CA2119673A1 - Substituted 1-aryltriazolinones - Google Patents

Abstract

Substituted 1-aryltriazolinones A b s t r a c t The invention relates to new substituted 1-aryltriazolin-ones of the general formula (I)

Description

' ~llY673 .~

The invention relate~ to new ~ub~tituted 1-aryltriazolin-ones, to a number of proces~es for their preparation, to a number of new intermediates, and to their use as herbi-cides.

It is known that certain substituted triazolinones auch a~, for example, the compound 3-methyl-4-propargyl-1-(2,5-difluoro-4-cyano-phenyl)-1,2,4-triazolin-5-one possess herbicidal properties (cf. e.g. DE 38 39 480).

However the herbicidal activity of these previously known compounds with regard to problem weeds, and al80 their toleration by important crop plants, is not completely satisfactory in all areas of application.

New substituted 1-aryltriazolinone~ of the general formula (I), -R R
N

,~X
R

R ~ R
R
have now been found in which LeA 29 658 - 1 - ;

repre~ent~ hydrogen, alkyl, halogenoalkyl, alkoxy, alkylthio, alkylsulphinyl, alkyl-~ulphonyl or cycloalkyl, R2 repre~ent~ a radical of the formula -NRaR9, R3, R6 and R7 indep~ndently of one another in each ca~e repre~ent hydrogen, haloge~, ami~o or nitro, R~ represents hydrogen, halogen, cyano or nitro, or one of the radicals -Rl, -O-Rl, -S-R10, -S (O) -Rl~ -So2-Rl, -So2-oRlo~ -S02-NRllRl, CO oR10 CO NR11R10 -O-SO2-R1, -N(R1l)-sO2-Rlo~
_ NR11Rlo -N~-p (O) (R11) (ORl) o r -NH-P (O) ~ORll) (OR,l), ~5 represent~ nitro, cyano, halogen or halogeno-alkyl, and X represents oxygen or sulphur, where RB represents hydrogen, alkyl, halogenoalkyl, a radical of the for~ula -CO-R12 or a radical o$
the formula -S(O)~-R12, R9 represent~ alkyl, halogenoalkyl, a radical of the formula -CO-R~2 or a radical of the formula -S(O)n-Rl2, R10 repre~ents hydrogen or r~pre~ents in ea~h case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl, arylalkyl or ~eterocyclyl, R11 repreoents hydrogen or represents in each case optionally ~ub~tituted alkyl, alke~yl, alkinyl, cycloalkyl, arylalkyl or aryl, R12 repre~ent~ in each case optionally sub~titutod alkyl, cycloalkyl, arylalkyl, aryl or hetero-cyclyl, and LeA 29 658 - 2 -~Ll~16 r~3 n repre~ents a number 0, 1 or 2.

Depending on the nature of the ~ubstituents, the com-pounds of the formula (I) may po~sibly be pre~ent a~
geometrical and/or optical isomer~ or i~omer mixture~ of different composition~ Both the pure ioomers and the isomer mixtures are claimed according to the invention.

It has alQo been found that the new substituted l-aryl-triazolinones of the general formula (I), R R
~ N
N~ ~ X
3 7 (1) R ~ R
R
in which Rl represent~ hydrogen, alkyl, halogenoalkyl, alkoxy, alkylthio, alkylsulphinyl, alkyl-sulphonyl or cycloalkyl, R2 represent~ a radical of the formula -NR8R9, R3, R6 and R7 independe~tly of one another i~ each case represent hydrogen, halogen, amino or nit~o, R4 repre~ents hydrogen, halogen, cyano or nitro, or one of the radical~ -Rl, -0-Rl, -S-Rl, -S () -Rl~ -S02-Rl~ -So2-oRlo~ -S02-NRllRl~

LeA 29 658 - 3 -~liY673 .

CO ORl CO NRll~Rl -O-S02-Rl, -N(Rll)-S02-R~, _ NRllRlo -N~ -P (O) (Rll) (ORl) o r -NH-P(O) (ORl~) (ORl) Rs repre~ents nitro, cyano, halogen or halogeno-alkyl, and X represant~ oxygen or sulphur, where R~ repre~ents hydro~en, alkyl, halogenoalkyl, a radical of the formula -CO-Rl2 or a radical of the ~ormula -S(O)~-Rl2, R9 repr~ents alkyl, halo~enoalkyl, a radical of the formula -CO-Rl2 or a radical of the formula -s (O~n-Rl2, : -Rl represents hydrogen or repre~ent~ in each case optionally sub~tituted alkyl, alkenyl, alki~yl, -~
cycloalkyl, aryl, arylalkyl or heterocyclyl, R~l represents hydrogen or repre~ent~ in each case optionally ~ubstituted alkyl, alkenyl, alkinyl, : :-cycloalkyl, arylalkyl or aryl, Rl2 repre~ent~ in each case optionally s~b~tituted al~yl, cycloalkyl, aryl, arylalkyl or hetsro~
cyclyl, and ~ -n repre~ents a nu~ber 0, 1 or 2 are obtained when a) 1~-triazolinones o~ the formula (II), LeA 29 658 - 4 ~

!

~11Y6 /3 ~ -N ~
N~`~X

in which Rl, R2 and X have the meaning given above, are reacted with halogenobenzene derivati~es of the formula (III), 11 ~
R ~ R

in which R3, R4, Rs, R6 and R7 have the meaning~ given above and Hall repre~ent~ halogen, ' ::

optionally in the presence of a diluent and optionally in the pre~ence of a reaction auxiliary, or when ~ :
b) substituted l-aryltriazolino~e3 of the formula (Ia~

LeA 29 658 - 5 , ~

- ~ 6 7 3 R R
~ N

N`N~X
~ .
R ~ H~
R
in which Rl, R2, R3, R6, Rs, R7 and X have the ~eanings given above and ~al2 repre~ent~ halogen, .

S are reacted with nucleophile of the formula (IV), :~

H-R13 (IV) : -in which Rl3 represents a radical o~ the ormula -O-Rl, -S-Rl or -NR1'R'0, where R10 and R11 have the meanings given above, :

optionally in the presence of a diluent and optionally : :
in the presence of a reaction auxiliary, or when c) substituted triazolinones of the formula (V), LeA 29 658 - 6 -rJ1 3 ~ .

/~
~ N

N~N~X

~R

R
in which Rl, R3, Rt, Rs, R6, R7 and X have the meanings given above are reacted with alkylating, acylating or sulphonylat- :
ing agents of the formula (VI), R9-E (VI) -: -in which R9 has the mea~ing given ~bove and --E represents an electron-attracting leaving group, optionally in the pre~ence of a diluent and optionally in the presence o$ a reaction auxiliary, or when d) 4-alkylideneimino-triazolinones of the formula (VII), LeA 29 6S8 - 7 --R N=C
N R
\~x 3 1 7 ( ~R ', R ~ R
R

in which R1, R3, R4, R5, ~6, R7 and X have the meaning~ given above, Rl~ represents hydrogen or alkyl and R1s represent~ alkyl or alkoxy, ..
are reacted with a reduc~ng agent, optionally in the ~;
presence o~ a diluent and optionally in the prs~ence of a reaction auxiliary. ~

Finally it ha~ been found that the new substituted . ~ :
l-aryltriazolinones of the general formula (I) posses~
herbicidal properties.

Surprisingly, the substituted 1-aryltriazoli~on~s o~ the general formul~ (I) according to the i~vention exhibit a con~iderably improvsd herbicidal activity againat problsm we~ds with a comparable tolerance by crop plants in : -~
comparison to the ~ub~tituted triazolinones known from : :- -:

LeA 29 658 - 8 -7 ~

the state of the art, ~uch as, for example, the compound 3-methyl-4-propargyl-1-(2,5-difluoro-4-cyanophenyl)-1,2,4-triazolin-5-one, which are closely related com-pounds in terms of their chemistry and their action.
The general definition of the ~ubstituted l-aryltriazoli-nones according to the invention i8 given by the formula (I). Preferred compounds of the formula (I) are tho~e in which Rl represents hydrogen or represents in each case straight-chain or branched alkyl, alkoxy, alkylthio or alkylsulphonyl having in each case from 1 to 8 carbon atoms, furthermore represent~ ~traight-~hain or branched halogenoalkyl having from 1 to 8 carbon atoms nd from 1 to 17 identical or different halogen atoms, or represents cycloalkyl ha~ing from 3 to 8 carbon atoms, R2 repre~ents a radical of the formula -NRsR9, R3, Rs and R7 independently of one another in each case repreaent hydrogen, fluorine, chlorine, bromine, -:
iodine, amino or nitro, ~::
R~ represents hydrogen, fluorine, chlorine, bromine, :~
iodine, cyano or nitro, or xepresents one of the radicals -Rl, -O-Rl, -S-RlD S(O) R~ SO lo -S2-ORl, -S2-NRllRl, -CO-ORl, -CO_NRi~R10 0 SO Rl -N(Rll)_so2_Rlo _NRllRlo -NH-P(O)(Rll)(ORl) or -NH-P(O)(ORll)(oRlo)~
Rs represents nitro, cyano, fluorine, chlorine, brom-ine, iodine or represents straight-chain or branched halogenoalkyl having from 1 ~o 6 carbon atoms and LeA 29 658 - 9 - : :

,, ~ , . . .. . .. . .. . . . . . . . .. ..

from 1 to 13 identieal or dlfferent halogen atom~
and X represent~ oxygen or ~ulphur, where Ra repre~ents hydrogen, straight-chain or branehed alkyl having from 1 to 8 earbon atom~ or ~tra~ght-chain or branched halogenoalkyl having from 1 to 8 carbon atom~ and from 1 to 17 identieal or different halogen atom~, and furthermore repre~ents a radieal of the ormula -CO-R1~ or a radical of the formula -S (O)n-Rl2, R9 represent~ ~traight-chain or branched alkyl having from 1 to 8 carbon atom~ or straight-chain or branehed halogenoalkyl having from 1 to 8 carbon atoms and from 1 to 17 identical or different halogen atoms, and furthermore repre~ents a radical of the formula -CO-Rl2 or a radical of the formula -S(O)U-R
R10 repre~ents hydrogen~
R10 $urthermore represent~ Rtraight-chain or branehed alkvl having from 1 to 14 carbon atom~ which iB
optionally ~ub~tituted once or more than once by identieal or different substituents, po~sible substituent~ being~
halogen - in particular ~luorine, chlorine, bromine and/or iodine - eyano, carboxyl, earbamoyl, in eaeh ~a~e ~traight-ehain or branched alkoxy, alkoxy-alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, N-alkylaminocarbonyl, N,N-dialkyl-aminocarbonyl or alkyl~ulphonylaminocarbonyl ha~ing in each case from 1 to 8 carbon atoms in the LeA 29 658 - 10 -7 ~

individual alkyl moieties, or heterocyclyl, the heterocyclyl radical being a five- to seven-mem-bered, optionally benzo-fused, saturated or unsatu-rated heterocycle having from 1 to 3 identical or different hetero atoms - in particular nitrogen, oxygen and/or sulphur;
R10 furthermore represents alkenYl or alkinyl having in each case from 2 to 8 carbon atoms, which are optionally substituted once or more than once by identical or different halogens - in particular fluorine, chlorine, bromine and/or iodine;
R10 furthermore represents cycloalkyl having from 3 to 7 carbon atoms which is optionally substituted once or more than once by identical or different substit- ~-uents comprising halogen - in particular fluorine, chlorine, bromine and/or iodine - and/or straight-chain or branched alkyl having from 1 to 4 carbon atoms; :-Rl furthermore represents arvlalkyl or aryl having in each case ~rom 6 to 10 carbon atom3 in the aryl moiety and optionally from 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, which are in each case optionally ~ubatituted in the aryl moiety once or more than once by identical or different substituents, or repre~ents a saturated or --unsaturated, five- to seven-membered heterocyclyl radical having from 1 to 3 identical or different -~ -hetero atoms - in particular nitrogen, oxygen and/or sulphur - which i~ optionally substituted once or more than once by identical or different :

LeA 29 658 - 11 --::, ~ ~
:~.-. .:

~lY673 substituents and/or i8 benzo-fused, possible sub~ti-tuents of the aryl and/or heterocyclyl being in each ca~e:
halogen, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each ca~e from l to 6 carbon atom~, in each caae straight-chain or branched halogenoalkyl, halogeno-alkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each ca~e from 1 to 6 carbon atom~ and from 1 to 13 identical or differ-ent halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each ca~e from 1 to 6 carbon atoms in the individual alkyl moietie~, and phe~yl which i8 optionally ~ubstituted once or more than once by identical or different substituents comprising halogen and/or ~traight-chain or branched alkyl or alkoxy having in each case from 1 to 6 carbon atom~ and/or straight-chain or branched haloge~oalkyl or halogenoalkoxy having in each case from 1 to 6 carbon atoms and from 1 to 13 identical or dif~sren~ halogen atoms;
R'l represents hydrogen;
Rll furthermore repre~ent~ ~traight-chain or bra~ched alkyl having from 1 to 14 carbon atoms which i8 optionally substituted once or more than once by identical or different sub~tituents, posaible ~ubstituent~ being:
halogen - in particular fluorine, chlorine, brom~ne and/or iodine - cyano, carboxyl, carbamoyl, in each LeA 29 658 - 12 -~.L.1.)673 ca~e straight-chain or branched alkoxy, alkoxy-alkoxy, alkylthio, alkyl~ulphinyl, alkyl~ulphonyl, alkoxycarbonyl, N-alkylaminocarbonyl, N,N-dialkyl-aminocarbonyl or alkylsulphonylaminocarbonyl ha~ing in each ca~e f~om 1 to 8 carbon atoms in the indivi-dual alkyl moietie~, or heterocyclyl, the hetero-cyclyl radical bein~ a five- to seven-m~hered, optionally benzo-fused, saturated or un~aturated heterocycle having from 1 to 3 identical or differ-ent hetero atoms - in particular nitrogen, oxygen and/or sulphur;
Rll furthermore repre6ents alkenyl or alkinYl having in each case from 2 to 8 carbon atoms, which are optionally ~ubstituted once or more than once by identical or different halogens - in particular fluorine, chlorins, bromine and/or iodine;
Rll furthermore represent~ cv-cloalkvl having from 3 to 7 carbon atoms which is optionally sub~tituted once or more than once by identical or different substit-uent~ compri~ing halogen - in particular fluorine, chlorine, bromine and/or iodine - and/or ~traight-chain or branched alkyl ha~ing from 1 to 4 carbon atoms;
Rll furthermore represent~ arylalkyl or arvl having in each case from 6 to 10 carbon atom3 in the aryl moiety and optionally 1 to 4 carbon atoma in the straight-chain or branched alkyl moiety, which are in each case optionally substituted in the aryl moiety once or more than once by identical or different substituents, pos~ible substituent~ of the LeA 29 658 - 13 -~ :

aryl being in each case:
halogen, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, al~oxy, alkylthio, alkyl~ulphinyl or alkyl~ulphonyl having in each ca~e from 1 to 6 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogeno-alkoxy, haloge~oalkylthio, halogenoalkyl~ulphinyl or halogenoalkylsulphonyl having in each case from 1 to 6 carbon atoms and from 1 to 13 identical or differ-lQ ent halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximino~lkyl having in each ca~e from 1 to 6 carbon atoms in the individual alkyl moietiea, and phenyl which i~ optionally substituted once or more than once by identical or di~ferent substituents comprising halogen and/or straight-chain or branched alkyl or alkoxy having in each case from 1 to 6 carbon atom~ and/or straight-chain or branched halogenoalkyl or halogenoalkoxy having in each case from 1 to 6 carbo~ atom~ and from 1 to 13 identical or different halogen atoms;
R'~ represents atraight-chain or branched alkvl having from 1 to 8 carbon at~ms which i~ optio~ally substi-tuted once or more than once by identical or differ-ent substituents, po~sible substituents being~
halogen - in particular fluorine, chlorine, bromine and/or iodine - cycloalkyl having from 3 to 8 carbon atoms or heterocyclyl, the heterocyclyl radical being a five- to seven-membered optionally ben~o-fu~ed, saturated or unsaturated heterocycle having from 1 to 3 identical or different hetero atom~ - in LeA 29 658 - 14 -. : - : :: :, :

particular nitrogen, oxygen and/or ~ulphur;
Rl2 furthermore represents cYcloalkyl having from 3 to 7 carbon atoms which is optionally substituted once or more than once by identical or different substit-uents comprising halogen - in particular fluorine, chlorine, bromine and/or iodine - and/or ~traight-chain or branched alkyl having from 1 to 4 carbon atoms;
Rl2 furthermore repre~ents arylalkYl or arYl having in each case fro~ 6 to lO carbon atom~ in the aryl moiety and optionally from 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, which are in each ca~e optionally substituted in the aryl moiety once or more than once by identical or different sub~tituents, or represents a saturated or unsaturated, five- to seven-membered heterocyclyl radical having from 1 to 3 identical or different hetero atoms - in particular nitrogen, oxygen and/or sulphur - which is optionally substituted once or more than once by identical or different substitu-ents, possible substituents of aryl or heterocyclyl being in each ca~e~
halogen, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, alkoxy, :~ :
alkylthio, alkylsulphinyl or alkylsulphonyl having in each ca~e from 1 to 6 ~arbon atoms, in each ca~e ~traight-chain or branched halogenoalkyl, halogeno-alkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl ha~ing in each case from 1 to : -:
6 carbon atom~ and from 1 to 13 identical or , . . .

'~

' ' ` ~ ~:
L~A 29 658 - 15 -, ~ . - . , -.,, ., : . , .:

;~11Y6 i/3 different halogen atoms, in each ca~e straight-cha~n or branched alkoxycarbonyl or alkoximlnoalkyl having in each case from 1 to 6 carbon atoms in the indi-vidual alkyl moieties, and phenyl which is optional-ly substituted once or more than once by identical or different sub~tituents comprising halogen and/or straight-chain or branched alkyl or alkoxy ha~ing in each case from 1 to 6 carbon atoms and/or straight-chain or branched halogenoalkyl or halogenoalkoxy ha~ing in each case from 1 to 6 carbon atom~3 and from 1 to 13 identical or different halogen aSoms and n represento a nu~ber 0, 1 or 2.

Particularly preferred compounds of the form~la (I) are those in which R1 represents hydrogen or in each case straight-chain or branched alkyl, alkoxy, alkylthio or alkyl-sulphonyl having in each case from 1 to 6 carbon ~:
atoms, or furthermore represents straight-chain or branched halogenoalkyl having from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms - in particular fluorine, ahlorine or bromine - or represents cycloalkyl ha~ing from 3 to 7 carbon a~oms, R2 represents a radical of the formula -NR3R9, -~
R3, R6 and R7 independeDtly of one another in each case represent hydrogen, fluorine, chlorine, bromine, amino or nitro, LeA 29 658 - 16 -~ J~73 R4 repre~ent~ hydrogen, fluorlne, chlorine, bromine, cyano or nitro, or repreaents one of the radical~
-Rl, -O-Rl, -S-Rl, -S (O) -Rl, -SO2-Rl, -SO2-ORl, -SO2-NRllRl, -CO-ORl, -C~O-NRllRl -o-sO2-Rl, -N(Rll)-S02-Rl, _NRllRlo -NH-~(O)(Rll)(ORl) or -NEI-P(O) (ORll) (ORl) R5 repre~ent~ nitro, cyano, fluorine, chlorine or brom-ine or repre~ents ~traight-chain or branched halo-genoalkyl having from 1 to 4 carbon atom~ and from 1 to 9 identlcal or different halogen atom~ - in particular fluorine, chlorine or bromine - and X represent~ oxygen or ~ulphur, where R8 represents hydrogen, straight-chain or branched alkyl ha~ing from 1 to 6 carbon atoms or straight-chain or branched halogenoalkyl having from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atom~ - in particular fluorine, chlorine or bromine - and furthermore represents a radical of the formula -CO-Rl2 or a radical of the formula -S(O)~-R
R9 represent~ straight-chain or bra~ched alkyl having from 1 to 6 carbon.atom~ or straight-chain or branched halogenoalkyl having from 1 to 6 carbon atom a~d from 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine or bromine - and furthermore represent~ a radical of the formula -CO-R12 or a radical of the formula -S (O) -Rl2, R10 repre~ent~ hydrogen;
R10 furthermore repre~ent~ Rtraight-chain or branched .-: ~
::

LeA 29 658 - 17 -- ~llY~73 alkyl having from 1 to 12 carbon atoms which is optionally ~ubatituted once or twice by identical or different substituents, possibleieubstituent~ being:
cyano, carboxyl, carbamoyl, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylaulphonyl, alkoxycarbonyl, N-alkyli~minocarbonyl, N,N-dialkylaminocarbonyl or alkylsulphonylaminocarbonyl ha~ing in each ca~e from 1 to 6 carbon atoms in the individual alkyl moietie~, or heterocyclyl, the heterocyclyl radical being a fi~e- to se~en-membered, optionally ben~o-fused, Raturated or unsaturated heterocycle ha~ing from 1 to 3 identical or different hetQro atoms - in particular nitrogen, oxygen and/or sulphur;
Rl furthermore represeat~ straight-chain or branched haloqenoalkyl having from 1 to 6 carbon atom~ and from 1 to 13 identical or different halogen atoms -in particular fluorine, chlorine and/or bromine, Rl furthermiore represefits alkenyl or alkin~l ha~ing in each case from 2 to 6 carbon atoms ~ which are in each case optionally sub~tituted on~e to three time~
by identical or different halogens - in particular fluorine, chlorine and/or bromine;
Rl furthermore representz cycloalkyl having from 3 to 7 carbon atoms which iB optionally sub~tituted once to three times by identical or dif f erent substit-uents co~prising halogen - in particular fluorine, chlorine and/or bromine - and/or straight-chain or branched alkyl ha~i~g from 1 to 3 carbon atoms;
Rl furthermore represents phenylalkyl or phenyl having LeA 2g 658 - 18 -optionally from 1 to 3 carbon atoms in the ~tralght-chain or branched alkyl moiety, which are in each case optionally sub~tituted in the phenyl moiety once to five times by identical or di$ferent sub-~tituents, or represents a saturated or unsaturated, five- to ~even-membered heterocyclYl radical havi~g from 1 to 3 identical or different hetero atoms - in particular nitrogen, oxygen and/or sulphur - which i8 optionally ~ubstituted once to three times by identiaal or diffsrent sub~tituent~ and/or is benzo-fu~ed, possible sub~tituents of phenyl or hetero-cyclyl being in each case:
fluorine, chlorine, bromine, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkyl-sulphonyl having in each ca~e from 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkyl~ulphonyl having in each case from 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atoms, in each case ~traight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each caae ~rom 1 to 4 carbon atomR in the individual alkyl moieties, and phenyl which i~ optionally sub~tituted onae to ~ive times by identical or dif~erent aubstituents com-prising fluorine, chlorine, bromine and/or straight-chain or branched alkyl or alkoxy haYing in each case from 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl or halogenoalkoxy having LeA 29 658 - 19 -in each ca~e from 1 to 4 carbon atom~ and from 1 to 9 identical or different halogen atoma;
R11 represents hydrogen:
R1l furthermore repre~ents straight-chain or branched alkyl having from 1 to 12 carbon atoms which i~
optionally substituted o~ce or twice by identical or different ~ubstituent~, pos ible ~ubstituents be~ng:
cyano, carboxyl, carbamoyl, in each ca~e ~traight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, N-alkylaminocar~onyl, N,N-dialkylaminocarbonyl or alkylsulphonylaminocarbonyl having in each ca~e from 1 to 6 carbon atom~ in the individual alkyl moieties, or heterocyclyl, the heterocyclyl radical being a five- to neven-membered, optionally ba~zo-fused, saturated or unsaturated heterocycle ha~ing from 1 to 3 identical or different hetero atoms - in particular nitrogen, oxygen and/or sulphur;
Rl' furthermore repra~ents straight-chain or branc~ed haloqenoal~yl having from 1 to 6 carbon atom~ and from 1 to 13 identical or different halogen atoms -in particular fluorine, chlorine and/or bromine, R11 furthermore repreaent~ alk~nyl or alkinyl ha~ing in each case from 2 to 6 carbon atoms, which are in each case optionally ~ubstituted once to thr~e time~
by identical or different halogen~ - in particular fluorine, chlorine and/or bromine;
Rll furthermore represents cycloalkyl having from 3 to 7 carbon atoms which is optionally ~ubstituted once to three times by identical or different LeA 29 658 - 20 -:`

~i.l..`J673 substituent~ comprising halogen - in particular fluorine, chlorine and/or bromine - and/or straight-chain or branched alkyl having from 1 to 3 carbon atoms;
~11 furthermore repre~ent~ phe~YlalkYl or ~henYl having optionally from 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, which are in each case optionally substituted in the phenyl moiety once to five time~ by identical or different ~ub~ti-tuents, pos~ible ~ubstituenta of phenyl being in ~ach case:
fluorine, chlorine, bromine, cyano, nitro, amino, N-acetylamino, in each caee straight-chain or branched alkyl, alkoxy, alkylthio, alkyl~ulphi~yl or alkyl-sulphonyl having in each case from 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogonoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkyl~ulphonyl having in each ca~e ~rom 1 to 4 carbon ato~ and from 1 to 9 identical or different haloge~ atom~, in each ca~e straight-chain or branched alkoxycarbonyl or alkoxi~inoalkyl having in each caee from 1 to 4 carbon atoms in the individual alkyl moietie~, and phenyl which i8 optionally substituted once to five times by identical or different aubstitu~nto com-pri~ing fluorine, chlorine, bromine and/or ~traight~
chain or branched alkyl or alkoxy having in each ca~e from 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl or halogenoalkoxy ha~ing in each ca~e from 1 to 4 carbon atoms and from 1 to LeA 29 65~ - 21 -t673 9 identical or different halogen atom~;
Rl2 represent~ straight-chain or branched alkyl having from 1 to 12 carbon atoms which i~ optionally substitutad once or twice by identical or different substituents, possible substituent~ being:
cycloalkyl having from 3 to 7 carbon atoms or heterocyclyl, the heterocyclyl radical being a five-to seven-membered, optionally benzo-fused, ~aturated or unsaturated heterocycle having from 1 to 3 identical or different hetero atoms - in partiaular nitrogen, oxygen and/or ~ulphur;
R12 furthermore represents haloaenoalkyl having from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms - in particular fluorine, chlorine and/or bromine, Rl2 furthermore repre~ents cvcloalkyl having from 3 to 7 carbon atoms which i8 optionally substituted once to three times by identical or dif$erent s~bstit-uents com~rising halogen - in particular fluorine, chlorine and/or bromine - and/or ~traight-chain or branched alkyl having from 1 to 3 carbon atoms;
Rl2 furthermore represents DhenylalkYl or ~henvl having optionally from 1 to 3 carbon atom~ in the ~traight-chain or branched alkyl moiety, which are in each case optionally ~ubstituted in the phenyl moiety once to five times by identical or different substi-tuents, or repre~ent~ a saturated or un~aturated, five- to eeven-membered heterocyclyl radical having from 1 to 3 identical or different hetero atoms -in particular nitrogen, oxygen and/or sulphur - which ~eA 29 658 - 22 -~.L1~73 i~ optionally substituted once to three tlmes by identical or different ~ub~tituents and/or is benzo-fused, pos~ible sub~tituents of phenyl or hetero-cyclyl being in each case:
fluorine, chlorine, bromine, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkyl~ulphinyl or alkyl-sulphonyl having in each case from 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case from 1 to 4 carbon atom~ and from 1 to 9 identical or different halogen atoms, in each case ~traight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each ca~e from 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl wh~ch i~ optionally substituted once to five times by identical or different subetituents com-pri~ing fluorine, chlorine, bromine and/or straight-chain or branched alkyl or alkoxy having in each case from 1 to 4 carbon atom~ and/or straight-chain or bra~ched halogenoalkyl or halogenoalkoxy having in each case from 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atoms and 25 n represents a number 0, 1 or 2.
-Very particularly preferred co~pounds of the formula are those in which Rl repre~ents hydrogen or repre~ents in each case LeA 29 658 - 23 - ::

~::

~l~JG7~

straight-chain or branched alkyl, alkoxy, alkylth~o or alkyl~ulphonyl having in each case from 1 to 4 carbon atoms, or furthermore represents ~traight-chain or branched halogenoalkyl having from 1 to 4 carbon atoms and from 1 to 9 identical or dif4erent halogen atom~ - in particular fluori~e, chlorine or bromine - or represents cycloalkyl having 3, 5 or 6 carbon atoms, R2 represents a radical of the formula -NR0R9, R3, R6 and R7 independently of one another in each case represent hydrogen, fluorine, chlorine, bromine,--amino or nitro, R~ repre~ent~ hydrogen, fluorine, chlorine, bromine, cyano or nitro, or repre~ent~ one of the radicals -R10, -O-Rl, -S-R10, -S(O)-R10, -SO2-R1, -SO2-OR', -SO2-NRllRl, -CO-ORl, -CO-NRllRl -o-So2-Rl, -N(~ll)-SO2_Rlo~ _NRllRlo -N~-P(O)(R1l)(ORl0) or -NH-P (O) (ORll) (ORl) R5 repre~ents nitro, cyano, fluorine, chlorine or brom-ine, or straight-chair, or branched halogenoalkyl having from 1 to 3 carbon atoms and from 1 to 7 ~dentical or dif~erent halogen atoms, and X represents oxygen or sulphur, w~ere R8 represents hydrogen, straight-chain or branched alkyl having from 1 to 4 carbon atoms or straight-chain or branched halogenoalkyl having 4rom 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine or bromine - and furthermore repre~ents a radical of the formula -CO-Rl2 or a radical of the formula LeA 29 658 - 24 -.,, : ,. . , .. ' ' .. ~ ', ' ' - S ( ) n~ Rl2 ~
R9 repre~ents straight-chain or branched alkyl having from 1 to 4 carbon atoms or straight-chain or branched halogenoalkyl having from 1 to 4 carbon atom~ and from 1 to 9 identical or different halogen atoms - in particular fluorine, chlorine or bromine - or furthermore represents a radical of the formula -CO-Rl2 or a radical of the formula -S~O)j~-Rl2, Rl represents hydrogen;
Rl~ furthermore represents ~traight-chain or branched alkyl having from 1 to 8 carbon atoms which is :
optionally aubstituted once, possible ~ub~tituents being: -cyano, carboxyl, carba~oyl, in each case ~traight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkyl~ulphonyl, alkoxycarbonyl, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl or alkylsulphonylaminocarbonyl having in each case from --1 to 4 carbon atoms in the individual alkyl ~oieties, or heterocyclyl, the heterocyclyl radical being a five- or ~ix-membered, optionally benzo-fused, saturated or aromatic heterocycle ha~ing from 1 to 3 identical or different hetero atomQ - in particular nitrogen, oxygen and/or sulphur: :
Rl ~urther~ore represents straight-chain or branched halogenoalk~l having from 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atom~ -in :
particular fluorine, chlorine and/or bromine, ~: ;
Rl ~urthermore repre~ent~ alkenyl or alkinyl having in each case from 2 to 6 carbon atoms, which are in LeA 29 658 - 25 ~

: ~ h ~

each case optionally substituted once to three tlmes by identical or different halogens - in particular fluorine, chlorine and/or bromine;
Rl furthermore represents cvcloalkyl having 3, 5 or 6 carbon atoms which is optionally substituted once to three times by identical or different substituents comprising halogen - in particular fluorine, chlorine and/or bromine - and/or stralght-chain or branched alkyl having from 1 to 3 carbon atoms;
Rl furthermore repre~ents henylalkvl or ~henyl having optionally from 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, which are in each aase optionally 6ub~tituted in the phenyl moiety once to three times by identical or different ~ub-stituents, or repre~ents a saturated or aromatic, five- or six-membered heterocyclyl radical having from 1 to 3 identical or different hetero atoms - in particular nitrogen, oxygen and/or sulphur - which is optionally substituted once to three times by identical or different subetituents and/or is benzo-fused, possible substituents of phenyl or hetero-cyclyl being in each case~
fluorine, chlorine, bromine, cyano, nitro, amino, N-acetylamino, in each ca~e straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or al~yl-sulphonyl having in each case from 1 to 3 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, haogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case from l to 3 carbon atoms and , ~

LeA 29 658 - 26 -~1 L~73 from 1 to 7 identical or different halogen atom~, in each ca~e straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case from l to 3 carbon atom~ in the individual alkyl moieties, and phenyl which i8 optionally substituted once to three times by identical or dif~erent substituents com-prising fluorine, chlorine, bromine and/or straight-chain or branched alkyl or alkoxy having in each case from 1 to 3 carbon atoms and/or straight-chain or branched halogenoalkyl or halogenoalkoxy having in each ca~e 1 to 3 carbon atom~ and 1 to 7 identi-cal or different halogen atoms;
R11 represents hydrogen;
Rll furthermore rapresent~ straight-chain or branched alkyl having from 1 to 8 carbon atom~ which is optionally substituted once, possible ~ubstituents being:
cyano, carboxyl, carbamoyl, in each case ~traight-chain or branched alkoxy, alkoxyal~oxy, alkylthio, alkylsulphinyl, alkyl~ulphonyl, alkoxycarbonyl, N-alkyla~i~ocarbonyl, N,N-dialkylami~ocarbonyl or alkylsulphonylaminocarbonyl having in each case rom 1 to 4 carbon atoms in the individual alkyl moieti~s, or heterocyclyl, the heterocyclyl radical being a five- or 6ix-membered, optionally benzo~
fused, saturated or aromatic heterocycle having from 1 to 3 identical or different hetero atom~ - in particular nitrogen, oxygen and/or sulphur; :: ~:
R'l furthermore repre~ents straight-chain or branched halogenoalk~l having from 1 to 4 carbon atoms and LaA 29 658 - 27 -~llY~ ~3 from 1 to 9 identical or different halogen atoms -in particular fluorine, chlorine and/or bromine, Rll furthermore represent~ alkenyl or alkinyl having in each case from 2 to 6 carbon atoms, which are in S each ca~e optionally sub~ti uted once to three times by identical or different halogens - in particular fluorine, chlorine and/or bromine;
Rll furthermore representa cycloalkyl having 3, 5 or 6 carbon atoms which i8 optionally sub~tituted once to three time~ by identical or different ~ub~tituents comprising halogen - in particular fluorine, chlorine and/or bromine - and/or etraight-chain or branched alkyl ha~ing from 1 to 3 carbon atom~;
Rll furthermore repre~entg phenYlalkvl or ~henYl ha~ing optionally fro~ 1 to 3 carbon atoms in the ~traight-chain or branched alkyl moiety, which are in each ca~e optionally substituted in the phenyl moiety once to three timeR by identical or different sub~titu0nts, possible ~ub~tituent~ o phenyl being in each case:
fluorine, chlori~e, bromine, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkyl-~ulphonyl having in each case from 1 to 3 carbon .~5 atom~, in each case straight-chain or branched halogenoal~yl, halogenoalkoxy, halogenoalkylthio, halogenoalkylaulphinyl or halogenoalkyl~ulphonyl having in each case from 1 to 3 carbon atGm~ and from 1 to 7 identical or different halogen atom~, in each caue ~traight-chain or branched al~oxycarbonyl LeA 29 658 - 28 -", ~ ~ . .r ~ ~

Y~73 or alkoximinoalkyl having in each ca~e ~rom 1 to 3 carbon atoms in the individual alkyl moietle~, and phenyl which i8 optionally ~ubstituted once to three times by identical or dif~erent ~ubstituent~ com-prising fluorine, chlorine, bromine and/or ~traight-chain or branched alkyl or alkoxy having in each case from l to 3 carbon atom~ and/or ~tra~ght-chain or branched halogenoalkyl or halogenoalkoxy~ having in each caEe 1 to 3 carbon atom~ and 1 to 7 identi-7 0 cal or different halogen atoms;
R~2 repre3ent~ ~traight-chain or branched al~vl having from 1 to 4 carbon atom~ whiah i~ optionally ~ub~ti-tuted on~e, po~sible sub~tituent~ being: :
cycloalkyl having 3, 5 or 6 carbon atom~ or hetero-cyclyl, the heterocyclyl radical being a five- or six-membered, optionally benzo-fused, saturated or aromatic heterocycle having from 1 to 3 identical or differe~t hetero atom~ - in particular nitrogen, oxygen and/or sulphur; -~ :
R12 furth~rmore represent~ straight-chain or branched haloaenoalk~l ha~ing fro~ 1 to 4 carbon atom~ and -from 1 to 9 identical or di~ferent halogen atoms -in particular fluorine, chlorine and/or bromine, R1~ furthermore represents cycloalkyl having 3, 5 or 6 carbon atoms which is optionally sub~tituted once to three times by identical or di~ferent ~ubstituent~
compri~ing halogen - in particular fluori~e, chlorine and/or bromine - and/or ~traight-chain or branched alkyl having from 1 to 3 carbon atoma;
R12 furthermore represent~ phenvlalkYl or phenvl having Le~ 29 658 - 29 -optionally from 1 to 3 carbon atom~ in the stralght-chain or branched alkyl moiety, which are in each case optionally substituted in the phenyl moiety once to three times by identical or different substituents, or repre6ent~ a saturated or aromatic, five- or six-membered heterocyclyl radical having from 1 to 3 id~ntical or different hetero atoms - in particular nitrogen, oxygen and/or sulphur - which i5 optionally sub~tituted once to three times by identical or different substituents and/or i~ benzo-fused, pos~ible substituents of phenyl or hetero-cyclyl being in each case:
fluorine, chlorine, bromine, cyano~ nitro, amino, N-acetylamlno, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkyl-sulphonyl having in each case from 1 to 3 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkyl~ulphonyl having in each case from 1 to 3 carbon atoms and from 1 to 7 identical or differenS halogen atoms, in each ca~e atraight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each ca~e ~rom 1 to 3 carbon atoms in the individual alkyl moieties/ and phenyl which i8 optionally sub~tituted once to three time~ by identical or dif~erent substituents com-pri~ing fluorine, chlorine, bromine and/or straight-chain or branched alkyl or alkoxy having in each case ~rom 1 to 3 carbon atoms and/or str~ight-chain or branched halogenoalkyl or halogenoalkoxy having eA 29 658 - 30 -, in each case from 1 to 3 carbon atoms and from 1 to 7 identical or different halogen atoms and n represents a number O, 1 or 2.

Individually, and apart from the compounds li~ted in the Preparation Example~, the following eubstituted triazoli-none~ of the general formula (I) may be mentioned:

LeA 29 658 - 31 - ~.

- ~l.L~673 ~N
N~N~
3 1 7 (1) ll R ~R
R

Rl R2 R3 R4 Rs R~ R7 X
: - .
CH3 -NH-CH3 H OH CN H ~ O
CH3 -NH-CH3 H OH CN H ~
CH3 -NH-CH3 H OH No2 H F O
CH3 -NH-CH3 H OH N2 H Cl O
CH3 -NH-CH3 H OH CF3 H ~ O
CH3 -NH-CH3 Cl OH No2 H ~ O

CH3 -NH-CH3 N2 ~ CF3 H N02 0 CH3 -NH-CH3 H -O-CH3 CF3 ~ H O
CH3 -NH-CH3 H -O-CH3 No2 H F O

LeA 29 fi58 - 32 -~ilJ~)3 Rl R2 R3 R4 Rs R6 R7 X
CH3 -NH-CH3 H ~ CN H H O
CH3 -NH-CX3 H -O-CH(CH3)-COOC2H5 CN H Cl O
CH3 -~nH-CH3 H -O-CH2-CN CN H F O
CH3 -NH-CH3 H _o~O CN H Cl O

CH3 -NH-CH3 H -- C~O N2 H F O

CH3 -NH-CH3 H -O-CH2-C(Cl)=cH2 CN H H O
CH3 -NH-CH3 H -O-CH2-C(CI)=CH2 CN H ~ O
CH3 -rnH-CH3 F F CF3 H H O
CH3 -~nH-CH3 H -O-S02-CH3 CN H F O
CH3 -~nH-CH3 H -O-S02-CH3 CN H Cl O
CH3 ~NH-CH3 H -O-S02-CH3 N2 H Cl O

CH3 -NH-CH3 H -O-CHF2 CN H Cl O

CH3 -NH-CH3 H -O-CHF2 N2 H Cl O
CH3 -NH-CH3 H -SCH3 N2 H Cl O
CH3 -~nH-CH3 H -SCH3 N2 H F O

L~A 29 658 - 33 -~ i ~L ~

Rl R2 R3 R4 Rs R6 R7 X

CH3 -NH-CH3 H-SCH3 CF3 H Cl O
CH3 -NH-CH3 ~-SCH3 CF3 H Cl O
CH3 -NH-CH3 H-NH-CH3 CN H Cl O
CH3 -NH-CH3 H-NH-CH~ CN H F O

CH3 -NH-CH3 ~-NH-CH3 CF3 H ~i O
CH3 -NH-CH3 ~-N(CH3)2 CF3 H Cl O
CH3 -NH-CH3 H-N(CH3)2 CN H Cl O
CH3 -NH-CH3 H-N(CH3)2 CN H F O
CH3 -NH-CH3 H-N(CH3)2 N2 H ~ O

CH3 -NH-CH3 H. -NH-CH2-CH=CH2 N2 H F O
CH3 -MH-CH3 H -NH-cH2-cH=c~i2 CN H Cl O
CH3 -NH-CH3 H-NH-SO2-CH3 N2 H Cl O
CH3 -NH-C~3 H-N(CH3)-s02-cH3 N2 H Cl O

CH3 -NH-CH3 H-COOCH3 CN H Cl O :.
CH3 -MH-CH3 H-CO-NH-CH3 CN H ~ O
CH3 -NH-CH3 H-CO-N(CH3)2 CN H F O
CH3 -NH-CH3 H-S(O)-CH3 CN H F

LeA 29 658 - 34 - ~ :
~ '; ~ ' 6 7 ~

R~ R~ R3 R~ R5 R6 R7 X
-CH3 -NH-CH~ H-S02-CH~, N2 H F O
CH3 -NH-CH3 H-S02-NH-CH3 N2 H Cl O

CH3 -NH-CH3 H ( ) CN H F O
P~

CH3 -NH-CH3 H CN H Cl O
-N~P(Oc2~)2 C2Hs -NH-CH3 Cl H CN H Cl O
C2Hs -NH-CH3 N2 H CF3 H NO2 O
C2Hs -NH-CH3 H CH3 NO2 H H O
C2Hs -NH-CH3 H C2H5 NO2 H H O
C2Hs -NH-CH3 Cl F CF3 H Cl O

C2Hs -NH-CH3 ~ a CN a H O
C2Hs -NH-CH3 H -OCH3 CN H F O
C2Hs -NH-C2H5 H-OCH3 CN H F O
C2Hs -NH-C2Hs Cl F CF3 H C9 C2Hs -NH-C2H5 H-NH-SO2-CH3 CN H F O
C2Hs -NH-C2H5 H-O-CH(CH3)-C~CH CN H F O
C2Hs -NH-C2H5 H-S-C2Hs CN H F O
n-C3H7 -NH-CH3 N2 H CF3 H N02 LeA 29 658 - 3s -Rl R~ R3 R~ ~5 R6 R7 X
.
n-C3H7 -NH-CH3 H OH CN H Cl O
n-C3H7 -NH-CH3 H -OCH3 CN H F O
n-C3H7 -NH-CH3 H -NH-S02-CH3 CN H Cl O
n-C3H7 -NH-CH3 H -O-CH(CH3)-C_CH CN H F O
n-C3H7 -NH-CH3 H -S-CH(CH3)-COOCH3 CN H F O
n-C3H7 -NH-CH3 H -O-CH2-COOCH3 CN H F O

n-C~H7 -NH-CH3 H CH3 N02 H H O
i-C3H7 -NH-CH3 H CH3 N02 H H O
i-C3H7 -NH-CH3 H C~ CN H F O
-o~C~ -i-C3H7 -NH-CH3 H H NO2 H H Oi-C3H7 -NH-CH3 H -cooc2Hs CN H F O
i-C3H7 -NH-CH3 H -CO-NH-CH3 CN H Cl O

i-C3H7 -NH-CH3 H -S-C2Hs CN H F O
i-C3H7 -NH-CH3 H -S-(CH2)2-Oc2HS CN H F O
-NH-CH3 N2 H CF3 H NO2 ~ --NH-CH3 H OH CN H F O .;~

~ -NH-CH3 H -OCH3 CN H F O

LeA 29 658 - 36 ~
, ~ :

7c3 Rl R2 R3 R~ Rs R6R7 X
-NH-CH?, H -CO-NH-CH3 CN H F O

-NH-CH3 H ~ SO2~ CN H F O

-NH-CH3 H ,n CN H F O

-NH-CH3 H J~ CN H F O

-NH-cH3 H 0 ~ CN H F O

~ -N(CH3)2 N02 H CF

LeA 29 658 - 37 -~.Li~673 Rl R~ R3 R4 R5 R6 R7 X
. ~
-N(CH3)2 Cl H CF3 H H O

-N(CH3)2 H OH CN H Cl O

-NH-CH3 H-N(CH3)2 CN H F O ~ ~

~ -NH-CH3 H -O-CH(CH3)-COO-C2H5 CN H F O - --N(CH~)2 H CN ~ F O
P(OC2H~)2 CH3 -N(CH3)2 H ~ CN H F O ~ ~ ---N~-P~, LeA 29 658 - 38 -' ' Rl R2 R3 R4 R5 R6 R7 X
CH3 -N(C~3)2 H OH CN H F O
CH3 -N(cH3)2 H OH CN H ~ O
CH3 -N(CH3)2 H OH No2 H a o CH3 -N(CH3)2 H OH No2 H F O
CH3 -N(CH3)2 H -NH2 CN H F O
CH3 -N(CH3)2 H -NH2 CN H ~ O
CH3 -N(cH3)2 H -OC~3 CN H F O
CH3 -N(CH3)2 H -OCH3 CN H F S

CH3 -N(CH3~2 H -S-CH3 CN H F O
CH3 -N(CH3)2 H -S-CH3 CN H F S
CH3 -N(CH3)2 H -CO-NH-CH3 CN H F O
CH3 -N(CH3)2 H -CO-N(CH3)2 CN H ~ O
CH3 -N(CH3)2 H -NH-SO2CH3 CN H` Cl CH3 -N(CH3~2 H -NH-SO2-C2Hs CN H F S

CH3 -N(cH3)2 H -OCHF2 CN H F O
CH3 -N(cH3)2 H -OCHF2 CN H F O
CH3 -N(CH3)2 H -N(CH3)2 CN H F O
CH3 -N(CH3)2 H -NH-C2H5 CN H F O
CH3 -N(CH3)2 H -O-CH2-C(CI)=CH2 CN H F O
CH3 -N(CH3)2 H -O-SO2-CH3 CN ~ F O
CH3 -N(CH3)2 H -SO2-O-cH3 CN H ~ O

LeA 29 658 - 39 _ Rl R' R3 R4 R5 R6 R7 X
CH~ -N(cH3)2 H ~ CN H F O
--O
CH3 -N(CH3)2 H -o-cH2-c6Hs CN H F O
CH~ -N(cH3)2 H _o ~ CN H F O

CH3 -N(CH3)2 H _o ~ CN H F O
' -CH3 -N(CH3)2 H -O-CH(CH3)-COOCH3 CN H F O
CH3 -N(CH3)2 H -O-CH(CH3)-COOCH3 NO2 H F O :~
CH3 -N(CH3)2 Cl -O-CH(CH3)-COOCH3 CF3 H ~ o -:
CH3 -N(cH3)2 ~ -O-CH(CH3)-C=CH CF3 H ~ O ~
CH3 -N(CH3)2 H -O-CH(CH3)-C=CH N2 H F O ~ :
C2HS -N(CH3)2 H -O-CH(CH3)-C=CH N2 H F O
C2H5 -N(CH3)2 H -O-CH2-C--CH N2 H F O
-:' -:' .~
C2H5 -N(CH3)2 H-o-cH2-c6Hs CN H P O -C2H5 -N(CH3)2 H -N(CH3)2 CN H F O
C2H5 -N(C~3)2 H -N(CH3)2 N2 H F O
C2H5 -N(cH3)2 H -OCH3 N2 H F O
C2H5 -N(CH3)2 H -OCH3 CN H ~ O
C2H5 -N(cH3)2 H OH CN H ~ O
CH3 -N(CH3)2 H SH CN. H F O

, , LQA 29 658 - 40 - ~

' ' ~ 7 3 Rl R2 R3 R~ R5 R6 R7 X__ CH~ -N(CH3)2 H SH CN H F O
i-C3H7 -N(CH3)2 H SH CN H F O
i-C3H7 -N(CH3)2 H OH CN H F O
i-C~H7 -N(CH3)2 H OCH3 CN H F O
jC~H7 -N(cH3)2 N2 H CF3 H N2 i-C3H7 -N(CH3)2 Cl H CN H ~ O
i-C3H7 -N(CH3)2 H Cl CN ~ H O
i-C3H7 -N(CH3)2 H -S-CH(CH3)-COOCH3 CN H F O

i-C3H7 -N(CH3)2 H -G-CH2-CN CN H F O
i-C3H7 -N(CH3~2 Ho-c(cl)=cH2 CN H F O
i-C3H7 -N(CH3)2 H-COOCH3 CN H P O
i-C3H7 -N(CH3)2 H-N(CH3)-SO2-CH3 CN H F O
i-C3H7 -N(CH3)2 H-N(CH3)-s02-c2H5 CN H F O
i-C3H7 -N(cH3)2 H-CO-NH-CH3 CN H F O
i-C3H7 -N(CH3)2 H-N(C2Hs)-SO2-CH3 CN H Cl O

CH3 -N(CH3)2 H -NH-SO2-CH3 CN H F O
CH3 -N(CH3)2 H -O-CH(CH3)-C=CH CN H F O
CH3 -N(cH3)2 H -O-CH2-CH=CH2 CN H F O
CH3 -N(CH3)2 H -O-CH2-C---CH CN H F O
CH3 -N(CH3)2 H -NH-S02-C2H5 CN H F O
CH3 -N(cH3)2 Cl -NH-S02-CH3 N2 H Cl O

LeA 29 658 - 41 -6 7 ~

Rl R2 R3 R~ R5 R6 R7 X
CH3 -N(CH3)2 H -NH2 CN H F O
CH3 -N(CH3)2 H OH CN H F O
CH3 -NtcH3)2 H SH CN ~ F O
CH3 -N(CH3)2 H SH CN H F O
CH~ -N(CH3)2 H -OCH3 CN H F O

CH3 -N(CH3)2 H -O-CH(CH3)-C=CH CN H F O
CH3 -N(CH3)2 H -O-CH2-CH=CH2 CN H F O
CH3 -N(CH3)2 H -O-CH2-C=CH CN H Cl O
CH3 -N(CH3)2 H -NH-SO2-C2Hs CN H F O
CH3 -N(CH3)2 H -NH-SO2-CH3 CN H F O

CF3 -NH-CH3 H F CN H ~ S

CF3 -NH-CH3 H OH No2 H F O

CF3 -NH-CH3 H -COOCH3 CN H Cl O
CF3 -NH-CH3 H -N(C~3)-s02-c2H~ CN
' ' ' ~ ~ .
: ~

LeA 29 658 - 42 - ~

6 7 ~

Rl R2 R3 R4 R5 R6 R7 X
_ . _ CF3 -NH-CH~ H Cl CN Cl H O
CF3 -NH-CH3 H-O-CH2-CH=CH2 CN H F O
CF3 -NH-CH3 H-NH-CH2-CH-~H2 CN H F O

F2C~H- -NH-CH3 H F CN H Cl O

F2CH- -NH-CH3 H-O-CH2-CH~CH2 CN H F O
F2CH- -NH-CH3 H-O-CH2-CH=CH2 CN H F S

F2CH- -NH-CH3 H-NH-so2-n-c4H9 CN H F O

F2CH- -N(CH3)2 H-S-C2H5 CN H F O
F2CH- -N(CH3)2 H-NH-SO2-C2H~ CNH Cl O
F2CH- -N(CH3)2 H CH3 NO2 H H O

F2CH- -N(cH3)2 H -O-CH2-C-CH NO2 ~ F O
F2CH- -N(cH3)2 H-COOC2H5 CN H F O
F2CH- -N(CH3)2 H-S~H(CH3)-COOCH3 CN H F O
CF3 -N(CH3)2 H-NH-S02-CH3 N2 H Cl O
CF3 -N(CH3)2 HO-SO2-CH3 CN H F O
CF3 -N(CH3)2 H -S02-CH3 CN H F O

,~

L~A 29 658 - 43 -: ` .

~.LlY673 ~`~

Rl R2 R3 R~ Rs R6 R7 X
CF3 -N(CH3)2 H -NH-CH(CH3)2 CN H Cl O
CF3 -N(CH3)2 H -O-CH2-C=CH CN H F O
CF3 -N(CH3)2 H -COOC2H5 CN H F O -~
CF3 -N(CH3)2 H -CO-NH-CH3 CN H F O
CF3 -N(CH3)2 H o-S02-CH3 CN H Cl O

CH3-S- -NtCH3)2 H -CH3 NO2 H H O
CH3-S- -N(CH3)~ H OH CN H F O
CH3-S- -N(CH3)2 H OH CN H Cl O
CH3-S- -N(cH3)2 H -S-C2H5 CN H F O :-CH3-S- -N(CH3)2 H -O-CH2-C~CH NO2 H F O -::
CH3-S- -N(CH3)2 H -COOCH3 CN H F O : --:
CH3-S- -N(CH3)2 H -NH-CH(CH3)2 CN H F O
CH3-S- -N(CH3)2 H -N(cH3)-so2-cH3 CN H F O ~ :
CH3-S- -NH-CH3 H -S-C2H5 CN H F O :
CH3-S- -NH-CH3 H -NH-cH2-cH=cH2 CN H F O 3~ ~
CH3-~- -NH-CH3 H -O-CH2-CN CN H F O ~:. -~: :

LeA 29 658 - 44 Rl R~ R~ R~ Rs RC R7 X
CH3-S- -NH-CH~ H -O-CH(CH3)-COOCH3 CN H F O
CH3-S- -NH-CH3 H -O-CH2-CfiH5 CN H F O
CH3-S- -NH-CH3 H -O-CH2-c6Hs N02 H F O
CH3-S- -NH-CH3 H -COOCH3 CN H Cl O
CH3-S- -NH-CH3 H ~ CN H F O
--O~ O

CH3-S(O~- -N(cH3)2 H -CH~ NO2 H H
CH3-S(O)- -N(cH3)2 ~ OH CN H F O
CH3-S(O)- -N(CH3)2 H OH CN H ~
CH3-S(O)- -N(CH3)2 H -S-C2H5 CN H F O
CH3-S(O)- -N(CH3)2 H -O-CH2-C=CH N02 H F O
CH3-S(O)- -N(CH3)2 H -COOCH~ CN H F O
CH3-S(O)- -N(CH3)2 H -NH-CH(CH3)2 CN H F O
CH3-S(O)- -N(CH3)2 ~ -N(CH3)-S02-CH3 CN H F O
CH3-S(O~- -NH-CH3 H -S-C2H5 CN H F O

CH3-S(O)- -NH-C~3 H -NH-CH2-CH=CH2 CN H F O
CH3-S(O)- -NH-CH3 H -O-CH2-CN CN H F O
CH3-S(O)- -NH-CH3 H -O-SO2-CH3 CN H . F O
CH3-S(O)- -NH-CH3 H -O-CH(CH3)-COOCH3 CN H F O
CH3-S(O)- -NH-CH3 H -O-CH2-C6HS CN H F O
CH3-S(O)- -NH-CH3 H -O-CH2-C~H5 NO2 H F O
CH3-S(O)- -NH-CH3 H -COOCH3 CN H Q O
:

LeA 29 658 - 45 ~
~. -lY673 Rl R2 R3 R4R5 R6 R7 x CH3-S(O)- -NH-CH3 H ~ CN H F O
--O-C~ O
CH3-SO2- -N(CH3)2 H -CH3NO2 H H O
CH3-SO2- -N(CH3)2 H OHCN H F O
CH3-SO2- -N(CH3)2 H OHCN H Cl O

CH3-SO2- -N(CH3)2 H -S-C2H5 CN H F O
CH3-SO2- -N(cH3)2 H -O-CH2-C=CH NO2 H F O
CH3-SO2- -N(CH3)2 H-COOCH3 CN H F O
CH3-S02- -N(CH3)2 H-NH-CH(CH3)2 CN H F O
CH3-S02- -N(CH3)2 H-N(CH3)-SO2-CH3 CN H F

CH3-SO2- -NH-CH3 H -NH-CH2-CH=CH2 CN H F O

CH3-SOk- -NH-CH3 H -O-CH(CH3)-COOCH3 CN H F O
CH3-S02- -NH-CH3 H-o-cH2-c6H5 CN H F O

CH3-SO2- -NH-CH3 H-COOCH3 CN H Cl O
CH3-SO2- ~NH-CH3 Hn CN H F O
--O-c~2`O :~ :

LeA 29 658 - 46 6 ~ ~

Rl R2 R3 R4 Rs R6 R7 X
.
CH30 -N(CH3)2 N2 H CF3 H N2 CH30 -N(CH3)2 H F CN H H O
CH30 -N(CH3)2 H Cl CN Cl H O
CH30 -N(cH3)2 H -OCH3 CN H F O
CH30 -N(CH3)2 H -S-C2Hs CN H F O
CH30 N(CH3)2 H -O-CH2-CH=CH2 CN H Cl O

CH30 -N(CH3)2 H NH2 CN H F O
CH30 -N(CH3~2 H -N(CH3)-S02-CH3 CN H F O
CH30 -N(CH3)2 H -COOCH3 CN H F O
CH30 -N(CH3)2 Q H N02 H Cl O
CH30 -N(CH3)2 H -S-CH(CH3)-COOCH3 CN H Cl O
CH30 -N(CH3)2 H -O-CH(CI)=CH2 CN H F O

CH30 -NH-CH3 H -OCH3 CN H Cl O
C~30 -NH-CH3 H -SCH3 CN H Cl O
CH30 -NH-CH3 H -O-CH(CH3)-C--CH CN H F O
CH30 -NH-CH3 H -O-CH~CH3)-C_CH CN H F S
CH30 -NH-CH3 H -O-CH2-CH=CH2 CN H F
.-LeA 29 658 - 47 -.

R' R2 R3 R~ Rs R6 R7 X
CH30 -NH-CH3 H -NH-CH2-CH=CH2 CN H F O
CH30 -NH-CH3 H -NH-CH2-CH=CH2 N02 H F O

CH30 -NH-CH3 H -NH-S02-C2H5 CN H Cl O
CH30 -NH-CH3 H -NH-S02-c2H5 CN H F O

~H3 -NH-CF3 H -OCH3 CN H F O

CH3 -NH-CF3 H -O-CH(CH3)-C-~H CN H F O
CH~ -MH-CF3 H -NH-S02-C2~5 CN H F O

~H3 -NH-CF3 H -NH-S02-C2H5 CN H ~ O

CH~ -MH-CF3 H -COOCH3 CN H F O

H -N(cH3)2 H F CN H P O
H -N(CH3)2 H OH CN H F O
H -N(CH3)2 H -O-CH(CH3)-C_CH CN H F O
H -N(CH3)2 H -NH-S02-CH3 CN H F O

:: :
: ~,.', ~' - ,, LeA 29 658 - 48 -7 ~

Rl R2 R3 R~ Rs R6 R7 X
H -N(cH3)2 H -N(CH3)2 CN H F O
H -N(cH3)2 H -N(CH~)SO2-C2H5 CN H F O
H -N(CH3)2 H -NH-SO2-C2H5 CN H ~ O
H -N(CH3)2 ~ F CF3 H Cl O
H -NH-CH3 H -O-CH(CH3)-C_CH CN X F O

H -NH-CH3 H -O-CH(CH3)2 CN H F O

H -NH-CH3 H -O-CH(CH3)-CH2-OCH3 CN H F O

H -NH-CH3 H -O-(CH~2-NH-CH3 CN H F O

H -NH-CH3 H-O-CH2-C_CH CN H F O
H -N(CH3)2 HOH CN ~ F O
H -N(CH3)2 H-O-C2H5 CN H ~ O
H -NH-CH3 H-S-C2H5 CN H ~ O
H -N(CH3)2 H-NH-S02-CH3 CN H ~
H -N(CH3)2 H-O-CH2-C_CH C~ H F O

LeA 29 658 - 49 -U8 ing, for example, 3-m~thyl-4-dimethylamino-1,2,4-triazolin-5-one and 2,4,5-trlfluorobenzonitrile ac starting material~, the ~equence of reaction of proce~
(a) according to the invention can be repre~ented by the S following formula ~cheme:
F

~C ~ ,N(C~)2 F ~

N~o ~ F
H CN ~C\ ,N( ~ N
N~N/~o ,.
- HF
base ~ -F ~
CN , ~ , U~ing, for example, 1-(4-cyano-2,5-difluorophenyl)-3-methyl-4-dimethylamino-1,2,4-triazolin-5-oneandl-butin- -3-ol as ~tarting materials, the ~equence of reaction of proca~ (b) according to the invention can be repre~ented by the following formula sch~me~

LeA 29 658 - so -. , .

i 7 c~

~C N(~)2 N
N~o + HO CH~ G CH
F ~
F ~C ~ ,N~C02 N~o base ~1~¦ CE~
~0--CH-C~CH
CN -Using, for example, 1-(4-cyano-2-fluoro-S-methoxy-phenyl)-4-amino-3-methyl-1,2,4-triazolin-5-one as the :
starting compound and acetyl chloride as the acylating agent, the ~equence of rea~tion of process (c~ according to the invention can be represented by the ~ollowing formula scheme:

~o n~O
F~ ~ + acetyl chloridelb e F~ h CN CN ' LeA 29 658 ~ 51 - ~;

' ~, Using, for example, 1-(4-cyano-2-fluoro-5-methoxy-phenyl)-3-methyl-4-isopropylideneimino-1,2,4-triazolln-S-one as the starting compound and ~odium borohydride as the reducing agent, the ~equence of reaction of process (d) according to the invention can be represented by the following formula scheme:
N= ~C~)2 ~ ~ ,NKC~C~32 N~N ~ N~N ~

+ so~um borohydride F ~

CN CN ~ -:

A general definition of the lH-triazolinone3 re~uired as starting materials for carrying out proce~s (a) according to the lnvention is given by the formula (II). In this formula (II), R1, R2 and X preferably and particularly preferably represent those radicals which have already been mentioned as preferred and particularly preferred for the~e substituents in connection with the description of the compounds of the ~ormula (I) according to the invention.
The lH-triazolinones of the formula (II) are known or are obtainable by analogy with ~nown proces~eR (cf. e.g.
Chimica Acta Turcica 9, 381 ~1981]; EP 399 294; EP
422 469; J. Heterocycl. Chem. 10, 387-390 11973]; Indian J. Chem. 7, 959-963 [1969]; D~ 37 19 575; DE 38 03 523;
Liebigs Ann. Chem. 637, 135 [1960]; J. Heterocycl. Chem.

LeA 29 658 - 52 -16, 403 ~1979]; J. Heterocycl. Chem. 17, 1691 ~1980]t J.
Indian Chem. Soc. 57, 270-272 [1980~; Indian J. Chem.
Sect. B 22B, 270-271 [1983]: Chem. Ber. 98, 3025 [1965]:
~P 52-125168; Europ. J. Med. Chem. 18, 215 [1983]).

A general definition of the halogenobenzene derivatives furthermore required as starting materials for carrying out process (a) according to the invention is given by the formula (III). In this formula (III~, R3, R4, Rs, R6 - and R7 preferably and particularly preferably represent those radical~ which have already been mentioned as preferred and particularly preferred for these subetitu-ents in connection with the description of the compounds of the formula (I) according to the invention. Hal~
repre~ents preferably ~luorine, chlorine or bromine, in particular fluorine or chlorine.
The halogenobenzene derivatives of the formula (III) are generally known or are obtainable by analogy with known processes (cf. e.g. EP 191 181; EP 441 004; EP 431 373).
The compound 5-chloro-2,4-difluorobenzonitrile is not already known. It i~ obtained by reacting the known compound 2,4,5-trichloroben~onitrile (cf. e.g. EP -441 004) with potas~ium fluoride, optionally in the presence of a diluent such as, for example, tetramethyl-ene ~ulphone at temperatures o~ between 100C and 200C
(compare also in this respect the Preparation Examples).

A general definition of the substituted triazolinones -required a~ starting materials for carrying out process (b) according to the invention is given by the formula , ~eA 29 658 - 53 - ~ -- : .:

~l 3 ~673 (Ia). In this formula (Ia), R1, R2, R3, R6, R5, R7 and X
preferably and particularly preferably repre~ent thoee radicals which have already been mentionsd as being preferred and particularly preferred for the~e substitu-ents in connection with the description of the ~ubstancesof the formula (I) according to the invention. Hal2 represents preferably fluorine, chlorine or bromine, in particular fluorine or chlorine.
The substituted triazolinones of the formula (Ia) com-pounds according to the invention and obtainable by means of processe~ (a), (c) and/or (d) according to the inven-tion.

A general definition of the nucleophiles furthermore reguired as starting materials for carrying out process (b) according to the invention is given by the formula (IV). In this formula (IV), Rl3 preferably represents a radical of the formula -0-R1, -S-Rl or -NRl~Rl, where R10 and R1l preferably repre~ent those radicals which have already been mentioned as being preferred and particu-larly preferred for these sub~tituents in connection withthe desoription of the substances of the formula (I) according to the invention. The nucleophiles of the formula (IV) are generally known compounds of organic chemistry.

A general de~inition of the substituked triazolinone~ -required as ~tarting materials for carrying out process ;- i~
(c) according to the invention is given by the formula (V). In this formula (V), Rl, R3, R~, R5, R6, R' and X

LeA 29 658 - 54 --~ ~11Y673 :

preferably and particularly preferably ropro~ent tho~e radicale which have already been mentioned as being preferred and particularly preferred for the~e substitu-ent~ in connection with the description of the ~ub~tance~
of the formula (I) according to the invention.
Substituted triazolinones of the formula (V) aro not already ~nown. Thoy are, howevor, to a large extent the subject of the Applicant'~ a~ yet unpublished patent applications and are obtainable by means of the proces~e~
described theroin, for example by reacting 4-amino-lH-triazolinones of the formula (VIII), R ,N~
~ N ~Vl~
~0 H

in which Rl hao the meaning given above, with halogenobenzone derivative~ of the formula (III), 3 1 7 : - ~

~,~R6 :-. ~ ~ :
R - --in which :, ...

.: : ~ :
. .:: .' '~' ~ `.

. :, ~
:''-: ::: "
::: : ~: ~

LeA 29 658 - 55 - ~ ;

, ~ :~::

R3, R4, R5, R6 and R7 have the meaning given above and ~al1 repre~entr~ halogen, optionally in the pre~ence of a diluent and optionally in the presence of a reaction auxiliary, in analogy to the implementation o$ proceri~ (a) according to the invention.

4-Amino-lH-triazolinones of the formula ~VIII) are known or are obtainable by analogy with known proce~se~ (cf.
e.g. EP 294 666; J. Heterocycl. Chem. 10, 387-390 119731;
Indian J. Chem. 7, 959-963 l1969]; DE 37 19 575; DE
38 03 523; Liebigs Ann. Chem. 637, 135 [1960~; J. Hetero-cycl. Chem. 16, 403 11979]; J. ~eterocycl. Chem. 17, 1691 [1980]: ~. Indian Chem. Soc. 57, 270-272 ~1980~; Indian J. Chem. Sect. B 22B, 270-271 [1983]; Chem. Ber. 98, 3025 [1965]; JP 52-125168; Europ. J. ~ed. Chem. 18, 215 rl983]).

A general definition of the alkylating, acylating and sulphonylating agents furthermore requirad a~ starting ~aterials for carrying out procoss (c) according to the invention is given by the formula (VI). In thi~ formula ~VI), R9 represents pr~fsrably and particularly prefer-ably tho3e radicale which have already been mentioned a~
preferred and particularly preferred for these sub~titu-ent~ in connection with the deacription of the substances of the formula (I~ according to the in~ention. E repres-ent~ a conventional electron-attracting leaving radical such as, for example, halogen, in particular chlorine, bromine or iodine or, in the ca~e of the alkylating LeA 29 658 - 56 -" ~ ; ""~ " ~ " ~

agents, represents in each case optionally substitutedalkylsulphonyloxy, alkoxysulphonyloxy or arylsulphonyl-oxy, such as, in particular, methanesulphonyloxy, tri-~luoromethanesulphonyloxy, methoxysulphonyloxy, ethoxy-sulphonyloxy or p-toluenesulphonyloxy.
The alkylating, acylating and sulphonylating agent~ of the formula (VI) are generally known compounds of orga~ic chemistry.

A general de~inition of the substituted 4-alkylidene-imino-triazolinones required as starting material~ for carry~ng out process (d) according to the invention i8 given by the formula (VII). In this formula (VII), Rl, R3, R~, Rs, R6, R' and X preferably and particularly pre~erably represent those radicals which have already been men-tioned as being preferred and particularly preferred forthese substituents in connection with the description of the substances of the formula (I) accordi~g to the invention. Rl~ represents preerab1y hydrogen or straight~
chain or branched alkyl having rom 1 to 4 carbon atoms, in particular hydrogen, methyl or ethyl. R1s repre~ents pref~rably in each ~a~e straight-chain or branched alkyl or alkoxy having in each ca~e from 1 to 4 carbon atom~
in particular methyl, ethyl, methoxy or ethoxy.

The 4-alkylideneimino-triazolinone~ of the formula (VII) -~5 are not already known. They are, however, to a large ~ -extent the subject of the Applicant's aa yet unpublished -~
patent applications and are obtainable by means of the processes described therein, for example by reacting , ~

LeA 29 658 - 57 -~ L1~73 4-alkylideneimino-lH-triazolinone~ of the formula ~IX), R
R N=C
~ N R
N~o H

in which Rl, Rl4 and R~s have the meaning given above, with haloge~obenzene derivatives of the ~ormula (III), F~ .
11 ~
R ~ R
R -~
in which R3, R~, Rs, Rs and R7 have the me~ning given 2bove a~d ~al1 reprosent~ halogen, optionally in the presence of a diluent and optionally in the presence of a reaction auxiliary, in analogy to the implementation of prooe~s (a) according to the invention.

4-Alkylidenimino-lH-triazolinonee of the formula (IX) are known or are obtainable by analogy with known proce~se~

LeA 29 658 - 58 -` -~ 6 7 3 (cf. e.g. EP 294 666; EP 399 294).
Suitable diluents for carrying out process (a) according to the invention are inert organic eolvente. Theeo include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, diehlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, ehloroform or carbon tetrachloride~
ethers such ae diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; ketones such as acetone, butanone or methyl isobutyl ketone; nitriles sueh as aeetonitrile, prop$o~
nitrile or benzonitrile; amido~ sueh as N,N-dimethylform-amide, N,N-dimethylaeetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphorie triamide oresters sueh as methyl aeetate or ethyl aeetate.

Proeees (a) aeeording to the invention is preferably earried out in the presenee of a suitable reaction auxiliary. Suitable sueh auxiliaries are all conventional inorganic or organie bases. These include, for example, alkaline earth metal or alkali metal hydroxides sueh as sodium hydroxide, ealeium hydroxide, potaesium hydroxide or else ammonium hydroxide, alkali metal earbonatee such as sodium carbonate, potassium carbonate, potassium hydrogen carbonate, eodium hydrogen carbonate or ammonium earbonate, alkali metal or alkaline earth metal aeetates sueh as sodium aeetate, potassium aeetate, calcium acetate or ammonium acetate, and tertiary aminee euch as trimethylamine, triethylamine, tributylamine, . . :
:, :-: ~ . :::
.
LeA 29 658 - 59 -_ N,N-dimethylaniline, pyr~d~ne, piperidine, N-methyl-piperidine,N,N-dimethylaminopyridine,diazabicyclooctane (DABC0), diazabicyclononene (DBN) or diazabicycloundecene (DBU).

When carrying out process (a) ac~ording to the invention, the reaction temperatures can be ~aried within a rela-tively wide range. It is in general carried out at temperature~ of between 0C and +~80C, preferably at temperatures of between l20C and tl20C.

Process (a) according to the invention is usually carried out under at~ospheric pre~sure. However, it i8 al80 possible to work under increased or reduced pre~ure.

To carry out process (a) according to the invention reguire~ the use, per mole of l~-triazolinone of the formula (II), of in general from 1.0 to 3.0 mol, prefer-ably from 1.0 to 1.5 mol, of halogenobenzene derivati~e of the formula (III) and optionally from 1.0 to 3.0 mol, preferably from 1.0 to 1.5 mol, of base as reaction auxiliary. The reaction procedure, work-up and isolation of the reaction products are carried out by known pro-cQsses which are generally conventional (compare al80 the Preparation Examples).

Suitable diluent~ for carrying out process (b) according to the invention are inert organic solvents. It is preferred to use the solvents listed in the description of the implementation of pro e~8 (a) according to the LeA 29 658 - 60 -~llY673 invention.

Process (b) according to the invention i~ pre~erably carried out in the presence of a suitable reaction auxiliary. Suitable such auxiliaries are all conventional inorganic or organic bases. These include, for example, alkaline earth metal or alkali metal hydride~, hydrox-ides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such a~, for example, sodium hydride, sodium amide, ~odium methylate, sodium ethylate, pota~-~ium tert-butylate, ~odium hydroxide, pota~sium hydrox-ide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, a~monium acetate, sodium carbonate, potassium carbonate, potassium hydrogen carbonate, ~odium hydrogen carbonate or ammonium carbon-ate and tertiary amines such a~ trimethylamine, triethyl-amine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabi-cyclooctane (DABC0), diazabicyclononene (DBN) or diazabi-cycloundecene (DBU).
~:~
When carrying out process (b) according to the invention, the reaction t~mperatures can be varied within a rela-tively wide range. It i8 generally carried out at temperatures of between -20C and +150C, preferably at temperatures of between 0C and ~120C.

Process (b) according to the invention is usually carried out under atmospheric pres~ure. However, it is also possible to work under increased or reduced pressure. !

LeA 29 658 - 61 -To carry out proces~ (b) according to the invention requires the use, per mole of substituted triazolinone of the ~ormula (Ia), of in general from 1.0 to 3.0 mol, preferably from 1.0 to 1.5 mol, of nucleophile of the formula (IV) and optionally from 0.1 to 3.0 mol, prefer-ably from 1.0 to 1.5 mol, of ba~e as reaction auxiliary.
The reaction procedure, work-up and isolation of the reaction products are carried out by known processe~
which are generally conventional.

Suitable diluents for carrying out process (c) according to the invention are inert organic sol~ent~. These include, in particular, aliphatic, alicyclic or aromatic, optionally halogenated hydrocarbons ~uch as, for example, benzine, benzene, toluene, xylene, chlorobenzene, dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform, carbon tetrachloride; ether~
such as diethyl ether, diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl or diethyl ether; nitrile~ ~uch as acetonitrile, propionitrile or benzonitrile; amide~, such as N,N-dimethylformamide, N,N-dimethylacetamide, N-methylformanilide, N-methylpyrro-lidone or hexamethylphosphoric triamide; esters ~uch as methyl acetate or ethyl acetate or sulphoxide6 such as dimethyl sulphoxide.

Proce~ (c) according to the in~ention can optionally also be carried out in a two-phase system such a~, for example, water/toluene or water/dichloro~ethane, option-ally in the presence of a suitable phase-transfer LeA 29 658 - 62 ~

catalyst. Examples of such catalysts which may be men-tioned are: tetrabutylammonium iodide, tetrabutylammonium bromide, tetrabutylammonium chloride, tributyl-methyl-phosphonium bromide, trimethyl-C13/C1s-alkylammonium chloride, trimethyl-C13/Cls-alkylammonium bromide, dibenzyl-dimethyl-ammonium methyl sulphate, dimethyl-C12/
C1~-alkyl-benzylammonium chloride, dimethyl-Cl2/Cl~-alkyl-benzylammonium bromide, tetrabutylammonium hydroxide, triethylbenzylammonium chloride, methyltrioctylammonium chloride, trimethylbenzylammonium chloride, 15-crown-5, 18-crown-6 or tris-~2-(2-methoxyethoxy3-ethyl]-amine.

Process (c) according to the in~ention is preferably carried out in the presence of a suitable reaction auxiliary. Suitable such auxiliaries are all con~entional inorganic or organic bases. These include, for example, alkaline earth metal or alkali metal hydrides, hydrox-ides, amides, alcoholates, acetates, carbonates or hydrogen carbonates such as, for example, sodium hydride, sodium amide, sodium methylate, sodium ethylate, potas-sium ~ert-butylate, sodium ~ydroxide, potassium hydrox-ide, ammonium hydroxide, sodium acetate, potassium acetate, calcium acetate, ammonium acetate, ~odium carbonate, potassium carbonate, potassium hydrogen carbonate, sodium hydrogen carbonate or ammonium carbon-ate and tertiary amines such as trimethylamine, triethyl-amine, tributylamine, N,N-dimethylaniline, pyridine, N-methylpiperidine, N,N-dimethylaminopyridine, diazabi-cyclooctane (DABC0), diazabicyclononene (DBN) or diazabi-cycloundecene (DBU).

LeA 29 658 - 63 -~11Y~73 . .

When carrying out proces~ (c) according to the invention, the reaction temperatures can be varied within a rela-tively wide range. It is in general carried out at temperatures of between -20C and tl50C, preferably at temperatures of between 0C and +120C.

Process (c) according to the invention is usually carried out under atmospheric pressure. However, it i~ also possible to work under increaeed or reduced pressure.

To carry out process (c) according to the invention requires the use, per mole of substituted triazolinone of the formula (V), of in general from 1.0 to 3.0 1, preferably from 1.0 to 2.0 mol, of alkylating, acylating or sulphonylating agent of the formula (VI) and option-ally from 1.0 to 3.0 mol, preferably from 1.0 to 2.0 mol, of base as reaction auxiliary.
The reaction proceduro, work-up and isolation of the reaction products are carried out in both cases by known procosses which are generally conventional.

Suitable reducing agents for carrying out process (d) according to the invention are conventional reducing agents. It i8 particularly preferred to use complex hydrides such as, for example, lithium aluminium hydride --~
or sodium borohydride.
..
Suitable diluents for carrying out process (d) according --to the invention are, depending on the reducing agent ;
used, conventional organic or inorganic solvent~. Thé

., ~ , LeA 29 658 - 64 ~
`"~

: , ~, ' ', '` ' ,, ',.,, '".., ~ ;, ' ,.,,., '. ' preferred diluents u~ed are alcohols such as methanol, ethanol, propanol or butanol, ether alcohols such as methoxyethanol or ethoxyethanol, ether~ ~uch as diethyl ether, diisopropyl ether, dioxane or tetrahydrofuran, and their mixtures with water, or wat~r alone.

When carrying out process (d) according to the i~vention, the reaction temperatures can be varied within a rela-tively wide range. It i~ generally carried out at tem-peratures of between -20C and ~100C, preferably at temperature~ of between 0C and +80C.

Proce~ (d) according to the invention is usually carried out under atmospheric pre~sure. However, it ia also possible to work under increased or reduced pre~sure.

To carry out proce~s (d) according to the invention requires the u~e, per mole of 4-alkylidenimino-triazolin-one of the fermula (VII), of in general from 0.5 to 5.0 mol, preferably from 1.0 to 3.0 mol, of reducing agent. The reaction procedure, work-up and isolation of the reaction products are carried out by known processes which are generally conventional. ~`

The purification of the end products of the formula (I) i~ carried out by means of known methods, for example by column chromatography or by recrystallization.
Characterization i8 made via the melting point or, in the case of non-crystallizing compounds, by means of proton nuclear magnetic re~onance ~pectroscopy ~lH-NMR).

LeA 29 658 - 65 -'-:

The active compounds according to the invention can be used as defoliants, de~iccants, agents for destroylng broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to be understood all plants which grow in locations where they are undesired. Whether the substances according to the in~en-tion act as total or selective herbicides depends essen-tially on the amount used.
The active compounds according to the invention can be used, for example, in coDnection with the following plants:
Dicotvledon weeds of the aenera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galin~oga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipo ea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver Centaurea, Trifolium, Ranunculus and Taraxacum. --Dicotvledon cultures of the aenera: Gossypium, Glycine, ~ -Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicot$ana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledon weeds of the aenera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, - -~
Brachiaria, Lol;um, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristyli~, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
Monocotvledon cultures of the aenera: Oryza, Zea, ~ ~ ~

::'.'.," ~"
'` ~ '~ "" - ' LeA 29 658 - 66 - ~

Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, Ananas, Asparagus and Allium.
However, the use of the active compound~ according to the invention i8 in no way restriated to these genera, but also extends in the ~a~e manner to other plants.

The compounds are suitable, depending on the concentra-tion, for the total combating of weeds, for example on indu~trial terrain and rail tracks and on paths and ~quares with or without trees planted. Equally, the compounds can be employed for combating weed~ in peren-nial culture~, for example afforestations, decorative tree plantings, orchards, vineyards, citrus groves, nut orchards, banana plantation~, coffee plantation~, tea plantation~, rubber plantations, oil palm plantations, cocoa plantations, soft fruit planting~ and hopfields, in lawns, turf and pasture-land, and for the selective combating of weeds in annual cultures.

In this context, the acti~e compounds according to the invention can be e~ployed with particularly good success for co~bating dicotyledon weed~ in mo~o- and dicotyledon culture~ such as, for example, soya, sunflower or barley. ~-In addition, the active co~pounds according to the invention also pos~ess, at corresponding application -~
rates, fungicidal activity and can be employed for combating di~eases in rice, such a~, for example, against the causative organism of rice blast disea~e (Pyricularia oryzae).

~-LeA 29 658 - 67 - -~

~` :
Depending on their particular physical and/or chemical properties, the active compounds can be converted to the customary formulation~, such as solutions, emulsions, suspensions, powders, foams, pastes, granule~, aerosols, natural and synthetic material~ impregnated with active compound, very fine cap3ules in polymeric substances and in coating compositions for seed, and furthermore in formulations used with burning equipment, such as fumi-gating cartridges, $umigating cans, fumigating coils and the like, as well a~ ULV cold mi~t and warm mist fo~mula-tions.

These formulations are produced in a known manner, for example by mixing the ac~ive compou~ds with extenders, that is, liquid solvent~, liquefied gases under pressure, and/or solid carriers, optionally with the use of sur-face-active agents, that i8, emulsifying agent~ and/or dispersing agents, and/or foam-forming agents. In the case of the use of water a~ an extender, organic solvents can, for example, also be used as auxiliary ~olvent~. As liquid ~olvents, there are suitable in the main: aroma-tics, such as xylene, toluene or alkyl~aphthalenes, chlorinated aromatic~ or chlorinated aliphatic hydro-carbons, such as chlorobenzenes, chloroethylenes or methylene chloride, aliphatic hydrocarbons, such as cyclohexane or paraffins, for example mineral oil frac~
tions, alcohols, such as butanol or glycol as well a~
their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone, ~trongly polar solvents, such as dimethylfonmamide and ~eA 29 658 - 68 -dimethyl sulphoxide, as well a6 water: by liquefied gaseous extender~ or carriers are meant those liquids which are gaseous at ambient temperature and under atmospheric pressure, for example aerosol propellants, such as halogenated hydrocarbons as well a~ butane, propane, nitrogen and carbon dioxide; as solid carrier~
there are suitable: for example ground natural minerals, such as kaolins, clays, talc, chalk, quartz, attapulgite, montmorillonite or diatamaceous earth, and ground syn-thetic minerals, such as highly disperse silica, al~minaand silicates: as solid carriers for granules there are suitable: for example crushed and fractionated natural rocks such as calcite, marble, pumice, sepiolite and dolomite, as well as synthetic granules of inorganic and organic meals, and granules of organic material ~uch as sawdust, coconut shells, maize cobs and tobacco ~talks;
a~ emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters, polyoxy-ethylene fatty alcohol ethexs, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates as well as albumen hydrolysis products~
as dispersing agents there are suitablQ: for example lignin-sulphite waste liquors and methylcellulose.

Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latices, such as gum arabic, poly~inyl alcohol and polyvinyl acetate, as well as natural phospholipids, such as cephalins and lecithins, and synthetic phospholipids, LeA 29 658 - 69 -can be used in the $ormulations. Other add~ tives can be mineral and vegetable oils.

It is po~sible to use colorants such a~ inorganic pig-ment~, for example iron oxide, titanium oxide and Prus-sian Blue, and organic dyestuffs, such a~ alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dye-stuffs, and trace nutrients ~uch as salts of iron, manganese, boron, copper, cobalt, molybdenum and tin.

~he formulaticns in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.

For controlling weeds, the active compounds according to the invention, a~ such or in the form of their formula-tions, can also be used as mixture~ with known herbi-cides, finished formulation~ or tank mixes being pos-sible .
Rnown herbicide~ are ~uitable for the mixtures, for example anilides, such as for example diflufenican and propanil; arylcarboxylis acids, for example dichloropicolinic acid, dicamba or picloram; aryloxy-alkanoic acids, for example 2,4-D, 2,4-DB, 2,4-DP, fluroxypyr, MCPA, NCPP and triclopyr; aryloxy-phenoxy-alkanoic acid esters, for example diclofop-methyl, fenoxaprop-ethyl, fluazifop-butyl, haloxyfop-methyl and quizalofop-ethyl; azinone~, for example chloridazon and norflurazon; carbamates, for example chlorpropham, desmedipham, phenmedipham and propham;

LeA 29 658 - 70 -;~lY673 chloroacetanilides, $or example alachlor, acetochlor, butachlor, metazachlor, metolachlor, pretilachlor and propachlor; dinitroanilines, for example oryzalin, pendimethalin and tri$1uralin; diphenyl ethers, for example acifluorfen, bifenox, fluoroglycofen, fomesafen, halosafen, lactofen and oxyfluorfen; ureas, for example chlortoluron, diuron, fluometuron, isoproturon, linuron and methabenzthiazuron; hydroxylamines, for example alloxydim, clethodim, cycloxydim, sethoxydim and tralkoxydim; imidazolinone~, for example imazethapyr, imazamethabenz, imazapyr and imazaquin; nitriles, for example bromoxynil, dichlobenil and ioxynil; oxyacet~
amides, for example mefenacet; sulphonylureas, for example amidosulfuron, bensulfuron-methyl, chlorimuron-ethyl, chlorsulfuron, cinosulfuron, metsulfuron-methyl, nicosulfuron, primisulfuron, pyrazosulfuron-ethyl, thifensulfuron-methyl, triasulfuron and tribenuron-methyl; thiocarbamate~, for example butylate, cycloate, diallate, EPTC, esprocarb, molinate, prosulfocarb, thiobencarb and triallate; triazines, for example atra-zine, cyanazine, simazlne, simetryne, terbutryne and terbutylazine; triazinones, for example hexazinon~, metamitron and metribuzin; and others, for example aminotriazole, benfuresate, bentazone, cinmethylin, clomazone, clopyralid, difenzoquat, dithiopyr, ethofumes-ate, fluorochloridone, glufosinate, glyphosate, isoxaben, pyridate, quinchlorac, quinmerac, sulphosate and tridi-phane.

Mixtures with other known acti~e compounds, such as LeA 29 658 - 71 -.. - ;- , fungicides, insecticides, acaricides, nematicide~, bird repellants, plant nutrients and agents which improve soil structure, are also possible.

The active compounds can be used as such, in the form of their formulations or in the u~e forms prepared therefrom by further dilution, such as ready-to-use solutions, suspen~ions, emulsions, powders, paste~ and granules.
They are u~ed in the custo~ary manner, for example by watering, spraying, atomizing or ~cattering.

The active compounds according to the invention c~n be applied either before or after emergence of the plants.
They can al~o be iDcorporated into the 80il before sowing.

The amount of active compound used can vary within a relatively wide range. It depends e~entially on the nature of the desired effect. In general, the application rates are between 0.01 and 10 kg of active compound per hectare of soil ~urface, preferably between 0.05 and 5 kg per hectare.

The prepara~tion and use of the active compounds according to the invention can be ~een from the following examples.

LeA 29 658 - 72 -Preparation Exam~les:

Exa~ple 1:
~C~ N(CE~)2 ,~N

~
F ~

' (Proces~ a) 83 g (0.06 mol) of pota~sium carbonate are added to 71 g (0.5 mol)of4-dimethylamino-3-methyl-lH-1,2,4-triazolin-5-one (cf. e.g. EP 422 469) and 78.5 g (0.5 mol) of 2,4,5-trifluorobenzonitrile (cf. e.g. EP 191 181) in 400 ml of dimethyl sulphoxide at room temperature and the mixture i8 then stirred at 40C to 50C for two hour~.
For working up, tha ~ooled reaction mixture i~ filtered, the filtrate iB con~entrated in vacuo, the residue i~
stirred together with water, the precipitated ~olid iB
filtered o~f with ~uction, wa~hed with water and dried.

111 g (80% of theory) of 1-(4-cyano-2,5-difluorophe~yl)-3-methyl-4-dimethylamino-1,2,4-triazolin-5-one are o~tained with a melting point of 116C.

.

LeA 29 658 - 73 -l 3 EXamD1~ 2:
E~C

N~o F~O~ C_CH

(Pro~e~s b) 0.6 g (0.015 mol) of sodium hy~ride (60% in paraffin oil) i~ added at room temperature to 1.05 g (0.915 mol~ of 3-butin-1-ol in 100 ml of acetonitrile, the mixture i~
etirred for 10 minutes at room te~perature, then 2.12 g (0.008 mol)ofl-(4-cyano-2,5-difluorophenyl~-3-methyl-4-5N-methylamino)-1,2,4-triazolin-5-one are added and the mixture i8 ~tirred for a further 16 hour~ at room tem-perature. For working up, the reaction mixture i8 fil-tered, the filtrate iB concentrated in ~acuo, the residue i8 ~tirred together with water, a~d the pre~ipitated ~olid i8 filtered of with ~uction, washed with water and dried. ---1.96 g (78% of theory) of 1-(4-cyano-2-fluoro-5-but-1-in- ::
3-yl-oxyphenyl)-3-methyl-4-(N-methylamino)-1,2,4-triazo- ~ :~
lin-5-one i~ obtained with a melting point of 184-185C.

', ;'~ ' '~,':
LeA 29 658 - 74 ~

' 3 Example 3:
~C ,~
\~N
~0 ~' CN

(Proce~s a) 16.5 g (0.12 mol) of pota~ium carbonate are added to 12.8 g (0.1 mol) of 4-(N-methylamino)-3-methyl-1~-1,2,4-triazolin-5-one (cf. e.g. EP 399 294) and 15.7 g (0.1 mol) of 2,4,5-trifluorobenzonitrile (cf. e.g. EP
191 181) in 200 ml of dimethyl ~ulphoxide at room tem-perature, and the mixture i~ then ~tirr~d at 40C to 50C
for three hours. For working up, the cool~d reaction mixture i~ filter~d, the filtrate i8 concentrated in vacuo, the residu~ tirred together with water, and the precipitated solid i~ ~iltered of with suction, washed with water and dried.

12.8 g (48% of theory) of 1-(4-cyano-2,5-difluoro-phenyl)-3-methyl-4-(N-met~ylamino)-1,2,4-triazolin-5-one are obtained with a melting point of 128-131C. -,~ :

LeA 29 658 - 75 -., - . : : : . . .

Example 4.
H~C ~ 1)2 N
N~o F~F
CN

(Proc2ss a) 1.9 g (0.014 mol) of potassiu~ c~rbonate i~ added to 1.9 g (0.012 mol) of 3-methyl-4-(N-i~opropylEmi~o)-1~-1,2,4-triazolin-5-one (preparation analogous to EP
399 294) and 1.9 g (0.012 mol) of 2,4,5-trifluorobenzo-nitrile (cf. e.g. EP 191 181) in 100 ml of dimethyl sulphoxide at room temper~ture, a~d the mlxture iB then ~tirred at room temperature for two hours and at 40-50C
for 1.5 hours. For working up, the cooled reaction mixture i8 placed i~ water, a~d the precipitated solid is filtered off with ~uctio~, wa~hed with water and dried.

1.3 g (54.3% of theory) of 1-(4-cyano-2,5-difluoro-phenyl)-3-methyl-4-(N-i~opropylamino)-1,2,4-triazolin-5-ono ic obtaincd w~th ~ ~eltiDg point ol 35-35C.

', : ~-LeA 29 658 - 76 ~

:"~
-' Preparation of the starting compounds:

Example III-1:
CN

F
220 g (1.06 mol) of 2,4,5-Srichlorobenzonitrile are added with stirring at roo~ temperature to 250 g (4.31 mol) of pota~ium fluoride in 400 ml of distilled tetramethylene sulpho~e, and the mixture i~ then ~tirred at 195C to 200C for 10 hours. For working up, the mixture i~
cooled, 500 ml of water are added, and the mixture i8 ~ubjected to steam distillation. The organic fraction is taken up in dichloromethane, dried over sodium ~ulphate, concentrated in vacuo and di~tilled.

108 g (58% of theory) of 2,4-difluoro-5-chlorobenzo-nitrile are obtained with a boiling point of 105-107C at 30 mbar and with a melting point of 48-50C.

In a corre~sponding m~nner, and in accordance with the general instruction~ for the preparation, the following substituted triazolinone~ of the general formula (I) are obtained:

LeA 29 658 - 77 -R R
~N
N~ ~X
N

R ~R
R
~ No ?~X ~R P Y rt~ u ~ ~ ~

~C~ ,N(CE~)2 ~ m.p. 120-122C ~--~ O--~I-~CH ' ' ~' ' N~o ~ ; ~
.

n ~ SO~H m.p. 211-213C ;~

F

. ,: . -~ ~ :.

LeA 29658 - 78 -~ / R3 R
13x . No . ~N X R5 phy8is:al R~R6 propertie~

N~ ~O 50~m.p. >250C

8H~C2~ ,N(CE~)2 F m.p. 81C

N~N~O ~=~CN
F

9 ~ ,N(~)2 ~' lH-NI~*) 0 OEI GCH 1.73-1.75; 3-0;
N~N/~O ~ 4.92-5.0 ~ N(CE~)2 o--CH2~ H-NMR ):
~N~O ~ 2.6-2 7, 3.02;

p LeA 29 658 - 79 -2 3 ~
\~N R R
~x.No.N ~ ~ ~R5 physical X ~ propertieel R7 ~R6 :
11~C2~ ,N(C~)2 ,~(O~2~ )2-N(C~)2 lH NMR ) N~ ~CN 230, 3 0;

12H5C2 'N~ 2 (~i~)l~ lH-NMR*): - ~ ~ -~N ~ 2.6-2.7; 3.0; ~ -N~N~--o ~ 3.4; 4.25-4.3 P
13 ~C2 ,N(CH~)2 N}~SO2~ m.p. 154C
/~N
N~

' ': :.'-"' LeA 29 658 - 80 -~.LlY673 l~x.No. ~X ~ R5 phy~ical ~ propertie~
R R
14 ~c~ ,N(CE~)2 N~s4~ .p. 192-193C
~N ~S
~0 ~ ~CN
F
O~-GCH m.p,l6~161C

N$~o ~(~N

16 ~ m.p. 67-68C
~N O CH-C~-O-CF~
~0 ~'1 L.eA 29 658 - 81 -R ,R R
Bx.No. /~N ~-- R5 phy~ical R~R6 propertie~
17 ~C\,N~, (~ ~) ~N ~ , ~0 ~ ~CN 2 35; 2 76 F 4.25~.3 18 ~t~ ,N~C~ ,~C~-OECH~ m.p.l37-138C :

N ~o ~CN
p : ~ ~

m.p. 168-169C

N~o :

F

LeA 29 ~58 - 82 - -~ ~1Y~73 ~R2 R 4 E~.No. ~N ~R5 physical R~R6 prop~rties /~ ~ m.p. 158-160C

N~N~O
,~ ~2 ~/ \~CN

F

21 E~C\ ~N~~(CE~)2-S~2~m.p. 107-109C

~O ~--CN
F
22 ~I F m.p. 87C
~~_ ,N~C~), LeA 29 658 - 83 -~lJ~73 Ibc.No. ~ Rs phyuical 23 ~ SO2-C2H~m.p. 185-187C
,N(CE~)2 ~

~0 : ' ' P ; :-24 ~ m.p. 106C - ~
--l\ ,N((~)2 o--CH{~CEI '~

N~o ~ ~ ~;

25~C2~ ,NE~ Fm.p. 144145C

~0 F

LeA 29 658 - 84 .L.jb'73 R~R2 R3 R
15x . No . ~X ~Rs phyElical R~R6properties 26 E3,ffC2 ~N~ N~SO2-C2E~ m.p. 170C

N~N>~o ~

27~C2~ ~N~g Nl}sO2-~Cff~f m.p. 183-lB5C
N~N>c~o ~ ~

28HjC2~ '?~fff ~SO2~Ag m.p. 176C
N~o ~(~

29H~fC~ ,Nf~Ag ~O{~2-CH=CH2m.p. 10~102C

N~N~O ~ : - I
F
,~,, ,- ~, ~

LeA 2 96 5 8 - 8 5 R~ ,R R R

~c . No . N ~X R phy~ical R~R6 propertiQs ~0 ~ m.p. 112-113C

31 ~I F m.p. 136-138C
--~N ~CN
N~o F

32 ~ i\ ,N~3 f~ m.p. 121-123C

~N ~---CN ~

~ ' LeA 29 658 - 86 -.~ ~ . ~, .. . ... .... ......... .

G~3 R ,R2 R R
E~c.No. ~ ~ ~ propertio~

.__ 33 ~7C3~ ~ m.p. 168-170C

N~S4-CE~ m.p. 155-157C

~ /~N ~CN
N`N~o F

H3C~C~ SO,~ m.p.202-204C

~ . . . . . .. .. ...

R ,R R R
l3x.No. ~N ~Rs phyE~ical R R propertie~

36 H,C~ ,r~ HI m.p. 188-190C

37 ~C\ ~N~3 N~CE~=CH2 m.p. 158-160C

N~o F

C~ S-C2}~ m.p. 117-119C

~o ~SO .Il-C~l~ m.p. 128-130C

P

LeA 29 658 - 88 - ~

2 3 ~1 >--N R R
Ex.No. N~X ~R5 phy~ical propertie R R
~C ,N(CE~)2N~SO2-n-C~ m.p. 146-148C
1/ \ ~ i ~0 ~ ~ . .
F

41 ~ NE~g N~SO2-~-C8H~ m.p. 106-108C

N~o ~ :
F
42 H;~C~ ~N~ F m.p. 146-148C

N$~o ~CN.

LeA 29658 - 89 -.

R ,R R R
.No. /~N ~R5 phy~ical properties R7~--\R6 43 H3C\ ,N~3 F m.p. 125-126C

N~o ~CF3 F
44 ~3C~ ~N~ Cl m.p. 107-108C

N~o ~CE7 H3~ m.p. 115-118C

Cl ' ' ' LeA 29 658 - 90 -Ebc.No. /~N ~R5 phy~ical ~ ~ propertie~
R7~\R6 46 ~C ,N(C~)2 ~ m.p. 85-87C
~N O~ O-CE~ :
~ ~ , , ,~, 4? ~C\ ~N(~)2 fi~ ~ lH-NMR )~
~N O~o CH-COOc2}~ 2~22; 2.98;
N~o ~ 4.684.75;
~/ 6.9-6.95 ~ . .
F

~eA 29 658 - 91 ~llYb'73 R ,R2 3 4 Ex.No. N~--X -- R5 phy~ical R7~R6 proE~erties .
48 ~C~c~l~2 ~Q' m.p. 115-116C

49 E~C~ ~N(CH~), F -S02~ m.p. 153-lSSC

LeA 29 658 - 92 -lY~73 R ~R2 R R
13x.No. N X R5 physical ~ properties R R
-E~C~ ,N(C~)2Nf~S02-U-c~E~7 m.p. 151-152C
N~o ~CN

~N ~ m.p. 178-179C

52 ~C~ ,N~ Cl m.p. æ7-2280c N~ ~_ ~ .
53 E~N(CH~)2 ~C H2{~--CH m.p. 87-89C

N~o ~CN

:
LeA 29 658 - 93 ~

~ilY6~7'3 R~ R R R
Ex.No. ~N~X ~ ~R5 phy~ical ~ ~ propertie~
R R
54~C\ ,N~C~ Cl N~SO ~ m.p. 187-188C 1 ,r ~ ~
Cl ~CS ,~}~H3 N}~SO2-(-'2~5 m.p. 160~161C
\~N ~
N~N~o ~ ~ CN

56 E~ N(CEO2 -aH2~2-SC2H5 m.p. 95-97C
~0 ~

LeA 29 658 - 94 -R ,R2 R R
l~x.No. ~N ~R5 ~hysical R~R6 propertie~
. _ 57 H3C\ ,N(cE~)2O-CH2~F2-CF3 m.p. 113C

N~o F

~'-Y ~C~C~ m,p.212-214C

N~S02 ~

~ .
F

'~

" ' . ~', LeA 2 9 6 5 8 - 9 5 - ~

.

;~ y ~ 7 3 R ~R2 R3 4 13x No $x ~R5 phy~ical ~ properties R R
59 F3C\ ~N(~CH3)2 F lH Nl~*):
~N ~ 2.52; 7.55-7.65 N~,j~o ~CN
F
60F3C\ ,N~CO-CF3 F lH-N~ ):
~N ~ 7.55-7.60 N~o F

61 ~C~ N(CE~)2 N(CE~ S02-n~ ~,p. 121-123C
~o ~CN
. - "
F

62 ~;\ ,NE~CE~ F m.p. 150-151C
~N ,~/ -:
N~N~o ~
F - :
- '~'' --.

LeA. 29658 96 -~LlY673 R ~R2 R R
~N
~x . No . N )~ ~ R5 phy~ical X ~ ~ properties R R
63 F3C N~C~CF3 N~SOrc2~ lH-NMR~):
~N ~ 1.45; 3.2-3.25;
N~,~o ~ 7.7; 7.95-7.98 64 H3C N~C3H, N~SO2-CzHs lH-NMR ):
N`~o ~ N 3.65-3.75; 4-58 F
H3C ~N(C~)2 F m.p. 130C

N~o LeA ~9658 - 97 . ~ , .

.. - . :. - :

, . ... .

Y~73 Ex. No. R1 R2 Rs R4 Physical N ~ properties ~ I ~X ~ R5 66 H3C/NHCH3 ,__(F m.p.101C
CN
_ 67 H3CN(CH3)2 O l-C3H7 1.40-1.42,2.3;
~ I ~0 ~CN 3.0; 4.6-4.7 ~ ~ -68 CH/NHCH3 SC2H5 m.p. l 17-119C
3 I~NI ~o ~CN ; ~;

_ 69 CH3/NHCH3 NH2 m.p. 151-152C

` N~O ~ NO2 I ~: ~
_ _ CH3S~NH-CO-CF3 F m.p.84-86C

` IN~O ~CN
_ 71 CH3S~ /NH-CO-CF3 NH-S02-C2Hs m.p.137-138C
N`N~O ~C~

Le A 29 658 - 98 -.

~. .. . . ... .. . . ..

~ 11Y~73 :`

¦ Ex. No. R1 R2 R3 R4 Phy3ical properlies NHCH3 C~ m p. I 17-119( _ ICH3 F m.p. 120-122~( CH3~ / 3 ~2H3 m p 1610C

, .
1 75 CH N CH3)2 ~-SO2-CH~ m.p. 149C

NH-SOz-CH3 m.p. 143C

)2 ¦ , ~_2Hs ¦ m.p. 89C

Le A 29 658 99 - ~ ~:

. . , . , ~ , . . .

- , .

. . __ Ex. No. R1 R2 R3 R4 Physical I--~ ~R5 properties ~ N~,H3)2 F m.p. 103C

L ~ N~N~oN HCH~ F m.p. 145C

, *) The IH-NMR spectra were recorded in deuterochloroform (CDCl3) using tetramethylsilane (TMS) as the internal standard. The value given is the chemical shift o in ppm.

Le A 29 658 - 100 -ApFlication Example~

In the following Application Example, the compound li~ted below wa~ employed a~ compari~on ~ub~tance:
~C~ ,C~-C--=CH

~0 ' '' - ' F ~ (A) :

~ ' CN '. -3-Methyl-4-propargyl-1-(2,5-difluoro-4-cyano-phenyl)- .~ :
1,2,4-triazolin-5-one (know~ from DE 38 39 480) - ;' ' ; '~

' '~ , , :' LeA 29 658 - 101 ~
.

E~ample A:

Pre-emergence test Solvent: 5 parts by weight of acetone Emulsifier: 1 part by weight of alkylaryl polyglycol ether To produce a suitable preparation of active compound, one part by weight of active compound is mixed with the stated amount of ~olvent, the stated amou~t of emulsifier i~ added and the concentrate i~ diluted with water to the desired concentration.

Seeds of the test plants are 80wn in normal 80il and, after 24 hours, watered with the preparation of the active compound. It is axpedient to keep con~tant the amount of water per unit area. Th~ concentration of an a~tive ~ompound in the preparation i8 of no importance, only the amount of active compound applied per unit area being deci6ive. After three weeks, the degree of damage to the plants i~ rated in % damage in comparison to the development o~ the untreated control.
The figure~ de~oto: -0% = no action (li~e untreated control) 100% z total de~truction In this te~t, for example tho compound~ a~cording to Preparation Examples 5 and 6 exhibit a distinctly ~uperior activity at a rate of 250 g/ha corrpared to the prior art, in cultures like soy-bean (0-30%), sunflcwers (0%), barley (0-100~) against weeds like abuthilon (95-100%), chenopodium (100%), galium (80-95%), matricaria (95-100%) and solanum (95-100%) although the prior art has been applicated at a rate of 500 g/ha.

Le~ 29 65~ - 102 -

Claims (21)

1. A substituted 1-aryltriazolinone of the general formula (I):

(I) in which R1 represents hydrogen, alkyl, halogenalkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or cycloalkyl, R2 represents a radical of the formula -NR8R9, R3, R6 and R7 independently of one another in each case represents hydrogen, halogen, amino or nitro, R4 represents hydrogen, halogen, cyano or nitro, or one of the radicals -R10 -O-R10 -S-R10, -S(O)-R10, -SO2-R10, -SO2-OR10, -SO2-NR11R10, -CO-OR10, -CO-NR11R10, -O-SO-R10, -N(R11)-SO-R10, -NR11R10, -NH-P(O)(R11)(OR10) or -NH-P(O)(OR11)(OR10), R5 represents nitro, cyano, halogen or halogenoalkyl, and X represents oxygen or sulphur, where R8 represents hydrogen, alkyl, halogenoalkyl, a radical of the formula -CO-R12 or a radical of the formula -S(O)n-R12, R9 represents alkyl, halogenoalkyl, a radical of the formula -CO-R12 or a radical of the formula -S(O)n-R12, R10 represents hydrogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, aryl, arylalkyl or heterocyclyl, R11 represents hydrogen or represents in each case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl, arylalkyl or aryl, R12 represents in each case optionally substituted alkyl, cycloalkyl, arylalkyl, aryl or heterocyclyl, and n represents a number 0, 1 or 2.

2. A substituted 1-aryltriazolinone of the general formula (I) according to claim 1, characterized in that R1 represents hydrogen or represents in each case straight-chain or branched alkyl, alkoxy, alkylthio or alkyl-sulphonyl having in each case from 1 to 8 carbon atoms, further-more represents straight-chain or branched halogenoalkyl having from 1 to 8 carbon atoms and from 1 to 17 identical or different halogen atoms, or represents cycloalkyl having from 3 to 8 carbon atoms, R2 represents a radical of the formula -NR8R9, R3, R6 and R7 independently of one another in each case represent hydrogen, fluorine, chlorine, bromine, iodine, amino or nitro, R4 represents hydrogen, fluorine, chlorine, bromine, iodine, cyano or nitro, or represents one of the radicals -R10, -O-R10, -S-R10, -S(O)-R10, -SO2-R10, -SO2-OR10, -SO2-NR11R10, -CO-OR10 -CO-NR11R10, -O-SO2-R10, -N(R11)-SO2-R10, -NR11R10, -NH-P(O)(R11)(OR10) or -NH-P(O)(OR11)(OR10), R5 represents nitro, cyano, fluorine, chlorine, bromine, iodine or represents straight-chain or branched halogenoalkyl having from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms and X represents oxygen or sulphur, where R8 represents hydrogen, straight-chain or branched alkyl having from 1 to 8 carbon atoms or straight-chain or branched halogenoalkyl having from 1 to 8 carbon atoms and from 1 to 17 identical or different halogen atoms, and furthermore represents a radical of the formula -CO-R12 or a radical of the formula -S(O)n-R12, R9 represents straight-chain or branched alkyl having from 1 to 8 carbon atoms or straight-chain or branched halogeno-alkyl having from 1 to 8 carbon atoms and from 1 to 17 identical or different halogen atoms, and furthermore represents a radical of the formula -CO-R12 or a radical of the formula -S(O)n-R12, R10 represents hydrogen, R10 furthermore represents straight-chain or branched alkyl having from 1 to 14 carbon atoms which is optionally substituted once or more than once by identical or different substituents of halogen, cyano, carboxyl, carbamoyl, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, N-alkylamino-carbonyl, N,N-dialkylaminocarbonyl or alkylsulphonylaminocarbonyl having in each case from 1 to 8 carbon atoms in the individual alkyl moieties, or heterocyclyl, the heterocyclyl radical being a five- to seven-membered optionally benzo-fused, saturated or unsaturated heterocycle having from 1 to 3 identical or different hetero atoms of nitrogen, oxygen and/or sulphur, R10 furthermore represents alkenyl or alkinyl having in each case from 2 to 8 carbon atoms, which are optionally substituted once or more than once by identical or different halogens, R10 furthermore represents cycloalkyl having from 3 to 7 carbon atoms which is optionally substituted once or more than once by identical or different substituents of halogen and/or straight-chain or branched alkyl having from 1 to 4 carbon atoms, R10 furthermore represents arylalkyl or aryl having in each case from 6 to 10 carbon atoms in the aryl moiety and optionally from l to 4 carbon atoms in the straight-chain or branched alkyl moiety, which are in each case optionally substituted in the aryl moiety once or more than once by identical or different substituents, or represents a saturated or unsaturated, five- to seven-membered heterocyclyl radical having from 1 to 3 identical or different hetero atoms of nitrogen, oxygen and/or sulphur, which is optionally substituted once or more than once by identical or different substituents and/or is benzo-fused, wherein substituents of the aryl and/or heterocyclyl are halogen, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkyl-sulphinyl or alkylsulphonyl having in each case from 1 to 6 carbon atoms, in each case straight-chain or branched halogeno-alkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoxy-iminoalkyl having in each case from 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally substituted once or more than once by identical or different substituents of halogen and/or straight-chain or branched alkyl or alkoxy having in each case from 1 to 6 carbon atoms and/or straight-chain or branched halogenoalkyl or halogenoalkoxy having in each case from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms, R11 represents hydrogen, R11 furthermore represents straight-chain or branched alkyl having from 1 to 14 carbon atoms which is optionally substituted once or more than once by identical or different substituents of fluorine, chlorine, bromine, iodine, cyano, carboxyl, carbamoyl, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl, N-alkylaminocarbonyl, N,N-dialkylaminocarbonyl or alkylsulphonylaminocarbonyl having in each case from 1 to 8 carbon atoms in the individual alkyl moieties, or heterocyclyl, the heterocyclyl radical being a five- to seven-membered, optionally benzo-fused, saturated or unsaturated heterocycle having from 1 to 3 identical or different hetero atoms of nitrogen, oxygen and/or sulphur, R11 furthermore represents alkenyl or alkinyl having in each case from 2 to 8 carbon atoms, which are optionally substituted once or more than once by identical or different halogen atoms of fluorine, chlorine, bromine and/or iodine, R11 furthermore represents cycloalkyl having from 3 to 7 carbon atoms which is optionally substituted once or more than once by identical or different substituents of fluorine, chlorine, bromine, iodine and/or straight-chain or branched alkyl having from 1 to 4 carbon atoms, R11 furthermore represents arylalkyl or aryl having in each case from 6 to 10 carbon atoms in the aryl moiety and optionally from 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, which are in each case optionally substituted in the aryl moiety once or more than once by identical or different substituents, wherein substituents of the aryl are in each case halogen, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case from 1 to 6 carbon atoms, in each case straight-chain or branched halogeno-alkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoxy-iminoalkyl having in each case from 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally substituted once or more than once by identical or different substituents of halogen and/or straight-chain or branched alkyl or alkoxy having in each case from 1 to 6 carbon atoms and/or straight-chain or branched halogenoalkyl or halogenoalkoxy having in each case from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms, R12 represents straight-chain or branched alkyl having from 1 to 8 carbon atoms which is optionally substituted once or more than once by identical or different substituents of fluorine, chlorine, bromine, iodine, cycloalkyl having from 3 to 8 carbon atoms or heterocyclyl, the heterocyclyl radical being a five- to seven-membered optionally benzo-fused, saturated or unsaturated heterocycle having from 1 to 3 identical or different hetero atoms of nitrogen,oxygen and/or sulphur, R12 furthermore represents cycloalkyl having from 3 to 7 carbon atoms which is optionally substituted once or more than once by identical or different substituents of fluorine, chlorine, bromine, iodine and/or straight-chain or branched alkyl having from 1 to 4 carbon atoms, R12 furthermore represents arylalkyl or aryl having in each case from 6 to 10 carbon atoms in the aryl moiety and optionally from 1 to 4 carbon atoms in the straight-chain or branched alkyl moiety, which are in each case optionally substituted in the aryl moiety once or more than once by identical or different substituents, or represents a saturated or unsaturated, five- to seven-membered heterocyclyl radical having from 1 to 3 identical or different hetero atoms of nitrogen, oxygen and/or sulphur, which is optionally substituted once or more than once by identical or different substituents, wherein the substituents of aryl or heterocyclyl are in each case halogen, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkyl-sulphinyl or alkylsulphonyl having in each case from 1 to 6 carbon atoms, in each case straight-chain or branched halogeno-alkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximino-alkyl having in each case from 1 to 6 carbon atoms in the individual alkyl moieties, and phenyl which is optionally substituted once or more than once by identical or different substituents of halogen and/or straight-chain or branched alkyl or alkoxy having in each case from 1 to 6 carbon atoms and/or straight-chain or branched halogenoalkyl or halogenoalkoxy having in each case from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms, and n represents a number 0, 1 or 2.

3. A substituted 1-aryltriazolinone of the general formula (I) according to claim 1, characterized in that R1 represents hydrogen or in each case straight-chain or branched alkyl, alkoxy, alkylthio or alkylsulphonyl having in each case from 1 to 6 carbon atoms, or furthermore represents straight-chain or branched halogenoalkyl having from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms of fluorine, chlorine or bromine, or represents cycloalkyl having from 3 to 7 carbon atoms, R2 represents a radical of the formula -NR8R9, R3, R6 and R7 independently of one another in each case represent hydrogen, fluorine, chlorine, bromine, amino or nitro, R4 represents hydrogen, fluorine, chlorine, bromine, cyano or nitro, or represents one of the radicals -R10, -O-R10, -S-R10, -S(O)-R10, -SO2-R10, -SO2-OR10, -SO -NR11R10, -CO-OR10, -CO-NR11R10, -O-SO2-R10, -N(R11)-SO2-R10, -NR11R10, -NH-P(O)(R11)(OR10) or -NH-P(O)(OR11)(OR10), R5 represents nitro, cyano, fluorine, chlorine or bromine or represents straight-chain or branched halogenoalkyl having 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atoms of fluorine, chlorine or bromine, and X represents oxygen or sulphur, where R8 represents hydrogen, straight-chain or branched alkyl having from 1 to 6 carbon atoms or straight-chain or branched halogenoalkyl having from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms of fluorine, chlorine or bromine, and furthermore represents a radical of the formula -CO-R12 or a radical of the formula -S(O)n-R12, R9 represents straight-chain or branched alkyl having from 1 to 6 carbon atoms or straight-chain or branched halogeno-alkyl having from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms of fluorine, chlorine or bromine, and furthermore represents a radical of the formula -CO-R12 or a radical of the formula -S(O)n-R12, R10 represents hydrogen, R10 furthermore represents straight-chain or branched alkyl having from 1 to 12 carbon atoms which is optionally substituted once or twice by identical or different substituents of cyano, carboxyl, carbamoyl, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkyl-sulphonyl, alkoxycarbonyl, N-alkylaminocarbonyl, N,N-dialkylamino-carbonyl or alkylsulphonylaminocarbonyl having in each case from 1 to 6 carbon atoms in the individual alkyl moieties, or hetero-cyclyl, the heterocyclyl radical being a five- to seven-membered, optionally benzo-fused, saturated or unsaturated heterocycle having from 1 to 3 identical or different hetero atoms of nitrogen, oxygen and/or sulphur, R10 furthermore represents straight-chain or branched halogenoalkyl having from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms of fluorine, chlorine and/or bromine, R10 furthermore represents alkenyl or alkinyl having in each case from 2 to 6 carbon atoms, which are in each case optionally substituted once to three times by identical or different halogen atoms of fluorine, chlorine and/or bromine, R10 furthermore represents cycloalkyl having from 3 to 7 carbon atoms which is optionally substituted once to three times by identical or different substituents of fluorine, chlorine, bromine and/or straight-chain or branched alkyl having from 1 to 3 carbon atoms, R10 furthermore represents phenylalkyl or phenyl having optionally from 1 to 3 carbon atoms in the straight-chain or branched akyl moiety, which are in each case optionally substituted in the phenyl moiety once to five times by identical or different substituents, or represents a saturated or unsaturated, five- to seven-membered heterocyclyl radical having from 1 to 3 identical or different hetero atoms of nitrogen, oxygen and/or sulphur, which is optionally substituted once to three times by identical or different substituents and/or is benzo-fused, wherein the substituents of phenyl or heterocyclyl are in each case fluorine, chlorine, bromine, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case from 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkylthio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case from 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case from 1 to

4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally substituted once to five time by identical or different substituents of fluorine, chlorine, bromine and/or straight-chain or branched alkyl or alkoxy having in each case from 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl or halogenoalkoxy having in each case from 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atoms, R11 represents hydrogen, R11 furthermore represents straight-chain or branched alkyl having from 1 to 12 carbon atoms which is optionally substituted once or twice by identical or different substituents of cyano, carboxyl, carbamoyl, in each case straight-chain or branched alkoxy, alkoxyalkoxy, alkylthio, alkylsulphinyl, alkyl-sulphonyl, alkoxycarbonyl, N-alkylaminocarbonyl, N,N-dialkyl-aminocarbonyl or alkylsulphonylaminocarbonyl having in each case from 1 to 6 carbon atoms in the individual alkyl moieties, or heterocyclyl, the heterocyclyl radical being a five- to seven-membered, optionally benzo-fused, saturated or unsaturated hetero-cycle having from 1 to 3 identical or different hetero atoms of nitrogen, oxygen and/or sulphur, R11 furthermore represents straight-chain or branched halogenoalkyl having from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms of fluorine, chlorine and/or bromine, R11 furthermore represents alkenyl or alkinyl having in each case from 2 to 6 carbon atoms, which are in each case optionally substituted once to three times by identical or different halogen atoms of fluorine, chlorine and/or bromine, R11 furthermore represents cycloalkyl having from 3 to 7 carbon atoms which is optionally substituted once to three times by identical or different substituents of fluorine, chlorine, bromine and/or straight-chain or branched alkyl having from 1 to 3 carbon atoms, R11 furthermore represents phenylalkyl or phenyl having optionally from 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, which are in each case optionally substituted in the phenyl moiety once to five times by identical or different substituents, wherein the substituents of phenyl are in each case fluorine, chlorine, bromine, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case from 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkyl-thio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case from 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case from 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally substituted once to five times by identical or different substituents of fluorine, chlorine, bromine and/or straight-chain or branched alkyl or alkoxy having in each case from 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl or halogenoalkoxy having in each case from 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atoms;
R12 represents straight-chain or branched alkyl having from 1 to 12 carbon atoms which is optionally substituted once or twice by identical or different substituents of cycloalkyl having from 3 to 7 carbon atoms or heterocyclyl, the heterocyclyl radical being a five- to seven-membered, optionally benzo-fused, saturated or unsaturated heterocycle having from 1 to 3 identical or different hetero atoms of nitrogen, oxygen and/or sulphur, R12 furthermore represents halogenoalkyl having from 1 to 6 carbon atoms and from 1 to 13 identical or different halogen atoms of fluorine, chlorine and/or bromine, R12 furthermore represents cycloalkyl having from 3 to 7 carbon atoms which is optionally substituted once to three times by identical or different substituents of fluorine, chlorine, bromine and/or straight-chain or branched alkyl having from 1 to 3 carbon atoms, R12 furthermore represents phenylalkyl or phenyl having optionally from 1 to 3 carbon atoms in the straight-chain or branched alkyl moiety, which are in each case optionally substituted in the phenyl moiety once to five times by identical or different substituents, or represents a saturated or unsaturated, five- to seven-membered heterocyclyl radical having from 1 to 3 identical or different hetero atoms of nitrogen, oxygen and/or sulphur, which is optionally substituted once to three times by identical or different substituents and/or is benzo-fused, wherein the substituents of phenyl or heterocyclyl are in each case fluorine, chlorine, bromine, cyano, nitro, amino, N-acetylamino, in each case straight-chain or branched alkyl, alkoxy, alkylthio, alkylsulphinyl or alkylsulphonyl having in each case from 1 to 4 carbon atoms, in each case straight-chain or branched halogenoalkyl, halogenoalkoxy, halogenoalkyl-thio, halogenoalkylsulphinyl or halogenoalkylsulphonyl having in each case from 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atoms, in each case straight-chain or branched alkoxycarbonyl or alkoximinoalkyl having in each case from 1 to 4 carbon atoms in the individual alkyl moieties, and phenyl which is optionally substituted once to five times by identical or different substituents of fluorine, chlorine, bromine and/or straight-chain or branched alkyl or alkoxy having in each case from 1 to 4 carbon atoms and/or straight-chain or branched halogenoalkyl or halogenoalkoxy having in each case from 1 to 4 carbon atoms and from 1 to 9 identical or different halogen atoms and n represents a number 0, 1 or 2.

4. The compound 1-(4-cyano-2,5-difluorophenyl)-3-methyl-4-dimethylamino-1,2,4-triazolin-5-one of the formula .

5. The compound 1-(4-cyano-2,5-difluorophenyl)-3-methyl-4-(N-methylamino)-1,2,4-triazolin-5-one of the formula .

6. A compound according to claim 1 wherein R1 is methyl, R2 is -N(CH3)2, R3 is fluorine, R4 is hydrogen, R5 is cyano, X is oxygen and R7 is .

7. A compound according to claim 1 wherein R1 is methyl, R2 is -N(CH3)2, R3 is fluorine, R4 is hydrogen, R5 is cyano, X is oxygen and R7 is NH-SO2-CH3.

8. A herbicidal composition comprising a herbicidally effective amount of a compound according to any one of claims 1 to 7 in admixture with a suitable carrier or diluent.

9. A herbicidal composition comprising a herbicidally effective amount of a compound according to any one of claims 1 to 7 in admixture with a solid diluent or carrier, a liquified normally gaseous diluent or carrier, or a liquid diluent or carrier containing a surface active agent.

10. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 7.

11. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a composition containing a compound according to any one of claims 1 to 7 in admixture with a suitable carrier or diluent.

12. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a composition containing between 0.1 and 95% by weight of a compound according to any one of claims 1 to 7 in admixture with a suitable carrier or diluent.

13. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a composition containing between 0.5 and 90% by weight of a compound according to any one of claims 1 to 7 in admixture with a suitable carrier or diluent.

14. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 7 wherein the compound is applied as a pre-emergence herbicide.

15. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 7 wherein the compound is applied as a post-emergence herbicide.

16. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 7 wherein the compound is applied to an area of cultivation at a rate of between 0.01 and 10 kg/ha.

17. A method of combating weeds which comprises applying to the weeds, or to a habitat thereof, a herbicidally effective amount of a compound according to any one of claims 1 to 7 wherein the compound is applied to an area of cultivation at a rate of between 0.05 and 5 kg/ha.

18. A process for preparing a compound of formula (I) as defined in claim 1 and R1, R2, R3, R4, R5, R6, R7 and X are as defined in claim 1, which process comprises:
a) reacting a 1H-triazolinone of the formula (II) (II) in which R1, R2 and X have the meaning given above, with a halogenobenzene derivative of the formula (III) (III) in which R3, R4, R5, R6 and R7 have the meanings given above and Hal1 represents halogen, or b) reacting a substituted 1-aryltriazolinone of the formula (Ia) (Ia) in which R1, R2, R3, R6, R5, R7 and X have the meanings given above and Hal2 represents halogen, with a nucleophile of the formula (IV) H-R13 (IV) in which R13 represents a radical of the formula -O-R10, -S-R10 or -NR11R10, where R10 and R11 have the meanings given above, or c) reacting a substituted triazolinone of the formula (V) (V) in which R1, R3, R4, R5, R6, R7 and X have the meanings given above, with an alkylating, acylating or sulphonylating agent of the formula (VI) R9-E (VI) in which R9 has the meaning given above and E represents an electron-attracting leaving group, or d) reacting a 4-alkylideneimino-triazolinone of the formula (VII) (VII) in which R1, R3, R4, R5, R6, R7 and X have the meanings given above, R14 represents hydrogen or alkyl and R15 represents alkyl or alkoxy.

19. A process for preparing a herbicidal composition which comprises admixing a compound of formula (I) as defined in any one of claims 1 to 7 together with an extender or surface active agent.

20. A substituted 1-aryltriazolinone of the formula (Ia) (Ia) in which R1, R2, R3, R5, R6, R7 and X are as defined in claim 1 and Hal2 represents halogen.

21. A substituted triazolinone of the formula (V) (V) in which R1, R3, R4, R5, R6, R7 and X are as defined in claim 1.