DE3922107A1 - New N-fused heterocyclyl-substd. azole derivs. - useful as herbicides, plant growth regulators and fungicides and new intermediates - Google Patents

Abstract

N-(fused heterocyclyl)-aza-heterocycles of formula (I) are new, where R1 and R2 = H or alkyl, or together and alkandiyl; R3 = H or (all opt. substd.) alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or heteroarylalkyl; X = H or halo; Y and Z = O or S; A = O, CHR4, NR4 or -C=CR1R2; R4 = H or (all opt. substd.) alkyl, alkenyl, alkynyl, cycloalkyl, aryl or alkoxycarbonyl; B = bond, CH2, CHMe or CMe2. 9 USE/ADVANTAGE - (I) are herbicides (total or selective depending mainly on application rate), more active against 'problem weeds' and with better tolerance by crops than known cpds. of similar structure. (I) can be applied pre- or post-emergence and are esp. useful for selective use against dicotyledon weeds in mono- or di-cotyledonouse crops esp. at 0.01-2 kg/hectare. (I) are also useful as plant-growth regulators, partic. desiccants and defoliants for cotton, and additionally have fungicidal activity e.g. against Pyricularia oryzae with both protection and systemic effects.

Description

The invention relates to new N-aryl nitrogen heterocycles, several processes for their manufacture and their Use as herbicides and plant growth regulators.

It is already known that certain N-aryl nitrogen heterocycles, such as the 2- (4-carbamoyl- methyl-7-fluoro-2H-1,4-benzoxazin-3 (4H) -on-6-yl) - 4,5,6,7-tetrahydro-2H-isoindole-1,3-dione, herbicidal Possess properties (cf. EP-A 2 90 863, EP-A 1 90 755, EP-A 2 55 601, EP-A 2 41 559, EP-A 2 62 428 or DE-OS 36 42 372).

The herbicidal activity of these previously known compounds against problem weeds, however, is just like their tolerance to certain crops not completely satisfied in all areas of application lend.

New N-aryl nitrogen heterocycles of the general my formula (I)  

in which
R¹ and R² either independently of one another each represent hydrogen or alkyl or together represent a double-linked alkanediyl radical,
R³ represents hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or heteroarylalkyl,
X represents hydrogen or halogen,
Y represents oxygen or sulfur,
Z represents oxygen or sulfur,
A for oxygen, for a -CH-R⁴ group, for one

or for one

stands where
R⁴ represents hydrogen, each optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or alkoxycarbonyl, and
B for a direct bond or for methylene (-CH₂-), ethylidene

or isopropylidene

stands, found.

It was also found that the new N-aryl Nitrogen heterocycles of the general formula (I)

in which
R¹ and R² either independently of one another each represent hydrogen or alkyl or together represent a double-linked alkanediyl radical,
R³ represents hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or heteroarylalkyl,
X represents hydrogen or halogen,
Y represents oxygen or sulfur,
Z represents oxygen or sulfur,
A for oxygen, for a -CH-R⁴ group, for one

or for one

stands where
R³ represents hydrogen, each optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or alkoxycarbonyl, and
B for a direct bond or for methylene (-CH₂-), ethylidene

or isoproylidene

stands, by one of the methods described below receives:

• (a) N-aryl nitrogen heterocycles of the formula (Ia) are obtained, in which
  A¹ for a -CH-R⁴ group or for one stands and
  R¹, R², R³, R⁴, X, Y and B have the meaning given above,
  if alkylidosuccinic anhydrides of the formula (II) in which
  A¹, R¹ and R² have the meaning given above,
  with anilines of the formula (III), in which
  X, Y, R³ and B have the meaning given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary,
• (b) N-aryl nitrogen heterocycles of the formula (Ib) are obtained. in which
  R¹, R², X, Y, A¹ and B have the meaning given above,
  if compounds of the formula (IV) in which
  R¹, R², X, Y, A¹ and B have the meaning given above and
  Q represents cyano, carboxy or C₁-C₄-alkoxy-carbonyl,
  with a reducing agent, optionally in the presence of a catalyst and in the presence of a diluent,
• (c) N-aryl nitrogen heterocycles of the formula (Ic) are obtained in which
  R¹, R², X and A¹ have the meaning given above,
  if compounds of the formula (V) in which
  R¹, R², X and A¹ have the meaning given above,
  diazotized in the presence of acids and / or diluents and, if appropriate, subsequently reacted with bases,
  or if you
• (d) the N-aryl nitrogen heterocycles of the formula (Ib) obtainable by process (a), (b) or (c) in which
  R¹, R², X, Y, A¹ and B have the meaning given above,
  with alkylating agents of the formula (VI) R³-E (VI) in which
  E stands for an electron-withdrawing leaving group and
  R³ has the meaning given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary;
• (e) N-nitrogen heterocycles of the formula (Id) are obtained in which
  R¹, R², R³, X, Y and B have the meaning given above and
  A² for one or stands for oxygen,
  wherein R⁴ has the meaning given above, if one carboxylic acid ester of the formula (VII), R⁵-COOR⁶ (VII) in which
  R⁵ for a residue of the formula and
  R⁶ represents alkyl, wherein
  R¹, R² and A² have the meaning given above,
  or their acid addition salts with iso (thio) cyanides of the formula (VIII) in which
  R³, X, Y, Z and B have the meaning given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary; or if you
• (f) the N-aryl nitrogen heterocycles of the formula (Id) obtainable by process (e) in which
  R¹, R², R³, X, Y and B have the meaning given above,
  with alkylating agents of the formula (IX) R⁴-E (IX) in which
  E stands for an electron-withdrawing leaving group and
  R⁴ has the meaning given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.

The new N-aryl nitrogen heterocycles of the general Formula (I) have a strong herbicidal action from and can also be used to regulate plant wax tums are used.

Surprisingly, the N-aryl Nitrogen heterocycles of the general formula (I) against a stronger herbicidal activity problem herbs at the same time an improved ver tolerance to important crops in ver equal to the N- known from the prior art Aryl nitrogen heterocycles such as 2- (4-carbamoylmethyl-7-fluoro-2H-1,4-benzoxazin-3 (4H) -one- 6-yl) -4,5,6,7-tetrahydro-2H-isoindole-1,3-dione, which chemically and functionally obvious compounds are.

The N-aryl nitrogen heterocycles according to the invention are generally defined by formula (I).

Compounds of the formula (I) in which
R¹ and R² either independently of one another each represent hydrogen or straight-chain or branched alkyl having 1 to 4 carbon atoms or together stand for a double-linked alkanediyl radical having 2 to 7 carbon atoms,
R³ for hydrogen, for each straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkynyl having 3 to 8 carbon atoms, haloalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, haloalkenyl having 2 to 8 carbon atoms and 1 to 15 identical or different halogen atoms, haloalkynyl having 3 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, cyanoalkyl, alkoxy alkyl, alkylthioalkyl, haloalkoxyalkyl, alkoxy alkoxyalky, bis (alkoxy) alkyl, bis (alkylthio ) alkyl, alkylcarbonylalkyl, alkoxycarbonylalkyl or alkoxyalkoxycarbonylalkyl, each having 1 to 8 carbon atoms in the individual alkyl parts and optionally 1 to 9 identical or different halogen atoms or for each optionally optionally mono- or polysubstituted, identically or differently substituted cycloalkyl, cycloalkyloxycarbonylalkyl or cycloalkylalkyl, each with 3 to 7 coals ffatoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part, the substituents in the cycloalkyl part being suitable in each case: Ha and each straight-chain or branched alkyl or alkoxy each having 1 to 4 carbon atoms, R³ also for each optionally substituted heteroarylalkyl from the series furyl alkyl, thienylalkyl, Oxazolylalkyl, Oxadiazolylal kyl, thiazolylalkyl, Thiadiazolylalkyl, pyridinyl alkyl and Pyrimidinylalkyl, Oxetanylalkyl, tetrahydro drofuranylalkyl or Tetrahydropyranylalkyl each weils 1, and up to 3 carbon atoms in the respective alkyl moieties, finally, for the given substituted one or more times the same or different substituted aralkyl with 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the straight-chain or branched alkyl part, where the following are suitable as aryl substituents: halogen, cyano, nitro, in each case straight-chain or two g tes alkyl, alkoxy, alkylthio or alkoxycarbonyl each having 1 to 4 carbon atoms or each straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
X represents hydrogen, fluorine, chlorine or bromine,
Y represents oxygen or sulfur,
Z represents oxygen or sulfur,
A for oxygen, for a -CH-R⁴ group, for one

or for one

stands where
R⁴ for hydrogen, for each straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkynyl having 3 to 8 carbon atoms, haloalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, haloalkenyl having 2 to 8 carbon atoms and 1 to 15 identical or different halogen atoms, haloalkynyl having 3 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, cyanoalkyl, alkoxyalkyl, alkylthioalkyl, haloalkoxyalkyl, alkoxyalkoxy alkyl, bis (alkoxy) alkyl, bis (alkylthio ) alkyl, alkylcarbonylalkyl, alkoxycarbonylalkyl or alkoxyalkoxycarbonyl, each having 1 to 8 carbon atoms in the individual alkyl parts and, if appropriate, 1 to 9 identical or different halogen atoms or for each optionally mono- or polysubstituted, identically or differently substituted cycloalkyl, cycloalkyloxycarbonylalkyl or cycloalkylalkyl 3 to 7 carbon each atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part, where the substituents in the cycloalkyl part are in each case: halogen and in each case straight-chain or branched alkyl or alkoxy each having 1 to 4 carbon atoms, and
R¹ and R² have the meanings preferably given above, and
for a direct bond or for methylene (-CH₂-), ethylidene

or isopropylidene

stands.

The group of compounds of the formula (I) in which
R¹ and R² either independently of one another each represent hydrogen, methyl, ethyl, n- or i-propyl or together represent a double-linked alkanediyl radical having 2 to 5 carbon atoms,
R³ for hydrogen, for methyl, n- or i-propyl, n-, i-, s- or t-butyl, for allyl, propargyl, for each straight-chain or branched pentyl, hexyl, butenyl, pentenyl, hexenyl, butinyl, Penti nyl or hexinyl also stands for straight-chain or branched haloalkyl with 1 to 4 carbon atoms or haloalkenyl with 3 to 5 carbon atoms and 1 to 8 identical or different halogen atoms, in particular fluorine, chlorine or bromine, for each straight-chain or branched Cyanoalkyl, alkoxyalkyl, alkylthioalkyl, haloalkoxyalkyl, alkoxyalkoxyalkyl, alkylcarbonylalkyl, alkoxycarbonylalkyl or alkoxyalkoxycarbonylalkyl each having 1 to 5 carbon atoms in the individual alkyl parts, moreover optionally for each one to three times, identically or differently by methyl, methoxy, fluorine or chlorine-substituted cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyloxycarbonylmethyl, cyclopentylcarbonylm e thyl, cyclohexyloxycarbonylmethyl, cyclopropyl, cyclopentyl or cyclohexyl, represents in each case ge optionally substituted by methyl and / or ethyl oxetanylmethyl, oxetanylethyl, tetrahydrofuranylmethyl, tetrahydrofuranylethyl, tetrahydropyranylmethyl or tetrahydropylylethyl, oxythydadylmethyl, oxythydropylmethyl, oxythydropylmethyl, oxythydropylmethyl, oxythydropylmethyl, oxythydropylmethyl, oxythydropylmethyl, oxythydropylmethyl, oxythydropylmethyl, oxythydropylmethyl, oxythydropylmethyl, oxythydropylmethyl, oxyethyl pyridylmethyl, oxythyrylethylmethyl, oxyethyl pyridylmethyl, oxyhydroethylmethyl, oxyethyl pyridylmethyl, oxyhydroethylmethyl, oxyethyl, oxyethyl methyl oxy, methyl fetyl, oxyethyl methyl oxy, oxy, methyl, oxy, methyl, oxy, oxy, Thiadiazolylmethyl, pyridinylmethyl and pyrimidinylmethyl or for benzyl or phenylethyl which is monosubstituted to trisubstituted in the same way or differently, where in each case suitable as substituents: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i Propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methoxycarbonyl, ethoxycarbonyl, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
X represents hydrogen, fluorine or chlorine,
Y represents oxygen or sulfur,
Z represents oxygen or sulfur,
A for oxygen, for a -CH-R⁴ group, for one

or for one

stands where
R⁴ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for allyl, propargyl, for each straight-chain or branched pentyl, hexyl, butenyl, pentenyl, hexenyl, Butynyl, pentynyl or hexynyl also stands for straight-chain or branched haloalkyl with 1 to 4 carbon atoms or haloalkenyl with 3 to 5 carbon atoms and 1 to 8 identical or different halogen atoms, in particular fluorine, chlorine or bromine, for each straight-chain term or branched cyanoalkyl, alkoxyalkyl, alkylthioalkyl, haloalkoxyalkyl, alkoxyalkoxyalkyl, alkylcarbonylalkyl, alkoxycarbonylalkyl or alkoxyalkoxycarbonylalkyl, each having 1 to 5 carbon atoms in the individual alkyl parts, and also each optionally one to three times, identically and differently by methyl, methoxy, fluorine or chlorine substituted cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyl oxycarbonylmethyl, cyclopentyloxyca rbonylmethyl, cyclohexyloxycarbonylmethyl, cyclopropyl, cyclo pentyl or cyclohexyl, for each optionally substituted by methyl and / or ethyl oxetanylmethyl, oxetanylethyl, tetrahydrofuranyl methyl, tetrahydrofuranylethyl, tetrahydropyranyl methyl or tetrahydropyranyl
R¹ and R² have the meanings given above as being particularly preferred, and
B for a direct bond or for methylene (-CH₂-), ethylidene

or isopropylidene

stands.

The group of compounds of the formula (I) in which
R¹ and R² either independently of one another each represent hydrogen or methyl or together represent an ethane-1,2-diyl radical, a butane-1,4-diyl radical or a pentane-1,5-diyl radical and
R³ for hydrogen, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for allyl, propargyl, for each straight-chain or branched pentyl, hexyl, butylene, pentenyl, hexenyl, butinyl, pentinyl or He xinyl, furthermore each represents straight-chain or branched haloalkyl having 1 to 4 carbon atoms or haloalkenyl having 3 to 5 carbon atoms and each having 1 to 5 identical or different halogen atoms, in particular fluorine, chlorine or bromine, each representing straight-chain or branched cyanoalkyl, Alkoxyalkyl, alkoxyalkoxy alkyl or alkoxycarbonylalkyl each having 1 to 5 carbon atoms in the individual alkyl parts, moreover in each case optionally cyclopropylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, substituted by methyl, methoxy, fluorine and chlorine , Cyclohexyloxycarbonylmethyl, Cyclo propyl, Cyclopentyl or Cyclohexl stands for jewei If oxetanylmethyl, oxetanylethyl, tetrahydrofuranylmethyl or tetrahydropyranylmethyl is optionally substituted by methyl or ethyl, or stands for benzyl or phenylethyl which is monosubstituted to trisubstituted identically or differently in each case, the substituents being in each case: fluorine, chlorine, bromine, cyano , Nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methoxy carbonyl, ethoxacarbonyl, trifluoromethyl, trifluor methoxy or trifluoromethylthio,
X represents hydrogen or fluorine,
Y represents oxygen or sulfur,
Z represents oxygen or sulfur, and
A for oxygen, for a -CH-R⁴ group, for one

or for one

stands, and
R⁴ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for allyl, propargyl, for each straight-chain or branched pentyl, hexyl, butenyl, pentenyl, hexenyl, Butynyl, pentynyl or hexynyl also stands for straight-chain or branched haloalkyl with 1 to 4 carbon atoms or haloalkenyl with 3 to 5 carbon atoms and 1 to 5 identical or different halogen atoms, in particular fluorine, chlorine or bromine, for each straight-chain term or branched cyanoalkyl, alkoxyalkyl, alkoxyalkoxyalkyl or alkoxycarbonylalkyl, each having 1 to 5 carbon atoms in the individual alkyl parts, moreover for cyclopropylmethyl, cyclopentylmethyl, cyclopentylmethyl, which is optionally mono- to trisubstituted, identically or differently, by methyl, methoxy, fluorine and chlorine, Cyclohexylmethyl, cyclopropyloxycarbonylmethyl, cyclopentyloxycarbonylmethyl, cyclohexyloxycarbonylmethyl, cyclopropyl, cyclopentyl or cyclohe xyl represents oxetanylmethyl, oxetanylethyl, tetrahydrofuranylmethyl or tetrahydropyranylmethyl optionally substituted by methyl and / or ethyl and
R¹ and R² have the meanings given above as being particularly preferred, and
B for a direct bond or for methylene (-CH₂-), ethylidene

or isopropylidene

stands.

Particularly noteworthy are the compounds of the formula (I) in which
R¹ and R² either independently of one another each represent hydrogen or methyl or together represent an ethane-1,2-diyl radical, a butane-1,4-diyl radical or a pentane-1,5-diyl radical,
R³ represents hydrogen, methyl, ethyl, n- or i-propyl, allyl, propargyl, cyanomethyl, cyanoethyl, cyano-n-propyl, cyano-iso-propyl, methoxycarbonylmethyl or ethoxycarbonylmethyl,
X represents hydrogen or fluorine,
Y represents oxygen or sulfur,
Z represents oxygen,
A for

stands and
B stands for a direct bond or -CH₂-.

Examples of the compounds of the invention Formula (I) are shown in Table 1 below leads - cf. also the manufacturing examples.

Table 1: Examples of the compounds of the formula (I)

If the process (a) according to the invention is used, for example 6-amino-7-fluoro-2-methyl-3,4-dihydro-3- oxo-2H-1,4-benzoxazine and isopropylidenesuccinic acid anhydride as starting materials, the Reaction Ver run through the following formula scheme the:

Is used for the process (b) according to the invention for example 1- (4-methoxycarbonyl-methoxy-5-nitrophe nyl) -3-cylohexylidene succinimide and hydrogen as starting materials, the course of the reaction can the following formula scheme can be reproduced:

Is used for process (c) according to the invention for example 1- (2-amino-6-fluorobenzthiazol-5-yl) -3- isopropylidene succinimide, sodium nitrite and salt acid as starting materials, so the course of the reaction can be represented by the following formula:

Is used for process (d) according to the invention for example 1- (6-fluoro-2-oxo-1,3-bezoxazoidin-5- yl) -3-cyclopentylidene succinimide and allyl bromide as starting materials, the course of the reaction can the following formula scheme can be reproduced:  

If one uses for process (e) according to the invention for example 2-hydroxy-3-methyl-3-butenoic acid methyl ester and 7-fluoro-6-isocyanato-4-isopropyl-3,4-dihydro- 3-oxo-2H-1,4-benzothiazine as starting materials, so the Reaction course through the following formula scheme again are given:

If one uses for process (e) according to the invention for example ethyl 1-amino-2,2-dimethylacrylate and 6-fluoro-5-isocyanato-2,3-dihydro-2-oxo-3-propargyl- 1,3-benzothiazoline as starting materials, so the Reak tion course represented by the following formula will be:

If one uses for process (f) according to the invention for example 3- (7-fluoro-2,4-dimethyl-3,4-dihydro-3- oxo-2H-1,4-benzoxazin-6-yl) -5-isopropylidenimidazole-2,4- dione and methyl iodide as starting materials, so the Reaction course through the following formula scheme again are given:

To carry out the method according to the invention (a) Alkylidene amber required as starting materials Acid anhydrides are generally de by the formula (II) finishes. In this formula (II), A1 is preferably a -CH-R⁴ group or for one

in which
R¹, R² and R⁴ preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention.

The anhydrides of the formula (II) are known or are obtained Lich in analogy to known processes (see e.g. Te trahedron 25, 4099-4108 [1969]; Liebigs Note Chem. 461, 191).

To carry out the method according to the invention (a) are still anilines required as starting materials generally defined by formula (III). In this Formula (III) are preferably R³, X, Y and B for those residues that are already in connection with the Be Description of the substances of the formula (I) according to the invention were mentioned as preferred for these substituents.

The anilines of the formula (III) are known or have been obtained in analogy to known methods (see e.g. EP-A 2 37 899; EP-A 1 70 191; EP-A 2 18 972).  

The process for producing (b) according to the invention of compounds of formula (I) as starting materials compounds using the formula (IV) generally defined.

In formula (IV), R¹, R², X, Y, A¹ and B preferably have or especially those meanings that already above in connection with the description of the inventions compounds of formula (I) according to the invention are preferred or as particularly preferred for R¹, R², X, Y, A¹ and B has been specified and Q preferably represents cyano, Carboxy, methoxycarbonyl or ethoxycarbonyl.

Examples of the starting materials of the formula (IV) are listed in the table below:

Table 2

Examples of the starting stage of the formula (IV)

The new intermediates of the formula (IV) are obtained, if compounds of the general formula (X)

in which
R¹, R², X, Y, A¹, B and Q have the meanings given above,
with nitrating agents, such as. B. nitric acid, where appropriate in the presence of sulfuric acid, at temperatures between -20 ° C and + 50 ° C and reacted by conventional methods or if N-aryl nitrogen heterocycles of the formula (XI),

in which
R¹, R², X and A¹ have the meaning given above,
with compounds of the formula (XII)

HY-B-Q (XII)

in which
Y, B and Q have the meaning given above,
in the presence of an acid acceptor, such as. As potassium tert-butoxide, and in the presence of a diluent such. As toluene or ethoxyethane, at temperatures between 0 ° C and 100 ° C.

The - also new - intermediates of formula (X) can, starting from appropriate anilines of the general my formula (XIII)

in which
X, Y, B and Q have the meanings given above, analogously to process (a) according to the invention.

The anilines of the formula (XIII) are known and / or can NEN are produced by methods known per se.  

The intermediates of the formula (X) are also obtained if phenol derivatives of the formula (XIV)

in which
R¹, R², X, Y and A¹ have the meanings given above,
with alkylating agents of the formula (XV)

Hal-B-Q (XV)

in which
B and Q have the meanings given above and
Hal stands for halogen,
in the presence of an acid acceptor, such as. B. potassium car bonate, and in the presence of a diluent, such as. B. toluene or acetronitrile, at temperatures between 0 ° C and 100 ° C.

The - also new - intermediates of formula (XI) can, starting from appropriate anilines of the general my formula (XVI)

in which
X has the meaning given above,
analogous to the process (a) according to the invention.

The anilines of the formula (XVI) are known and / or can NEN according to known methods the.

The intermediates of the formula (XI) are also obtained if you have N-aryl nitrogen heterocycles of the formula (XVII),

in which
R¹, R², X and A¹ have the meaning given above,
with nitrating agents, such as. B. nitric acid, where appropriate in the presence of sulfuric acids, at temperatures between -20 ° C and + 50 ° C and processed by conventional methods.

To carry out the method according to the invention (c) N-aryl nitrogen heterocycles required as starting materials the formula (V) are not yet out of the litera known. The new intermediate products of Formula (V), when compounds of the general formula (XVIII),

in which
R¹, R², X and A¹ have the meanings given above,
with thiocyanates, such as. B. ammonium thiocyanate, where appropriate in the presence of a diluent, such as. As chlorobenzene, at temperatures between -20 ° C and + 150 ° C, and the thiourea derivatives thus obtained cyclized with halogen.

The - also new - intermediates of the formula (XVIII) can, starting from appropriate nitrover bonds of the general formula (XIX),  

in which
R¹, R², X and A¹ have the meaning given above,
by reaction with reducing agents, such as. B. iron powder or hydrogen, optionally in the presence of a diluent, such as. B. acetic acid, and optionally in the presence of a catalyst, such as. B. palladium, at temperatures between -20 ° C and + 50 ° C.

The - also new - intermediates of the formula (XIX), based on the corresponding anilines of the general formula (XX),

in which
X has the meaning given above,
analogous to process (a) according to the invention.

The anilines of the formula (XX) are known and / or can be produced by methods known per se.

To carry out the method according to the invention (d) N-aryl nitrogen heterocycles required as starting materials are generally defi by the formula (Ib) kidney. In this formula (Ib) R¹, R¹, X, Y, A¹ and B preferably for those residues that are already in the Zu connection with the description of the invention Substances of formula (I) as preferred for this substituent were called ducks.

The N-aryl nitrogen heterocycles of formula (Ib) are Compounds according to the invention and obtainable with the help process (a), (b) or (c) according to the invention.

To carry out the method according to the invention (d) Alkyly still required as starting materials Means are generally defi by the formula (VI) kidney. In this formula (VI), R³ is preferably those leftovers already related to the Description of the substances of the formula (I) according to the invention were mentioned as preferred for these substituents.

E stands for a customary one for alkylating agents Leaving residue, preferably for halogen, in particular for chlorine, bromine or iodine, or for each given optionally substituted alkylsulfonyloxy with before preferably 1 to 4 carbon atoms, alkoxysulfo nyloxy preferably having 1 to 4 carbon atoms  or arylsulfonyloxy preferably having 6 to 10 carbon atoms, such as in particular methanesulfonyloxy, Trifluoromethanesulfonyloxy, methoxysulfonyloxy, Ethoxysulfonyloxy or p-toluenesulfonyloxy.

The alkylating agents of formula (VI) are general known compounds of organic chemistry.

To carry out the method according to the invention (e) are carboxylic acid esters required as starting materials generally defined by formula (VII). In this Formula (VII) R⁵ is preferably a radical of formula

in which
R¹, R² and A² preferably represent those radicals which have already been mentioned as preferred for these substituents in connection with the description of the substances of the formula (I) according to the invention,
R⁶ is preferably straight-chain or branched alkyl having 1 to 4 carbon atoms, in particular methyl or ethyl.

The carboxylic acid esters of the formula (VII) are generally be known compounds of organic chemistry or receives in analogy to known methods (see e.g. J. Org. Chem. 37, 943-946 [1972]; EP-A 1 53 692; Chem. Pharm. Bull. 32, 3934-3944 [1984]; Chem. Ber. 110, 942-947 [1977]).

To carry out the method according to the invention (e) Iso (thio) still required as starting materials cyanates are generally defi by the formula (VIII) kidney. In this formula (VIII) R³, X, Y, Z and B preferably for those residues that are already in the Zu connection with the description of the invention Substances of formula (I) as preferred for these substi were mentioned.

The iso (thio) cyanates of the formula (VIII) are known or available in analogy to known processes (cf. e.g. B. EP-A 2 63 299; EP-A 2 55 601; EP-A 2 30 874) for example, if anilines of the formula (III),

in which
R³, X, Y and B have the meaning given above,
with phosgene, thiophosgene or diphosgene (Cl₃C-O-CO-Cl) optionally in the presence of a diluent such as toluene at temperatures between 20 ° C and 120 ° C.

To carry out the method according to the invention (f) N-aryl nitrogen heterocycles required as starting materials are generally defined by the formula (Id). In this formula (Id) R¹, R², X, Y and B are preferred wise for those leftovers that are already related with the description of the substances of the invention Formula (I) mentioned as preferred for these substituents were.

The N-aryl nitrogen heterocycles of formula (Id) are Compounds according to the invention and obtainable with the help of the method (e) according to the invention.

To carry out the method according to the invention (f) Alkyly still required as starting materials Means are generally defi by the formula (IX) kidney. In this formula (IX) R⁴ is preferably those leftovers already related to the Description of the substances of the formula (I) according to the invention were mentioned as preferred for these substituents. It preferably stands for the description of the Formula (VI) radicals.

The alkylating agents of formula (IX) are general known compounds of organic chemistry.  

As a diluent for carrying out the invention According to process (a) there are inert organic solvents means in question. These include in particular ali phatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as Ben zin, benzene, toluene, xylene, chlorobenzene, petroleum ether, Hexane, cyclohexane, dichloromethane, chloroform, tetra chlorocarbon, ethers such as diethyl ether, dioxane, Te trahydrofuran or ethylene glycol dimethyl or diethyl ethers, ketones, such as acetone or butanone, nitriles, such as Acetonitrile or propionitrile, amides, such as dimethyl form amide, dimethylacetamide, N-methylformanilide, N-methyl pyrrolidone or hexamethylphosphoric triamide, esters, such as ethyl acetate, sulfoxides such as dimethyl sulfate oxide or carboxylic acids, such as acetic acid or propion acid.

Process (a) according to the invention can, if appropriate in the presence of a suitable reaction auxiliary be performed. Anorga is preferably used niche or organic acids, such as vinegar acid or p-toluenesulfonic acid, anhydrides such as wise acetic anhydride or acid chlorides such as acetyl chloride as a reaction aid. It is also possible for others usual water-releasing agents, such as N, N'-dicyclohexylcarbodiimide or customary acylation catalysts, such as 4- (N, N-dimethylamino) - to use pyridine as a reaction aid.

The reaction temperatures can be carried out process (a) according to the invention in a larger one  Range can be varied. Generally one works at Temperatures between 20 ° C and 180 ° C, preferably at Temperatures between 50 ° C and 150 ° C.

To carry out process (a) according to the invention is used per mole of alkylidene succinic anhydride Formula (II) generally 1.0 to 1.5 moles, preferably 1.0 to 1.2 mol of aniline of the formula (III) and given optionally 0.01 to 1.2 mol, preferably 0.1 to 1.0 mol of reaction aids. The implementation of the reaction, Processing and isolation of the reaction products follows according to generally accepted methods (cf. also the Manufacturing examples).

Process (b) is carried out in the presence of a diluent carried out. Alcohols such as metha are preferred nol, ethanol, propanol or isopropanol, ether, such as Gly coldimethyl ether, diglycol dimethyl ether, tetrahydrofuran or dioxane, or esters, such as methyl acetate or Ethyl acetate, and optionally also water used as solvent for process (b).

Process (b) according to the invention for producing the new compounds of formula (I) is used performed a reducing agent. As a reduction The main means for process (b) are hydrogen in Presence of a catalyst or iron in combination with an acid such as B. hydrochloric acid.

Process (b) according to the invention is, if appropriate carried out using a catalyst. As  Examples include Raney nickel, platinum and palla called dium. Raney nickel is preferred for process ren (b) used.

The reaction temperatures in the fiction method (b) varied over a wide range will. Generally one works at temperatures between 0 ° C and 150 ° C, preferably at temperatures between 20 ° C and 100 ° C.

Process (b) is generally carried out at normal pressure or increased pressure up to about 200 bar, preferably up to about 100 bar.

Process (b) can be used in catalytic hydries conditions are carried out. In a preferred embodiment of method (b) the starting compound of formula (IV) with the diluent mixed with the catalyst and then like this long metered hydrogen until no consumption of what more substance can be determined. After the end of the hy The reaction mixture is filtered and obtained after concentrating the filtrate, the crude product as a return stood, which in the usual way, for example by Column chromatography, can be purified.

In another preferred embodiment of Ver drive (b) iron with an acid, preferably Hydrochloric acid, placed in a suitable solvent, the starting compound of formula (IV) is given if added at elevated temperature, slowly and  the reaction mixture is ge until the end of the reaction leads. The processing takes place according to usual methods.

As a diazotizing agent to carry out the process (c) all come usual for such diazotizations Diazotizing agents in question. Preferably used Sodium or potassium nitrite.

As a diluent for carrying out the invention according to method (c) are usually all for such diazotization reactions usable solution medium in question. Preferably used as the rea genien in question acids or their mixtures with catalyst acid, such as (aqueous) Sulfuric acid, hydrochloric acid or acetic acid, simultaneously as a diluent.

As bases for carrying out the method according to the invention rens (c) are preferably potassium hydroxide solution or sodium hydroxide solution in question.

The reaction temperatures can be carried out process (c) according to the invention in a larger one Range can be varied. Generally one works at Temperatures between -10 ° C and + 50 ° C, preferably at Temperatures between 0 ° C and 30 ° C.  

To carry out process (c) according to the invention is generally per mole of compound of formula (V) mean 1.0 to 2.0 moles, preferably 1.0 to 1.2 moles of diaziotizing agents. The implementation of the reaction, Processing and isolation of the reaction products of the Formula (Ic) is carried out according to customary, generally known Method.

To carry out method (d) according to the invention come as a diluent, inert organic solutions medium in question. Aliphati is preferably used cal, alicyclic or aromatic, optionally ha logenated hydrocarbons such as Ben zin, benzene, toluene, xylene, pentane, hexane, heptane, cyc lohexane, petroleum ether, ligroin, methylene chloride, chloro form, carbon tetrachloride, chlorobenzene or dichlor benzene, ethers, such as diethyl ether, diisopropyl ether, di oxane, tetrahydrofuran or ethylene glycol diethyl ether or dimethyl ether, ketones such as acetone, butanone, Me thylisopropyl ketone or methyl isobutyl ketone, esters such as Ethyl acetate, nitriles, such as acetronitrile or Pro pionitrile, amides, such as dimethylformamide, dimethylacet amide, N-methylpyrrolidone or hexamethylphosphoric acid triamid. Alkyly is used as the reactant  agent of the formula (VI) in liquid form it is also possible to use this in a corresponding excess to be used simultaneously as a diluent.

As a reaction aid to carry out the inventions Process (d) according to the invention are all customary usable inorganic and organic bases in Question. Alkali metal hydrides are preferably used, hydroxides, amides, carbonates or bicarbonates, such as sodium hydride, sodium amide, sodium hydroxide, sodium carbonate or sodium hydrogen carbonate, or also tertiary amines, such as triethyl amine, N, N-dimethylaniline, pyridine, 4- (N, N-dimethyl amino) pyridine, diazabicyclooctane (DABCO), diazabicyc ionone (DBN) or diazabicycloundecene (DBU).

The reaction temperatures can be carried out process (d) according to the invention in a larger one Range can be varied. Generally you work between -20 ° C and + 150 ° C, preferably between 0 ° C and + 100 ° C.

To carry out method (d) according to the invention for each mole of N-aryl nitrogen heterocycle of For mel (Ib) in general 1.0 to 20.0 mol, respectively preferably 1.0 to 15.0 mol each, of alkylation with tel of formula (VI) and optionally 1.0 to 3.0 mol, preferably 1.0 to 2.0 mol of reaction auxiliary, a. The implementation of the reaction, workup and isolation tion of the reaction products of formula (I) takes place after usual methods.  

As a diluent for carrying out the invention According to process (s) there are inert organic solutions medium in question. These include in particular aliphati cal, alicyclic or aromatic, optionally ha logenated hydrocarbons such as Ben zin, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, Petroleum ether, hexane, cyclohexane, dichloromethane, chloro form, carbon tetrachloride, ethers, such as diethyl ether, Dioxane, tetrahydrofuran or ethylene glycol dimethyl or -diethyl ether, nitriles, such as acetonitrile or propioni tril, amides, such as dimethylformamide, dimethylacetamide, N-methylpyrrolidone or hexamethylphosphoric triamide.

The process (e) according to the invention is optionally in the presence of a suitable reaction auxiliary carried out. As such come all the usual inorganic or organic bases in question. These include for example alkali metal hydroxides such as sodium hy hydroxide or potassium hydroxide, alkali metal carbonates, such as Sodium carbonate, potassium carbonate or sodium hydrogen carbonate, and also tertiary amines, such as triethylamine, N, N-dimethylaniline, pyridine, N, N-dimethylaminopyridine, Diazabicyclooctane (DABCO), diazabicyclonones (DBN) or Diazabicycloundecene (DBU).

The reaction temperatures can be carried out process (e) according to the invention in a larger one Range can be varied. Generally one works at Temperatures between 0 ° C and 150 ° C, preferably at Temperatures between 20 ° C and 120 ° C.  

To carry out method (e) according to the invention are used per mole of carboxylic acid ester of the formula (VII) or a corresponding acid addition salt in space mean 0.5 to 5.0 moles, preferably 0.8 to 1.5 moles on iso (thio) cyanate of the formula (VIII) and, if appropriate 1.0 to 10.0 moles, preferably 1.0 to 5.0 moles of reak aids. It is also possible to Iso (thio) cyanate of formula (VIII) in an upstream th reaction of amines of the formula (III) and phosgene, Thiophosgene or diphosgene (Cl₃C-O-CO-Cl) directly in Re production vessel and without insulation in the "one pot process "with the carboxylic acid esters of the formula (VII) continue to implement.

The implementation of the reaction, workup and isolation the reaction products are carried out according to generally customary methods Methods (see also the manufacturing examples).

To carry out method (f) according to the invention come as a diluent, inert organic solutions medium in question. Aliphati is preferably used cal, alicyclic or aromatic, optionally ha logenated hydrocarbons such as Ben zin, benzene, toluene, xylene, pentane, hexane, heptane, cy clohexane, petroleum ether, ligroin, methylene chloride, chloro form, carbon tetrachloride, chlorobenzene or dichlor benzene, ethers, such as diethyl ether, diisopropyl ether, di oxane, tetrahydrofuran or ethylene glycol diethyl ether or dimethyl ether, ketones such as acetone, butanone, Me thylisopropyl ketone or methyl isobutyl ketone, esters such as  Ethyl acetate, nitriles, such as acetonitrile or Pro pionitrile, amides, such as dimethylformamide, dimethylacet amide, N-methylpyrrolidone or hexamethylphosphoric acid triamid. Alkyly is used as the reactant agent of formula (IX) in liquid form it is possible to equal this in a corresponding excess to be used early as a diluent.

As a reaction aid to carry out the inventions Process (f) according to the invention are all customary usable inorganic or organic bases in Question. Alkali metal hydrides are preferably used, hydroxides, amides, carbonates or bicarbonates, such as sodium hydride, sodium amide, sodium hydroxide, sodium carbonate or sodium hydrogen carbonate, or also tertiary amines, such as triethyl amine, N, N-dimethylaniline, pyridine, 4- (N, N-dimethylami no) pyridine, diazabicyclooctane (DABCO), diazabicyclo nonen (DBN) or diazabicycloundecene (DBU).

The reaction temperatures can be carried out process (f) according to the invention in a larger one Range can be varied. Generally you work between -20 ° C and + 150 ° C, preferably between 0 ° C and + 100 ° C.

To carry out method (f) according to the invention for each mole of N-aryl nitrogen heterocycle of For mel (Id) in general 1.0 to 20.0 mol, respectively preferably 1.0 to 15.0 mol each, of alkylation with tel of formula (IX) and optionally 1.0 to 3.0 mol,  preferably 1.0 to 2.0 mol of reaction auxiliary, a. The implementation of the reaction, workup and isolation tion of the reaction products of formula (I) takes place after usual methods.

The active compounds according to the invention can be used as defoliants, Desiccants, herbicides and especially as Weed killers are used. Under Un herb in the broadest sense, all plants can be understood hen who grow up in places where they are undesirable. Whether the substances according to the invention as total or selek effective herbicides depend essentially on the applied amount.

The active compounds according to the invention can, for. B. at the following plants can be used:

Dicotyledon weeds of the genera:
Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Cheno podium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Am brosia, Cirsium, Carduus, Sonchus, Solanum, R Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea.

Dicotyledon cultures of the genera:
Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis, Cucurbita.

Monocot weeds of the genera:
Echinochloa, Se taria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleu sine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Sphenum, Ioclema Dactyloctenium, Agrostis, Alopecurus, Apera.

Monocot cultures of the genera:
Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ana nas, Asparagus, Allium.

The use of the active compounds according to the invention is however, in no way limited to these genera, son it extends in the same way to others Plants.

The connections are suitable depending on the con center for total weed control z. B. on industrial and track systems and on paths and squares with and without Tree growth. Likewise, the connections to weeds control in permanent crops, e.g. B. forest, ornamental wood, Fruit, wine, citrus, nut, banana, coffee, tea, Gum, oil palm, cocoa, berry fruit and hop plants and for selective weed control in annuals Cultures are used.

The active compounds according to the invention are suitable for selek tive weed control, especially of dicotyledon weeds tern in mono- and dicotyledon cultures before and after baking procedure.  

The active compounds according to the invention are also suitable as Plant growth regulators, especially for defluxing Leaving and drying of the leaves in cotton.

The active substances according to the invention reach into the Metabo lism of plants and can therefore be used as wax regulators are used.

For the mode of action of plant growth regulators Experience has shown that an active ingredient also several different effects on plants can exercise. The effects of the substances depend essentially from the time of application based on the stage of development of the plant as well as from the on active ingredient applied to the plants or their surroundings quantities and the type of application. In any case growth regulators should be the crops in be influence the desired way.

Under the influence of growth regulators Leaves of the plants are controlled so that a Defoliate the plants at a desired time is achieved. Such defoliation plays at mechanical harvesting of cotton plays a major role but is also in other cultures such. B. in viticulture to facilitate the harvest of interest. An entlau Exercise of the plants can also be made to the Transpiration of plants before transplanting put.  

In appropriate application rates show the fiction active ingredients also have a fungicidal activity and can be used, for example, to combat fungal diseases in rice cultivation, such as against the pathogen of rice stain disease (Pyricularia oryzae) put. In this area of application, the inventions Active ingredients according to the invention in addition to good protective agents systemic properties.

The active ingredients can be in the usual formulations are transferred, such as solutions, emulsions, spray powder ver, suspensions, powders, dusts, pastes, sol Liche powders, granules, suspension emulsion concentrates trat, active ingredient-impregnated natural and synthetic Fabrics and very fine encapsulation in polymeric fabrics fen.

These formulations are produced in a known manner provides, e.g. B. by mixing the active ingredients with Extenders, i.e. liquid solvents and / or solid carriers, optionally using of surface-active agents, i.e. emulsifiers and / or dispersants and / or foam generators Means.

In the case of the use of water as an extender z. B. also organic solvents as auxiliary sol be used. As a liquid solvent essentially come into question: aromatics, such as xylene, Toluene, or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as  Chlorobenzenes, chlorethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or Paraffins, e.g. B. petroleum fractions, mineral and vegetable oils, alcohols such as butanol or glycol as well their ethers and esters, ketones such as acetone, methylethylke clay, methyl isobutyl ketone or cyclohexanone, strongly polar Solvents such as dimethylformamide and dimethyl sulfate oxide, as well as water.

The following are suitable as solid carriers:
e.g. B. ammonium salts and natural rock powders such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and synthetic rock powders such as highly disperse silica, aluminum oxide and silicates, as solid carriers for granules come into question: z. B. broken and fractional natural Liche rocks such as calcite, marble, pumice, sepiolite, dolomite and synthetic granules from inorganic and organic flours and granules from organic material such as sawdust, coconut shells, corn cobs and tobacco stalks; as emulsifying and / or foam-generating agents come into question: z. B. non-ionic and anionic cal emulsifiers such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for. B. alkylaryl polyglycol ethers, alkyl sulfonates, alkyl sulfates, aryl sulfonates and protein hydrolyzates; as dispersants come into question: z. B. lignin sulfite and Me methyl cellulose.

Adhesives such as carboxy can be used in the formulations methyl cellulose, natural and synthetic powder, granular or latex-shaped polymers can be used, such as  Gum arabic, polyvinyl alcohol, polyvinyl acetate, as well natural phospholipids such as cephalins and lecithins and synthetic phospholipids. Other additives can mineral and vegetable oils.

Dyes such as inorganic pigments, e.g. B. Iron oxide, titanium oxide, ferrocyan blue and organic Dyes such as alizarin, azo and metal phthalocya nin dyes and trace nutrients such as salts of iron, Use manganese, boron, copper, cobalt, molybdenum and zinc be det.

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

The active compounds according to the invention can be used as such or in their formulations also in a mixture with known ones Weed herbicides find where possible with finished formulations or tank mixes are.

Known herbicides such as z. B. 2.4D; 2.4DP; 2,4DB; MCPA; MCPP; Fluoroxypyr; Dichlofop methyl; Fenoxaprop; Fluazifop-butyl; Aluizalofop; Haloxyfrop; Clopyralid; Norflurazon; Alachlor; Metolachlor; Oryzalin; Pendimethalin; Trifluralin; Acifluorfen; Bifenox; Fomesafen; Lactofen; Oxyfluorfen; Chlorotoluron; Isoproturon; Methabenzthiazuron; Alloxy dim; Sethoxydim; Imazamethabenz; Imazaquin; Bromoxynil;  Ioxynil, Mefenacet, Chlorimuron, Chlorsulfuron, Metsul furon, thiameturon, EPTC, triallates, atrazine, cyanazine, Simazin, Simetryne, Terbutryne, Ethiozin, Hexazinon, Metamitron, Metribuzin, Bentazone, Cinmethylin, Pyridate and dimethazone in question. Some blends show over surprisingly also synergistic effect.

Also a mixture with other known active ingredients, such as fungicides, insecticides, acaricides, nematicides, Protection against bird feed, plant nutrients and Soil improvers are possible.

The active ingredients as such, in the form of their formu or the resulting from further dilution riding application forms, such as ready-to-use solutions genes, suspensions, emulsions, powders, pastes and Granules can be applied. The application happens in the usual way, e.g. B. by pouring, spraying, spraying hen, scatter.

The active compounds according to the invention can be used both before as well as applied after emergence of the plants will.

You can also work in the soil before sowing be tested.

The amount of active ingredient used can be greater Fluctuate range. It essentially depends on the Type of effect desired. Generally lie  the application rates between 0.01 and 10 kg of active ingredient fabric per hectare of soil, preferably between 0.01 and 5 kg per ha, in particular between 0.01 and 2 kg per ha.

The production and use of the fiction The active ingredients are shown in the examples below forth.  

Manufacturing examples example 1 Procedure (a)

A mixture of 7.06 g (0.064 mol) of methylene succinic acid reanhydride, 9.85 g (0.06 mol) of 6-amino-3,4-dihydro-3-oxo 2H-1,4-benzoxazine and 180 ml of glacial acetic acid are added for 5 hours 135 ° C stirred. After cooling and concentrating the back was recrystallized from methanol.

9.32 g (60.2% of theory) of 1- (3,4-dihydro-3-oxo-2H-1,4-benzoxazin-6-yl) -3-methylenesuccinimide of melting point 230 to 234 ° C. are obtained .
1 H-NMR (80 MHz, CDCl₃ / DMSO, δ): 10.78 (s, 1H); 6.99 (d, 1H, J = 9.0 Hz); 6.91 (d, 1H, J = 1.0 Hz); 6.86 (dd, 1H, J = 9.0 Hz, J = 1.0 Hz); 6.34 (t, 1H, J = 1.0 Hz); 5.74 (t, 1H, J = 1.0 Hz); 4.56 (s. 2H); 3.51 (t, 2H, J = 1.0 Hz).

Example 2 Procedure (a)

4.44 g (0.02 mol) of 5-amino-6-fluoro-2,3-dihydro-2-oxo-3- are added to a solution of 2.94 g (0.021 mol) of isopropylidene succinic anhydride in 60 ml of glacial acetic acid. proparg yl-1,3-benzothiazoline with stirring and then heated to 135 ° C for five hours. The mixture is cooled and the precipitate (1.87 g) is filtered off with suction. After concentration, the residue is separated by column chromatography on silica gel and a further 2.72 g is obtained. A total of 4.59 g (66.7% of theory) of 1- (6-fluoro-2,3-dihydro-2-oxo-3-propargyl-1,3-benzothiazolin-5-yl) -3-isopropylidene is obtained succinimide from melting point 239 to 243 ° C.
1 H-NMR (80 MHz, CDCl₃ / DMSO, δ): 7.60 (d, 1H, J = 9.0 Hz); 7.30 (d, 1H = 7.0 Hz); 4.75 (d, 2H, J = 1 Hz), 3.49 (bs, 2H); 2.84 (t, 1H, J = 1 Hz); 2.36 (s, 3H); 1.97 (s, 3H).

Example 3 Procedure (a)

A mixture of 3.60 g (0.102 mol) of 3-cyclohexylidene succinic anhydride and 4.18 g (0.019 mol) 6-amino-7- fluoro-3,4-dihydro-3-oxo-4-propargyl-2H-1,4-benzoxazine and 75 ml of glacial acetic acid is stirred at 135 ° C for 5 hours heated. After distilling off the volatile component the residue is recrystallized from methanol.

5.53 g (76.2% of theory) of 1- (7-fluoro-3,4-dihydro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6-yl) -3- are obtained. cyclohexylidene succinimide from melting point 135 to 139 ° C.
1 H-NMR (80 MHz, CDCl₃, δ): 7.05 (d, 1H, J = 8.0 Hz); 6.91 (d, 1H, J = 9.0 Hz); 4.67 (s, 4H); 3.44 (s, 2H); 3.07 (s, 2H); 2.29 (m, 3H); 1.68 (m, 6H).

Example 4 Procedure (a)

A solution of 1.14 g (0.0063 mol) diiso is heated propylidene succinic anhydride and 1.32 g (0.006 mol) 6-amino-7-fluoro-3,4-dihydro-3-oxo-4-propargyl-2H-1,4- benzoxazine in 20 ml glacial acetic acid for five hours at 135 ° C. After cooling, the mixture is concentrated and the resultant is transferred Succinic acid monoamide with 0.2 g (0.0024 mol) sodium acetate and 5 ml acetic anhydride.

The reaction mixture is heated at 95 ° C. for two hours, cooled and concentrated. Separation by column chromatography on silica gel gives 0.41 g (17.5% of theory) of 1- (7-fluoro-3,4-dihydro-3-oxo-4-propargyl-2H-1,4-benzoxazin-6- yl) -3,4-diisopropylidene amine acid imide melting point 189 to 191 ° C.
1 H-NMR (80 MHz, CDCl₃, δ): 7.09 (d, 1H, J = 8.0 Hz); 6.90 (d, 1H, J = 9.0 Hz); 4.67 (s, 4H); 2.40 (s, 4H); 1.95 (s, 3H).

Example 5 Method (d)

A mixture of 2.90 g (0.01 mol) of 1- (6-fluoro-2,3-dihy dro-2-oxo-1,3-benzoxazolin-5-yl) -3-isopropylidene succinimide, 2.07 g (0.015 mol) potassium carbonate and 15 ml of acetonitrile is refluxed for one hour Boiling heated. After cooling to 25 ° C an 80% Solution of 1.79 g (0.015 mol) of propargyl bromide in toluene added and the reaction mixture for 4 hours reflux heated to boiling. After constriction, with Extracted methylene chloride, the extraction solution with saturated sodium bicarbonate solution and with what washed, dried with sodium sulfate and fil trated. After concentration, the residue is separated by columns Chromatography purified on silica gel.

2.12 g (64.6% of theory) of 1- (6-fluoro-2,3-dihydro-2-oxo-3-propargyl-1,3-benzoxazolin-5-yl) -3-isopropylidene succinimide are obtained from melting point 150 to 158 ° C.
1 H-NMR (80 MHz, CDCl₃, δ): 7.18 (d, 1H, J = 9.0 Hz); 7.08 (d, 1H, J = 8.0 Hz); 4.61 (d, 2H, J = 2.0 Hz); 3.48 (d, 1H, J = 18.0 Hz); 3.39 (d, 1H, J = 18.0 Hz); 2.41 (t, 1H, J = 2.0 Hz); 2.39 (s, 3H); 1.97 (s, 3H).

Example 6 Method (s)

2.41 g (0.006 mol) of the compound are dissolved in accordance with the un The aforementioned intermediate 6a in 40 ml of toluene, adds 0.20 g (0.003 mol) sodium methylate and boil after five Hours at reflux temperature. After cooling, you narrow a.

1.79 g (86.7% of theory) of 3- (7-fluoro-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-6-yl) -5-isopropylidene-1 are obtained. 3-oxazolidin-2,4-dione with melting point 157 to 163 ° C.
1 H-NMR (80 MHz, CDCl₃, δ): 7.13 (d, 1H, J = 8.0 Hz); 6.94 (d, 1H, J = 9.0 Hz); 4.70 (s, 2H); 4.68 (d, 2H, J = 1 Hz); 2.31 (s, 3H); 2.32 (t, 1H, J = 1 Hz); 2.07 (s, 3H).

Intermediate 6a

A solution of 5.76 g (0.04 mol) of 2-hydroxy-3-methyl-3-butenoic acid ethyl ester and 4.92 g (0.02 mol) of 7-fluoro-6-isocyanato-4-propargyl-3,4 dihydro-3-oxo-2H-1,4-benzoxa zin in 100 ml of toluene is heated at 80 ° C for six hours. After cooling, the precipitate is filtered off and concentrated. Separation by column chromatography on silica gel gives 3.28 g (42.1% of theory) of 2- [N- (7-fluoro-3,4-dihydro-3-oxo-2H-1,4-benzoxazin-6-yl ) - carbamoyloxy] -3-methyl-3-butenoic acid ethyl ester as an oil.
1 H-NMR (80 MHz, CDCl₃, δ): 8.00 (bs, 1H); 7.98 (d, 1H, J = 8.0 Hz); 6.79 (d, 1H, J = 9.0 Hz); 5.51 (s, 1H); 5.25 (bs, 1H); 5.15 (s, 1H); 4.70 (s, 2H); 4.68 (d, 2H, J = 1 Hz); 4.26 (q, 2H, J = 8.0 Hz); 2.28 (6, 1H, J = 1 Hz); 1.85 (s, 3H); 1.33 (t, 3H, J = 8.0 Hz).

Example 7 Method (s)

To a mixture of 23.5 g (0.085 mol) of N-benzyloxy carbonyl-α, β-dehydrovaline ethyl ester, 8.59 g (0.085 mol)  Triethylamine and 120 ml of o-dichlorobenzene are added to 20.91 g (0.085 mol) 7-fluoro-6-isocyanato-4-propargyl-3,4-dihy dro-3-oxo-2H-1,4-benzoxazin and heats the reak tion mixture for 15 hours at 140 ° C. Sucks after cooling the precipitation.

3.50 g (12.0% of theory) of 3- (6-fluoro-3,4-dihydro-3-oxo-2H-benzoxazin-6-yl) -5-isopropylidene-3H-imidazol-2 are obtained, 4-dione with melting point <300 ° C.
1 H-NMR (80 MHz, CDCl₃ / DMSO, δ): 10.30 (bs, 1H); 7.21 (d, 1H, J = 8.0 Hz); 6.99 (d, 1H, J = 9.0 Hz); 4.73 (s, 2H); 4.69 (d, 2H, J = 1 Hz); 2.83 (t, 1H, J = 1 Hz); 2.24 (s, 3H); 1.94 (s, 3H).

Example 8 Method (f)

A mixture of 1.72 g (0.005 mol) of 3- (6-fluoro-3,4-dihydro-3-oxo-2H-benzoxazin-6-yl) -5-isopropylidene-1H-imidazole-2,4 -dione, 1.04 g (0.075 mol) of potassium carbonate and 20 ml of acetonitrile is refluxed for two hours. The mixture is cooled and 1.42 g (0.0075 mol) of methyl iodide are added dropwise at 25 ° C. After four hours of reflux, the mixture is concentrated and the residue is extracted with methylene chloride. The organic phase is washed with a saturated sodium hydrogen carbonate solution and water, dried over sodium sulfate and concentrated. After recrystallization from a mixture of methylene chloride / petroleum ether, 1.47 g (82.3% of theory) of 3- (6-fluoro-3,4-dihydro-3-oxo-2H-benzoxazin-6-yl) are obtained. -5-iso propylidene-1-methylimidazole-2,4-dione with a melting point of 209 to 216 ° C.
1 H-NMR (80 MHz, CDCl₂, δ): 7.10 (d, 1H, J = 8 Hz); 6.90 (d, 1H, J = 9.0 Hz); 4.67 (s, 4H); 3.47 (s, 3H); 2.38 (s, 3H); 2.29 (t, 1H, J = 1 Hz); 2.21 (s, 3H).

Analogous to Examples 1 to 8 and according to the general my description of the manufacturing according to the invention the procedure in Table 3 below led compounds of formula (I) can be obtained.

Table 3

Preparation examples for the compounds of the formula (I)

Examples of use

In the following application examples, the next one Compound (A) listed as comparison substance used:

(known from EP-A 2 90 863)  

Example A Post emergence test

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

To produce a suitable preparation of active ingredients tion, 1 part by weight of active ingredient is mixed with the specified amount of solvent, gives the specified Amount of emulsifier and dilute the concentrate with Water to the desired concentration.

With the preparation of the active ingredient you inject test plants, which have a height of 5-15 cm so that the each because desired amounts of active ingredient per unit area be applied. The concentration of the spray liquor is chosen so that in 2000 l of water / ha each desired amounts of active ingredient are applied. To The degree of damage to the plants is three weeks rated in% damage compared to development the untreated control. It means:

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

In this test, the compounds according to the invention show according to production example 2, 5, 14, 15 and 16 a Deut Lich better herbicidal activity, especially in the Be fighting z. B. Galium and Polygonum, as the Ver direct connection (A).  

Example B Post emergence test

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

To produce a suitable preparation of active ingredients tion is mixed 1 part by weight of active ingredient with the specified Amount of solvent, gives the specified amount of emulsifier and dilute the concentrate with water on the desired concentration.

Seeds of the test plants are sown in normal soil and watered with the active ingredient preparation after 24 hours. The amount of water per unit area is kept expediently constant. The drug concentration in the preparation does not matter, it is crucial only the application rate of the active ingredient per unit area. After three weeks, the degree of damage to the plants rated in% damage compared to development the untreated control. It means:

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

In this test, the compounds according to the invention show 2, 5, 14, 15, 16, 20 a much better herbicidal we kung, especially in the fight against z. B. Galium, Ipomoea and Stellaria, as the comparison compound (A).  

Example C Defoliation and drying of the leaves of cotton

Solvent: 30 parts by weight of dimethylformamide
Emulsifier: 1 part by weight of polyoxyethylene sorbitan monolaurate

To produce a suitable preparation of active ingredients tion, 1 part by weight of active ingredient is mixed with the specified amounts of solvent and emulsifier and fills to the desired concentration with water.

Cotton plants are grown to the full in the greenhouse Unfolding of the 5th following sheet attracted. In this Sta dium the plants are dripping wet with the active ingredient sprayed riding. After 1 week the leaf fall and the drying out of the leaves compared to the cones troll plants rated.

In this test, the compounds according to the invention show 2, 3, 5, 16 and 17 have a very good effect.

Claims (10)

1. N-aryl nitrogen heterocycles of the general formula (I) in which
R¹ and R² either independently of one another each represent hydrogen or alkyl or together represent a double-linked alkanediyl radical,
R³ represents hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or heteroarylalkyl,
X represents hydrogen or halogen,
Y represents oxygen or sulfur,
Z represents oxygen or sulfur,
A for oxygen, for a -CH-R⁴ group, for one or for one stands where
R⁴ represents hydrogen, each optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or alkoxycarbonyl, and
B for a direct bond or for methylene (-CH₂-), ethylidene or isopropylidene stands 2. N-aryl nitrogen heterocycles of the formula (I) according to claim 1, in which
R¹ and R² either independently of one another each represent hydrogen or straight-chain or branched alkyl having 1 to 4 carbon atoms or together represent a double-linked alkanediyl radical having 2 to 7 carbon atoms,
R³ for hydrogen, for each straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkynyl having 3 to 8 carbon atoms, haloalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, haloalkenyl having 2 to 8 carbon atoms and 1 to 15 identical or different halogen atoms, haloalkynyl having 3 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, cyanoalkyl, alkoxyalkyl, alkylthioalkyl, haloalkoxyalkyl, alkoxyalkoxyalkyl, bis (alkoxy) alkyl, bis (alkylthio ) alkyl, alkylcarbonylalkyl, alkoxycarbonylalkyl or alkoxyalkoxycarbonylal kyl each having 1 to 8 carbon atoms in the individual alkyl parts and optionally 1 to 9 identical or different halogen atoms or for each optionally optionally mono- or polysubstituted, identically or differently substituted cycloalkyl, cycloalkyloxycarbonylal alkyl or cycloalkylalkyl 3 to 7 Kohlens each toffatomen in the cycloalkyl part and optionally 1 to 4 carbon atoms in the ge radkettigen or branched alkyl part, where as substituents in the cycloalkyl part each come into question: halogen and straight-chain or branched alkyl or alkoxy each with 1 to 4 carbon atoms, R³ also for each optionally substituted heteroarylalkyl from the series furylalkyl, thienylalkyl, oxazolylalkyl, oxadiazolylalkyl, thiazolylalkyl, thiadiazolylalkyl, pyridinylalkyl and pyrimidinylalkyl, oxetanylalkyl, tetrahydrofuranylalkyl or tetrahydropyranylalkyl, each with 1 to 3 carbon atoms and finally, in each case, for 1 or 3 carbon atoms, and in each case optionally represents 1 or 3 carbon atoms and finally each represents a single atom or carbon atom Aralkyl having 6 to 10 carbon atoms in the aryl part and 1 to 4 carbon atoms in the rad-chain or branched alkyl part which is substituted several times or differently, aryl substituents being suitable: halogen, cyano, nitro, in each case straight-chain or ver branched alkyl, alkoxy, alkylthio or alkoxycarbonyl each having 1 to 4 carbon atoms or straight-chain or branched haloalkyl, haloalkoxy or haloalkylthio each having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms,
X represents hydrogen, fluorine, chlorine or bromine,
Y represents oxygen or sulfur,
Z represents oxygen or sulfur,
A for oxygen, for a -CH-R⁴ group, for one or for one stands where
R⁴ for hydrogen, for each straight-chain or branched alkyl having 1 to 8 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkynyl having 3 to 8 carbon atoms, haloalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, haloalkenyl 2 to 8 carbon atoms and 1 to 15 identical or different halogen atoms, haloalkynyl having 3 to 8 carbon atoms and 1 to 13 identical or different halogen atoms, cyanoalkyl, alkoxyalkyl, alkylthioalkyl, haloalkoxyalkyl, alkoxyalkoxyalkyl, bis- (alkoxy) alkyl, bis- (Alkylthio) alkyl, alkylcarbonylalkyl, alkoxycarbonylalkyl or alkoxyalkoxycarbonylal kyl each having 1 to 8 carbon atoms in the individual alkyl parts and optionally 1 to 9 identical or different halogen atoms or for each optionally mono- or polysubstituted, identically or differently substituted cycloalkyl, cycloalkyloxycarbonylal or Cycloalkylalkyl with 3 to 7 cabbages each Substance atoms in the cycloalkyl part and optionally 1 to 4 carbon atoms in the straight-chain or branched alkyl part, where the substituents in the cycloalkyl part are suitable: halogen and straight-chain or branched alkyl or alkoxy each with 1 to 4 carbon atoms, and
R¹ and R² have the meanings given above, and
B for a direct bond or for methylene (-CH₂-), ethylidene or isopropylidene stands. 3. N-aryl nitrogen heterocycles of the formula (I) according to claim 1, in which
R¹ and R² either independently of one another each represent hydrogen, methyl, ethyl, n- or i-propyl or together represent a doubly linked alkanediyl radical having 2 to 5 carbon atoms,
R³ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for allyl, propargyl, for straight-chain or branched pentyl, hexyl, butenyl, pentenyl, hexenyl, Butynyl, pentynyl or hexynyl also represents in each case straight-chain or branched haloalkyl having 1 to 4 carbon atoms or haloalkenyl having 3 to 5 carbon atoms and each having 1 to 8 identical or different halogen atoms, for each rad-chain or branched cyanoalkyl, alkoxyalkyl, Alkylthioalkyl, haloalkoxyalkyl, alkoxyalkoxyalkyl, alkylcarbonylalkyl, alkoxycarbonylalkyl or alkoxyalkoxycarbonylalkyl each having 1 to 5 carbon atoms in the individual alkyl parts, moreover for cyclopropylmethyl, cyclopentylmethyl, which is optionally monosubstituted to trisubstituted, identically or differently, by methyl, methoxy, fluorine or chlorine, Cyclohexylmethyl, Cyclopro pyloxycarbonylmethyl, Cyclopentylcarbonylmethyl, Cyclohexyloxycarbonylmethyl, C yclopro pyl, cyclopentyl or cyclohexyl, each optionally substituted by methyl and / or ethyl, oxetanylmethyl, oxetanyl ethyl, tetrahydrofuranylmethyl, tetrahydro furanylethyl, tetrahydropyranlymethyl or tetra hydropyranylethyl, furylmethyl, thienylmethylmethylmethyl, oxadylmethylmethylmethyl, oxienylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethyl, oxyethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxyethylmethylmethylmethyl, oxymethylmethyl represents in each case optionally one to three times, identical or differently substituted benzyl or phenyl ethyl, the substituents in each case being: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n -, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, methoxy carbonyl, ethoxycarbonyl, trifluoromethyl, trifluoromethoxy or trifluoromethylthio,
X represents hydrogen, fluorine or chlorine,
Y represents oxygen or sulfur,
Z represents oxygen or sulfur,
A for oxygen, for a -CH-R⁴ group, for one or for one stands where
R⁴ for hydrogen, for methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, for allyl, propargyl, for each straight-chain or branched pentyl, hexyl, butenyl, pentenyl, hexenyl, Butynyl, pentynyl or hexynyl also stands for straight-chain or branched haloalkyl with 1 to 4 carbon atoms or haloalkenyl with 3 to 5 carbon atoms and each with 1 to 8 identical or different halogen atoms, for each rad-chain or branched cyanoalkyl, alkoxyalkyl, Alkylthioalkyl, haloalkoxyalkyl, alkoxyalkoxyalkyl, alkylcarbonylalkyl, alk oxycarbonylalkyl or alkoxyalkoxycarbonyl alkyl each having 1 to 5 carbon atoms in the individual alkyl parts, moreover for cyclopropylmethyl, cyclopentylmethyl, cyclopentylmethyl which is optionally monosubstituted to trisubstituted by methyl, methoxy, fluorine or chlorine, Cyclohexylmethyl, Cyclopro pyloxycarbonylmethyl, Cyclopentyloxycarbonyl methyl, Cyclohexyloxycarbonylmethyl , Cyclopro pyl, Cyclopentyl or Cyclohexyl, represents in each case optionally substituted by methyl and / or ethyl oxetanylmethyl, oxetanyl ethyl, tetrahydrofuranylmethyl, tetrahydro furanylethyl, tetrahydropyranylmethyl or tetrahydropyranylethyl and
R¹ and R² have the meanings given above, and
B for a direct bond or for methylene (-CH₂-), ethylidene or isopropylidene stands. 4. Process for the preparation of N-aryl nitrogen heterocycles of the general formula (I) in which
R¹ and R² either independently of one another each represent hydrogen or alkyl or together stand for a double-linked alkanediyl radical,
R³ represents hydrogen, in each case optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aralkyl or heteroarylalkyl,
X represents hydrogen or halogen,
Y represents oxygen or sulfur,
Z represents oxygen or sulfur and
A for oxygen, for a -CH-R⁴ group, for one or for one stands where
R⁴ represents hydrogen, each optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or alkoxycarbonyl, and
B for a direct bond or for methylene (-CH₂-), ethylidene or isopropylidene stands, characterized in that one

• (a) N-aryl nitrogen heterocycles of the formula (Ia), in which
  A¹ for a -CH-R⁴ group or for one stands and
  R¹, R², R³, R⁴, X, Y and B have the meaning given above,
  obtained when alkylidosuccinic anhydrides of the formula (II) in which
  A¹, R¹ and R² have the meaning given above,
  with anilines of the formula (III), in which
  X, Y, R³ and B have the meaning given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or in that
• (b) N-aryl nitrogen heterocycles of the formula (Ib) are obtained. in which
  R¹, R², X, Y, A¹ and B have the meaning given above,
  obtained when compounds of the formula (IV) in which
  R¹, R², X, Y, A¹ and B have the meaning given above and
  Q represents cyano, carboxy or C₁-C₄ alkoxycarbonyl,
  with a reducing agent, optionally in the presence of a catalyst and in the presence of a diluent, or that
• (c) N-aryl nitrogen heterocycles of the formula (Ic) are obtained in which
  R¹, R², X and A¹ have the meaning given above,
  obtained when compounds of the formula (V) in which
  R¹, R², X and A¹ have the meaning given above,
  diazotized in the presence of acids and / or diluents and, if appropriate, subsequently reacted with bases,
  or that one
• (d) the N-aryl nitrogen heterocycles of the formula (Ib) obtainable by process (a), (b) or (c) in which
  R¹, R², X, Y, A¹ and B have the meaning given above,
  with alkylating agents of the formula (VI) R³-E (VI) in which
  E stands for an electron-withdrawing leaving group and
  R³ has the meaning given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or in that
• (e) N-aryl nitrogen heterocycles of the formula (Id) in which
  R¹, R², R³, X, Y and B have the meaning given above and
  A² for one or represents oxygen, where R⁴ has the meaning given above,
  obtained when carboxylic acid esters of the formula (VII), R⁵-COOR⁶ (VII) in which
  R⁵ for a residue of the formula and
  R⁶ represents alkyl, wherein
  R¹, R² and A² have the meaning given above,
  or their acid addition salts with iso (thio) cyanates of the formula (VIII) in which
  R³, X, Y, Z and B have the meaning given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary, or if one
• (f) the N-aryl nitrogen heterocycles of the formula (Id) obtainable by process (e) in which
  R¹, R², R³, X, Y and B have the meaning given above,
  with alkylating agents of the formula (IX) R⁴-E (IX) in which
  E stands for an electron-withdrawing leaving group and
  R⁴ has the meaning given above,
  if appropriate in the presence of a diluent and if appropriate in the presence of a reaction auxiliary.

5. Herbicides and plant growth regulators, ge characterized by a content of at least one N-aryl nitrogen heterocycle of the formula (I) according to claims 1 or 4.   6. Procedures to control unwanted plants zen and to regulate plant growth, because characterized in that N-aryl nitrogen heterocycles of formula (I) according to claim 1 or 4 on the plants and / or their habitat lets work. 7. Use of N-aryl nitrogen heterocycles Formula (I) according to claim 1 or 4 for combating of unwanted plants and to regulate the Plant growth. 8. Process for the preparation of herbicides and plants zen growth regulating agents, characterized net that you can N-aryl nitrogen heterocycles Formula (I) according to claim 1 or 4 with extenders and / or surface-active substances mixed. 9. Compounds of formula (IV) in which
Q represents cyano, carboxy or C₁-C₄-alkoxy-carbonyl,
R¹ and R² either independently of one another each represent hydrogen or alkyl or together stand for a double-linked alkanediyl radical,
X represents hydrogen or halogen,
Y represents oxygen or sulfur,
Z represents oxygen or sulfur,
A¹ for a -CH-R⁴ group or a stands,
R⁴ represents hydrogen for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or alkoxycarbonyl and
B for a direct bond or for methylene (-CH₂-), ethylidene or isopropylidene stands. 10. Compounds of the formula (V) in which
R¹ and R² either independently of one another each represent hydrogen or alkyl or together stand for a double-linked alkanediyl radical,
X represents hydrogen or halogen and
A¹ for a -CH-R⁴ group or a stands and
R⁴ stands for hydrogen or for optionally substituted alkyl, alkenyl, alkynyl, cycloalkyl, aryl or alkoxycarbonyl.