CA1228357A - N'-(s-triazinyl)-n"-(di)substituted-n"'- benzenesulphonylguanidines - Google Patents

Abstract

Abstract The invention relates to new sulphonylguanidino-triazine derivatives of the general formula (I)

Description

1228~57 The invention relates to new sulphonylguanidinotriazine derivatives, processes for their preparation and their use as herbicides.
A divisional application, divided out of this application relates to new sulphonyl-iso-thioureido-triazine derivatives of the formula VIVA (hereinafter defined) and to their preparation.
The compounds of formula VIVA are intermediates useful in preparing the herbicidally active compounds of the present invention.
Various guanidine derivatives have been disclosed as potential herbicides from patent specifications (compare DE-AS
(German Published Specification) 1,089,210 and East German Patent Specifications 71,016 and 84,530), but they have not hitherto achieved relatively great importance as agents for combating weeds and/or regulating plant growth. Other guanidine derivatives are known (compare DEMOS (German Published Specification) 3,344,455).
According to one aspect of the present invention there is provided new sulphonylguanidinotriazine derivatives of the general formula (I) R4 Rl-SO2-N \ / N I/ N

I R5 (I) / N \
R2 \ R3 in which M represents hydrogen or one equivalent of a metal, Al represents an optionally substituted phenol radical I' ~2283S7 wherein R6 and R7 are identical or different and represent hydrogen, halogen (such as, in particular, fluorine, chlorine, and/or bromide), cyan, vitro or Cl-C4-alkyl (which is optionally substituted by fluorine, chlorine, bromide, cyan, Cl-C4-alkoxy-carbonyl, C1-C4-alkylamino-carbonyl, di-(Cl-C4-alkyl)-amino-carbonyl, Cl-C4-al.koxy, - lo -;

` 1228357

- 2 -C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkyl-sulphonyl), or represent C1-C4-alkoxy (which is optionally substituted by fluorine, chlorine, bromide, cyan, C1-C4-alkoxy-carbonyl, C1-C4-alkXY~ C1-C4-alkylthio, C1-C4-alkyl-sulphinyl or C1-c4-alkylsulphonyl)~ or represent C1-C4-aLkylthjo~ C1-c4-alkYlsulphinyl~ or represent C1-c4-alkylsulphonyl (whir are optionally substituted by fluorine, chlorine, bromide, cyan or C1-c4-alkoxy-carbonyl)~ or represent C1-C4-alkylamino-sulphonyl, di-(C1-C4-alkYl)-amino-sulphonyl, C1-C4-alkoxyamino-sulphonyl, benzyloxy~
aminosulphonyl or C1-C4-alkoxy-C1-C4~alkYl-aminosulphonyl, or represent phenol or phonics, or represent C1-C4-alkoxysulphonyl, or represent C~-c6-alkenyl (which is optionally substituted by fluorine, chlorine, bromide, cyan, C1-C4-alkoxy-carbonyl, carboxyl or phenol), or represent C2-C6-alkinyl (which is optionally substituted by fluorine, chlorine, bromide, c / C1-C4 alkoxY car y or represent Schick (which is optionally substituted by fluorine, chlorine, bromide, cyan or C1-C4-alkoxycarbonyl), or represent C3-C6-alkenylthio (which is optionally substituted by I fluorine, chlorine, bromide, cyan or C1-C4-alkoxy-carbonyl), or represent C1-c6-alkoxy-carbonyL
(which is optionally substituted by fluorine, chlorine, bromide, cyan or C1-C4-alkoxy)~ or represent C3-C6-cycloalkoxy-carbonyl, or represent C1-C6-alkylthio-carbonyl (which is optionally substituted by fluorine, chlorine, bromide, cyan or C1-C4-alkoxy-carbonyl), or represent aminocarbonyl, C1-C4-alkylamino-carbonyl, di-(c1-c4-alkyl)-amino-carbonyl, C1-C4-alkoxyamino-carbonyl, C3-C4-alkenyloxy-amino-carbonyl, benzyloxyamino-carbonyl, lo A 23 308 - Foreign Countries ` - 3 - 1228~57 C1~C4~alkoXY~C1~C4-alkyl-amino-carbonyl, dimethyl-hydrazino-carbonyl, or dimethyl-hydrazino-sulphonyl, or represent C3-C6-alkinyloxy or C3-C6-alkinylthio, or in which, furthermore, R1 represents an optionally substituted bouncily radical B

SHEA-wherein R8 and R9 are identical or different and represent hydrogen, halogen (such as, in particular, fluorine, chlorine or bromide), cyan, vitro, C1-colloquial (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy which is optionally substituted by fluorine and/or color-fine), C1-C4-alkoxycarbonyl, Cl-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl or di~(C1-C4-alkyl)-aminosulphonyl;
and in which, furthermore, R2 represents hydrogen, C1-c4-alkyl or a AL sulphonyl radical R10-so2 wherein R10 represents C1-C12-alkyl (which is optionally substituted by fluorine, chlorine, bromide, cyan, vitro, C1-C4-alkoxy-carbonyl, C1-C4-alkylamino-carbonyl, di-(C1-C4-alkyl)-amino-carbonyl, C1-c4-alkoxy~ C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkYl sulphonyl), or represents C1-C12-alkoxy (which is optionally substituted by fluorine, chlorine, bromide, cyan, vitro, C1-C4-alkoxycarbonyl, C1-C4-alkXY~ Cl~C4-alkylth joy C1-C4-alkyl-sulphinyl or C1-C4-alkylsulphonyl)~ or represents C2-C12-alkenyl (which is optionally substituted lo A 23 308 - Foreign Countries _ 4 _ ~22~57 by fluorine, chlorine, bromide, cyan, vitro, C1-C4-alkoxy, C1-C4-alkYlthio or phenol), or represents C~-c1z-alkenyloxy which is optionally substituted by fluorine, chlorine, bromide, cyan, vitro, C1-C4-alkoxy, C1-C4-alkylthio or phenol), or represents C1-C8~
alkylamino, di~(C1-c4-alkyl)-amino~ C3-C6-cycloalkylamino or di-(C3-C6-cycloalkyl)-amino (which are optionally substituted by fluorine, chlorine, bromide, cyan, vitro, phenol, phonics, C1-c4-alkoxy, C1~C4-alkylthio~ C1-C4-alkylsulphinyl or c1-c4-alkylsulphonyl)~ or represents C2-c~-alkenylamino (which is optionally substituted by fluorine, chlorine, bromide, cyan, vitro or phenol), or represents phenylamino or benzylamino (which are optionally substituted by fluorine, chlorine, bromide, C1-Colloquial, trifluoromethyl, C1-C4-alkoxy, C1-C2-f~UOrOaLkOXY, C1-c4-alkylthio~ C1-C4~alkY~sUlPhinY~, C1-c4-a~kylsulphony~
cyan, vitro and/or C1-c4-alkoxy-carbonyl)~ or represents bouncily (which is optionally substituted by fluorine, chlorine, bromide, cyan, vitro, C1-Colloquial, trifluoromethyl, C1-C4-alkoxY-carbonyl, Cl-c4-alkoxy or di-(c1-c4-alkyl)-aminosulphonyl), or represents an optionally subset-tuned phenol radical R1l wherein R11 an R12 are identical or different and have the meanings given above for R6 and R7, but are not ides-tidal to R6 and R7 in each individual case;
and in which, furthermore, R3 represents the radical -o'er, lo A 23 308 - Foreign Countries wherein R13 represents C1-C12-alkyl (which is optionally substituted by fluorine, chlorine, bromide, C1-C4-alkoxy~ C1-C4-alkYlthiO, Cl-c4-alkylsulphinyl or C1-C4-alkylsulphonyl), or represents C3-C6-cycloalkyl, C3-c6-cycloalkyl-c1-c2-alkyl~ C3-c6-alkenYl (which is optionally substituted by fluorine, chlorine or bromide), C3-C6-alkinyl, C1-C4-alkoxy-carbonyl-C1-C2~alkyl~ amino-I carbonyl-methyl, C1-c4-alkylamino-carbonyl-methyl or di-(cl-c4-alkyl)-amino-carbonyl-methyl~ or represents phenol, bouncily or phenethyl which are optionally substituted by fluorine, chlorine, vitro, cyan, Cl-c4-alkyl~ C1-C4-alkoxy or C1-c4-alkoxycarbonyl)i or in which, furthermore, R14 R3 represents the radical -No wherein R14 represents hydrogen or C1-C4-alkyl and I R15 represents hydrogen, C1-C4-alkyl (which is optionally substituted by fluorine, chlorine, brow mine, cyan, C~-C4-alkoxy or C1-C4-alkoxy-carbo-nil), or represents C3-C~-cycLoalkyl, or repro-sets phenol, bouncily or phenethyl (which are opt tonally substituted by fluorine, chlorine, brow mine, cyan, vitro, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxy-carbonyl), or represents C1-C4-alkyl-carbonyl, C1-C4-alkoxy-carbonyl, C1-C4-alkyl-sulphonyl, or phenylsulphonyl (which is optionally I substituted by fluorine, chlorine, bromide, cyan, vitro or methyl);
or in which, furthermore - in the case where R2 represents a sulphonyl radical RUSS

- lo A I 308 - Foreign Countries i228357 wherein R1~ has the above mentioned meaning -R3 also represents hydrogen;
and in which, furthermore, R4 represents fluorine, chlorine, bromide, cycle-propel or C1-C4-alkyl (which is optionally subset-tuned by fluorine and/or chlorine), or represents C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represents C1-C4-MU alkylthio (which is optionally substituted by fluorine and/or chlorine), or represents C1-C4-alkyd- or di-(c1-c4-alkyl)-amino (which are option-ally substituted by fluorine) and R5 represents fluorine, chlorine, bromide, cycle-propel, C1-c4-alkyl (which is optionally subset-tuned by fluorine and/or chlorine), or represents C1-c4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represents C1-C4-alkylthio (which is optionally substituted by fluorine and/or chlorine), or represents C1-C4-alkyd- or di~(C1-C4-alkyl)-amino (which are optionally substituted by fluorine), and 1:1 adduces of compounds of the formula (I) with strong acids, have now been found, the following compounds being excluded: N'-(4-methoxy-6-methyl-s-triazin-2'yl)-h"-dimethylamino-N"'-(2-difluoromethoxy-benzenesullphonyl)-guanidine, N'-(4,6-dimethoxy-s-triazin-2-yl)-N"-methoxy-N",h"'-bis-(2-trifluoromethyl-benzenesulphonyl)-guundone, N'-(4-dimethylamino-6-methyl-s-triazin-Z-yl)-N"-meethics-MU ~"'-(2-methyl-benzenesulphonyl)-guanidine and N'-(4-di-methylamino-6-methyl-s-triazin-2-yl)-N"-dimethylamMinoan"'-(2-methyl-benzenesulphonyl)-guanidine.
If I represents hydrogen, the general formula (I) represents the individual tautomers of the formulae (IA) and (IT) lo A us 30~ - Foreign Countries lZ28:357 R 1 - 5 0 .. - N NH </ ON
G I\ / N=~R5 ( I A ) \ 3 N No R5 (It) R2 \R3 in which R1, R2, R3, R4 and R5 have the above mentioned 5 meanings, and mixtures of the tautomers (IA) and (IT).
The mixing ratio IAMB depends on factors which determine the state of aggregation, such as, for example, the temperature, solvent and concentration.
In the case where R2 also represents hydrogen, in addition to M, another tautomeric form (IT) is possible:
N~R4 Rl-502-NH NO
C/ N~R5 tic in which R3 R1, R3, R4 and R5 have the above mentioned meanings.
to The new sulphonylguanidinotriazine derivatives of the formula I) are obtained by a process in which (a) in the case where M represents hydrogen, guanidinotri-amine derivatives of the formula IT
H ' No; R4 C/ No R5 (II) / \ 3 lo A 23 308 - Foreign Countries 12~8357 in which R3, R4 and R5 have the above mentioned meanings, are reacted with sulphonyl chlorides of the formula (III ) Al -Seiko Tao ) in which R1 has the above mentioned meaning, in the presence of acid acceptors and if appropriate in the presence of delineates; or (b) in the case where M represents hydrogen and R2 repro-sets hydrogen or C1-C4-alkyl~ the sulphonylguanidino~
treason derivatives obtainable by the process described above under (a), of the formula (ID) ` H No R4 N No 5 (ID) Al -S02 . -Rl 3 in which R1, R4, R5 and R13 have the above mentioned meanings, are reacted with amino compounds of the formula (IV) MU R2 (IV) HO ~R3 in which I represents hydrogen or C1-C4-alkyl and R3 has the above mentioned meaning, or with hydrochloride of amino compounds of the formula (IV), if appropriate in the presence of acid acceptors and if appropriate in the presence of delineates; or (c) in the case where M represents hydrogen and R2 repro-sets an optionally substituted sulphonyl radical R1~_S02_ lo A 23 30B - Foreign Countries _ 9 _ wherein Rho has the above mentioned meaning, sulphonylguanidinotriazine derivatives of the formula (If) Rl-502-N HO I/ N (If) H' N I
in which R1, R3, R4 and R5 have the above mentioned meanings, are reacted with sulphonyl chlorides of the formula (V) R10-S02-Cl (V) in which R10 has the above mentioned meaning in the presence of acid acceptors and if appropriate in the presence of delineates; or (d) also in the case where M represents hydrogen and I represents an optionally substituted sulphonyl radical R1 Sue_ wherein R10 has the above mentioned meaning, sulphonylguanidinotriazine derivatives of the formula (VI) OH ,' No R

RlO_So~ R3 lo A 23 3~8 - Foreign Countries - 1 o - ~2~8~57 in which R3, R4, R5 and R10 have the above mentioned meanings, are reacted with sulphonyl chlorides of the formula ( I I I ) Rl-SOz~C l ~III) in which R1 has the above mentioned meaning, in the presence of acid acceptors and if appropriate in the presence of delineates; or (e) in the case where M represents hydrogen and RZ repro-sets hydrogen or C1-C4-alkyl, sulphonylisothioureido-Rosen derivatives of the formula (VII) I N=CR5 (VII) s \R16 in which R1, R4 and R5 have the above mentioned meanings and R16 represents C1-C4-alkyl or bouncily, are reacted with amino compounds of the formula tip) Ho (IV) in which RZ represents hydrogen or C1-C4-alkyl-and R3 has the above mentioned meaning if appropriate in the presence of delineates; or (f) in the case where M represents one equivalent of a me-tat, the compounds obtainable by the processes described above under (a), tub), (c), id) and (e) of the formula tip in which if represents hydrogen and R1, RZ, R3, R4 and R5 have the above mentioned meanings, are reacted with metal hydroxides, hydrides or alkanolates or with organometallic lo A 2-S 3~8 - Foreign Countries I :8~5~7 compounds, if appropriate in the presence of delineates; or (go in the case where 1:1 adduces of compounds of the for mute (I) with strong acids are to be prepared, compounds of the formula (I) in which M represents hydrogen and R1, R2, R3, R4, and R5 have the above mentioned meanings, are reacted with strong acids, if appropriate in the pros-once of delineates.
The new sulphonyLguanidinotriazine derivatives of the formula (I) and their addicts with strong acids are 0 distinguished by a powerful herbicidaL activity.
Surprisingly, the new compounds of the formula (I) exhibit a considerably better herbicidaL action than already known guanidines of the same type of action.
The invention preferably relates to compounds of the formula (I) in which represents hydrogen or one equivalent of sodium, potassium or calcium, R1 represents an optionally substituted phenol MU radical R6 wherein R6 and R7 are identical or different and repro-sent hydrogen, fluorine, chorine, bromide, cyan, I vitro or methyl (which is optionally substituted by fluorine, chlorine, cyan, C1-C3-aLkoxy-carbo-Noah C1-Cs~aLkOXY~ C1~C3-aLkyLthjo~ C1-C3-alkyLsuLphinyL or C1-c3-alkylsulphonyL)~ or rep-resent C1-c~-alkoxy (which is optionally sub-I stituted by fluorine, chlorine, cyan, c1-c3-alkoxY
carbonyl, C1-c3-alkOxy~ C1-C3-alkylthio, I
Cs-alkyLsulphinyl or C1-C3-aLkYlsuLphonyl), or represent C1-C3-alkyLthio, C1-C3-alkyLsulphinyl or C1-C3-aLkyLsuLphonyl (which are optionally lo A 23 308 - Foreign Countries ~21~357 substituted by fluorine, chlorine, cyan or C1-C3-alkoxy-carbonyl), or represent Dick-C3-alkyl)-aminosulphonyl, C1-C3-alkoxy-methyl-aminosulphonyl, phenol or phonics, or represent C1-C4-alkoxy-carbonyl (which is optionally substituted by fluorine, chlorine, brom;ne, cyan or C1-C3-alkoxy), C3-C6-cycloalkyloxy-carbonyl, C1-C4-alkYlthio-carbonyl, di-(C1-C3-alkyl)-amino-carbonyl or C1-C3-alkoxy-methylamino-carbonyl or no-present C2-C4-alkenyl (which us optionally substituted by fluorine, chlorine, cyan or C1-C3-alkoxy-carbonyl);
or in which, furthermore, R1 represents an optionally substituted bouncily radical R8 SHEA--wherein R9 R8 and R9 are identical or different and represent hydrogen, fluorine, chlorine, cyan, vitro, methyl, methoxy or C1-C3-alkoxy-carbonyl;
and in which, furthermore, R2 represents hydrogen, methyl or a sulphonyl radical R10-S02_ wherein R10 represents C1-C8-alkyl (which is optionally substituted by fluorine, chlorine or cyan), or . represents C1-C8-alkoxy (which us optionally substituted by fluorine, chlorine or cyan), or represents C2-C8-alkenyl (which is optionally substituted by fluorine, chlorine, cyan or phenol), or represents C2-C8-alkenyloxy (which is optionally substituted by fluorine, chlorine, cyan lo A 23 308 - Foreign Countries ~228357 or phenol), or represents C1-C6-alkylamino, C3-C6-cycloalkylamino or di-(C3-C6-alkyl)-amino (which are optionally substituted by fluorine, chlorine, cyan, phenol, phonics or C1-C2-alkoxy), or represents C2-C6-alkenylamino (which is optionally subset-tuned by fluorine, chlorine, cyan or phenol), or represents phenylamino or benzylamino (which are optionally substituted by fluorine, chlorine, bromide, C1-C4-alkyl, trifluoromethyl, C1-C3-alkoxy, C1-C2-fluoroalkoxy, C1-C3-alkylthio, C1-alkylsulphinyl, C1-C3-alkylsulphonyl, cyan, vitro and/or C1-C3-alkoxy-carbonyl), or represents bouncily (which is optionally substituted by fluorine, chlorine, cyan, vitro, methyl, methoxy and/or C1-C2-alkoxy-carbonyl), or represents an optionally substituted phenol radical Al wherein R11 and R12 are identical or different and have the preferred meanings given above for R7 and R8, but are not identical to R7 and R8 in each individual case;
and in which, furthermore, R3 represents the radical -o'er, wherein R13 represents C1-C8-alkyl which is optionally substituted by fluorine or chlorine), or represents C3-C6-alkenyl which is optionally substituted by chlorine), or represents C1-C3-alkoxy-carbonyl-C1-C2-alkyl, phenol, phenethyl or bouncily which is optionally substituted by fluorine, chlorine lo A 23 308 - Foreign Countries ` - 14 - 1228357 vitro, methyl, methoxy or C1-C2-alkoxy-carbonyl);
or in which, furthermore, R3 represents the radical /Rl4 -N

wherein R14 represents hydrogen or methyl and 5 represents hydrogen, C1-C3-alkyl (which is optionally substituted by fluorine, chlorine, I cyan, C1-C~-alkoxy or C1-C2-alkoxY-carbonyl), or represents C3-c6-cyc~oa~ky~ phenol, bouncily or phenethyl (which is optionally substituted by fluorine, chlorine, bromide, vitro, cyan, C1-C2-alkyl, C1-C~-alkoxy or C1-C2-alkoxy-car-bony), or represents acutely, methoxycarbonyl, benzenesulphonyl or toluenesu~phonyl;
and in which, furthermore, R4 represents fluorine, chlorine, cyclopropyl or methyl (which is optionally substituted by flu-fine and/or chlorine), or represents C1-C3-alkoxy (which is optionally substituted by fluorine and/
or chlorine), or represents C1-C3-alkylthio (which is optionally substituted by fluorine and/
or chlorine), or represents C1-C3-a~ky~- or di-(C1-C3-I alkyl)-amino (which are optionally substituted by fluorine) and US represents fluorine, chlorine, cyclopropyl or methyl (which is optionally substituted by fluorine and/or chlorine), or represents C1-C3-I alkoxy (which is optionally substituted by flu-fine and/or chlorine), or represents C1-C~-alkyl-trio (which is optionally substituted by fluorine and/or chlorine), or represents C1-C3-alkyl- or dip lo A I 308 - Foreign Countries - 15 - 12~8~57 (C1-C3-alkyl)-amino (which are optionally sub-stituted by fluorine), the compounds mentioned individually above being excluded.
The invention furthermore preferably relates to 1:1 adduces of compounds of the formula (I) - as defined above, wherein M represents hydrogen - with hydrogen halide acids, such as hydrogen chloride, hydrogen bromide and hydrogen iodide, with sulfuric acid or triflers-tic acid, with alkanesulphonic acids which have up to 4 I carbon atoms and are optionally substituted by fluorine or chlorine, or with Bunsen- or naphthalene- sulphonic acids, which are optionally substituted by fluorine, Shelley-fine, bromide or methyl.
The invention particularly relates to compounds of the formula (I) in which I represents hydrogen or one equivalent of sodium, potassium or calcium, R1 represents a substituted phenol radical 211 R~7 6 wherein I represents fluorine chlorine, bromide, methyl, trifluoromethyl, methoxy, difluoromethoxy, in-fluoromethoxy, C1-C3-alkylthio, C1-C3-alkylsul I phenol, c1-c3-alkYlsulphonyl~ dimethylaminosul-phony, diethylaminosulphonyl, methoxymethylamino-sulphonyl, phenol C1-C4 alkoxy-carbonyl, difluoromethylthio or trifler-methylthio and R7 represents hydrogen; L and in which, furthermore, R2 represents hydrogen, methyl or a sulphonyl radical lo A 23 I - Foreign Countries - 16 - i2~8357 ROY_ wherein R10 represents Cl-c4-aLkyL (which is optionally substituted by fluorine or chlorine), or represents C1-C4-aLkyLamino or Dick-C-~alkyl)-amino (which are optionally sub-stituted by fluorine), or represents an optionally substituted phenol radical R l lo ill wherein R11 and R12 are identical or different and repro-sent hydrogen, fluorine, chlorine, bromide, cyan, vitro, methyl, trifluoromethyl, C1-C2-alkoxy (which is optionally substituted by fluorine, Shelley-fine, cyan or C1-C3-alkoxy-carbonyl), C1-C3-aLkylthio~ C1-C3-alkylsulphinyL or C1-C3-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylamino-MU sulphonyl, phenol or C1-C4-alkoxy-carbonyl (which .
is optionally substituted by fluorine, chlorine, cyan or C1-C2-alkoxy~, and in which, furthermore, R3 represents the radical -o'er, 25 wherein R13 represents C1-C4-alkyl~ C3-C4-alkenyl, C1-C4-alkoxy-carbonyl-methyl, phenol, phenethyl or bouncily (which is optionally substituted by fluorine, chlorine, vitro, cyan, methyl, methoxy MU or methoxycarbonyl), -or in which, furthermore, R3 represents the radical lo A us MU - Foreign Countries ` - 17 - 12~8~7 ~R15 wherein R~4 represents hydrogen or methyl and R15 represents hydrogen, C1-C-S-alkYl~ C3-C6-cycloalkyl, phenol, acutely, methoxycarbonyl, bent zenesulphonyl or toLuenesulphonyl;
and in which, furthermore, R4 represents methyl, methoxy, ethics, methylthio, ethylthio, methyl amino, ethyl amino, dimethylamino or diethylamino and R5 represents methyl, methoxy, ethics, methylthio, ethylthio~ methyl amino, ethyl amino, dimethylamino or aiethylamino, - the compounds mentioned individually above being exile-dyed - and - in the case where M represents hydrogen - the 1:1 adduces of the compounds defined above with hydrochloric acid, sulfuric acid, trifluoroacetic acid, methanesulpho-nix acid, benzenesulphonic acid and toluenesulphonic acid.
the compounds mentioned individually above are also excluded in the preferred and particularly preferred range.
If, for example, 2-fluoro-benzenesulphonyl Shelley-ride and Nl-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-ethoxy-guanidine are used as starting substances for process variant (a), the course of the reaction can be outlined by the following equation:

2 Scholl No C

lo A US I - Foreign Countries - 18 122~3357 - 2 Hal C No OUCH
/ \

If, for example, N'-(4-methoxy-6-methylthio-s~tri-azin-2-yl)-N"-methoxy-N",N"'-bis-(~-trifluoromethyyl-ben-zenesulphonyL)-guanidine and phenyLhydrazine are used as S starting substances for process variant (b), the course of the reaction can be outlined by the following equation:

~52 OUCH
I<
CF3 _ >

- SO - NASH
OF

NH
NO
If, for example, N'-(4,6-dimethoxy-s-triazin-2-yl)-N"-benzyLoxy-~ (2-chlorophenylmethylsulphonyl)-guanidine I and 2-trifluoromethanesulphonic acid chloride are used Lo A 23 3~8 - Foreign Countries ~2~8~S7 as starting substances for process variant (c), the course of the reaction can be outlined by the following equation:
N 3 CF3-5O2-Cl H OUCH

I N OUCH
- Hal CF352 OUCH

If, for example, N'-(4-ethoxy-6-methyl-s-triazin~
2-yl)-N"-methoxy-N"-(2-ethoxycarbonyl~benzenesulphHoneywell guan~dine and 2-dimethylaminosulphonyl-benzenesulphonyl chloride are used as starting substances for process vary-ant (d), the course of the reaction can be outlined by the following equation:
I OH, ON SHEA
I N OOZE synch N
SO OUCH
COOK

SOz-N(CH3~2 OH N SHEA

C N OOZE
- Hal No lo A I ~08 - Foreign Countries 12;~ ~33~7 - Jo If, for example, N'-(4-methoxy~6~methyl~s~triazin~
2-yl)-N"-(2-methyl-benzenesulphonyl)-S-methyl-isotThor and h,N-dimethylhydrazine are used as starting substances for process variant (e), the course of the reaction can be outlined by the following equation:

SHEA H ' N SHEA

C OUCH + H2NN(CH312 So SHEA

C N SHEA
- HSCH3 No H N~CH3)2 If, for example, N'-(4,6-dimethoxy-s-triazin~2~yl)~
N"-isopropoxy-N"'-~2~methoxycarbonylphenyLmethylsuulphonyl)~
guanldine and potassium ethanol ate are used as starting I substances for process variant (f), the course of the reaction can be outlined by the following equation:
COUCH ` H ON OUCH
N

H OCH~CH3)2 COUCH G, No OUCH

COOK I No OUCH
- HAYAKAWA ON
H OCH(CH3)2 lo A I 3~8 - Foreign Countries - 21 - 12~8357 If, for example, N'-(4-methylamino-6-methylthio-s-triaz;n-2-yl)-N"-methoxy-N"-(2-chloro-benzenesullphonyl)-N"'-(2-difluoromethoxy-benzenesulphonyl)-guanidineeland methanesulphonic acid are used as starting substances for process variant tug), the course of the reaction can be outlined by the following equation:

fishwife H N NHCH3 I N SC + SHEA

SO / KOCH

\ / ON
C SHEA X CHIHUAHUAS

SO \ OUCH

Formula (II) provides a general definition of the guanid;notriazine derivatives to be used as starting sub-MU stances for process variant (a). In formula (II), R3,R4 and R5 preferably and particularly have the same meanings as are given above as preferred or as portico-laxly preferred in the context of the definition of the substituents of formula (I).
Examples which may be mentioned of starting substances of the formula tip) are: N'-(4,6-dimethyl-s-triazin-2-yl)-, N'-(4-methoxy-6-methyl-s-triazin-yule)-, N'-(4-ethoxy-6-methyl-s-triazin-2-yl)-, N'-(4,6-dimethoxy-s-triazin-2-yl)-, N'-(4,6-diethoxy-s-triazin-2-yl)-, N'-(4-ethoxy-6-methoxy-s-triazin-2-ye)-, N'-(4-methyl-6-methylthio-s-triazin-2-yl)-, lo A 23 308 - Foreign Countries 12~8357 N'-(4-ethylth;o-6-methyl-s-triazin-2-yl)-, N'-(4-methoxy-6-methylthio-s-triazin-2-yl)-, N'-(4-ethoxy-6-methylthio-s-triazin-2-yl)-~ N'-(4-ethylthio-6-methoxy-s-triazin-2-ye)-, N'-(4-ethoxy-6-ethylthio-s-triazin-2-yl)-, N'-(4,6-bis-methylthio-s-triazin-2-yl)-, N'{4,6- bis-ethylthio-s-triazin-2-yl)-, N'-(4-methyl-6-methylamino-s-triazin-2-ye)-, N'-(4-ethylamino-6-methyl-s-tr;azin-2-yl)-, No dimethylamino-6-methyl-s-triazin-2-yl)-, N'-(4-diethyl-amino-6-methyL-s-triazin-2-yl)-, N'-(4-methoxy-6-methyl-amino-s-triazin-2-yl)-, N'-(4-ethylamino-6-methoxy-s-tri-azin-2-yl)-, N'-(4-dimethylamino-6-methoxy-s-triazin-2-yl)-, N'-(4-diethylamino-6-methoxy-s-triazin-2-yl)-, No ethoxy-6-methylamino-s-triazin-2-yl)-, Nighthawks-ethylamino-s-triazin-2-yl)-, N'-(4-dimethylamino-6-ethoxy-s-triazin-2-yl)-, N'-(4-diethylamino-6-ethoxy-s-triazin-yule)-, N'-(4-methylamino-6-methylthio-s-triazin-2-yl)-, N'-(4-ethylamino-6-methylthio-s-triazin-2-yl)-, N'-t4-di-methylamino-6-methylthio-s-triazin-2-yl)-, N'-(4-diethyl-amino-6-methylthio-s-triazin-2-yl)-, N'-(4-ethylthio-6-methylamino-s-triazin-2-y~)-, N'-(4-dimethylamino-6-ethyl-thio-s-triazin-2-yl)- and N'-(4-diethylamino-6-ethylthio-s-triazin-2-yl)-N"-methoxy-guanidine, -N"-ethoxy-guan-iodine, -N"-propoxy-guanidine, -N"-isopropoxy-guanidine, -N"-butoxy-guanidine, -N"-isobutoxy-guanidine, -N"-sec.-butoxy-guanidine, -N"-pentoxy-guanidine, -N"-isopentoxy-guanidine, -N"-hexyloxy-guanidine, -N"-octyloxy-guan-iodine, -N"-allyloxy-guanidine, -N"-(2-chloro-ethoxy)-guanidine, -N"-(2-fluoro-ethoxy)-guanidine, -N"-(2-chloro-propoxy)-guanidine, -N"-(2-fluoro-propoxy)-guanidine, -N"-(3-chloro-propoxy)-guanidine, -N"-(4-chloro-butoxy)-guanidine, -N"-methoxycarbonylmethoxy-guanidine, -N"-ethoxy-carbonyl-methoxy-guanidine, -N"-(1-methoxy-carbo-nyl-ethoxy)-guanidine, -N"-(1-ethoxy-carbonyl-ethoxy)-guanidine, -N"-dimethylamino-carbonyl-methoxy-guanidine, -N"-(2-phenyl-ethoxy)-guanidine, -N"-phenoxy-guanidine, -N"-(4-methyl-benzyloxy)-guanidine, -N"-(4-fluoro-benzyloxy)-lo A 23 308 - Foreign Countries - guanidine, -N"-t4-chloro-benzyloxy)-guanidine, No nitro-benzyloxy)-guanidine, -N"-~2,6-dichloro-benzyloxy)-guanidine, -N"-(4-methoxycarbonyl-benzyloxy)~guanidine and -N"-(4-ethoxycarbonyl-benzyloxy)-guanidine.
The starting substances of the formula (II) are known compare DEMOS (German Published Specification)

3,334,455).
The guanidinotriazine derivatives of the formula (II) are obtained by a process in which cyanoaminotriazine derivatives of the formula (YO-YO) < (VI I I ) No R5 in which R4 and R5 have the above mentioned meanings, are reacted with amino compounds of the formula (IX) HzN-R3 (IX) in which R3 has the above mentioned meaning, or with hydrochloride thereof, if appropriate in the pro-since of delineates, such as, for example, ethanol, isopropa-I not or buttonhole at temperatures between 20C and 150C, preferably between 50C and 120C, and, if appropriate, the reaction products are treated with acid acceptors, such as, for example, ammonia, sodium hydroxide solution or sodium carbonate.
The cyanoaminotriazine derivatives of the formula (VIII) are known (compare DEMOS (German Published Spew suffocation) 3,334,455).
The compounds of the formula (~III) are essentially lo A 23 308 - Frown Countries 12~8357 obtained by the following synthesis routes:
aye) by reactions of alkali metal or alkaline earth metal salts of cyanamide - such as, for example, sodium cyan-mode or calcium cyanamide - with chlorotriazines of the formula (X) Of I/ N (X) No R5 in which R4 and R5 have the above mentioned meanings, if appropriate in the presence of inert delineates, such as, for example, ethanol, acetone, acetonitrile or dim ethyl-formamide, at temperatures between 0C and 100C. After the mixture has been concentrated and the residue has been dissolved in water, the cyanoaminotriazine derivatives of the formula (VIII) can be precipitated by acidification, for example with hydrochloric acid, and isolated by lit-traction with suction.
Alternatively, cyanoaminotriazine derivatives of the formula (VIII) are obtained by a process in which (a) aminotriazines of the formula (XI) I No R4 H2N4 N (XI ) in which R4 and R5 have the above mentioned meaning, are reacted with carbonyl isothiocyanates of the formula tXII) O
R17-C-N=C=s (XII) in which R17 represents ethics or phenol, lo A 23 I - Foreign Countries - 25 1228~57 if appropriate in the presence of inert delineates, such as, for example, acetone, acetonitrile or Tulane, at temperatures between 0C and 100C, the carbonyl-Theresa thereby formed of the formula (XIII) R 1 7 _ C - NH - C - NH ON ( X I I I ) No R5 in which R4, R5 and R17 have the above mentioned meanings, are isolated by filtration with suction, if appropriate after concentration of the mixture, and are reacted with aqueous alkali metal or alkaline earth metal hydroxide solutions, such as, for example, sodium hydroxide solution, if appropriate in the presence of an organic solvent, such as, for example, tetrahydrofuran or Dixon, at tempera lures between 0C and okay an the Theresa obtained in crystalline form after acidification, for example with hydrochloric acid, of the formula (XIV) H2N-C-NH ON ~XIV) in which R4 and R5 have the above mentioned meanings, are isolated by filtration with suction and reacted with metal compounds which can bind hydrogen sulfide, such as, for example, with Lydia) acetate, Cooper) acetate, men-query) acetate or iron) acetate, in the presence of aqueous alkali metal or alkaline earth metal hydroxide 25 solutions, such as, for example, sodium hydroxide soul-lion, at temperatures between 20C and 100C, the mixture is filtered, when the reaction has ended, and the filtrate is acidified with an acid, such as, for example, acetic acid.
The products of the formula (YO-YO) thereby ox-lo A 23 30~ - Foreign Countries 12;;~8357 twined as crystals can be isolated by filtration with-suction.
The chlorotriazines of the formula (X), aminotri-azines of the formula I and carbonyl isoth;ocyanates of the formula (XII) to be used as starting substances for the preparation processes described above under (a) and (a) for the cyanoaminotriazine derivatives of the for-mute (VIII) are known and/or can be prepared by processes which are known per so (compare US. Patent Specification 3,154,547 and US. Patent Specification 4,160,037).
In another alternative process, cyanoaminotri-amine derivatives of the formula (VIII) are obtained when (a) dichlorotriazines of the formula (Pa) Nil Of I/ N
N R5 (Pa) in which R5 has the abovement;oned meaning, are reacted with alkali metal salts or alkaline earth metal salts of cyanamide, such as, for example, with disod;um cyanamide, on the presence of a fluent such as, for example, water, at temperatures between -10C
and +50C, and the resulting metal salt of the moo-chloro-cyanoaminotriazine of the formula (Vow) (Vow) N:~CR5 lo A 23 308 - Foreign countries on which R5 has the meaning given above, is converted to the free monochloro-cyanoam;notriazine of the formula (Vow) with an acid, such as, for example, hydrochloric acid.
The corresponding cyanoaminotriazines of the formula tVIII), in which R4 represents alkoxy, alkylthio, alkylamino or dialkylamino, can be prepared from the monochloro-cyanoaminotriazines of the formula (Vow) by reaction with alcohols or alkanethiols or with monoalkyl- or dialkylamines.
In a further alternative process, cinnamon-treason derivatives of the formula (VIII) are obtained if (a) aminotriazines of the formula (XI) HEN I/ N (XI) in which R4 and R5 have the above mentioned meaning, are reacted with cyanogen chloride CLAN in the presence of a base, such as, for example, bottle-lithium, and in the presence of a delineate, such as tetrahydrofuran, at temperatures between 0C and 50C, and when the reaction is complete, the mixture is evaporated down and the residue is diluted with water and acidified.
The amino compounds of the formula (IX) also to be used as starting substances are likewise known and lo A 23 308 - Foreign countries - 28 - 12~8357 can be prepared by processes which are known per so (compare Chum. Harm. Bull. 15, (1967), 345; Bull.
Sock Chimp France 1958, 664; Synthesis 1976, 682; J.
Chum. Sock 193U, 228 and Help. Chimp Act 45, (1962), 1387).
Formula (III) provides a general definition of the sulphonyl chlorines also to be used as starting sub-stances for process variant (a). In formula (III), R1 preferably and particularly has the same meaning as is given above as preferred or as particularly preferred in the context of the definition of the substituents of formula (I).
Examples which may be mentioned of starting sub-stances of the formula (III) are: sheller-, sheller-, sheller-, 2,5-dichloro-, flyer-, flyer-, Brigham-, Brigham-, nutria-, nutria-, Sweeney-, 2-methyl-, 4-methyl-, 2-chLoromethyl-, 2-trifluoromethyl-, 2-methoxy-, 2-djfluoromethoxy-, 2-trifluoromethoxy-, 2-methylthio-, 2-methy~thiomethyl-, 2-methylsulphinylmethyl-, 2-methyl-sulphonylmethyl-, 2-dimethylaminosulphonyl-, deathly-aminosulphonyl-, phenol-, 2-methoxycarbonyl-, ethics-carbonyl-, 2-propoxycarbonyl-, 2-isopropoxycarbonyl-, 2-butoxycarbonyl-, 2-dimethylaminocarbonyl-, 2-diethylamino-carbonyL-, phonics-, 2-methyl-5-chloro-, 2-chloro-5-tri-fluoromethyl-, 2-methylsulphonyl-, 2-ethylsulphonyl-, Z-chLoro-4-trifluoromethoxy-, 3-chloro-4-trifluoromethoxy-, 2-trifluoromethoxy-5-chloro- and 3,5-dichloro-benzenesulpho-nil chloride; (2-chloro-phenyl)-, (2-cyano-phenyl)- and (2-methoxycarbonyl-phenyl)-methanesulphonyl chloride; and also methane-, chloromethane-, trifluoromethane-, ethanes-, 2-chloroethane-, ethene-, propane-, butane-, perfluorobutane-and perfluorooctanesulphonyl chloride and methyl-, ethyl-, propel-, isopropyl-, cyclohexyl-, dim ethyl- and deathly-sulphamyl chloride.
The sulphonyl chlorides of the formula (III) are known and/or can be prepared by processes which are lo A 23 308 - Foreign Countries - 29 - 1228~57 known per so compare J. Org. Chum. 33 (1968), 2104; J.
Org. Chum. 25 t1960), 1824; DE-AS German Published Specie ligation) 2,308,262; EGOS (European Published Specific-lions) 23,140, 23,141, 23,422, 35,893, 48,143, 51,466, 64,322, 70,041, 44,808 and 44,809; and US. Patent Specie fixations ~,929,82U, 4,282,242, 4,348,220 and 4,372,778 and Anger. Chum. 93 (1981), 151).
These compounds are essentially obtained by the following two synthesis routes:
(1) by reaction of the corresponding sulphonic acids R1-S03-H or of alkali metal or alkaline earth metal salts thereof with halogenating agents, such as, for example, phosphorus-V chloride phosphorus pentachloride), pros-furl chloride phosphorus oxychloride), thinly Shelley-ride, phosgene or benzotrichloride, if appropriate in the presence of catalysts, such as, for example, pardon or dimethylformamide~ and if appropriate using inert delineates, such as, for example, ethylene chloride, chloroform, acetonitrile, chlorobenzene and/or sulpholane, at tempera-I lures between -OKAY and +150C, preferably between C
and +100C; after dilution with water, the sulphonyl chlorides - where these are obtained as crystals - can be isolated by filtration with suction or purified by extract lion with a water-immiscible solvent, such as, for example, ethylene chloride, deathly ether or hexane, washing and drying of the extracts, concentration and recrystallize-lion or distillation; or also Org.
(2) in a manner which is known per so (compare J.VChem.
25 (1960), 1824; DEMOS (German Published Specification) I 2,308,2~2 and EGOS (European Published Specification) 59,241)~ by reaction of corresponding amino compounds R1-NH2 with sodium nitrite and hydrochloric acid, if appropriate in the presence of acetic acid, at tempera-lures between -ltJC and +20C, preferably between -5C
and +10C, and subsequently (in situ) with Selfware dioxide or a salt of sulfurs acid, such as, for example, lo A 23 308 - Foreign Countries 12;~8357 sodium bisulphite, in the presence of a copper compound, such as, for example, copper chloride or copper sulfite, as a catalyst, at temperatures between 0C and 80C, preferably between 1~C and 60C.
Working up can be carried out in the usual manner:
on dilution with water, the sulphonyl chlorides are in general obtained as crystals and can be isolated by filtration with suction. However, they can also be ox-treated from the aqueous dispersion with a solvent which I is virtually water-immiscible, such as, for example, me-ethylene chloride or deathly ether, dried and purified by vacuum distillation.
Formula (ID) provides a general definition of the sulphonylguanidinotriazine derivatives to be used as starting substances for process variant (by. In formula (ID, R1, R4, R5 and R13 preferably and particularly have the same meanings as are given above as preferred or as particularly preferred in the context of the define-lion of the substituents of formula (I).
I Examples which may be mentioned of the compounds of the formula (ID) are: N'-(4,6-dimethoxy-s-triazin-2-yl)-N"-methoxy-N", _N"'-bis-(2-trifluoromethyl-benzenesul-phonyl)-guanidine, N'-~4-diethylamino-6-methoxy-s-triazin-~-yl)-N"-methoxy-N",N"'-bis-(2-chloro-benzenesulphonnil)-guanidine and N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-methoxy-N",N"'-bis-(2^chloro-benzenesulphonyl)-guaaniline.
The compounds of the formula (ID) can be prepared by the process described above under (a).
Formula tip) provides a general definition of the I amino compounds to be used as starting substances in process variant (b). In formula (IV), R2 and R3 preferably and particularly have the same meanings as are given above as preferred or as particularly preferred in the context of the definition of the substituents of formula (I).
Examples which may be mentioned of starting sub-stances of the formula (IV) are: N,N-dimethylhydrazine, lo A 23 3~8 - Foreign Countries 12~8357 phenylhydrazine, 0-methyl-hydroxylamine~ (J-ethyl-hydroxyl-amine, Us dimethylhydroxylamine~ and propel-, 0-isopro-ply-, li-butyl-~ 0-isobutyl-, 0-sec.-butyl-, ponytail-, 0-isopentyl-, 0-sec.-pentyl-, exile-, 0-isohexyl-, 0-hep-5 twill-, 0-isoheptyl-, 0-octyl-, 0-isooctyl-, allele-, 0-crotyl-, 0-(2-chloro-ethyl)-~ 0-(2-fluoro-ethyl)-, 0-(2-chloro-propyl)-, 0-(3-chloro-propyl)-, 0-(4-chloro-butyl)-, U-methoxycarbonylmethyl-~ 0-~thoxycarbonylmethyl-, 0-(1-methoxycarbonyl)-ethyl-, 0-(1-ethoxycarbonyl)-ethyl-, 0-10 aminocarbonylmethyl-, 0-(2-phenyl-ethyl)-, phenol-, 0-(4-methyl-benzyl)-, 0-(4-fluoro-benzyl)-, 0-(4-chloro-ben-Zulu)-, 0-(4-nitro-benzyl)-, ~-(2,6-dichloro-benzyl)-, 0-(4-methoxycarbonyl-benzyl)- and li-(4-ethoxycarbonyl-benzyl)-hydroxylamine.
Amino compounds of the formula (IV) are known and can be prepared by processes which are known per so (coy-pare Chum. Harm. pull. 15 (1967), 345; Bull. Sock Chimp France 1958, 664; Synthesis 1976, 6~2; J. Chum. Sock 193~, 228 and Help. Chimp Act 45 (1962), 1387).
I Formula IT provides a general definition of the sulphonylguanidinotriazine derivatives to be used as starting substances in process variant (c). In formula (If), R1, R3, R4 and R5 preferably and particularly have the same meanings as are given above as preferred or 25 as particularly preferred in the context of the definition of the substituents of formula (I).
Examples which may be mentioned of the compounds of the formula (If) are: N'-(4,6-dimethyl-s-triazin-2-yl)-, N'-(4-methoxy-6-methyl-s-triazin-2-yl)-, Nighthawks-30 methyl-s-triazin-2-yl)-, N'-(4,6-dimethoxy-s-triazin-2-ye)-, N'-(4,6-diethoxy-s-triazin-2-yl)-, Nighthawks-methoxy-s-triazin-2-yl)-, N'-(4-methyl-6~methylthio-s~
treasonously)-, N'-(4-ethylthio-6-methyl-s-triazin-2-y l)-, N'(4-methoxy-6-methylthio-s-triazin-Z-yl)-, N'-35 (4-ethoxy-6-methylthio-s-triazin-2-yl)-, No ethylthio-6-methoxy-s-triazin-2-yl)-, Nighthawks lo A 23 30~ - Foreign Countries 6-ethylthio-s-triazin-Z-yl)-, N'-(4,6-bis-methylth;o-s-triazin-2-yl)-, N'-(4,6-bis-ethylthio-s-triazin-2-yl)-, N'-(4-methyl-6-methylamino-s-triazin-2-yl)-, Knothole-amino-6-methyl-s-triazin-2-yl)-, N'-(4-dimethylamino-6-methyl-s-triazin-2-yl)-, N'-(4-diethylamino-6-methyl-s-triazin-2-yl)-, N'-(4-methoxy-6-methylamino-s-triazin-2-ye)-, N'-(4-ethylamino-6-methoxy-s-triazin-2-yl)-, No dimethylamino 6-methoxy s-triazin-2-yl)-, N'-(4-diethyl-amino-6-methoxy-s-triazin-2-yl)-, N'-(4-ethoxy-6-methyl-amino-s-triazin-2-yl)-, N'-(4-ethoxy-6-ethylamino-s-tria-z;n-2-yl)-, N'-(4-dimethylam;no-6-ethoxy-s-tr;azin-2-yl)-, N'-(4-diethylamino-6-ethoxy-s-triazin-2-yl)-, No methyl amino 6-methylthio-s-triazin-2-yl)-, Knothole-amino-6-methylthio-s-triazin-2-yl)-, N'-(4-dimethylamino-6-methylthio-s-triazin-2-yl)-, N'-(4-diethylamino-6-methylthio-s-triazin-2-yl)-, N'-(4-ethylthio-6-methyl-amino-s-tr;azin-2-yl)-, N'-(4-dimethylamino-6-ethylthio-s-tr;az;n-2-yl)- and N'-(4-d;ethylamino-6-ethylthio-s-triaz;n-2-yl)- N"-methoxy-, -Nighthawks-, -N"-propxy-, -N"-;sopropoxy-, -N"-butoxy-, -N"-isobutoxy-, -N"-sec.-buttocks-, -N"-pentoxy-, -N"-hexyloxy-, -N"-octyloxy-, -N"-allyloxy-, -N"-crotyloxy-, -N"-t3-chloro-propoxy)-, -N"-methoxycarbonyl-methoxy-, -N"-ethoxycarbonylmethoxy, -N"-(1-methoxycarbonyl-ethoxy)-, -N"-(1-ethoxycarbonyl-ethics)-, -N"-(2-phenyl-ethoxy)-, -N"-phenoxy-, Ben zyloxy-, -N"-(4-methyl-benzyloxy)-, N"-(4-fluoro-benzyl-ox)-, -N"-(4-chloro-benzyloxy)-, -N"-(4-n;tro-benzyloxy)-, -N"-(2,6-d;chloro-benzyloxy)-, -N"-(4-methoxycarbonyl-ben-zyloxy)- and -N"-(4-ethoxycarbonyl-benzyloxy)-, Ben zenesulphonyl-, -N"'-(2-chloro-benzenesulphonyl)-, No chloro-benzenesulphonyl)-, -N"'-(4-chloro-benzenesulpho-nil)-, -N"'-(2-fluoro-benzenesulphonyl)-, -N"'-(4-fluoro-benzenesulphonyl)-, -N"'-(2-bromo-benzenesulphonyl)-, -N"'-(4-bromo-benzenesulphonyl)-, -N"'-(2-cyano-benzene-sulphonyl)-, -N"'-(2-nitro-benzenesulphonyl)-, -N"'-35 (4-nitro-benzenesulphonyl)-,~-N"'-(2-methyl-benzenno-lo A 23 308 - Foreign Countries 12;~83~7 sulphonyl)-, -N"'-(4-methyl-benzenesulphonyl)-, No chloromethyl-benzenesulphonyl)-, -N"'-~2-trifluoromethyl-benzenesulphonyl)-, -N"'-~2-methoxy-benzenesulphonyl)-, -N"'-(4-methoxy-benzenesulphonyl)-, -N"'-(2-methylthio-ben-zenesulphonyl)-, -N"'-(2-difluoromethoxy-benzenesulpho-nil)-, -N"'-(2-trifluoromethoxy-benzenesulphonyl)-, No methylthio-methyl-benzenesulphony~)-, -N"'-(2-dimethylami-no-sulphonyl-benzenesulphonyl)-, -N"'-(2-phenyl-benzene-sulphonyl)-, -N"'-(2-methoxysulphonyl-benzenesulphonyl)-, -N"'-(2-methoxycarbonyl-benzenesulphonyl)-, -Nighthawks-carbonyl-benzenesulphonyl)-, -N"'-(2-propoxycarbonyl-ben-zenesulphonyl)-, -N"'-t2-methylaminocarbonyl-benzenesul-phony)-, -N"'-(2-ethylaminocarbonyl-benzenesulphonyl)-, -N"'-(2-propylaminocarbonyl-benzenesulphonyl)-, No methoxyaminocarbonyl-benzenesulphonyl)-, -Nighthawks-aminocarbonyl-benzenesulphonyl)-, -N"'-(2-propoxyaminocar-bonyl-benzenesulphonyl)-, -N"'-(2-dimethylaminocarbonyl-benzenesulphonyl)- and -N"'-(2-diethylaminocarbonyl-ben-zenesulphonyl)-guanidine.
The compounds of the formula (If) can be prepared by the processes described above under (a) and (b).
Formula (V) provides a general definition of the sulphonyl chlorides also to be used as starting sub-stances on process variant (c). In formula (V), R10 preferably and particularly has the same meaning as us given above as preferred or as particularly preferred in the context of the definition of the substituents of formula (I).
The sulphonyl chlorides which have been men-toned above as examples of compounds of the formula (Iamb apply as examples of the starting substances of the formula (V).
The sulphonyl chlorides of the formula (V) are known andtor can be prepared by processes which are known per so (compare the literature and synthesis routes for the compounds of the formula (III) above).
lo A 23 308 - Foreign Countries _ 34 _ 1228357 Formula (VI) provides a general definition of the sulphonylguanidinotriazine derivatives to be used as starting substances for process variant (d). In formula TV), R3 , R4, R5 and R10 preferably and portico-laxly have the same meanings as are given above as pro-furred or as particularly preferred in the context of the definition of the substituents of formula (I).
Examples which may be mentioned of the compounds of the formula TV) are: N'-(4,~-dimethyl-s-triazin-2-I ye)-, N'-(4-methoxy-6-methyl-s-triazin-2-yl)-, No ethoxy-6-methyl-s-triazin-2-yl)-~ N'-(4,6-dimethoxy-s-triazin-2-yl)-, N'-(4,6-diethoxy-s-triazin-2-yl)-, No ethoxy-6-methoxy-s-triazin-2-yl)-, N'-(4-methyl-6-methyl-thio-s-triazin-2-yl)-, N'-(4-ethylthio-6-methyl-s-tria-zanily)-, N'-(4-methoxy-6-methylthio-s-triazin-2-yl)-, N'-(4-ethoxy-6-methylthio~s-triazin~2-yl)~, Knothole-thio-6-methoxy-s-triazin-2-yl)-, N'~(4~ethoxy-6~ethyl-thio-s-triazin-2-yl)-, N'-(4,6-bis-methylthio-s-tri~
assign)-, N'-(4,6-bis-ethylthio-s-triazin-2-yl)-, N'-(4-methyl-6-methylamino-s-triazin-2-yl)-, N'-(4-ethylamino-6-methyl-s-triazin-2~yl)~, N'-(4-dimethylamino-6-methyl-s-triazin-2-yl)-, N'-(4-diethylamino-6-methyl-s-triazin-yule)-, N'-(4-methoxy-6-methylamino-s-triazin-2-yl)-, N'-(4-ethylamino-6-methoxy-s-triazin-2-yl)-~ N'-(4-dimethyl-amino-6-methoxy-s-triazin-2-yl)-, N'-(4-diethylamino~6-methoxy-s-triazin-2-yl)-, N'-(4-ethoxy-6-methylamino-s-triazin-2-yl)-, N'-(4-ethoxy-6-ethylamino-s-triazin-2-ye)-, N'-(4-dimethylamino-6-ethoxy-s-triazin-2-yl)-, N'-(4-diethylamino-6-ethoxy-s-triazin-2-yl)-, N'-(4-methyl-AL amino-6-methylthio-s-triazin-2-yl)-, N'-(4-ethylamino-6-methylthio-s-triazin-2-yl)-, N'-(4-dimethylamino-6-methyl-thio-s-triazin-2-yl)-, N'-(4-diethylamino-6-methylthio-s-triazin-2-yl)-, N'-(4-ethylthio-6-methylamino-s-triazin-yule)-, N'-(4-dimethylamino-6-ethylthio-s-triazin~2~yl)~
and N'-(4~diethylamino-6-ethylthio-s-triazin-2~yl)-N"-methoxy-, -Nighthawks-, -N"-propoxy-, -N"-isopropoxy-, lo A 23 I - Foreign Countries _ 35 _ 1228357 -N"-butoxy-, -N"-isobutoxy-, -N"-sec.-butoxy-, -N"-pentyloxy-, -N"-hexyloxy-, -N"-octyloxy-, -N"-allyloxy~, -N"-t3-chloro-propoxy)-, -N"-methoxycarbonylmethoxy-, -N"-ethoxycarbonyl~
methoxy-, -N"-~Z-phenyl-ethoxy)-, -N"-benzyloxy-, No methyl~benzyloxy)-, -N"-(4-fluoro-benzyloxy)-, No chloro-benzyloxy)-, -N"-(4-nitro-benzyloxy)- and No methoxycarbonyl-benzyloxy)-, N"-benzenesulphonyl-, -N"-(2-chloro-benzenesulphonyl)-~ -N"-(4-chloro-benzenesulphonyl)-, -h"-(2-fluoro-benzenesulphonyl)-, -N"-(4-fluoro-benzene-sulphonyl)-, -h"-(2-bromo-benzenesulphonyl)-, -h"-(3-chloro-benzenesulphonyl)-, -N"-(2-cyano-benzenesulphonyL)-, -N"-(2-nitro-benzenesulphonyl)-, -N"-(4-nitro-benzenesulpho-nil)-, -N"-(2-methyl-benzenesulphonyL)-, -N"-(4~methyL-benzenesuLphonyl)-, -N"-(2-chloromethyl-benzenesulphonyl)-, -N"-(2-trifluoromethyL-benzenesulphonyl)-, -N"-(2-methoxy-benzenesuLphonyl)-, -N"-(4-methoxy-benzenesulphonyL)-, -N"-(2-methylthio-benzenesulphonyl)-, -N"-(2-difLuorome-thoxy-benzenesulphonyl)-~ -N"-(2-trifluoromethoxy-benzene-sulphonyl)-, -N"-(2-methylthiomethyl-benzenesulphonyl)-, -N"-(2-dimethylamino-sulphonyl-benzenesulphonyl)-~ -N"-(Z-phenyl-benzenesulphonyl)-, -N"-(methoxysulphonyl-benzenesulpho-nil)-, -h"-(2-methoxycarbonyl-benzenesuLphonyL)-, No ethoxycarbonyl-benzenesulphonyl)-, -N"-(2-propoxycarbonyl-benzenesuLphonyl)-, -N"-C2-(N-methyl-N-methoxy-amino-carbonyl-benzenesulphonyl]-, -N"-(2-dimethylaminocarbonyl-benzene-sulphonyl)- and -N"-(2-diethylaminocarbonyl-benzenesul-phonyl)-guanidine.
The sulphonylguanidinotriazine derivatives of the formula (VI) are new and can be prepared by a process analogous to process (a) by reacting guanidinotriazine derivatives of the formula (II) with somewhat equimolar amounts of sulphonyl chlorides of the formula (V).
Formula (III) provides a general definition of the sulphonyl chlorides also to be used as starting sub-stances in process variant (d). In formula Tao), R1preferably and particularly has the same meaning as is lo A 23 30~ - Foreign Countries 36 _ i228357 given above as preferred or as particularly preferred in the context of the definition of the substituents of formula I}).
Examples of the sulphonyl chlorides of the formula (III) and their preparation processes for this have already been given above in connection with the descrip-lion of the starting substances for process (a).
Formula VOW) provides a general definition of the sulphonylisothioureidotriazine derivatives to be used as I starting substances in process variant I In formula (VII), R1, R4 and R5 preferably and particularly have the same meanings as are given above as preferred or as particularly preferred in the context of the definition of the substituents of the formula (I), and R16 preferably and also particularly represents methyl.
Examples which may be mentioned of the compounds of the formula (VOW are: N'-(4,b-dimethyl-s-triazin-2-ye)-, N'-(4-methoxy-6-methyl-s-triazin-Z-yl)~, No ethoxy-6-methyl~s-triazin-2-yl)-, N'-(4,6-dimethoxy-s-I triazin-2-yl)-, N'-(4,6-diethoxy-s~triazin-2-y~)-, No ethoxy-6-methoxy-s-triazin-2-yl)-, N'-(4-methyl-6-methyl-thio-s-triazin-2-yl)-~ N'-(4-ethylthio-6-methyl-s-tria-zanily)-, N'-(4-methoxy-6-methylthio-s-triazin-Z-yl)-, N'-(4-ethoxy-6-methylthio-s-triazin-2-yl)-, Knothole-thio-o-methoxy-s-triazin-2-yl)-, N'-(4-ethoxy-6~ethylthio~
s-triazin-2-yl)-, N'-(4,6-bis-methylthio-s-triazin-yule N'-(4,6-bis-ethylthio-s-triazin-Z-yl)-, N'-(4-methyl-6-methylamino-s-triazin-2-yl)-, N'-(4-ethylamino-6-methyl-s-triazin-2-yl)-, N'-(4-dimethylamino-6-n1ethyl-I s-triazin-2-yl)-, N'~(4-diethylamino-6~methyl-s-triazin-yule)-, h'-(4-methoxy-6-methylamino-s-triazin-2-yl)-, N'-(4-ethylamino-6-methoxy-s-triazin-2-yl)-, N'-~4-dimethyl-amino-o-methoxy-s-triazin-2-yl)-, N'-(diethylamino-6-methoxy-s-triazin-2-yl)-, N'~(4~ethoxy-6-methylamino~s-triazin-2-yl)-, N'-(4-ethoxy-6-ethylamino-s-triazin-2-yl)-, N'-(4-dimethylamino-6-ethoxy-s-triazin-Z-yl)-~ N'-(4-di-lo A US 3~8 - Foreign Countries ~228357 ethylamino-6-ethoxy-s-triazin-2-yl)-, N'-(4-methylamino-6-methyl-thio-s-triazin-2-yl)-, N'-(4-ethylamino-6-methylthio-s-triazin-2-ye)-,N'-(4-dimethylamino-6-methylthio-s-triazin-2-yl)-,, No diethylamino-6-methylthio-s-triazin-2-yl)-, N'-(4-ethylthio-6-methylamino-s-triazin-2-yl)-, N'-(4-dimethylamino-6-ethylthio-s-triazin-2-yl)- and N'-(4-diethylamino-6-ethylthio-s-triazin-2-yl)-N"-(2-fluoro-benzenesulphonyl)-, -N"-(2-chloro-benzenesul-phony)-, -N"-(2-bromo-benzenesulphonyl)-, -N"-(2-methyl-benzene-sulphonyl)-, -N"-(2-methoxy-benzenesulphonyl)-, -N"-(2-methoxy-carbonyl-benzenesul.phonyl)-, -N"-(2-ethoxy-carbonyl- benzene-sulphonyl)-, -N"-(2-propoxycarbonyl-benzenesulphonyl)-, -N"-~2-isopropoxycarbonyl-benzenesulphonyl)-, -N"-(2-phenyl-benzene-sulphonyl)-, -N"-(2-trifluoromethyl-benzenesulphonyl)-, No difluoromethoxy-benzenesulphonyl)- and -N"-(2-trifluoromethoxy-benzenesulphonyl)-S-methyl-isothiourea.
Some of the sulphonylisothioureidotriazine derivatives of the formula (VII) are known and/or can be prepared by processes which are known so (compare EGOS (European Published Specification) 5,986).
It is to be noted however, that compounds of the formula (VII), in which Al represents a phenol radical substituted in ortho-position by Cl-C4-fluoroalkoxy, Cl-C4-alkylthio, Cluck-alkylsulphinyl or Cl-C4-alkylsulphonyl, and in which R4, R5 and R16 have the above mentioned meanings, are not yet known and are the subject of the divisional application.
According to one aspect of the invention of the divisional application there is provided a sulphonylisothioureido-treason derivative of the general formula (VIVA) 12~:8357 N
R -SWEENEY , N I/ N

I R5 (VIVA) in which Ala represents a substituted phenol radical ROY

wherein ROY represents Cl-C4-fluoroalkoxy, Cl-C4-alkylthio, Cl-C4-alkylsulphinyl or Cl-C4-alkylsulphonyl;
R4 represents fluorine, chlorine, bromide, cyclopropyl or Cl-C4-alkyl (which is optionally substituted by fluorine or chlorine), or represents Cl-C4-alkoxy (which is optionally substituted by fluorine or chlorine), or represents Cl-C4-alkylthio (which is optionally substituted by fluorine or chlorine), or represents Cl-C4-alkyl- or di-(Cl-C4-alkyl)-amino (which are optionally substituted by fluorine);
R5 represents fluorine, chlorine, bromide, cyclopropyl, Cl-C4-alkyl (which is optionally substituted by fluorine or chlorine), or represents Cl-C4-alkoxy (which is optionally substituted by fluorine or chlorine), or represents Cl-C4-alkylthio (which is optionally substituted by fluorine or chlorine), or represents Cl-C4-alkyl- or di-(Cl-C4-alkyl)-amino (which are optionally substituted by fluorine); and _ aye -isle R16 represents Cl-C4-alkyl or bouncily.
According to a further aspect of the invention of the divisional application there is provided a process for the preparation of sulphonylisothioureidotriazine derivative of the formula (VIVA) as defined above, which process comprises reacting an N-sulphonyl-imino-dithiocarbonic acid ester of the formula (EVA) S 2 (EVA) in which Ala and R16 have the meanings given above, with an aminotriazine of the formula (XI) N
HEN I/ N (XI) in which R4 and R5 have the meanings given above, and, when the reaction has ended, diluting the mixture with water and acidifying with a strong acid.
The compounds of the formula (VII) are obtained by a process in which N-sulphonyl-imino-dithiocarbonic acid esters of the formula (XV) Al -SO 2 NO ( XV ) in which ,:
- 37b -835~

Al and R16 have the above mentioned meanings, are reacted with aminotriazines of the formula (XI) HEN I/ N (XI) in which R4 and R5 have the above mentioned meanings, - 37c -38 _ 12~8357 if appropriate in the presence of bases, such as, for example, sodium hydrides or potassium tert.-butyLate, and if appropriate in the presence of delineates such as, for example, tetrahydrofuran, Dixon or dimethylformamide, at temperatures between C and 100C, and, when the reaction has ended, the mixture is diluted with water and acidified with a strong acid, such as, for example, hydra-caloric acid, and the products of the formula (VII) ox-twined as crystals are isolated by filtration with suction.
AL Formula (XV) provides a general definition of the N-sulphonyl-imino-dithiocarbonic acid esters required here as starting substances. In formula (XV), R1 and R16 preferably end particularly have the same meanings as are given above as preferred or as particularly preferred in the context of the definition of the substituents of formula (I) or formula (VII ) .
Examples which may be mentioned of the compounds of the formula TV are: S,S-dimethyl N-(2-fluoro-ben-zenesulphonyl)-, h-(2-chloro-benzenesulphonyl)-, No 2b bromo-benzenesulphonyl)-, N-(2-methyl-benzenesulphonyl)-, N-(2-methoxycarbonyl-benzenesulphonyl)-, N-(2-ethoxycar-bonyL-benzenesulphonyl)-, N-(2-propoxycarbonyl-benzene-sulphonyl)-, N-(2-isopropoxycarbonyl-benzenesulphonyl)-, N-(2~phenyl-benzenesulphonyl)~, N-(2-trifluoromethyl-ben-zenesulphonyl)-; N-(2-difluoromethoxy-benzenesulphonyl)-anN-(2-trifluoromethoxy-benzenesulphonyl)-iminodithito-carbonate.
The N-sulphonyl-iminodithiocarbonic acid esters of the formula (XV) are known and/or can be prepared by I processes which are known per so (compare Chum. Ben. 99 (1900), 2~5 and EGOS (European Published Specification) o ) .
The compounds of the formula (XV) are obtained by a process in which sulfonamides of the formula (XVI) R1-SO~-NH2 (XVI) in which lo A 23 SOS - Foreign Countries 12~8357 _ I _ R1 has the above mentioned meaning, are reacted with carbon disulphide in the presence of a strong base, such as, for example, sociium hydroxide, and if appropriate in the presence of delineates, such as, for example, water an dimethy~formamide, at temperatures bet-wren UC and 1UuC, and then (in situp with an alkylating agent of the formula (ZOO) X-R16 (XVII) in which R16 has the above mentioned meaning and represents chlorine, bromide or iodine, at temperatures between 0C and 1U0C.
The products of the formula (XV) obtained as cry-slats after dilution of the mixture with water can be is-US fated by filtration with suction.
Formula (XVI) provides a general definition of thesulphonamides required as starting substances. In formula (ZOO), R1 preferably and particularly has the same meaning as given above as preferred or as particularly AL preferred in the context of the definition of the substituents of formula (I).
Examples which may be mentioned of the compounds of the formula (ZOO) are: flyer-, sheller Brigham-, methyl 2-methoxycarbonyl-~ Z-ethoxycarbonyl-, 2-pro-US poxycarbonyl-, 2-isopropoxycarbonyl-, phenol-, try-fluoromethyl-, 2-difluoromethoxy- and 2-trifluoromethoxy-benzenesulphonamide.
The sulfonamides of the formula (ZOO) are known and/or can be prepared by processes which are known 30 per so compare EGOS European Published Specifications) Z3,4~2, 3U,140, ~5,893, owe, 44,~0h, 44,~09, 51,466, owe, 70,041 and USE; US. Patent Specification

4,3?2,77~ an Oh. Org. Kim. [J. Org. Chum. USSR] 8 (1972), 1U~3-1026 English 1032-1U34]).
These compounds are obtained in a manner which is known per so, by reacting sulphonyl chlorides of the lo A us 30~ - Foreign Countries formula (Ill) - above - with ammonia, if appropriate in the presence of delineates, such as, for example, deathly ether, tetrahydrofuran or water, at temperatures between LJOC and 10~C. The products of the formula (ZOO) S thereby obtained as crystals can be isolated by filtration with suction Examples of suitable starting compounds of the formula Tao) and preparation methods for these are given above in the description of the starting substances for I process (a).
Examples which may be mentioned of the starting substances of the formula (ZOO) are: methyl chloride, methyl bromide, methyl iodide, ethyl chloride, ethyl brow mile and ethyl iodide, and bouncily chloride and bouncily bromide.
The compounds of the formula (ZOO) are known.
Formula (XI) provides a general definition of the aminotriazines also to be used as starting substances. In formula (ZOO, R4 and US preferably and particularly have the same meanings as are mentioned above as preferred or as particularly preferred in the context of the definition of the substituents of formula (I).
Examples which may be mentioned of the compounds of the formula (XI) are: 4,6-dimethyl-, 4-methoxy-6-me-thy-, 4-ethoxy-6-methyl-, 4,6-dimethoxy-, 4,6-diethoxy-, 4-ethoxy-6-methoxy-, 4-methyl-6-me~hylthio-, 4-ethylthio-methyl-, 4-methoxy-6-methylthio-, 4-ethoxy-6-methylthio-, 4-ethylthio-6-methoxy-, 4-ethoxy-6-ethylthio-, Boyce-methylthio-, 4,6-bis~ethylthio-, 4-methyl-o-methylamino-, I 4-ethylamino-6-methyl-, 4-dimethylamino-6-methyl-, Dow-ethylamino-o-methyl-, 4-methoxy-6-methylamino-, 4-ethyl-amino-6-methoxy-, 4-dimethylamino-6-methoxy-, deathly-amino-6-methoxy-, 4-ethoxy-6-methylamino-, ethics-ethyl amino-, 4-dimethylamino-6-ethoxy-, 4~diethylamino~6-ethics-, 4-methylamino-6-methylthio-, 4-ethylamino-6-methylthio-, 4-dimethylamino~6~methylthio~, lo A I 3U8 - Foreign Countries 12~8~57 4-diethylamino-6-methylthio-, 4-ethylthio-6-methylamino-, 4-dimethylamino-6-ethylthio and 4-diethylamino-6-ethylthio-2-amino-s-triazine.
The aminotriazines of the formula (XI) are known and/or can be prepared by processes which are known per so.
Formula (IV) provides a general definition of the amino compounds also to be used as starting substances in process van-ant (e). In formula (IV), R2 preferably represents hydrogen or methyl, in particular hydrogen, and R3 preferably and particularly has the same meaning as is given above as preferred or as particularly preferred in the context of the definition of the substituents for formula (I).
Examples of suitable starting substances of the formula (IV) and literature references for these are given above in the description of the starting substances for process (b).
Formula (I) - with the proviso that M represents hydrogen - provides a general definition of the compounds to be used as starting substances in process variant (f). In formula (I) -where this relates to the compounds to be used as starting sub-stances for process (f) - M represents hydrogen and Al, R2, R3, R4 and R5 preferably and particularly have the same meanings as are given above as preferred or as particularly preferred in the context of the definition of the substituents of formula (I).
The compounds of the formula (I) to be used as starting substances for process (f) can be prepared by the processes desk cried under (a), (b), (c), (d) and (e).
Examples which may be mentioned of the metal hydroxides, hydrides and alkanolates and organometallic compounds to be used in process (f) are: the hydroxides of lithium, sodium, potassium, magnesium and calcium, the hydrides of lithium, sodium and calcium, sodium methanol ate and ethanol ate, potassium methanol ate, ethanol late and potassium tert.-butanolate, and butyl-lithium and is-propyl-magnesium chloride.
Formula (I) - with the proviso that M represents hydrogen - provides a general definition of the compounds to be used as starting substances in process variant (g). In formula (I) - where this relates to the compounds to be used as starting substances for process (g) - M represents hydrogen and Al, R2, R , R4 and R5 preferably and particularly have the same meanings as are given above as preferred or as particularly preferred in the context of the definition of the substituents of formula (I).
The compounds of the formula (I) to be used as starting substances for process (g) can be prepared by the processes described under (a), (b), (c), (d) and (e).
Strong acids are used as starting substances in process (g). These are preferably hydrogen halide acids, such as hydrogen chloride, hydrogen bromide or hydrogen iodide, and furthermore sulfuric acid or alkanesulphonic acids which have up to 4 carbon atoms and are optionally substituted by fluorine or chlorine, such as, for example, methanesulphonic acid, ethanesulphonic acid, chloromethanesulphonic acid, 2-chloroethanesulphonic acid and in-fluoromethanesulphonic acid, trifluoroacetic acid and furthermore benzenesulphonic acid, p-toluenesulphonic acid, naphthalene-l-sulphonic acid, naphthalene-2-sulphonic acid and naphthalene-1,4-, -1,5-, -1,6-, -2,6- and -2,7-disulphonic acid.
Process (a) according to the invention for the prepare-lion of the new compounds of the formula (I) is preferably carried 8;~S7 - aye - 23189-6066 out using delineates. Possible delineates are virtually all the inert organic solvents, but preferably aprotic polar solvents. These in-elude optionally substituted hydrocarbons, such as, for example, ethylene chloride, chloroform, 1,2-dichloroethane, Tulane, zillion and chlorobenzene, nitrites, such as acetonitrile and propionitrile, ethers, such as, for example, ` _ 43 _ 1228357 1~2-dimelhoxyethane~ tetrahy~rofuran and dnoxane, and I-methylformamiae, dimethylacetam1~e, dim ethyl suLphoxide, sulpholane, pardon and 2-methyl-5-ethyL-pyridine.
Virtually all the acid-binding agents which are usually employed can be used as acid acceptors in pro-cuss (a). These include, in particular, alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal Horace, organometallic compounds, such as butyl-lithium, and furthermore aliphatic, aromatic or MU heterocyclic amine, such as trimethylamine, triethylamine, h,N-dimethylar,iline, ~,N-dimethyl-benzylamine, Disobeys-clooctane (DABCO), diazabicyclononene (DUB), diazabicyclo-undecene (DUB), pardon, 2-methyl-5-ethyl-pyridine and 4-dimethylamino-pyridine.
The reaction temperatures can be varied within a substantial range in process (a). In general, the react lion is carried out between -I and +10~C, preferably between -I and +5~C. Process (a) according to the invention is in general carried out under normal pressure.
For carrying out process (a), in general between 1 and 5 moles, preferably between 2 an 3 moles, of sulk phony chloride of the formula Tao) are employed per mole of guanidinotriazine derivative of the formula (II).
The reaction components are usually brought to-tether at room temperature or with external cooling and the reaction mixture is stirred until the reaction has ended.
The new compounds are worked up and isolated by customary methods. The mixture is shaken with water and So a water-immiscible solvent, such as, for example, methyl tone chloride, chloroform or Tulane, if appropriate after the volatile components have been distilled off, and the organic phase is washed with water, dried, filtered and concentrated The products of the formula (It which no-main in the residue are made to crystallize by digestion with organic solvents, such as, for example, deathly ether, lo A 23 3~8 - Foreign Countries -12~8~57 ethyl acetate, ethanol or isopropanol, and, if appropriate, are purified by recrystallization.
Process (b) according to the invention is prefer-ably carried out using delineates. Possible delineates are virtually all the inert organic solvents. These include, in particular, alcohols, such as methanol, ethanol and n- or i-propanol, ethers, such as tetrahydrofuran, Dixon and 1,~-dimethoxyethane, esters, such as methyl acetate and ethyl acetate, nitrites, such Astor example, acetonitrile I or propionitrile, and dimethylformamide and water.
Acld-binding agents winch do not have nucleophilic properties which noticeably compete with those of the amino compounds of the formula (IV) can be used as acid acceptors in process (b). As acid acceptors of this type US there may be mentioned alkali metal and alkaline earth me-tat carbonates, such as, for example, potassium carbonate and calcium carbonate, tertiary amine, such as, for example, triethylamine, ~i,N-dimethylaniline and India methylbenzylamine and nitrogen-containing heterocyclic I compounds, such as, for example, pardon, diazabicyclo-octane (DABC0) and diazabicycloundecene DUB
The reaction temperature can be varied within a substantial range in process (b). In general, the react lion is carried out between bC and 150C, preferably I between 1~C and 10~C. Process (b) according to the invention is in general carried out under normal pressure.
For carrying out process (b) according to the in-mention, in general between 1 and MU moles, preferably between and 5 moles, of amino compound of the formula I (IV) or hydrochloride thereof are employed per mole of the compound of the formula (ID).
In general, the compound of the formula (ID) and the delineate are taken at 2~1C or with gentle cooling, and the amino compound of the formula (IV) or the hydrochloride I thereof and, if appropriate, a suitable acid acceptor are added. The reaction nlixture is then in general stirred lo A 8 - Foreign Countries _ 45 _ 12~8357 at room temperature or elevated temperature until the no-action has ended.
Working up can be carried out by customary methods.
If the products of the formula (I) are obtained as cry-

5 slats from the reaction mixture, they can be isolated by filtration with suction. Otherwise - if appropriate after concentration the mixture is diluted with water and ox-treated with a solvent which is virtually water-immiscible, such as, for example, ethylene chloride. The products MU of the formula (I) can be obtained in a pure form by wash-in the extraction solution with water, crying, filtration, concentration of the filtrate an recrystallization of the residue.
Process lo) according to the invention is prefer-ably carried out using delineates. Possible delineates are virtually all the inert organic solvents, but preferably aprot1c polar solvents, such as have been mentioned above in connection with the description, of process (a) accord-in to the invention.
MU virtually all the acid-binding agents which are usually employed can be used as acid acceptors in pro-cuss (c). These include, in particular, the acid-binding agents mentioner above in connection with the description of process (a) according to the invention.
I The reaction temperatures can be varied within a substantial range in process (c). In general, the react lion is carried out between -~UC and +1U~C, preferably between -3UOC and ~5UC. Process (c) is in general carried out under normal pressure.
I For carrying out process (c), in general between 1 and moles, preferably between 1.1 and 1.5 moles, of sulphonyl chloride of the formula (V) are employed per mole of sulphonylguanidinotriazine derivative of the formula (If).
The procedure and working up in process (c) can be analogous to process to).
lo A I I - Foreign Countries - 46 - 12~8357 Process (d) according to the invention is prefer-ably carries out using ailments. Possible delineates are virtually all the inert organic solvents, but preferably aprotic polar solvents, such as have been mentioned above in connection with the description of process (a) accord-in to the invention.
All the acid-binding agents which are usually employed can be used as acid acceptors in process (d).
These induce, in particular, the acid-binding agents men-I Sheehan above in connection with the description of process according to the invention.
The reaction temperatures can be varied within a substantial range in process (d). In general, the react lion is carried out between -8~C and +1~C, preferably I between -SKYE and +5~C. Process (d) is in general carried out under normal pressure.
For carrying out process (d), in general between - 1 and 2 nulls, preferably between 1.1 and 1.5 moles, of sulphonyl chloride of the formula (III) are employed I per mole of sulphonylguanidinotriazine derivative of the formula (I
The procedure and working up in process (d) can be analogous to process (a).
Process (e) according to the invention is prefer-I ably carries out using delineates. Possible delineates are virtually all the inert organic solvents, but preferably aprotic polar solvents. These include, in particular, tetrahydrofuran, axon, 1,~-dimethoxyethane, acetone-trite, acetone, methyl ethyl kitten, methyl isobutyl key I tone, ailnethylformamide~ dimethylacetamide and dimethylsulphoxiae.
The reaction temperature can be varied within a substantial range in process (e). In general, the react lion is carried out between C and 15~C, preferably between 1~C and 1~C. Process (e) is in general car-fled out under normal pressure or slightly reduced lo A 23 3~8 - Foreign Countries pressure.
For carrying out process (e) according to the in-mention, in general between 1 and I moles, preferably be-tweet 1 and 5 moles, of amino compound of the formula (IV) are employed per mole of sulphonylisothioureidotria-zinc derivative of the formula IT
In general, the sulphonylisothioureidotriazine de-rivatives of the formula (VII) and the delineate are taken and the amino compound of the formula (IV) is metered in.
I The reaction mixture is then stirred until the reaction has ended. The products of the formula (It are usually obtained as crystals, after cooling and if appropriate after acidification, for example with hydrochloric acid, and can be isolated by filtration with suction.
Process I according to the invention is prefer-ably carried out using delineates. Possible delineates are virtually all the inert organic solvents. These include, in particular, alcohols, such as, for example, ethanol and n- or lso-propanol, ethers, such as, ion example, twitter-I hydrofuran, Dixon and 1,2-dimethoxyethane, esters, such as, ion example, ethyl acetate and methyl acetate, and nitrites, such as, for example, acetonitrile.
The reaction temperature can be varied within a substantial range in process (f). In general, the react US lion is carried out between -2~C and +5~C, preferably between C and 3~C. Process (f) is in general carried out under normal pressure.
For carrying out process I according to the in-venison in general between by and 1.2 moles, preferably I between ~.95 and 1.1 moles, of metal compound are employed per mole of the compound of the formula (I).
In general, the compounds of the formula (It and the delineate are taken and - if appropriate with gentle external cooling - the metal compound - if appropriate dissolved in the delineate - is metered in. The reaction mixture is stirred until the reaction has ended. The lo A I I - Foreign Countries I ~228~57 salt-like products of the formula (I) are in general ox-twined as crystals and can be isolated by filtration with suction.
Process (g) according to the invention is prefer-ably carried out using delineates. Possible delineates are virtually all the inert organic solvents. These include, in particular, alcohols, such as, for example, methanol, ethanol and n- or iso-propanol, ethers, such as, for example, tetrahyarofur3n, Dixon and 1,2-dimethoxy-I ethanes esters, such as, for example, methyl acetate and ethyl acetate, an kittens, such as acetone, methyl ethyl kitten and methyl isobutyl kitten.
If the acids used as starting substances are em-ply in aqueous solution, acetic android can Avon-I tageously also be used as the ailment.
The reaction temperature can be varied within substantial range in process (9). In general, the react lion is carried out between -2~C and +5~C, preferably between C and +~C. process (g) is in general car-fled out under normal pressure.
For carrying out process (g) according to the in-mention, in genera between 1 and I moles, preferably 1 an 5 moles, of a strong acid are employed per mole of the compound of the formula (I).
In general, the compounds of the formula (I) and the delineate are taken and - if appropriate with gentle ox-vernal cooling - the strong acid is metered in. The react lion mixture is stirred until the reaction has ended. The 1:1 abducts are in general obtained as crystals and can I be isolated by filtration with suction.
The active compounds according to the invention, can be used as defoliants, desiccants, agents for destroy-in broad-leaved plants and, especially, as weed killers.
By weeds, in the broadest sense, there are to be understood I all plants which grow in locations where they are undo-sired. whether the substances according to the invention lo A I so - Foreign Countries act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the following plants:
Vicotyledon weeds of the genera: Synapse, Lipid-I'm, Gallium, Styler, Motorcar, Anthems, Galinsoga, Chenopodium, Utica, Synch, Amaranths, Portulaca, Ken-thrum, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Keywords, Sonchus, Selenium, Rewrap, Rotate, Lint AL hernia, Lamium, Veronica, Abutilon, Emex, Dotter, ~iola,Galeopsis, Palaver and Sinatra.
cotyledon cultures of the genera: 60ssypium, Gleason, Beta, Caucus, Fossils, Possum, Selenium, Linus, Ipomoea, itch, ~icotiana, Lycopersicon, Arachis, Brusque, lag-tuna, Cucumis and Cucurbita.~lonocotyledon weeds of the genera: Echinochloa, Satyr, ~anicum, Digit aria, Phlegm, Poe, Fistic, Eleusine, Brush-aria, Lolium, Browns, Arena, Cyprus, Sorghum, Agropyron, Sundown, Monkery, FimbristyLis, Sagittaria, Eleocharis, Lo Syrups, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Opera.
Monocotyledon cultures of the genera: Ours, Zeal Trill-gum, H~r~eum, Arena, Scale, Sorghum, Panicum, Saccharum, Bananas, Asparagus and Gallium.
I 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 con-cent ration, for the total combating of weeds, for example I on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equally, the cow-pounds can be employed for combating weeds in perennial cultures, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut ouch-ends, banana plantations, coffee plantations, tea plant-lions, rubber plantations, oil palm plantations, cocoa lo A I AL - Foreign Countries 28~S7 - MU
plantations, soft fruit plantings and hop fields, and for the selective combating of weeds in annual cultures.
The active compounds according to the invention can be used for selectively combating weeps in monocotyLedon and S dicoty~edon crops, such as, for example, cotton, rice, cereals and maize. [The active compounds according to the invention also exhibit a fungicidal action against Pyrrhic-lane ours in rice.]
The active compounds can be converted to the gusto-I many formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concern-trades, natural and synthetic materials impregnated with active compound, and very fine capsules in polar substances.
These formulations are produced in known manner, for example by mixing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying I agents and/or dispersing agents and/or foam-forming agents.
In the case of the use of water an an extender, organic solvents can, for example, also be used as Audi-diary solvents. As liquid solvents, there are suitable in the main: aromatics, such as zillion, Tulane or alkyd I naphthalenes, chlorinated aromatics and chlorinated alit phatic hydrocarbons, such as chlorobenzenes, chloroethyl-ones or ethylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example petroleum free-lions, mineral and vegetable oils, alcohols, such as but-I not or gawkily as well as their ethers and esters, ketones,such as acetone, methyl ethyl kitten, methyl isobutyl key tone or cyclohexanone, strongly polar solvents such as dimethylformamide and dim ethyl sulphoxicle, as well as water.
As solid carriers there are suitable: for example ammonium salts and round natural minerals, such as kayo-fins, clays, talc, chalk, quartz, attapulgite, lo A I by - Foreign Countries - 51 - 12~8357 montmorillonite or diatomaceous earth, and ground Cynthia-tic minerals, such as highly disperse silicic acid, alum-no an silicates, as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolor mite, as well as synthetic granules of inorganic and organ nix meals, and granules of organic material such as saw-aunt, coconut shells, maize cobs and tobacco stalks; as emulsifying and/or foam-~orminy agents there are suitable:
I for example non-ionic and anionic emulsifiers, such as polyoxyethylene-fatty acid esters, polyoxyethylene-fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsuLphonates, alkylsulphates, ary~sulphonates as well as albumin hydrolysation products; as dispersing agents there are suitable: or example lignin-sulphite waste liquors and methyl cellulose.
Adhesives such as carboxymethylcellulose and NATO-fat and synthetic polymers in the form of powders, gray nulls or lattices, such as gum Arabic polyvinyl alcohol I and polyvinyl acetate, as well as natural phospholipids such as cephalins and lecithins, and synthetic phospholi-pods, can be used in the formulations. Further additives can be mineral and vegetable oils.
It is possible to use colorants such as inorganic I pigments, for example iron oxide, titanium oxide and Prows Sian Blue, and organic distaffs, such as alizarin aye-stuffs, ago distaffs and metal phthalocyanine distaffs, 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 I and 90X.
The active compounds according to the invention, as such or in the form of their formulations, can also be 35 used, for combating weeds, as mixtures with known herb-aides, finished formulations or tank mixes being possible.
lo A I 30~ - Foreign Countries 1228~S7 For the mixtures come known herbicides, such as, for example, N-(2-benzothiazolyl)-N,N'-dimethylurea, 3-(3-chloro-4-methylphenyl)-1,1-dimethyl urea, 3-(4-isopropylphenyl)-1,1-dimethyl urea, Amman-dimethylethyl)-3-methylthio-1,2,4-triazin-5(4H)-onno, 4-amino-6-(1,1-dimethyl-ethyl)-3-ethylthio-1,2,4-triiazin-5-(one, 1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4-(1H,3H)-dione, 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one, 2-chloro-4-ethylamino-6-1û ;sopropyl-amino-1,3,5-tr;azine, the R-enantiomer of (tr;methylsilyl)-methyl 2-~4-(3,5-dichloro-pyridyl-2-oxy)-phenoxy]-propionate, the R-enantiomer of (bouncily-oxy)-ethyl 2-C4-(3,5-dichloropyridyl-2-oxy)-phenoxy~-pro-pinnate, 2,4-dichlorophenoxyacetic acid, 2-(2,4-dichloro-phenoxy)-propionic acid, 4-chloro-2-methyl-phenoxy-ace-tic acid, 2-(2-methyl-4-chloro-phenoxy)-propionic acid, 3,5-diiodo-4-hydroxy-benzonitrile, 3,5-dibromo-4-hydroxy-benzonitrile and diphenyl ethers and phenylpyridazines, such as, for example, peridots. Surprisingly, some mixtures also show a synergistic action.
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 soul-lions, suspensions, emulsions, powders, pastes and grant vies. They are used in the customary 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 lo A 23 308 - Foreign Countries ~228357 - I -a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are between U.UU1 and 15 kg of active compound per Hector of soil surface, preferably between USE and 10 kg per ha.
S The preparation and use of the active compounds according to the invention can be seen from the following examples.
Preparation examples Example 1 1 Jo ONE N I/

\

(Process (a)) 2.5 9 (0.14 mole) of 2-chloro-benzenesulphonyl chloride are addle to a mixture, cooled to -7C, of Lowe g (U.U37 mole) of N'-(4-diethylamino-6-methoxy-s-triazin-2-yL)-h"-methoxy-guanidine and 70 ml of pardon, with stir-ring, and the reaction mixture is stirred at 2UC for 3 days. It is then diluted with water and deathly ether.
Tune product thereby obtained as crystals is isolated by filtration with suction.
MU 15.~ 9 I of theory) of N'-(4-diethylamino-6-methoxy-s-triazin-2-yl)-N"-methoxy-N",N"'-bis-(2-csheller-benzenesulphonyl)-guanidine of melting point 133C are obtained.
Example 2 I H N OH

lo A 23 huh - Foreign Countries 54 12~8357 (Process (c)) 54 9 (U.256 mole) of 2-chloro-benzenesulphonyl chloride are added drops to a mixture, cooled to -2UOC~
of 97 g Us mole) of h'-(4-methoxy-6-methyl-s-triazin-2-yl)-5h"-methoxy-li"'-(~-chloro-benzenesu~phonyl)-guaniddine and 30U ml of pardon, with stirring. The reaction mixture is stirred it 2~C fox lo hours and concentrated. The residue is taken up in 3UU ml of ethylene chloride and this solution is washed twice with 15U ml of dilute hydra-I caloric acid each time, filtered and concentrated. Theproauct obtainer as crystals on trituration of the residue with ethanol is isolated by filtration with suction.
U 9 oh of theory) of ~'-(4-methoxy-6~methyl-s~
triazin-2-yl)-N"-methoxy-N"-N"'-bis-(2-chloro-benzzenesul-phonyl~-guanidine of melting point 164C are obtained.
Example 3 N OUCH

H OUCH

(Process (e)) A mixture of 1U.0 9 Us mole) of N'-(4~6-dime-thoxy-s-triazin-Z-yl)-h"-(2-chloro-benzenesulphonyyules-methyl-isothiourea, I g (~.065 mole) of U-methyl-hydroxyl-amine and ml of Dixon s stirred at 2UC for MU hours.
It is then concentrated, the residue is triturated with ethanol and the product obtained as crystals is isolated I by filtration with suction.
I 9 (57X of theory) of N'-(4,6-dimethoxy-s-tri~
azin-2-yl)-N"-methoxy-N"'-(2-chloro-benzenesulphonnil)-undone of melting point 15~C are obtained.

lo A Z3 I - Foreign Countries - 55 _ 1228357 Example 4 N a) C No OUCH

~50/ OKAY

(process (f)) A mixture of Us 9 (0.~1 mole) of N'-(4-methoxy-56-methyl-s-triazin-Z-yl)-N"-methoxy-h",N"'-bis-(2--sheller benzenesulphonyL)-yuanidine~ 54 9 01 mole) of so-drum methyl ate and 5 ml of methanol is stirred at ~UC
for 1 hour. The product obtained as crystals is then is-fated by filtration with suction.
MU Us 9 (YO-YO. of theory) of the sodium salt of N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-methoxy-N",Nibs ~2-chloro-benzenesulphonyl)-guanidine of melting point C are obtained.
Example 5 US H N SHEA x H2504 N
Of process go A mixture of 5.7 9 ~.01 mole) of N'-(4-methoxy-~-methyl-s-triazin-~-yl)-N"-methoxy-N" ,N"'-bis-~2-chloro-benzenesu~phonyl)~guanidine, 1.0 9 (OWE mole) of concern-MU treated sulfuric acid and 30 ml of acetone is stirred Attica for 15 hours. The product obtained as crystals is then isolated by filtration with suction.
5.3 9 (81X of theory) of the 1:1 adduce of No methoxy-~-methyl-s-triazin-2-yl)-N"-methoxy-N",N"''-bus-lo A I MU& - Foreign Countries -12~:8357 (~-chloro-benzenesulphonyl)-guanidine and sulfuric acid of melting point 148C are obtained.
The compounds of the formula (I) listed in the following Table 1 can be prepared by the processes described by way of example in the preceding Examples:

` No R (I ) No lo A I Jo - Foreign Countries _ 5 7 .

, ~17 D I
C _ I J _ _ ,, I O O O O
a) o s Q

N
N N
1 5 I I" 5 urn ON
Z Z O Z Z Z

I

to try I
O O

I
I

N

Z O O O O O
I

I I I to I I
N T N No N N
O O O Tao Lo O O
Us O Us OUT O Us Us N I --I I O I OX O I -- I

O o ' o O I o It 1 C ' a Q
_ E
D 11~ ' I
_ X O Do I I

lo A 23 foreign Countries 12;; :835~
I
, In , t_ c L I L
, I O
E N
O I _ _, to O O O O

T to O O G

I; , O O O O O O

I T N N N N S N N
l I.) O O l") O O O O
I O Us IL Us IS. Us O Us O Us Us N I O to O I O I

N
C N try ., I" T
c I I I

I

D (11 ' I
`` U ZOO I N ' Lo lo A 23 308- Foreign Countries .;

12;~8357 - I - .

Jo , I Of O , c _ , o N E
C I N O
, Jo ., --, _, _ I<
Q O
S CAL
I

I I _ Jo 5 5 T

Us ;') 1 5 t'" t" to 5 I; I 0 o 5 5 r N

Z O O O O
I

I 5 t O ~_~

I

I , O O O O O O
I

N
D
N l T
O
., I
I
I
I
C I
I) , I I
_ E
X O , 0 O -- N to 1-- US Z , ,_ N N N N

lo A 23 308- Foreign Countries _ 60 _ Jo , .
C L
., _ I
I N
_ c S o Q

I S I
O O O O
I .

try t_) S
o o I N

N
O O O O O

N
Us T' if I , , I
., , I, k.

C`

I , I Q
_ E
11 .
I, X O I U ED to lo A 23 308- Foreign Countries , 12,~8357 7, I .
C o , . o _ c i on N i , S I: S

i i S T I or O O O O . O O

Jo '.
T I) S
it I O I'm I'm O I O

i ON N N
S = or it 1 5 I O
O O Z Z Z Z

i i I
i 5 I: S
C
O
., 1 I
N
I

if I, ill Z ' O ...

lo A 23 308- ion Countries 122~3357 -- 6 2 -- o o I .
C _ , o -- v I E
C I O
N
o Q. I

I
I

N I 3 5 or Us I o O o o O O

o O N

N N

Z o I-) I O

N to N
N I C Jo 5 I N
C I t"
O

Q
,_ E
x O I o . --I
Jo z , or lo A 23 foreign Countries l'Z28357 _ 63 _ , ; .
or o ' O
N E -- E
O

T T ;

I: , O O O O O O

Us ~'~ 5 eye 1 5 N NUN 5 :;:
N

N
O

N , O N
T To lo I N
C , or Al Q
_ E
.
to x o I N to I' Lo Z I

lo A 23 308- Fore gun Count n en -- I --O
Q
an , L.
HO
_ I
a O
S Q

I ,(.~ 0 I
N or N N
O Z O O I) O I I O

to) to I I T
T N T N N on N O O O O O Us T C O I

h . IL --,~ e ho L ~[~

a E
n .
O 0 O -- N to _ LIT z , Lo lo A 23 308- Foreign Countries _ 65 _ C _ I
., , C:
C I o o' I

r _ 2 Lo s _ s s U) I V V to to , o o o o O O

' s T 5 S
V I_) V t) N
S S S
I; , S o Vow o o O

N
I:
Us N I N I S
N N to N V N V N V N
O o S o o o o o o o N I --I Us O Us O Us O Us ~v~3v~

N
I) C , S

S
C , N N S
O

V~o,~V~[~3V~3 I

I I .
nix o I I, "I ED
U- Z I Us lo A 23 308- Foreign Countries - 66 - :1228357 , I
C
, I
I
Of I
S T . T S T 5 I

to to t I I O O O O O O

I

to to to to I, 5 T T 5 I 5 I

to try try try to try if) , 5 to 5 5 5 5 C; I O O O O O O
N
N -- N
Us _ try ON 5 Al t t_) to try _ 1 5 N t.) N Z N Z N Z N N

O O O N O N O N O N O
N I -- U) OUT O O Us O Us O Us N
N
C I -- 11~
., I 5 T N
Jo I try to 1 5 _ _ T
so I to Z Z to I O N N AL N
_ l O O O
_ tot ~0~3 to x o I to I N try Lo US Z

lo A 23 frown Countries cur c -- I
, I
c a o I

I
or 5 5 5 if: 1 5 r 5 5 5 O o o o o O

1'" 1 U') N N N
I 5 Jo N I
O O O
O O O

N
N I N N N to N to N N
; 1 0 0 0 5 0 h o I O
I L us us h us C aye owe c , I h o I; my h I h , a _ E
JO .
at x O I O` O --I
LUG Z

lo A 23 308- Foreign Countries Jo , Lo I
I. o C _. , I, C
J
-a) o Q

T I I T
O O O O O O

I I
2 or 5 2 V "I V V to " ~0~0~
IN IN N TN TN
V V V
I O O O O O O
N N
N
T
N
2 I N I T I T l _ I
I_) N N t,) N Lo N Z N Z N
I O O O O O O O O N O N O
N I O to O Us OUT O Us O Us O Us V~0V~

, _ N
C , ^ I
T N
C I if) 5 --O T N `' I V V V Z Z
I O O . O N N
l ! l O O l O l --I l O l O

no x O N
_. LUG Z
.

lo A 23 308- Foreign Countries 1228~357

6 9 , .
O I
C
.,_ 5- , T T T I T

I I I I :;:
C: , O O O O O O

I ; T T

N N N
) to N
U
X S S I I
I; I S TN TN N Jo O O O O O O

I I I
N I to N N
N I I I_) O to N O O O
I I N O Us h O to Us O Us I:
e I L 3 0 ., 1 5' or C -I I O O O
O I L O to O O O

Do . I
X o I I --' N try _IIJ Z

lo A 23 308- Foreign Countries i228357 -- 70 '--_ I
. , , C
O
a: n, So Jo 5 S, :~:

I T T T T T
I N N N N N N
O O O O O O

I

T 5 = S S T
I I O O O O O- O

N
N
I Us S
I US
N I I I I I T
t ) N N N t'') N N Z N
N I O O O O O S O N O N O
I; I O Us O Us L Us O Us O Us O , _ N
._ , I" _ T S
N T
z I O O Jo N N
I I ~3 ' _ E

X O , lo A 23 308- Foreign Countries _ I - 71 -I
C -- , , I
I- C
, I

T
I I) on T T T

.. I .
I' I I T T T ,~, c to T T
N N N
.) T

7 O O
N
N T
I t''-) O Jo N N Z N to N
, I ohs- O O I O

T
_ I; I h o o ox T

Do O , O --I N 1.

lo A 23 308- Foreign Countries 1228~57 I) I

-- l Y C
a) o Q

O O O O O O

D:; , O O O O O O

, 2 2 2 5 2 or I: I O O O O O O
N

2 _ , 2 I N 1 2 I No N
N o N o N to) N 0 2 0 I lo. 0 o o o o o o Lug N , O O O

._ , N
I
' I
C I Lo ` C 0 0 0 2 1 `[~3 go I
_ E
no ., CUD o -I
X o I ox o o Z I Jo lo A 23 Ryan Countries _ 73- ~228357 , ago C _ . ., ., C
. . .
a O
S I, I T T ' 5 or I

O O O

., I
O O O O
I

O O ,. O O O O

N N
2:
N t,) Us N Z N N N I) N to N
N O N O O O O O O O O
I O Us O I O Us Us O Us O U) O 3 No ., , I ^
C I
T , N
C Jo I N N O O T o o O I: I O O I O I O to O I O

_ E
a I N u) a x o l O O O O O O
z ,, _, . _ lo A 23 308- Foreign Countries .

C -- I .
., ,- I
C
' J Jo O
I

T T T T

I
to T
If ) I T I T T 5 to I S T T C T Lo I

N
N N S

i 2 I 3:
N -- N N
to I T T T T Tao Y. I
O O O O
I . l O l l O
I

N
T
, S I I -- I ' I N l I
I N N Z N N k N , N
N I O O O N O k o T O l O
I O US Us O Us Us 3 my I 0 ._ , N
3 1 :~:
C I I) _ , T z to) k I\
C , o N k T

3 my I 0~3 I
a c ' I Of` D N I
l x O I D C
It ILL Z I

lo A 23 foreign Countries _ 75 _ 1;228357 I D
I
I
_ Jo I
a O
Q

or O O O

S
O

I) [I N
N r) N

O O O O

N
N O
N O Us O Us I
lo N I I
L) to t.) C
O
._ I
I
1~1 r- I I I
I O O
O I O . L O

a _ E
D
X o I --' _ ELI Z I -- --' --.

lo A 23 308- Foreign Countries - 76 - 12~8357 (pa) 1:1 adduce of Example (2) with p-toluenesulphonic acid (oil).

(aye) 1:1 adduce of Example (44) with sulfuric acid (amorphous).

(aye) 1:1 adduce of Example ~45) with sulfuric acid, having a melting point of 163C.

(aye) 1:1 adduce of Example (49) with sulfuric acid (amorphous).

lo A 23 308 - Foreign Countries _ 77 _ 1228357 Preparation of starting compounds of the formula (II) Example (II-1 ) Ho No OUCH
HO N _(/ \ N
C No N ( C2H5 ) 2 N
H OUCH

A nlixture of 66.5 9 I mole) of cinnamon-5 diethylamino-6-methoxy-s-triazine, I 9 (0.8 mole) of I-methylhydroxylarnine hydrochloride and I ml of ethanol is heated at the boiling point under reflex for 15 hours.
It is then filtered, the filtrate is concentrated, the residue is taken up in about rnl of water, the mixture AL is rendered alkaline with sodium hydroxide solution and the product thereby obtained as crystals is isolated by filtration with suction.
I 9 (43/. of theory) of N'-(4-diethylamino-6-methoxy-s-triazin-2-yl)-N"-methoxy-guanidine of melting point 112C are obtained.
The compounds of the formula (II) listed in the following Table can be prepared analogously:

` H, No HO No/ \ N
C N~CR5 (II) N
H/ \R3 lo A So - Foreign Countries - I _ 1228~57 Tibet Example welting No; R3 R4 R5 point~oC
________________________________________________________ it- 2 OUCH SHEA NHC2H5 117 5 II- 4 OUCH Of N(C2H5~2 If- 5 C2H5 OUCH N~C2H5)2 If- 6 Ozone SHEA NHC2H5 If- 7 OCH(CH3)2 OUCH NHCH3 If- 8 OCH2-CH=CH2 OUCH N~CH3)2 10 If- 9 Ozone OUCH N~CH3)2 Isle OUCH OUCH N~CH3)2 lo A 23 aye- Foreign Countries 1~28357 Table 2 - Continuation Example Melting No R3 R4 R5polnt tic) 1]-11 OCH2COOC2H5 OCH3N(CH3)2 II-12 OUCH SHEA OUCH N~CH3)2 10 11-18 OUCH SHEA C2H5(amorphous) 11-19 ooze SHEA SHEA

lo A 23 308- Foreign Countries -Table 2 - Continuation Example Melting No. R3 R4 R5 point DC) ________________________________________________________ 11-21 OCH2-CH=CH2 SHEA SHEA

Isle OCH2-C~cH3)3 SHEA SHEA

IJ-26 OCH2CH2-Oc2H5 SHEA OUCH

10 11-27 OCH2CH2-ScH3 SHEA C2H5 r 11-28 OCH2CH2-Sc2Hs SHEA SHEA

Toe A 23 3D8- Foreign Countries . .

Table 2 - Continuation Example Melting No. R3 R4 R5 point ___________________ ___ _ _____________________________ Isle CHICANO OUCH OUCH

Isle OCH2-CH=CHCl SHEA OUCH

5 ~I-31 OUCH 2 SHEA SHEA

II-32 OX ( ) SHEA SHEA

Lo A 23 308- foreign Countries 12~:8357 so reparation of starting compounds of the formula (III) Example (I If -1 ) Of Scholl 295 ml of phosphoryl chloride ("phosphorus ox-S chloride") are added drops to a mixture of 172 y Us mole of sodium 2-chloro-benzenesulphonate, 300 ml of acetoni~riLe and 3UU ml of sulpholane at 2UC to 30C.
The reaction mixture is stirred at 7UC for 4 hours and then cooled to SAC and diluted with ice-water. After extraction with petroleum ether, washing of the extraction solution with water, drying, filtration and concentration, the product remaining in the residue is purified by vacuum distillation.
117 9 MU of theory) of 2-chloro-benzenesulphonyl chloride of boiling point okay mar are obtained.
Example (III-2) COUCH
clue 75.5 9 (0.5 mole) of methyl ~-aminobenzoate are dissolved in 170 ml of concentrated hydrochloric acid and MU 1UU ml of acetic acid. A solution of 34.4 9 of sodium nitrite in MU ml of water is added drops at UC. After the reaction mixture has been subsequently stirred for 15 minutes, it is slowly added to a saturated solution, cooled to C, of Selfware dioxide in 45U ml of acetic acid.
I After the cooling bath has been removed, the mixture is stirred until the evolution of gas has ended, MU g of cop-pyre) chloride being introduced in portions. After dill-lion with ice water extraction with ethylene chloride, washing of the extraction solution with water, drying, SO filtration and concentration, the product remaining in the lo A 23 MU - Foreign Countries lZ28357 residue is purified by vacuum distillation.
45 9 ~38Xo of theory) of ~-methoxycarbonyL-ben~ene~
sulphonyl chloride of boiling point 15UC/1.33 mar are obtained.
The compounds of the formula (III) Listed in the following Table 3 can be prepared analogously:
R1-SO Jo L (III ) lo A I MU Foreign Countries _ 84 _ Table 3 , Example No. R1 Boiling point/
D reassure _________ _ _ _____ __ _ __ _~____ .______ ______ _ OUCH (owl, decomposition III- 3 . on d;st1llatlon) .

III- 4 (melting point:100C) I 11- 5 (Of l) Ill- 6 or 142C/4 mar III- 7 106C/4 mar OSSIFY
III- 8 (molting poetic) ,_~OCHF2 (owe, decomposition _ . III- 9 on d;st;llat;on) S ON SHEA ) 2 1û Ill-10 (melting poetic) - . SHEA oily, decomposition Isle on dist;llat;on) lo A 23 308- Foreign Countries ~228357 Table 3 -continuation Example No. R1 Boiling point/pressure __ _ __ __ __ _ __ _ _ _____________ _____ SCH(CH3)2 IOTA 90C/1.33 mar CH2502cH3 III-13 molting punt C) COOK
III-14 155 C/5.32 mar SHEA
III-16 (melting point:128C) lo A 23 308- Foreign Countries Preparation of starting substance of the formula (VI) Example VOW) "H, No SHEA
HO No N
C OKAY

/

4.2 9 Tao mole) of 2-chloro-benzenesulphonyl S chloride are added to a mixture of 6.0 9 (0.02 mole) of N'-(4-ethoxy-6-methyl-s-tr;az;n-2-yl~-N"-benzyloxyy-guan;d;ne and 30 ml of pardon which has been cooled to okay - 5C, and the mixture us stirred for 48 hours at 20C. After the mixture has been concentrated, the residue us taken up on ethylene chloride, the solution is washed with ON hydrochloric acid, dried and filtered, and the filtrate is carefully concentrated.
6.1 9 (64X of theory) of N'-(4'-ethoxy-6-methyl-s-tr;az;n-2-yl)-N"-benzyloxy-N"-(2-chloro-benzene--sulphonyl)-guan;d;ne are obtained as an only residue.
The compounds of the formula (VI) which are lusted on Table 4 below can be prepared analogously:

HO NH No No R S ( V I ) No Al -S02 R3 lo A 23 308 - Foreign Countries 12;~8357 U) , I o on O I
C
.,. I L
C I O
E
(It O I to S'` a.

LO
us I .5 I: I to N
I I_) T
O O O I.) O O

to N S
N to S N
N
N N N Us N
I" " N S
O l l O O

to I S Z
I O --I to I N
o So r So' a I
a I , N Us _ E l l l l l l I
I X O I
Z I
.

lo A 23 308- Foreign Countries .
` 1228357 Preparation of starting substances of the formula (VII) Example) " , No OUCH

SHEA-11 g ~0.4 mole of sodium hydra (~0/. pure) are 5 added in portions to a suspension of 31.2 9 (OOZE mole) of 2-amino-4,~-dimethoxy-s-triazine in 20C ml of tetrahydro~
Furman at ~UC. After the mixture has been stirred for 12 hours, MU g (0.2 mole) of S',S"-dimethyl N-(2-chloro-benzenesulphonyL)-imino-dithiocarbonate are added, where-upon the reaction temperature rises to 60C. the reaction mixture is stirred at 20c for 5 hours, diluted with ~00 ml of water and filtered. After acidification with concentrated hydrochloric acid, the product crystallizes and is isolated by filtration with suction.
42 9 OX of theory) of N'-(4,~-dimethoxy-s-tri-azin-2-yL)-N"- Czech loro-benzenesulphonyl)-S-methyL-iso-Thor of melting point 176C are obtained.
The compounds of the formula (VII) listed in the following Table 5 can be prepared analogously:

I, lo A I I - Foreign Countries 9 - 1228~57 H N R4 (Ill) \R16 Try -I

Example Melting No. Al R4 R5 R16point(C) ________________________________________________________ VII- I l OUCH OCH3CH3 159 VII- clue SHEA N(CH3)2 SHEA 175 SHEA

SHEA

SHEA

SHEA

lo A 23 aye- Foreign Countries . - 90 Table S - Continuation Example Melting no. Al R4 R5 R16 p`oint(C

Of Ill- 9 SHEA- SHEA SHEA SHEA 165 VII-10 l SHEA SHEA SHEA 151 OSSIFY
5 Vll-ll SHEA OUCH SHEA to Vll-13 SHEA OUCH SHEA

-- , SHEA
Vll-14 SHEA OUCH
SYNCH

SYNCH
Vll-16 OUCH OUCH SHEA

COOK

lo A 23 30~- Foreign Countries _ 91 -Table 5 - Continuation - Example Melting No. Al R4 R5 R16 p`o;nt~C) _______________ ________________________________________ COOCH~CH3~2 F

Vll-l9 SHEA OUCH SHEA
By OUCH

SCH~CH3)2 Vll-24 SHEA OUCH SHEA 136 Of VII-25 g C2H5 OUCH SHEA 132 OSSIFY
lo VII-26 SHEA C2H5 SHEA 103 lo A 23 308- Foreign Countries 1.%28357 Preparation of starting substances of the formula VOW) Example (VIII-1 ) No ooze NC - NO N
No -52.7 9 (0.3 mole) of 2-chloro-4,6-dimethoxy-s-tri-S amine are added to a solution of 30 9 (0.3 mole) of thedisodium salt of cyanamide in 600 ml of acetone, and the reaction mixture is heated at the boiling point under no-flux for 6 hours. After the solvent has been distilled off, the crystalline residue is dissolved on 250 ml of water and the solution is acidified with concentrated hydrochloric acid. The product obtained as crystals is isolated by filtration with suction.
33 9 (61X of theory) of 2-cyanoamino-4,6-dimethoxy-s-triazine with a melting point above 300C are obtained.
Example (VIII-2) (a) NC-N -I ON
No N--~C1 4.5 9 (0.05 mole) of disodium salt of cyanamide 50 ml of water are added drops to a suspension of 8.2 9 (0.05 mole) of 2,4-dichloro-6-methyl-1,3,5-triazine in 100 ml 20 of ice-water at a temperature of 0C to 5C in such a way that a pi value of 9.5 is not exceeded. Thereafter, stirring is continued for another hour at 20C, 40 9 of sodium chloride are added, and stirring is continued for approx. 0.5 to 1 hour at 20C
After the product has been filtered off with suction and dried, 9.1 9 (95X of theory) of the sodium salt of 4-chloro-2-cyanoamino-6-methyl-1,3,5-triazine of lo A 23 308 - Foreign Countries melting point 190C (decomposition) are obtained.
(b) N SHEA
NC-NH / N
' No 1 ml of concentrated hydrochloric acid is added to a suspension of 2 9 (0.01 mole) of the sodium salt of 4-chloro-2-cyanoamino-6-methyl-1,3,5-triazine in 50 ml of water at 0C to 10C. The precipitate formed is filtered off with suction and dried.
In this manner, 1.3 9 (77% of theory) of 4-chloro-2-cyanoamino-6-methyl-1,3,5-triazine of melting point 105C (decomposition) are obtained.
lo) N SHEA
NC-N I/ N
No N OOZE

A solution of 3.7 9 (0.16 mole) of sodium in 100 ml of ethanol is added drops to a solution of 29 9 (0.15 mole) of the sodium salt of 4-chloro-2-cyano-amino-6-methyl-1,3,5-triazine in 500 ml of ethanol in such a way that a reaction temperature of 30C is not exceeded. Thereafter, stirring is continued for 3 hours at 20C, and the mixture is diluted with 400 ml of ethanol and filtered. The filtrate is concentrated in vacua, the temperature not exceeding 45C.
In this manner, 29.9 9 (99X of theory) of the sodium salt of 2-cyanoamino-4-ethoxy-6-methyl-1,3,5-tri-amine of melting point 200C (decomposition) reobtained.
(d) N SHEA
NC-NH I/ N
N OKAY

lo A 23 308 - Foreign Countries - 94 _ ~228357 50 ml of 20X. strength hydrochloric acid are added to a solution of 30.1 9 (0.15 mole) of the sodium salt of 2-cyanoamino-4-ethoxy-6-methyl-1,3,5-triazine in 300 ml of water at 0C to 10C, and stirring is con-5 tinted for 15 minutes at 10C. The precipitate is filtered off with suction and dried.
26.5 9 ~98X of theory) of 2-cyanoamino-4-ethoxy-6-methyl-1,3,5-triazine of melting point 195C (deco-position) are obtained.
10 (e) No SHEA
NC-NH~ N
No OOZE

8.5 9 (0.05 mole) of 4-chloro-2-cyanoamino-6-methyl-1,3,5-triazine are added in portions to a solution of 2.5 9 (0.11 mole) of sodium in 100 ml of 15 ethanol in such a way that the temperature does not exceed 35C. Thereafter, stirring is continued for one hour at 20C, and the mixture is concentrated in vacua in such a way that the bath temperature does not exceed 50C. The residue is dissolved in 50 ml 20 of water, and the solution is acidified with 6 ml of con-cent rated hydrochloric acid. The crystals formed are filtered off with suction and dried.
8.1 9 (91X of theory) of tsunami nighthawks-6-methyl-1,3,5-triazine of melting point 195C (deco-25 position) a no obtained.
The compounds of the formula (VIII) listed in the following Table 6 can be prepared analogously:
No (VIII) NC-NH N
N~R5 lo A 23 308 - Foreign Countries 122~3S7 Tab Le. 6.

Exam l e Me L t i no No. R4 R5 Po;nt~oc) ______. ___ ____________________________________ _______ VIII- 3 OUCH N(C2H5)2 114 VIII- 6 Of N~C2H5)2 156 VIII- 8 OCH(CH3)2 SHEA

Vowel SCH(CH3)2 SHEA

lo A 23 308-. Foreign Countries Tab to 6 - wont 1 nut i on Exam to Me Lang No. R4 R5 point ________________________________________________________ VI I 1-13 NHCH(CH3)2 SHEA
.

5 VI I I-14 N(CH3)2 SHEA

lo A 23 foreign Countries _ 97 _ 12283S7 Preparation of starting confounds of the formula (XV) Example (hV-1) Of ~;2-N=C/
SHEA
8 g Us mole) of sodium hydroxide - dissolved in 15 ml of water - and 6 ml (0.11 mole) of carbon disulphide are simultaneously added drops (from different dropping funnels) to a solution of MU 9 (0.1 mole) of sheller-benzenesulphonamide in 80 ml of dimethylformamide at 2~C After the mixture has been stirred for 1 hour, MU 13 ml (0.22 mole) of methyl iodide are added drops and the reaction mixture is stirred at 20C for a further hour. The product is precipitated by addition of MU ml of water an is isolated by filtration with suction.
22.1 9 (75'~ of theory) of S',S"-dimethyl No chloro-benzenesulphonyl)-isothiocarbamate of melting point 112C are obtained.
The compounds of the formula (XV) listed in the following Tale 7 can be prepared analogously:

Rl-502-N=C (XV) SO l 6 lo A S08 Foreign Countries _ I

.

Tubule Example Melting No. R1 R16 point DO
__ _ _ __ _ _ _ ____ ________ . _ ____ SHEA

SHEA

-OSSIFY

Of SNOWSHOE
_ XV- 8 SHEA

XV-10 Of SHEA 94 lo A 23 forgone Countries .

_ 99 _ Table 7 - continuation Example Melting No. Al R16 point~C~
___~_______ __ _ ____ _ _ _____ __ _ _ __ ___ XV-ll H3C - SHEA 107 o COOCH~CH3)2 By lo A 23 308- Foreign Countries Tubule - continuation Example Melting Jo-. R1 R16 po;nt~C) ________________________________________________________ XV-20~ OUCH OH

XV-21 l SHEA

XV-23 l CH~CH3)2 65-67 SCH~CH3)2 XV-25 Of SHEA a Lo A 23 308---~oreign Countries Preparation of starting substances of the formula tXVI) Example (XVI-1) SHEA

50 ml of concentrated ammonia are added drops to a mixture of 60 9 (0.27 mole) of 2-methylthiobenzene-sulphonyl chloride and 60 ml of acetone at 20C to 30C, with stirring. The reaction mixture is subsequently stirred at 20C for 1 hour and then poured into 600 ml of 10X strength sodium hydroxide solution. This solution is filtered and then acidified with concentrated hydra-caloric acid. The product thereby obtained as crystals is isolated by filtration with suction.
19 9 (30X of theory) of 2-methylthio-benzenesul-phonamide of melting point 149C are obtained The compounds of the formula (XVI) listed in the following Table 8 can be prepared by the process described by way of example in the preceding Example:

R1-S0z-NH2 (XVI) lo A 23 308 - Foreign Countries . _ Table 8 Example Melting No. Al put _______________________________~._______________ _______ SCH~CH3~2 SHEA

502N~CH3)2 XVI- 5 g_ 142 OSSIFY

XVI- a SHEA-CHz502CH3 COOK

lo A 23 foreign Countries . , Table 8 - continuation Example Melting No. R1 point tic) _______ ___ _ _ _ __ _ __ __ _____ _ _____ _ _____ COUCH ( SHEA ) 2 XVI -l 1 Jo Shekel -XVI-12 (I

lo A 23 30~- Foreign Countries Example A
Reemergence test/Greenhouse Solvent: parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active come pound, 1 oat by weight of active compound is mixed with the stated amount of solvent, the stated amount of Emil-sifter is added and the concentrate is diluted with water to the desired concentration.
I Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. Toe concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in Jo damage in comparison to the development of the untreated control. The figures denote:
Ox. = no action trike untreated control) 10UX = total destruction In this test, for example, the following compounds from the preparation examples exhibit an excellent activity: (2) and I

Lo A 23 Us - Foreign Countries _ 105 _ ~228357 Example B
Post-emergence test/~reenhouse Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active come pound, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsi~
lien 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 so chosen that the particular amounts of active lo compound desired are applied in ZOO l of water/ha. After three weeks, the degree of damage to the plants is rated in damage in comparison to the development of the untreated control. The figures denote:
= no action (like untreated control) MU 1UU~ = total destruction In this test, for example, the following compounds from the preparation examples exhibit an excellent activity: (Z), I and I

lo A Z3 Us - Foreign Countries

Claims (21)

THE EMBODIMENTS OF THE INVENTION IN WHICH AN EXCLUSIVE
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:

1. A sulphonylguanidinotriazine derivative or the general formula (I) (I) in which M represents hydrogen or one equivalent of a metal, R1 represents an optionally substituted phenyl radical wherein R6 and R7 are identical or different and represent hydrogen, halogen, cyano, nitro, or C1-C4-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, C1-C4-alkylamino-carbonyl, di-(C1-C4-alkyl)-amino-carbonyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkyl-sulphonyl), or represent C1-C4-alkoxy, (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkyl-sulphinyl or C1-C4-alkylsulphonyl), or represent C1-C4-alkylthio, C1-C4- alkylsulphinyl, or represent C1-C4-alkylsulphonyl (which is optionally substituted by fluorine, chlorine, bromine cyano or C1-C4-alkoxy-carbonyl), or represent C1-C4-alkyl-amino-sulphonyl, di-(C1-C4-alkyl)-amino-sulphonyl, C1-C4-alkoxyamino-sulphonyl, benzyloxy- aminosulphonyl or C1-C4-alkoxy-C1-C4-alkyl-aminosulphonyl, or represent phenyl or phenoxy, or represent C1-C4-alkoxysulphonyl, or represent C2-C6-alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, carboxyl or phenyl), or represent C2-C6-alkinyl (which is option-ally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-carbonyl), or represent C3-C6-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxycarbonyl), or represent C3-C6-alkenylthio (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-carbonyl), or represent C1-C6-alkoxy-carbonyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy), or represent C3-C6-cycloalkoxy-carbonyl, or represent C1-C6-alkylthio-carbonyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C4-alkoxy-carbonyl), or represent aminocar-bonyl, C1-C4-alkylamino-carbonyl, di-(C1-C4-alkyl)-amino-carbonyl, C1-C4-alkoxyamino-carbonyl, C3-C4-alkenyloxy-amino-carbonyl, benzyloxyamino-carbonyl, C1-C4-alkoxy-C1-C4-alkyl-amino-carbonyl, dimethyl-hydrazino-carbonyl, or dimethyl-hydrazino-sulphonyl, or represent C3-C6-alkinyloxy or C3-C6-alkinylthio, or in which, furthermore, R1 represents an optionally substituted benzyl radical - 107a -wherein R8 and R9 are identical or different and represent hydrogen, halogen, cyan, vitro, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlor-rine), C1-C4-alkoxycarbonyl, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl or di-(C1-C4-alkyl)-aminosulphonyl;
and in which, furthermore, R2 represents hydrogen, C1-C4-alkyl or a sulphonyl radical wherein R10-SO2-R10 represents C1-C12-alkyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkoxy-carbonyl, C1-C4-alkylamino-carbonyl, di-(C1-C4-alkyl)-amino-carbonyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkyl-sulphonyl), or represents C1-C12-alkoxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkoxycarbonyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkyl-sulphinyl or C1-C4-alkylsulphonyl), or represents C2-C12-alkenyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkoxy, C1-C4-alkylthio or phenyl), or represents C2-C12-alkenyloxy (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkoxy, C1-C4-alkylthio or phenyl), or represents C1-C8-alkylamino, di-(C1-C4-alkyl)-amino, C3-C6-cycloalkylamino or di-(C3-C6-cycloalkyl)-amino (which are optionally substituted by fluorine, chlorine, bromine, cyano, nitro, phenyl, phenoxy, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl), or represents C2-C8-alkenylamino (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro or phenyl), or represents phenylamino or benzylamino (which are optionally substituted by fluorine, chlorine, bromine, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy, C1-C2-fluoroalkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl, C1-C4-alkylsulphonyl, cyano, nitro and/or C1-C4-alkoxy-carbonyl), or represents benzyl which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro, C1-C4-alkyl, trifluoromethyl, C1-C4-alkoxy-carbonyl, C1-C4-alkoxy or di-(C1-C4-alkyl)-aminosulphonyl), or represents an optionally substi-tuted phenyl radical wherein R11 and R12 are identical or different and have the meanings given above for R6 and R7, but are not iden-tical to R6 and R7 in each individual case;
and in which, furthermore, R3 represents the radical -O-R13, wherein R13 represents C1-C12-alkyl (which is optionally substituted by fluorine, chlorine, bromine, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulphinyl or C1-C4-alkylsulphonyl), or represents C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C2-alkyl, C3 C6-alkenyl (which is optionally substituted by fluorine, chlorine or bromine), C3-C6-alkinyl, C1-C4-alkoxy-carbonyl-C1-C2-alkyl, amino-carbonyl-methyl, C1-C4-alkylamino-carbonyl-methyl or di-(C1-C4-alkyl)-amino-carbonyl-methyl, or represents phenyl, benzyl or phenethyl (which are optionally substituted by fluorine, chlorine, nitro, cyano, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxycarbonyl);
or in which, furthermore, R3 represents the radical wherein R14 represents hydrogen or C1-C4-alkyl and R15 represents hydrogen, C1-C4-alkyl (which is optionally substituted by fluorine, chlorine, bro-mine, cyano, C1-C4-alkoxy or C1-C4-alkoxy-carbo-nyl), or represents C3-C6-cycloalkyl, or repre-sents phenyl, benzyl or phenethyl (which are op-tionally substituted by fluorine, chlorine, bro-mine, cyano, nitro, C1-C4-alkyl, C1-C4-alkoxy or C1-C4-alkoxy-carbonyl), or represents C1-C4-alkyl-carbonyl, C1-C4-alkoxy-carbonyl, C1-C4-alkyl-sulphonyl, or phenylsulphonyl (which is optionally substituted by fluorine, chlorine, bromine, cyano, nitro or methyl);
or in which, furthermore - in the case where R2 represents a sulphonyl radical wherein R10 has the abovementioned meaning -R3 also represents hydrogen;
and in which, furthermore, R4 represents fluorine, chlorine, bromine, cyclo-propyl or C1-C4-alkyl (which is optionally substi-tuted by fluorine and/or chlorine), or represents C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represents C1-C4-alkylthio (which is optionally substituted by fluorine and/or chlorine), or represents C1-C4-alkyl- or di-(C1-C4-alkyl)-amino (which are option-ally substituted by fluorine) and R5 represents fluorine, chlorine, bromine, cyclo-propyl, C1-C4-alkyl (which is optionally substituted by fluorine and/or chlorine), or represents C1-C4-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represents C1-C4-alkylthio (which is optionally substituted by fluorine and/or chlorine), or represents C1-C4-alkyl- or di-(C1-C4-alkyl)-amino (which are optionally substituted by fluorine), or a 1:1 adduct of a compound of the formula (I) with a strong acid, providing that the following compounds are excluded: N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-dimethylamino-N'''-(2-difluoromethoxy benzenesulphonyl)-guanidine, N'-(4,6-dimethoxy-s-triazin-2-yl)-N"-methoxy-N",N'''-bis-(2-trifluoromethyl-benzenesulphonyl)guanidine, N'-(4-dimethyl-amino-6-methyl-s-triazin-2-yl)-N"-methoxy-N'''-(2-methyl-benzenesulphonyl)-guanidine and N'-(4-dimethyl-amino-6-methyl-s-triazin-2-yl)-N"-dimethyl-amino-N'''-(2-methyl-benzenesulphonyl)-guanidine.

2. A compound or adduct of the formula (I) according to claim 1, in which M represents hydrogen or one equivalent of sodium, potassium or calcium, R1 represents an optionally substituted phenyl radical wherein R6 and R7 are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, or methyl (which is optionally substituted by fluorine, chlorine, cyano, C1-C3-alkoxy-carbonyl, C1-C3-alkoxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl or C1-C3-alkylsulphonyl), or represent C1-C2-alkoxy (which is optionally substituted by fluorine, chlorine, cyano, C1-C3-alkoxy-carbonyl, C1-C3-alkoxy, C1-C3-alkylthio, C1-C3-alkylsuphinyl or C1-C3-alkylsulphonyl), or represent C1-C3-alkylthio, C1-C3-alkylsulphinyl or C1-C3-alkylsulphonyl (which are optionally substituted by fluorine, chlorine, cyano or C1-C3-alkoxy-carbonyl), or represent di-(C1-C3-alkyl)-aminosulphonyl, C1-C3-alkoxy-methyl-amino-sulphonyl, phenyl or phenoxy, or represent C1-C4-alkoxy-carbonyl (which is optionally substituted by fluorine, chlorine, bromine, cyano or C1-C3-alkoxy), C3-C6-cycloalkyloxy-carbonyl, C1-C4-alkylthio-carbonyl, di-(C1-C3-alkyl)-amino-carbonyl or C1-C3-alkoxy-methylamino-carbonyl or represent C2-C4-alkenyl (which is optionally substituted by fluorine, chlorine, cyano or C1-C3-alkoxy-carbonyl);
R1 represents an optionally substituted benzyl radical wherein R8 and R9 are identical or different and represent hydrogen, fluorine, chlorine,cyano, nitro, methyl, methoxy or C1-C3-alkoxy-carbonyl;
R2 represents hydrogen, methyl or a sulphonyl radical wherein R10 represents C1-C8-alkyl (which is optionally substituted by fluorine, chlorine or cyano), or represents C1-C8-alkoxy (which is optionally substituted by fluorine, chlorine or cyano), or represents C2-C8-alkenyl (which is optionally substituted by fluorine, chlorine, cyano or phenyl), or represents C2-C8-alkenyloxy (which is optionally substituted by fluorine, chlorine, cyano or phenyl), or represents C1-C6-alkylamino, C3-C6-cyclo-alkylamino or di-(C3-C6-alkyl)-amino (which are optionally substituted by fluorine, chlorine, cyano, phenyl, phenoxy or C1-C2-alkoxy), or represents C2-C6-alkenylamino ( which is optionally substituted by fluorine, chlorine, cyano or phenyl), or represents phenylamino or benzylamino ( which are optionally substituted by fluorine, chlorine, bromine, C1-C4-alkyl, trifluoromethyl, C1-C3-alkoxy, C1-C2-fluoroalkoxy, C1-C3-alkylthio, C1-alkylsulphinyl, C1-C3-alkylsulphonyl, cyano, nitro and/or C1-C3-alkoxy-carbonyl), or represents benzyl (which is optionally substituted by fluorine, chlorine, cyano, nitro, methyl, methoxy and/or C1-C2-alkoxy-carbonyl), or represents an optionally substituted phenyl radical wherein R11 and R12 are identical or different and have the meanings given above for R7 and R8, but are not identical to R7 and R8 in each individual case;
R3 represents the radical -O-R13, wherein R13 represents C1-C8-alkyl (which is optionally substituted by fluorine or chlorine), or represents C3-C6-alkenyl (which is optionally substituted by chlorine), or represents C1-C3-alkoxy-carbonyl-C1-C2-alkyl, phenyl, phenethyl or benzyl (which is optionally substituted by fluorine, chlorine, nitro, methyl, methoxy or C1-C2-alkoxy-carbonyl);
R3 represents the radical wherein R14 represents hydrogen or methyl and R15 represents hydrogen, C1-C3-alkyl (which is optionally substituted by fluorine, chlorine, cyano, C1-C2-alkoxy or C1-C2-alkoxy-carbonyl), or represents C3-C6-cycloalkyl, phenyl, benzyl or phenethyl (which is optionally substituted by fluorine, chlorine, bromine, nitro, cyano, C1-C2-alkyl, C1-C2-alkoxy, or C1-C2-alkoxy-carbonyl), or represents acetyl, methoxycarbonyl, benzenesulphonyl or toluenesulphonyl;
R represents fluorine, chlorine, cyclopropyl or methyl (which is optionally substituted by fluorine and/or chlorine), or represents C1-C3-alkoxy ( which is optionally substituted by fluorine and/or chlorine), or represents C1-C3-alkylthio (which is optionally substituted by fluorine and/or chlorine), or represents C1-C3-alkyl- or di-(C1-C3-alkyl)-amino (which are optionally substituted by fluorine) and R5 represents fluorine, chlorine, cyclopropyl, or methyl (which is optionally substituted by fluorine and/or chlorine), or represents C1-C3-alkoxy (which is optionally substituted by fluorine and/or chlorine), or represents C1-C3-alkylthio (which is optionally substituted by fluorine and/or chlorine), or represents C1-C3-alkyl- or di-(C1-C3-alkyl)-amino (which are optionally substituted by fluorine), with the compounds individually named in claim 1 being excluded.

3. A compound or adduct of the general formula (I) according to claim 1, in which M represents hydrogen or one equivalent of sodium, potassium or calcium, R1 represents a substituted phenyl radical wherein R represents fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, C1-C3-alkylthio, C1-C3-alkylsulphinyl, C1-C3-alkylsulphonyl, dimethylaminosulphonyl, diethyl-aminosulphonyl, methoxymethylaminosulphonyl, phenyl, C1-C4-alkoxy-carbonyl, difluoromethylthio or trifluoromethylthio and R7 represents hydrogen;
R8 represents hydrogen, methyl or a sulphonyl radical wherein R10 represents C1-C4-alkyl (which is optionally substituted by fluorine or chlorine), or represents C1-C4-alkylamino or di-(C1-C2-alkyl)-amino (which are optionally substituted by fluorine), or represents an optionally substituted phenyl radical wherein R11 and R12 are identical or different and represent hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, trifluoromethyl, C1-C2-alkoxy (which is optionally substituted by fluorine, chlorine, cyano or C1-C3-alkoxy-carbonyl), C1-C3-alkylthio, C1-C3-alkylsulphinyl or C1-C3-alkylsulphonyl (which are optionally substituted by fluorine and/or chlorine), dimethylaminosulphonyl, diethylaminosulphonyl, N-methoxy-N-methylamino-sulphonyl, phenyl or C1-C4-alkoxy-carbonyl (which is optionally substituted by fluorine, chlorine, cyano or C1-C2-alkoxy), R3 represents the radical -O-R13, wherein R13 represents C1-C4-alkyl, C3-C4-alkenyl, C1-C4-alkoxy-carbonyl-methyl, phenyl, phenethyl or benzyl (which is optionally substituted by fluorine, chlorine, nitro, cyano, methyl, methoxy or methoxycarbonyl), R3 represents the radical wherein R14 represents hydrogen or methyl and R15 represents hydrogen, C1-C3-alkyl, C3-C6-cycloalkyl, phenyl, acetyl, methoxycarbonyl, benzenesulphonyl or toluenesulphonyl;
R4 represents methyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino or diethylamino and R5 represents methyl, methoxy, ethoxy, methylthio, ethylthio, methylamino, ethylamino, dimethylamino, or diethylamino, with the compounds individually named in claim 1 being excluded.

4. A 1:1 adduct of a compound according to claim 2 with a strong acid wherein the strong acid is hydrogen chloride, hydrogen bromide, hydrogen iodide, sulphuric acid, trifluoroacetic acid, an alkanesulphonic acid which has up to 4 carbon atoms and is optionally substituted by fluorine or chlorine, or benzene- or naphthalenesulphonic acid which is optionally substituted by fluorine, chlorine, bromine or methyl.

5. A compound or adduct of the general formula (I) according to claim 1, in which M represents hydrogen or one equivalent of sodium, potassium or calcium, R1 represents a substituted phenyl radical of the formula wherein R6 represents chlorine, mathoxycarbonyl, trifluoromethoxy, difluoromethoxy, methylthio, dimethylaminosulphonyl, methyl, ethoxycarbonyl, phenyl, fluorine, isopropylthio, bromine, isopropoxycarbonyl, diethyl-aminosulphonyl, methylsulphonyl, or trifluoromethyl, and R7 represents hydrogen; or R1 represents a substituted benzyl radical of the formula wherein R8 represents methoxycarbonyl and R9 represents hydrogen;
R2 represents hydrogen or sulphonyl radical R10-SO2-wherein R10 represents methyl, n-butyl, perfluorooctyl or an optionally substituted phenyl radical of the formula wherein R11 represents 2-chloro, 2-methoxycarbonyl, 2-trifluoromethoxy, 2-methylthio, 4-nitro, 2-difluoromethoxy, 2-ethoxycarbonyl, 2-isopropoxy-carbonyl, 2-dimethylaminosulphonyl, 2-diethylaminosulphonyl, 2-methylsulphonyl, 2-bromo, 2-fluoro, 2-trifluoromethyl, 2-diethylaminosulphonyl or phenyl, and R12 represents hydrogen;
R3 represents the radical -O-R13 or wherein R13 represents methyl, benzyl, isopropyl, allyl, ethyl, 4-methyl-benzyl, ethoxycarbonylmethyl, isobutyl, phenyl or 3-chloropropyl, R14 represents methyl, R15 represents methyl;

R4 represent methoxy, methyl, methylthio or ethyl, and R5 represents dimethylamino, diethylamino, methyl, methoxy, ethoxy or ethylamino, with the compounds individually named in claim 1 being excluded.

6. A 1:1 adduct of a compound according to claim 3 or 5 with a strong acid, wherein the strong acid is hydrochloric acid, sulphuric acid, trifluoroacetic acid, methanesulphonic acid, benzenesulphonic acid or toluenesulphonic acid.

7. N'-(4-Methoxy-6-methyl-s-triazin-2-yl)-N"-methoxy-N",N'''-bis (2-chlorobenzenesulphonyl)guanidine of the formula

8. N'-(4-Methoxy-6-methyl-s-triazin-2-yl)-N"-methoxy-N'''-(2-chloro-benzenesulphonyl)guanidine of the formula

9. N'-(4-Methoxy-6-methyl-s-triazin-2-yl)-N"-dimethylamino-N'''-(2-chlorobenzensulphonyl)guanidine of the formula

10. A process for the preparation of a sulphonylguanidino-triazine derivative of the general formula (I) as defined in claim 1, which process comprises:
(a) to obtain a compound of formula (I) wherein M represents hydrogen, and R2 is R1-SO2-, reacting a guanidinotriazine derivative of the formula (II) (II) in which R3, R4 and R5 have the meanings as defined in claim 1 with a sulphonyl chloride of the formula (III) R1-SO2-Cl (III) in which R1 has the meanings as defined in claim 1, in the presence of an acid acceptor and if appropriate in the presence of a diluent;

(b) to produce a compound of formula (I) wherein M represents hydrogen and R2 represents hydrogen or C1-C4-alkyl, reacting a sulphonylguanidinotriazine derivative obtainable by the process described above under (a), of the formula (ID) (ID) in which R1, R4, R5 and R13 have the meanings as defined in claim 1, with an amino compound of the formula (IV) (IV) in which R2 represents hydrogen or C1-C4-alkyl and R3 has the meanings as defined in claim 1, or with the hydrochloride of the amino compound of the formula (IV), if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent;
(c) to obtain a compound of formula (I) wherein M represents hydrogen and R2 represents an optionally substituted sulphonyl radical wherein R10 has the meanings as defined in claim 1, reacting a sulphonyl-guanidinotriazine derivative of the formula (IE) (IE) in which R1, R3, R4 and R5 have the meanings as defined in claim 1, with a sulphonyl chloride of the formula (V) R10-SO2-Cl (V) in which R10 has the abovementioned meaning, in the presence of an acid acceptor and if appropriate in the presence of a diluent;
(d) to obtain a compound of formula (I) wherein M represents hydrogen and R2 represents an optionally substituted sulphonyl radical wherein R10 has the abovementioned meaning, reacting a sulphonylguanidino-triazine derivative of the formula (VI) (VI) in which R3, R4, R5 and R10 have the abovementioned meanings, with a sulphonyl chloride of the formula (III) R1-SO2-Cl (III) in which R1 has the abovementioned meaning, in the presence of an acid acceptor and if appropriate in the presence of a diluent;
(e) to obtain a compound of formula (I) wherein M represents hydrogen and R2 represents hydrogen or C1-C4-alkyl, reacting a sulphonylisothioureido-triazine derivative of the formula (VII) (VII) in which R1, R4 and R5 have the abovementioned meanings and R16 represents C1-C4-alkyl or benzyl, with an amino compound of the formula (IV) (IV) in which R2 represents hydrogen or C1-C4-alkyl and R3 has the abovementioned meaning, if appropriate in the presence of a diluent;
(f) to obtain a compound of formula (I) wherein M represents one equivalent of a metal, reacting a compound obtainable by the processes described above under (a), (b), (c), (d), and (e) of the formula (I) in which M represents hydrogen and R1, R2, R3, R4 and R5 have the abovementioned meanings, with a metal hydroxide, hydride or alkanolate or with an organometallic compound, if appropriate in the presence of a diluent; or (g) to obtain a 1:1 adduct of a compound of the formula (I) with a strong acid, reacting a compound of the formula (I) in which M represents hydrogen and R1, R2, R3, R4, and R5 have the abovementioned meanings, with a strong acid, if appropriate in the presence of a diluent.

11. A method of combating weeds which comprises applying to the weeds or to their habitat a herbicidally effective amount of a compound according to claim 1.

12. A method according to claim 11 wherein the compound is applied in the form of a composition containing said compound as active ingredient in admixture with a suitable carrier or diluent.

13. A method according to claim 12 wherein the active ingredient concentration in said composition is between 0.1 and 95 % by weight.

14. A method according to claim 12 wherein the active ingredient concentration in said composition is between 0.5 and 90 % by weight.

15. A method according to claim 11, 12 or 13 wherein the compound is applied as a pre-emergence herbicide.

16. A method according to claim 11, 12 or 13 wherein the compound is applied as a post-emergence herbicide.

17. A method according to claim 11, 12 or 13 wherein the compound is applied to an area of cultivation at a rate of between 0.001 and 15 kg/ha.

18. A method according to claim 11, 12 or 13 wherein the compound is applied to an area of cultivation at a rate of between 0.005 and 10 kg/ha.

19. A method according to claim 11, 12 or 13 wherein such compound is N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-methoxy-N",N'''-bis(2-chloro-benzenesulphonyl)guanidine.

20. A method according to claim 11, 12 or 13 wherein such compound is N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-methoxy--N"'-(2-chlorobenzenesulphonyl)guanidine.

21. A method according to claim 11, 12 or 13 wherein such compound is N'-(4-methoxy-6-methyl-s-triazin-2-yl)-N"-dimethyl-amino-N"'-(2-chlorobenzenesulphonyl)guanidine.