DE3921271A1 - New purine-8-sulphonamide derivs. - useful as herbicides and plant growth regulators - Google Patents

Abstract

Purine-8-sulphonamides of formula (I) and their salts are new: the dotted line denotes a 7,8 double bond when R2 is on N or an 8,9 double bond when R2 is on N7; R1 = H or 1-4C alkyl; R2 = (a) H, (b) 1-6C alkyl opt. substd. by 1-5 halogen atoms and/or one of 1-4C alkoxy, 1-4C haloalkoxy, 1-4C alkylthio, 1-4C haloalkylthio, Ph, OPh or SPh, (c) 3-4C alkenyl or alkynyl, or (d) satd. or monounsatd. opt. substd. 5- to 7-membered heterocyclyl; R3 and R4 = (a) halogen, (b) 1-4C alkoxy, 1-4C alkylthio, 2-6C alkenyl, 2-6C alkenyloxy, 2-6C alkenylthio, 2-6C alkynyloxy or 2-6C alkynylthio, all opt. substd. by 1-5 halogen atoms and/or one of 1-4C alkoxy, 1-4C haloalkoxy, 2-4C alkylthio, 1-4C haloalkylthio, Ph, OPh and SPh, (c) 3-6C cycloalkyl, 3-6C cycloalkylthio, 5-6C cycloalkenyl, 3-6C cycloalkoxy, 5-6C cycloalkenyloxy, 5-6C cycloalkenylthio, phenyl, phenoxy, phenylthio, benzyl, benzyloxy or benzylthio, all being opt. substd.; (d) gps. as defined for R2, or (e) NR7R8; R7 and R8 = H, 1-6C alkyl, 3-6C alkenyl, 3-6C alkynyl, 3-6C cycloalkyl, 5-6C cycloalkenyl, or opt. ring-substd. phenyl or benzyl; or R7 + R8 = 4-6C alkylene opt. interrupted by O, S or N and opt. substd. by up to three 1-4C alkyl gps.; X = N or CR5; R5 is as defined for R3; n = 0 or 1; A = mono- or bicyclic aryl or heteroaryl contg. 0-2 N, O and/or S atoms, opt. substd. by 1-5 halogen atoms and/or 1-3 of CN, NO2, SCN, COR6, S(O)mR6 and gps. as defined for R3; R6 = OH, NH2 or as defined for R3; m = 1 or 2. USE - (I) are herbicides and plant growth regulators (no test data given).

Description

The present invention relates to general purine sulfonamides Formula I.

in which the dotted line of the Puringer structure denotes a double bond in the 7- or 8-position and the substituents and indices have the following meaning:
R¹ is hydrogen or a C₁-C₄ alkyl group,
R² is hydrogen,
a C₁-C₆-alkyl group which can be substituted by one to five halogen atoms and / or one of the following radicals: C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, phenyl, Phenoxy or phenylthio;
a C₃-C₄ alkenyl group; a C₃-C₄ alkynyl group;
a saturated or monounsaturated 5- to 7-membered heterocycle containing one to two nitrogen, oxygen and / or sulfur atoms, which can carry one to three of the following substituents: halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy , C₁-C₄ haloalkyl, C₁-C₄ haloalkoxy, C₁-C₄ alkylthio, C₁-C₄ haloalkylthio, phenyl, phenoxy and / or phenylthio;
R³, R⁴ halogen;
C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkenylthio, C₂-C₆-alkynyl, C₂-C₆-alkynyloxy and / or C₂-C₆-alkynylthio, wherein said radicals can be substituted by one to five halogen atoms and / or by one of the following groups: C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₄-alkylthio, C₁-C₄-haloalkylthio, phenyl, phenoxy or phenylthio ;
C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylthio, C₅-C₆-cycloalkenyl, C₃-C₆-cycloalkoxy, C₅-C₆-cycloalkenyloxy, C₅-C₆-cycloalkenylthio, phenyl, phenoxy, phenylthio, benzyl, benzyloxy or benzylthio, these cyclic groups can be substituted by one to five halogen atoms and / or one to three of the following radicals: C₁-C₄-alky, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄ haloalkylthio, phenyl, phenoxy, phenylthio, benzyl, benzyloxy and / or benzylthio;
the groups mentioned under R² or
NR⁷R⁸, in which
R⁷ and R⁸ are hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl, phenyl and / or benzyl, the aromatic rings in turn one to can be substituted five times by halogen and / or once to three times by C₁-C₄-alkyl, C₁-Calkyl-haloalkyl, C₁-C₄-alkoxy and / or C₁-C₄-haloalkoxy or together a C₄-C₆-alkylene bridge, which by an oxygen, sulfur or nitrogen atom can be interrupted, this bridge in turn can carry one to three C₁-C₄ alkyl groups;
X is a nitrogen atom or a group = CR⁵-, where R⁵ is one of the radicals R³,
n 0 or 1 and
A is a mono- or dinuclear aromatic radical which can contain one to two nitrogen, oxygen and / or sulfur atoms, which radical can carry one to five halogen atoms and / or one to three of the following groups: cyano, nitro, thiocyanato, COR⁶, in which R⁶ is hydroxy, amino or one of the radicals R³, SO _m R⁶, in which m has the value 1 or 2 and / or the radicals mentioned under R³,
and their environmentally compatible salts.

Furthermore, the invention relates to a method for producing this Compounds and their use for combating undesirable plant growth.  

EP-A-1 50 974 describes sulfonamides which are herbicidal Have an effect. However, they do not meet all requirements, e.g. B. after Selectivity and specific effects.

The invention was therefore based on the object, substances with satisfactory Finding and synthesizing properties.

In accordance with this task, the sulfonamides I defined at the outset found.

The invention also includes processes for the preparation of these compounds I, herbicides and plant growth regulators, the contain the new compounds as active ingredients, and a process for Influencing and controlling plant growth with these compounds.

The compounds I according to the invention are analogous to in a variety of ways known implementation methods available, the following four Process A to D is of particular importance.

Procedure A

Compounds I are obtained in a manner known per se by reaction a corresponding amine II in an inert organic solvent in the presence of a base with a heteroarylsulfonyl halide III according to the following scheme.

Hal in formula III means a halogen atom such as fluorine, chlorine, bromine and iodine. Compounds III in which Hal is chlorine are particularly suitable or fluorine.

Appropriately, solvents such as are used for these reactions Halogenated hydrocarbons, e.g. B. tetrachloroethane, methylene chloride, Chloroform, dichloroethane, chlorobenzene and 1,2-dichlorobenzene; Ether z. B. Diethyl ether, methyl tert-butyl ether, dimethoxyethane, diethylene glycol dimethyl ether, Tetrahydrofuran and dioxane; dipolar aprotic solvents, e.g. B. acetonitrile, dimethylformamide, dimethylacetamide, dimethyl sulfoxide, N-methylpyrrolidone, 1,3-dimethyltetrahydro-2 (1H) -pyrimidinone and  1,3-dimethylimidazolidin-2-one; Aromatics, e.g. B. benzene, toluene, xylene, Pyridine and quinoline; Ketones, e.g. B. acetone, methyl ethyl ketone; Alcohols, e.g. B. methanol, ethanol, iso-propanol and tert-butanol or equivalent Mixtures.

The reaction can take place at temperatures from -100 ° C to the reflux temperature of the respective solvent or mixture, preferably at -60 ° C to 150 ° C, are carried out.

Aromatic nitrogen bases serve as catalytically active bases such as pyridine, 4-dimethylaminopyridine and quinoline; tertiary aliphatic Amines such as triethylamine, N-ethyl-diisopropylamine and N-methylmorpholine; bi- and tricyclic amines such as B. diazabicycloundecane (DBU) or Diazabicyclooctane (DABCO) as well as hydroxides, hydrides, alkoxides, carbonates and hydrogen carbonates of alkali metal and alkaline earth metal cations, in particular NaOH, KOH, NaH, KH, CaH₂, LiH, NaOMe, NaOEt, KOtBu, Na₂CO₃, K₂CO₃, NaHCO₃, KHCO₃. Sometimes it is also useful to combine the bases listed above.

The molar ratios in which the required starting compounds reacted with each other are generally 0.3: 1 to 1: 1 for the ratio of amine II to heteroarylsulfonyl halide III and 1: 1 to 1: 3 for the ratio of amine II to catalytically active base.

The concentration of the starting materials in the solvent is generally 0.1 up to 5 mol / l, preferably 0.2 to 2 mol / l.

It is particularly preferred to work in aprotic dipolar solvents such as Acetonitrile, dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone, 1,3-dimethyltetrahydro-2 (1H) pyrimidinone, 1,3-dimethylimidazolin-2-one or ethers such as 1,2-dimethoxyethane, diethylene glycol dimethyl ether, Tetrahydrofuran, or dioxane at temperatures between 50 ° C and 150 ° C using triethylamine, DBU or DABCO as bases. At The use of basic solvents such as pyridine makes this unnecessary Add another base.

The heteroarylsulfonyl halides required for the reaction Formula III can be used in analogy to a number of methods known from the literature can be synthesized from the corresponding mercapto compounds. To These methods include the oxidation of the mercapto compounds with elemental chlorine in dilute aqueous hydrochloric acid, acetic acid or aqueous potassium hydroxide solution or with chlorine in the presence of an excess of potassium hydrogen fluoride or potassium fluoride / hydrofluoric acid in methanol / water mixtures as solvents (A.G. Beaman,  (1961),. O. Robin, J.W. Clapp, J. Am. Chem. Soc. 72: 4890 (1950); D. J. Brown, R.K. Robins, J. Chem. Soc. 83, 4038 J.A. Harkins, J. Chem. Soc., Perkin Trans. I, 522 (1972).

Instead of the mercapto compounds, the corresponding ones can also be used Use disulfide or thiobenzyl ether. Those needed as educts 8-mercaptopurines and 2-mercaptoimidazolo (4,5-b) pyridines are in part known or can be synthesized in analogy to methods known from the literature (Shaw, Comprehensive Heterocyclic Chemistry; The Structure, Reaction, Synthesis and Uses of Heterocyclic Compounds, Vol. 5, 1std ed. (1984), Chap. 4.09, p. 499 ff; Montgomery, J.A. Secrist III in Comprehensive Heterocyclic Chemistry, Vol. 5, 1st ed. (1984) Chap. 4.10, p. 615 ff and p. 635 ff; Lister, The Chemistry of Heterocyclic Compounds, Fused Pyrimidines, Part II, Purines (1971) and Robins, Heterocyclic Compounds, Vol. 8, pp. 162 ff (1967)).

The conversion of the mercapto derivatives into corresponding disulfides or Thiobenzyl ether is carried out analogously to known processes (Houben-Weyl, "Methods of Organic Chemistry", Volume 9, sulfur, selenium, Tellurium compounds, G. Thieme Verlag, Stuttgart, 1955).

The amines of the general formula II are commercial in many cases available or can be represented in a manner known per se.

Procedure B

Compounds I in which neither R¹ nor R² are hydrogen is obtained one by using a corresponding Purinsulfonamid IV in known per se Manner in an organic solvent in the presence of a base with a Alkylation reagent V, wherein Nu is a nucleophilic starting group and R¹ does not mean hydrogen, implemented according to the following scheme.

Inert solvents are expediently used for this reaction and corresponding mixtures, as already listed in process A.

These reactions can take place at temperatures from -100 ° C to the reflux temperature of the solvent or mixture, preferably at -60 ° C to 150 ° C, are carried out.  

The bases that have already been listed in process A serve as bases. If the base also functions as a solvent, the no additional use of a solvent is required.

The molar ratio of the starting compounds is generally 1: 1 up to 1: 3 (compound IV to electrophile V) or 1: 1 to 1: 5 (compound IV to base). The concentration of the starting materials in the solvent is generally 0.1 to 5 mol / l, preferably 0.2 to 2 mol / l.

C₁-C₄ alkyl chlorides in particular serve as alkylating reagents V, bromides, iodides, benzenesulfonates, p-bromobenzenesulfonates, p-methylbenzenesulfonates, C₁-C₄ dialkyl sulfates and C₁-C₄ trialkyloxonomium tetrafluoroborates. Compounds V are generally commercial available or can be prepared by known methods.

The sulfonamides of the general formula IV with R² ≠ H are already after described method A accessible.

Procedure C

Compounds of the general formula I in which R³ and / or R⁴ a Alcoholate, thiolate, phenolate, or a substituted amino group and X Nitrogen is obtained particularly advantageously by reaction a purine sulfonamide derivative VIa or VIb, in which Hal is halogen such as fluorine, Chlorine, bromine, in particular chlorine and R³ in formula VIb does not Halogen or phenoxy means, with a corresponding alcohol, thiol, Phenol or amine VIIa or VIIb in a manner known per se in one organic solvents in the presence of a base according to the following Scheme:

In principle, those mentioned in process A can be used for such reactions Solvents and bases and their combinations can be used. The reagent of the formula VIIa or VIIb is preferably in a ratio of 1: 1 to 5: 1, in particular 3: 1 to 5: 1, based on the sulfonamide VIa or VIb in a solvent such as alcohol e.g. B. methanol, ethanol, propanol, iso-propanol, n-butanol, iso-butanol, tert-butanol, ether z. B. diethyl ether, Methyl tert-butyl ether, 1,2-dimethoxyethane, tetrahydrofuran, Dioxane or aprotic dipolar solvent z. B. acetonitrile, dimethylformamide or dimethyl sulfoxide at reaction temperatures from -100 ° C to 130 ° C, preferably -70 ° C to 90 ° C, implemented.

Procedure D

In a modification of the process described under C, compounds are obtained of the general formula I, in which R³ and R⁴ are identical and alcoholate, Thiolate, phenolate, alkylamino, dialkylamino or alkylene amino groups and X is nitrogen by reacting a corresponding sulfonamide derivative VIc with the derivative VIIa or VIIb in an organic solvent in the presence of a base according to the following scheme.

In formula VIc, Hal has the meaning fluorine, chlorine or bromine, especially chlorine.

The implementation is generally and in particular analogous to that in Procedure C conditions.

The nucleophiles of the general formula VIIa or VIIb are in general commercially available or can be in simple and generally known Be prepared from known starting materials. The sulfonamides VIa, VIb and VIc are according to the methods A-C described above accessible.  

With regard to the intended use of the compounds I, the following radicals are preferably suitable as substituents:
R¹ is hydrogen or C₁-C₄-alkyl such as methyl, ethyl, n-propyl, iso-propyl, n-butyl, sec-butyl, iso-butyl and tert-butyl, especially methyl, ethyl, propyl and iso-propyl
R² is hydrogen, allyl; Propargyl; Alkyl as mentioned under R¹, and pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, hexyl, 1-methylpentyl, 2 -Methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethyl, 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 and 1-ethyl-2-methylpropyl, especially methyl, ethyl, propyl and isopropyl, which by one to five halogen atoms, in particular fluorine and / or chlorine atoms or one of the following radicals can be substituted: alkoxy such as methoxy, ethoxy, n-propoxy, 2-methylethoxy, n-butoxy, 1-methypropoxy, 2-methylpropoxy and 1,1 -Dimethylethoxy, especially methoxy, ethoxy, 1-methylethoxy and 1,1-dimethylethoxy;
Haloalkoxy such as difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, 1-fluoroethoxy, 2-fluoroethoxy, 2,2-difluoroethoxy, 1,1,2,2-tetrafluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-1, 1,2-trifluoroethoxy and pentafluoroethoxy, especially trifluoromethoxy and pentafluoroethoxy;
Alkylthio such as methylthio, ethylthio, peropylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio, especially methylthio and ethylthio;
Haloalkylthio such as difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoroethylthio, especially difluoromethylthio and pentafluoroethylthio;
Phenyl or phenylthio;
a 5- to 7-membered saturated or monounsaturated heterocycle such as tetrahydrofuranyl, tetrahydrothiophenyl, dioxolanyl, dithiolanyl, Oxathiolanyl, pyrazolidinyl, dihydropyrazolyl, imidazolidinyl, dihydroimidazolyl, isoxazolidinyl, dihydroisoxazolyl, oxazolidinyl, dihydrooxazole, Isothioazolidinyl, Dihydroisothiazolyl, thiazolidinyl, dihydrothiazolyl, tetrahydropyran-3 -yl, dihydropyran-3-yl, tetrahydropyran-4-yl, tetrahydropyran-2-yl, dihydropyran-4-yl, tetrahydrothiopyran- 3-yl, dihydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, dihydroth and dioxepan-5-yl, piperidinyl, tetrahydron-1,3-oxazinyl, tetrahydro-1,4-oxazinyl, tetrahydro-1,3-thiazinyl, tetrahydro-1,4-thiaszinyl, perhydro-1,3-oxazepinyl, perhydro -1,4-oxazepinyl, perhydro-1,3-thiazepinyl, perhydro-1,4-thiazepinyl, and perhydroazepinyl, which ring can make one to three of the following substitutions:
Halogen such as fluorine, chlorine, bromine and iodine, especially fluorine and chlorine;
Alkyl as mentioned under R¹, in particular methyl, ethyl, propyl and isopropyl;
Alkoxy as mentioned above, in particular methoxy, ethoxy, 1-methylethoxy and 1,1-dimethylethoxy;
Haloalkyl such as fluoromethyl, difluoromethyl, trifluoromethyl, chlorodifluoromethyl, dichlorofluoromethyl, trichloromethyl, 1-fluoroethyl, 2-fluoroethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2- Dichloro-2-fluoroethyl, 2,2,2-trichloroethyl and pentafluoroethyl, especially trifluoromethyl;
Haloalkoxy as mentioned above, in particular trifluoromethoxy, trifluoroethoxy and chloroethoxy;
Alkylthio as mentioned above, in particular mewthylthio and ethylthio;
Haloalkylthio as mentioned above, in particular difluoromethylthio and pentafluoroethylthio and / or phenyl phenoxy or phenylthio;
R³, R⁴ independently of one another halogen as mentioned under R², in particular fluorine and chlorine;
Alkoxy as mentioned under R², in particular methoxy, ethoxy, 1-methylethoxy and 1,1-dimethylethoxy;
Alkylthio as mentioned under R², in particular methylthio and ethylthio;
Alkenyl such as ethenyl, 1-propenyl, 2-propenyl, 1-methylethenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-methyl-1-propenyl, 1-methyl-2-propenyl, 2-methyl-1- propenyl, 2-methyl-2-propenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-1-butenyl, 2-methyl-1-butenyl, 3-methyl-2-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, 1,1-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-dimeth yl-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, 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 and 1-ethyl-2-methyl-2-propenyl, in particular allyl or in general and in special alkenyloxy and / or alkenylthio;
Alkynyl such as ethynyl, 1-propynyl, propargyl, 1-butynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 1-pentynyl, 2-pentynyl, 3-pentynyl, 4-pentynyl, 1-methyl- 3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 3-methyl-1-butynyl, 1,1-dimethyl-2-propynyl, 1-ethyl-2-propynyl, 1-hexynyl, 2-hexynyl, 3-hexynyl, 4-alkynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl-4-pentynyl, 2-methyl-3-pentynyl, 2- Methyl-4-pentinyl, 3-methyl-1-pentinyl, 3-methyl-4-pentinyl, 4-methyl-1-pentinyl, 4-methyl-2-pentinyl, 1,1-dimethyl-2-butinyl, 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 and 1-ethyl-1-methyl-2-propynyl, in particular propargyl or in general and in particular corresponding alkynyloxy and / or alkynylthio;
these radicals can be substituted by one to five halogen atoms and / or by one of the following groups: alkoxy, haloalkoxy, alkylthio and haloalkylthio as mentioned under R², in particular fluorine, chlorine, methoxy, ethoxy, 1-methylethoxy, 1,1-dimethylethoxy , Trifluoromethoxy, pentafluoroethoxy, methylthio, ethylthio, difluoromethylthio and pentafluoroethylthio as well as phenyl, phenoxy or phenylthio;
Cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl and cyclohexyl, in particular cyclopropyl, cyclopentyl and cyclohexyl or corresponding cycloalkoxy and / or cycloalkylthio, cyclohexylthio;
Cycloalkenyl such as cyclopentenyl, cyclohexenyl, cyclohexadienyl, in particular cyclopentenyl and cyclohexenyl or corresponding cycloalkenyloxy and / or cycloalkenylthio, in particular cyclopentenyloxy, cyclohexenyloxy, cyclopentenylthio and cyclohexenylthio;
Phenyl, phenoxy, phenylthio, benzyl, benzyloxy, and / or benzylthio, where these cyclic radicals can carry one to five halogen atoms as mentioned under R², in particular fluorine and chlorine and / or one or three of the following groups: alkyl as mentioned under R¹, in particular Methyl, ethyl, propyl, isopropyl;
Haloalkyl as mentioned under R², in particular trifluoromethyl, alkoxy as mentioned under R², in particular methoxy, ethoxy, 1-methylethoxy and 1,1-dimethylethoxy;
Haloalkoxy as mentioned under R², in particular trifluoromethoxy and trifluoroethoxy and chloroethoxy; Alkylthio as mentioned under R², in particular methylthio and ethylthio; Haloalkylthio as mentioned under R², in particular difluoromethylthio and pentafluoroethylthio; Phenyl, phenoxy, phenylthio, benzyl, benzyloxy and / or benzylthio;
in general and in particular the groups mentioned under R² or
a residue NR⁷R⁸, wherein
R⁷, R⁸ hydrogen; Alkyl as mentioned for R², in particular as mentioned in general for R¹; Alkenyl, alkynyl or cycloalkyl, each having 3 to 6 carbon atoms, as mentioned in general and in particular for R³;
Cycloalkenyl as mentioned in general and in particular for R³;
Phenyl and or benzyl, the aromatic rings in turn one to five times by the halogen atoms mentioned in R³ and / or one to three times by alkyl, haloalkyl, alkoxy and / or haloalkoxy each having 1 to 4 carbon atoms as in general and in particular in R² called may be substituted or
R⁷, R⁸ together C₄-C₆-alkylene, which can be interrupted by a heteroatom such as oxygen, sulfur or nitrogen, such as - (CH₂) ₄-, - (CH₂) ₅-, - (CH₂) ₆-, - (CH₂) ₂ -O- (CH₂) ₂-, - (CH₂) ₂-S- (CH₂) ₂- and - (CH₂) ₂-NH- (CH₂) ₂-, these bridges in turn one to three of the in general and in particular can carry in alkyl groups mentioned R¹.
X is a nitrogen atom or a group = CR⁵-, where R⁵ in general and in particular one of the groups mentioned for R³,
n the value 0 or 1 and
A is an aryl or heteroaryl group such as phenyl, naphthyl, six-membered heterocycles with one or more heteroatoms such as pyridyl, pyridazinyl, pyrimidinyl, pyrazinyl, 1,3,5-triazinyl, 1,2,4-triazinyl, 1,2,3-triazinyl , Tetrazinyl, five-membered heterocycles with one or more heteroatoms such as pyrryl, furyl, thienyl, pyrazolyl, imidazolyl, oxazolyl, isoxazolyl, thiazolyl, isothiazolyl, 1,2,3-triazolyl, 1,2,4-triazolyl, tetrazolyl, annelladiazolyl and benzo-fused heteroatoms, such as indolyl, isoindolyl, thionaphthyl, quinolyl, isoquinolyl, cinnalolyl, phthalazinyl, quinozolyl, cinoxalyl, indazolyl, naphthyrindinyl, benzthiazolyl, benzimidazolyl, benzofuryl, benzoxazolylyl, especially phenyl, phenylylolyl, pyryl, benzylazylyl, pyridyl, benzylazylyl, benzylazylyl, and benzylazylyl, benzenediazolyl, pyrid these aromatic rings can carry one to five halogen atoms, in particular fluorine, chlorine and bromine and / or one to three of the following radicals: cyano, nitro, thiocyanato, -COR⁶ wherein R⁶ is hydroxy, amine o or one of the radicals R³, -SO _m R⁶ wherein m has the value 1 or 2 and / or the radicals mentioned under R³.

Particularly preferred compounds are purine sulfonamides of the general Formula Ia

in which the substituents have the following meanings in particular:
R1 is hydrogen or methyl;
R² is hydrogen or methyl, and in the cases in which R² is hydrogen it is not possible to distinguish which of the two nitrogen atoms (N- 7 or N- 9 ) the hydrogen is due to tautomerism;
R³, R⁴ hydrogen, fluorine, chlorine, methyl, ethyl, n-propyl, iso-propyl, trifluoromethyl, methoxy, ethoxy, propoxy, 1-methylethoxy, methylthio, ethylthio, allyl, propargyl, allyloxy, allylthio, propargyloxy, propargylthio, trifluoromethoxy , N-methylamino, N-phenylamino, N, N-dimethylamino, pyrrolidino, piperidino, morpholino, 3,5-dimethylmorpholino, phenoxy, benzyloxy, phenylthio, benzylthio and / or phenyl;
A phenyl, pyridyl, naphthyl, quinolinyl, thienyl or pyrazolyl, where these aromatic radicals can in particular carry one to three of the following groups: nitro, cyano, fluorine, chlorine, ethyl, propyl, isopropyl, trifluoromethyl, methoxy, ethoxy, 1-methylethoxy , 1,1-dimethylethoxy, trifluoromethoxy, trifluoroethoxy, chloroethoxy, methoxymethyl, ethoxymethyl, methoxyethyl, ethoxyethyl, methoxyethoxy, ethoxyethoxy, methylthio, ethylthio, methyl- and ethylsulfonyl, methoxycarbonyl, ethoxycarbonyl, iso-propoxycarbonyl, methyl and ethylcarbonyl -Dimethylsulfonamido and N, N-Dimethylcarboxamido and their salts.

Furthermore, the compounds Ib are preferred

in which R¹, R², R³ and dR⁴ have the meaning given under formula Ia and their salts.

Preferred compounds are also sulfonamides of the general formula Ic

in which R¹, R², R³, R⁴ and A have the meaning given for formula Ia and R⁵ is hydrogen, methyl, fluorine or chlorine and their salts.

Furthermore, sulfonamides of the formula Id are preferred

in which R¹, R², R³, R⁴, R⁵ and A have the meaning given for formula Ic and their salts.

Examples of very active compounds of the formulas Ia, Ib, Ic and Id sidn listed in Tables I, II, III and IV below.  

Table I

Table II

Table III

Table IV

The substituted purine sulfonamides I or the herbicides containing them Agents can be, for example, in the form of directly sprayable solutions, Powders, suspensions, also high-proof aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, Pastes, dusts, sprinkles or granules by spraying, Nebulization, dusting, scattering or pouring can be used. The Forms of use depend on the purposes; they should be in in any case the finest possible distribution of the invention Ensure active ingredients.

The compounds I are generally suitable for the preparation of directly sprayable solutions, emulsions, pastes or oil dispersions Mineral oil fractions from medium to high boiling point, such as kerosene or Diesel oil, also coal tar oils and vegetable or animal oils Origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. B. toluene, xylene, paraffin, tetrahydronaphthalene, alkylated naphthalenes or their derivatives, methanol, ethanol, propanol, butanol, cyclohexanol, Cyclohexanone, chlorobenzene, isophorone or strongly polar solvents, such as N, N-dimethylformamide, dimethyl sulfoxide, N-methylpyrrolidone or water.

Aqueous use forms can be made from emulsion concentrates, dispersions, Pastes, wettable powders or water-dispersible granules by adding be prepared by water. For the production of emulsions, pastes or oil dispersions, the substrates as such or in an oil or Solvent dissolved, using wetting agents, adhesives, dispersants or emulsifiers be homogenized in water. But it can also be more effective Substance, wetting, adhesive, dispersing or emulsifying agent and possibly Solvents or oil existing concentrates are produced, which are used for Dilution with water are suitable.

The alkali, alkaline earth, ammonium salts come as surface-active substances aromatic sulfonic acids, e.g. B. lignin, phenol, naphthalene and dibutylnaphthalenesulfonic acid, as well as fatty acids, alkyl and alkylarylsulfonates, Alkyl, lauryl ether and fatty alcohol sulfates, and salts sulfated hexa-, hepta- and octadecanols, as well as fatty alcohol glycol ether, Condensation products of sulfonated naphthalene and its Derivatives with formaldehyde, condensation products of naphthalene or Naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl, octyl or nonylphenol, alkylphenol, Tributylphenyl polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, Fatty alcohol ethylene oxide condensates, ethoxylated castor oil, Polyoxyethylene alkyl ether or polyoxypropylene, lauryl alcohol polyglycol ether acetate, Sorbitol esters, lignin sulfite liquors or methyl cellulose into consideration.  

Powders, materials for spreading and dusts can be mixed or combined Grinding the active substances with a solid carrier will.

Granules, e.g. B. coating, impregnation and homogeneous granules by binding the active ingredients to solid carriers. Solid carriers are mineral soils such as silicas, 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 corn flour, Tree bark, wood and nutshell flour, cellulose powder or other solid Carriers.

The formulations generally contain between 0.1 and 95% by weight, preferably between 0.5 and 90 wt .-%, active ingredient.

The active ingredients are formulated as follows, for example:

• I. 90 parts by weight of compound no. 1001 are mixed in 10 parts by weight of N-methyl-α-pyrrolidone and receives a solution which is suitable for use in the form of tiny drops.
• II. 20 parts by weight of compound no. 1001 are in one Mixture dissolved, consisting of 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide 1 mol of oleic acid-N-monoethanolamide, 5 parts by weight of calcium salt Dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 moles of ethylene oxide to 1 mole of castor oil. By pouring out and finely distributing the solution in 100,000 parts by weight Water gives an aqueous dispersion that Contains 0.02% by weight of the active ingredient.
• III. 20 parts by weight of compound no. 1002 are in one Dissolved mixture consisting of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 moles of ethylene oxide to 1 mole of isooctylphenol and 10 parts by weight of the adduct of 40 moles of ethylene oxide of 1 mole of castor oil. By pouring and finely distributing the solution in 100,000 parts by weight of water gives one aqueous dispersion containing 0.02% by weight of the active ingredient.  
• IV. 20 parts by weight of active ingredient No. 1001 are in a Dissolved mixture consisting of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction from boiling point 210 to 280 ° C and 10 parts by weight of the adduct of 40 moles There is ethylene oxide in 1 mol of castor oil. By pouring and finely distribute the solution in 100,000 parts by weight of water an aqueous dispersion containing 0.02% by weight of the active ingredient is obtained contains.
• V. 20 parts by weight of active ingredient no. 1002 with 3 parts by weight the sodium salt of diisobutylnaphthalene-α-sulfonic acid, 17 parts by weight of the sodium salt of a lignosulfonic acid a sulfite waste liquor and 60 parts by weight of powdered silica gel well mixed and ground in a hammer mill. By finely distributing the mixture in 20,000 parts by weight Water gives a spray mixture which contains 0.1% by weight of the active ingredient contains.
• VI. 3 parts by weight of active ingredient No. 1002 become 97 parts by weight finely divided kaolin mixed. You get this way a dust containing 3% by weight of the active ingredient.
• VII. 30 parts by weight of active ingredient No. 1002 are with a Mixture of 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil on the surface of this Silica gel was sprayed, mixed intimately. You get on in this way a preparation of the active ingredient with good adhesiveness.
• VIII. 20 parts by weight of active ingredient no. 1001 are mixed with 2 parts by weight Calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight Fatty alcohol polyglycol ether, 2 parts by weight of sodium salt one Phenol-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil intimately mixed. You get one stable oily dispersion.

The application can be done pre- or post-emergence. If the active ingredients are less compatible for certain crops, so application techniques can be applied in which the herbicides Means are sprayed with the aid of sprayers so that the Leaves of sensitive crops should not be hit if possible while the active ingredients on the leaves underneath are growing undesirable Plants or the uncovered floor area (postdirected, lay-by).  

Depending on the target, the amount of active ingredient is Season, target plants and growth stage 0.001 to 3.0 kg / ha, preferably 0.01 to 1.0 kg / ha of active substance (a.s.).

In view of the versatility of the application methods, the Compounds according to the invention or compositions containing them in one another number of crops to eliminate unwanted plants be used

Some of the purine sulfonamides of the general formula I can also practically all stages of development of a plant are different influence and are therefore also used as growth regulators. The variety of effects of the connections depends on various factors. The most important are

• a) plant type and variety,
• b) time of application, with regard to the development stage of Plant and season,
• c) Application site and method (seed dressing, soil treatment or Leaf application)
• d) climatic factors, e.g. B. temperature, rainfall, also from day length and light intensity
• e) soil conditions (including fertilization),
• f) formulation or use form of the active ingredient and
• g) application rate and active substance content of the agents.

From the series of different possible uses of the invention Plant growth regulators in crop cultivation, in agriculture and in horticulture, some examples are listed below.

• A) With the growth-regulating sulfonamides I, the vegetative growth of the plants can be strongly inhibited, which manifests itself in particular in a reduction in the growth in length. The treated plants accordingly have a compact stature; a darker leaf coloration can also be observed.
  As an advantage in practice, z. B. the reduction of grass cover on roadsides, hedges, canal embankments and on lawns such as parks, sports and orchards, ornamental lawns and airfields, so that the labor and costly grass clippings can be reduced.
  In the case of fruit trees and other trees or shrubs, costly cutting measures can be reduced.
  It is also of economic interest to increase the stability of crops that are susceptible to storage, such as cereals, rice, corn, sunflowers and soybeans. The resulting shortening and strengthening of the straw reduce or eliminate the risk of "storing" (twisting) of plants under unfavorable weather conditions before harvesting.
  It is also important to use it to inhibit the growth in length and to change the maturity of cotton over time. This enables fully mechanized harvesting of these important crops.
  By using the compounds I, the lateral branching of the plants can also be increased or inhibited. There is interest if, for. B. in tobacco plants the formation of side shoots (stinging shoots) should be inhibited in favor of leaf growth.
  With the compounds I, for example in winter rape, the frost resistance can also be increased considerably. On the one hand, the growth in length and the development of a lush (and therefore particularly susceptible to frost) leaf or plant mass are inhibited. On the other hand, the young rapeseed plants are retained in the vegetative development stage after sowing and before the onset of winter frosts, despite favorable growth conditions. This also eliminates the risk of frost for plants that tend to prematurely degrade flowering and switch to the generative phase. Also with other cultures, e.g. B. Winter cereals, it is advantageous if the stocks are well stocked by treatment with compounds according to the invention in autumn, but do not go into the winter too abundantly. This can prevent increased sensitivity to frost and - due to the relatively low leaf or plant mass - infestation with various diseases (e.g. fungal disease). The inhibition of vegetative growth also enables denser planting of the soil in many crop plants, so that an additional yield, based on the soil area, can be achieved.
• B) With the growth-regulating agents based on purine sulfonamides, additional yields can be achieved both on parts of plants and on plant constituents. For example, it is possible to induce the growth of larger quantities of buds, flowers, leaves, fruits, seeds, roots and tubers, to increase the sugar content in sugar beets, sugar cane and citrus fruits, to increase the protein content in cereals or soybeans or to grow rubber trees to stimulate the increased latex flow.
  The purine sulfonamides of the formula I can increase yields by interfering with plant metabolism or by promoting or inhibiting vegetative and / or generative growth.
• C) With the purine sulfonamides I, both a shortening or lengthening of the developmental stages and an acceleration or deceleration of the ripeness of the harvested plant parts can be achieved before or after the harvest.
  Ease of harvest, for example, is of economic interest, which is made possible by the time-related falling or decreasing of the adhesive strength on the tree in the case of citrus fruits, olives or other types and varieties of pome, stone and nuts. The promotion of the formation of a separating tissue between the leaf and shoot axis is also for a well controlled defoliation of crops such. B. Cotton essential.
• D. The purine sulfonamides I can further reduce the water consumption of plants. This is particularly important for agricultural land that has to be artificially irrigated at a high cost, e.g. B. in arid or semi-arid areas. By using the substances according to the invention, the intensity of the irrigation can be reduced and thus more economical management can be carried out. Under the influence of growth regulators there is a better use of the water available because, among other things
  • - The opening width of the stomata is reduced
  • - A thicker epidermis and cuticle are formed
  • - The root penetration of the soil is improved
  • - The microclimate in the crop is favorably influenced by a more compact growth.

The active compounds to be used according to the invention can be used in crop plants both from the seed (as a seed dressing) and via the soil, d. H. through the root and by spraying over the leaf.

Due to the high tolerance of the plants to the growth regulators Compounds I, the application rate can be varied widely. In the seed treatment, amounts of active ingredient are generally 0.001 up to 50 g per kilogram of seed, preferably 0.01 to 1 g, is required. For leaf and soil treatment are generally from 0.01 to 10 gk / ha, 0.1 to 5 kg / ha sufficient.

To broaden the spectrum of activity and to achieve synergistic The purine sulfonamides of the formula I can have numerous effects Representatives of other herbicidal or growth-regulating groups of active ingredients mixed and applied together. For example, come as Mixing partner diazines, 4H-3,1-benzoxazine derivatives, benzothiadiazinones, 2,6-dinitroanilines, N-phenyl carbamates, thiol carbamates, halocarboxylic acids, Triazines, amides, ureas, diphenyl ethers, triazinones, uraciles, Benzofuran derivatives, imidazolinones, sulfonylureas, cyclohexane-1,3- dione derivatives, quinoline carboxylic acid derivatives, phenyloxy or heteroaryloxyphenylpropionic acids as well as their salts, esters and amides and others in Consider.

It may also be useful to use the new compounds of the formula I. alone or in combination with other herbicides and growth regulators also mixed with other crop protection products spread, for example with pest control agents or phytopathogenic fungi or bacteria. The is also of interest Miscibility with mineral salt solutions, which are used to eliminate Nutritional and trace element deficiencies are used. It can too non-phytotoxic oils and oil concentrates can be added.

The procedure outlined in the synthesis examples below with the corresponding modification of the starting compounds Production of further compounds I used. The compounds thus obtained are in the following table 1 with physical information listed.

Example 1 a) 2,6-dichloro-8-mercapto-7-methylpurine

A solution of 80.0 g (0.34 mol) of 7-methyl.2,6,8-trichloropurine and 500 ml of ethanol was added in portions at 0 ° C with 25.8 g (0.34 mol) of thiourea. The mixture was then stirred at 25 ° C. for 24 hours, the product being obtained as a solid.
Yield: 69.7 g (87%); 1 H-NMR (300 MHz, d⁶-DMSO, δ in ppm): 3.8 (s, 3H); 14.3 (s, 1H).

b) 2-chloro-8-mercapto-4-methoxy-7-methylpurine

A mixture of 39.6 g (0.17 mol) of the compound obtained in a) and 200 ml of methanol was mixed with 91.8 g (0.51 mol) of 30% sodium methylate solution. The reaction mixture thus obtained was first stirred for 5 hours at 30 ° C. to 40 ° C., then cooled to approx. 25 ° C. and freed from the solvent under reduced pressure. The above crude product thus obtained was dissolved in water. The product crystallized on acidification of the aqueous solution.
Yield: 36.9 g (94%); 1 H-NMR (300 MHz, d⁶-DMSO, δ in ppm): 3.70 (s, 3H); 4.05 (s, 3H); 13.7 (s, 1H),

c) 2-chloro-4-methoxy-7-methylpurin-8-sulfonic acid fluoride

A mixture of 36.9 g (0.16 mol) of the compound obtained in b), 125 g (1.60 mol) of potassium hydrogen difluoride and 165 ml of methanol / water (1: 1) was at temperatures from -15 ° C to - 10 ° C with 113 g (1.60 mol) of elemental chlorine. After a further 0.5 hours at -10 ° C., the product which had precipitated as a solid was isolated.
Yield: 35.0 g (78%); 1 H-NMR (250 MHz, CDCl₃ δ in ppm): 4.25 and 4.35 each s, 3H).

d) 2-chloro-6-methoxy-7-methylpurine-8-sulfonic acid- (2-methoxycarbonyl) -an-ilide

A mixture of 4.90 g (20.2 mmol) of the product from c), 3.00 g (20.0 mmol) of anthranilic acid methyl ester, 2.02 g (20.0 mmol) of triethylamine and 100 ml of dioxane was added for 5 hours Heated to reflux. After cooling, the reaction mixture was freed from the solvent under reduced pressure. The crude product thus obtained was taken up in water. When the aqueous solution was acidified, the product was obtained as a solid.
Yield: 2.30 g (28%); Active ingredient example 1001.

Table 1

Examples of use

The herbicidal action of the purine sulfonamides of the formula I on growth the test plants are shown by the following greenhouse experiments.

Plastic flower pots with a content of 300 cm³ were used to grow the test plants and loamy sand with about 3.0% humus as a substrate. The seeds of the Test plants were sown separately according to species.

With pre-emergence treatment, the processed active ingredients became immediate then applied to the earth's surface. They were here in water as Distribution medium suspended or emulsified and by means of finely distributing Sprayed nozzles. After the agents were applied, the vessels became light calculated to get germination and growth going. Then you covered cover the jars with clear plastic covers until the plants had grown. This cover caused an even germination of the Test plants, unless this was affected by the active ingredients.

For the purpose of post-emergence treatment, they were either sown directly or in plants grown in the same containers or were selected only grown separately as seedlings and a few days before Treatment transplanted into the test vessels. Depending on the growth habit, the Test plants at a height of 3-15 cm then with the in water as Distribution agents suspended or emulsified active ingredients by finely distributing nozzles were sprayed, treated.

The test vessels were set up in the greenhouse, whereby for heat-loving species warmer areas (20 to 35 ° C) and for such temperate climates 10 to 20 ° C were preferred. The trial period spanned 2 to 4 weeks. During this time the Plants have been cared for and their response to each treatment has been improved evaluated.

It was rated on a scale from 0 to 100. 100 means no Emergence of the plants or complete destruction of at least the above ground Parts and 0 no damage or normal growth.

Claims (9)

1. Purinsulfonamides of the general formula I in which the dotted line of the Puringer structure denotes a double bond in the 7- or 8-position and the substituents and indices have the following meaning:
R¹ is hydrogen or a C₁-C₄ alkyl group,
R² is hydrogen,
a C₁-C₆-alkyl group which can be substituted by one to five halogen atoms and / or one of the following radicals: C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, phenyl, Phenoxy or phenylthio;
a C₃-C₄ alkenyl group; a C₃-C₄ alkynyl group;
a saturated or monounsaturated 5- to 7-membered heterocycle containing one to two nitrogen, oxygen and / or sulfur atoms, which can carry one to three of the following substituents: halogen, C₁-C₄-alkyl, C₁-C₄-alkoxy, C₁ -C₄-haloalkyl, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄-haloalkylthio, phenyl, phenoxy and / or phenylthio;
R³, R⁴ halogen;
C₁-C₄-alkoxy, C₁-C₄-alkylthio, C₂-C₆-alkenyl, C₂-C₆-alkenyloxy, C₂-C₆-alkenylthio, C₂-C₆-alkynyl, C₂-C₆-alkynyloxy and / or C₂-C₆-alkynylthio, wherein said radicals can be substituted by one to five halogen atoms and / or by one of the following groups: C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₂-C₄-alkylthio, C₁-C₄-haloalkylthio, phenyl, phenoxy or phenylthio ;
C₃-C₆-cycloalkyl, C₃-C₆-cycloalkylthio, C₅-C₆-cycloalkenyl, C₃-C₆-cycloalkoxy, C₅-C₆-cycloalkenyloxy, C₅-C₆-cycloalkenylthio, phenyl, phenoxy, phenylthio, benzyl, benzyloxy or benzylthio, these cyclic groups can be substituted by one to five halogen atoms and / or one to three of the following radicals: C₁-C₄-alkyl, C₁-C₄-haloalkyl, C₁-C₄-alkoxy, C₁-C₄-haloalkoxy, C₁-C₄-alkylthio, C₁-C₄ haloalkylthio, phenyl, phenoxy, phenylthio, benzyl, benzyloxy and / or benzylthio;
the groups mentioned under R² or
NR⁷R⁸, in which
R⁷ and R⁸ are hydrogen, C₁-C₆-alkyl, C₃-C₆-alkenyl, C₃-C₆-alkynyl, C₃-C₆-cycloalkyl, C₅-C₆-cycloalkenyl, phenyl and / or benzyl, the aromatic rings in turn one to can be substituted five times by halogen and / or once to three times by C₁-C₄-alkyl, C₁-Calkyl-haloalkyl, C₁-C₄-alkoxy and / or C₁-C₄-haloalkoxy or together a C₄-C₆-alkylene bridge, which by an oxygen, sulfur or nitrogen atom can be interrupted, this bridge in turn can carry one to three C₁-C₄ alkyl groups;
X is a nitrogen atom or a group = CR⁵-, where R⁵ is one of the radicals R³,
n 0 or 1 and
A is a mono- or dinuclear aromatic radical which can contain one to two nitrogen, oxygen and / or sulfur atoms, which radical can carry one to five halogen atoms and / or one to three of the following groups: cyano, nitro, thiocyanato, COR⁶, in which R⁶ is hydroxy, amino or one of the radicals R³, SO _m R⁶, in which m has the value 1 or 2 and / or the radicals mentioned under R³,
and their environmentally compatible salts. 2. A process for the preparation of the compounds I according to claim 1, characterized in that an amine II A- (CH₂) _n -NHR¹ (II) in a conventional manner in an inert organic solvent in the presence of a base with a heteroarylsulfonyl halide III converts, in which Hal represents a halogen atom. 3. A process for the preparation of the compounds I according to claim 1, in which R¹ and R² are not hydrogen, characterized in that a purine derivative IV, in which R² is not hydrogen, in a manner known per se in an inert organic solvent in the presence of a base with an alkylating reagent V, R¹-Nu (V) in which Nu is a nucleophilic leaving group and R¹ is not hydrogen. 4. A process for the preparation of the compounds I according to claim 1, in which either R³ or R⁴ is a nucleophilic group and X is a nitrogen atom, characterized in that a purine derivative of the formulas VIa or VIb wherein Hal has the meaning given in claim 2, in a manner known per se in the presence of a base in an inert organic solvent with the corresponding compound VIIa or VIIbR³-H (VIIa); R⁴-H (VIIb) implemented. 5. A process for the preparation of the compounds I according to claim 1, in which R³ and R⁴ are the same nucleophilic group and X is nitrogen, characterized in that a purine derivative VIc wherein Hal has the meaning given in claim 2, in a manner known per se in the presence of a base in an inert organic solvent with a corresponding compound VIIa or VIIb according to claim 4. 6. Herbicidal agent containing a general Purinsulfonamid Formula I, according to claim 1, or its salt and conventional Formulation aids. 7. Process for combating undesirable plant growth, thereby characterized in that a purine sulfonamide of the formula I according to Claim 1, or its salt on the plants and / or their Living space. 8. Agent for influencing plant growth, containing a Purine sulfonamide of the formula I according to claim 1, or its salt and usual formulation aids. 9. Process for influencing plant growth, thereby characterized in that a purine sulfonamide of the formula I according to Claim 1, or its salt on the plants and / or their Living space.