431291, EP 507171, EP 534266, DE 4029753). The action of these compounds, however, is not in every respect satis factory
USO0RE39607E
(19) United States (12) Reissued Patent Miiller et a]. (54)
US RE39,607 E
(10) Patent Number:
(45) Date of Reissued Patent:
HERBICIDAL SULPHONYLAMINO(THIO) CARBONYL COMPOUNDS
(75) Inventors: Klaus-Helmut (DE); Rolf Kirsten, Miiller, Monheim Dusseldorf (DE);
FOREIGN PATENT DOCUMENTS DE
42 34 801 Al
4/1994
EP
135452 0 482 349 A2
M1992
EI‘IlSt RlldOlf F. Gesing, Erkrath
EP
0 534 266 A1
3/1993
Joachim Kluth, Langenfeld (DE); Mark Wilhelm DreWes, Langenfeld (DE); Kurt Findeisen, Leverkusen (DE); Johannes Rudolf Jansen,
EP W0 W0 W0
0 708 087 A1 WO 95/27703 W0 96/ 11188 WO 96/22982
4/1996 4/ 1994 4/1996 8/1996
Monheim (DE); Hans-Jochem (DE); KlausRlebel, Konig,Selters Odenthal
W0
WO 96/35680
11/1996
(DE); Otto Schallner, Monheim (DE); Markus Dollinger, Leverkusen (DE);
May 1, 2007
Hans-Joachim Santel, Leverkusen
Primary ExamineriPatricia L. Morris (74) Attorney, Agent, or FirmiNorris McLaughlin &
(DE)
Marcus PA.
(73) Assignee: Bayer Aktiengesellschaft, Leverkusen
(DE)
ABSTRACT
The invention relates to novel sulphonylamino(thio) carbo
nyl compounds of the formula (I),
(21) Appl. No.: 10/603,997 (22) Filed:
(57)
Jun. 25, 2003 Related US. Patent Documents
/
Reissue of:
(64) Patent No.: Issued:
6,251,831 Jun. 26, 2001
Appl. No.:
09/223,246
Filed:
Dec. 30, 1998
US. Applications:
(1)
R1
R2—\ I
(I) A/
0 so2
\NH
i R3
in Which A represents a single bond, oxygen, sulphur or the group
NiR, in Which R represents hydrogen, alkyl, alkenyl, (63)
Continuation of application No. 90/006,686, ?led on Jan. 8, 1998, now abandoned, which is a continuation-in-pait of application No. PCT/EP96/02826, ?led on Jun. 28, 1996.
(30)
Foreign Application Priority Data
Jul. 11, 1995 Jun. 28, 1996
(51)
(DE) ....................................... .. 195 25 162 (EP) ........................................... .. 96 02826
(2006.01) (2006.01)
(52)
US. Cl. ............... .. 504/273; 548/263.2; 548/263.4;
(58)
Field of Classi?cation Search ............... .. 504/273;
548/263.8; 548/264.2; 548/264.6 548/263.2, 263.4, 263.8, 264.2, 264.6 See application ?le for complete search history. References Cited U.S. PATENT DOCUMENTS 5,057,144 5,085,684 5,238,910 5,252,540 5,300,480 5,488,028 5,534,486 5,552,369
A A A A A A A A
6,525,211 B1
case optionally substituted alkyl, alkenyl, alkinyl,
alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl, cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl, R2 represents cyano or halogen or represents in each case
Int. Cl. A01N 43/653 C07D 249/12
(56)
alkinyl or cycloalkyl, Q represents oxygen or sulphur, Rl represents hydrogen or formyl or represents in each
10/1991 2/1992 8/1993 10/1993 4/1994 1/1996 7/1996 9/1996 2/2003
Daum et a1. Muller et al. Muller et al. Heistracher et a1. Haas et al. Haas et al. Muller et al. Findeisen et a1. Muller et al. ............. .. 558/413
optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, and R3 represents in each case optionally substituted hetero cyclyl having 5 ring members of Which at least one is oxygen, sulphur or nitrogen and from one to three
?lrther ring members can be nitrogen, and salts of compounds of the formula (I),
the previously known compounds 4,5-dimethoxy-2-(2,5
dimethoxy-phenylsulphonylaminocarbonyl)-2,4 dihydro-3H-l,2,4-triaZol-3-one, 4,5-diethoxy-2-(2,5 dimethoxy-phenylsulphonylaminocarbonyl)-2,4 dihydro-3H- 1 ,2,4-triaZol-3 -one
and N-(2,5-dimethoxy-phenylsulphonyl)-1,S-dimethyl lH-pyraZole-3-carboxamide being excluded by dis
claimer; and also to processes and novel intermediates for the preparation of the novel substances and to their use as herbicides.
6 Claims, No Drawings
US RE39,607 E 1
2 The novel sulphonylamino(thio)carbonyl compounds of
HERBICIDAL SULPHONYLAMINO(THIO)
the general formula (I) are obtained if
CARBONYL COMPOUNDS
(a) aminosulphonyl compounds of the general formula (ll)
Matter enclosed in heavy brackets [ ] appears in the original patent but forms no part of this reissue speci? cation; matter printed in italics indicates the additions made by reissue.
R1
/
This is a Continuation ofU.S. Ser. No. 09/006,686, ?led on Jan. 8, 1998 (now abandoned); which is a Continuation
R2—
on Jun. 28, 1996. The invention relates to novel sulphonylamino(thio) car
are reacted with (thio)carboxylic acid derivatives of the
herbicides.
general formula (III)
It is already known that certain sulphonylaminocarbonyl compounds, such as, for example, the compounds 4,5
factory.
A/ so2 \NHZ
A, R1 and R2 have the meanings given above
intermediates for their preparation, and to their use as
triaZol-3-one and N-(2,5-dimethoxy-phenylsulphonyl)-1,5 dimethyl-lH-pyraZole-3-carboxamide possess herbicidal properties (of. EP 341489, EP 422469, EP 425948, EP 431291, EP 507171, EP 534266, DE 4029753). The action of these compounds, however, is not in every respect satis
I
in which
bonyl compounds, to a number of processes and to novel
dimethoxy-2-(2-methoxy-phenylsulphonylaminocarbonyl) 2,4-dihydro-3H-1,2,4-triaZol-3-one, 4,5-dimethoxy-2-(2,5 dimethoxy-phenylsulphonylaminocarbonyl)-2,4-dihydro 3H-1,2,4-triaZol-3-one, 4,5-diethoxy-2-(2,5-dimethoxy phenylsulphonylaminocarbonyl)-2,4-dihydro-3H-1,2,4
0
\
in-Part of International Application PCT/EP96/02826, ?led
(11)
(111)
Q
2A,,
20
in which 25
Q and R3 have the meanings given above and Z represents halogen, alkoxy, aryloxy or arylalkoxy, optionally in the presence of an acid acceptor and option ally in the presence of a diluent, or if
The novel sulphonylamino(thio)carbonyl compounds
30
(b) sulphonyl iso(thio)cyanates of the general formula (IV)
have now been found of the ageneral formula (I), R1
(IV)
R]
(1) 35
0
/
R2—\ I
0
A/
so2
\NH
1 R3 40
in which
in which
A, Q, R1 and R2 have the meanings given above are reacted with heterocycles of the general formula (V)
A represents a single bond, oxygen, sulphur or the group
NiR, in which R represents hydrogen, alkyl, alkenyl, alkinyl or cycloalkyl, Q represents oxygen or sulphur, Rl represents hydrogen or formyl or represents in each
(V)
in which
R3 has the meaning given above,
case optionally substituted alkyl, alkenyl, alkinyl,
alkylcarbonyl, alkoxycarbonyl, alkylsulphonyl,
HiR3
45
50
cycloalkyl, cycloalkylcarbonyl or cycloalkylsulphonyl,
optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, or if
(c) chlorosulphonyl compounds of the general formula (V1)
R2 represents cyano or halogen or represents in each case
optionally substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy, and R3 represents in each case optionally substituted hetero cyclyl having 5 ring members of which at least one is
R1
55
/
oxygen, sulphur or nitrogen and from one to three
further ring members can be nitrogen, and salts of compounds of the formula (I),
R2—
\
60
(V1)
0
I A/ so; \Cl
the previously known compounds 4,5-dimethoxy-2-(2,5
dimethoxy-phenylsulphonylaminocarbonyl)-2,4 dihydro-3H-1,2,4-triaZol-3-one, 4,5-diethoxy-2-(2,5 dimethoxy-phenylsulphonylaminocarbonyl)-2,4 dihydro-3H-1,2,4-triaZol-3-one and N-(2,5-dimethoxy phenylsulphonyl)-1,5 -dimethyl-1H-pyraZole-3 -
carboxamide being excluded by disclaimer;
in which
A, R1 and R2 have the meanings given above are reacted with heterocycles of the general formula (V) 65
HiR3
(V)
US RE39,607 E 4
3 in Which
in Which
R3 has the meaning given above and metal (thio)cyanates of the general formula (VH)
are reacted With chlorosulphonyl iso(thio)cyanate, option
MOCN
R3 has the meaning given above, ally in the presence of a diluent, and the adducts formed in this reaction are reacted in situ With benZene derivatives of
(VII)
the general formula Q()
in Which (X)
Q has the meaning given above, and M represents an alkali metal or alkaline earth metal
equivalent, optionally in the presence of a reaction auxiliary and optionally in the presence of a diluent, or if
(d) chlorosulphonyl compounds of the general formula (V1) in Which R]
/
R2—
A, R1 and R2 have the meanings given above,
(V1)
optionally in the presence of an acid acceptor and option ally in the presence of a diluent,
o
I
20
A/ so2 \Cl
\ in Which
25
A, R1 and R2 have the meanings given above
and, if desired, the compounds of the formula (I) obtained by processes (a), (b), (c), (d), (e) or (f) are converted into salts by customary methods. The novel sulphonylamino(thio)carbonyl compounds of the general formula (I) are distinguished by a strong herbi cidal activity. The invention relates preferably to compounds of the formula (I) in Which A represents a single bond, oxygen, sulphur or the group
are reacted With (thio)carboxamides of the general formula
NiR, in Which R represents hydrogen, CliC6-alkyl, CfC6-alkenyl, CfC6-alkinyl or C3£6-cycloalkyl,
(V111) (V111)
Q HZN
A
30
Q represents oxygen or sulphur, Rl represents hydrogen or formyl or represents in each case optionally cyano-, ?uoro-, chloro-, bromo-,
phenyl- or Cl£4-alkoxy-substituted alkyl, alkenyl, alkinyl, alkylcarbonyl, alkoxycarbonyl or alkylsulpho
R3
nyl having in each case up to 6 carbon atoms, or 35
in Which
Q and R3 have the meanings given above,
represents in each case optionally cyano-, ?uoro-, chloro-, bromo- or CliC4-alkyl-substituted C3iC6
cycloalkyl, C3iC6-cycloalkyl-carbonyl or C3iC6
cycloalkyl-sulphonyl,
optionally in the presence of an acid acceptor and option ally in the presence of a diluent, or if
(e) sulphonylamino(thio)carbonyl compounds of the general formula (IX)
40
R2 represents cyano, ?uoro, chloro or bromo or represents in each case optionally cyano-, ?uoro-, chloro-, bromo
or Cl£4-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy or alkinyloxy having in each case up to 6 carbon atoms, and
R3 represents in each case optionally substituted hetero
(1X)
cyclyl of the formulae beloW, 45
50
in Which
A, Q, R1 and R2 have the meanings given above, and Z represents halogen, alkoxy, aryloxy or arylalkoxy,
in Which
Q1, Q2 and Q3 each represent oxygen or sulphur, and
are reacted With heterocycles of the general formula (V) HiR3
R4 represents hydrogen, hydroxyl, amino or cyano, or represents CfClO-alkylideneamino, or represents
(V)
optionally ?uoro-, chloro-, bromo-, cyano-, CliC4 alkoxy-, CliC4-alkyl-carbonyl- or CliC4-alkoxy
in Which
R3 has the meaning given above,
60
optionally in the presence of an acid acceptor and option ally in the presence of a diluent, or if
(f) heterocycles of the general formula (V) 65
HiR3
(V)
carbonyl-substituted CliC6_-alkyl, or represents in each case optionally ?uoro-, chloro- and/or bromo substituted C2£6-alkenyl or CfC6-alkinyl, or repre sents in each case optionally ?uoro-, chloro-, bromo-, cyano-, CliC4-alkoxy- or CliC4-alkoxy-carbonyl
substituted CliC6-alkoxy, CliC6-alkylamino or Cl*C6-alkyl-carbonylamino, or represents C3iC6 alkenyloxy, or represents di-(CliC6-alkyl)-amino, or
represents in each case optionally ?uoro-, chloro-,
US RE39,607 E 6
5
i-propyl, n-, i- or s-butyl, propenyl, butenyl, propinyl,
bromo-, cyano- and/or C liC4-alkyl-substituted C3£6 cycloalkyl, C3iC6-cycloalkylamino or C3iC6
butinyl, cyclopropyl, cyclobutyl, cyclopentyl or cyclo
hexyl.
cycloalkyl-Cl£4-alkyl, or represents in each case
optionally ?uoro-, chloro-, bromo-, cyano-, nitro-, CliC4-alkyl-, tri?uoromethyl- and/or CliC4-alkoxy
Q represents oxygen or sulphur, Rl represents hydrogen or formyl, or represents in each case optionally ?uoro-, chloro-, bromo-, methoxy- or
substituted phenyl, phenylamino or phenyl-CFC‘,
alkyl,
ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i- or
R5 represents hydrogen, hydroxyl, mercapto, amino,
s-butyl, propenyl, butenyl, propinyl, butinyl, acetyl, propionyl, butyroyl, methoxycarbonyl,
cyano, ?uoro, chloro, bromo or iodo, or represents
optionally ?uoro-, chloro-, bromo-, cyano-, C1£4
ethoxycarbonyl, n- or i-propoxycarbonyl, methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, n-, i-, s- or t-butylsulphonyl, or represents in each case optionally ?uoro-, chloro- or
alkoxy-, CliC4-alkyl-carbonyl- or CliC4-alkoxy carbonyl-substituted C l£6-alkyl, or represents in each case optionally ?uoro-, chloro- and/or bromo substituted C2£6-alkenyl or C2£6-alkinyl, or repre sents in each case optionally ?uoro-, chloro-, cyano-,
methyl-sub stituted cyclopropyl, cyclopropylcarbonyl
CliCé-alkoxy- or Cl£4-alkoxy-carbonyl-substituted
or cyclopropylsulphonyl, R2 represents cyano, ?uoro, chloro or bromo, or repre
CFC -alkoxy, CliC6-alkylthio, CliC6-alkylamino or C1*C6-alkyl-carbonylamino, or represents C3iC6
sents in each case optionally ?uoro-, chloro-, methoxy
alkenyloxy, C3iC6-alkinyloxy, C3iC6-alkenylthio,
or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-,
C3iC6-alkinylthio, C3iC6-alkenylamino or C3iC6 alkinylamino, or represents di-(CliC4-alkyl)-amino, or represents in each case optionally methyl- and/ or ethyl
20
propenyloxy, butenyloxy, propinyloxy or butinyloxy
substituted aZiridino, pyrrolidino, piperidino or
and R3 represents in each case optionally substituted hetero
morpholino, or represents in each case optionally
?uoro-, chloro-, bromo-, cyano- and/or CliC4-alkyl
substituted C3iC6-cycloalkyl, CsiC6-cycloalkenyl, C3£6-cycloalkyloxy, C3iC6-cycloalkylthio, C3iC6 cycloalkylamino, C3iC6-cycloalkyl-CliC4-alkyl, C3iC6-cycloalkyl-C1*C4-alkoxy, C3iC6-cycloalkyl
i- or s-butyl, propenyl, butenyl, propinyl, butinyl, methoxy, ethoxy, n- or i-propoxy, n-, i- or s-butoxy,
25
cyclyl of the formulae beloW,
CliC4-alkylthio or C3iC6-cycloalkyl-CliC alkylamino, or represents in each case optionally
?uoro-, chloro-, bromo-, cyano-, nitro-, CliC4-alkyl-, tri?uoromethyl-, CliC4-alkoxy- and/or CliC4-alkoxy
carbonyl-substituted phenyl, phenyl-CliC4-alkyl, phenoxy, phenyl-CliC4-alkoxy, phenylthio, phenyl CliC4-alkylthio, phenylamino or phenyl-CFC‘,
in Which
alkylamino, or
Q1, Q2 and Q3 each represent oxygen or sulphur, and
R4 and R5 together represent optionally branched
R4 represents hydrogen, hydroxyl or amino, or represents
alkanediyl having 3 to 11 carbon atoms, and also R6, R7 and R8 are identical or different and represent hydrogen, cyano, ?uoro, chloro or bromo, or represent in each case optionally ?uoro-, chloro-, bromo- or
optionally ?uoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-,
CyCs-alkyli-deneamino, or represents in each case 40
s- or t-butyl, or represents in each case optionally
CliC4-alkoxy-substituted alkyl, alkenyl, alkinyl, alkoxy, alkenyloxy, alkinyloxy, alkylthio, alkenylthio, alkinylthio, alkylsulphinyl and alkylsulphonyl having in each case up to 6 carbon atoms, or represents in each
?uoro-, chloro- or bromo-substituted propenyl, butenyl, propinyl or butinyl, or represents in each case 45
case optionally cyano-, ?uoro-, chloro-, bromo- or CliC4-alkyl-substituted cycloalkyl having 3 to 6 car bon atoms,
n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, or represents
propenyloxy or butenyloxy, or represents dimethy
the previously knoWn compounds 4,5-dimethoxy-2-(2,5
dimethoxy-phenylsulphonylaminocarbonyl)-2,4 dihydro-3H-l,2,4-triaZol-3-one, 4,5-diethoxy-2-(2,5 dimethoxy-phenylsulphonylaminocarbonyl)-2,4
lamino or diethylamino, or represents in each case 50
phenylsulphonyl)- l ,5 -dimethyl- l H-pyraZole-3 55
potassium, magnesium, calcium, ammonium, CliC4-alkyl ammonium, di-(CliC4-alkyl)-ammonium, tri-(CliC4
and/or methoxy-substituted phenyl or benZyl,
R5 represents hydrogen, hydroxyl, mercapto, amino,
alkyl)-ammonium, tetra-(CliC4-alkyl)-ammonium, tri ammonium and di-(Cl*CZ-alkyD-benZyl-ammonium salts of compounds of the formula (I) in Which A, Q, R1, R2 and R3 have the meanings indicated above as preferred. The invention relates in particular to compounds of the formula (I) in Which A represents a single bond, oxygen or the group NiR, in Which R represents hydrogen, methyl, ethyl, n- or
ethyl or cyclohexylmethyl, or represents in each case
optionally ?uoro-, chloro-, methyl-, tri?uoromethyl
The invention also relates preferably to sodium,
(CliC4-alkyl)-sulphonium, C5- or C6-cycloalkyl
optionally ?uoro-, chloro-, methyl- and/or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl,
cyclohexyl, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylm
dihydro-3H-l ,2,4-triaZol-3-one and N-(2,5-dimethoxy carboxamide being excluded by disclaimer.
optionally ?uoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy,
?uoro, chloro or bromo, or represents in each case 60
optionally ?uoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents in each case optionally
?uoro-, chloro- or bromo-sub stituted ethenyl, propenyl, butenyl, propinyl or butinyl, or represents in each case 65
optionally ?uoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or
US RE39,607 E 7 i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or
t-butylamino, or represents propenyloxy, butenyloxy,
propinyloxy, butinyloxy, propenylthio, propadienylthio, butenylthio, propinylthio, butinylthio, propenylamino, butenylamino, propinylamino or butinylamino, or represents dimethylamino, diethy lamino or dipropylamino, or represents in each case
optionally ?uoro-, chloro-, methyl- and/or ethyl substituted cyclopropyl, cyclobutyl, cyclopentyl,
cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexymethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino,
in Which
Ql represents oxygen or sulphur, and R4 represents in each case optionally ?uoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents propenyl or propinyl, or represents methoxy, ethoxy, n- or
i-propoxy, or represents cyclopropyl, and R5 represents hydrogen, chloro or bromo, or represents in each case optionally ?uoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, or represents in each case optionally ?uoro
20
and/or chloro-substituted propenyl or propinyl, or
represents in each case optionally ?uoro-, chloro-, cyano-, methoxy- or ethoxy-substituted methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or 25
i-propylthio, or represents propenyloxy or cyclopro
Pyl
or represents in each case optionally ?uoro-, chloro-,
methyl-, tri?uoromethyl-, methoxy- and/or methoxy carbonyl substituted phenyl, benZyl, phenoxy, benZyloxy, phenylthio, benZylthio, phenylamino or
30
benZylamino, or
of the preparation. These radical de?nitions can be com bined as desired With one another, thus including combina
R4 and R5 together represent optionally branched
tions betWeen the preferred ranges indicated.
alkanediyl having 3 to 11 carbon atoms, and also R6, R7 and R8 are identical or different and represent hydrogen, cyano, ?uoro, chloro or bromo, or represent in each case optionally ?uoro-, chloro-, methoxy- or
35
Using, for example, 2-?uoro-6-methoxy benZenesulphonamide and 5-ethoxy-4-methyl-2 phenoxycarbonyl-2,4-dihydro-3H-l,2,4-triaZol-3-thi one as
starting materials, the course of reaction in the process (b) according to the invention can be illustrated by the folloWing
ethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, propenyl, butenyl, propinyl, butinyl methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,
The radical de?nitions listed above, Whether general or listed in ranges of preference, apply not only to the end products of the formula (I) but also, correspondingly, to the starting materials and/or intermediates required in each case
equation: 40
propenyloxy, butenyloxy, propinyloxy, butinyloxy,
ocH3
methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or
t-butylthio, propenylthio, butenylthio, propinylthio, butinylthio, methylsulphinyl, ethylsulphinyl, methyl
+
sozNn2
45
sulphonyl or ethylsulphonyl, or represent cyclopropyl,
F
the previously knoWn compounds 4,5-dimethoxy-2-(2,5
dimethoxy-phenylsulphonylaminocarbonyl)-2,4 dihydro-3H-l,2,4-triaZol-3-one, 4,5-diethoxy-2-(2,5 dimethoxy-phenylsulphonylaminocarbonyl)-2,4
O
HC \o X N i N/ CH 5
50
s
s
HOC H 4
5
N
oczn5 ocH3
phenylsulphonyl)-l ,5-dimethyllH-pyraZole-3 55
O
ing to the invention are the compounds of the formula (I), in Which
s
so2 \NH X N i N/ CH3 F
A represents a single bond,
Q represents oxygen or sulphur,
°
\ _
dihydro-3H-l ,2,4-triaZol-3-one and N-(2,5-dimethoxy carboxamide being excluded by disclaimer. Avery particularly preferred group of compounds accord
3
\
60
Rl represents methyl, ethyl, n- or i-propyl,
Using, for example, 2-ethoxy-6-methyl-phenylsulphonyl isothiocyanate and 5-ethyl-4-methoxy-2,4-dihydro-3H-l,2,
R2 represents chloro or methyl- in each case in position 5 or 6- and
R3 represents optionally substituted triaZolinyl of the formula beloW,
65
4-triaZol-3 -one as starting materials, the course of reaction in
the process (b) according to the invention can be illustrated
by the folloWing equation:
US RE39,607 E -continued 0 N
HZN
_>
/ \O
-HC1
N:
