CA2003208C

CA2003208C - Substituted triazolinones

Info

Publication number: CA2003208C
Application number: CA002003208A
Authority: CA
Inventors: Klaus Konig; Klaus Lurssen; Hans-Joachim Santel; Robert R. Schmidt; Harry Strang; Klaus-Helmut Muller; Markus Lindig; Kurt Findeisen
Original assignee: Bayer AG
Current assignee: Bayer AG
Priority date: 1988-11-19
Filing date: 1989-11-17
Publication date: 1997-08-26
Anticipated expiration: 2009-11-17
Also published as: JP2793862B2; EP0370293A3; DE58904344D1; AU626595B2; EP0370293B1; EP0370293A2; JPH02180874A; AU4392189A; DE3839206A1; CA2003208A1

Abstract

Herbicidal triazolinones of the formula (see fig. I) (I) in which R1 represents alkyl having 3 to 4 carbon atoms, or represents cyclopropyl, and R2 represents hydrogen, alkyl, alkenyl, alkinyl, halogenoalkyl, halogenoalkenyl, halogenoalkinyl, cyanoalkyl, hydroxyalkyl, alkoxyalkyl, alkoxy-carbonylalkyl, alkoxycarbonylalkenyl, alkylamino-alkyl or dialkylaminoalkyl, or represents cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, each of which is optionally substituted, or represents optionally substituted hetero-cyclylalkyl, or represents aralkyl, aroyl, aryl, aralkyloxy or aryloxy, each of which is optionally substituted, or represents alkoxy, alkenyloxy or alkinyloxy.

Description

- 2 0 0 3~2 0 8 The lnventlon relates to new substituted trlazollnones, to several processes for their preparatlon, and to thelr use as herblcldes.
It ls known that certaln substltuted trlazollnones, such as, for example, the compound 4-amlno-1-(N-lsopropylcarbamoyl)-3-methylthlo(lH,4H)-1,2,4-trlazolln-5-one or the compound 4-amino-l-(N-propylcarbamoyl)-3-methylthlo-tlH,4H)-1,2,4-trlazolln-5-one or the compound 4-amlno-1-(N-butylcarbamoyl)-3-methylthio-(lH,4H)-1,2,4-triazolin-5-one or the compound 4-amlno-1-lN-cyclohexylcarbamoyl)-3-methylthlo-(lH,4H)-1,2,4-trlazolln-5-one (cf., for example, JP
52/125,168), have herblcldal propertles.
However, the herblcldal actlvlty of these prevlously known compounds towards problem weeds, as well as thelr tolerance by important crop plants, ls not entirely satlsfactory ln all flelds of appllcatlon.
Furthermore, certaln substltuted trlazollnones, such as, for example l-(N,N-dlmethylcarbamoyl)-3-phenyl-4-amlno-1,2,4-trlazolln-5-one, are known (cf. J. Heterocycl.
Chem. 17, 1691 - 1696 [1980]; Org. Mass, Spectrom. 14, 369 -378 [1979~).
Nothlng was known hltherto about an actlvlty of these prevlously known trlazollnones as herblcldes.
Accordlng to one aspect of the present lnventlon there ls provlded a substltuted trlazollnone of the general formula (I) ~-~ 23189-7020 .

R ~

i ~
// \NH R2 ln whlch Rl repreæents alkyl havlng 3 to 4 carbon atoms, or represents cyclopropyl, and R represent 8 hydrogen, or represents ln each case stralght-chaln or branched alkyl havlng 1 to 18 carbon atoms, alkenyl havlng 2 to 8 carbon atoms, alklnyl havlng 2 to 8 carbon atoms, halogenoalkyl havlng 1 to 8 carbon atoms and 1 to 17 ldentlcal or dlfferent halogen atoms, halogenoalkenyl or halogenoalklnyl, each of whlch has 2 to 8 carbon atoms and 1 to 15 or 13 ldentlcal or different halogen atoms, cyanoalkyl havlng 1 to 8 carbon atoms, hydroxyalkyl havlng 1 to 8 carbon atoms and 1 to 6 hydroxyl groups, alkoxyalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkenyl, each havlng up to 6 carbon atoms ln the lndlvldual alkyl or alkenyl moletles, or alkylamlnoalkyl or dlalkylamlnoalkyl each havlng 1 to 6 carbon atoms ln the lndlvldual alkyl moletles, or represents cycloalkyl havlng 11 carbon atoms, or represents cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, each of whlch has 3 to 8 carbon atoms ln the cycloalkyl or cycloalkenyl molety and lf approprlate 1 to 6 carbon atoms ln the alkyl molety, and each of whlch ls A~ 23l89-7o2o 2~3208 optionally monosubstituted or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano as well as ln each case straight-chain or branched alkyl or halogenoalkyl, each of which has 1 to 4 carbon atoms and if appropriate 1 to 9 identical or different halogen atoms, stralght-chain or branched halogenoalkenyl having up to 4 carbon atoms and 1 to 5 identical or different halogen atoms, and in each case double-linked alkanediyl or alkenediyl, in each case having up to 4 carbon atoms; R2 furthermore represents heterocycloalkyl which has 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and 1 to 9 carbon atoms and 1 to 3 hetero atoms in the heterocyclo moiety and which is optionally monosubstituted or polysubstituted in the heterocyclyl moiety by identical or different substltuents selected from the group consisting of halogen, cyano, nltro, and in each case straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio and alkoxycarbonyl, each of which has 1 to 5 carbon atoms and if appropriate 1 to 9 identical or different halogen atoms; R2 furthermore represents in each case straight-chain or branched alkoxy having 1 to 8 carbon atoms, alkenyloxy having 2 to 8 carbon atoms or alkinyloxy having 2 to 8 carbon atoms, and finally represents aralkyl, aroyl, aryl, aralkyloxy or aryloxy, each of which has 6 to 10 carbon atoms in the aryl moiety and if appropriate 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted or polysubstituted by identical or different 20n~2~8 substltuents, the alkyl substituents when present selected from the group conslstlng of halogen and cyano, and the aryl substltuents when present being selected from the group conslstlng of halogen, cyano, nitro, hydroxyl, ln each case stralght-chaln or branched alkyl, alkoxy, alkylthlo, halogenoalkyl, halogenoalkoxy, halogenoalkylthlo, alkylsùlphlnyl, alkylsulphonyl, halogenoalkylsulphlnyl, halogenoalkylsulphonyl, alkanoyl and alkoxycarbonyl, each of which has 1 to 6 carbon atoms ln the alkyl molety and lf approprlate 1 to g ldentlcal or different halogen atoms, and cycloalkyl havlng 3 to 6 carbon atoms and phenoxy; or R
represents benzyl wlth an O-~H2-O- group fused to the phenyl molety.
Where approprlate, the compounds of the formula (I) can be ln the form of geometrlc and~or optlcal lsomers or mlxtures of lsomers of varlous composltlons, dependlng on the type of the substltuents Rl and R2. The lnventlon clalms both the pure lsomers and the mlxtures of lsomers.
Furthermore, lt has been found that the new substltuted trlazollnones of the general formula (I) as deflned above are obtalned when (a) hydrazones of the formula (II) 2~n~208 .

Rl R3 N-N-C ~ 4 IN~o (~) \NH R2 in whlch Rl and R2 have the abovementioned meaning and R3 and R4 lndependently of one another each represent hydrogen, or represent stralght-chaln or branched alkyl having 1 to 4 carbon atoms, or represent phenyl or benzyl, are reacted with an acid, lf approprlate ln the presence of a diluent, or when (b) lH-triazolinones of the formula (III) R ~N-NH2 lN~o in which Rl has the abovementioned meaning are reacted with isocyanates of the formula (IV) R2-N=C=O (IV) in whlch R2 has the abovementloned meaning, if appropriate ln the presence of a dlluent and lf approprlate ln the A

2~Q3~2 ~8 presence of a reactlon auxlllary, or ln that (c) trlazollnones of the formula (V) N-~ 2 I ~o o// \o RS

ln whlch Rl has the abovementloned meaning and R5 represents stralght-chain or branched alkyl havlng 1 to 4 carbon atoms, or represents phenyl or benzyl, each of whlch ls optlonally monosubstltuted to trlsubstituted by halogen, cyano, nltro, ln each case stralght-chaln or branched alkyl, alkoxy or alkylthio, each of whlch has 1 to 4 carbon atoms, or ln each case a stralght-chaln or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthlo, each of whlch has 1 to 4 carbon atoms and 1 to 9 ldentlcal or dlfferent halogen atoms are reacted wlth amlnes of the formula (VI) R2-NH2 (VI) ln whlch R has the abovementloned meanlng, lf approprlate ln the presence of a dlluent and lf approprlate ln the presence of a reactlon auxlllary, or when (d) lH-trlazollnones of the formula (III) - 5a -A 23l89-7020 ~03~8 Rl ~"~NH2 ln whlch Rl has the abovementioned meaning are reacted wlth urethanes of the formula (VII) o RS

ln which R2 and R5 have the abovementloned meanlng and if approprlate ln the presence of a dlluent and lf approprlate ln the presence of a reactlon auxlllary.

- 5b -Z0032~)8 - Finally, it has been found that the new sub-stituted triazolinones of the general formula (I) have herbicidal properties.
Surprisingly, the substituted triazolinones of the general formula (I) according to the invention show a considerably higher herbicidal potency towards problem weeds than the substituted triazolinones which are known from the prior art, such as, for example, 4-amino-1-(N-isopropylcarbamoyl)-3-methylthio-(lH,4H)-1,2,4-triazolin-5-one or the compound 4-amino-1-(N-propylcarbamoyl)-3-methylthio-(lH,4H)-1,2,4-triazolin-5-one or the compound 4-amino-1-(N-butylcarbamoyl)-3-methylthio-(lH,4H)-1,2,4-triazolin-5-one or the compound 4-amino-1-(N-cyclohexyl-carbamoyl)-3-methylthio-(lH,4H)-1,2,4-triazolin-5-one, which are compounds of a similar chemical structure and a similar type of action.
Formula (I) provides a general definition of the substituted triazolinones according to the invention.
Preferred compounds of the formula (I) are those in which Rl- represents n~propyl, i~propyl, n-butyl, i-butyl, s-butyl, t-butyl or cyclopropyl and R2 represents hydrogen, or represents in each case straight-chain or branched alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl or halo-genoalkinyl, each of which has 2 to 8 carbon atoms and 1 to 15 or 13 identical or different halogen atoms, cyanoalkyl having 1 to 8 carbon atoms, Le A 26 538 - 6 -~ hydroxyalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxyl groups, alkoxyalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkenyl, each having up to 6 carbon atoms in the individual alkyl or alkenyl moieties, or alkylaminoalkyl or dialkylaminoalkyl, each having 1 to 6 carbon atoms in the individual alkyl moie-ties, or represents cycloalkyl having 11 carbon atoms, or represents cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, each of which has 3 to 8 carbon atoms in the cycloalkyl or cyclo-alkenyl moiety and if appropriate 1 to 6 carbon atoms in the alkyl moiety, and each of which is optionally monosubstituted or polysubstituted by identical or different substituents, suitable substituents in each case being: halogen, cyano as well as in each case straight-chain or branched alkyl or halogenoalkyl, each of which has 1 to 4 carbon atoms and if appropriate 1 to 9 identical or different halogen atoms, or straight-chain or 2C branched halogenoalkenyl having up to 4 car~on atoms and 1 to 5 identical or different halogen atoms, or in each case double-linked alkanediyl or alkene-diyl, in each case having up to 4 carbon atoms; R2 furthermore represents heterocyclylalkyl which has 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and 1 to 9 carbon atoms and 1 to 3 hetero atoms - in particular nitrogen, oxygen and/or sulphur - in the heterocyclyl moiety and which is optionally monosubstituted or polysub-stituted in the heterocyclyl moiety by identical or Le A 26 538 - 7 -v - -ZQ0320~3 ~ different substituents, suitable substituents being:
halogen, cyano, nitro, and in each case straight-chain or branched alkyl, alkoxy, alkylthio,halogeno-alkyl, halogenoalkoxy, halogenoalkylthio or alkoxy-carbonyl, each of which has 1 to 5 carbon atoms and if appropriate 1 to 9 identical or different halogen atoms; R2 furthermore represenls in each case straight-chain or branched alkoxy having 1 to 8 carbon atoms, alkenyloxy having 2 to 8 carbon atoms or alkinyloxy having 2 to 8 carbon atoms, and finally represents aralkyl, aroyl, aryl, aralkyloxy or aryloxy, each of which has 6 to 10 carbon atoms in the aryl moiety and if appropriate 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted or polysubstituted by identical or different substi-tuents, suitable alkyl substituents, where appro-priate, being halogen and cyano, and suitable aryl substituents in each case being: halogen, cyano, ~itro; hydroxyl, in each Gase straight-ch~in or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkylsulphinyl, halogeno-alkylsulphonyl, alkanoyl or alkoxycarbonyl, each of which has 1 to 6 carbon atoms in the alkyl moiety and if appropriate 1 to 9 identical or different halogen atoms, or cycloalkyl having 3 to 6 carbon atoms and phenoxy; or R2 represents benzyl with an -O-CH2-O- group fused to the phenyl moiety.
Particularly preferred compounds of the formula Le A 26 538 - 8 -~- (I) are those in which Rl represents n-propyl, i-propyl, i-butyl, s-butyl, t-butyl or cyclopropyl and R2 represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, in each case straight-chain or branched pentyl, hexyl, heptyl, octyl, nonyl, decyi or doaecyl, or represents allyl, in each case straight-chain or branched butenyl, pentenyl or hexenyl, propargyl, in each case straight-chain or branched butinyl, pentinyl or hexinyl, or represents straight-chain or branched halogenoalkyl having 1 to 8 carbon atoms and 1 to 9 identical or different halogen atoms, in particular fluorine, chlorine or bromine, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl, each of which has 3 to 8 carbon atoms and 1 to 3 halogen atoms, in particular fluorine or chlorine, or represents in each case straight-chain or branched cyanoalkyl having 1 to 6 carbon atoms in the alkyl moiety, hydroxyalkyl having 1 to 6 carbon atGms ~nd 1 to 3 hydroxyl groups, or alkoxyalkyl, alkoxy-carbonylalkyl or alkoxycarbonylalkenyl, alkylamino-alkyl or dialkylaminoalkyl, each of which has up to 4 carbon atoms in the individual alkyl or alkenyl moieties, or represents cyclopropyl, cyclopropyl-methyl, cyclopropylethyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclohexylmethyl, cyclo-hexylethyl, cyclohexenyl or cyclohexenylmethyl, each of which is optionally monosubstituted to trisubsti-tuted by identical or different substituents, Le A 26 538 - 9 -suitable substituents in each case being: fluorine, chlorine, bromine, methyl, ethyl, n- or i-propyl, n-,i-, s- or t-butyl, cyano, methanediyl, ethane-diyl, butanediyl or butadienediyl or dichloroallyl;
R2 furthermore represents heterocyclylmethyl, hetero-cyclylpropyl or heterocyclylethyl, each of which is optionally monosubstituted to trisubstituted in the heterocyclyl moiety by identical or different substituents, suitable heterocycles in each case being:

~Z~l; N~Z~; N~l --N~>

~ --N O or --N~ N}~ ' Z in each case representing oxygen or sulphur and suit-able substituents in each case being:
fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio;
R2 additionally represents in each case straight-chain or branched alkoxy having 1 to 6 carbon atoms, Le A 26 538 - 10 -.

2003;~08 -- alkenyloxy having 3 to 6 carbon atoms or alkinyloxy having 3 to 6 carbon atoms, or represents benzyl, phenylethyl, phenylpropyl, phenylbutyl, phenyl-pentyl, phenylhexyl, phenylheptyl, phenylcyano-methyl, phenylcyanoethyl, phenylcyanopropyl, benzyl-oxy, phenylethyloxy, phenoxy, benzoyl, phenyl or naphthyl, where approprlate straight-chain or branched, each of which is optionally monosubsti-tuted to trisubstituted by identical or different substituents, suitable phenyl substituents in each case being: fluorine, chlorine, bromine, hydroxyl, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, tri-fluoromethyl,trifluoromethoxy,trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, methylsulphinyl, methylsulphonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, cyclohexyl or phenoxy.
Very particularly preferred compounds of the formula (I) arç those in which Rl represents isopropyl, cyclopropyl or s-butyl and R2 represents methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, allyl, propargyl, in each case straight-chain or branched pentyl, hexyl, heptyl, octyl, butenyl, pentenyl, hexenyl, butinyl, pentinyl or hexinyl, each of which is optionally monosubstituted to trisubstituted by fluorine and/or chlorine;
additionally represents cyclopropyl, cyclopentyl, cyclohexyl, cyclohexenyl, cyclopropylmethyl, cyclo-propylethyl, cyclohexylmethyl, cyclohexylethyl or Le A 26 538 - 11 -2003;~08 -- cycloheptyl, each of which is optionally monosubsti-tuted to trisubstituted by identical or different substituents from the series comprising fluorine, chlorine, methyl, ethyl and/or cyano, and finally represents benzyl or phenylethyl.
The following substituted triazolinones of the general formula (I) may be mentioned individually:

Rl~N-NH2 N~NI ~ O (I) Le A 26 538 - 12 --200;~208 - Rl R2 (CH3~2CH-(CH3)2CH- ~

(CH3~2CH- \ CH2 (CH3)2CH- H3C

(CH~)2CH- C2H5 (CH3)2CH- H3C

(CH3)2CH- C2H5 ~

(CH3)2CH- -CH2 ~ l (CH3)2CH- -CH2-CH2 ~ l ~CH2F
30 (CH3)2CH ~CH2F
fH3 (CH3)2CH- -f-CH=CH2 Le A 26 538 - 13 -~003Z(~8 Rl R2 .
fH3 (CH3)2CH- -f -CH2 CH cH2 C!H3 10 (CH3)2CH- -f-CH2F

fH3 (CH3)2CH- -f-CH2Cl fH2F
(CH3)2CH- -f-CH~

(CH3)2CH- -fH-CH2-Cl fH2Cl 25 (CH~)2CH- -f-CH3 (CH3)2CH- -IC-CHCl2 (CH3)2CH- -CH-CH2-CH(cH3)2 Le A 26 538 - 14 -!~'' ' '' ' ' 200320~3 Rl R2 (CH3)2CH- -fH-(CH2)2-CH(cH3)2 (CH3)2CH- -CH-(CH2)3-CH(cH3)2 (CH3)2CH- -C-CF3 (CH3)2CH- -(CH2)2-CH3 (CH3~2CH- -(CH2)3-CH3 (CH3)2CH- -CH(CH3)2 (CH3)2CH- -CH-C2H5 (CH3)2CH- -fH-CH(CH3)2 (CH3)2CH- -CH

(CH3)2CH- -CH

(CH3)2CH- - 1~3 CH~

Le A 26 538 - 15 -e Rl R2 (CH3)2CH- -C-C-CH

10 (CH3)2CH- -C-C2H5 15 (CH3)2CH- f ( CH2~2 CH3 (CH3)2CH- -C-(CH2)3-CH3 (CH3)2CH- -C(CH3)3 ¦ CH-H2C~' H21C~

H2C~
H2C~ /CH2 ¦ CH- -CH
H2C~ \CH2 . .
H21~ H3C ~

H2C~ C 2H5~0 Le A 26 538 - 16 -5 H2f~ H3C

H2 IC~ C 2H5 H2C~

H2C~ - CH2{~C 1 H2 IC~ _CH2_cH2{~C
H2C~
H2C~ ~cH2F
CH - - CH
H2C~ ~CH2F

H2C~
20 H2C~ - f CH=CH2 H2C~
H2C~ -C-CH2-CH=CH2 H2C~
¦ CH- -C-CH2F
H2C~

H2C~
¦ CH- -C-CH2Cl H2C~

Le A 26 538 - 17 -.. . .

Z00~20~3 Rl R2 H2C~
¦ CH- -C-CH3 H2C~

H2C~ -CH;CH2-Cl ¦ CH- -C-CH~
H2C~
CH2Cl H2C~
¦ CH- -C-CHCl2 H2C ~ CH3 H21C~ -cH-cH2-cHtcH3)2 H2C~ rH3 H2CI~ -CH-(CH2)2-CH(cH3)2 25 H2C~ CH~

H2C~
¦ CH- -CH-(CH2)3-~H(CH3)2 H2C~

H2C~
¦ CH- -C-CF3 H2C~ CH3 Le A 26 538 - 18 -s - ~

Z00;~208 Rl R2 H2C~
¦ CH- -(CH2)2-CH3 H2C~
H2C`
¦ CH- -(CH2)3-CH3 H2C~
H2C`
¦ CH- -CH(CH3)2 H2C~
¦ CH- -CH-C2H5 H2C~

H2C`
¦ CH- -CH-CH(CH3)2 H2C~

2¦ CH- -CH

H2C~ -CH

H2CI ~ - C~3 H2C~

H2C~
¦ CH- -C-C-CH
H2C~

Le A 26 538 - 19 -- ~003208 - -- Rl R2 H2C~

H2C~

10 H2CI~ C (CH2)2 CH3 H C~

H2f~ -C-(CH2)3-CH3 15 H2C ~ CH3 H21C~ -C(CH3)3 C2H5 fH

C2H5-CH- \ CH2 ~ C2H5-CH- H3C

Le A 26 538 - 20 -2003~i0~3 - Rl R2 _ C2H5 fH- C2H5 C~H~-fH- H3C

C2H5 fH C2H5 C2H5-fH; -CH2 ~ 1 C2H5-CH- -CH2-CH2 ~ 1 ~CH2F
C2H5 fH ~CH2F

fH3 C2H5 fH- -f-CH=CH2 fH3 30 C2H5-fH- -f-CH2-CH=cH2 Le A 26 538 - 21 -Rl R2 fH3 C2Hs-fH- -f-CH2F

~H3 10C2H5-fH- -f-CH2Cl fH2F
C2Hs-fH- -f-CH3 C2Hs-fH -fH-CH2-Cl fH2Cl C2H5-CH- f -CH3 CH3 CH2Cl fH3 25 C2Hs-fH- -f-CHC12 C2H5 fH-fH-CH2-CH(cH3~2 C2H5 CIH-fH-(CH2)2-CH(CH3)2 C2H5 fH-fH-(CH2)3-CH(cH3)2 Le A 26 538 - 22 -2003;208 Rl R2 fH3 C2H5 fH -C-CF3 C2H5 fH -(CH2)2-CH3 C2H5 fH -(CH2)3-CH3 C2H5-fH- -CH(CH3)2 c~3 C2H5 fH -fH-C2H5 20 C2H5-fH- -fH-CH(CH3)2 C2H5-fH-C2H5 fH

C2H5 ICH f Le A 26 538 - 23 -. ......

~003Z08 - Rl R2 fH3 15 C2H5-CH- f (CH2)2 CH3 C2H5-CH- -C-(CH2)3-CH3 C2H5-CH- -C(CH3)3 CH~

Le A 26 538 - 24 -i, . . .

If, for example, l-(N-isobutylcarbamoyl)-4-isopropylideneimino-3-isopropyl-1,2,4-triazolin-5-one is used as the starting compound, the course of the reaction of process (a) according to the invention may be repre-sented by the following equation:

~CH3 N`N~o >
I -(CH3)2CO
~C~
o NH-CH2-CH(cH3)2 ~CH3)2-CH~ NH2 N`N o o NH-CH2-CH~CH3)2 If, for example, 4-amino-3-cyclopropyl-1,2,4-(lH)-tri-azolin-5-one and t-butyl isocyanate are used as the starting substances, the course of the reaction of process (b) according to the invention may be represented by the following equation:

H2C \
H2C/ ~Nl -NH2 t ~ CH3)3C-N=C=O
N`N~o H2C\
I f ~N - NH 2 > N`IN o O=C-NH-C(CH3)3 Le A 26 538 - 25 -~003~)8 If, for example, l-phenoxycarbonyl-4-amino-3-s-butyl-1,2,4-triazolin-5-one and N,N-diethylpropane-1,3-diamine are used as starting substances the course of the reac-tion of process (c) according to the invention may be represented by the following equation:
CH
j 3 C2H5-CH~N-NH2 ~52H5 ll ~ H2N-CH2-CH2-cH2 N
N~N~ ~0 ~C2H5 O=C-OC6H5 Cl H3 C2H5 - CH~_N- NH2 - C6H5-OH ll l > N`N~o ~C2H5 O=C-NH-CH2 CH2 CH2 N

If, for example, 4-amino-3-isopropyl-1,2,4-(lH)-tri-azolin-5-one and N-isopropyl phenylcarbamate are used as the starting substances, the course of the reactiGn of process (d) according to the invention may be represented - by the following equation:
o H3C~ 11 ~ ( CH3 ) 2CH~r--N-NH2 CH-NH-C-O~ ~ 1 1 H3C~ N`NI ~o H

( CH3 ~ 2C~_N-NH2 N`N~o ~CH3 O=C-NH-CH

Le A 26 538 - 26 -, 200;~08 - ~~ Formula (II) provides a general definition of the hydra-zones required as starting substances for carrying out process (a) according to the invention. In this formula (II), Rl and R2 preferably represent those radicals which have already been mentioned in connection with the description of the substances of the formula (I) accord-ing to the invention as being preferrea ~or these sub-stituents. R3 and R4 in each case independently of one another represent hydrogen, or represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or repre-sent phenyl or benzyl.
The hydrazones of the formula (II) were hitherto unknown. They are likewise the subject-matter of the present invention. However, they are obt~ine~ in analogy to known processes (cf., for example, Acta Pol. Pharm.
38, 153 - 162 tl981] or C.A. 95: 203841j), for example by reacting l-unsubstituted 4-aminotriazolinones of the formula (III) R 1 ~T--N'NH 2 I l (III) N`NI ~0 in which R1 has the abovementioned meaning, with aldehydes or ketones of the formula (VIII) c = o (VIII) R4~

Le A 26 538 - 27 -ZQ03~08 in which R3 and R4 have the abovementioned meaning, if appropriate in the presence of a diluent, such as, for example, dichloromethane or toluene, and if appropriate in the presence of a catalyst, such as, for example, p-toluenesulphonic acid, at temperatures between 40C and 120C, an~ reacting the resulting l-unsubstituted tri-azolinone hydrazones of the formula (IX) R~ N-N=C
¦ ~R4 (IX) H

in which --R1, R3 and R4 have the abovementioned meaning either in a subsequent 2nd step with isocyanates of the formula (IV) R2 - N = C =

in which R2 has the abovementioned meaning, if appropriate in the presence of a diluent, such as, for example, dichloromethane or dioxane, and if appropriate in the presence of a reaction auxiliary, such as, for example, triethylamine, at temperatures between 50C and 150C;
or alternatively in a subsequent 2nd step with chloro-formic acid esters of the formula (X) Le A 26 538 - 28 -o R5 - o - C - C~ (X) in which R5 represents alkyl, aryl or arylalkyl, if appropriate in the presence of a diluent, sucn as, for example, tetrahydrofuran, and if appropriate in the presence of a reaction auxiliary, such as, for example, sodium hydride or potassium t-butoxide, at temperatures between -20C and +40C, and reacting the resulting triazolinones of the formula (XI) R1 N-N=C (XI3 ¦ ~ R4 N~IN~o o=c -o-R5 in which ln Rlo R30 R4 ~nd R5 hav~ the abovementioned ~eaning in a subsequent 3rd step with amines of the formula (VI) R2 - N~2 (~I) in which R2 has the abovementioned meaning, if appropriate in the presence of a diluent, such as, for example, tetrahydrofuran, and if appropriate in the presence of a base, such as, for example, sodium hydrox-ide, potassium hydroxide or diazabicycloundecene (DBU), Le A 26 538 - 29 -at temperatures between 20C and 50C.
In this context, it is also possible and may be advantageous to carry out the reaction of the 1-unsubsti-tuted triazolinone hydrazones of the formula (IX) with chloroformic acid esters of the formula (x) and the sub-sequent reaction of the resulting triazolinones (XI) with amines of the formula (VI) in one reaction step in a so-called one-pot process.
Some of the l-unsubstituted 4-amino-triazolinones of the formula (III) are known and can be obtAine~ in analogy to known processes (cf., for example, J. Hetero-cycl. Chem. 16, 403 tlg79]; J. Heterocycl. Chem. 17, 1691 [1980]; Europ. J. Med. Chem. 18, 215 [1983]; Chem. Ber.
98, 3025 [1965]; Liebigs Ann. Chem. 637, 135 [1960]; J.
Heterocycl. Chem. 21, 1769 - 1774 [1984]; Chim. Acta Turc. 7, 269 - 290 [1979] or CA 106 (17): 138338e [1986]).
The aldehydes or ketones of the formula (VIII) are generally known compounds of organic chemistry.
Some of the 1-unsubstituted triazolinone hydra-zones of the formula (IX) are known (cf., for example, Chim. Acta. Turc. 7, 269 - 290 [1979]).
The chloroformic acid esters of the formula (X) are generally known compounds of organic chemistry.
The triazolinones of the formula (XI), which are mentioned as intermediates, were hitherto unknown and are also the subject-matter of the invention.
Rl in this context preferably represents those radicals which have already been mentioned in connection with the description of the substances of the formula (I) Le A 26 538 - 30 -- - - . .. . .

according to the invention as being preferred for this substituent.
R3 and R4 in each case independently of one another preferably represent hydrogen, or representstraight-chain or branched alkyl having 1 to 4 carbon atoms, or represent phenyl or benzyl, and R' preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, or represents phenyl or benzyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents, suitable substituents in each case being: halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkyl-thio, each of which has 1 to 4 carbon atoms, or in each case a straight-chain or branched halogeno-alkyl, halogenoalkoxy or halogenoalkylthio, each of which has 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
R5 in particular represents methyl, ethyl, n- or i-2G propyl, n-, i-, s- or t-butyl, or represen~s phenyl or benzyl, each of which is optionally monosubsti-tuted to disubstituted by identical or different substituents, suitable substituents in each case being: fluorine, chlorine, bromine, cyano, nitro, 2S methyl, ethyl, n- or i-propyl, n-~ i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio.
Formula (III) provides a general definition of the lH-triazolinones required as starting substances for Le A 26 538 - 31 -f ` ` - . .

~~ carrying out processes (b) and (d) according to the invention. In this formula (III), R1preferably represents those radicals which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention as being preferred for this substituent.
The lH-triazolinones of the formula (III) are either known, or they can be obtained in analogy to known processes (cf., for example, B.J. Heterocycl. Chem. 16, 10403 [1979]. J. Heterocycl. Chem. 17, 1691 [1980]; Europ.
J. med. Chem. 18, 215 [1983]; Chem. Ber. 98, 3025 [1965];
Liebigs Ann. Chem. 637, 135 [1960]; J. Heterocycl. Chem.
21, 1769 - 1774 [1984]; Chim. Acta. Turc. 7, 269 - 270 [1979]; CA 106 (17): 138338e [1986]).
15l-Unsubstituted 4-aminotriazolinones of the formula (IIIa) Rl_ l~N-NH2 1 (IIIa) H

in which R1-1 represents n-butyl, i-butyl, s-butyl or cyclopropyl, in particular represents s-butyl or cyclopropyl, were hitherto unknown and are also the subject-matter of the invention.
They are obtained in analogy to known processes (cf., for example, J. Heterocycl. Chem. 21, 1769 [1984], and Chem. Ber. 98, 3025 [1965]), for example when Le A 26 538 - 32 -- hydrazine hydrate is reacted with diphenyl carbonate in a customary manner, and the resulting carbonic acid hydrazide is cyclized, likewise in a customary manner, with carboxylic acid derivatives of the formula (XII) R1-1 - COOR6 (~II) in which R1-l has the abovementioned meaning and R6 represents hydrogen, or represents straight-chain or branched alkyl having 1 to 4 carbon atoms, at temperatures between 150C and 250C (cf. also the preparation examples).
Carboxylic acid derivatives of the formula (XII) are generally known compounds of organic chemistry.
Formula (IV) provides a general definition of the isocyanates fur~hermore required as starting substances for carrying out process (b) according to the invention.
In this formula (IV), R2 preferably represents those radicals which have already-been mentioned in connectiDn with the description of the substances of the formula (I) according to the invention as being preferred for this substituent.
The isocyanates of the formula (IV) are generally known compounds of organic chemistry. The compounds 2,2,2-trifluoroisopropylcyanate and 2,2,2-trifluoro-1,1-dimethylethyl cyanate were hitherto unknown, but they can be prepared by known methods.
Formula (V) provides a general definition of the triazolinones required as starting substances for Le A 26 538 - 33 -carrying out process (c) according to the invention. In this formula (V), R1 preferably represents those radicals which have already been mentioned in connection with the description of the substances of the formula (I) accord-ing to the invention as being preferred for this substituent.
R5 preferably represents straight-chain or branched alkyl having 1 to 4 carbon atoms, or represents phenyl or benzyl, each of which is optionally monosubsti-tuted to trisubstituted by identical or different sub-stituents, suitable substituents in each case being:
halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio, in each case having 1 to 4 carbon atoms, or in each case straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkyl-thio, in each case having 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms;
R5 in particular represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents phenyl or benzyl, each of which is optionally monosubstl-tuted to disubstituted by identical or different substituents, suitable substituents in each case being: fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio.
The triazolinones of the formula (V) were hither-to unknown.
They are obt~ine~ in analogy to known processes, Le A 26 538 - 34 -r-200320~3 ~ by reacting lH-triazolinones of the formula (III) R1 ~ N-NH2 (III) N~N O
H

in which Rl has the abovementioned meaning with chloroformic acid esters of the formula (X) R5 - O - C - Cl (x) in which R5 has the abovementioned meaning, if appropriate in the presence of a diluent, such as, for example, tetrahydrofuran, and if appropriate in the presence of a reaction auxiliary, such as; for example, potassium t-butoxide or sodium hydride, at temperatures between -20C and +40C (cf. also the preparation examples).
Formula (VII) provides a general definition of the ureth~nes furthermore required as starting substances for carrying out process (d) according to the invention.
In this formula (VII), R2 preferably represents those radicals which have already been mentioned in connection with the description of the substances of the formula (I) according to the invention as being preferred for these Le A 26 538 - 35 -- ~ substituents. R5 preferably represents those radicals which have already been mentioned in connection with the description of the precursors of the formula (V) as being preferred, or particularly preferred, for this substituent.
The urethanes of the formula (VII) are generally known compounds of organic chemistry, or they can be obt~i ne~ with the aid of generally known processes.
Suitable acids for carrying out process (a) according to the invention are all inorganic and organic acids which can customarily be used for hydrazone cleav-ages. Inorganic mineral acids, such as hydrochloric acid, sulphuric acid or phosphoric acid, are preferably used.
Suitable diluents for carrying out process (a) according to the invention are all customary organic or inorganic solvents. Polar, water-miscible organic sol-vents, in particular alcohols, such as methanol, ethanol, propanol or butanol, or their mixtures with water, or pure water, are preferably used as the diluents.
~hen carrying out process (a) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 20C and 150C, preferably at temperatures between 50C and 120C.
Process (a) according to the invention is conven-tionally carried out under atmospheric pressure or under reduced pressure. If the process is carried out under reduced pressure, suitable pressure ranges are those between 20 and 400 mbar, preferably between 100 and 200 mbar.

Le A 26 538 - 36 -200;~20~3 - ~~ For carrying out process (a) according to the invention, 1 to 50 moles, preferably 1 to 20 moles, of acid are generally employed per mole of hydrazone of the formula (II). For this purpose, the hydrazone of the formula (II) is dissolved in a suitable amount of dilu-ent, the required amount of acid is then added, and the mixture is slowly concentrated under reduced pressure in the course of several hours.
In a special embodiment of the procedure, it is also possible to carry out process (a) according to the invention and the preparation of the precursors of the formula (II) required for this, in one reaction step in a so-called one-pot process.
One possibility in this process is to choose the triazolinones of the formula (XI) as starting compounds, and to react these in succession in a one-pot process with amines of the formula (VI) and then with acid, in accordance with process (a) according to the invention (cf. in this context, also the preparation examples), or, alternatively, to choose the trlaæoline hydr~zones of the formula (IX) as the starting compounds and to react these in succession in a one-pot process with chloroformic acid esters of the formula (X), then with amines of the formula (VI) and subsequently with acid, in accordance with process (a) according to the invention.
Suitable diluents for carrying out process (b) according to the invention are inert organic solvents.
These particularly include aliphatic, alicyclic or aro-matic, optionally halogenated hydrocarbons, such as, for example, benzine, benzene, toluene, xylene,chlorobenzene, Le A 26 538 - 37 -.
petroleum ether, hexane, cyclohexane, dichloromethane, chloroform and carbon tetrachloride, ethers, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether, nitriles, such as acetonitrile or propionitrile, amides, such as dimethylformamide, dimethylacetamide, N-methylformanilide, N-methylpyrrolidone or hexamethyl-phosphoric triamide, or esters, such as ethyl acetate.
If appropriate, process (b) according to the invention is carried out in the presence of a suitable reaction auxiliary. Suitable reaction auxiliaries are all customary inorganic or organic bases. These include, for example, tertiary amines, such as triethylamine, N,N-dimethylaniline, N,N-diethylbenzylamine, N,N-dimethyl-cyclohexylamine or dibutyltin dilaureate, pyridine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
When carrying out process (b) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the process is carried out at temperatures between 0C and 150C, preferably at temperatures between 20C and 100C.
For carrying out process (b) according to the invention, 1.0 to 2.0 moles, preferably 1.0 to 1.5 moles, of isocyanate of the formula (IV) and, if appropr~ate, 0.001 to 2.0 moles, preferably 0.001 to 1.0 mole, of reaction auxiliary are generally employed per mole of lH-triazolinone of the formula (III). The reaction is carried out and the reaction products are worked up and isolated by generally customary methods.

Le A 26 538 - 38 -- Suitable diluents for carrying out processes (c) and (d) according to the invention are inert organic solvents. These in particular include aliphatic, ali-cyclic or aromatic, optionally halogenated hydrocarbons, S such as, for example, benzine, benzene, toluene, xylene, chlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane, chloroform and carbon tetrachloride, ethers, such as diethyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethyl ether or ethylene glycol diethyl ether, nitriles, such as acetonitrile or propio-nitrile, amides, such as dimethylformamide, dimethyl-acetamide, N-methylformanilide, N-methylpyrrolidone or hexamethylphosphoric triamide, or esters, such as ethyl acetate, or sulphoxides, such as dimethyl sulphoxide.
If appropriate, processes (c) and (d) according to the invention can be carried out in the presence of a suitable reaction auxiliary. Suitable reaction aux-iliaries are all customary inorganic or organic bases.
These preferably include alkali metal hydroxides, such as 2~ sodium hydroxide or potassium hydoxide, alhali me~di carbonates, such as sodium carbonate, potassium carbonate or sodium hydrogen carbonate, and also tertiary amines, such as triethylamine, N,N-dimethylaniline, pyridine, N,N-dimethylaminopyridine, diazabicyclooctane (DABCO), diazabicyclononene (DBN) or diazabicycloundecene (DBU).
When carrying out processes (c) and (d) according to the invention, the reaction temperatures can be varied within a substantial range. In general, the processes are carried out at temperatures between 0C and 120C, pre-ferably at temperatures between 20C and 50C.

Le A 26 538 - 39 -- 2003~08 For carrying out process (c) according to the invention, 1.0 to 5.0 moles, preferably 1.0 to 2.5 moles, of amine of the formula (VI) and if appropriate 1.0 to 2.0 moles, preferably 1.0 to 1.2 moles, of reaction auxiliary are generally employed per mole of triazolinone of the formula (V).
The reaction is carried out and the reaction products are worked up and isolated by generally customary methods.
In a special embodiment of the procedure, it is also possible to carry out process (c) according to the invention and to prepare the precursors of the formula (V) required for this, in one reaction step in a so-called one-pot process.
In this way of carrying out the reaction, the starting materials are lH-triazolinones of the formula (III), which are reacted in succession in a one-pot process, initially with chloroformic acid esters of the formula (X) and subsequently with amines of the formula (VI), in accordance with process (c) according to the invention.
For carrying out process (d) according to the invention, 1.0 to 5.0 moles, preferably 1.0 to 2.5 moles, of urethane of the formula (VII) and, if appropriate, 1.0 to 5.0 moles, preferably 1.0 to 2.5 moles, of reaction auxiliary are generally employed per mole of lH-triazoli-none of the formula (III).
The reaction is carried out and the reaction products are worked up and isolated by generally customary methods.
Another method to obtain compounds of the formula (I) according to the invention comprises reacting Le A 26 538 - 40 -- ~ oxadiazolinones of the formula (XIII) Rl o ~1 ~ (XIII) 0~ NH-R2 in which R1 and R2 have the abovementioned meaning, with hydrazine hydrate in the presence of a suitable diluent, such as, for example, methanol or ethanol, at temperatures between 20C and 100C, and thermally cycliz-ing the resulting carbacic acid derivatives of the formula (XIV) O O
Il 11 Rl -C-NH-N-C-NH-NH2 I (XIV) O=C-NH-R2 in which Rl and R2 have the abovementioned meaning in the presence of a suitable diluent, such as, for example, toluene, chlorobenzene or dichlorobenzene, at temperatures between 80C and 200C.
Oxadiazolinones of the formula (XIII) are known (cf., for example, FR 1,415,605 or C.A. 64: P5105g, and NL 6,510,645 or C.A. 65: P2274d-f), or they can be Le A 26 538 - 41 -- - obtained by generally known processes, for example by reacting the corresponding 4H-oxadiazolinones with isocyanates of the formula (IV) in analogy to the proce-dure of process (b) according to the invention or to the synthesis of the precursors of the formula (II).
The end products of the formula (I) are purified with the aid of customary processes, for example by means of column chromatography or by recrystallization.
They are characterized with the aid of the melting point or, in the case of non-crystallizing compounds, with the aid of the proton nuclear magnetic resonance spectrum.
The active compounds according to the invention can be used as defoliants, desiccants, agents for des-troying broad-leaved plants and, especially, as weed-killers. By weeds, in the broadest sense, there are to beunderstood all plants which grow in locations where they are undesired. Whether the substances according to the invention act as total or selective herbicides depends essentially on the amount used.
The active compounds according to the invention can be used, for example, in connection with the follow-ing plants:
Dicotyledon weeds of the genera: Sinapis, Lepidium, Galium, Stellaria, Matricaria, Anthemis, Galinsoga, Chenopodium, Urtica, Senecio, Amaranthus, Portulaca, Xanthium, Convolvulus, Ipomoea, Polygonum, Sesbania, Ambrosia, Cirsium, Carduus, Sonchus, Solanum, Rorippa, Rotala, Lindernia, Lamium, Veronica, Abutilon, Emex, Datura, Viola, Galeopsis, Papaver, Centaurea and Mercurialis.

Le A 26 538 - 42 -- Dicotyledon cultures of the genera: Gossypium, Glycine, Beta, Daucus, Phaseolus, Pisum, Solanum, Linum, Ipomoea, Vicia, Nicotiana, Lycopersicon, Arachis, Brassica, Lactuca, Cucumis and Cucurbita.
Monocotyledon weeds of the genera: Echinochloa, Setaria, Panicum, Digitaria, Phleum, Poa, Festuca, Eleusine, Brachiaria, Lolium, Bromus, Avena, Cyperus, Sorghum, Agropyron, Cynodon, Monochoria, Fimbristylis, Sagittaria, Eleocharis, Scirpus, Paspalum, Ischaemum, Sphenoclea, Dactyloctenium, Agrostis, Alopecurus and Apera.
Monocotyledon cultures of the genera: Oryza, Zea, Triticum, Hordeum, Avena, Secale, Sorghum, Panicum, Saccharum, AnAn~, Asparagus and Allium.
However, the use of the active compounds accord-ing to the invention is in no way restricted to these genera, but also extends in the same manner to other plants.
The compounds are suitable, depending on the concentration, for the total combating of weeds, for example on industrial terrain and rail tracks, and on paths and squares with or without tree plantings. Equal-ly, the compounds can be employed for combating weeds in perennial cultures, for example afforestations, decor-ative tree plantings, orchards, vineyards, citrus groves, nut orchards, h~n~n~ plantations, coffee plantations, tea plantations, rubber plantations, oil palm plantations, cocoa plantations, soft fruit plantings and hopfields, and for the selective combating of weeds in annual cultures.

Le A 26 538 - 43 -r ` ` `

2003Z0~
- ~~ In this context, the active compounds according to the invention can be employed with particularly good success for combating monocotyledon and dicotyledon weeds in monocotyledon and dicotyledon crops, such as, for example, sugar beet, maize, wheat and barley.
The active compounds can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusting agents, pastes, soluble powders, granules, suspension-emulsion concentrates, natural and synthetic materials impregnated with active compound, and very fine capsules in polymeric substances.
These formulations are produced in a known manner, for example by ~;xing the active compounds with extenders, that is liquid solvents and/or solid carriers, optionally with the use of surface-active agents, that is emulsifying agents and/or dispersing agents and/or foam-forming agents.
In the case of the use of water as an exten~er, organic solvents can, for example, alsG be used as auxiliary solvents. As liquid solvents,there are suitable in the main: aromatics, such as xylene, toluene or alkyl-naphthalenes, chlorinated aromatics and chlorinated ali-phatic hydrocarbons, such as chlorobenzenes, chloroethy-lenes or methylene chloride, aliphatic hydrocarbons, suchas cyclohexAne or paraffins, for example petroleum fractions, mineral and vegetable oils, alcohols, such as butanol or glycol as well as their ethers and esters, ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents, Le A 26 538 - 44 -such as dimethylformamide and dimethyl sulphoxide, as well as water.
As solid carriers there are suitable: for example ammonium salts and ground natural minerals, such as S kaolins, clays, talc, chalk, quartz, attapulgite, montmo-rillonite or diatomaceous earth, and ground synthetic minerals, such as highly disperse silica, alumina and 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 such as sawdust, coconut shells, maize cobs and tobacco stalks;
as emulsifying and/or foam-forming agents there are suitable: for example non-ionic and anionic emulsifiers, such as polyoxyethylene fatty acid esters,polyoxyethylene fatty alcohol ethers, for example alkylaryl polyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonat-es as well as albumen hydrolysis products; as dispersing agents there are suitable: for example lignin-sulphite waste liquors and methylcellulose.
Adhesives such as carboxymethylcellulose and natural and synthetic polymers in the form of powders, granules or latexes, such as gum arabic, polyvinyl alcohol and polyvinyl aGe~ate,as well as natural phospho-lipids, such as cephalins and lecithins, and synthetic phospholipids, can be used in the formulations. Further additives can be mineral and vegetable oi~ls.
It is possible to use colorants such as inorganic pigments, for example iron oxide, titanium oxide and Le A 26 538 - 45 -- - Prussian Blue, and organic dyestuffs, such as alizarin dyestuffs, azo dyestuffs and metal phthalocyanine dye-stuffs, and trace nutrients such as salts of iron, man-ganese, boron, copper, cobalt, molybdenum and zinc.
The formulations in general contain between 0.1 and 95 per cent by weight of active compound, preferably between 0.5 and 90%.
For controlling weeds, the active compounds according to the invention, as such or in the form of their formulations, can also be used as mixtures with known herbicides, finished formulations or tank mixes being possible.
Possible components for the mixtures are known herbicides, such as, for example, 1-amino-6-ethylthio-3-(2,2-dimethylpropyl)-1,3,5-triazine-2,4(lH,3H)-dione (Ahh~YvIONE) or N-(2-benzothiazolyl)-N,N'-dimethyl-urea (ME~AR~N~THIAZURON) for combating weeds in cereals; 4-amino-3-methyl-6-phenyl-1,2,4-triazin-5(4H)-one (METAMITRON) for combating weeds in sugar beet and 4-2Q amino-6-(1,1-dimethylethyl)-3-methylthio-1,2,4-triazin-5(4H)-one (METRIBUZIN) for combating weeds in soya beans.
Other possible mixtures are those with 2,4-dichloro-phenoxyacetic acid (2,4-D); 4-(2,4-dichlorophenoxy)-butyric acid (2,4-DB); 2,4-dichlorophenoxypropionic acid (2,4-DP); N-(methoxymethyl)-2~6-diethyl-chloroacet~nilide ~C~T.OR); 2-chloro-4-ethylamino-6-isopropylamino-1,3,5-triazine (ATRAZINE); methyl 5-(2,4-dichlorophenoxy)-2-nitrobenzoate (BIFENOX); 3,5-dibromo-4-hydroxy-benzo-nitrile (BROMOXYNIL); 2-chloro-N-{~(4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino]-carbonyl}-benzenesulphonamide Le A 26 538 - 46 -, - (CHLORSULFURON); N,N-dimethyl-N'-(3-chloro-4-methyl-phenyl)-urea (CHLORTOLURON); 2-chloro-4-ethylamino-6-(3-cyanopropylamino)-1,3,5-triazine (CYANAZINE); 2-[4-(2,4-dichlorophenoxy)-phenoxy]-propionic acid, its methyl ester or its ethyl ester (DICLOFOP); 3,6-dichloro-2-pyridinecarboxylic acid (CLOPYRALID); S-ethyl N,N-di-n-propyl-thiocarbamate (EPTAME); 4-amino-6-t-butyl-3-ethylthio-1,2,4-triazin-5(4H)-one (ETHIOZIN); 2-{4-[(6-chloro-2-benzoxazolyl)-oxy]-phenoxy}-propanoic acid, its methyl ester or its ethyl ester (FENOXAPROP); [(4-amino-3,5-dichloro-6-fluoro-2-pyridinyl)-oxy]-acetic acid or its l-methylheptyl ester (FLUROXYPYR); methyl 2-[4,5-dihydro-4-methyl-4-(1-methylethyl)-5-oxo-lH-imidazol-2-yl]-4(5)-methylbenzoate ( TMA~AM~T~AR~NZ ); 3,5-diiodo-4-hydroxybenzonitrile (IOXYNIL); N,N-dimethyl-N'-(4-iso-propylphenyl)-urea (ISOPROTURON); (2-methyl-4-chloro-phenoxy)-acetic acid (MCPA); (4-chloro-2-methylphenoxy)-propionic acid (MCPP); N-methyl-2-(1,3-benzothiazol-2-yloxy)-acetanilide (MEFENACET); 2-ethyl-6-methyl-N-(1-methyl 2-methoxyethyl)-chloroacetanilide (METor~A~FToR)~
2-{[((4-methoxy-6-methyl-1,3,5-triazin-2-yl)-amino)-carbonyl]-amino]-sulphonyl}-benzoic acid or its methyl ester (METSULFURON); 2-chloro-4-trifluoromethylphenyl 3-ethoxy-4-nitro-phenyl ether (OXYFLUORFEN); N-(1-ethyl-propyl)-3,4-dimethyl-2,6-dinitroaniline (PENDIMETHALIN);
2-chloro-N-isopropylacetanilide (PROPACHLOR); 0-(6-chloro-3-phenyl-pyridazin-4-yl) S-octyl thiocarbonate (PYRIDATE); 2-chloro-4,6-bis-(ethylamino)-1,3,5-triazine (SIMAZINE); 4-ethylamino-2-t-butylamino-6-methylthio-s-triazine (TER~UlK~N~); methyl 3-[[[[(4-methoxy-6-methyl-Le A 26 538 - 47 -Z003~0~3 -1,3,5-triazin-2-yl)-amino]-carbonyl]-amino]-sulphonyl]-thiophene-2-carboxylate (THIAMETURON); S-(2,3,3-tri-chloroallyl) N,N-diisopropylthiolcarbamate (TRI-ALLATE) and 2,6-dinitro-4-trifluoromethyl-N,N-dipropylaniline (TRIFLURALIN). Surprisingly, some mixtures also show a synergistic action.
Mixtures with other known active compounds, such as fungicides, insecticides, acaricides, nematicides, 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 use forms prepared therefrom by further dilution, such as ready-to-use solutions, suspensions, emulsions, powders, pastes and granules. They are used in the customary manner, for example by watering, spraying, atomizing or scattering.
The active compounds according to the invention can be applied either before or after emergence of the plants.
20They can also be incorporated into the ~oil before sowing.
The amount of active compound used can varywithin a substantial range. It depends essentially on the nature of the desired effect. In general, the amounts used are 25between 0.01 and 10 kg of active compound per hectare of soil surface, preferably between 0.05 and 5 kg per ha.
The preparation and use of the active compounds according to the invention can be seen from the following examples.

Le A 26 538 - 48 -200;~2~)~

Preparation Examples Example 1 (CH3)2C ~ N-NH2 N`N~:O
O=C-NI~

(Process (b)) 6.1 g (0.055 mol) of cyclopentyl isocyanate and a small amount of diazabicycloundecene (DBU) are added to 7.1 g (0.05 mol) of 4-amino-3-isopropyl-(lH)-1,2,4-triazolin-5-one in 100 ml of absolute acetonitrile, the mixture is stirred for 12 hours at room temperature and then concen-trated in vacuo, the residue is taken up in dichloro-methane, the solution is washed with water to neutrality,dried over magnesium sulphate and concentrated, and the residue is crystallized by trituration with diethyl ether.
10.0 g (78 % of theory) of 4-amino-1-(N-cyclo-pentylcarbamoyl)-3-isopropyl-1,2,4-triazolin-5-one of melting point 109C are obtained.

Le A 26 538 - 49 -" .,. ,., . ., .. , :

Example 2 H2C`
H2C~ H~
N`N~
¦ CH3 ~C~ I
~H-f-C--CH

(Process (a) - one-pot variant) 5.5 g (0.05 mol) of 3-methyl-3-butinyl isocyanate and a small amount of diazabicycloundecene (DBU) are added to 11.1 g (0.05 mol) of 4-(4-methylpent-2-ylideneimino)-3-cyclopropyl-1,2,4-(lH)-triazolin-5-one in 150 ml of absolute acetonitrile, the mixture is stirred for 12 hours at 20C and subsequently concentrated in vacuo, the residue is taken up in aqueous ethanol, 2 ml of concen-trated hydrochloric acid are added, the mixture is slowly concentrated at 60C under reduced pressure, the residue is taken up in dichloromethane, the solution is washed using saturated sodium hydrogen carbonate solution, dried over magnesium sulphate and concentrated, and the residue is crystallized by trituration with diethyl ether.
10.4 g (84 % of theory) of 4-amino-3-cyclopropyl-l-[N-(3-methyl-3-butinyl)-carbamoyl]-1,2,4-triazolin-5-one of melting point 160C are obtained.
The following substituted triazolinones of the general formula (I) are obtAine~ in a corresponding manner and following the general preparation instructions:

Le A 26 538 - 50 -. ~ 2003208 - , Rl~N'NH2 1 ~ 0 (I) 0~ NH-R2 Ex. ~1 R2 Physica~
No. constant 3 (CH3)3c -(CH2~5-CH3 n20: 1,4980 CH3-(CH2)2 -C-C-CH m.p 106 C

fH3 (CH3)2CH- -C-C--CH m.p. 90 C

6 (CH3)2CH ~ I m.p. 133 C
~2 ~CH2 CH3-(CH2)2 ~CH2 m.p. 98 C

8 (CH3)3C ~ICH2 m.p. 158 C
~CH2 9 CH3-(CH2)2 {~3 m.p. 100 C

(CH3)2CH ~ nD: 1,5168 Le A 26 538 - 51 -r . - .

- ~ Ex. R1 RZ Physical No. constant fH3 11 CH3-(CH2)2 -C-CH2Cl nD: 1,5890 12 (CH3)2CH- IH3 n20: 1.5650 1H-NMR*):
13 (CH3)3C- ~ 4 48 (2H) 1H-NMR*):
14 (CH3)3C- ~ 1,44 (9H), (CH3)3C- -C(CH3)3 m.p. 142 C

16 (CH3)3C- {~Cl m.p. 203 C

17 CH3-(CH2)2 -C~CH3~? m.p. 112 C

18 (CH3)2CH- -C(CH~)3 m.p. 108 C
19 ~ -CtCH3)3 m.p. 151 C

(CH3)3C- -CH ~ n20: 1~5171 (S-) config, 21 (CH3)3C- -CH ~ n20: 1,5411 (R~ ) conf i 9 .

Le A 26 538 - 52 -2003~08 Ex. Rl R2 Physical No. constant fH3 22 (CH3)3C- -f-CH2-Cl m.p. 133 C

23 (CH3~3c- -IC-C--CH m.p. 148 C

fH3 24 (CH3)3C- f (CH2)3 CH3 n20: 1,4844 (CH3)3C- -fH-CH(CH3)2 m . P 135 C

26 (CH3)3C- -C-CH2F m . p . 141 C

27 (CH3)3C- -CH2 ~ l m.p- 208 C

28 (CH3)3C- f ~ nD: 1,5520 29 (CH3)3C- (CH2)2 ~ 1 m.p. 172 C

(CH3)2CH -fH-C2H5 m.p. 83 C

Le A 26 538 - 53 -Ex. Rl R2 Physical No. constant 3~ (CH3)2CH -f-C2H5 n20 1,4801 32 H2f` ~ m.p. 177 C

33 ¦ CH- n m.p. 107 C
H2C~
fH3 34 ~CH3~2CH -c-cH2F m.p. 124 C

CH2Cl lH-NMR*):
¦ 1,34 (6H), 20 35 (CH )2CH- -C-CH3 3,12 (lH), 3 1 . 4,40 (2H) (CH3)2CH- -f-CHCl2 m.p. 121 C

37 (CH3)2CH -CH(CH3)2 m.p. 124 C

38 (CH3)2CH- -f (CH2)3 CH3 nD: 1~4874 39 (CH3)2CH -f-(CH2)3 CH3 nD: 1,4847 Le A 26 538 - 54 -Ex. R1 R2 Physical No. constant (CH3)2CH- -cH-cH(cH3)2 nD: 1~4860 41 (CH3)2CH- -CH~3 nD: 1.5308 CH3 (S-) conf jg.

42 (CH3)2CH ¢{~ n20: 1,5355 43 (CH3)2CH- H3C~1 n20: 1,5011 H2C~ fH3 44 ¦ CH- -C-CH2Cl m.p. 94 C
H2C~

H2C~
H2C~ -C-CH2F m.p. 138 C

~--~ amorphous 46 (CH3)2CH- ~ H > ~ = 1.34 Duplett (2CH3) ~~ 3,13 Multiplett (lH) Cl 3.90 Multiplett (2H) 4.48 Singulett (NH2) 8.04 Duplett (NH) Le A 26 538 . .

Ex.Rl R2 Physical No. constant amorphous H C r--~ S = 1.05 Multiplett ~2H, 21 ~ ~ 1.16 Multiplett (2H, Cl cyclopropyl) 2,06 Multiplett (lH, cyclopropyl) 3.89 Multiplett (2H) 4.55 Singulett (NH2) 8,03 Duplett (NH) 48(CH3)2CH -C4H9-n n~: 1,4969 49¦ ~CH -C4H9-n mp: 84C

The lH-NMR spectra were recorded in deuterochloroform (CDCl3) with tetramethylsilane (TMS) as the internai st~n~rd. The chemical shift is indicated as a value in ppm.

Le A 26 538 ~ . . ... . ... . . . .

ZOO;~Z08 - Preparation of the starting compounds _____________________________________ Example III-l H2C`
H2C~ ~ ~ N~2 N~N O
H

1892 g (8.84 mol) of diphenyl carbonate are added in portions to 884 g (17.68 mol) of hydrazine hydrate with stirring and ice-cooling, so that the temperature of the reaction mixture does not exceed 30C. When the addition is complete, the mixture is stirred for about 3 hours at 80C, any reaction water formed during this process is removed in vacuo, 760 g (8.84 mol) of cyclopropane-carboxylic acid are then added, the mixture is subse-quently heated to 200C in the course of 6 hours and under an atmosphere of inert gas, and any reaction water liberated is simultaneously distilled off. When the reaction is complete, the mixture is evaporated in vacuo to dryness, the residue is extracted using 3000 ml of boiling ethanol, the extract is filtered and cooled, and the crystalline precipitate which has formed is filtered off with suction and dried.
420 g (34 % of theory) of 4-amino-3-cyclopropyl-1,2,4-(lH)-triazolin-5-one of melting point 181C are obt~ine~.
The following are obt~ineA in a corresponding manner:

Le A 26 538 Example III-2 fH3 C 2H5 - C~ IN- NH2 N~N~o melting point 168C

Example III-3 (CH3~2C ~ _I-NH2 N`NI ~0 melting point 168C

5 Example III-4 CH3~
CH ~CH CH2~ N-NH2 N~N~o H

ExamPle III-5 CH3-(CH2)3 ~ N-NH2 N~H~O

Le A 26 538 r ExamPle (III-6) (CH3)3C~ r NI-NH2 i I -melting point 261C

Example VIII-1 H2C~ ~H ~CH~
H2C~ ~ ~CH2-CH(CH3)2 N` I O

142 g (1.0 mol) of 4-amino-3-cyclopropyl-1,2,4-(lH)-triazolin-5-one in 1000 ml of methyl isobutyl ketone with the addition of 100 mg of p-toluenesulphonic acid are refluxed in a water sep~rator until the liberation of further reaction water has ceased. For working up, the mixture is concentrated in vacuo, and the residue is crystallized by trituration with petroleum ether.
66 g (30 % of theory) of 4-(4-methylpent-2-ylideneimino)-3-cyclopropyl-1,2,4-(lH)-triazolin-5-one of melting point 64C are obtained.
Use Examples In the use examples which follow, the compounds listed below were employed as comparison substances:

Le A 26 538 ,. . .. . .

_ CH3S~N-NH2 N~NI ~ O (A) o=c-NH-cH(cH3)2 4-amino-1-(N-isopropylcarbamoyl)-3-methylthio(lH,4H)-1,2,4-triazolin-5-one CH3S~I ~ NH2 (B) N~7 o O=C-NH-(CH2)2-cH3 4-amino-1-(N-propylcarbamoyl)-3-methylthio-(lH,4H)-1,2,4-triazolin-5-one CH35 ~ ~ NH2 N`IN o (C) O=C-NH-(CH2)~-CH3 4-amino-1-(N-butylcarbamoyl)-3-methylthio-(lH,4H)-1,2,4-triazolin-5-one and CH35~r_lN- NH2 N~IN~o (D) ~C~ \
o NH ~

4-amino-1-(N-cyclohexylcarbamoyl)-3-methylthio-(lH,4H)-1,2,4-triazolin-5-one;
all disclosed in JP 52/125,168.

Le A 26 538 - Example 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, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Seeds of the test plants are sown in normal soil and, after 24 hours, watered with the preparation of the active compound. It is expedient to keep constant the amount of water per unit area. The concentration of the active compound in the preparation is of no importance, only the amount of active compound applied per unit area being decisive. After three weeks, the degree of damage to the plants is rated in % damage in comparison to t~e development of the untreated control. The figures denote:
0% = no action (like untreated control) 100% = total destruction In this test, a clearly superior activity, combined with a comparably good selectivity towards crop plants, compared with the prior art, is shown in this test, for example, by the compounds of the following preparation examples: (1), (10), (18), (30), (31), (34), (37) and (40).

Le A 26 538 Example B

Post-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, 1 part by weight of active compound is mixed with the stated amount of solvent, the stated amount of emulsifier is added and the concentrate is diluted with water to the desired concentration.
Test plants which have a height of 5 - 15 cm are sprayed with the preparation of the active compound in such a way as to apply the particular amounts of active compound desired per unit area. The concentration of the spray liquor is chosen so that the particular amounts of active compound desired are applied in 2,000 l of water/ha. After three weeks, the degrea of ddmaga to the plants is rated in % damage in comparison with the development of the untreated control. The figures denote:
0% = no action (like untreated control) 100% = total destruction In this test, a clearly superior astivity, combined with a comparably good selectivity towards crop plants, compared with the prior art, is shown in this test, for example, by the compounds of the following preparation examples: (12), (18), (19), (30), (34), (36), (37), (38), (39) and (40).

Le A 26 538

Claims

1. A substituted triazolinone of the general formula (I) (I) in which R1 represents alkyl having 3 to 4 carbon atoms, or represents cyclopropyl, and R2 represents hydrogen, or represents in each case straight-chain or branched alkyl having 1 to 18 carbon atoms, alkenyl having 2 to 8 carbon atoms, alkinyl having 2 to 8 carbon atoms, halogenoalkyl having 1 to 8 carbon atoms and 1 to 17 identical or different halogen atoms, halogenoalkenyl or halogenoalkinyl, each of which has 2 to 8 carbon atoms and 1 to 15 or 13 identical or different halogen atoms, cyanoalkyl having 1 to 8 carbon atoms, hydroxyalkyl having 1 to 8 carbon atoms and 1 to 6 hydroxyl groups, alkoxyalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkenyl, each having up to 6 carbon atoms in the individual alkyl or alkenyl moieties, or alkylaminoalkyl or dialkylaminoalkyl each having 1 to 6 carbon atoms in the individual alkyl moieties, or represents cycloalkyl having 11 carbon atoms, or represents cycloalkyl, cycloalkylalkyl, cycloalkenyl or cycloalkenylalkyl, each of which has 3 to 8 carbon atoms in the cycloalkyl or cycloalkenyl moiety and if appropriate 1 to 6 carbon atoms in the alkyl moiety, and each of which is optionally monosubstituted or polysubstituted by identical or different substituents selected from the group consisting of halogen, cyano as well as in each case straight-chain or branched alkyl or halogenoalkyl, each of which has 1 to 4 carbon atoms and if appropriate 1 to 9 identical or different halogen atoms, straight-chain or branched halogenoalkenyl having up to 4 carbon atoms and 1 to 5 identical or different halogen atoms, and in each case double-linked alkanediyl or alkenediyl, in each case having up to 4 carbon atoms; R2 furthermore represents heterocyclylalkyl which has 1 to 6 carbon atoms in the straight-chain or branched alkyl moiety and 1 to 9 carbon atoms and 1 to 3 hetero atoms in the heterocyclyl moiety and which is optionally monosubstituted or polysubstituted in the heterocyclyl moiety by identical or different substituents selected from the group consisting of halogen, cyano, nitro, and in each case straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio and alkoxycarbonyl, each of which has 1 to 5 carbon atoms and if appropriate 1 to 9 identical or different halogen atoms; R2 furthermore represents in each case straight-chain or branched alkoxy having 1 to 8 carbon atoms, alkenyloxy having 2 to 8 carbon atoms or alkinyloxy having 2 to 8 carbon atoms, and finally represents aralkyl, aroyl, aryl, aralkyloxy or aryloxy, each of which has 6 to 10 carbon atoms in the aryl moiety and if appropriate 1 to 8 carbon atoms in the straight-chain or branched alkyl moiety and each of which is optionally monosubstituted or polysubstituted by identical or different substituents, the alkyl substituents when present selected from the group consisting of halogen and cyano, and the aryl substituents when present being selected from the group consisting of halogen, cyano, nitro, hydroxyl, in each case straight-chain or branched alkyl, alkoxy, alkylthio, halogenoalkyl, halogenoalkoxy, halogenoalkylthio, alkylsulphinyl, alkylsulphonyl, halogenoalkylsulphinyl, halogenoalkylsulphonyl, alkanoyl and alkoxycarbonyl, each of which has 1 to 6 carbon atoms in the alkyl moiety and if appropriate 1 to 9 identical or different halogen atoms, and cycloalkyl having 3 to 6 carbon atoms and phenoxy; or R
represents benzyl with an O-CH2-0- group fused to the phenyl moiety.

2. A substituted triazolinone according to claim 1 in which R1 represents n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl or cyclopropyl.

3. A substituted triazolinone according to claim 1, in which R1 represents n-propyl, i-propyl, i-butyl, s-butyl, t-butyl or cyclopropyl and R represents hydrogen, methyl, ethyl, n- or i-propyl, n-, i-, s-, or t-butyl, in each case straight-chain or branched pentyl, hexyl, heptyl, octyl, nonyl, decyl or dodecyl, or represents allyl, in each case straight-chain or branched butenyl, pentenyl or hexenyl, propargyl, in each case straight-chain or branched butinyl, pentinyl or hexinyl, or represents straight-chain or branched halogenoalkyl having 1 to 8 carbon atoms and 1 to 9 identical or different halogen atoms, or represents in each case straight-chain or branched halogenoalkenyl or halogenoalkinyl, each of which has 3 to 8 carbon atoms and 1 to 3 halogen atoms, or represents in each case straight-chain or branched cyanolalkyl having 1 to 6 carbon atoms in the alkyl moiety, hydroxyalkyl having 1 to 6 carbon atoms and 1 to 3 hydroxyl groups, or alkoxyalkyl, alkoxycarbonylalkyl or alkoxycarbonylalkenyl, alkylaminoalkyl or dialkylaminoalkyl, each of which has up to 4 carbon atoms in the individual alkyl or alkenyl moieties, or represents cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclo-pentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclohexyl-methyl, cyclohexylethyl, cyclohexenyl or cyclohexenylmethyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, methyl, ethyl, n-or i-propyl, n-,i-, s- or t-butyl, cyano, methanediyl, ethanediyl, butanediyl, butadienediyl and dichloroallyl;
or R2 represents heterocyclylmethyl, heterocyclylpropyl or heterocyclylethyl, each of which is optionally monosubstituted to trisubstituted in the heterocyclyl moiety by identical or different substituents, selected heterocycles in each case being:

; ; ; ;

; ; ; ;

; and ' Z in each case representing oxygen or sulphur, and selected substituents in each case being:

fluorine, chlorine, bromine, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy or trifluoromethylthio; or R2 additionally represents in each case straight-chain or branched alkoxy having 1 to 6 carbon atoms, alkenyloxy having 3 to 6 carbon atoms or alkinyloxy having 3 to 6 carbon atoms, or represents benzyl, phenylethyl, phenylpropyl, phenylbutyl, phenylpentyl, phenylhexyl, phenylheptyl, phenylcyanomethyl, phenylcyanoethyl, phenylcyanopropyl, benzyloxy, phenylethyloxy, phenoxy, benzoyl, phenyl or naphthyl, where appropriate straight-chain or branched, each of which is optionally monosubstituted to trisubstituted on the phenyl by identical or different substituents selected from the group consisting of fluorine, chlorine, bromine, hydroxyl, cyano, nitro, methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, methylthio, trifluoromethyl, trifluoromethoxy, trifluoromethylthio, trifluoromethylsulphinyl, trifluoromethylsulphonyl, methlysulphinyl, methylsulphonyl, acetyl, propionyl, methoxycarbonyl, ethoxycarbonyl, cyclohexyl and phenoxy.

4. A substituted triazolinone according to claim 1, in which R1 represents isopropyl, cyclopropyl or s-butyl and R2 represents methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, allyl, propargyl, in each case straight-chain or branched pentyl, hexyl, heptyl, octyl, butenyl, pentenyl, hexenyl, butinyl, pentinyl or hexinyl, each of which is optionally monosubstituted to trisubstituted by fluorine and/or chlorine; additionally represents cyclopropyl, cyclopentyl, cyclohexyl, cyclohexenyl, cyclopropylmethyl, cyclopropylethyl, cyclohexylmethyl, cyclohexylethyl or cycloheptyl, each of which is optionally monosubstituted to trisubstituted by identical or different substituents from the group consisting of fluorine, chlorine, methyl, ethyl and/or cyano, or represents benzyl or phenylethyl.

5. 4-Amino-1-[N-(chloro-t-butyl) carbamoyl]
-3-isopropyl-1,2,4-triazolin-5-one of the formula

6. 4-Amino-1-(N-5-butylcarbamoyl)-3-isopropyl-1,2,4-triazolin-5-one of the formula

7. 4-Amino-1-[N-(fluoro-t-butyl) carbamoyl]-3-isopropyl-1,2,4-triazolin-5-one of the formula

8. 4-Amino-1-(N-isopropylcarbamoyl)-3-isopropyl-1,2,4-triazolin-5-one of the formula

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

10. A herbicidal composition comprising a herbicidally effective amount of a compound according to any one of claims 1 to 8 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.

11. 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 8.

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 a compound according to any one of claims 1 to 8 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 0.1 and 95% by weight of a compound according to any one of claims 1 to 8 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 composition containing between 0.5 and 90% by weight of a compound according to any one of claims 1 to 8 in admixture with a suitable carrier or diluent.

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 8 wherein the compound is applied as a pre-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 8 wherein the compound is applied as a post-emergence herbicide.

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 8 wherein the compound is applied to an area of cultivation at a rate of between 0.1 and 10 kg/ha.

18. 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 8 wherein the compound is applied to an area of cultivation at a rate of between 0.05 and 5 kg/ha.

19. A process for preparing a compound according to claim 1 wherein R1 and R2 are as defined in claim 1, which process comprises (a) reacting a hydrazone of the formula (II) (II) in which R1 and R2 have the abovementioned meaning and R3 and R4 independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or represent phenyl or benzyl, with an acid, or (b) reacting a 1H-triazolinone of the formula (III) (III) in which R1 has the abovementioned meaning with an isocyanate of the formula (IV) R2-N=C=O (IV) in which R2 has the abovementioned meaning, or (c) reacting a triazolinone of the formula (V) (V) in which R1 has the abovementioned meaning and R5 represents straight-chain or branched alkyl having 1 to 4 carbon atoms, or represents phenyl or benzyl, each of which is optionally monosubstituted to trisubstituted by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio, each of which has 1 to 4 carbon atoms, or in each case a straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio, each of which has 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms with an amine of the formula (VI) R2-NH2 (VI) in which R2 has the abovementioned meaning, or (d) reacting a 1H-triazolinone of the formula (III) (III) in which R1 has the abovementioned meaning with a urethane of the formula (VII) (VII) in which R2 has the abovementioned meaning and R5 is as defined above.

20. A process for preparing a herbicidal composition comprising admixing a compound according to any one of the claims 1 to 8 with a diluent or surface-active agent.

21. A hydrazone of the formula (II) (II) in which R1 and R2 are as defined in claim 1 and R3 and R4 independently of one another each represent hydrogen, or represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or represent phenyl or benzyl.

22. A 1-unsubstituted 4-aminotriazolinone of the formula (IIIa) (IIIa) in which R1 1 represents n-butyl, i-butyl, s-butyl or cyclopropyl.

23. A triazolinone of the formula (XI) (XI) in which R1 is as defined in claim 1, R3 and R4 independently of one another represent hydrogen, or represent straight-chain or branched alkyl having 1 to 4 carbon atoms, or represent phenyl or benzyl, and R5 represents straight-chain or branched alkyl having 1 to 4 carbon atoms, or represents phenyl or benzyl, each of which is optionally monosubstituted to trisubstituted by halogen, cyano, nitro, in each case straight-chain or branched alkyl, alkoxy or alkylthio, each of which has 1 to 4 carbon atoms, or in each case a straight-chain or branched halogenoalkyl, halogenoalkoxy or halogenoalkylthio, each of which has 1 to 4 carbon atoms and 1 to 9 identical or different halogen atoms.