WO2001010853A1

WO2001010853A1 - Substituted 2-imino-thiazolines

Info

Publication number: WO2001010853A1
Application number: PCT/EP2000/007265
Authority: WO
Inventors: Klaus-Helmut Müller; Mark-Wilhelm Drewes; Peter Dahmen; Dieter Feucht; Rolf Pontzen
Original assignee: Bayer Aktiengesellschaft
Priority date: 1999-08-10
Filing date: 2000-07-28
Publication date: 2001-02-15
Also published as: AR025092A1; DE19937771A1; AU6567400A

Abstract

The invention relates to novel, substituted 2-imino-thiazolines of general formula (I), wherein R?1, R2, R3, R4¿, 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

Substituted 2-imino-thiazolines

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

It is known that certain substituted 2-imino-thiazolines have herbicidal properties (cf. EP-A-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 significance.

New substituted 2-imino-thiazolines 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] -C ₄ alkyl, dC ₄ haloalkyl, QC ₄ alkoxy, C _t -C ₄ haloalkoxy, CC ₄ alkylthio, CC ₄ haloalkylthio, C _r C ₄ -

Alkylsulfmyl, -C-C ₄ -haloalkylsulfιnyl, C] -C ₄ -alkylsulfonyl, C] -C ₄ -halo-alkylsulfonyl, Cι-C ₄ -alkylamino, di- (Cι-C ₄ -alkyl) amino, Cι-C ₄ -alkoxy- carbonyl, -CC ₄ -alkylamino-carbonyl, di- (-C-C ₄ -alkyl) -amino-carbonyl, di- (-C-C ₄ -alkyl) -aminosulfonyl, C ₃ -C ₆ -cycloalkyl, or ₄ -haloalkoxy-substituted phenyl, phenoxy or phenylthio by in each case optionally substituted by cyano, nitro, halogen, Cι-C ₄ -alkyl, C ₄ haloalkyl, Cι-C ₄ alkoxy or Cι-C substituted monocyclic or bicyclic heterocyclyl , wherein 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 and optionally additionally 1 to 3 oxo groups (C = O) and / or thioxo groups (C = S),

R ^{2 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,

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

R 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 ₄ -

Alkyl, dC ₄ -haloalkyl, -C-C - alkoxy, - -haloalkoxy, Cι-C - alkylthio, Cι-C -haloalkylthio, Cι-C ₄ -alkylsulfmyl, Cι-C -halo-alkylsulfinyl, Cι-C ₄ -alkylsulfonyl , -C-C ₄ -haloalkylsulfonyl, C - C ₄ -alkylamino, di- (-C-C ₄ -alkyl) -amino, Cι-C ₄ -alkoxy-carbonyl, dC ₄ -alkyl-amino-carbonyl, di- ( C 1 -C ₄ -alkyl) -amino-carbonyl or di- (dC ₄ -alkyl) - amino-sulfonyl-substituted phenyl or naphthyl, or for optionally by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, C - C ₄ alkyl, C ₄ -C haloalkyl, C 1 -C alkoxy, CC ₄ haloalkoxy, C _r C ₄ alkylthio, CC ₄ -Halogenalkylthio, -C-C ₄ -alkylsulfmyl, Q- C ₄ -Halogenalkylsulfιnyl, C i -C ₄ - alkylsulfonyl, C ι -C ₄ -haloalkylsulfonyl, Cι-C ₄ -alkylamino, di- (C [-C ₄ - alkyl) amino, C] -C ₄ alkoxycarbonyl, C] -C ₄ -

Alkylamino-carbonyl, di- (-C ₄ -alkyl) -amino-carbonyl or di- (C] -C ₄ -alkyl) -aminosulfonyl-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 (CC ₄ -alkyl), N (C ₂ -C ₄ -alkenyl) or N (C ₂ -C ₄ -alkynyl),

found.

The general formula (I) includes the possible E and Z isomers of the compounds of the formula (I).

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

Preferred substituents or ranges of the radicals listed in the formulas given above and below are defined below.

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

Q preferably represents oxygen or sulfur. 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, difluorophenyl, di-chlorofluoromethyl, fluorofluoromethyl Ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, trifluoroethoxy, trichloroethoxy,

Chlordifluorethoxy, Fluordichlorethoxy, Fluoφropoxy, Chloφropoxy, Di-fluoφropoxy, Dichloφropoxy, Trifluoφropoxy, Methylthio, Ethylthio, n- or i-Propylthio, n-, i-, s- or t-Butylthio, Difluormethylthio, Fluorodiochloro, Trifluoromethyl Fluoroethylthio, chloroethylthio, difluoroethylthio, dichloroethylthio, trifluoroethylthio, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propyl-methyll-methyll-methyll-methyll-methyll-methyll-methyl-fluoryl-methyl-fluoryl or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, Dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl, diethylaminosulfonyl, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, or by counter in each case also phenyl 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, 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 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-l, 2,4-triazol-2-yl (aka 4,5-dihydro-5-oxo -lH-l, 2,4-triazol-l-yl), pyridinyl, quinolinyl, pyrimidinyl, triazinyl, pyrrolidinyl, piperidinyl, Moφholinyl.

R ² preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, methoxycarbonyl, ethoxycarbonyl, n- or i- propoxycarbonyl.

R ³ preferably represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, or methyl, ethyl, n- or i-propyl, n- or n-propyl, 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, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy -Butoxy, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, each 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, trifluoro- methoxy, chlorodifluoromethoxy, methylthio, ethylthio, n- or i-propylthio,

Difluoromethylthio, trifluoromethylthio, chlorodifluoromethyl thio, Methylsul- finyl, Ethylsulfmyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl , n- or i-

Propylaminocarbonyl, dimethylaminocarbonyl, diefhylamino-carbonyl, di- methylaminosulfonyl or diethylaminosulfonyl substituted phenyl or naphthyl, or for each optionally by nitro, cyano, 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, methoxy Chlordifluor-, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorine fluoroethoxy, trifluoroethoxy, trichloroethoxy, Chlordifluorethoxy, Fluordi- chloroethoxy, Fluoφropoxy, Chloφropoxy, Difluoφropoxy, Dichloφropoxy, Trifluoφropoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, fluoroethylthio, chloroethylthio, difluoroethylthio, di- chloroethylthio, trifluoroethylthio, Mefhylsulfinyl, ethylsulfinyl, n- or i- propylsulfinyl, trifluoromethylsulfinyl , Methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylam ino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, mefhylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylaminocarbonyl, diethylamino-carbonyl , Dimethylaminosulfonyl or Diethylaminosulfonyl substituted, monocyclic or bicyclic heterocyclic from the series furyl, benzofüryl, thienyl, benzothienyl, oxazolyl, benzoxazolyl, isoxazolyl, thiazolyl, benzothiazolyl, isothiazolyl, 1,3,2-oxadiazol , 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.

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, dichloroethoxy, chlorofluoroethoxy, trifluoroethoxy, methylthio, ethylthio, n- or i-propylthio, trifluoromethylthiothio, thio, difluoromethylthiothio, Fluoroethylthio, chloroethylthio, methylsulfinyl,

Ethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl, dimethylamino, carbonyl, carbonyl, carbonyl 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 bicyclic heterocyclyl from the series furyl, benzofüryl, 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-l, 2,4-triazol-2-yl (alias 4.5 Dihydro-5-oxo-lH-l, 2,4-triazol-l-yl), pyridinyl, quinolinyl, pyrimidinyl, triazinyl, pyrrolidinyl, piperidinyl,

Moφholinyl. 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, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulfmylylethyl, ethylsulfinyl, trifluoromethylsulfonylmethyl, methyltrifluoromethylsulfonyl, methyltrifluoromethylsulfonyl n- or i-Propoxycarbonyl, dimethylaminocarbonyl or dimethylammosulfonyl 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, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, methylsulfmyl, ethylsulfinyl, trifluoromethylsulfylyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methylsulfyl, methyltrifluoromethyl difluoromethylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, dimethylaminocarbonyl, dimethylammosulfonyl, or by in each case optionally substituted by cyano, nitro, fluorine, chlorine, bromine, methyl, ethyl, trifluoromethyl, methoxy, ethoxy, difluoromethoxy, trifluoromethoxy or chlorodifluoromethoxy or phenyl, phenyl, phenio, phenyl or phenyl 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-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-l, 2,4-triazol-2-yl (aka 4,5-dihydro-5-oxo-lH-l, 2,4-triazol-l-yl), pyridinyl, quinolinyl, pyrimidinyl , Triazinyl, pyrrolidinyl, piperidinyl, Moφholinyl.

R, 2 very particularly preferably represents methyl.

R ³ very particularly preferably represents hydrogen.

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

Y very particularly preferably represents a single bond.

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

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

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

The new substituted 2-imino-thiazolines of the general formula (I) have interesting biological properties. They are particularly characterized by their 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)

_^ R ¹

Y '

(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)

QON-R ¹ (IV)

in which

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

optionally in the presence of a reaction auxiliary and optionally in

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 substituent 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 reaction can run in the method according to the invention are outlined by 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} specified.

The starting materials of the general formula (II) are known and / or can be prepared by processes known per se (cf. US Pat. No. 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 ; 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 synthetic 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 ,

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

The process according to the invention for the preparation of compounds of general

Formula (I) is optionally carried out using a reaction auxiliary. The usual inorganic or organic bases or acid acceptors are generally suitable as reaction aids for the process according to the invention. These preferably include alkali metal or alkaline earth 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 methanolate, ethanolate, -n- or -i-propanolate, -n-, -i-, -s- or -t-butanolate; also basic organic nitrogen compounds, such as, for example, trimethylamine, triethylamine, tripropylamine, tributylamine, ethyldiisopropylamine, N, N-dimethylcyclohexylamine, dicyclohexylamine, ethyldicyclohexylamine, N, N-dimethylaniline, 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-methylpiperidine, 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,

Benzyl-trimethylammonium chloride, benzyl-triethylammonium chloride, benzyl-trimethylammonium hydroxide, benzyl-triethylammonium hydroxide, benzyl-tributylammonium chloride, benzyl-tributylammonium bromide, tetrabutylphosphonium bromide, tetrabutylphomide hexadecylphosphonium bromide, butyl triphenylphosphonium chloride, ethyl trioctylphosphonium bromide, tetraphenylphosphonium bromide.

The process according to the invention for the preparation of the compounds of the general formula (I) is preferably carried out using diluents. In addition to water, diluents for carrying out the processes according to the invention are in particular inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, gasoline, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; Ethers, such as diethyl ether, diisopropyl ether,

Dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; Ketones, such as acetone, butanone or methyl isobutyl ketone; Nitriles, such as acetonitrile, propionitrile or butyronitrile; Amides such as N, N-dimethylformamide, N, N-dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric acid triamide; Esters such as methyl acetate or ethyl acetate, sulfoxides such as

Dimethyl sulfoxide, alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, their mixtures with water or pure water.

The reaction temperatures can be carried out when carrying out the process according to the invention

Process can be varied over a wide range. In general, 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. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.

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

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

The active compounds according to the invention can be used, for example, 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, Gupopsisia, Euphorbia , Galium, Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercurialis, Mullugo, Myosotis, Papaver,

Pharbitis, Plantago, Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex, Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanth.

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, Sagaria, Setaria, Setaria.

Monocot cultures of the genera: Allium, pineapple, asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Seeale, Sorghum, Triticale, Triticum, Zea.

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

Plants.

Depending on the concentration, the active compounds according to the invention are suitable for combating total weeds, for example on industrial and rail tracks and on paths and squares with and without tree growth. The active compounds according to the invention for combating weeds in permanent crops, for example forest, ornamental wood, Fruit, wine, citrus, nut, banana, coffee, tea, rubber, oil palm, cocoa, berry fruit and hop plants, used on ornamental and sports turf and pasture land and for selective weed control in annual crops become.

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

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

The treatment of the plants and parts of plants with the active compounds according to the invention is carried out directly or by acting on their surroundings, living space or storage space using the customary treatment methods, e.g. by dipping, spraying, evaporating, atomizing, scattering, spreading and, in the case of propagation material, in particular in the case of seeds, furthermore by means of one or more layers

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

Substances.

These formulations are prepared in a known manner, e.g. B. by mixing the active ingredients with extenders, ie liquid solvents and / or solid carriers, optionally using surface-active agents

Agents, ie emulsifiers and / or dispersants and / or foam-generating agents.

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

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

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

Coconut shells, corn cobs and tobacco stems; as emulsifying and / or foaming Generating agents are possible: for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; Possible dispersing agents are, for example, lignin sulfite waste liquor and methyl cellulose.

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

Additives can be mineral and vegetable oils.

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

Molybdenum and zinc can be used.

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

The active compounds according to the invention, as such or in their formulations, can also be used in a mixture with known herbicides and / or with substances which improve crop tolerance ("safenem") for weed control, finished formulations or tank mixes being possible. Mixtures are therefore also possible possible with weed control agents which contain one or more known herbicides and a safener.

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), benfüresate, bensulfuron (-methyl), bentazone, Benzobicyclone, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac- (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chloramethoxy , Chloridazon, chlorimuron (-ethyl), chloronitrofen, chlorosulfuron, chlorotoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim,

Clethodim, Clodinafop (-propargyl), Clomazone, Clomeprop, Clopyralid, Clopyra-sulfüron (-methyl), Cloransulam (-methyl), Cumyluron, Cyanazine, Cybutryne, Cycloate, Cyclosulfamuron, Cycloxydim, Cyhalofop (-butyl) 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, Dithiopyr, Diuron, Dymron, Epropodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulfuron (-methyl), Ethofümesate, Ethoxyfen, Ethoxysulfidon, Fenoxenz- ethyl), fentrazamide, flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop- (-methyl), flazasulftiron, florasulam, fluazifop (-P-butyl), fluazolate, flucarbazone,

Flufenacet, Flumetsulam, Flumiclorac (-pentyl), Flumioxazin, Flumipropyn, Flumet-sulam, Fluometuron, Fluorochloridone, Fluoroglycofen (-ethyl), Flupoxam, Fluprop-acil, Fluφyrsulfüron (-methyl, -sodium), Flurenol (-uryl), , Fluroxypyr- (-meptyl), Fluφrimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glufosinate (-ammonium), Glyphosate (-isopropylammonium), Halosafen, Haloxyfop-

(-ethoxy ethyl), Haloxyfop (-P -methyl), Hexazinone, Imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfüron (-methyl, -sodium), Ioxynil, Isalin , Isoproturon, Isouron, Isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, Metobromuronamobluron, Metobenzuron, Metobromuron, Mobro , Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Napropamide, Neburon, Nicosulfuron, Norflurazon, Orbencarb, Oryzalin, Oxadiargyl, Oxadiazon, Oxasulfuron, Oxaziclomefone, Oxyfluorfen, Paraquat, Penthalone, Pelargonic acid , Phenmedipham, Piperophos, Pretilachlor, Primisulfüron (-methyl), Prometryn, Propachlor, Propanil, Propaquizafop, Propisochlor, Propyzamides, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolates, pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxime, pyributicarb, pyridates, pyriminobac- (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerine, quinmerac, quinmerac, quinmerac - fop (-P-ethyl), quizalofop (-P-tefüryl), rimsulfüron, sethoxydim, Simazine, Simetryn, Sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate, sulfosulfuron, tebutam, tebuthiuron, tepralylaxzimine, terbutylaxzimine, terbutyloxydim, terbutyloxydim , Thenylchlor, Thiafluamide, Thiazopyr, Thidiazimin, Thifensulfuron (-methyl), Thiobencarb, Tio-carbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Triclopyr, Tri-diphane, Trifluralin and Triflusulfüron.

A mixture with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellants, plant nutrients and agents which improve soil structure, is also possible.

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

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

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

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

example 1

1.6 g (8.8 mmol) of 6-chloro-pyridine-3-carboxylic acid chloride become a mixture of 2.4 g (8.0 mmol) of 2-imino-5 at room temperature (approx. 20 ° C) -methyl- 3- (3-trifluoromethyl-phenyl) thiazoline hydrochloride, 2.4 g (24 mmol) of triethylamine and 50 ml of ethyl acetate. The reaction mixture is stirred at room temperature for about 30 minutes, then washed with IN hydrochloric acid, with

Dried sodium sulfate and filtered. The solvent is carefully distilled off from the filtrate under reduced pressure.

2.6 g (82% of theory) of 6-chloro-N- [5-methyl-3- (3-trifluoromethylphenyl) -1, 3-thiazole-2 (3H) -ylidene] pyridine-3 are obtained 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, 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)

Application examples:

Example A

Pre-emergence test

Solvent: 5 parts by weight of acetone

Emulsifier: 1 part by weight of alkylaryl polyglycol ether

To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the specified amount is given

Amount of emulsifier and dilute the concentrate with water to the desired 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 active ingredient concentration in the spray liquor is chosen so that the desired amount of active ingredient is applied in 1000 liters of water per hectare.

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

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

In this test, for example, the compounds according to Preparation Examples 1, 4, 7 and 8, with good tolerance to cultivated plants, such as, for example, barley, corn and wheat, show a strong action against weeds. Example B

Post-emergence test

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

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

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

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 destruction

In this test, for example, the compounds according to the preparation example show

1, 4, 6 and 7 with good tolerance to cultivated plants, e.g. Corn and wheat, strong weed control.

Claims

claims

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 represents in each case optionally substituted by nitro, amino, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, Cι-C ₄ - alkyl, _Cι-C4 halo-alkyl, Cι-C ₄ - alkoxy, Cι-C ₄ haloalkoxy, Cι-C ₄ alkylthio, Cι-C ₄ - haloalkylthio, C ι -C ₄ - alkylene Isulfinyl, C ι -C ₄ -Halogenalky Isulfinyl, Cι-C ₄ alkylsulfonyl, Cι-C ₄ haloalkylsulfonyl, C] -C ₄ -alkylamino, di- (-CC ₄ -alkyl) -amino, -CC ₄ -alkoxy-carbonyl, C] -C ₄ -alkylamino-carbonyl, di- (C ₁ -C ₄ -alkyl) -amino- carbonyl, di- _(Cι-C4 alkyl) amino- sulfonyl, C ₃ -C ₆ cycloalkyl, or in each case optionally substituted by cyano, nitro, halogen, Cι-C ₄ -alkyl, C ₄ haloalkyl, Cι-C ₄ - Alkoxy or dC 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 Contains oxygen atoms or sulfur atoms and optionally additionally 1 to 3 oxo groups (C = O) and / or thioxo groups (C = S),

R ² for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally by cyano, halogen or

C 1 -C ₄ -alkoxy-substituted alkyl or alkoxycarbonyl each having up to 6 carbon atoms,

R ³ for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or for each optionally by cyano, halogen or

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 by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, Cj _. -C ₄ - alkyl, -C-C ₄ -halo-alkyl, -C-C ₄ -alkoxy, Cι-C ₄ -haloalkoxy, CC ₄ -alkylthio, Cι-C ₄ -

Haloalkylthio, C] -C ₄ -alkylsulfinyl, Cι-C ₄ -haloalkylsulfinyl, C] -C ₄ -alkylsulfonyl, Cι-C ₄ -haloalkylsulfonyl, CrC ₄ -alkylamino, di- (CrC ₄ -alkyl) -amino, Cι- C ₄ -alkoxy-carbonyl, CrC ₄ -alkylamino-carbonyl, di- (-C-C ₄ -alkyl) -amino-carbonyl or di- (-C-C ₄ -alkyl) - amino-sulfonyl-substituted phenyl or naphthyl, or for in each case optionally substituted by nitro, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, Cι-C ₄ -alkyl, C ₄ haloalkyl, Cj-C ₄ - alkoxy, _{Cι-C4-haloalkoxy,} Cι-C ₄ alkylthio, -C-C ₄ -Halogenalkyl- thio, -C-C ₄ -Alkylsulfmyl, - -Halogenalkylsulfinyl, Cι-C ₄ -Alkyl-sulfonyl, Cι-C ₄ -Halogenalkylsulfonyl, C] -C ₄ -alkylamino, di- (Cι-C ₄ - alkyl) amino, Cι-C ₄ -alkoxy-carbonyl, C] _-C4 alkylamino-carbonyl, Di- (-C-C ₄ alkyl) amino carbonyl or di (C _! -C ₄ alkyl) amino sulfonyl substituted, monocyclic or bicyclic heterocyclyl is, the heterocyclyl group having up to 10 carbon atoms and additionally 1 to 4 Contains nitrogen atoms and / or 1 or 2 oxygen atoms or sulfur atoms, and

Y represents a single bond or NH, N (dC-alkyl), N (C ₂ -C ₄ -alkenyl) or N (C ₂ -C ₄ -alkynyl).

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, fluorodichloromethyl, Chlorodifluoromethyl, fluoroethyl, chloroethyl, difluoroethyl, dichloroethyl, fluorochloroethyl, trifluoroethyl, trichloroethyl, di-fluorochloroethyl, dichlorofluoroethyl, fluoropropyl, chloropropyl, difluoropropyl, trifluoropropyl, methoxy, ethoxy, n- or i-propoxy, n-, , s- or t-butoxy, difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, trifluoroethoxy, trichloroethoxy, chlorodifluoroethoxy,

Fluorodichloroethoxy, Fluoφropoxy, Chloφropoxy, Difluoφropoxy, Dichloφropoxy, Trifluoφropoxy, Methylthio, Ethylthio, n- or i-Propylthio, n-, i-, s- or t-Butylthio, Difluormethylthio, Trifluormethylthio, Chloromethylioio, Chlorlethylifluoromethyl, Chlordethylifluoromethyl Difluoroethylthio, dichloroethylthio, trifluoroethylthio, methylsulfmyl, ethylsulfinyl, n- or i-propylsulfinyl, tri- fluoromethylsulfinyl, chlorodifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, n- or i-propylsulfonyl, trifluoromethylsulfonyl, chlorodifluoromethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-, or t-methylamylcarbonyl , Ethoxycarbonyl, n- or i-propoxycarbonyl,

Methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, 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 chlorodifluoromethoxy substituted phenyl, phenoxy or phenylthio substituted, monocyclic or bicylic heterocyclyl from the furyl series , 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, 2,4-dihydro-3H- 3-oxo-1, 2,4-triazol-2-yl (alias 4,5-dihydro-5-oxo-1 H-1, 2,4-triazol-1-yl), pyridinyl, quinolinyl, pyrimidinyl, triazinyl , Pyr rolidinyl, piperidinyl, Moφholinyl,

R ² for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, fluorine,

Chlorine, bromine, or for methyl, ethyl, n- or i-propyl, methoxycarbonyl, optionally substituted by fluorine or chlorine,

Ethoxycarbonyl, n- or i-propoxycarbonyl,

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

Chlorine, bromine, or for methyl, ethyl, n- or i-, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy Propyl, n-, i-, s- or t-butyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,

for hydrogen, cyano, fluorine, chlorine, bromine, for any substituted by cyano, fluorine, chlorine, methoxy or ethoxy

Methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, for each cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, each for 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, difluoro- methylthio, trifluoromethylthio, chlorodifluoromethylthio, Methylsulfmyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, Methylamino, ethylamino, n- or i-propylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i-propylaminocarbonyl, dimethylamino- carbonyl, diethylamino-carbonyl, dimethylammosulfonyl or diethylaminosulfonyl-substituted phenyl or naphthyl, or for in each case optionally by nitro, cyano, 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, chloro-phylo , Trifluoropropyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,

Difluoromethoxy, trifluoromethoxy, chlorodifluoromethoxy, fluoroethoxy, Chloroethoxy, difluoroethoxy, dichloroethoxy, chlorofluoroethoxy, trifluoroethoxy, trichloroethoxy, chlorodifluoroethoxy, fluorodichloroethoxy, fluoropropoxy, chloropropoxy, difluoropropoxy, dichloropropoxy, trifluoropropoxy, methylthio, ethylthio, n-, or i-, n-, or i-, i-, n-, or- t-butylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, fluoroethylthio, chloroethylthio, difluoromethylthio, dichloroethylthio, trifluorethylthio, methylsulfinyl, ethylsulfinyl, n- or i-propylsulfylonylsulfyl, trifluorosulfonyl, trifluoromethylsulfylonyl, Methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylaminocarbonyl, ethylaminocarbonyl, n- or i- Propylaminocarbonyl, dimethylaminocarbonyl, diethylaminocarbonyl, dimethylaminosulfonyl or diethylaminosulfonyl substituted, monocyclic ode bicyclic heterocyclyl from the series furyl, benzofüryl, 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, quinoline, 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 for a single bond or for methylene (CH ₂ ) or dimethylene

(CH ₂ CH ₂ ) stands, 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, di-fluoroethoxy, dichloroethoxy, chlorofluorethoxy, methyl, trifluoromethoxy, methylthio, trio i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, fluoroethylthio, chloroethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, chlorodifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, Chlordifluormethylsulfonyl, methylamino, ethylamino, n- or i-propylamino, dimethylamino, methoxycarbonyl, ethoxycarbonyl , n- or i-propoxycarbonyl, dimethylaminocarbonyl, dimethylammosulfonyl, 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 bicylic heterocyclyl from the series furyl, benzofüryl,

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-l, 2,4-triazole- 2-yl (alias 4,5-dihydro-5-oxo-lH-l, 2,4-triazol-l-yl), pyridinyl, quinolinyl, pyrimidinyl, triazinyl, pyrrolidinyl, piperidinyl, Moφholinyl,

R ^{2 represents} chlorine, bromine, methyl or ethyl,

R ^{3 represents} hydrogen, chlorine, bromine, methyl or ethyl, R ⁴ for each optionally by 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, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, methylsulphinyl, ethylsulphinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoro- methylsulfonyl, dimethylamino, methoxycarbonyl, ethoxycarbonyl, 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, trifluoromethoxy, chlorodifluoromethoxy, methylthio, ethylthio, difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, fluorodichloromethylthio, methylsulfinyl, ethylsulfonyl, trifluoromethylsulfyl, methylsulfylifylmethylsulfylifluoromethylsulfonyl

Methoxycarbonyl, ethoxycarbonyl, dimethylaminocarbonyl, di- methylaminosulfonyl, or by 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 , Benzofyl, 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-benzothiaediazolyl, 1,2,3-thiadiazolyl, 1,2,4-thiadiazolyl, 1,3,4-thiadiazolyl, 2,4-dihydro-3H-3-oxo -l, 2,4-triazol-2-yl (alias 4,5-dihydro-5-oxo-lH-l, 2,4-triazol-l-yl), pyridinyl, quinolinyl, pyrimidinyl, triazinyl, pyrrolidinyl, piperidinyl , Moφholinyl stands,

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 optionally a further substituent from the series fluorine, chlorine, trifluoromethyl contains, 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-COJ-YR ¹ ,

or with iso (thio) cyanates of the general formula (IV)

Q = C = N-R '(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,

6. A method for controlling unwanted vegetation, characterized in that at least one compound according to one of claims 1 to 4 is allowed to act on undesired plants and / or their habitat.

7. Use of at least one compound according to one of 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 conventional extenders and / or surface-active agents.