CA2248068C - Substituted aryl sulphonyl(thio)ureas used as herbicides - Google Patents

Abstract

The invention relates to novel substituted arylsulphonyl(thio)ureas (see formula I) in which A ~represents nitrogen or a CH grouping, Q ~represents oxygen or sulphur, R1 ~represents hydrogen, halogen or respectively optionally substituted alky l, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or hetero- cyclyloxy, R2 ~represents hydrogen, halogen or respectively optionally substituted alky l, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or hetero- cyclyloxy, R3 ~represents hydrogen or optionally substituted alkyl, R4 ~represents respectively optionally substituted alkyl, alkoxy, alkenyl, alkinyl, alkenyloxy, alkinyloxy, cycloalkyl, cycloalkyloxy or cycloalkylalkyl, and R5 ~represents hydrogen, formyl or respectively optionally substituted alkyl , alkyl- carbonyl, alkoxycarbonyl, alkylsulphonyl, alkenyl, alkinyl, cycloalkyl, cycl o- alkylcarbonyl, cycloalkylsulphonyl or heterocyclyl, and to salts of compounds of the formula (I), except for the compound N-(4,6-dimethyl-pyrimidin-2-yl)-N'-[2-(1,1,2,2- tetrafluoro- ethoxy)-6-methyl-phenylsulphonyl]-urea, to processes for preparing the novel compounds and to their use as herbicide s.

Description

Le A 31 571 - Foreign Countries / Bi/bo/S-P

Substituted a~ylsulphonyl(thio)ureas The present invention relates to novel substituted arylsulphonyl(thio)ureas, to processes for their preparation and to their use as herbicides.
It is already known that certain substituted sulphonylureas have herbicidal properties (cf. DE 2715786, EP 1514, EP 23422). However, the herbicidal activity and the crop plant safety of these compounds is not satisfactory in all aspects.
This invention, accordingly, provides the novel substituted arylsulphonyl(thio)ureas of the general formula (I) R' Rs A~N Q
(I) R N N N /
~s R H
Ra in which A represents nitrogen or a CH grouping, Q represents oxygen or sulphur, R' represents hydrogen, halogen or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or hetero cyclyloxy, R'- represents hydrogen, halogen or respectively optionally substituted alkyl, alkoxy, alkylthio, alkylamino, dialkylamino, cycloalkyl, cycloalkyloxy or hetero-cyclyloxy, R3 represents hydrogen or optionally substituted alkyl, R9 represents respectively optionally substituted alkyl, alkoxy, alkenyl, alkinyl, alkenyloxy, alkinyloxy, cycloalkyl, cycloalkyloxy or cycloalkylalkyl, and R5 represents hydrogen, formyl or respectively optionally substituted alkyl, alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, alkenyl, alkinyl, cycloalkyl, cycloalkylcarbonyl, cycloalkylsulphonyl or heterocyclyl, and salts of compounds of the formula (I), except for the prior-art compound N-(4,6-dimethyl-pyrimidin-2-yl)-N'-[2-(1,1,2,2-tetra-fluoro-ethoxy)-6-methyl-phenylsulphonyl]-urea (cf. EP 23422) which is excluded by disclaimer.
In one aspect, the invention provides a substituted arylsulphonyl(thio)urea of the general formula (I):
R~
s A i 'N Q O~R
R2~N~N~N~S02 / ( I ) ~3 Ra \
wherein:
(a) A represents N;
Q represents 0;
R1 represents: (i) H or a halogen atom, (ii) alkyl or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or (iii) optionally halo-substituted alkoxy having 1 to 4 carbon atoms;

' 28976-299 - 2a -R2 represents: (i) alkyl, alkylthio or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or (ii) optionally halo-substituted alkoxy having 1 to 4 carbon atoms;
R3 represents H;
R4 represents: (i) optionally halo-substituted alkyl or alkoxy having in each case 1 to 6 carbon atoms, or (ii) cycloalkyloxy having 3 to 6 carbon atoms; and RS represents: (i) optionally halo-substituted alkyl having 1 to 6 carbon atoms, or (ii) cycloalkyl having 3 to 6 carbon atoms; or (b) A represents CH;
Q represents O or S;
R1 represents: (i) H or a halogen atom, (ii) optionally cyano-, halo- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, (iii) optionally cyano-, halo-, C1-C4-alkyl- or C1-C4-alkoxy-substituted cycloalkyl or cyeloalkyloxy having in each case 3 to 6 carbon atoms, or (iv) optionally cyano-, halo-, C1-C4-alkyl- or C1-C4-alkoxy-substituted oxetanyloxy, furyloxy or tetrahydrofuryloxy;
R2 represents: (i) optionally cyano-, halo- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, (ii) optionally cyano-, halo-, C1-C4-alkyl-or C1-C4-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or (iii) optionally - 2b -cyano-, halo-, Cl-C4-alkyl- or C,,-C4-alkoxy-substituted oxetanyloxy, furyloxy or tetrahydrofuryloxy;
R3 represents: (i) H, or (ii) optionally C1-C4 alkoxy, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms;
R4 represents halo-substituted Cl-C6-alkyl; and RS represents: (i) H or formyl, (ii) optionally cyano-, halo- or Cl-C4-alkoxy-substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, (iii) optionally halo-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, (iv) optionally cyano-, halo- or C1-C4-alkyl-substituted cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups, or (v) optionally cyano-, halo-, C1-C4-alkyl- or C1-C4-alkoxy substituted oxetanyl, furyl or tetrahydrofuryl; or (c) A represents CH;
Q represents O;
R1 represents H, C1, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, or n- or i-propoxy;
Rz represents H, C1, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, or n- or i-propoxy;
R3 represents H;
R4 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s-or t-butoxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, or cyclohexyloxy; and - 2c -R5 represents: (i) optionally F- or C1-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s- or t-butyl, or (ii) cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
except for the compound N-(4,6-dimethyl-pyrimidin-2-yl)-N'-(2-(1,1,2,2-tetrafluoroethoxy)-6-methyl-phenylsulphonyl]-urea;
or a salt of the compound of the general formula (I).
The novel substituted arylsulphonyl(thio)ureas of the general formula (I) are obtained when (a) aminoazines of the general formula (II) Ai 'N (II) ~ ~I
R2' 'N "NH

in which A, R1 and RZ are each as defined above, are reacted with arylsulphonyl iso(thio)cyanates of the general formula (III) Le A 31 571 - Foreign Countries Rs O
Q=C=N-S02 (III) R
in which Q, R4 and RS are each as defined above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or (b) substituted aminoazines of the general formula (IV) R' A~N Q
(IV) Rz~N~N~Z

in which A, Q, R' and R' are each as defined above, Z represents halogen, alkoxy or aryloxy and R' is as defined above or represents the grouping -C(Q)-Z
are reacted with arenesulphonamides of the general formula (V) Le A 31 571 - Foreign Countries SOz ~ (V) R
in which R~ and RS are each as defined above, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, or (c) aminoazines of the general formula (II) R' A~ N (II) RZ~N~NH
z in which A, R~ and R'- are each as defined above, are reacted with substituted arenesulphonamides of the general formula (VI) O~Rs Z~NH~S02 / (VI) R

Le A 31 571 - Foreign Countries -S-in which Q, R4 and RS are each as defined above and Z represents halogen, alkoxy or aryloxy, if appropriate in the presence of a reaction auxiliary and if appropriate in the presence of a diluent, and the compounds of the formula (I) obtained by processes (a), (b) and (c) are, if appropriate, converted into salts by customary methods.
The novel substituted arylsulphonyl(thio)ureas of the general formula (I) have strong herbicidal activity.
The invention preferably provides compounds of the formula (I) in which A represents nitrogen or a CH grouping, Q represents oxygen or sulphur, R~ represents hydrogen, halogen, represents respectively optionally cyano-, halogen- or C,-C4 alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or di-1 S alkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, represents respectively optionally cyano-, halogen-, C,-C~-alkyl- or C,-C4-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or represents respectively optionally cyano-, halogen-, C,-C4-alkyl- or C,-C4-alkoxy-substituted oxetanyloxy, furyloxy or tetrahydrofuryloxy.
R'- represents hydrogen or halogen, represents respectively optionally cyano-, halogen- or C,-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or di-alkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, Le A 31 571 - Foreign Countries represents respectively optionally cyano-, halogen-, C,-C4-alkyl- or C,-C4-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or represents respectively optionally .cyano-, halogen-, C,-C4-alkyl- or C,-C4-alkoxy-substituted oxetanyloxy, furyloxy or tetrahydrofuryloxy, R3 represents hydrogen or optionally C,-Ca-alkoxy, C,-C~-alkyl-carbonyl- or C,-C,-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms, R4 represents respectively optionally cyano-, halogen- or C,-C~-alkoxy-substituted alkyl or alkoxy having in each case 1 to 6 carbon atoms in the alkyl groups, represents respectively optionally halogen-substituted alkenyl, alkinyl, alkenyloxy or alkinyloxy having in each case 2 to 6 carbon atoms in the alkenyl or alkinyl groups, or represents respectively optionally cyano-, halogen- or C,-C4-alkyl-substituted cycloalkyl, cycloalkyloxy or cycloalkylalkyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups and optionally 1 to 4 carbon atoms in the alkyl moiety, RS represents hydrogen, formyl, represents respectively optionally cyano-, halogen-or C,-C4-alkoxy-substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case I to 6 carbon atoms in the alkyl groups, represents respectively optionally halogen-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, represents respectively optionally cyano-, halogen- or C,-C4-alkyl-substituted cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups, or represents respectively optionally cyano-, halogen-, C,-C~-alkyl-or C,-C4-alkoxy-substituted oxetanyl, furyl or tetrahydrofuryl, except for the prior-art compound N-(4,6-dimethyl-pyrimidin-2-yl)-N'-[2-(1,1,2,2 tetrafluoro-ethoxy)-6-methyl-phenylsulphonyl]-urea (cf. EP 23422) which is excluded by disclaimer.
The invention furthermore preferably provides sodium, potassium, magnesium, calcium, Le A 31 571 - Foreign Countries -7_ ammonium, C,-C4-alkyl-ammonium, di-(C,-C4-alkyl)-ammonium, tri-(C,-C4-alkyl)-ammonium, tetra-(C,-C4-alkyl)-ammonium, tri-(C,-C4-alkyl)-sulphonium, CS- or cycloalkyl-ammonium and di-(C,-CZ-alkyl)-benzyl-ammonium salts of compounds of the formula (I) in which A, Q, R', R'-, R3, R' and RS are each preferably as defined above.
The invention provides in particular compounds of the formula (I) in which A represents nitrogen or a CH grouping, Q represents oxygen or sulphur, R' represents hydrogen, fluorine, chlorine, bromine or respectively optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, R'- represents fluorine, chlorine, bromine or respectively optionally cyano-, fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino, R' represents hydrogen or optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl or ethyl, R~ represents respectively optionally cyano-, fluorine-, chlorine-, methoxy-or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl, butinyl, propenyloxy, butenyloxy, propinyloxy or butinyloxy, or represents respectively Le A 31 571 - Foreign Countries _g_ optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, RS represents hydrogen, formyl, represents respectively optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulphonyl, ethylsulphonyl, n-or i-propylsulphonyl, represents respectively optionally fluorine-, chlorine- or bromine-substituted propenyl, butenyl, propinyl or butinyl, or represents respectively optionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylsulphonyl, cyclobutylsulphonyl, cyclopentylsulphonyl or cyclohexylsulphonyl, except for the prior-art compound N-(4,6-dimethyl-pyrimidin-2-yl)-N'-[2-(1,1,2,2-tetrafluoro-ethoxy)-6-methyl-phenylsulphonyl]-urea (cf. EP 23422) which is excluded by disclaimer.
The abovementioned general or preferred radical definitions apply both to the end products of the formula (I) and, correspondingly, to the starting materials or intermediates required in each case for the preparation. These radical definitions can be combined with one another as desired, that is to say combinations between the ranges of preferred compounds indicated are also possible.

Le A 31 571 - Foreign Countries Examples of the compounds of the formula (I) according to the invention are listed in the groups below.
Gwup 1 R' A~N Q O~CH3 RZ~N~N~N~SO i (Ia_1) R H

A, Q, R~, R' and R' have, for example, the meaning listed below:
A Q R' R' R' CH O OCH; OCH; H

CH O CH; OCH; H

CH O CH; CH; H

CH O Cl OCH; H

CH O H CH; H

N O CH3 OCH; CH;

N O OCH; OCH; CH;

N O OCH; OCH; H

N O CH; CH; H

N O OCHF, N(CH;), H

N O CH; SCH; H

N O C,HS OCH; H

N O CH3 OC,HS H

Le A 31 571 - Foreign Countries A Q R' R' R3 N O CH; N(CH;), H

O
CH O O O H
O~ O-' CH O CH; O H
O
CH O Cl O H
N O O O H
O~ O
H
N O CH; O

Le A 31 571 - Foreign Countries A Q R' RZ R3 N O H
H
N S CH; OCH; H

Le A 31 571 - Foreign Countries Group 2 R' A~N Q O'CZHS
R2~N~N~N~SO / (IA_2) R H

A, Q, R', Rz and R3 have, for example, the meaning given above in group 1.
Group 3 R' A~N O O'C3H' n R2~N~N~N~SO / (IA_g) R H

A, Q, R', RZ and R3 have, for example, the meaning given above in group 1.
Grog 4 R' A~N D O'C3H' i R2~N~N~N~SO / (IA-4) R H

A, Q, R', RZ and R3 have, for example, the meaning given above in group 1.

Le A 31 571 - Foreign Countries Group 5 R' O
A N Q O
R2~N~N~N~SO / (IA-5) R H

A, Q, R', Rz and R3 have, for example, the meaning given above in group 1.
Grou 6 R' A~N Q O~CH3 R2~N~N~N~SO / (IA-6) R H

A, Q, R', Rz and R' have, for example, the meaning given above in group 1.
Group 7 R' A~N O O~CZHs R2~N~N~N~SO / (IA_7) R H

A, Q, R', Rz and R3 have, for example, the meaning given above in group 1.

Le A 31 571 - Foreign Countries Group 8 R, A~N O O~C3H~ n R2~N~N~N~SO / (IA_8) R H

A, Q, R', RZ and R3 have, for example, the meaning given above in group 1.
GrouR 9 R' A~N Q O~C3H' i R2~N~N~N~SO / (IA_g) R H

A, Q, R', Rz and R3 have, for example, the meaning given above in group 1.
Group 10 R' A~N Q
R2~N~N~N~ (IA-10) R H

A, Q, R', RZ and R' have, for example, the meaning given above in group 1.

Le A 31 571 - Foreign Countries Group 11 . R, A~N Q p R2~N~N~N~SO / (IA-11) R H

A, Q, R', Rz and R' have, for example, the meaning given above in group 1.
Grou,~ 12 R' A ~ N D O . C2Hs R2~N~N~N.SO / ( ) ' ' (CH3)2CH
A, Q, R', RZ and R3 have, for example, the meaning given above in group I.
Groin 13 R' A~N Q ~CHFZ
O
R2~N~N~N~SO / (IA-13) R H

A, Q, R', RZ and R~ have, for example, the meaning given above in group I.

' Le A 31 571 - Foreign Countries Group 14 R' A~N Q O~CF3 ~I ~
R2~N~N~N~S~ ~ (IA-14) R H

A, Q, R', Rz and R3 have, for example, the meaning given above in group 1.
Using, for example, 2-amino-4-methoxy-6-methyl-pyrimidine and 2-ethoxy-6-trifluoromethyl-phenylsulphonyl isocyanate as starting materials, the course of the reaction in the process (a) according to the invention can be illustrated by the following equation:

OCH3 OC2Hs O=C=N-SOz / ~ N O OC H
/ ~ N + / --~ I z s ~ ~ ~S02 w I ~ I H3C N"N"N /

Using, for example, 2-methoxycarbonylamino-4-methoxy-6-trifluoromethyl-1,3,5-triazine and 2-methyl-6-trifluoromethoxy-benzenesulphonamide as starting materials, the course of the reaction in the process (b) according to the invention can be illustrated by the following equation:

N ~ N O + SO N ~ N p OCF3 i z /
H2N ~ ~ I ~ S02 F3~N~N~OCH3 w I - HOCH3 F3~N~N~N

Using, for example, 2-amino-4-chloro-6-methoxy-pyrimidine and N-(2,6-dimethoxy-phenylsulphonyl)-O-phenyl-urethane as starting materials, the course of the reaction in ' Le A 31 571 - Fore~n Countries _ 17_ the process (c) according to the invention can be illustrated by the following equation:

N ~ SO ~ N O OCH3 N / 2 / ~ ~ ~ ~ SO
CI N NHZ H CI N N N ~ 2 H3C0 ~ - HOCsHS
i i The formula (II) provides a general definition of the aminoazines to be used as starting materials in the processes (a) and (c) for preparing compounds of the general formula (I). In the formula (II), A, R' and RZ each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for A, R' and R2.
The aminoazines of the formula (II) are known chemicals for synthesis, some of which are commercially available.
The formula (III) provides a general definition of the arylsulphonyl iso(thio)cyanates further to be used as starting materials in the process (a) according to the invention. In the formula (III), Q, R4 and RS each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for Q, R4 and R5.
The starting materials of the formula (III) are known and/or can be prepared by processes known per se (cf. DE 3208189, EP 23422, EP 64322, EP 44807, EP
216504, Preparation Examples).
The arylsulphonyl iso(thio)cyanates of the formula (III) are obtained when arenesulphonamides of the general formula (V) - above - are reacted with phosgene or thiophosgene, if appropriate in the presence of an alkyl isocyanate, such as, for example, butyl isocyanate, if appropriate in the presence of a reaction auxiliary, such Le A 31 571 - Foreign Countries as, for example, diazabicyclo[2.2.2]-octane, and in the presence of a diluent, such as, for example, toluene, xylene or chlorobenzene, at temperatures between 80°C and 150°C, and the volatile components are distilled off under reduced pressure after the reaction has ended.
The formula (IV) provides a general definition of the substituted aminoazines to be used as starting materials in the process (b) according to the invention for preparing compounds of the formula (I). In the formula (IV), A, Q, R' and R' each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for A, Q, R' and Rz; Z preferably represents fluorine, chlorine, bromine, C'-C4-alkoxy or phenoxy, in particular chlorine, methoxy, ethoxy or phenoxy.
The starting materials of the formula (IV) are known and/or can be prepared by processes known per se (cf. US 4690707, DE 19501174, Preparation Examples).
The formula (V) provides a general definition of the arenesulphonamides further to be used as starting materials in the process (b) according to the invention. In the formula (V), R' and RS each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for R4, and R5.
The starting materials of the formula (V) are known and/or can be prepared by a process known per se (cf. DE 3208189, EP 23422, EP 64322, EP 44807, EP 216504, DE 19525162, Preparation Examples).
The formula (VI) provides a general definition of the substituted arenesulphonamides to be used as starting materials in the process (c) according to the invention for preparing the compounds of the formula (I). In the formula (VI), Q, R4 and RS
each preferably or in particular have those meanings which have already been indicated above, in connection with the description of the compounds of the formula (I), as being preferred or particularly preferred for Q, R4 and RS; Z preferably represents fluorine, Le A 31 571 - Foreign Countries chlorine, bromine, C,-C4-alkoxy or phenoxy, in particular chlorine, methoxy, ethoxy or phenoxy.
The starting materials of the formula (VI) are known and/or can be prepared by processes known per se (cf. the Preparation Examples).
Suitable diluents for carrying out the processes (a), (b) and (c) according to the invention are inert organic solvents. These include in particular aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ethers, such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether;
ketones, such as acetone, butanone or methyl isobutyl ketone; nitrites, such as acetonitrile, propionitrile or benzonitrile; amides, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methyl-formaW lode, N-methyl-pyrrondone or hexamethylphosphoric triamide; esters, such as methyl acetate or ethyl acetate;
sulphoxides, such as dimethyl sulphoxide; alcohols, such as methanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, diethylene glycol monomethyl ether, diethylene glycol monoethyl ether, mixtures thereof with water or pure water.
The processes (a), (b) and (c) according to the invention are preferably carried out in the presence of a suitable reaction auxiliary. Suitable reaction auxiliaries are all customary inorganic or organic bases. These include, for example, alkaline earth metal or alkali metal hydrides, hydroxides, amides, alkoxides, acetates, carbonates or bicarbonates, such as, for example, sodium hydride, sodium amide, sodium methoxide, sodium ethoxide, potassium tert-butoxide, sodium hydroxide, potassium hydroxide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, sodium carbonate, potassium carbonate, potassium bicarbonate, sodium bicarbonate or ammonium carbonate and also tertiary amines, such as trimethylamine, triethylamine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or ' Le A 31 571 - Fore~n Countries diazabicycloundecene (DBU).
When carrying out the processes (a), (b) and (c) according to the invention, the reaction temperatures can be varied within a relatively wide range. In general, the reaction is carried out at temperatures between -20°C and +150°C, preferably between 0°C and +120°C.
The processes (a), (b) and (c) according to the invention are generally carried out under atmospheric pressure. However, it is also possible to carry out the process according to the invention under elevated or reduced pressure - generally between 0.1 bar and 10 bar.
In the practice of the processes (a), (b) and (c) according to the invention, the starting materials are generally employed in approximately equimolar amounts. However, it is also possible to employ one of the components in a relatively large excess.
The reaction is generally carried out in a suitable diluent in the presence of a reaction auxiliary, and the reaction mixture is generally stirred for a number of hours at the temperature required. Work-up is carried out by customary methods (cf. the Preparation Examples).
If required, salts can be prepared from the compounds of the general formula (I) according to the invention. Such salts are obtained in a simple manner by customary methods of forming salts, for example by dissolving or dispersing a compound of the formula (I) in a suitable solvent, such as, for example, methylene chloride, acetone, tert-butyl methyl ether or toluene, and addition of a suitable base. The salts can then be isolated - if required after prolonged stirring - by concentration or filtration with suction.
The active compounds according to the invention can be used as defoliants, desiccants, haulm killers and, especially, as weed killers. By weeds in the broadest sense, there are to be understood all plants which grow in locations where they are undesirable.
Whether the substances according to the invention act as total or selective herbicides Le A 31 571 - Foreign Countries depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Dicotyledonous weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, S Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea, Trifolium, Ranunculus and Taraxacum.
Dicotyledonous cry plants of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledonous weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, 1 S Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
Monocotyledonous crop plants of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compounds according to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The compounds are suitable, depending on the concentration, for the total control of weeds, for example on industrial terrain and railway tracks, and on paths and squares with or without tree plantings. Likewise, the compounds can be employed for controlling weeds in perennial cultures, for example forests, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantations, coffee plantations, Le A 31 571 - Foreig_n Countries tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hop fields, on lawns, sports fields and pasture-land, and for the selective control of weeds in annual cultures.
The compounds of the formula (I) according to the invention are suitable in particular for controlling monocotyledonous and dicotyledenous weeds, both pre-emergence and post-emergence. They have strong herbicidal activity and a broad spectrum of activity when applied to the soil and to the above-ground parts of plants.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspo-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surfactants, that is emulsifiers and/or dispersing agents and/or foam-forming agents.
If the extender used is water, it is also possible to employ for example organic solvents as auxiliary solvents. Essentially, suitable liquid solvents are: aromatics, such as xylene, toluene or alkylnaphthalenes, chlorinated aromatics and chlorinated aliphatic hydrocarbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol and their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strongly polar solvents, such as dimethylformamide and dimethyl sulphoxide, and water.
Suitable solid carriers are:
for example ammonium salts and ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth, and ground synthetic Le A 31 571 - Foreign Countries minerals, such as finely divided silica, alumina and silicates, suitable solid carriers for granules are: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material such as sawdust, coconut shells, maize cobs and tobacco stalks; suitable emulsifiers and/or foam-forming agents are:
for example nonionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as protein hydrolysates;
suitable dispersing agents are: for example lignin-sulphite waste liquors and methylcellulose.
Tackifiers such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Prussian Blue, and organic dyes, such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, such as or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
Possible components for the mixtures are known herbicides, for example anilides such as, for example, diflufenican and propanil; arylcarboxylic acids such as, for example, dichloropicolinic acid, dicamba and picloram; aryloxyalkanoic acids such as, for Le A 31 571 - Foreign Countries example, 2,4 D, 2,4 DB, 2,4 DP, fluroxypyr, MCPA, MCPP and triclopyr; aryloxy-phenoxy-alkanoic esters such as, for example, diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinones such as, for example, chloridazon and norflurazon; carbamates such as, for example, chlorpropham, S desmedipham, phenmedipham and propham; chloroacetanilides such as, for example, alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor;
dinitroanilines such as, for example, oryzalin, pendimethalin and trifluralin;
diphenyl ethers such as, for example, acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas such as, for example, chlortoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines such as, for example, alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinones such as, for example, imazethapyr, imazamethabenz, imazapyr and imazaquin; nitrites such as, for example, bromoxynil, dichlobenil and ioxynil; oxyacetamides such as, for example, mefenacet; sulphonylureas such as, for example, amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamates such as, for example, butylate, cycloate, di-allate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and tri-allate;
triazines such as, for example, atrazine, cyanazine, simazine, simetryn, terbutryn and terbutylazine; triazinones such as, for example, hexazinone, metamitron and metribuzin;
others such as, for example, aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumesate, fluorochloridone, glufo-sinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridiphane.
Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, bird repellents, plant nutrients and agents which improve soil structure, are also possible.
The active compounds can be used as such, in the form of their formulations or in the use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary Le A 31 571 - Foreign Countries manner, for example by watering, spraying, atomizing or scattering.
The active compounds according to the invention can be applied either before or after emergence of the plants. They can also be incorporated into the soil before sowing.
The amount of active compound used can vary within a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between 1 g and 10 kg of active compound per hectare of soil surface, preferably between Sg and 5 kg per ha.
The preparation and use of the active compounds according to the invention can be seen from the examples below.

- Le A 31 571 - Foreign Countries Preparation Examples:
Example 1 N O O~CH3 ~ S02 H H

(Process (b)) At about 20°C, a mixture of 1.43 g (5.6 mmol) of 2-methoxy-6-trifluoromethyl-benzenesulphonamide, 1.24 g (5.1 mmol) of 2-phenoxycarbonylamino-4,6-dimethyl-pyrimidine, 0.85 g (5.6 mmol) of diazabicycloundecene (DBU) and SO ml of acetonitrile is stirred for 15 hours. The mixture is then concentrated using water pump vacuum and the residue is stirred with 50 ml of 1 N hydrochloric acid and 50 ml of methylene chloride. The organic phase is separated off, washed with water, dried with sodium sulphate and filtered. The filtrate is concentrated using water pump vacuum, the residue is digested with i-propanol and the crystalline product is isolated by filtration with suction.
This gives 1.6 g (62% of theory) of N-(4,6-dimethyl-pyrimidin-2-yl)-N'-(2-methoxy-6-trifluoromethyl-phenylsulphonyl)-urea of melting point 190°C.
Example 2 O~CH3 N-' N O O~CH3 O~N~N~N~S02 I I I
CH3 H H H C \

Le A 31 571 - Foreign Countries (Process (b)) At about 20°C, a mixture of 2.0 g (10 mmol) of 2-methoxy-6-methyl-benzenesulphonamide, 4.0 g ( 10 mmol) of N,N-bis-phenoxycarbonyl-2-amino-4,6-dimethoxy-1,3,5-triazine, 1.1 g (10 mmol) of potassium t-butoxide and 50 ml of acetonitrile is stirred for 15 hours. The mixture is then concentrated using water pump vacuum and the residue is stirred with SO ml of 1N hydrochloric acid and 50 ml of methylene chloride. The organic phase is separated off, washed with water, dried with sodium sulphate and filtered. The filtrate is concentrated using water pump vacuum, the residue is digested with i-propanol and the resulting crystalline product is isolated by filtration with suction.
This gives 2.1 g (55% of theory) of N-(4,6-dimethoxy-1,3,5-triazin-2-yl)-N'-(2-methoxy-6-methyl-phenylsulphonyl)-urea of melting point 163°C.
Example 3 O~CH3 N O O~C2H5 O N N N

(Process (c) with precursor) At about 20°C, 1.6 g (10 mmol) of phenyl chloroformate are added dropwise to a mixture of 2.2 g ( 10 mmol) of 2-ethoxy-6-methyl-benzenesulphonamide, 2.0 g (20 mmol) of triethylamine and 30 ml of acetonitrile, and the mixture is stirred at the temperature stated for about 30 minutes. 1.0 g ( 10 mmol) of methanesulphonic acid and 1.6 g (10 mmol) of 2-amino-4,6-dimethoxy-pyrimidine are then added, and the reaction mixture is stirred at about 60°C for about 15 minutes. The mixture is cooled to about 20°C and filtered with suction, the filtrate is concentrated using water pump vacuum and the residue is stirred with 30 ml of 1N hydrochloric acid. Filtration with suction and drying gives a crude product which is purified by rinsing with diethyl ether.

Le A 31 571 - Foreign Countries Yield: 2.2 g (55%) of theory) of N-(4,6-dimethoxy-pyrimidin-2-yl)-N'-(2-ethoxy-methyl-phenylsulphonyl)-urea of melting point 184°C.
Similar to Preparation Examples 1 to 3, and in accordance with the general description of the preparation processes according to the invention, it is also possible to prepare, S for example, the compounds of the formula (I) listed in Table 1 below.

' Le A 31 571 - Foreign Countries R' s A~N Q O~R
p ~ ~ i SO (I) R N N N
~s R H
R
Table 1: Examples of compounds of the formula (I) Ex. A Q R' Rz R' R4 RS Melting No. point (°C) 4 N O CH3 OCH3 H CF3 CzHs I15 8 CH O CH3 CH3 H CF3 CzHS 214 9 N O CH3 OCH3 H CFA C3H~-n 142 N O OCH3 OCH3 H CF; C3H~-n 162 11 CH O CH3 CH3 H CF3 C3H~-n 212 12 N O CH3 OCH3 H CF3 C3H~-i 168 13 N O OCH3 OCH3 H CF3 C3H~-i 200 14 CH O CH3 CH3 H CF3 C3H,-i 221 16 CH O Cl OCH3 H CF3 C,HS 176 17 CH O Cl OCH3 H CF3 C3H,-n 169 18 N O N(CH3)2 OCHZCF3 H CF3 CHI 222 19 N O N(CH3)2 OCHZCF3 H CF3 CZHS 209 N O N(CH3)z OCHZCF3 H CFj C3H~-n 175 21 N O N(CH3)2 OCHZCF3 H CF3 C3H~-i 204 (decomp.) Le A 31 571 - Foreign Countries Table 1 (continued):
Ex. A Q R' RZ R3 R'~ RS Melting No. _ point (C) (decomp.) 24 CH O OCH3 OCH3 H CF3 C3H,-n 180 25 CH O OCH3 OCH3 H CF3 C3H,-i 98 (decomp.) 26 CH O CH3 CH3 H CH3 CzHS 217 29 CH O CH3 CH3 H CH3 C3H,-n 194 30 CH O H CH3 H CH3 C3H,-n 176 31 N O OCH3 OCH3 H CH3 CzHs 181 33 CH O CH3 OCHj H CH3 C3H,-i 196 34" CH O OCH3 OCH3 H CH3 ~ ~ 204 35 CH O CH3 CH3 H CH3 C3H,-i 231 36 CH O OCH3 OCH3 H CH3 C3H,-i 190 37 CH O H CH3 H CH3 C3H,-i 206 38 N O OCH3 OCH3 H CH3 C3H,-i 191 39 N O OCH3 OCH3 H CH3 C3H,-i 205 45 N O N(CH3)2 OCHzCF3 H CH3 CzHs 187 ' Le A 31 571 - Foreign Countries Table 1 (continued):
Ex. A Q R~ Rz R3 R° RS Melting No. point (°C) 46 CH O CH3 OCH3 H CH3 C~H7-n 147 47 CH O OCH3 OCH3 H CHI C3H~-n 164 48 N O OCH3 OCH3 H CH3 C3H~-n 156 49 N O CH3 OCH3 H CHI C3H~-n 150 50 CH O OCH3 OCH3 H C3H~-i CZHS 184 51 N O OCH3 OCH3 H C3H~-i CzHS 157 52 N O N(CH3)Z OCHZCF3 H CH3 CHj 214 53 N O N(CH3)2 OCHZCF3 H CH3 C3H~-i 202 57 N O OCH3 OCH3 H CH3 C4H9 s 174 58 CH O CH3 OCH3 H CH3 C4H9 s 186 59 N O CHj OCH3 H CH3 C4H9-s 177 60 CH O CH3 CHj H CH3 C4H9 s 228 61 CH O OCH3 OCH3 H CH3 C4H9-s 207 62 CH O CH3 CF3 H CH3 C~H~-i 192 64 N O CH3 OCH3 H CjH~-i CH3 136 65 CH O OCH3 OCH3 H CH3 CHF~ 170 66 N O CH3 OCH3 H CH3 CHFz 197 67 N O OCH3 OCH3 H OC3H.,-n C3H,-n 140 ' Le A 31 571 - Foreign_ Countries Table 1 (continued):
Ex. A Q R' RZ R3 R4 RS Melting No. . point (C) 68 CH O C1 OCH3 H OCH3 C~H,-i 148 69 N O CH3 OCH3 H OCH3 C~H,-i 152 n n 71 N O CH3 OCH3 H OC~H,-i C~H,-i 80 72 N O CH3 OCH3 H OCZHS C3H,-i 118 73 N O CHj OCH3 Na OCH3 CH3 203 74 CH O OCH3 OCHj H C3H,-i CH3 164 75 CH O OCH~ OCH3 H C3H,-i C3H,-n 157 76 CH O CH3 CF3 H CH3 C~HS 179 79 N O CH3 N(CH3)2 H CFA CH3 213 80 N O CH3 OCzHS H CF3 CH3 121 82 N O OCH=CF=CHF,N(CH3)z H CF3 CHI 185 83 N O CH3 OCH3 Na C~H,-i CH3 170 84 N O OCH3 OCH3 H C3H,-i C3H,-n 149 85 N O OCH3 OCH~ H C3H,-i CH3 187 86 N O CH3 OCH3 H C3H,-i CZHS 163 87 CH O CH3 OCH3 H C3H,-i CH3 175 88 CH O CH3 OCH3 H C3H,-i C3H,-i 152 89 CH O OCH3 OCH3 H C3H,-i C3H,-i 138 90 N O CH3 OCH3 Na CH3 CH; 149 ~ 125 -Le A 31 571 - Fore~n Countries Table 1 (continued):
Ex. A Q R' R'- R3 R4 RS Melting No. ~ point (°C) 92 N O CH3 OCH3 Na OC~H,-i C;H,-i 178 93 N O Cl OCH~ Na OCH3 C3H,-i 172 94 N O CH3 OCH3 Na OOHS CZHS 145 952' N O CH3 OCH3 Na OCH3 C;H,-n NMR data 98 N O OCH3 OCH3 H OCH3 C~H,-n 188 99 N O OCH3 OCH3 H OCZHS C4H9 s 136 100 CH O CI OCH3 H OCH3 C,HS 146 101 CH O C1 OCH3 H OCH3 C3H,-n 110 102 CH O C1 OCH3 H OCH3 C4H9 n 117 103 CH O Cl OCH3 H OC4H9-n C4H9 n 135 104 CH O C1 OCH3 H OCzHS C4H9 n 128 105 N O CHI OCH3 H OCZHS C3H,-n 110 108 N O CH3 OCH~ H OCzHS C4H9 i 85 109 N O CH3 OCH3 H OCH3 CzHS 148 110 N O CH3 OCH3 H OCH3 C4H9 n 125 112 CH O OCH3 OCH~ H CH3 CFA 178 Le A 31 571 - Foreign Countries Table 1 (continued):
Ex. A ~Q R' RZ R3 R4 RS Melting No. point (C) 115 N O CH3 OCH3 H CzHS CF3 140 116 CH O OCHj OCH3 H CH3 CFZCHFZ 169 121 N O CH3 OCH3 H C,HS CHFz 157 122 CH O OCH3 OCH3 H CjH~-n CF3 147 123 N O CH3 OCH3 H C3H~-n CFA 77 Notes:
" In Example 34, ( ~ is propargyl = CHz-C---CH
z' NMR data for Example 95:
'H-NMR (300MHz; DZO): b = 0.96 (t, CH3); 1.77 (m, O-CHz-CHZ-CH3); 2.42 (s, CH3); 3.87 (s, OCH3); 3.98 (s, OCH~); 4.04 (t, O-CHz-); 6.79 (brd.d, 2 aromat. H); 7.48 (brd.t, 1 aromat. H) ppm.

Le A 31 571 - Foreign Countries Stactin~ material of the formula (~:
Example (III-1) C2Hs O
S02-N=C=O

21.5 g (0.1 mol) of 2-ethoxy-6-methyl-benzenesulphonamide and 10 g (0.1 mol) of n-butyl isocyanate are heated to the boil in 100 ml of chlorobenzene. At reflux temperature, phosgene is introduced for 4 hours. The clear solution is concentrated under reduced pressure and the residue is subjected to precision distillation.
At a pressure of 0.8 mbar and an overhead temperature of 135-140°C, 2-ethoxy-6-methyl-phenylsulphonyl isocyanate passes over and solidifies in the receiving flask.
This gives 7.9 g of 2-ethoxy-6-methyl-phenylsulphonyl isocyanate as a colourless product of melting point 40°C.
Starting materials of the fomlula (IV):
Example (IV-1) ,OCHs O N/~j\N
HSC6 O~N~N~OCH

O O

70 g (0.44 mol) of phenyl chloroformate are added dropwise with stirring to a mixture of 31 g (0.20 mol) of 2-amino-4,6-dimethoxy-s-triazine and 100 ml of pyridine.
The Le A 31 571 - Foreign Countries reaction mixture is stirred at 20°C to 25°C for about 15 hours and subsequently concentrated using water pump vacuum. The residue is taken up in water and then acidified using conc. hydrochloric acid. The resulting crystalline product is isolated by filtration with suction.
This gives 74.2 g (91 % of theory) of 2-(N,N-bis-phenoxycarbonyl-amino)-4,6-dimethoxy-s-triazine of melting point 125°C.
Starting materials of the formula (V1:
Example (V-1) CH(CH3)2 O
w At 20°C, 64.6 g (0.26 mol) of 2-isopropoxy-6-methyl-benzenesulphonyl chloride are stirred in 350 ml of 25% strength aqueous ammonia solution for 12 hours. The resulting crystalline product is subsequently isolated by filtration with suction.
This gives 54 g (90% of theory) of 2-isopropoxy-6-methyl-benzenesulphonamide of melting point 78°C.

Le A 31 571 - Foreig_n Countries Use Examples:
Example A
Pre-emergence test Solvent: S parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil. After about 24 hours, the soil is sprayed with the preparation of the active compound. Advantageously, the amount of water per unit area is kept constant. The active compound concentration in the preparation is not important, only the active compound application rate per unit area is critical.
After three weeks, the degree of damage to the plants is rated in % damage in comparison with the development of the untreated control.
The figures denote:
0% = no effect (like untreated control) 100% = total destruction In this test, for example, the compounds of Preparation Example 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13, 14, 1 S, 16, 22, 27, 31, 32, 33, 34, 38, 39, 40, 41, 43, 44, 46, 48, 49, 56, 65 and 66 exhibit, at application rates between 30 g and 125 g of a.i. per hectare, very strong activity against weeds.
"a.i." - "active ingredient"

Le A 31 571 - Foreign Countries Table A: Pre-emergence tesdgreenhouse Active compound Application Alope- Lo- Sor- Amaran- Cheno- Stel-of Preparation rate (g of cures lium ghum thus podium taria Example No. ai./ha) ' Le A 31 571 - Foreign Countries Example B
Post-emergence test Solvent: S parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants which have a height of 5 - 15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the amounts of active compound desired in each case are applied in 1000 1 of water/ha.
After three weeks, the degree of damage to the plants is rated in % damage in comparison with the development of the untreated control.
The figures denote:
0% = no effect (like untreated control) 100% = total destruction In this test, for example, the compounds of Preparation Example 2, 3, 4, 5, 6, 7, 8, 9, 12, 15, 16, 17, 22, 23, 24, 25, 27, 31, 32, 34, 38, 39, 40, 41, 43, 44, 48, 49, 51, 65 and 66 exhibit very strong activity against weeds.

Le A 31 571 - Foreign Countries Table B: Post-emergence testlgreenhouse Active compound Application Alope- Echino- Abu- Matri-of Preparation rate Gurus chloa tilon caria Example No. (g of ai./ha) Sl 60 80 90 100 90

Claims (8)

CLAIMS:

1. ~A substituted arylsulphonyl(thio)urea of the general formula (I):
~
wherein:~
(a) A represents N;
Q represents O;
R1 represents: (i) H or a halogen atom, (ii) alkyl or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or (iii) optionally halo-substituted alkoxy having 1 to 4 carbon atoms;
R2 represents: (i) alkyl, alkylthio or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, or (ii) optionally halo-substituted alkoxy having 1 to 4 carbon atoms;
R3 represents H;
R4 represents: (i) optionally halo-substituted alkyl or alkoxy having in each case 1 to 6 carbon atoms, or (ii) cycloalkyloxy having 3 to 6 carbon atoms; and R5 represents: (i) optionally halo-substituted alkyl having 1 to 6 carbon atoms, or (ii) cycloalkyl having 3 to 6 carbon atoms; or (b) A represents CH;
Q represents O or S;
R1 represents: (i) H or a halogen atom, (ii) optionally cyano-, halo- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, (iii) optionally cyano-, halo-, C1-C4-alkyl- or C1-C4-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or (iv) optionally cyano-, halo-, C1-C4-alkyl- or C1-C4-alkoxy-substituted oxetanyloxy, furyloxy or tetrahydrofuryloxy;
R2 represents: (i) optionally cyano-, halo- or C1-C4-alkoxy-substituted alkyl, alkoxy, alkylthio, alkylamino or dialkylamino having in each case 1 to 4 carbon atoms in the alkyl groups, (ii) optionally cyano-, halo-, C1-C4-alkyl-or C1-C4-alkoxy-substituted cycloalkyl or cycloalkyloxy having in each case 3 to 6 carbon atoms, or (iii) optionally cyano-, halo-, C1-C4-alkyl- or C1-C4-alkoxy-substituted oxetanyloxy, furyloxy or tetrahydrofuryloxy;
R3 represents: (i) H, or (ii) optionally C1-C4 alkoxy, C1-C4-alkyl-carbonyl- or C1-C4-alkoxy-carbonyl-substituted alkyl having 1 to 4 carbon atoms;
R4 represents halo-substituted C1-C6-alkyl; and R5 represents: (i) H or formyl, (ii) optionally cyano-, halo- or C1-C4-alkoxy-substituted alkyl, alkylcarbonyl, alkoxycarbonyl or alkylsulphonyl having in each case 1 to 6 carbon atoms in the alkyl groups, (iii) optionally halo-substituted alkenyl or alkinyl having in each case 2 to 6 carbon atoms, (iv) optionally cyano-, halo- or C1-C4-alkyl-substituted cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl having in each case 3 to 6 carbon atoms in the cycloalkyl groups, or (v) optionally cyano-, halo-, C1-C4-alkyl- or C1-C4-alkoxy-substituted oxetanyl, furyl or tetrahydrofuryl; or (c) A represents CH;
Q represents O;
R1 represents H, Cl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, or n- or i-propoxy;
R2 represents H, Cl, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, or n- or i-propoxy;
R3 represents H;
R4 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s-or t-butoxy, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, or cyclohexyloxy; and R5 represents: (i) optionally F- or Cl-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s- or t-butyl, or (ii) cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
except for the compound N-(4,6-dimethyl-pyrimidin-2-yl)-N'-[2-(1,1,2,2-tetrafluoroethoxy)-6-methyl-phenylsulphonyl]-urea;
or a salt of the compound of the general formula (I).

2. A compound of the general formula (I) according to claim 1, wherein the salt is selected from the group consisting of the sodium, potassium, magnesium, calcium, ammonium, C1-C4-alkyl-ammonium, di- (C1-C4-alkyl) -ammonium, tri- (C1-C4-alkyl) -ammonium, tetra- (C1-C4-alkyl) -ammonium, tri-(C1-C4-alkyl)-sulphonium, C5- or C6-cycloalkyl-ammonium and di- (C1-C2-alkyl) -benzyl-ammonium salts.

3. ~A compound of the general formula (I) according to claim 1 or 2, wherein:
(a) R1 represents: (i) H, F, Cl, Br, methyl, ethyl, n- or i-propyl, dimethylamino or diethylamino, or (ii) optionally F- or C1-substituted methoxy, ethoxy, or n- or i-propoxy;
R2 represents: (i) methyl, ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, dimethylamino or diethylamino, or (ii) as defined for R1;
R4 represents: (i) optionally F- or Cl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, or n-, i-, s- or t-butoxy, or (ii) as defined in claim 1; and R5 represents: (i) optionally F- or Cl-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s- or t-butyl, or (ii) as defined in claim 1; or (b) R1 represents: (i) H, F, Cl or Br, or (ii) optionally cyano-, F-, Cl-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino;
R2 represents optionally cyano-, F-, Cl-, methoxy-or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n-or i-propylthio, methylamino, ethylamino, n- or i-propylamino, dimethylamino or diethylamino;
R3 represents: (i) H, or (ii) optionally methoxy-, ethoxy-, n- or i-propoxy-, acetyl-, propionyl-, n- or i-butyroyl-, methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted methyl or ethyl;
R4 represents F- or Cl-substituted methyl, ethyl, n- or i-propyl, or n-, i-, s- or t-butyl;
R5 represents: (i) H or formyl, (ii) optionally cyano-, F-, Cl-, methoxy-, ethoxy-, or n- or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulphonyl, ethylsulphonyl, or n- or i-propylsulphonyl, (iii) optionally F-, Cl- or Br-substituted propenyl, butenyl, propinyl or butinyl, or (iv) optionally cyano-, F-, Cl-, Br-, methyl-, ethyl-, or n- or i-propyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylcarbonyl, cyclobutylcarbonyl, cyclopentylcarbonyl, cyclohexylcarbonyl, cyclopropylsulphonyl, cyclobutylsulphonyl, cyclopentylsulphonyl or cyclohexylsulphonyl.

4. A process for preparing a compound of the general formula (I) according to any one of claims 1 to 3, comprising:
(a) reacting, optionally in the presence of a reactive auxiliary and a diluent, an aminoazine of the general formula (II):
wherein A, R1 and R2 are as defined in claim 1 or 3, (a), (b) or (c), with an arylsulphonyl iso(thio)cyanate of the general formula (III):

wherein Q, R4 and R5 are as defined in claim 1 or 3, (a), (b) or (c); or (b) reacting, optionally in the presence of a reactive auxiliary and a diluent, a substituted aminoazine of the general formula (IV):

wherein:

A, Q, R1 and R2 are as defined in claim 1 or 3, (a), (b) or (c), Z represents a halogen atom, alkoxy or aryloxy, and R3 is as defined in claim 1 or 3, (a), (b) or (c), or represents the grouping -C(Q)-Z, wherein Q and Z are as defined above, with an arenesulphonamide of the general formula (V):

wherein R4 and R5 are as defined in claim 1 or 3, (a), (b) or (c); or (c) reacting, optionally in the presence of a reactive auxiliary and a diluent, an aminoazine of the general formula (II) as defined in step (a), with a substituted arenesulphonamide of the general formula (VI):

wherein Q, R4 and R5 are as defined in claim 1 or 3, (a), (b) or (c), and Z is as defined in step (b); and optionally converting a compound of the general formula (I) obtained by processes (a), (b) and (c) into a salt thereof.

5. A herbicidal composition, comprising at least one compound of the general formula (I) or a salt thereof according to any one of claims 1 to 3, and an extender, a surfactant or a mixture thereof.

6. Use of a compound of the general formula (I) or a salt thereof according to any one of claims 1 to 3, or a composition according to claim 5, for controlling undesirable plant growth.

7. A method for controlling weeds, wherein a compound of the general formula (I) or a salt thereof according to any one of claims 1 to 3, or a composition according to claim 5, is allowed to act on the weeds or their habitat.

8. A process for preparing a herbicidal composition, wherein a compound of the general formula (I) or a salt thereof according to any one of claims 1 to 3, is mixed with an extender, a surfactant or a mixture thereof.