DE19900824A1 - Substituted 2-imino-thiazolines - Google Patents

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

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

It is known that certain substituted 2-imino-thiazolines have herbicidal properties have shafts (cf. EP-A-446802, EP-A-529481, EP-A-529482, EP-A-531970, WO-A-98/42 703). So far, however, these compounds have no special Be interpreted.

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

in which
Q represents oxygen or sulfur,
R ¹ for optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy alkyl having 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 C ₁ -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 in each case optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ - haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ - Alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ -alkoxy-carbonyl, C ₁ -C ₄ -alkylamino-carbonyl, di- (C ₁ - C ₄ -alkyl) -amino-carbonyl or di- (C ₁ -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, thio carbamoyl, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₁ - haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkyl sulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylamino, di (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkoxy carbonyl, C ₁ -C ₄ alkylamino carbonyl, di (C ₁ -C ₄ alkyl) amino carbonyl or di (C ₁ -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,
R ^{2 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each alkyl or alkoxycarbonyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms,
R ^{3 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each alkyl or alkoxycarbonyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms, and
R ⁴ for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C ₁ -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 by nitro, cyano, carboxy, Carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ - C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ -haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ - haloalkylsulfonyl, C ₁ -C ₄ alkylamino, di- (C ₁ - C ₄ alkyl) amino, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylamino carbonyl, di (C ₁ -C ₄ alkyl) amino carbonyl or di (C ₁ -C _4- alkyl) -aminosulfonyl-substituted aryl or aryl alkyl, each having 6 or 10 carbon atoms in the aryl groups and, if appropriate, 1 to 4 carbon atoms in the alkyl part, or for each where appropriate by nitro, cyano, carboxy, carbamoyl, Thiocarbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ halo alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ Haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ - C ₄ alkylamino, di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ -alkoxy-carbonyl, C ₁ -C ₄ - alkylamino-carbonyl, di- (C ₁ -C ₄ alkyl) amino-carbonyl or di- (C ₁ -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 atoms Isomers of the compounds of formula (I) found.

In the definitions, the hydrocarbon chains, such as alkyl - also in combination with heteroatoms, such as in alkoxy - are each straight-chain or branched.
Q is preferably oxygen or sulfur.
R ¹ preferably represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s-, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy. or t-pentyl for ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, each optionally substituted by cyano, fluorine, chlorine or bromine, for each optionally substituted by cyano, fluorine, chlorine, methyl, ethyl, n- or i -Propyl-substituted cyclopro pyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, for each given 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, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propyl 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 Methyl sulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, M ethylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted, monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, benzofuryl, furylmethyl, thiazyl, methylazolylylethyl, oxazolyl Oxadiazolyl, oxadiazoylmethyl, thiadiazolyl, thiadiazolylmethyl, pyridinyl, quinolinyl, isoquinolinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl.
R ² preferably represents hydrogen, cyano, carboxy, carbamoyl, thio carbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i, each optionally substituted by fluorine or chlorine Propoxycarbonyl.
R ³ preferably represents hydrogen, cyano, carboxy, carbamoyl, thio carbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n- which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy. , i-, s- or t-butyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl.
R ⁴ preferably represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, 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, trifluorosyl, n-, methyl-, or methyl- Ethylamino, n- or i-propylamino, dimethyl amino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl s 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-propylsulfonyl, 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-propylethylaminocarbonyl substituted, monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, benzofuryl, furyl methyl, thienyl, benzothienyl, thienylmethyl, oxazolyl, oxazolylmethyl, isoxazolyl, I soxazolylmethyl, thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazoylmethyl, thiadiazolyl, thiadiazolylmethyl, pyridinyl, quinolinyl, isoquinolinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl.
Q preferably represents oxygen or sulfur.
R ¹ preferably represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl optionally substituted by fluorine or chlorine, propenyl, butenyl, propynyl or propylene optionally substituted by fluorine or chlorine Butinyl, 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, trifluor methyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfinyl Ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylamino sulfonyl substituted P henyl 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, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylamyloxy, dimethylcarbonyl, dimethylcarbonyl, dimethylcarbonyl or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylamino sulfonyl substituted, monocyclic or bicylic heterocyclyl or heterocyclylalkyl from the series furyl, benzofuryl, furylmethyl, thienyl, benzothienyl, thienylmethyl, pyridinyl, quinolinyl, pyridinylmethyl.
R ² preferably represents chlorine or bromine, or methyl, ethyl, n- or i-propyl which is optionally substituted by fluorine or chlorine.
R ³ preferably represents hydrogen, cyano, fluorine, chlorine, bromine or methyl which is optionally substituted by fluorine or chlorine.
R ⁴ preferably represents cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, each optionally substituted by fluorine, chlorine or methyl, each in each case 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, ethyl sulfinyl, n- or i-propylsulfinyl , Trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl, substituted for phenyl or benzyl, in each case optionally by carbon, nitro 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, di fluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, nylsulfonyl, ethylsulfonyl, ethylsulfonyl or ethylsulfonyl , Trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl-substituted, monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, benzofuryl, furyl methyl, thienyl, methylolynyl, methylolynyl, benzothylidyl, methylothylidyl, methylothylyl, methylothienyl, methylothienyl, benzothylidyl, methylothienyl, methylothienyl, methylothienyl, methylothienyl, methylothinyl, benzothylyl, methylothienyl, methylothenyl, methyl Pyridinylmethyl, pyrimidinyl or pyrimidinylmethyl.
Q particularly preferably represents oxygen or sulfur.
R ¹ particularly preferably represents methyl, ethyl, n- or i-propyl, optionally substituted by fluorine or chlorine, n-, i- or s-butyl, in each case propenyl, butenyl, propynyl or butinyl, optionally substituted by fluorine or chlorine in each case optionally substituted by fluorine, chlorine or methyl, cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyl methyl, cyclopentylmethyl or cyclohexylmethyl, for any given case 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, trifluoromethylsulfyl, ethylsulfonyl, methylsulfonyl, methylsulfonyl or i-propyl sulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethyl aminosulfonyl substitui first phenyl or benzyl, or for pyridinylmethyl substituted in each case optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy.
R ² particularly preferably represents chlorine or bromine, or for methyl or ethyl which is optionally substituted by fluorine or chlorine.
R ³ particularly preferably represents hydrogen, chlorine, bromine, or for each methyl optionally substituted by fluorine or chlorine.
R ⁴ particularly preferably represents in each case optionally through nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoro methoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfyl, methylylmethyl, Ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl, or for each optionally substituted 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-Pr opylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, di-methylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted hetero cyclyl from the series comprising oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, Thia diazolyl, pyridinyl, pyrimidinyl.
Q very particularly preferably represents oxygen or sulfur.
R ¹ very particularly preferably represents methyl, ethyl, n- or i-propyl, n-, i- or s-butyl, each optionally substituted by fluorine or chlorine, and propenyl, butenyl, propynyl or butinyl, each optionally substituted by fluorine or chlorine , for each cyclopropyl, cyclopentyl, cyclohexyl, cyclopropyl methyl, cyclopentylmethyl or cyclohexylmethyl optionally substituted by fluorine, chlorine or methyl, for each given if necessary 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-Propyl sulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxy carbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethyl aminosulfonyl sub substituted phenyl or benzyl, or pyri dinylmethyl substituted for any given nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy or trifluoromethoxy.
R ² very particularly preferably represents chlorine or bromine, or methyl or ethyl which is 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 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 radicals listed above or listed in preferred areas definitions apply both to the end products of the formula (I) and correspondingly for the starting or intermediate products required for the production. This Residual definitions can be between themselves, that is, between the specified ones areas can be combined as required.  

According to the invention, preference is given to the compounds of the formula (I) in which one Combination of the meanings listed above as preferred (preferred) is present.

According to the invention, particular preference is given to the compounds of the formula (I), in which a combination of the Be listed as particularly preferred above interpretations are available.

According to the invention, very particular preference is given to the compounds of the formula (I), in which are 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 through insecticidal - effectiveness out.

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)
  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 the presence of a metal compound and if appropriate in the presence of a diluent, and the latter Compounds of the general formula (IV) obtained
  in which
  Q, R ² , R ³ 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:

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 using the following formula:

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

Formula (II) provides a general definition of the 2-imino thiazolines 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 or in particular have those meanings which, in connection with the description of the compounds of the general formula (I) according to the invention, are preferred or particularly preferred 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 according to processes known per se can be prepared (cf. US-A-5459277, EP-A-545431).

Formula (III) provides a general definition of the halogen (di) thioformic acid esters to be used as starting materials in process (a) according to the invention. In the general formula (III), Q and R ¹ preferably or in particular have the meaning which has been described above in connection with the description of the compounds of the general formula (I) according to the invention, preferably or as particularly preferred for Q and R ¹ have been specified; X preferably represents fluorine, chlorine or bromine.

The starting materials of the general formula (III) are known synthesis 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 has preferably or in particular that meaning which has already been given above in connection with the description of the compounds of the general formula (I) according to the invention preferably or as 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 synthesis chemicals.

Process (a) according to the invention for the preparation of compounds of the general my formula (I) is optionally using a reaction auxiliary carried out by means. As a reaction aid for the process according to the invention generally come the usual inorganic or organic bases or Acid acceptors into consideration. These preferably include alkali metal or earth  alkali metal acetate, 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 methoxide, ethanolate, n or i-propanolate, n, i, i or -t-butanolate; also basic organic nitrogen compounds, such as for example trimethylamine, triethylamine, tripropylamine, tributylamine, ethyl-di isopropylamine, N, N-dimethyl-cyclohexylamine, 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).

Coming as further reaction aids for process (a) according to the invention also phase transfer catalysts into consideration. As examples of such Catalysts are mentioned:

Tetrabutylammonium bromide, tetrabutylammonium chloride, tetraoctylammonium chloride, tetrabutylammonium hydrogen sulfate, methyl trioctylammonium chloride, Hexadecyl-trimethylammonium chloride, hexadecyl-trimethylammonium bromide, Benzyl trimethyl ammonium chloride, benzyl triethyl ammonium chloride, benzyl tri methylammonium hydroxide, benzyl triethylammonium hydroxide, benzyl tributyl ammonium chloride, benzyl tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphosphonium chloride, tributyl hexadecylphosphonium bromide, Butyl triphenylphosphonium chloride, ethyl trioctylphosphonium bromide, tetra phenylphosphonium bromide.

Process (b) according to the invention for the preparation of compounds of the general My formula (I) is carried out in the presence of a metal compound. It  come preferably alkali metal or alkaline earth metal acetate, amide, -carbonates, -hydrogencarbonate, -hydride, -hydroxide or -alkanolate, such as 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 in Be dress.

Processes (a) and (b) according to the invention for the preparation of the compounds of general formula (I) are preferably using diluents carried out means. As a diluent for performing the fiction In addition to water, the most important processes are inert organic solvents into consideration. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as gasoline, benzene, Toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloro methane, 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-dimethyl acetamide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphorus acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides, such as dimethyl sulfoxide, alcohols such as methanol, ethanol, n- or 1-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 carried out when carrying out the inventive Processes (a) and (b) can be varied over a wide range. In general one works at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.  

Processes (a) and (b) according to the invention are generally below normal printing done. However, it is also possible to use the method according to the invention under increased or reduced pressure - generally between 0.1 bar and 10 bar - to be carried out.

To carry out processes (a) and (b) according to the invention, the off Common materials generally used in approximately equimolar amounts. It is ever but it is also possible to add one of the components in a larger excess use. The reaction is generally in a suitable dilution carried out medium and the reaction mixture is generally several hours stirred at the required temperature. The processing is done according to usual Methods carried out (see the manufacturing examples).

The active compounds according to the invention can be used as defoliants, desiccants, kraut tabs killers and especially used as a weed killer. Weeds in the broadest sense are understood to mean all plants that are found in places grow where they are undesirable. Whether the substances according to the invention as total or Selective herbicides act essentially depends on the amount used.

The active compounds according to the invention can, for. B. ver used in the following plants:
Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduippum, Sonuanum , Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, 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.
Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagiftaria, Iochasemirumum, Scalumumum, Scarumum , Sphenoclea, Dactyloctenium, Agrostis, Alopecurus, Apera, Aegilops, Phalaris.
Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Pineapple, Asparagus, Allium.

The use of the active compounds according to the invention is by no means limited to these Limited genres, but extends in the same way to others Plants.

The active compounds according to the invention are suitable depending on the con center for total weed control, e.g. B. on industrial and track systems and on Because of and places with and without tree cover. Likewise, the fiction active agents for weed control in permanent crops, e.g. B. Forst, 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 areas and for selective weed control in annual crops become.

The compounds of formula (I) according to the invention show strong herbicidal activity solvency and a wide range of effects when used on and on the floor aerial parts of plants. To a certain extent, they are also suitable for selective use Control of monocot and dicot weeds in monocot and di cotyledon cultures, both pre-emergence and post-emergence.  

The active ingredients can be converted into the usual formulations, such as Solutions, emulsions, wettable powders, suspensions, powders, dusts, pastes, soluble powders, granules, suspension emulsion concentrates, active ingredient-impregnated nated natural and synthetic substances as well as very fine encapsulation in polymers Fabrics.

These formulations are prepared in a known manner, e.g. B. by mixing of the active ingredients with extenders, i.e. liquid solvents and / or solid Carriers, optionally using surface-active agents, thus emulsifiers and / or dispersants and / or foam-producing Means.

In the case of the use of water as an extender, e.g. B. also organic Solvents are used as auxiliary solvents. As a liquid solvent essentially come into question: aromatics, such as xylene, toluene, or alkyl naphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, e.g. B. petroleum fractions, mineral and vegetable Oils, alcohols such as butanol or glycol and 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.

As solid carriers come into question: B. ammonium salts and natural Ge stone powders such as kaolins, clays, talc, chalk, quartz, attapulgite, Mont morillonite or diatomaceous earth and synthetic rock powder, such as highly disperse Silicic acid, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractionated natural rocks such as calcite, Marble, pumice, sepiolite, dolomite and 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 foam  Generating funds are possible: z. B. non-ionic and anionic Emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol Ethers, e.g. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates so such as protein hydrolyzates; as dispersants come into question: z. B. Lignin sulfite lye and methyl cellulose.

Adhesives such as carboxymethyl cellulose, natural, can be used in the formulations and synthetic powdery, granular or latex-shaped polymers are used, such as gum arabic, polyvinyl alcohol, polyvinyl acetate, and natural phospho lipids such as cephalins and lecithins and synthetic phospholipids. Further Additives can be mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan 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 Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are 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), Chlomethoxyfen,  Chloramben, chloridazon, chlorimuron (-ethyl), chloronitrofen, chlorsulfuron, Chlortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulfuron, Clethodim, Clodina fop (-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron (-methyl), Cloransulam (methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfame uron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, Di allate, dicamba, diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimeffiachlor, Dimetha metryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithio pyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulf uron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxa prop (-P-ethyl), flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop (-methyl), Flazasulfuron, fluazifop (-P-butyl), fluazolate, flucarbazone, flufenacet, flumet sulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluomet uron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyr sulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glu fosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, haloxy fop (-ethoxyethyl), haloxyfop (-P-methyl), hexazinones, imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazo sulfuron, iodosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop amide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, Oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, Pendimethalin, Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Primisulf uron (-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, Propyzamides, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolates, pyrazo sulfuron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyrimino  bac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, Quizalofop (-P-ethyl), quizalofop (-P-tefuryl), rimsulfuron, sethoxydim, simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulf uron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenyl chlorine, thiafluamides, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobes carb, Tiocarbazil, Tralkoxydim, Triallate, Triasuliron, Tribenuron (-methyl), Tri clopyr, tridiphane, trifluralin and triflusulfuron.

A mixture with other known active ingredients, such as fungicides, Insecticides, acaricides, nematicides, bird repellants, plants nutrients and soil structure improvers are possible.

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used become. The application is done in the usual way, e.g. B. by pouring, spraying, Spray, sprinkle.

The active compounds according to the invention can be used both before and after emergence of the plants are applied. They can also be planted in the soil before sowing be working.

The amount of active ingredient used can vary over a wide range. she depends essentially 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 area, preferably between 5 g and 5 kg per ha.

The manufacture and use of the active compounds according to the invention start out the following examples.

Manufacturing examples

example 1

(Method (a))

2.0 g (19 mmol) of methyl chlorothiooformate are at room temperature (approx. 20 ° C) with stirring to a mixture of 2.4 g (8 mmol) 2-imino-5-methyl-3- (3-trifluoromethyl-phenyl) thiazoline hydrochloride, 2.4 g (24 mmol) triethylamine and Given 60 ml of ethyl acetate. The mixture is about 30 minutes at room stirred temperature, then washed with 1N hydrochloric acid, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue with Diisopropyl ether digested and the crystalline product by suction isolated.

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

Example 2

(Method (b))

2.4 g (8 mmol) of 2-imino-5-methyl-3- (3-trifluoromethyl-phenyl) thiazoline hydro chloride with 1.8 g (24 mmol) of carbon disulfide (carbon disulfide) and 2.4 g (24 mmol) triethylamine in 100 ml ethyl acetate at room temperature (approx. 20 ° C) stirred and then mixed with 3.8 g (24 mmol) of ethyl iodide. The reaction mixture is stirred for 15 hours at room temperature, then with 1N hydrochloric acid wash, dry with sodium sulfate and filter. The filtrate is in a water jet concentrated in vacuo, the residue digested with diisopropyl ether and the crystalline accrued product 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 prepare a suitable preparation of active compound, 1 Ge is mixed most of the active ingredient with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with water to the desired level Concentration.

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

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 the preparation example show 1, 2, 3, 4, 5, 6, 7 and 8 with largely good tolerance to culture plants, such as B. cotton, corn, soy, barley and wheat, strong effect against weeds.  

Example B Post emergence test

Solvent: 5 parts by weight of acetone
Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the specified amount of solvent, specifies the added amount of emulsifier and dilute the concentrate with water to the ge wanted concentration.

With the active ingredient preparation, test plants are sprayed, which have a height of 5 to 15 cm so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l water / ha the desired amounts of active ingredient are applied. 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 the preparation example show 1, 2, 3, 4 and 5 with largely good tolerance to crops, such as e.g. B. wheat, strong action against weeds.

Claims (9)

1. Substituted 2-imino-thiazolines of the general formula (I)
in which
Q represents oxygen or sulfur,
R ¹ for alkyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy having 1 to 6 carbon atoms, for alkenyl or alkynyl or alkynyl substituted in each case optionally by cyano or halogen, each having 2 to 6 carbon atoms, if appropriate by cyano , Halogen or C ₁ -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 in each case optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ -halogen alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ -haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - haloalkylthio, C ₁ -C _4- alkylsulfinyl, C ₁ -C ₄ -haloalkylsulfinyl, C ₁ -C ₄ -alkylsulfonyl, C ₁ -C ₄ -haloalkylsulfonyl, C ₁ -C ₄ -alkylamino, di- (C ₁ -C ₄ -alkyl) -amino, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylamino carbonyl, di- (C ₁ -C ₄ alkyl) aminocarbonyl or di- (C ₁ -C ₄ alkyl) - am inosulfonyl-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 ₁ -C ₄ -alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ - C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ - haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkyl sulfonyl, C ₁ -C ₄ alkylamino, di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ -Alkoxy carbonyl, C ₁ -C ₄ alkylamino-carbonyl, di- (C ₁ -C ₄ -alkyl) -amino carbonyl or di- (C ₁ -C ₄ -alkyl) -aminosulfonyl 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,
R ^{2 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or represents alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms,
R ^{3 stands} for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms, and
R ⁴ for cycloalkyl or cycloalkylalkyl, each optionally substituted by cyano, halogen or C ₁ -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 by nitro, cyano, carboxy, carbamoyl , Thiocarbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ halo alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C _4- haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ halo alkylsulfonyl, C ₁ -C ₄ alkylamino, di- (C ₁ -C ₄ alkyl) amino, C ₁ -C ₄ alkoxycarbonyl, C ₁ -C ₄ alkylamino carbonyl, di (C ₁ -C ₄ alkyl) amino carbonyl or di (C ₁ -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, or for in each case optionally by nitro, cyano, carboxy, carbamoyl, Th iocarbamoyl, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ -halogen alkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ - haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl, C ₁ -C ₄ alkylamino, di- (C ₁ -C ₄ -alkyl) -amino, C ₁ -C ₄ -alkoxy-carbonyl, C ₁ -C ₄ -alkylamino-carbonyl, di- (C ₁ -C ₄ -alkyl) -amino-carbonyl or di- (C ₁ -C ₄ - alkyl) - amino-sulfonyl-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 atoms 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 ethenyl, propenyl, butenyl, pentenyl, ethynyl, propynyl, butynyl or pentynyl, each optionally substituted by cyano, fluorine, chlorine or bromine, for each optionally by cyano, fluorine, chlorine, 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, methylsulfonyl, Et hylsulfonyl, n- or i-propyl sulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, methylaminosulfonyl 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-propylsulfinylsulfinyl, trif , Ethylsulfonyl, n- or i-propyl sulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl , Ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl or di methylaminosulfonyl substituted monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, benzofuryl, furylmethyl, thienyl, benzothienyl, thienylmethyl, oxazolyl, oxazolylmethyl, isoxazolyl, isoxazolylmethyl, thiazolyl, thiazolyl methyl, Oxadiazolyl, oxadiazoylmethyl, thiadiazolyl, thiadiazolyl methyl, pyridinyl, quinolinyl, isoquinolinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl,
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 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n-, i-, optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy. , s- or t-butyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, and
R ⁴ for cyclopropyl, cyclobutyl, cyclo pentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclo pentylmethyl or cyclohexylmethyl, each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, cyclo pentylmethyl 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, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethyl sulfonyl, trifluoromethylsulfonyl, n- or methyl- Ethylamino, n- or i-propylamino, dimethylamino, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino carbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, 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, trifluoromethylsulfyl sulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methyl amino, ethylamino, n- or i-propylamino, dimethylamino, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino carbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, di methylaminocarbonyl or dimethylaminosulfonyl substituted, monocyclic or bicyclic heterocyclyl or heterocyclyl alkyl from the series furyl, benzofuryl, furylmethyl, thienyl, benzothienyl, thienylmethyl, oxazolyl, oxazolylmethyl, isoxazolyl, isoxazolyl methyl, thiazolyl, thiazolylmethyl, oxadiazolyl, oxadiazoyl methyl, thiadiazolyl, thiadiazolylmethyl, pyridinyl, quinolinyl, isoquinolinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl. 3. 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 butinyl, for in each case cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl, optionally substituted by fluorine, chlorine or methyl, for in each case optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy , n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethyl thio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, nyl -Propyl sulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl or benzyl, o 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, ethyl thio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propyl sulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, methoxycarbonyl Dimethylaminocarbonyl or Dimethylaminosulfonyl substituted, monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series furyl, benzofuryl, furylmethyl, thienyl, benzothienyl, thienylmethyl, pyridinyl, quinolinyl, pyridinylmethyl,
R ^{2 represents} fluorine or chlorine or methyl, ethyl, n- or i-propyl, which is optionally substituted by fluorine or chlorine,
R ^{3 stands} for hydrogen, cyano, fluorine, chlorine, bromine or for methyl 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 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, trifluoromoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-pro pylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl, optionally substituted by phenyl or benzyl, phenyl or benzyl, phenyl or benzyl, benzyl, benzyl, benzyl, or substituted by phenyl or benzyl, phenyl or benzyl, optionally substituted by phenyl or benzyl, benzyl, benzyl, Carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, Difluoromethoxy, trifluoromethoxy, methylthio, ethyl thio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, dimethyl, sulfonyl, sulfonyl, n- or methyl- Methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl-substituted, monocyclic or bicyclic heterocyclyl or heterocyclylalkyl from the series consisting of furyl, benzofuryl, furylmethyl, thienyl, benzothienyl, thienylmethyl, pyridinylidylmethyl, pyridinylidylmethyl, pyridinylmethylmolimethyl, pyridinylmethylmethyl, pyridinylmethylmethyl, pyridinylmethylmethyl, pyridinylmethylmethyl, pyridinylmethylmolimethyl, pyridinylmethylmolimethyl, pyridinylmethylmolimethyl, pyridinylmethylmolimethyl, pyridinylmethylmoliminyl, . 4. 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 butinyl, for each optionally cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl 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, ethyl thio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, nylsulfonyl, ethyl Propyl sulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl or benzyl, or it represents pyridinylmethyl which is 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 represents} hydrogen, chlorine, bromine, or methyl which is optionally substituted by fluorine or chlorine, 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, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethyl sulfonyl, n- or i-propylsulfonyl, trifluoromethylcarbonyl n- or i-Propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl, or for each optionally substituted 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, trifluoromet hylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoro methylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethyl aminosulphonyl substituted heterocyclyl from the series comprising oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl, Pyrimidinyl stands. 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 butinyl, for each optionally cyclopropyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclopentylmethyl or cyclohexylmethyl 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, ethyl thio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, nylsulfonyl, ethyl Propyl sulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl or benzyl, or it is in each case 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 represents} hydrogen, chlorine, bromine, or methyl which is optionally substituted by fluorine or chlorine, 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, if appropriate, a further substituent from the series fluorine, chlorine, tri contains fluoromethyl. 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 ^{1 have} the meaning given in one of claims 1 to 5 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 that one
• b) 2-imino-thiazolines of the general formula (II) - above - in a first step with carbon oxide sulfide (COS) or carbon disulfide (CS ₂ ) if appropriate in the presence of a metal compound and optionally in the presence of a diluent and the here he received compounds of the general formula (IV)
  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, and if appropriate subsequently carries out substitution reactions in the usual manner within the scope of the substituent definition.

7. A method for controlling unwanted plants, characterized records that according to at least one substituted 2-imino-thiazoline one of claims 1 to 5 on undesirable plants and / or their Living space. 8. Use of at least one substituted 2-imino-thiazoline according to one of claims 1 to 5 for controlling undesirable 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 above union extenders and / or surface-active agents.