DE19937771A1 - Substituted 2-imino-thiazolines - Google Patents

Abstract

The invention relates to novel, substituted 2-imino-thiazolines of general formula (I), wherein R<1>, R<2>, R<3>, R<4>, A, Q and Y are defined as given in the description. The invention also relates to a method for the production thereof and to the use thereof 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 properties (cf. EP-A-446 802, EP-A-529 481, EP-A-529 482, EP-A- 531,970, WO-A-98/42703). However, these connections have so far had no particular effect acquired its meaning.

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

in which
A stands for a single bond or for alkanediyl (alkylene) with 1 to 6 carbon atoms,
Q represents oxygen or sulfur,
R ¹ for each optionally by nitro, amino, 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 halo alkylsulfonyl , 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, di- (C ₁ -C ₄ -alkyl) -aminosulfonyl, C ₃ -C ₆ -cycloalkyl, or by in each case optionally by cyano, nitro, halogen, C ₁ -C ₄ - alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy-substituted phenyl, phenoxy or phenylthio substituted monocyclic or bicyclic heterocyclyl, where the heterocyclyl group of up to 10 carbon atoms and additionally 1 to 4 Nitrogen atoms and / or 1 or 2 oxygen atoms or sulfur atoms and optionally additional h contains 1 to 3 oxo groups (C = O) and / or thioxo groups (C = S),
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 alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 6 carbon atoms,
R ⁴ for hydrogen, cyano, halogen, for alkoxy with 1 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, for each cycloalkyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl, each with 3 to 6 carbon atoms, each optionally with 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 haloalkyl sulfinyl, C ₁ -C ₄ alkylsulfonyl, C ₁ -C ₄ haloalkylsulfonyl , C ₁ -C ₄ alkyl amino, 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 phenyl or naphthyl, or 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 -Alkylsulfiriyl, C ₁ -C ₄ haloalkyl sulfinyl, 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) amino sulfonyl substituted, monocyclic or bicyclic heterocyclyl, the heterocyclyl group having up to 10 carbon atoms and additionally 1 to Contains 4 nitrogen atoms and / or 1 or 2 oxygen atoms or sulfur atoms, and
Y represents a single bond or NH, N (C ₁ -C ₄ -alkyl), N (C ₂ -C ₄ -alkenyl) or N (C ₂ -C ₄ -alkynyl),
found.

The general formula (I) excludes the possible E and Z isomers of Compounds of formula (I) with.

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

Preferred substituents or ranges indicated in the above and below Residues listed in formulas are defined below.

A preferably represents a single bond or methylene (CH ₂ ), di methylene (CH ₂ CH ₂ ) or trimethylene (CH ₂ CH ₂ CH ₂ ).

Q preferably represents oxygen or sulfur.  

R ¹ preferably represents in each case optionally by nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t- Butyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, fluorochloroethyl, trifluoroethyl, trichloroethyl, difluorochloroethyl, di chlorofluoromethyl, fluoropropyl, fluoropropyl, fluoropropyl, fluoropropyl, fluoropropyl, fluoropropyl, methypropyl, fluoropropyl, fluoropropyl, fluoropropyl, methypropyl, fluoropropyl, fluoropropyl, fluoropropyl, fluoropropyl, fluoropropyl, fluoropropyl, fluoropropyl, fluoropropyl, methylpropyl, fluoropropyl, fluoropropyl, fluoropropyl, fluoropropyl, fluoropropyl, methylpropyl, fluoropropyl , n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, trifluoroethoxy, trichloroethoxy, chlorodifluoroethoxy, fluoropropoxychloro Di fluoropropoxy, dichloropropoxy, trifluoropropoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, Fl uordichloromethylthio, fluoroethylthio, chloroethylthio, difluoroethylthio, dichloroethylthio, trifluoroethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfonyl, methylsulfonyl, methyl- sulfonyl, methyl- sulfonyl, methyl- or i-propylamino, n-, i-, s- or t-butylamino, dimethyl amino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxy carbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino carbonyl, dimethylaminocarbonyl, diethylaminocarbonyl , Dimethylamino sulfonyl, diethylaminosulfonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or by in each case optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or chlorofluoromethoxy substituted phenyl, phenoxy or phenylthio substituted, monocyclic or bicyclic heterocyclyl from the series furyl, benzo furyl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, 1,3,2-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4- Oxadiazolyl, 1,3,2-thiadiazolyl, 1,3,2-benzothiadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 2,4-dihydro-3H- 3-oxo-1,2,4-triazol-2-yl (also known as 4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl), pyridinyl, quinolinyl, pyrimidinyl, triazinyl, Pyrrolidinyl, piperidinyl, morpholinyl.

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 hydrogen, cyano, fluorine, chlorine, bromine, for methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy t-butoxy, for each cyclo propyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for each optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, Ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , Chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlordifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylamino, ethyl, or iamethylamino, ethyl, or iamylamethylamino, ethyl, or iamylamethylamino, ethyl, or iamethylamino, ethyl, or iamethylamino, ethyl, or iamethylamino, ethyl, or iodomethylamino, ethyl, or iodomethylamino, ethyl or methyl, ethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylamino-carbonyl, dimethylaminosulfonyl or diethylaminosulfonyl, or phenyl or naphthyl, optionally substituted by nitro, or nitano Carboxy, carbamoyl, thiocarbamoyl, halogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, fluoroethyl, Chloroethyl, difluoroethyl, dichloroethyl, fluorochloroethyl, trifluoroethyl, trichloroethyl, difluorochloroethyl, dichlorofluoroethyl, fluoropropyl, chloropropyl, difluoropropyl, trifluoropropyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, Difluoromethoxy, trifluoromethoxy, chlorodifluoromoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, trifluoroethoxy, trichloroethoxy, chlorodifluoroethox y, fluorodi chloroethoxy, fluoropropoxy, chloropropoxy, difluoropropoxy, dichloropropoxy, trifluoropropoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chloromethyldioethyl, chlorodifluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl, chlorodifluoromethyl , Difluoroethylthio, di chloroethylthio, trifluoroethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, ethylamino, ethylamino, ethylamino, ethylamino, ethylamino or ethylamino, , s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino carbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethyl aminocarbonyl, diethylamino-carbonyl, dimethylaminosulfonyl or di-ethylamino-sulfon monocyclic or bicyclic heterocyclic from the series furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, isoxaz olyl, thiazolyl, benzothiazolyl, isothiazolyl, 1,3,2-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,2-thiadiazolyl, 1,3,2-benzothiadiazolyl, 1 , 2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, pyridinyl, quinolinyl, pyrimidinyl.

Y preferably represents a single bond or NH, N (methyl), N (ethyl), N (allyl) or N (propargyl).

A particularly preferably represents a single bond or methylene (CH ₂ ) or dimethylene (CH ₂ CH ₂ ).

Q particularly preferably represents oxygen or sulfur.

R ¹ particularly preferably represents in each case optionally through nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloro ethoxy, Chlorfluorethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i- propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, fluoroethylthio, chloroethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, methyl sulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, Chlordifluormethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxy carbonyl, ethoxycarbonyl , n- or i-Propoxycarbonyl, Dimethylamino carbonyl, Dimethylaminosulfonyl, or by jewei Is optionally substituted by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or chlorodifluoromethoxy Phenyl, phenoxy or phenylthio substituted, monocyclic or bicyclic heterocyclyl from the series furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, 1,3,2-oxadiazolyl, 1,2,4-oxadiazol 1,3,4-oxadiazolyl, 1,3,2-thiadiazolyl, 1,3,2-benzothiadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 2, 4-dihydro-3H-3-oxo-1,2,4-triazol-2-yl (also known as 4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl), pyridinyl, Quinolinyl, pyrimidinyl, triazinyl, pyrrolidinyl, piperidinyl, morpholinyl.

R ² particularly preferably represents chlorine, bromine, methyl or ethyl.

R ³ particularly preferably represents hydrogen, chlorine, bromine, methyl or ethyl.

R ⁴ particularly preferably represents in each case optionally through nitro, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methyl thio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulphinyl, ethylsulphinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, n - or i-propoxycarbonyl, dimethyl aminocarbonyl or dimethylaminosulfonyl substituted phenyl or pyridinyl.

Y particularly preferably represents a single bond or NH.

A very particularly preferably represents a single bond.

Q very particularly preferably stands for oxygen.  

R ¹ very particularly preferably represents in each case optionally through nitro, amino, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, difluoro methylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethyl thio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulphinyl, Chlordifluor methylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, difluoromethylsulfonyl chlorine, dimethylamino, methoxycarbonyl, ethoxycarbonyl , Dimethylaminocarbonyl, Dimethylaminosulfonyl, or by in each case optionally substituted by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or chlorine difluoromethoxy-substituted phenyl, phenoxy or phenylthio-substituted, monocyclic heterocyclic or monylcyclic cyclo from the series furyl, benzo furyl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, 1,3,2-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1, 3,2-thiadiazolyl, 1,3,2-benzothiadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 2,4-dihydro-3H-3-oxo- 1,2,4-triazol-2-yl (also known as 4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl), pyridinyl, quinolinyl, pyrimidinyl, triazinyl, pyrrolidinyl, piperidinyl, Morpholinyl.

R ² very particularly preferably represents methyl.

R ³ very particularly preferably represents hydrogen.

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 group 3-trifluoromethylphenyl being particularly emphasized for R ⁴ .

Y very particularly preferably represents a single bond.

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 activity.

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

in which
A, R ² , R ³ and R ^{4 have} the meaning given above,
- or acid adducts of compounds of the general formula (II) -
with (thio) carbonyl compounds of the general formula (III)

in which
Q, R ¹ and Y have the meaning given above and
X represents halogen, alkoxy, aryloxy, arylalkoxy or the grouping -OC (Q) -YR ¹ ,
or with iso (thio) cyanates of the general formula (IV)

Q = C = NR ¹ (IV)

in which
Q and R ^{1 have} the meaning given above,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and optionally the compounds of the general formula (I) thus obtained are converted into other compounds of the general formula (I) within the scope of the above substitution definition by customary methods.

If, for example, 2-imino-5-methyl-3- (3-trifluoromethyl-phenyl) thiazoline and furan-3-carboxylic acid chloride are used as starting materials, the course of the reaction in the process according to the invention can be outlined using the following formula:

Formula (II) provides a general definition of the 2-imino-thiazolines to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (II), A, 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 A, R ² , R ³ and R ^{4 have been} given.

The starting materials of the general formula (II) are known and / or can be according to known processes can be prepared (cf. US-A-5 459 277, EP-A- 545 431).  

Formula (III) provides a general definition of the (thio) carbonyl compounds to be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (III), Q and R ¹ preferably or in particular have those meanings which have been given above or 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 are; X preferably represents fluorine, chlorine, bromine, C ₁ -C ₄ alkoxy, phenoxy or benzyloxy, in particular chlorine, methoxy or phenoxy.

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

Formula (IV) provides a general definition of the iso (thio) cyanates which may be used as starting materials in the process according to the invention for the preparation of compounds of the general formula (I). In the general formula (IV), Q and R ¹ preferably or in particular have those meanings which have already been mentioned 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 are.

The starting materials of the general formula (IV) are known organic synthesis chemicals.

The process according to the invention for the preparation of compounds of general Formula (I) is optionally carried out using a reaction auxiliary guided. As reaction aids for the inventive method come in general the usual inorganic or organic bases or Acid Accept gates into consideration. These preferably include alkali metal or alkaline earth metal acetate, amides, carbonates, bicarbonates, hydrides, hydroxides or alkano  latex, such as sodium, potassium or calcium acetate, lithium, sodium, Potassium or calcium amide, sodium, potassium or calcium carbonate, sodium, Potassium or calcium bicarbonate, 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; also basic organic nitrogen compounds, such as tri methylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, 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-diaza bicyclo [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 the process 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, benzylammonium benzylammonium benzyl -hydroxide, benzyl-triethylammonium-hydroxide, benzyl-tributyl ammonium-chloride, benzyl-tributylammonium-bromide, tetrabutylphosphonium-bromide, tetrabutylphosphonium-chloride, tributyl-hexadecylphosphonium-bromide, butyl-triphenylphosphoniumphylium phosphonium phosphonium phosphonium phosphonium phosphonium phosphonium chloride -bromide.

The process according to the invention for the preparation of the compounds of the general Formula (I) is preferably carried out using diluents  leads. As a diluent for carrying out the processes according to the invention In addition to water, inert organic solvents are particularly suitable. Here to include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as 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, propio nitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacet amide, N-methyl-formanilide, N-methyl-pyrrolidone or hexamethylphosphoric acid triamid; 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 mono methyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be carried out when carrying out the process according to the invention Process can be varied over a wide range. Generally you work at temperatures between 0 ° C and 150 ° C, preferably between 10 ° C and 120 ° C.

The process according to the invention is generally carried out under normal pressure leads. However, it is also possible to increase the process according to the invention or reduced pressure - generally between 0.1 bar and 10 bar to lead.

To carry out the process according to the invention, the starting materials in generally used in approximately equimolar amounts. However, it is also possible Lich to use one of the components in a larger excess. The The reaction is generally carried out in a suitable diluent  leads and the reaction mixture is generally several hours at which required temperature stirred. The processing is carried out 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. be used in the following plants:
Dicotyledon weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura, Desmodium, Emex, Erysimum, Gupopsis, Euphorbia , Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsesb, Senania, Senecio , Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

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

Monocotyledonous weeds of the genera: Aegilops, Agropyron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis, Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium,  Monochoria, Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Monocot cultures of the genera: Allium, Pineapple, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale, Triticum, Zea.

However, 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 concentration tration 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 moderate active substances for weed control in permanent crops, e.g. B. 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 pastures as well for selective weed control in annual crops.

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 Ver mixing the active ingredients with extenders, i.e. liquid solvents and / or solid carriers, optionally using surface-active agents Agents, ie emulsifiers and / or dispersants and / or foam the 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 emulsions goals such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, e.g. B. Alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolysates; as dispersants come into question: z. B. lignin sulfite 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, Benzobicyclone, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), bromobutide, bromofenoxim, bromoxynil, butachlor, butroxydim, Butylates, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlo methoxyfen, chloramben, chloridazon, chlorimuron (-ethyl), chloronitrofen, chlorine sulfuron, chlorotoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim, Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyra sulfuron (methyl), chlorosulam (methyl), cumyluron, cyanazine, cybutryne, Cycloate, cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP,  Desmedipham, Diallate, Dicamba, Diclofop (-methyl), Diclosulam, Diethatyl (-ethyl), Difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimethametryn, Dimethenamid, Dimexyflam, Dinitramine, Diphenamid, Diquat, Di thiopyr, diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin, ethametsulf uron (-methyl), ethofumesate, ethoxyfen, ethoxysuliron, etobenzanide, fenoxaprop- (-P-ethyl), fentrazamide, flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop (-methyl), flazasulfuron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone, Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumet sulam, fluometuron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, fluprop acil, flurpyrsulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop (-ethoxyethyl), haloxyfop (-P-methyl), hexazinones, imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazo sulfuron, iodosulfuron (-methyl, -sodium), ioxynil, isopropalin, isoproturon, isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiaz uron, metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop amide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, oxa diazon, oxasulirone, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, pendi methalin, pendralin, pentoxazone, phenmedipham, piperophos, pretilachlor, primi sulfuron (-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, Propyzamides, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolates, pyrazosulf uron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyriminobac (-methyl), pyrithiobac (-sodium), quinchlorac, quimnerac, quinoclamine, quizalo fop (-P-ethyl), quizalofop (-P-tefuryl), rimsulfuron, sethoxydim, Simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulf uron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenylchlor, Thiafluamides, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thiobencarb, Tio  carbazil, tralkoxydim, triallates, triasulfuron, tribenuron (-methyl), triclopyr, tri diphane, trifluralin and triflusulfuron.

Also a mixture with other known active ingredients; like fungicides, insect ticides, acaricides, nematicides, bird repellants, plant nutrients substances 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 solder solutions, suspensions, emulsions, powders, pastes and granules 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

1.6 g (8.8 mmol) of 6-chloro-pyridine-3-carboxylic acid chloride are at room temperature (approx. 20 ° C) with stirring to a mixture of 2.4 g (8.0 mmol) of 2-imino-5-methyl 3- (3-trifluoromethyl-phenyl) thiazoline hydrochloride, 2.4 g (24 mmol) triethylamine and 50 ml of ethyl acetate. The reaction mixture turns 30 Stirred for minutes at room temperature, then washed with 1N hydrochloric acid, with Dried sodium sulfate and filtered. The solvent is removed from the filtrate under ver carefully distilled off under reduced pressure.

2.6 g (82% of theory) of 6-chloro-N- [5-methyl-3- (3-trifluoromethyl- phenyl) -1,3-thiazole-2 (3H) -ylidene] -pyridine-3-carboxamide with a melting point of 177 ° C.

Analogously to Example 1 and in accordance with the general description of the production process according to the invention, the compounds of the general formula (I) listed in Table 1 below can also be prepared, for example.

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 24 hours the soil is sprayed with the active ingredient preparation so that the desired one Amount of active ingredient is applied per unit area. The drug concentration in 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, 4, 7 and 8 with good tolerance to crops, such as. B. barley, Corn and wheat, strong weed control.  

Example B Post 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.

With the active ingredient preparation, test plants are sprayed, which have a height of 5-15 cm have so that the desired amounts of active ingredient per 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, 4, 6 and 7 with partially good tolerance to crops, such as. B. Corn and wheat, strong weed control.

Claims (8)

1. Compounds of the general formula (I)
in which
A represents a single bond or alkanediyl (alkylene) having 1 to 6 carbon atoms,
Q represents oxygen or sulfur,
R ¹ for each optionally by nitro, amino, 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) amino carbonyl, di (C ₁ -C ₄ alkyl) amino sulfonyl, C ₃ -C ₆ cycloalkyl, or by in each case optionally by cyano, nitro, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy or C ₁ -C ₄ haloalkoxy substituted phenyl, phenoxy or phenylthio substituted, monocyclic or bicylic heterocyclyl, the heterocyclyl group having up to 10 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 or 2 oxygen atoms or sulfur atoms and optionally additionally Contains 1 to 3 oxo groups (C = O) and / or thioxo groups (C = S),
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 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 ⁴ for hydrogen, cyano, halogen, for alkoxy optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy having 1 to 6 carbon atoms, for each cycloalkyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl 3 to 6 atoms each carbon, in each case optionally substituted 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) -amino-carbonyl or di- (C ₁ -C ₄ -alkyl) -aminosulfonyl-substituted phenyl or naphthyl, or for in each case 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 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 alkylaminocarbonyl , Di- (C ₁ -C ₄ alkyl) amino carbonyl or di (C ₁ -C ₄ alkyl) amino sulfonyl is substituted, monocyclic or bicyclic heterocyclyl, the heterocyclyl group having up to 10 carbon atoms and additionally contains 1 to 4 nitrogen atoms and / or 1 or 2 oxygen atoms or sulfur atoms, and
Y represents a single bond or NH, N (C ₁ -C ₄ alkyl), N (C ₂ -C ₄ alkenyl) or N (C ₂ -C ₄ alkynyl). 2. Compounds according to claim 1, characterized in that
A represents a single bond or methylene (CH ₂ ), dimethylene (CH ₂ CH ₂ ) or trimethylene (CH ₂ CH ₂ CH ₂ ),
R ¹ for each optionally by nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, Fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, fluorine dichloromethyl, chlorodifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, fluorochloroethyl, trifluoroethyl, trichloroethyl, di fluorochloroethyl, dichlorofluoromethyl, fluoropropyl, chlorifluoropropyl, methifluoropropyl, chlorofluoropropyl, chlorofluoropropyl, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, trifluoroethoxy, trichloroethoxy, chlorodifluoroethoxy, fluoropropoxy, fluoropropoxypoxy , Dichloropropoxy, trifluoropropoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethyl thio, fluoroethylthio, chloroethylthio, difluoroethylthio, dichloroethylthio, trifluoroethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, methyllifylamyl, trifluoromethyl, - or i- propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethyl amino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylamino carbonyl, dimethylaminocarbonyl, diethylaminocarbonyl , Dimethyl aminosulfonyl, diethylaminosulfonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or by in each case optionally by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or chlorodifluoromethoxy substituted phenyl, phenoxy or phenylthio substituted, monocyclic or he bicyclic heterocyclyl from the series furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, 1,3,2-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4 -Oxa diazolyl, 1,3,2-thiadiazolyl, 1,3,2-benzothiadiazolyl, 1,2,3-thia diazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 2,4-dihydro -3H-3-oxo-1,2,4-triazol-2-yl (aka 4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl), pyridinyl, quinolinyl, pyrimidinyl , Triazinyl, pyrrolidinyl, piperidinyl, morpholinyl,
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,
R ⁴ for hydrogen, cyano, fluorine, chlorine, bromine, for methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t- which is optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy Butoxy, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for each optionally substituted by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorodifluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, methylthio Ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or dimethylamino hoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino carbonyl, diethylamino-carbonyl, dimethylaminosulfonyl or diethylaminosulfonyl, substituted phenyl or naphthyl, or for each optionally substituted by nitro, cyano , Carbamoyl, thiocarbamoyl, halogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, fluoromethyl, difluoromethyl, trifluoromethyl, chloromethyl, dichloromethyl, trichloromethyl, fluorodichloromethyl, chlorofluoromethyl, fluoroethyl , Chloroethyl, difluoroethyl, dichloroethyl, fluorochloroethyl, trifluoroethyl, trichloroethyl, difluorochloroethyl, di chlorofluoroethyl, fluoropropyl, chloropropyl, difluoropropyl, trifluoropropyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy , Difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, tri fluoroethoxy, trichloroethoxy, chlorodifluoroethoxy, fluorodichloro thoxy, fluoropropoxy, chloropropoxy, difluoropropoxy, dichloropropoxy, trifluoropropoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthioethyl, chloro-dichloro, fluorodichloro Difluoroethylthio, dichloroethylthio, trifluoroethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, nyl-, ethyl-, nyl-, nyl-, nyl-, methyl- s- or t-butylamino, dimethylamino, diethylamino, methoxy carbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylamino carbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylamino-carbonyl, dimethylamino sulfonyl or diethylamino-sulfonyl monocyclic or bicyclic heterocyclyl from the series furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, Benzothiazolyl, isothiazolyl, 1,3,2-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,2-thiadiazolyl, 1,3,2-benzothiadiazolyl, 1,2,3- Thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, pyridinyl, quino linyl, pyrimidinyl, and
Y represents a single bond or NH, N (methyl), N (ethyl), N (allyl) or N (propargyl). 3. Compounds according to claim 1, characterized in that A represents a single bond or methylene (CH ₂ ) or dimethylene (CH ₂ CH ₂ ),
R ¹ for each optionally by nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, difluoromethyl, Trifluoromethyl, dichloromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluorethoxy, trifluoroethoxy, trifluoroethoxy, trifluoroethoxy, trifluoroethoxy, trifluoroethoxy, trifluoroethoxy, trifluoroethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethoxy, trifluoromethyl -Propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, fluoroethylthio, chloroethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, methyllifylethyl, trifluoromethyl, trifluoromethyl , Ethoxycarbonyl, n- or i-propoxycarbonyl, dimethyl aminocarbonyl, dimethylaminosulfonyl, or by in each case by dur ch cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or chlorodifluoromethoxy substituted phenyl, Phenoxy or phenylthio substituted, monocyclic or bicylic heterocyclyl from the series furyl, benzofuryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, 1,3,2-oxadiazolyl, 1,2,4-oxadiazolyl 3,4-oxadiazolyl, 1,3,2-thiadiazolyl, 1,3,2-benzothiadiazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 2,4- Dihydro-3H-3-oxo-1,2,4-triazol-2-yl (aka 4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl), pyridinyl, quinolinyl, Pyrimidinyl, triazinyl, pyrrolidinyl, piperidinyl, morpholinyl,
R ^{2 represents} chlorine, bromine, methyl or ethyl,
R ^{3 represents} hydrogen, chlorine, bromine, methyl or ethyl,
R ⁴ for each optionally with nitro, cyano, carbamoyl, thio carbamoyl, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, di fluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, chlorofluoromethyl, fluorodichloromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulfinyl, ethylsulfonyl, trifluoromethylsulfonyl, methylifylylyloxyethyl, trifluoromethylsulfonyl, methyliflmethyloxyethyl, trifluoromethylsulfonyl, methylifluoromethyl, trifluoromethylsulfonyl, methylifluoromethyl, trifluoromethylsulfonyl, methylifluoromethyl, trifluoromethyl, , n- or i-propoxycarbonyl, dimethylaminocarbonyl or dimethylaminosulfonyl substituted phenyl or pyridinyl, and Y represents a single bond or NH. 4. Compounds according to claim 1, characterized in that
A stands for a single bond,
Q represents oxygen,
R ¹ for each optionally by nitro, amino, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl, fluorodichloromethyl, chlorodifluoromethyl, methoxy, ethoxy, n- or i propoxy, difluoromethoxy, tri- fluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, difluoro methylthio, trifluoromethylthio, chlorodifluoromethylthio, Fluordichlor methylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoro methylsulfonyl, Chlordifluormethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, dimethylaminocarbonyl, Di methylaminosulfonyl, or phenyl, phenoxy or phenylthio substituted, monocyclic or bicyclic heterocyclyl from the series Fur, optionally substituted by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or chlorodifluoromethoxy Benzo furyl , Thienyl, benzothienyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, 1,3,2-oxadiazolyl, 1,2,4-oxadiazolyl, 1,3,4-oxadiazolyl, 1,3,2-thiadiazolyl, 1,3,2-benzothia diazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 2,4-dihydro-3H-3-oxo-1,2,4 triazol-2-yl (also known as 4,5-dihydro-5-oxo-1H-1,2,4-triazol-1-yl), pyridinyl, quinolinyl, pyrimidinyl, triazinyl, pyrrolidinyl, piperidinyl, morpholinyl,
R ^{2 represents} methyl,
R ^{3 represents} hydrogen,
R ^{4 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 fluorine, chlorine, Tri contains fluoromethyl, and
Y stands for a single bond. 5. A process for the preparation of compounds according to any one of claims 1 to 4, characterized in that 2-imino-thiazolines of the general formula (II)
in which
A, R ² , R ³ and R ^{4 have} the meaning given in one of claims 1 to 4,
- or acid adducts of compounds of the general formula (II) -
with (thio) carbonyl compounds of the general formula (III)
in which
Q, R ¹ and Y have the meaning given in one of claims 1 to 4 and
X represents halogen, alkoxy, aryloxy, arylalkoxy or the grouping -OC (Q) -YR ¹ ,
or with iso (thio) cyanates of the general formula (IV)
Q = C = NR ¹ (IV)
in which
Q and R ^{1 have} the meaning given in one of claims 1 to 4,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and optionally the compounds of the general formula (I) thus obtained are converted into other compounds of the general formula (I) in the context of the above definition of substituents by customary methods. 6. Process for controlling unwanted vegetation, thereby ge indicates that at least one connection according to one of the An say 1 to 4 on unwanted plants and / or their habitat lets work. 7. Use of at least one compound according to one of the claims 1 to 4 for controlling unwanted plants. 8. Herbicidal agent, characterized by a content of a compound according to one of claims 1 to 4 and conventional extenders and / or Surface-active agents according to one of claims 1 to 4 and customary Extenders and / or surfactants.