BRPI0715451A2 - substituted furyl sulfonylamino (thio) carbonyl triazolin (thi) - Google Patents

Abstract

FURIL-SULFONYLAMINO (UNCLE) CARBONIL-TRIAZO-LIN (TI) ON REPLACED. The present invention relates to novel substituted furyl sulfonylamino (thio) carbonyl triazolin (thi) ones of the general formula (1), salts of the compounds of the formula (1), processes for their preparation as well as their use. as herbicides.

Description

Report of the Invention Patent for "FURIL-SULFONYLAMINO (UNCLE) CARBONIL-TRIAZOLIN (TI) ONAS REPLACED".

The present invention relates to novel furyl sulfonylamino (thio) carbonyl triazolin (thi) ones, processes and novel intermediate products for their preparation as well as their use as herbicides.

It is well known that certain substituted thienyl sulfonylamino (thio) carbonyl triazolin (thi) ones have herbicidal properties (compare WO-A-1997/016449, WO-A-1998/024787, WO-A-2001 / 005788, WO-A-2003/037086). However, the effect of these compounds is not satisfactory in all interests.

Now the new substituted furyl sulfonylamino (thio) carbonyl triazolin (thi) ones of the general formula (I) have been developed.

in which

Q1 represents O (oxygen) or S (sulfur), Q2 represents O (oxygen) or S (sulfur),

Ra represents hydrogen, cyano, nitro, halogen or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, alkenyloxy or alkynyloxy in each case optionally substituted, Rb represents hydrogen, cyano, nitro, halogen or alkyl, alkoxy, alkylthio, alkylsulfinyl alkylsulfonyl, alkenyl, alkynyl, alkenyloxy or alkynyloxy in each case optionally substituted, R c represents CO-Y

R6 represents hydrogen, hydroxy, amino, cyano, represents alkylidenamino or represents alkyl, alkenyl, alkynyl, alkoxy, alkylamino, alkylcarbonylamino, alkenyloxy, dialkylamino, cycloalkyl, cycloalkylalkyl, aryl or arylalkyl in each case optionally substituted; represents hydrogen, hydroxy, mercapto, amino, cyano, halogen or represents alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, alkylcarbonylamino, alkenyloxy, alkynyloxy, alkenylthio, alkynylamino, alkynylamino, dialkylamino, pyrrolidine, piperidino, morpholino, cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio, aryl, arylalkyl, arylalkyl, arylalkylalkyl, optionally substituted arylalkyl or

R7 and R6 together represent optionally branched alkanediyl and Y represents one of the groups OR8 or N (R9R10) 1 wherein R8 represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl in each case optionally substituted,

R 9 represents hydrogen or represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl in each case optionally substituted,

R10 represents hydrogen or represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl in each case optionally substituted, as well as salts of compounds of formula (I).

Saturated or unsaturated hydrocarbon groups such as alkyl, alkanediyl, alkenyl or alkynyl - also in bonds with heteroatoms such as alkoxy - where possible are in each case straight chain or branched chain.

Optionally substituted radicals may be substituted one or more times, and in the multiple substitution the substituents may be the same or different. Preferred substituents or scopes of the radicals present in the

formulas cited above and below are defined below. Q1 preferably represents O (oxygen) or S (sulfur). Q2 preferably represents O (oxygen) or S (sulfur). Ra preferably represents hydrogen, cyano, nitro, halogen, represents alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having respectively 1 to 6 carbon atoms in the alkyl group, in each case optionally substituted by cyano, halogen or (C1 -C4) alkoxy or represents alkenyl, alkynyl, alkenyloxy or alkynyloxy having respectively 2 to 6 carbon atoms in the alkenyl or alkynyl group, in each case optionally substituted by cyano or halogen,

Rb preferably represents hydrogen, cyano, nitro, halogen, represents alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having respectively 1 to 6 carbon atoms in the alkyl group, in each case optionally substituted by cyano, halogen or (C1 -C4) alkoxy or represents alkenyl, alkynyl, alkenyloxy or alkynyloxy having respectively 2 to 6 carbon atoms in the alkenyl or alkynyl group, in each case optionally substituted by cyano or halogen,

Rc preferably represents CO-Y,

R preferably represents hydrogen, hydroxy, amino, cyano, represents (C 2 -C 10) alkylidenamino, represents alkyl of 1 to 6 carbon atoms optionally substituted by fluorine, chlorine, bromine, cyano, (C 1 -C 4) alkylcarbonyl or (C1 -C4) alkoxycarbonyl represents alkenyl or alkynyl having respectively 2 to 6 carbon atoms, in each case optionally substituted by fluorine, chlorine and / or bromine, represents alkoxy, alkylamino or alkylcarbonylamino with respectively 1 to 6 carbon atoms in the alkyl group, in each case optionally substituted by fluorine, chlorine, bromine, cyano, (C1 -C4) alkoxy or (C1 -C4) alkoxycarbonyl, represents alkenyloxy of 3 to 6 carbon atoms. dialkylamino having respectively 1 to 4 carbon atoms in the alkyl groups represents cycloalkyl, cycloalkylamino or cycloalkylalkyl having respectively 3 to 6 carbon atoms in the alkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety in each c as optionally substituted by fluorine, chlorine, bromine, cyano and / or (C1 -C4) alkyl or represents aryl or arylalkyl having respectively 6 or carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety in each if appropriate substituted by fluorine, chlorine, bromine, cyano, nitro, (C1 -C4) alkyl, trifluoromethyl and / or (C1 -C4) alkoxy. R7 preferably represents hydrogen, hydroxy, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, represents alkyl of 1 to 6 carbon atoms optionally substituted by fluorine, chlorine, bromine, cyano, (C1 -C4) alkoxy (C1 -C4 ) -alkylcarbonyl or (C1 -C4) alkoxycarbonyl represents alkenyl or alchemy having respectively 2 to 6 carbon atoms in each case optionally substituted by fluorine, chlorine and / or bromine, represents alkoxy, alkylthio, alkylamino or alkylcarbonylamino having from 1 to 6 carbon atoms in the alkyl group, in each case optionally substituted by fluorine, chlorine, cyano, (C1 -C4) alkoxy or (C1 -C4) alkoxycarbonyl, represents alkenyloxy, alkynyloxy, alkenylthio alkynylthio, alkenylamino or alkynylamino having respectively 3 to 6 carbon atoms in the alkenyl or alkynyl group, represents dialkylamino with respectively 1 to 4 carbon atoms in the alkyl groups, represents aziridino, pyrrolidino, piperidino or morphol in each case optionally substituted by methyl and / or ethyl, represents cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having respectively 3 to 6 carbon atoms in the cycloalkenyl or cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by fluorine, chlorine, bromine, cyano and / or (C1 -C4) alkyl or represents aryl, arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or arylalkylamino having respectively 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by fluorine, chlorine, bromine, cyano, nitro (C 1 -C 4) alkyl, trifluoromethyl (C 1 -C 4) alkoxy and / or (C 1 -C 4) alkoxycarbonyl, R 6 and R 7 also preferably together represent optionally branched 3 to 6 carbon atoms alkanediyl. each.

Y is preferably one of the groups OR8 or N (R9R10) 1 wherein R8 represents alkyl of 1 to 6 carbon atoms optionally substituted by cyano, halogen or (C1 -C4) alkoxy, represents alkenyl or alkynyl having respectively 2 to 6 atoms. carbon, in each case eventually substituted by cyano or halogen, represents cycloalkyl or cycloalkylalkyl having respectively 3 to 6 carbon atoms in the cycloalkyl group and possibly 1 to 4 carbon atoms in the alkyl moiety, in each case, respectively. substituted by cyano, halogen or (C1 -C4) alkyl represents aryl or arylalkyl having respectively 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano halogen, (C1 -C4) alkyl or (C1 -C4) alkoxy or represents heterocyclyl or heterocyclylalkyl having respectively up to 6 carbon atoms and additionally 1 to 4 nitrile atoms. hydrogen and / or 1 to 2 oxygen or sulfur atoms in the heterocyclyl group and possibly 1 to 4 carbon atoms in the alkyl moiety, in each case eventually substituted by nitro, cyano, halogen (CrC4) -alkyl or (C1 -C4) alkoxy, R9 represents hydrogen or represents alkyl of 1 to 6 carbon atoms optionally substituted by cyano, halogen or (C1 -C4) alkoxy represents alkenyl or alkynyl with respectively 2 to 6 carbon atoms, each optionally substituted by cyano or halogen, represents cycloalkyl or cycloalkylalkyl having respectively 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by cyano, halogen or ( C1 -C4 alkyl represents aryl or arylalkyl having respectively 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nit cyano, halogen, (C 1 -C 4) alkyl or (C 1 -C 4) alkoxy or represents heterocyclyl or heterocyclylalkyl of up to 6 carbon atoms and respectively 1 to 4 nitrogen atoms and / or 1 to 2 oxygen atoms or sulfur in the heterocyclyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano, halogen, (C1 -C4) alkyl or (C1 -C4) alkoxy and

R10 represents hydrogen or alkyl of 1 to 6 carbon atoms optionally substituted by cyano, halogen or (C1 -C4) alkoxy, represents alkenyl or alkynyl with respectively 2 to 6 carbon atoms, in each case optionally substituted by cyano or halogen, represents cycloalkyl or cycloalkylalkyl having respectively 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by cyano, halogen or (C 1 -C 4) - alkyl represents aryl or arylalkyl having respectively 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano, halogen (C1 -C4 ) -alkyl or (C1 -C4) -alkoxy or represents heterocyclyl or heterocyclylalkyl of up to 6 carbon atoms respectively and additionally 1 to 4 nitrogen atoms and / or 1 to 2 oxygen or sulfur atoms re in the heterocyclyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano, halogen, (C1 -C4) alkyl or (C1 -C4) alkoxy.

Q1 is particularly preferably O (oxygen) or S (sulfur). Q2 is particularly preferably O (oxygen) or S (sulfur). R a particularly preferably represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy or represent propenyl, butenyl, propynyl, butynyl propenyloxy, butenyloxy, propynyloxy or butynyloxy in each case optionally substituted by cyano, fluorine or chlorine. Rb is particularly preferably hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy or represents propenyl, butenyl, propynyl, butynyl propenyloxy, butenyloxy, propynyloxy or butynyloxy in each case optionally substituted by cyano, fluorine or chlorine, Rc is particularly preferably CO-Y R6 is particularly preferably hydrogen, hydroxy, amino, methyl, ethyl, n- or i -propyl, n-, i-, s- or t-butyl in each case which is substituted by fluorine, chlorine, cyano, methoxy or ethoxy in each case represents ethenyl, propenyl, butenyl, propynyl or butynyl in each case optionally substituted by fluorine , chlorine and / or bromine, represent me toxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, represents propenyloxy or butenyloxy, represents dimethylamino or diethylamino, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino, cyclohexylamino, cyclobutylmethylmethyl cyclopentylmethyl or cyclohexylmethyl where appropriate substituted by fluorine, chlorine, methyl and / or ethyl or phenyl or benzyl in each case optionally substituted by fluorine, chlorine, methyl, trifluoromethyl and / or methoxy.

R 7 is particularly preferably hydrogen, chlorine, bromine, methyl, ethyl, n- or t-propyl, n-, i-, s- or t-butyl in each case which is substituted by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyryl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl represents ethenyl, propenyl, butenyl, ethinyl, propynyl or butynyl in each case optionally substituted by fluorine, chlorine and / or bromine represents methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i- , s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, acetylamino or propionylamino in each case optionally substituted by fluorine, chlorine, cyano, methoxy, ethoxy n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, represents propenyloxy, butenyloxy, ethinyloxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propinyl io, butynylthio, propenylamino, butenylamino, propynylamino or butynylamino represents dimethylamino, diethylamino or dipropylamino represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopentenyl, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclobutyloxy, cyclo cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclohexylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclopropylmethyl, cyclopentylmethyl, hexylmethoxy, cyclopropylmethylthio, cyclobutylmethylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino in each case optionally substituted with fluoro, chloro, methyl and / or phenyl, benzoyl, benzoyl, phenylthio phenylamino or benzylamino in each case optionally substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy or methoxycarbonyl.

R 6 and R 7 also particularly particularly preferably represent trimethylene (propan-1,3-diyl), tetramethylene (butan-1,4-diyl) or pentamethylene (pentan-1,5-diyl).

Y is particularly preferably one of the groups OR8 or N (R9R10) 1 wherein

R 8 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl in each case optionally substituted by cyano, fluoro, chloro, methoxy or ethoxy, represents propenyl, butenyl, propynyl or butinyl in each case optionally substituted by cyano, fluorine or chlorine, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl. represents phenyl, phenylmethyl or phenylethyl in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoride - methoxy or represents heterocyclyl or heterocyclylmethyl in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, with the heterocyclyl group is selected in each case oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl series, R 9 represents hydrogen or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl if any substituted by cyano, fluorine, chlorine, methoxy or ethoxy, represents propenyl, butenyl, propynyl or butynyl in each case optionally substituted by cyano, fluorine or chlorine, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, represents phenyl, phenylmethyl or phenylethyl in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, η- or i -propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy or represents heterocyclyl or heterocyclylmethyl in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, the heterocyclyl group being in each case selected from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl and

R10 represents hydrogen or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, represents propenyl, butenyl, propynyl or butynyl in each case optionally substituted by cyano, fluorine or chlorine, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, represents phenyl, phenylmethyl or phenylethyl in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluent ormethoxy or trifluoromethoxy or represents heterocyclyl or heterocyclylmethyl in each case optionally substituted by cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, with the hetero cyclila is in c See if selected from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl.

Q1 most particularly preferably represents O (oxygen). Q2 most particularly represents O (oxygen). Most particularly preferably Ra represents hydrogen, fluorine, chlorine, bromine, iodine or represents methyl, ethyl, n- or i-propyl, in which case it is preferably substituted by fluorine, chlorine, methoxy or ethoxy.

Rb most particularly preferably represents hydrogen, fluorine, chlorine, bromine, iodine or represents methyl, ethyl, n- or i-propyl, in each case preferably substituted by fluorine, chlorine, methoxy or ethoxy. Rc very particularly preferably represents CO-Y. R6 most particularly preferably represents methyl, ethyl, n- or i-propyl in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy, represents ethenyl, propenyl or propynyl in each case optionally substituted by fluorine or chlorine, represents methoxy, ethoxy, n- or i-propoxy in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy, represents dimethylamino or cyclopropyl.

R7 most particularly preferably represents hydrogen, chlorine, bromine, represents methyl, ethyl, n- or i-propyl in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, represents ethenyl, propenyl, butenyl, propynyl or butynyl in each case optionally substituted by fluorine or chlorine represents methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i -propylamino in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, represents propenyloxy, propynyloxy, propenylthio, propynylamino or propynylamino, represents dimethylamino or diethylamino, represents cyclopropyl, cyclopropyloxy, cyclopropylmethyl or cyclopropylmethoxy in each case optionally substituted by fluorine, chlorine or methyl, Y most particularly represents the group OR8, where

R represents methyl, ethyl, n- or i-propyl in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy.

Preferably the object of the invention is also sodium, potassium, magnesium, calcium, ammonium, (C1 -C4) alkylammonium, di ((C1 -C4) alkyl) ammonium, tri - ((C1 -C4) alkyl) salts ) -ammonium, tetra - ((C1 -C4) alkyl) ammonium, tri ((C1 -C4) alkyl) sulfonium, C5- or C6-cycloalkyl ammonium and di - ((C1 -C2) alkyl) benzyl -ammonium of compounds of formula (I), wherein Q1, Q2, R1, R2, R6, R7 and Y have the meanings indicated above as preferred, particularly preferred or very particularly preferred.

Definitions of the radicals generally cited above or cited in the preferred scope apply to both the end products of formula (I) and correspondingly to the starting or intermediate products respectively required for preparation. These radical definitions may eventually be combined with each other, that is, also between the preferred areas mentioned.

According to the invention, those compounds of formula (I) in which there is a combination of the meanings mentioned above are preferred as being preferred.

According to the invention, particularly preferred are those compounds of formula (I), in which there is a combination of the meanings mentioned above as being particularly preferred.

According to the invention, those compounds of formula (I) in which there is a combination of the meanings mentioned above are most particularly preferred.

A very particularly preferred group are the compounds of

formula (IA)

R2 represents Ra and R5 represents Rb and wherein Q11 Q2, Ra, Rb1 R61 R7 and Y have the meanings mentioned above as being preferred, particularly preferred or very particularly preferred.

Hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R 5 represent hydrogen or methyl and Q 1, Q 2, R 6, R 7 and Y have the meanings mentioned above as being very particularly preferred.

Another particularly preferred group is the compounds of formula (IB).

in which

In this case R2 represents very particularly preferably

(IB)

Y

wherein R4 represents Ra and R5 represents Rb and wherein Q1, Q21 Ra1 Rb, R61 R7 and Y have the meanings mentioned above as being preferred, particularly preferred or very particularly preferred.

In this case, R4 represents very particularly preferably hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R5 represents hydrogen or methyl and Q1, Q21 R6, R7 and Y have the meanings mentioned above as being very particularly preferred.

Another particularly preferred group is the compounds of formula (IC).

Q '

(IC)

the WH

R5

in which

R4 represents Ra and R5 represents Rb and wherein Q11 Q2, Ra1 Rb1 R61 R7 and Y have the meanings mentioned above as being preferred, particularly preferred or very particularly preferred.

In this case, R4 represents very particularly preferably hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R5 represents hydrogen or methyl and Q1, Q2, R61 R7 and Y have the meanings mentioned above as being very particularly preferred.

The novel substituted substituted furyl sulfonylamino (thio) carbonyl triazolin (thi) ones of the general formula (I) have interesting biological properties. They stand out especially for their strong herbicidal efficacy.

The novel substituted substituted furyl sulfonylamino (thio) carbonyl triazolin (thi) ones of the general formula (I) are obtained

(a) reacting substituted furanesulfonamides of the general formula (II)

H3N

SOi

* fV

Λ · in which

Ra1 Rb and Rc have the meaning given above,

are reacted with substituted triazolin (thi) ones of general formula (III)

o1 Qi

Λ-Α- *

ζ f (WI)

N = /

Rr

in which

Q11 Q21 R6 and R7 have the meaning given above and Z represents halogen, alkoxy, aryloxy or arylalkoxy,

possibly in the presence of a reaction aid and possibly in the presence of a diluent or

(b) reacting substituted furyl sulfonyl iso (thio) cyanates of the general formula (IV)

0} $ - N = C = Q '

Rc-

(IV) R '

in which

Q11 Ra, Rb and Rc have the meaning given above with triazolin (thi) ones of the general formula (V)

J (V)

in which

Q2, R6 and R7 have the meaning given above,

possibly in the presence of a reaction aid and possibly in the presence of a diluent or

(c) reacting substituted furan sulfonic acid chlorides of the general formula (VI) \ so.

(Vt)

in which

Ra1 Rb and Rc have the meaning given above,

<V)

in which

Q 2, R 6 and R 7 have the meaning given above and metal (thio) cyanates of general formula (VII)

M-Q1-CN (VlI)

in which

Q1 has the meaning given above,

possibly in the presence of a reaction aid and possibly in the presence of a diluent or

(d) reacting substituted furan sulfonic acid chlorides of the general formula

(SAW)

in which

Ra, Rb and Rc have the meaning given above with triazolin (ti) on- (thio) carboxamides of the general formula (VIII)

(Vlll)

in which

Q1, Q2, R6 and R7 have the meaning given above, possibly in the presence of a reaction aid and possibly in the presence of a diluent or

(e) reacting substituted furyl sulfonylamino (thio) carbonyl compounds of general formula (IX)

in which

Q2, R6 and R7 have the meaning given above,

possibly in the presence of a reaction aid and possibly in the presence of a diluent.

and optionally converting the compounds of formula (I) obtained by processes (a), (b), (c), (d) or (e) to salts by standard methods.

Using, for example, 2-chloro-4-ethoxycarbonyl-furan-3-sulfonamide and 4,5-dimethoxy-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazole-3 as starting materials, then the course of the reaction in process (a) according to the invention can be schemated by the following formula:

Hn

(IX)

in which

Q1, Ra, Rb and Rc have the meaning given above and Z represents halogen, alkoxy, aryloxy or arylalkoxy; with triazolin (ti) onas of the general formula (V)

(V) Using, for example, (2-fluoro-4-methoxycarbonyl-fur-3-yl-sulfonyl-isothiocyanate and 5-ethoxy-4-methyl-2,4-dihydro-3H-1,2,4 -triazol-3-one as starting materials, so the course of the reaction in process (b) according to the invention can be schemated by the following scheme of formula:

Using, for example, 4-methoxycarbonyl-2-trifluoromethyl-furan-3-sulfonic acid chloride, 5-ethyl-4-methoxy-2,4-dihydro-3H-1,2,4-triazole-3 and potassium cyanate as starting materials, so the course of the reaction in process (c) according to the invention can be schemated by the following formula: Using, for example, 2-ethoxycarbonyl-4-methyl acid chloride - furan-3-sulfonic and 4-ethyl-5-methoxy-2,4-dihydro-3H-1,2,4-triazol-3-on-2-carboxamide as starting materials, then the course of the reaction in process (d) according to the invention may be schemated by the following formula:

Using, for example, N- (2-ethyl-4-i-propoxycarbonyl-fur-3-yl-sulfonyl) -0-phenyl-urethane and 4,5-dimethyl-2,4-dihydro-3H-1 2,4-triazol-3-one as starting materials, so the course of the reaction in the process (e) according to the invention can be schemated by the following scheme of formula:

Substituted furan-3-sulfonamides to be used as starting materials in process (a) according to the invention for the preparation of compounds of formula (I) are generally defined by formula (II). In formula (II), Ra, Rb and Rc preferably or especially have those meanings, which have already been indicated above in the context of the description of the compounds of formula (I) according to the invention, preferably or as especially preferred. for Ra1 Rb and Rc.

In part, substituted furan sulfonamides of the general formula (II) are not yet known from the literature; as new substances they are also the subject of this application.

The new substituted furan sulfonamides of the general formula (II) are obtained when substituted furan sulfonic acid chlorides of the general formula (VI)

Cl

\

(Saw)

in which

Ra, Rb and Rc have the meaning given above,

are reacted with ammonia or with ammonium salts, such as, for example, ammonium acetate or ammonium carbonate, optionally in the presence of a diluent, such as, for example, water and / or methylene chloride, at temperatures between 100C and 100C (compare preparation examples). The substituted triazolin (thi) ones to be used later

As starting materials in process (a) according to the invention, for the preparation of compounds of general formula (I), they are generally defined by formula (III). In the general formula (III), Q1, Q2, R6 and R7 preferably or especially have those meanings, which have already been indicated above in the context of the description of the compounds of the general formula (I) according to the invention, preferably or as especially preferred. for Q1, Q2, R6 and R7.

The starting materials of general formula (III) are known and / or may be prepared by processes known per se (compare EP-A-341,489, EP-A-422,469, EP-A-425,948, EP-A-431,291, EP-A-507,171, EP-A-534,266).

Substituted furyl sulfonyl iso (thio) cyanates to be used as starting materials in process (b) for the preparation of compounds of formula (I) according to the invention are generally defined by formula (IV). . In the general formula (IV), Q11 Ra1 Rb and Rc have preferably or especially those meanings, which have already been indicated above in the context of the description of the compounds of general formula (I) according to the invention, preferably or as especially preferred for Q1. , Ra, Rb and Rc.

The starting materials of formula (IV) may be prepared by processes known per se, for example by phosgenation of corresponding furansulfonamides of formula (II) by standard methods.

The triazolin (thi) ones to be used as starting materials in processes (b), (c) and (e) for the preparation of compounds of formula (I) according to the invention are generally defined. by formula (V). In the general formula (V), Q 2, R 6 and R 7 have preferably or especially those meanings, which have already been indicated above in the context of the description of the compounds of the general formula (I) according to the invention, preferably or as follows. especially preferred for Q2, R6 and R7.

The starting materials of general formula (V) are known and / or may be prepared by processes known per se (compare EP-A-341,489, EP-A-422,469, EP-A-425,948, EP-A-431,291, EP-A-507,171, EP-A-534,266).

The substituted furan sulfonic acid chlorides to be used

As starting materials in processes (c) and (d) for the preparation of compounds of general formula (I) according to the invention, they are generally defined by formula (VI). In formula (VI), Ra, Rb and Rc preferably or especially have those meanings, which have already been indicated above in the context of the description of the compounds of formula (I) according to the invention, preferably or as especially preferred for Ra, Rb and Rc.

Substituted furan sulfonic acid chlorides of formula (VI) are known and / or may be prepared by known processes (compare WO-A-2003/029245, WO-A-2003/082777, WO-A-2004/100946).

The triazolin (ti) on (thio) carboxamides to be used as starting materials in process (d) for the preparation of compounds of general formula (I) according to the invention are generally defined. by formula (VIII). In this general formula (VIII), Q1, Q2, R6 and R7 preferably or especially have those meanings, which have already been indicated above in the context of the description of the compounds of general formula (I) according to the invention, preferably or as especially preferred for Q1, Q2, R6 and R7.

The starting materials of general formula (VIII) may be prepared by processes known per se. The furyl sulfonylamino (thio) carbonyl compounds substituted by

Used as starting materials in process (e) for the preparation of compounds of formula (I) according to the invention are generally defined by formula (IX). In this general formula (IX) Q1, Ra, Rb and Rc preferably or especially have those meanings, which have already been indicated above in the context of the description of the compounds of formula (I) according to the invention, preferably or as especially preferred for Q1, Ra, Rb and R0.

The starting materials of formula (IX) may be prepared by processes known per se. The processes (a), (b), (c), (d) and (e) for the preparation of new

The compounds of formula (I) according to the invention are preferably made using diluents. As diluents, in this case practically all inert organic solvents are taken into account. These preferably include halogenated aliphatic and aromatic hydrocarbons, such as pentane, hexane, heptane, cyclohexane, petroleum ether, benzine, ligroin, benzene, toluene, xylene, methylene chloride, chloride of ethylene, chloroform, tetrachloromethane, chlorobenzene and o-dichlorobenzene, ethers such as diethyl and dibutyl ether, glyphimethylmethyl ether and diglycoldimethyl ether, tetrahydrofuran and dioxane, ketones such as acetone, methylethyl, methyl isopropyl - and methyl isobutyl ketone, esters such as acetic acid methyl and ethyl ester, nitriles such as, for example, acetonitrile and propionitrile, amides such as, for example, dimethylformamide, dimethylacetamide and N- methylpyrrolidone as well as dimethylsulfoxide, tetramethylenesulfone and hexamethylphosphoric acid triamide.

As reaction auxiliary agents in processes (a), (b), (c), (d) and (e) according to the invention, it is possible to apply all commonly used acid binding agents for such reactions. Preferably, alkali metal hydroxides such as, for example, sodium and potassium hydroxide, alkaline earth metal hydroxides, such as, for example, calcium hydroxide, carbonates and alkali metal alcoholates, such as sodium and potassium carbonate, sodium and potassium tert-butylate, in addition, basic nitrogen compounds such as trimethylamine, triethylamine, tripropylamine, tributylamine, diisobutylamine, dicyclohexylamine, ethyldiisopropylamine, ethyldicyclohexylamine, N, N- dimethylbenzylamine, β, β-dimethyl aniline, pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-, 2-ethyl-, 4- ethyl and 5-ethyl-2-methyl-pyridine, 1,5-diazabicyclo [4,3,0] -non-5-ene (DBN), 1,8-diazabicyclo- [5,4,0] -undec -7-ene (DBU) and 1,4-diazabicyclo- [2,2,2] octane (DABCO).

The reaction temperatures in processes (a), (b), (c), (d) and (e) according to the invention may vary over a larger range. In general, it works at temperatures between -20 ° C and + 150 ° C, preferably at temperatures between 0 ° C and + 150 ° C.

Processes (a), (b), (c), (d) and (e) according to the invention are generally performed under normal pressure. However, it is also possible to work under high or low pressure.

For carrying out the processes (a), (b), (c), (d) and (e) according to the invention, the necessary starting materials in each case are generally applied in approximately equimolar amounts. However, it is also possible to use one of the components applied in each case to a greater excess. In general, the reactions are carried out in a suitable diluent in the presence of an acid receptor and the reaction mixture is stirred for several hours at the required temperature in each case. The process for processes (a), (b), (c), (d) and (e) according to the invention is carried out in each case by usual methods (compare the preparation examples) .

Salts may optionally be produced from the compounds of general formula (I) according to the invention. Such salts are simply obtained by standard salt formation methods, for example by dissolving or dispersing a compound of formula (I) in a suitable solvent, such as, for example, methylene chloride, acetone, ether. tert-butyl methyl or toluene and addition of a suitable base. Then the salts - possibly after prolonged stirring - can be isolated by concentration or aspiration.

The active substances according to the invention may be used as defoliants, desiccants, weed killers and especially as weed exterminators. By weed in the broadest sense is meant all plants that grow in places where they are unwanted. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount applied.

The compounds of formula (I) according to the invention and their salts, hereinafter referred to together as the compounds of formula (I) (according to the invention), exhibit excellent herbicidal efficacy against a broad spectrum of mono- and economically important dicotyledons. Also hard-to-fight perennial weeds that grow from rhizomes, roots or other permanent organs are well covered by the active substances. In this case, it is irrelevant whether the substances are applied in the pre-seeding, preemergence or postemergence process. If the compounds according to the invention are applied before germination on the earth's surface, then either the emergence of weeds is completely prevented or weeds grow to the leaf germination stage, however, they then adjust their growth and die entirely, finally, after three to four weeks. By applying the active substances to the green parts of the plants in the postemergence process, drastic growth arrest is also initiated very quickly after treatment and weeds stop at the growth stage present at the time of application. or they die completely after a while, thereby prematurely and permanently moving away from harmful weed competition to cultivated plants.

Although the compounds according to the invention have excellent herbicidal activity relative to mono- and dicotyledonous weeds, cultivated plants of economically significant crops such as, for example, wheat, barley, rye, rice, maize, beets, cotton, and soy are only insignificantly damaged or not. For these reasons, the present compounds are very well suited for the selective combat of undesirable plant growth in useful agricultural crops.

In addition, the substances according to the invention have pronounced growth-regulating properties on cultivated plants. They penetrate by regulating the plant's own metabolism and can therefore be applied to visibly influence plant constituent substances and to facilitate harvesting, such as causing dissection and stunting of growth. In addition, they are also suitable for general control and inhibition of undesirable vegetative growth without killing plants. Inhibition of vegetative growth plays an important role in many single- and dicotyledonous crops, as by this means support can be diminished or totally prevented. Based on their herbicidal and plant growth regulating properties, the active substances can also be applied to counter weeds in known or genetically modified plant crops to be further developed. Transgenic plants generally stand out for particular advantageous properties, for example, resistance to certain pesticides, particularly certain herbicides, resistance to plant diseases or plant disease pathogens. such as certain insects or microorganisms such as fungi, bacteria or viruses.

Other particular properties relate, for example, to material harvested with respect to quantity, quality, storage capacity, composition and special constituent substances. In this way, transgenic plants with high starch or modified starch quality or those with other fatty acid composition of the harvested material are known. Application of the compounds of formula (I) according to the invention, or salts thereof, is preferred in economically important useful transgenic and ornamental plant crops such as cereals such as wheat, barley, rye, oats, millet, rice, cassava and maize or also in crops of beet, cotton, soya, rapeseed, potatoes, tomatoes, peas and other vegetable species.

Preferably, the compounds of formula (I) may be applied as herbicides in useful plant crops that are resistant to the phytotoxic effects of herbicides or have been made genetically resistant.

Conventional processes for the production of new plants, which

They have modified properties compared to existing plants up to now, for example, they consist of classical cultivation processes and the production of mutants. Alternatively, plants with modified properties can be produced using genetic engineering processes (see, for example, EP-A-0221044, EP-A-0131624). In several cases, for example,

- genetic modifications of cultivated plants for the purpose of modifying synthesized starch in plants (e.g. WO 92/11376, WO 92/14827, WO 91/19806),

- transgenic crops which are resistant against

certain glufosinate-type herbicides (compare, for example, EP-A-0242236, EP-A-242246) or glyphosate (WO 92/00377) or sulfonylureas (EP-A-0257993, US-A-5013659),

- transgenic crops, eg cotton, capable of producing Bacillus thuringiensis toxins (Bt toxin), which make plants resistant to certain parasites (EP-A-0142924, EP-A-0193259), - plants transgenic plants with modified fatty acid composition (WO 91/13972).

In principle, numerous molecular biological techniques are known, with which it is possible to produce new transgenic plants with modified properties; see, for example, Sambrook et al., 1989, Molecular Cloning, A Laboratory Manual, 2nd edition Cold Spring Harbor Laboratory Press, Cold Spring Harbor, NY; or Winnacker "Gene und Klone", VCH Weinheim 2nd Edition 1996 or Christou, "Trends in Plant Science" 1 (1996) 423-431).

For such genetically engineered manipulations, nucleic acid molecules can be introduced into plasmids, which allow for mutagenesis or sequence modification by recombining DNA sequences. With the aid of the standard processes mentioned above, for example, base changes can be performed, partial sequences removed or natural or synthetic sequences added. For the binding of DNA fragments to one another, adapters or linkers may be applied to the fragments.

The production of plant cells with low activity of a genetic product can be obtained, for example, by expressing at least one corresponding "antisense RNA", an "sense RNA" to obtain a co-effect. deletion or expression of at least one correspondingly constructed rhizome that specifically dissociates transcripts from the genetic product mentioned above.

For this, DNA molecules can be used, which cover the entire coded sequence of a genetic product, including flanking sequences that may be present, as well as DNA molecules, which cover only parts of the coded sequence. parts should be long enough to cause an antisense effect on the cells. It is also possible to use DNA sequences, which have a high homology content with respect to the coded sequences of a genetic product, but are not completely identical. In the expression of nucleic acid molecules in plants, the synthesized protein may be located in each desired compartment of the plant cell. But to obtain location in a particular compartment, for example, the coding region can be joined with DNA sequences, which secure the location in a particular compartment. Such sequences are known in the art (see, for example, Braun et al., EMBO J. (1992), 3219-3227; Wolter et al., Proc. Natl. Acad. Sci USA 85 (1988), 846-850; Sonnewald et al., Plant J. 1 (1991), 95-106).

Transgenic plant cells can be regenerated to whole plants by known techniques. In the case of transgenic plants, they may in principle be plants of any desired plant species, ie both monocotyledonous and dicotyledonous plants.

In this way, transgenic plants are obtained, which have modified properties through overexpression, suppression or inhibition of homologous (= natural) genes or gene sequences or heterologous (= foreign) gene expression or gene sequences.

Preferably, the compounds (I) according to the invention may be applied to transgenic crops which are resistant to sulfonylurea group herbicides, glufosinate ammonium or glyphosinate isopropylammonium and analogous active substances.

In the application of the active substances according to the invention to transgenic crops, in addition to the effects on weeds to be observed in other crops, there are often effects which are specific for application to the respective transgenic crop, for example. a modified or especially broadened spectrum of weeds that can be countered, modified application amounts that can be used for application, preferably good combining ability with herbicides against which the transgenic crop is resistant. , as well as influence of the growth and yield of the cultivated transgenic plants.

Accordingly, the object of the invention is also the use of the compounds of formula (I) according to the invention as herbicides to combat weeds in transgenic cultivated plants.

The compounds according to the invention may be applied in the usual preparations in the form of spray powders, emulsifiable concentrates, sprinkling solutions, dusting powders or granulates. Therefore, the object of the invention are also plant growth regulating compositions containing compounds of formula (I).

The compounds of formula (I) may be formulated differently depending on which biological and / or chemical-physical parameters are predetermined. Formulation possibilities are considered, for example: spray powders (WP), water soluble powders (SP), water soluble concentrates, emulsifiable concentrates (EC), emulsions (EW), such as oil-in-water emulsions. and water-in-oil, sprayable solutions, suspension concentrates (SC), oil or water based dispersions, oil miscible solutions, capsule suspensions (CS), dusting powders (DP), disinfectants, pellets for spreading and soil application, pellets (GR) in the form of microgranulates, spray, coating and adsorption pellets, water dispersible pellets (WG), water soluble pellets (SG), ULV formulations, microcapsules and waxes . Such types of individual formulations are in principle known and are described, for example, in: Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th Edition, 1986, Wade van Valkenburg, "Pesticide Formulations", Mareei Dekker, NY, 1973; K. Martens, "Spray Drying" Handbook, 3rd Ed. 1979, G. Goodwin Ltd. London.

Necessary formulation auxiliary agents such as inert materials, solvent surfactants and other additives are also known and are described, for example, in: Watkins, "Handbook of Insecticide Dust Diluents and Carriers", 2nd Ed., Darland Books, Caldwell NJ, Hv Olphen, "Introduction to Clay Colloid Chemistry", 2nd Ed., J. Wiley & Sons, N.Y., C. Marsden, "Solvents Guide"; 2nd Ed., Interscence, N.Y. 1963; McCutcheon's "Detergents and Emulsifiers Annual", MC Publ. Corp., Ridgewood N.J .; Sisley and Wood, "Encyclopedia of Surface Aetive Agents", Chem. Publ. Co. Inc., N.Y. 1964; Schonfeldt, "Grenzflächenaktive Àthylenoxidaddukte", Wiss. Verlagsgesell., Stuttgart 1976; Winnacker-Küchler, "Chemische Technologie", Volume 7, C. Hanser Verlag Munich, 4th Edition 1986.

Based on these formulations, combinations with other pesticidal substances may also be prepared, such as, for example, insecticides, acaricides, herbicides, fungicides, as well as protectors, fertilizers and / or growth regulators, for example. as a ready-made formulation or as a tank mix.

Spray powders are prepared uniformly dispersible in water which, in addition to the active substance, next to an inert diluent or substance, also contains ionic and / or nonionic surfactants (humectants, dispersing agents), for example, polyoxyethylated alkylphenols, polyoxyethylated fatty alcohols, polyoxyethylated fatty amines, fatty alcohol polyglycol ether sulfates, alkane sulfonates, sodium benzenesulfonates, 2,2'-dinaftylmethane-6,6'- sodium disulfonate, sodium dibutylnaphthalenesulfonate or also sodium oleoylmethyltaurinate. For the preparation of the powder for spraying, the herbicidal active substances are finely ground, for example, in standard apparatus such as hammer mills, fan mills and air jet mills and simultaneously or subsequently mixed with the auxiliary agents of formulations.

Emulsifiable concentrates are prepared by dissolving the active substance in an organic solvent, for example, butanol, cyclohexanone, dimethylformamide, xylene or also high boiling aromatic compounds or hydrocarbons or mixtures of organic solvents with the addition of one or more surfactants. ionic and / or nonionic type (emulsifiers). As emulsifiers may be used, for example: calcium alkylarylsulfonate salts such as Ca dodecylbenzenesulfonate or nonionic emulsifiers such as polyglycolic fatty acid ester, alkylaryl polyglycol ether, fatty alcohol polyglycol ether, condensation products propylene oxide-ethylene oxide, alkylpolyethers, sorbitan esters such as, for example, sorbitan fatty acid ester or polyoxyethylene sorbitan ester, such as, for example, polyoxyethylene sorbitanograx acid ester.

Sprinkling powders are obtained by mixing the active substance with finely distributed solids, for example talc, natural clays such as kaolin, bentonite and pyrophyllite or infusory earth. Suspension concentrates may be water or oil based. They may be prepared, for example, by wet grinding through commercially available pearl mills and optionally addition of surfactants such as, for example, are already cited above in the other types of formulations.

Emulsions, for example oil-in-water (EW) emulsions, may be prepared, for example, by agitators, colloid mills and / or static mixers using aqueous organic solvents and optionally surfactants such as, for example, are already cited above in the other types of formulations.

Granulates may be prepared by either spraying the active substance on granular inert material capable of adsorption or applying the active substance concentrates by adhesives, for example polyvinyl alcohol, sodium polyacrylate or also mineral oils, on the surface of vehicles, such as sand, kaolinite or granular inert material. Suitable active substances may also be granulated in the usual manner for the preparation of fertilizer granules - if desired in admixture with fertilizers -. Water dispersible granules are usually prepared according to the usual processes such as spray drying, swirl bed granulation, plate granulation, mixing with high speed mixers and extrusion without solid inert material. For the preparation of dish, swirl bed granules, extrusion and atomization, see for example processes in Spray-Drying Handbook 3rd ed. 1979, G. Goodwin Ltd., London; J.E. Browing, "Agglomeration", Chemical and Engineering 1967, pages 147 and following; Perry's Chemical Engineer's Handbook, 5th Ed., McGraw-HiII, New York 1973, page 8-57. For other particularities in formulating plant protection preparations, see for example GC Klingman, "Weeds Control as a Science," John Wiley and Sons, Inc., New York, 1961, pages 81-96 and JD Freyer, SA Evans. , "Weed Control Handbook", 5th Ed., Blackwell Scientific Publications, Oxford, 1968, pages 101-103.

As a rule, agrochemicals contain 0.1 to 99%

by weight, preferably 0.1 to 95% by weight, especially preferably 0.5 to 90% by weight, of active substance of formula (I).

In spray powders, the concentration of the active substance matters, for example, from about 10 to 90% by weight, the remainder to 100% by weight, consists of components of usual formulations. At emulsifiable concentrates the concentration of the active substance may be from about 1 to 90, preferably 5 to 80% by weight. Powder formulations contain from 1 to 30% by weight of active substance, preferably most often from 5 to 20% by weight of active substance, sprayable solutions contain about 0.05 to 80, preferably 2 to 50 % by weight of active substance. In water-dispersible granules, the content of the active substance depends in part on whether the effective compound is present in liquid or solid and what granulation aids, fillers and the like are used. In water dispersible granules the content of the active substance is, for example, from 1 to 95% by weight, preferably from 10 to 80% by weight.

In addition, the formulations of the active substances mentioned may optionally contain adhesives, wetting, dispersing, emulsifying, penetration, preservation, frost and solvent protection, fillers, vehicles and dyes, defoamers, evaporation inhibitors and influencing agents. the usual pH and viscosity in each case. If water is used as a diluent, for example, organic solvents may also be used as auxiliary solvents. As liquid solvents the following may be essentially taken into consideration: aromatic compounds such as xylene, toluene or alkylnaphthalenes, chlorinated aromatic compounds and chlorinated aliphatic hydrocarbons such as chlorobenzenes, chloroethylene or methylene chloride, aliphatic hydrocarbons such as cyclohexane or paraffins, for example, petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol, as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, solvents strongly polar, such as dimethylformamide and dimethyl sulfoxide, as well as water.

As solid carriers are considered: for example, ammonium salts and natural mineral mills such as kaolin, alum, talc, chalk, quartz, attapulgite, montmorillonite or infusory earth and synthetic mineral mills, such as highly dispersed silicic acid, aluminum oxide and silicates as solid granular carriers are considered: for example, broken and fractionated natural mills such as calcite, marble, pumice, sepiolite, dolomite, as well as as synthetic granules of inorganic and organic flour as well as granules of organic material such as sawdust, coconut shells, maize spikes and tobacco stalks; as emulsifiers and / or foaming agents are considered: for example, nonionogenic and anionic emulsifiers such as polyoxyethylene fatty acid ester, polyoxyethylene fatty alcohol ether, for example alkylaryl polyglycolic ether, sulfonates alkyl, alkyl sulfates, aryl sulfonates as well as albumin hydrolysates; Dispersing agents include: residual residues of lignin and methylcellulose.

Adhesives such as carboxymethylcellulose, natural and synthetic polymers, powdered, granulated or latex form such as gum arabic, polyvinyl alcohol, polyvinyl acetate as well as natural phospholipids such as cephalins and Iecithins and phospholipids may be used in the formulations. synthetic. Other additives may be mineral and vegetable oils.

Dyes such as inorganic pigments may be used, for example iron oxide, titanium oxide, ferrocyan blue and organic dyes such as alizarin dyes, metal colorants and phthalocyanine dyes and traces of nutritive substances such as salts of iron, manganese, boron, copper, cobalt, molybdenum and zinc. The compounds of formula (I) or salts thereof may be applied as such or in the form of their preparations (formulations) combined with other pesticidal efficacy substances, such as, for example, insecticides, acaricides, nematicides, herbicides, fungicides, protectors, fertilizers and / or growth regulators, for example, as a ready formulation or as tank mixtures. As combination participants for the active substances according to the invention, in admixture formulations or in the tank mix it is possible to use, for example, known active substances, which are based on an inhibition of, for example, acetolactate synthase, ace. - tilcoenzyl-A-carboxylase, PS I, PS II, HPPDO, phytoene denaturase, protoporphyrogenogen oxidase, glutamine synthetase, cellulose biosynthesis, 5-enolpyruvylchiquimate-3-phosphate synthetase. Such compounds as well as other applicable compounds with partially unknown or other mechanism of effect are described, for example, in Weed Research 26, 441-445 (1986), or "The Pesticide Manual", 11th edition 1997 (a). also abbreviated "PM") and 12th edition 2000, The British Crop Protection Council and the Royal Soe. of Chemistry (editor) and literature cited therein. Known herbicides in the literature which may be combined with the compounds of formula (I) include, for example, the following active substances (note: the compounds are designated or have the "common name" according to Internati - Organization for Standardization (ISO) or chemical name, possibly together with a usual code number):

acetochlor; acifluorfen (-sodium); aclonifen; AKH 7088, ie [[[1- [5- [2-chloro-4- (trifluoromethyl) -phenoxy] -2-nitrophenyl] -2-methoxyethylene] -amino] acid or methyl ester -oxy] -acetic; alachlor; alloxidim (sodium); ametrin; amicarbazone, α-midochlor, amidosulfuron; amitrol; AMS1 ie ammonium sulfamate; anilophos; asulam; atrazin; azafenidin, azimsulfuron (DPX-A8947); aziprotrin; barban; BAS 516 H, i.e. 5-fluoro-2-phenyl-4H-3,1-benzoxazin-4-one; beflubutamide, benazolin (-ethyl); benfluralin; benfuresate; bensulfuron (methyl); bensulide; benzazone; benzobicyclon, benzophenap; benzofluorine; benzoylprop (ethyl); benzthiazuron; bialaphos; bifenox; bispyribac (sodium), bromacil; bromobutide; bromophenoxy; bromoxynil; bromuron; buminafos; busoxinone; butachlor; butafenacil, buffalos; butenachlor; butidazole; butralin; butroxydim, butylate; cafenstrol (CH-900); carbetamide; carfentrazon (ethyl); caloxidim, CDAA, i.e. 2-chloro-N, N-di-2-propenylacetamide; CDEC1 ie diethyl dithio carbamic acid 2-chloroallyl ester; clomethoxyfen; chloramben; chlorazifop-butyl; chlormesulon; chlorbromuron; chlorinate; chlorphenac; chlorflurecol methyl; chloridazone; chlorimuron (-ethyl); chlornitrofen; chlorotoluron; chloroxuron; chlorprofam; chlororsulfuron; chlortalimethyl; chlortiamide; chlortoluron, cinidon (-methyl and -ethyl), cinmethylin; cinosulfuron; klephoxidim, clethodim; clodinafop and its ester derivatives (for example, clodinafop-methyl); chloransulam (methyl), cumyluron (JC 940); cyanazine; cycloate; cyclosulfamuron (AC 104); cycloxidim; cycluron; cyhalofop and its ester derivatives (e.g., butyl ester, DEH-112); cyperquat; cyprazine; cyprazole; daimuron; 2,4-D; 2,4-DB; dalapon; unmeasured; desmethrin; di-alate; dicamba; diclobenyl; dichlorprop; diclofop and its esters, such as diclofop-methyl; dichloroam; diethyl (ethyl); diphenoxuron; difenzoquat; diflufenican; diflufenzopyr; dimuron; dimepiperate; dimetachlor; dimetamethrin; dimethenamid (SAN-582H); dimetazone; dimexiflam; dimetipin; dimethasulfuron; dinitramine; dinoseb; di-noterb; diphenamide; dipropetrin; diquat; dithiopyr; diuron; DNOC; eglinazin-ethyl; EL 77, i.e. 5-cyano-1- (1,1-dimethylethyl) -N-methyl-1H-pyrazol-4-carboxamide; endotal; epoprodan; EPTC; esprocarb; etalfluralin; etametsulfuron-methyl; ethididonon; etiozine; ethofumesate; ethoxyphen and its esters (e.g., ethyl ester, HN-252); ethoxysulfuron, etobenzanide (HW 52); F5231, that is, N- [2-chloro-4-fluoro-5- [4- (3-fluorpropyl) -4,5-dihydro-5-oxo-1H-tetrazol-1-yl] -phenyl ] - ethanesulfonamide; fenoprop; fenoxan; fenoxaprop and fenoxaprop-P, as well as their esters, for example fenoxaprop-P-ethyl and fenoxaprop-ethyl; phenoxydim; phentrazamide; fenuron; flamprop (-methyl or -isopropyl or -isopropyl-L); flazasulfuron; floazulate; florassulam; fluazifop and fluazifop-P and their esters, for example fluazifop-butyl and fluazifop-P-butyl; flucarbazone (-sodium); flucloralin; flumetsulam; flumeturon; flumichlorac (-pentyl); flumioxazine (S-482); flumipropyn; fluometuron; fluorchloridone; fluorodifen; fluoroglycofen (ethyl); flupoxam (KNW-739); flupropacil (UBIC-4243); flupirsulfuron (methyl or sodium); fluorolin (butyl); fluridone; fluorchloridone; fluroxipyr (meptyl); flurprimidol; flurtamen; flutiacet (methyl); flutiamide; fomesafen; foramsulfuron; phosamine; furyloxyphen; glufosinate (-ammonium); glyphosate (-isopropylammonium); halosafen; halosulfuron (methyl) and its esters (for example methyl ester, NC-319); haloxifop and its esters; haloxyphop-P (= R-haloxyphop) and its esters, hexazinone; imaza-metabenz (methyl); imazapyr; imazaquin and salts, such as the ammonium salt; imazametapyr; imazamox; imazapic; imazetametapyr; imazethapyr; imazosulfuron; indanofan; oxyninyl; isocarbamide; isopropaline; isoproturon; isouron; isoxaben; isoxachlortol; isoxaflutol; isoxapyrifop; karbutylate; lactofen; lenacil; Immunon; MCPA; MCPB; mecoprop; mefenacet; mefluidid; mesosulfuron, mesotrio, metamitron; metazachlor; metabenzthiazuron; metam; metazole; methoxyfen; methyldimron; metabenzuron, metobenzuron; metobromuron; (alpha) metolachlor; metosulam (XRD 511); methoxuron; metribuzin; metsulfuron methyl; MH; molinate; monalide; monocarbamide dihydrogen sulfate; monolinuron; monuron; MT 128, i.e. 6-chloro-N- (3-chloro-2-propenyl) -5-methyl-N-phenyl-3-pyridazine-mine; MT 5950, that is, N- [3-chloro-4- (1-methylethyl) phenyl] -2-methylpentanamide; naproanilide; napropamide; naptalam; NC 310, i.e. 4- (2,4-dichlorobenzoyl) -1-methyl-5-benzyloxypyrazole; neburon; nicosulfuron; nipira-clofen; nitralin; nitrofen; nitrofluorfen; norflurazon; orbencarb; orizalin; oxadic clay (RP-020630); oxadiazone; oxasulfuron; oxaziclomephon; oxyfluorfen; paraquat; pebulate; pelargonic acid; pendimethalin; pentoxazon; perfluidone; fenenosifam; fenmedifam; picloram; picolinfen; pinoxaden; piperophos; pyributyl carb; pyriphenop-butyl; pretylachlor; primisulfuron (methyl); procynazine; prodiamine; profluralin; proglinazine (ethyl); prometon; prometrin; propachlor; propanyl; propaquizafop and its esters; propazine; profam; propisochlor; propoxycarbazone (sodium); propyzamide; prosulfalin; prosulfocarb; prosulfuron (CGA-152005); prinachlor; pyraflufen (ethyl); pyrazolinate; pyrazon; pyrazosulfuron (ethyl); pyrazoxifen; pyribenzoxim; pyributicarb; pyridafol; pyridate; pyrimidobac (methyl); pyritiobac (-sodium) (KIH-2031); piroxofop and its esters (e.g. propargyl ester); quinclorac; quinmerac; quinoclamine; quinofop and its ester derivatives, quizalofop and quizalofop-P and their ester derivatives, for example, quizalofop-ethyl; chizalofop-β-tefuryl and -ethyl; renriduron; rimsulfuron (DPX-E 9636); S 275, that is, 2- [4-chloro-2-fluoro-5- (2-propynyloxy) phenyl] -4,5,6,7-tetrahydro-2H-indazole; secbumeton; methoxydim; siduron; simazine; simetrin; SN 106279, that is, 2 - [[7- [2-chloro-4- (trifluoromethyl) phenoxy] -2-naphthalenyl] oxy] propanoic acid and methyl ester; sulcotrione; sulfentrazone (FMC-97285, F-6285); sulfazuron; sulfometuron (methyl); sulfosate (ICI-A0224); sulfosulfuron; TCA; tebutam (GCP-5544); tebutiuron; tepraloxidim; terbacil; terbucarb; terbuchlor; terbumeton; terbuthylazine; terbutrin; TFH 450, i.e. N, N-diethyl-3 - [(2-ethyl-6-methylphenyl) sulfonyl] -1H-1,2,4-triazole-1-carboxamide; tenylchlor (NSK-850); thiafluamide; thiazafluron; thiazopyr (Mon-13200); thiadiazimin (SN-24085); thifensulfuron (methyl); thiobencarb; thiocarbazyl; tralcoxidim; tri-alate; triasulfuron; triaziflam; triazophenamide; tribenuron (methyl); triclopyr; tridiphan; trietazine; trifluralin; trifluorulfuron and esters (e.g. methyl ester, DPX-66037); trimeturon; tritosulfuron; tsitodef; vernolate; WL-110547, i.e. 5-phenoxy-1- [3- (trifluoromethyl) phenyl] -1H-tetrazole; BAY MKH 6561, UBH-509; D-489; LS 82-556; KPP-300; NC-324; NC-330; KH-218; DPX-N8189; SC-0774; DOWCO-535; DK-8910; V-53482; PP-600; MBH-001; KIH-9201; ET-751; KIH-6127, KIH-485 and KIH-2023.

Selective weed control in useful and ornamental plant crops is particularly interesting. Although compounds (I) already show very good to satisfactory selectivity in many crops, in principle in some crops and especially also in the case of mixtures with other herbicides, which are poorly selective, phytotoxicities may occur in cultivated plants. In this connection, particularly interesting combinations of compounds of formula (I) are those containing the compounds of formula (I) or combinations thereof with other herbicides or pesticides and protectors. Protectors, which are applied with an antidote efficacy content, reduce the phytotoxic side effects of herbicides / pesticides applied, for example, to economically significant crops such as cereals (wheat, barley, rye, maize, rice, millet), beet, sugar cane, rapeseed, cotton and soya, preferably cereals. The following groups of compounds are considered, for example, as protectors for compounds (I) and their combinations with other pesticides: a) compounds of formulas (S-II) to (S-IV)

<R ")„, - H-

α

The

(S-II)

(S-III)

(S-IV)

wherein the symbols and indices have the following meanings: n 'is a natural number from 0 to 5, preferably 0 to 3; T is a (C1 or C2) alkanediyl chain which is unsubstituted or is substituted by one or two (C1 -C4) alkyl radicals or with [(C1 -C3) alkoxy] carbonyl; W is an unsubstituted or substituted divalent heterocyclic radical of the partially unsaturated or aromatic five-ring heterocycle group having 1 to 3 N or O type hetero ring atoms, where at least one N atom and at most an atom of O is contained in the ring, preferably a radical from group (W1) to (W4)

m 'is 0 or 1;

R171 R19 same or different, are halogen, (C1 -C4) alkyl, (C1 -C4) alkoxy, nitro or (C1 -C4) haloalkyl;

The same or different R18, R20 are OR24, SR24 or NR24R25 or a 3- to 7-membered saturated or unsaturated heterocycle with at least one N atom and up to 3 heteroatoms, preferably from the O and S group, which is attached to the carbonyl group at (S-II) or (S-III) through the N atom and is unsubstituted or substituted by optionally substituted (C1 -C4) alkyl, (C1 -C4) alkoxy or phenyl radicals, preferably a radical of formula OR24, NHR25 or N (CH3) 2, especially of formula OR24;

R24 is hydrogen or an unsubstituted or substituted aliphatic hydrocarbon radical, preferably having a total of 1 to 18 carbon atoms;

(Wl)

(W2)

(W3)

(W4) R25 is hydrogen, substituted or unsubstituted (C1 -C6) alkyl, (C1 -C6) alkoxy or phenyl;

Rx is H1 (C1 -C8) -alkyl, (C1C8) -haloalkyl, (C1 -C6 alkoxyKCrC3 O-alkyl, cyano or COOR261 wherein R26 is hydrogen, (C1C8) -alkyl, (C1-C8) haloalkyl (CrC4) C 1 -C 4 alkoxyalkyl, C 1 -C 6 alkylhydroxyalkyl, C 3 -C 12 cycloalkyl or tri (C 1 -C 4) alkyl silyl;

R271 R28, R29 are the same or different substituted or unsubstituted (C1-C8) -alkyl, (C1-C8) -haloalkyl, (C3-C12) -cycloalkyl or phenyl; R 21 is (C 1 -C 4) ^ alkyl, (C 1 -C 4) haloalkyl, (C 2 -C 4) alkenyl, (C 2 -C 4) haloalkenyl, (C 3 -C 7) cycloalkyl, preferably dichloromethyl;

R221 R23 is the same or different hydrogen, (C1-C4-4 alkyl), (C2-C4) -alkenyl, (C2-C4) -alkyl, (C1-C4) -haloalkyl, (C2-C4) -haloalkenyl, (C1-C4) - C 1 -C 4 alkylcarbamoylC 1 -C 6 alkyl, C 1 -C 4 alkenylcarbamoyl C 1 -C 4 alkyl, C 1 -C 4 alkoxyalkyl, dioxolanyl C 1 -C 4 alkyl, thiazolyl, furyl, furylalkyl, thienyl, piperidyl, substituted or unsubstituted phenyl or R22 and R23 together form a substituted or unsubstituted heterocyclic ring, preferably an oxazolidine, thiazolidine, piperidine, morpholine, hexahydropyrimidine or benzoxazine ring; one or more compounds of the group: 1,8-naphthalic acid anhydride, methyl diphenylmethoxy acetate, 1- (2-chlorobenzyl) -3- (1-methyl-1-phenylethyl) urea (cumiluron), 0.0- diethyl S-2-ethylthioethyl phosphorditioate (disulfoton), 4-chlorophenyl methylcarbamate (mefenate), 0,0-diethyl-0-phenylphosphorothioate (dietolate),

4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, CAS Registry: 31541-57-8),

cyanomethoxyimino (phenyl) acetonitrile (cytetrinyl), 1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrinyl), 4'-chloro-2,2,2-trifluoracetophenon-0-1,3-dioxolan-2-ylmethyloxime (fluxophenim), 4,6-dichloro-2-phenylpyrimidine (phenlorim), benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole), 2-dichloromethyl-2-methyl-1, 3-dioxolane (MG-191), N- (4-methylphenyl) -N '- (1-methyl-1-phenylethyl) urea (dimron), (2,4-dichlorophenoxy) acetic acid (2,4-d) (4-chlorophenoxy) acetic acid, (R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB) (4-chloro-o-tolyloxy) acetic acid (MCPA), 4- (4-chloro-o-tolyloxy) butyric acid, 4- (4-chlorophenoxy) butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba),

1- (ethoxycarbonyl) ethyl-3,6-dichloro-2-methoxybenzoate (lactide) as well as salts and esters thereof, preferably (C1 -C8); c) N-acylsulfonamides of formula (S-V) and their salts

R30 represents hydrogen, a hydrocarbon radical, a hydrocarbon-oxide radical, a thio hydrocarbon radical or a heterocyclyl radical, which is preferably attached via a carbon atom, wherein each of the four last mentioned radicals is not substituted or is substituted by one or more same or different radicals of the halogen, cyano, nitro, amino, hydroxy, carboxy, formyl, carbonamide, sulfonamide and radicals of the formula -Za-Ra1

wherein each hydrocarbon moiety preferably has 1 to 20 carbon atoms and a R 30 radical containing C including substituents, preferably 1 to 30 carbon atoms; R 31 represents hydrogen or (C 1 -C 4) alkyl, preferably hydrogen or R 30 and R 31 together with the group of the formula -CO-N- represent the radical of a 3- to 8-membered saturated or unsaturated ring; R32 the same or different represents halogen, cyano, nitro, amino, hydroxy, carbon

(S-V)

wherein boxy, formyl, CONH2, SO2NH2 or a radical of the formula -Zb-Rb '; R33 represents hydrogen or (C1 -C4) alkyl, preferably H; R34 is the same or different, represents halogen, cyano, nitro, amino, hydroxy, carbonoxy, CHO1 CONH2, SO2NH2 or a radical of the formula -Zc'-Rc '; Ra represents a hydrocarbon radical or a heterocyclyl radical, wherein each of the two last mentioned radicals is unsubstituted or is substituted by one or more same or different radicals from the halogen, cyano, nitro, amino, hydroxy, mono- and di - [(C1 -C4) alkyl] amino or an alkyl radical, wherein several, preferably 2 or 3 non-neighboring CH2 groups are in each case substituted by an oxygen atom; The same or different Rb1Rc represent a hydrocarbon radical or a heterocyclyl radical, wherein each of the two radicals mentioned last is unsubstituted or is substituted by one or more equal or different radicals of the halogen, cyano, nitro, amino, hydroxy, phosphoryl, halo (C1 -C4) alkoxy, mono- and di - [(C1 -C4) alkyl] amino or an alkyl radical in which several, preferably 2 or 3 non-neighboring CH2 groups are in each case substituted. by an oxygen atom;

Za 'represents a divalent group of the formula -O-, -S-, -CO-, -CS-, -CO-O-, -CO-S-, -O-CO-, -S-CO-, -S0 -, -SO 2 -, -NR * -, -CO-NR * -, -NR * -CO-, -SO 2 -NR * - or -NR * -SO 2 -, where the bond indicated to the right of the respective divalent group is the bond for the radical Rb 'or Rc' and wherein R * in the 5 radicals mentioned last independently of each other represents in each case H, (C1 -C4) alkyl or halo (C1 -C4) alkyl;

η represents an integer from 0 to 4, preferably 0, 1 or 2, especially 0 or 1 and

m represents an integer from 0 to 5, preferably O, 1, 2 or 3, especially O, 1 or 2;

(d) acylsulfamoylbenzoic acid amides of the general formula (S-VI), optionally also in salt form;

(S-W) in which

X 3 represents CH or N;

R35 represents hydrogen, heterocyclyl or a hydrocarbon radical, wherein the last two mentioned radicals are optionally substituted by one or more radicals equal to or different from the group halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH2, SO2NH2 and Za -Frog'; R36 represents hydrogen, hydroxy, (C1 -C6) alkyl, (C2 -C6) alkenyl, (C2 -C6) alkynyl, (C1 -C6) alkoxy, (C2 -C6) alkenyloxy, wherein the five radicals mentioned finally they are optionally substituted by one or more same or different radicals of the group halogen, hydroxy, (C1 -C4) alkyl, (C1 -C4) alkoxy and (C1 -C4) alkylthio or

R35 and R36 together with the nitrogen atom carrying them represent a saturated or unsaturated 3- to 8-membered ring;

R37 represents halogen, cyano, nitro, amino, hydroxy, carboxy, CHO, CONH2, SO2NH2OuZb-Rb ';

R38 represents hydrogen, (C1 -C4) alkyl, (C2 -C4) alkenyl or (C2 -C4) alkynyl;

R39 represents halogen, cyano, nitro, amino, hydroxy, carboxy, phosphoryl, CHO, CONH2, SO2NH2 or Z0 -Rc '; Ra 'represents a (C2 -C20) alkyl radical whose carbon chain is interrupted one or more times by oxygen atoms, represents heterocyclyl or a hydrocarbon radical. wherein the two radicals mentioned above are optionally substituted by one or more radicals equal to or different from the group halogen, cyano, nitro, amino, hydroxy, mono- and di - [(C 1 -C 4) alkyl] - amino;

The same or different Rb 'and Rc' represent (C2 -C20) alkyl radical, whose carbon chain is interrupted one or more times by oxygen atoms, represents heterocyclyl or a hydrocarbon radical. wherein the two last mentioned radicals may optionally be substituted by one or more equal or different radicals from the group halogen, cyano, nitro, amino, hydroxy, phosphoryl, (C1-C4) -Iaylaoxy, mono- and di- [( C1 -C4 alkyl] amino; Za 'represents a divalent unit of the group O, S, CO, CS, C (O) O, C (O) S, SO, SO2, NRd', C (O) NRd 'or SO2NRd';

The same or different Zb1Zc represent a direct bond or a divalent unit of the group O, S, CO, CS, C (O) O, C (O) S, SO1 SO2, NRd ', SO2NRd' or C (O) NRd ' ;

R d 'represents hydrogen, (C 1 -C 4) -alkyl or (C 1 -C 4) -Iaylaalkyl; η represents an integer from 0 to 4 and

m, where X represents CH, represents an integer from 0 to 5, and where X represents N, represents an integer from 0 to 4; e) acylsulfamoylbenzoic acid amide type compounds, for example of the following formula (X-VII), which are known, for example, from WO 99/16744

for example those where

R21 represents cyclopropyl and R22 is H (S-3-1 = 4-cyclopropylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide), R21 is cyclopropyl and R22 is 5-CI (S-3-2), R21 is ethyl and R22 is H (S-3-3), R21 is isopropyl and R22 is 5-CI (S-3-4) and R21 is isopropyl and R22 is H (S-3-5);

f) N-acylsulfamoylphenylurea-type compounds of formula (S-VIII), which are known, for example, from EP-A-365484,

(S-Vll)

OCH

R »

(S-VIII)

in which

A represents a radical of the group R0 and Rp 'independent of each other, represent hydrogen, (C1-C8) alkyl, (C3-C8) -cycloalkyl, (C3-C6) -alkenyl, (C3-C6) ^ IquiniIa1

-The:

or represent (C1 -C4) alkoxy substituted by (C1 -C4) alkoxy or by

-Gt:

or

R0 'and Rp' together represent a (C4-C6) -alkylene bridge or a (C4-C6) -alkylene bridge interrupted by oxygen, sulfur, SO1 SO2, NH or -N ((C1-C4) -alkyl),

Ry 'represents hydrogen or (C1 -C4) alkyl,

Ra and Rb independent of each other represent hydrogen, halogen, cyano, nitro, trifluoromethyl, (C1 -C4) alkyl, (C1 -C4) alkylthio, (C1 -C4) alkylsulfinyl, (CrC4) -alkylsulfonyl, -COOR1 -CONRkRm ', -CORn', -SO2NRkRm 'or -SO2- (C1 -C4) alkyl, or Ra' and Rb 'together represent a (C3 -C4) alkylene bridge, which may be substituted for halogen or (C 1 -C 4) alkyl or a (C 3 -C 4) alkenylene bridge which may be substituted by halogen or (C 1 -C 4) alkyl or a C 4 -C 6 alkadienylene bridge which may be replaced by halogen or (C 1 -C 4) alkyl and

R 9 and Rh independently of each other represent hydrogen, halogen, (C 1 -C 4 alkyl, trifluoromethyl, methoxy, methylthio or -COOR 1 "wherein R c represents hydrogen, halogen (C 1 -C 4) alkyl or methoxy, R d 'represents hydrogen , halogen, nitro, (C1 -C4) alkyl, (C1 -C4) alkoxy, (C1 -C4) alkylthio, (C1 -C4) alkylsulfinyl, (C1 -C4) alkylsulfonyl, -COOR1 'or -CONRkRm',

Re 'represents hydrogen, halogen, (C1 -C4) -alkyl, -COORr1 trifluoromethyl or methoxy or Rd' and Re 'together represent a (C3 -C4) -alkylene bridge, Rf represents hydrogen, halogen or (C1C4) -alkyl,

X'V

ReRs independent of each other represent hydrogen, halogen, (C1 -C4) alkyl, (C1 -C4) alkoxy, (C1 -C4) alkylthio, -COOR1 ', trifluoromethyl, nitro or cyano,

R 1, R k and R m independent of each other represent hydrogen or (C 1 -C 4) alkyl,

Rk 'and Rm' together represent a C4 -C6 alkylene bridge or an oxygen interrupted C4 -C6 alkylene bridge, NH or -N ((C1 -C4) alkyl and Rn represents (C1 -C4) alkyl, phenyl or halogen substituted phenyl, (C1 -C4) alkyl, methoxy, nitro or trifluoromethyl, preferably

1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea, 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3,3-dimethylurea, 1- [4- (N-4, 5-dimethylbenzoylsulfamoyl) phenyl] -3-methylurea, 1- [4- (N-naphthoylsulfamoyl) phenyl] -3,3-dimethylurea,

(g) compounds of the acylsulfamoylbenzoic acid amide type of formula (X-IX), known from EP-A-1019368, optionally also in salt form;

in which

R101 represents methyl, methoxy or trifluoromethoxy;

R102 represents hydrogen, chlorine or methyl;

R103 represents hydrogen, ethyl or propargyl;

R104 represents ethyl, cyclopropyl, isopropyl or propargyl or

R103 and R104 together form the (CH2) 4 group,

including stereoisomers and salts common in agriculture. Preference is given to herbicide-protective combinations, containing (A) an amount of herbicidal efficacy of one or more compounds of formula (I) or salts thereof and (B) an amount of antidote efficacy of one or more protectors.

Amounts of herbicidal efficacy in the sense of the invention means an amount of one or more herbicides which is suitable for negatively influencing plant growth. Amount of antidote efficacy in the sense of the invention means an amount of one or more protectors, which is suitable, for reducing the phytotoxic effect of active substances in plant protection preparations (e.g., herbicides) on cultivated plants.

The compounds of formula (S-II) are known, for example, from EP-AO 333 131 (ZA-89/1960), EP-AO 269 806 (US-A-4,891,057), EP-AO 346 620 (AU- A-89/34951), EP-AO 174 562, EP-AO 346 620 (WO-A-91/08 202), WO-A-91/07 874 or WO-A 95/07 897 (ZA 94/7120 ) and the literature cited therein or may be prepared by or in a manner analogous to the processes described therein. The compounds of formula (S-III) are known from EP-AO 086 750, EP-AO 94349 (US-A-4,902,340), EP-AO 191736 (US-A-4,881,966) and EP-AO 492 366 and literature therein. cited or may be prepared by or analogous to the processes described therein. Some compounds are further described in EP-A-0.582.198 and WO 2002/34048.

The compounds of formula (S-IV) are known from numerous patent applications, for example, US-A-4,021,224 and US-A-4,021,229.

Group B (b) compounds are further known from CN-A-87 / 102.789, EP-A-365484 as well as from The Pesticide Manual, The British Crop Protection Council and the Royal Society of Chemistry, 11th edition, Farnham 1997. The compounds of group B (c) are described in WO-A-97/45016, those of group B (d) in WO-A-99/16744, those of group B (e) in EP-A-365484 and those of group B (g) in EP-A-1019368.

The cited reports contain detailed information on preparation processes and starting materials and mention preferred compounds. With express reference to these reports, they are cited as a component of this descriptive report.

Preference is given to herbicide-protective combinations containing protectors of the formula (S-II) and / or (S-111), wherein the symbols and indices have the following meanings: R24 is hydrogen, (CrC18) - (C3 -C12) cycloalkyl, (C2 -C8) alkenyl and (C2 -C8) alkynyl, wherein the groups containing C may be substituted by one or more, preferably up to three R50 radicals; R50 is the same or different, halogen, hydroxy, (C1 -C8) alkoxy, (C1 -C8) alkylthio, (C2 -C8) alkenylthio, (C2-C8) alkynylthio, (C2-C8) -alkenyloxy, (C2-C8) (C 3 -C 7) -alkyloxyoxy, (C 3 -C 7) cycloalkyl, cyano, mono- and di ((C 1 -C 4) alkyl) amino, carboxy (C 1 -C 8) alkoxycarbonyl, (C 2 -C 8) (C1 -C8) -alkyloxycarbonyl, (C2 -C8) -alkyloxycarbonyl, (C1 -C8) -alkylcarbonyl, (C2 -C8) -alkylcarbonyl, 1- (Mdroxyimino) - (C1 -C6) -alkyl 1 - [(C 1 -C 4) -alkylimino] - (C 1 -C 4) -alkyl, 1 - [(C 1 -C 4) alkoxyiminoHC 1 -C 6) -alkyl, (C 1 -C 8) alkylcarbonylamino, (C 2 (C8) -Alkynylcarbonylamino, aminocarbonyl, (C1-C8) -Bialkylaminocarbonyl, di ((C1 -C6) alkyl) -aminocarbonyl, (C2-C6) -alkenylaminocarbonyl, (C2-C6) -alkynylaminocarbonyl, (C1-8) C8) -alkoxycarbonylamino, (C1 -C8) -alkylaminocarbonylamino, (C1 -C6) -alkylcarbonyloxy, which is unsubstituted or substituted by R511 (C2-C6) -alkenylcarbonyloxy, (C2-C6) -alkylalkyl arbonyloxy, (C1 -C8) alkylsulfonyl, phenyl, phenyl (C1 -C6) alkoxy, phenyl (C1 -C6) alkoxycarbonyl, phenoxy, phenoxy (C1 -C6) alkoxy, phenoxy (C1 -C6) alkoxycarbonyl, phenylcarbonyloxy, phenylcarbonylamino, phenyl (C1 -C6) alkylcarbonylamino, wherein the last 9 radicals are not substituted on the phenyl ring or are substituted one or more times, preferably up to three times by R52 radicals; SiR13, -O-SiR13, R'3S- (C1 -C8) alkoxy, -CO-O-NR12, -ON = CR12, -N = CR12, -O-NR12, -NR12, CH (OR1) 2, -O- (CH2) m -CH (OR1) 2, -CRmi (OR1) 2, -O- (CH2) mCR111 (OR11) 2 or by R "0-CHR" 'CHCO0 "- (C1 -C6) alkoxy;

The same or different R51 is halogen, nitro, (C1 -C4) alkoxy and phenyl unsubstituted or substituted with one or more, preferably up to three R52 radicals;

R52 the same or different is halogen, (C1 -C4) alkyl, (C1 -C4) alkoxy, (C1 -C4) haloalkyl, (C1 -C4) haloalkoxy or nitro;

The same or different R 'is hydrogen, (C1 -C4) alkyl, unsubstituted phenyl or

substituted with one or more, preferably with up to three radicals R52 or

two R 'radicals together form a (C 2 -C 6) alkanediyl chain;

R "same or different is (C 1 -C 4) -alkyl or two radicals R" together form a

(C 2 -C 6) alkanediyl chain;

R "'is hydrogen or (C1 -C4) alkyl;

m is 0, 1, 2, 3, 4, 5 or 6.

Particular preference is given to herbicide-protector combinations according to the invention, containing protectors of formula (S-II) and / or (S-111), in which the symbols and indices have the following meanings:

24

R is hydrogen, (C1 -C8) alkyl or (C3 -C7) cycloalkyl, wherein the above C-containing radicals are unsubstituted or are substituted one or more times by halogen or once or twice, preferably once, by R50 radicals. ,

R50 is the same or different, hydroxy, (C1 -C4) alkoxy, carboxy, (C1-C4) alkoxycarbonyl, (C2-C6) alkenyloxycarbonyl, (C2-C6) -alkynyloxycarbonyl, 1- (hydroxyimino) - (CrC4) - alkyl, 1 - [(C 1 -C 4) alkylimino] - (C 1 -C 4) alkyl and 1 - [(C 1 -C 4) alkoxyimino] - (C 1 -C 4) alkyl; -SiR13, -ON = CR12, -N = CR12, -NR12, and -O-NR12, where same or different R 'is hydrogen, (C1 -C4) alkyl or in pairs represents a (C4 -C5) -alkanediyl chain ,

The same or different R27, R28, R29 are hydrogen, (C1 -C8) alkyl, (C1 -C6) haloalkyl, (C3 -C7) cycloalkyl or phenyl, which is unsubstituted or substituted by one or more of the radicals of the halogen, cyano, nitro, amino, mono- and di - [(C 1 -C 4) alkyl] amino group, (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) alkoxy, (C 1 -C 4) haloalkoxy (C 1 -C 4) Alkylthio and (C 1 -C 4) Alkylamphonyl; Rx 'is hydrogen or COOR26, where R26 is hydrogen, (C1-C8) ^ C1-6 alkyl, (C1-C8) -IIAIoa-alkyl, (C1 -C4) -alkoxy- (C1-C6) alkyl, (C1-C6) -Ndroxy-alkyl, ( C3 -C7) cycloalkyl or tri (C1 -C4) alkylsilyl,

The same or different R17, R19 are halogen, methyl, ethyl, methoxy, ethoxy, (C1 or C2) -haloalkyl, preferably hydrogen, halogen or (C1 or C2) -haloalkyl. Very particular preference is given to protectors in which the symbols and indices in formula (S-II) have the following meanings: R17 is halogen, nitro or (C1 -C4) -haloalkyl; n is 0, 1.2 or 3;

R18 is a radical of the formula OR24,

R24 is hydrogen, (C1 -C8) alkyl or (C3 -C7) cycloalkyl, wherein the above C-containing radicals are unsubstituted or are substituted one or more times, preferably up to three times, by equal or different halogen radicals or up to twice, preferably once, by the same or different radicals of the hydroxy group, (C1 -C4) alkoxy, (C1 -C4) alkoxycarbonyl, (C2 -C6) alkenyloxycarbonyl, (C2 -C6) alkynyloxycarbonyl, 1- (Ndroxyimino) - (C 1 -C 4) alkyl, 1 - [(C 1 -C 4) alkylimino] - (C 1 -C 4) alkyl, 1 - [(C 1 -C 4) alkoxyimino] - (C 1 -C 4) alkyl and radicals of the formulas -SiR 13, - ON = R12, -N = CR12, -NR12 and -O-NR12, wherein the same or different radicals R 'in the mentioned formulas represent hydrogen, (C1 -C4) alkyl or in pairs, (C4 or C5) alkanediyl; The same or different R 27, R 28, R 29 are hydrogen, (C 1 -C 6) alkyl, (C 1 -C 6) haloalkyl, (C 3 -C 7) cycloalkyl or phenyl which is unsubstituted is substituted by one or more of the radicals of halogen group, (C1 -C4) -alkyl, (C1-C4) - alkoxy, nitro, (C1-C4) -IaIoaoalkyl and (CrC4) -haloalkoxy and Rx 'is hydrogen or COOR26, where R26 is hydrogen, (CrC8) - alkyl, (C1 -C8) -haloalkyl, (C1 -C4) -alkoxy- (C1 -C4) -alkyl, (C1-C6) -Ndroxyalkyl, (C3-C7) -cycloalkyl or tri- (C1-C4) -alkylsilyl.

Very particular preference is also given to the protectors of formula (S-11), wherein the symbols and indices have the following meanings:

R19 is halogen or (C1 -C4) haloalkyl;

n 'is 0, 1, 2 or 3, wherein (R19) n' is preferably 5-CI;

R20 is a radical of formula OR24;

T is CH 2 or CH (COO - ((C 1 -C 3) alkyl)) and

R 24 is hydrogen, (C 1 -C 8) alkyl, (C 1 -C 8) haloalkyl or (C 1 -C 4 alkoxy-C 1 -C 4) alkyl, preferably hydrogen or (C 1 -C 8) alkyl.

In this case, especially preferred are protectors of formula (II), in which symbols and indices have the following meanings: W is (W1);

R17 is halogen or (C1-C2) -I-IaIoaIchiIa; n 'is 0, 1, 2 or 3, wherein (R 17) n' preferably 2,4-CI 2 is; R18 is a radical of formula OR24;

R24 is hydrogen, (C1-C8) alkyl, (C1-C4) -Ilyloyl, (C1-C4) -hydroxyalkyl, (C3-C7) -cycloalkyl, (C1-C4) -Bloxy- (C1-C4) -Blyl or tri (C1 -C2) alkylsilyl, preferably (C1 -C4) alkyl;

R27 is hydrogen, (C1-C8) -alkyl, (C1-C4) -ialylalkyl or (C3-C7) -cycloalkyl, preferably hydrogen or (C1-C4) -alkyl and

Rx 'is COOR26, wherein R26 is hydrogen, (C 1 -C 8) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) Hydroxyalkyl, (C 3 -C 7) cycloalkyl, (C 1 -C 4) alkoxy (C 1 -C 4) alkyl or tri (C 1 -C 2) alkylsilyl, preferably hydrogen or (C 1 -C 4) alkyl.

Especially preferred are also herbicidal compositions containing a protector of the formula (S-11), wherein the symbols and indices have the following meanings: W is (W2);

R17 is halogen or (C1-C2) haloalkyl; n 'is 0, 1, 2 or 3, wherein (R 17) n 1 preferably 2,4-CI 2 is; R18 is a radical of formula OR24;

R24 is hydrogen, (C1 -C8) -alkyl, (C1-C4) -Ilyloyl, (C1-C4) -Ndroxyalkyl, (C3-C7) -cycloalkyl, ((CrCO-alkoxyHCrC3 -alkyl or tri- (CrC2) -alkyl) silyl, preferably (C1 -C4) alkyl and

R27 is hydrogen, unsubstituted or substituted (C1 -C4) -alkyl, (C1-C4) -alkyl, (C3-C7) -cycloalkyl or phenyl, preferably hydrogen, (C1-C4) -alkyl or phenyl, which is not substituted or is substituted by one or more halogen radicals, (C1 -C4) alkyl, (C1 -C4) haloalkyl, nitro, cyano or (C1 -C4) alkoxy.

Especially preferred are also protectors of formula (S-11), wherein the symbols and indices have the following meanings: R17 is halogen or (C1 -C2) haloalkyl; n 'is O, 1, 2 or 3, wherein (R 17) n' is preferably 2,4-CI 2; R18 is a radical of formula OR24;

R 24 is hydrogen, (C 1 -C 8) alkyl, (C 1 -C 4) haloalkyl, (C 1 -C 4) hydroxyalkyl, (C 3 -C 7) -Cycloalkyl, (C 1 -C 4) alkoxy (C 1 -C 4) alkyl or tri- (C 1 -C 2) ) -alkylsilyl, preferably (C1 -C4) alkyl and R28 is (C1 -C8) alkyl or (C1 -C4) -haloalkyl, preferably Crhaloalkyl.

Especially preferred are also protectors of the formula (S-M), wherein the symbols and indices have the following meanings: W is (W4);

R 17 is halogen, nitro, (C 1 -C 4) alkyl, (C 1 -C 2) Aliaalkyl, preferably CF 30 O (C 1 -C 4) alkoxy; n 'is 0, 1, 2 or 3; m'éOou 1;

R18 is a radical of formula OR24;

R 24 is hydrogen, (C 1 -C 4) alkyl, Carboxy (C 1 -C 4) -alkyl, (C 1 -C 4) alkoxycarbonyl- (C 1 -C 4) alkyl, preferably (C 1 -C 4) alkoxy-CO-CH 2 -, ( C1 -C4 alkoxy-CO-C (CH3) H-, HO-CO-CH2- or HO-CO-C (CH3) H- and

R29 is hydrogen, (C1 -C4) -alkyl, (C1C4) -haloalkyl, (C3-C7) -cycloalkyl or phenyl, which is unsubstituted or substituted by one or more halogen radicals, (CrC4) -alkyl, (C1 -C4) haloalkyl, nitro, cyano and (C1 -C4) alkoxy. The following groups of compounds are especially suitable for

as protective agents for the herbicidal active substances of formula (I):

a) dichlorophenylpyrazolin-3-carboxylic acid type compounds (i.e. of formula (S-11), wherein W is (W1) and (R17) rv is 2,4-CI2), preferably compounds such as 1- (2,4-dichlorophenyl) -5- acid ethyl ester

(ethoxycarbonyl) -5-methyl-2-pyrazolin-3-carboxylic (S-11-1, mefenpir-diethyl), metepyr-dimethyl and mefenpir (S-II-O) and related compounds as described in WO-A 91/07874;

b) dichlorophenylpyrazolecarboxylic acid derivatives (i.e. of formula (S-11), wherein W is (W2) and (R17) n 'is 2,4-Cl 2), preferably

such as 1- (2,4-dichlorophenyl) -5-methyl-pyrazol-3-carboxylic acid ethyl ester (S-11-2), 1- (2,4-dichlorophenyl) -5- isopropyl pyrazol-3-carboxylic acid (S-11-3), 1- (2,4-dichlorophenyl) -5- (1,1-dimethylethyl) pyrazol-3-carboxylic acid ethyl ester (S-11- 4), 1- (2,4-Dichlorophenyl) -5-phenyl-pyrazol-3-carboxylic acid ethyl ester (S-11-5) and related compounds as described in EP-A-0.333.131 and EP-A-0,269,806;

c) triazolecarboxylic acid-type compounds (i.e. of formula (S-11), wherein W is (W3) and (R17) rv is 2,4-Cl 2), preferably compounds such as phenolazole-ethyl, that is, 1- (2,4-dichlorophenyl) -5-trichloromethyl- (1H) -1,2,4-triazole-3-carboxylic acid ethyl ester (S-11-6) and related compounds (see EP-A-0.174.562 and EP-A-0.346.620);

d) compounds of the type 5-benzyl- or 5-phenyl-2-isoxazolin-3-carboxylic acid or 5,5-diphenyl-2-isoxazolin-3-carboxylic acid such as isoxa

diphen (S-11-12), (where W is (W 4)), preferably compounds such as 5- (2,4-dichlorobenzyl) -2-isoxazolin-3-carboxylic acid ethyl ester (S-11- 7) or 5-phenyl-2-isoxazolin-3-carboxylic acid ethyl ester (S-11-8) and related compounds as described in WO-A-91/08202 or 5-acid ethyl ester , 5-diphenyl-2-isoxazolinecarboxylic acid (S-11-9, isoxadiphenyl) or 5,5-diphenyl-2-isoxazolinecarboxylic acid n-propyl ester (S-11-10) 5- (4-Fluorphenyl) -5-phenyl-3-isoxazolin-3-carboxylic acid ethyl ester (S-11-11) as described in WO-A-95/07897.

e) Compounds of the 8-quinolinoxyacetic acid type, for example those of formula (S-11), wherein (R19) n 'is 5-CI, R20 is OR24 and T is CH2,

preferably the compounds

(5-chloro-8-quinolinoxy) acetic acid (1-methylhexyl) ester (S-11-1-chloro-quinocet-mexyl),

(5-Chloro-8-quinolinoxy) acetic acid (1,3-dimethyl-but-1-yl) ester (S-III-), (5-chloro-8-methyl-4-allyl-butyl ester) (5-chloro-8-quinolinoxy) acetic acid (S-11-3), (5-chloro-8-quinolinoxy) acetic acid 1-allyloxy-prop-2-yl ester (5-chloro-8) -acetic acid ethyl ester 8-quinolinoxy) acetic acid (S-11-15), (5-chloro-8-quinolinoxy) acetic acid methyl ester (S-11-11), (5-chloro-8-quinolinoxy) acetic acid allylic ester ( S-11-7), (5-Chloro-8-quinolinoxy) acetic acid 2- (2-propyliden-iminoxy) -1-ethyl ester (S-11-8),

(5-Chloro-8-quinolinoxy) acetic acid 2-oxo-prop-1-yl ester (S-11-11), (5-chloro-8-quinolinoxy) acetic acid (S-111-10) and their salts as described for example in WO0-A-2002/34048

and related compounds such as are described in EP-A-0.860.750, EP-A-0.094.349 and EP-A-0.191.736 or EP-A-0.492.366. f) Compounds of the type (5-chloro-8-quinolinoxy) -malonic acid, that is, of formula (S-11), wherein (R19) n. is 5-CI, R 20 is OR 24, T is -CH (COO-alkyl) -, preferably the compounds of (5-chloro-8-quinolinoxy) malonic acid diethyl ester (S-111-11), diallyl acid ester ( 5-chloro-8-quinolinoxy) malonic acid, (5-chloro-8-quinolinoxy) malonic acid methyl ethyl ester and related compounds as described in EP-A-0.582.198.

(g) Dichloracetamide-type compounds, ie formula (S-IV), preferably:

N, N-diallyl-2,2-dichloracetamide (dichlormid (S-IV-1) of US-A 4,137,070), 4-dichloracetyl-3,4-dihydro-3-methyl-2H-1, 4-benzoxazine (IV-2, benoxacor, from EP 0.149.974),

N1, N2-diallyl-N2-dichloracetylglycinamide (DKA-24 (IV-3), from HU 2143821), 4-dichloracetyl-1-oxa-4-aza-spiro [4,5] decane (AD-67), 2 2,2-Dichloro-N- (1,3-dioxolan-2-ylmethyl) -N- (2-propenyl) acetamide (PPG-1292), 3-dichloracetyl-2,2,5-trimethyloxazolidine (R-29148, S -IV-4), 3-dichloracetyl-2,2-dimethyl-5-phenyloxazolidine, 3-dichloracetyl-2,2-dimethyl-5- (2-thienyl) oxazolidin,

3-dichloracetyl-5- (2-furanyl) -2,2-dimethyloxazolidine (furilazole (S-IV-5), MON 13900),

1-dichloracetylhexahydro-3,3,8a-trimethylpyrrolo [1,2-a] pyrimidin-6 (2H) -on (dicyclonon, BAS 145138),

(h) compounds of group B (b), preferably 1,8-naphthalic acid anhydride (S-b-1), methyl diphenylmethoxyacetate (S-b-2), cyanomethoxyimino (phenyl) acetonitrile (cytometrinyl) (S-b-3),

1- (2-chlorobenzyl) -3- (1-methyl-1-phenylethyl) urea (cumyluron) (S-b-4), 0,0-diethyl S-2-ethylthioethyl phosphorodithioate (disulfoton) (S-b-5),

4-chlorophenyl methylcarbamate (mefenate) (S-b-6), 0,0-diethyl-0-phenylphosphorothioate (dietolate) (S-b-7),

4-carboxy-3,4-dihydro-2H-1-benzopyran-4-acetic acid (CL-304415, CAS Registry 31541-57-8) (S-b-8),

1,3-dioxolan-2-ylmethoxyimino (phenyl) acetonitrile (oxabetrinyl) (Sb-9), 4'-chloro-2,2,2-trifluoracetophenone 0-1,3-dioxolan-2-ylmethyloxime (fluxophenim) (Sb -10),

4,6-dichloro-2-phenylpyrimidine (phenlorim) (Sb-11), benzyl-2-chloro-4-trifluoromethyl-1,3-thiazole-5-carboxylate (flurazole) (Sb-12), 2-dichloromethyl 2-methyl-1,3-dioxolane (MG-191) (Sb-13), N- (4-methylphenyl) -N '- (1-methyl-1-phenylethyl) urea (dimron) (Sb-14_, acid (2,4-dichlorophenoxy) acetic (2,4-D), (4-chlorophenoxy) acetic acid,

(R, S) -2- (4-chloro-o-tolyloxy) propionic acid (mecoprop), 4- (2,4-dichlorophenoxy) butyric acid (2,4-DB), (4-chloro-o- tolyloxy) acetic (MCPA), 4- (4-chloro-o-tolyloxy) butyric acid, 4- (4-chlorophenoxy) butyric acid, 3,6-dichloro-2-methoxybenzoic acid (dicamba), 1- (ethoxycarbonyl) ethyl-3,6-dichloro-2-methoxybenzoate (lactidichlor), as well as salts and esters thereof, preferably (C1 -C8).

Protectors are furthermore preferred for compounds of formula (S-V) or salts thereof, wherein

R30 represents hydrogen, (C1 -C6) alkyl, (C3 -C6) cycloalkyl, furanyl or thienyl, wherein each of the last 4 radicals mentioned is unsubstituted or is substituted by one or more substituents on the halogen group, ( C1 -C4 alkoxy, halo (C1 -C6) alkoxy and (C1 -C4) alkylthio and in the case of cyclic radicals also (C1 -C4) alkyl and (C1 -C4) haloalkyl, R31 represents hydrogen,

R32 represents halogen, halo (C1 -C4) alkyl, halogen (C1 -C4) alkoxy, (C1 -C4) alkyl, (C1 -C4) alkoxy, (C1 -C4) alkylsulfonyl, (C1 -C4) alkoxycarbonyl or (C1C4) ) -alkylcarbonyl, preferably halogen, (C1 -C4) haloalkyl such as trifluoromethyl, (C1 -C4) alkoxy, halo (C1 -C4) alkoxy, (C1 -C4) alkoxycarbonyl or (C1 -C4) alkylsulfonyl, R33 represents hydrogen,

R34 represents halogen, (C1 -C4) alkyl, halogen (C1 -C4) alkyl, halogen (C1 -C4) alkoxy, (C3 -C6) cycloalkyl phenyl, (C1 -C4) alkoxy, cyano, (C1 -C4) ) - (C 1 -C 4) alkylsulfinyl, (C 1 -C 4) alkylsulfonyl, (C 1 -C 4) alkoxycarbonyl or (C 1 -C 4) alkylcarbonyl, preferably halogen, (C 1 -C 4) alkyl, (C 1 -C 4) haloalkyl, such as trifluoromethyl, halogen - (C1 -C4) alkoxy, (C1 -C4) alkoxy or (C1 -C4) alkylthio, η represents 0, 1 or 2 and represents 1 or 2.

Particularly preferred are compounds of formula (S-V) in which

which are

R30 = H3C-O-CH2-, R31 = R33 = H, R34 = 2-OMe-5-CI is (SV-2), R30 = cyclopropyl, R31 = R33 = H, R34 = 2-OMe is (SV- 3), R30 = cyclopropyl, R31 = R33 = H, R34 = 2-OMe-5-CI is (SV-4), R30 = cyclopropyl, R31 = R33 = H, R34 = 2-Me is (SV-5) , R 30 = tert-butyl, R 31 = R 33 = H, R 34 = 2-OMe is (SV-6).

In addition, protectors of formula (S-VI), wherein X 3 represents CH;

R35 represents hydrogen, (C1 -C6) alkyl, (C3 -C6) cycloalkyl, (C2 -C6) alkenyl, (C5 -C6) cycloalkenyl, phenyl or heterocyclyl with up to three heteroatoms of the group nitrogen, oxygen and sulfur, where the last six mentioned radicals are optionally substituted by one or more same or different substituents on the (C1-C6) -alkoxy, (C1-C6) -haloalkoxy, (C1-C2) -alkylsulfinyl halogen group, ( (C 1 -C 2) alkylsulfonyl, (C 3 -C 6) cycloalkyl, (C 1 -C 4) alkoxycarbonyl, (C 1 -C 4) alkylcarbonyl and phenyl and in the case of cyclic radicals, also (C 1 -C 4) alkyl and (C 1 -C 4) haloalkyl; R 36 represents hydrogen, (C 1 -C 6) alkyl, (C 2 -C 6) alkenyl, (C 2 -C 6) alkynyl, wherein the last three radicals are optionally substituted by one or more same or different substituents on the halogen group hydroxy, (C1 -C4) alkyl, (C1 -C4) alkoxy and (C1 -C4) alkylthio; R37 represents halogen, (C1 -C4) haloalkyl, (C1 -C4) haloalkoxy, nitro, (C1-10

15

(C4) alkyl, (C1 -C4) alkoxy, (C1 -C4) alkylsulfonyl, (C1 -C4) alkoxycarbonyl or

(C1 -C4 alkylcarbonyl);

R38 represents hydrogen;

R39 represents halogen, nitro, (C1 -C4) alkyl, (C1 -C4) haloalkyl, (C1 -C4) haloalkoxy, (C3 -C6) cycloalkyl, phenyl, (C1C4) alkoxy, cyano, (C1C4) alkylthio, (C1 -C4) alkylsulfinyl, (C1 -C4) alkylsulfonyl, (C1 -C4) alkoxycarbonyl or (C1 -C4) alkylcarbonyl; η represents 0, 1 or 2 and m represents 1 or 2.

Preferred protectors of the formula (S-VII) are (S-3-1), (S-3-2), (S-3-3), (S-3-4) and (S-3-5).

Preferred protectors of formula (VIII) are 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3-methylurea (S-VIII-1), 1- [4- (N-2-methoxybenzoylsulfamoyl) phenyl] -3 , 3-dimethylurea (S-VIII-2), 1- [4- (N-4,5-fimethylbenzoylsulfamoyl) phenyl] -3-methylurea (S-VIII-3) and 1- [4- (N-naphthoylsulfamoyl) phenyl] -3,3-dimethylurea (S-VIII-4).

Preferred protectors of formula S-IX are compounds of formulas S-IX-A1 through S-IX-A4

-CH,

S-IX-A1

S-IX-A3

^ CH1

of which again compound S-IX-A3 is very particularly preferred as a protector.

Particularly preferred herbicidal active substance combinations (A) as mentioned in table (I) and protectors (B) are those in which protector (B) is selected from the group of protectors consisting of the compounds of formulas S- Il-I (mefenpyr-diethyl), S-11-9 (isoxadifen-ethyl), S-11-1 (cloquintocet-mexyl), Sb-11 (phenlorim), Sb-14 (dimon), S -IX-A3 (4-Cyclopropylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide N - ({4 - [(cyclopropylamino) carbonyl] phenyl} sulfonyl) -2-methoxybenzamides, compounds S-Il-I and S- IX-A3 are very particularly preferred as protectors (B).

For rice application is particularly preferred isoxadiphenyl ethyl. Particularly preferred for cereals are methenhydropyridyl, cloquintocet-mexyl and 4-cyclopropylaminocarbonyl-N- (2-methoxybenzoyl) benzenesulfonamide N - ({4 - [(cyclopropylamino) carbonyl] phenyl} sulfonyl) -2-methoxybenzamide, especially isoxadifen-ethyl and 4-cyclopropyl-aminocarbonyl-N- (2-methoxy-benzoyl) benzenesulfonamide N - ({4 - [(cyclopropyl-amino) carbonyl] phenyl} sulfonyl) -2-methoxy -benzamide. For sugar cane application isoxadifen-ethyl is preferred.

Mixing with other known active substances such as fungicides, insecticides, acaricides, nematicides, bird-eating substances, plant nutrients and soil structure improving agents is also possible.

Some of the protectors are already known as herbicides and thus, in addition to the weed herbicidal effect, they also develop a protective effect on cultivated plants.

The weight ratios of the herbicide (blend) to protector generally depend on the amount of herbicide applied and the effectiveness of the protector and may vary within broad limits, for example in the range of 200: 1 to 1: 200, preferably 100. : 1 to 1: 100, especially 20: 1 to 1:20. Protectors may be formulated analogously to the compounds of formula (I) or mixtures thereof with other herbicides / pesticides and prepared and applied as a ready formulation or tank mix with the herbicides.

With external conditions such as temperature, humidity, the type of herbicide used and others, the amount of application required of the compounds of formula (I) varies. It may oscillate within wide limits, for example between 0.001 and 10.0 kg / ha or more active substance, however, it is preferably between 0.005 and 5 kg / ha.

The active substances according to the invention may be used, for example, in the following plants:

Dicotyledonous weeds of the genera: Abutilon, Amaranthus, Ambrosia, Anoda, Anthemis, Afanes, Atriplex, Bellis, Bidens, Capsella, Carduus, Cassia, Centaurea1 Chenopodium, Cirsium, Convolvulus, Datura, Desmodim, Emex, Erisimum, Euphorbia , Galeopsis, Galinsoga, Galium, Hibiscus lpomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria, Mentha, Mercury, Mullugo, Miosotis, Papaver, Farbitis, Plantago, Poligonum, Portulaca, Ranunculus, Rafanus, Rorippa Rotala, Rotala , Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sfenoclea, Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola, Xanthium.

Dicotyledonous cultures of the genera: Arachis, Beta, Brassica, Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossipium, Lpomoea, Lacuca, Linum, Lycopersicon, Nicotiana, Faseolus, Pisum, Solanum, Vicia.

Monocotyledonous weeds of the genera: Aegilops1 Agro-piron, Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus, Commelina, Cinodon, Ciperus, Dactiloctenium, Digitaria, Echinochloa, Eleocharis, Eleusine, Erochrostis, Festois , Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria, Panicum, Paspalum, Falaris, Fleum, Poa, Rottboellia, Sagittaria, Scirpus, Setaria, Sorghum.

Monocotyledonous cultures of the genera: Allium, Ananas, Asparagus, Avena, Hordeum, Oryza, Panicum, Saccharum, Secale1 Sorghum1 Triticale1 Triticum1 Zea. The use of the active substances according to the invention continues

However, it is by no means limited to these genera, but extends in the same way to other plants as well.

Depending on the concentration, the active substances according to the invention are suitable for the total control of weeds, for example in industrial and railway installations and on paths and squares with and without tree growth. Similarly, the active substances according to the invention may be used for weed control in permanent crops, for example forestry, ornamental woods, fruit, wineries, citrus, nuts, bananas, coffee, tea. , rubber, oil palm, cocoa, berry fruits and hops, on ornamental and sporting lawns and pastures, as well as for selective weed control in annual crops.

The compounds of formula (I) according to the invention show strong herbicidal efficacy and a broad spectrum of action on application to land and aerial plant parts. To some extent they are also suitable for the selective combat of monocotyledonous and dicotyledonous weeds in monocotyledonous and dicotyledonous crops, both in the preemergence and postemergence processes.

The preparation and use of the active substances according to the invention are shown in the following examples: Preparation Examples: Example 1

i 1 -tC '

H ^ .O ^ 1S * - * '

O-CH3

^ CH3

(IA-1)

(Process (a))

0.44 g (1.76 mmol) of 5-methoxy-4-methyl-2-phenoxycarbonyl-2,4-dihydro-3H-1,2,4-triazol-3-one are dissolved in 40 ml of acetonitrile and at room temperature (about 20 ° C), added in portions to 0.45 g (1.93 mmol) of 2,5-dimethyl-4-methoxycarbonyl-furan-3-sulfonamide and then 0.29 g ( 1.93 mmol) of 1,8-diazabicyclo- [5,4,0] -undec-7-ene (DBU). The reaction mixture is stirred for 12 hours at room temperature and then concentrated under low pressure. The residue is taken up in 100 ml of methylene chloride, washed twice with 5% hydrochloric acid and once with water. The organic phase is dried over sodium sulfate and filtered. The filtrate is concentrated under water jet vacuum and the remaining residue is crystallized from isopropanol. The resulting colorless solid is aspirated, 10

post-washed with diethyl ether and air dried. 0.45 g (66% of theory) of 4 - [[[[(3-methoxy-4,5-dihydro-4-methyl-5-oxo-1H-1] acid methyl ester] is obtained. 2,4-triazol-1-yl) carbonyl] amino] sulfonyl] -2,5-dimethyl-furan-3-carboxylic (allyl, 5-methoxy-4-methyl-2 - [(4- methoxycarbonyl-2,5-dimethyl-3-furyl) sulfonyl-aminocarbonyl] -2,4-dihydro-3H-1,2,4-triazol-3-one) (compound with example number (IA-1) - from the melting point of 205 ° C.

In a manner analogous to example 1 and correspondingly to the general description of the preparation processes according to the invention, the compounds of formula (I) - or formulas (IA) may also be prepared, for example. a (IE) listed in table 1 below.

the XjL *

Y- / hT ij

'so ° V

rj

CT ^ R *

(IA)

Example 1a for compounds of formula (IA) Example No. 1 Q 2 Q R 2 R 5 R 6 R 7 I melting point (0C) (IA-2) O (CH 2 CH 2) OCH 3 156 (IA-3 O O CH3 CH3 CH3 OC2H5 OCH3 195 (IA-4) O CH3 CH3 CH3 OC3H7-n OCH3 187 (IA-5) O CH3 CH3 CH3 OC3H7-I OCH3 184 (IA-6) O CH3 CH3 A OCH3 OCH3 189 ( IA-7) O CH3 CH3 OC3H7-n OCH3 144 example n0 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-8) O CH3 CH3 Λ OC3H7-I OCH3 156 (IA-9) O O CH3 CH3 OCH2CF3 OCH3 158 (IA-10) O O CH3 H CH3 OCH3 OCH3 (IA-11) O O CH3 H CH3 OC2H5 OCH3 (IA-12) O O CH3 H CH3 OC3H7-n OCH3 (IA-13) O O CH3 H CH3 OC3H7-I OCH3 (IA-14) O O CH3 H Λ OCH3 OCH3 (IA-15) O O CH3 H OC2H5 OCH3 (IA-16) O O CH3 H ^ A OC3H7-n OCH3 (IA- 17) O O CH3 H Λ OC3H7-I OCH3 (IA-18) O O CH3 H CH3 OCH3 OC2H5 (IA-19) O O CH3 H CH3 OCH3 OC3H7-n (IA-20) O O CH3 H CH3 OCH3 OC3H7- I (IA-21) O C2H5 H CH3 OCH3 OCH3 (IA-22) O O C2H5 H CH3 OCH3 OC2H5 (IA-23) O C2H5 H CH3 OCH3 OC3H7-n (IA-24) O C2H5 H CH3 OCH3 OC3H7-I (IA-25) O C2H5 H CH3 OC2H5 OCH3 (IA-26) O O C2H5 H CH3 OC2H5 OC2H5 (IA-27) O C2H5 H CH3 OC2H5 OC3H7-n (IA-28) O C2H5 H CH3 OC2H5 OC3H7 -I (IA-29) O C2H5 H CH3 OC3H7-n OCH3 Example n0 1 Q Q2 R2 R5 R6 R7 I Melting Point (0C) (IA-30) O O C2H5 H CH3 OC3H7 -II OC2H5 (IA-31 ) O O C2H5 H CH3 OC3H7-Ii OC3H7-Ii (IA-32) O O C2H5 H CH3 OC3H7-Ii OC3H7-I (IA-33) O C2H6 H CH3 OC3H7-I OCH3 (IA-34) O O C2H5 H CH3 OC3H7-I OC2H5 (IA-35) O C2H5 H CH3 OC3H7-I OC3H7-n (IA-36) O C2H5 H CH3 OC3H7-I OC3H7-I (IA-37) O C2H5 H ^ OCH3 OCH3 (IA-38) O C2H5 H OCH3 OC2H5 (IA-39) O C2H5 H OCH3 OC3H7-n (IA-40) O C2H5 H A OCH3 OC3H7-I (IA-41) O O C2H5 H Λ OC2H5 OCH3 (IA-42) O C2H5 H / A OC2H5 OC2H5 (IA-43) O C2H5 H Λ OC2H5 OC3H7-n (IA-44) O C2H5 H OC2H5 OC3H7-I (IA-45) O C2H5 H Λ OC3H7-n OCH3 example n0 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-46) O O C2H5 H OC3H7-n OC2H5 (IA-47) O O C2H5 H OC3H7-n OC3H7-n ( IA-48) O O C2H5 H A OC3H7-n OC3H7-I (IA-49) O C2H5 H Λ OC3H7-I OCH3 (IA-50) O C2H5 H A OC3H7-I OC2H5 (IA-51) O C2H5 H Λ OC3H7-n (IA-52) O O C2H5H OC3H7-I OC3H7-I (IA-53) O O C3H7-IH CH3 OCH3 OCH3 (IA-54) O C3H7 -HI CH3 OCH3 OC2H5 (IA-55) O O C3H7-n H CH3 OCH3 OC3H7-n (IA-56) O C3H7-n H CH3 OCH3 OC3H7-I (IA-57) O C3H7-n H CH3 OC2H5 OCH3 (IA-58) O C3H7-n H CH3 OC2H5 OC2H5 (IA- 59) O C3H7-H CH3 OC2H5 OC3H7-n (IA-60) O C3H7-n H CH3 OC2H5 OC3H7-I (IA-61) O C3H7-n H CH3 OC3H7-n OCH3 (IA-62) O O C3H7-H CH3 OC3H7-n OC2H5 (IA-63) O O C3H7-n H CH3 OC3H7-n OC3H7-n (IA-64) O C3H7-n H CH3 OC3H7-n OC3H7-I (IA- 65) O C3H7-n H CH3 OC3H7-I OCH3 example n0 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-66) O C3H7-n H CH3 OC3Hyi OC2H5 O O C3H7-n H CH3 OC3Hyi OC3Hyn (IA-68) O C3H7-n H CH3 OC3Hyi OC3Hyi (IA-69) O C3H7-n H OCH3 OCH3 (IA-70) O C3H7-n H Λ OCH3 OC2H5 (IA-71) O C3Hyn H OCH3 OC3Hyn (IA-72) O C3Hyn H OCH3 OC3Hyi (IA-73) O C3Hyn H O C2H5 OCH3 (IA-74) O C3Hyn H Λ OC2H5 OC2H5 (IA-75) O C3Hyn H OC2H5 OC3Hyn (IA-76) O C3Hyn H OC2H5 OC3Hyi (IA-77) O C3Hyn H OC3H7-n OCH3 ( IA-78) O O C3H7-nH OC3Hyn OC2H5 (IA-79) O O C3Hyn H OC3Hyn OC3Hyn example n0 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-80) O O C3H7-II H A OC3H7-n OC3H7-I (IA-81) O C3Hrn H A OC3H7-I OCH3 (IA-82) O C3H7-n H OC3H7-I OC2H5 (IA-83) O O C3H7-n H OC3H7- I OC3H7-n (IA-84) O C3H7-n H OC3H7-I OC3H7-I (IA-85) O C3H7-I H CH3 OCH3 OCH3 (IA-86) O C3H7-I H CH3 OCH3 OC2H5 ( IA-87) O C3H7-I H CH3 OCH3 OC3H7-n (IA-88) O C3H7-IH CH3 OCH3 OC3H7-I (IA-89) O C3H7-IH CH3 OC2H5 OCH3 (IA-90) O C3H7-I H CH3 OC2H5 OC2H5 (IA-91) O C3H7-IH CH3 OC2H5 OC3H7-n (IA-92) O C3H7-I H CH3 OC2H5 OC3H7-I (IA-93) O O C3H7- IH CH3 OC3H7-I OCH3 (IA-94) O C3H7-IH CH3 OC3H7-n OC2H5 (IA-95) O C3H7-IH CH3 OC3H7-n (IA-96) O C3H7- IH CH3 OC3H7-n OC3H7-I (IA-97) O C3H7-I H CH3 OC3H7-I OCH3 (IA-98) O C3H 7-I H CH3 OC3H7-I OC2H5 (IA-99) O C3H7-IH CH3 OC3H7-I OC3H7-n (IA-100) O C3H7-IH CH3 OC3H7-I OC3H7-I (IA-101) O o C3H7-I H OCH3 OCH3 example n0 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-102) O O C3H7-I H OCH3 OC2H5 (IA-103) O O C3H7-I H A OCH3 OC3H7-n (IA-104) O O C3H7-I H O OCH3 OC3H7-I (IA-105) O O C3H7-I H OC2H5 OCH3 (IA-106) O O C3H7-I H Λ OC2H5 OC2H5 ( IA-107) O C3H7-I H Λ OC2H5 OC3H7-n (IA-108) O C3H7-I H OC2H5 OC3H7-I (IA-109) O C3H7-I H A OC3H7-n OCH3 (IA-110) ) O O C3H7-I H Λ OC3H7-n OC2H5 (IA-111) O O C3H7-I H OC3Hrn OC3H7-n (IA-112) O C3H7-I H Ά OC3H7-n OC3H7-I (IA-113) O O C3H7-I H OC3H7-I OCH3 Example # 1 Q 2 Q R2 R5 R6 R7 I Melting Point (0C) (IA-114) O O C3H7-I H OC3H7-I OC2H5 (IA-115) O O C3H7 -I H A OC3H7-I OC3H7-n (IA-116) O O C3H7-I H / Λ OC3H7-I OC3H7-I (IA-117) O CH3 CH3 CH3 OCH3 OC2H5 179 (IA-118) O O CH3 CH3 CH3 OC2H5 OC2H5 166 (IA-119) O CH3 CH3 CH3 CH3 OC3H7-n OC2H5 170 (IA-120) O CH3 CH3 CH3 OC3H 7-I OC2H5 179 (IA-121) O CH3 CH3 CH3 CH3 OCH3 OC3H7-n 141 (IA-122) O CH3 CH3 CH3 OC2H5 OC3H7-Ii 124 (IA-123) O CH3 CH3 CH3 OC3H7-n OC3H7- 134 (IA-124) O CH3 CH3 CH3 CH3 OC3H7-I OC3H7-n 153 (IA-125) O CH3 CH3 CH3 OCH3 OC3H7-I 174 (IA-126) O CH3 CH3 CH3 OC2H5 OC3H7-I 186 ( IA-127) O CH3 CH3 CH3 CH3 OC3H7-n OC3H7-I 152 (IA-128) O CH3 CH3 CH3 CH3 OC3H7-I OC3H7-I 202 (IA-129) O CH3 CH3 OCH3 OC2H5 183 (IA-130) O O CH3 CH3 OC2H5 OC2H5 149 (IA-131) O O CH3 CH3 OC3H7-n OC2H5 125 (IA-132) O O CH3 CH3 OC3H7-I OC2H5 176 Example No. 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-133) O CH3 CH3 CH3 OCH3 OC3H7-n 146 (IA-134) O CH3 CH3 OC2H5 OC3H7-n 142 (IA-135) O CH3 CH3 OC3H7-Pi OC3H7-n 60 (IA -136) O CH3 CH3 CH3 OC3H7-I OC3H7-n 159 (IA-137) O O CH3 CH3 OCH3 OC3H7-I 161 (IA-138) O CH3 CH3 Λ OC2H5 OC3H7-I 163 (IA-139) O CH3 CH3 OC3H7-n OC3H7-I 158 (IA-140) O CH3 CH3 OC3H7-I OC3H7-I 173 (IA-141) O H H CH3 OCH3 OCH3 (IA-142) O O H H CH3 OC2H5 OCH3 ( IA-143) O H H CH3 OC3 Hyn OCH3 (IA-144) O H H CH3 OC3H7-I OCH3 (IA-145) O H H A OCH3 OCH3 (IA-146) OC3H7-n OCH3 example n0 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-148) O O H H OC3H7-I OCH3 (IA-149) O H H CH3 OCH3 OC2H5 (IA-150 ) O O H H CH3 OC2H5 OC2H5 (IA-151) O O H H CH3 OC3H7-IO OC2H5 (IA-152) O O H H CH3 OC3H7-I OC2H5 (IA-153) O O H H OCH3 OC2H5 (IA -154) O H H A OC2H5 OC2H5 (IA-155) O O H H A OC3H7-n OC2H5 (IA-156) O O H H A OC3H7-I OC2H5 (IA-157) O O H H CH3 OCH3 OC3H7 -n (IA-158) OH H CH3 OC2H5 OC3H7-n (IA-159) OH H CH3 OC3H7-n OC3H7-n (IA-160) OH H CH3 OC3H7-I OC3H7-n (IA -161) O H H O OCH3 OC3H7-Ii (IA-162) O O H H OC2H5 OC3H7-n (IA-163) O O H H Λ OC3H7-n OC3H7-n (IA-164) O O H H OC3H7-I OC3H7-n (IA-165) Example n0 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-166) O3 H2 CH3 OC2H5 OC3H7- I (IA-167) O (H-CH3 OC3H7-n OC3H7-I (IA-168) O-H H CH3 OC3H7-I OC3H7-I (IA- 169) O H H Λ OCH3 OC3H7-I (IA-170) O O H H Λ OC2H5 OC3H7-I (IA-171) O O H H OC3H7-n OC3H7-I (IA-172) O H H OC3H7 -I OC3H7-I (IA-173) O CH3 H CH3 OC2H5 OC2H5 (IA-174) O CH3 H CH3 OC3H7-n OC2H5 (IA-175) O CH3 H CH3 OC3H7-I OC2H5 (IA-176) O O CH3 H OCH3 OC2H5 (IA-177) O O CH3 H OC2H5 OC2H5 (IA-178) O O CH3 H OC3H7-n OC2H5 (IA-179) O O CH3 H -A OC3H7-I OC2H5 (IA-180) O CH3 H CH3 OC2H5 OC3H7-II (IA-181) O O CH3 H CH3 OC3H7-n OC3H7-n (IA-182) O CH3 H CH3 OC3H7-I 'OC3H7-II (IA-183) O CH3 H OCH3 OC3H7-n Example n0 1 Q 2 Q R2 R5 R6 R7 I Melting point (0C) (I A-184) O O CH3 H OC2H5 OC3H7-n (IA-185) O O CH3 H OC3H7-n OC3H7- n (IA-186) O O CH3 H OC3H7-I OC3H7-n (IA-187) O O CH3 H CH3 OC2H5 OC3H7-I (IA-188) O O CH3 H CH3 OC3H7-n OC3H7-I (IA-189 ) O O CH3 H CH3 OC3H7-I OC3H7-I (IA-190) O O CH3 H A OCH3 OC3H7-I (IA-191) O O CH3 H A OC2H5 OC3H7-I (IA-192) O O CH3 H A OC3H7-n OC3H7-I (IA-193) O CH3 H / A OC3H7-I OC3H7-I (IA-194) O CH3 H CH3 SC H3 OCH3 (IA-195) CH3 H SCH3 OCH3 (IA-196) CH3 H CH3 SC2H5 OCH3 (IA-197) CH3 H SC2H5 OCH3 (IA-198) CH3 H CH3 N (CH3) 2 OCH 3 (IA-199) O CH 3 H N (CH 3) 2 OCH 3 example n0 1 Q 2 Q R 2 R 5 R 6 R 7 I melting point (0C) (IA-200) O CH 3 H CH 3 CH 3 OCH 3 (IA-201 ) O O CH3 H CH3 OCH3 (IA-202) O O CH3 H CH3 C2H5 OCH3 (IA-203) O O CH3 H C2H5 OCH3 (IA-204) O O CH3 H CH3 OCH3 (IA-205) O O CH3 H A OCH3 (IA-206) O O CH3 H CH3 CH2OCH3 OCH3 (IA-207) O O CH3 H CH2 OCH3 OCH3 (IA-208) O O CH3 H CH3 Cl OCH3 (IA-209) O O CH3 H Cl OCH3 (IA -210) O O CH3 H CH3 Br OCH3 (IA-211) O O CH3 H / A Br OCH3 (IA-212) O O CH3 H OCH3 OCH3 OCH3 (IA-213) O O CH3 H OCH3 OC2H5 OCH3 (IA- 214) O O CH3 H OC2H5 OCH3 OCH3 (IA-215) O O CH3 H OC2H5 OC2H5 OCH3 (IA-216) O O CH3 H OCH3 C3H7-n OCH3 (IA-217) O O CH3 H OC2H5 C2H5 OCH3 (IA- 218) O O C4Hg-I CH3 CH3 OCH3 OC2H5 146 (IA-219) O O C4H9 -CH3 CH3 OC3H7-I OC2H5 165 example n0 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-220 ) O O C 4H9-CH3 OCH3 OC2H5 121 (IA-221) O C4H9-CH3 A OC2H5 OC2H5 151 (IA-222) O C4H9-CH3 OC3H7-n OC2H5 138 (IA-223) O C4H9-CH3 CH3 OCH2CF3 OC2H5 142 (IA-224 O C4H9-CH3 Λ OCH2CF3 OC2H5 145 (IA-225) O C4H9-CH3 CH2 OC2H5 OC2H5 163 (IA-226) O CH3 CH3 CH3 OCH2CF3 OC3H7-I 138 (IA-228) O (CH-CH3 CH3) OCH2CF3 OC3H7-I 144 (IA-228) O CH3 CH3 OCH2CF3 OC2H5 132 (IA-229) O C4Hg-1 CH3 CH3 OC3H7-n OC2H5 143 (IA-230) O O C4H9- CH3 OC3H7-I OC2H5 129 (IA-231) O CH3 C3H7 -n CH3 OCH3 OC2H5 126 (IA-232) O CH3 C3H7 -n CH3 OC2H5 OC2H5 102 (IA-233) O CH3 C3H7 -n CH3 OC3H7 -n OC2H5 96 (IA-234) O n CH3 C3H7 -n CH3 OC3H7-I OC2H5 114 example n0 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-235) O CH3 C3H7 -n OCH3 OC2H5 122 (IA-236) O CH3 C3H7 -n OC2H5 OC2H5 191 (IA-237) O CH3 C3H7 -n Λ OC3H7-n OC2H5 195 (IA-238) O CH3 C3H7 -n A OC3H7-I OC2H5 246 (IA-239) CH3 C3H7 -n CH3 OCH2CF3 OC2H5 138 (IA-240) CH3 C3H7 -n OCH2CF3 OC2H5 144 (IA-241) CH3 C3H7 - n ^ A OC2H5 133 (IA-242) O CH3 C3H7 -n C2H5 OCH3 OC2H5 115 (IA-243) O CH3 C3H7 -n Λ CH2OCH3 OC2H5 193 (IA-244) O C3H7-I CH3 CH3 OCH3 OCH3 177 (IA-245) O O C3H7-I CH3 CH3 OC2H5 OCH3 170 (IA-246) O O C3H7-I CH3 CH3 OC3H7-I OCH3 180 (IA-247) O CH3H7 -i CH3 A OCH2CF3 OCH3 161 (IA- 248) Example n0 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-249) O C3H7-I CH3 CH2OCH3 OCH3 167 (IA-250) O O C3H7- I CH3 CH3 OC3H7-n OCH3 134 (IA-251) O C3H7-I CH3 A OCH3 OCH3 171 (IA-252) O C3H7-I CH3 A OC2H5 OCH3 166 (IA-253) O O C3H7-I CH3 A OC3H7-n OCH3 140 (IA-254) O C3H7-I CH3 A OC3H7-I OCH3 143 (IA-255) O C3H7-I CH3 CH3 OCH2CF3 OCH3 265 (IA-256) O C3H7-I CH3 C2H5 OCH3 OCH3 155 (IA-257) O CH3 CH3 CH3 CH3 OCH2CF3 OC3H7-n 153 (IA-258) O CH3 CH3 A OCH2CF3 OC3H7-H 145 (IA259) O CH3 CH3 A OC3H7-Pi 156 (IA-260) O CH3 CH3 C2H5 OCH3 OC3H7-n 142 (IA-261) O CH3 CH3 CH2OCF3 OC3H7-n 129 (IA-262) O C3H7-n CH3 CH3 OCH3 OCH3 131 (IA-263) O O C3H7-n CH3 CH3 OC 2H5 OCH3 142 (IA-264) O C3H7-n CH3 CH3 OC3H7-n OCH3 132 (IA-265) O C3H7-n CH3 CH3 OC3H7-I OCH3 187 (IA-266) O C3H7-n CH3 OCH3 OCH3 123 example no. 1 Q 2 Q R2 R5 R6 R7 I melting point (0C) (IA-267) O O C3H7-n CH3 Λ OC2H5 OCH3 151 (IA-268) O O C3H7 -II CH3 Λ OC3H7-n OCH3 129 (IA-269) O C3H7-n CH3 OC3H7-I OCH3 145 (IA-270) O O C3H7-n CH3 Λ OCH2CF3 OCH3 144 (IA-271) O C3H7-II CH3 A OCH3 154 (IA-277 ) O O C 3 H 7 -I CH 3 CH 2 OCH 3 OCH 3 136 (IA-278)

(IB)

Table 1b: Examples for the compounds of formula (IB)

example

(IB-I) (IB-2) CB-3)

Q_ O

_Q_ O

THE

CH3 CH3

CH3

CH3 CH3

CH,

CH3 CH3

CH3

R7

OCH3

OC2H5 OC3H7-II

OCH3 OCH3

OCH3

point of

melting (° C)

(IB-4)

THE

CH3

CH3

CH3

OC3H7-I

OCH3 example n0 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IB-5) O O CH3 CH3 Λ OCH3 OCH3 (IB-G) O O CH3 CH3 A OC2H5 OCH3 (IB-7) O O CH3 CH3 Λ OC3H7-I OCH3 (IB-8) O CH3 CH3 CH OC3H7-I OCH3 (IB-9) O CH3 CH3 CH2CF3 OCH3 (IB-10) O CH3 H CH3 OCH3 OCH3 (IB- 11) O CH3 H CH3 OC2H5 OCH3 (IB-12) O CH3 H CH3 OC3H7-n OCH3 (IB-13) O CH3 H CH3 OC3H7-I OCH3 (IB-14) O CH3 H ^ OCH3 OCH3 ( IB-15) O CH3 H A OC2H5 OCH3 (IB-16) O O CH3 H OC3H7-n OCH3 (IB-17) O CH3 H OC3H7-I OCH3 (IB-18) O CH3 H CH3 OCH3 OC2H5 ( IB-19) O CH3 H CH3 OCH3 OC3H7-n (IB-20) O O CH3 H CH3 OCH3 OC3H7-I (IB-21) O C2H5 H CH3 OCH3 OCH3 (IB-22) O C2H5 H CH3 OCH3 OC2H5 Example n0 1 Q 2 Q R4 R5 R6 R7 I Melting Point (0C) (IB-23) O O C2H5 H CH3 OCH3 OC3H7-n (IB-24) O C2H5 H CH3 OCH3 OC3H7-I (IB-25) ) O O C2H5 H CH3 OC2H5 OCH3 (IB-26) O O C2H5 H CH3 OC2H5 OC2H5 (IB-27) O C2H5 H CH3 OC2H5 OC3H7-n (IB-28) O O C2H5 H CH3 OC2H5 OC3H7-I (IB -29) O O C2H5H CH3 OC3H7-n OCH 3 (IB-30) O C2H5 H CH3 OC3H7-n OC2H5 (IB-31) O C2H5 H CH3 OC3H7-Ii OC3H7-n (IB-32) O C2H5 H CH3 OC3H7-n OC3H7-I (IB- 33) O O C2H5 H CH3 OC3H7-I OCH3 (IB-34) O O C2H5 H CH3 OC3H7-I OC2H5 (IB-35) O C2H5 H CH3 OC3H7-I (IB-36) O O C2H5 H CH3 OC3H7-I OC3H7-I (IB-37) O C2H5 H A OCH3 OCH3 (IB-38) O C2H5 H OCH3 OC2H5 (IB-39) O C2H5 H OCH3 OC3H7-II (IB-40) O O C2H5 H A OCH3 OC3H7-I (IB-41) O C2H5 H / A OC2H5 OCH3 (IB-42) O O C2H5 H OC2H5 OC2H5 Example # 1 Q 2 Q R4 R5 R6 R7 I Melting Point (0C) (IB -43) O C2H5 H OC2H5 OC3H7-n (IB-44) O O C2H5 H OC2H5 OC3H7-I (IB-45) O C2H5 H / Λ OC3H7-n OCH3 (IB-46) O C2H5 H OC3H7- n OC2H5 (IB-47) O C2H5 H A OC3H7-n OC3H7-II (IB-48) O O C2H5 H A OC3H7-n OC3H7-I (IB-49) O C2H5 H OC3H7-I OCH3 (IB- 50) O O C2H5 H A OC3H7-I OC2H5 (IB-51) O O C2H5 H OC3H7-I OC3H7-n (IB-52) O C2H5 H A OC3H7-I OC3H7-I (IB-53) O C3H7 CH 3 OCH 3 OCH 3 (IB-54) O C 3 H 7 -I H CH 3 OCH 3 OC 2 H 5 (IB-55) H3 OCH3 OC3H7-n (IB-56) O C3H7-n H CH3 OCH3 OC3H7-I (IB-57) O C3H7-n H CH3 OC2H5 OCH3 (IB-58) O C3H7-n H CH3 OC2H5 OC2H5 n0 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IB-59) O O C3H7-IH CH3 OC2H5 OC3H7-n (IB-60) O C3H7 -HI CH3 OC2H5 OC3H7-I (IB -61) O C3H7-n H CH3 OC3H7-n OCH3 (IB-62) O C3H7-IH CH3 OC3H7-n OC2H5 (IB-63) O C3H7-IH CH3 OC3Hrn OC3H7-n (IB-64) ) O O C3H7-n H CH3 OC3H7-n OC3H7-I (IB-65) O O C3H7-IH CH3 OC3H7-I OCH3 (IB-66) O C3H7-nH CH3 OC3H7-I OC2H5 (IB-67 ) O O C3H7-n H CH3 OC3H7-I OC3H7-n (IB-68) O O C3H7-n H CH3 OC3H7-I OC3H7-I (IB-69) O C3H7-n H A OCH3 OCH3 (IB-70) ) O O C3H7-n H A OCH3 OC2H5 (IB-71) O O C3H7-n H OCH3 OC3H7-n (IB-72) O C3H7-n H OCH3 OC3H7-I (IB-73) O O C3H7-n H OC2H5 OCH3 (IB-74) O C3H7-n H OC2H5 OC2H5 (IB-75) O C3H7-n H A OC2H5 OC3H7-n (IB-76) O C3H7-nH A OC2H5 OC3H7-I Example n0 1 Q 2 Q R 4 R 5 R 6 R 7 I melting point (0C) (IB-77) O O C 3 H 7 -I H H OC 3 H 7 -n OCH 3 (IB-78) O O C 3 H7-Ii H A OC3H7-n OC2H5 (IB-79) O C3H7-IIH OC3H7-n OC3H7-n (IB-80) O C3H7-n H Λ OC3H7-n OC3H7-I (IB-81) O O C3H7-n H OC3H7-I OCH3 (IB-82) O C3H7-IH A OC3H7-I OC2H5 (IB-83) O C3H7-n H A OC3H7-I OC3Hyn (IB-84) O C3H7- IH H A OC3H7-I OC3H7-I (IB-85) O C3H7-I H CH3 OCH3 OCH3 (IB-86) O C3H7-I H CH3 OCH3 OC2H5 (IB-87) O C3H7-I H CH3 OCH3 OC3H7-n (IB-88) O C3H7-I H CH3 OCH3 OC3H7-I (IB-89) O C3H7-I H CH3 OC2H5 OCH3 (IB-90) O C3H7-I H CH3 OC2H5 OC2H5 (IB- 91) O C3H7-H CH3 OC2H5 OC3H7-n (IB-92) O C3H7-H CH3 OC2H5 OC3H7-I (IB-93) O C3H7-H CH3 OC3H7-n OCH3 (IB-94) O O C3H7-IH CH3 OC3H7-n OC2H5 (IB-95) O O C3H7-IH CH3 OC3H7 -n OC3H7-n Example n0 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IB-96 ) O C3H7-IH CH3 OC3H7-n OC3H7-I (IB-97) O C3H7-IH CH3 OC3H7-I OCH3 (IB-98) O C3H7-IH CH3 OC3H7-I OC2H5 (IB-99) ) O O C3H7-I H CH3 OC3H7-I OC3H7-n (IB-100) O O C3H7-I H CH3 OC3H7-I OC3H7-I (IB-101) O C3H7-I H OCH3 OCH3 (IB-102) ) THE C3H7-IH OCH3 OC2H5 (IB-103) O C3H7-IH OCH3 OC3H7-n (IB-104) O C3H7-! H Λ OCH3 OC3H7-I (IB-105) O C3H7-I H OC2H5 OCH3 (IB-106) O O C3H7-IH2OC2H5 OC2H5 (IB-107) O O C3H7-IH OC2H5 OC3Hrn (IB-108) ) O O C3H7-IH OC2H5 OC3Hri (IB-109) O O C3H7-IH OC3H7-n OCH3 (IB-110) O C3H7-IH OC3H7-n OC2H5 Example # 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IB-111) O C3H7-I H OC3H7-II OC3H7-n (IB-112) O C3H7-I H OC3H7-n OC3H7-I (IB-113) O O C3H7 -I H Λ OC3H7-I OCH3 (IB-114) O C3H7-I H OC3H7-I OC2H5 (IB-115) O C3H7-I H OC3H7-I OC3H7-n (IB-116) O O C3H7-I H A OC3H7-I OC3H7-I (IB-117) O CH3 CH3 CH3 OCH3 OC2H5 (IB-118) O CH3 CH3 CH3 OC2H5 OC2H5 (IB-119) O CH3 CH3 CH3 OC3H7-n OC2H5 (IB-120 ) O O CH3 CH3 CH3 OC3H7-I OC2H5 (IB-121) O O CH3 CH3 CH3 OCH3 OC3H7-n (IB-122) O CH3 CH3 CH3 OC2H5 OC3H7-n (IB-123) O O CH3 CH3 CH3 OC3H7- n OC3Hrn (IB-124) O CH3 CH3 CH3 CH3 OC3H7-I OC3H7-n (IB-125) O CH3 CH3 CH3 OCH3 OC3Hri (IB-126) O CH3 CH3 CH3 OC2H5 OC3H7-I (IB-127) O CH3 CH3 CH3 OC3H7-n OC3H7-I (IB-128) O CH3 CH3 CH3 OC3H7-I OC3H7-I (IB-129) Example N0 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IB-130) CH3 CH3 A OC2H5 OC2H5 (IB- 131) O CH3 CH3 / A OC3H7-n OC2H5 (IB-132) O CH3 CH3 A OC3H7-I OC2H5 (IB-133) O CH3 CH3 OCH3 OC3H7-n (IB-134) O CH3 CH3 A OC2H5 OC3H7-n (IB-135) O CH3 CH3 CH3 OC3H7-n OC3H7-II (IB-136) O CH3 CH3 OC3H7-I OC3H7-II (IB-137) O CH3 CH3 OCH3 OC3H7-I (IB-138) ) O O CH3 CH3 OC2H5 OC3H7-I (IB-139) O O CH3 CH3 OC3H7-n OC3H7-I (IB-140) O CH3 CH3 OC3H7-I OC3H7-I (IB-141) O O H H CH3 OCH3 OCH3 (IB-142) OCH3OC2H5 OCH3 (IB-143) OCH3OC3H7-n OCH3 (IB-144) OCH3OC3H7-I OCH3 Example n0 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IB-145) O O H H O OCH3 OCH3 (IB-146) O O H H O OC2H5 OCH3 (IB-147) O O H H OC3H7-I OCH3 (IB-148 ) O O H H OC3H7-I OCH3 (IB-149) O O H H CH3 OCH3 OC2H5 (IB-150) O O H H CH3 OC2H5 OC2H5 (IB-151) O O H H CH3 OC3H7-n OC2H5 (IB- 152) O O H H CH3 OC3H7-I OC2H5 (IB-1 53) O H H OCH3 OC2H5 (IB-154) O O H H / Δ OC2H5 OC2H5 (IB-155) O O H H A OC3H7-n OC2H5 (IB-156) O H H A OC3H7-I OC2H5 ( IB-157) O H H CH3 OCH3 OC3H7-n (IB-158) O O H H CH3 OC2H5 OC3H7-II (IB-159) O H H CH3 OC3H7-n OC3H7-n (IB-160) O O H H CH3 OC3H7-I OC3H7-n (IB-161) O H H A OCH3 OC3H7-II Example n0 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IB-162) O O H H OC2H5 OC3H7-n (IB-163) O H H Λ OC3H7-n OC3H7-II (IB-164) O O H H OC3H7-I OC3H7-n (IB-165) O H H CH3 OCH3 OC3H7-I (IB -166) O H H CH3 OC2H5 OC3H7-I (IB-167) O O H H CH3 OC3H7-II OC3H7-I (IB-168) O H H CH3 OC3H7-I OC3H7-I (IB-169) O O H H OCH3 OC3H7-I (IB-170) O O H H Λ OC2H5 OC3H7-I (IB-171) O H H Λ OC3H7-n OC3H7-I (IB-172) O O H H OC3H7-I OC3H7 -I (IB-173) O CH3 H CH3 OC2H5 OC2H5 (IB-174) O CH3 H CH3 OC3H7-II OC2Hs (IB-175) O CH3 H CH3 OC3H7-I OC2H5 (IB-176) O CH3 H A OCH3 OC2H5 (IB-177) O O CH3 H OC2H5 OC2H5 Example n0 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IB-178) O CH3 H A OC3H7-II OC2H5 (IB-179) O CH3 H A OC3H7-I OC2H5 (IB-180) O CH3 H CH3 OC2H5 OC3H7-n (IB-181) O O CH3 H CH3 OC3H7-n OC3H7-n (IB-182) O CH3 H CH3 OC3H7-I OC3H7-I (IB-183) O CH3 H J \ OCH3 OC3H7-n (IB-184) O CH3 H OC2H5 OC3H7 -n (IB-185) O CH3 H OC3H7-II OC3H7-n (IB-186) O CH3 H OC3H7-I OC3H7-n (IB-187) O CH3 H CH3 OC2H5 OC3H7-I (IB-188 ) O O CH3 H CH3 OC3H7-I OC3H7-I (IB-189) O O CH3 H CH3 OC3H7-I OC3H7-I (IB-190) O CH3 H A OCH3 OC3H7-I (IB-191) O O CH3 H A OC2H5 OC3H7-I (IB-192) O CH3 H A OC3H7-n OC3H7-I (IB-193) O CH3 H OC3H7-I OC3H7-I Example n0 1 Q 2 Q R4 R5 R6 R7 I melting (0C) (IB-194) O CH3 H CH3 SCH3 OCH3 (IB-195) O CH3 H Λ SCH3 OCH3 (IB-196) O CH3 H CH3 SC2H5 OCH3 (IB-197) O CH3 H SC2H5 OCH3 (IB-198) O O CH3 H CH3 N (CH3) 2 OCH3 (IB-199) O O CH3 H N (CH3) 2 OCH3 (IB-200) O O CH3 H CH3 CH3 OCH3 (IB-201) O CH3 H CH3 OCH3 (IB-202) O CH3 H CH3 C2H5 OCH3 (IB-203) O CH3 H C2H5 OCH3 (IB -204) O CH3 H CH3 OCH3 (IB-205) O O CH3 H Λ OCH3 (IB-206) O CH3 H CH3 CH2OCH3 OCH3 (IB-207) O CH3 H CH2OCH3 OCH3 (IB-208) O O CH3 H CH3 Cl OCH3 (IB-209) O O CH3 H Cl OCH3 example n0 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IB-210) O O CH3 H CH3 Br OCH3 (IB-211) O O CH3 H Br OCH3 (IB-212) O O CH3 H OCH3 OCH3 OCH3 (IB-213) O O CH3 H OCH3 OC2H5 OCH3 (IB-214) O O CH3 H OC2H5 OCH3 OCH3 (IB-215) O O CH3 H OC 2 H 5 OC 2 H 5 OCH 3 (IB-216) O Example CH 3 H OCH 3 C 3 H 7 -I OCH 3 (IB 217) O CH 3 H OC 2 H 5 C 2 H 5 OCH 3 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IC-8) O CH3 CH3 OC3H7-I OCH3 (IC-9) O CH3 H CH3 OCH3 OCH3 (IC-10) O O CH3 H CH3 OC2H5 OCH3 (IC-11) O CH3 H CH3 OC3H7-n OCH3 (IC-12) O CH3 H CH3 OC3H7-I OCH3 (IC-13) O CH3 H OCH3 OCH3 (IC-14) O O CH3 H Λ OC2H5 OCH3 (IC-15) O CH3 H OC3H7-n OCH3 (IC-16) O CH3 H OC3H7-I OCH3 (IC-17) O H CH3 CH3 OCH3 OCH3 (IC-18) O H CH3 CH3 OC2H5 OCH3 (IC-19) O O H CH3 CH3 OC3H7-n OCH3 (IC-20) O O H CH3 CH3 OC3H7-I OCH3 (IC-21) O H CH3 OCH3 OCH3 (IC-22) O O H CH3 OC2H5 OCH3 (IC-23) O O H CH3 Λ OC3H7-n OCH3 (IC-24) O O H CH3 OC3H7-I OCH3 (IC-25) O H H CH3 OCH3 OCH3 Example # 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IC-26) O IC H CH3 OC2H5 OCH3 (IC-27) O IC H CH3 OC3H7-II OCH3 (IC-28) O H H CH3 OC3H7-I OCH3 (IC-29) O O H H OCH3 OCH3 (IC-30) O O H H OC2H5 OCH3 (IC-31) O O H H OC3H7-n OCH3 (IC-32) O O H H OC3H7-I OCH3 (IC -33) O O CH3 CH3 CH3 OCH3 OC2H5 (IC-34) O O CH3 CH3 CH3 OC2H5 OC2H5 ( IC-35) CH3 CH3 CH3 CH3 OC3H7-n OC2H5 (IC-36) CH3 CH3 CH3 OC3H7-I OC2H5 (IC-37) CH3 CH3 OCH3 OC2H5 (IC-38) CH3 CH3 / A OC2H5 OC2H5 (IC-39) O CH3 CH3 OC3H7-n OC2H5 (IC-40) O CH3 CH3 OC3H7-I OC2H5 (IC-41) O CH3 H CH3 OCH3 OC2H5 (IC-42) O CH3 H CHa OC2H5 OC2H5 (IC-43) O CH3 H CH3 OC3H7-n OC2H5 (IC-44) O CH3 H CH3 OC3H7-I OC2H5 Example # 1 Q Q2 R4 R5 R6 R7 I Melting Point (0C) (IC-45 ) O CH3 H OCH3 OC2H5 (IC-46) O CH3 H / / OC2H5 OC2H5 (IC-47) O CH3 H / Λ OC3H7-Ii OC2H5 (IC-48) O CH3 H OC3H7-I OC2H5 (IC -49) H CH3 CH3 CH3 OCH3 OC2H5 (IC-50) H CH3 CH3 CH3 OC2H5 OC2H5 (IC-51) H CH3 CH3 OC3H7-n OC2H5 (IC-52) H CH3 CH3 OC3H7-I OC2H5 (IC-53) H CH3 OCH3 OC2H5 (IC-54) H H CH3 Λ OC2H5 OC2H5 (IC-55) H CH3 OC3H7-Ii OC2H5 (IC-56) H H CH3 Ά OC3H7-I OC2H5 (IC-57) O H H CH3 OCH3 OC2H5 (IC-58) O O H H CH3 OC2H5 OC2H5 (IC-59) O H H CH3 OC3H7-n OC2H5 (IC-60) O H H CH3 OC3H7- I OC2H5 (IC-61) O H H OCH3 OC2H5 example no. 1 Q 2 Q R4 R5 R6 R7 I melting point (0C) (IC-62) O H H A OC2H5 OC2H5 (IC-63) O H H A OC3H7-II OC2H5 (IC-64) O O H H Λ OC3H7-I OC2H5 (IC-65) O CH3 CH3 CH3 OCH3 OC3H7-n (IC-66) O CH3 CH3 CH3 OC2H5 OC3Hrn (IC-67) O CH3 CH3 CH3 OC3H7-Ii OC3H7-n (IC- 68) O O CH3 CH3 CH3 OC3H7-I OC3H7-n (IC-69) O O CH3 CH3 A OCH3 OC3H7-n (IC-70) O O CH3 CH3 OC2H5 OC3H7-n (IC-71) O O CH3 CH3 A OC3H7-n OC3H7-n (IC-72) O CH3 CH3 OC3H7-I OC3H7-n (IC-73) O CH3 H CH3 OCH3 OC3Hrn (IC-74) O CH3 H CH3 OC2H5 OC3H7-n (IC- 75) O O CH3 H CH3 OC3H7-n OC3H7-n (IC-76) O O CH3 H CH3 OC3H7-I OC3Hrn (IC-77) O CH3 H OCH3 OC3Hrn (IC-78) O O CH3 H OC2H5 OC3H7- n example n0. 1 Q 2 Q R 4 R 5 R 6 R 7 I melting point (0C) (IC-79) O CH 3 H OC 3 H 7 -i (IC-80) O CH 3 H OC 3 H 7 -I OC 3 H 7 -n (IC-81) O O H CH3 CH3 OCH3 OC3H7-n (IC-82) O O H CH3 CH3 OC2H5 OC3H7-n (IC-83) O O H CH3 CH3 OC3H7-n OC3H7-n (IC-84) O O H CH3 CH3 OC3H7 -I OC3H7-n (IC-85) O H CH3 A OCH3 OC3H7-n (IC-86) O H CH3 OC2H5 OC3H7-n (IC-87) O H CH3 OC3H7-II OC3H7-n (IC- 88) O H H CH3 OC3H7-I OC3H7-n (IC-89) O H H CH3 OCH3 OC3H7-n (IC-90) O H H CH3 OC2H5 OC3H7-n (IC-91) O H H CH3 OC3H7-n OC3H7-n (IC-92) O H H CH3 OC3H7-I OC3H7-n (IC-93) O H H OCH3 OC3H7-II (IC-94) O H H OC2H5 OC3H7-n (IC -95) O H H OC3H7-n OC3H7-n Example # 1 Q 2 Q R4 R5 R6 R7 I Melting Point (0C) (IC-96) O H H OC3H7-I OC3H7-n (IC-97 ) O O CH3 CH3 CH3 OCH3 OC3H7-I (IC-98) O O CH3 CH3 CH3 OC2H5 OC3H7-I (IC-99) O CH3 CH3 CH3 OC3H7-n OC3H7-I (IC-100) O CH3 CH3 CH3 OC3H7-I OC3H7-I (IC-101) O CH3 CH3 Λ OCH3 OC3H7-I '(IC-102) O CH3 CH3 OC2H5 OC3H7-I (IC-103) O O CH3 C H3 Λ OC3H7-n OC3H7-I (IC-104) O CH3 CH3 OC3H7-I OC3H7-I (IC-105) O CH3 H CH3 OCH3 OC3H7-I (IC-106) O CH3 H CH3 OC2H5 OC3H7- I (IC-107) O CH3 H CH3 OC3H7-n OC3H7-I (IC-108) O CH3 H CH3 OC3H7-I OC3H7-I (IC-109) O CH3 H4 OCH3 OC3H7-I (IC- 110) O CH3 H OC2H5 OC3H7-I (IC-111) O O CH3 H OC3H7-n OC3H7-I (IC-112) O CH3 H4A OC3H7-I OC3H7-I (IC-113) O O H CH3 CH3 OCH3 OC3H7-I example no. 1 Q 2 Q R 4 R 5 R 6 R 7 I melting point (0C) (IC-114) CH 3 CH 3 OC 2 H 5 OC 3 H 7 -I (IC-115) O H CH 3 CH 3 OC 3 H 7 -N OC 3 H 7 -I (IC-116) O H CH3 CH3 OC3H7-I OC3H7-I (IC-117) O H CH3 OCH3 OC3H7-I (IC-118) O H CH3 OC2H5 OC3H7-I (IC-119) O H CH3 OC3H7-Ii OC3H7 -I (IC-120) O H CH3 Λ OC3H7-I OC3H7-I (IC-121) O H H CH3 OCH3 OC3H7-I (IC-122) O H H CH3 OC2H5 OC3H7-I (IC-123 ) O H H CH3 OC3H7-I OC3H7-I (IC-124) O O H H CH3 OC3H7-I OC3H7-I (IC-125) O H H A OCH3 OC3H7-I (IC-126) O O H H OC2H5 OC3H7-I (IC-127) O H H OC3H7-n OC3H7-I (IC-128) O H H OC3H7-I OC3H7-I Starting materials of formula (II): Example (11-1)

H3Cv J HiN ° / 2 ° JrL

(IIA-1))

In a solution of 3.0 g, (11.9 mmols) of 2,5-dimethyl-4-methoxycarbonyl-furan-3-sulfonic acid chloride in 40 ml of methylene chloride, 1.5 g of ammonia gas are introduced. at 0 ° C to 10 ° C. Then the reaction mixture is stirred for 15 hours at room temperature (about 20 ° C) and then filtered. The filtrate is concentrated under low pressure, the resulting solid residue is mixed with petroleum ether and the crystalline product is isolated by aspiration. 2.2 g (79% of theory) of 2,5-dimethyl-4-methoxycarbonyl-furan-3-sulfonamide is obtained as a light beige solid from the melting point of 155 ° C.

In a manner analogous to example (11-1), for example, the following compounds of general formula (II) may also be prepared:

,The

, SOj-NHj (iia)

OK

jela 2a: Examples for the

compounds of formula (IIA)

Example No. R2 R5 I Melting Point (0C) (IIA-2) CH3 CH3 OC2H5 134 (IIA-3) CH3 CH3 OC3H7-n 105 (IIA-4) CH3 CH3 OC3H7-I 103 (IIA-5) C2H5 CH3 OCH3 (IIA-6) C2H5 CH3 OC2H5 (IIA-7) C2H5 CH3 OC3H7-n (IIA-8) C2H5 CH3 OC3H7-I (IIA-9) C3H7-n CH3 OCH3 118 (IIA-10) C3H7-n CH3 OC2H5 Example n0 R2 R5 I melting point (OC) (IIA-11) C3H7-II CH3 OC3H7-n (IIA-12) C3H7-n CH3 OC3H7-I (IIA-13) C3H7-CH3 OCH3 124 (IIA-14) C3H7-CH3 OC2H5 (IIA-15) C3H7-CH3 OC3H7-n (IIA-16) C3H7-CH3 OC3H7-I (IIA-17) CH3 H OCH3 (IIA-18) CH3 H OC2H5 (IIA-19) CH3 H OC3H7 -n (IIA-20) CH3 H OC3H7-I (IIA-21) C2H5 H OCH3 (IIA-22) C2H5 H OC2H5 (IIA-23) C2H5 H OC3H7-n (IIA-24) C2H5 H OC3H7-I (IIA -25) C3H7-n H OCH3 (IIA-26) C3H7-n H OC2H5 (IIA-27) C3H7-n H OC3H7-n (IIA-28) C3H7-n H OC3H7-I (IIA-29) C3H7-H OCH3 (IIA-30) C3H7-H OC2H5 (IIA-31) C3H7-H OC3H7-n (IIA-32) C3H7-H OC3H7-I (IIA-33) H H OCH3 (IIA-34) H H OC2H5 (IIA -35) H H OC3H7-n (IIA-36) H H OC3H7-I (IIA-37) CF3 H OCH3 (IIA-38) CF3 H OC2H5 (IIA-39) CF3 H OC3H7-n (IIA-40) CF3 H OC3H7-I Example n0 R2 R5 I Melting Point (0C) (I IA-41) C4H9-I CH3 OC2H5 67 (IIA-42) CH3 C3H7-n OC2H5 92

(IB) 1a and 2b: Examples for the compounds of formula (IIB): Example No. R4 R5 I melting point (0C) CliB-1) CH3 CH3 OCH3 (IIB-2) CH3 CH3 OC2H5 (IIB-3) CH3 CH3 OC3H7-n (IIB-4) CH3 CH3 OC3H7-I (IIB-5) C2H5 CH3 OCH3 (IIB-6) C2H5 CH3 OC2H5 (IIB-7) C2H5 CH3 OC3H7-n (IIB -S) C2H5 CH3 OC3H7-I (IIB-9) C3H7-n CH3 OCH3 (IIB-10) C3H7-II CH3 OC2H5 (I IB-11) C3H7-n CH3 OC3H7-n (I IB-12) C3H7-n CH3 OC3H7-I (IIB-13) C3H7-I CH3 OCH3 (IIB-14) C3H7-I CH3 OC2H5 (IIB-15) C3H7-I CH3 OC3H7-n (IIB-16) C3H7-I CH3 OC3H7-I (IIB -17) CH3 H OCH3 (IIB-18) CH3 H OC2H5 (I IB-19) CH3 H OC3H7-n (IIB-20) CH3 H OC3H7-I (IIB-21) C2H5 H OCH3 (IIB-22) C2H5 H OC2H5 example n0 R4 R5 I melting point (0C) (IIB-23) C2H5 H OC3H7-n (IIB-24) C2H5 H OC3H7-I (IIB-25) C3H7-n H OCH3 (IIB-26) C3H7-n H OC2H5 (IIB-27) C3H7-II H OC3H7-n (IIB-28) C3H7-IIH OC3H7-I (IIB-29) C3H7-I H OCH3 (IIB-30) C3H7-I H OC2H5 (IIB-31 ) C3H7-I H OC3H7-II (IIB-32) C3H7-I H OC3H7-I (IIB-33) H H OCH3 (IIB-34) H H OC2H5 (IIB-35) H H OC3H7-n (IIB-36) H H OC3H7-I (IIB-37) CF3 H OCH3 (IIB-38) CF3 H OC2H5 (IIB-39 ) CF3 H OC3H7-I (IIB-40) CF3 H OC3H7-I

(ItC)

Example N ° R4 R5 I Melting Point (O C) (MC-1) CH3 CH3 OCH3 (IIC-2) CH3 CH3 OC2H5 (IIC-3) CH3 CH3 OC3H7-n (IIC-4) CH3 CH3 OC3H7-I (IIC -5) C2H5 CH3 OCH3 example n0 R4 R5 I melting point (0C) (IIO-6) C2H5 CH3 OC2H5 (110-7) C2H5 CH3 OC3H7-n (110-8) C2H5 CH3 OC3H7-I (110-9) C3H7-n CH3 OCH3 (110-10) C3H7-II CH3 OC2H5 (IIC-11) C3H7-n CH3 0C3H7-n (110-12) C3H7-II CH3 OC3H7-I (IIC-13) C3H7-I CH3 OCH3 ( IIC-14) C3H7-I CH3 OC2H5 (110-15) C3H7-I CH3 0C3H7-n (IIC-16) C3H7-I CH3 OC3H7-I (110-17) CH3 H OCH3 (110-18) CH3 H OC2H5 ( 110-19) CH3 H OC3H7-n (IIC-20) CH3 H OC3H7-I (110-21) C2H5 H OCH3 (IIC-22) C2H5 H OC2H5 (IIC-23) C2H5 H OC3H7-II (IIC-24) C2H5H OC3H7-I (IIC-25) C3H7 -nH OCH3 (IIC-26) C3H7 -nH OC2H5 (IIC-27) C3H7 -nH OC3H7-n (IIC-28) C3H7 -nH OC3H7-I ( IIC-29) C3H7-H OCH3 (IIC-30) C3H7-H OC2H5 (110-31) C3H7-H OC3H7-n (IIC-32) C3H7-H OC3H7-I (IIC-33) H H OCH3 (IIC- 34) H H OC 2 H 5 (IIC-35) H H OC 3 H 7 -I Example R 4 R5 I melting point (C) (IIC-36) H H OC3H7-! (IIC-37) CF3 H OCH3 (IIC-38) CF3 H OC2H5 (IIC-39) CF3 H OC3H7-n (IIC-40) CF3 H OC3H7-I

Starting materials of formula (V0: Example (VI-1)

Stage 1: 2,5-Dimethyl-furyl-3-carboxylic acid ethyl ester

CjHsO- /

CHi

11.5 g of sodium are previously introduced into 75 ml of anhydrous dioxane under argon. A solution of 71.5 g (0.55 mol) of acetacetic acid ethyl ester in 75 ml of anhydrous dioxane is added dropwise within 30 minutes. Upon completion of gas release, the solution is heated to 50 - 60 ° C and 68.5 g (0.5 mol) bromacetone is added by dripping. It is then heated at 90 - 95 ° C for 5 hours. After cooling, the formed sodium bromide is filtered, the solution is centrifuged in vacuo and the residue is distilled. The boiling point fraction of 88 - 95 ° C / 0.1 kPa (1 mbar) is dissolved in 100 ml of toluene, added to 0.3 ml of perchloric acid and heated to reflux in the water separator. Upon completion of water formation, the solution is vacuum distilled. 67.2 g (0.4 mol) of 2,5-dimethyl-furyl-3-carboxylic acid ethyl ester are isolated. Boiling point 99-101 ° C / 1.4 kPa (14 mbar). 10

Stage 2: 2,5-Dimethyl-4-ethoxycarbonyl-3-chlorosulfonyl-furan

,The

Η, ο ^ α

C2H8O -— &

\ SO2-Ct

· * - <Χ

15.12 g (0.09 mol) of 2,5-dimethyl-furyl-3-carboxylic acid ethyl ester are dissolved in 30 ml of chloroform and added to 11.1 g (0.096 mol) of freshly distilled chlorosulfonic acid. Heat for one hour at 65 ° C, cool to room temperature and with intense stirring add to phosphorus pentachloride (22.6 g, 0.108 mol) portionwise. Then 30 ml of orthoxylene are added and at normal pressure chloroform, phosphorus oxychloride and xylene are distilled off. The residue is vacuum distilled. 2,5-Dimethyl-4-ethoxycarbonyl-3-chlorosulfonyl-furan is obtained as colorless oil. Yield: 11.1 g (52% of theory), boiling point 118-119 ° C / 0.1 kPa (1 mbar).

Similarly to example (VI-1), the following compounds of general formula (VI) may also be prepared, for example:

The

y ~~ ν

so — α

Rz

(VIA)

Table 3a: Examples

for the compounds of the formula

Example No. R2 R5 I Melting Point (cC) (VIA-2) CH3 CH3 OC2H5 (VIA-3) CH3 CH3 OC3H7-n (VIA-4) CH3 CH3 OC3H7-I (VIA-5) C2H5 CH3 OCH3 (VIA -6) C2H5 CH3 OC2H5 (VIA-7) C2H5 CH3 OC3H7-n (VIA-8) C2H5 CH3 OC3H7-I (VIA-9) C3H7-n CH3 OCH3 (VIA-10) C3H7-n CH3 OC2H5

VIAL example n0 R2 R5 I melting point (0C) (VIA-11) C3H7-n CH3 OC3H7-n (VIA-12) C3H7-n CH3 OC3H7-I (VIA-13) C3H7-CH3 OCH3 (VIA-14) C3H7-CH3 OC2H5 (VIA-15) C3H7-CH3 OC3H7-n (VIA-16) C3H7-CH3 OC3H7-I (VIA-17) CH3 H OCH3 (VIA-18) CH3 H OC2H5 (VIA-19) CH3 H OC3H7 -n (VIA-20) CH3 H OC3H7-I (VIA-21) C2H5 H OCH3 (VIA-22) C2H5 H OC2H5 (VIA-23) C2H5 H OC3H7-n (VIA-24) C2H5 H OC3H7-I (VIA -25) C3H7-n H OCH3 (VIA-26) C3H7-IIH OC2H5 (VIA-27) C3H7-IIH OC3H7-n (VIA-28) C3H7-nH OC3H7-I (VIA-29) C3H7-H OCH3 (VIA-30) C3H7-H OC2H5 (VIA-31) C3H7-H OC3H7-n (VIA-32) C3H7-H OC3H7-I (VIA-33) H H OCH3 (VIA-34) H H OC2H5 (VIA -35) H H OC3H7-n (VIA-36) H H OC3H7-I (VIA-37) CF3 H OCH3 (VIA-38) CF3 H OC2H5 (VIA-39) CF3 H OC3H7-n (VIA-40) CF3 H OC3H7-I y

Table 3b: Examples for compounds of formula (VIB)

example nr R4 R5 I melting point (C) (VIB-1) CH3 CH3 OCH3 (VIB-2) CH3 CH3 OC2H5 (VIB-3) CH3 CH3 OC3H7-n (VIB-4) CH3 CH3 OC3H7-I (VIB -5) C2H5 CH3 OCH3 (VIB-6) C2H5 CH3 OC2H5 (VIB-7) C2H5 CH3 OC3H7-n (VIB-8) C2H5 CH3 OC3H7-I (VIB-9) C3H7-n CH3 OCH3 (VIB-10) C3H7 CHI OC3H7 (VIB-11) C3H7-II CH3 OC3H7-n (VIB-12) C3H7-n CH3 OC3H7-I (VIB-13) C3H7-I CH3 OCH3 (VIB-14) C3H7-I CH3 OC2H5 (VIB -15) C3H7-I CH3 OC3H7-n (VIB-16) C3H7-I CH3 OC3H7-I (VIB-17) CH3 H OCH3 (VIB-18) CH3 H OC2H5 (VIB-19) CH3 H OC3H7-n (VIB -20) CH3 H OC3H7-I (VIB-21) C2H5 H OCH3 (VIB-22) C2H5 H OC2H5 (VIB-23) C2H5 H OC3H7-n (VIB-24) C2H5 H OC3H7-I (VIB-25) C3H7 -n H OCH3 example R4 R5 I melting point (C) (VIB-26) C3H7-IIH OC2H5 (VIB-27) C3H7-IIH OC3H7-n (VIB-28) C3H7-IIH OC3H7-I (VIB-29) C3H7-IH OCH3 (VIB-30) C3H7-IH OC2H5 (VIB-31) C3H7-IH OC3H7-n (VIB-32) C3H7-IH OC3H7-I (VIB-33) H H OCH3 (VIB-34) H H OC2H5 (VIB-35) H H OC3H7-n (VIB-36) H H OC3H7-I (VIB-37) CF3 H OCH3 (VIB-38) CF3 H OC2H5 (VIB-39) CF3 H OC3H7-n (VIB-40) CF3 H OC3H7-I

(VIC)

Table 3c: Examples for the

compounds of formula (VIC)

Example N ° R4 R5 I Melting Point (0C) (VIC-1) CH3 CH3 OCH3 (VIC-2) CH3 CH3 OC2H5 (VIC-3) CH3 CH3 OC3H7-n (VIC-4) CH3 CH3 OC3H7-I (VIC -5) C2H5 CH3 OCH3 (VIC-6) C2H5 CH3 OC2H5 (VIC-7) C2H5 CH3 OC3H7-n (VIC-8) C2H5 CH3 OC3H7-I Example n0 R4 R5 I Melting Point (0C) (VIC-9) C3H7-II CH3 OCH3 (VIC-10) C3H7-II CH3 OC2H5 (VIC-11) C3H7-n CH3 OC3H7-n (VIC-12) C3H7-n CH3 OC3H7-I (VIC-13) C3H7-CH3 OCH3 (VIC -14) C3H7-CH3 OC2H5 (VIC-15) C3H7-CH3 OC3H7-n (VIC-16) C3H7-CH3 OC3H7-I (VIC-17) CH3 H OCH3 (VIC-18) CH3 H OC2H5 (VIC-19) CH3 H OC3H7-n (VIC-20) CH3 H OC3H7-I (VIC-21) C2H5 H OCH3 (VIC-22) C2H5 H OC2H5 (VIC-23) C2H5 H OC3H7-n (VIC-24) C2H5 H OC3H7- I (VIC-25) C3H7-n H OCH3 (VIC-26) C3H7-n H OC2H5 (VIC-27) C3H7-n H OC3H7-n (VIC-28) C3H7-n H OC3H7-I (VIC-29) C3H7-H OCH3 (VIC-30) C3H7-H OC2H5 (VIC-31) C3H7-H OC3H7-n (VIC-32) C3H7-H OC3H7-I (VIC-33) H H OCH3 (VIC-34) H H OC2H5 (VIC-35) H H OC3H7-n (VIC-36) H H OC3H7-I (V IC-37) CF3 H OCH3 (VIC-38) CF3 H OC2H5 Example No R4 R5 I Melting Point (0C) (VIC-39) CF3 H OC3H7-n (VIC-40) CF3 H OC3H7-I

Starting materials of formula (IV):

Sulphonylisocyanates are prepared by known methods from a corresponding sulfonamide of formula (II), an alkylisocyanate such as n-butyl isocyanate, phosgene and a catalytic amount of 1,4-diaza [2,2,2] bicyclooctane. (DABCO) in xylene or another sufficiently high boiling inert solvent (> 135 ° C), compare H. Ulrich and AAY Sayigh, Newer Methods of Preparative Organic Chemistry, volume VI, page 223-241, Academic Press, New York and London, W. Foerst Ed., Also compare WO 2003/033459.

ibela 4a: Examples for compounds of formula VAT) Example No. R2 R5 I O1 Melting Point (0C) (IVA-2) CH3 CH3 OC2H5 O (IVA-3) CH3 CH3 OC3H7-n O (IVA-4) CH3 CH3 OC3H7-I O (IVA-5) C2H5 CH3 OCH3 O (IVA-6) C2H5 CH3 OC2H5 O (IVA-7) C2H5 CH3 OC3H7-n O (IVA-8) C2H5 CH3 OC3H7-I O (IVA-9) ) C3H7-n CH3 OCH3 O (VAT-10) C3H7-n CH3 OC2H5 O (VAT-11) C3H7-n CH3 OC3H7-n O (VAT-12) C3H7-n CH3 OC3H7-I O (VAT-13) C3H7 - CH3 OCH3 O (IVA-14) C3H7- CH3 OC2H5 O (IVA-15) C3H7- CH3 OC3H7-n Example n0 R2 R5 I O1 Melting Point (0C) (IVA-16) C3H7-I CH3 OC3H7-I O (IVA-17) CH3 H OCH3 O (IVA-18) CH3 H OC2H5 O (IVA-19) CH3 H OC3H7-n O (IVA-20) CH3 H OC3H7-I O (IVA-21) C2H5 H OCH3 O (IVA-22) C2H5 H OC2H5 O (IVA-23) C2H5 H OC3H7-N O (IVA-24) C2H5 H OC3H7-I O (IVA-25) C3H7-n H OCH3 O (IVA-26) C3H7-Ii H OC2H5 O (VAT-27) C3H7-n H OC3H7-IO (VAT-28) C3H7-n H OC3H7-I O (VAT-29) C3H7-I H OCH3 O (VAT-30) C3H7-I H OC2H5 O (IVA-31) C3H7-I H OC3H7-n O (IVA-32) C3H7-I H OC3H7-I O (IVA-33) H H OCH3 O (IVA-34) H H OC2H5 O (IVA-35) H H OC3H7-n O (IVA-36) H H OC3H7-! O (IVA-37) CF3 H OCH3 O (IVA-38) CF3 H OC2H5 O (IVA-39) CF3 H OC3H7-n O (IVA-40) CF3 H OC3H7-I O SOrN = C = Q1

(IVB)

OK

by 4b: Examples for compounds of formula (IVB)

Example No. R4 R5 I Q1 Melting Point (C) (IVB-1) CH3 CH3 OCH3 O (IVB-2) CH3 CH3 OC2H5 O (IVB-3) CH3 CH3 OC3H7-n O (IVB-4) CH3 CH3 OC3H7 -I O (IVB-5) C 2 H 5 CH 3 OCH 3 O (IVB-6) C 2 H 5 CH 3 OC 2 H 5 O (IVB-7) C 2 H 5 CH 3 OC 3 H 7 -N (IVB-8) C 2 H 5 CH 3 OC 3 H 7 -I O (IVB-9) C 3 H 7- n CH3 OCH3 O (IVB-10) C3H7-n CH3 OC2H5 O (IVB-11) C3H7-Ii CH3 OC3H7-nO (IVB-12) C3H7-n CH3 OC3H7-I O (IVB-13) C3H7-I CH3 OCH3 O (IVB-14) C3H7-I CH3 OC2H5 O (IVB-15) C3H7-I CH3 OC3H7-IO (IVB-16) C3H7-I CH3 OC3H7-IO (IVB-17) CH3 H OCH3 O (IVB -18) CH 3 H OC 2 H 5 O (IVB-19) CH 3 H OC 3 H 7 -N (IVB-20) CH 3 H OC 3 H 7 O (IVB-21) C 2 H 5 H OCH 3 O (IVB-22) C 2 H 5 H OC 2 H 5 O (IVB- 23) C2H5H OC3H7-nO (IVB-24) C2H5H OC3H7-IO (IVB-25) C3H7 -nHOCH3O (IVB-26) C3H7 -nH OC2H5 Example # R4 R5 I O1 fusion (C) (IVB-27) C3H7-IH H OC3H7-n O (IVB-28) C3H7-nH OC3H7-IO (IVB-29) C3H7-IH OCH3 O (IVB-30) C3H7-IH OC2H5O (IVB-31) C3H7-IH OC3H7-nO (IVB-32) C3H7-IH OC3H7-IO (IVB-33) H H OCH3O (IVB-34) H H OC2H5O (IVB-35) H H OC3H7-IO (IVB-36) H H OC3H7-IO (IVB-37) CF3 H OCH3 O (IVB-38) CF3 H OC2H5 O (IVB-39) CF3 H OC3H7 -n O (IVB-40) CF3 H OC3H7-I O

SOs-N = C-Q '

(IVC)

Table 4c: Examples for the compounds of the formula

Example R4 R5 IO1 Melting Point (cC) (IVC-1) CH3 CH3 OCH3 O (IVC-2) CH3 CH3 OC2H5 O (IVC-3) CH3 CH3 OC3H7-n O (IVC-4) CH3 CH3 OC3H7 -I O (IVC-5) C 2 H 5 CH 3 OCH 3 O (IVC-6) C 2 H 5 CH 3 OC 2 H 5 O (IVC-7) C 2 H 5 CH 3 OC 3 H 7 -N (IVC-8) C 2 H 5 CH 3 OC 3 H 7 -I O (IVC-9) C 3 H 7 - n CH3 OCH3 O (IVC-10) C3H7-n CH3 OC2H5 O

Example 4 R4 R5 I Q1 Melting Point (C) (IVC-11) C3H7-n CH3 OC3H7-n O (IVC-12) C3H7-n CH3 OC3H7-I O (IVC-13) C3H7-CH3 OCH3 O (IVC-14) C 3 H 7 -CH 3 OC 2 H 5 O (IVC-15) C 3 H 7 -CH 3 OC 3 H 7 -I (IVC-16) C 3 H 7 -CH 3 OC 3 H 7 -I O (IVC-17) CH 3 H OCH 3 O (IVC-18) CH 3 H OC 2 H 5 O (IVC-19) CH 3 H OC 3 H 7 -I (IVC-20) CH 3 H OC 3 H 7 -O (IVC-21) C 2 H 5 H OCH 3 O (IVC-22) C 2 H 5 H OC 2 H 5 O (IVC-23) C 2 H 5 H OC3H7-n O (IVC-24) C2H5 H OC3H7-IO (IVC-25) C3H7-nH OCH3 O (IVC-26) C3H7-nH OC2H5 O (IVC-27) C3H7-nH OC3H7-n O (IVC-28) C3H7-H1 OC3H7-IO (IVC-29) C3H7-H OCH3O (IVC-30) C3H7-H OC2H5 O (IVC-31) C3H7-H OC3H7-n O (IVC-32) C3H7-H OC3H7-I O (IVC-33) H H OCH3 O (IVC-34) H H OC2H5 O (IVC-35) H H OC3H7-n O (IVC-36) H H OC3H7-I O (IVC- 37) CF3 H OCH3 O (IVC-38) CF3 H OC2H5 O (IVC-39) CF3 H OC3H7-IO (IVC-40) CF3 H OC3H7-I O Application Examples: Example A

1. Herbicidal effect on pre-emergence

Seeds of weed or mono- or dicotyledonous plants are scattered in wood fiber pots on sandy muddy soil and covered with soil. Test compounds formulated as wettable powders (WP) or as emulsion concentrates (EC) are then applied as an aqueous suspension with a converted water application amount of 800 l / ha adding 0.2% umectan - on the surface of the covering earth.

After treatment, the pots are placed in the greenhouse and kept in good growing condition for the test plants. Visual assessment of lesions on the test plants is performed after a trial time of 3 weeks compared to untreated controls. Mean:

0% = no effect (such as untreated control) 100% = total extermination

In the following, the efficacies of some of the claimed compounds are represented in several tested weeds. Mean:

AVESA = Avena sativa LOLMU = Lolium multifIorum SETVI = Setaria viridis AMARE = Amaranthus retroflexus SIGN = Sinapis alba STEME = Stellaria media

compound g application of active substance / ha AVESA LOLMU SETVI AMARE SIGN STEME IA-1 80 90 100 100 90 90 100

compound active substance g application / ha AVESA LOLMU SETVI AMARE SIGNAL STEME IA-2 80 80 90 100 90 90 100 compound active substance g application / ha AVESA LOLMU SETVI AMARE SIGN IA-3 80 80 80 90 90 90

Active substance application g / ha LOLMU AMARE STEME IA-6 80 90 100 80

compound application g active substance / ha LOLMU STEME IA-7 80 80 100

compound active substance g application / ha LOLMU AMARE SIGNAL STEME IA-8 80 80 100 80 80

In this test, for example, compounds according to preparation example IA-1, IA-2, IA-3, IA-6, IA-7 and IA-8 with partially good plant tolerance. cultivated crops such as corn and wheat show a strong effect against weeds.

Example B

2. Post-emergence herbicidal effect

Seeds of single- or dicotyledonous weeds or cultivated plants are scattered in wood fiber pots on sandy muddy soil, covered with soil and grown in the greenhouse with good growing conditions. Two to three weeks after sowing, the test plants are treated at the leaf stage. Thesis compounds formulated as wettable powders (WP) or as emulsion concentrates (EC) are then sprayed as an aqueous suspension with a converted active substance application amount of 800 l / ha adding 0.2% humectant. , on the green parts of plants. After a time of exposure of the test plants to the greenhouse of approximately 3 weeks with optimal growing conditions, the effect of the preparations is visually evaluated compared to untreated controls (percentage herbicidal effect (%): 100% effect = plants died, 0% effect = as control plants). Mean:

0% = no effect (such as untreated control) 100% = total extermination. AVESA = Avena sativa ECHCG = Echinochloa crus-galli LOLMU = Lolium multifIorum SETVI = Setaria viridis

AMARE = Amaranthus retrofIexus SIGN = Sinapis alba STEME = Stellaria media

compound application g of active substance / ha AVESA ECHCG LOLMU SETVI AMARE SIGNAL STEME IA-1 80 90 90 100 100 100 100 90 compound application of g of active substance / ha AVESA ECHCG LOLMU SETVI AMARE SIGN STEME IA -2 80 90 90 100 100 100 90 100 compound application g of active substance / ha AVESA ECHCG LOLMU SETVI IA-3 80 80 80 90 90

compound application g of active substance / ha AVESA ECHCG LOLMU IA-5 80 90 80 80 composite application g of active substance / ha AVESA ECHCG LOLMU SETVI AMARE STEME IA-6 80 80 80 90 80 90 90

compound g application of active substance / ha AVESA ECHCG LOLMU SETVI IA-7 80 80 80 80 80

compound g application of active substance / ha E-CHCG AMARE STEME IA-8 80 80 80 80

compound application g of active substance / ha AVESA ECHCG LOLMU SETVI AMARE SIGN IA-9 80 80 90 90 80 90 90

In this test, for example, compounds according to

preparation examples IA-1, IA-2, IA-3, IA-5, IA-6, IA-7, IA-8 and IA-9 with partially good tolerance to cultivated plants such as For example, corn and wheat show a strong effect against weeds.

Claims (16)

1. Substituted Fürylsulfonylamino (thio) carbonyl triazolin (thi) of the general formula (I) wherein Q1 represents oxygen or sulfur, Q2 represents oxygen or sulfur, Ra represents hydrogen, cyano, nitro, halogen or alkyl, alkoxy, alkylthio, alkylsulfinyl, alkylsulfonyl, alkenyl, alkynyl, alkenyloxy or alkynyloxy in each case optionally substituted, Rb represents hydrogen, cyano, nitro, halogen or alkyl, alkoxy, alkylthio, alkylsulfonyl, alkylsulfonyl, alkenyl, alkynyl, alkenyloxy or alkenyloxy optionally each substituted Rc represents CO-Y ρ R represents hydrogen, hydroxy, amino, cyano, represents alkylidenamino or represents alkyl, alkenyl, alkynyl, alkoxy, alkylamino, alkylcarbonylamino, alkenyloxy, dialkylamino, cycloalkyl, cycloalkylamino, cycloalkylalkyl, aryl or arylalkyl in each case optionally substituted, R7 represents hydrogen, hydroxy, mercapto, amino, cyano, halog indium or represents alkyl, alkenyl, alkynyl, alkoxy, alkylthio, alkylamino, alkylcarbonylamino, alkenyloxy, alkynyloxy, alkenylthio, alkynylthio, alkenylamino, alkynylamino, dialkylamino, aziridino, pyrrolidine, piperidine, cycloalkyl, morpholino , cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio, cycloalkylalkylamino, aryl, arylalkyl, aryloxy, arylthio, arylalkylthio, arylamino or optionally substituted R 6 (together substituted) and Y represents one of the groups OR8 or N (R9R10) 1 wherein R8 represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl in each case optionally substituted, R9 represents hydrogen or represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, optionally substituted alkyl, heterocyclyl or heterocyclylalkyl in each case R10 represents hydrogen or represents alkyl, alkenyl, alkynyl, cycloalkyl, cycloalkylalkyl, aryl, arylalkyl, heterocyclyl or heterocyclylalkyl in each case optionally substituted, as well as salts of compounds of the formula ( I). Compounds of formula (I) as defined in claim 1, characterized in that in this Q1 represents oxygen or sulfur, Q2 represents oxygen or sulfur, Ra represents hydrogen, cyano, nitro, halogen, represents alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl having respectively 1 to 6 carbon atoms in the alkyl group, in each case optionally substituted by cyano, halogen or (C1 -C4) alkoxy or represents alkenyl, alkynyl, alkenyloxy or alkynyloxy having respectively 2 to 6 carbon atoms in the group alkenyl or alkynyl, in each case optionally substituted by cyano or halogen, Rb represents hydrogen, cyano, nitro, halogen, represents alkyl, alkoxy, alkylthio, alkylsulfinyl or alkylsulfonyl with respectively 1 to 6 carbon atoms in the alkyl group, in each case optionally substituted by cyano, halogen or (C1 -C4) alkoxy or represents alkenyl, alkynyl, alkenyloxy or alkynyloxy with respectively 2 to 6 carbon atoms in the alkenyl or alkynyl group, in each case optionally substituted by cyano or halogen, R c represents CO-Y, R 6 represents hydrogen, hydroxy, amino, cyano represents (C 2 -C 10) -alkylidenamino, represents alkyl of 1 to 6 carbon atoms substituted by (C 1 -C 4) alkylcarbonyl or (C 1 -C 4) alkoxycarbonyl represents alkenyl or alkynyl having respectively 2 to 6 carbon atoms, in each case optionally substituted by fluorine, chlorine and / or bromine represents alkoxy, alkylamino or alkylcarbonylamino having respectively 1 to 6 carbon atoms in the alkyl group, in each case optionally substituted by fluorine, chlorine, bromine, cyano, (C1 -C4) alkoxy or (C1 -C4) alkoxy -carbonyl, represents alkenyloxy of 3 to 6 carbon atoms, represents dialkylamino with respectively 1 to 4 carbon atoms in alkyl groups, represents cycloalkyl, cycloalkylamino or cycloalkylalkyl with respect to 3 to 6 carbon atoms in the alkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by fluorine, chlorine, bromine, cyano and / or (C1 -C4) alkyl or represents aryl or arylalkyl with respectively 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by fluorine, chlorine, bromine, cyano, nitro (C1 -C4) alkyl, trifluoromethyl and / or (C1 -C4) alkoxy, R7 represents hydrogen, hydroxy, mercapto, amino, cyano, fluorine, chlorine, bromine, iodine, represents alkyl of 1 to 6 carbon atoms optionally substituted by fluorine, chlorine, bromine, cyano (C 1 -C 4) alkoxy, (C 1 -C 4) alkylcarbonyl or (C 1 -C 4) alkoxycarbonyl represents alkenyl or alkynyl having respectively 2 to 6 carbon atoms in each case optionally substituted by fluorine, chlorine and / or bromine. alkoxy, alkylthio, alkylamino or alkylcarbonylamino with respect to 1 to 6 carbon atoms in the alkyl group, in each case optionally substituted by fluoro, chloro, cyano, (C1 -C4) alkoxy or (C1 -C4) alkoxycarbonyl, represents alkenyloxy, alkynoxy, alkenylthio, alkynylthio, alkenylamino or alkynylamino having respectively 3 to 6 carbon atoms in the alkenyl or alkynyl group, represents dialkylamino with respectively 1 to 4 carbon atoms in the alkyl groups, represents aziridine, pyrrolidine, piperidino or morpholine in each case optionally substituted by methyl. and / or ethyl represents cycloalkyl, cycloalkenyl, cycloalkyloxy, cycloalkylthio, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy, cycloalkylalkylthio or cycloalkylalkylamino having respectively 3 to 6 carbon atoms in the cycloalkyl or cycloalkenyl group and optionally 1 to 4 carbon atoms alkyl, in each case optionally substituted by fluorine, chlorine, bromine, cyano and / or (C1 -C4) alkyl or represents air arylalkyl, aryloxy, arylalkoxy, arylthio, arylalkylthio, arylamino or arylalkylamino having respectively 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by fluorine, chlorine, bromine, cyano, nitro, (C1 -C4) alkyl, trifluoromethyl, (C1 -C4) alkoxy and / or (C1 -C4) alkoxycarbonyl, R6 and R7 together represent alkanediyl of 3 to 6 eventually branched carbon atoms, Y represents one of the groups OR8 or N (R9R10) 1 wherein R8 represents alkyl of 1 to 6 carbon atoms optionally substituted by cyano, halogen or (C1 -C4) alkoxy, represents alkenyl or alkynyl having respectively 2 to 6 carbon atoms, in each case eventually substituted by cyano or halogen, represents cycloalkyl or cycloalkylalkyl having respectively 3 to 6 carbon atoms in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case eventually. substituted by cyano, halogen or (C1 -C4) alkyl, represents aryl or arylalkyl having respectively 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano, halogen, (C1 -C4) alkyl or (C1 -C4) alkoxy or represents heterocyclyl or heterocyclylalkyl having respectively up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 to 2 oxygen or sulfur atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano, halogen, (C1 -C4) alkyl or (C1 -C4) alkoxy, R9 represents hydrogen or represents alkyl of 1 to 4. 6 carbon atoms optionally substituted by cyano, halogen or (C1 -C4) alkoxy, represents alkenyl or alkynyl having respectively 2 to 6 carbon atoms, in each case optionally substituted by cyano or halogen, represents cycloalkyl or cycloalkylalkyl having respectively 3 to 6 carbon atoms in the cycloalkyl group and possibly 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by cyano, halogen or (C 1 -C 4) alkyl, represents aryl or arylalkyl having respectively 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano, halogen, (C1 -C4) alkyl or (C1 -C4) alkoxy or represents heterocyclyl or heterocyclylalkyl having respectively up to 6 carbon atoms and additionally 1 to 4 nitrogen atoms and / or 1 to 2 oxygen or sulfur atoms in the heterocyclyl group and possibly 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano, halogen, (C1 -C4) alkyl or (C1 -C4) alkoxy and R10 represents hydrogen or alkyl of 1 to 6 carbon atoms which may be substituted. cyano, halogen or (C 1 -C 4) alkoxy, represents alkenyl or alkynyl having 2 to 6 carbon atoms respectively, in each case optionally substituted by cyano or halogen, represents cycloalkyl or cycloalkylalkyl having respectively 3 to 6 carbon atoms. carbon in the cycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by cyano, halogen or (C1 -C4) alkyl, represents aryl or arylalkyl having respectively 6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in the alkyl moiety, in each case optionally substituted by nitro, cyano, halogen, (C1 -C4) alkyl or (C1 -C4) alkoxy or represents heterocyclyl or heterocyclylalkyl of up to 6 atoms respectively. carbon and in addition 1 to 4 nitrogen atoms and / or 1 to 2 oxygen or sulfur atoms in the heterocyclyl group and optionally 1 to 4 carbon atoms in the alkyl moiety at c in the event of any substitution by nitro, cyano, halogen, (C1 -C4) alkyl or (C1 -C4) alkoxy, as well as sodium, potassium, magnesium, calcium, ammonium, (C1 -C4) alkyl ammonium, di (( (C 1 -C 4) alkyl) ammonium, tri - ((C 1 -C 4) alkyl) ammonium, tetra - ((C 1 -C 4) alkyl) ammonium, tri ((C 1 -C 4) alkyl) sulfonium, C 5 - or C 6 cycloalkyl -ammonium and di - ((C 1 -C 2) alkyl) benzyl ammonium of compounds of formula (I). Compounds of formula (I) as defined in claim 1, characterized in that in this Q1 represents oxygen or sulfur, Q2 represents oxygen or sulfur, Ra represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, methyl, ethyl , n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulfinyl, ethylsulfinyl, methylsulfonyl or ethylsulfonyl in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy or represents propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy in each case optionally substituted by cyano, fluorine or chlorine, Rb represents hydrogen, cyano, fluorine, chlorine, bromine, iodine, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl in each case and substituted by cyano, fluorine, chlorine, methoxy or ethoxy or represents propenyl, butenyl, propynyl, butynyl, propenyloxy, butenyloxy, propynyloxy or butynyloxy in each case optionally substituted by cyano, fluorine or chlorine, Rc represents CO-Y, R6 represents hydrogen, hydroxy, amino, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, represents ethenyl, propenyl, butenyl, propynyl or butynyl in each case optionally substituted by fluorine, chlorine and / or bromine, represents methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino in each case optionally substituted by fluorine, chlorine, cyano, methoxy or ethoxy, represents propenyloxy or butenyloxy, represents dimethylamino or diethylamino, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylamino, cyclobutylamino , cyclopentylamino, cyclohexylamino, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl in each case optionally substituted by fluorine, chlorine, methyl and / or ethyl or represents phenyl or benzyl in each case optionally substituted by fluorine, chlorine, methyl, trifluoromethyl and / or methoxy, R7 represents hydrogen, chlorine, bromine, represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl in each case optionally substituted by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, acetyl, propionyl, n- or i-butyryl, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, represents ethenyl, propenyl, butenyl, ethinyl, propynyl or butynyl in each case. substituted by fluorine, chlorine and / or bromine, represents methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino, acetyl amino or propionylamino in each case optionally substituted by fluorine, chlorine, cyano, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, represents propenyloxy, butenyloxy, ethinyl alkoxy, propynyloxy, butynyloxy, propenylthio, butenylthio, propinylthio, butynylthio, propenylamino, butenylamino, propynylamino or butynylamino, represents dimethylamino, diethylamino or dipropylamino, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclohexyl, cyclopropyl, cyclobutyloxy, cyclopentyloxy, cyclohexenyl, cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy, cyclopropylthio, cyclobutylthio, cyclopentylthio, cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylmethylmethyl, cyclopropylamino, cyclopropyloxy cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylthio, cyclobutylmethyl methylthio, cyclopentylmethylthio, cyclohexylmethylthio, cyclopropylmethylamino, cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino in each case optionally substituted by fluorine, chlorine, methyl and / or ethyl or represents phenyl, benzyl, phenoxy, benzyloxy, phenylthio benzylthio, phenylamino or benzylamino in each case optionally substituted by fluorine, chlorine, bromine, methyl, trifluoromethyl, methoxy or methoxycarbonyl, R 6 and R 7 together represent trimethylene (propan-1,3-diyl), tetramethylene (butanol). -1,4-diyl) or pentamethylene (pentan-1,5-diyl), Y represents one of the groups OR 8 or N (R 9 R 10 C), wherein R 8 represents methyl, ethyl, n- or i-propyl, n-, i -, s- or t-butyl in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy, represents propenyl, butenyl, propynyl or butynyl in each case optionally substituted by cyano, fluorine or chlorine, represents cyclopropyl, cyclobutyl , cyclopentyl, cyclohexyl, cyclopropylmethyl a, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, represents phenyl, phenylmethyl or phenylethyl in each case possibly substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl , n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy or represents heterocyclyl or heterocyclylmethyl in each case possibly substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl , n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, the heterocyclyl group being selected in each case from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl, R 9 represents hydrogen or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl in each case optionally substituted by cyano, fluorine, chlorine, methoxy or ethoxy, represents propenyl, butenyl, propynyl or butynyl in each case eventually replaced cyano, fluorine or chlorine represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl in each case optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, represents phenyl, phenylmethyl or phenylethyl in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy, ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy or represents heterocyclyl or heterocyclylmethyl in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n- or i-propoxy, each heterocyclyl group being selected in each case. oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl series and R10 represents hydrogen or represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl in each case replaced by cyan, fluorine, c loro, methoxy or ethoxy, represents propenyl, butenyl, propynyl or butynyl in each case optionally substituted by cyano, fluorine or chlorine, represents cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl in each case. optionally substituted by cyano, fluorine, chlorine, methyl or ethyl, represents phenyl, phenylmethyl or phenylethyl in each case optionally substituted by cyano, fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, trifluoromethyl, methoxy , ethoxy, n- or i-propoxy, difluoromethoxy or trifluoromethoxy or represents heterocyclyl or heterocyclylmethyl in each case optionally substituted by cyano, fluoro, chloro, bromo, methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n - or i-propoxy, the heterocyclyl group being in each case selected from the series oxetanyl, thietanyl, furyl, tetrahydrofuryl, thienyl, tetrahydrothienyl. Compounds of formula (I) as defined in claim 1, characterized in that in this Q1 represents oxygen, Q2 represents oxygen, Ra represents hydrogen, fluorine, chlorine, bromine, iodine or represents methyl, ethyl, n- or i- propyl, in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy, Rb represents hydrogen, fluorine, chlorine, bromine, iodine or represents methyl, ethyl, n- or i-propyl, in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy, R 0 represents CO-Y, and R represents methyl, ethyl, n- or i-propyl in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy, represents ethenyl, propenyl or propyl. pinyl in each case optionally substituted by fluorine or chlorine, represents methoxy, ethoxy, n- or i-propoxy in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy, represents dimethylamino or cyclopropyl, R7 represents hydrogen, chlorine, bromine, represents methyl, et ila, n- or i-propyl in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, represents ethenyl, propenyl, butenyl, propynyl or buynyl in each case optionally substituted by fluorine or chlorine represents methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n- or i-propylamino in each case optionally substituted by fluorine, chlorine, methoxy, ethoxy, n- or i-propoxy, represents propenyloxy, propynyloxy, propenylthio, propinylthio, propenylamino or propynylamino, represents dimethylamino or diethylamino, represents cyclopropyl, cyclopropyloxy, cyclopropylmethyl or cyclopropylmethoxy in each case optionally substituted by fluorine, Y or chloro, Y represents the group OR8, where R8 represents methyl, ethyl, n- or i-propyl in each case optionally substituted by fluorine, chlorine, methoxy or ethoxy. Compounds of formula (IA) wherein R2 represents Ra and R5 represents Rb and wherein Q1, Q2, Ra, Rb, R6, R7 and Y have the meanings as defined in one of claims 1 to 4. Compounds of formula (IA) according to claim 5, wherein R2 represents hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R5 represents hydrogen or methyl. Compounds of formula (IB) wherein R4 represents Ra and R5 represents Rb and wherein Q1, Q2, Ra, Rb, R6, R7 and Y have the meanings as defined in one of claims 1 to 4. Compounds of formula (IB) according to claim 7, wherein R 4 represents hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R 5 represents hydrogen or methyl. Compounds of formula (IC) wherein R4 represents Ra and R5 represents Rb and wherein Q11 Q21 Ra1 Rb1 R61 R7 and Y have the meanings as defined in one of the claims 1 to 4. Compounds of formula (IC) according to claim 9, wherein R 4 represents hydrogen, methyl, trifluoromethyl, ethyl, propyl, isopropyl and R 5 represents hydrogen or methyl. Process for the preparation of compounds of formula (I) as defined in claim 1, characterized in that (a) substituted furansulfonamides of the general formula (II) in which: Ra, Rb and Rc have the meaning as defined in claim 1, are reacted with substituted triazolin (thi) ones of the general formula (III) wherein Q1, Q21 R6 and R7 have the meaning as defined in claim 1 and Z represents halogen, alkoxy, aryloxy or arylalkoxy, optionally in the presence of a reaction aid and possibly in the presence of a diluent or if (b) furyl sulfonyl iso (thio) cyanates of formula (IV) wherein Q21 R6 and R7 have the meaning as defined in claim 1 possibly in the presence of a reaction auxiliary agent and if any. even in the presence of a diluent or if (c) substituted furan sulfonic acid chlorides of the general formula (VI) <formula> formula see original document page 127 </formula> where Q11 Ra, Rb and Rc have the meaning as defined in claim 1 are reacted with triazolin (thi) ones of the general formula (V) wherein Ra1 Rb and Rc have the meaning as defined in claim 1 are reacted with triazolin (th). ti) one of general formula (V) <formula> formula see original document page 128 </formula> wherein Q2, R6 and R7 have the meaning given in claim 1, and metal thiocyanates of general formula (VII) <formula> where Q1 has the meaning as defined in claim 1, possibly in the presence of a reaction aid and possibly in the presence of a diluent or if (d) furan sulfonic acid chlorides Substituted formula g In which Ra, Rb and Rc have the meaning as defined in claim 1, they are reacted with triazolin (ti) on- (thio) carboxamides of the general formula (VIII) <formula> formula see original document page 128 </ wherein Q11 Q2, R6 and R7 have the meaning as defined in claim 1, optionally in the presence of a reaction aid and possibly in the presence of a diluent or if (e) furylsulfonylamino (thio) carbonyl compounds of formula (IX) wherein Q1, Ra1 Rb and Rc have the meaning as defined in claim 1, and Z represents halogen, alkoxy, aryloxy or arylalkoxy, are reacted with triazolin (thi) one of the general formula (V) wherein Q2, R6 and R7 have the meaning as defined in claim 1 optionally in the presence of a reaction auxiliary agent and possibly in the presence of a diluent and optionally the compounds of formula (I) obtained according to processes (a), (b), (c), (d) or (e) are converted to salts by usual methods. Process for the preparation of substituted furan sulfonamides of the formula (II) <formula> formula see original document page 129 </formula> characterized in that the furan sulfonic acid chlorides of the general formula (VI) <formula in which Ra1 Rb and Rc have the meaning as defined in claim 1, are reacted with ammonia or as ammonium salts, optionally in the presence of a diluent, at temperatures between 0 ° C and 100 ° C. Ç. Herbicidal compositions, characterized by a content of at least one compound of formula (I) as defined in claim 1. Use of compounds of general formula (I) as defined in claim 1 for combating undesirable plant growth. Weed control process, characterized in that compounds of the general formula (I) as defined in claim 1 are allowed to act on the weeds or their habitat. Process for the preparation of herbicidal compositions, characterized in that compounds of general formula (I) as defined in claim 1, are mixed with diluents and / or surface active agents.