruiting bodies, Fruits and seeds as well as roots, tubers and rhizomes are listed. The plant parts also include crops and vegetative and generative propagation material, for example cuttings, tubers, rhizomes, offshoots and seeds.

The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings. Habitat or storage space according to the usual treatment methods, e.g. by dipping, spraying, vaporizing, atomizing, scattering, brushing and, in the case of propagation material, in particular seeds, furthermore by single- or multi-layer coating.

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

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria,

Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Dutilon, Emo Viola, galeopsis, papaver, centaurea, trifolium, ranunculus, taraxacum.

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

Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Iochasumirumum, Scalumumum, Scalumumum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops, Phalaris. Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Seeale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

However, the use of the active compounds according to the invention is by no means restricted to these genera, but extends in the same way to others

Plants.

Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, e.g. on industrial and track systems and on paths and squares with and without tree cover. The active compounds according to the invention for weed control in permanent crops, e.g. Forest, ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, on ornamental and sports turf and pasture land as well as for selective purposes Weed control can be used in annual crops.

The compounds of formula (I) according to the invention show strong herbicidal activity and a broad spectrum of activity when used on the soil and on above-ground parts of plants. To a certain extent, they are also suitable for the selective control of monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, both in the pre-emergence and in the post-emergence process.

The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active substance-impregnated natural and synthetic substances and very fine encapsulations in polymeric substances.

These formulations are made in a known manner, e.g. by mixing the active ingredients with extenders, that is liquid solvents and / or solid

Carriers, optionally using surface-active agents, thus emulsifiers and / or dispersants and / or foam-generating agents.

If water is used as an extender, e.g. organic solvents can also be used as auxiliary solvents. The following are essentially suitable as liquid solvents: aromatics, such as xylene, toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. Petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well as their ethers and esters, ketones such as

Acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents such as dimethylformamide and dimethyl sulfoxide, and water.

Possible solid carriers are: e.g. Ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates are suitable as solid carriers for granules: e.g. broken and fractionated natural rocks such as calcite, marble, pumice, sepiolite, dolomite as well as synthetic granules from inorganic and organic flours as well as granules from organic material such as sawdust,

Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming agents are possible: e.g. non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersants are: e.g. Lignin sulfite leaching and methyl cellulose.

It can be used in the formulations adhesives such as carboxymethylcellulose, natural and synthetic powdered, granular or latexfb ^'-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate and natural phospholipids lipids such as cephalins and lecithins and synthetic phospholipids. Other additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. Iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc can be used.

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

The active compounds according to the invention, as such or in their formulations, can also be used for combating weeds, in a mixture with known herbicides, finished formulations or tank mixes being possible.

Known herbicides are suitable for the mixtures, for example acetochlor, acifluorfen (sodium), aclonifen, alachlor, alloxydim (sodium), ametryne, amidochlor, amidosulfuron, anilofos, asulam, atrazine, azafenidin, azimsulfuron, benazolin (-ethyl), benfuresate , Bensulfuron (-methyl), bentazone, benzofenap, benzoylprop (-ethyl), bialaphos, bifenox, bispyribac (-sodium),

Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfcii, Chloramben, Chloridazon, Chlorimuron (-ethyl), Chlornitrofen, Chlorsulfuron, Chloridonmethyl (Chlorodonolurin) Cinosulfuron, Clethodim, Clodina-fop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyrasulfuron (-methyl),

Cloransulam (-methyl), cumyluron, cyanazines, cybutryne, cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, dialate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquronur, Diquatur, Diquatur, Diquatur Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulf- uron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxaprop (-P-ethyl), flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop (-methyl), flazasulfuron, fluazifop (-P -butyl), fluazolate, flucarbazone, flufenacet, flumet-sulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpethyl- sulfur sodium), Flurenol (-butyl), Fluridone, Fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxy- fop (-ethoxy ethyl), Haloxyfop (-P-methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfonone, Iodosulfuron, Ioxynil, Isopropalin, Isoproturonaben, Isouronaben Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthi azuron, metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, metribuzin, metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide, neburon, nicosulfuron, norflurazon, orbenadadon, oxyzalonon, oxyzalin, orzalin Oxaziclomefone, Oxyfluorfen, Paraquat, Pelargonic Acid, Pendimethalin, Pentoxazone, Phenmedipham, Picolinafen, Piperophos, Pretilochlor, Primisulfuron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamide, Prosulfuron (Prosulfuron), Prosulfuron (Prosulfuron)

Pyrazolate, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridate, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop (-P-ethyl), quizalofop (-P, tefuryl Rimsulfuron, Sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron- (-methyl), Sulfosate, Sulfosulfuron, Tebutam, Tebuthiuron, Tepraloxydim, Terbuthylazine, Terbutryn, Thenylchlor, Thiafluamide, Thiaziminononium, Thiazopyronium, Thiazopyronium, Thiazopyronium, Thiazopyronium, Thiazopyronium, Thiazopyronium, Thiazopyronium , Thiobencarb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tridiphane, Trifluralin and Triflusulfuron, Tritosulfuron. A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

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

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

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

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

Manufacturing examples:

example 1

(Method (a))

2.0 g (19 mmol) of methyl chlorothiooformate are stirred at room temperature (approx. 20 ° C) with a mixture of 2.4 g (8 mmol) of 2-imino-5-methyl-3- (3-trifluoromethyl- phenyl) thiazoline hydrochloride, 2.4 g (24 mmol) of triethylamine and 60 ml of ethyl acetate. The mixture is stirred at room temperature for about 30 minutes, then washed with IN hydrochloric acid, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with diisopropyl ether and the crystalline product is isolated by suction.

1.7 g (64% of theory) of 5-methyl- (2-methylthio-carbonylimino) -3- (3-trifluoromethyl-phenyl) thiazoline with a melting point of 134 ° C. are obtained.

Example 2

(Method (b)) 2.4 g (8 mmol) of 2-imino-5-methyl-3- (3-trifluoromethyl-phenyl) thiazoline hydrochloride are mixed with 1.8 g (24 mmol) of carbon disulfide (carbon disulfide) and 2.4 g (24 mmol) of triethylamine in 100 ml of ethyl acetate at room temperature (about 20 ° C) and then mixed with 3.8 g (24 mmol) of ethyl iodide. The reaction mixture is stirred for 15 hours at room temperature, then washed with 1N hydrochloric acid, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue is digested with diisopropyl ether and the crystalline product is isolated by suction.

2.2 g (75.5% of theory) of 5-methyl- (2-ethylthio-thiocarbonylimino) -3- are obtained.

(3-trifluoromethyl-phenyl) thiazoline, melting point 148 ° C.

Analogously to Examples 1 and 2 and in accordance with the general description of the production processes according to the invention, it is also possible, for example, to prepare the compounds of the general formula (I) listed in Table 1 below.

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

Examples of use:

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

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

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

It means: 0% = no effect (like untreated control)

100% = total annihilation

In this test, for example, the compounds according to Preparation Examples 1, 2, 3, 4, 5, 6, 7 and 8, with largely good tolerance to crop plants, such as cotton, corn, soybean, barley and wheat, show a strong action against weeds. Example B

Post emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

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

It means:

0% = no effect (like untreated control) 100% = total destruction

In this test, for example, the compounds according to Preparation Examples 1, 2, 3, 4 and 5 show with largely good tolerance to crop plants, such as e.g. Wheat, effective against weeds.

Claims

claims

1. Substituted 2-imino-thiazolines of the general formula (I)

in which

Q represents oxygen or sulfur,

R ¹ for alkyl with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ¹ -C ₄ -alkoxy, for each alkenyl or alkynyl with 2 to 6 carbon atoms optionally substituted by cyano or halogen, for each optionally substituted by cyano, Halogen or C, -C ₄ alkyl-substituted cycloalkyl or cycloalkylalkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the

Alkyl part, for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C, -C ₄ -alkyl, C, -C ₄ -haloalkyl, C _r C ₄ -alkoxy, C _r C ₄ -haloalkoxy, C, -C ₄ alkylthio, C, -C ₄ - haloalkylthio, C, -C ₄ alkylsulfinyl, C _r C ₄ haloalkylsulfinyl, C, -C ₄ alkylsulfonyl, C, -C ₄ haloalkylsulfonyl, C _r C ₄ -alkylamino,

Di- (C, -C ₄ -alkyl) -amino, C, -C ₄ -alkoxy-carbonyl, C, -C ₄ -alkylamino-carbonyl, di- (C, -C ₄ -alkyl) -amino-carbonyl or Di- (C, -C ₄ -alkyl) ~ aminosulfonyl-substituted aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by

Nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C, -C ₄ alkyl, C, -C ₄ haloalkyl, C, -C ₄ alkoxy, C, -C ₄ haloalkoxy, C, -C ₄ alkylthio, C, -C ₄ haloalkylthio, C, -C ₄ alkylsulfinyl, C, -C ₄ - haloalkylsulfinyl, C, -C ₄ alkylsulfonyl, C, -C ₄ haloalkylsulfonyl, C, -C ₄ alkylamino, di (C, -C ₄ alkyl) amino, C _r C ₄ alkoxycarbonyl, C, -C ₄ alkylamino carbonyl, di (C, -C ₄ - alkyl) -aminocarb-onyl or di- (C _r C ₄ -alkyl) -aminosulfonyl-substituted, monocyclic or bicyclic heterocyclyl or heterocyclylalkyl, the heterocyclyl group having up to 10 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 or 2 Contains oxygen atoms or sulfur atoms,

R ⁴ for each cycloalkyl or cycloalkylalkyl optionally substituted by cyano, halogen or C, -C ₄ -alkyl, each having 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl part, for each optionally substituted by nitro, cyano, carboxy, carbamoyl , Thiocarbamoyl, halogen,

C, -C ₄ alkyl, C, -C ₄ haloalkyl, C, -C ₄ alkoxy, C, -C ₄ haloalkoxy, C, -C ₄ alkylthio, C, -C ₄ haloalkylthio, C _r C ₄ alkylsulfinyl, C, -C ₄ haloalkylsulfonyl, C, -C ₄ alkylsulfonyl, C _r C ₄ haloalkylsulfonyl, C _r C ₄ alkylamino, di (C _r C ₄ alkyl) - amino, C, -C ₄ - alkoxy-carbonyl, C, -C ₄ -alkylamino-carbonyl, di- (C, -C ₄ -alkyl) - amino-carbonyl or di- (C, -C ₄ -alkyl) - amino sulfonyl substituted Aryl or arylalkyl each having 6 or 10 carbon atoms in the aryl groups and optionally 1 to 4 carbon atoms in the alkyl part, or for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C, -C ₄ alkyl, C, -C ₄ -haloalkyl, C, -C ₄ -alkoxy, C, -C ₄ -haloalkoxy, C, -C ₄ -alkylthio, C, -C ₄ -

Haloalkylthio, C, -C ₄ -alkylsulfinyl, C, -C ₄ -haloalkylsulfinyl, C, -C "-alkylsulfonyl, C, -C ₄ -haloalkylsulfonyl, C, -C ₄ -alkylamino, di- (C, -C ₄ -alkyl) -amino, C, -C ₄ -alkoxy-carbonyl, C, -C ₄ -alkylamino-carbonyl, di- (C, -C ₄ -alkyl) -amino-carbonyl or di- (C _r C ₄ - alkyl) - amino-sulfonyl substituted, monocyclic or bicyclic

Heterocyclyl or heterocyclylalkyl, the heterocyclyl group containing up to 10 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 or 2 oxygen atoms or sulfur atoms,

including the possible E and Z isomers of the compounds of

Formula (I).

2. Substituted 2-imino-thiazolines according to claim 1, characterized in that

Q represents oxygen or sulfur,

R ¹ for each methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy Pentyl for each optionally by cyano,

Fluorine, chlorine or bromine substituted ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, for each cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl, ethyl, n- or i-propyl , Cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, for each optionally by nitro, cyano, carboxy, Carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethyl, trifluoromethyl, trifluoromethyl, - Propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl, benzyl or phenylethyl, or for each optionally substituted by nitro, cyanol, carboxy, carboxy, carboxy Thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio ,

Ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluinoamyl- nyl, ethyl, methyl- or methyl- Dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-prcpylaminocarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted, monocyclic or bicylic heterocyclyl, heterocycyllylyl, benzyl, methyl, furyl, benzyl Oxazolyl, oxazolylmethyl, isoxazolyl, isoxazolylmethyl, thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazoylmethyl, thiadiazolyl, thiadiazolylmethyl, pyridinyl, quinolinyl, isoquinolinyl, pyridinylmethyl, pyrimidinyl, pyrimidinyl, pyrimidinyl R ^{2 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or represents methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, which are optionally substituted by fluorine or chlorine ,

R ³ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine,

Chlorine, bromine, or for each optionally by cyano, fluorine,

Chlorine, methoxy or ethoxy substituted methyl, ethyl, n- or i-

Propyl, n-, i-, s- or t-butyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and

R ⁴ for cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by nitro , Cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i- propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoro- methylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino , Ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl Phenyl, benzyl or phenylethyl, or for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy,

Trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoro- methylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, methyloxy, methyloxy, methyloxy, methyloxy, methyloxy, methyloxy, methyloxy, methyloxy, methyloxy, methyloxy, methyloxy, methyloxy, methyloxy, methyl, methylyl - or i-Propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted, monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, benzofuryl, furylmethyl, thienyl, oxazylylylylylylylylylylylylmethyl, benzylmethyl, benzylmethyl, oxazylmethyl, benzylmethyl, methylazylyl, benzylmethyl, oxazylmethyl, benzylmethyl, methylazolyl, benzylmethyl, benzylmethyl, benzylmethyl, oxazylmethyl , Isoxazolylmethyl, thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazoylmethyl, thiadiazolyl, thiadiazolylmethyl, pyridinyl, quinolinyl, isoquinolinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl.

Substituted 2 imino-thiazolines according to claim 1, characterized in that

Q represents oxygen or sulfur,

R ¹ for each optionally substituted by fluorine or chlorine

Methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, for propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine or chlorine, for cyclopropyl, cyclopentyl, each optionally substituted by fluorine, chlorine or methyl , Cyclohexyl, Cyclopropylmethyl, Cyclopentylmethyl or Cyclohexylmethyl, for each optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propyl- sulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl, substituted phenyl or benzyl, or for each optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfonyl, trifluoromethylsulfonyl n- or i-propylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl,

Ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted, monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, benzofuryl, furylmethyl, thienyl, benzothienyl, thienylmethyl, pyridinyl, quinolinyl, pyridinyl

R ^{2 represents} fluorine or chlorine or methyl, ethyl, n- or i-propyl, which is optionally substituted by fluorine or chlorine,

R ^{3 represents} hydrogen, cyano, fluorine, chlorine, bromine, or methyl which is optionally substituted by fluorine or chlorine, and

R ⁴ for cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by fluorine, chlorine or methyl, for in each case optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n - or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl Trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl or benzyl, or for each optionally substituted by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, fluorine

Methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, methylsulfinyl trifluoro, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, Benzofuryl, furylmethyl, thienyl, benzothienyl, thienylmethyl,

Pyridinyl, quinolinyl, isoquinolinyl, pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl.

4. Substituted 2 imino-thiazolines according to claim 1, characterized in that

Q represents oxygen or sulfur,

R ¹ for in each case optionally substituted by fluorine or chlorine methyl, ethyl, n- or i-propyl, n-, i- or s-butyl for in each case optionally substituted by fluorine or chlorine propenyl, butenyl, propynyl or butinyl, for in each case optionally by Fluorine, chlorine or methyl substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally with nitro, cyano, fluorine, chlorine, bromine,

Methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, nyl sulfonyl, ethyl sulfonyl, ethyl sulfonyl, ethyl sulfonyl, ethyl sulfonyl Trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl,

Ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl or benzyl, or for pyridinylmethyl optionally substituted by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy,

R ^{2 represents} chlorine or bromine, or represents methyl or ethyl optionally substituted by fluorine or chlorine,

R ³ for hydrogen, chlorine, bromine, or for each optionally by

Fluorine or chlorine substituted methyl, and

R ⁴ for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy,

Trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoimethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylifoxy, methylyloxyethyl, methylylsulfonyl, methylylsulfonyl, methyl-, , n- or i-propoxycarbonyl,

Dimethylaminocarbonyl or Dimethylaminosulfonyl substituted phenyl, or for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy , Difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-

Propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, Ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or oxyl-lysyl-oxy-lysyl-oxy-lysyl-oxy-lysyl-oxy-lysyl-oxy-lysyl-oxy-lysyl-oxy-lysyl-from-methyl-lysyl-oxy-lysyl-oxy-lysyl-oxyl-aminocylsulfonyl,

Isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, pyrimidinyl.

5. Substituted 2 imino-thiazolines according to claim 1, characterized in that

Q represents oxygen or sulfur,

R ¹ for each optionally substituted by fluorine or chlorine, methyl, ethyl, n- or i-propyl, n-, i- or s-butyl for in each case optionally substituted by fluorine or chlorine, propenyl, butenyl, propynyl or butynyl, for each optionally by Fluorine, chlorine or methyl substituted cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally with nitro, cyano, fluorine, chlorine, bromine,

Methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromcLhoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl, optionally substituted by phenyl or phenyl, phenyl or phenyl or nitro, or substituted by nityl or phenyl or nitro, or substituted by phenyl or phenyl or nitro, or substituted by nityl or phenyl or nitro, or substituted by phenyl or nitro for phenyl or methyl, optionally substituted by phenyl or substituted nityl or phenyl for nitro or methyl, , Fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy substituted pyridinylmethyl. R ^{2 represents} chlorine or bromine, or methyl or ethyl which is optionally substituted by fluorine or chlorine,

R ³ for hydrogen, chlorine, bromine, or for each optionally by

Fluorine or chlorine substituted methyl, and

R ⁴ for phenyl, which contains a substituent from the series fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy in the 3- or meta position and optionally contains a further substituent from the series fluorine, chlorine, trifluoromethyl .

6. A process for the preparation of substituted 2-imino-thiazolines according to any one of claims 1 to 5, characterized in that

(a) 2-imino-thiazolines of the general formula (II)

in which

R ² , R ³ and R ^{4 have} the meaning given in one of claims 1 to 5,

- or acid adducts of compounds of the general formula (II) - with halogen (di) thioformic acid esters of the general formula (III)

in which

Q and R 'have the meaning given in one of claims 1 to 5 and

X represents halogen,

- or with corresponding pyro (di) thioesters -

or that one

(b) 2-imino-thiazolines of the general formula (II) - above - in a first stage with carbon oxide sulfide (COS) or carbon disulfide (CS ₂ ), if appropriate in the presence of a metal compound and if appropriate in the presence of a diluent, and the compounds of the general formula (IV) obtained in this way

in which

Q, R ² , R ³ and R ^{4 have} the meaning given in one of claims 1 to 5 and M stands for a metal equivalent,

in a second stage with compounds of the general formula (V) YR ¹ (V) in which

R ^{1 has} the meaning given in one of claims 1 to 5 and

Y represents halogen or alkylsulfonyl,

if appropriate in the presence of a diluent,

7. A method for controlling unwanted plants, characterized in that at least one substituted 2-imino-thiazoline according to one of claims 1 to 5 is allowed to act on undesired plants and / or their habitat.

8. Use of at least one substituted 2-imino-thiazoline according to one of claims 1 to 5 for controlling unwanted plants.

9. Herbicidal agent, characterized by a content of at least one substituted 2-imino-thiazoline according to one of claims 1 to 5 and conventional extenders and / or surface-active agents.