DE19856965A1 - Substituted 2-imino-thiazolines - Google Patents

Abstract

The invention relates to novel substituted 2-imino-thiazolines of general formula (I), wherein A represents a simple bond or optionally substituted alkanediyl (alkylene), R<1> represents optionally substituted alkyl, optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl, R<2> represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl or optionally substituted alkoxycarbonyl, R<3> represents hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl or optionally substituted alkoxycarbonyl, and R<4> represents hydrogen, cyano, halogen or alkoxy, or optionally substituted cycloalkyl, optionally substituted aryl or optionally substituted heterocyclyl, including the possible E- and Z-isomers of these compounds. The invention also relates to methods for producing the inventive substituted 2-imino-thiazolines and to their use as plant treatment agents especially as herbicides and insecticides.

Description

The invention relates to new substituted 2-imino-thiazolines, processes for their manufacture position and their use as plant treatment agents, in particular as a bicidal and insecticidal.

It is known that certain substituted 2-imino-thiazolines have herbicidal properties ten (cf. EP-A-446802, EP-A-529481, EP-A-529482, EP-A-531970, WO- A-98/42703). However, these connections have so far had no particular meaning acquired.

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

in which
A represents a single bond or optionally substituted alkanediyl (alkylene),
R ^{1 represents} in each case optionally substituted alkyl, cycloalkyl, aryl or heterocyclic,
R ^{2 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or optionally substituted alkyl or alkoxycarbonyl,
R ^{3 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each optionally substituted alkyl or alkoxycarbonyl, and
R ^{4 represents} hydrogen, cyano, halogen or alkoxy, or any optionally substituted cycloalkyl, aryl or heterocyclyl,
including the possible E and Z isomers of the compounds of formula (I) found.

In the definitions, the hydrocarbon chains, such as alkyl or alkanediyl - also in connection with heteroatoms, such as in alkoxy - in each case straight-chain or ver branches.

The invention preferably relates to substituted 2-imino-thiazolines of the formula (I) in which
A represents a single bond or alkanediyl (alkylene) with 1 to 4 carbon atoms which is optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy,
R ¹ represents optionally cyano-, halogen or C ₁ -C gen ₄ -alkoxy-substituted alkyl having 1 to 6 carbon atoms, optionally substituted by cyano, halo or C ₁ -C men ₄ alkyl substituted cycloalkyl having 3 to 6 Kohlenstoffato, optionally substituted by nitro, cyano, 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, or C ₁ -C ₄ haloalkylsulfonyl substituted aryl having 6 or 10 carbon atoms, or represents in each case optionally cyano-, halo gen , C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C, -C ₄ haloalkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ halo alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl or C ₁ -C ₄ haloalkylsulfonyl substituted, monocyclic or bicyclic heterocyclyl having 1 to 9 carbon atoms, 1 to 4 S tickstoffatomen and / or 1 or 2 oxygen or sulfur atoms,
R ^{2 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halogen, or each alkyl or alkoxycarbonyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy, each having up to 4 carbon atoms,
R ^{3 represents} hydrogen, cyano, carboxy, carbamyl, thiocarbamoyl, halogen, or each alkyl or alkoxycarbonyl optionally substituted by cyano, halogen or C ₁ -C ₄ alkoxy and each having up to 4 carbon atoms, and
R ⁴ for hydrogen, cyano, halogen or alkoxy, for cycloalkyl with 3 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl, for optionally with nitro, cyano, 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 or C ₁ -C ₄ haloalkylsulfonyl substituted aryl having 6 or 10 carbon atoms, or for each optionally substituted by cyano, 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 finyl -Alkylsul, C ₁ -C ₄ haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl or C ₁ -C ₄ halo alkylsulfonyl substituted, monocyclic or bicyclic heterocyclyl having 1 to 9 carbon atoms, 1 to 4 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms marries
including the possible E and Z isomers of the compounds of formula (I).

The invention relates in particular to compounds of the formula (I) in which
A for a single bond or for methylene (CH ₂ ), dimethylene (ethane-1,2-diyl, CH ₂ CH ₂ ) or trimethylene (propane-1,3-diyl, CH) which is optionally substituted by cyano, fluorine and / or chlorine ₂ CH ₂ CH ₂ )
R ¹ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for each optionally substituted by cyano, fluorine, chlorine, Methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl , Trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfonyl, trifluoromethylsulfmyl or trifluorosulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, methylsulfonyl, for each optionally by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy , Trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, Tr ifluoromethylthio, methylsulfmyl, ethylsulfinyl, trifluoromethylsulfonyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted heterocycly1 from the series furyl, thienyl, oxazolyl, isoxazolyl, thiazoyl, oxadiazolyl, pyridylolidyl, pyrid
R ^{2 represents} methyl, ethyl, chlorine or bromine,
R ^{3 represents} hydrogen or methyl, and
R ⁴ for hydrogen, cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for optionally by nitro , Cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, Methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, methylenedioxy, ethylenedioxy, difluorodioxylenedioxy, tri, or difluoromethylenedioxyethylene, trifluoromethylenedioxylenedioxy, trifluoromethylenedioxylenedioxy, trifluorodioxylenedioxy, phenyl, or difluorodioxylenedioxy, Chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n - or i-propylthi o, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulphinyl, Methylsulfonyh ethylsulfonyl or tri- fluoromethylsulfonyl-substituted, optionally benzannelliertes hetero cyclyl from the series comprising furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, Isothia zolyl, S, S-dioxo-isothiazolyl, oxadiazolyl, thiadiazolyl , Pyridinyl or pyrimidinyl,
including the possible E and Z isomers of the compounds of formula (I).

A particularly preferred group are those compounds of the formula (I) in which
A represents a single bond or methylene (CH ₂ ),
R ¹ for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, Trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl, or phenyl which is substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfonyl, methylsulfonyl, trifluoromethylsulfonyl or ethylsulfonylsulfonyl Heterocyclyl from the series furyl, thienyl, oxazolyl, isoxazolyl, thiazo lyl, oxadiazolyl, thiadiazolyl, pyridinyl or pyrimidinyl,
R ^{2 represents} methyl or ethyl,
R ^{3 represents} hydrogen or methyl, and
R ⁴ for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, Trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, methylenedioxy, ethylenedioxy, difluoromethylenedioxy, trifluoroethylenedioxy or tetrafluoroethylenedioxy, or phenyl substituted in each case by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-i-n -, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, tr ifluormethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted heterocyclyl from the series furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl or pyrimidinyl, including the possible E- and Z-isomers of the isomers of the

Another particularly preferred group are those compounds of the formula (I) in which
A for methylene (CH ₂ ), dimethylene (ethane-1,2-diyl, CH ₂ CH ₂ ) or trimethylene (propane-1,3-diyl, CH ₂ CH ₂ CH) optionally substituted by cyano, fluorine and / or chlorine ₂ ) stands
R ¹ for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, Trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl, or phenyl which is substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, Methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfonyl, methylsulfonyl, trifluoromethylsulfonyl or ethylsulfonylsulfonyl Heterocyclyl from the series furyl, thienyl, oxazolyl, isoxazolyl, thiazo lyl, oxadiazolyl, ihiadiazolyl, pyridinyl or pyrimidinyl,
R ^{2 represents} methyl or ethyl,
R ^{3 represents} hydrogen or methyl, and
R ^{4 represents} hydrogen, cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy,
including the possible E and Z isomers of the compounds of formula (I).

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.

The new substituted 2-imino-thiazolines of the general formula (I) have inter essential biological properties. They are particularly characterized by strong herbicidal and insecticidal 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 compounds of the general formula (III)

XR ¹ (III)

in which
R ^{1 has} the meaning given above and
X represents halogen or the group -SO ₂ alkyl,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, subsequently carries out substitution reactions in the customary manner as part of the definition of substituents.

In principle, the compounds of the general formula (I) can also be synthesized as shown schematically in the following:
Isomerization of 5-alkylidene-2-imino-thiazolidines of the general formula (IV) - where A, R ¹ , R ³ and R ^{4 have} the meaning given above and R ^2-1 is hydrogen or alkyl - at elevated temperature:

If, for example, 5-ethyl-2-imino-3- (3-trifluoromethyl-phenyl) thiazoline and 2-fluoro-benzonitrile 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 are preferred or particularly preferred for the description of the compounds of the general formula (I) according to the invention 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 processes known per se can be prepared (cf. US-A-5459277, EP-A-545431).

The compounds to be used as starting materials in the process according to the invention are generally defined by the formula (III). In the general formula (III), R ¹ preferably or in particular has the meaning which have 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 R ¹ ; X preferably represents fluorine, chlorine, bromine or the group -SO ₂ - (C ₁ -C ₄ alkyl), in particular fluorine, chlorine or methylsulfonyl.

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

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 generally the usual inorganic or organic bases or acid acceptors other. 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 hydrogen carbonate, lithium, sodium, potassium or cal cium hydride, lithium, sodium, potassium or calcium hydroxide, sodium or Potassium methoxide, ethanolate, n- or i-propanolate, n-, i-, -s or t-butanolate; also basic organic nitrogen compounds, such as tri methylamine, triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine, N, N-dimethyl-cyclohexylamine, dicyclohexylamine, ethyl-dicyclohexylamine, N, N- Dimethyl-anhin, 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-triphenylphosphoniumphonium-phosphonium-phosphonium-phosphonium-phosphonium-phosphonium-phosphonium-phosphonium-phosphonium-phosphonium-phosphonium-phosphonium-phosphoronium -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 method according to the invention In addition to water, inert organic solvents are particularly suitable. These include in particular aliphatic, alicyclic or aromatic, given if 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 200 ° C, preferably between 10 ° C and 150 ° 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 order settlement is generally in a suitable diluent in the presence carried out a reaction auxiliary and the reaction mixture is in general mine stirred for several hours at the required temperature. The processing tion is carried out according to customary methods (cf. 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. use in the following plants be:

Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xan thium, convolvulus, ipomoea, polygonum, sesbania, ambrosia, cirsium, carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus, Taraxacum. Dicot cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, lactuca, cucumis, cucurbita.

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

Monocot cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, sorghum, panicum, saccharum, pineapple, asparagus, allium.

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

The active compounds according to the invention are suitable depending on the concentration tion 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 are also suitable for controlling animal pests preferably arthropods and nematodes, especially insects and. Arachnids, those in agriculture, in forests, in the protection of stocks and materials as well as on the Hygiene sector occur. They are against normally sensitive and resistant species effective against all or individual stages of development. To the above mentioned Pests include:  

From the order of the Isopoda z. B. Oniscus asellus, Armadillidium vulgare, Porcellio scaber.

From the order of the Diplopoda z. B. Blaniulus guttulatus.

From the order of the Chilopoda z. B. Geophilus carpophagus, Scutigera spec.

From the order of the Symphyla z. B. Scutigerella immaculata.

From the order of the Thysanura z. B. Lepisma saccharina.

From the order of the Collembola z. B. Onychiurus armatus.

From the order of Orthoptera z. B. Blatta orientalis, Periplaneta americana, Leu cophaea maderae, Blattella germanica, Acheta domesticus, Gryllotalpa spp., Locusta migratoria migratorioides, Melanoplus differentialis, Schistocerca gregaria. From the order of the Dermaptera z. B. Auricular Forficula.

From the order of the Isoptera z. B. Reticulitermes spp.

From the order of the Anoplura z. B. Pediculus humanus corporis, Haematopinus spp., Linognathus spp.

From the order of the Mallophaga z. B. Trichodectes spp., Damalinea spp.

From the order of the Thysanoptera z. B. Hercinothrips femoralis, Thrips tabaci.

From the order of Heteroptera z. B. Eurygaster spp., Dysdercus intermedius, Piesma quadrata, Cimex lectularius, Rhodnius prolixus, Triatoma spp.  

From the order of Homoptera z. B. Aleurodes brassicae, Bemisia tabaci, Trialeu rodes vaporariorum, Aphis gossypü, Brevicoryne brassicae, Cryptomyzus ribis, Aphis fabae, Aphis pomi, Eriosoma lanigerum, Hyalopterus arundinis, Macrosiphum avenae, Myzus spp., Pemphigus spp., Phorodon humuli, Phylloxera vastatrix, Rhopa losiphum padi, Empoasca spp., Euscelis bilobatus, Nephotettix cincticeps, Lecanium corni, Saissetia oleae, Laodelphax striatellus, Nilaparvata lugens, Aonidiella aurantü, Aspidiotus hederae, Pseudococcus spp. Psylla spp.

From the order of the Lepidoptera z. B. Pectinophora gossypiella, Bupalus piniarius, Cheimatobia brumata, Lithocolletis blancardella, Hyponomeuta padella, Plutella maculipennis, Malacosoma neustria, Euproctis chrysorrhoea, Lymantria spp. Buccu latrix thurberiella, Phyllocnistis citrella, Agrotis spp., Euxoa spp., Feltia spp., Earias insulana, Heliothis spp., Spodoptera exigua, Mamestra brassicae, Panolis flammea, Prodenia litura, Spodoptera spp., Trichoplusia ni, Carpocapsa pomonella, Pieris spp., Chilo spp., Pyrausta nubilalis, Ephestia kuehniella, Galleria mellonella, Tineola bisselliella, tinea pellionella, Hofmannophila pseudospretella, Cacoecia podana, Capua reticulana, Choristoneura fumiferana, Clysia ambiguella, Homona magna nima, Tortrix viridana.

From the order of the Coleoptera z. B. Anobium punctatum, Rhizopertha dominica, Acanthoscelides obtectus, Bruchidius obtectus, Hylotrupes bajulus, Agelastica alni, Leptinotarsa decemlineata, Phaedon cochleariae, Diabrotica spp., Psylliodes chry socephala, Epilachna varivestis, Atomaria spp., Oryzaephilus surinamensis, Antho nomus spp., Sitophilus spp., Otiorrhynchus sulcatus, Cosmopolites sordidus, Ceuthorrhynchus assirnilis, Hypera postica, Dermestes spp., Trogoderma spp., Anthrenus spp., Attagenus spp., Lyctus spp., Meligethes aeneus, Ptinus spp., Niptus hololeucus, Gibbium psylloides, Tribolium spp., Tenebrio molitor, Agriotes spp., Conoderus spp., Melolontha melolontha, Amphimallon solstitialis, Costelytra zealandica.  

From the order of the Hymenoptera z. B. Diprion spp., Hoplocampa spp., Lasius spp., Monomorium pharaonis, Vespa spp.

From the order of the Diptera z. B. Aedes spp., Anopheles spp., Culex spp., Drosophila melanogaster, Musca spp., Fannia spp., Calliphora erythrocephala, Lucilia spp., Chrysomyia spp., Cuterebra spp., Gastrophilus spp., Hyppobosca spp., Stomoxys spp., Oestrus spp., Hypoderma spp., Tabanus spp., Tannia spp., Bibio hortulanus, Oscinella frit, Phorbia spp., Pegomyia hyoscyami, Ceratitis capitata, Dacus oleae, Tipula paludosa.

From the order of the Siphonaptera z. B. Xenopsylla cheopis, Ceratophyllus spp.

From the order of the Arachnida z. B. Scorpio maurus, Latrodectus mactans.

From the order of Acarina z. B. Acarus siro, Argas spp., Ornithodoros spp., Dermanyssus gallinae, Eriophyes ribis, Phyllocoptruta oleivora, Boophilus spp., Rhipicephalus spp., Amblyomma spp., Hyalomma spp., Ixodes spp., Psoroptes spp., Chorioptes spp., Sarcoptes spp., Tarsonemus spp., Bryobia praetiosa, Panonychus spp., Tetranychus spp ..

The plant parasitic nematodes include z. B. Pratylenchus spp., Radopholus spp., Ditylenchus spp., Tylenchulus spp., Heterodera spp., Globodera spp., Meloidogyne spp., Aphelenchoides spp., Longidorus spp., Xiphinema spp., Trichodorus spp., Tylenchus spp., Helicotylenchus spp., Rotylenchus spp., Tylenchulus spp.

The compounds according to the invention are very suitable for controlling plants harmful insects, such as. B. Cabbage cockroaches (Plutella spp.).

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-imp gnated 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 Vermi 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 alkylnaph thaline, chlorinated Aromatemiud 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 Rock flours, 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 emulsifier ren, 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. More addi mineral and vegetable oils can be used.

Dyes such as inorganic pigments, e.g. B. iron oxide, titanium oxide, ferro cyan and organic dyes such as alizarin, azo and metal phthalocyanine dyes and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, Molybdenum and zinc can be used.

The formulations generally contain between 0.1 and 95 percent by weight Active ingredient, preferably between 0.5 and 90%.

The active compounds according to the invention can be used as such or in their formulations also used in a mixture with known herbicides for weed control find, where ready formulations or tank mixes are possible.

Known herbicides are suitable for the mixtures, for example Acetochlor, acifluorfen (-sodium), aclonifen, alachlor, alloxydim (-sodium), Ametryne, Amidochlor, Amidosulfuron, Anilofos, Asulam, Atrazine, Azafenidin, Azimsulfuron, benazolin (-ethyl), benfuresate, bensulfuron (-methyl), bentazone, Benzofenap, Benzoylprop (-ethyl), Bialaphos, Bifenox, Bispyribac (-sodium), Bromobutide, Bromofenoxim, Bromoxynil, Butachlor, Butroxydim, Butylate, Cafenstrole, Caloxydim, Carbetamide, Carfentrazone (-ethyl), Chlomethoxyfen, Chloramben, chloridazon, chlorimuron (-ethyl), chloronitrofen, chlorsulfuron, Chiortoluron, Cinidon (-ethyl), Cinmethylin, Cinosulfuron, Clethodim, Clodina fop (-propargyl), clomazone, clomeprop, clopyralid, clopyrasulfuron (-methyl),  Cloransulam (methyl), cumyluron, cyanazine, cybutryne, cycloate, cyclosulfame uron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB, 2,4-DP, desmedipham, Di apate, dicamba, diclofop (-methyl), diclosulam, diethatyl (-ethyl), difenzoquat, Diflufenican, Diflufenzopyr, Dimefuron, Dimepiperate, Dimethachlor, Dimetha metryn, dimethenamid, dimexyflam, dinitramine, diphenamid, diquat, dithio pyr, Diuron, Dymron, Epoprodan, EPTC, Esprocarb, Ethalfluralin, Ethametsulf uron (-methyl), ethofumesate, ethoxyfen, ethoxysulfuron, etobenzanide, fenoxa prop (-P-ethyl), flamprop (-isopropyl), flamprop (-isopropyl-L), flamprop (-methyl), Flazasulfuron, fluazifop (-P-butyl), fluazolate, flucarbazone, flufenacet, flumet sulam, flumiclorac (-pentyl), flumioxazin, flumipropyn, flumetsulam, fluomet uron, fluorochloridone, fluoroglycofen (-ethyl), flupoxam, flupropacil, flurpyr sulfuron (-methyl, -sodium), flurenol (-butyl), fluridone, fluroxypyr (-meptyl), Flurprimidol, Flurtamone, Fluthiacet (-methyl), Fluthiamide, Fomesafen, Glu fosinate (-ammonium), glyphosate (-isopropylammonium), halosafen, haloxyfop (- ethoxyethyl), haloxyfop (-P-methyl), hexazinones, imazamethabenz (-methyl), Imazamethapyr, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazo sulfuron, iodosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, Isoxachlortole, Isoxaflutole, Isoxapyrifop, Lactofen, Lenacil, Linuron, MCPA, MCPP, Mefenacet, Mesotrione, Metamitron, Metazachlor, Methabenzthiazuron, Metobenzuron, metobromuron, (alpha-) metolachlor, metosulam, metoxuron, Metribuzin, Metsulfuron (-methyl), Molinate, Monolinuron, Naproanilide, Naprop amide, neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl, Oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat, pelargonic acid, Pendimethalin, Pentoxazone, Phenmedipham, Piperophos, Pretilachlor, Primisulf uron (-methyl), prometryn, propachlor, propanil, propaquizafop, propisochlor, Propyzamides, prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazolates, pyrazo sulfuron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb, pyridate, pyrimino bac (-methyl), pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, Quizalofop (-P-ethyl), quizalofop (-P-tefuryl), rimsulfuron, sethoxydim, simazine, Simetryn, Sulcotrione, Sulfentrazone, Sulfometuron (-methyl), Sulfosate, Sulfosulf  uron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine, terbutryn, thenyl chlorine, thiafluamides, thiazopyr, thidiazimin, thifensulfuron (-methyl), thiobes carb, Tiocarbazil, Tralkoxydim, Triallate, Triasulfuron, Tribenuron (-methyl), Tri clopyr, tridiphane, trifluralin and triflusulfuron.

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

The active substances can be used as such, in the form of their formulations or in the form thereof application forms prepared by further dilution, such as ready-to-use Solutions, suspensions, emulsions, powders, pastes and granules are used the. 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

A mixture of 1.5 g (5 mmol) of 2-imino-5-methyl-3- (3-trifluoromethyl-phenyl) - thiazoline hydrochloride, 1.2 g (5 mmol) 2-methylsulfonyl-5-trifluoromethyl-1,3,4- thiadiazole, 6.5 g (20 mmol) of cesium carbonate and 50 ml of acetonitrile is used for 60 minutes heated under reflux. After cooling to room temperature, the filtrate is filtered concentrated in a water jet vacuum, the residue taken up in methylene chloride, washed with 1N hydrochloric acid, dried with sodium sulfate and filtered. The filtrate is concentrated in a water jet vacuum, the residue with diisopropyl ether dige and crystallized product isolated by suction.

0.5 g (24% of theory) of 5-methyl-3- (3-trifluoromethylphenyl) -2- (5- trifluoromethyl-1,3,4-thiadiazol-2-yl) -imino-thiazoline with a melting point of 159 ° 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 about 24 hours the soil is sprayed with the active ingredient preparation so that the ge desired amount of active ingredient is applied per unit area. The concentration the spray liquor is chosen so that the ge in 1000 liters of water per hectare desired amount of active ingredient is applied.

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

It means:
0% = no effect (like untreated control)
100% = total annihilation

In this test, for example, the compounds according to the preparation example show 1, 3 and 7 with good tolerance to crops, such as. B. Wheat and soybeans, strong against weeds.  

Example B

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

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

The active ingredient preparation is used to inject test plants which are 5 - 15 cm so that the desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 1000 l water / ha the desired amounts of active ingredient are applied. After three weeks, the degree of damage to the plants is rated in% damage compared to the development of the untreated control.

It means:
0% = no effect (like untreated control)
100% = total annihilation

In this test, for example, the compounds according to the preparation example show 1, 3, 6 and 7 with good tolerance to crops, such as. B. Corn and wheat, strong weed control.  

Example C Plutella test / artificial feed

Solvent: 100 parts by weight of acetone
Emulsifier: 1900 parts by weight of methanol

To produce a suitable preparation of active compound, mix 1 Part by weight of active ingredient with the specified amount of solvent and dilutes it Concentrate with methanol to the desired concentrations.

A specified amount of active ingredient is added to a standardized amount of synthetic feed pipetting of the desired concentration. After the methanol evaporates , a film can lid with about 100 plutella eggs is placed on each cavity puts. The newly hatched larvae migrate to the treated synthetic food. In this test, e.g. B. the following compound of Preparation 6 good Effectiveness.

Claims (9)

1. Substituted 2-imino-3-thiazolines of the general formula (I)
in which
A represents a single bond or optionally substituted alkane diyl (alkylene),
R ¹ represents optionally substituted alkyl, cycloalkyl, aryl or heterocyclyl,
R ^{2 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halo, or optionally substituted alkyl or alkoxy carbonyl,
R ^{3 represents} hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halo, or optionally substituted alkyl or alkoxy carbonyl, and
R ^{4 represents} hydrogen, cyano, halogen or alkoxy, or optionally optionally substituted cycloalkyl, aryl or heterocyclyl,
including the possible E and Z isomers of these compounds. 2. Substituted 2-imino-thiazolines according to claim 1, characterized in that
A represents a single bond or alkanediyl (alkylene) having 1 to 4 carbon atoms which is optionally substituted by cyano, halo or C ₁ -C ₄ alkoxy,
R ¹ represents optionally cyano-, halogen or C ₁ -C ₄ alkoxy substitu iertes alkyl having 1 to 6 carbon atoms, represents optionally cyano-, halogen- or C ₁ -C ₄ -alkyl-substituted cycloalkyl having 3 to 6 carbon atoms, optionally substituted by Nitro, cyano, halogen, C ₁ -C ₄ alkyl, C ₁ -C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C, -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 or C ₁ -C ₄ halo alkylsulfonyl substituted aryl having 6 or 10 carbon atoms, or for each optionally substituted by Cyano, 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 halo alkylsulfinyl, C ₁ -C ₄ alkylsulfonyl or C ₁ -C ₄ haloalkylsulfonyl substituted, monocyclic or bicyclic heterocyclyl having 1 to 9 carbon atoms, 1 to 4 S. tickstoffatomen and / or 1 or 2 oxygen or sulfur atoms,
R ^{2 stands} for hydrogen, cyano, carboxy, carbamoyl, thiocarbamoyl, halo or for alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, each having up to 4 carbon atoms,
R ^{3 represents} hydrogen, cyano, carboxy, carbamyl, thiocarbamoyl, halo, or alkyl or alkoxycarbonyl, each optionally substituted by cyano, halogen or C ₁ -C ₄ -alkoxy, each having up to 4 carbon atoms, and
R ⁴ for hydrogen, cyano, halogen or alkoxy, for cycloalkyl having 3 to 6 carbon atoms optionally substituted by cyano, halogen or C ₁ -C ₄ alkyl, for optionally substituted by nitro, cyano, 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 or C ₁ -C ₄ haloalkylsulfonyl substituted aryl having 6 or 10 carbon atoms, or for each optionally substituted by cyano, halogen, C ₁ -C ₄ alkyl, C ₁ - C ₄ haloalkyl, C ₁ -C ₄ alkoxy, C ₁ -C ₄ halo alkoxy, C ₁ -C ₄ alkylthio, C ₁ -C ₄ haloalkylthio, C ₁ -C ₄ alkylsulfinyl, C ₁ -C ₄ Haloalkylsulfinyl, C ₁ -C ₄ alkylsulfonyl or C ₁ -C ₄ halo alkylsulfonyl substituted, monocyclic or bicyclic heterocyclic having 1 to 9 carbon atoms, 1 to 4 nitrogen atoms and / or 1 or 2 oxygen or sulfur atoms eht. 3. Substituted 2-imino-thiazolines according to claim 1, characterized in that
A for a single bond or for methylene (CH ₂ ), dimethylene (ethane-1,2-diyl, CH ₂ CH ₂ ) or trimethylene (propane-1,3-diyl, CH) which is optionally substituted by cyano, fluorine and / or chlorine ₂ CH ₂ CH ₂ )
R ¹ for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, each optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, for in each case optionally by cyano, fluorine, chlorine, Methyl or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl, for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluor methyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethyl or for each optionally by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, Difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, tri fluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl substituted heterocyclyl from the series furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl
R ^{2 represents} methyl, ethyl, chlorine or bromine,
R ^{3 represents} hydrogen or methyl, and
R ⁴ for hydrogen, cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy, for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for optionally by Nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy , methylthio, ethylthio, n- or i-propylthio, difluoro methylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, tri fluormethylsulfmyl, methylsulfonyl, ethylsulfonyl, fonyl Trifluormethylsul, methylenedioxy, ethylenedioxy, difluoromethylenedioxy, ethylenedioxy trifluoro or tetrafluoroethylenedioxy substituted phenyl, or represents in each case optionally cyano- , Fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio , Ethylthio, n- or i-propyl thio, difluoromethyl thio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoro methylsulfinyl, methylsulfonyl, ethylsulfonyl or Trifluormethylsul fonyl substituted, optionally benzannelliertes heterocyclyl from the series comprising furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, Isothiazo lyl, S, S-dioxo-isothiazolyl, oxadiazolyl , Thiadiazolyl, pyridinyl or pyrimidinyl. 4. Substituted 2-imino-thiazolines according to claim 1, characterized in that
A represents a single bond or methylene (CH ₂ ),
R ¹ for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethyl thio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, Trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl-substituted phenyl, or for each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, trifluoromethyl , Methoxy, ethoxy, n- or i-propoxy, di fluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonomethylsulfonyl or trifluoromethylsulfonyl erocyclyl from the series furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl or pyrimidinyl,
R ^{2 represents} methyl or ethyl,
R ^{3 represents} hydrogen or methyl, and
R ⁴ for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethyl thio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, Trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl, trifluoromethylsulfonyl, methylenedioxy, ethylenedioxy, difluoromethylenedioxy, trifluoroethylenedioxy or tetrafluorethylenedioxy or phenyl which is optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl or n-, n- i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, tr ifluoromethylsulfmyl, methylsulfonyl, ethylsulfonyl or trifluoromethylsulfonyl-substituted heterocyclyl from the series furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl or pyrimidinyl. 5. Substituted 2-imino-thiazolines according to claim 1, characterized in that A for methylene (CH ₂ ), dimethylene (ethane-1,2-diyl, CH ₂ CH ₂ ) optionally substituted by cyano, fluorine and / or chlorine ) or trimethylene (propane-1,3-diyl, CH ₂ CH ₂ CH ₂ ),
R ¹ for cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, for optionally by nitro, cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfmyl, ethylsulfinyl, Trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonyl or trifluoromethyl sulfonyl substituted phenyl, or for each optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-, 1-, s- or t-butyl, trifluoromethyl , Methoxy, ethoxy, n- or i-propoxy, di fluoromethoxy, trifluoromethoxy, methylthio, ethylthio, n- or i-propylthio, difluoromethylthio, trifluoromethylthio, methylsulfinyl, ethylsulfinyl, trifluoromethylsulfinyl, methylsulfonyl, ethylsulfonomethylsulfonyl or trifluoromethylsulfonyl rocyclyl from the series furyl, thienyl, oxazolyl, isoxazolyl, thiazolyl, oxadiazolyl, thiadiazolyl, pyridinyl or pyrimidinyl, R ^{2 represents} methyl or ethyl,
R ^{3 represents} hydrogen or methyl, and
R ^{4 represents} hydrogen, cyano, fluorine, chlorine, bromine, methoxy, ethoxy, n- or i-propoxy. 6. Substituted 2-imino-3-thiazolines according to one of claims 1 to 5, characterized in that R ^{4 is} phenyl or pyridinyl substituted by trifluoromethyl and / or fluorine or chlorine. 7. A process for the preparation of substituted 2-imino-thiazolines according to one of claims 1 to 6, characterized in that 2-imino-thia zolines 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 6,
- or acid adducts of compounds of the general formula (II) -
with compounds of the general formula (III)
XR ¹ (III)
in which
R ^{1 has} the meaning given in one of claims 1 to 5 and
X represents halogen or the group -SO ₂ alkyl,
if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent,
and, if appropriate, subsequently carries out substitution reactions in the customary manner as part of the substituent definition. 8. Use of at least one substituted 2-imino-thiazoline according to one of claims 1 to 6 for controlling undesirable plants and / or against animal pests, especially insects. 9. Plant treatment products, characterized by the content of at least a substituted 2-imino-thiazoline according to any one of claims 1 to 6 and usual extenders.