DE102010042866A1 - New thioamide compounds, useful for controlling undesirable plant growth or weeds in cultural plants e.g. Arachis hypogaea, Allium cepa, Elaeis guineensis and Gossypium herbaceum - Google Patents

Abstract

Thioamide compounds (I) and their N-oxides or salts are new. Thioamide compounds of formula (I) and their N-oxides or salts are new. R1 : O-RA, S(O) n-RA or O-S(O) n-RA, where R1 is optionally substituted by R1b; RA : H, 1-4C-(halo)alkyl, Z-3-6C-cycloalkyl, 2-6C-alkenyl, Z-3-6C-cycloalkenyl, 2-6C-alkynyl, Z-(tri-1-4C-alkyl)silyl, Z-C(=O)-R1a, Z-NRa1-C(O)-NRa1Ra2, Z-P(=O)(R1a) 2, NRa1Ra2 or 3-7 membered monocyclic or 9- or 10-membered bicyclic, optionally saturated or aromatic heterocycle containing 1-4 heteroatoms of O, N or S, where the heterocycle is bonded via C or N, and optionally partially or completely substituted by R1a and/or R1b; R1a : H, OH, 1-8C-alkyl, 1-4C-haloalkyl, Z-3-6C-cycloalkyl, 2-8C-alkenyl, Z-5-6C-cycloalkenyl, 2-8C-alkynyl, Z-1-6C-alkoxy, Z-1-4C-haloalkoxy, Z-3-8C-alkenyloxy, Z-3-8C-alkynyloxy, NRa1Ra2, 1-6C-alkylsulfonyl, Z-(tri-1-4C-alkyl)silyl, Z-phenyl, Z-phenoxy, Z-phenylamino or 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1-4 heteroatoms of O, N or S, where the cyclic groups are optionally substituted by 1-5 R1b; either Ra1, Ra2 : H, 1-8C-alkyl, 1-4C-haloalkyl, 3-8C-alkenyl, 3-8C-alkynyl, Z-3-6C-cycloalkyl, Z-1-8C-alkoxy, Z-1-8C-haloalkoxy, Z-C(= O)-R1a, Z-phenyl or 3-7 membered monocyclic or 9- or 10-membered bicyclic, optionally saturated or aromatic heterocycle containing 1-4 heteroatoms of O, N or S, where the heterocycle is bonded via Z; or Ra1NRa2 : 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1-4 heteroatoms of O, N or S; Z : a covalent bond or 1-4C-alkylene; n : 0-2; R2 : phenyl, naphthyl or 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1-4 heteroatoms of O, N or S, where the cyclic groups are optionally substituted by 1-4 R1b; either R1b : Z-CN, Z-OH, Z-NO 2, Z-halo, 1-8C-alkyl, 1-4C-haloalkyl, 2-8C-alkenyl, 2-8C-alkynyl, Z-1-8C-alkoxy, Z-1-8C-haloalkoxy, Z-3-10C-cycloalkyl, O-Z-3-10C-cycloalkyl, Z-C(=O)-R1a, NRa1-Ra2, Z-(tri-1-4C-alkyl)silyl, Z-phenyl or S(O) nRbb; or R1bCR1b : 5- or 6-membered optionally partially or completely unsaturated ring, which additionally contains 1-3 heteroatoms comprising O, N or S; Rbb : 1-8C-alkyl or 1-6C-haloalkyl; Y1 : O or S; A, E, G, M : N or C-R1c, where one or more two groups comprise N; and R1c : H or R1b. Provided that A is not N, when E, G and M are CH. An independent claim is included for a composition comprising (I) and auxiliary additives. [Image] ACTIVITY : Herbicide. MECHANISM OF ACTION : None given.

Description

worin die Variablen folgende Bedeutung haben
R¹ O-R^A, S(O)_n-R^A oder O-S(O)_n-R^A;
R^A Wasserstoff, C₁-C₄-Alkyl, Z-C₃-C₆-Cycloalkyl, C₁-C₄-Haloalkyl, C₂-C₆-Alkenyl, Z-C₃-C₆-Cycloalkenyl, C₂-C₆-Alkinyl, Z-(Tri-C₁-C₄-alkyl)silyl, Z-C(=O)-R^a, Z-NRⁱ-C(O)-NRⁱRⁱⁱ, Z-P(=O)(R^a)₂, NRⁱRⁱⁱ, 3- bis 7-gliedriger monocyclischer oder 9- oder 10-gliedriger bicyclischer gesättigter, ungesättigter oder aromatischer Heterocyclus, enthaltend 1, 2, 3 oder 4 Heteroatome ausgewählt aus O, N und S, der teilweise oder vollständig durch Gruppen R^a und/oder R^b substituiert sein kann,
R^a Wasserstoff, OH, C₁-C₈-Alkyl, C₁-C₄-Haloalkyl, Z-C₃-C₆-Cycloalkyl, C₂-C₈-Alkenyl, Z-C₅-C₆-Cycloalkenyl, C₂-C₈-Alkinyl, Z-C₁-C₆-Alkoxy, Z-C₁-C₄-Haloalkoxy, Z-C₃-C₈-Alkenyloxy, Z-C₃-C₈-Alkinyloxy, NRⁱRⁱⁱ C₁-C₆-Alkylsulfonyl, Z-(Tri-C₁-C₄-alkyl)silyl, Z-Phenyl, Z-Phenoxy, Z-Phenylamino und 5- oder 6-gliedriger monocyclischer oder 9- oder 10-gliedriger bicyclischer Heterocyclus, enthaltend 1, 2, 3 oder 4 Heteroatome ausgewählt aus O, N und S, wobei die cyclischen Gruppen unsubstituiert oder durch 1, 2, 3, 4 oder 5 Gruppen R^b substituiert sind, bedeutet;
Rⁱ, Rⁱⁱ unabhängig voneinander Wasserstoff, C₁-C₈-Alkyl, C₁-C₄-Haloalkyl, C₃-C₈-Alkenyl, C₃-C₈-Alkinyl, Z-C₃-C₆-Cycloalkyl, Z-C₁-C₈-Alkoxy, Z-C₁-C₈-Haloalkoxy, Z-C(=O)-R^a, Z-Phenyl, über Z gebundener 3- bis 7-gliedriger monocyclischer oder 9- oder 10-gliedriger bicyclischer gesättigter, ungesättigter oder aromatischer Heterocyclus, enthaltend 1, 2, 3 oder 4 Heteroatome ausgewählt aus O, N und S;
Rⁱ und Rⁱⁱ können auch gemeinsam mit dem N-Atom, an das sie gebunden sind, einen 5- oder 6-gliedrigen monocyclischen oder 9- oder 10-gliedrigen bicyclischer Heterocyclus bilden, enthaltend 1, 2, 3 oder 4 Heteroatome ausgewählt aus O, N und S;
Z eine kovalente Bindung oder C₁-C₄-Alkylen;
n 0, 1 oder 2;
R² Phenyl, Naphthyl oder und 5- oder 6-gliedriger monocyclischer oder 9- oder 10-gliedriger bicyclischer aromatischer Heterocyclus, enthaltend 1, 2, 3 oder 4 Heteroatome ausgewählt aus O, N und S, wobei die cyclischen Gruppen unsubstituiert oder durch 1, 2, 3, 4 oder 5 Gruppen R^b substituiert sind, bedeutet;
R^b unabhängig voneinander Z-CN, Z-OH, Z-NO₂, Z-Halogen, C₁-C₈-Alkyl, C₁-C₄-Haloalkyl, C₂-C₈-Alkenyl, C₂-C₈-Alkinyl, Z-C₁-C₈-Alkoxy, Z-C₁-C₈-Haloalkoxy, Z-C₃-C₁₀-Cycloalkyl, O-Z-C₃-C₁₀-Cycloalkyl, Z-C(=O)-R^a, NRⁱRⁱⁱ, Z-(Tri-C₁-C₄-alkyl)silyl, Z-Phenyl und S(O)_nR^bb, wobei
R^bb C₁-C₈-Alkyl und C₁-C₆-Haloalkyl bedeutet und n für 0, 1 oder 2 steht;
R^b kann auch gemeinsam mit der an das benachbarte C-Atom gebundene Gruppe R^b einen fünf- oder sechsgliedrigen gesättigten, teilweise oder vollständig ungesättigten Ring bilden, der neben Kohlenstoff-1, 2 oder 3 Heteroatome ausgewählt aus O, N und S enthalten kann;
Y O oder S;
A, E, G, M N und C-R^c, wobei eine oder zwei Gruppen davon N bedeuten, mit der Maßgabe, dass nicht A für N steht, wenn E, G und M C-H bedeuten;
R^c Wasserstoff oder eine der bei R^b genannten Gruppen;
wobei in Gruppen R^A, R³ und deren Untersubstituenten die Kohlenstoffketten und/oder die cyclischen Gruppen teilweise oder vollständig durch Gruppen R^b substituiert sein können,
sowie deren N-Oxide und landwirtschaftlich geeignete Salze.The present invention relates to substituted thioamides of the formula I.

wherein the variables have the following meaning
R ¹ OR ^A , S (O) _n -R ^A or OS (O) _n -R ^A ;
R ^{A is} hydrogen, C ₁ -C ₄ -alkyl, ZC ₃ -C ₆ -cycloalkyl, C ₁ -C ₄ -haloalkyl, C ₂ -C ₆ -alkenyl, ZC ₃ -C ₆ -cycloalkenyl, C ₂ -C ₆ - alkynyl, Z- (tri-C ₁ -C ₄ alkyl) silyl, ZC (= O) -R ^a, Z-NR ^i, -C (O) -NR ⁱ R ^ii, ZP (= O) (R ^a) ₂ , NR ⁱ R ⁱⁱ , 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S, partially or completely may be substituted by groups R ^a and / or R ^b ,
R ^{a is} hydrogen, OH, C ₁ -C ₈ -alkyl, C ₁ -C ₄ -haloalkyl, ZC ₃ -C ₆ -cycloalkyl, C ₂ -C ₈ -alkenyl, ZC ₅ -C ₆ -cycloalkenyl, C ₂ -C ₈ alkynyl, ZC ₁ -C ₆ alkoxy, ZC ₁ -C ₄ haloalkoxy, ZC ₃ -C ₈ alkenyloxy, ZC ₃ -C ₈ alkynyloxy, NR ⁱ R ⁱⁱ C ₁ -C ₆ alkylsulfonyl, Z- (Tri-C ₁ -C ₄ alkyl) silyl, Z-phenyl, Z-phenoxy, Z-phenylamino and 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 Heteroatoms selected from O, N and S, wherein the cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or 5 groups R ^b ;
R ⁱ , R ⁱⁱ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₄ -haloalkyl, C ₃ -C ₈ -alkenyl, C ₃ -C ₈ -alkynyl, ZC ₃ -C ₆ -cycloalkyl, ZC C ₁ -C ₈ -alkoxy, ZC ₁ -C ₈ -haloalkoxy, ZC (= O) -R ^a , Z-phenyl, Z-linked 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S;
R ⁱ and R ⁱⁱ may also together with the N-atom to which they are attached form a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S;
Z is a covalent bond or C ₁ -C ₄ -alkylene;
n is 0, 1 or 2;
R ^{2 is} phenyl, naphthyl or and 5- or 6-membered monocyclic or 9- or 10-membered bicyclic aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S, wherein the cyclic groups unsubstituted or by 1 , 2, 3, 4 or 5 groups R ^{b are} substituted;
R ^b independently of one another Z-CN, Z-OH, Z-NO ₂ , Z-halogen, C ₁ -C ₈ -alkyl, C ₁ -C ₄ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ Alkynyl, ZC ₁ -C ₈ alkoxy, ZC ₁ -C ₈ haloalkoxy, ZC ₃ -C ₁₀ cycloalkyl, OZC ₃ -C ₁₀ cycloalkyl, ZC (= O) -R ^a , NR ⁱ R ⁱⁱ , Z - (tri-C ₁ -C ₄ alkyl) silyl, Z-phenyl and S (O) _n R ^bb , wherein
R ^{bb is} C ₁ -C ₈ alkyl and C ₁ -C ₆ haloalkyl and n is 0, 1 or 2;
R ^b can also form, together with the group R ^b attached to the adjacent carbon atom, a five- or six-membered saturated, partially or completely unsaturated ring which, besides carbon-1, 2 or 3, can contain heteroatoms selected from O, N and S. ;
YO or S;
A, E, G, MN and CR ^c , wherein one or two groups thereof are N, with the proviso that not A is N when E, G and M are CH;
R ^{c is} hydrogen or one of the groups mentioned for R ^b ;
in groups R ^A , R ³ and their sub-substituents, the carbon chains and / or the cyclic groups may be partially or completely substituted by groups R ^b ,
and their N-oxides and agriculturally suitable salts.

Moreover, the invention relates to processes and intermediates for the preparation of the thioamides of the formula I and their N-oxides, their agriculturally useful salts, as well as active ingredient combinations containing them, agents containing them and their use as herbicides, d. H. for controlling harmful plants, and a method for controlling undesired plant growth, which comprises allowing a herbicidally effective amount of at least one thioamide of the formula I or an agriculturally useful salt of I to act on plants, their seeds and / or their habitat.

Further embodiments of the present invention can be taken from the claims, the description and the examples. It is understood that the features mentioned above and those yet to be explained of the article according to the invention not only in each of the specified Combination, but also usable in other combinations, without departing from the scope of the invention.

In WO 2009/090401 and WO 2009/090402 herbicidal pyridopyrazines or naphthyridinones are described, however, their herbicidal action at low application rates or compatibility with crop plants remains in need of improvement.

An object of the present invention is to provide compounds having herbicidal activity. In particular, active ingredients should be made available which have a high herbicidal action, in particular even at low application rates, and their compatibility with crop plants for commercial exploitation is sufficient.

These and other objects are achieved by the compounds of the formula I defined above and by their N-oxides, as well as their agriculturally suitable salts.

The compounds of the invention can analogously to in WO 2008/009908 and WO 2008/071918 described synthetic routes are prepared by standard methods of organic chemistry, for example according to the synthesis route described below. Alternatively, the off WO 2009/090401 and WO 2009/090402 known compounds are converted by sulfurization in the thioamides of the formula I.

Pyridinecarboxylic acids of the formula II can be reacted with carbonyl compounds of the formula III to give compounds of the formula IV. In formulas II and III, the variables have the meaning given for formula I. The group Hal represents a halogen atom or another suitable nucleophilic leaving group, such as alkoxy or phenoxy.

This reaction is usually carried out at temperatures of -78 ° C to 120 ° C, preferably -20 ° C to 50 ° C, in an inert organic solvent in the presence of a base such as. B. triethylamine ( see. J. Agric. and Food Chem. 1994, 42 (4), 1019-1025 .), A catalyst such. B. dicyclohexylcarbodiimide (see. Egyptian Journal of Chemistry 1994, 37 (3), 273-282 .) or other known coupling reagents.

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane , Anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide, dimethylformamide and dimethylacetamide, more preferably halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene. It is also possible to use mixtures of the solvents mentioned.

As bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, Sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and alkali metal hydrogencarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyl lithium and phenyllithium, alkyl magnesium halides such as methyl magnesium chloride and alkali metal and alkaline earth metal alkoxides such as sodium, sodium, potassium, potassium tert. Butanolate and Dimethoxymagnesium, also organic bases, eg. B. tertiary amines such as trimethylamine, triethylamine, tributylamine, di-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred are tertiary amines such as trimethylamine, triethylamine, tributylamine, di-isopropylethylamine. The bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.

The starting materials are generally reacted with one another in equimolar amounts.

The compounds of formula IV are activated by introducing a leaving group L ¹ . Suitable leaving groups L ¹ are generally those groups which increase the electrophilicity of the carbonyl group, for example O-alkyl, O-aryl, halides, activated esters or aldehydes (such as, for example, Weinreb amide), in particular pentafluorophenoxy.

This reaction is usually carried out at temperatures of -78 ° C to 120 ° C, preferably -20 ° C to 50 ° C, in an inert organic solvent in the presence of a base such as. For example, triethylamine (see. J. Agric. and Food Chem. 1994, 42 (4), 1019-1025 .), A catalyst such. B. dicyclohexylcarbodiimide (see. Egyptian Journal of Chemistry 1994, 37 (3), 273-282 ) or other known coupling reagents. Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane , Anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide, dimethylformamide and dimethylacetamide, more preferably methylene chloride and toluene. It is also possible to use mixtures of the solvents mentioned.

As bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, Sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate and calcium carbonate and alkali metal hydrogencarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyl lithium, butyl lithium and phenyllithium, alkyl magnesium halides such as methyl magnesium chloride and alkali metal and alkaline earth metal alkoxides such as sodium, sodium, potassium, potassium tert. Butanolate and Dimethoxymagnesium, also organic bases, eg. B. tertiary amines such as trimethylamine, triethylamine, tributylamine, di-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred are alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate, calcium carbonate, cesium carbonate and rubidium carbonate. The bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.

The starting materials are generally reacted with one another in equimolar amounts.

As agent HL ¹ are alcohols, optionally subst. Phenols, N, O-dialkylhydroxylamine, in particular pentafluorophenol or N, O-dimethylhydroxylamine in question.

The compounds of formula V are cyclized to the compounds of formula VI. In Formula VI, the variables have the meaning as in Formula I.

This reaction is usually carried out at temperatures of -78 ° C to 120 ° C, preferably -20 ° C to 50 ° C, in an inert organic solvent in the presence of a base, or a Lewis acid or a catalyst [see. Silverman, Richard BJ Am. Chem. Soc. 1981, 103 (13), 3910 ].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane , Anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, and dimethyl sulfoxide, dimethylformamide and dimethylacetamide, particularly preferably acetonitrile and dimethylformamide. It is also possible to use mixtures of the solvents mentioned.

As bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as lithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, Sodium amide and potassium amide, alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate, calcium carbonate, cesium carbonate and rubidium carbonate and alkali metal hydrogencarbonates such as sodium bicarbonate, organometallic compounds, in particular alkali metal alkyls such as methyllithium, butyl lithium and phenyllithium, alkyl magnesium halides such as methyl magnesium chloride and alkali metal and alkaline earth metal alkoxides such as sodium, sodium Potassium tert-butoxide and dimethoxy magnesium, as well as organic bases, e.g. B. tertiary amines such as trimethylamine, triethylamine, tributylamine, di-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and bicyclic amines into consideration. Particularly preferred are alkali metal and alkaline earth metal carbonates such as lithium carbonate, potassium carbonate, calcium carbonate, cesium carbonate and rubidium carbonate.

The bases are generally used in catalytic amounts, but they can also be used equimolar, in excess or optionally as a solvent.

The starting materials are generally reacted with one another in equimolar amounts.

Alternatively, the compounds of the formula VI can also be obtained via a reverse reaction sequence, ie from the reaction of the compounds of the formula II with compounds HL ¹ , the activated derivatives of the formula VII are obtained.

This reaction takes place per se under the conditions mentioned for the reaction of formula IV with HL ¹ .

The compounds of the formula VII can then be reacted with compounds III to give the derivatives of the formula V.

This reaction takes place per se under the conditions mentioned for the reaction of the formula II with III.

The sulfurization of the compounds of formula VI is carried out under known conditions with a Schwefelungsagenz [S], it is usually carried out at temperatures from 0 ° C to 180 ° C, preferably 20 ° C to 140 ° C, in an inert organic solvent [cp , Liebigs Ann Chem., P. 177 (1989) ].

Suitable solvents are aliphatic hydrocarbons such as pentane, hexane, cyclohexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as methylene chloride, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane , Anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, and dimethyl sulfoxide, particularly preferably toluene and tetrahydrofuran. It is also possible to use mixtures of the solvents mentioned.

Suitable sulfurizing agents are, for example, phosphorus pentasulfide or Lawesson's reagent.

The reaction mixtures are worked up in a conventional manner, for. B. by mixing with water, separation of the phases and optionally chromatographic purification of the crude products. The intermediate and end products fall z. T. in the form of colorless or pale brownish, viscous oils, which are freed or purified under reduced pressure and at moderately elevated temperature of volatile fractions. If the intermediate and end products are obtained as solids, the purification can also be carried out by recrystallization or trituration.

If individual compounds I are not accessible in the above-described ways, they can be prepared by derivatization of other compounds I.

However, if isomeric mixtures are involved in the synthesis, separation is generally not necessary because some of the isomers may partially interconvert during processing for use or in use (eg, exposure to light, acids, or bases) , Corresponding conversions may also take place after use, for example in the treatment of plants in the treated plant or in the harmful plant to be controlled.

The organic molecular moieties mentioned for the substituents of the compounds according to the invention are collective terms for individual listings of the individual group members. All hydrocarbon chains, such as alkyl, halo (gen) alkyl, alkenyl, alkynyl, and the alkyl moieties and alkenyl moieties in alkoxy, halo (gen) alkoxy, Alkylamino, dialkylamino, N-alkylsulfonylamino, alkenyloxy, alkynyloxy, alkoxyamino, alkylaminosulfonylamino, dialkylaminosulfonylamino, alkenylamino, alkynylamino, N- (alkenyl) -N- (alkyl) -amino, N- (alkynyl) -N- (alkyl) -amino, N- (alkoxy) -N- (alkyl) -amino, N- (alkenyl) -N- (alkoxy) -amino or N- (alkynyl) -N- (alkoxy) -amino may be straight-chain or branched.

The prefix C _n -C _m - indicates the particular carbon number of the hydrocarbon moiety. Unless otherwise stated, halogenated substituents preferably carry one to five identical or different halogen atoms, in particular fluorine atoms or chlorine atoms.

The meaning halogen is in each case fluorine, chlorine, bromine or iodine.

Furthermore, for example:
Alkyl and the alkyl moieties, for example, in alkoxy, alkylamino, dialkylamino, N-alkylsulfonylamino, alkylaminosulfonylamino, dialkylaminosulfonylamino, N- (alkenyl) -N- (alkyl) -amino, N- (alkynyl) -N- (alkyl) -amino, N- (Alkoxy) -N- (alkyl) -amino: saturated, straight-chain or branched hydrocarbon radicals having one or more carbon atoms, for. B. 1 to 2, 1 to 4, or 1 to 6 carbon atoms, for. C ₁ -C ₆ alkyl, such as methyl, ethyl, propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, 1,1-dimethylethyl, pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2- Dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, 1-ethyl-1-methylpropyl, 1-ethyl-2-methylpropyl. In one embodiment of the invention, alkyl is small alkyl groups such as C ₁ -C ₄ alkyl. In another embodiment of the invention, alkyl is greater alkyl groups such as C ₅ -C ₆ alkyl.

Haloalkyl (also referred to as haloalkyl): an alkyl radical as mentioned above, whose hydrogen atoms are partially or fully substituted by halogen atoms such as fluorine, chlorine, bromine and / or iodine, for. Chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2- Difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2, 3,3,3-pentafluoropropyl, heptafluoropropyl, 1- (fluoromethyl) -2-fluoroethyl, 1- (chloromethyl) -2-chloroethyl, 1- (bromomethyl) -2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4- Bromobutyl and nonafluorobutyl.

Cycloalkyl and cycloalkyl parts, for example, in cycloalkoxy or cycloalkylcarbonyl: monocyclic saturated hydrocarbon groups having three or more carbon atoms, eg. B. 3 to 6 carbon ring members such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl.

Alkenyl and alkenyl moieties, for example, in alkenylamino, alkenyloxy, N- (alkenyl) -N- (alkyl) -amino, N- (alkenyl) -N- (alkoxy) -amino: monounsaturated, straight-chain or branched hydrocarbon radicals having two or more carbon atoms. Atoms, z. B. 2 to 4, 2 to 6 or 3 to 6 carbon atoms and a double bond in any position, for. C ₂ -C ₆ alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 2-methyl-1 propenyl, 1-methyl-2-propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-1-butenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-butenyl, 2-methyl-3-butenyl, 3 Methyl 3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-1-propenyl, 1,2-dimethyl-2-propenyl, 1-ethyl-1-propenyl, 1-ethyl-2- propenyl, 1-hexenyl, 2-hexenyl, 3-hexenyl, 4-hexenyl, 5-hexenyl, 1-methyl-1-pentenyl, 2-methyl-1-pentenyl, 3-methyl-1-pentenyl, 4-methyl 1-pentenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 3-methyl-2-pentenyl, 4-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3 pentenyl, 3-methyl-3-pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl, 2-methyl-4-pentenyl, 3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-1-butenyl, 1, 2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-1-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2, 2-dimethyl-3-butenyl, 2,3-dimethyl-1-butenyl, 2,3-dimethyl-2-butenyl, 2,3-dimethyl-3-butenyl, 3,3-dimethyl-1-butenyl, 3, 3-dimethyl-2-butenyl, 1-ethyl-1-butenyl, 1-ethyl-2-butenyl, 1-ethyl-3-butenyl, 2-ethyl-1-butenyl, 2-ethyl-2-butenyl, 2- Ethyl 3-butenyl, 1,1,2-trimethyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-1-propenyl, 1-ethyl-2-methyl 2-propenyl.

Cycloalkenyl: monocyclic, monounsaturated hydrocarbon groups having 3 to 6, preferably 5 to 6, carbon ring members, such as cyclopenten-1-yl, cyclopenten-3-yl, cyclohexen-1-yl, cyclohexen-3-yl, cyclohexen-4-yl.

Alkynyl and alkynyl moieties, for example, in alkynyloxy, alkynylamino, N- (alkynyl) -N- (alkyl) -amino or N- (alkynyl) -N- (alkoxy) -amino: straight-chain or branched hydrocarbon groups having two or more carbon atoms, eg , B. 2 to 4, 2 to 6, or 3 to 6 carbon atoms and a triple bond in any position, for. B. C ₂ -C ₆ alkynyl such as ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3 Pentynyl, 4-pentynyl, 1-methyl-2-butynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1 Ethyl 2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-hexynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-1-pentynyl, 3-methyl-4-pentynyl, 4-methyl-1-pentynyl, 4-methyl-2-pentynyl, 1, 1-Dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3-butynyl, 3,3-dimethyl-1-butynyl, 1- Ethyl 2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl, 1-ethyl-1-methyl-2-propynyl.

Alkoxy: alkyl, as defined above, which is bonded via an oxygen atom: z. Methoxy, ethoxy, n-propoxy, 1-methylethoxy, butoxy, 1-methylpropoxy, 2-methylpropoxy or 1,1-dimethylethoxy, pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethylpropoxy, 1-ethylpropoxy, hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3- Dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1 methylpropoxy or 1-ethyl-2-methylpropoxy.

3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S may be bonded via C or N. Of these, preferred are 5- or 6-membered heterocycles.

N-linked saturated or unsaturated heterocyclic groups such as: pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazine-2-yl, 2-furyl , 3-furyl, 2-thienyl, 3-thienyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazole 3-yl, isothiazol-4-yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazole-5 -yl, thiazol-2-yl, thiazol-4-yl and thiazol-5-yl.

Via C-linked heteroaromatic groups, such as: pyrazol-3-yl, imidazol-5-yl, oxazol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazol-5-yl, pyridin-2-yl , Pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-4-yl, pyrazine-2-yl, [1H] -tetrazole-5 -yl and [2H] -tetrazol-5-yl.

Depending on the substitution pattern, the compounds of the formula I can contain one or more further chiral centers. The compounds according to the invention can therefore be present as pure enantiomers or diastereomers or as mixtures of enantiomers or diastereomers. The invention relates to both the pure enantiomers or diastereomers and mixtures thereof.

The compounds of the formula I can also be present in the form of the N-oxides and / or their agriculturally useful salts, the type of salt generally not being important. In general, the salts of those cations or the acid addition salts of those acids come into consideration whose cations, or anions, do not adversely affect the herbicidal activity of the compounds I.

The cations used are in particular ions of the alkali metals, preferably lithium, sodium or potassium, the alkaline earth metals, preferably calcium or magnesium, and the transition metals, preferably manganese, copper, zinc or iron. It is likewise possible to use ammonium as cation, in which case one to four hydrogen atoms are optionally replaced by C ₁ -C ₄ -alkyl, hydroxy-C ₁ -C ₄ -alkyl, C ₁ -C ₄ -alkoxy-C ₁ -C ₄ -alkyl, Hydroxy-C ₁ -C ₄ alkoxy-C ₁ -C ₄ alkyl, phenyl or benzyl may be replaced, preferably ammonium, dimethylammonium, diisopropylammonium, tetramethylammonium, tetrabutylammonium, 2- (2-hydroxyeth-1-oxy) eth-1 -ylammonium, di (2-hydroxyeth-1-yl) ammonium, trimethylbenzylammonium. Also suitable as the ammonium cation is the pyridine nitrogen atom of the formula I quaternized by alkylation or arylation. Further suitable are phosphonium ions, sulfonium ions, preferably tri (C ₁ -C ₄ -alkyl) sulfonium or sulfoxonium ions, preferably tri (C ₁ -C ₄ -alkyl) sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and the anions of C ₁ -C ₄ alkanoic acids, preferably formate, acetate, Propionate, butyrate or trifluoroacetate.

The particularly preferred embodiments of the intermediates with respect to the variables correspond to those of the groups of the formula I.

worin die Gruppen R^c1, R^c2 und R^c3 jeweils einer Gruppe R^c entsprechen und bevorzugt folgende Bedeutungen haben:
R^c1 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H;
R^c2 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H;
R^c3 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H, Br, OH und OCH₃;In a particular embodiment, the variables of the compounds of the formula I have the following meanings, these being considered both individually and in combination with one another in particular embodiments of the compounds of the formula I:
In a preferred embodiment of the compounds of the formula I, A, E and G are CR ^c and M is N. These compounds correspond to the formula I.1,

wherein the groups R ^c1 , R ^c2 and R ^c3 each correspond to a group R ^c and preferably have the following meanings:
R ^{c1 is} H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, especially H;
R ^{c2 is} H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, especially H;
R ^{c3 is} H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, especially H, Br, OH and OCH ₃ ;

worin die Gruppen R^c1, R^c2 und R^c4 jeweils einer Gruppe R^c entsprechen und bevorzugt folgende Bedeutungen haben:
R^c1 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H, Br, OH und OCH₃;
R^c2 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H;
R^c3 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H.In a further embodiment of the compounds of the formula I, A, G and M are CR ^c and E is N. These compounds correspond to the formula I.2,

wherein the groups R ^c1 , R ^c2 and R ^c4 each correspond to a group R ^c and preferably have the following meanings:
R ^{c1 is} H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, especially H, Br, OH and OCH ₃ ;
R ^{c2 is} H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, especially H;
R ^c3 H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H.

worin die Gruppen R^c1 und R^c3 jeweils einer Gruppe R^c entsprechen und bevorzugt folgende Bedeutungen haben:
R^c1 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H, Br, OH und OCH₃;
R^c3 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H, Br, OH und OCH₃.In a further embodiment of the compounds of the formula I, A and G are CR ^c and E and M are N. These compounds correspond to the formula I.3,

wherein the groups R ^c1 and R ^c3 each correspond to a group R ^c and preferably have the following meanings:
R ^{c1 is} H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, especially H, Br, OH and OCH ₃ ;
R ^{c3 is} H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and OCH ₃ .

worin die Gruppen R^c2 und R^c3 jeweils einer Gruppe R^c entsprechen und bevorzugt folgende Bedeutungen haben:
R^c2 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H;
R^c3 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H, Br, OH und OCH₃;In a further embodiment of the compounds of the formula I, A, E and G are CR ^c and M is N. These compounds correspond to the formula I.4,

wherein the groups R ^c2 and R ^c3 each correspond to a group R ^c and preferably have the following meanings:
R ^{c2 is} H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, especially H;
R ^{c3 is} H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, especially H, Br, OH and OCH ₃ ;

worin die Gruppen R^c3 und R^c4 jeweils einer Gruppe R^c entsprechen und bevorzugt folgende Bedeutungen haben:
R^c1 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H.
R^c2 H, OH, CN, Halogen, Alkyl, Alkoxy, Haloalkyl, insbesondere H, Br, OH und OCH₃.In a further embodiment of the compounds of the formula I, A and E are CR ^c and G and M is N. These compounds correspond to the formula I.5,

wherein the groups R ^c3 and R ^c4 each correspond to a group R ^c and preferably have the following meanings:
R ^{c1 is} H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H.
R ^{c2 is} H, OH, CN, halogen, alkyl, alkoxy, haloalkyl, in particular H, Br, OH and OCH ₃ .

Particularly preferred embodiments of the compounds of the formula I relate to those of each of the formulas I.1 to I.5, in which the variables have the meanings preferred for formula I.

In a first preferred embodiment of the invention, R ^{1 is} OR ^A.

In a further preferred embodiment of the invention, R ^{1 is} S (O) _n -R ^A , where n is preferably 0 or 2, in particular 2.

In a further preferred embodiment, R ^{1 is} OS (O) _n -R ^A , where n is preferably 0 or 2, in particular 2, for example OS (O) ₂ -CH ₃ , OS (O) ₂ -C ₂ H ₅ , OS (O) ₂ -C ₃ H ₇ , OS (O) ₂ -C ₆ H ₅ or OS (O) ₂ - (4-CH ₃ -C ₆ H ₄ ).

In a further preferred embodiment, R ^{1 is} OS (O) _n -NR ⁱ R ⁱⁱ , in particular with the groups NR ⁱ R ⁱⁱ mentioned below as preferred.

R ^A is in particular H, C ₁ -C ₆ -alkylcarbonyl, such as C (O) CH ₃ , C (O) CH ₂ CH ₃ , C (O) CH (CH ₃ ) ₂ or C (O) C (CH ₃ ) ₃ ; C ₁ -C ₆ cycloalkylcarbonyl, such as cyclopropylcarbonyl, cyclopentylcarbonyl or cyclohexylcarbonyl; C ₂ -C ₆ alkenylcarbonyl, such as C (O) CH = CH ₂ or C (O) CH ₂ CH = CH ₂ , optionally subst. Benzoyl, such as C (O) C ₆ H ₅ , C (O) [2-CH ₃ -C ₆ H ₄ ], C (O) [4-CH ₃ -C ₆ H ₄ ], C (O) [2 -FC ₆ H ₄ ], C (O) [4-FC ₆ H ₄ ], or optionally subst. Heteroaryl, such as pyridine, which is bonded via a carbonyl group. More preferably, R ^{A is} H or C ₁ -C ₆ alkylcarbonyl.

More preferably, R ^{A is} selected from the group H, OCH ₃ , C (O) CH ₃ , C (O) CH ₂ CH ₃ , C (O) CH (CH ₃ ) ₂ , C (O) C (CH ₃ ) ₃ , C (O) -cC ₃ H ₅ , C (O) -C ₆ H ₅ , C (O) -CH ₂ C ₆ H ₅ , C (O) CH ₂ Cl, C (O) CF ₃ , C (O) CH ₂ OCH ₃ , C (O) N (CH ₃ ) ₂ and C (O) OCH ₂ CH ₃ .

In a further preferred embodiment of the invention R ^{A is} NR ⁱ R ⁱⁱ .

In a further preferred embodiment of the invention, R ^{A is} Z-NR ⁱ -C (O) -NR ⁱ R ⁱⁱ , where R ⁱ and R ^{ii are} as initially defined and preferably as defined below. In further embodiments -C ₄ alkoxy-C for R ⁱ and also independently C ₁ -C ₄ alkoxy, C _{1 4} haloalkoxy and C ₁ -C ₁ -C ₄ alkyl in question, in particular OCH _3, OC ₂ H ₅ , CH ₂ CH ₂ OCH ₃ and CH ₂ CH ₂ Cl.

R ⁱ and R ⁱⁱ are preferably C ₁ -C ₈ -alkyl, C ₁ -C ₄ -haloalkyl, ZC ₃ -C ₆ -cycloalkyl, ZC ₁ -C ₈ -alkoxy, ZC ₁ -C ₈ -haloalkoxy, Z- Phenyl, ZC (= O) -R ^a or Z-hetaryl. Preferred are CH ₃ , C ₂ H ₅ , n-propyl, CH (CH ₃ ) ₂ , butyl, 2-chloroethyl, cyclopentyl, cyclohexyl, 2-ethoxymethyl, 2-chloroethoxy, phenyl, pyrimidines or triazines, which rings unsubstituted or are substituted. Preferred substituents are C ₁ -C ₄ -alkylcarbonyl or C ₁ -C ₄ -haloalkylcarbonyl, in particular C (OO) -CH ₃ , C (OO) -C ₂ H ₅ , C (OO) -C ₃ H ₇ , C (= O) -CH (CH ₃ ) ₂ , butylcarbonyl and C (= O) -CH ₂ Cl. Particularly preferred embodiments of the group NR ⁱ R ⁱⁱ are N (di-C ₁ -C ₄ -alkyl), in particular N (CH ₃ ) -C ₁ -C ₄ -alkyl, such as N (CH ₃ ) ₂ , N (CH ₃ ) CH ₂ CH ₃ , N (CH ₃ ) C ₃ H ₇ and N (CH ₃ ) CH (CH ₃ ) ₂ .

Further particularly preferred embodiments of NR ⁱ R ⁱⁱ are NH-aryl, wherein aryl is preferably phenyl which is substituted, in particular in the 2- and 6-position, by one to three identical or different groups. Halogen, CH ₃ , halo-C ₁ -C ₂ -alkyl, haloC ₁ -C ₂ -alkoxy and carboxyl, such as 2-Cl-6-COOH-C ₆ H ₃ , 2,6-Cl ₂ -C ₆ H ₃ , 2,6-F ₂ -C ₆ H ₃ , 2,6-Cl ₂ -3 -CH ₃ -C ₆ H ₂ , 2-CF ₃ -6-CH ₂ CHF ₂ -C ₆ H ₃ , 2 -CF ₃ -6-OCF ₃ -C ₆ H ₃ and 2-CF ₃ -6-CH ₂ CHF ₂ -C ₆ H ₃ .

Further embodiments of NR ⁱ R ⁱⁱ are NH-heteroaryl, where heteroaryl preferably represents one of the preferred heteroaromatic groups below, in particular triazinyl, pyrimidinyl or triazolopyrimidinyl, such as [1,2,4] triazolo [1,5-a] pyrimidine 2-yl, which groups may be substituted, in particular by C ₁ -C ₄ alkoxy and / or halogen. Particularly preferred are 5,7-dimethoxy- [1,2,4] triazolo [1,5-a] pyrimidin-2-yl, 5,7-diethoxy- [1,2,4] triazolo [1,5-a ] pyrimidin-2-yl, 5-fluoro-7-methoxy- [1,2,4] triazolo [1,5-a] pyrimidin-2-yl and 5-fluoro-7-ethoxy- [1,2,4 ] triazolo [1,5-a] pyrimidin-2-yl.

In particularly preferred embodiments of the compounds of the formula I and especially those of the formula I.1, R ^{1 is} selected from OH, OCH ₃ , OC (O) CH ₃ , OC (O) CH ₂ CH ₃ , OC (O) CH (CH ₃ ) ₂ , OC (O) C (CH ₃ ) ₃ , OC (O) -cC ₃ H ₅ , OC (O) -C ₆ H ₅ , OC (O) -CH ₂ C ₆ H ₅ , OC (O ) CH ₂ Cl, OC (O) -CF ₃ , OC (O) -CH ₂ OCH ₃ , OC (O) -N (CH ₃ ) ₂ and OC (O) -OCH ₂ CH ₃ .

In particularly preferred embodiments of the compounds of the formula I and especially those of the formula I.1, R ^{2 is} phenyl which is substituted by a group selected from 2-Br, 2-Cl, 2,4-Cl ₂ , 2-Cl-4 F, 2-Cl-5-F, 2-Cl-6-F, _2-Cl-4-CF3, 2-Cl-5-CF ₃ 2-Cl-6-CF _3, 2-Cl 3,6-F ₂ , 2-F, 2,4-F ₂ , 2,5-F ₂ , 2,6-F ₂ , 2-F-4-CF ₃ , 2-F-5-CF ₃ , 2-F-6-CF ₃ , 2,3,6-F ₃ , 2-NO ₂ , 2-NO ₂ -4-F, 2-NO ₂ -5-F, 2-NO ₂ -6-F, 2-NO ₂ -4-CF ₃ , 2-NO ₂ -5-CF ₃ , 2-NO ₂ -6-CF ₃ , 2-NO ₂ -3,6-F ₂ , 2-CN, 2-CH ₃ , 2-CH ₃ -4-F, 2-CH ₃ -5-F, 2-CH ₃ -6-F, 2-CH ₃ -4-CF ₃ , 2-CH ₃ -5-CF ₃ , 2- CH ₃ -6-CF ₃ , 2-CH ₃ -3,6-F ₂ , 2-OCH ₃ , 2-OCH ₃ -4-F, 2-OCH ₃ -5-F, 2-OCH ₃ -6- F, 2-OCH ₃ -4-CF ₃ , 2-OCH ₃ -5-CF ₃ , 2-OCH ₃ -6-CF ₃ , 2-OCH ₃ -3,6-F ₂ , 2-CHF ₂ , 2 -CHF ₂ -4-F, 2-CHF ₂ -5-F, 2-CHF ₂ -6-F, 2-CHF ₂ -4-CF ₃ , 2-CHF ₂ -5-CF ₃ , 2-CHF ₂ -6-CF ₃ , 2-CHF ₂ -3,6-F ₂ , 2-CF ₃ , 2-CF ₃ -4-F, 2-CF ₃ -5-F, 2-CF ₃ - 6-F, 2-CF ₃ -4-CF ₃ , 2-CF ₃ -5-CF ₃ , 2-CF ₃ -6-CF ₃ , 2-CF ₃ -3,6-F ₂ , 2-OCHF ₂ , 2-OCHF ₂ -4-F, 2-OCHF ₂ -5-F, 2-OCHF ₂ -6-F, 2-OCHF ₂ -4-CF ₃ , 2-OCHF ₂ -5-CF ₃ , 2 OCHF ₂ -6-CF ₃ , 2-OCHF ₂ -3,6-F ₂ , 2-OCF ₃ , 2-OCF ₃ -4-F, 2-OCF ₃ -5-F, 2-OCF ₃ -6- F, 2-OCF ₃ -4-CF ₃ , 2-OCF ₃ -5-CF ₃ , 2-OCF ₃ -6-CF ₃ or 2-OCF ₃ -3,6-F ₂ .

In a further preferred embodiment of the invention, R ^{A is} a 5- or 6-membered heterocycle optionally substituted by R ^b as defined above, which is preferably either 1, 2, 3 or 4 nitrogen atoms or 1 oxygen or 1 sulfur atom and optionally 1 or Has 2 nitrogen atoms as ring members and which is unsubstituted or may have 1 or 2 substituents selected from R ^b . Preferred are bonded via N saturated or unsaturated groups, such as. B .:
Heteroaromatic groups: pyridazin-3-yl, pyridazin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyrazine-2-yl, 2-furyl, 3-furyl, 2-thienyl , 3-Thienyl, pyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, isoxazol-3-yl, isoxazol-4-yl, isoxazol-5-yl, isothiazol-3-yl, isothiazole-4 -yl, isothiazol-5-yl, imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, oxazol-2-yl, oxazol-4-yl, oxazol-5-yl, thiazol-2-yl , Thiazol-4-yl and thiazol-5-yl.

In another embodiment, R ^{A is} a C-bonded heteroaromatic group such as pyrazol-3-yl, imidazol-5-yl, oxazol-2-yl, thiazol-2-yl, thiazol-4-yl, thiazole-5 yl, pyridin-2-yl, pyridin-3-yl, pyridin-4-yl, pyrimidin-2-yl, pyrimidin-4-yl, pyrimidin-5-yl, pyridazin-4-yl, pyrazine-2-yl, [1H] -tetrazol-5-yl and [2H] -tetrazol-5-yl, where the heterocycles 1 or 2 mentioned here by way of example from R ^{b may have} selected substituents. In particular, preferred groups R ^b are F, Cl, CN, NO ₂ , CH ₃ , C ₂ H ₅ , OCH ₃ , OC ₂ H ₅ , OCHF ₂ , OCF ₃ and CF ₃ .

In a further preferred embodiment, R ^{2 is} phenyl which is unsubstituted or partially or completely substituted by groups R ^b . Particularly preferred are those compounds in which a group R ^{b is} in the ortho position. Such compounds of the formula I are described by the formula IA:

In formula IA, the subscript m is zero or an integer from one to four, preferably 0, 1 or 2, in particular 0 or 1. R ⁵ and R ⁶ are groups Rb, as defined above, preferably halogen, NO ₂ , C ₁ -C ₄ -alkyl, C ₁ -C ₂ -haloalkyl and C ₁ -C ₄ -alkoxy. A group R ⁶ is preferably in position 5. A group R ⁶ in position 3 represents a further preferred embodiment.

R ⁵ particularly preferably represents Br, F, NO ₂ , CN, CH ₃ , OCH ₃ , CF ₃ , OCF ₃ , CHF ₂ or OCHF ₂ . R ⁶ particularly preferably represents halogen or halomethyl, such as Cl, F or CF ₃ . More preferably, (R ⁶ ) _{m is} selected from 4-F, 5-F, 5-Cl, 6-F, 4-CF ₃ , 5-CF ₃ and 3,6-F ₂ .

In a preferred embodiment, Y is O.

In another embodiment Y stands for S.

Another embodiment relates to the N-oxides of the compounds of the formula I.

A further embodiment relates to salts of the compounds of the formula I, in particular those obtainable by quaternization of the pyridine nitrogen atom, which can preferably be effected by alkylation or arylation of the compounds of the formula I. Accordingly, preferred salts of the compounds are the N-alkyl, especially the N -Methyl, or the N-phenyl salts.

In particular, with regard to their use, the compounds of the formula I compiled in the following tables, which correspond to the formulas I.1A *, I.2A *, I.3A *, I.4A * and I.5A *, are preferred. The groups mentioned in the tables for a substituent are also considered individually, regardless of the combination in which they are mentioned, a particularly preferred embodiment of the substituent in question.

Table 1

Compounds of the formula I.1A * in which Y is oxygen, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 2

Compounds of the formula I.1A * in which Y is oxygen, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 3

Compounds of the formula I.1A * in which Y is oxygen, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 4

Compounds of the formula I.1A * in which Y is oxygen, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 5

Compounds of the formula I.1A * in which Y is oxygen, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 6

Compounds of the formula I.1A * in which Y is oxygen, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 7

Compounds of the formula I.1A * in which Y is oxygen, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 8

Compounds of the formula I.1A * in which Y is oxygen, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 9

Compounds of the formula I.1A * in which Y is oxygen, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 10

Compounds of the formula I.1A * in which Y is sulfur, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 11

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 12

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 13

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 14

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 15

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 16

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 17

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 18

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 19

Compounds of the formula I.1A * in which Y is sulfur, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 20

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 21

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 22

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 23

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 24

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 25

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 26

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 27

Compounds of the formula I.1A * in which Y is sulfur, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 28

Compounds of the formula I.2A * in which Y is oxygen, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 29

Compounds of the formula I.2A * in which Y is oxygen, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 30

Compounds of the formula I.2A * in which Y is oxygen, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 31

Compounds of the formula I.2A * in which Y is oxygen, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 32

Compounds of the formula I.2A * in which Y is oxygen, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 33

Compounds of the formula I.2A * in which Y is oxygen, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 34

Compounds of the formula I.2A * in which Y is oxygen, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 35

Compounds of the formula I.2A * in which Y is oxygen, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 36

Compounds of the formula I.2A * in which Y is oxygen, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 37

Compounds of the formula I.2A * in which Y is sulfur, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 38

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 39

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 40

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 41

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 42

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 43

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 44

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 45

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 46

Compounds of the formula I.2A * in which Y is sulfur, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 47

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 48

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 49

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 50

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 51

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 52

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 53

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 54

Compounds of the formula I.2A * in which Y is sulfur, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 55

Compounds of the formula I.3A * in which Y is oxygen, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 56

Compounds of the formula I.3A * in which Y is oxygen, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 57

Compounds of the formula I.3A * in which Y is oxygen, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 58

Compounds of the formula I.3A * in which Y is oxygen, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 59

Compounds of the formula I.3A * in which Y is oxygen, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 60

Compounds of the formula I.3A * in which Y is oxygen, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 61

Compounds of the formula I.3A * in which Y is oxygen, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 62

Compounds of the formula I.3A * in which Y is oxygen, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 63

Compounds of the formula I.3A * in which Y is oxygen, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 64

Compounds of the formula I.3A * in which Y is sulfur, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 65

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 66

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 67

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 68

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 69

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 70

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 71

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 72

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 73

Compounds of the formula I.3A * in which Y is sulfur, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 74

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 75

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 76

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 77

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 78

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 79

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 80

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 81

Compounds of the formula I.3A * in which Y is sulfur, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 82

Compounds of the formula I.4A * in which Y is oxygen, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 83

Compounds of the formula I.4A * in which Y is oxygen, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 84

Compounds of the formula I.4A * in which Y is oxygen, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 85

Compounds of the formula I.4A * in which Y is oxygen, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 86

Compounds of the formula I.4A * in which Y is oxygen, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 87

Compounds of the formula I.4A * in which Y is oxygen, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 88

Compounds of the formula I.4A * in which Y is oxygen, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 89

Compounds of the formula I.4A * in which Y is oxygen, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 90

Compounds of the formula I.4A * in which Y is oxygen, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 91

Compounds of the formula I.4A * in which Y is sulfur, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 92

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 93

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 94

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 95

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 96

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 97

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 98

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 99

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 100

Compounds of the formula I.4A * in which Y is sulfur, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 101

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 102

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 103

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 104

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 105

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 106

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 107

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 108

Compounds of the formula I.4A * in which Y is sulfur, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 109

Compounds of the formula I.5A * in which Y is oxygen, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 110

Compounds of the formula I.5A * in which Y is oxygen, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 111

Compounds of the formula I.5A * in which Y is oxygen, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 112

Compounds of the formula I.5A * in which Y is oxygen, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 113

Compounds of the formula I.5A * in which Y is oxygen, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 114

Compounds of the formula I.5A * in which Y is oxygen, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 115

Compounds of the formula I.5A * in which Y is oxygen, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 116

Compounds of the formula I.5A * in which Y is oxygen, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 117

Compounds of the formula I.5A * in which Y is oxygen, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 118

Compounds of the formula I.5A * in which Y is sulfur, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 119

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 120

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 121

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 122

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 123

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 124

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 125

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 126

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 127

Compounds of the formula I.5A * in which Y is sulfur, the index m in (R ⁶ ) _{m is} zero and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 128

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 4-Cl and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 129

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 3-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 130

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 4-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 131

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 5-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 132

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 6-F and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 133

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 4-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 134

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 5-CF ₃ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A.

Table 135

Compounds of the formula I.5A * in which Y is sulfur, (R ⁶ ) _{m is} 3,6-F ₂ and the combination of R ¹ and R ⁵ for a compound corresponds in each case to one row of Table A corresponds to Table A

The compounds I and their agriculturally useful salts are suitable - both as mixtures of isomers and in the form of pure isomers - as herbicides. They are suitable as such or as appropriately formulated agent. The herbicidal compositions containing the compound I, in particular the preferred embodiments thereof, control plant growth on non-crop surfaces very well, especially at high application rates. In crops such as wheat, rice, corn, soybean and cotton, they act against weeds and grass weeds, without appreciably damaging the crops. This effect occurs especially at low application rates.

Depending on the particular application method, the compounds I, in particular the preferred embodiments thereof, or agents containing them can be used in a further number of crop plants for the removal of undesirable plants. For example, the following cultures may be considered:
Allium cepa, pineapple comosus, Arachis hypogaea, Asparagus officinalis, Avena sativa, Beta vulgaris spec. altissima, Beta vulgaris spec. rapeseed, Brassica napus var. napobrassica, Brassica rapa var. silvestris, Brassica oleracea, Brassica nigra, Camellia sinensis, Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica) , Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia , Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, Phaseolus vulgaris, Picea abies, Pinus spec. Pistacia vera, Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Prunus armeniaca, Prunus cerasus, Prunus dulcis and Prunus domestica, Ribes sylvestre, Ricinus communis, Sac charum officinarum, Secale cereale, Sinapis alba, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticale, Triticum durum, Vicia faba, Vitis vinifera, Zea mays.

The term crops also includes those that have been modified by breeding, mutagenesis or genetic engineering methods. Genetically modified plants are plants whose genetic material has been altered in a way that does not occur under natural conditions by crossing, mutations or natural recombination (i.e., rearrangement of genetic information). As a rule, one or more genes are integrated into the genome of the plant in order to improve the properties of the plant.

The term crops thus also includes plants that by breeding and genetic engineering measures tolerance to certain herbicide classes, such as hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors, acetolactate synthase (ALS) inhibitors, such as. B. sulfonylureas ( EP-A 257 993 . US 5,013,659 ) or imidazolinones (see eg. US 6,222,100 . WO 01/82685 . WO 00/26390 . WO 97/41218 . WO 98/02526 . WO 98/02527 . WO 04/106529 . WO 05/20673 . WO 03/14357 . WO 03/13225 . WO 03/14356 . WO 04/16073 ), Enolpyruvylshikimat 3-phosphate synthase (EPSPS) inhibitors such as. Glyphosate (see eg. WO 92/00377 ), Glutamine synthetase (GS) inhibitors such. Glufosinate (see eg. EP-A 242 236 . EP-A 242 246 ) or oxynil herbicides (see eg US 5,559,024 ).

With the help of classical breeding methods (mutagenesis) numerous crops, eg. Clearfield ^® rapeseed, which produces tolerance to imidazolinones, e.g. As imazamox, have. Using genetic engineering methods, crop plants such as soybean, produces cotton, corn, beets and rape, which are resistant to glyphosate or glufosinate, and sold under the trade name RoudupReady ^® (glyphosate) and Liberty Link ^® (glufosinate) are available.

The term crops thus also includes plants that use genetic engineering measures one or more toxins, eg. As those from the bacterial strain Bacillus ssp., Produce. Toxins produced by such genetically engineered plants include e.g. B. insecticidal proteins of Bacillus spp., In particular of B. thuringiensis, such as the endotoxins Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9c, Cry34Ab1 or Cry35Ab1; or vegetative insecticidal proteins (VIPs), e.g. VIP1, VIP2, VIP3, or VIP3A; insecticidal proteins of nematode-colonizing bacteria, e.g. B. Photorhabdus spp. or Xenorhabdus spp .; Toxins from animal organisms, eg. B. Wepsen, spider or scorpion toxins; fungal toxins, e.g. B. from streptomycetes; herbal lectins, e.g. From pea or barley; agglutinins; Proteinase inhibitors, e.g. Trypsin inhibitors, serine protease inhibitors, patatin, cystatin or papain inhibitors; Ribosome Inactivating Proteins (RIPs), e.g. Ricin, corn RIP, abrin, luffin, saporin or bryodin; Steroid metabolizing enzymes, e.g. 3-hydroxysteroid oxidase, ecdysteroid IDP glycosyltransferase, cholesterol oxidase, ecdysone inhibitors or HMG-CoA reductase; Ion channel blocker, z. B. inhibitors of sodium or calcium channels; Juvenile hormone esterase; Receptors for the diuretic hormone (helicokinin receptors); Stilbene synthase, bibenzyl synthase, chitinases and glucanases. These toxins can also be produced in the plants as proteoxins, hybrid proteins, truncated or otherwise modified proteins. Hybrid proteins are characterized by a new combination of different protein domains (see eg WO 2002/015701 ). Other examples of such toxins or genetically modified plants, the These toxins are produced in EP-A 374 753 . WO 93/007278 . WO 95/34656 . EP-A 427 529 . EP-A 451 878 . WO 03/018810 and WO 03/052073 disclosed. The methods for producing these genetically modified plants are known in the art and z. As set forth in the publications mentioned above. Many of the aforementioned toxins confer on the plants that produce them a tolerance to pests of all taxonomic arthropod classes, in particular to beetles (Coeleropta), diptera and butterflies (Lepidoptera) and nematodes (Nematoda).

Genetically engineered plants that produce one or more genes encoding insecticidal toxins, e.g. As described in the publications mentioned above and partly commercially available, such as. B. YieldGard ^® (corn cultivars producing the toxin Cry1Ab), YieldGard ^® Plus (corn cultivars producing the toxins Cry1Ab and Cry3Bb1), StarLink ^® (corn cultivars producing the toxin Cry9c), Herculex ^® RW (corn cultivars toxins which Cry34Ab1, Cry35Ab1 and the enzyme phosphinothricin N-acetyltransferase [PAT] produce); NuCOTN ^® 336 (cotton cultivars producing the Cry1Ac toxin), Bollgard ^® I (cotton cultivars producing the Cry1Ac toxin), Bollgard ^® II (cotton cultivars producing the Cry1Ac toxins and Cry2Ab2); VIPCOT ^® (cotton varieties that produce a VIP toxin); NewLeaf ^® (potato cultivars producing the Cry3A toxin); Bt Xtra ^®, NatureGard® ^®, KnockOut ^®, BiteGard ^®, Protecta ^®, Bt11 (z. B. Agrisure ^® CB) and Bt176 from Syngenta Seeds SAS, France (corn varieties which produce the toxin Cry1Ab and the PAT enzyme) , MIR604 from Syngenta Seeds SAS, France (maize varieties that produce a modified version of the toxin Cry3A, see WO 03/018810 ), MON 863 from Monsanto Europe SA, Belgium (maize varieties that produce the toxin Cry3Bb1), IPC 531 from Monsanto Europe SA, Belgium (cotton varieties that produce a modified version of the toxin Cry1Ac) and 1507 from Pioneer Overseas Corporation, Belgium (maize varieties producing the toxin Cry1F and the PAT enzyme).

The term crops thus also includes plants that produce by genetic engineering measures one or more proteins that cause increased resistance or resistance to bacterial, viral or fungal pathogens, such as. B. so-called pathogenesis-related proteins (PR proteins, see EP-A 392 225 ), Resistance proteins (eg potato varieties that produce two resistance genes against Phytophthora infestans from the Mexican wild potato Solanum bulbocastanum) or T4 lysozyme (eg potato varieties that are resistant to bacteria such as Erwinia amylvora as a result of the production of this protein).

The term crops thus also includes plants whose productivity has been improved by means of genetic engineering methods by z. For example, yield (eg biomass, grain yield, starch, oil or protein content), tolerance to drought, salt or other limiting environmental factors or resistance to pests and fungal, bacterial and viral pathogens may be increased.

The term crops also includes plants whose ingredients have been modified in particular to improve the human or animal diet using genetic engineering methods by z. For example, oil plants produce health-promoting long-chain omega-3 fatty acids or monounsaturated omega-9 fatty acids (eg Nexera ^® oilseed rape).

The term crops also includes plants that have been modified for the improved production of raw materials by means of genetic engineering methods by z. B. the amylopectin content of potatoes (Amflora ^® potato) was increased.

Furthermore, it has been found that the compounds of the formula I are also suitable for the defoliation and / or desiccation of plant parts, for which crop plants such as cotton, potato, oilseed rape, sunflower, soybean or field beans, in particular cotton, come into consideration. In this regard, compositions for the desiccation and / or defoliation of plants, processes for the preparation of these agents and methods for the desiccation and / or defoliation of plants with the compounds of formula I have been found.

Desiccants are the compounds of formula I in particular for dehydration of the aerial parts of crop plants such as potato, oilseed rape, sunflower and soybean but also cereals. This allows a completely mechanical harvesting of these important crops.

Of economic interest is also the harvest relief, which is made possible by the time-concentrated dropping or reducing the adhesion to the tree in citrus fruits, olives or other types and varieties of pome, stone and peel fruit. The same mechanism, d. h., The promotion of the formation of separation tissue between fruit or leaf and Sprossteil the plants is also essential for a well controllable defoliation of crops, especially cotton.

In addition, shortening the time interval in which the individual cotton plants ripen results in increased fiber quality after harvest.

The compounds I or the herbicidal compositions containing them can, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, even high-percentage aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, scattering agents or granules by spraying, atomizing , Dusting, scattering, pouring or treatment of the seed or mixing with the seed. The forms of application depend on the intended use; In any case, they should ensure the finest possible distribution of the active compounds according to the invention.

The herbicidal compositions contain a herbicidally effective amount of at least one compound of the formula I or an agriculturally useful salt of I and auxiliaries customary for the formulation of pesticides.

Examples of the formulation of pesticides conventional auxiliaries are inert excipients, solid carriers, surfactants (such as dispersants protective colloids, emulsifiers, wetting agents and adhesives), organic and inorganic thickeners, bactericides, antifreeze, defoamers, if necessary dyes and adhesives for seed formulations.

Examples of thickeners (ie compounds which impart to the formulation modified flow properties, ie, high viscosity at rest and low viscosity in motion) are polysaccharides, such as Xanthan Gum (Kelzan ^® from. Kelco), Rhodopol ^® 23 (Rhone Poulenc) or Veegum ^® (RT Vanderbilt) and organic and inorganic layer minerals such as Attaclay ^® (Engelhardt).

Examples of antifoams are silicone emulsions (such as. Eg. Silicone ^® SRE, from Wacker, or Rhodorsil ^® from Rhodia), long-chain alcohols, fatty acids, salts of fatty acids, organofluorine compounds and mixtures thereof.

Bactericides may be added to stabilize the aqueous herbicidal formulation. Examples of bactericides are bactericides based on dichlorophen and benzyl alcohol (Proxel ^® from. Messrs. ICI or Acetide ^® RS from Thor Chemie and Kathon ^® MK from Rohm & Haas) and isothiazolinone derivatives such as alkylisothiazolinones and benzisothiazolinones (Acticide MBS. Thor Chemicals )

Examples of antifreeze agents are ethylene glycol, propylene glycol, urea or glycerol.

Examples of colorants are both water-insoluble pigments and water-soluble dyes. Examples which may be mentioned under the names rhodamine B, C.I. Pigment Red 112 and C.I. Solvent Red 1 known dyes, as well as Pigment blue 15: 4, Pigment blue 15: 3, Pigment blue 15: 2, Pigment blue 15: 1, Pigment blue 80, Pigment yellow 1, Pigment yellow 13, Pigment red 112, Pigment red 48 : 2, Pigment red 48: 1, Pigment red 57: 1, Pigment red 53: 1, Pigment orange 43, Pigment orange 34, Pigment orange 5, Pigment green 36, Pigment green 7, Pigment white 6, Pigment brown 25, basic violet 10, basic violet 49, acid red 51, acid red 52, acid red 14, acid blue 9, acid yellow 23, basic red 10, basic red 108.

Examples of adhesives are polyvinyl pyrrolidone, polyvinyl acetate, polyvinyl alcohol and Tylose.

Suitable inert additives are, for example:
Mineral oil fractions of medium to high boiling point, such as kerosene or diesel oil, coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, eg. As paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, alkylated benzenes or their derivatives, alcohols such as methanol, ethanol, propanol, butanol, cyclohexanol, ketones such as cyclohexanone or strongly polar solvents, eg. As amines such as N-methylpyrrolidone or water.

Solid carriers are mineral earths such as silicic acids, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bolus, loess, clay, dolomite, diatomaceous earth, calcium and magnesium sulfate, magnesium oxide, ground plastics, fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, Ureas and vegetable products such as cereal flour, tree bark, wood and nutshell flour, cellulose powder or other solid carriers.

As surfactants (adjuvants, wetting agents, adhesives, dispersants and emulsifiers) are the alkali, alkaline earth, ammonium salts of aromatic sulfonic acids, eg. For example, lignosulfonic acids (eg Borrespers types, Borregaard), phenolsulfonic acids, naphthalenesulfonic acids (Morwet types, Akzo Nobel) and dibutylnaphthalenesulfonic acid (Nekal types, BASF SE), as well as fatty acids, alkyl and alkylarylsulfonates, alkyl, lauryl ether and fatty alcohol sulfates, as well as salts of sulfated hexa-, hepta- and octadecanols and of fatty alcohol glycol ethers, condensation products of sulfonated naphthalene and its derivatives with formaldehyde, condensation products of naphthalene or naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethyleneoctylphenol ether, ethoxylated isooctyl, octyl or nonylphenol , Alkylphenyl, tributylphenyl polyglycol ethers, alkylarylpolyether alcohols, isotridecyl alcohol, fatty alcohol ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, lignin sulphite liquors and proteins, denatured proteins, polysaccharides (for example methyl cellulose), hydrophobically modified starches, polyvinyl alcohol (Mowiol types Clariant), polycarboxylates (BASF SE, Sokalan types), polyalkoxylates, polyvinylamine (BASF SE, lupamine types), polyethylenimine (BASF SE, Lupasol types), polyvinylpyrrolidone and their copolymers into consideration.

Powders, dispersants and dusts may be prepared by mixing or co-grinding the active substances with a solid carrier.

Granules, for. B. coated, impregnated and homogeneous granules can be prepared by binding the active compounds to solid carriers.

Aqueous application forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the compounds of the formula I or Ia, as such or dissolved in an oil or solvent, can be homogenized in water by means of wetting agents, tackifiers, dispersants or emulsifiers. However, it is also possible to prepare concentrates consisting of active substance, wetting, adhesion, dispersing or emulsifying agent and possibly solvent or oil, which are suitable for dilution with water.

The concentrations of the compounds of the formula I in the ready-to-use formulations can be varied within wide limits. The formulations generally contain from 0.001 to 98% by weight, preferably from 0.01 to 95% by weight, of at least one active ingredient. The active ingredients are used in a purity of 90% to 100%, preferably 95% to 100% (according to NMR spectrum).

The compounds I according to the invention can be formulated, for example, as follows:

1. Products for dilution in water

A Water-soluble concentrates

10 parts by weight of active compound are dissolved with 90 parts by weight of water or a water-soluble solvent. Alternatively, wetting agents or other adjuvants are added. When diluted in water, the active ingredient dissolves. This gives a formulation with 10 wt .-% active ingredient content.

B Dispersible concentrates

20 parts by weight of active compound are dissolved in 70 parts by weight of cyclohexanone with the addition of 10 parts by weight of a dispersant z. B. dissolved polyvinylpyrrolidone. Dilution in water gives a dispersion. The active ingredient content is 20% by weight

C Emulsifiable concentrates

15 parts by weight of active compound are dissolved in 75 parts by weight of an organic solvent (for example alkylaromatics) with the addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). Dilution in water results in an emulsion. The formulation has 15% by weight active ingredient content.

D emulsions

25 parts by weight of active compound are dissolved in 35 parts by weight of an organic solvent (for example alkylaromatics) with addition of calcium dodecylbenzenesulfonate and castor oil ethoxylate (in each case 5 parts by weight). These Mixture is added by means of an emulsifying machine (eg Ultraturax) in 30 parts by weight of water and brought to a homogeneous emulsion. Dilution in water results in an emulsion. The formulation has an active ingredient content of 25% by weight.

E suspensions

20 parts by weight of active compound are comminuted with the addition of 10 parts by weight dispersing and wetting agents and 70 parts by weight of water or an organic solvent in a stirred ball mill to a fine active substance suspension. Dilution in water results in a stable suspension of the active ingredient. The active ingredient content in the formulation is 20% by weight.

F Water-dispersible and water-soluble granules

50 parts by weight of active compound are finely ground with the addition of 50 parts by weight of dispersants and wetting agents and prepared by means of industrial equipment (eg extrusion, spray tower, fluidized bed) as water-dispersible or water-soluble granules. Dilution in water results in a stable dispersion or solution of the active ingredient. The formulation has an active ingredient content of 50% by weight.

G Water-dispersible and water-soluble powders

75 parts by weight of active compound are ground with the addition of 25 parts by weight of dispersants and wetting agents and silica gel in a rotor-Strator mill. Dilution in water results in a stable dispersion or solution of the active ingredient. The active ingredient content of the formulation is 75% by weight.

H gel formulations

In a ball mill, 20 parts by weight of active ingredient, 10 parts by weight of dispersant, 1 part by weight of gelling agent and 70 parts by weight of water or an organic solvent are ground to a fine suspension. Dilution with water results in a stable suspension with 20% by weight active ingredient content.

2. Products for direct application

I dusts

5 parts by weight of active compound are finely ground and intimately mixed with 95 parts by weight of finely divided kaolin. This gives a dust with 5 wt .-% active ingredient content.

J Granules (GR, FG, GG, MG)

0.5 parts by weight of active compound are finely ground and combined with 99.5 parts by weight of carriers. Common processes are extrusion, spray drying or fluidized bed. This gives a granulate for direct application with 0.5 wt .-% active ingredient content.

K ULV solutions (UL)

10 parts by weight of active compound are dissolved in 90 parts by weight of an organic solvent z. B. dissolved xylene. This gives a product for direct application with 10 wt .-% active ingredient content.

The application of the compounds I or the herbicidal compositions containing them can be carried out in the pre-emergence, postemergence or together with the seed of a crop. It is also possible to apply the herbicidal compositions or active ingredients characterized in that with the herbicidal agents or active ingredients pretreated seed of a crop plant is applied. If the active ingredients are less compatible with certain crops, then application techniques may be employed whereby the herbicidal agents are sprayed by the sprayers so as not to hit the leaves of the sensitive crop if possible, while the active ingredients affect the leaves underneath growing undesirable plants or the uncovered floor surface (post-directed, lay-by).

In a further embodiment, the application of the compounds of the formula I or of the herbicidal compositions can be carried out by treating seed.

The treatment of seed comprises essentially all techniques familiar to the skilled worker (seed dressing, seed coating, seed dusting, seed soaking, seed film coating, seed multilayer coating, seed encrusting, seed dripping and seed pelleting) based on the compounds of the formula according to the invention I or agents produced therefrom. Here, the herbicidal agents can be diluted or applied undiluted.

The term seed includes seeds of all kinds, such as. As grains, seeds, fruits, tubers, cuttings and similar forms. The term seed preferably describes grains and seeds here.

Seeds of the abovementioned crops but also the seeds of transgenic or obtained by conventional breeding methods plants can be used as seeds.

Depending on the control target, season, target plants and growth stage, the application rates of active ingredient are 0.001 to 3.0, preferably 0.01 to 1.0 kg / ha of active substance (a. S.). For seed treatment, the compounds I are usually used in amounts of 0.001 to 10 kg per 100 kg of seed.

It may also be advantageous to use the compounds of the formula I in combination with safeners. Safeners are chemical compounds that prevent or reduce damage to crops without significantly affecting the herbicidal activity of the compounds of formula I on undesirable plants. They can be used both before sowing (for example in seed treatments, cuttings or seedlings) as well as in the pre- or post-emergence of the crop. The safeners and the compounds of formula I can be used simultaneously or sequentially. Suitable safeners are, for example, (quinolin-8-oxy) acetic acids, 1-phenyl-5-haloalkyl-1H-1,2,4-triazole-3-carboxylic acids, 1-phenyl-4,5-dihydro-5-alkyl-1H pyrazole-3,5-dicarboxylic acids, 4,5-dihydro-5,5-diaryl-3-isoxazolecarboxylic acids, dichloroacetamides, alpha-oximinophenylacetonitriles, acetophenone oximes, 4,6-dihalo-2-phenylpyrimidines, N - [[4- ( Aminocarbonyl) phenyl] sulfonyl] -2-benzoic acid amides, 1,8-naphthalic anhydride, 2-halo-4- (haloalkyl) -5-thiazolecarboxylic acids, phosphorothiolates and N-alkyl-O-phenylcarbamates and their agriculturally acceptable salts, and provided they have an acid function, their agriculturally useful derivatives such as amides, esters and thioesters.

To widen the spectrum of action and to achieve synergistic effects, the compounds of formula I can be mixed with numerous representatives of other herbicidal or growth-regulating active ingredient groups or with safeners and applied together. For example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, aryloxy / heteroaryloxyalkanoic acids and their derivatives, benzoic acid and derivatives thereof, benzothiadiazinones, 2- (hetaroyl / Aroyl) -1,3-cyclohexanediones, heteroaryl-aryl ketones, benzylisoxazolidinones, meta-CF ₃ -phenyl derivatives, carbamates, quinolinecarboxylic acid and derivatives thereof, chloroacetanilides, cyclohexenone oxime ether derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones , Dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy and heteroaryloxyphenoxypropionic acid esters, phenylacetic acid and their derivatives, 2-phenylpropionic acid and its derivatives, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and derivatives thereof, Pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, Triazolcarboxamide, uracils and phenylpyrazolines and isoxazolines and derivatives thereof.

In addition, it may be useful to use the compounds I alone or in combination with other herbicides or even mixed with other crop protection agents, together, for example, with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are used for the elimination of nutritional and trace element deficiencies. Other additives such as non-phytotoxic oils and oil concentrates may also be added.

• b1) aus der Gruppe der Lipid-Biosynthese-Inhibitoren: Alloxydim, Alloxydim-natrium, Butroxydim, Clethodim, Clodinafop, Clodinafop-propargyl, Cycloxydim, Cyhalofop, Cyhalofop-butyl, Diclofop, Diclofop-methyl, Fenoxaprop, Fenoxaprop-ethyl, Fenoxaprop-P, Fenoxaprop-P-ethyl, Fluazifop, Fluazifop-butyl, Fluazifop-P, Fluazifop-P-butyl, Haloxyfop, Haloxyfop-methyl, Haloxyfop-P, Haloxyfop-P-methyl, Metamifop, Pinoxaden, Profoxydim, Propaquizafop, Quizalofop, Quizalofopethyl, Quizalofop-tefuryl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Sethoxydim, Tepraloxydim, Tralkoxydim, Benfuresat, Butylat, Cycloat, Dalapon, Dimepiperat, EPTC, Esprocarb, Ethofumesat, Flupropanat, Molinat, Orbencarb, Pebulat, Prosulfocarb, TCA, Thiobencarb, Tiocarbazil, Triallat und Vernolat;
• b2) aus der Gruppe der ALS-Inhibitoren: Amidosulfuron, Azimsulfuron, Bensulfuron, Bensulfuron-methyl, Bispyribac, Bispyribacnatrium, Chlorimuron, Chlorimuron-ethyl, Chlorsulfuron, Cinosulfuron, Cloransulam, Cloransulam-methyl, Cyclosulfamuron, Diclosulam, Ethametsulfuron, Ethametsulfuronmethyl, Ethoxysulfuron, Flazasulfuron, Florasulam, Flucarbazon, Flucarbazon-natrium, Flucetosulfuron, Flumetsulam, Flupyrsulfuron, Flupyrsulfuron-methyl-natrium, Foramsulfuron, Halosulfuron, Halosulfuron-methyl, Imazamethabenz, Imazamethabenzmethyl, Imazamox, Imazapic, Imazapyr, Imazaquin, Imazethapyr, Imazosulfuron, Iodosulfuron, Iodosulfuron-methyl-natrium, Mesosulfuron, Metosulam, Metsulfuron, Metsulfuron-methyl, Nicosulfuron, Orthosulfamuron, Oxasulfuron, Penoxsulam, Primisulfuron, Primisulfuron-methyl, Propoxycarbazon, Propoxycarbazon-natrium, Prosulfuron, Pyrazosulfuron, Pyrazosulfuron-ethyl, Pyribenzoxim, Pyrimisulfan, Pyriftalid, Pyriminobac, Pyriminobac-methyl, Pyrithiobac, Pyrithiobac-natrium, Pyroxsulam, Rimsulfuron, Sulfometuron, Sulfometuron-methyl, Sulfosulfuron, Thiencarbazon, Thiencarbazon-methyl, Thifensulfuron, Thifensulfuron-methyl, Triasulfuron, Tribenuron, Tribenuron-methyl, Trifloxysulfuron, Triflusulfuron, Triflusulfuron-methyl und Tritosulfuron;
• b3) aus der Gruppe der Photosynthese-Inhibitoren: Ametryn, Amicarbazon, Atrazin, Bentazon, Bentazon-natrium, Bromacil, Bromofenoxim, Bromoxynil und seine Salze und Ester, Chlorobromuron, Chloridazon, Chlorotoluron, Chloroxuron, Cyanazin, Desmedipham, Desmetryn, Dimefuron, Dimethametryn, Diquat, Diquat-dibromid, Diuron, Fluometuron, Hexazinon, Ioxynil und seine Salze und Ester, Isoproturon, Isouron, Karbutilat, Lenacil, Linuron, Metamitron, Methabenzthiazuron, Metobenzuron, Metoxuron, Metribuzin, Monolinuron, Neburon, Paraquat, Paraquat-dichlorid, Paraquat-dimetilsulfat, Pentanochlor, Phenmedipham, Phenmediphamethyl, Prometon, Prometryn, Propanil, Propazin, Pyridafol, Pyridat, Siduron, Simazin, Simetryn, Tebuthiuron, Terbacil, Terbumeton, Terbuthylazin, Terbutryn, Thidiazuron und Trietazin;
• b4) aus der Gruppe der Protoporphyrinogen-IX-Oxidase-Inhibitoren: Acifluorfen, Acifluorfen-natrium, Azafenidin, Bencarbazon, Benzfendizon, Bifenox, Butafenacil, Carfentrazon, Carfentrazon-ethyl, Chlomethoxyfen, Cinidon-ethyl, Fluazolat, Flufenpyr, Flufenpyr-ethyl, Flumiclorac, Flumiclorac-pentyl, Flumioxazin, Fluoroglycofen, Fluoroglycofen-ethyl, Fluthiacet, Fluthiacet-methyl, Fomesafen, Halosafen, Lactofen, Oxadiargyl, Oxadiazon, Oxyfluorfen, Pentoxazon, Profluazol, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Saflufenacil, Sulfentrazon, Thidiazimin, 2-Chlor-5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluormethyl)-1(2H)-pyrimidinyl]-4-fluor-N-[(isopropyl)methylsulfamoyl]benzamid (H-1; CAS 372137-35-4), [3-[2-Chlor-4-fluor-5-(1-methyl-6-trifluormethyl-2,4-dioxo-1,2,3,4,-tetrahydropyrimidin-3-yl)phenoxy]-2-pyridyloxy]essigsäureethylester (H-2; CAS 353292-31-6), N-Ethyl-3-(2,6-dichlor-4-trifluormethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamid (H-3; CAS 452098-92-9), N-Tetrahydrofurfuryl-3-(2,6-dichlor-4-trifluormethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamid (H-4; CAS 915396-43-9), N-Ethyl-3-(2-chlor-6-fluor-4-trifluormethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamid (H-5; CAS 452099-05-7) und N-Tetrahydrofurfuryl-3-(2-chlor-6-fluor-4-trifluormethylphenoxy)-5-methyl-1H-pyrazol-1-carboxamid (H-6; CAS 45100-03-7);
• b5) aus der Gruppe der Bleacher-Herbizide: Aclonifen, Amitrol, Beflubutamid, Benzobicyclon, Benzofenap, Clomazon, Diflufenican, Fluridon, Flurochloridon, Flurtamon, Isoxaflutol, Mesotrion, Norflurazon, Picolinafen, Pyrasulfutol, Pyrazolynat, Pyrazoxyfen, Sulcotrion, Tefuryltrion, Tembotrion, Topramezon, 4-Hydroxy-3-[[2-[(2-methoxyethoxy)methyl]-6-(trifluormethyl)-3-pyridyl]carbonyl]bicyclo[3.2.1]oct-3-en-2-one (H-7; CAS 352010-68-5) und 4-(3-Trifluormethylphenoxy)-2-(4-trifluormethylphenyl)pyrimidin (H-8; CAS 180608-33-7);
• b6) aus der Gruppe der EPSP-Synthase-Inhibitoren: Glyphosat, Glyphosat-isopropylammonium und Glyphosat-trimesium (Sulfosat);
• b7) aus der Gruppe der Glutamin-Synthase-Inhibitoren: Bilanaphos (Bialaphos), Bilanaphos-natrium, Glufosinat und Glufosinat-ammonium;
• b8) aus der Gruppe der DHP-Synthase-Inhibitoren: Asulam;
• b9) aus der Gruppe der Mitose-Inhibitoren: Amiprophos, Amiprophos-methyl, Benfluralin, Butamiphos, Butralin, Carbetamid, Chlorpropham, Chlorthal, Chlorthal-dimethyl, Dinitramin, Dithiopyr, Ethalfluralin, Fluchloralin, Oryzalin, Pendimethalin, Prodiamin, Propham, Propyzamid, Tebutam, Thiazopyr und Trifluralin;
• b10) aus der Gruppe der VLCFA-Inhibitoren: Acetochlor, Alachlor, Anilofos, Butachlor, Cafenstrol, Dimethachlor, Dimethanamid, Dimethenamid-P, Diphenamid, Fentrazamid, Flufenacet, Mefenacet, Metazachlor, Metolachlor, Metolachlor-S, Naproanilid, Napropamid, Pethoxamid, Piperophos, Pretilachlor, Propachlor, Propisochlor, Pyroxasulfon (KIH-485) und Thenylchlor; Verbindungen der Formel 2:
  
  worin die Variablen folgende Bedeutungen haben: Y Phenyl oder 5- oder 6-gliedriges Heteroaryl wie eingangs definiert, welche durch eine bis drei Gruppen R^aa substituiert sein können; R²¹, R²², R²³, R²⁴ H, Halogen, oder C₁-C₄-Alkyl; X O oder NH; n 0 oder 1.

Examples of herbicides which can be used in combination with the pyridine compounds of the formula I according to the present invention are:

• b1) from the group of lipid biosynthesis inhibitors: alloxydim, alloxydim sodium, butroxydim, clethodim, clodinafop, clodinafop-propargyl, cycloxydim, cyhalofop, cyhalofop-butyl, diclofop, diclofop-methyl, fenoxaprop, fenoxaprop-ethyl, fenoxaprop- P, fenoxaprop-P-ethyl, fluazifop, fluazifop-butyl, fluazifop-P, fluazifop-p-butyl, haloxyfop, haloxyfop-methyl, haloxyfop-P, haloxyfop-P-methyl, metamifop, pinoxaden, profoxydim, propaquizafop, quizalofop, Quizalofopethyl, Quizalofop-tefuryl, Quizalofop-P, Quizalofop-P-ethyl, Quizalofop-P-tefuryl, Sethoxydim, Tepraloxydim, tralkoxydim, benfuresate, butylate, cycloate, dalapon, dimepiperate, EPTC, esprocarb, ethofumesate, flupropanate, molinate, orbencarb, pebulate, prosulfocarb, TCA, thiobencarb, tiocarbazil, triallate and vernolate;
• b2) from the group of ALS inhibitors: amidosulfuron, azimsulfuron, bensulfuron, bensulfuron-methyl, bispyribac, bispyribac sodium, chlorimuron, chlorimuron-ethyl, chlorosulfuron, cinosulfuron, cloransulam, cloransulam-methyl, cyclosulfamuron, diclosulam, ethametsulfuron, ethametsulfuronmethyl, ethoxysulfuron, Flazasulfuron, florasulam, flucarbazone, flucarbazone sodium, flucetosulfuron, flumetsulam, flupyrsulfuron, flupyrsulfuron-methyl-sodium, foramsulfuron, halosulfuron, halosulfuron-methyl, imazamethabenz, imazamethabenzemethyl, imazamox, imazapic, imazapyr, imazaquin, imazethapyr, imazosulfuron, iodosulfuron, iodosulfuron- methylsodium, mesosulfuron, metosulam, metsulfuron, metsulfuron-methyl, nicosulfuron, orthosulfamuron, oxasulfuron, penoxsulam, primisulfuron, primisulfuron-methyl, propoxycarbazone, propoxycarbazone-sodium, prosulfuron, pyrazosulfuron, pyrazosulfuron-ethyl, pyribenzoxime, pyrimisulfan, pyriftalid, pyriminobac, Pyriminobac-methyl, Pyrithiobac, Pyrithiobac Sodium, Pyroxsulam, rimsulfuron, sulfometuron, sulfometuron-methyl, sulfosulfuron, thiencarbazone, thiencarbazone-methyl, thifensulfuron, thifensulfuron-methyl, triasulfuron, tribenuron, tribenuron-methyl, trifloxysulfuron, triflusulfuron, triflusulfuron-methyl and tritosulfuron;
• b3) from the group of photosynthesis inhibitors: ametryn, amicarbazone, atrazine, bentazone, bentazone sodium, bromacil, bromofenoxime, bromoxynil and its salts and esters, chlorobromuron, chloridazon, chlorotoluron, chloroxuron, cyanazine, desmedipham, desmetryn, dimefuron, dimethametryn , Diquat, diquat-dibromide, diuron, fluometuron, hexazinone, ioxynil and its salts and esters, isoproturon, isourone, carbutilate, lenacil, linuron, metamitron, methabenzthiazuron, metobenzuron, metoxuron, metribuzin, monolinuron, neburon, paraquat, paraquat dichloride, Paraquat-dimetilsulfate, pentanochlor, phenmedipham, phenmediphamethyl, prometon, prometryn, propanil, propazine, pyridafol, pyridate, siduron, simazine, simetryn, tebuthiuron, terbacil, terbumetone, terbuthylazine, terbutryn, thidiazuron and trietazine;
• b4) from the group of protoporphyrinogen IX oxidase inhibitors: acifluorfen, acifluorfen sodium, azafenidine, bencarbazone, benzfendizone, bifenox, butafenacil, carfentrazone, carfentrazone-ethyl, chlomethoxyfen, cinidon-ethyl, fluazolate, flufenpyr, flufenpyr-ethyl, Flumiclorac, Flumiclorac-pentyl, Flumioxazine, Fluoroglycofen, Fluoroglycofen-ethyl, Fluthiacet, Fluthiacet-methyl, Fomesafen, Halosafen, Lactofen, Oxadiargyl, Oxadiazon, Oxyfluorfen, Pentoxazone, Profluazol, Pyraclonil, Pyraflufen, Pyraflufen-ethyl, Saflufenacil, Sulfentrazone, Thidiazimin, 2-chloro-5- [3,6-dihydro-3-methyl-2,6-dioxo-4- (trifluoromethyl) -1 (2H) -pyrimidinyl] -4-fluoro-N - [(isopropyl) methylsulfamoyl] benzamide (H-1; CAS 372137-35-4), [3- [2-chloro-4-fluoro-5- (1-methyl-6-trifluoromethyl-2,4-dioxo-1,2,3,4, tetrahydropyrimidin-3-yl) phenoxy] -2-pyridyloxy] acetic acid ethyl ester (H-2; CAS 353292-31-6), N-ethyl-3- (2,6-dichloro-4-trifluoromethylphenoxy) -5-methyl- 1H-pyrazole-1-carboxamide (H-3; CAS 452098-92-9), N-tetrahydrofurfuryl-3- (2,6- dichloro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole-1-carboxamide (H-4; CAS 915396-43-9), N-ethyl-3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole-1-carboxamide (H-5; CAS 452099-05-7 ) and N-tetrahydrofurfuryl-3- (2-chloro-6-fluoro-4-trifluoromethylphenoxy) -5-methyl-1H-pyrazole-1-carboxamide (H-6; CAS 45100-03-7);
• b5) from the group of bleacher herbicides: aclonifen, amitrole, beflubutamide, benzobicyclone, benzofenap, clomazone, diflufenican, fluridone, flurochloridone, flurtamone, isoxaflutole, mesotrione, norflurazon, picolinafen, pyrasulfutole, pyrazolynate, pyrazoxyfen, sulcotrione, tefuryltrione, tembotrione, Topramezone, 4-hydroxy-3 - [[2 - [(2-methoxyethoxy) methyl] -6- (trifluoromethyl) -3-pyridyl] carbonyl] bicyclo [3.2.1] oct-3-en-2-one (H -7; CAS 352010-68-5) and 4- (3-trifluoromethylphenoxy) -2- (4-trifluoromethylphenyl) pyrimidine (H-8; CAS 180608-33-7);
• b6) from the group of EPSP synthase inhibitors: glyphosate, glyphosate isopropylammonium and glyphosate trimesium (sulfosate);
• b7) from the group of glutamine synthase inhibitors: bilanaphos (bialaphos), bilanaphos-sodium, glufosinate and glufosinate-ammonium;
• b8) from the group of DHP synthase inhibitors: asulam;
• b9) from the group of mitosis inhibitors: Amiprophos, Amiprophos-methyl, Benfluralin, Butamiphos, Butraline, Carbetamide, Chlorpropham, Chlorthal, Chlorthal-dimethyl, Dinitramine, Dithiopyr, Ethalfluralin, Fluchloralin, Oryzalin, Pendimethalin, Prodiamine, Propham, Propyzamide, Tebutam, thiazopyr and trifluralin;
• b10) from the group of VLCFA inhibitors: acetochlor, alachlor, anilofos, butachlor, cafenstrol, dimethachlor, dimethanamide, dimethenamid-P, diphenamid, fentrazamide, flufenacet, mefenacet, metazachlor, metolachlor, metolachlor-S, naproanilide, napropamide, pethoxamide, Piperophos, pretilachlor, propachlor, propisochlor, pyroxasulfone (KIH-485) and thenylchloro; Compounds of the formula 2:
  
  wherein the variables have the following meanings: Y is phenyl or 5- or 6-membered heteroaryl as defined above, which may be substituted by one to three groups R ^aa ; R ²¹ , R ²² , R ²³ , R ^{24 are} H, halogen, or C ₁ -C ₄ alkyl; X is O or NH; n 0 or 1.

wobei # die Bindung zu dem Molekülgerüst bedeutet; und
R²¹, R²², R²³, R²⁴ H, Cl, F oder CH₃; R²⁵ Halogen, C₁-C₄-Alkyl oder C₁-C₄-Haloalkyl; R²⁶ C₁-C₄-Alkyl; R²⁷ Halogen, C₁-C₄-Alkoxy oder C₁-C₄-Haloalkoxy; R²⁸ H, Halogen, C₁-C₄-Alkyl, C₁-C₄-Haloalkyl oder C₁-C₄-Haloalkoxy; m 0, 1, 2 oder 3; X Sauerstoff; n 0 oder 1.In particular, compounds of the formula 2 have the following meanings:

where # is the bond to the molecular skeleton; and
R ²¹ , R ²² , R ²³ , R ^{24 are} H, Cl, F or CH ₃ ; R ^{25 is} halogen, C ₁ -C ₄ -alkyl or C ₁ -C ₄ -haloalkyl; R ^{26 is} C ₁ -C ₄ -alkyl; R ^{27 is} halogen, C ₁ -C ₄ -alkoxy or C ₁ -C ₄ -haloalkoxy; R ^{28 is} H, halogen, C ₁ -C ₄ -alkyl, C ₁ -C ₄ -haloalkyl or C ₁ -C ₄ -haloalkoxy; m is 0, 1, 2 or 3; X oxygen; n 0 or 1.

R²¹ H; R²², R²³ F; R²⁴ H oder F; X Sauerstoff; n 0 oder 1.Preferred compounds of the formula 2 have the following meanings:

R ²¹ H; R ^22, R ²³ F; R ²⁴ H or F; X oxygen; n 0 or 1.

• b11) aus der Gruppe der Cellulose-Biosynthese-Inhibitoren: Chlorthiamid, Dichlobenil, Flupoxam und Isoxaben;
• b12) aus der Gruppe der Entkoppler-Herbizide: Dinoseb, Dinoterb und DNOC und seine Salze;
• b13) aus der Gruppe der Auxin-Herbizide: 2,4-D und seine Salze und Ester, 2,4-DB und seine Salze und Ester, Aminopyralid und seine Salze wie Aminopyralid-tris(2-hydroxypropyl)ammonium und seine Ester, Benazolin, Benazolin-ethyl, Chloramben und seine Salze und Ester, Clomeprop, Clopyralid und seine Salze und Ester, Dicamba und seine Salze und Ester, Dichlorprop und seine Salze und Ester, Dichlorprop-P und seine Salze und Ester, Fluroxypyr, Fluroxypyr-butometyl, Fluroxypyr-meptyl, MCPA und seine Salze und Ester, MCPA-thioethyl, MCPB und seine Salze und Ester, Mecoprop und seine Salze und Ester, Mecoprop-P und seine Salze und Ester, Picloram und seine Salze und Ester, Quinclorac, Quinmerac, TBA (2,3,6) und seine Salze und Ester, Triclopyr und seine Salze und Ester, und 5,6-Dichlor-2-cyclopropyl-4-pyrimidincarbonsäure (H-9; CAS 858956-08-8) und seine Salze und Ester;
• b14) aus der Gruppe der Auxin-Transport-Inhibitoren: Diflufenzopyr, Diflufenzopyrnatrium, Naptalam und Naptalam-natrium;
• b15) aus der Gruppe der sonstigen Herbizide: Bromobutid, Chlorflurenol, Chlorflurenol-methyl, Cinmethylin, Cumyluron, Dalapon, Dazomet, Difenzoquat, Difenzoquat-metilsulfate, Dimethipin, DSMA, Dymron, Endothal und seine Salze, Etobenzanid, Flamprop, Flamprop-isopropyl, Flamprop-methyl Flamprop-M-isopropyl, Flamprop-M-methyl, Flurenol, Flurenol-butyl, Flurprimidol, Fosamin, Fosamine-ammonium, Indanofan, Maleinsäure-hydrazid, Mefluidid, Metam, Methylazid, Methylbromid, Methyl-dymron, Methyljodid. MSMA, Ölsäure, Oxaziclomefon, Pelargonsäure, Pyributicarb, Quinoclamin, Triaziflam, Tridiphan und 6-Chlor-3-(2-cyclopropyl-6-methylphenoxy)-4-pyridazinol (H-10; CAS 499223-49-3) und seine Salze und Ester.

Particularly preferred compounds of the formula 2 are:
3- [5- (2,2-Difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-ylmethanesulfonyl] -4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole ( 2-1); 3 - {[5- (2,2-difluoro-ethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] -fluoro-methanesulfonyl} -5,5-dimethyl-4,5-dihydro- isoxazole (2-2); 4- (4-Fluoro-5,5-dimethyl-4,5-dihydroisoxazol-3-sulfonylmethyl) -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-3); 4 - [(5,5-dimethyl-4,5-dihydro-isoxazol-3-sulfonyl) -fluoromethyl] -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-4); 4- (5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonylmethyl) -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-5); 3 - {[5- (2,2-difluoro-ethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] difluoro-methanesulfonyl} -5,5-dimethyl-4,5-dihydro- isoxazole (2-6); 4 - [(5,5-Dimethyl-4,5-dihydroisoxazol-3-sulfonyl) difluoro-methyl] -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2-7) ; 3 - {[5- (2,2-difluoroethoxy) -1-methyl-3-trifluoromethyl-1H-pyrazol-4-yl] difluoro-methanesulfonyl-fluoro-} -4-4,5-5,5-dimethyl dihydro-isoxazole (2-8); 4- [Difluoro (4-fluoro-5,5-dimethyl-4,5-dihydroisoxazole-3-sulfonyl) -methyl] -2-methyl-5-trifluoromethyl-2H- [1,2,3] triazole (2 -9);

• b11) from the group of cellulose biosynthesis inhibitors: chlorthiamide, dichlobenil, flupoxam and isoxaben;
• b12) from the group of decoupling herbicides: dinoseb, dinoterb and DNOC and its salts;
• b13) from the group of auxin herbicides: 2,4-D and its salts and esters, 2,4-DB and its salts and esters, aminopyralid and its salts, such as aminopyralid tris (2-hydroxypropyl) ammonium and its esters, Benazoline, Benazoline-ethyl, Chloramben and its salts and esters, Clomeprop, Clopyralid and its salts and esters, Dicamba and its salts and esters, Dichlorprop and its salts and esters, Dichlorprop-P and its salts and esters, Fluroxypyr, Fluroxypyr-butometyl , Fluroxypyr-meptyl, MCPA and its salts and esters, MCPA-thioethyl, MCPB and its salts and esters, mecoprop and its salts and esters, mecoprop-P and its salts and esters, picloram and its salts and esters, Quinclorac, Quinmerac, TBA (2,3,6) and its salts and esters, triclopyr and its salts and esters, and 5,6-dichloro-2-cyclopropyl-4-pyrimidinecarboxylic acid (H-9; CAS 858956-08-8) and its salts and esters;
• b14) from the group of auxin transport inhibitors: diflufenzopyr, diflufenzopyrnatrium, naptalam and naptalam sodium;
• b15) from the group of the other herbicides: bromobutide, chlorofluorol, chlorofluorolmethyl, cinmethylin, cumyluron, dalapon, dazomet, difenzoquat, difenzoquat-metylsulfate, dimethipine, dsma, dymron, endothal and its salts, etobenzanide, flamprop, flamprop-isopropyl, Flamprop-methyl Flamprop-M-isopropyl, Flamprop-M-methyl, Flurenol, Flurenol-butyl, Flurprimidol, Fosamine, Fosamine-ammonium, Indanofan, maleic hydrazide, Mefluidide, Metam, Methylazide, Methylbromide, Methyl-dymron, Methyliodide. MSMA, oleic acid, oxaziclomefon, pelargonic acid, pyributicarb, quinoclamine, triaziflam, tridiphan and 6-chloro-3- (2-cyclopropyl-6-methylphenoxy) -4-pyridazinol (H-10; CAS 499223-49-3) and its salts and esters.

Examples of preferred safeners C are Benoxacor, Cloquintocet, Cyometrinil, Cyprosulfamide, Dichlormid, Dicyclonon, Dietholate, Fenchlorazole, Fenclorim, Flurazole, Fluxofenim, Furilazole, Isoxadifen, Mefenpyr, Mephenate, Naphthalic Anhydride, Oxabetrinil, 4- (Dichloroacetyl) -1-oxa 4-azaspiro [4.5] decane (H-11; MON4660, CAS 71526-07-3) and 2,2,5-trimethyl-3- (dichloroacetyl) -1,3-oxazolidine (H-12; R-29148, CAS 52836-31-4). The active compounds of groups b1) to b15) and the safeners C are known herbicides and safeners, see, for example, US Pat. B. The Compendium of Pesticide Common Names (http://www.alanwood.net/pesticides/); B. Hock, C. Fedtke, RR Schmidt, herbicides, Georg Thieme Verlag, Stuttgart 1995 , Other herbicidal active ingredients are made WO 96/26202 . WO 97/41116 . WO 97/41117 . WO 97/41118 . WO 01/83459 and WO 2008/074991 as well as out W. Krämer et al. (ed.) "Modern Crop Protection Compounds", Vol. 1, Wiley VCH, 2007 and the literature cited therein.

The invention also relates to compositions in the form of a plant protection composition formulated as a 1-component composition comprising a combination of active substances comprising at least one pyridine compound of the formula I and at least one further active ingredient, preferably selected from the active substances of groups b1 to b15, and at least one solid or liquid carrier and / or one or more surface-active substances and, if desired, one or more further auxiliaries customary for crop protection agents.

The invention also relates to compositions in the form of a plant protection composition formulated as a 2-component composition comprising a first component comprising at least one pyridine compound of the formula I, a solid or liquid carrier and / or one or more surface-active substances, and a second component containing at least one another active ingredient selected from the active compounds of groups b1 to b15, a solid or liquid carrier and / or one or more surface-active substances, wherein in addition both components may also contain other, customary for crop protection agents.

In binary compositions containing at least one compound of the formula I as component A and at least one herbicide B, the weight ratio of the active compounds A: B is generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and particularly preferably in the range of 1:75 to 75: 1.

In binary compositions which comprise at least one compound of the formula I as component A and at least one safener C, the weight ratio of the active compounds A: C is generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and particularly preferably in the range of 1:75 to 75: 1.

In ternary compositions containing both at least one compound of the formula I as component A, at least one herbicide B and at least one safener C, the relative proportions by weight of the components A: B are generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range from 1: 250 to 250: 1 and more preferably in the range from 1:75 to 75: 1, the weight ratio of component A: C is generally in the range of 1: 1000 to 1000: 1, preferably in the range of 1: 500 to 500: 1, in particular in the range of 1: 250 to 250: 1 and more preferably in the range of 1:75 to 75: 1, and the weight ratio of the components B: C is generally in the range from 1: 1000 to 1000: 1, preferably in the range from 1: 500 to 500: 1, in particular in the range from 1: 250 to 250: 1 and particularly preferably in the range from 1:75 to 75: 1st The weight ratio of components A + B to component C is preferably in the range from 1: 500 to 500: 1, in particular in the range from 1: 250 to 250: 1 and particularly preferably in the range from 1:75 to 75: 1.

Examples of particularly preferred compositions according to the invention, containing in each case an individualized compound of the formula I and a mixing partner, or a mixture partner combination are given in the following Table B.

The compounds I and the compositions according to the invention may also have a plant-strengthening effect. They are therefore suitable for mobilizing plant-own defenses against infestation by undesirable microorganisms, such as harmful fungi, but also viruses and bacteria. In this context, plant-strengthening (resistance-inducing) substances are to be understood as meaning those substances which are capable of stimulating the defense system of treated plants in such a way that they develop extensive resistance to these microorganisms during subsequent inoculation with undesired microorganisms.

The compounds I can be used to protect plants against attack by undesired microorganisms within a certain period of time after the treatment. The period within which protection is provided generally extends from 1 to 28 days, preferably 1 to 14 days after treatment of the plants with the compounds I or after treatment of the seed, up to 9 months after sowing.

The compounds I and the compositions according to the invention are also suitable for increasing crop yield.

They are also low toxicity and have good plant tolerance.

QUOTES INCLUDE IN THE DESCRIPTION

This list of the documents listed by the applicant has been generated automatically and is included solely for the better information of the reader. The list is not part of the German patent or utility model application. The DPMA assumes no liability for any errors or omissions.

Cited patent literature

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Cited non-patent literature

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Claims (14)

Thioamides of the formula I

wherein the variables have the following meaning R ¹ OR ^A , S (O) _n -R ^A or OS (O) _n -R ^A ; R ^{A is} hydrogen, C ₁ -C ₄ -alkyl, ZC ₃ -C ₆ -cycloalkyl, C ₁ -C ₄ -haloalkyl, C ₂ -C ₆ -alkenyl, ZC ₃ -C ₆ -cycloalkenyl, C ₂ -C ₆ - alkynyl, Z- (tri-C ₁ -C ₄ alkyl) silyl, ZC (= O) -R ^a, Z-NR ^i, -C (O) -NR ⁱ R ^ii, ZP (= O) (R ^a) ₂ , NR ⁱ R ⁱⁱ , C or N bonded 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S. which may be partially or completely substituted by groups R ^a and / or R ^b , R ^{a is} hydrogen, OH, C ₁ -C ₈ alkyl, C ₁ -C ₄ haloalkyl, ZC ₃ -C ₆ cycloalkyl, C ₂ -C ₈ alkenyl, ZC ₅ -C ₆ cycloalkenyl, C ₂ -C ₈ alkynyl, ZC ₁ -C ₆ alkoxy, ZC ₁ -C ₄ haloalkoxy, ZC ₃ -C ₈ alkenyloxy, ZC ₃ -C _8- alkynyloxy, NR ⁱ R ⁱⁱ , C ₁ -C ₆ alkylsulfonyl, Z- (tri-C ₁ -C ₄ alkyl) silyl, Z-phenyl, Z-phenoxy, Z-phenylamino and 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S, wherein the cyclic groups are unsubstituted or substituted by 1, 2, 3, 4 or 5 groups R ^b ; R ⁱ , R ⁱⁱ independently of one another are hydrogen, C ₁ -C ₈ -alkyl, C ₁ -C ₄ -haloalkyl, C ₃ -C ₈ -alkenyl, C ₃ -C ₈ -alkynyl, ZC ₃ -C ₆ -cycloalkyl, ZC C ₁ -C ₈ -alkoxy, ZC ₁ -C ₈ -haloalkoxy, ZC (= O) -R ^a , Z-phenyl, Z-linked 3- to 7-membered monocyclic or 9- or 10-membered bicyclic saturated, unsaturated or aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S; R ⁱ and R ⁱⁱ may also together with the N-atom to which they are attached form a 5- or 6-membered monocyclic or 9- or 10-membered bicyclic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S; Z is a covalent bond or C ₁ -C ₄ -alkylene; n is 0, 1 or 2; R ^{2 is} phenyl, naphthyl or and 5- or 6-membered monocyclic or 9- or 10-membered bicyclic aromatic heterocycle containing 1, 2, 3 or 4 heteroatoms selected from O, N and S, wherein the cyclic groups unsubstituted or by 1 , 2, 3 or 4 groups R ^{b are} substituted, means; R ^b independently of one another Z-CN, Z-OH, Z-NO ₂ , Z-halogen, C ₁ -C ₈ -alkyl, C ₁ -C ₄ -haloalkyl, C ₂ -C ₈ -alkenyl, C ₂ -C ₈ Alkynyl, ZC ₁ -C ₈ alkoxy, ZC ₁ -C ₈ haloalkoxy, ZC ₃ -C ₁₀ cycloalkyl, OZC ₃ -C ₁₀ cycloalkyl, ZC (= O) -R ^a , NR ⁱ R ⁱⁱ , Z - (tri-C ₁ -C ₄ -alkyl) silyl, Z-phenyl and S (O) _n R ^bb , where R ^{bb is} C ₁ -C ₈ -alkyl and C ₁ -C ₆ -haloalkyl and n is 0, 1 or 2 stands; R ^b can also form, together with the group R ^b attached to the adjacent carbon atom, a five- or six-membered saturated, partially or completely unsaturated ring which, in addition to carbon atoms, can contain 1, 2 or 3 heteroatoms selected from O, N and S. ; YO or S; A, E, G, MN and CR ^c , wherein one or two groups thereof are N, with the proviso that not A is N when E, G and M are CH; R ^{c is} hydrogen or one of the groups mentioned for R ^b ; wherein in groups R ¹ , R ³ and their sub-substituents, the carbon chains and / or the cyclic groups may be partially or completely substituted by groups R ^b , and their N-oxides and agriculturally suitable salts. Compounds of formula I according to claim 1, wherein Y is O. Compounds of formula I according to claim 1 or 2, wherein R ^{1 is} OR ^A or OS (O) _n -R ^A. Compounds of the formula I according to one of Claims 1 to 3, which correspond to the formula I.1,

in which R ^c1 , R ^c2 and R ^c3 each correspond to a group R ^c , in particular hydrogen. Compounds of the formula I according to one of Claims 1 to 3, which correspond to the formula I.2,

in which R ^c1 , R ^c2 and R ^c4 each correspond to a group R ^c , in particular hydrogen. Compounds of the formula I according to one of Claims 1 to 3, which correspond to the formula I.3,

in which R ^c1 and R ^c3 each correspond to a group R ^c , in particular hydrogen. Compounds of the formula I according to one of Claims 1 to 3, which correspond to the formula I.4,

in which R ^c2 and R ^c3 each correspond to a group R ^c , in particular hydrogen. Compounds of the formula I according to one of Claims 1 to 3, which correspond to the formula I.5,

in which R ^c1 and R ^c2 each correspond to a group R ^c , in particular hydrogen. Compounds of the formula I according to one of Claims 1 to 8, which correspond to the formula IA,

in which R ⁵ and R ^{6 are} groups R ^b and m are zero or an integer from one to four. Compounds of the formula I which correspond to the formulas I.1, I.2, I.3, I.4 or I.5 according to one of claims 4 to 8, in which R ^{1 is} OH, OCH ₃ , OC (O) CH ₃ , OC (O) CH ₂ CH ₃ , OC (O) CH (CH ₃ ) ₂ , OC (O) C (CH ₃ ) ₃ , OC (O) -cC ₃ H ₅ , OC (O) -C ₆ H ₅ , OC (O) -CH ₂ C ₆ H ₅ , OC (O) CH ₂ Cl, OC (O) -CF ₃ , OC (O) -CH ₂ OCH ₃ , OC (O) -N (CH ₃ ) ₂ or OC (O) -OCH ₂ CH ₃ ; R ^{2 is} phenyl which is substituted by a group selected from 2-Br, 2-Cl, 2,4-Cl ₂ , 2-Cl-4-F, 2-Cl-5-F, 2-Cl-6-F , 2-Cl-4-CF ₃ , 2-Cl-5-CF ₃ , 2-Cl-6-CF ₃ , 2-Cl-3,6-F ₂ , 2-F, 2,4-F ₂ , 2,5-F ₂ , 2,6-F ₂ , 2-F-4-CF ₃ , 2-F-5-CF ₃ , 2-F-6-CF ₃ , 2,3,6-F ₃ , 2-NO ₂ , 2-NO ₂ -4-F, 2-NO ₂ -5-F, 2-NO ₂ -6-F, 2-NO ₂ -4-CF ₃ , 2-NO ₂ -5-CF ₃ , 2-NO ₂ -6-CF ₃ , 2-NO ₂ -3,6-F ₂ , 2-CN, 2-CH ₃ , 2-CH ₃ -4-F, 2-CH ₃ -5-F , 2-CH ₃ -6-F, 2-CH ₃ -4-CF ₃ , 2-CH ₃ -5-CF ₃ , 2-CH ₃ -6-CF ₃ , 2- CH ₃ -3,6-F ₂ , 2-OCH ₃ , 2-OCH ₃ -4-F, 2-OCH ₃ -5-F, 2-OCH ₃ -6-F, 2-OCH ₃ -4-CF ₃ , 2-OCH ₃ -5-CF ₃ , 2-OCH ₃ -6-CF ₃ , 2-OCH ₃ -3,6-F ₂ , 2-CHF ₂ , 2-CHF ₂ -4-F, 2 CHF ₂ -5-F, 2-CHF ₂ -6-F, 2-CHF ₂ -4-CF ₃ , 2-CHF ₂ -5-CF ₃ , 2-CHF ₂ -6-CF ₃ , 2-CHF ₂ -3,6-F ₂ , 2-CF ₃ , 2-CF ₃ -4-F, 2-CF ₃ -5-F, 2-CF ₃ -6-F, 2-CF ₃ -4-CF ₃ , 2-CF ₃ -5-CF ₃ , 2-CF ₃ -6-CF ₃ , 2-CF ₃ -3,6-F ₂ , 2-OCHF ₂ , 2-OCHF ₂ -4-F, 2-OCHF ₂ 5-F, 2-OCHF ₂ -6-F, 2-OCHF ₂ -4-CF ₃ , 2-OCHF ₂ -5-CF ₃ , 2-OCHF ₂ -6-CF ₃ , 2-OCHF ₂ -3 , 6-F ₂ , 2-OCF ₃ , 2-OCF ₃ -4-F, 2-OCF ₃ -5-F, 2-OCF ₃ -6-F, 2-OCF ₃ -4-CF ₃ , 2 OCF ₃ -5-CF ₃ , 2-OCF ₃ -6-CF ₃ or 2-OCF ₃ -3,6-F ₂ ; and Y is O or S. Agent comprising a herbicidally effective amount of at least one thioamide of the formula I or an agriculturally suitable salt thereof according to one of claims 1 to 10 and auxiliaries customary for the formulation of crop protection agents. Agent according to claim 11, containing at least one further active ingredient. Agent according to claim 11 or 12, containing two further active ingredients from the group of herbicides and / or safeners. A process for controlling undesired plant growth, which comprises allowing a herbicidally effective amount of at least one thioamide of the formula I or an agriculturally useful salt thereof according to one of claims 1 to 10 to act on plants, their seeds and / or their habitat.