JPS6160669A - Sulfonylguanidinopyrimidine derivative - Google Patents

Abstract

(57) [Abstract] This bulletin contains application data before electronic filing, so abstract data is not recorded.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to novel sulfonylguanidinopyrimidine derivatives, processes for their preparation and their use as herbicides.

Various guanidine derivatives have been patented (:DB-As (German patent application publication specification i!f) ml, 089,210
and East German patents f471,016 and 8
4.530] as effective herbicides, but hitherto they have not played a relatively large role as agents for controlling weeds and/or regulating plant growth.

Other guanidine derivatives are disclosed in the previous patent application EP-
O8 (European Patent Application Publication Specification) No. 121.08
This is the subject of issue 2.

According to the present invention, υ, general formula (I), where M represents hydrogen or one equivalent of metal, 几1 represents optionally substituted phenyl, where R7 and R'ld are the same or different; Hydrogen, halogen [especially Vc7, chlorine and/or bromine]
, cyan, nitro or C3-C-alkyl [wherein optionally fluorine, chlorine, bromine, cyano, C1-C4-alkoxy-carbonyl, C1-C6-alkylamino-sulfonyl, C-(C1-C,-furkyl) )-7mi/-carbonyl, 01-C1-alkoxy, C,NC,-alkylthio, C,-C4-alkylsulfinyl or C,
May be substituted with NC,-alkylsulfonyl]
CI""C4-alkoxy
optionally substituted with carbonyl, C1-C,-alkoxy, C8-C3-alkylthio, 01-C1-alkylsulfinyl or C1-C4-alkylsulfonyl], or C3-C,-alkylthio, C1-C
4-alkylsulfinyl or C, to C3-alkylsulfonyl, which groups may optionally be substituted with fluorine, mono, bromine, cyano or C1-C6-alkoxy-carbonyl; or C1-C3- Alkylamino-sulfonyl, di(Ct-C3-alkyl)-
Amino-sulfonyl, C1-C6-alkoxyamino-
Sulfonyl, benzyloxy-aminosulfonyl, C,
, C,-alkoxy-01-C3-alkyl-aminosulfonyl, phenyl or phenoxy, C2-C4-alkoxy-sulfonyl, or C2-C6-alkenyl [wherein optionally fluorine,
optionally substituted with chlorine, bromine, cyano, C,,C,-alkoxycarbonyl, carboxyl or phenyl], C8-C6-alkynyl [the iron group is optionally substituted with fluorine, chlorine, bromine, cyano or C,-C , -alkoxycarbonyl], C1-C3-alkenoxy [the iron group may optionally be substituted with fluorine, chlorine, bromine, cyano or C9-C4-alkoxy-carbonyl], C8-C0-alkenylthio [the iron group may optionally be substituted with fluorine, salt, bromine, cyano or C,,C,-alkoxy-carbonyl], C1
~C,-alkoxy-carbonyl [the group MIII 7
Z), C may be substituted with nitrogen, chlorine, bromine, cyano or FiCl-C<-alkoxy.

~C6-cycloalkoxy-carbonyl, C1-C6-
Alkylthiocarbonyl (the iron group may optionally be substituted with fluorine, chlorine, bromine, cyano or C1-C6-alkoxy-carbonyl), amino-carbonyl, Cl
-C4-alkylamino-carbonyl, di(aS~C
1-Alkyl)-amino-carbonyl, C,,C,-alkoxyamino-carbonyl, C5-C,-alkenyloxyamino-carbonyl, benzyloxy-aminocarbonyl, C2-C,-alkoxy-C,,C,- ruaminocarbonyl in alkali, dimethylhydrazinocarbonyl, dimethylhydrazinosulfonyl, C1-C@-alkynyloxy or C3-C6-alkynylthio; or further R1 represents a benzyl group Q optionally substituted with F; , where 几9 and R+IO are the same or different, and
hydrogen, halogen (for example, in particular fluorine, chlorine or bromine), cyanide, nitro, C8-C1-alkyl iron radicals optionally optionally substituted with nitrogen and/or chlorine],
C1-C4-alkoxy [iron group is optionally 7] and/-!
! : may be substituted with bamboo chlorine], C, ~C4-
alkoxycarbonyl, C1-C3-alkylthio,
01-C6-alkylsulfinyl, C1-C,-alkylsulfonyl or di(CI-04-alkyl)-
represents diminosulfonyl, and furthermore, R”Ifi
water cloud, Ct~C3-alkyl or tajasulfonyl group 1(,1l-8O,-; C,-Alkoxycarbonyl, C1-C2-alkylamino-carbonyl, di(C1-C,-furkyl)-7 minocarbonyl, 01-C2-alkoxy, 01-C4-alkylthio, C1-C1-alkylsulfinyl or HcI
- may be substituted with C4-alkylsulfonyl]
, 01-C+z-alkoxy [the iron group is optionally fluorine, chlorine, bromine, cyano, nitro, CI-C4-alkoxy-carbonyl, C1-C4-alkoxy, C1-C4-alkylthio, C1-C4-alkylsulfinyl or C
5-C4-alkylsulfonyl], C1-C1t-alkenyl [the iron group is optionally substituted with fluorine, chlorine, bromine, cyano, nido aSC, ~C3-alkoxy,
01-C4-alkylthio or phenyl], C7-C12-alkenyloxy [the iron group is optionally substituted with 7-, chlorine, bromine, 7-ano, nitro, C3-C
optionally substituted with 6-alkoxy, C,-C,-alkylthio or phenyl], 01-C6-alkylamino, di(C+-C,-alkyl)-amino, C8
~C6-cycloalkylamino or di(CS-C
6-cycloalkyl)-amino [These groups optionally include fluorine, chlorine, bromine, cyano, nitro, phenyl, phenoxy, ClNC4-alkoxy, C1-C3-alkylthio, C1-C3-alkylsulfinyl or FiCl
Substituted with NC4-alkylsulfonyl]
, C1-C6-alnylamino [iron group is optionally fluorine,
may be substituted with chlorine, bromine, cyano, nitro or phenyl], phenylamino or benzylamino [these groups may optionally be substituted with fluorine, chlorine, bromine, C3-C
4-Alkyl, trifluoromethyl, C1-C,-alkoxy, 01-C,-yfluoroalkoxy, C,,C,
-alkylthio, 01-C4-alkylsulfinyl,
C1-C6-alkylsulfonyl, cyano, nitro and h/tf, ti may be substituted with C+-C3-alkoxycarbonyl], benzyl [the iron group is optionally substituted with fluorine, chlorine, bromine, cyano, nitro, C1- C1-alkyl, trifluoromethyl, CI~C,-alkoxy-carbonyl, C,-04-alkoxy or di(C
1NC2-alkyl)-amino-sulfonyl] or an optionally substituted phenyl group, where R+1'' and R13 are the same or different, and the above for R7 and Ra has meaning, but,
R in each individual case? and not identical to R6; and furthermore, R3 represents a group -0R14, where Rl 4 ti 01~CI! -Alkyl [iron group is optionally fluorine, chlorine, bromine, 01-C4-alkoxy, ClN
C3-alkylthio, 01-C2-alkylsulfinyl or C8-C3-alkylsulfonyl], C5-C0-cycloalkyl, 03-C,-7chloroalkyl-01-C,-furkyl, C3-C8-alkenyl [the iron group may optionally be substituted with fluorine, chlorine or bromine], C1-C6-alkynyl, C1-C1-alkoxy-carbonyl-08
~C,-furkyl, aminocarbonylmethyl, Cl-0
4-alkylamino-carbonyl-methyl or di(
CI-c, -alkyl)-amino-carbonyl-methyl, or phenyl, benzyl, benzhydrylmodi<haphenethyl [these groups may optionally be fluorine, chlorine, nitro, sia, C1-C4-alkyl, 01- C4-
or further \rl+1' represents hydrogen or C1-C1-alkyl, and 16 is hydrogen or C2-C4-alkyl [iron group is optionally substituted with fluorine, chlorine, bromine, cyano, C8-C1-alkoxy or 01-C3-alkoxy-carbonyl], or represents C8-C8-cycloalkyl, phenyl, benzyl or enethyl [These groups may be optionally substituted with fluorine, chlorine, bromine, cyano, nitro, C1-C, -7/l/kyl, C,NC,-alkoxy or C8-C4-alkoxy-carbonyl] −] or C,,C,−
Alkyl-carbonyl, 01-C4-alcokyne-carbonyl, C,%C,-alkyl-sulfonyl matah phenyl-sulfonyl (the iron group may optionally be substituted with fluorine, chlorine, bromine, cyanide, nitro or methyl); ; and furthermore, R2 is a sulfonyl group R11-80!
-1 However, when Rden 1 has the above meaning,
Further, R1 represents hydrogen; , C1-C4-alkoxy [the iron group may optionally be substituted with fluorine and/or chlorine] or 01-C4-alkylthio [the iron group may optionally be substituted with fluorine and/or chlorine] R5 represents hydrogen, fluorine, chlorine, bromine or C1-C4-alkyl [the iron group may optionally be substituted with fluorine and chlorine], or cyano, hol-poor, , C1-C2-alkyl-carbonyl or 01-C4
-alkoxy-carbonyl, f) L; (- and R' is hydrogen or C3-C6-alkyl [iron group is
Tsumoto and/-! or 01-C3-alkoxy [the iron group may optionally be substituted with fluorine and/l or chlorine],
or represents amino, Cl-04-alkylamino or di(01-C2-alkyl)-amino, with the condition that 几6 and 几6 do not represent methyl at the same time, and a novel sulfonylguanidinopyrimidine derivative and strong acid 1:1 adducts of compounds of formula (I) were found according to 2N'-(4,6-dimethoxy-pyrimidin-2-yl)-N〃-methoxy-N
"'-(2-trifluoromethoxy-benzenesulfonyl)-guanidine, N/-(4-methquin-6-methyl-pyrimidin-2-yl)-N//-dimethylamino-
N"-(2-methyl-benzenesulfonyl)-guanidine, N'-(4-methoxy-6-methyl-pyrimidiso-2-yl)-N"-methoxy-Nll/(2-chloro-benzenesulfonyl)-quanidine and hiN'-(4
-methoxy-6-methyl-pyrimidin-2-yl)-N
“-Dimethylamino-N///-(2-chloro-benzenesulfonyl)-guanidine potassium salt.

When M represents hydrogen, the general formula (I) is represented by the formulas (IA) and (rB), where R1, R1, R,! , R4, R6 and R6 are E
represents the individual tautomers and mixtures of the tautomers (IA) and (IB') with the meanings given below.

The mixing ratio (1 person)/(IB) depends on factors that determine the state of aggregation, such as temperature, solvent and concentration.

In addition to MK, further tautomers (IC) can exist if R1 represents hydrogen: the novel sulfonylguanidinopyrimidine derivatives of formula (I) are of the formula (a) when M represents hydrogen; II) wherein the guanidinopyrimidine derivative of the formula (I R1-80, -C1α) in which R1 has the above meaning; (b) M
represents hydrogen, and R2 is hydrogen or C1-C1-
When alkyl is represented, a sulfonylguanidinopyrimidine derivative of the formula (ID) obtained by the method described in (a) In the presence of an acid acceptor and if appropriate in the presence of a diluent, a compound of the formula (1'V) in which R1 represents hydrogen or 01-C4-alkyl and R3 has the meaning given above, or react with an amino compound or a hydrochloride of an amino compound of formula (IV); (c) M represents hydrogen and R1 is a sulfonyl group of the formula %, where 几+1 has the above meaning; In the case of expression (IE), 几1.
33, R4,1 (5 and R6 have the meanings given above), the sulfonylguanidinobi IJ midine derivative of 2M R,1l-8o, - in the presence of an acid acceptor and if appropriate in the presence of a diluent. CI (V>RI in the formula
I has the above meaning, and is reacted with the sulfonic acid chloride: (d) Similarly, M represents water or element, and R2 is 2R11-8
o! In the formula (Yl), when R1 represents a sulfonyl group having the above meaning, in the formula (Yl), R1,
■, R, R, 6 and R11 have the above meanings, in the presence of an acid acceptor and if appropriate in the presence of a diluent, the sulfonylguanidinopyrimidine derivative of formula (1) % formula % (5) (c) When M represents hydrogen and 几2 represents hydrogen or 01-C6-alkyl, the formula (I'll) °\8,7 where R1, l' (4, R1 and R6 have the abovementioned meanings and R1? represents C1-C4-alkyl or benzyl, if appropriate) or react with an amino compound of formula (IV) in the presence of a diluent, where R1 represents hydrogen or C,,C,-alkyl and R3 has the above meaning; When representing 1 equivalent of metal, the above (a), Φ
), (C), (dl and (e)), where M represents hydrogen and 3+, I
f, 11(, 3, 1(, 4, 几6 and R5'' have the abovementioned meanings), if appropriate in the presence of a diluent, as a metal hydroxide, hydride or alkaloid, or as an organic or (g) when preparing a 1:1 adduct of a compound of formula (I) with a strong acid, M represents hydrogen and I, W,
1(+3, rl+', R1' and R6 have the abovementioned meanings) with a strong acid, if appropriate in the presence of a diluent.

The novel sulfonylguanidinopyrimidine derivatives of formula (1) and their adducts with strong acids are characterized by strong herbicidal activity.

Surprisingly, the new compounds of formula (I) exhibit a considerably better herbicidal action than the already known guanidines of a similar type of action.

The present invention preferably uses the formula (I), where M represents hydrogen or one equivalent of a metal, and R1 represents phenyl6, which may optionally be monosubstituted, where 几7 and FL'tt are the same or different. My heart is deep,
Hydrogen, fluorine, chlorine, bromine, cyanide, nitro or methyl [nucleus may be fluorine, chlorine, cyano, C4-C8-alkoxysulfonyl, C2-C1-alkoxy, 01
-C1-alkylthio, C8-C3-alkylsulfinyl or Ir1cI-C3-alkyl, which may be substituted with C1-C1-alkoxy; -Alkoxycarbonyl, C8-C3-alkoxy, C,,
C,-alkylthio,C,~C8-alkylsulfinyltttf Cr~C1-furkylsulfonyl]; Or C1~
C3-alkylsulfonyl [These groups optionally contain fluorine,
chlorine, cyano (optionally substituted with C3-C1-alcokyne-carbonyl) or di(C2-
C1-alkyl)-amino-sulfonyl, CI~C,-
Alkoxy 7-methylaminosulfonyl, phenylmataha phenoxy or 01-C4-alkoxy-carbonyl [the nucleus may optionally be substituted with fluorine, chlorine, bromine, cyano or C,-C1-alkoxy]
,]C1-C0-cycloalkoxycarbonyl 01-
C4-furkylthio-carbonyl, C(C3-C5-
alkyl)-amino-carbonyl ii: C+~C5
-alkoxymethylamino-carbonyl, or C! ~C4-' alkenyl [the nucleus may be optionally substituted with fluorine, chlorine, cyano or C,,C,-alkoxy-carbonyl]; or further, R1 is optionally substituted benzyl represents the group,
Here, 11.9 and R'' are the same or different,
represents hydrogen, fluorine, chloride, cyano, nitro, methyl, methoxy or C3-C,-alkoxycarbonyl; and furthermore, R1 represents hydrogen methyl or a sulfonyl radical truncated t-SO,-, where R is ~C8-alkyl [the group may optionally be substituted with fluorine, chlorine or cyano], C2-C6-
Alkoxy [the nucleus may optionally be substituted with fluorine, chlorine or cyano], C2-C6-alkenyl [the nucleus may optionally be substituted with fluorine, chlorine, cyano or phenyl], 02- C3-alkenyloxy [the nucleus may optionally be substituted with fluorine, chlorine, cyano or phenyl], C8-C6-alkylamino, C8
~C6-cycloargylamino or di(C+-C
s-”alkyl)-amino [these groups optionally contain fluorine,
Chlorine, cyano, phenyl, phenoxy or 01-C1
- may be substituted with alkoxy], C7-C6-
alkenylamino [the nucleus may optionally be substituted with fluorine, chlorine, cyano or phenyl], phenylaminomo or benzylamino [these groups can optionally be substituted with fluorine, chlorine, bromine, 01-C4-alkyl, trifluoro Methyl, C3-C8-alkoxy, 01-C2-fluoroalkoxy, C2-C1-alkylthio, 01-C5-
Alkylsulfinyl, C1PvC1-alkylsulfonyl, cyano, nido-O and/or optionally substituted with C1-C8-alkoxy-carbonyl], benzyl [optionally substituted with fluorine, chlorine, cyano, nitro, methyl, methoxycarbonyl] or C1-C1-alkoxy-carbonyl] or optionally substituted phenyl! and 1 (1s are the same or different and have the meanings given above as preferred for R? and R', provided that in each individual case R7 and R8
furthermore R3 represents the group -Qll, +4, where [(, +4
r, 1 C, ~C8-alkyl [the third optionally may be substituted with fluorine or chlorine], or C5-C
6-alkenyl [the optionally substituted with chlorine], 01-C,-alkoxy-carbonyl-C,NC,-alkyl, phenyl, phenethyl or benzyl [the optionally substituted with fluorine, optionally substituted with chlorine, nitro, methoxy or 01-C2-alkoxy-carbonyl; or further p, l! 1 represents hydrogen and methyl, and R1”
U water P! or C8-C1-arlekyl [which optionally may be substituted with fluorine, chlorine, cyano, C2-C1-alkoxy or C3-C2-alkylsulfonyl], or C1-C6-cycloalkyl, Phenyl, benzyl or phenethyl [wherein optionally fluorine, chlorine, bromine, nitro, cyano, C2-C! -alkyl, 0
1-C2-alkoxy or 01-Ct-alkoxy-
or acetyl, methoxycarbonyl, benzenesulfonyl or toluenesulfonyl; and also fluorine, chlorine or methyl, optionally substituted with fluorine and/or chlorine; C
1~C! -alkoxy, optionally substituted with fluorine and/or chlorine, or B C
l-Ct-alkylthio [said number may be optionally substituted with 7 and/or chlorine] as shown in Table 4, R6 is hydrogen, fluorine, chlorine, bromine, methylpacetyl or C4-C2-alkoxy- represents carbonyl and R6 represents C5-C8-atrekyl, optionally substituted with fluorine and/or chlorine;
C, ~C1-alkoxy [wherein optionally fluorine and/-!
, optionally substituted with chlorine], or amino, C1-C1-alkylamino or di(C
1-C1-alkyl)-amino, as a condition,
R4 and R6 do not represent methyl at the same time, and relate to the compound button.

Furthermore, the invention preferably provides hydrohalic acids such as hydrogen chloride, hydrogen bromide and hydrogen iodide, sulfuric acid or trifluoroacetic acid, having up to 4 carbon atoms and optionally substituted with fluorine or chlorine. good alkanesulfonic acid,
or by benzene- or nanthalene-sulfone, optionally substituted with fluorine, chlorine, bromine or methyl, as defined above, in which M represents hydrogen (1
).

The present invention particularly relates to the formula (I), where M represents water or one equivalent of sodium, potassium or calcium, and R represents a substituted phenyl group, where R. Fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy, difluoromethoxy, trifluoromethoxy, C3-C3-alkylthio, C2-C1-alkylsulfinyl, C1-C,-alkylsulfonyl,
Dimethylaminosulfonyl, diethylamino.

represents sulfonyl, N-methoxy-N-methylamino-sulfonyl, phenyl, ClNC4-alkoxy-carbonyl, difluoromethylthio or trifluoromethylthio, and R8 represents hydrogen; further K R2 is hydrogen, methyl or a sulfonyl group R11-8o ,
-, where R,lIc,,C,-alkyl [:m group tiliff
or C1-C3-alkylamino or Id') -
(ClNC2-alkyl)-amino [these groups Vi may be optionally substituted with fluorine] or optionally substituted phenyl group, where R'' and R1'' are the same They are different, hydrogen, fluorine, chlorine, bromine, cyano, nitro, methyl, trifluoromethyl, C,,C,-alkoxy [this number is optionally fluorine, salt L7ano or C1-C5-alkoxy- optionally substituted with carbonyl], 01-C8-
alkylthio, 01-C1-alkylsulfinyl or 01-C8-alkylsulfonyl [these groups may optionally be substituted with fluorine and/or chlorine],
represents dimethylaminosulfonyl, diethylaminosulfonyl, N-methoxy-N-methylaminosulfonyl, phenyl or ClNC6-alkoxy-carbonyl, optionally substituted with fluorine, chlorocyano or CO-C8-alkoxy; Furthermore, H and s represent the group -OR+4, where R's is C1 to C
3-alkyl [this number may be optionally substituted with chlorine], C1-C4-alkenyl [this number may optionally be substituted with chlorine], or hc+
~C,-alkoxy-carbonyl-methyl, fenino 7-enethyl, tahbenzyl [wherein optionally fluorine, chlorine,
Nitro, cyano, methyl, methoxy or 01-C1-
substituted with alkoxy-carbonyl, R1' represents hydrogen or methyl, and R,+8 is hydrogen, C8-
C8-alkyl, C8-C6-cycloalkyl, phenyl, acetyl, methoxycarbonyl, benzenesulfonyl or toluenesulfonyl; ] II5 represents hydrogen, methoxycarbonyl, ethoxycarbonyl or acetyl; ] or C0～
C1-alkoxy (which number may optionally be substituted with fluorine and/or chlorine), hydric acid, sulfuric acid, trifluoroacetic acid, methanesulfonic acid,
Concerning the 1:1 adduct of the above defined compound with benzenesulfonic acid and 0:toluenesulfone rRK.

Also excluded from the preferred and especially preferred range are the nine individually mentioned compounds.

For example, the method (2-fluoro-benzenesulfonyl chloride and N'-(4-
Methoxy-6-methyl-pyrimidin-2-y/L/)
When using -Nl〃-ethoxy-guanidine, the reaction process is shown by the following reaction formula, e.g. method Φ)
As starting material for K When using phenylhydrazine and phenylhydrazine, the reaction process can be shown by the following reaction formula: For example, method (C) N/-(4
,6-dimethoxy-pyrimidin-2-yl)-N"-benzyloxy-N/// (2-chloro-phenylmethylsulfonyl)-guanidine l"2-trifluoromethane-sulfonylchlorytra, the reaction process is For example, as starting material for process (d) N/-(4-
etoyac-6-methyl-pyrimidin-2-yl)-N”
When using -methoxy-N"-(2-ethoxycarbonyl-benzenesulfonyl)-guanidine and 2-dimethylaminosulfonyl-benzenesulfonyl chloride, the reaction process can be illustrated by the following reaction scheme: e.g. method (e) N/(4
-methoxy-6-methyl-pyrimidin-2-yl)-N
When using “-(2-methyl-benzenesulfonyl)-5-methyl-isothiourea and N,N-dimethylhydrazine, the reaction process can be illustrated by the following equation: For example, method (f) for Ic N/-(4
,6-dimethoxy-pyrimidin-2-yl)-N/-
isobutoxyN///(2-methoxycarbonyl-
When using phenylmethylsulfonyl)-guanidine and potassium etallate, the reaction process can be illustrated by the following reaction scheme: + KOC,Hl For example, N'-(5
-acetyl-4-methyl-pyrimidin-2-yl)-N
“-Methoxy-N”-(2-chloro-benzenesulfonyl) N///-(2-difluoromethoxy-benzenesulfonyl)-When using guanidine and methanesulfonic acid, the reaction process is shown by the following reaction formula. Method (a) The guanidinopyrimidine derivatives used as starting materials for K are generally defined by 20) K.

In the formula (U), R, 3, R', R' and R6 have the same meanings indicated as preferred or especially preferred with respect to the description of the substituents of the formula (I) and in particular with respect to the description of the substituents of the formula (I). have

Possible examples of starting materials of formula (Il) are =
N/(4-methyl-pyrimidi/-2-yl)-1
N'-(4-ethyl-pyrimidin-2-yl)-1N'
-(4-Methoxy-6-methyl-pyrimidin-2-yl)-1N'-(4-ethoxy-6-methyl-pyrimidin-2-yl)-1N'-(4-propoxy-6-methyl-2- yl)-1N/-(4-inpropoxy-6-methyl-pyrimidin-2-yl)-1N'-(4-chloro-6-methoxy-pyrimidin-2-yl)-1N'-(
4-chloro-6-nidoxy-pyrimidine-2-yl)
-1N'-(4-chloro-6-dimethylamino-pyrimidin-2-yl, N'-(4-methyl-6-methylthio-pyrimidin-2-yl)-1N'-(4,6-dimethoxy-pyrimidin-2-yl) -yl)-1N'-(4-difluoromethoxy-6-methyl-pyrimidin-2-yl)-
and N/-(4-dimethylamino-6-methyl-pyrimidin-2-yl)-N"-methoxy-guanidine,
-N"-Ethoxyquanidine, -N"-Propoxy-
Guanidine, -N"-isopropoquine-guanidine, -
N//-butoxy-guanidine, -N//-isobutoxyguanidine, -N"-56c, -butoxyguanidine, -N'-pentoxy-guanidine, -N"-isopentoxy-guanidine, -N" -Hexyt-leoquin-guanidine, -N"-Octero-oxeguanidine, -
N"-allyloxy-guanidine, -N"-(2-chloro-ethoxy)-guanidine N//(2-fluor.

-ethoxy)-guanidine, -N"-(2-lyropropoxy)-guanidine, -N"-(2-fluoro-propoquine)-guanidino, -N-(3-chloro-propoquine)-guanidino, -N "-(4-chloro-butoxy)-guanidine, -N"-methoxy-carbonylmethoxy-guanidine, -N"-ethoxyluponylmethoxy7-guanidine, -N"-(1-methoxycarbonyl-ethoxy)-guanidino, -N"-(1-ethoxycarbonyl-ethoxy)-guanidine, -N//-dimethyl-aminocarbonyl-methoxy)-guanidine, -N
"-(2-phenyl-ethoxy)-guanidine-N"-
7 Dinoxyguanidine, -N"-(4-methyl-benzyloxy)-guanidine, -N"-(4-fluoro-
benzyloxy)-guanidine, -N''-(4-chloro-benzyloxy)-guanidine N//-(4-
Nitro-benzyloxy)-guanidine, -N"-(2
,6-')chloro-benzyloxy)-guanidine,-
N // ++ (4-methoxycarbonyl-benzyloxy)-guanidine, l'-N''-(4-ethoxycarbonyl-benzyloxy)-guanidine.

The starting material of 2G) is covered by the already filed patent [EP-O8(
However, formula (n)
, However, (a) R' represents chlorine, R' represents hydrogen, Ra is CI~C4-alkoxy [the nucleus crystal may be optionally substituted with fluorine and /'+take chlorine], C1~ C
4-alkylamino or di(1,4-alkyl)-
represents amino, 0) 4 represents 01-C6-alkyl [the nucleus may be optionally substituted with fluorine and/or chlorine], B, s represent hydrogen, and R' C8-C4 is substituted with fluorine and/or chlorine
-alkoxy, or C,,C,-alkylamino or di(C+ to C4-alkyl)-amino, or (c) R' and Bs represent hydrogen and R6 is C8
The compounds of ~C3-alkyl and in each case 3 has the meaning given above are new.

Guanidinopyrimidine derivatives of formula (TI) - thus also formula (ff) as defined in (a), Φ) and (C) above
The new compounds of a), <'ab) and (rIC) have the formula (
ii) A cyanoaminopyrimidine derivative of the formula, in which R4, R5 and R6 have the above meanings, is added to a cyanoaminopyrimidine derivative of
An amino compound of the formula (IX) HtN-R' (M) in which R1 has the abovementioned meaning at a temperature between 20°C and 150°C, preferably between 50°C and 120°C, in the presence of It is obtained by reaction with its hydrochloride and, if appropriate, treatment of the reaction product with an acid acceptor, such as ammonia, sulfur hydroxide solution or sodium carbonate.

Cyanoaminopyrimidine derivatives of formula (1) constitute the subject matter of an already filed patent (see EP-O8 (European Patent Application Publication No. 121,082)); however, formula (■), with the proviso that (al 几4 represents chlorine, R5 represents hydrogen, and 几6 represents C,,C,-alkoxy [the nucleus crystals may optionally be substituted with fluorine and/or chlorine], Cl-C4-
alkylamino or di(01-C6-alkyl)-
(b) R4 represents C3-C3-alkyl, which optionally may be substituted with fluorine and/or chlorine, R2 represents hydrogen, and H, e fluorine; and/or C substituted with chlorine, C
, -alkoxy or C+~C4-alkylamino represents di(C8-C4-alkyl)-amino; or (c) R' and FLs represent hydrogen and R6
is C! The compounds represented by ~C5-alkyl are new.

Compounds of formula (W) - thus also formulas (Ia), 0'lb) and (C) as defined above (a), (b) and (C)
C) The novel compound - is obtained essentially by the following synthetic route: (al) an inert diluent, if appropriate, e.g. ethanol;
An alkali metal or alkaline earth metal salt of cyanamide, such as sodium cyanamide or calcium cyanamide, is prepared by the formula (
X) wherein R4, R' and R6 have the above meanings. Concentrate the mixture;
After dissolving the residual liquid in water, the cyanoaminopyrimidine derivative of formula (■) can be precipitated by acidification, for example with hydrochloric acid, and isolated by suction filtration.

Alternatively, the cyanoaminopyrimidine derivatives of formula (■) may be prepared by converting cyanoguanidine ("dicyanodiamide") into a suitable β-dicarbonyl compound - or derivative thereof - when (at) R and/or Ra represent hydroxyl. For example, 1,1-dimethoxy-3-oxo-butane, methyl acetoacetate or ethyl acetoacetate [J, Prakt.
, Chem,) 77.542 (1908) and Journal Op.
, Chem, Soc, ) 194 B, 586] or dimethyl malonate or diethyl malonate (
(see German Patent No. 158.591).

2-cyanoamino-4-hydroxymethyl- or - obtained from acetoacetic ester or malonic ester
4,6-Dihydroxy-pyrimidines are prepared in a known manner, if appropriate in the presence of a diluent such as water, methanol, ethanol, n- or imbrobanonohedioxane or dimethylformamide and an acid binder such as sodium hydroxide or The corresponding 2-
cyanoamino-4-alkoxy-6-methyl- or-
It can be converted to 4,6-dialkoxy-pyrimidine. To avoid N-alkylation, the acylation may be carried out using an acylating agent, such as anhydrous vinegar! 1 or acetyl chloride, and after alkylation the product is deacylated again with aqueous acid or base.

In another alternative, the cyanoaminopyrimidine derivative of formula (■) is an optionally inert aminopyrimidine of formula (1) in which R4, R5 and R6 have the meanings given above. in the presence of a diluent such as acetone, acetonitrile or toluene at a temperature between 0°C and 100°C with a carbonyl inthiocyanate of the formula %, in which R16 represents ethoxy or phenyl, resulting in a compound of the formula K. (XI') where R', R,', R' and R1'a as above.

The carbonylthiourea having the meaning is isolated, if appropriate after concentrating the mixture, and treated with aqueous alkali gold g4 at a temperature between 0°C and 120°C, if appropriate in the presence of an organic solvent such as tetrahydrofuran or dioxane. or the thiourea of the formula (XIV) obtained as crystals after reaction with an alkaline earth metal hydroxide solution and acidification, for example with hydrochloric acid, in which R4, R5 and R6 have the meanings given above, is isolated by suction filtration. , in the presence of an aqueous alkali gold F% or alkaline earth metal hydroxide solution, such as sodium hydroxide solution, from 20°C to 10°C.
Metal compounds capable of binding hydrogen sulfide at temperatures between 0 °C, such as copper acetate (■), mercury acetate (II) or iron acetate (I
I), and when the reaction is complete, filter the mixture;
Then, it is obtained by acidifying the F solution with an acid, for example, acetic acid.

The product of formula (■) thus obtained as crystals can be isolated by filtration.

The starting materials for the above processes for producing (a'), (a) and (R3) for the cyanoaminopyrimidine fatty conductor of formula (■) are known and/or can be produced by methods known per se. I can do it.

These substances include chloropyrimidines of formula (x) (:J
, Ch6m, Soc, (c) 1966.2031:
Chem Farm Bu/L/ (Cb, em, Ph
arm, Bull I, ) 11.1382-13
88 (1963) and Arch Farm (Arch,
Pharm, ) 2 g 5.649-657 (196
2)], aminopyrimidines of formula (Xl) [chem-
7 arm-bu tv (Chem, Pharm, Bu tv
11. ) 11.1382-1388 (1963): J
,Chem.

Soc, 1946.81 and U.S. Patent No. 4.299.
960] and carbonyl isothiocyanate of formula (■) [Journal of Heterocyclic φ Chemistry (J, H6t6rocycle, Chem,
) 5.837 (1968) and U.S. Patent No. 4.160.
037] is included. .

Similarly, the amino compound of formula (ff) used as a starting material is already known and can be produced by a method known per se [Ch6m
, Pharm, Bu I 1.15.345 (196
7); Bu l l,
Soc, Chim, France) 1958
．． 664; Synthesis 19
76.682; J, Chem, Soc, l 930
．． 228 and Helheti h・Himika・1 Kuta (Hel
v, Ch6m, Acta) 45.1387 (1962)
reference〕.

The sulfonic acid chloride used as a starting material for method (a) K is also generally defined by formula (1).

In the formula (IQ, R11 is preferably and K, the formula (
Preferences or particularly preferences regarding the description of the substituents in I) have the same meanings as indicated above.

Possible examples of starting materials of formula (1) are: 2
-chloro13-chloro14-chloro-12,5-dichloro-,2-sluo0-14-fluoro-12-bromo-14-bromo-12-nitro-14-nitro-12
-cyano-12-methyl-14-methyl-12-chloromethyl-12-trifluoromethyl-22-methoxy-
12-difluoromethoxy-12-trifluoromethoxy-12-methylthio-12-methylthiomethyl-12
-methylsulfinylmethyl-,2-methylsulfonylmethyl-12-')methylaminosulfonyl+,2-diethylaminosulfonyl-22-phenyl-12-methoxycarbonyl-12-ethoxy7carbonyl-,2-7
'Ropoxycarbonyl-, 2-inpropΦdicarbonyl-12-butquinecarbonyl-12-dimethylaminocarbonyl-12-diethylaminocarbonyl-12-
7 enoxy, 2-methyl-5-chloro-12-chloro-5-trifluoromethyl-12-methylsulfonyl-
12-ethylsulfonyl-12-chloro-4-trifluoromethoxy-13-chloro-4-trifluoromethoxy-12-trifluoromethoxy-5-chloro-13,
5-diclogoo 12-difluoromethylthio- and 2-
Trifluoromethylthiobenzenesulfonyl chloride, and also methane-, chloromethane-, trifluoromethane-, ethane-12-chloroethane-, ethene-, propane-, butane-, perfluorobutane- and perfluoro-octane-sulfonyl chloride; methyl- ,
Ethyl-, propyl-, inpropyl-, cyclohexyl-, dimethyl- and U')ethylsul7amino acid chloride and (2-chloro-phenyl)-1(2-cyano-
phenyl)- and (2-methoxycarbonyl-phenyl)-methanesulfonyl chloride.

The sulfonic acid chloride of formula (11) is a known one,
and/or by methods known per se [: J, Org, Chem, 33.
2104 (1968); J, Org, Chem, 25
．． 1824 (1960): DB-As (German Patent Application Publication Specification) No. 2,308,262; BP-O
8 (European Patent Application Publication Specification) No. 23.140, European Patent Application No. 23,141, European Patent Application No. 2 422, European Patent Application No. 35,
No. 893, No. 48,143, No. 51°466-Feng, No. 64.322, No. 70.041, No. 4, No. 808 and No. 44,809: U.S. Patent No. 4929
．． No. 820, No. 4.282.242, No. 4.34
No. 8,220 and No. 4,372,778 and Angew, Ch6m 93.1
51 (1981)] These compounds are obtained essentially by two synthetic routes: (1) The corresponding sulfonic acid rL180. H or an alkali metal or alkaline earth metal salt thereof, if appropriate in the presence of a catalyst such as pyridine or dimethylformamide, and if appropriate an inert diluent such as methylene chloride, chloroform, acetonitrile, chlorobenzene and/or or using sulfolane at a temperature between -20°C and +150°C, preferably between 0°C and +100°C, with a halogenating agent such as phosphorus pentachloride, phosphoryl chloride (phosphorus oxychloride), thionyl chloride, phosgene or pencitrichloride. After dilution with water, the sulfonic acid chloride can be isolated by suction filtration, if it is obtained as crystals, or in water-immiscible solvents such as methylene chloride, diethyl ether, etc. or (2) in a manner known per se (: J, Org.
Chem.

25.1 s 24 (1960); DE-O8 (
4308.262 and European Patent No. 59,241], the corresponding amino compound R1-NH, if appropriate in the presence of acetic acid, between -10C and +20C. Reaction with sodium nitrite and hydrochloric acid, preferably at a temperature between -5°C and +10°C, then 1c (in situ) in the presence of a copper compound such as copper chloride or copper fluoride as a catalyst, between 0°C and 80°C.
℃, preferably between 10°C and 60°C with a salt of sulfur dioxide or sulfite, such as sodium sulfite spray or sodium bisulfite.

The work-up can be carried out in the usual manner: upon dilution with water, the sulfonic acid chloride is generally obtained as crystals, which can be isolated by suction filtration. However, they can also be extracted from the aqueous dispersion with solvents which are practically immiscible with water, such as methylene chloride or diethyl ether, dried and purified by vacuum distillation.

The sulfonylguanidinopyrimidine derivatives used as starting materials for process (b) K are generally identical compounds of the formula (ID)' and, in particular, as indicated as preferred or particularly preferred with respect to the description of the substituents of the formula (1). has the meaning of

Examples which may be mentioned of compounds of formula (ID) are: N
/(4-ri0ro6-methoxy-pyrimidin-2-yl)-N"-methoxy-N" N11l -bis-(2-
chloro-benzenesulfonyl)-1-N", N"-bis-(2-bromo-benzenesulfonyl)-1-N//,
N”-bis-(2-fluoro-benzenesulfonyl)-
1-N", N"-bis-(2-methyl-benzenesulfonyl)+, -N".

N'//-bis-(2-trifluoromethyl-benzenesulfonyl)-1-Ntt, N//F-bis-(
2-methoxy-penmensulfonyl)-1-N” N/
//-Bis(2-phenyl-benzenesulfonyl)-
1 and -N//, N///-bis-(2-methoxycarbonyl-benzenesulfonyl)-guanipan
N/-(4-methyl-pyrimidin-2-yl)-N"-
Methoxy-N", N"-bis-(2-coulolobenzenesulfonyl)-1-N", N"-bis-(2-cytoki7carbonyl-benzenesulfonyl)-1-N", N"
-bis-(2-cyfureoloftoxy-benzenesulfonyl)-1-N" N/// ++ His-(2-diethylaminosulfonyl-benzenesulfonyl)-1-N
//, N'/'-bis-(2-bromo-benzenesulfonyl)-1-N"N///-bis-(2-trifluoromethylthio-benzenesulfonyl)-1-N",N"
-bis-(2-phenoxy-benzenesulfonyl)-1
and -N" Nl//-his-(2-methyl-sulfonyl-benzenesulfonyl)-guanidine, N'-(4,
6-dimethoxy-pyrimidin-2-yl-N''-methoxy-N''.

N″-bis-(2-chloro-benzenesulfonyl)-1
-N",N"-bis-(2-methoxycarbonyl-benzenesulfonyl)-1-N",N"-his-(2-difluoromethoxy-benzenesulfonyl)-1-N",
N"-bis-(2-trifluoromethoxy-benzenesulfonyl)+, -N", N/"-bis-(2-dimethylaminosulfonyl-benzenesulfonyl)-1-N"
, N″-bis-(2-methylthio-benzenesulfonyl)-1-N″.

N l//-bis-(2-ethoxycarbonyl-benzenesulfonyl)-1-N", N"-bis-(2-phenyl-benzenesulfonyl)-1-N tt , N//
/-bis-(2-cyclopropyloxycarbonyl-benzenesulfonyl)-1-N /I, N'//-bis-(2-trifluoromethylsulfonyl-benzenesulfonyl)-1-N//N''-bis -(2-nitro-benzenesulfonyl)- and N tt , Nr
n-bis-(2-cyano-benzenesulfonyl)-guanidine, N'-(4-methoxy-6-methyl-repyrimidin-2-yl)-N"-methoxy-N".

N″-bis-(2-chloro-benzenesulfonyl)-1
N tt , N-bis-(2-methoxycarbonyl-
benzenesulfonyl) -1-N" Nl//-bis-
(2-methoxycarbonyl-benzenesulfonyl)-1
-N",N"-bis-(2-methylresulfonylpenzunesulfonyl)-1-N",N"-bis-(2-methylthio-benzenesulfonyl)-1-N",N"-bis -(2-trifluorometho-7-benzenesulfonyl)
-1+ No, N///-bis-(2-ethoxycarbonyl-benzenesulfony)-1-N", N
″-bis-(2-trifluoromethyl-benzenesulfonyl)-1-N″ Nl1l-bis-(2-isopropylthio-benzenesulfonyl)-1+ Nw,
N/#-bis-(2-N-methoxy-N-methylaminosulfonyl-benzenesulfonyl-, -N", N"-
Bis-(2-triphlheolomethylthiobenzenesulfonyl)-, -Nu,N"t'-his-(2, 5
-')chloro-benzenesulfonyl)-, -pJ //
, Nl//-bis-(2-phenoxy-benzenesulfonyl)- and -N", N"-bis-(2-phenyl-benzenesulfonyl)-4 ayudine, N'-(4-difluoromethoxy-6-methyl -pyrimidin-2-yl) -N"-methoxy-N", N"-bis-(2-ethoxycarbonyl-benzenesulfonyl)-, N tt
, Nl//-bis-(2-bromo-benzenesulfonyl)-, -Nl/N//'-bis-(2-methylsulfonylmethyl-benzenesulfonyl)-1-N",
N″-bis-(2-trifluoromethylthio-benzenesulfonyl) +, -N″.

N″-bis-(2-methoxy-benzenesulfonyl)-
1-N", N"-bis-(2-methoxycarbonyl-benzenesulfonyl')- and H-N〃, N'〃-bis-
(2-Chloro-benzenesulfonyl)-guanidine.

Compounds of formula (rD) can be prepared by the method described in (a) Ic.

The amino compound used as a starting material in method (b) is also generally defined by formula (ff). Expression (IT
), 1'4z and R3 are preferably and especially
Regarding the definition of the substituents of formula (1), they preferably have the same meanings as mentioned above.

Possible examples of starting materials of formula (ff) are:
N,N-dimethylhydrazine, phenylhydrazine, 0
-Methyl-hydroxyfluamine, O-ethyl-hydroxylamine, 0. N-dimethylhydroxylamine and O-propyl-1O-eventylene, 0-ynepentylene, O-5 (4c.

- Benthru, 0-hexyl-10-ynehexyl-1
0-hebutyl-10-isohebutyl-10-octyl-
10-Inoctyl-10-allyl-10-crotyl-
10-(2-chloro-ethyl)-10-(2-fluoro-ethyl)-10-(2-chloro-propyl-10-(
3-chloro-propyl)-10-(4-chloro-butyl)-10-methoxycarbonylremethyl-, 0-ethoxycarbonylmethyl-1o-(1-methoxycarbonyl)-ethyl-1o-(1-ethoxycarbonyl )-ethyl-10-aminocarbonylmethyl, o-(2-phenyl-ethyl)-10-phenyl-10-(4-methyl-benzyl)-10-(4-fluoro-benzyl)
, -1O-(4-chloro-benzyl)-10-(4-nitro-benzyl)-10-(2,6-dichloro-benzyl)-1O-(4-methoxy7carponyl-benzyl)-
and 0-(4-ethoxycarbonyl-benzyl)-hydroxylamine.

The amino compound of formula (lY) is a known compound and can be produced by a method known per se (Chem.
, Pharm, Bul 1.15.345 (196
7); Bull, Soc, Chim, France
1958.664;5ynthesis l 97
6.682; J, Chem, Soc.

1930.228 and He1v, Chim, Act
a45, tLR7 (see 196:l).

The lephonylguanidinopyrimidine derivatives used as starting materials in the method (c>Ic) are generally defined by the formula (TE).RIJ in the formula (TE).

R4, R1 and R6 preferably and in particular have the same meaning as mentioned above in the definition of the substituents of formula (1) as rn+, preferably b or particularly preferred.

Possible examples of compounds of formula (TE) are: N
'-(4,6-dimethoxy-pyrimidin-2-yl)-
N"-Metquin-NI// (z-chloro-benzenesulfonyl)-guanidine N/// +(3-chloro-benzenesulfonyl)-1N///-(4-chloro-benzenesulfonyl)-1-N" -(2-fluoro-
benzenesulfonyl)-1-N/// (4-fluoro-benzenesulfonyl)-1N#/ (2-bromo-benzenesulfonyl)-1+ N/// -(4-bromo-benzenesulfonyl)-1-Nl/ / (2-
cyano-benzenesulfonyl)-1-N/// (2
-nitro-benzenesulfonyl)-1Nl// (4
-nitro-benzenesulfonyl)-1N'// -(2
-Methyl-benzenesulfonyl)-1-N”-(4-methyl-benzenesulfonyl)-1-N///-(2-
Chloromethyl-benzenesulfonyl") -1-N"-
(2-trifluoromethyl-benzenesulfonyl)-1
-NI/l (2-methoxy-benzenesulfonyl)
-1pJI/! (4-methoxy-benzenesulfonyl)-1-N''-(2-methylthio-benzenesulfonyl) -1N///+ ('l-difluoromethoxybenzenesulfonyl)-1-N''-(2-tri Fluoromethosulfonate (benzenesulfonyl) -1-Nut
(2-methylthiomethyl-benzenesulfonyl) -1
N///-(2-';methylaminosulfonylbenzenesulfonyl)-1-N""-(2-phenyl-W
Zensu? (2-methoxysulfonyl-benzenesulfonyl)-1-N///
(2-methoxycarbonyl-benzenesulfonyl)-1-N/// (2-ethoxycarbonyl-benzenesulfonyl)-1-N''-(2-propoxycarbonyl-benzenesulfonyl)-1pqll/-(2- Methylaminocarbonyl-benzenesulfonyl)-1-N
""-(2-ethylaminocarbonyl-benzenesulfonyl)+,-N"-(2-y'-pyramid-7carbonyl-benzenesulfonyl)-1-N"IF (2-
methoxyaminocarbonyl-benzenesulfonyl)-1
-N/// (2-ethoxyaminocarbonyl-benzenesulfonyl) -1-N'a-(2-propoxyaminocarbonyl-benzenesulfonyl)+, -N" -
(2-dimethylaminocarbonyl-benzenesulfonyl) x HeN///-(2-diethylami7carbonyl-benzenesulfonyl)-guanidine;
N'-(4゜6-dimethoxy-pyrimidin-2-yl)
-N”-ethoxy-N22-benzenesulfonyl-1-
N″-(2-chloro-benzenesulfonyl)-1-N″
-(3-chloro-benvinsulfonyl'l-1-N"'
-(4-chloro-benzenesulfonyl)-1N///-
(2,4-dichloroO-benzenesllephonyl)-1-N
”-(2,5-')chloro-benzenesulfony)-
5-N/// (2-difluoromethoxy-benzenesulfonyl)-1-N/// (2-triflunalomethoxybenzenesulfonyl)+, -N11l-(2-
Methylthio-benzenesulfonyl)-1N///-(2
-Methyl-benzenesulfonyl)-1-Nta(2-
methylthiomethyl-benzenesulfonyl)+, -N"-
(2-dimethylaminosulfonyl-benzenesulfonyl)-1-N/// (2-methoxysulfonyl-benzenesulfonyl)-1-N/#, -(2-methoxycarbonyl-benzenesulfonyl)-1-Nl/l - (2
-ethoxycarbonyl-benzenesulfonyl)+, -N
/〃-(z-, t-thylaminocarbonyl-benzenesulfonyl)-1-N/// (2-dithylaminocarbonyl-benzenesulfonyl)+, -N”-(2-methoxyami7carbonyl-benzenesulfonyl)- and H-N
"-(2-dimethylaminocarbonyl-benzenesulfonyl)-guanidine; and further KN'-(4゜6-dimethoxy-pyrimidin-2-yl)-N"-propoxy-
N"-isopropoxy-1-NLI-butoxy7-1-N
"-isobutoxy-1-N"-56c, -butoxy-1
-N"-pentoxy-1-N"-hexyloxy-1-
N"-octyloxy-1-N"-allyloxy-1-
N"-crotyloxy-1-N"-(3-chloro-propoxy)-1-N"-methoxycarbonyl-methoxy-
1-N"-Ethoxycarbonyl-methoxy-1-N"-
(1-methoxycarbonyl-ethoxy)+, -N"-(
1-ethoxycarbonyl-ethoxy)-1-N''-(2
-phenyl-ethoxy)+, -N"-7dinoxy, -
N"-benzyloxy-1-N"-(4-methyl-benzyloxy)-1-N"-(4-fluoro-benzyloxy)-1-N"(4-chloro-benzyloxy)-1
-N"-(4-nitro-benzyloxy)-1-N"-
(2,6-dichloro-benzyloxy)-1-N“-(
4-Methoxycarbonyl-benzyloxy')- and H-
N”-(4-ethoxyca I levonyl benzyloxy)
-1-N/// (2-chloro-benzenesulfonyl)-guanidine 1-Nl〃-(2-methoxycarbonyl-benzenesulfonyl)-guanidine;
N'-(4-methoxy-6-methyl-pyrimidine-2-
yl)-N“-methoxy-N/// (2-chloro-
benzenesulfonyl)-1-N/// (2-methyl-benzenesulfonyl) +, -N'// (2-methylthio-benzenesulfonyl)-, -Nl//-(?
, -Ufluoromethoxy-benzenesulfonyl)- and -N/// (2-trifluoromethoxy-benzenesulfonyl)-guanidine; and further KN'-(4-nitoxy-6-methyl-pyrimidin-2-yl) -and-
N″ (4-methyl-pyrimidin-2-yl) N
//-MethoxyN/// (2-chloro-benzenesulfonyl)-guanidine; and further <N'-(4-/'rolo-6-methoxypyrimidine-2
-yl)-N"-methoxy-NIII (2-chloro-benzenesulfonyl)-1-NIII (2-methoxycarbonyl-benzenesulfonyl)-, -NIII
-(2-difluoromethylthio-benzenesulfonyl)
- and QN''-(2-silf-aminomethyl-benzenesulfonyl)-guanidine; and further KN'-(4-chloro-5-ethoxy-pyrimidine-2
-yl)-N"-ethoxy-N'// (2-bromo-benzenesulfonyl)-1NIII -(2-phenylbenzenesulfonyl)+, -N"-(2-dimethylaminocarbonyl-benzenesulfonyl)+, - N'〃-
(2-methylthiomethyl-benzenesulfonyl)-1W
//(2-)Futukishibenzenesulfonyl)- and-
N”-(2-inpropoxy-benzenesulfonyl)
-guanidine; and further N/++ (4-chloro-6-dimethylamino-pyrimidin-2-yl)-N"-methoxy-NIII-(
2-Fluoro-benzenesulfonyl)+, -N"-(
2-:)fluoromethylthio-benzenesulfonyl)-
1++ NIII-(2-methyl-benzenesulfonyl)-1-NIII (2-ethoxycarbonylbenzenesulfonyl)- and -N''-(2-cyano-benzenesulfonyl)-guanidine; and further K N'-(4- Methyl-6-methylthio-pyrimidine-2
-yl)-N"-oriruoxy-N//l (2-chloro-benzenesulfonyl)-1-NIII (2-
Isopropoxy-benzenesulfonyl”)-1-Nm-
(2-phenoxy-benzenesulfonyl)-1-NII
I (2-methylsulfonyl-benzenesulfonyl)
- and -N''-(2-cyclopropyloxycarbonyl-benzenesulfonyl)-guanidine; -Nrtt-(2
-chloro-benzenesulfonyl)-, -N"'-(2-
Chlorodifluoromethyl-benzenesulfonyl)-1-
N"'-(2-N-methoxyN-methyl-aminosulfonyl-benzenesulfonyl)-1-N'-(2-
phenyl-benzenesulfonyl) - and H-Nht-(
2-isopropylthio-benzenesulfonyl)-guanidine; and further k N/-(4-difluoromethoxy-6-methyl-pyrimidin-2-yl) -N"-methoxycarbonyl-
NIII-(2-methyl-benzenesulfonyl)-1
-N'1I-(2-ethylaminosulfonyl-benzenesulfonyl) +, -N''-(2-difluoromethoxy-benzenesulfonyl)-1-NIII (
z-nitrobenzenesulfonyl)-1NIII (
2-methylthio-benzenesulfonyl) - and 0:
NIII, -(2-ethoxycarbonyl-benzenesulfonyl)-guanidine.

Compounds of formula (IE') can be prepared by methods (a) and (b) as described above.
) can be manufactured by

The sulfonic acid chloride used as a starting material in method (C) is generally defined by the formula Bacteria. Formula (l
In which R11 preferably and especially K has the same meanings as indicated above as preferred or particularly preferred with respect to the definition of the substituents of formula (1).

The sulfonic acid chloride mentioned above as an example of the compound of 2〇) can be applied as an example of the starting material of formula (g).

The sulfonic acid chloride of formula (g) is a known one,
and/or can be prepared by methods known per se (see literature and synthetic routes for compounds of formula G above).

The sulfonylguanidinopyrimidine conductor used as starting material for process (d) is generally defined by formula (1'J). Formula (M) K Oite, R, 3, 几4, R5
, R6 and R11 preferably and especially with respect to the definition of the substituents of formula (1) have the same meanings as indicated above as preferred or particularly preferred.

Examples which may be mentioned of compounds of formula (Vl) are: N
'-1-(4-methyl-pyrimidin-2-yl)-1N
l (4-methoxy-6-methyl-pyrimidine-2-
yl)-1N/(4-ethquin-6-methyl-pyrimidin-2-yl)-1N'-(4-chloro-6-methoxy-pyrimidin-2-yl)-1N/(4-chloro-
6-nidoxy-pyrimidin-2-yl)-1N'-(4
-chloro-6-dimethylamino-pyrimidin-2-yl)-SN'-(4-methyl-6-methylthio-pyrimidin-2-yl)-1"-(4-dimethylamino-6-methyl-pyrimidin-2- yl)-1N/-(4,6-dimethoxy-pyrimidin-2-yl)- and N/(4-difluoromethoxy-6-methyl-pyrimidin-2-yl)-N"-methoxy-1-N"-ethoxy -1-N"-
Isopropoxy-1-N"-propoxy-1-N"-butoxy-1-N"-isobutoxy-1-N#-5ec,
-butquin+, -N"-pentoxy-1-N"-octyloxy, -N"-allyloxy-1-N"-(3-
chloropropyloxy)+, -N"-ethoxycarbonylmethoxy-, -N"-ethoxycarbonylmethoxy-
1-N"-(2--yenylethoxy)-1-N"-
Benzyloxy-1-N"-(4-methyl-benzyloquine)-1-N"-(4-fluoro-benzyloxy)
+, -N"-(4-chloro-benzyloxy)+, -N
"-(4-nitro-benzyloxy)- and -N//
(4-methoxycarbonyl-benzyloxy)-1-
N"-benzenesulfonyl-1-N"-(2-chloro-
benzenesulfonyl)+, -N"-(3-chloro-benzenesulfonyl)++, -N"-(4-chloro-benzenesulfonyl)-5-N"-(2-fluoro-benzenesulfonyl)-5-N"-(4-Fluoro-benzenesulfonyl,)-1-N"-(2τpromobenzenesulfonyl)-1-N"-(2-ananobenzenesulfonyl)-1-N"-(2-nitro-benzenesulfonyl)
-1-N"-(4-nitro-benzenesulfonyl)-1
-N"-(2-methyl-benzenesulfonyl)+, -N
"-(4-methyl-benzenesulfonyl)+, -N"-
(2-trifluoromethyl-benzenesulfonyl)+,
-N"-(2-methquin-benzenesulfonyl)-1-
N"-(4-methoxy7-benzenesulfonyl'l-1-
N“-(2-methylthiohensensulfonyl)-1-
N"-(2-sifleophylophoxy-benzenesulfonyl)+, -N"-(2-trifluoromethoxy-benzenesulfonyl)-1-N"-(2-methylthiomethyl-
benzenesulfonyl)+, -N"-(2-dimethylaminosulfonyl-benzenesulfonyl)-1-N"-(2
-phenyl-benzenesulfonyl)-1-N"-(2
-methoxysulfonyl-benzenesulfonyl)-1-N
"-(2-Methoxycarbonylbenzenesulfonyl)-1-N"-(2-ethoxycarbonyl-benzenesulfonyl), -N"-(2-7"Ropoxycarbonyl-benzenesulfonyl)-1-N" -(2-methylmethoxy-aminocarbonyl-benzenesulfonyl) -
1N//-(2-dimethylaminocarbonyl-benzenesulfonyl)- and -N"-(2-diethylaminocarbonyl-benzenesulfonyl)-guanidino.

The sulfonyl, guanidinopyrimidine derivative of formula (Vl) is novel, and the guanidinopyrimidine derivative of formula (11) is reacted with approximately equimolar amounts of sulfonic acid chloride of the formula fungus by a method similar to method (a). It can be manufactured by Kotoku.

The sulfonic acid chloride used as a starting material in method (d) is generally defined by formula (1)K. Formula 0[)K, in which R1 preferably and especially represents formula (1
) have the same meanings as indicated above as preferred or particularly preferred.

Examples of sulfonic acid chlorides of the formula and methods for their preparation have been described above in connection with the description of the starting materials for process (a)K.

The sulfonylisothioureidopyrimidine derivatives used as starting materials in process (e) generally have the formula (■')V
Defined by C. In formula (■), R1, 11 (
, 4, R1 and 几6 preferably and especially with respect to the definition of the substituents of formula (1) have the same meanings as mentioned above as preferred or particularly preferred;
f preferably and especially represents methyl.

Examples which may be mentioned of compounds of formula (vIl) are:
N'-(4-chloro-6-methylthio-pyrimidine-2
-yl)-1N'-(4-methyl-pyrimidin-2-yl)-1N'-(4-methoxy-6-methyl-pyrimidin-2-yl)! -1N/-(4-ethoxy-6-methyl-pyrimidin-2-yl)-1N'-(4-chloro-
6-methoxy-pyrimidin-2-yl)-1N/
(4-ri0-6-ethoxypyrimidin-2-yl)
, N/-(4-chloro-6-dimethylamino-pyrimidin-2-yl)-1N'-(4-methyl-6-methylthio-pyrimidin-2-yl)-1N'-(4-dimethylamino-6- Methyl-pyrimidin-2-yl)-1N
'-(4,6-dimethoxy-pyrimidin-2-yl)-
and N'-(4-difluoromethoxy-6-methyl-
pyrimidin-2-yl)-1-N"-(2-fluoro-
benzenesulfonyl)-1-N"-(2-chloro-benzenesulfonyl)-1-N"-(2-7"lomobenzenesulfonyl)-1-N"-(2-methyl-benzenesulfonyl)+,-N"-(2-methoxycarbonyl-benzenesulfonyl)-1-N"-(2-ethoxycarbonyl-benzenesulfonyl)-1-N"-(2-7'lopoxycarbonyl-benzenesulfonyl)-1-N" −
(2-isopropoquinecarbonyl-benzenesulfonyl)+, -N“-(2-phenyl-benzenesulfonyl”)
l+, +N"-(2-IJfluoromethyl-benzenesulfonyl)+, -N"-(2-difluoromethoxy-
Benzenesulfonyl") - and C) NiN" -(2-
Trifluoromethoxy7-benzenesulfonyl)-8-methyl-thiourea.

The sulfonylinthioureido pyrimidine rust conductor of formula (1) is a known one and/or can be produced by a method known per se (Ep-O5 (European Patent Application Publication Specification) No. 5.986].

R' is CαC4 allooalkoxy, '1~(
'4-Furkylthio, (', <, -alkylsulfinyl or 'ri Cr= represents a phenyl group substituted in the ortho position by C4-furkylsulfonyl,
It should be noted that compounds of formula (■) in which miR6 and Rlf have the above meanings are not yet known. These new compounds are represented by the formula (■
A).

° 1, 7 Compounds of formula (■) are prepared by converting the N-sulfonyl-imino-dithiocarbonic ester of formula (XV) in which R1 and R17 have the abovementioned meanings, if appropriate with a base, e.g. sodium hydride. or potassium tCrt
, -butyrate and, if appropriate, in the presence of a diluent such as tetrahydrofuran, dioxane or dimethylformamide, at a temperature between 0°C and 100°C, where R+4, R5 and R6 have the above meanings. When the reaction is completed,
It is obtained by diluting the mixture with water, acidifying it with a strong acid, for example hydrochloric acid, and isolating the product of formula (~'It) obtained as crystals by suction filtration.

The N-sulfonyl-imino-dithiocarbonate required as a starting material is generally defined by formula (Xv) I7C. In the formula (XV') R, l and ll'F preferably have the same meanings as indicated above as preferred or particularly preferred with respect to the substituents of the formula (I) or (■) .

Examples which may be mentioned of compounds of formula (Xv) are: S
, S-dimethyl N-(2-fluoro-benzenesulfonyl)-1N-(2-chloro-benzenesulfonyl)-1
N-(2-furomobenzenesulfonyl)-1N-(2
-methyl-benzenesulfonyl)-1N-(2-methoxycarbonyl-benzenesulfonyl)-1N-(2-dicarbonyl-benzenesulfonyl)-1N-(2
-propoΦdicarbonylbenzenesulfonyl)-1N
-(2-impropoxycarbonyl-benzenesulfonyl) -1N-(2-phenyl-benzenesulfonyl)
-1N-(2-trifluoromethyl-benzenesulfonyl) -1N-(2-difluoromethoxy-benzenesulfonyl) -1N-(2-trifluoromethoxy-benzenesulfonyl) -2N-(2-1fluoromethylthio-benzenesulfonyl) ) -, N -(2-difluoromethylthio-benzenesulfonyl)-1N-(2-phenoxy-benzenesulfonyl)-1N-(2-pyroxycarbonyl-benzenesulfonyl)-1N
-(2-1 tilthio-benzenesulfo=tv)-1
N-(2-isopropylthio-benzenesulfonyl')
-1N-(2-IJ fluoromethylsulfonyl-benzenesulfonyl)-1N-(2-')methylaminosulfonyl-benzenesulfonyl)-1N-(2-N-Metoyac-N-methylaminosulfonyl-benzenesulfonyl)- 1N-(2-cyano-benzenesulfonyl)-5
N-(2-nitro-benzenesulfonyl)-1N-(2
-Dimedelaminocarbonylbenzene sulfol)-
and N-(2-methylsulfonylmethyl-benzenesulfonyl)-imino-dithiocarbonate.

The N-sulfonyl-imino-dithiocarbonic acid ester of formula (XV) is a known one and/or can be produced by a method known per se [Hemitschier Berichte (C116m, Ber, ) 99. 2885(
196G) and F! See P-O8 (European Patent Application Publication No. 4F) No. 5.986].

The compound of formula (XV) is prepared by treating a sulfonic acid amide of formula (XVI) R,1-80,-NH, (xvn, where R1 has the above meaning) in the presence of a strong base such as sodium hydroxide and 0°C to 10°C, if appropriate in the presence of diluents such as water and dimedelformamide.
React with carbon disulfide at a temperature between 0℃ and then (in situ) at a temperature between 0℃ and 100℃ to form the formula (X■) and X represents chlorine, bromine or iodine.

The formula (XV
) can be isolated by suction filtration.

The sulfonic acid amide required as a starting material generally has the formula (X
VI) Defined by K. In formula (XYI),
R+1 preferably and especially has the same meaning as indicated above as preferred or particularly preferred with respect to the definition of the substituents of formula (1).

Examples which may be mentioned of compounds of formula (XVT) are:
2-trifluoro-medelthio, 2-difluoromethylthio-12-7dinoxy, 2-cyclopropoxycarbonyl-12-methylthio-1,2-isopropylthio-12-trifluoromethylsulfonyl-12-dimethylaminocarbonyl-12-dimethyl Aminosulfonyl-12-cyano-12-fluoro-12-chloro-12
-Bromo-12-mesol-,2-methoxycarbonyl-
12-ethoxycarbonyl-12-propoxycarbonyl-12-impropoxycarbonyl-12-phenyl, 2-trifluoromesol-, 2-difluoromethoxy- and 2-trifluoromethoxy-12-N-methoxycarbonyl-N-methylamino Sulfonyl-12-nitro- and 2-methylsulfonylmethyl-benzenesulfonamide.

The sulfonic acid amide of formula (XVI) is a known one,
and/or by methods known per se (BP-O8 (European Patent Publication) Nos. 23,422, 30,140, 35).
．． No. 893, No. 44.807, No. 44.808, No. 44809, gsz.

No. 466, No. 64,804, No. 70.041 and No. 70.802; U.S. Patent No. 4,372,778
No.; Line Itc Zh, Org, Kh in CJ
, Org, Chem.

USSR) 8.1023-1026 (UK 1032-1
034) (1972)].

These compounds can be prepared by adding a diluent, if appropriate, to the sulfonic acid a-ride of formula (7) in a manner known per se.
For example, it can be obtained by reaction with ammonia in the presence of diethyl ether, tetrahydrofuran or water at temperatures between 0°C and 100°C. The product of formula (XVI) obtained as crystals can thus be isolated by suction filtration.

Examples of suitable starting materials of formula (1) and methods for their preparation are given above in the description of starting materials for process (a).

Possible examples of starting materials of formula (X■) are:
Methyl chloride, methyl bromide, methyl iodide, ethyl chloride,
Ethyl bromide and ethyl iodide, and benzyl chloride and benzyl bromide.

The compound of formula (X■) is a known compound.

The aminopyrimidine required as a starting material is generally defined by the formula (XI'lK. In the formula (XI),
R+4, R5 and R6 preferably and especially have the formula (
Regarding the definitions of the substituents in 1), they have the same meanings as indicated above as preferred or especially preferred.

Examples which may be mentioned of compounds of formula (XI) are: 4
-ri0 mouth-6-methoxy, 4-chloro-6-nitoxy7
．． 4-chloro-6-dimethylamino-,4-methyl-6
-methylthio-14-dimethylamino-6-mesole,
4-difluoromethoxy-6-methyl-14,6-simethoxy, 4-methoxy-6-methyl-14-ethoxy-6-methyl- and 4-methyl-2-amino-pyrimidine.

Aminopyrimidines of formula (xI) are known and/or can be prepared by methods known per se.
．． 81: Chem, Pharm, Bull, 1
1.1382-1388 (1963); U.S. Pat.
299.960: EP-O3 (European Patent Application Publication) No. 19,811; AU-08 (Austrian Patent Application Publication No. 8) No. & 316.181 EP-O8 No. 70.804 .

The amino compounds used as starting materials in process (e)K are generally defined by formula (IV)K. Formula (IY)t
In =C, R2 preferably represents hydrogen or methyl, in particular hydrogen, and Bs has the same meanings as indicated above with respect to the definition of the substituents of formula (I) as preferred or particularly preferred. has.

Examples of suitable starting materials of formula (IV) and literature for these compounds are given above in the description of starting materials for methods).

The compound used as starting material for method (0) is generally defined by formula (I), where M represents hydrogen. In case of
M represents hydrogen, and 几1.31, R3, R4,
R, @ and R6 preferably have the same meanings as indicated above as preferred or particularly preferred, especially with respect to the definition of the substituents of formula (1).

Compounds of formula (1) used as starting materials for process (f) are suitable for processes (a), Φ), (C), (d) and (e) V
C. can be manufactured by the method described above.

Examples which may be mentioned of metal hydroxides, hydrides and alkaline or organometallic compounds used in process (f) are: hydroxides of lithium, sodium, potassium, magnesium and calcium; lithium, sodium; and calcium hydride, sodium mesolate and ethylate, potassium mesolate, ethylate and t6rt
, -butyrate, and butyllithium and isopropyl-magnesium chloride.

The compounds used as starting materials in process (g) VC are generally defined by the formula (I), K, where M represents hydrogen. In formula (I) 17C, VC when this relates to the compound used as starting material for process (g), M represents hydrogen and B, t, 1'(
" , R" , R' , R' and R,'H where L<H and in particular the same meanings as indicated above as preferred or particularly preferred with regard to the definition of the substituents of formula (1) has.

Method (g) Compounds of formula (I) used as starting materials for K can be used in methods (a), (1)), (c),
) It can be manufactured by the method described in . A strong acid is used as a starting material in the process.

The strong acids are preferably hydrogen halides, such as hydrogen chloride, hydrogen bromide or hydrogen iodide, and also PC sulfuric acid or alkanesulfonic acids having up to 411 g of carbon atoms and optionally substituted with fluorine or chlorine, For example, methanesulfonic acid, ethanesulfonic acid, chloromethanesulfonic acid, 2-chloroethanesulfonic acid and trifluoromethanesulfonic acid, trifluoroacetic acid at l', and also benzenesulfonic acid, p-4 luenesulfonic acid, naphthalene-1- Sulfonic acid, naphthalene-2-sulfonic acid, naphthalene-1,4, -1,5-1-1,6-1-
2°6- and -2,7-disulfonic acids.

Process (a) according to the invention for preparing the novel compounds of formula (1) is preferably carried out using a diluent.

Diluents that can be used are in fact entirely inert organic solvents, provided that they are preferably aprotic polar solvents. These solvents include optionally substituted hydrocarbons such as methylene chloride, chloroform, 1,2-dichloroethane, toluene, xylene and chlorobenzene, nitriles such as acetonitrile and propionitrile, ethers such as 1,2 -dimethoxyethane, tetrahydro-7rane and dioxane, as well as dimedelformamide, dimethylacetamide, dimethylsulfoxide, sulfolane, pyridine and 2-methyl-5-ethyl-
Contains pyridine.

As acid acceptor in process (a)K it is possible to use practically all acid binders commonly used. These are in particular alkali metal and alkaline earth metal hydroxides, alkali metal and alkaline earth metal hydrides, organometallic compounds such as butyllithium, and also aliphatic, aromatic and heterocyclic amines, such as Trimethylamine, triethylamine, N,N-dimedelaniline, N,N-dimethyl-benzylamine, diazabicyclooctane (D
ABCO), diazabi7chrononene (DBN), diazabicycloundecene (DBU), pyridine, 2-methyl-5-ethyl-pyridine and 4-dimethylamino-pyridine.

The reaction temperature can be varied within a substantial range in process (a). Generally, this reaction is carried out at -80 to +100℃
The temperature is preferably between -30°C and +50°C. Generally, process (a) according to the invention is carried out under normal pressure.

When carrying out process (a), between 1 and 5 mol, preferably between 2 and 3 mol of sulfonic acid chloride of formula (4) are used per mole of guanidinopyrimidine derivative of formula 1).

The reaction components are combined at room temperature or with external cooling, and the reaction mixture is stirred until the reaction is complete.

'FrFr gold compounds are treated and isolated by conventional methods: the mixture is shaken with water and a water-immiscible solvent such as methylene chloride, chloroform or toluene, if appropriate after distilling off the volatile constituents. , the organic phase is washed with water, dried, filtered and concentrated. The product of formula (n) remaining in the residue is crystallized by trituration with an organic solvent such as diethyl ether, ethyl acetate, ethanol or isopropanol and, if appropriate, purified by recrystallization.

Process (b) according to the invention is preferably carried out using a diluent. Diluents that can be used are virtually all inert organic solvents. These solvents include alcohols such as methanol, ethanol and n- or impropanol,
Included are ethers such as tetrahydrofuran, dioxane and 1,2-dimethoxyethane, esters such as methyl acetate and ethyl acetate, nitriles such as acetonitrile or propionitrile, and dimethylformamide and water.

As acid acceptors in process (b) VC, acid binders can be used which do not have nucleophilic properties that significantly compete with the properties of the amino compounds of formula (IV). Possible acid acceptors of this type are alkali metal and alkaline earth metal carbonates, such as potassium carbonate and calcium carbonate, tertiary amines, such as triethylamine, N,N-dimethylaniline and N,N-dimethylbenzylamine, and Nitrogen-containing alpha-cyclic compounds, such as pyridine, diazabicyclooctane (
DABCO) and diazabicycloundecene (DBU)
It is.

In process (b) the reaction temperature can be varied within a substantial range. Generally, this reaction is carried out between oc and 150°C.
Preferably, the process is carried out at a temperature between 10°C and 100°C. Process (b) is generally carried out under normal pressure.

When carrying out the method (b) according to the invention, generally the formula (ID)
Between 1 and 10 mol, preferably between 2 and 5 mol of the amino compound of formula (ff'l) or its hydrochloride is used per mol of the compound.

Generally, a compound of formula (ID) is cooled to 20°C or gently mixed with a diluent from the table and a compound of formula (lV'l or its hydrochloride salt and, if appropriate, a suitable acid acceptor) is added.Then the reaction The mixture is generally stirred at room temperature or at elevated temperature until the reaction is complete.

Processing can be carried out by conventional methods.

If the product of formula (T) is obtained as crystals from the reaction mixture, it can be isolated by suction filtration. Otherwise, if appropriate after concentration, the mixture is diluted with water and extracted with a solvent which is virtually immiscible with water, for example methylene chloride. The product of formula (I) can be obtained in pure form by washing the extract with water, drying, filtering, concentrating the filtrate and recrystallizing the residue. .

Process (c) according to the invention is preferably carried out using a diluent. Diluents that can be used are in fact all inert organic solvents, but preferably aprotic polar solvents, such as those mentioned above in connection with the process according to the invention (a). be.

Practically all acid binders commonly used as acid acceptors in process (c) can be used. In particular these include the acid binders mentioned in connection with the description of process (a) according to the invention.

In process (C) the reaction temperature can be varied within a substantial range. Generally, this reaction is carried out at temperatures between -80°C and +100°C.
C., preferably between -30.degree. C. and +50.degree. Generally, process (C) is carried out under normal pressure.

When carrying out process (C), generally between 1 and 2 moles, preferably between 1.1 and 1.5 moles of sulfonic acid chloride of formula (g) are used per mole of sulfonylguanidinopyrimidine derivative of formula (iE). .

Method (C) The procedure and processing for K are the same as method (a).

Process (d) according to the invention is preferably carried out using a diluent. Diluents that can be used are in fact all inert organic solvents, but preferably aprotic polar solvents, such as those mentioned above in connection with the description of process (a) according to the invention. be.

As acid acceptors in process (6'I) it is possible to use practically all acid binders customarily used; in particular these include the acid binders mentioned in connection with the description of process (a) according to the invention. included.

In process (d) 1C the reaction temperature can be varied within a substantial range. Generally, this reaction takes place between -80°C and +10°C.
It is carried out at a temperature between 0°C, preferably between -30°C and +50°C. Generally process (d) is carried out under normal pressure.

When carrying out process (d), generally between 1 and 2 moles, preferably between 1.1 and 1.5 moles of sulfonic acid chloride of formula (9) are used per mole of sulfonylguanidinopyrimidine derivative of formula (Ml). .

The steps and treatments in method (d) are similar to method (a).

Process (e) according to the invention is preferably carried out using a diluent. Diluents that can be used are virtually all inert organic solvents, but preferably aprotic polar solvents. In particular, these solvents include tetrahydrofuran,
Included are dioxane, 1,2-dimethoxyethane, acetonitrinopeacetone, methyl ethyl ketone, methyl isobutyl, ketone, dimethyl formamide, dimethyl acetamide and dimethyl sulfoyacito.

In process (e) the reaction temperature can be varied within a substantial range. Generally, this reaction is carried out between 0°C and 150°C.
Preferably it is carried out at a temperature between 10°C and 100°C. Generally, process (e) is carried out under normal pressure or slightly reduced pressure.

When carrying out the process (d) according to the invention, generally between 1 and 10 mol, preferably between 1 and 5 mol, of an amino compound of formula (IV) are used per mol of sulfonylantithioureido pyrimidine salt conductor of formula (■). .

Generally, the sulfonylisothioureido pyrimidine derivative of formula (■) and a diluent are combined and the amino compound of formula (IV) is metered in. The reaction mixture is then stirred until the reaction is complete. The product of formula (I) is usually obtained after cooling and, if appropriate, acidification, for example with hydrochloric acid, as crystals which can be isolated by suction filtration.

The process according to the invention (0) is preferably carried out using a diluent. Possible diluents are virtually all inert organic solvents. In particular, these solvents include alcohols, such as ethanol and n- or Improper tools, ethers such as tetrahydrofuran, dioxane and 1,2-
Included are dimethoxyethane, esters such as ethyl acetate and methyl acetate, and nitriles such as acetonitrile.

The reaction temperature in the process (O) can be varied within a substantial range. Generally the reaction is carried out at a temperature between -20°C and +50°C, preferably between 0°C and 30°C. It is done under pressure.

When carrying out the method according to the invention (0), compound 1 of formula (1)
Between 0.9 and 1.2 mol, preferably between 0.95 and 1.1 mol of the metal compound per mol is used.

Generally, the compound of formula (I) and the diluent are combined and, if appropriate with mild external cooling, the metal compound, if appropriate dissolved in the diluent, is metered in. until the reaction is finished.
Stir the reaction mixture. Generally, salt-like products of formula (I) are obtained as crystals, which can be isolated by suction filtration.

The process according to the invention (JZ) is preferably carried out using a diluent. Diluents that can be used are virtually all inert organic solvents. In particular, these solvents include alcohols such as methanol, ethanol and n- or impropanol, ethers such as tetrahydro7ran, dioxane and 1,2-dimethoxyethane, esters such as methyl acetate and ethyl acetate, and Included are ketones such as acetone, methyl ethyl ketone and methyl imbutyl ketone.

If the acid used as starting material is used as an aqueous solution, it is also advantageous to use acetic anhydride as diluent.

In process (2)) the reaction temperature can be varied within a substantial range. Generally, this reaction takes place between -20°C and +50°C.
It is carried out at a temperature between 0°C and 30°C, preferably between 0°C and 30°C.

General button method (g) is carried out under normal pressure.

When carrying out the method according to the invention (JZ), generally the formula (1)
1 to 10 mol, preferably 1 to 5 mol, of the strong acid is used per mol of the compound.

Generally, the compound of formula (■) and the diluent are combined and the strong acid is metered in, if appropriate with mild external cooling. The reaction mixture is stirred until the reaction is complete. A 1:1 adduct is generally obtained as crystals, which can be isolated by suction filtration.

The active compounds according to the invention can be used as defoliants, desiccants, hardwood destroyers and, in particular, as weedicides. Weeds, in the broadest sense of the word, are any plants that grow where you don't want them. The substances according to the invention act as complete herbicides or as selective herbicides, depending essentially on the method used.

The active compounds according to the invention can be used, for example, in connection with the following plants: Leipidium, Gallium, Chickweed, 1% (8tell).
aria'), Shikagiku R (Matricaria)
, Anth6mis, Galiisoga F4, Chenop
odium), Iraq fJf4 (Urales - ca), Chio yJIJ (Senecio), Millet (Amara-1)
thus'l,su/'<POrtulaCa
), Xantium f4 (Xantium), Convolvulus (Con+volvu-lus'l, f '7 ¥ (
Ipomo ea, Po ly
gonum), Sespania (8esbania), Ambrosia (Ambrosia), Thistle (Cirs)
i -um), I=L/7 Zami 23 (Carduu
s'), S o n c b u s
, eggplant f4 (Solanum), (y, Iraq J!
! 1 (Rorippa), Kikashigusa 1! (I(ota
la), Adze+M (Lindernia), Lamiu 1h
ff4 (Lamium), stag beetle f, (Ve
ronica 'r, Abutilon,
Emex IA (Em 6
), Chi7 Maodoriko, f4 (Ga 1eops i
s ), )) f4 (Papav6r) and Centaurea.

Dicotyledonous plants in the following rivers: Gossyp iu
m), Glycine, Chard Fj
a(Beta"l, Ninji 7M ('Daucus")
), French bean-v/Jli (Pha-s6Qlu
s), Pisum rPisum”), NaXF (Sola
num), 7-rJFi (Linum), 7? Ipomo6a"l, Vicia"l
, Nicotiana, Ly
cop6rsicon), Lacquer 1R (Ara
chis), Bra-ssica, Lactuca, Cucumber JR (Cu
Cumis ) and Cucurbita pg (Cucurbita).

Monocotyledonous weeds of the following genera: Echinochlo
a), Enocologusa Ji (8etaria 'I,
Pani-cum JJ (Pani-cum), Pani-cum JQ (Di
gitaria), Awagarie FJ (Phle
um), Poa, Unnogegu?
Jii (Festuca), Ohishiba 114 (Ele-
usin6), Brachiaria
'), Bro-mus (I, olium), Bro-mus, Av6na
, Cyperus IA (C)'perus), Sorghum, Sorghum 114 (Agr.
opyron), Gid7! A (Cyno-don)
Monochor ia, Fimbristylis, Sa
gitta-ria'), Eleochar
is”l, Hop /L/Scirpus, Paspalum, Platypus f4 (I
scha6mum), Sphiniculea (Sph6no
cJea), Dacderoctenium J! i(Da-cty
loctenium), Nukabo fi (Agrostis)
), Sparrow Notebook 1! A(A1op6curus
) and Apera rA (Apera).

Maize ff1 (Zea), Triticum spp.
icum), barley If% (Hordeum), oat (Avena), 2 wheat Jf4 (Secal
e), Moo:y Shif4 (Sorghum), Millet Ji (Panicum), Sato* Hif5 (Sac
cha-rum), Ananas Jli (Ananas
), Asparagus IA and Allium.

(-However, the use of the active compounds according to the invention is in no way restricted to these genera, but extends in the same way to other plants.

Depending on the concentration, the compounds are suitable for complete control of weeds, for example on industrial areas and on railway lines, on roads and squares with or without trees. Similarly, compounds are used for perennial cultivated plants, such as silviculture, ornamental trees, orchards, vineyards, citrus groves, walnut orchards, banana plantations, coffee plantations, tea plantations, rubber tree plantations, oil palm plantations. plantations, cocoa plantations, small fruit tree plantings and weed control in cultivated plants of hops, and can be used for selective control of weeds in annual cultivated plants.

The active compounds according to the invention can be used for selectively controlling monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, such as soybean, cotton, rice, cereals and corn.

The active compounds can be used in the usual G4 preparations, such as solutions, emulsions, wettable powders, suspensions, powders, powders, liniments, soluble powders, granules, suspension-emulsion concentrates, impregnated with the active compound. Ultra-thin capsules can be converted into natural and synthetic materials, as well as polymeric materials.

These compositions are prepared in known manner, for example by mixing the active compound with extenders, i.e. liquid solvents and/or solid carriers, and optionally surfactants, i.e. emulsifiers and/or dispersants and/or blowing agents. Manufactured.

Furthermore, when water is used as an extender, for example, an organic solvent can also be used as an auxiliary solvent. As liquid solvents, mainly aromatic hydrocarbons such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic and chlorinated aliphatic hydrocarbons such as chlorobenzene, chloroethylene or methylene chloride, aliphatic hydrocarbons such as e.g. cyclohexane, or paraffins such as petroleum distillates, mineral and vegetable oils, alcohols such as butanol or glycols and their ethers and esters, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, strong polar solvents such as dimethylformamide and dimethyl sulfoyacite and water. is suitable.

As solid carriers, ammonium salts and ground natural minerals such as kaolin, clay, talc, chalk, quartz, attapulgite, montmorillonite or diatomaceous earth and ground synthetic minerals such as highly dispersed silicic acids, aluminas and silicates are used. are suitable; as solid carriers for the granules, crushed and fractionated natural rocks, such as calcite 6.16.-1ika-iv, @E.1 foam 2
and 'White 1--as well as inorganic and organic millet synthetic granules and granules of organic substances such as sawdust, coconut, corncobs and tobacco stalks; as emulsifiers and/or blowing agents non-ionic and Suitable anionic emulsifiers are, for example, polyoxyethylene fatty acid esters, polyoxyethylene fatty alcohol ethers, evalkyl aryl polyglycol ethers, alkyl sulphurinates, alkyl sulphates, aryl sulphonates and albumin hydrolysis products; dispersion. Suitable agents include, for example, lignin sulfite waste liquor and methylcellulose.

Adhesives such as carboxymethyl cellulose as well as powders,
Particulate or latex natural and synthetic polymers such as gum arabic, polyvinyl alcohol and polyvinyl acetate, as well as natural phospholipids such as cephalin and lecithin, and synthetic phospholipids may be used in the composition.

Further additives can be mineral and vegetable oils.

Colorants such as inorganic pigments such as iron oxide, titanium oxide and Prussian blue and organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes, and trace nutrients such as salts of iron, manganese, boron, copper, cobalt, molybten and zinc. can be used.

The preparations generally contain between 0.1 and 95% by weight, preferably between 0.5 and 90% by weight of active compound.

The active compounds according to the invention can also be used for controlling weeds, either as such or in the form of their preparations, in mixtures with known herbicides, finished formulations or seed mixtures being possible.

Known herbicides such as N-(2-benzothiazolyl)-N
, N/-dimethylurea, 3-(3-chloro-4-
methylphenyl)-1, 1-:) methylurea, 3-(
4-Inpropyl-phenyl)-1,1-dimethylurea, 4-amino-6-(1.

1-dimethylethyl)-3-methylthio-1,2゜4-
triazin-5-(4H)-one, 4-amino-6-(
1,1-dimethylethyl)-3-ethylthio-1,2,
4-triazine-5-(4H”1-one, 1-amino-
6-ethylthio 3-(2゜2-dimethylpropyl)-
1,3,5-triazine-2,4-(IH,3H)-dione, 4-amino-3-methyl-6-phenyl-1,2
, 4-triazin-5-(4H)-one, 2-chloro-
4-ethylamino-6-isopropylamino 1.3
．． 5-triazine, (trimethylsilyl)-methyl 2-
°R-enantiomer of (4-(3,5-dichloropyridyl-2-oxy)-phenoxy]-propionate,
(2-benzyloxy)-ethyl 2-[4-(3,5-
Dichloropyridyl-2-oxy)-7enoxy]-propionate oR-enantiomer, 2,4-dichloropheno Φ'10 acid, 2-(z, 4-dichlorophenoxy)-propionic acid, 4-chloro-2-methylpheno Palm-hO12-(2-methyl-4-chlorophenoxy)
-Propionic acid, 3,5-Jimido-4-hydroxy-benzonitrile, 3,5-dibromo-4-hydroxy-
Mixtures with benzonitrile and diphenyl ethers and phenylpyridazines, such as pyridates, are possible. Surprisingly, the mixture also exhibits a synergistic effect.

Furthermore, other known active compounds, such as fungicides (f.
ungicides), insecticides (insectici-
mixtures with acaricides (des), acaricides (acaric 1des), nematicides (nematicid 6 g), bird repellents, plant nutrients and soil amendments are possible.

The active compounds may be used as such or in the form of preparations or further diluted forms of use, such as v4 ready-made solutions, emulsions, clouding agents, powders, liniments and granules. I can do it.

These forms can be applied in the customary manner, for example by spraying, spraying, atomizing or granulating.

The active compounds according to the invention can be applied before or after germination of the plants.

The compounds can also be mixed into the soil before sowing seeds.

The amount of active compound used can vary within a substantial range. This amount essentially depends on the nature of the desired effect.

Generally the amount used is from 0.001 to 15 to 9, preferably from 0.05 to 10,000 active compounds per hectare of soil surface.
kl? It is between Zha.

The preparation and use of the active compounds according to the invention can be seen from the examples below.

Preparation Examples Example 1 [Method (a)] 2-chloro-benzenesulfonyl chloride 10,1
ti (0.04 s mol) as N' in pyridine 3Qaj
-(4,6-dimethoxy-pyrimidin-2-yl)-
It was added to a solution of 4.5 g (0.02 mol) of N"-methoxy-guanidine at -10°C. The reaction mixture was heated at 20°C for 2 hours.
The mixture was stirred for several days. After addition of a further 1.5 g F of 1c2-chlorobenzenesulfonyl chloride, the mixture was stirred at 20° C. for a further 24 hours. The mixture was concentrated at a maximum temperature of 40° C., the residue was taken up in methylene chloride, and the mixture was washed with pentahydrochloric acid. The organic phase was dried, filtered and concentrated.

The oily residue was crystallized from isoprono(nol).

N'-(4,6-dimethoxy-
pyrimidin-2-yl)-N"-methquin-N" Nu
ll-bis-(2-chloro-benzenesulfonyl)-guanidine Z6i (theoretical amount of 23) was obtained.

Example 2 ρ1 [Method] N'-(4,6-dimethoxy-pyrimidin-2-yl)
-N"-methoxy-N", N"-bis-(2-chloro-
benzenesulfonyl)-guanidine 5.8p (0,01
mol), N,N-dimethylhydrazine 1.5 g (0,
A mixture of 025 mol), 20 d of ethanol and IQd of water was heated to boiling under reflux for 1 hour. After cooling the mixture, the product obtained as crystals is isolated by suction filtration,
Recrystallized from ethyl acetate.

N′-(4,6-dimethoxy-pyrimidin-2-yl)-N“-dimethylaminoNl// −(
z p chlorobenzenesulfonyl)-guanidine 1.
39 (31% of theory) was obtained.

Example 3 [Method (e)] N'-(4-methoyac-6-methyl-pyrimidine-2-
-N"-(2-methylthio-benzenesulfonyl'1-8-methyl-isothiourea16.09 (0
, 04 mol), 0-mesol-hydroxylamine 4.0
A mixture of p (0,085 mol) and dioxane 80- was stirred at 30°C to 33°C for 15 hours. The mixture was then concentrated, the residue crystallized by trituration with ethanol, and the product was isolated by suction filtration.

N/(4-methoxy-6-methyl-pyrimidin-2-yl)-N"-methoyasi-N"'- with a melting point of 134°C
8.4% (53% of theory) of (2-methylthio-benzenesulfonyl)-guanidine was obtained.

Example 4 [Method (g)] N'-(4,6-dimethoxy-pyrimidin-2-yl)
-N"-methoxy-N", N/"-bis-(2-')
A mixture of 5.4 F (methylaminosulfonyl-benzenesulfonyl)-guanidine (0,0075 mol), methanesulfonic acid 0.75 g (0,00 75 mol) and acetone 10 m was stirred at 20°C for 24 hours. The product obtained as crystals was then isolated by suction filtration.

N'-(4,6-dimethoxy-pyrimidin-2-yl)-N"-methoxy-N", melting point 145<0>C.

N///-bis-(dimethylaminosulfonyl-benzenesulfonyl)-guanidine and methanesulfonic acid 1
1.6 g (26 theoretical amounts) of :1 adduct were obtained.

- Similarly, the following compounds were obtained; Example 5, melting point 155°C. Above-CH3H-QC) 13H Eave top 1'' Σ -C) 13H-QC) 138 Breasts, Eimyu Sumire Σ -CH3H-QC) (3H -C) 13H-QC2) 15H Eaves U Ihiro-CI H-0CH3H -C) (3H-0CHF2 H Musi Retired Emperor Mu菫Σ -CH3H-OCHF2) ( -C)13H-N(CH3)2H 1st line (system) -CM3H-5C) (3H -C)13HHH128 (Two Sumires on the Eaves Σ -CH38HH9l-93 -QC) I3H-QC) I3H177 Anari Tomoyama Gen- -OCH3H-QC) 13H158 HH-CH3H160 Hole, Inu Yu Sumire Σ H) I-CH3H118 HH-C) 13H130匪YO 1 ■ Sumire Σ H) f-CH3H170 HH-C) I3H 丑工人Go赳Σ ) IH-C) 13H HH-C) I3 H 丑入入A燕Σ HH-C) I3H -QC) (3H- QC) (3H Table 1 (continued) -CH3H-OCH3) (163 C1) I-QC) 13H Animal friend -C2H5HHH148 Niragami Mutual” Sumire Σ -CM, H)l )I 114-11
67a) p-Toluenesulfonate of Example 7, amorphous, 8a)-,43m p-1-Toluenesulfonate of Example 8, amorphous, 8b) Sulfate of Example 8, amorphous quality, 9a) p-toluenesulfonate of Example 9,
9b) Sulfonate salt of Example 9, having a melting point of 175°C (decomposed)
p-Toluenesulfonate (oil) of Example 22, having
.

Example for the preparation of starting material of formula (■) (I[-1) 2-cyanoamino-4,6-cymethoxypyrimidine 3
6.0? (0,2 mol), O-mesol-hydroxylamine [fi[33,41 (0,4 mol)] and 200 Lt of hyethanol were heated to boiling under reflux for 6 hours. Further KO-methyl-hydroquinylamine hydrochloride 16
．． After adding 79 (0.2 mol), the mixture was heated under reflux for a further 6 hours. After cooling, it was filtered through diatomaceous earth, solution F was concentrated, and the residue was diluted with 200 lig of water. pH value 7 K by diluted sodium hydroxide
The product obtained as crystals was isolated by suction filtration.

N'-(4,6-dimethoxy-pyrimidin-2-yl) with a melting point of 122°C after recrystallization from Impropatool.
A theoretical amount of -N"-nodoxy-guanidine x, e, 4 gc (36 g) was obtained.

The compound of formula (IT) shown in Table 2 below could be produced in the same manner (2):
E m4 1+j HH1-4x
x spoon mutually! X grave L! ! -10-QC4H, (-n> -
CH3H-QC)+3II-11-0CBH,7(-n
) -0CH3H-CM311-12 -
0CI-+2CH2CH2C1-QC)l
)I-OCI(Cocoll-13-OCH2COOC)(3-OCI(3H-
QCH3II-14-QC) (2COOC2H5-0C
H3H-QC)(311(S-0C31(7(
-n) -0CH3)(-0CH3
Milk Arashi Gotan Σ ll-35-0C2H5-CH5H-0C2H5II-
36-QC)! 3-CI H-OCH31121
1-37-QC3)1. (-i) -CI
H-0CH3II-38-0CH3-CH3H-Q
C2H5II-39-OCH3-CH3H-0CHF2
II-41-〇〇3H, (-,) -
CH3H-5C)-13II-42-QC48g(-n
) -CH5H-N(CH3)21! -43-
QC2H5-OCHH-0CH3ll-44-OCH3
-OCH3H-NfCH3)2:c:c E E E E E E E E E
-CH3H-5CH311-46-QC2H5-CH3
HH95II-47-QC)+2-CO0C2)(5-
CH3HHII-48-OCI-120-CH5H)I
150xx-4q -ocH20-CI H-
QC2H511-50-QC3H7(-r)
-CI H-N (CH co)
2II-51-OCH3-CI H-5CH3I
I-52-OCI(2CF3-CH3H-5CH3II
-53-OCH2-C)IllCH2-CH3H-QC
)(F2II-54-0CH2(I)COOC21(5
-CH,H-0C2+ (5tt-ss -o<IIE)
-C) (3H-5CH311-56-00~CH
3H-N (CH3) 2 beds and springs” Mackerel Σ ll-57-0CH2CH2CH2C1-C2H-OC
H311-61-OCH3HH-C2)159811-
62-QC)I2C)12C)12CI HH-
C1-13102n-63-ocH2(II>-
C2)(, H811211-64-OCH2-C(CH
3) 3HH-C) (3TI-65-QCH2CH2-Q
C) 13 HH-CH 242
11-66 -0CH2CH2-QC2H5HH-
CM.

Summer 1-67 -0CH2CH2-5C) (3HH-
0M3晟11ゆうdanΣ IT-68-OCH2CH2-5C2H5HH-CH3
TI-69-OCH2-COOC21H-CH511-
70-0CH2-C)! XiCHCl HH-
CH Coll-71-OCHO)2H)I-CH3165
If-72-ocQ3HH-CH3! ! -73-OCH, HHH107-10911-74
-QC)! 3-QC2H5H-QC2H5IJ-75-
OCH2-C)I=C)(28H-C2H583N-7
6-0CH2-CH-CH2-CI-13-COOC2
H5)+ 143 Preparation Example of Starting Material of Formula (1) ([-1) C1 Phosphoryl Chloride ("Phosphorus Oxychloride") 295i
g to sodium 2-chlorobenzenesulfonate 172
y (0.8 mol), acetonitrile 30017 and sulfolane 300d at 20C to 30C.

The reaction mixture was stirred at 70°C for 4 hours, then cooled to 5°C and diluted with ice water.

Extracted with petroleum ether, washed the extract with water, dried,
After filtration and evaporation, the product remaining in the residue was purified by vacuum distillation.

2-chloro-benzenesulfonyl chloride xx7F with a boiling point of 110°C/1.1 mbar (Article 70 of Rifit)
was gotten.

Example ([-2'1 Methyl 2-aminobenzoate 75.59 (0.5 mol)
was dissolved in 176 d of concentrated hydrochloric acid and 100 at of acetic acid.

A solution of 34.4 g of sodium nitrite in 70 ml of water was added dropwise at 0°C. After stirring the reaction mixture for 15 minutes, it was diluted with 0% sulfur dioxide in 450 tit of acetic acid.
Add slowly to the saturated solution cooled to °C. After removing the cooling bath, the mixture was stirred until gas evolution had ceased, during which time 10 g of steel(I) chloride were introduced in portions. After dilution with ice water and extraction with methylene 11, washing the extract with water, drying, filtering, and concentration, the product remaining in the residue was purified by vacuum distillation.

45 g (theoretical amount of 38 g) of 2-methoxycarbonyl-benzenesulfonyl chloride with a boiling point of 150 DEG C./1.33 mbar were obtained.

Compounds of the formula 0 [) shown in the following Table 3 could be prepared in a similar manner: Δ; 32 mm par 11/milk 1 衷 Adan L Uyu violet Σ ward 1! Preparation Example (Ml-t) of the starting material for the formula (■) 2-methoxycarbonyl-benzenesulfonylchloride 18 p(0,01
2 mol) of N'-(4,6-dimethoxy-pyrimidin-2-yl)-N"-methoxy7-guanidine λ3p
(0.01 mol) and 39 ag of tetrahydro7ran at -5°C with stirring. Next, Tetra Crack 0
1.3 g of diazabicyclooctane in 10 mt of furan (
A solution of 0.012 mol) was added dropwise at -5°C, and the mixture was stirred at 20°C for 2 hours. After adding a further 0.5 p of 2-methoxycarbonyl-benzenesulfonyl chloride and 0.25 p of diazabicyclooctane, the mixture was stirred for a further 2 hours at 20°C. After filtration, concentrate the F solution,
The residual solution was crystallized by evaporation with toluene, and the crystals were isolated by suction-purification.

N'-(4,6-dimethoxy-
pyrimidin-2-yl)-N"-methoxy-N"-(2
-methoxycarbonyl-benzenesulfonyl)-guanidine Z2551 (57th theoretical amount) was obtained.

Compounds of the formula CVI) shown in Table 4 below could be prepared in a similar manner:
x engineering ===
＾Dish Chef' Ki Σ Vl-26-OCH3-CH3H H(n-,)C6F14- Example for the production of starting material of formula (VII) (■-1) Sodium hydride (in oil) 8.451 ( 0,35
A suspension of 2-amino-4-methoxy-6-methyl-pyrimidine 2&0p (0.2 mol) was added with stirring and the mixture was stirred at 20° C. for 15 hours. Next, the reaction mixture was heated so that the reaction temperature did not rise above 40°C, and S/,S''-dimethyl N-(2-chloro-benzenesulfonyl)-imino-dithiocarbonate 61(0
, 2 mol) were added in portions. After stirring the mixture at 20° C. for 5 hours, 1 t of ice water was added and the mixture was filtered. The furnace liquor was acidified with concentrated hydrochloric acid and the product thus obtained as crystals was isolated by suction filtration.

N'-(4-Methoxy-6-methyl-pyrimidin-2-yl)-N"-(2-lyrolobenzenesulfonyl)-8-methyl-isothiourea 67 (theoretical amount 87 width), melting point 148°C was gotten.

The following compound of formula (■) shown in Table 5 could be prepared in a similar manner:
Di〉〉 σ σ 宜 宜 宜 宜 宜 宜X Sumire Σ H-〇c H3-CH3 -CH5H-CH3150 Example for the preparation of starting material of formula (■) (~100-1) Potassium hydroxide 24.9 (0,42
9.2 g (0,043 mol) of 4,6-dimethoxy-pyrimidin-2-yl-thiourea in 7 oats of water was heated to 100°C with stirring.
was added to the mixture. The mixture was then stirred for 2 minutes at 100°C and poured into 3Qd of water. l Lead (■) 16.2g (0,
A solution of 0.05 mol) heated to 100° C. was added. The mixture was heated under reflux for an additional 5 minutes, then cooled to 0°C to 5°C and 30 #It of glacial acetic acid was added to the aqueous solution. The product, which thus precipitated as crystals, was isolated by suction.

2-cyanoamino-4,6-simethoxypyrimidine 6,39 with melting point 202°C (a 1.5% of theory >
was gotten.

- to Ub - 54 g (1,0 mol) of sodium methylate to 84 g (1,0 mol) of cyphanodiamide in methanol solution
,0 mol) and the mixture was stirred for 15 minutes. Acetylacetaldehyde dimedelacecool 1
After adding 32 g (1,0 mol), the mixture was heated under reflux for 3
Stir for hours. The clear dark red reaction solution was evaporated to dryness under vacuum, the residue was dissolved in 15001 KL of water and the solution was diluted with concentrated hydrochloric acid to a H value of 3 KL. The product, which precipitated in crystalline form during this step, was isolated by suction.

2-cyanoamino-4-methyl-pyrimidine 103M theoretical 78H) having a melting point of 203 DEG C. (decomposed) was obtained.

Compounds of formula (Yl'') shown in Table 6 below could be prepared in a similar manner:
” Base Σ VI I! -11-CH3-COCH3VIII-1
2-C2H5H VIII-138H VIII-14"0C285H VIII-15-OH-COOC2H5Vr[-16-
OHH VIII-17-CI H H174 H146 H186 -QC2H5235-237 H220 (consolidation) H) 300 CH3 Preparation example (XI-1) of starting material of formula (XI) 2-Amino-4,6-simethoxy pyrimidine 15.5
p (0.1 mol), ethoxycarbonyl isodeocyanate 13.1! A mixture of i+ (0.1 mol) and acetonitrile 2001117 was stirred at 60° C. for 2 hours. This was then cooled to 10° C. and the product obtained as crystals was isolated by suction filtration.

1-(ethoxycarbonyl) with a melting point of 194°C (decomposed)
-3-(4,6-dimethoxy-pyrimidin-2-yl)
-thiourea 22.55i+ (theoretical amount of 75i) was obtained.

As shown in Table 7 below: 1. A compound of formula (X[) could also be produced in a similar manner:
-10-CI H-CIXIII-11-C
I H-N(CH3)2XIII-
128HH XrII-13-QC2H5H-QC2H5XII! −
14-0C2H5H-QC2H5XIII-1s-CH
2O-QC2H5XIII-16-CI H-
CH5-QC2)! 5160-162 -QC2H5132-1:36 -QC2H5168 -QC2H59 Preparation example (XIV-1) of starting material of formula cxrv) 1-(Ethoxycarbonyl)-3-(4,6-dimethoxy-pyrimidin-2-yl )-thiourea s,,oy(
o, o17s mol), sodium hydroxide 4.0g (0,
A mixture of 1 mol) and 100 ml of water was stirred at 20° C. for 2 days. Dilute hydrochloric acid was then stirred until the solution became acidic and the evolution of CO8 had ceased.

The product obtained as crystals was isolated by suction filtration.

4,6-dimethoxy, melting point 245-248°C (decomposition)
3.5 g (94% of theory) of pyrimidine-2-ylthiourea were obtained.

Compounds of formula (XiV) shown in Table 8 below could be prepared in a similar manner: ) 8 g (0.2 mol) of sodium hydroxide □ dissolved in 15 m of water □ and 6 d (0.11 mol) of carbon disulfide, 2
Simultaneously (in separate drops) into a solution of 2-chloro-benzenesulfonic acid amide 20 Q (,0,1 mol) in dimethylformamide BQ ml at 0 °C (separate dropwise additions) 5
Ta. After stirring the mixture for 1 hour, methyl iodide 13 a
t (0.22 mol) was added dropwise and the reaction mixture tube was heated to 20
The mixture was further stirred at 7°C for 1 hour. The product was precipitated by addition of 500 d of water and isolated by suction filtration.

Sl with a melting point of 112°C, SlI-dimethyl N-(2-diO
lowbenzenesulfonyl)-isoditeocarbamate z
zl (75th factor of the theoretical quantity) was obtained.

Compounds of formula (XV) shown in the following f49 table could be prepared in a similar manner: Example (XVI-1) for the preparation of starting material of formula (XVI) 5Qaj of concentrated ammonia aqueous solution was added dropwise to a mixture of 2-methylthiobenzene-sulfonichloride 60p (0.27 mol) and acetone 6011 with stirring at 20°C to 30°C. The mixture was then stirred at 20° C. for 1 hour and then poured into 1(l) sodium hydroxide solution. This solution was heated with F and acidified with concentrated hydrochloric acid. The product was isolated by suction filtration.

2-Methylthio-benzenesulfonic acid amide 19 (30 parts of theory) having a melting point of 149° C. was obtained, the compound of formula (XVI) given in the following table 10 mentioned by way of example in the above examples. Milk LDLG could be produced by the above Example A Pre-germination test/hotbed Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether In order to produce a suitable preparation of the active compound, One part by weight of the active compound was mixed with the solvent in 1. above, the above amount of emulsifier was added, and the thick material was diluted with water to achieve the desired concentration.

The offspring of the test plants are sown in normal soil and after 24 hours are sprayed with a preparation of the active compound. It is advantageous to keep the amount of water per unit area constant. The concentration of the compound is not critical, only the amount of active compound applied per unit area determines. After 3 weeks, the degree of damage to the plants was evaluated as chi damage in comparison with the development of untreated controls. Figures represents the following meanings: 0chi = no effect, same as untreated control) 100chi = total eradication In this test, for example, production examples (3) and (11)
) The compound according to Ic showed excellent activity.

Example B Post-emergence test/hotbed Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To prepare a suitable preparation of the active compound, 1 part by weight of the active compound is mixed with the above solution. Then add the emulsifier listed above and dilute this concentrate with water to the desired 1 vol. ! I did it to the degree.

Trial plants with a height of 5 to 15 cm were sprayed with the active compound preparation in such a way that a specific amount of the desired active compound was applied per unit area. The concentration of the spray solution was selected so that the specific fleas of the desired active compound were applied at 2000 tons of water per hectare.

After 3 weeks, the degree of damage to the plants was evaluated as φ damage compared to the development of untreated controls. The next number is 1! Denotes the taste: 0% = no effect, same as untreated control) 100% = all eradicated In this test, for example Manufacturing Examples (3), (10)
, (11) and (39) showed excellent activity.

Part 8: A (continued) n　rv　-u　t’n.

Claims (1)

[Claims] 1. General formula (I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (I) In the formula, M represents 1 equivalent of hydrogen or metal, and R^1 may be optionally substituted. represents a good phenyl group, where R^7 and R^8 are the same or different,
hydrogen, halogen [especially fluorine, chlorine and/or bromine], cyano, nitro or C_1-C_4-alkyl [the radicals may optionally be fluorine, chlorine, bromine, cyano, C_1-C_4-alkoxy-carbonyl, C_1-C_4-alkyl amino-carbonyl,
optionally substituted with di-(C_1-C_4-alkyl)-amino-carbonyl, C_1-C_4-alkoxy, C_1-C_4-alkylthio, C_1-C_4-alkylsulfinyl or C_1-C_4-alkylsulfonyl] , C_1-C_4-alkoxy [the group may optionally be fluorine, chlorine, bromine, cyano, C_1-C_4-alkoxy-carbonyl, C_
1-C_4-alkoxy, C_1-C_4-alkylthio, C_1-C_4-alkylsulfinyl or C_
optionally substituted with 1-C_4-alkylsulfonyl], C_1-C_4-alkylthio, C_
1-C_4-alkylsulfinyl or C_1-C_
4-alkylsulfonyl, which groups may optionally be substituted with fluorine, chlorine, bromine, cyano or C_1-C_4-alkoxy-carbonyl; or C_1-C_4-alkylaminosulfonyl, di-(C_1 ~C_4-alkyl)-amino-sulfonyl, C_1-C_4-alkoxyamino-sulfonyl, benzyloxy-aminosulfonyl, C_1-C_4-alkoxy-C_
1-C_4-alkyl-aminosulfonyl;
represents phenyl or phenoxy, represents C_1-C_4-alkoxy-sulfonyl, or represents C_2-C_6-alkenyl, optionally substituted with fluorine, chlorine, bromine, cyano, C_1-C_4-alkoxy-carbonyl, carboxyl or phenyl; ], C_2-C_6-alkynyl [the group may optionally be substituted with fluorine, chlorine, bromine, cyano or C_1-C_4-alkoxy-carbonyl], C_3-C_6-alkenoxy [the group may be substituted with [optionally substituted with fluorine, chlorine, bromine, cyano or C_1-C_4-alkoxy-carbonyl], C_3-C_6-alkenylthio [the group is optionally substituted with fluorine, chlorine, bromine, cyano or C_1-C_4-alkoxy-
may be substituted with carbonyl], C_1 to C_6
-alkoxy-carbonyl [the group optionally includes fluorine, chlorine,
May be substituted with bromine, cyano or C_1-C_4-alkoxy]
, C_3-C_6-cycloalkoxy-carbonyl, C
_1-C_6-alkylthiocarbonyl (which group may optionally be substituted with fluorine, chlorine, bromine, cyano or C_1-C_4-alkoxy-carbonyl), amino-carbonyl, C_1-C_4-alkylamino-carbonyl, di- (C_1-C_4-alkyl)-amino-carbonyl, C_1-C_4-alkoxyamino-carbonyl, C_3-C_4-alkenyloxyamino-carbonyl, benzyloxy-aminocarbonyl, C_1-C_4-alkoxy-C_1-C_4-alkylamino- Carbonyl, dimethylhydrazinocarbonyl, dimethylhydrazinosulfonyl, C_3-C_6-alkynyloxy or C_
3~C_6-alkynylthio; or further, R^1 represents an optionally substituted benzyl group ▲There are mathematical formulas, chemical formulas, tables, etc.▼, where R^9 and R^1^0 are the same or different, hydrogen, halogen [e.g., especially fluorine, chlorine or bromine], cyano, nitro, C_1-C
_4-alkyl [the group may optionally be substituted with fluorine and/or chlorine], C_1-C_4-alkoxy [the group may optionally be substituted with fluorine and/or chlorine], C_1-C_4- alkoxy-carbonyl,
C_1-C_4-alkylthio, C_1-C_4-alkylsulfinyl, C_1-C_4-alkylsulfonyl or di-(C_1-C_4-alkyl)-aminosulfonyl, and furthermore R^2 is hydrogen, C_1-C_4-alkyl or represents a sulfonyl group R^1^1-SO_2-, where R^1^1 is C_1-C_1_2-alkyl [the group can optionally be fluorine, chlorine, bromine, cyano, nitro, C_1-C_
4-Alkoxy-carbonyl, C_1-C_4-alkylamino-carbonyl, di-(C_1-C_4-alkyl)-amino-carbonyl, C_1-C_4-alkoxy, C_1-C_4-alkylthio, C_1-C_4-
optionally substituted with alkylsulfinyl or C_1-C_4-alkylsulfonyl], C_1-C_1
_2-Alkoxy [The group may optionally be fluorine, chlorine, bromine, cyano, nitro, C_1-C_4-alkoxy-carbonyl, C_1-C_4-alkoxy, C_1-C_4-
optionally substituted with alkylthio, C_1-C_4-alkylsulfinyl or C_1-C_4-alkylsulfonyl], C_2-C_1_2-alkenyl [the radicals are optionally substituted with fluorine, chlorine, bromine, cyano, nitro, C_1
~C_4-alkoxy, C_1-C_4-alkylthio or phenyl may be substituted], C_2-C
_1_2-alkenyloxy [the group may optionally be substituted with fluorine, chlorine, bromine, cyano, nitro, C_1-C_4-alkoxy, C_1-C_4-alkylthio or phenyl], C_1-C_8-alkylamino, di- (C_1-C_4-alkyl)-amino, C_3
~C_6-cycloalkylamino or di-(C_1
~C_6-cycloalkyl)-amino [These groups optionally include fluorine, chlorine, bromine, cyano, nitro, phenyl, phenoxy, C_1-C_4-alkoxy,
optionally substituted with C_1-C_4-alkylthio, C_1-C_4-alkylsulfinyl or C_1-C_4-alkylsulfonyl], C_2-C_8-alkenylamino [wherein the group is optionally substituted with fluorine, chlorine, bromine, cyano, nitro or phenyl] ], phenylamino or benzylamino [these groups may optionally be substituted with fluorine, chlorine, bromine, C_1-C_4-alkyl, trifluoromethyl, C_
1-C_4-alkoxy, C_1-C_2-fluoroalkoxy, C_1-C_4-alkylthio, C_1-C
_4-alkylsulfinyl, C_1-C_4-alkylsulfonyl, optionally substituted with cyano, nitro and 1- or C_1-C_4-alkoxy-carbonyl], benzyl [the radicals optionally substituted with fluorine, chlorine, bromine, cyano, nitro, C
_1-C_4-alkyl, trifluoromethyl, C_1
~C_4-alkoxy-carbonyl, C_1-C_4-
Alkoxy or di-(C_1-C_4-alkyl)-
[optionally substituted with amino-sulfonyl] or optionally substituted phenyl group ▲ Numerical formula, chemical formula, table, etc. ▼ , where R^1^2 and R^1^3 are the same or are distinct and have the above meanings for R^7 and R^8, provided that they are not identical to R^7 and R^8 in each individual case: and furthermore, R^3 is a group -OR represents ^1^4, where R^1^4
is C_1-C_1_2-alkyl [the group is optionally fluorine,
Chlorine, bromine, C_1-C_4-alkoxy, C_1-C
_4-alkylthio, C_1-C_4-alkylsulfinyl or C_1-C_4-alkylsulfonyl], C_3-C_6-cycloalkyl, C_1-C_6-cycloalkyl-C_
1-C_2 alkyl, C_3-C_6-alkenyl (the group may optionally be substituted with fluorine, chlorine or bromine), C_3-C_6-alkynyl, C_1-C_
4-Alkoxy-carbonyl-C_1-C_2-alkyl, aminocarbonylmethyl, C_1-C_4-alkylamino-carbonyl-methyl or di-(C_1-C_4-alkyl)-amino-carbonyl-methyl, or phenyl, benzyl , benzhydryl or phenethyl [these groups may optionally be fluorine, chlorine, nitro, cyano, C_1-C_4-alkyl, C
_1~C_4-alkoxy or C_1~C_4-alkoxy-carbonyl]; or further, R^3 represents a group ▲which may be a mathematical formula, chemical formula, table, etc.▼, where R^1 ^5 represents hydrogen or C_1-C_4-alkyl, and R^1^6 represents hydrogen or C_1-C_4-alkyl [the group may optionally be fluorine, chlorine, bromine, cyano, C_1-C_4
-alkoxy or C_1-C_4-alkoxy-carbonyl] or C_3-C_6-cycloalkyl, phenyl, benzyl or phenethyl [these groups may optionally be substituted with fluorine, chlorine, bromine, cyano , nitro, C_1-C_4-alkyl, C_1-C_
4-alkoxy or C_1-C_4-alkoxy-carbonyl], or C_1-C_4-alkyl-carbonyl, C_1-C_4-alkoxy-carbonyl, C_1-C_4-alkyl-sulfonyl or phenylsulfonyl [the group may optionally be substituted with fluorine, chlorine, bromine, cyano, nitro or methyl]:
Furthermore, R^2 is a sulfonyl group R^1^1-SO_
2-, provided that R^1^1 has the above meaning, and R^3 represents hydrogen; R^4 is hydrogen, fluorine, chlorine, bromine or C_1 to C_
4-alkyl [the group may optionally be substituted with fluorine and/or chlorine] or C_1-C_4-alkoxy [the group may optionally be substituted with fluorine and/or chlorine] or C_1-C_4-alkylthio [the group may optionally be substituted with fluorine and/or chlorine]; R^5 is hydrogen, fluorine, chlorine, bromine or C_1-C_
4-alkyl, optionally substituted with fluorine and/or chlorine, or cyano, formyl, C_1-C_4-alkyl-carbonyl or C_1-C_4-alkoxy-carbonyl; and R ^6 represents hydrogen or C_1-C_4-alkyl [the group may optionally be substituted with fluorine and/or chlorine] or C_1-C_4-alkoxy [the group may optionally be substituted with fluorine and/or chlorine]; or represents amino, C_1-C_4-alkylamino or di-(C_1-C_4-alkyl)-amino, with the condition that R^4 and R^6 do not simultaneously represent methyl. 1:1 adduct of a compound of formula (I) with a sulfonylguanidinopyrimidine derivative of and a strong acid, excluding the following compounds: N'-(4,6-dimethoxy-pyrimidin-2-yl)- N″-methoxy-N″-(2-trifluoromethoxy-benzenesulfonyl)-guanidine,
N'-(4-methoxy-6-methyl-pyrimidine-2-
yl)-N''-dimethylamino-N''-(2-methyl-benzenesulfonyl)-guanidine, N'-(4-methoxy-6-methyl-pyrimidin-2-yl)-N''-
Methoxy-N''-(2-chloro-benzenesulfonyl)-guanidine and N'-(4-methoxy-6-methyl-pyrimidin-2-yl)-N''-dimethylamino-N
Potassium salt of ``-(2-chloro-benzenesulfonyl)-guanidine. 2. In producing the sulfonylguanidinopyrimidine derivative of general formula (I) according to claim 1, (a) M represents hydrogen; In the case, formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) In the formula, R^3, R^4, R^5 and R^6 have the above meanings, and the guanidinopyrimidine derivative of is acidified. In the presence of an acceptor and if appropriate in the presence of a diluent, it is reacted with a sulfonic acid chloride of the formula (III) R^1-SO_2-Cl(III), where R^1 has the meaning given above. (b) M represents hydrogen and R^2 is hydrogen or C
When representing _1-C_4-alkyl, the formula obtained by the method described in (a) above (ID) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(ID) In the formula, R^1, R^4, R^5, R^6 and R^1^4
has the above meaning, if appropriate in the presence of an acid acceptor and if appropriate in the presence of a diluent, a sulfonylguanidinopyrimidine derivative of the formula (IV) ▲Mathematical formula, chemical formula, table, etc.▼(IV) (c) where R^2 represents hydrogen or C_1-C_4-alkyl and R^3 has the above meaning; M represents hydrogen, and R^2 has the formula R^1^1
-SO_2- In the formula, R^1^1 When representing a sulfonyl group having the above meaning, the formula (IE) ▲There are numerical formulas, chemical formulas, tables, etc.▼(IE) In the formula, R^1, R^3, R^4, R^5 and R^6 have the meanings given above, in the presence of an acid acceptor and if appropriate in the presence of a diluent, a sulfonylguanidinopyrimidine derivative of formula (V) R (d) Similarly, M represents hydrogen and R^ 2 is the formula R
^1^1-SO_2- In the formula, R^1^1 has the above meaning. When representing a sulfonyl group, the formula (VI) ▲There are numerical formulas, chemical formulas, tables, etc.▼(VI) In the formula, R ^3, R^4, R^5, R^6 and R^1^1
has the abovementioned meaning, in the presence of an acid acceptor and if appropriate in the presence of a diluent, the sulfonylguanidinopyrimidine derivative of formula (III) R^1-SO_-Cl(III) where R^1 (e) M represents hydrogen and R^2 is hydrogen or C
When representing _1-C_4-alkyl, the formula (VII) ▲ includes numerical formulas, chemical formulas, tables, etc. ▼ (VII) In the formula, R^1, R^4, R^3 and R^6 have the above meanings. and R^1^7 represents C_1-C_4-alkyl or benzyl, if appropriate in the presence of a diluent, the sulfonylisothioureido pyrimidine derivative of formula (IV) ▲ is a mathematical formula, chemical formula, table, etc. ▼ (IV) in which R^2 represents hydrogen or C_1-C_4-alkyl and R^3 has the above meaning; (f) M represents 1 equivalent of the metal; In the case of (a) above, (
Formula (I) obtained by the method described in b), (c), (d) and (e), where M represents hydrogen and R^1, R^2, R^3, R^4 , R^5 and R^6 have the meanings given above, with a metal hydroxide, hydride or alkanolate, or an organometallic compound, if appropriate in the presence of a diluent; or (g ) When preparing a 1:1 adduct of a compound of formula (I) with a strong acid, M represents hydrogen and R^1, R^
2. Claims characterized in that compounds of formula (I) in which R^3, R^4, R^5 and R^6 have the meanings given above are reacted with a strong acid, if appropriate in the presence of a diluent. The range of the general formula described in item 1 (
I) Method for producing a sulfonylguanidinopyrimidine derivative. 3. A herbicide containing at least one sulfonylguanidinopyrimidine derivative of general formula (I) according to claim 1. 4. Use of the sulfonylguanidinopyrimidine derivative of general formula (I) according to claim 1 for controlling undesirable plant growth. 5. A method for producing a herbicide, which comprises mixing the sulfonylguanidinopyrimidine derivative of the general formula (I) according to claim 1 with an extender and/or a surfactant. 6. General formula (VI) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (VI) In the formula, R^3 represents the group -O-R^1^4, where R
^1^4 is C_1-C_1_2-alkyl [the group may optionally be fluorine, chlorine, bromine, C_1-C_4-alkoxy, C
_1-C_4-alkylthio, C_1-C_4-alkylsulfinyl or C_1-C_4-alkylsulfonyl], or C_3-C
_6-cycloalkyl, C_3-C_6-cycloalkyl-C_1-C_2-alkyl, C_3-C_6-alkenyl [the group may optionally be substituted with fluorine, chlorine or bromine], C_3-C_6-alkynyl, C_1- C
_4-Alkoxy-carbonyl-C_1-C_2-alkyl, aminocarbonylmethyl, C_1-C_4-alkylamino-carbonyl-methyl or di-(C_1-
C_4-alkyl)-amino-carbonyl-methyl, or phenyl, benzyl, benzhydryl or phenethyl, which groups optionally represent fluorine, chlorine, nitro, cyano, C_1-C_4-alkyl, C_1-C_4-alkoxy or C_1- C_
Optionally substituted with 4-alkoxy-carbonyl]
or, furthermore, R^3 represents a group ▲which may be a mathematical formula, a chemical formula, a table, etc.▼, where R^1^5 represents hydrogen or C_1-C_4-alkyl, and R^1^6 represents hydrogen or C_1-C_4-alkyl [the group may optionally be fluorine, chlorine, bromine, cyano, C_1-C_4
-alkoxy or C_1-C_4-alkoxy-carbonyl], or C_3-
C_6-cycloalkyl, phenyl, benzyl or phenethyl [these groups may optionally be fluorine, chlorine, bromine, cyano, nitro, C_1-C_4-alkyl, C
C_1-C_4-alkyl-carbonyl, C_1-C_4-alkoxy-carbonyl, C_1-C_4-alkyl-sulfonyl or represents phenylsulfonyl [the group may optionally be substituted with fluorine, chlorine, bromine, cyano, nitro or methyl]; R^4 is hydrogen, fluorine, chlorine, bromine or C_1-C_
4-alkyl [the group may optionally be substituted with fluorine and/or chlorine] or C_1-C_4-alkoxy [the group may optionally be substituted with fluorine and/or chlorine] or C_1-C_4-alkylthio [the group may optionally be substituted with fluorine and/or chlorine]; R^5 is hydrogen, fluorine, chlorine, bromine or C_1-C_
4-alkyl (which group may optionally be substituted with fluorine and/or chlorine), or cyano, formyl, C_1-C_4-
represents alkyl-carbonyl or C_1-C_4-alkoxy-carbonyl; and R^6 represents hydrogen or C_1-C_4-alkyl, optionally substituted with fluorine and/or chlorine; or C_1- represents C_4-alkoxy [the group may optionally be substituted with fluorine and/or chlorine], or represents amino, C_1-C_4-alkylamino or di-(C_1-C_4-alkyl)-amino, and the conditions , R^4 and R^6 must not simultaneously represent methyl;
4-Alkoxy-carbonyl, C_1-C_4-alkylamino-carbonyl, di-(C_1-C_4-alkyl)-amino-carbonyl, C_1-C_4-alkoxy, C_1-C_4-alkylthio, C_1-C_4-
optionally substituted with alkylsulfinyl or C_1-C_4-alkylsulfonyl], C_1-C_1
_2-Alkoxy [the group is optionally fluorine, chlorine, bromine, cyano, nitro, C_1-C_4-alkoxy-carbonyl, C_1-C_4-alkoxy, C_1-C_4-alkylthio, C_1-C_4-alkylsulfinyl or C_1-C_4-alkyl optionally substituted with sulfonyl], C_2-C_1_2-alkenyl [the group may optionally be substituted with fluorine, chlorine, bromine, cyano, nitro, C_1-C_4-alkoxy, C
C_1-C_4-alkylthio or phenyl], C_2-C_1_2-alkenyloxy [the group may optionally be substituted with fluorine, chlorine, bromine, cyano, nitro, C_1-C_4-alkoxy, C_1-C_4-alkylthio or phenyl ], C_1-C_8-alkylamino, di-(C_1-C_4-alkyl)-amino, C_
3-C_6-cycloalkylamino or di-(C_
3-C_6-cycloalkyl)-amino [These groups optionally include fluorine, chlorine, bromine, cyano, nitro, phenyl, phenoxy, C_1-C_4-alkoxy,
optionally substituted with C_1-C_4-alkylthio, C_1-C_4-alkylsulfinyl or C_1-C_4-alkylsulfonyl], C_2-C_8-
alkenylamino (which radicals are optionally substituted with fluorine, chlorine, bromine, cyano, nitro or phenyl), phenylamino or benzylamino (which radicals are optionally substituted with fluorine, chlorine, bromine, C_1-C_4-alkyl, Trifluoromethyl, C_
1-C_4-alkoxy, C_1-C_2-fluoroalkoxy, C_1-C_4-alkylthio C_1-C
_4-alkylsulfinyl, C_1-C_4-alkylsulfonyl, optionally substituted with cyano, nitro and/or C_1-C_4-alkoxy-carbonyl], benzyl [the radicals optionally substituted with fluorine, chlorine, bromine, cyano, nitro, C
_1-C_4-alkyl, trifluoromethyl, C_1
~C_4-alkoxy-carbonyl, C_1-C_4-
Alkoxy or di-(C_1-C_4-alkyl)-
[optionally substituted with amino-sulfonyl] or optionally substituted phenyl group ▲ Numerical formula, chemical formula, table, etc. ▼ , where R^1^2 and R^1^3 are the same or hydrogen, halogen [especially fluorine, chlorine and/or bromine], cyano, nitro or C_1-C_4-alkyl [the radicals can optionally be fluorine, chlorine, bromine, cyano, C_1-C_4-alkoxy-carbonyl]. , C_1-C_4-alkylamino-carbonyl, di-(C_1-C_4-alkyl)-amino-carbonyl, C_1-C_4-alkoxy, C_1-C_4-
alkylthio, C_1-C_4-alkylsulfinyl or C_1-C_4-alkylsulfonyl], or C_1-C_4-alkoxy, optionally substituted with fluorine, chlorine, bromine, cyano, C_1-C_4-alkoxy -carbonyl, C
_1-C_4-alkoxy, C_1-C_4-alkylthio, C_1-C_4-alkylsulfinyl or C
optionally substituted with C_1-C_4-alkylsulfonyl], C_1-C_4-alkylthio, C
_1-C_4-alkylsulfinyl or C_1-C
_4-Alkylsulfonyl [These groups optionally contain fluorine,
chlorine, bromine, cyano or C_1-C_4-alkoxy-carbonyl], C_1-C_4-alkylamino-sulfonyl, di-(C_1-C_4-alkyl)-amino-sulfonyl, C_1- C_4-alkoxyamino-sulfonyl, benzyloxy-aminosulfonyl, C_1-C_4-alkoxy-C_
1-C_4-alkyl-aminosulfonyl;
represents phenyl or phenoxy, represents C_1-C_4-alkoxy-sulfonyl, or represents C_2-C_6-alkenyl, optionally substituted with fluorine, chlorine, bromine, cyano, C_1-C_4-alkoxy-carbonyl, carboxyl or phenyl; ], C_2-C_6-alkynyl [the group may optionally be substituted with fluorine, chlorine, bromine, cyano or C_1-C_4-alkoxy-carbonyl], C_3-C_6-alkenoxy [the group may be substituted with [optionally substituted with fluorine, chlorine, bromine, cyano or C_1-C_4-alkoxy-carbonyl], C_3-C_6-alkenylthio [the group is optionally substituted with fluorine, chlorine, bromine, cyano or C_1-C_4-alkoxy- C_1-C_6-alkoxy-carbonyl [the group may optionally be substituted with fluorine, chlorine, bromine, cyano or C_1-C_4-alkoxy], C_3-C_6-cycloalkoxy -carbonyl, C_1-C_6-alkylthiocarbonyl (the group may optionally be substituted with fluorine, chlorine, bromine, cyano or C_1-C_4-alkoxy-carbonyl), amino-carbonyl, C_1-C_4-alkylamino-
Carbonyl, di-(C_1-C_4-alkyl)-amino-carbonyl, C_1-C_4-alkoxyamino-
Carbonyl, C_3-C_4-alkenyloxyamino-carbonyl, benzyloxy-aminocarbonyl, C_1-C_4-
Alkoxy-C_1-C_4-alkylamino-carbonyl, dimethylhydrazinocarbonyl, dimethylhydrazinosulfonyl, C_3-C
A sulfonylguanidinopyrimidine derivative of _6-alkynyloxy or C_3-C_6-alkynylthio. 7. The guanidinopyrimidine derivative of formula (II) according to claim 2 in the presence of an acid acceptor and, if appropriate, in the presence of a diluent, to the formula (V) according to claim 2 General formula (VI) according to claim 6, characterized in that it is reacted with a sulfonic acid chloride of
A method for producing a sulfonylguanidinopyrimidine derivative. 8. General formula (VIIA) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (VIIA) In the formula, R^1 represents a substituted phenyl group ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ , where R^7 is C_1-C_4-fluoroalkoxy, C_1
~C_4-alkylthio, C_1-C_4-alkylsulfinyl or C_1-C_4-alkylsulfonyl or di-(C_1-C_4-alkyl)-aminosulfonyl, R^4 is hydrogen, fluorine, chlorine, bromine or C_1-C_4- represents alkyl [the group may be optionally substituted with fluorine and/or chlorine] or C_1-C_4-alkoxy [the group may optionally be substituted with fluorine and/or chlorine]; or represents C_1-C_4-alkylthio [the group may be optionally substituted with fluorine and/or chlorine], and R^5 is hydrogen, fluorine, chlorine, bromine or C_1-C_
4-alkyl (which group may optionally be substituted with fluorine and/or chlorine), or cyano, formyl, C_1-C_4-
represents alkylcarbonyl or C_1-C_4-alkoxy-carbonyl, and R^6 represents hydrogen or C_1-C_4-alkyl [
[the group may optionally be substituted with fluorine and/or chlorine], C_1-C_4-alkoxy [the group may optionally be substituted with fluorine and/or chlorine], or amino , C_1~C_4-alkylamino or di-(C_1~C_4-alkyl)-amino, with the condition that R^4 and R^6 do not represent methyl at the same time, and R^1^7 represents C_1~ A sulfonylisothioureidopyrimidine derivative of C_4-alkyl or benzyl. 9. Formula (XVA) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (XVA) In the formula, R^1 and R^1^7 have the meanings described in claim 8, N-sulfonylimino -dithiocarbonic acid ester, if appropriate, in the presence of a base, and if appropriate, in the presence of a diluent, the formula (X I) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(X I) In the formula, R^4, R ^5 and R^6 are claim 8
The formula according to claim 8, characterized in that the compound of the formula VIIA)
A method for producing a sulfonylisothioureido pyrimidine derivative. 10. Formula (II) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(II) In the formula, R^3 represents the group -O-R^1^4, where R
^1^4 is C_1-C_1_2-alkyl, and the group is optionally fluorine, chlorine, bromine, C_1-C_4-alkoxy, C
_1-C_4-alkylthio, C_1-C_4-alkylsulfinyl or C_1-C_4-alkylsulfonyl], or C_3-C_6-cycloalkyl, C_3-
C_6-cycloalkyl-C_1-C_2-alkyl,
C_3-C_6-alkenyl (the group may optionally be substituted with fluorine, chlorine or bromine), C_3-C_6-alkynyl, C_1-C_4
-Alkoxy-carbonyl-C_1-C_2-alkyl, aminocarbonylmethyl, C_1-C_4-alkylamino-carbonyl-methyl or di-(C_1-C_
4-alkyl)-amino-carbonyl-methyl, or phenyl, benzyl, benzhydryl or phenethyl [these groups optionally represent fluorine, chlorine, nitro, cyano, C_1-C_4-alkyl, C_1-C_4-alkoxy or C_1- C_4
furthermore, R^3 represents a group ▲a mathematical formula, a chemical formula, a table, etc.▼, where R^1^5 is hydrogen or C_1-C_4-alkyl; and R^1^6 is hydrogen or C_1-C_4-alkyl [the group may optionally be fluorine, chlorine, bromine, cyano, C_1-C_4
-alkoxy or C_1-C_4-alkoxycarbonyl] or C_1-C_6-cycloalkyl, phenyl, benzyl or phenethyl [these groups may optionally be substituted with fluorine, chlorine, bromine, cyano, Nitro, C_1-C_4-alkyl, C_1-C_
4-alkoxy or C_1-C_4-alkoxy-carbonyl], or C_1-C_4-alkyl-carbonyl, C_1-C_4-alkoxy-carbonyl, C_1-C_4-alkyl-sulfonyl or phenylsulfonyl [the group may optionally be substituted with fluorine, chlorine, bromine, cyano, nitro or methyl];
Furthermore, (a) R^4 represents chlorine, R^5 represents hydrogen, and R^6 represents C_1-C_4-alkoxy, which group may optionally be substituted with fluorine and/or chlorine. or C_1-C_4-alkylamino or di-(1,4-
(b) R^4 represents C_1-C_4-alkyl [the group may optionally be substituted with fluorine and/or chlorine], and R^5 represents hydrogen; and R^6 represents C_1-C_4-alkoxy substituted with fluorine and/or chlorine, or C_1-C_4-alkylamino or di-(C_1
~C_4-alkyl)-amino, or (c) R^4 and R^5 represent hydrogen and R^6
represents C_2-C_3-alkyl, a guanidinopyrimidine derivative of 11. Formula (VIII) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (VIII) In the formula, R^4, R^5 and R^6 have the above meanings, and the cyanoaminopyrimidine derivative of is diluted if appropriate. with an amino compound of formula (IX) H_2N-R^3(IX), where R^3 has the abovementioned meaning, or its hydrochloride in the presence of an acidic agent, and if appropriate, the reaction product is acidified. 11. A method for producing a guanidinopyrimidine derivative of formula (II) according to claim 10, which comprises treating with a receptor. 12. Formula (VIII) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (VIII) In the formula, (a) R^4 represents chlorine, R^5 represents hydrogen, and R^6 represents C_1 to C_4- (b) R ^4 represents C_1-C_4-alkyl, which group may optionally be substituted with fluorine and/or chlorine; R^5 represents hydrogen; and R^6 is substituted with fluorine and/or chlorine. or (c) R^4 and R^5 represent hydrogen; or (c) R^4 and R^5 represent hydrogen; A cyanoaminopyrimidine derivative of R^6 represents C_2-C_3-alkyl. 13. (a) An alkali metal or alkaline earth metal salt of cyanamide, if appropriate in the presence of an inert diluent, is prepared by the formula (X) ▲Mathematical formula, chemical formula, table, etc.▼(X) where R^4 , R^5 and R^6 have the above meanings, (b) cyanoguanidine is reacted with a dicarbonyl compound or a derivative thereof, or (c) formula (X I ) ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (X I ) where R^4, R^5 and R^6 have the above meanings, and if appropriate in the presence of a diluent, the aminopyrimidine of formula (XII) ▲There are mathematical formulas, chemical formulas, tables, etc.▼(XII) In the formula, R^1^8 represents ethoxy or phenyl, and the resulting formula (XIII) is produced by reacting with carbonyl isothiorianate.▲Mathematical formulas, chemical formulas, tables, etc. ▼(XIII) in which R^4, R^5, R^6 and R^1^8 have the meanings given above, the carbonylthiourea of is isolated, if appropriate after concentrating the mixture, and Then, in the presence of an organic solvent,
The formula (XI
V) ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (XIV) In the formula, R^4, R^5 and R^6 have the above meanings. Claims characterized in that in the presence of an earth metal hydroxide solution, hydrogen sulfide is reacted with a metal compound capable of binding, and when the reaction has ended, the mixture is filtered and the filtrate is made acidic. The formula (V
III) Method for producing a cyanoaminopyrimidine derivative.