DE3813886A1 - 1-Triazinyl-1H-1,2,4-triazole-3-sulphonamides, processes for their preparation, and their use as herbicides, fungicides and plant growth regulators - Google Patents

Abstract

The invention relates to novel 1-triazinyl-1H-1,2,4-triazole-3-sulphonamides of the general formula I <IMAGE> in which Ar, R<6>, R<7>, R<11> and R<12> have the meanings given in the description, to processes for their preparation and to their use as herbicides, fungicides and plant growth regulators.

Description

The invention relates to new 1-triazinyl-1H-1,2,4-triazole-3-sulfonic acid amides, Process for their preparation and their use as herbicidal compositions, fungicidal and plant growth regulating effect.

It is already known that triazole sulfonamides have a herbicidal action (EP applications 01 42 152, 01 50 974 and 02 46 749). However, is common the herbicidal activity of the known compounds is insufficient, respectively With a corresponding herbicide effect, selectivity problems arise in major agricultural crops.

The object of the present invention is to provide new compounds, which do not have these disadvantages and in their biological Properties are superior to previously known compounds.

It has now been found that 1-triazinyl-1H-1,2,4-triazole-3-sulfonic acid amides of the general formula I

in the

Ar is a phenyl, naphthyl, pyridyl, pyrazolyl or thienyl group of general formulas

or another simple or condensed heterocyclic group,
R¹, R², R³, R⁴ and R⁵, which are the same or different, represent a hydrogen atom, a C₁-C₆-alkyl radical, one or more, the same or different, by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁- C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl substituted C₁-C₆-alkyl, a C₂-C₆-alkenyl, one or more, the same or differently C₂-C Hydrox substituted by halogen, hydroxy, halogen-C₁-C₁-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl -Alkenyl radical, a C₂-C₆-alkynyl radical, one or more, the same or different, by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄- Alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl-substituted C₂-C₆-alkynyl, a halogen atom, a C₁-C₄-alkoxy group, a halogen-C₁-C₄-alkoxy group, a group R¹⁰-O-CO-, an aminocarbonyl group R⁸R⁹N-CO-, an amino group R⁸R⁹N-, a cyanog group, a nitro group, a sulfur-containing group R¹⁰-S (O) _n -, an acyl group R¹⁰-CO-, a group R¹⁰-O-CO- (CH₂) _n -, one by C₁-C₄-alkyl, halogen or nitro substituted phenyl radical or a phenoxy radical substituted by C₁-C₄-alkyl, halogen or nitro,
R⁶ is a hydrogen atom, an acyl group R¹⁰-CO-, a group R¹⁰-O-CO-, a C₁-C₆-alkyl radical, a C₂-C₆-alkenyl radical, a C₂-C₆-alkynyl radical, a phenyl-C₁-C₄-alkyl radical, an aminocarbonyl group R⁸R⁹N-CO-, an alkali metal atom, a monovalent metal equivalent from the group of alkaline earth metals and other metals, an ammonium radical, an ammonium radical substituted by C₁-C₆alkyl or a pyridinium radical,
R⁷ represents a hydrogen atom or an amino group R¹³R¹⁴N-,
R⁸ is a hydrogen atom, a C₁-C₆-alkyl radical, a one or more, identical or differently substituted by halogen, hydroxy or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl radical, a C₂-C₆-alkenyl radical, a one or more of the same or differently substituted by halogen, hydroxy or C₁-C₄-alkoxy, C₂-C₆-alkenyl, a C₂-C₆-alkynyl radical, one or more, identically or differently, substituted by halogen, hydroxy or C₁-C₄-alkoxy, C₂-C₆- Alkynyl radical,
R⁹ is a hydrogen atom, a C₁-C₆-alkyl radical, a C₁-C₆-alkyl radical substituted one or more times, identically or differently by halogen, hydroxy or C₁-C₄-alkoxy, a C₂-C₆-alkenyl radical, a one or more times the same or differently substituted by halogen, hydroxy or C₁-C₄-alkoxy, C₂-C₆-alkenyl, a C₂-C₆-alkynyl radical, one or more, identically or differently, substituted by halogen, hydroxy or C₁-C₄-alkoxy, C₂-C₆- Alkynyl radical, or
R⁸ and R⁹ together with the adjacent nitrogen atom represent a pyrolidinyl group, a piperidino group or a morpholino group,
R¹⁰ is a hydrogen atom, a C₁-C₆-alkyl radical, a C₁-C Alkyl-alkyl radical, substituted one or more times, identically or differently by halogen, hydroxyl or C₁-C Alk-alkoxy, a C₂-C₆-alkenyl radical, one or more, the same or different halogen, hydroxy or C₁-C₄-alkoxy substituted C₂-C₆-alkenyl radical, a C₂-C₆-alkynyl radical, a one or more, the same or different, halogen or hydroxy or C₁-C₄-alkoxy substituted C₂-C₆ -Alkynyl radical, a phenyl-C₁-C alkyl-alkyl radical, a one or more, identically or differently substituted by halogen, hydroxy or C₁-C₄-alkoxy-substituted phenyl-C₁-C Alk-alkyl radical, a phenyl radical or by halogen, nitro or C₁ -C₄-alkyl substituted phenyl radical,
R¹¹ is a hydrogen atom, a C₁-C₆-alkyl radical, one or more, the same or different, by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄ -Alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl-substituted C₁-C₆-alkyl radicals, a C₂-C₆-alkenyl radical, one or more, identical or different, by halogen, hydroxy, halogen-C₁-C--alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl substituted C₂-C₆-alkenyl radical, a C₂-C₆-alkynyl radical, one or more times , identical or different by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl substituted C₂ -C₆-alkynyl, a halogen atom, a C₁-C₄-alkoxy, a halogen-C₁-C₄-alkoxy, a group R¹⁰-O-CO-, an aminocarbonyl group R⁸R⁹N-CO-, an amino group R⁸R⁹N-, a cyano group, a nitro group , a group containing sulfur pe R¹⁰-S (O) _n -, an acyl group R¹⁰-CO-, a group R¹⁰-O-CO- (CH₂) _n -, a phenyl radical, a phenyl radical substituted by C₁-C₄-alkyl, halogen or nitro, a phenoxy radical or a phenoxy radical substituted by C₁-C₄-alkyl, halogen or nitro,
R¹² is a hydrogen atom, a C₁-C₆-alkyl radical, one or more, identical or different by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄ -Alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl-substituted C₁-C₆-alkyl radicals, a C₂-C₆-alkenyl radical, one or more, identical or different, by halogen, hydroxy, halogen-C₁-C--alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl substituted C₂-C₆-alkenyl radical, a C₂-C₆-alkynyl radical, one or more times , identical or different by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl substituted C₂ -C₆-alkynyl, a halogen atom, a group R¹⁰-O-CO-, an aminocarbonyl group R⁸R⁹N-CO-, an amino group R⁸R⁹N-, a cyano group, a nitro group, a sulfur-containing group R¹⁰-S (O) _n -, an acyl group R¹⁰-CO-, a group R¹ ⁰-O-CO- (CH₂) _n -, a phenyl radical, a phenyl radical substituted by C₁-C₄-alkyl, halogen or nitro, a phenoxy radical or a phenoxy radical substituted by C₁-C₄-alkyl, halogen or nitro,
n 0, 1 or 2,
R¹³ is a hydrogen atom, a C₁-C₆-alkyl radical, a C₁-C₆-alkyl radical substituted by halogen and / or C₁-C₄-alkoxy, a C₂-C₆-alkenyl radical, a C₂- substituted by halogen and / or C₁-C₄-alkoxy C₆-alkenyl, a C₂-C₆-alkynyl, a halogen and / or C₁-C₄-alkoxy substituted C₂-C₆-alkynyl or an acyl group R¹⁰-CO-,
R¹⁴ is a hydrogen atom, a C₁-C₆-alkyl radical, a C₁-C₆-alkyl radical substituted by halogen and / or C₁-C₄-alkoxy, a C₂-C₆-alkenyl radical, a C₂- substituted by halogen and / or C₁-C₄-alkoxy C₆-alkenyl, a C₂-C₆-alkynyl, a halogen and / or C₁-C₄-alkoxy substituted C₂-C₆-alkynyl or an acyl group R¹⁰-CO-, or
R¹³ and R¹⁴ together are an alkylidene group of the formula = CAB,
A is a hydrogen atom or a C₁-C₄ alkyl radical,
B is a C₁-C₄ alkoxy or a C₁-C₄ alkylamino or
R¹³ and R¹⁴ together with the adjacent nitrogen atom represent a piperidino group, one or more, the same or different, by halogen, nitro, cyano, phenyl, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl, C₁ -C₄-acyl or C₁-C₄-alkoxy substituted piperidino group, a morpholino group, one or more, the same or different, by halogen, nitro, cyano, phenyl, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, C₁- C₄-Alkoxycarbonyl, C₁-C₄-acyl or C₁-C₄-alkoxy substituted morpholino group, a pyrrolidinyl group, one or more, the same or different, by halogen, nitro, cyano, phenyl, C₁-C₄-alkyl, halogen-C₁-C₄ -Alkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-acyl or C₁-C₄-alkoxy substituted pyrrolidinyl group, a pyrrolyl group or a one or more, the same or different, by halogen, nitro, cyano, phenyl, C₁-C₄-alkyl , Halogen-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-acyl or C₁-C₄-alkoxy substituted pyrrolyl group

mean an interesting herbicidal, fungicidal and plant growth regulating Show effects.

The term "halogen" in connection with alkyl, alkenyl, alkynyl or Phenyl means that one or more hydrogen atoms are replaced by one or more Halogen atoms are replaced. The term "halogen" includes fluorine, Chlorine, bromine and iodine.

Such 1-triazinyl-1H-1,2,4-triazole-3-sulfonic acid amides have proven particularly effective of general formula I, in which Ar is a phenyl group of the general formula  

R¹ and R⁵, which are the same or different, represent a hydrogen atom, a halogen atom, a methyl group, a trifluoromethyl group, a nitro group, a methoxy group, a difluoromethoxy group or a methoxycarbonyl group,
R², R³ and R⁴, which are the same or different, represent a hydrogen atom, a halogen atom, a trifluoromethyl group or a C₁-C₄ alkyl group,
R⁶ is a hydrogen atom, a monovalent metal equivalent, a pyridinium radical or a C₁-C₄ acyl group,
R⁷ is a hydrogen atom or an amino group
R¹¹ is a halogen atom, a C₁-C₂-alkyl group, a C₁-C₂-alkoxy group, a C₁-C₂-alkylthio group, a halogen-C₁-C₂-alkyl group or a hydrogen atom and
R¹² is a halogen atom, a C₁-C₂ alkyl group, a C₁-C₂ alkoxy group, a C₁-C₂ alkylthio group, a halogen C₁-C₂ alkyl group or a hydrogen atom

mean.

The compounds of general formula I according to the invention can Example made by

• A) Amines of the general formula II, Ar-NH-R⁶ (II) in which Ar has the meaning given above and R⁶ is a hydrogen atom, a C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl group , with a sulfonic acid chloride of the general formula III in which R⁷, R¹¹ and R¹² have the meanings given above, in a suitable solvent in the presence of an acid acceptor, or
• B) a compound of the general formula IV in which Ar, R⁷, R¹¹ and R¹² have the meanings given above and R¹⁵ represents a hydrogen atom or a monovalent metal equivalent, with a compound of the general formula VR¹⁰-X (V) or a compound of the general formula VI in which R¹⁰ has the meaning given above, but does not represent hydrogen, and X represents a chlorine or bromine atom, or a compound of the general formula VII in which R¹⁰ has the meaning given above, in a suitable solvent, or
• C) a compound of the general formula VIII in which Ar, R⁶ and R⁷ have the meanings given above, with a compound of the general formula IX in which Z represents chlorine, bromine or a group R¹⁰-SO₂- and R¹⁰, R¹¹ and R¹² have the meanings given above, in a suitable solvent in the presence of a catalyst and / or acid-binding agent, or
• D) a compound of the general formula X in which Ar, R⁷, R¹¹ and R¹² have the meanings given above, with a compound of the general formula XIM-Y (XI) in which M is a monovalent metal equivalent and Y is a hydrogen atom, a hydroxyl, lower alkyl, lower alkoxy or amino group , reacted in a solvent.

The individual process variants are preferably in the presence of a Diluent carried out. For this purpose, everyone can face the solvents used are inert solvents.

Examples of such solvents or diluents are Water, aliphatic, alicyclic and aromatic hydrocarbons, the each may optionally be chlorinated, such as hexane, Cyclohexane, petroleum ether, ligroin, benzene, toluene, xylene, methylene chloride, Chloroform, carbon tetrachloride, ethylene chloride and trichlorethylene, Ethers, such as, for example, diisopropyl ether, dibutyl ether, propylene oxide, Dioxane and tetrahydrofuran, ketones such as acetone, methyl ethyl ketone, Methyl isopropyl ketone and methyl isobutyl ketone, nitriles such as Acetonitrile and propionitrile. Alcohols, such as methanol, Ethanol, isopropanol, butanol and ethylene glycol, esters such as Ethyl acetate and amyl acetate, acid amides such as dimethylformamide and Dimethylacetamide, sulfones and sulfoxides, such as dimethyl sulfoxide and Sulfolane, and bases such as pyridine.

The presence of a reaction catalyst can be advantageous. As catalysts Potassium iodide and onium compounds are suitable, such as quaternary ones Ammonium, phosphonium and arsonium compounds as well as sulfonium compounds. Also suitable are polyglycol ethers, especially cyclic, such as 18-crown-6, and tertiary amines such as tributylamine. Preferred compounds are quaternary ammonium compounds, such as Example benzyltriethylammonium chloride and tetrabutylammonium bromide.  The reactions are preferably between room temperature and the boiling point carried out the respective reaction mixture. Let the reactions perform themselves at the pressure of the environment, even if they increase or reduced pressure can be performed.

Process variant A) is preferably used in chlorinated hydrocarbons, such as dichloromethane or dichloroethane, in the presence of a catalyst or acid acceptor performed. examples for this are tertiary amines, such as triethylamine, diisopropylethylamine, N-methylmorpholine, 4-dimethylaminopyridine and pyridine. Pyridine can both used as a catalyst as well as a solvent in this reaction will.

Process variant B) is preferably carried out in inert solvents, such as for example dimethylformamide or tetrahydrofuran, carried out by a compound of general formula IV with an alkylation or Acylating agents of the general formulas V, VI or VII are implemented.

Process variant C) is preferred in internal solvents such as Dioxane, tetrahydrofuran, dimethylformamide or N-methylpyrrolidinone, if necessary carried out in the presence of a catalyst. examples for Acid-binding agents are metal hydrides, tert. Amines such as triethylamine or diisopropylethylamine and bases such as 1,5-diazabicyclo (4,3,0) non-5-ene (DBN), 1,8-diazabicyclo (5,4,0) undec-7-ene (DBU) or 1,4-diazabicyclo (2,2,2) octane (DABCO).

Process variant D) is preferably carried out in such a way that a Compound of general formula XI in a suitable solvent with a metal base, such as a metal hydroxide, metal hydride, metal alkyl or Metallamide or an amine, and the usually less soluble Salts filtered off or obtained after evaporation of the solvents.

The compounds according to the invention produced by the abovementioned processes can be isolated from the reaction mixture by the customary methods be, for example by distilling off the solvent used  at normal or reduced pressure, through precipitation with water or by extraction.

An increased degree of purity can usually be determined by column chromatography Purification and by fractional distillation or crystallization be preserved.

The compounds according to the invention are generally colorless and odorless Liquids, as well as crystals, are soluble in water, slightly soluble in aliphatic hydrocarbons, such as petroleum ether, hexane, pentane and cyclohexane, readily soluble in halogenated hydrocarbons, such as Chloroform, methylene chloride and carbon tetrachloride, aromatic hydrocarbons, such as benzene, toluene and xylene, ethers such as diethyl ether, Tetrahydrofuran and dioxane, carbonitriles, such as acetonitrile, alcohols, such as methanol and ethanol, carboxamines, such as dimethylformamide, and sulfoxides such as dimethyl sulfoxide.

The sulfonic acid chlorides of the general formula III are new and can be from processes described in the literature or by known processes representable 1-triazinyl-3-benzylthio-1H-1,2,4-triazoles of the general Formula XII

in which R⁷, R¹¹ and R¹² have the meanings given above, by reaction Prepare with chlorine in water or water / acetic acid mixtures.

1H-1,2,4-triazole-3-sulfonic acid amides of the general formula VIII and triazines of the general formula IX are known, or in the literature described, process can be represented.  

The compounds according to the invention show a good herbicidal activity broad-leaved weeds and grasses. A selective use of the invention Active ingredients are possible in different cultures, for example in rapeseed, beets, soybeans, cotton, rice, barley, wheat and other cereals. Individual active ingredients are selective herbicides in beets, Cotton, soybeans and cereals are particularly suitable. Likewise, the connections for weed control in permanent crops, such as forestry, Ornamental wood, fruit, wine, citrus, nut, banana, coffee, tea, rubber, Oil palm, cocoa, berry fruit and hop plants, and for selective weed control be used in annual crops.

The compounds according to the invention can be used, for example, in the following plant genera:
Dicotyledon weeds of the genera Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Brassica, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirschum, Carduanus, Carduan Rorippa, Lamium, Veronica, Abutilon, Datura, Viola, Galeopsis, Papaver, Centaurea and Chrysanthemum.

Monocot weeds of the genera Avena, Alopecurus, Echinochloa, Setaria, Panicum, Digitaria, Poa, Eleusine, Brachiaria, Lolium, Bromus, Cyperus, Agropyron, Sagittaria, Monochoria, Fimbristylis, Eleocharis, Ischaemum and Apera.

Depending on the type of application, the application rates fluctuate in the pre- and post-emergence between 0.01 and 5 kg / ha.

The active compounds according to the invention can also be used as defoliants, desiccants and can be used as an herbicide. They also affect plant growth and can therefore influence the growth of crops be used. Some of these active ingredients also show a fungicidal effect Effect.  

The compounds according to the invention can either be used alone or in a mixture with one another or with other active ingredients. Possibly other pesticides or pesticides depending on desired purpose can be added. If a broadening of the spectrum of activity other herbicides may also be added. For example, those suitable as herbicidally active mixture partners Active ingredients described in Weed Abstracts, Vol. 36, No. 12, 1987, under the title "List of common names and abbreviations employed for currently used herbicides and plant growth regulators in Weed Abstracts ".

A promotion of the intensity and speed of action can Example by adding additives, such as organic solvents, Wetting agents and oils can be achieved. Such additives may therefore be left out a reduction in drug dosage.

The labeled active ingredients or their mixtures are expediently in Form of preparations, such as powders, sprinkling agents, granules, solutions, Emulsions or suspensions, with the addition of liquid and / or solid Carriers or diluents and, if necessary, adhesives, Wetting, emulsifying and / or dispersing aids applied.

Suitable liquid carriers are, for example, aliphatic and aromatic Hydrocarbons, such as benzene, toluene, xylene, cyclohexanone, isophorone, Dimethyl sulfoxide, dimethylformamide, mineral oil fractions and Vegetable oils.

Minerals are suitable as solid carriers, for example bentonite, silica gel, Talc, kaolin, attapulgite, limestone, and herbal products, for Example flour.

Examples of surface-active substances include calcium lignin sulfonate, Polyethylene alkylphenyl ether, naphthalenesulfonic acids and their salts, Phenolsulfonic acids and their salts, formaldehyde condensates, fatty alcohol sulfates as well as substituted benzenesulfonic acids and their salts.  

The proportion of the active ingredient (s) in the different preparations can vary widely. For example, the Average about 10 to 90 percent by weight of active ingredient, about 90 to 10 percent by weight liquid or solid carriers and optionally up to 20 Weight percent surfactants.

The funds can be applied in the customary manner, for example with water as a carrier in spray liquor quantities about 100 to 1000 liters / ha. A Use of the funds in the so-called low-volume and ultra-low-volume process is just as possible as their application in the form of so-called microgranules.

These preparations can be prepared in a manner known per se and Way, for example by grinding or mixing processes. If desired, preparations of the individual components can also be made only briefly be mixed before use, for example in the so-called Tank mix procedure is carried out in practice.  

For the preparation of the various preparations, for example following components:

A) wettable powder

1.)
25 percent by weight of active ingredient
60 weight percent kaolin
10 weight percent silica
5 percent by weight of a mixture of the calcium salt of lignosulfonic acid and the sodium salt of N-methyl-N-oleyl-taurine
2.)
40 percent by weight of active ingredient
25% by weight of clay minerals
25 weight percent silica
10 percent by weight of a mixture of the calcium salt of lignin sulfonic acid and alkylphenyl polyglycol ethers

B) paste

45 percent by weight of active ingredient
5% by weight sodium aluminum silicate
15 percent by weight cetyl polyglycol ether with 8 moles of ethylene oxide
2% by weight spindle oil
10% by weight polyethylene glycol
23 weight percent water

C) Emulsion concentrate

25 percent by weight of active ingredient
15 weight percent cyclohexanone
55% by weight xylene
5 percent by weight of a mixture of the calcium salt of dodecylbenzenesulfonic acid and nonylphenylpolyoxyethylene

The following examples illustrate the preparation of the invention Links:

example 1 1- (4-methoxy-6-methyl-s-triazin-2-yl) -1H-1,2,4-triazol-3-sulfonic acid - 2,6-di chloro-3-methylanilide

3.1 g (10 mmol) of 1H-1,2,4-triazole-3-sulfonic acid-2,6-dichloro-3-methylanilide, 1.6 g (10 mmol) of 2-chloro-4-methoxy-6- methyl-s-triazine and 1.5 g (11 mmol) of potassium carbonate are stirred in 20 ml of dimethylformamide for 24 hours at room temperature. After evaporation (oil pump vacuum), the residue is mixed with 100 ml of water and acidified with 2 N hydrochloric acid solution (pH 4). The crystals are filtered off and dried in vacuo (200 mbar) at 70 ° C.
Yield: 3.4 g = 79% of theory
Mp .: 212 ° C (dec.)

The following compounds according to the invention were also prepared analogously:

The following examples explain the possible uses of the invention Links:

Example A

The plant species listed were in the greenhouse before emergence with the listed compounds at a rate of 0.03 kg of active ingredient / ha treated. The compounds were used as emulsions for this purpose sprayed evenly over the plants with 500 liters of water / ha. Here showed the compounds of the invention three weeks after treatment a high crop selectivity in wheat and typical subsequent crops such as sugar beet, Brassica sp., sunflower and cotton with excellent Effect against weeds. The comparative agent did not show the high selectivity.

In the following table mean:

0 = not damaged
4 = totally destroyed
TRZAX = Triticum aestivum
BEAVX = Beta vulgaris
BRSSS = Brassica sp.
HELAN = Helianthus annuus
GOSHI = Gossypium hirsutum
MATCH = Matricaria chamomilla
VERPE = Veronica persica

Example B

The plant species listed were in the greenhouse before emergence with the listed compounds at a rate of 0.1 kg of active ingredient / ha treated. The compounds were used as emulsions for this purpose sprayed evenly over the plants with 500 liters of water / ha. Here showed the compounds of the invention three weeks after treatment a high crop selectivity in sunflower with excellent Effect against weeds. The comparison means did not show the same level Selectivity.

In the following table mean:

0 = not damaged
4 = totally destroyed
HELAN = Helianthus annuus
VIOSS = Viola sp.

Example C

The plant species listed were in the greenhouse after emergence with the listed compounds at a rate of 0.01 kg of active ingredient / ha treated. The compounds were used as emulsions for this purpose sprayed evenly over the plants with 500 liters of water / ha. Here showed the compounds of the invention two weeks after treatment high crop selectivity in cotton with excellent effects against the weeds. The comparison means did not show the same level Selectivity.

In the following table mean:

0 = not damaged
4 = totally destroyed
GOSHI = Gossypium hirsutum
SOLSS = Solanum sp.

Example D

In the greenhouse, the compounds listed in the table with the also applied application rate applied. For this purpose, the active ingredients placed in vessels with 1500 ml of water. Echinochloa was used as the test plant species crus-galli (ECHCG), Sagittaria sp. (SAGSS), Scirpus juncoides (SCPJU), Eleocharis kuroguwai (ELOKU) and Cyperus sp. (CYPSS) in the 2- to 5-leaf stage used. Three weeks after the application, the damage to the Plants rated according to the following scheme:

0 = no damage
1 = slight damage
2 = moderate damage
3 = severe damage
4 = totally destroyed
- = not tested

As the table shows, the compounds according to the invention are very effective against important rice weeds.

Claims (8)

1. 1-triazinyl-1H-1,2,4-triazole-3-sulfonic acid amides of the general formula I in the Ar a phenyl, naphthyl, pyridyl, pyrazolyl or thienyl group of the general formulas or another simple or condensed heterocyclic group,
R¹, R², R³, R⁴ and R⁵, which are the same or different, represent a hydrogen atom, a C₁-C₆-alkyl radical, one or more, the same or different, by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁- C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl substituted C₁-C₆-alkyl, a C₂-C₆-alkenyl, one or more, the same or differently C₂-C Hydrox substituted by halogen, hydroxy, halogen-C₁-C₁-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl -Alkenyl radical, a C₂-C₆-alkynyl radical, one or more, the same or different, by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄- Alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl-substituted C₂-C₆-alkynyl, a halogen atom, a C₁-C₄-alkoxy group, a halogen-C₁-C₄-alkoxy group, a group R¹⁰-O-CO-, an aminocarbonyl group R⁸R⁹N-CO-, an amino group R⁸R⁹N-, a cyanog group, a nitro group, a sulfur-containing group R¹⁰-S (O) _n -, an acyl group R¹⁰-CO-, a group R¹⁰-O-CO- (CH₂) _n -, one by C₁-C₄-alkyl, halogen or nitro substituted phenyl radical or a phenoxy radical substituted by C₁-C₄-alkyl, halogen or nitro,
R⁶ is a hydrogen atom, an acyl group R¹⁰-CO-, a group R¹⁰-O-CO-, a C₁-C₆-alkyl radical, a C₂-C₆-alkenyl radical, a C₂-C₆-alkynyl radical, a phenyl-C₁-C₄-alkyl radical, an aminocarbonyl group R⁸R⁹N-CO-, an alkali metal atom, a monovalent metal equivalent from the group of alkaline earth metals and other metals, an ammonium radical, an ammonium radical substituted by C₁-C₆alkyl or a pyridinium radical,
R⁷ represents a hydrogen atom or an amino group R¹³R¹⁴N-,
R⁸ is a hydrogen atom, a C₁-C₆-alkyl radical, a one or more, identical or differently substituted by halogen, hydroxy or C₁-C₄-alkoxy-substituted C₁-C₆-alkyl radical, a C₂-C₆-alkenyl radical, a one or more of the same or differently substituted by halogen, hydroxy or C₁-C₄-alkoxy, C₂-C₆-alkenyl, a C₂-C₆-alkynyl radical, one or more, identically or differently, substituted by halogen, hydroxy or C₁-C₄-alkoxy, C₂-C₆- Alkynyl radical,
R⁹ is a hydrogen atom, a C₁-C₆-alkyl radical, a C₁-C₆-alkyl radical substituted one or more times, identically or differently by halogen, hydroxy or C₁-C₄-alkoxy, a C₂-C₆-alkenyl radical, a one or more times the same or differently substituted by halogen, hydroxy or C₁-C₄-alkoxy, C₂-C₆-alkenyl, a C₂-C₆-alkynyl radical, one or more, identically or differently, substituted by halogen, hydroxy or C₁-C₄-alkoxy, C₂-C₆- Alkynyl radical, or
R⁸ and R⁹ together with the adjacent nitrogen atom represent a pyrolidinyl group, a piperidino group or a morpholino group,
R¹⁰ is a hydrogen atom, a C₁-C₆-alkyl radical, a C₁-C Alkyl-alkyl radical, substituted one or more times, identically or differently by halogen, hydroxyl or C₁-C Alk-alkoxy, a C₂-C₆-alkenyl radical, one or more, the same or different halogen, hydroxy or C₁-C₄-alkoxy substituted C₂-C₆-alkenyl radical, a C₂-C₆-alkynyl radical, a one or more, the same or different, halogen or hydroxy or C₁-C₄-alkoxy substituted C₂-C₆ -Alkynyl radical, a phenyl-C₁-C alkyl-alkyl radical, a one or more, identically or differently substituted by halogen, hydroxy or C₁-C₄-alkoxy-substituted phenyl-C₁-C Alk-alkyl radical, a phenyl radical or by halogen, nitro or C₁ -C₄-alkyl substituted phenyl radical,
R¹¹ is a hydrogen atom, a C₁-C₆-alkyl radical, one or more, the same or different, by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄ -Alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl-substituted C₁-C₆-alkyl radicals, a C₂-C₆-alkenyl radical, one or more, identical or different, by halogen, hydroxy, halogen-C₁-C--alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl substituted C₂-C₆-alkenyl radical, a C₂-C₆-alkynyl radical, one or more times , identical or different by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl substituted C₂ -C₆-alkynyl, a halogen atom, a C₁-C₄-alkoxy, a halogen-C₁-C₄-alkoxy, a group R¹⁰-O-CO-, an aminocarbonyl group R⁸R⁹N-CO-, an amino group R⁸R⁹N-, a cyano group, a nitro group , a group containing sulfur pe R¹⁰-S (O) _n -, an acyl group R¹⁰-CO-, a group R¹⁰-O-CO- (CH₂) _n -, a phenyl radical, a phenyl radical substituted by C₁-C₄-alkyl, halogen or nitro, a phenoxy radical or a phenoxy radical substituted by C₁-C₄-alkyl, halogen or nitro,
R¹² is a hydrogen atom, a C₁-C₆-alkyl radical, one or more, identical or different by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄ -Alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl-substituted C₁-C₆-alkyl radicals, a C₂-C₆-alkenyl radical, one or more, identical or different, by halogen, hydroxy, halogen-C₁-C--alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl substituted C₂-C₆-alkenyl radical, a C₂-C₆-alkynyl radical, one or more times , identical or different by halogen, hydroxy, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxy, halogen-C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₁-C₄-alkylsulfinyl or C₁-C₄-alkylsulfonyl substituted C₂ -C₆-alkynyl, a halogen atom, a group R¹⁰-O-CO-, an aminocarbonyl group R⁸R⁹N-CO-, an amino group R⁸R⁹N-, a cyano group, a nitro group, a sulfur-containing group R¹⁰-S (O) _n -, an acyl group R¹⁰-CO-, a group R¹ ⁰-O-CO- (CH₂) _n -, a phenyl radical, a phenyl radical substituted by C₁-C₄-alkyl, halogen or nitro, a phenoxy radical or a phenoxy radical substituted by C₁-C₄-alkyl, halogen or nitro,
n 0, 1 or 2,
R¹³ is a hydrogen atom, a C₁-C₆-alkyl radical, a C₁-C₆-alkyl radical substituted by halogen and / or C₁-C₄-alkoxy, a C₂-C₆-alkenyl radical, a C₂- substituted by halogen and / or C₁-C₄-alkoxy C₆-alkenyl, a C₂-C₆-alkynyl, a halogen and / or C₁-C₄-alkoxy substituted C₂-C₆-alkynyl or an acyl group R¹⁰-CO-,
R¹⁴ is a hydrogen atom, a C₁-C₆-alkyl radical, a C₁-C₆-alkyl radical substituted by halogen and / or C₁-C₄-alkoxy, a C₂-C₆-alkenyl radical, a C₂- substituted by halogen and / or C₁-C₄-alkoxy C₆-alkenyl, a C₂-C₆-alkynyl, a halogen and / or C₁-C₄-alkoxy substituted C₂-C₆-alkynyl or an acyl group R¹⁰-CO-, or
R¹³ and R¹⁴ together are an alkylidene group of the formula = CAB,
A is a hydrogen atom or a C₁-C₄ alkyl radical,
B is a C₁-C₄ alkoxy or a C₁-C₄ alkylamino or
R¹³ and R¹⁴ together with the adjacent nitrogen atom represent a piperidino group, one or more, the same or different, by halogen, nitro, cyano, phenyl, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl, C₁ -C₄-acyl or C₁-C₄-alkoxy substituted piperidino group, a morpholino group, one or more, the same or different, by halogen, nitro, cyano, phenyl, C₁-C₄-alkyl, halogen-C₁-C₄-alkyl, C₁- C₄-Alkoxycarbonyl, C₁-C₄-acyl or C₁-C₄-alkoxy substituted morpholino group, a pyrrolidinyl group, one or more, the same or different, by halogen, nitro, cyano, phenyl, C₁-C₄-alkyl, halogen-C₁-C₄ -Alkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-acyl or C₁-C₄-alkoxy substituted pyrrolidinyl group, a pyrrolyl group or a one or more, the same or different, by halogen, nitro, cyano, phenyl, C₁-C₄-alkyl , Halogen-C₁-C₄-alkyl, C₁-C₄-alkoxycarbonyl, C₁-C₄-acyl or C₁-C₄-alkoxy substituted pyrrolyl mean. 2. 1-triazinyl-1H-1,2,4-triazole-3-sulfonic acid amides according to claim 1, characterized in that in the general formula I
Ar is a phenyl group of the general formula R¹ and R⁵, which are the same or different, represent a hydrogen atom, a halogen atom, a methyl group, a trifluoromethyl group, a nitro group, a methoxy group, a difluoromethoxy group or a methoxycarbonyl group,
R², R³ and R⁴, which are the same or different, represent a hydrogen atom, a halogen atom, a trifluoromethyl group or a C₁-C₄ alkyl group,
R⁶ is a hydrogen atom, a monovalent metal equivalent, a pyridinium radical or a C₁-C₄ acyl group,
R⁷ is a hydrogen atom or an amino group
R¹¹ is a halogen atom, a C₁-C₂-alkyl group, a C₁-C₂-alkoxy group, a C₁-C₂-alkylthio group, a halogen-C₁-C₂-alkyl group or a hydrogen atom and
R¹² represents a halogen atom, a C₁-C₂ alkyl group, a C₁-C₂ alkoxy group, a C₁-C₂ alkylthio group, a halogen C₁-C₂ alkyl group or a hydrogen atom. 3. Process for the preparation of 1-triazinyl-1H-1,2,4-triazole-3-sulfonamides of the general formula I, characterized in that

• A) Amides of the general formula II, Ar-NH-R⁶ (II) in which Ar has the meaning given above and R⁶ is a hydrogen atom, a C₁-C₆-alkyl, C₂-C₆-alkenyl or C₂-C₆-alkynyl group , with a sulfonic acid chloride of the general formula III in which R⁷, R¹¹ and R¹² have the meanings given above, in a suitable solvent in the presence of an acid acceptor, or
• B) a compound of the general formula IV in which Ar, R⁷, R¹¹ and R¹² have the meanings given above and R¹⁵ represents a hydrogen atom or a monovalent metal equivalent, with a compound of the general formula VR¹⁰-X (V) or a compound of the general formula VI in which R¹⁰ has the meaning given above, but does not represent hydrogen, and X represents a chlorine or bromine atom, or a compound of the general formula VII in which R¹⁰ has the meaning given above, in a suitable solvent, or
• C) a compound of the general formula VIII in which Ar, R⁶ and R⁷ have the meanings given above, with a compound of the general formula IX in which Z represents chlorine, bromine or a group R¹⁰-SO₂- and R¹⁰, R¹¹ and R¹² have the meanings given above, in a suitable solvent in the presence of a catalyst and / or acid-binding agent, or
• D) a compound of the general formula X in which Ar, R⁷, R¹¹ and R¹² have the meanings given above, with a compound of the general formula XIM-Y (XI) in which M is a monovalent metal equivalent and Y is a hydrogen atom, a hydroxyl, lower alkyl, lower alkoxy or amino group , reacted in a solvent.

4. Agents with herbicidal, fungicidal and plant growth regulating Effect, characterized by a content of at least one compound according to claims 1 and 2.   5. Use of agents according to claims 4 for combating monocotyledons and dicotyledonous weed species in main agricultural crops. 6. Use of agents according to claim 4 for combating a fungal attack in agricultural crops. 7. Use of agents according to claim 4 for influencing growth of crops. 8. Process for the preparation of compositions with herbicidal and growth-regulating Effect, characterized in that compounds of general Formula I according to claims 1 and 2 with carrier and / or Auxiliary materials mixed.