CA2250044A1

CA2250044A1 - Substituted 1-methyl-3-benzyluracils

Info

Publication number: CA2250044A1
Application number: CA002250044A
Authority: CA
Inventors: Olaf Menke; Gerhard Hamprecht; Elisabeth Heistracher; Ralf Klintz; Peter Schafer; Cyrill Zagar; Markus Menges; Karl-Otto Westphalen; Helmut Walter; Ulf Misslitz
Original assignee: Individual
Current assignee: BASF SE
Priority date: 1996-03-27
Filing date: 1997-03-10
Publication date: 1997-10-02
Also published as: WO1997035845A1; AU1926397A; JP2000507250A; EP0891336A1; DE19612032A1; EP0891336B1; AR006444A1; DE59707428D1; ZA972591B

Abstract

The invention concerns substituted 1-methyl-3-benzyluracils (I) and their salts and enol ethers as herbicides or desiccating/defoliating agents. In formula (I), R1 is C1-C4 alkyl halide; R2 is H or halogen; R3 is R2, CN, SCN, C1-C4 alkyl halide, C1-C4 alkoxy halide or C1-C4 alkylthio halide; R4 is R3, C1-C4 alkyl, C1-C4 alkoxy or (C1-C6 alkylamino)-CO-; R5 is R2, CN, NO2, OH, optionally substituted amino, alkoxy, alkylthio, alkyl-CO2-, alkyl-COS-, alkyl-SO2-O- or alkyl-SO2-, the six last-mentioned groups optionally being functionalized and/or substituted; R6, if it is in the .alpha. position with R5 then being in the .beta. position, is OH, SH, alkyl, alkoxy, alkylthio, alkyl-CO2-, alkyl-COS-, alkoxy-CO-, alkoxy-CO2-, alkyl-SO2-O-, alkyl-SO2-, alkyl-CO-, alkyl-CS-, alkyl-(N-alkyl)-imino or alkyl-(N-alkoxy)-imino, the thirteen last-mentioned groups optionally being functionalized and/or substituted, or methyl substituted twice by optionally substituted alkoxy and alkylthio and optionally substituted once by alkyl; or R6 in the .beta.
position, with R5 then being in the .alpha. position, has the above meanings, as well as alkyl-amino-CO-, alkoxy-CO-, alkylthio-CO-, alkyl-CO-, alkylimino-oxycarbonyl, alkyl-(N-alkoxy)-imino, alkoxy-(N-alkoxy)-imino or alkylthio-(N-alkoxy)-imino, the eight last-mentioned groups optionally being functionalized and/or substituted, or methyl substituted three times by optionally substituted alkoxy, alkylthio and alkylamino.

Description

0050/46725 CA 022~0044 1998-09-24 Substituted l-methyl-3-benzyluracils The present invention relates to novel substituted 5 1-methyl-3-benzyluracils of the formula I

H3C o N ~ ~ R5;R6 Rl ~ N- CH2 ~ ~ I

where:
X is oxygen or sulfur;
Rl is Cl-C4-haloalkyl;

20 R2 is hydrogen or halogen;

R3 is hydrogen, cyano, thiocyanato, halogen, Cl-C4-haloalkyl, C1-C4-haloalkoxy or Cl-C4-hAloAlkylthio;

25 R4 is hydrogen, cyano, thiocyanato, halogen, Cl-C4-alkyl, Cl-C4-haloalkyl, Cl-C4-alkoxy, Cl-C4-haloAlkoxy, Cl-C4-haloalkylthio or (cl-c6-alkylamino)carbonyl;

R5 in position a or ~ is hydrogen, cyano, nitro, hydroxyl, amino, halogen, Cl-C4-alkylamino, which may be substituted by Cl-C4-alkyl, (Cl-C4-alkyl)carboxyl or (Cl-C4-alkoxy)carbonyl, Cl-C6-haloAlkoYy, Cl-C6-haloalkylthio, Cl-C6-alkoxy, Cl-C6-alkylthio, C3-C6-cycloalkyloxy, C3-C6-cycloalkylthio, C3-C6-alkenyloxy, C3-C6-alkenylthio, C3-C6-alkynyloxy, C3-C6-alkynylthio, (Cl-C6-alkyl)carbonyloxy, (Cl-C6-alkyl)-carbonylthio, (c3-c6-alkenyl)carbonyloxy~ (C3-C6-alkenyl)-carbonylthio, (C3-C6-alkynyl)carbonyloxy, (C3-C6-alkynyl)-carbonylthio, Cl-C6-alkylsulfonyloxy or Cl-C6-alkylsulfonyl, where each of the last-mentioned 16 radicals may, if desired, carry from one to three substituents, each selected from the group consisting of - halogen, nitro, cyano, hydroxyl, C3-C6-cycloalkyl, Cl-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, Cl-C6-alkoxy-Cl-C6-alkoxy, 0050/46725 CA 022~0044 1998-09-24 Cl-C6-alkylthio, Cl-C6-alkylsulfynyl, Cl-C6-alkylsulfonyl, Cl-C6-alkylidene~m;noxy, - a phenyl, phenoxy or phenylsulfonyl group which may be unsubstituted or may carry from one to three substituents each selected from the group consisting of halogen, nitro, cyano, Cl-C6-alkyl, Cl-C6-alkoxy and Cl-C6-haloalkyl, - a 3- to 7-membered heterocyclyl or heterocyclyloxy group which may carry from one to three substitutents each selected from the group consisting of halogen, nitro, cyano, Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6-alkoxy and (Cl-C6-alkyl)carbonyl, - -Co-R7, -Co-oR7, -Co-SR7, -Co-N(R7)R8, -oCo-R7, -oCo-oR7, -oCo-SR7, -oCo-N(R7 )R8 or -N(R7 )R8, where R7 iS hydrogen, Cl-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, Cl-C6-alkoxy-Cl-C6-alkyl, (Cl-C6-alkoxy)carbonyl-C1-C6-alkyl, (C3-C6-alkenyloxy)-carbonyl-Cl-C6-alkyl, phenyl or phenyl-Cl-C6-alkyl, where the phenyl group and the phenyl ring of the phenalkyl group may be unsubstituted or may carry from one to three radicals each selected from the group consisting of halogen, nitro, cyano, Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6-alkoxy and (cl-c6-alkyl)carbon and R8 is hydrogen, hydroxyl, Cl-C6-alkyl, C3-C6-cycloalkyl, Cl-C6-alkoxy, (Cl-C6-alkoxy)carbonyl-Cl-C6-alkoxy, C3-C6-alkenyl or C3-C6-alkenyloxy;

or R7 and R3 together with the common nitrogen atom form a 3- to 7-membered heterocyclyl group which may in turn carry from one to three substituents each selected from the group consisting of halogen, nitro, cyano, Cl-C6-alkyl, C1-C6-haloalkyl, Cl-C6-alkoxy and (cl-c6-alkyl)carbonyl;
R6 in position a, R5 then being in position ~, is 1) hydroxyl, mercapto, Cl-C6-haloalkoxy, Cl-C6-haloalkylthio, 2) C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C5-C7-cy alkenyloxy, C2-C6-alkenylthio, C2-C6-alkynyloxy, -- . . . .. .

CA 022~0044 1998-09-24 C2-C6-alkynylthio, (Cl-C6-alkyl)carbonyloxy, (Cl-C6-alkyl)carbonylthio, (cl-c6-alkoxy)carbonyloxy~
(C2-C6-alkenyl)carbonyloxy, (C2-C6-alkenyl)carbonylthio, (C2-C6-alkynyl)carbonyloxy, (C2-C6-alkynyl)carbonylthio, Cl-C6-alkylsulfonyl or Cl-C6-alkylsulfonyloxy, where each of the last-mentioned 18 radicals may, if desired, carry from one to four substituents each selected from the group consisting of - halogen, nitro, cyano, hydroxyl, C3-C6-cycloalkyl, Cl-C6-alkoxy, C3-C6-cyclo~lko~y, C3-C6-alkenyloxy, C3-C6-alkynyloxy, Cl-C6-alkoxy-Cl-C6-alkoxy, Cl-C6-alkylthio, Cl-C6-alkylsulfinyl, Cl-C6-alkylsulfonyl, Cl-C6-alkylideneaminoxy, - a phenyl, phe~oxy or phenylsulfonyl group which may be unsubstituted or may carry from one to three substituents each selected from the group consisting of halogen, nitro, cyano, Cl-C6-alkyl, Cl-C6-halo-alkyl, Cl-C6-alkoxy and (Cl-C6-alkoxy)carbonyl, - a 3- to 7-membered heterocyclyl or heterocyclyloxy group which may carry from one to three substituents each selected from the group consisting of halogen, nitro, cyano, Cl-C6-alkyl, Cl-C6-alkoxy, Cl-C6-haloalkyl and (cl-c6-alkyl)carbon - an oxygen atom bonded via a double bond, - a -CO-R9, -CO-OR9, -CO-SR9, -CO-N(R9)Rl0, -OCO-R9, --OCO-OR9,--OCO-SR9, --OCO--N(R9)Rl0 or --N(R9)Rl~, where R9 has one of the meanings of R7 and Rl~ has one of the meanings of R8, - =N-OR20, -C(R2l)=N-OR20 or Si(R30, R3l, R32), where R30, R3l, R32, indepen~ently of one another are each Cl-C6-alkyl or C2-C6-alkenyl;

3) -CY-Rll, -C(Rll)(ZlRl2)(Z2Rl3), where zl and z2 are in each case oxygen or sulfur, --C(Rll)=C(R14)--CN, --C(Rll)=C(R14)--CO--R15, _CH(Rll)_CH(R14)_Co--R15, --c(Rll)=c(Rl4)-cH2 - co - R
_C(Rll)=c(Rl4) - c(Rl6)=c(Rl7) - co - Rls~
--C(Rll)=C(R14)--CH2--CH(R13)--CO--R15, --CO--ORl9, --C--C--CO--NH--OR20, --C--C--CO--N(Rl9)--OR20, --C----C--CS--NH--OR20, -c-c-CS-N(Rl9)-oR2o~ -C-C-C(R2l)=N-oR20 0050/46725 CA 022~0044 1998-09-24 -c(Rll)=c(Rl4)-co-NH-oR2o~ -c(Rll)=c(Rl4)-cO-N(Rl9)-oR2o -c(Rll)=c(Rl4)-cs-NH-oR2o~ -c(Rll)=c(Rl4)-cs-N(Rl9)-oR2o --C(Rll)=C(R14)--C(R21)=N--oR20, -N(R23)R24, o - Alk S - Alk C-- C ~C~N~O , -- C-- C ~C~N ~
o Alk C(Rll) = C(Rl4) N or S Alk C(R1l) = C(Rl4) ~ N
where Alk is Cl-C3-alkylene which may carry a Cl-C6-alkyl substituent;

20 Rll is hydrogen, cyano, Cl-C6-alkyl, Cl-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, Cl-C6-alkoxy-C1-C6-alkyl or (Cl-C6-alkoxy)carbonyl;

Rl2 and Rl3, inde~en~ently of one another, are each Cl-C6-alkyl, Cl-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl or Cl-C6-alkoxy-Cl-C6-alkyl or R12 and R13 together form a saturated or unsaturated, two- to four-membered carbon chain which may carry an oxo substituent, where a member of this chain may be replaced by an oxygen, sulfur or nitrogen atom, which is not adjacent to Zl and Z2 and where the carbon chain may furthe -re carry from one to three radicals each selected from the group consisting of cyano, nitro, amino, halogen, Cl-C6-alkyl, C2-C6-alkenyl, Cl-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyl-oxy, Cl-C6-haloalkyl, cyano-Cl-C6-alkyl, hydroxy-Cl-C6-alkyl, Cl-C6-alkoxy-Cl-C6-alkyl, C3-C6-alkenyloxy-Cl-C6-alkyl, C3-C6-alkynyloxy-Cl-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cy alkoxy, carboxyl, (C1-C6-alkoxy)carbonyl, (Cl-C6-alkyl)car-bonyloxy-C1-C6-alkyl and phenyl which in turn may be unsubstituted or may carry from one to three substituents each selected from the group consisting of cyano, nitro, amino, halogen, Cl-C6-alkyl, C1-C6-haloalkyl, Cl-C6-alkoxy and (cl-c6-alkoxy)carbonyl~
and where the carbon chain may also be one or two members of part of a three- to seven-membered ring which may contain one or two heteroatoms as ring members selected from oxygen, .. . .

0050/46725 CA 022~0044 1998-09-24 sulfur, nitrogen and Cl-C6-alkyl-substituted nitrogen, and which, if desired, may in turn carry one or two of the following substituents: cyano, Cl-C6-alkyl, C2-C6-alkenyl, Cl-C6-alkoxy, cyano-Cl-C6-alkyl, Cl-C6-haloalkyl and (Cl-C6-alkoxy)carbonyl;

Rl4 is hydrogen, cyano, halogen, Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6-alkoxy, (Cl-C6-alkyl)carbonyl or (Cl-C6-alkoxy)-carbonyl;
R15 is hydrogen, 0-R22, S-R22, Cl-C6-alkyl which may furthermore carry one or two Cl-C6-alkoxy substituents, or C2-C6-alkenyl, C2-C6-alkynyl, Cl-C6-haloalkyl, C3-C6-cycloalkyl, Cl-C6-alkylthio-Cl-C6-alkyl, Cl-C6-alkyliminoxy, -N(R23)R24 or phenyl which may be unsubstituted or may carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, Cl-C6-alkyl, C2-C6-alkenyl, Cl-C6-haloalkyl, Cl-C6-alkoxy and (Cl-C6-alkoxy)carbonyl, where R22 has one of the meanings of Rl9 and R23, R24, independently of one another, are each hydrogen, Cl-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cy alkyl, Cl-C6-haloalkyl, Cl-C6-alkoxy-Cl-C6-alkyl, (Cl-C6-alkyl)carbonyl, (cl-c6-alkoxy)carbonyl~ (Cl-C6-alkoxy)carbonyl- Cl-C6-alkyl, (C1-C6-alkoxy)-carbonyl-C2-C6-alkenyl, where the alkenyl chain may additionally carry from one to three halogen and/or cyano radicals, or are each Cl-C6-alkylsulfonyl, (Cl-C6-alkoxy)carbonyl-Cl-C6-alkylsulfonyl, phenyl or phenylsulfonyl, where the two phenyl rings may be unsubstituted or may in turn carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, Cl-C6-alkyl, Cl-C6-haloalkyl, C3-C6-alkenyl, Cl-C6-alkoxy and (Cl-C6-alkoxy)carbonyl, or where R23 and R24, together with the common nitrogen atom, form a saturated or unsaturated 4- to 7-membered azaheterocyclic structure which, in addition to carbon ring members, may, if desired, contain one of the following members: -0-, -S-, -N=, -NH- or -N(Cl-C6-alkyl)-;

0050/46725 CA 022~0044 1998-09-24 R16 is hydrogen, cyano, halogen, Cl-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, Cl-C6-alkoxy-C1-C6-alkyl, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, -N(R25)R26, where R25 and R26 have one of the ~n;ngs of R23 and R24, or phenyl, which in turn may furthermore carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, Cl-C6-alkoxy and (C1-C6-alkoxy)carbonyl;

10 Rl7 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, (C1-C6-alkyl)carbonyl or (C1-C6-alkoxy)carbonyl;

R13 is hydrogen, cyano, C1-C6-alkyl or (Cl-C6-alkoxy)carbonyl;
Rl9 is hydrogen, Cl-C6-alkyl, Cl-C6-haloalkyl, C2-C6-alkenyl or C2-C6-alkynyl, where the 4 last-mentioned groups may each carry one or two of the following radicals: cyano, halogen, hydroxyl, hydroxycarbonyl, Cl-C6-alkoxy, Cl-C6-alkylthio, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)carbonyloxy, (C3-C6-alkenyloxy)carbonyl or a 3-to 7-membered azaheterocyclic structure which is bonded to the nitrogen atom by a carbonyl bridge and, in addition to carbon ring members, may furthermore contain an oxygen or sulfur atom as a ring member;
or (Cl-C6-alkyl)carbonyl, (Cl-C6-haloalkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkylamino)carbonyl, di(C1-C6-alkyl)aminocarbonyl, C1-C6-alkoximino-C1-C6-alkyl, C3-C6-cycloalkyl, phenyl or phenyl-C1-C6-alkyl, where the phenyl rings may be unsubstituted or may in turn carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R20 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, hydroxy-Cl-C6-alkyl, Cl-C6-alkoxy-Cl-C6-alkyl, Cl-C6-alkylthio-Cl-C6-alkyl, cyano-C1-C6-alkyl, (C1-C 6- alkyl)carbonyl-C1-C6-alkyl, (C1-C6-alkoxy)carbonyl-C1-C6-alkyl, (C1-C6-alkoxy)carbonyl-C2-C6-alkenyl, (C1-C6-alkyl)carbonyloxy-Cl-C6-alkyl or phenyl-Cl-C6-alkyl, where the phenyl ring may, if desired, carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;

R2l _ is hydrogen, halogen, 0050/46725 CA 022~0044 1998-09-24 - Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6-alkoxy, Cl-C6-haloalkoxy, C3-C6-alkenyloxy, Cl-C6-alkylthio, C1-C6-haloalkylthio, (C1-C6-alkyl)carbonyloxy, (C1-C6-haloalkyl)carbonyloxy, C1-C6-alkylsulfonyloxy or Cl-C6-haloalkylsulfonyloxy, where the 11 last-mentioned radicals may carry one of the following substituents: hydroxyl, cyano, hydroxycarbonyl, C1-C6-alkoxy, C1-C6-alkylthio, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkylamino)carbonyl, di(C1-C6-alkyl)aminocarbonyl, (cl-c6-alkyl)carbon - a 3- to 7-membered azaheterocyclic structure which is bonded to the nitrogen atom by a carbonyl bridge and, in addition to carbon ring members, may also contain an oxygen or sulfur atom as ring member, _ (C1-C6-alkyl)carbonyl, (C1-C6-haloalkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkoxy)carbonyloxy, (C1-C6-alkyl)carbonylthio, (C1-C6-haloalkyl)carbonylthio, (C1-C6-alkoxy)carbonylthio, C2-C6-alkenyl, C2-C6-alkenylthio, C3-C6-alkynyl, C3-C6-Alkynyloxy, C3-C6-alkynylthio, (C2-C6-alkynyl)-carbonyloxy, C3-C6-alkynylsulfonyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cyc loalkylthio, (C3-C6-cycloalkyl)carbonyloxy, C3-C6-Cyc loalkyl-sulfonyloxy, - phenyl, phenoxy, phenylthio, benzoyloxy, phenylsulfonyloxy, phenyl-C1-C6-alkyl, phenyl-C1-C6-alkoxy, phenyl-C1-C6-alkylthio, phenyl-(C1-C6-alkyl)carbonyloxy or phenyl-C1-C6-alkylsulfonyloxy, where the phenyl rings of the 10 last-mentioned radicals may be unsubstituted or may in turn carry from one to three substituents each selected from the qroup consisting of cyano, nitro, halogen, Cl-C6-alkyl, Cl-C6-haloalkyl, Cl-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
Y is oxygen, sulfur or -N(R27)-, where R27 is hydrogen, hydroxyl, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, Cl-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkoxy, C5-C7-cycloalkenyloxy, Cl-C6-haloA1koxy, C3-C6-haloalkenyloxy, hydroxy-Cl-C6-alkoxy, cyano-Cl-C6-alkoxy, C3-C6-cycloalkyl-Cl-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxy-C3-C6-alkenyloxy, (C1-C6-alkyl)carbonyloxy, (cl-c6-haloalkyl)carbonyloxy~
(C1-C6-alkyl)carbamoyloxy, (C1-C6-haloalkyl)carbamoyloxy, (C1-C6-alkyl)carbonyl-C1-C6-alkyl, (C1-C6-alkyl)carbonyl-CA 022~0044 1998-09-24 Cl-C6-alkoxy, (Cl-C6-alkoxy)carbonyl-Cl-C6-alkyl, (Cl-C6-alkoxy)carbonyl-Cl-C6-alkoxy, Cl-C6-alkylthio-Cl-C6-alkoxy, di(Cl-C6-alkyl)amino-Cl-C6-alkoxy, phenyl which in turn may furthermore carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, Cl-C6-alkyl, Cl-C6-haloalkyl, C2-C6-alkenyl, Cl-C6-alkoxy and (Cl-C6-alkoxy)carbonyl, phenyl-Cl-C6-alkoxy, phenyl-C3-C6-alkenyloxy or phenyl-C3-C6-alkynyloxy, where in each case one or two methylene groups of the carbon chain may be replaced by -O- , -S- or -N(Cl-C6-alkyl)- and where each phenyl ring may be unsubstituted or may in turn carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, Cl-C6-alkyl, Cl-C6-haloalkyl, C2-C6-alkenyl, Cl-C6-alkoxy and (Cl-C6-alkoxy)carbonyl, heterocyclyl, heterocyclyl-Cl-C6-alkoxy, heterocyclyl-C3-C6-alkenyloxy or heterocyclyl-C3-C6-alkynyloxy, where in each case one or two methylene groups of the carbon chains may be replaced by -O- , -S- or -N(Cl-C6-alkyl)- and where each heterocyclic structure is three- to 7-membered and may in turn carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, Cl-C6-alkyl, Cl-C6-haloalkyl, C2-C6-alkenyl, Cl-C6-alkoxy and (Cl-C6-alkoxy)carbonyl, or -N(R28)R29, where R28 and R29 are Z5 each hydrogen, Cl-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, Cl-C6-haloalkyl, Cl-C6-alkoxy-Cl-C6-alkyl, (Cl-C6-alkyl)carbonyl, (Cl-C6-alkoxy)carbonyl, (Cl-C6-alkoxy)carbonyl-Cl-C6-alkyl, (Cl-C6-alkoxy)carbonyl-C2-C6-alkenyl, where the alkenyl chain may additionally carry from one to three halogen and/or cyano radicals, or is phenyl which may be unsubstituted or may in turn furthermore carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, Cl-C6-alkyl, Cl-C6-haloalkyl, C3-C6-alkenyl, Cl-C6-alkoxy and (Cl-C6-alkoxy)carbonyl, or R28 and R29, together with the common nitrogen atom, form a saturated or unsaturated 4- to 7-membered heterocyclic structure which, in addition to carbon ring members, may if desired furthermore contain one of the following members:
-O-, -S-, -N=, -NH- or -N(Cl-C6-alkyl)-;

or R6 in position ~, R5 then being in position a, has one of the meanings stated above for R6 and additionally 45 4) -CO-N(Rl9)-OR20, -C(R2l)=N-OR20, -C(ZlRl2)(Z2Rl3)oR
--C(ZlR12) (Z2R13)SR22, --C(ZlRl2) (Z2R13)NR23R24 0050/46725 CA 022~0044 1998-09-24 o Alk S - Alk ~C~ ,o ~C~ ,o N ' N
5 -COO-R22, -cos-R22l -CoN(R23)R24 Cl-C6-alkylthio-(Cl-C6-alkyl)carbonyl or (Cl-C6-alkyl)iminoxycarbonyl;
and the agriculturally useful salts and enol ethers of the 10 co..,~ounds I.

The present invention furthermore relates to - the use of the compounds I as herbicides and/or for the desiccation and/or defoliation of plants, - herbicides and plant desiccants and/or defoliants which contain the compounds I as active ingredients, - processes for the preparation of the compounds I and of herbicides and plant desiccants and/or defoliants using the compounds I, - methods for controlling undesirable plant growth and for desiccating and/or defoliating plants with the compounds I
and - novel intermediates of the formula III and IV.
wo 95/04461 describes 3-benzyl-1-methyl-6-trifluoromethyluracils of the formula II

Ra (Halogen 30\ / H 0 H/Cl ~ N ~ N~ CH3 II

Rb ~ CF3 where Ra is hydrogen, cyano, halogen, Cl-C3-alkoxy, C1-C3-alkylaminocarbonyl or propargyloxy and Rb is hydrogen, cyano, halogen, Cl-C3-alkylamino-carbonyl or carboxyl, as herbicides.
However, the herbicidal action of the known compounds with respect to weeds is still not completely satisfactory. It is an 45 object of the present invention to provide novel herbicidal compounds by means of which undesirable plants can be more readily controlled in a specific manner. It is a further object .. ..

0050/46725 CA 022~0044 1998-09-24 of the present invention to provide novel compounds having desiccant/defoliant activity.

We have found that these objects are achieved by the substituted 1-methyl-3-benzyluracils of the formula I which are defined at the outset. We have also found herbicides which contain the compounds I and have a very good herbicidal action. We have furthermore found processes for the preparation of these agents and methods for controlling undesirable plant growth with the compounds I.

We have furthermore found that the compounds I were also suitable for defoliating and desiccating plant parts, crops such as cotton, potatoes, rape, sunflower, soybean or field beans, in particular cotton, being suitable for this purpose. In this context, we have found plant desiccants and/or defoliants, processes for the preparation of these agents and methods for desiccating and/or defoliating plants with the compounds I.

Depen~ing on the substitution pattern, the compounds of the formula I may contain one or more centres of chirality and are then present as an enantiomer or diastereomer mixture. The present invention relates to both the pure enantiomers or diastereomers and to mixtures thereof.
The compounds I may also be represented as enol ethers by the tautomeric formula I' and I ' ' [ -N ( CH3 ) -CO- < > -N=C ( OCH3 ) - ]:

N=( /~ R5; R6 ~ ~ R5; R6 Rl~N--CH2 ~ ~ Rl~N--CH2 ~ ~

I' I'' Particularly suitable agriculturally useful salts include the salts in which the cations, or the acid addition salts of those acids in which the cations or anions, do not adversely affect the herbicidal action of the compounds I. Thus, particularly suitable cations are the ions of the alkali metals, preferably sodium and potassium, of the alkaline earth metals, preferably calcium, magnesium and barium, and of the transition metals, preferably manganese, copper, zinc and iron, and the ammonium ion, which, if desired, may carry from one to four Cl-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably 0050/46725 CA 022~0044 1998-09-24 diisopropylammonium, tetramethylammonium, tetrabutylammonium or trimethylbenzylammonium, and furthermore phosphonium ions, sulfonium ions, preferably tri(Cl-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(Cl-C4-alkyl)sulfoxonium.

Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, bicarbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate and 10 the anions of Cl-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate.

The organic moieties stated in the definition of Rl, R3 to R32 and Alk are general terms for the individual lists of individual 15 group members. All carbon ch~;ns, ie. all alkyl, haloalkyl, hydroxyalkyl, cyanoalkyl, phenylalkyl, alkylene, alkoxy, haloalkoxy, hydroxyalkoxy, cyanoalkoxy, alkylthio, haloalkylthio, alkylsulfinyl, alkylsulfonyl, haloalkylsulfonyl, alkylamino, dialkylamino, alkyloximino, alkyliminoxy, alkylideneaminoxy, 20 alkenyl, alkenyloxy, haloalkenyloxy, alkenylthio, alkynyl, alkynyloxy and alkynylthio moieties, may be straight-chain or branched.
Halogenated substituents preferably carry from one to five 25 identical or different halogen atoms.
Halogen is in each case fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
30 Furthermore, for example, - Cl-C4-alkyl is methyl, ethyl, n-propyl, l-methylethyl, n-butyl, l-methylpropyl, 2-methylpropyl or l,l-dimethylethyl, in particular methyl or ethyl;
- Cl-C4-haloalkyl is a Cl-C4-alkyl radical as stated above, which is partially or completely substituted by fluorine, chlorine, bromine and/or iodine, eg. chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, chlorofluoromethyl, dichlorofluoromethyl, chlorodifluoromethyl, 2-fluoroethyl, 2-chloroethyl, 2-bromoethyl, 2-iodoethyl, 2,2-difluoroethyl, 2,2,2-trifluoroethyl, 2-chloro-2-fluoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoroethyl, 2,2,2-trichloroethyl, pentafluoroethyl, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, CA 022~0044 l998-09-24 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, l-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloroethyl, 1-(bromomethyl)-2-bromoethyl, 4-fluorobutyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, in particular chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;

10 - C1-C6-alkyl is C1-C4-alkyl as stated above and, for example, n-pentyl, 1-methylbutyl, 2-methylbutyl, 3-methylbutyl, . 2.2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1,1-dimethylpropyl, 1,2-dimethylpropyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,1-dimethylbutyl, 1,2-dimethylbutyl, 1,3-dimethylbutyl, 2,2-dimethylbutyl, 2,3-dimethylbutyl, 3,3-dimethylbutyl, 1-ethylbutyl, 2-ethylbutyl, 1,1,2-trimethylpropyl, 1,2,2-trimethylpropyl, l-ethyl-l-methylpropyl or l-ethyl-2-methylpropyl, in particular methyl, ethyl, n-propyl, l-methylethyl, n-butyl, l,l-dimethylethyl, n-pentyl or n-hexyl;

- C1-C6-haloalkyl is C1-C6-alkyl as stated above, which is partially or completely substituted by fluorine, chlorine, bromine and/or iodine, for example one of the radicals stated under C1-C4-haloalkyl, or is S-fluoro-l-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 6-fluoro-1-hexyl, 6-chloro-1-hexyl, 6-bromo-1-hexyl, 6-iodo-1-hexyl, 6,6,6-trichloro-1-hexyl or dodecafluorohexyl, in particular chloromethyl, fluoromethyl, difluoromethyl, trifluoromethyl, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;

35 - hydroxy-C1-C6-alkyl is, for example, hydroxymethyl, 2-hydroxyeth-1-yl, 2-hydroxyprop-1-yl, 3-hydroxyprop-1-yl, 1-hydroxyprop-2-yl, 2-hydroxybut-1-yl, 3-hydroxybut-1-yl, 4-hydroxybut-1-yl, 1-hydroxybut-2-yl, 1-hydroxybut-3-yl, 2-hydroxybut-3-yl, 1-hydroxy-2-methylprop-3-yl, 2-hydroxy-2-methylprop-3-yl or 2-hydroxymethylprop-2-yl, in particular 2-hydroxyethyl;

- cyano-C1-C6-alkyl is, for example, cyanomethyl, l-cyanoeth-l-yl, 2-cyanoeth-1-yl, l-cyanoprop-l-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl, l-cyanobut-l-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, CA 022~0044 1998-09-24 2-cyanobut-2-yl, 1-cyanobut-3-yl, 2-cyanobut-3-yl, l-cyano-2-methylprop-3-yl, 2-cyano-2-methylprop-3-yl, 3-cyano-2-methylprop-3-yl or 2-cyanomethylprop-2-yl, in particular cyanomethyl or 2-cyanoethyl;

- phenyl-Cl-C6-alkyl is, for example, benzyl, l-phenylethyl, 2-phenylethyl, l-phenylprop-l-yl, 2-phenylprop-1-yl, 3-phenylprop-1-yl, l-phenylbut-l-yl, 2-phenylbut-1-yl, 3-phenylbut-1-yl, 4-phenylbut-1-yl, 1-phenylbut-2-yl, 2-phenylbut-2-yl, 3-phenylbut-2-yl, 4-phenylbut-2-yl, l-(phenylmethyl)eth-l-yl, l-(phenylmethyl)-l-(methyl)eth-l-yl or l-(phenylmethyl)prop-;-yl, in particular benzyl or 2-phenylethyl;

15 - phenyl-(Cl-C6-alkyl)carbonyloxy is, for example, benzylcarbonyloxy, l-phenylethylcarbonyloxy, 2-phenylethylcarbonyloxy, l-phenylprop-l-ylcarbonyloxy, 2-phenylprop-1-ylcarbonyloxy, 3-phenylprop-1-ylcarbonyloxy, l-phenylbut-l-ylcarbonyloxy, 2-phenylbut-1-ylcarbonyloxy, 3-phenylbut-1-ylcarbonyloxy, 4-phenylbut-1-ylcarbonyloxy, l-phenylbut-2-ylcarbonyloxy, 2-phenylbut-2-ylcarbonyloxy, 3-phenylbut-2-ylcarbonyloxy, 4-phenylbut-2-ylcarbonyloxy, l-(phenylmethyl)eth-l-ylcarbonyloxy, l-(phenylmethyl)-l-(methyl)eth-l-ylcarbonyloxy or l-(phenylmethyl)prop-l-ylcarbonyloxy~ in particular benzylcarbonyloxy or 2-phenylethylcarbonyloxy;
- phenyl-Cl-C6-alkylsulfonyloxy is, for example, benzylsulfonyloxy, l-phenylethylsulfonyloxy, 2-phenylethylsulfonyloxy, l-phenylprop-l-ylsulfonyloxy, 2-phenylprop-1-ylsulfonyloxy, 3-phenylprop-1-ylsulfonyloxy, l-phenylbut-l-ylsulfonyloxy, 2-phenylbut-1-ylsulfonyloxy, 3-phenylbut-1-ylsulfonyloxy, 4-phenylbut-1-ylsulfonyloxy, l-phenylbut-2-ylsulfonyloxy, 2-phenylbut-2-ylsulfonyloxy, 3-phenylbut-2-ylsulfonyloxy, 4-phenylbut-2-ylsulfonyloxy, l-(phenylmethyl)eth-l-ylsulfonyloxy, l-(phenylmethyl)-l-(methyl)eth-l-ylsulfonyloxy or l-(phenylmethyl)prop-l-ylsulfonyloxy, in particular benzylsulfonyloxy or 2-phenylethylsulfonyloxy;
- (Cl-C6-alkyl)carbonyl is methylcarbonyl, ethylcarbonyl, n-propylcarbonyl, l-methylethylcarbonyl, n-butylcarbonyl, l-methylpropylcarbonyl, 2-methylpropylcarbonyl, l,l-dimethylethylcarbonyl, n-pentylcarbonyl, l-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, l,l-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, CA 022~0044 1998-09-24 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-methylpentylcarbonyl, 2-methylpentylcarbonyl, 3-methylpentylcarbonyl, 4-methylpentylcarbonyl, 1,1-dimethylbutylcarbonyl, 1,2-dimethylbutylcarbonyl, 1,3-dimethylbutylcarbonyl, 2,2-dimethylbutylcarbonyl, 2,3-dimethylbutylcarbonyl, 3,3-dimethylbutylcarbonyl, 1-ethylbutylcarbonyl, 2-ethylbutylcarbonyl, 1,1,2-trimethylpropylcarbonyl, 1,2,2-trimethylpropylcarbonyl, 1-ethyl-1-methylpropylcarbonyl or 1-ethyl-2-methylpropylcarbonyl, in particular methylcarbonyl, ethylcarbonyl or 1-methylethylcarbonyl;

- (C1-C6-alkyl)carbonyl-Cl-C6-alkyl is C1-C6-alkyl substituted by (C1-C6-alkyl)carbonyl as stated above, eg.
methylcarbonylmethyl;

- (C1-C4-alkyl)carboxyl is methylcarboxyl, ethylcarboxyl, n-propylcarboxyl, 1-methylethylcarboxyl, n-butylcarboxyl, l-methylpropylcarboxyl, 2-methylpropylcarboxyl or l,l-dimethylethylcarboxyl, in particular methylcarboxyl;

- (C1-C6-haloalkyl)carbonyl is a (C1-C6-alkyl)carbonyl radical as stated above, which is partially or completely substituted by fluorine, chlorine, bromine and/or iodine, eg.
chloroacetyl, dichloroacetyl, trichloroacetyl, fluoroacetyl, difluoroacetyl, trifluoroacetyl, chlorofluoroacetyl, dichlorofluoroacetyl, chlorodifluoroacetyl, 2-fluoroethylcarbonyl, 2-chloroethylcarbonyl, 2-bromoethylcarbonyl, 2-iodoethylcarbonyl, 2,2-difluoroethylcarbonyl, 2,2,2-trifluoroethylcarbonyl, 2-chloro-2-fluoroethylcarbonyl, 2-chloro-2,2-difluoroethylcarbonyl, 2,2-dichloro-2-fluoroethylcarbonyl, 2,2,2-trichloroethylcarbonyl, pentafluoroethylcarbonyl, 2-fluoropropylcarbonyl, 3-fluoropropylcarbonyl, 2,2-difluoropropylcarbonyl, 2,3-difluoropropylcarbonyl, 2-chloropropylcarbonyl, 3-chloropropylcarbonyl, 2,3-dichloropropylcarbonyl, 2-bromopropylcarbonyl, 3-bromopropylcarbonyl, 3,3,3-trifluoropropylcarbonyl, 3,3,3-trichloropropylcarbonyl, 2,2,3,3,3-pentafluoropropylcarbonyl, heptafluoropropylcarbonyl, l-(fluoromethyl)-2-fluoroethylcarbonyl, 1-(chloromethyl)-2-chlorethylcarbonyl, 1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl, nonafluorobutylcarbonyl, (5-fluoro-1-pentyl)carbonyl, 0050/46725 CA 022~0044 1998-09-24 (S-chloro-l-pentyl)carbonyl, (5-bromo-l-pentyl)carbonyl, (5-iodo-1-pentyl)carbonyl, (5,5,5-trichloro-1-pentyl)carbonyl, undecafluoropentylcarbonyl, (6-fluoro-1-hexyl)carbonyl, (6-chloro-1-hexyl)carbonyl, (6-bromo-1-hexyl)carbonyl, (6-iodo-1-hexyl)carbonyl, (6,6,6-trichloro-1-hexyl)carbonyl or dodecafluorohexylcarbonyl, in particular trifluoroacetyl;

- (C1-C6-alkyl)carbonyloxy is acetoxy, ethylcarbonyloxy, n-propylcarbonyloxy, l-methylethylcarbonyloxy, n-butylcarbonyloxy, l-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, l,l-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, l-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, l,l-dimethylpropylcarbonyloxy, 1,2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, l-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, l-methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, l,l-dimethylbutylcarbonyloxy, 1,2-dimethylbutylcarbonyloxy, 1,3-dimethylbutylcarbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutylcarbonyloxy, 3,3-dimethylbutylcarbonyloxy, l-ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy, 1,2,2-trimethylpropylcarbonyloxy, l-ethyl-l-methylpropylcarbonyloxy or 1-ethyl-2-methylpropylcarbonyloxy, in particular acetoxy;
- (Cl-C6-haloalkyl)carbonyloxy is a (C1-C6-alkyl)carbonyloxy radical as stated above, which is partially or completely substituted by fluorine, chlorine, bromine and/or iodine, eg.
chloroacetoxy, dichloroacetoxy, trichloroacetoxy, fluoroacetoxy, difluoroacetoxy, trifluoroacetoxy, chlorofluoroacetoxy, dichlorfluoroacetoxy, chlorodifluoroacetoxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoroethylcarbonyloxy, 2-chloro-2-fluoroethylcarbonyloxy, 2-chloro-2,2-difluoroethylcarbonyloxy, 2,2-dichloro-2-fluoroethylcarbonyloxy, 2,2,2-trichloroethylcarbonyloxy, pentafluoroethylcarbonyloxy, 2-fluoropropylcarbonyloxy, 3-fluoropropylcarbonyloxy, 2,2-difluoropropylcarbonyloxy, 2,3-difluoropropylcarbonyloxy, 2-chloropropylcarbonyloxy, 3-chloropropylcarbonyloxy, 2,3-dichloropropylcarbonyloxy, 2-bromopropylcarbonyloxy, 3-bromopropylcarbonyloxy, 3,3,3-trifluoropropylcarbonyloxy, 3,3,3-trichloropropylcarbonyloxy, .

OOSO/46725 CA 022~0044 1998-09-24 2,2,3,3,3-pentafluoropropylcarbonyloxy, heptafluoropropylcarbonyloxy, 1-(fluoromethyl)-2-fluoroethylcarbonyloxy, 1-(chloromethyl)-2-chloroethylcarbonyloxy, 1-(bromomethyl)-2-bromoethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutylcarbonyloxy or nonafluorobutylcarbonyloxy, in particular trifluoroacetoxy;

10 - (Cl-C6-alkyl)carbonyloxy-Cl-C6-alkyl is Cl-C6-alkyl substituted by (C1-C6-akyl)carbonyloxy as stated above, eg.
methylcarbonyloxymethyl, ethylcarbonyloxymethyl, l-(methylcarbonyloxy)ethyl, 2-(methylcarbonyloxy)ethyl, 2-(ethylcarbonyloxy)ethyl, 3-(methylcarbonyloxy)propyl, 4-(methoxycarbonyloxy)butyl, 5-(methoxycarbonyloxy)pentyl or 6-(methoxycarbonyloxy)hexyl;

- (Cl-C6-alkyl)carbonylthio is acetylthio, ethylcarbonylthio, n-propylcarbonylthio, l-methylethylcarbonylthio, n-butylcarbonylthio, l-methylpropylcarbonylthio, 2-methylpropylcarbonylthio, l,l-dimethylethylcarbonylthio, n-pentylcarbonylthio, l-methylbutylcarbonylthio, 2-methylbutylcarbonylthio, 3-methylbutylcarbonylthio, 1,1-dimethylpropylcarbonylthio, 1,2-dimethylpropyl-carbonylthio, 2,2-dimethylpropylcarbonylthio, 1-ethylpropylcarbonylthio, n-hexylcarbonylthio, l-methylpentylcarbonylthio, 2-methylpentylcarbonylthio, 3-methylpentylcarbonylthio, 4-methylpentylcarbonylthio, l,l-dimethylbutylcarbonylthio, 1,2-dimethylbutylcarbonylthio, 1,3-dimethylbutylcarbonylthio, 2,2-dimethylbutylcarbonylthio, 2,3-dimethylbutylcarbonylthio, 3,3-dimethylbutylcarbonylthio, l-ethylbutylcarbonylthio, 2-ethylbutylcarbonylthio, 1,1,2-trimethylpropylcarbonylthio, 1,2,2-trimethylpropyl-carbonylthio, 1-ethyl-1-methylpropylcarbonylthio or 1-ethyl-2-methylpropylcarbonylthio, in particular acetylthio;

- (Cl-C6-haloalkyl)carbonylthio is a (Cl-C6-alkyl)carbonylthio radical as stated above, which is partially or completely substituted by fluorine, chlorine, b.~ ine and/or iodine, eg.
chloroacetylthio, dichloroacetylthio, trichloroacetylthio, fluoroacetylthio, difluoroacetylthio, trifluoroacetylthio, chlorofluoroacetylthio, dichlorofluoroacetylthio, chlorodifluoroacetylthio, 2-fluoroethylcarbonylthio, 2-chloroethylcarbonylthio, 2-bromoethylcarbonylthio, 2-iodoethylcarbonylthio, 2,2-difluoroethylcarbonylthio, 2,2,2-trifluoroethylcarbonylthio, 2-chloro-2-fluoroethylcarbonylthio, 0050/46725 CA 022~0044 1998-09-24 2-chloro-2,2-difluoroethylcarbonylthio, 2,2-dichloro-2-fluoroethylcarbonylthio, 2,2,2-trichloroethylcarbonylthio, pentafluoroethylcarbonylthio, 2-fluoropropylcarbonylthio, 3-fluoropropylcarbonylthio, 2,2-difluoropropylcarbonylthio, 2,3-difluoropropylcarbonylthio, 2-chloropropylcarbonylthio, 3-chloropropylcarbonylthio, 2,3-dichloropropylcarbonylthio, 2-bromopropylcarbonylthio, 3-bromopropylcarbonylthio, 3,3,3-trifluoropropylcarbonylthio, 3,3,3-trichloropropylcarbonylthio, 2,2,3,3,3-pentafluoropropylcarbonylthio, heptafluoropropylcarbonylthio, 1-(fluoromethyl)-2-fluoroethylcarbonylthio, l-(chloromethyl)-2-chloroethylcarbonylthio, 1-(bromomethyl)-2-bromoethylcarbonylthio, 4-fluorobutylcarbonylthio, 4-chlorobutylcarbonylthio, 4-bromobutylthio or nonafluorobutylthio, in particular trifluoroacetylthio;

- Cl-C4-alkoxy is OCH3, OC2H5, n-propoxy, OCH(CH3)2, n-butoxy, l-methylpropoxy, OCH2-CH(CH3)2 or OC(CH3)3, in particular OCH3 or OC2Hs;

- Cl-C6-alkoxy is Cl-C4-alkoxy as stated above and, for example, n-pentyloxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, l,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethyl-propoxy, l-ethylpropoxy, n-hexyloxy, l-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, l,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, l-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, l-ethyl-l-methylpropoxy and 1-ethyl-2-methylpropoxy, in particular methoxy, ethoxy or l-methylethoxy;

35 - Cl-C4-haloalkoxy is a Cl-C4-alkoxy radical as stated above, which is partially or completely substituted by fluorine, chlorine, bromine and/or iodine, eg. chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromethoxy, dichlorofluoromethoxy, chlorodifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy, 2-bromoethoxy, 2-iodoethoxy, 2,2-difluoroethoxy, 2,2,2-trifluoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxy, 2,2-dichloro-2-fluoroethoxy, 2,2,2-trichloroethoxy, pentafluoroethoxy, 2-fluoropropoxy, 3-fluoropropoxy, 2,2-difluoropropoxy, 2,3-difluoropropoxy, 2-chloropropoxy, 3-chloropropoxy, 2,3-dichloropropoxy, 2-bromopropoxy, ~ . . .

0050/46725 CA 022~0044 1998-09-24 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, l-(fluoromethyl)-2-fluoroethoxy, l-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, in particular 2-chloroethoxy or 2,2,2-trifluoroethoxy;
- Cl-C6-haloAlkoxy is a Cl-C6-alkoxy radical as stated above, which is partially or completely substituted by fluorine, chlorine, bromine and/or io~ine, for example one of the radicals stated under Cl-C4-haloalkoxy, or is 5-fluoro-1-pentyloxy, 5-chloro-1-pentyloxy, 5-bromo-1-pentyloxy, 5-iodo-1-pentyloxy, 5,5,5-trichloro-1-pentyloxy, undecafluoropentyloxy, 6-fluoro-1-hexyloxy, 6-chloro-1-hexyloxy, 6-bromo-1-hexyloxy, 6-iodo-1-hexyloxy, 6,6,6-trichloro-1-hexyloxy or dodecafluorohexyloxy, in particular chloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy;

- phenyl-Cl-C6-alkoxy is, for example, benzyloxy, l-phenylethoxy, 2-phenylethoxy, l-phenylprop-l-yloxy, 2-phenylprop-1-yloxy, 3-phenylprop-1-yloxy, l-phenylbut-l-yloxy, 2-phenylbut-1-yloxy, 3-phenylbut-1-yloxy, 4-phenylbut-1-yloxy, l-phenylbut-2-yloxy, 2-phenylbut-2-yloxy, 3-phenylbut-2-yloxy, 3-phenylbut-2-yloxy, 4-phenylbut-2-yloxy, l-(phenylmethyl)eth-l-yloxy, l-(phenylmethyl)-l-(methyl)eth-l-yloxy or l-(phenylmethyl)prop-l-yloxy, in particular benzyloxy or 2-phenylethoxy;

- phenyl-Cl-C6-alkylthio is, for example, benzylthio, l-phenylethylthio, 2-phenylethylthio, l-phenylprop-l-ylthio, 2-phenylprop-1-ylthio, 3-phenylprop-1-ylthio, l-phenylbut-l-ylthio, 2-phenylbut-1-ylthio, 3-phenylbut-1-ylthio, 4-phenylbut-1-ylthio, l-phenylbut-2-ylthio, 2-phenylbut-2-ylthio, 3-phenylbut-2-ylthio, 3-phenylbut-2-ylthio, 4-phenylbut-2-ylthio, l-(phenylmethyl)eth-l-ylthi l-(phenylmethyl)-l-(methyl)eth-l-ylthio or l-(phenylmethyl)prop-l-ylthio, in particular benzylthio or 2-phenylethylthio;

0050/46725 CA 022~0044 1998-09-24 - (cl-c4-alkoxy)carbonyl is CO-OCH3, CO-OC2H5, n-propoxycarbonyl, CO-OCH(CH3)2, n-butoxycarbonyl, 1-methylpropoxycarbonyl, C0-OCH2-CH( CH3)2 or C0-OC( CH3)3, in particular CO-OCH3, CO-OC2H5, Co-ocH(cH3)2 or CO-CH2-CH(CH3)2;

- (c~-c6-alkoxy)carbonyl is (C1-C4-alkoxy)carbonyl as stated above and, for example, n-pentyloxycarbonyl, l-methylbutoxycarbonyl, 2-methylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexyloxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentyloxycarbonyl, 2-methylpentyloxycarbonyl, 3-methylpentyloxycarbonyl, 4-methylpentyloxycarbonyl, l,l-dimethylbutoxycarbonyl, 1,2-dimethylbutoxycarbonyl, 1,3-dimethylbutoxycarbonyl, 2,2-dimethylbutoxycarbonyl, 2,3-dimethylbutoxycarbonyl, 3,3-dimethylbutoxycarbonyl, 1-ethylbutoxycarbonyl, 2-ethylbutoxycarbonyl, 1,1,2-trimethylpropoxycarbonyl, 1,2,2-trimethylpropoxycarbonyl, 1-ethyl-1-methylpropoxycarbonyl or 1-ethyl-2-methylpropoxycarbonyl, in particular methoxycarbonyl, ethoxycarbonyl or 1-methylethoxycarbonyl;
- (cl-c6-alkoxy)carbonyloxy is methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methylpropoxycarbonyloxy, 1,1-dimethylethoxycarbonyloxy, n-pentyloxycarbonyloxy, 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 2,2-dimethylpropoxycarbonyloxy, 1-ethylpropoxycarbonyloxy, n-hexyloxycarbonyloxy, 1,1-dimethylpropoxycarbonyloxy, 1,2-dimethylpropoxycarbonyloxy, 1-methylpentyloxycarbonyloxy, 2-methylpentyloxycarbonyloxy, 3-methylpentyloxycarbonyloxy, 4-methylpentyloxycarbonyloxy, 1,1-dimethylbutoxycarbonyloxy, 1,2-dimethylbutoxycarbonyloxy, 1,3-dimethylbutoxycarbonyloxy, 2,2-dimethylbutoxycarbonyloxy, 2,3-dimethylbutoxycarbonyloxy, 3,3-dimethylbutoxycarbonyloxy, 1-ethylbutoxycarbonyloxy, 2-ethylbutoxycarbonyloxy, 1,1,2-trimethylpropoxycarbonyloxy, 1,2,2-trimethylpropoxycarbonyloxy, 1-ethyl-1-methylpropoxycarbonyloxy or 1-ethyl-2-methylpropoxycarbonyloxy, in particular methoxycarbonyloxy, ethoxycarbonyloxy or 1-methylethoxycarbonyloxy;

0050/46725 CA 022~0044 1998-09-24 - (Cl-C6-alkoxy)carbonylthio is methoxycarbonylthio, ethoxycarbonylthio, n-propoxycarbonylthio, l-methylethoxycarbonylthio, n-butoxycarbonylthio, l-methylpropoxycarbonylthio, 2-methylpropoxycarbonylthio, l,l-dimethylethoxycarbonylthio, n-pentyloxycarbonylthio, 1-methylbutoxycarbonylthio, 2-methylbutoxycarbonylthio, 3-methylbutoxycarbonylthio, 2,2-dimethylpropoxycarbonylthio, 1-ethylpropoxycarbonylthio, n-hexyloxycarbonylthio, 1,1-dimethylpropoxycarbonylthio, 1,2-dimethylpropoxycarbonylthio, 1-methylpentyloxycarbonylthio, 2-methylpentyloxycarbonylthio, 3-methylpentyloxycarbonylthio, 4-methylpentyloxycarbonylthio, l,l-dimethylbutoxycarbonylthio, 1,2-dimethylbutoxycarbonylthio, 1,3-dimethylbutoxycarbonylthio, 2,2-dimethylbutoxycarbonylthio, 2,3-dimethylbutoxycarbonylthio, 3,3-dimethylbutoxycarbonylthio, l-ethylbutoxycarbonylthio, 2-ethylbutoxycarbonylthio, 1,1,2-trimethylpropoxycarbonylthio, 1,2,2-trimethylpropoxycarbonylthio, l-ethyl-1-methyl-propoxycarbonylthio or l-ethyl-2-methylpropoxycarbonylthio, in particular methoxycarbonylthio, ethoxycarbonylthio or l-methylethoxycarbonylthio;
- C1-C6-alkylthio is methylthio, ethylthio, n-propylthio, l-methylethylthio, n-butylthio, l-methylpropylthio, 2-methylpropylthio, l,l-dimethylethylthio, n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, l-ethylpropylthio, n-hexylthio, l,l-dimethylpropylthio, 1,2-dimethylpropylthio, l-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, l,l-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, l-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, l-ethyl-l-methylpropylthio and l-ethyl-2-methylpropylthio, in particular methylthio or ethylthio;

- Cl-C4-haloalkylthio is Cl-C4-alkylthio, such as methylthio, ethylthio, n-propylthio, l-methylethylthio, n-butylthio, l-methylpropylthio, 2-methylpropylthio or l,l-dimethylethylthio, preferably methylthio or ethylthio, which is partially or completely substituted by fluorine, chlorine and/or bromine, 0050/46725 CA 022~0044 1998-09-24 eg. difluoromethylthio, trifluoromethylthio, chlorodifluoromethylthio, bromodifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio, 2-bromoethylthio, 2-iodoethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2,2,2-trichloroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, pentafluoroethylthio, 2-fluoropropylthio, 3-fluoropropylthio, 2-chloropropylthio, 3-chloropropylthio, 2-bromopropylthio, 3-bromopropylthio, 2,2-difluoropropylthio, 2,3-difluoropropylthio, 2,3-dichloropropylthio, 3,3,3-trifluoropropylthio, 3,3,3-trichloropropylthio, 2,2,3,3,3-pentafluoropropylthio, heptafluoropropylthio, l-(fluoromethyl)-2-fluoroethylthio, l-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutylthio, 4-bromobutylthio or nonafluorobutylthio, in particular trifluoromethylthio or difluoromethylthio;

- Cl-C6-haloalkylthio is Cl-C6-alkylthio as stated above, which is partially or completely substituted by fluorine, chlorine and/or bromine for example one of the radicals stated under Cl-C4-haloalkylthio, or is 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio or 6-chlorohexylthio, in particular chloromethylthio, fluoromethylthio, difluoromethylthio, trifluoromethylthio, 2-fluoroethylthio, 2-chloroethylthio or 2,2,2-trifluoroethylthio;

30 - Cl-C6-alkylsulfinyl is methylsulfinyl, ethylsulfinyl, n-propylsulfinyl, l-methylethylsulfinyl, n-butylsulfinyl, l-methylpropylsulfinyl, 2-methylpropylsulfinyl, l,l-dimethylethylsulfinyl, n-pentylsulfinyl, l-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, l,l-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, l-ethylpropylsulfinyl, n-hexylsulfinyl, l-methylpentylsulfinyl,-2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, l,l-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, l-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, l-ethyl-l-methylpropylsulfinyl or l-ethyl-2-methylpropylsulfinyl, in particular methylsulfinyl;

CA 022~0044 1998-09-24 - Cl-C6-alkylsulfonyl is methylsulfonyl, ethylsulfonyl, n-propylsulfonyl, l-methylethylsulfonyl, n-butylsulfonyl, l-methylpropylsulfonyl, 2-methylpropylsulfonyl, l,l-dimethylethylsulfonyl, n-pentylsulfonyl, l-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, l,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, l-ethylpropylsulfonyl, n-hexylsulfonyl, l-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, l,1-dimethylbutylsulfonyl, 1,2-dimethylbutylsulfonyl, 1,3-dimethylbutylsulfonyl, 2,2-dimethylbutylsulfonyl, 2,3-dimethylbutylsulfonyl, 3,3-dimethylbutylsulfonyl, 1-ethylbutylsulfonyl, 2-ethylbutylsulfonyl, 1,1,2-trimethylpropylsulfonyl, 1,2,2-trimethylpropylsulfonyl, l-ethyl-l-methylpropylsulfonyl or l-ethyl-2-methylpropylsulfonyl, in particular methylsulfonyl;

- Cl-C6-alkylsulfonyloxy is methylsulfonyloxy, ethylsulfonyloxy, n-propylsulfonyloxy, 1-methylethylsulfonyloxy, n-butylsulfonyloxy, l-methylpropylsulfonyloxy, 2-methylpropylsulfonyloxy, 1,1-dimethylethylsulfonyloxy, n-pentylsulfonyloxy, 1-methylbutylsulfonyloxy, 2-methylbutylsulfonyloxy, 3-methylbutylsulfonyloxy, l,l-dimethylpropylsulfonyloxy, 1,2-dimethylpropylsulfonyloxy, 2,2-dimethylpropylsulfonyloxy, l-ethylpropylsulfonyloxy, n-hexylsulfonyloxy, l-methylpentylsulfonyloxy, 2-methylpentylsulfonyloxy, 3-methylpentylsulfonyloxy, 4-methylpentylsulfonyloxy, l,l-dimethylbutylsulfonyloxy, 1,2-dimethylbutylsulfonyloxy, 1,3-dimethylbutylsulfonyloxy, 2,2-dimethylbutylsulfonyloxy, 2,3-dimethylbutylsulfonyloxy, 3,3-dimethylbutylsulfonyloxy, l-ethylbutylsulfonyloxy, 2-ethylbutylsulfonyloxy, 1,1,2-trimethylpropylsulfonyloxy, 1,2,2-trimethylpropylsulfonyloxy, l-ethyl-l-methylpropylsulfonyloxy or 1-ethyl-2-methylpropylsulfonyloxy, in particular methylsulfonyloxy;

- Cl-C6-haloalkylsulfonyloxy is Cl-C6-alkylsulfonyloxy as stated above, which is partially or completely substituted by fluorine, chlorine, bromine and/or iodine, eg. ClCH2-S02-0-, CH(Cl)2-S02-0-, C(Cl)3-S02-0-, FCH2-S02-0-, CHF2-S02-0-, CF3-S02-0-, chlorofluoromethyl-S02-0-, dichlorofluoromethyl-S02-0-, chlorodifluoromethyl-S02-0-, l-fluoroethyl-S02-0-, 2-fluoroethyl-S02-0-, 2-chloroethyl-S02-0-, 2-bromoethyl-S02-0-, 2-iodoethyl-S02-0-, 2,2-difluoroethyl-S02-0-, 2,2,2-trifluoroethyl-S02-0-, CA 022~0044 1998-09-24 2-chloro-2-fluoroethyl-S02-0-, 2-chloro-2,2-difluoroethyl-S02-0-, 2,2-dichloro-2-fluoroethyl-S02-0-, 2,2,2-trichloroethyl-S02-0-, C2F5-SO2-0-, 2-fluoropropyl-S02-0-, 3-fluoropropyl-S02-0-, 2,2-difluoropropyl-S02-0-, 2,3-difluoropropyl-S02-0-, 2-chloropropyl-SO2-O-, 3-chloropropyl-S02-0-, 2,3-dichloropropyl-S02-0-, 2-bromopropyl-S02-0-, 3-bromopropyl-S02-0-, 3,3,3-trifluoropropyl-S02-0-, 3,3,3-trichloropropyl-S02-0-, 2,2,3,3,3-pentafluoropropyl-S02-0-, C2F5-CF2-S02-0-, l-(fluoromethyl~-2-fluoroethyl-S02-0-, l-(chloromethyl)-2-chlorethyl-S02-0-, l-(bromomethyl)-2-bromoethyl-S02-0-, 4-fluorobutyl-S02-0-, 4-chlorobutyl-S02-0-, 4-bromobutyl-S02-0-, C2F5-CF2-CF2-S02-O-, 5-fluoropentyl-S02-0-, 5-chloropentyl-S02-0-, 5-bromopentyl-S02-0-, 5-iodopentyl-S02-0-, 5,5,5-trichloropentyl-S02-0-, C2F5-CF2-CF2-CF2-S02-0-, 6-fluorohexyl-S02-0-, 6-chlorohexyl-S02-0-, 6-bromohexyl-S02-0-, 6-iodohexyl-S02-0-, 6,6,6-trichlorohexyl-S02-0- or dodecafluorohexyl-S02-0-, in particular CF3-S~2-~-;
- Cl-C4-alkylaminO is methylamino, ethylamino, n-propylamino, 2s l-methylethylamino, n-butylamino, l-methylpropylamino, 2-methylpropylamino or l,l-dimethylethylamino, in particular methylamino or ethylamino;
- (Cl-C4-alkylamino)carbonyl is CO-NH-CH3, CO-NH-C2H5, n-propylaminocarbonyl, CO-NH-CH(CH3)2, n-butylaminoc~rbonyl, 1-methylpropylaminocarbonyl, C0-NH-CH2-CH( CH3)2 or CO-NH-C(CH3)3, in particular CO-NH-CH3 or C0-NH-C2H5;

- (Cl-C6-alkylamino)carbonyl is (Cl-C4-alkylamino)carbonyl as stated above and, for example, n-pentyla~;nocArbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylam;nocArbonyl, l-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, l-methylpentyla~inocArbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, l,l-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, l-ethylbutylaminocarbonyl, .

0050/46725 CA 022~0044 1998-09-24 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, l-ethyl-l-methylpropylaminocarbonyl or 1-ethyl-2-methylpropyl~inocarbonyl, in particular C0-NH-CH3, C0-NH-C2H5 or C0-NH-CH(CH3)2;

- di-(C1-C6-alkyl)aminocarbonyl is, for example, N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-dipropylaminocarbonyl, N,N-di-(l-methylethyl)aminocarbonyl, N,N-dibutylaminocarbonyl, N,N-di-(l-methylpropyl)aminocarbonyl, N,N-di-(2-methylpropyl)aminocarbonyl, N,N-di-(l,l-dimethylethyl)-aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N-(l-methylethyl)-aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(l-methylpropyl)am;nocArbonyl, N-methyl-N-(2-methylpropyl)-aminocarbonyl, N-(l,l-dimethylethyl)-N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(l-methylethyl)-a~inoc~rbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(l-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)-aminocarbonyl, N-ethyl-N-(l,l-dimethylethyl)aminocarbonyl, N-(l-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N-(l-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, N-(l,l-dimethylethyl)-N-propylaminocarbonyl, N-butyl-N-(l-methylethyI)aminocarbonyl, N-(l-methylethyl)-N-(l-methylpropyl)aminocarbonyl, N-(l-methylethyl)-N-(2-methylpropyl)aminocarbonyl, N-(l,l-dimethylethyl)-N-(l-methylethyl)aminocarbonyl, N-butyl-N-(l-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)aminocarbonyl, N-butyl-N-(l,l-dimethylethyl)aminocarbonyl, N-(l-methylpropyl)-N-(2-methylpropyl)aminocarbonyl, N-(l,l-dimethylethyl)-N-(l-methylpropyl)aminocarbonyl or N-(l,l-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl, in particular N,N-dimethylaminocarbonyl or N,N-diethylaminocarbonyl;

- (Cl-C6-alkyl)iminoxycarbonyl is methyliminoxycarbonyl, ethyliminoxycarbonyl, n-propyliminoxycarbonyl, l-methylethyliminoxycarbonyl, n-butyliminoxycarbonyl, l-methylpropyliminoxycarbonyl, 2-methylpropyliminoxycarbonyl, l,l-dimethylethyliminoxycarbonyl, n-pentyliminoxycarbonyl, .

0050/46725 CA 022~0044 1998-09-24 l-methylbutyliminoxycarbonyl, 2-methylbutyliminoxycarbonyl, 3-methylbutyliminoxycarbonyl, l,l-dimethylpropyliminoxycarbonyl, 1,2-dimethylpropyliminoxycarbonyl, 2,2-dimethylpropyliminoxycarbonyl, l-ethylpropyli~;noxycarbonyl, n-hexyliminoxycarbonyl, l-methylpentyliminoxycarbonyl, 2-methylpentyliminoxycarbonyl, 3-methylpentyliminoxycarbonyl, 4-methylpentyliminoxycarbonyl, l,l-dimethylbutyliminoxycarbonyl, 1,2-dimethylbutyliminoxycarbonyl, 1,3-dimethylbutyliminoxycarbonyl, 2,2-dimethylbutyliminoxycarbonyl, 2,3-dimethylbutyliminoxycarbonyl, 3,3-dimethylbutyliminoxycarbonyl, l-ethylbutyliminoxycarbonyl, 2-ethylbutyliminoxycarbonyl, 1,1,2-trimethylpropyliminoxycarbonyl, 1,2,2-trimethylpropyliminoxycarbonyl, l-ethyl-1-methylpropyliminoxycarbonyl or l-ethyl-2-methylpropyliminoxycarbonyl, in particular methyliminoxycarbonyl, ethyliminoxycarbonyl or l-methylethyliminoxycarbonyl;

- C1-C6-alkylideneaminoxy is acetylideneaminoxy, l-propylideneaminoxy, 2-propylideneaminoxy, l-butyli~eneaminoxy, 2-butyli~ene~;noxy or 2-hexyli~eneaminoxy, in particular acetylideneaminoxy or 2-propylideneaminoxy;

- C1-C6-alkyliminoxy is methyliminoxy, ethyliminoxy, n-propyliminoxy, l-methylethyliminoxy, n-butyliminoxy, l-methylpropyliminoxy, 2-methylpropyliminoxy, n-pentyliminoxy, n-hexyliminoxy, l-methylpentyliminoxy, 2-methylpentyliminoxy, 3-methylpentyliminoxy or 4-methylpentyliminoxy, in particular methyliminoxy, ethyliminoxy or l-methylethyliminoxy;

- C1-C6-~lkox;mino-Cl-C6-alkyl is C1-C6-alkyl, substituted by Cl-C6-alkoximino, such as methoximino, ethoximino, l-propoximino, 2-propoximino, l-methylethoximino, n-butoximino, sec.-butoximino, tert.-butoY;~ino, l-methyl-l-propoximino, 2-methyl-1-propoximino, l-methyl-2-propoximino, 2-methyl-2-propoximino, n-pentoximino, 2-pentox;~ino, 3-pentoximino, 4-pentoximino, l-methyl-1-butoximino, 2-methyl-1-buto~i ino~
3-methyl-1-butoxi~ino, 1-methyl-2-butoximino, 2-methyl-2-buto~i ino, 3-methyl-2-butoximino, 1-methyl-3-butoximino, 2-methyl-3-butoximino, 3-methyl-3-butoximino, 0050/46725 CA 022~0044 1998-09-24 -1,1-dimethyl-2-propoximino, 1,2-dimethyl-1-propoxir;no, 1,2-dimethyl-2-propox;m;no, l-ethyl-l-propox; m; no, l-ethyl-2-propoximino, n-hexyloximino, 2-hexyloximino, 3-hexyloximino, 4-hexyloximino, 5-hexylox;m;no, l-methyl-l-pentoximino, 2-methyl-1-pentox;~;no, 3-methyl-1-pentoximino, 4-methyl-1-pentoximino, l-methyl-2-pentoximino, 2-methyl-2-pentoximino, 3-methyl-2-pentoximino, 4-methyl-2-pentox;m;no, l-methyl-3-pentoximino, 2-methyl-3-pentox;m;no, 3-methyl-3-pentoximino, 4-methyl-3-pentoximino, 1-methyl-4-pentoximino, 2-methyl-4-pentoximino~ 3-methyl-4-pentoximino, 4-methyl-4-pentoximino, 1,1-dimethyl-2-butox;m;no, 1,1-dimethyl-3-butoximino, 1,2-dimethyl-1-butoximino, 1,2-dimethyl-2-butoximino, 1,2-dimethyl-3-butoximino, 1,3-dimethyl-1-butoximino, 1,3-dimethyl-2-butoximino, 1,3-dimethyl-3-butoximino, 2,2-dimethyl-3-butoximino, 2,3-dimethyl-1-butoximino, 2,3-dimethyl-2-butoximino, 2,3-dimethyl-3-butoximino, 3,3-dimethyl-1-butoximino, 3,3-dimethyl-2-butoximino, l-ethyl-l-butoximino, l-ethyl-2-butox;~;no, 1-ethyl-3-butoximino, 2-ethyl-1-butox;m;no, 2-ethyl-2-butoximino, 2-ethyl-3-butoximino, 1,1,2-trimethyl-2-propox;~;no, 1-ethyl-1-methyl-2-propoximino, l-ethyl-2-methyl-1-propoximino or 1-ethyl-2-methyl-2-propoximino, eg. methoximinomethyl;
- Cl-C6-alkoxy-C1-C6-alkyl is C1-C6-alkyl substituted by C1-C6-alkoxy as stated above, eg. methoxymethyl, ethoxymethyl, n-propoxymethyl, (l-methylethoxy)methyl, n-butoxymethyl, (l-methylpropoxy)methyl, (2-methylpropoxy)methyl, (l,l-dimethylethoxy)methyl, 2-(methoxy)ethyl, 2-(ethoxy)ethyl, 2-(n-propoxy)ethyl, 2-(1-methylethoxy)ethyl, 2-(n-butoxy)ethyl, 2-(1-methylpropoxy)ethyl, 2-(2-methylpropoxy)ethyl, 2-(1,1-dimethylethoxy)ethyl, 2-(methoxy)propyl, 2-(ethoxy)propyl, 2-(n-propoxy)propyl, 2-(1-methylethoxy)propyl, 2-(n-butoxy)propyl, 2-(1-methylpropoxy)propyl, 2-(2-methylpropoxy)propyl, 2-(1,1-dimethylethoxy)propyl, 3-(methoxy)propyl, 3-(ethoxy)-propyl, 3-(n-propoxy)propyl, 3-(1-methylethoxy)propyl, 3-(n-butoxy)propyl, 3-(1-methylpropoxy)propyl, 3-(2-methylpropoxy)propyl, 3-(1,1-dimethylethoxy)propyl, 2-(methoxy)-butyl, 2-(ethoxy)butyl, 2-(n-propoxy)butyl, 2-(1-methylethoxy)butyl, 2-(n-butoxy)butyl, 2-(1-methylpropoxy)butyl, 2-(2-methylpropoxy)butyl, 2-(1,1-dimethylethoxy)butyl, 3-(methoxy)butyl, 3-(ethoxy)butyl, 3-(n-propoxy)butyl, 3-(1-methylethoxy)butyl, CA 022~0044 1998-09-24 ..

~ 3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(ethoxy)butyl, 4-(n-propoxy)butyl, 4-(1-methylethoxy)butyl, 4-(n-butoxy)butyl, 4-(1-methylpropoxy)butyl, 4-(2-methylpropoxy)butyl or 4-(1,1-dimethylethoxy)butyl, in particular methoxymethyl or 2-methoxyethyl;

- Cl-C6-alkoxy-Cl-C6-alkoxy is Cl-C6-alkoxy substituted by Cl-C6-alkoxy as stated above, eg. methoxymethoxy, ethoxymethoxy, n-propoxymethoxy, (1-methylethoxy)methoxy, . n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, (l~l-dimethylethoxy)methoxy~
2-(methoxy)ethoxy, 2-(ethoxy)ethoxy, 2-(n-propoxy)ethoxy, 2-(1-methylethoxy)ethoxy, 2-(n-butoxy)ethoxy, 2-(1-methylpropoxy)ethoxy, 2-(2-methylpropoxy)ethoxy, 2-(1,1-dimethylethoxy)ethoxy, 2-(methoxy)propoxy, 2-(ethoxy)propoxy, 2-(n-propoxy)propoxy, 2-(1-methylethoxy)propoxy, 2-(n-butoxy)propoxy, 2-(1-methylpropoxy)propoxy, 2-(2-methylpropoxy)propoxy, 2-(1,1-dimethylethoxy)propoxy, 3-(methoxy)propoxy, 3-(ethoxy)propoxy, 3-(n-propoxy)propoxy, 3-(1-methylethoxy)propoxy, 3-(n-butoxy)propoxy, 3-(1-methylpropoxy)propoxy, 3-(2-methylpropoxy)propoxy, 3-(1,1-dimethylethoxy)propoxy, 2-(methoxy)butoxy, 2-(ethoxy)butoxy, 2-(n-propoxy)butoxy, 2-(1-methylethoxy)butoxy, 2-(n-butoxy)butoxy, 2-(1-methylpropoxy)butoxy, 2-(2-methylpropoxy)butoxy, 2-(1,1-dimethylethoxy)butoxy, 3-(methoxy)butoxy, 3-(ethoxy)-butoxy, 3-(n-propoxy)butoxy, 3-(1-methylethoxy)butoxy, 3-(n-butoxy)butoxy, 3-(1-methylpropoxy)butoxy, 3-(2-methylpropoxy)butoxy~ 3-(1,1-dimethylethoxy)butoxy, 4-(methoxy)butoxy~ 4-(ethoxy)butoxy, 4-(n-propoxy)butoxy, 4-(1-methylethoxy)butoxy, 4-(n-butoxy)butoxy, 4-(1-methylpropoxy)butoxy, 4-(2-methylpropoxy)butoxy, 4-(1,1-dimethylethoxy)butoxy, 5-(methoxy)pentyloxy, 5-(ethoxy)pentyloxy, S-(n-propoxy)pentyloxy, 5-(1-methylethoxy)pentyloxy, 5-(n-butoxy)pentyloxy, 5-(1-methylpropoxy)pentyloxy, 5-(2-methylpropoxy)pentyloxy, 5-(1,1-dimethylethoxy)pentyloxy, 6-(methoxy)hexyloxy, 6-(ethoxy)hexyloxy, 6-(n-propoxy)hexyloxy, 6-(1-methylethoxy)hexyloxy, 6-(n-butoxy)hexyloxy, 6-(1-methylpropoxy)hexyloxy, 6-(2-methylpropoxy)hexyloxy or 6-(1,1-dimethylethoxy)hexyloxy, in particular methoxymethoxy or ethoxymethoxy;

CA 022~0044 1998-09-24 -- (Cl-C6-alkoxy)carbonyl-Cl-C6-alkoxy is Cl-C6-alkoxy substituted by (Cl-C6-alkoxy)carbonyl as stated above, eg.
OCH2-CO-OCH3, OCH2--CO--OC2H5, OCH2--CO-OCH2-C2H5, OCH2-C0-OCH(CH3)2, n-butoxycarbonylmethoxy, l-(methoxycarbonyl)ethoxy, 2-(methoxycarbonyl)ethoxy, 2-(ethoxycarbonyl)ethoxy, 2-(n-propoxycarbonyl)ethoxy, 2-(n-butoxycarbonyl)ethoxy, 3-(methoxycarbonyl)propoxy, 3-(ethoxycarbonyl)propoxy, 3-(n-propoxycarbonyl)propoxy, 3-(n-butoxycarbonyl)propoxy~ 4-(methoxycarbonyl)butoxy, 4-(ethoxycarbonyl)butoxy, 4-(n-propoxycarbonyl)butoxy, 4-(n-butoxycarbonyl)butoxy, 5-(methoxycarbonyl)pentyloxy, 5-(ethoxycarbonyl)pentyloxy, 5-(n-propoxycarbonyl)pentyloxy, 5-(n-butoxycarbonyl)butoxy, 6-(methoxycarbonyl)hexyloxy, 6-(ethoxycarbonyl)hexyloxy, 6-(n-propoxycarbonyl)hexyloxy or 6-(n-butoxycarbonyl)hexyloxy, in particular OCH2-C0-OCH3 or l-(methoxycarbonyl)ethoxy;

- (C1-C6-alkoxy)carbonyl-Cl-C6-alkyl is Cl-C6-alkyl substituted by (Cl-C6-alkoxy)carbonyl as stated above, eg.
methoxycarbonylmethyl, ethoxycarbonylmethyl, l-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 4-(methoxycarbonyl)butyl, 5-(methoxycarbonyl)pentyl or 6-(methoxycarbonyl)hexyl;
- (Cl-C6-alkoxy)carbonyl-Cl-C6-alkylsulfonyl is Cl-C6-alkylsulfonyl substituted by (Cl-C6-alkoxy)carbonyl as stated above, eg. methoxycarbonylmethylsulfonyl, ethoxycarbonylmethylsulfonyl, l-(methoxycarbonyl)ethylsulfonyl, 2-(methoxycarbonyl)ethylsulfonyl, 2-(ethoxycarbonyl)ethylsulfonyl, 3-(methoxycarbonyl)propylsulfonyl, 4-(methoxycarbonyl)butylsulfonyl, 5-(methoxycarbonyl)pentylsulfonyl or 6-(methoxycarbonyl)hexylsulfonyl;

- Cl-C6-alkylthio-Cl-C6-alkyl is Cl-C6-alkyl substituted by Cl-C6-alkylthio as stated above, eg. CH2-SCH3, CH2-SC2H5, n-propylthiomethyl, CH2-SCH(CH3) 2~ n-butylthiomethyl, (l--methylpropylthio)methyl, CH2--SCH2-CH(CH3) 2, CH2-SC(CH3)3, 2-methylthioethyl, 2-ethylthioethyl, 2-(n-propylthio)ethyl, 2-(1-methylethylthio)ethyl, 2-(n-butylthio)ethyl, 2-(1-methylpropylthio)ethyl, 2-(2-methylpropylthio)ethyl, 2-(l~l-dimethylethylthio)ethyl~ 2-(methylthio)propyl, 3-(methylthio)propyl, 2-(ethylthio)propyl, 3-(ethylthio)propyl, 3-(propylthio)propyl, AMENDED SHEET

CA 022~0044 1998-09-24 3-(butylthio)propyl, 4-(methylthio)butyl, 4-(ethylthio)butyl, 4-(n-propylthio)butyl or 4-(n-butylthio)butyl, in particular 2-(methylthio)ethyl;

5 - Cl-C6-alkylthio(C1-C6-alkyl)carbonyl is (C1-C6-alkyl)carbonyl substituted by Cl-C6-alkylthio as stated above, preferably SCH3 or SC2H5, eg. methylthiomethylcarbonyl, ethylthiomethylcarbonyl, l-(methylthio)ethylcarbonyl, 2-(methylthio)ethylcarbonyl, 3-(methylthio)propylcarbonyl, 4-(methylthio)butylcarbonyl, 5(methylthio)pentylcarbonyl or 6-(methylthio)hexylcarbonyl, in particular CO-CH2-SCH3 or CO-CH(CH3)-SCH3;

- di-(Cl-C6-alkyl)amino-Cl-C6-alkoxy is Cl-C6-alkoxy substituted by di(cl-c6-alkyl)amino~ such as N(CH3) 2~ N(C2Hs) 2 N,N-dipropylamino, N,N-di-(l-methylethyl)amino, N,N-dibutylamino, N,N-di-(l-methylpropyl)amino, N,N--di--(2--methylpropyl)amino,N[C(CH3)3] 2~
N-ethyl-N-methylamino, N-methyl-N-propylamino, 20 N-methyl-N-(l-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(l-methylpropyl)amino, N-methyl-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-methylamino, N-ethyl-N-propylamino, N-ethyl-N-(1-methylethyl)amino, N-butyl-N-ethylamino, N-ethyl-N-(1-methylpropyl)amino, N-ethyl-N-(2-methylpropyl)amino, N-ethyl-N-(l,l-dimethylethyl)amino, N-(l-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(l-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(l,l-dimethylethyl)-N-propylamino, N-butyl-N-(l-methylethyl)amino, N-(l-methylethyl)-N-(l-methylpropyl)amino, N-(l-methylethyl)-N-(2-methylpropyl)-amino, N-(l,l-dimethylethyl)-N-(l-methylethyl)amino, N-butyl-N-(l-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(l,l-dimethylethyl)amino, N-(l-methylpropyl)-N-(2-methylpropyl)amino, N-(l,l-dimethylethyl)-N-(l-methylpropyl)amino or N-(l,l-dimethylethyl)-N-(2-methylpropyl)amino, preferably N,N--dimethylamino or N,N--diethylamino, eg. OCH2-N(CH3) 2~
OCH2-N(C2H5)2, OCH(CH3)-N(CH3) 2~ 2--(dimethylamino)ethoxy, OCH(CH3)-N(C2H5) 2~ 3--(dimethylamino)propoxy, 4-(dimethylamino)butoxy, 5-(dimethylamino)pentyloxy or 6-(dimethylamino)hexyloxy, in particular OCH2-N(CH3) 2 or OCH(cH3)-N(cH3)2;

AMENDED SHEET

0050/46725 CA 022~0044 1998-09-24 - C3-C6-alkenyl is, for example, prop-2-en-1-yl, n-buten-4-yl, l-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, 2-buten-l-yl, n-penten-3-yl, n-Penten-4-yl, l-methylbut-2-en-l-yl, 2-methylbut-2-en-1-yl, 3-methylbut-2-en-1-yl, 1-methylbut-3-en-1-yl, 2-methylbut-3-en-1-yl, 3-methylbut-3-en-1-yl, l,1-dimethylprop-2-en-1-yl, 1,2-dimethylprop-2-en-1-yl, 1-ethylprop-2-en-1-yl, n-hex-3-en-1-yl, n-hex-4-en-1-yl, n-hex-5-en-1-yl, l-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, l-methylpent-4-en-1-yl, 2-methylpent-4-en-1-yl, 3-methylpent-4-en-1-yl, 4-methylpent-4-en-1-yl, 1,1-dimethylbut-2-en-1-yl, 1,1-dimethylbut-3-en-1-yl, 1,2-dimethylbut-2-en-l-yl, 1,2-dimethylbut-3-en-1-yl, 1,3-dimethylbut-2-en-1-yl, 1,3-dimethylbut-3-en-1-yl, 2,2-dimethylbut-3-en-1-yl, 2,3-dimethylbut-2-en-1-yl, 2,3-dimethylbut-3-en-1-yl, 3,3-dimethylbut-2-en-l-yl, l-ethylbut-2-en-1-yl, 1-ethylbut-3-en-1-yl, 2-ethylbut-2-en-l-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-l-yl, 1-ethyl-1-methylprop-2-en-1-yl or 1-ethyl-2-methylprop-2-en-1-yl, in particular prop-2-en-1-yl or n-buten-4-yl;
- C2-C6-alkenyl is ethenyl or one of the radicals stated under C3-C6-alkenyl, in particular ethenyl or prop-2-en-1-yl;
- C3-C6-haloalkenyl is C3-C6-alkenyl as stated above, which is partially or completely substituted by fluorine, chlorine and/or bromine, eg. 2-chloroallyl, 3-chloroallyl, 2,3-dichloroallyl, 3,3-dichloroallyl, 2,3,3-trichloroallyl, 2,3-dichlorobut-2-enyl, 2-bromoallyl, 3-bromoallyl, 2,3-dibromoallyl, 3,3-dibromoallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl, in particular 2-chloroallyl or 3,3-dichloroallyl;
- phenyl-C3-C6-alkenyloxy is, for example, 3-phenylallyloxy, 4-phenylbut-2-enyloxy, 4-phenylbut-3-enyloxy or 5-phenylpent-4-enyloxy, preferably 3-phenylallyloxy or 4-phenylbut-2-enyloxy, in particular.3-phenylallyloxy;
- heterocyclyl-C3-C6-alkenyloxy is, for example, 3-heterocyclylallyloxy, 4-heterocyclylbut-2-enyloxy, 4-heterocyclylbut-3-enyloxy or S-heterocyclylpent-4-enyloxy, preferably 3-heterocyclylallyloxy or 4-heterocyclylbut-2-enyloxy, in particular 3-heterocyclylallyloxy;

.. .. . .

0050/46725 CA 022~0044 1998-09-24 - C3-C6-alkenyloxy is prop-l-en-l-yloxy, prop-2-en-1-yloxy, l-methylethenyloxy, n-buten-l-yloxy, n-buten-2-yloxy, n-buten-3-yloxy, l-methylprop-l-en-l-yloxy, 2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, n-penten-l-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, l-methylbut-l-en-l-yloxy, 2-methylbut-1-en-1-yloxy, 3-methylbut-1-en-1-yloxy, 1-methylbut-2-en-1-yloxy, 2-methylbut-2-en-1-yloxy, 3-methylbut-2-en-1-yloxy, 1-methylbut-3-en-1-yloxy, 2-methylbut-3-en-1-yloxy, 3-methylbut-3-en-1-yloxy, 1,1-dimethylprop-2-en-1-yloxy, 1,2-dimethylprop-1-en-1-yloxy, 1,2-dimethylprop-2-en-1-yloxy, l-ethylprop-l-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, n-hex-l-en-l-yloxy, n-hex-2-en-1-yloxy, n-hex-3-en-1-yloxy, n-hex-4-en-1-yloxy, n-hex-5-en-1-yloxy, l-methylpent-l-en-l-yloxy, 2-methylpent-1-en-1-yloxy, 3-me-thylpent-l-en-l-yloxy, 4-methylpent-1-en-1-yloxy, l-methyl-pent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy, 3-methyl-pent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy, l-methyl-pent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy, 3-methyl-pent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy, l-methyl-pent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy, 3-methyl-pent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy, l,l-dimethyl-but-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethyl-but-l-en-l-yloxy, 1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethyl-but-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy, 1,3-dimethyl-but-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethyl-but-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy, 2,3-dimethyl-but-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethyl-but-l-en-l-yloxy, 3,3-dimethylbut-2-en-1-yloxy, l-ethyl-but-l-en-1-yloxy, 1-ethylbut-2-en-1-yloxy, l-ethyl-but-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy, 2-ethyl-but-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy, 1,1,2-trimethyl-prop-2-en-1-yloxy, 1-ethyl-1-methylprop-2-en-1-yloxy, 1-ethyl-2-methylprop-1-en-1-yloxy or 1-ethyl-2-methyl-prop-2-en-1-yloxy, in particular prop-2-en-1-yloxy;

- C2-C6-alkenyloxy is ethenyloxy or one of the radicals stated under C3-C6-alkenyloxy, in particular ethenyloxy or prop-2-en-1-yloxy;

- C3-C6-haloalkenyloxy is C3-C6-alkenyloxy as stated above, which is partially or completely substituted by fluorine, chlorine and/or bl. ine eg. 2-chloroallyloxy, 3-chloroallyloxy, 2,3-dichloroallyloxy, 3,3-dichloroallyloxy, 2,3,3-trichloroallyloxy, 2,3-dichlorobut-2-enyloxy, 2-bromoallyloxy, 3-bromoallyloxy, 2,3-dibromoallyloxy, CA 022~0044 1998-09-24 3,3-dibL. -allyloxy, 2,3,3-tribromoallyloxy or 2,3-dibromobut-2-enyloxy, in particular 2-chloroallyloxy or 3,3-dichloroallyloxy;

5 - C3-C6-alkenylthio is prop-l-en-1-ylthio, prop-2-en-1-ylthio, l-methylethenylthio, n-buten-l-ylthio, n-buten-2-ylthio, n-buten-3-ylthio, l-methylprop-l-en-l-ylthio, 2-methylprop-1-en-1-ylthio, 1-methylprop-2-en-1-ylthio, 2-methylprop-2-en-1-ylthio, n-penten-l-ylthio, n-penten-2-ylthio, n-penten-3-ylthio, n-penten-4-ylthio, l-methylbut-l-en-l-ylthio, 2-methylbut-1-en-1-ylthio, 3-methylbut-1-en-1-ylthio, 1-methylbut-2-en-1-ylthio, 2-methylbut-2-en-1-ylthio, 3-methylbut-2-en-1-ylthio, l-methylbut-3-en-1-ylthio, 2-methylbut-3-en-1-ylthio, 3-methylbut-3-en-1-ylthio, 1,1-dimethylprop-2-en-1-ylthio, 1,2-dimethylprop-1-en-1-ylthio, 1,2-dimethylprop-2-en-1-ylthio, 1-ethyl-prop-1-en-2-ylthio, l-ethylprop-2-en-1-ylthio, n-hex-l-en-l-ylthio, n-hex-2-en-1-ylthio, n-hex-3-en-1-ylthio, n-hex-4-en-1-ylthio, n-hex-5-en-1-ylthio, l-methylpent-l-en-l-ylthio, 2-methylpent-1-en-1-ylthio, 3-methylpent-1-en-1-ylthio, 4-methylpent-1-en-1-ylthio, l-methylpent-2-en-1-ylthio, 2-methylpent-2-en-1-ylthio, 3-methylpent-2-en-1-ylthio, 4-methylpent-2-en-1-ylthio, 1-methylpent-3-en-1-ylthio, 2-methylpent-3-en-1-ylthio, 3-methylpent-3-en-1-ylthio, 4-methylpent-3-en-1-ylthio, l-methylpent-4-en-1-ylthio, 2-methylpent-4-en-1-ylthio, 3-methylpent-4-en-1-ylthio, 4-methylpent-4-en-1-ylthio, 1,1-dimethylbut-2-en-1-ylthio, 1,1-dimethylbut-3-en-1-ylthio, 1,2-dimethylbut-1-en-1-ylthio, 1,2-dimethylbut-2-en-1-ylthio, 1,2-dimethylbut-3-en-1-ylthio, 1,3-dimethylbut-1-en-1-ylthio, 1,3-dimethylbut-2-en-1-ylthio, 1,3-dimethylbut-3-en-1-ylthio, 2,2-dimethylbut-3-en-1-ylthio, 2,3-dimethylbut-1-en-1-ylthio, 2,3-dimethylbut-2-en-1-ylthio, 2,3-dimethylbut-3-en-1-ylthio, 3,3-dimethylbut-1-en-1-ylthio, 3,3-dimethylbut-2-en-1-ylthio, l-ethylbut-l-en-l-ylthio, l-ethylbut-2-en-1-ylthio, l-ethylbut-3-en-1-ylthio, 2-ethylbut-1-en-1-ylthio, 2-ethylbut-2-en-1-ylthio, 2-ethylbut-3-en-1-ylthio, 1,1,2-trimethylprop-2-en-1-ylthio, 1-ethyl-1-methyl-prop-2-en-1-ylthio, l-ethyl-2-methyl-prop-1-en-1-ylthio or l-ethyl-2-methylprop-2-en-1-ylthio, in particular prop-2-en-1-ylthio;

.. . . . . . ..

OOSO/46725 CA 022~0044 1998-09-24 ~ - C2-C6-alkenylthio is ethenylthio or one of the radicals stated under C3-C6-alkenylthio, in particular ethenylthio or prop-2-en-1-ylthio;

5 - C3-C6-alkynyl is prop-1-yn-1-yl, prop-2-yn-1-yl, n-but-1-yn-1-yl, n-but-1-yn-3-yl, n-but-1-yn-4-yl, n-but-2-yn-1-yl, n-pent-l-yn-l-yl, n-pent-l-yn-3-yl, n-pent-1-yn-4-yl, n-pent-l-yn-5-yl, n-pent-2-yn-1-yl, n-pent-2-yn-4-yl, n-pent-2-yn-5-yl, 3-methylbut-1-yn-3-yl, 3-methylbut-1-yn-4-yl, n-hex-l-yn-1-yl, n-hex-1-yn-3-yl, n-hex-1-yn-4-yl, n-hex-1-yn-5-yl, n-hex-1-yn-6-yl, n-hex-2-yn-1-yl, n-hex-2-yn-4-yl, n-hex-2-yn-5-yl, n-hex-2-yn-6-yl, n-hex-3-yn-1-yl, n-hex-3-yn-2-yl, 3-methylpent-1-yn-1-yl, 3-methylpent-1-yn-3-yl, 3-methylpent-1-yn-4-yl, 3-methylpent-1-yn-5-yl, 4-methylpent-1-yn-1-yl, 4-methylpent-2-yn-4-yl or 4-methylpent-2-yn-5-yl, in particular prop-2-yn-1-yl;

- C2-C6-alkynyl is ethynyl or one of the radicals stated under C3-C6-alkynyl, in particular ethynyl or prop-2-yn-1-yl;
- C3-C6-alkynyloxy is prop-1-yn-1-yloxy, prop-2-yn-1-yloxy, n-but-1-yn-1-yloxy, n-but-1-yn-3-yloxy, n-but-1-yn-4-yloxy, n-but-2-yn-1-yloxy, n-pent-1-yn-1-yloxy, n-pent-1-yn-3-yloxy, n-pent-l-yn-4-yloxy, n-pent-1-yn-5-yloxy, n-pent-2-yn-1-yloxy, n-pent-2-yn-4-yloxy, n-pent-2-yn-S-yloxy, 3-methylbut-1-yn-3-yloxy, 3-methylbut-1-yn-4-yloxy, n-hex-1-yn-1-yloxy, n-hex-1-yn-3-yloxy, n-hex-1-yn-4-yloxy, n-hex-1-yn-5-yloxy, n-hex-1-yn-6-yloxy, n-hex-2-yn-1-yloxy, n-hex-2-yn-4-yloxy, n-hex-2-yn-5-yloxy, n-hex-2-yn-6-yloxy, n-hex-3-yn-1-yloxy, n-hex-3-yn-2-yloxy, 3-methylpent-1-yn-1-yloxy, 3-methylpent-1-yn-3-yloxy, 3-methylpent-1-yn-4-yloxy, 3-methylpent-1-yn-5-yloxy, 4-methylpent-1-yn-1-yloxy, 4-methylpent-2-yn-4-yloxy or 4-methylpent-2-yn-5-yloxy, in particular prop-2-yn-1-yloxy;

- C2-C6-alkynyloxy is ethynyloxy or one of the radicals stated under C3-C6-alkynyloxy, in particular ethynyloxy or prop-2-yn-1-yloxy;
- C3-C6-alkynylthio is prop-l-yn-1-ylthio, prop-2-yn-1-ylthio, n-but-1-yn-1-ylthio, n-but-1-yn-3-ylthio, n-but-1-yn-4-ylthio, n-but-2-yn-1-ylthio, n-pent-1-yn-1-ylthio, n-pent-1-yn-3-ylthio, n-pent-1-yn-4-ylthio, n-pent-1-yn-5-ylthio, n-pent-2-yn-1-ylthio, n-pent-2-yn-4-ylthio, n-pent-2-yn-5-ylthio, 3-methylbut-1-yn-3-ylthio, 3-methylbut-1-yn-4-ylthio, n-hex-1-yn-1-ylthio, n-hex-1-yn-3-ylthio, n-hex-l-CA 022~0044 1998-09-24 yn-4-ylthio, n-hex-1-yn-5-ylthio, n-hex-1-yn-6-ylthio, n-hex-2-yn-1-ylthio, n-hex-2-yn-4-ylthio, n-hex-2-yn-5-ylthio, n-hex-2-yn-6-ylthio, n-hex-3-yn-1-ylthio, n-hex-3-yn-2-ylthio, 3-methylpent-1-yn-1-ylthio, 3-methylpent-1-yn-3-ylthio, 3-methylpent-1-yn-4-ylthio, 3-me-thylpent-l-yn-5-ylthio, 4-methylpent-1-yn-1-ylthio, 4-methyl-pent-2-yn-4-ylthio or 4-methylpent-2-yn-5-ylthio, in particu-lar prop-2-yn-1-ylthio;

10 - C2-C6-alkynylthio is ethynylthio or one of the radicals stated under C3-C6-alkynylthio, in particular ethynylthio or prop-2-yn-1-ylthio;

- (C3-C6-alkenyl)oxycarbonyl is prop-l-en-l-yloxycarbonyl, prop-2-en-1-yloxycarbonyl, l-methylethenyloxycarbonyl, n-buten-l-yloxycarbonyl, n-buten-2-yloxycarbonyl, n-buten-3-yloxycarbonyl, l-methylprop-l-en-l-yloxycarbonyl, 2-methylprop-1-en-1-yloxycarbonyl, l-methylprop-2-en-1-yloxycarbonyl, 2-methylprop-2-en-1-yloxycarbonyl, n-penten-l-yloxycarbonyl, n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl, n-penten-4-yloxycarbonyl, l-methylbut-l-en-l-yloxycarbonyl, 2-methylbut-1-en-1-yloxycarbonyl, 3-methylbut-1-en-1-yloxycarbonyl, 1-methylbut-2-en-1-yloxycarbonyl, 2-methylbut-2-en-1-yloxycarbonyl, 3-methylbut-2-en-1-yloxycarbonyl, l-methylbut-3-en-1-yloxycarbonyl, 2-methylbut-3-en-1-yloxycarbonyl, 3-methylbut-3-en-1-yloxycarbonyl, 1,1-dimethylprop-2-en-1-yloxycarbonyl, 1,2-dimethylprop-1-en-1-yloxycarbonyl, 1,2-dimethylprop-2-en-1-yloxycarbonyl, l-ethylprop-l-en-2-yloxycarbonyl, 1-ethylprop-2-en-1-yloxycarbonyl, n-hex-l-en-l-yloxycarbonyl, n-hex-2-en-1-yloxycarbonyl, n-hex-3-en-1-yloxycarbonyl, n-hex-4-en-1-yloxycarbonyl, n-hex-5-en-1-yloxycarbonyl, l-methylpent-l-en-1-yloxycarbonyl, 2-methylpent-1-en-1-yloxycarbonyl, 3-methylpent-1-en-1-yloxycarbonyl, 4-methylpent-1-en-1-yloxycarbonyl, 1-methylpent-2-en-1-yloxycarbonyl, 2-methylpent-2-en-1-yloxycarbonyl, 3-methylpent-2-en-1-yloxycarbonyl, 4-methylpent-2-en-1-yloxycarbonyl, l-methylpent-3-en-1-yloxycarbonyl, 2-methylpent-3-en-1-yloxycarbonyl, r CA 022~0044 1998-09-24 3-methylpent-3-en-1-yloxycarbonyl, 4-methylpent-3-en-l-yloxycarbonyl, l-methylpent-4-en-1-yloxycarbonyl, 2-methylpent-4-en-1-yloxycarbonyl, 3-methylpent-4-en-1-yloxycarbonyl, 4-methylpent-4-en-1-yloxycarbonyl, 1,1-dimethylbut-2-en-1-yloxycarbonyl, 1,1-dimethylbut-3-en-1-yloxycarbonyl, 1,2-dimethylbut-1-en-1-yloxycarbonyl, 1,2-dimethylbut-2-en-1-yloxycarbonyl, 1,2-dimethylbut-3-en-1-yloxycarbonyl, 1,3-dimethylbut-1-en-1-yloxycarbonyl, 1,3-dimethylbut-2-en-1-yloxycarbonyl, 1,3-dimethylbut-3-en-1-yloxycarbonyl, 2,2-dimethylbut-3-en-l-yloxycarbonyl, 2,3-dimethylbut-1-en-1-yloxycarbonyl, 2,3-dimethylbut-2-en-1-yloxycarbonyl, 2,3-dimethylbut-3-en-1-yloxycarbonyl, 3,3-dimethylbut-1-en-1-yloxycarbonyl, 3,3-dimethylbut-2-en-1-yloxycarbonyl, l-ethylbut-l-en-l-yloxycarbonyl, 1-ethylbut-2-en-1-yloxycarbonyl, 1-ethylbut-3-en-1-yloxycarbonyl, 2-ethylbut-1-en-1-yloxycarbonyl, 2-ethylbut-2-en-1-yloxycarbonyl, 2-ethylbut-3-en-1-yloxycarbonyl, 1,1,2-trimethylprop-2-en-1-yloxycarbonyl, l-ethyl-l-methylprop-2-en-1-yloxycarbonyl, l-ethyl-2-methylprop-1-en-1-yloxycarbonyl or 1-ethyl-2-methylprop-2-en-1-yloxycarbonyl, in particular prop-2-en-1-yloxycarbonyl;

- (C3-C6-alkenyloxy)carbonyl-Cl-C6-alkyl is Cl-C6-alkyl substituted by (c3-c6-alkenyloxy)carbonyl as stated above, preferably by prop-2-en-1-yloxycarbonyl, for example prop-2-en-1-yloxycarbonylmethyl;

- (C3-C6-alkenyl)carbonyloxy is prop-1-en-1-ylcarbonyloxy, prop-2-en-1-ylcarbonyloxy, l-methylethenylcarbonyloxy, n-buten-l-ylcarbonyloxy, n-buten-2-ylcarbonyloxy, n-buten-3-ylcarbonyloxy, l-methylprop-l-en-l-ylcarbonyloxy, 2-methylprop-1-en-1-ylcarbonyloxy, l-methylprop-2-en-1-ylcarbonyloxy, 2-methylprop-2-en-1-ylcarbonyloxy, n-penten-l-ylcarbonyloxy, n-penten-2-ylcarbonyloxy, n-penten-3-ylcarbonyloxy, n-penten-4-ylcarbonyloxy, l-methylbut-l-en-l-ylcarbonyloxy, 2-methylbut-1-en-1-ylcarbonyloxy, 0050/46725 CA 022~0044 1998-09-24 3-methylbut-l-en-1-ylcarbonyloxy, l-methylbut-2-en-1-ylcarbonyloxy, 2-methylbut-2-en-1-ylcarbonyloxy, 3-methylbut-2-en-1-ylcarbonyloxy, 1-methylbut-3-en-l-ylcarbonyloxy, 2-methylbut-3-en-l-ylcarbonyloxy, 3-methylbut-3-en-l-ylcarbonyloxy, l,1-dimethylprop-2-en-1-ylcarbonyloxy, 1,2-dimethylprop-1-en-1-ylcarbonyloxy, 1,2-dimethylprop-2-en-l-ylcarbonyloxy, l-ethylprop-l-en-2-ylcarbonyloxy, l-ethylprop-2-en-1-ylcarbonyloxy, n-hex-1-en-l-ylcarbonyloxy, n-hex-2-en-1-ylcarbonyloxy, n-hex-3-en-l-ylcarbonyloxy, n-hex-4-en-l-ylcarbonyloxy, n-hex-5-en-l-ylcarbonyloxy, l-methylpent-l-en-l-ylcarbonyloxy, 2-methylpent-l-en-l-ylcarbonyloxy, 3-methylpent-l-en-l-ylcarbonyloxy, 4-methylpent-l-en-1-ylcarbonyloxy, l-methylpent-2-en-l-ylcarbonyloxy, 2-methylpent-2-en-l-ylcarbonyloxy, 3-methylpent-2-en-l-ylcarbonyloxy, 4-methylpent-2-en-1-ylcarbonyloxy, 1-methylpent-3-en-1-ylcarbonyloxy, 2-methylpent-3-en-l-ylcarbonyloxy, 3-methylpent-3-en-l-ylcarbonyloxy, 4-methylpent-3-en-l-ylcarbonyloxy, 1-methylpent-4-en-l-ylcarbonyloxy, 2-methylpent-4-en-l-ylcarbonyloxy, 3-methylpent-4-en-l-ylcarbonyloxy, 4-methylpent-4-en-1-ylcarbonyloxy, l,1-dimethylbut-2-en-1-ylcarbonyloxy, 1,1-dimethylbut-3-en-l-ylcarbonyloxy, 1,2-dimethylbut-l-en-l-ylcarbonyloxy, 1,2-dimethylbut-2-en-1-ylcarbonyloxy, 1,2-dimethylbut-3-en-l-ylcarbonyloxy, 1,3-dimethylbut-l-en-l-ylcarbonyloxy, 1,3-dimethylbut-2-en-1-ylcarbonyloxy, 1,3-dimethylbut-3-en-1-ylcarbonyloxy, 2,2-dimethylbut-3-en-1-ylcarbonyloxy, 2,3-dimethylbut-1-en-1-ylcarbonyloxy, 2,3-dimethylbut-2-en-1-ylcarbonyloxy, 2,3-dimethylbut-3-en-l-ylcarbonyloxy, 3,3-dimethylbut-1-en-1-ylcarbonyloxy, 3,3-dimethylbut-2-en-1-ylcarbonyloxy, l-ethylbut-l-en-l-ylcarbonyloxy, l-ethylbut-2-en-l-ylcarbonyloxy, l-ethylbut-3-en-l-ylcarbonyloxy, 2-ethylbut-1-en-l-ylcarbonyloxy, 2-ethylbut-2-en-l-ylcarbonyloxy, 2-ethylbut-3-en-l-ylcarbonyloxy, 1,1,2-trimethylprop-2-en-l-ylcarbonyloxy, l-ethyl-l-methylprop-2-en-1-ylcarbonyloxy, l-ethyl-2-methylprop-1-en-1-ylcarbonyloxy or l-ethyl-CA 022~0044 1998-09-24 2-methylprop-2-en-1-ylcarbonyloxy, in particular prop-2-en-l-ylcarbonyloxy;

- (C2-C6-alkenyl)carbonyloxy is ethenylcarbonyloxy or one of the radicals stated under (c3-c6-alkenyl)carbonyloxy~ in particular ethenylcarbonyloxy or prop-2-en-1-ylcarbonyloxy;

- (C3-C6-alkenyl)carbonylthio is prop-l-en-l-ylcarbonylthio, prop-2-en-1-ylcarbonylthio, 1-methylethenylcarbonylthio, n-buten-l-ylcarbonylthio, n-buten-2-ylcarbonylthio, n-buten-3-ylcarbonylthio, l-methylprop-l-en-l-ylcarbonylthio, 2-methylprop-1-en-1-ylcarbonylthio, 1-methylprop-2-en-1-ylcarbonylthio, 2-methylprop-2-en-1-ylcarbonylthio, n-penten-l-ylcarbonylthio, n-penten-2-ylcarbonylthio, n-penten-3-ylcarbonylthio, n-penten-4-ylcarbonylthio, l-methylbut-l-en-l-ylcarbonylthio, 2-methylbut-1-en-1-ylcarbonylthio, 3-methylbut-1-en-1-ylcarbonylthio, 1-methylbut-2-en-1-ylcarbonylthio, 2-methylbut-2-en-1-ylcarbonylthio, 3-methylbut-2-en-1-ylcarbonylthio, l-methylbut-3-en-1-ylcarbonylthio, 2-methylbut-3-en-1-ylcarbonylthio, 3-methylbut-3-en-l-ylcarbonylthio, 1,1-dimethylprop-2-en-1-ylcarbonylthio, 1,2-dimethylprop-1-en-1-ylcarbonylthio, 1,2-dimethylprop-2-en-l-ylcarbonylthio, l-ethylprop-l-en-2-ylcarbonylthio, l-ethylprop-2-en-1-ylcarbonylthio, n-hex-l-en-l-ylcarbonylthio, n-hex-2-en-1-ylcarbonylthio, n-hex-3-en-1-ylcarbonylthio, n-hex-4-en-1-ylcarbonylthio, n-hex-5-en-1-ylcarbonylthio, l-methylpent-l-en-l-ylcarbonylthio, 2-methylpent-1-en-1-ylcarbonylthio, 3-methylpent-1-en-1-ylcarbonylthio, 4-methylpent-1-en-1-ylcarbonylthio, l-methylpent-2-en-1-ylcarbonylthio, 2-methylpent-2-en-1-ylcarbonylthio, 3-methylpent-2-en-1-ylcarbonylthio, 4-methylpent-2-en-1-ylcarbonylthio, 1-methylpent-3-en-1-ylcarbonylthio, 2-methylpent-3-en-1-ylcarbonylthio, 3-methylpent-3-en-1-ylcarbonylthio, 4-methylpent-3-en-1-ylcarbonylthio, l-methylpent-4-en-1-ylcarbonylthio, 2-methylpent-4-en-1-ylcarbonylthio, 3-methylpent-4-en-1-ylcarbonylthio, 4-methylpent-4-en-1-ylcarbonylthio, CA 022~0044 1998-09-24 1,1-dimethylbut-2-en-1-ylcarbonylthio, 1,1-dimethylbut-3-en-1-ylcarbonylthio, 1,2-dimethylbut-1-en-1-ylcarbonylthio, 1,2-dimethylbut-2-en-1-ylcarbonylthio, 1,2-dimethylbut-3-en-1-ylcarbonylthio, 1,3-dimethylbut-1-en-1-ylcarbonylthio, 1,3-dimethylbut-2-en-1-ylcarbonylthio, 1,3-dimethylbut-3-en-1-ylcarbonylthio, 2,2-dimethylbut-3-en-1-ylcarbonylthio, 2,3-dimethylbut-1-en-1-ylcarbonylthio, 2,3-dimethylbut-2-en-1-ylcarbonylthio, 2,3-dimethylbut-3-en-1-ylcarbonylthio, 3,3-dimethylbut-1-en-1-ylcarbonylthio, 3,3-dimethylbut-2-en-1-ylcarbonylthio, 1-ethylbut-1-en-1-ylcarbonylthio, l-ethylbut-2-en-1-ylcarbonylthio, l-ethylbut-3-en-1-ylcarbonylthio, 2-ethylbut-1-en-1-ylcarbonylthio, 2-ethylbut-2-en-1-ylcarbonylthio, 2-ethylbut-3-en-1-ylcarbonylthio, 1,1,2-trimethylprop-2-en-1-ylcarbonylthio, l-ethyl-l-methylprop-2-en-1-ylcarbonylthio, 1-ethyl-2-methylprop-1-en-1-ylcarbonylthio or 1-ethyl-2-methylprop-2-en-1-ylcarbonylthio, in particular prop-2-en-1-yl-carbonylthio;

- (C2-C6-alkenyl)carbonylthio is ethenylcarbonylthio or one of the radicals stated under (C3-C6-alkenyl)carbonylthio in particular prop-2-en-1-yl-carbonylthio;
- (C3-C6-alkynyl)carbonyloxy is prop-l-yn-l-ylcarbonyloxy, prop-2-yn-1-ylcarbonyloxy, n-but-1-yn-1-ylcarbonyloxy, n-but-1-yn-3-ylcarbonyloxy, n-but-1-yn-4-ylcarbonyloxy, n-but-2-yn-1-ylcarbonyloxy, n-pent-l-yn-1-ylcarbonyloxy, n-pent-1-yn-3-ylcarbonyloxy, n-pent-1-yn-4-ylcarbonyloxy, n-pent-1-yn-5-ylcarbonyloxy, n-pent-2-yn-1-ylcarbonyloxy, n-pent-2-yn-4-ylcarbonyloxy, n-pent-2-yn-5-ylcarbonyloxy, 3-methylbut-1-yn-3-ylcarbonyloxy, 3-methylbut-1-yn-4-ylcarbonyloxy, n-hex-1-yn-1-ylcarbonyloxy, n-hex-1-yn-3-ylcarbonyloxy, n-hex-1-yn-4-ylcarbonyloxy, n-hex-1-yn-5-ylcarbonyloxy, n-hex-1-yn-6-ylcarbonyloxy, n-hex-2-yn-1-ylcarbonyloxy, n-hex-2-yn-4-ylcarbonyloxy, n-hex-2-yn-5-ylcarbonyloxy, n-hex-2-yn-6-ylcarbonyloxy, n-hex-3-yn-1-ylcarbonyloxy, n-hex-3-yn-2-ylcarbonyloxy, 3-methylpent-1-yn-1-ylcarbonyloxy, 3-methylpent-1-yn-3-ylcarbonyloxy, 3-methylpent-1-yn-4-ylcarbonyloxy, , .

CA 022~0044 1998-09-24 3-methylpent-1-yn-5-ylcarbonyloxy, 4-methylpent-1-yn-1-ylcarbonyloxy, 4-methylpent-2-yn-4-ylcarbonyloxy or 4-methylpent-2-yn-5-ylcarbonyloxy, in particular prop-2-yn-1-ylcarbonyloxy;

- (C2-C6-alkynyl)carbonyloxy is ethynylcarbonyloxy or one of the radicals stated under (C3-C6-alkynyl)carbonyloxy, in particular ethynylcarbonyloxy or prop-2-yn-1-ylcarbonyloxy;
- C3-C6-alkynylsulfonyloxy is prop-1-yn-1-ylsulfonyloxy, prop-2-yn-1-ylsulfonyloxy, n-but-l-yn-l-ylsulfonyloxy, n-but-l-yn-3-ylsulfonyloxy, n-but-1-yn-4-ylsulfonyloxy, n-but-2-yn-1-ylsulfonyloxy, n-pent-1-yn-1-ylsulfonyloxy, n-pent-1-yn-3-ylsulfonyloxy, n-pent-1-yn-4-ylsulfonyloxy, n-pent-l-yn-5-ylsulfonyloxy, n-pent-2-yn-1-ylsulfonyloxy, n-pent-2-yn-4-ylsulfonyloxy, n-pent-2-yn-5-ylsulfonyloxy, 3-methylbut-1-yn-3-ylsulfonyloxy, 3-methylbut-1-yn-4-ylsulfonyloxy, n-hex-1-yn-1-ylsulfonyloxy, n-hex-1-yn-3-ylsulfonyloxy, n-hex-1-yn-4-ylsulfonyloxy, n-hex-1-yn-5-ylsulfonyloxy, n-hex-1-yn-6-ylsulfonyloxy, n-hex-2-yn-1-ylsulfonyloxy, n-hex-2-yn-4-ylsulfonyloxy, n-hex-2-yn-5-ylsulfonyloxy, n-hex-2-yn-6-ylsulfonyloxy, n-hex-3-yn-1-ylsulfonyloxy, n-hex-3-yn-2-ylsulfonyloxy, 3-methylpent-1-yn-1-ylsulfonyloxy, 3-methylpent-1-yn-3-ylsulfonyloxy, 3-methylpent-1-yn-4-ylsulfonyloxy, 3-methylpent-1-yn-5-ylsulfonyloxy, 4-methylpent-1-yn-1-ylsulfonyloxy, 4-methylpent-2-yn-4-ylsulfonyloxy or 4-methylpent-2-yn-5-ylsulfonyloxy, in particular prop-2-yn-1-ylsulfonyloxy;
- (c3-c6-alkynyl)carbonylthio is prop-1-yn-1-ylcarbonylthio, prop-2-yn-1-ylcarbonylthio, n-but-1-yn-1-ylcarbonylthio, n-but-1-yn-3-ylcarbonylthio, n-but-1-yn-4-ylcarbonylthio, n-but-2-yn-1-ylcarbonylthio, n-pent-1-yn-1-ylcarbonylthio, n-pent-1-yn-3-ylcarbonylthio, n-pent-1-yn-4-ylcarbonylthio, n-pent-1-yn-5-ylcarbonylthio, n-pent-2-yn-1-ylcarbonylthio, n-pent-2-yn-4-ylcarbonylthio, n-pent-2-yn-5-ylcarbonylthio, 3-methylbut-1-yn-3-ylcarbonylthio, 3-methylbut-1-yn-4-ylcarbonylthio, n-hex-1-yn-1-ylcarbonylthio, n-hex-1-yn-3-ylcarbonylthio, n-hex-1-yn-4-ylcarbonylthio, n-hex-1-yn-5-ylcarbonylthio, n-hex-1-yn-6-ylcarbonylthio, n-hex-2-yn-1-ylcarbonylthio, n-hex-2-yn-4-ylcarbonylthio, n-hex-2-yn-5-ylcarbonylthio, n-hex-2-yn-6-ylcarbonylthio, n-hex-3-yn-1-ylcarbonylthio, CA 022~0044 l998-09-24 n-hex-3-yn-2-ylcarbonylthio, 3-methylpent-1-yn-1-ylcarbonylthio, 3-methylpent-1-yn-3-ylcarbonylthio, 3-methylpent-1-yn-4-ylcarbonylthio, 3-methylpent-1-yn-5-ylcarbonylthio, 4-methylpent-1-yn-1-ylcarbonylthio, 4-methylpent-2-yn-4-ylcarbonylthio or 4-methylpent-2-yn-5-ylcarbonylthio, in particular prop-2-yn-1-ylcarbonylthio;
- (C2-C6-alkynyl)carbonylthio is ethynylcarbonylthio or one of the radicals stated under (C3-C6-alkynyl)carbonylthio, in particular ethynylcarbonylthio or prop-2-yn-1-ylcarbonylthio;

15 - (Cl-C6-alkoxy)carbonyl-C2-C6-alkenyl is C2-C6-alkenyl substituted by (C1-C6-alkoxy)carbonyl as stated above, for example methoxycarbonylprop-2-en-1-yl;

- C3-C6-alkenyloxy-Cl-C6-alkyl is Cl-C6-alkyl substituted by C3-C6-alkenyloxy as stated above, preferably by allyloxy, 2-methylprop-2-en-1-yloxy, but-1-en-3-yloxy, but-1-en-4-yloxy or but-2-en-1-yloxy, for example allyloxymethyl, 2-allyloxyethyl or but-1-en-4-yloxymethyl;

- C3-C6-alkynyloxy-cl-c6-alkyl is C1-C6-alkyl substituted by C3-C6-alkynyloxy as stated above, preferably by propargyloxy, but-l-yn-3-yloxy, but-1-yn-4-yloxy or but-2-yn-1-yloxy, for example propargyloxymethyl or 2-propargyloxyethyl;

30 - C3-C7-cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl or cycloheptyl, in particular cyclopentyl or cyclohexyl;

- C3-C6-cycloalkyl ic cyclopropyl, cyclobutyl, cyclopentyl or 3 5 cyclohexyl;

- C3-C8-cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl or cyclooctyl, in particular cyclopentyl or cyclohexyl;

- C3-CB-cycloalkyl-Cl-C4-alkyl is cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl, cyclohexylmethyl, cycloheptylmethyl, cyclooctylmethyl, l-(cyclopropyl)ethyl, l-(cyclobutyl)ethyl, l-(cyclopentyl)ethyl, l-(cyc lohexyl)ethyl, l-(cycloheptyl)ethyl, l-(cyclooctyl)ethyl, 2-(cyclopropyl)ethyl, 2-(cyclobutyl)ethyl, 2-(cyclopentyl)ethyl, , CA 022~0044 1998-09-24 ooso/4672s -2-(cyclohexyl)ethyl, 2-(cycloheptyl)ethyl, 2-(cyclooctyl)ethyl, 3-(cyclopropyl)propyl, 3-(cyclobutyl)propyl~ 3-(cyclopentyl)propyl, 3-(cyclohexyl)propyl~ 3-(cycloheptyl)propyl, 3-(cyclooctyl)propyl~ 4-(cyclopropyl)butyl, 4-(cyclobutyl)butyl, 4-(cyclopentyl)butyl, 4-(cyclohexyl)butyl~ 4-(cycloheptyl)butyl or 4-(cyclooctyl)butyl~ in particular cyclopentylmethyl or cyclohexylmethyl;
- C3-C6-cyCloalkoxy i8 cyclopropoxy, cyclobutoxy, cyclopentyloxy or cyclohexyloxy;

- C3-C6-cycloalkylthio is cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio;

- C3-C6-cycloalkylcarbonyloxy is cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or cyclohexylcarbonyloxy;
- C3-C6-cycloalkylsulfonyloxy is cyclo~Lo~ylsulfonyloxy, cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or cyclohexylsulfonyloxy;
25 - C3-C6-cycloalkoxy-C1-C4-alkyl is cyclo~lopoxymethyl, cyclobutoxymethyl, cyclopentyloxymethyl, cyclohexyloxymethyl, 1-(cyclopropoxy)ethyl, l-(cyclobutoxy)ethyl, 1-(cyclopentyloxy)ethyl, 1-(cyclohexyloxy)ethyl, 2-(cyclopropoxy)ethyl, 2-(cyclobutoxy)ethyl, 2-(cyclopentyloxy)ethyl, 2-(cyclohexyloxy)ethyl, 3-(cyclopropoxy)propyl, 3-(cyclobutoxy)propyl, 3-(cyclopentyloxy~propyl~ 3-(cyclohexyloxy)propyl, 4-(cyclopropoxy)butyl~ 4-(cyclobutoxy)butyl~
4-(cyclopentyloxy)butyl or 4-(cyclohexyloxy)butyl, in particular cyclopentyloxymethyl, cyclohexyloxymethyl or 2-(cyclopentyloxy)ethyl;

- C5-C7-cyclo~lkenyloxy is cyclopent-1-enyloxy, cyclopent-2-enyloxy, cylopent-3-enyloxy, cyclohex-1-enyloxy, cyclohex-2-enyloxy, cyclohex-3-enyloxy, cyclohept-1-enyloxy, cyclohept-2-enyloxy, cyclohept-3-enyloxy or cyclohept-4-enyloxy;
- Cl-C3-alkylene is methylene, 1,2-ethylene or 1,3-propylene.

CA 022~0044 1998-09-24 .

3- to 7-membered heterocyclyl, which can be linked directly or via an oxygen, alkoxy, alkenyloxy or alkynyloxy bridge, is to be understood as meaning both saturated or partially or completely unsaturated and aromatic heterocycles having from one to three 5 heteroatoms selected from the group consisting of - from one to three nitrogen atoms, - one or two oxygen atoms and - one or two sulfur atoms.

10 Examples of saturated heterocyclic structures which may contain a carbonyl or thiocarbonyl ring member are:
oxiranyl! thiiranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-l-yl, diaziridin-3-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, azetidin-l-yl, azetidin-2-yl, azetidin-3-yl, 15 tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, 1,3-dioxolan-2-yl, 1,3-dioxolan-4-yl, 1,3-oxathiolan-2-yl, 1,3-oxathiolan-4-yl, 1,3-oxathiolan-5-yl, 1,3-oxazolidin-2-yl, 20 1,3-oxazolidin-3-yl, 1,3-oxazolidin-4-yl, 1,3-oxazolidin-5-yl, 1,2-oxazolidin-2-yl, 1,2-oxazolidin-3-yl, 1,2-oxazolidin-4-yl, 1,2-oxazolidin-5-yl, 1,3-dithiolan-2-yl, 1,3-dithiolan-4-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-5-yl, tetrahydropyrazol-l-yl, tetrahydropyrazol-3-yl, 25 tetrahydropyrazol-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydL OPYL an-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydropyran-4-yl, piperidin-l-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, 1,3-dioxan-2-yl, 1,3-~;o~n-4-yl, 30 1,3-dioxan-5-yl, 1,4-dioxan-2-yl, 1,3-oxathian-2-yl, 1,3-oxathian-4-yl, 1,3-oxathian-5-yl, 1,3-oxathian-6-yl, 1,4-oxathian-2-yl, 1,4-oxathian-3-yl, morpholin-2-yl, morpholin-3-yl, morpholin-4-yl, hexahydropyridazin-l-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, 35 hexahydropyrimidin-l-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydLopyrimidin-5-yl, piperazin-l-yl, piperazin-2-yl, piperazin-3-yl, hexahydro-1,3,5-triazin-1-yl, hexahydro-1,3,5-triazin-2-yl, oxepan-2-yl, oxepan-3-yl, oxepan-4-yl, thiepan-2-yl, thiepan-3-yl, thiepan-4-yl, 40 1,3-dioxepan-2-yl, 1,3-dioxepan-4-yl, 1,3-dioxepan-5-yl, ; 1,3-dioxepan-6-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl, 1,3-dithiepan-2-yl, 1,4-dioxepan-2-yl, 1,4-dioxepan-7-yl, hexahydroazepin-l-yl, hexahydroazepin-2-yl, hexahydroazepin-3-yl, hexahydroazepin-4-yl, hexahydro-1,3-di-45 azepin-l-yl, hexahydro-1,3-diazepin-2-yl, hexahydro-1,3-di-, . . .

CA 022~0044 1998-09-24 azepin-4-yl, hexahydro-1,4-diazepin-1-yl and hexahydro-1,4-dia-zepin-2-yl;

examples of unsaturated heterocyclic structures which may contain 5 a carbonyl or thiocarbonyl ring member are:
dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl and 1,3-oxazolin-2-yl;
among the heteroaromatic structures, the 5- and 6-membered ones 10 are preferred, eg.
furyl, such as 2-furyl and 3-furyl, thienyl, such as 2-thienyl and 3-thienyl, pyrrolyl, such as 2-pyrrolyl and 3-pyrrolyl, iso-xazolyl, such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl, such as 3-isothiazolyl, 4-isothiazolyl and 5-iso-15 thiazolyl, pyrazolyl, such as 3-pyrazolyl, 4-pyrazolyl and 5-py-razolyl, oxazolyl, such as 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl, such as 2-th;Azolyl, 4-thiazolyl and 5-thiazolyl, imi-dazolyl, such as 2-imidazolyl and 4-~ AZO1Y1~ oYA~;Azolyl, such as 1,2,4--OYA~l; Azol--3--yl,1,2,4--oYAd;A 701--5--yland 1,3,4--o~rA~i A--20 zol--2--yl,thi A~l iAzolyl, such as 1,2,4--thiA-liA~7ol--3--yl, 1,2,4--th;A~liA 7O1--5--yland 1,3,4--thiA~iA 7O1--2--yl,triazolyl, such as 1,2,4-triazol-1-yl, 1,2,4-triazol-3-yl and 1,2,4-triazol-4-yl, pyridinyl, such as 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, py-ridazinyl, such as 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl, 25 such as 2-pyri~i~inyl, 4-pyrimidinyl and 5-pyrimidinyl, and furt-hermore 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in particular pyridyl, pyrimidinyl, furanyl and thienyl.
All phenyl and heterocyclic rings are preferably unsubstituted or 30 carry one substitute.
With regard to the use of the novel compounds of the formula I as herbicides and/or as compounds having defoliant/desiccant activity, the variables preferably have the following meanings, 35 alone or in combination:
X is oxygen;
R1 is trifluoromethyl;
R2 is hydrogen;
I

R3 is halogen, in particular chlorine;

CA 022~0044 1998-09-24 R4 is halogen, cyano or Cl-C4-alkoxy, in particular chlorine, cyano or Cl-C3-alkoxy, particularly preferably chlorine or cyano, especially chorine;

5 R5 is hydrogen, halogen or Cl-C4-alkoxy, in particular hydrogen, chlorine or methoxy, particularly preferably hydrogen;

R6 in position ais C1-C6-alkoxy or C3-C6-alkenyloxy, where each of these two radicals may carry one or two of the following substituents:
- phenyl which may be unsubstituted or may carry from one to three substituents each selected from the group consisting of halogen, nitro, cyano, Cl-C6-alkyl, Cl-C6-haloalkyl and (Cl-C6-alkoxy)carbonyl, - -CO-R9, -CO-OR9, -CO-SR9 or -CO-N(R9)Rl0, - =NOR20 or - C ( R2l)=N-OR20;
-CY-Rll, -c(Rll)=C(Rl4)-CO-Rl5, -c(Rll)=c(Rl4)-co-N(Rl9) -c(Rll)=c(Rl4)-c(R2l)=N-oR2o or -N(R23)R24;
in particular Cl-C6-alkoxy which carries one or two of the following substituents:
- -CO-OR9, -CO-N(R9)Rl0~ =NOR20 or -C(R2l)=N-OR20;
or C3-C6-alkenyloxy, -CY-Rll, -C(Rll)=C(Rl4)-Co-Rl5, C(Rll)=c(Rl4)_co - N(Rl9) - oR2o~ --c(Rll)=c(Rl4) - c(R2l)=N-oR2o or -N(R23)R24;

R7 is hydrogen, Cl-C6-alkyl, C3-C6-alkenyl, (Cl-C6-alkoxy)-carbonyl-Cl-C6-alkyl or phenyl which may be unsubstituted or may carry from one to three radicals each selected from the group consisting of halogen, nitro, Cl-C6-alkyl, Cl-C6-alkoxy and (Cl-C6-alkyl)carbonyl, in particular Cl-C3-alkyl, C3-C4-alkenyl or (Cl-C3-alkoxy)carbonyl-Cl-C3-alkyl;

R3 is hydrogen, Cl-C3-alkyl, Cl-C3-alkoxy, (Cl-C3-alkoxy)-carbonyl-Cl-C3-alkoxy or C3-C4-alkenyloxy, in particular hydrogen, Cl-C3-alkoxy, (Cl-C3-alkoxy)-carbonyl-Cl-C3-alkoxy or C3-C4-alkenyloxy;

R9 is hydrogen, Cl-C6-alkyl, C3-C6-alkenyl, (Cl-C6-alkoxy)-carbonyl-Cl-C6-alkyl or phenyl which may be unsubstituted or may carry from one to three radicals each selected from the group consisting of halogen, nitro, C1-C6-alkyl, Cl-C6-alkoxy and (Cl-C6-alkyl)carbonyl, CA 022~0044 1998-09-24 in particular Cl-C3-alkyl, C3-C4-alkenyl or (Cl-C3-alkoxy)carbonyl-Cl-C3-alkyl;

R10 is hydrogen, Cl-C3-alkyl, C1-C3-alkoxy, (Cl-C3-alkoxy)-carbonyl-Cl-C3-alkoxy or C3-C4-alkenyloxy, in particular hydrogen, C1-C3-alkoxy, (Cl-C3-alkoxy)-carbonyl-C1-C3-alkoxy or C3-C4-alkenyloxy;

Rl1 is hydrogen or methyl, in particular hydrogen;
R12 and Rl3, independently of one another, are each Cl-C6-alkyl, in particular C1-C3-alkyl or R12 and Rl3 together form a saturated or unsaturated, two- to four-membered carbon chain which may carry an oxo substituent, where the carbon chain may furthermore carry one or two radicals each selected from the group consisting of C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkenyloxy and (C1-C6-alkoxy)carbonyl, in particular a saturated two- or three-membered carbon chain which may be unsubstituted or may carry one or two radicals each selected from the group consisting of C1-C3-alkyl, C2-C4-alkenyl and (C1-C3-alkoxy)carbonyl;
Rl4 is hydrogen, halogen or Cl-C6-alkyl, in particular hydrogen, chlorine or methyl, particularly preferably chlorine;
Rl5 is O-R22, Cl-C4-alkyl, C3- or C4-alkenyl, C3- or C4-alkynyl, Cl-C6-alkyliminoxy or -N(R23)R24, in particular 0-R22 or -N(R23)R24;
R16 is hydrogen, halogen or Cl-C6-alkyl, in particular hydrogen, chlorine or methyl;
35 Rl7 is hydrogen, halogen or Cl-C6-alkyl, in particular hydrogen, chlorine or methyl;

Rl3 is hydrogen, C1-C4-alkyl or (cl-c4-alkoxy)carbonyl~
in particular hydrogen, methyl or (C1-C3-alkoxy)carbonyl;
Rl9 is hydrogen, C1-C3-alkyl or C3- or C4-alkenyl, where the last two groups may each carry one of the following radicals:
chlorine, (Cl-C6-alkyl)carbonyl, (Cl-C6-alkoxy)carbonyl or - (C3-C6-alkenyloxy)carbonyl, or (Cl-C6-alkylamino)carbonyl or di(Cl-C6-alkyl)aminocarbonyl;

CA 022~0044 1998-09-24 .

in particular hydrogen, Cl-C3-alkyl or C3- or C4-alkenyl, where the last two groups may each carry one of the following radicals: chlorine, (Cl-C3-alkoxy)carbonyl or (C3- or C4-alkenyloxy)carbonyl, or (Cl- or c2-alkyl)aminocarbonyl or dimethylaminocarbonyl;

R20 is Cl-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, (Cl-C6-alkyl)-carbonyl-Cl-C6-alkyl, (Cl-C6-alkoxy)carbonyl-Cl-C6-alkyl, (Cl-C6-alkoxy)carbonyl-C2-C6-alkenyl or benzyl, in particular Cl-C4-alkyl, C3- or C4-alkenyl or (Cl-C3-alkoxy)carbonyl-Cl-C3-alkyl;

R2l is hydrogen, methyl, Cl-C6-alkoxy, C3-C6-alkenyloxy or (Cl-C6-alkyl)carbonyloxy, where the 4 last-mentioned radicals may carry one of the following substituents:
(Cl-C6-alkyl)carbonyl, (cl-c6-alkoxy)carbonyl~
(Cl-C6-alkylamino)carbonyl or di(Cl-C6-alkyl)aminocarbonyl, or C3-C6-alkynyloxy, (C2-C6-alkynyl)carbonyloxy, phenoxy or benzoyloxy, where the phenyl rings of the two last-mentioned radicals may be unsubstituted or in turn may carry from one to three substituents each selected from the group consisting of halogen, Cl-C6-alkyl, Cl-C6-haloalkyl and Cl-C6-alkoxy, in particular C3- or C4-alkynyloxy, Cl-C3-alkoxy or C3-C6-alkenyloxy, where the last two radicals may each carry one of the following substituents: (Cl-C3-alkoxy)carbonyl, (Cl-C3-alkyl)aminocarbonyl or dimethylaminocarbonyl;

30 R22 has one of the preferred meanings of Rl9, and is in particular hydrogen, Cl-C3-alkyl or C3-C4-alkenyl, where the last two groups may each carry one of the following radicals: chlorine, (Cl-C3-alkoxy)carbonyl or (C3-C4-alkenyloxy)carbonyl, or (Cl- or C2-alkyl)aminocarbonyl or dimethylaminocarbonyl;

R23 and R24, independently of one another, are each hydrogen, Cl-C4-alkyl, C3-C4-alkenyl, C3-C6-cycloalkyl, (Cl-C6-alkyl)carbonyl, (Cl-C6-alkoxy)carbonyl, (Cl-C6-alkoxy)-carbonyl-Cl-C6-alkyl, Cl-C6-alkylsulfonyl, (Cl-C6-alkoxy)-carbonyl-Cl-C6-alkylsulfonyl or phenylsulfonyl which may be unsubstituted or in turn may furthermore carry from one to three substituents each selected from the group consisting of nitro, halogen, Cl-C6-alkyl, C3-C6-alkenyl, Cl-C6-alkoxy and (Cl-C6-alkoxy)carbonyl, .

CA 022~0044 1998-09-24 -in particular hydrogen, Cl-C3-alkyl, (Cl-C3-alkyl)carbonyl, Cl-C3-alkylsulfonyl or phenylsulfonyl whose phenyl ring carries a halogen, Cl-C3-alkyl or Cl-C3-alkoxy substituent, particularly preferably hydrogen, methyl, ethyl, methylsulfonyl or ethylsulfonyl;

Y is -N(R27)-, where R27 is Cl-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, Cl-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, (Cl-C6-alkyl)carbonyloxy, (Cl-C6-alkyl)carbamoyloxy, (Cl-C6-alkyl)carbonyl-Cl-C6-alkoxy, ~Cl-C6-alkoxy)carbonyl-Cl-C6-alkyl, (Cl-C6-alkoxy)carbonyl-Cl-C6-alkoxy, phenyl or phenyl-Cl-C6-alkoxy where each phenyl ring may be unsubstituted or in turn may furthermore carry from one to three substituents each selected from the group consisting of nitro, halogen, Cl-C6-alkyl, Cl-C6-alkoxy and (Cl-C6-alkoxy)carbonyl, in particular Cl-C6-alkoxy, C3-C6-alkenyloxy, (Cl-C6-alkoxy)carbonyl-Cl-C6-alkoxy or benzyloxy, particularly preferably Cl-C3-alkoxy, C3-C4-alkenyloxy, (Cl-Cg-alkoxy)carbonyl-Cl-C3-alkoxy or benzyloxy;

R6 in position ~
has one of the meanings stated above for R6 and in addition may be 25 -CO-N(Rl9)-OR20, -C(R2l)=N-OR20, -COO-R22 or -CON(R23)R24 in particular -CO-N(Rl9)-OR20 or -C(R2l)=NOR20.
Also preferred are - those compounds I in which R6 is Cl-C4-alkoxy which carries one or two -CO-OR9, -CO-N(R9)Rl0~ =N-OR20 and/or -C(R2l)=N-OR20 groups, - those compounds I, in which R6 is -CY-Rll , - those compounds I in which R6 is -C(Rll)=C(Rl4)-Co-Rl5, - those compounds I in which R6 is -C(Rll)=C(Rl4)-Co-N(Rl9)-oR2o and -- those compounds I, in which R6 is -C(Rll)=C(Rl 4)--C(R21)=N--oR20.

Very generally, those compounds I in which R6 is in position ~ are also preferred.

. . .

CA 022~0044 1998-09-24 The compounds Ia shown in Tables 1 and 2 below (~ I where X is oxygen, Rl is trifluoromethyl, R2 is hydrogen and R3 and R4 are each chlorine) are very particularly preferred:

Table l F3C ~ ~ - CH2 ~ R6 Ia (R6 at ~) H o Cl Cl No. R6 R5 Ia.1 OH H
Ia.2 OCH3 H
Ia.3 oC2Hs H
20 Ia.4 o(n-c3H7) H
Ia.5 OCH(CH3)2 H
Ia.6 o(n-C4Hs) H
Ia.7 O(i-C4Hs) H
25 Ia.8 O(s-C4Hs) H
Ia.9 OC(CH3)3 H
Ia.10 O-cyclopropyl H
I Ia.11 O-cyclobutyl H
; 30 Ia.12 O-cyclopentyl H
Ia.13 O-cyclohexyl H
Ia.14 O-cyclohex-2-enyl H
Ia.15 O-cycloheptyl H
Ia.16 O-cyclooctyl H
Ia.17 OCH2CN H
Ia.18 OCH2CH2CN H
- Ia.19 OCH(CH3)CN H
Ia.20 oC(CH3)2CN H
40 Ia.2l OC(CH3)2CH2cN H
Ia.22 OCH2Cl H
Ia.23 OCH2CH2Cl H
Ia.24 OCH(CH3)CH2Cl H
45 Ia.25 OCH2CF3 H
Ia.26 OCHCl2 H
Ia.27 OCF2Cl H

, CA 022~0044 1998-09-24 No. R6 RS
Ia.28 OCF3 H
Ia.29 OC2F5 H
5 Ia.30 OCF2H H
Ia.31 0CH2-CH=CH2 H
Ia.32 OCH2-CH=CH-CH3 H
Ia.33 OCH2-CH=CH-CO-OC2H5 H
Ia.34 0CH(CH3)-CH=CH2 H
Ia.35 OCH(CH3)-CH=CH-CO-OC2H5 H
Ia.36 OCH2-C(OC2C5)=CH-CO-OC2H5 H
Ia.37 OCH2--C3 CH H
Ia.38 OCH2-C--C-CH3 H
15 Ia.39 OCH(CH3)-C-CH H
Ia.40 OCH(CH3)-C-C-CH20-CO-CH3 H
Ia.41 0CH2CH2-CH=CH2 H
Ia.42 OC(CH3)2-C--CH H
20 Ia.43 oCH2-C-C-Si(CH3)3 H
Ia.44 OCH2-COOH H
Ia.45 OCH(CH3)-COOH H
Ia.46 OCH2-CO-OCH3 H
25 Ia.47 OCH2-CO-OC2H5 H
Ia.48 OCH2-CO-O(n-C3H7) H
Ia.49 0cH2-co-ocH(cH3)2 H
Ia.50 OCH2-CO-OC(CH3)3 H
Ia.51 OCH(CH3)-CO-OCH3 {racemate} H
30 Ia.52 OCH(CH3)-CO-OCH3 {R enantiomer} H
Ia.53 OCH(CH3)-CO-OC2Hs H
Ia.54 OCH(CH3)-CO-O(n-C3H7) H
Ia.55 OcH(cH3)-co-ocH(cH3)2 H
35 Ia.56 0cH2-co-ocH2-cH(cH3)2 H

Ia.57 0CH(CH3)-CO-OCH2-CH(CH3)2 H
Ia.58 0C(CH3)2-CO-Oc2HS H
Ia.59 OCH2-CH=C(CH3)-CO-OC2H5 H
40 Ia.60 OCH(co-oc2Hs)2 H
Ia.61 OCH2-COO-(CH2)2-OCH3 H
Ia.62 OCH2-COO-(CH2)2-OCH3 H
Ia.63 OCH(CH3)-COO-(CH2)2-OCH3 H
Ia.64 OCH(CH3)-COO-(CH2)2-OC2H5 H
Ia.65 OcH2-coNH2 H
Ia.66 OCH2-CONH-CH3 H

.

0050/46725 CA 022~0044 1998-09-24 No. R6 R5 Ia.67 OCH2-CONH-C2H5 H
Ia.68 OCH2-CON(CH3)2 H
5 Ia.69 OCH(CH3)-CONH2 H
Ia.70 OCH(CH3)-CONHCH3 H
Ia.71 OCH(CH3)-CONHC2H5 H
Ia.72 OCH(CH3)-CON(CH3)2 H
Ia.73 OCO-CH3 H
lO Ia.74 OCO-C2H5 H
Ia.75 OCO-CH(CH3)2 H
Ia.76 OCO-(n-C4Hg) H
Ia.77 OCO-cyclopropyl H
15 Ia.78 OCO-cyclopentyl H
Ia.79 OCO-CF3 H
Ia.80 OCO-OCH3 H
Ia.81 OCO-OC2H5 H
20 Ia.82 OCO-OCH(CH3) 2 H
Ia.83 OCO-OCH2-CO-OCH3 H
Ia.84 O-CO-OCH(CH3)-CO-OCH3 H
Ia.85 O-CO-OCH(CH3)-CO-OCH2-CO-OCH3 H
25 Ia.86 O-CO-OCH2-CO-OCH2-CO-OCH3 H
Ia.87 O-CO-OCH2-CH=CH2 H
Ia.88 O-co-N(cH3)2 H
Ia.89 O-CO-N(CH3)-CH2-CO-OCH3 H
Ia.90 O-CO-NH-CH2-CO-OCH3 H
Ia.91 O-CO-NH-CH(CH3)-CO-OCH3 H
Ia.92 o-SO2-CH3 H
Ia.93 OCH2-SCH3 H
Ia.94 O(CH2)2-SCH3 H
35 Ia.95 O(CH2)2--SC2Hs H

Ia.96 O(CH2)2-sO-cH3 H
Ia.97 O(CH2)2-SO2-CH3 H
Ia.98 OCH(CH3)-SO2-CH3 H
40 Ia.99 O(CH2)2-cyclopropyl H
Ia.100 O(CH2)2-cyclopentyl H
Ia.101 O(CH2)2-ON=C(CH3)2 H
Ia.102 O(CH2)3-ON=C(CH3)2 H
Ia.103 O(CH2)2-NO2 H
Ia.104 O(CH2)2-NH2 H
Ia.105 O(CH2)2-NH-CH3 H

CA 022~0044 1998-09-24 '' ' 51 No. R6 R5 Ia.106 O(CH2)2-N(CH3)z H
Ia.107 OCH2-OCH3 H
5 Ia.108 OCH(CH3)-OCH3 H
Ia.109 OCH(CH3)-OC2H5 H
Ia.110 OCH(CH3)CH2-OCH3 H
Ia.111 O(CH2)zOH H
Ia.112 OCH2-OC2H5 H
Ia.113 OCH2COO-(4-acetoxy-tetrahydrofuran-3-yl) H
Ia.114 OCH2OCOCH3 H
Ia.115 OCH2OCOC2H5 H
Ia.116 OCHz-(1,3-dioxolan-2-yl) H
15 Ia.117 OCH2-(1,3-dioxan-2-yl) H
Ia.118 OCH2-C6H5 H
Ia.119 O(CH2)2~C6Hs H
Ia.120 OCH2-(4-Cl-C6H4) H
20 Ia.12l OCH2-(4-CF3-C6H4) H
Ia.122 OCH2-(3-NO2-C6H4) H
Ia.123 OCH2-[2-(COOCH3)C6H4] H
Ia.124 OCH2-[3-(COOCH3)C6H4] H
25 Ia.125 OCH2-[4-(COOCH3)C6H4] H
Ia.126 OCH2-[3-(CH2-C2H5)-isoxazol-5-yl] H
Ia.127 OCH(CH3)CO-OCH2CO-OCH3 H
Ia.128 OCH(CH3)CO-OCH(CH3)CO-OCH3 H
Ia.129 OCH(CH3)CO-OCH2CO-OC2H5 H
3 Ia.130 OCH2CO-OCH2-CO-OCH3 H
Ia.131 OCH2CO-OCH(CH3)-CO-OCH3 H
Ia.132 OCH(CH3)CO-NH-CH2-CO-OCH3 H
Ia.133 OCH(CH3)-CON(CH3)-CH2-CO-OCH3 H
35 Ia.134 OCH(CH3)-CON(OCH3)-CH2-CO-OCH3 H
Ia.135 OCH(CH3)-CONH-CH(CH3)-CO-OCH3 H
Ia.136 OCH(CH3)-CONH-CH[CH(CH3)2]-CO-OCH3 H
Ia.137 OCH(CH3)-CONH-CH2-CO-OC2H5 H
40 Ia.138 OCH2-CONH-CH2-CO-OCH3 H
Ia.139 OCH2-CONH-CH(CH3)-CO-OCH3 H
Ia.140 OCH2-CONH-CH[CH(CH3)2]-OCH3 H
Ia.141 OCH(CH3)-CONH-OCH3 H
Ia.142 OCH2-C(NOCH3)-CO-OCH3 H
Ia.143 OCH(CH3)-C(NOCH3)-CO-OCH3 H
Ia.144 OCH2-C(NOCH3)-CO-OC2H5 H

. .

CA 022~0044 1998-09-24 -No. R6 R5 Ia.145 OCH2-C(NOCH3)-CO-OCH(CH3)2 H
Ia.146 OCH2-C(NOC2H5)-CO-OC2H5 H
5 Ia.147 OCH2-C(NOCH2-CH=CH2)-CO-OC2H5 H
Ia.148 OCH2-C(NOCH2-C6H5)-CO-OC2H5 H
Ia.149 OCH2-C(NOCH3)-CH2-CO-OCH3 H
Ia.150 OCH(CH3)-C(NOCH3)OCH2COCH3 H
Ia.151 OCH(CH3)-C(NOCH3)OCH(CH3)COOCH3 H
Ia.152 OCH(CH3)-C(NOCH3)OCH2-CH=CH2 H
Ia.153 OCH2-C(NOCH3)OCH2CO-OCH3 H
Ia.154 OCH(CH3)-C(NOCH3)-OCH2-CO-OCH3 H
Ia.155 OCH2-C(NOCH3)OCH(CH3)CO-OCH3 H
15 Ia.156 OCH2-C(NOCH3)OCH2-CH=CH2 H
Ia.157 OCH(CH3)-C(NOCH2CH=CH2)OCH2CO-OCH3 H
Ia.158 OCH(CH3)-C(NOCH2CH=CH2)OCH(CH3)CO-OCH3 H
Ia.159 OCH(CH3)-C(NOCH2CH=CH2)OCH2-CH=CH2 H
20 Ia.160 OCH2-C(NOCH2CH=CH2)OCH2-CO-OCH3 H
Ia.161 OCH2-C(NOCH2CH=CH2)OCH(CH3)CO-OCH3 H
Ia.162 OCH2-C(NOCH2CH=CH2)OCH2-CH=CH2 H
Ia.163 OCH(CH3)-C(=NOCH2COOCH3)OCH3 H
25 Ia.164 OCH(CH3)-C[=NOCH(CH3)COOCH3]0CH3 H
Ia.165 OCH2-C(=NOCH2COOCH3)OCH3 H
Ia.166 OCH2-C[=NOCH(CH3)COOCH3]OCH3 H
Ia.167 OCH(CH3)-C(=NOCH2COOCH3)OCH2CO-OCH3 H
Ia.168 OCH(CH3)-C(=NOCH2COOCH3)OCH2-CH=CH2 H
30 Ia.169 OCH2-C(=NOCH2COOCH3)OCH2COOCH3 H
Ia.170 OCH2-C(=NOCH2COOCH3)OCH2CH=CH2 H
Ia.171 OCH2-CO-C(NOCH3)-CO-OCH3 H
Ia.172 OCH2C(NOCH3)-C(NOCH3)-CO-OCH3 H
35 Ia.173 NH2 H
Ia.174 NH-CH3 H
Ia.175 NH-CH(CH3)2 H
Ia.176 N(CH3)2 H
40 Ia.177 NH-SO2CH3 H
Ia.178 NH-CH2CO-OCH3 H
Ia.179 NH-CH(CH3)CO-OCH3 H
Ia.180 NH-SO2CH2CO-OCH3 H
Ia.181 NH-SO2CH(CH3)CO-OCH3 H
45 Ia.182 N(cH3)-so2cH3 H
Ia.183 N(CH3)-CH2CO-OCH3 H

CA 022~0044 1998-09-24 No. R6 R5 Ia.184 N(CH3)-S02CH2CO-OCH3 H
Ia.185 N(CH3)-S02CH(CH3)CO-OCH3 H
5 Ia.186 OCH(CH3)-CO-OCH2-CH=CH2 H
Ia.187 OCH(CH3)-CO-OCH2-CO-OCH2-CH=CH2 H
Ia.188 OCH2-CO-OCH2-CH=CH2 H
Ia.189 OCH2-CO-OCH2-CO-OCH2-CH=CH2 H
Ia.l90 OCH(CH3)-CO-OCH(CH3)-CO-OCH2-CH=CH2 H
Ia.l91 OCH2-CO-OCH(CH3)-CO-OCH2-CH=CH2 H
Ia.192 CH(OCH3)2 H
Ia.193 CH(OC2H5)2 H
Ia.194 1,3-dioxolan-2-yl H
15 Ia.195 1,3-dithiolan-2-yl H
Ia.196 4-methyl-1,3-dithiolan-2-yl H
Ia.197 CH=C(Cl)-CO-OCH3 H
Ia.198 CH=C(Cl)-CO-OC2H5 H
20 Ia.l99 CH=C(Cl)-CO-OCH(CH3) 2 H
Ia.200 CH=C(Cl)-CO-OCH2-CO-OCH3 H
Ia.201 CH=C(Cl)-CO-OCH(CH3)-CO-OCH3 H
Ia.202 CH=C(Cl)-CO-OCH2-CO-OC2H5 H
25 Ia.203 CH=C(Cl)-CO-OCH(CH3)-CO-OC2H5 H
Ia.204 CH=C(Cl)-CO-OCH2-CH=CH2 H
Ia.205 CH=C(Cl)-CONH-CH3 H
Ia.206 CH=C(Cl)-CON(CH3)2 H
Ia.207 CH=C(Cl)-CONH-CH2CO-OCH3 H
30 Ia.208 CH=C(Cl)-CONH-CH(CH3)-CO-OCH3 H
Ia.209 CH=C(Cl)-CON(CH3)-CH2-CO-OCH3 H
Ia.210 CH=C(Cl)-CONH-CH2-CO-OC2H5 H
Ia.211 CH=C(Cl)-CONH-CH[CH(CH3)2]-CO-OCH3 H
35 Ia.212 CH=C(Cl)-CONH-CH2-CH=CH2 H
Ia.213 CH=C(Cl)-CONH-CH(CH3)2 H
Ia.214 CH=C(Cl)-CONH-OCH3 H
Ia.215 CH=C(Cl)-CONH-OCH2CH=CH2 H
40 Ia.216 CH=C(Cl)-CONH-OCH(CH3)2 H
Ia.217 CH=C(Cl)-CONH-OCH2-CO-OCH3 H
Ia.218 CH=C(Cl)-CONH-OCH(CH3)CO-OCH3 H
Ia.219 CH=C(Cl)-CONH-OCH(CH3)CO-OC2H5 H
Ia.220 CH=C(Cl)-CON(CH3)-OCH3 H
Ia.221 CH=C(Cl)-CON(CH2CH=CH2)-OCH3 H
Ia.222 CH=C(Cl)-CON(CH2CH=CH2)-OCH2-CH=CH2 H

. .
, .

CA 022~0044 1998-09-24 -No. R6 R5 Ia.223 CH=C(Cl)-CON(CH3)-CH2-CO-OCH3 H
Ia.224 CH=C(Cl)-C(NOCH3)-OCH2-CO-OCH3 H
5 Ia.225 CH=C(Cl)-C~NOCH2CH=CH2)-OCH2-CO-OCH3 H
Ia.226 CH=C(Cl)-C(NOCH3)-OCH3 H
Ia.227 CH=C(Cl)-C(NOCH3)-OCH(cH3)2 H
Ia.228 CH=C(Cl)-C(NOCH3)-OCH2-CH=CH2 H
Ia.229 CH=C(Cl)-C(NOCH3)-OCH(CH3)-CO-OCH3 H
Ia.230 CH=C(Cl)-C(NOCH3)-OCH2-CON(CH3) 2 H
Ia.231 CH=C(Cl)-C(NOCH2CO-OCH3)-OCH(CH3)CO-OCH3 H
Ia.232 CH=C(Cl)-CH=N-OCH3 H
Ia.233 CH=C(Cl)-CH=N-OC2Hs H
15 Ia.234 CH=C(Cl)-C(CH3)=N-OCH3 H
Ia.235 CH=C(Cl)-C(CH3)=N-OCH2CO-OCH3 H
Ia.236 CH=N-OCH3 H
Ia.237 CH=N-OCH(CH3)CO-OCH3 H
20 Ia-238 CH=N-OCH(CH3)-CON(CH3)2 H
Ia.239 CH=N-OCH(CH3)-CO-OCH2-CO-OCH3 H
Ia.240 CH=N-OCH(CH3)-CO-OCH(CH3)-CO-OCH3 H
Ia.241 CH=N-OCH(CH3)-CONH-CH2CO-OCH3 H
25 Ia.242 CH=N-OCH(CH3)-CONH-CH(CH3)CO-OCH3 H
Ia.243 CH=N-OCH(CH3)-CON(CH3)-CH2CO-OCH3 H
Ia.244 CH=N-OCH2-CON(CH3)-CH2CO-OCH3 H
Ia.245 CH=N-OC2H5 H
Ia.246 CH=N-OCH(CH3)2 H
Ia.247 CO-OCH3 H
Ia.248 CO-OC2H5 H
Ia.249 CONH-CH3 H
Ia.250 CO-OCH2-CO-OCH3 H
35 Ia.251 CO-OCH(CH3)-CO-OCH3 H
Ia.252 CONH-OCH3 H
~ Ia.253 CON(CH3)-OCH3 H
Ia.254 C(OCH3)N-OCH3 H
40 Ia.255 C(OCH3)N-OCH2-CO-OCH3 H
Ia.256 C(OCH3)N-OCH(CH3)-CO-OCH3 H
Ia.257 C(OCH2COOCH3)NOCH3 H
Ia.258 CtOCH(CH3)COOCH3]NOCH3 H
Ia.259 C(OCH2COOCH3)NOCH2-CH=CH2 H
Ia.260 OCH2-CH=N-OCH3 H
Ia.261 OCH2-CH=N-OCH2-CH=CH2 H

, CA 022~0044 1998-09-24 No. R6 R5 Ia.262 OCH2-C(CH3)=N-OCH2-CH=CH2 H
Ia.263 OH NO2 5 Ia.264 OCH3 NO2 Ia.265 OH NH2 Table 2 F3C ~ ~ - CH ~ R5 Ia (R6 at a) H o Cl Cl No. R5 R6 Ia.301 H OCH3 Ia.302 H OC2H5 20 Ia.303 H O(n-C3H7) Ia.304 H OCH(CH3)2 Ia.305 H O(n-C4Hg) Ia.306 H O(i-C4Hs) 25 Ia.307 H O(s-C4Hg) Ia.308 H OC(CH3)3 Ia.309 H O-cyclopropyl Ia.310 H O-cyclobutyl Ia.311 H O-cyclopentyl Ia.312 H O-cyclohexyl Ia.313 H O-cycloheptyl Ia.314 H O-cyclooctyl Ia.315 H OCH2CN
35 Ia.316 H OCH2CH2CN
Ia.317 H OCH(CH3)CN

Ia.318 H OC(CH3)2CN
Ia.319 H OC(CH3)2CH2CN
40 Ia.320 H OCH2Cl Ia.321 H OCH2CH2Cl Ia.322 H OCH(CH3)CH2Cl Ia.323 H OCH2CF3 45 Ia.324 H OCHCl2 Ia.325 H OCF2Cl Ia.326 H OCF3 No. R5 R6 Ia.327 H OC2F5 Ia.328 H OCF2H
5 Ia.329 H OCH2-CH=CH2 Ia.330 H OCH(CH3)-CH=CH2 Ia.331 H OCH2-CH=CH-CH3 Ia.332 H OCH2-C~CH
Ia.333 H OCH(CH3)-C-CH
Ia.334 H OC(CH3)2-C~CH
Ia.335 H OCH2-COOH
Ia.336 H OCH2-CO-OCH3 Ia.337 H OCH2-CO-OC2H5 15 Ia.338 H OCH2-CO-O(n-C3H7) Ia.339 H OCH2-CO-OCH(CH3)2 Ia.340 H OCH(CH3)-CO-OCH3 Ia.341 H OCH(CH3)-CO-OC2H5 20 Ia.342 H OCH(CH3)-CO-O(n-C3H7) Ia.343 H OCH(CH3)-CO-OC(CH3)2 Ia.344 H OCH2-COO-(CH2)2-OCH3 Ia.345 H OCH2-COO-(CH2)2-OCH3 25 Ia.346 H OCH(CH3)-COO-(cH2)2-OcH3 Ia.347 H OCH(CH3)-COO-(CH2)2-OC2H5 Ia.348 H OCH2-CONH2 Ia.349 H OCH2-CONH-CH3 Ia.350 H OCH2-CONH-C2H5 Ia.351 H OCH2-CON(CH3)2 Ia.352 H OCH(CH3)-CONH2 Ia.353 H OCH(CH3)-CONH-CH3 Ia.354 H OCH(CH3)-CONH-C2H5 35 Ia.355 H OCH(CH3)-CON(CH3)2 Ia.356 H OCO-CH3 Ia.357 H OCO-C2H5 Ia.358 H OCO-CH(CH3)2 40 Ia.359 H OCO-(n-C4Hg) Ia.360 H OCO-cyclopropyl Ia.361 H OCO-cyclopentyl Ia.362 H OCO-CF3 Ia.363 H OCO-OCH3 Ia.364 H OCO-OC2H5 Ia.365 H OCO-OCH(CH3)2 CA 022~0044 1998-09-24 -No. R5 R6 Ia.366 H OCO-OCH2-CO-OCH3 Ia.367 H OCO-OCH(CH3)-CO-OCH3 5 Ia.368 H OCO-OCH(CH3)-CO-OCH2-CO-OCH3 Ia.369 H OCO-OCH2-CO-OCH2-CO-OCH3 Ia.370 H OCO-OCH2-CH=CH2 Ia.371 H O-SO2-CH3 Ia.372 H OCH2-SCH3 Ia.373 H O(CH2)2-SCH3 Ia.374 H O(CH2)2-SC2Hs Ia.375 H O(CH2)2-SO-CH3 Ia.376 H O(CH2)2-SO2-CH3 15 Ia.377 H O(CH2)2-SO-C2Hs Ia.378 H O(CH2)2-cyclopropyl Ia.379 H O(CH2)2-cyclopentyl Ia.380 H O(CH2)2-ON=C(CH3)2 20 Ia.38l H O(CH2)3-ON=C(CH3)2 Ia.382 H O(CH2)2-NO2 Ia.383 H O(CH2)2-NH2 Ia.384 H O(CH2)2-NH-CH3 Ia.385 H O(CH2)2-N(CH3)2 Ia.386 H OCH2-OCH3 Ia.387 H OCH(CH3)-OCH3 Ia.388 H OCH(CH3)-OC2Hs Ia.389 H OCH(CH3)CH2-OCH3 30 Ia.390 H O(CH2)2OH
Ia.391 H OCH2-OC2H5 Ia.392 H OCH2COO-(4-acetoxy-tetrahydrofuran-3-yl) Ia.393 H OCH2OCOCH3 35 Ia.394 H OCH2OCOC2H5 Ia.395 H OCH2-C6H5 Ia.396 H O(CH2)2-C6Hs Ia.397 H OCH2-(4-Cl-C6H4) 40 Ia.398 H OCH2-(4-CF3-C6H4) Ia.399 H OCH2-(3-NO2-C6H4) Ia.400 H OCH(CH3)CO-OCH2CO-OCH3 Ia.401 H OCH(CH3)CO-OCH(CH3)CO-OCH3 Ia.402 H OCH(CH3)CO-OCH2CO-OC2H5 Ia.403 H OCH2CO-OCH2CO-OCH3 Ia.404 H OCH2-CO-OCH(CH3)CO-OCH3 . .

0050/46725 CA 022~0044 1998-09-24 No. RS R6 Ia.405 H OCH(CH3)CONH-CH2CO-OCH3 Ia.406 H OCH(CH3)CONH-CH(CH3)CO-OCH3 5 Ia.407 H OCH(CH3)-CONH-CH[CH(CH3)21-CO-OCH3 Ia.408 H OCH(CH3)-CONH-cH2-cO-oc2H5 Ia.409 H OCH2-CONH-CH2-CO-OCH3 Ia.410 H OCH2-CONH-CH(CH3)-CO-OCH3 Ia.411 H OCH2-CONH-CH[CH(CH3)2]-OCH3 Ia.412 H OCH(CH3)-CONH-OCH3 Ia.413 H OCH(CH3)C(NOCH3)OCH2-COCH3 Ia.414 H OcH(cH3)c(NocH3)ocH(cH3)co-ocH3 Ia.415 H OCH(CH3)C(NOCH3)OCH2-CH=CH2 15 Ia.416 H OCH2C(NOCH3)OCH2-CO-OCH3 Ia.417 H OCH2C(NOCH3)OCH(CH3)-CO-OCH3 Ia.418 H OCH2C(NOCH3)OCH2-CH=CH2 Ia.419 H OCH(CH3)C(NOCH2CH=CH2)OCH2-CO-OCH3 20 Ia.420 H OCH(CH3)C(NOCH2CH=CH2)OCH(CH3)-CO-OCH3 Ia.421 H OCH(CH3)C(NOCH2CH=CH2)OCH2-CH=CH2 Ia.422 H OCH2C(NOCH2CH=CH2)OCH2-CO-OCH3 Ia.423 H OCH2C(NOCH2CH=CH2)OCH(CH3)-CO-OCH3 25 Ia.424 H OCH2C(NOCH2CH=CH2)OCH2-CH=CH2 Ia.425 H OCH(CH3)C(=NOCH2COOCH3)OCH3 Ia.426 H OCH(CH3)C[C=NOCH(CH3)COOCH3]OCH3 Ia.427 H OCH2C(=NOCH2COOCH3)OCH3 Ia.428 H OCH2C[=NOCH(CH3)COOCH3]OCH3 30 Ia.429 H OCH(CH3)C(=NOCH2COOCH3)OCH2-CO-OCH3 Ia.430 H OCH(CH3)C(=NOCH2COOCH3)OCH2-CH=CH2 Ia.431 H OCH2C(=NOCH2COOCH3)OCH2-CO-OCH3 Ia.432 H OCH2C(=NOCH2COOCH3)OCH2-CH=CH2 35 Ia.433 H NH2 Ia.434 H NH-CH3 Ia.435 H NH-CH(CH3)2 Ia.436 H N(CH3)2 40 Ia-437 H NH-SO2-CH3 Ia.438 H NH-CH2-CO-OCH3 Ia.439 H NH-CH(CH3)CO-OCH3 Ia.440 H NH-SO2-CH2-CO-OCH3 Ia.441 H NH-SO2-CH(CH3)CO-OCH3 Ia.442 H N(CH3)-SO2-CH3 Ia.443 H N(CH3)-CH2-CO-OCH3 0050/46725 CA 022~0044 1998-09-24 .

No. R5 R6 Ia.444 H N(CH3)-SO2-CH2-CO-OCH3 Ia.44s H N(CH3)-SO2-CH(CH3)-CO-OCH3 5 Ia.446 H CH(OCH3)2 Ia.447 H CH(OC2H3)2 Ia.448 H 1,3-dioxolan-2-yl Ia.449 H 1,3-dithiolan-2-yl Ia.450 H 4-methyl-1,3-dithiolan-2-yl Ia.451 H CH=C(Cl)-CO-OCH3 Ia.452 H CH=C(Cl)-CO-OC2H5 Ia.453 H CH=C(Cl)-CO-OCH(CH3)2 Ia.454 H CH=C(Cl)-CO-OCH2-CO-OCH3 15 Ia.455 H CH=C(Cl)-CO-OCH(CH3)-CO-OCH3 Ia.456 H CH=C(Cl)-CO-OCH2-CO-OC2H5 Ia.457 H CH=C(Cl)-CO-OCH(CH3)-CO-OC2Hs Ia.458 H CH=C(Cl)-CO-OCH2-CH=CH2 20 Ia.4sg H CH=C(Cl)-CONH-CH3 Ia.460 H CH=C(Cl)-CON(CH3)2 Ia.461 H CH=C(Cl)-CONH-CH2-CO-OCH3 Ia.462 H CH=C(Cl)-CONH-CH(CH3)-CO-OCH3 25 Ia.463 H CH=C(Cl)-CON(CH3)-CH2-CO-OCH3 Ia.464 H CH=C(Cl)-CONH-CH2-CO-OC2H5 Ia.465 H CH=C(Cl)-CONH-CH[CH(CH3)2]-CO-OCH3 Ia.466 H CH=C(Cl)-CONH-CH2-CH=CH2 Ia.467 H CH=C(Cl)-CONH-CH(CH3)2 30 Ia.468 H CH=C(Cl)-CONH-OCH3 Ia.469 H CH=C(Cl)-CONH-OCH2-CH=CH2 Ia.470 H CH=C(Cl)-CONH-OCH(cH3)2 Ia.471 H CH=C(Cl)-CONH-OCH2-CO-OCH3 35 Ia.472 H CH=C(Cl)-CONH-OCH(CH3)-CO-OCH3 Ia.473 H CH=C(Cl)-CONH-OCH(CH3)-CO-OC2H5 Ia.474 H CH=C(Cl)-CONICH3)-OCH3 Ia.475 H CH=C(Cl)-CON(CH2CH=CH2)-OCH3 40 Ia-476 H CH=C(Cl)-CON(CH2CH=CH2)-OCH2-CH=CH2 Ia.477 H CH=C(Cl)-CON(CH3)-CH2-CO-OCH3 Ia.478 H CH=C(Cl)-C(NOCH3)-OCH2-CO-OCH3 Ia.479 H CH=C(Cl)-C(NOCH2CH=CH2)-OCH2-CO-OCH3 Ia.480 H CH=C(Cl)-C(NOCH3)-OCH3 Ia.481 H CH=C(Cl)-C(NOCH3)-OCH(CH3)2 Ia.482 H CH=C(Cl)-C(NOCH3)-OCH2-CH=CH2 0050/46725 CA 022~0044 1998-09-24 No. R5 R6 Ia.483 H CH=C(Cl)-C(NOCH3)-OCH(CH3)-CO-OCH3 Ia.484 H CH=C(Cl)-C(NOCH3)-OCH2-CON(CH3)2 5 Ia.485 H CH=C(Cl)-C(NOCH2CO-OCH3)-OCH(CH3)CO-OCH3 Ia.486 H CH=C(Cl)-CH=N-OCH3 Ia.487 H CH=C(Cl)-cH=N-Oc2H5 Ia.488 H CH=C(Cl)-C(CH3)=N-OCH3 Ia.989 H CH=C(Cl)-C(CH3)=N-OCH2CO-OCH3 Ia.490 H CH=N-OCH3 Ia.491 H CH=N-OCH(CH3)-CO-OCH3 Ia.492 H CH=N-OCH(CH3)-CON(CH3) 2 Ia.493 H CH=N-OCH(CH3)-CO-OCH2-CO-OCH3 15 Ia.494 H CH=N-OCH(CH3)-CO-OCH(CH3)-CO-OCH3 Ia.495 H CH=N-OCH(CH3)-CONH-CH2-CO-OCH3 Ia.496 H CH=N-OCH(CH3)-CONH-CH(CH3)-CO-OCH3 Ia.497 H CH=N-OCH(CH3)-CON(CH3)-CH2-CO-OCH3 20 Ia.498 H CH=N-OCH2-CON(CH3)-CH2-CO-OCH3 Ia.499 H CH=N-OC2H5 Ia.500 H CH=N-OCH(CH3) 2 Ia.501 H SCH3 25 Ia.502 H SO-CH3 Ia.503 H ScH(cH3)-cacH
Ia.504 H SCH(CH3)-CO-OCH3 Ia.505 OH CH=CH-CO-OC2H5 Ia.506 OH CH=C(Cl)-CO-OC2H5 30 Ia.507 OCH2CH=CH2 CH=CH-CO-OC2H5 Furthermore, the following substituted l-methyl-3-benzyluracils of formula I are particularly preferred:

- the compounds Ib.1 - Ib.265 and Ib.301 - Ib.507, which differ from the corresponding compounds Ia.l - Ia.265 and Ia.301 -Ia.307 merely in that R4 is methoxy:

N ~ ~ R5;R6 F3C ~ N CH2 ~ Ib H O Cl OCH3 0050/46725 CA 022~0044 1998-09-24 .

- the compounds Ic.l - Ic.262 and Ic.301 - Ic.504, which differ from the corresponding compounds Ia.l - Ia.262 and Ia.301 -Ia.504 merely in that R4 is methoxy and R5 is chlorine:

N ~ y~Cl;R6 F3C ~ CH2 ~ Ic H O Cl OCH3 - the compounds Id.l - Id.262 and Id.301 - Id. 504, which differ from the corresponding compounds Ia.l - Ia.262 and Id.301 - Ia.504 merely in that R5 is methoxy:

N ~ y~ OCH3;R6 F3C ~ ~ N--CH2 ~ Id H O Cl Cl the compounds Ie.l - Ie.262 and Ic.301 - Ia.504, which differ from the corresponding compounds Ia.l - Ia.262 and Ia.301 -25 Ia.504 merely in that R4 and R5 are each methoxy:
H3C~ O
N ~ ~ OCH3; R6 F3C ~ N CH2 ~ =~ Ie 30 H ~ Cl OCH3 - the compounds If.l - If.265 and If.301 - If.507, which differ from the corresponding compounds Ia.l - Ia.265 and Ia.301 Ia.507 merely in that X is sulfur:

F3C ~ ~X CH2 ~ R5;R6 If H S Cl Cl 45 - the compounds Ig.l - Ig.262 and Ig.301 - Ig.504, which differ from the corresponding compounds Ia.l - Ia.262 and Ia.301 -Ia.504 merely in that R5 is chlorine:

0050/46725 CA 022~0044 1998-09-24 . --N ~ y~Cl;R6 F3C ~ N CH2 ~ Ig / ~ / \
H O Cl Cl - the compounds Ih.1 - Ih.262 and Ih.301 - Ih.504, which differ from the corresponding compounds Ia.1 - Ia.262 73and Ia.301 -Ia.504 merely in that R4 is cyano:

F3C ~ ~; CH2 ~ R5,R6 Ih H O Cl CN

The substituted 1-methyl-3-benzyluracils of the formula I are obt~in~hle by different methods, in particular by one of the following processes:

25 Process A) Cyclization of an enaminoester of the formula III or of an enaminocarboxylate of the formula IV in the presence of a base:

\N ~ - NH CH2 ~ R5;R6 Rl--~\ OLl ) ~ R3 R4 ~ se R2 o III ~
I (X = O) H C ~

40 Rl _ ~ NH CH2 ~ R5;R6 R2 ~ R3 R4 IV

0O5O/46725 CA 022~0044 1998-09-24 L1 is low molecular weight alkyl, preferably Cl-C6-alkyl, or phenyl.

As a rule, cyclization is carried out in an inert organic solvent or diluent which is aprotic, for example in an aliphatic or cyclic ether, such as 1,2-dimethoxyethane, tetrahydrofuran or dioxane, in an aromatic, such as benzene or toluene or in a polar solvent, such as dimethylformamide or dimethyl sulfoxide. Mixtures of a polar solvent and a hydrocarbon, such as n-hex~ne, are also suitable. Depen~-ng on the starting compound, water may also be suitable as a diluent.

Preferred bases are alkali metal alcoholates, in particular the sodium alcoholates, alkali metal hydroxides, in particular sodium and potassium hydroxide, alkali metal carbonates, in particular sodium and potassium carbonate, and metal hydrides, in particular sodium hydride. When sodium hydride is used as the base, it is proven advantageous to carry out the reaction in an aliphatic or cyclic ether, in dimethyl formamide or in dimethyl sulfoxide.
In general, from 0.5 to twice the molar amount, based on the amount III or IV, of base is sufficient for successfully carrying out the reaction.
As a rule, the reaction temperature is from -78~C to the boiling point of the respective reaction mixture, in particular from -60 to 60~C.
Usually, the product is obtained as a metal salt, the metal corresponding to the cation of the base used. The salt can be isolated in a manner known per se and purified or, if desired, can be corrected into the free compound III by means of an acid.

Process B) Sulfurization of a l-methyl-3-benzyluracil of the formula I where X is oxygen:~0 I (X = o) Sulfurlzatlo~ I (X = S) The sulfurization is carried out as a rule in an inert solvent or diluent, for example in an aromatic hydrocarbon, such as toluene or the xylenes, in an ether, such as diethyl CA 022~0044 1998-09-24 ether, 1,2-dimethoxyethane or tetrahydrofuran, or in an organic amine, such as pyridine.

Preferably suitable sulfurization reagents are phosphorus(V) sulfide and 2,4-bis(4-methoxyphenyl)-1,3,2,4-dith;~Ai phosphetan-2,4-dithione (Lawesson's reagent).
Usually, from 1 to 5 times the molar amount, based on the starting compound to be sulfurized, is sufficient for a substantially complete reaction.

The reaction temperature is usually from 20 to 200~C, preferably from 40~C to the boiling point of the reaction mixture.

Process C) Methylation of a l-H-3-benzyluracil V in the presence of a base:

H\ ~ O R5;R6 N ~/ RS;R6 Rl ~ \ /N CH2 ~ Rl ~ \ N CH
~ \ ~ Base ~ \ ~
R2 X R3 R4 CH3~ R2 X R3 R4 V
Examples of suitable methylating agents are methyl halides, preferably methyl chloride, iodide or bromide, and dimethyl sulfate, methane sulfonate (methyl mesylate), methyl hen7ene sulfonate, methoxy(p-toluylsulfone) (methyl tosylate), p-bromobenzenesulfonylmethane (methyl brosylate), trifluoromethanesulfonylmethane (methyl triflate) and diazomethane.
As a rule, the reaction is carried out in an inert organic solvent or in an aprotic solvent, for example in an aliphatic or cyclic ether, preferably in 1,2-dimethoxyethane, tetrahydrofuran or dioxane, in an aliphatic ketone, preferably in acetone, in an amide, preferably in dimethylformamide, in a sulfoxide, preferably in dimethyl sulfoxide, in a urea, such as tetramethylurea or 1,3-dimethyltetrahydro-2(lH)-pyrimidinone, in a carboxylate, such as ethyl acetate, or in a halogenated aliphatic or aromatic hydrocarbon, such as dichloromethane or chlorobenzene.

0050/46725 CA 022~0044 1998-09-24 Suitable bases are inorganic bases, for example carbonates, such as sodium carbonate and potassium carbonate, bicarbonates, such as sodium and potassium bicarbonate, and alkali metal hydrides, such as sodium hydride and potassium hydride, and organic bases, for example amines, such as triethylamine, pyridine and N,N-diethylaniline, and alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium -tert-butylate.
The amount of base and methylating agent is preferably in each case from 0.5 to twice the molar amount, based on the amount of starting compound.

In general, the reaction temperature is from 0~C to the boiling point of the reaction mixture, in particular from 0 to 60~C.
The l-H-3-benzyluracils V are in turn obtA;n~hle, for example, by cyclization of en~minoesters VI or enamincarboxylates VII:

\N ~ NH CH2 ~ R5;R6 Rl--~\ OLl 25 ~ R3 R4 R2 o VI
V (X = O) H ~
30\ ~ OLl / ase ~ NH CH2 ~ R5;R6 R2 ~ R3 R4 VII
Regarding the solvent/diluents, bases, ratios and reaction temperature, the statements made under A) are applicable.

If desired, the product V where X is oxygen may be converted into V where X is sulfur according to process B).
A preferred process variant comprises methylating a salt of I, obt~; ne~ from the cyclization of VI or VII according to process A) without isolation from the reaction mixture, which 0050/46725 CA 022~0044 1998-09-24 may still contain excess base, eg. sodium hydride, sodium alcoholate or sodium carbonate.

Process D) 5 Reaction of a l-methyl-6-haloalkyluracil VIII with a benzyl hAl;~e IX in the presence of a base:

Rl ~ N - H + Hal CH2 ~ R5;R6 gaSe VIII IX

Hal is halogen, particularly preferably bromine.
Examples of suitable bases are alkali metal alcoholates, such as sodium methylate, AlkAl; metal carbonates, such as sodium and potassium carbonate, and alkali metal hydrides, such as sodium and potassium hydride.

It is also possible initially to convert VIII by means of a base into the alkali metal salt and then to react this with IX.
Usually, the reaction is carried out in an inert polar solvent or diluent, for example in dimethylformamide or N-methylpyrrolidone, in a sulfoxide, such as dimethyl sulfoxide, in a carboxylate, such as ethyl acetate, in a ketone, such as acetone, or in an ether, such as diethyl ether or tetrahydrofuran.

In general, the reaction temperature is from 0~C to the boiling point of the reaction mixture.
Process E) Ether cleavage of a l-methyl-3-benzyluracil of the formula I
where R5 and/or R6 are unsubstituted or substituted alkoxy, cycloalkoxy, alkenyloxy, alkynyloxy or benzyloxy:

OO50/46725 CA 022~0044 1998-09-24 -H3C\ o H3C\ o N ~/ ~R5;OR N ~/ ~R5;OH
R~ CH2 ~ R6;OR R ~ CH2 ~ ~R6;OH

I (R4 is unsubstituted or substituted Alkyl, Cycloalkyl, Alkenyl, Alkynyl) I ( R4 = H) ORb and ORC are the alcohol radicals defined under R5 and R6, respectively.

The ether cleavage is usually carried out by means of an acid, eg. hydrogen bromide, hydrogen iodide or pyridinium hydrochloride, by means of a Lewis acid, such as aluminum trichloride, tribromide or triiodide, or boron trichloride, tribromide or trifluoride, or iron trichloride, or by means of trimethylsilyl iodide. However, lithium salts, such as lithium chloride, or mixtures of an inorganic iodide and trimethylsilyl chloride may also be used for cleaving the ether bond. In specific cases, for example when R6 is benzyloxy, the bond may also be cleaved under hydrogenating conditions by means of hydrogen in the presence of a hydrogenation catalyst, platinum or palladium on active carbons.
Allyl ethers (where R5 or R6 is allyloxy) may furthe -re be converted into the corresponding phenols in a manner known per se for this purpose, for example by isomerization in the presence of a transition metal catalyst to given the enol ether and cleavage of the latter, preferably under slightly acidic conditions (cf. for example T. Greene and P.G.M. Wutz in Protective Groups in Organic Synthesis, John Wiley & Sons, 2nd Edition, New York 1991, page 42 et seq.).
Usually, the reaction is carried out in an inert solvent or diluent, for example in an aliphatic, cyclic or aromatic hydrocarbon, such as n-pentane, petroleum ether, cyclnheyAne~
benzene, toluene or xylene, an aliphatic or cyclic ether, such as diethyl ether, tert-butyl methyl ether, dimethoxy ethane or tetrahydrofuran, an aliphatic or aromatic halohydrocarbon, such as dichloromethane, chloroform, chlorobenzene, 1,2-dichloroethane or the dichlorobenzenes, an alcohol, such as a methanol, ethanol or tert-butanol, an amide, such as dimethylformamide or N-methylpyrrolidone, or an amine, such as ammonia, or in a mixture of such solvents.

.. _, . . . .

0050/46725 CA 022~0044 1998-09-24 Carrying out the reaction without a solvent may also be advantageous.

With regard to particularly preferred embodiments, reference may be made to Houben-Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag, 4th Edition, Stuttgart 1979, Vol. 6/la/1, page 309 et seq., and to R. C. Larock, Comprehensive Organic Transformations, VCH-Publishers, Weinheim 1989, page 501 et seq., and to the literature cited there.

Process F) Alkylation of a l-methyl-3-benzyluracil of the formula I, where R5 and/or R6 are hydroxyl, in the presence of a base:

Rl N CH2 ~ ~ R65,~OHH
~ <\ Base ~ I(R5/R6= are~-r~ t~.dor t-: :~
R2 X R3 R4 Alkynyioxy) (R5/R6 = OH) The alkylation may be carried out, for example, with the halide, preferably the chloride or bromide, the sulfate, sulfonate, preferably the methanesulfonate (mesylate), benzenesulfonate, p-toluenesulfonate (tosylate), p-bromobenzenesulfonate (brosylate), the trifluoromethanesulfonate (triflate) or the diazo compound of an unsubstituted or substituted AlkAne, cycloAlkAne, haloalkane, alkene or alkine.

Usually, the reaction is carried out in an inert organic solvent, aprotic solvents, for example aliphatic and cyclic ethers, such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, aliphatic ketones, such as acetone, amides, such as dimethylformamide, sulfoxides, such as dimethylsulfoxide, ureas, such as tetramethylurea and 1,3-dimethyltetrahydro-2(lH)-pyrimidinone, carboxylates, such as ethyl acetate. and halogenated aliphatic or aromatic hydrocarbons, such as dichloromethane and chlorobenzene, being particularly suitable.

Suitable bases are both inorganic bases, for example alkali metal carbonates, such as sodium carbonate and potassium carbonate, alkali metal bicarbonates, such as sodium and potassium bicarbonate, and alkali metal hydrides, such as .

0050/46725 CA 022~0044 1998-09-24 .

sodium hydride and potassium hydride, and organic bases, for example amines, such as triethylamine, pyridine and N,N-diethylaniline, and alkali metal alcoholates, such as sodium methylate, sodium ethylate and potassium tert-butylate.

The amount of base and alkylating agent is preferably from 0.5 to twice the molar amount, based on the amount of I where R5/R6 are hydroxyl.
In general, a reaction temperature of from 0~C to the boiling point of the reaction mixture is advisable, in particular from 0 to 60~C.

This method can also be used to prepare compounds I where R4 is Cl-C4-alkoxy from the corresponding hydroxy intermediates.

Process G) 20 Acylation of a l-methyl-3-benzyluracil of the formula I, where R5 and/or R6 are hydroxyl, with a suitable acylating agent:

I (R5/R6 = OH) Acylation I (Rs/~6 ~re (un)Jub-tituted Alkyl-, ~ Alkenyl-, Alkynylc~rbonyloxy) Suitable acylating agents are, for example, the acyl hA~ s, in particular the acyl chlorides, the anhydrides or isocyanates of AlkAne-, cycloAlkAne-, Alkene-, Alk;ne-, phenyl- or phenylAlk~necArboxylic acids. However, the free acids or anhydrides thereof are also suitable, provided that the reaction is then carried out in the presence of a condensing agent, such as carbonyldiimidazole or dicyclohexylcarbodiimide.

As a rule, the reaction is carried out in an inert organic solvent or diluent which is preferably aprotic, for example in an aliphatic or cyclic ether, such as 1,2-dimethoxyethane, tetrahydrofuran or dioxane, an aliphatic ketone, such as acetone, an amide, such as dimethylformamide, a urea, such as tetramethylurea or 1,3-dimethyltetrahydro-2(lH)-pyrimidinone, a carboxylate, such as ethyl acetate, or an Al iph~tic or aromatic halohydrocarbon, such as dichloromethane or chlorobenzene.

. -70With regard to suitable bases, the ratios and the reaction temperature, reference may be made to the statements under process F) .

5 Process H) A substitution of halide by cyanide:

(R3,R4 and/or CN0 I (R3,R4 and/or R5 = Halogen~)) R5 = CN) ~) preferably fluorine, bromine or iodine.

Suitable cyanides are in particular metal cyanides, for example the alkali metal cyanides, such as lithium, sodium and potassium cyanide, the alkali metal cyanides, such as magnesium cyanide, and transition metal cyanides, such as copper cyanide.
Usually, the reaction is carried out in an ether, such as tetrahydrofuran, dioxane or 1,2-dimethoxyethane, or in an aprotic, polar solvent, for example an alkyl nitrile, such as acetonitrile, propionitrile or butyronitrile, an alkyl urea, such as N,N,N~,N'-tetramethylurea, an open-chain or cyclic dialkylamide, such as dimethylformamide, N-methyl-2-pyrrolidone, 1,2-dimethylimidazolidin-2-one or 1,2-dimethyl-3,4,5,6-tetrahydro-2(lH)-pyrimidinone, a dialkyl sulfoxide, such as dimethyl sulfoxide, or in hexamethylphosphorotriamide.
on the basis of the knowledge to date, the presence of a catalyst can have an advantageous effect on the course of the reaction. Useful catalysts are, for example, transition metals and their complexes or salts, for example compounds of coppe~, such as copper(I) chloride, iodide or cyanide, or of nickel, such as bis-triphenylphospine nickel dibromide.

The starting compounds V where R3,R4 and/or R5 are halogen can also be converted into the corresponding compounds V where R3/R4/R5 are CN in a similar manner. However, it is advisable to carry out the reaction in the presence of a base, particular suitable bases being weakly nucleophilic bases, ie. both inorganic bases, for example alkali metal carbonates, such as sodium and potassium carbonate, alkali metal bicarbonates, such as sodium and potassium bicarbonate, or alkali metal hydrides, such as sodium hydride and .

0050/46725 CA 022~0044 1998-09-24 potassium hydride, and organic bases, for example amines, such as triethylamine, pyridine and N,N-diethylaniline.

The ratios are usually not critical. In general, from about 1 to 10 times the amount, based on the amount of starting compound I or V, of cyanide and base is sufficient.

The reaction temperature is usually from 50 to 250~C; in order to increase the selectivity of the reaction, however, it may also be advisable to carry out the reaction at lower temperatures, in particular at about 20~C.

With regard to various embodiments of this reaction, reference may be made to Houben-Weyl, Methoden der Organischen Chemie, Georg Thieme Verlag, 4th Edition, Stuttgart 1985, Vol. E5, page. 1444 et seq., and to the literature stated there.

Process K) 20 Halogenation of a 1-methyl-3-benzyluracil of the formula I where R2 is hydrogen:

H3C\ O H3C\ O
25 Rl ~ N - CH2 ~ R ;R N / ~ R5;R6 H X R3 R4 Halogen X R3 R4 I (R2 = H) I (R2 = Halogen) The halogenation is carried out as a rule in an inert organic solvent or diluent. For example, aliphatic carboxylic acids, such as acetic acid, or chlorinated aliphatic hydrocarbons, such as methylene chloride, chloroform or carbon tetrachloride, are suitable for the chlorination and bromination. Low-boiling aliphatic carboxylic acids, such as acetic acid, are particularly preferred for the iodination.

Elemental chlorine and bromine, respectively, or sulfuryl chloride and sulfuryl bromide, respectively, are particularly suitable for the chlorination and bromination, at a reaction temperature of, preferably, from 0 to 60~C, in particular from 10 to 30~C.

If desired, the chlorination and bromination may be carried out in the presence of an acid acceptor, sodium acetate and tertiary amines, such as triethylamine, dimethylaniline and pyridine being particularly preferred.

A particularly preferred iodinating agent is elemental iodine, in which case the reaction temperature is from 0 to 110~C, preferably from 10 to 30~C.

The iodination takes place particularly advantageously in the presence of a mineral acid, such as fuming nitric acid.
.
The amount of halogenating agent is not critical; usually, an equimolar amount of halogenating agent or an excess of up to about 200 mol%, based on the starting compound (I where R2 is H), is used.

Excess iodine can be removed, for example, by means of saturated aqueous sodium hydrogen sulfite solution after the reaction.
The corresponding intermediates V where R2 is H can also be halogenated by this method.
25 Process L) Substitution of the nitro group at Rs by unsubstituted or substituted alkoxy, cycloalkoxy, alkenyloxy or alkynyloxy:

I (R5 = unsubst./subst.
I (R5 = NO2) ~ Cl-C6-Alkoxy, C3-C6-Cyclo-MORd alkoxy, C3-C6-Alkenyloxy, C3-C6-Alkynyloxy ) V (R5 = unsubst./subst.
V (R5 = NO2~ MORd Cl-C6-Alkoxy, C3-C6-Cyclo-alkoxy, C3-C6 -Alkenyloxy, C3-C6-Alkynyloxy ) The substitution of the nitro group is usually carried out by reacting I or V (R5 = NO2) with an alcoholate MORd, where M is a metal atom, preferably lithium, sodium or potassium, and Rd is unsubstituted or substituted alkoxy, cycloalkoxy, alkenyloxy or alkynyloxy (cf. for example Org. Synth. Coll.
Vol. III, 293).

.

0050/46725 CA 022~0044 1998-09-24 Particularly preferred starting compounds for this type of reaction are compounds V in which R3~ R4 and/or R6 are electron-attracting substituents, such as cyano.

As a rule, the reaction is carried out either in the alcohol HORd, whose alcoholate is used or in an inert organic solvent or diluent, for example in an aromatic hydrocarbon, such as toluene or the xylenes, in an ether, such as diethylether, tetrahydrofuran or 1,2-dimethoxyethane, or in a halogenated hydrocarbon, such as dichloromethane or chlorobenzene.

The reaction temperature i~ in general from 0 to 150~C, preferably from room temperature (about 20~C) to the boiling point of the respective reaction mixture.
The amount of alcoholate is usually not critical; from about 1 to 3 equivalents of alcoholate per mol of I (R5 = N02) or V
(Rs = N02) are preferred.

Compounds I where R6 is unsubstituted or substituted Cl-C6-alkoxy, C3-C6-cycloalkyloxy, C3-C6-alkenyloxy or C3-C6-alkynyloxy are obtained in a similar manner.
Process M) 25 Acetalation of a compound I or V where R6 is -C0-Rll:
I {R6 = C0 Rll} ~
V {R6 = --CO Rll} \
\ + H - ZlR12 / H - z2R13 \or H - Zl(Rl2Rl3)z 7- H

I {R6 = - C(Rl1)(zlz12)(Z2Rl3)}
~ V {R6 = C(Rll)(Zlz12)(z2R13)}

The acetalation is generally carried out in an inert aprotic organic solvent, for example in an aliphatic or cyclic ether, such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran or dioxane, in an aromatic hydrocarbon, such as benzene, toluene, o-, m- or p-xylene or mesitylene, or in a chlorinated hydrocarbon, such as methylene chloride, chloroform or chlorobenzene, unless it is carried out in the absence of a solvent, in an excess of H-ZlRl2, H-Z2Rl3 or H_zl(Rl2Rl3)z2_H.

CA 022~0044 1998-09-24 The resulting water of reaction can be removed from the reaction mixture in a conventional manner, for example by means of water separation.

The acetalation is preferably carried out in the presence of an organic acid, such as p-toluene sulfonic acid, and/or of a Lewis acid, such as tin tetrachloride, tin(II) chloride, iron(III) chloride, tellurium tetrachloride or boron trifluoroetherate, or of a suitable catalyst, such as montmorillonite R lO, the amount of acid usually being from 0.5 to 100 mol%, based on the amount of starting material to be acetalated. - !

The ratios are not critical. For complete conversion, all reactants are used in roughly stoichiometric amounts, but an excess of H-ZlRl2 and H-Z2Rl3 or H-Zl(Rl2Rl3)Z2-H is preferably used.

If the starting materials H-ZlRl2 and H-Z2Rl3 or H-Zl(Rl2Rl3)Z2-H are used simultaneously as diluents, they are present in a relatively large excess.

In general, the reaction is carried out at from -78 to 180~C, preferably from -40 to 150~C.
If product mixtures are obtained, for example when R12 and R13 are not a common radical and ZlRl2 and Z2Rl3 are not identical, these mixtures can, if desired, be purified and separated by methods known per se, such as crystallization and chromatography.

In particular, compounds of the formula I where R6 is -C(Rll)(ZlRl2)(Z2Rl3)~ in which Rl2 and Rl3 are not a common radical and ZlR12 and R2R13 are not identical, can also be prepared by other methods known from the literature (cf. for example Tetrahedron Lett. 32, (l991) 467-470, and the literature cited there).

In some cases, it may also be advantageous to carry out the acetalation via the circuitous route of an acetalation to the dialkyl acetal, preferably dimethyl acetal, and subsequent transacetalation in the presence of a suitable catalyst. The solvents, catalysts and other reaction conditions used for the transacetalation correspond to those stated above for the acetalation.

CA 022~0044 1998-09-24 Process N) Acetal cleavage of a compound I or V where R6 is -C(R1l)(z1R12)(z2R13) I {R6 = - C(R11)(Z1Z12)(Z2R13)} H2Y ~ I (R6 = CY - Rl1) V {R6 = - C(R11)(Z1Z12)(Z2R13)} 2 ~ V (R6 = CY Rll) The acetal cleavage can be carried out without the addition of an acid, in the presence of an acid, for example of a mineral acid, such as hydrochloric acid or sulfuric acid, o~
of an organic carboxylic acid, such as formic acid, acetic acid, oxalic acid or trifluoroacetic acid, in the presence of an acidic ion exchanger, such as Amberlite~ (Trademark of Aldrich) IRl20 or IRC84, or in the presence of a transition metal salt, such as mercury(II) oxide, copper(I) oxide or iron(III) chloride.
Examples of suitable solvents or diluents are aromatics, such as benzene, toluene and o-, m-, p-xylene, aliphatic and cyclic ethers, such as 1,2-dimethoxyethane, diethylether, tetrahydrofuran and dioxane, alcohols such as methanol, ethanol and isopropanol, polar organic solvents, such as dimethylformamide, dimethyl sulfoxide and acetonitrile, ketones, such as acetone and butanone, and water.
The reaction is preferably carried out in the absence of a solvent in an excess of the acid used for the acetal cleavage, formic acid being particularly preferred.

For a complete conversion, the starting materials I or V, where R6 is -C(R11)(Z1R12)(Z2R13), and HzY are used in at least stoichiometric amounts, but an excess of H2Y, of up to about 200 mol% is also possible.

The amount of acid, ion exchanger or transition metal salt is not critical. In general, an amount of up to about 300 mol%, based on the amount of H2Y, is sufficient.
As a rule, the reaction temperature is from -78 to 180~C, preferably from 0~C to the boiling point of the respective diluent.

0050/46725 CA 022~0044 1998-09-24 Further methods which may be used for the preparation of the substituted l-methyl-3-benzyluracils I are described in Houben-Weyl, Methoden der Org. Chemie, 4th Edition, Vol. E3, page 362 et seq.

Process O) Olefination of compounds I {R6 = -CO-R1l}:

10 I {R6 = - CO - R11} ~ Phosphorylide X
Phosphonium salt XI
\ or Phosphonate XII
~ ' V {R6 = CO-- Rll} ~

I or V
{R6 = -C(Rll)=C(R14)-co-Rl5 -C ( Rll ) =C ( R14 ) -CH2-Co-R15 -C(Rll)=C(R14)-C(R16)=C(R17)-Co-R15 -c(Rll)=c(Rl4)-cH(Rl6) - cH(Rl7)-co-Rl5}

The reaction can be carried out with the following phosphorylides Xa to Xd, phosphonium salts XIa to XId and phosphonates XIIa to XIId:
Phosphorylides X:
R3P=C(R14)-Co-R15 Xa, R3P=C(R14)-CH2-Co-R15 Xb, R3P=C(Rl4)-c(Rl6)=c(Rl7)-co-Rl5 Xc, R3P=C(R14)-CH2-CH(R13)-Co-R15 Xd;
Phosphonium salts XI:
R3P~-CH(R14)-Co-R15 Hale XIa, R3P~-CH(R14)-CH2-Co-R15 Hal~ XIb, R3P~CH(R14)-C(R16)=C(R17)-Co-R15 Hale XIc, R3P~)--CH(R14)--CH2--CH(R18)--CO--R1 5 Hale XId;

Phosphonates XII:
(RO)2po-cH(Rl4)-co-Rl 5 XIIa, (Ro)2Po-CH(R14)-CH2-Co-Rl5 XIIb, (Ro)2Po-CH(R14)-C(R16)=C(Rl7)-Co-R1s XIIc, (Ro)2Po-CH(R14)-CH2-CH(R1)8-Co-Rl5 XIId.

Those phosphorylides Xb and Xd, phosphonium salts XIb and XId and phosphonates XIIb and XIId in which R15 is hydrogen, alkyl or cycloalkyl are not very suitable.

0050/46725 CA 022~0044 1998-09-24 The radicals R on the phosphorus may be identical or different and are, for exmaple, branched or straight-chain Cl-C8-alkyl, C5- or C6-cycloalkyl or in particular phenyl which may carry further substituents (inert in the reaction), for example Cl-C4-alkyl, such as methyl, ethyl or tert-butyl, C1-C4-alkoxy, such as methoxy, or halogen (such as fluorine, chlorine or bromine). Unsubstituted phenyl is preferred since the starting material triphenylphosphine used for the preparation of the phosphorylides X and phosphonium salts XI
is particularly economical and furthermore very poorly reactive and readily separable, solid triphenylphosphine o~.ide is fol-med in the reactions.

For example, the methods described in Houben-Weyl, Methoden der Organischen Chemie, Vol. E2, 1982, page 345 et seq., are suitable for the preparation of the phosphonates XII.

Suitable solvents are inert organic solvents, for example aromatics, such as toluene and o-, m- and p-xylene, ethers, such as 1,2-dimethoxyethane, diethyl ether, tetrahydrofuran and dioxane, polar organic solvents, such as dimethylformamide and dimethyl sulfoxide, and alcohols, such as methanol, ethanol and isopropanol.
The olefination of I or V, where R6 is -CO-Rl1, with a phosphonium salt XI or a phosphonate XII, is carried out in the presence of a base, alkali metal alkyls, such as n-butyllithium, alkali metal hydrides and alcoholates, such as sodium hydride, sodium ethylate and potassium tert-butylate, and alkali metal and alkaline earth metal hydroxides, such as calcium hydroxide, are particularly suitable.
For complete conversion, all reactants are used in roughly stoichiometric amounts; however, an excess of base of up to about 10 mol% is preferably used.

In general, the reaction temperature is from -40 to 150~C.

The compounds of the formulae X, XI and XII are known or can be prepared in a known manner (cf. for example Houben-Weyl, Methoden d. Org. Chemie, Vol. E1, page 636 et seq., Georg Thieme Verlag, Stuttgart 1982, Chem. Ber. 95 (1962), 3993, or Houben-Weyl, Methoden d. Org. Chemie, Vol. E2, page 345 et seq., Georg Thieme Verlag, Stuttgart 1982).

0050/46725 CA 022~0044 1998-09-24 A further possibility for the preparation of 1-methyl-3-benzyluracils I where R6 is -C(R1l)=C(R14)-Co-R15 and Rl5 is, in particular, hydrogen, alkyl, alkenyl, haloalkyl, cycloalkyl, phenyl or alkoxyalkyl is the aldol condensation known per se. Conditions suitable for this purpose are described, for example, in Nielsen, Org. React. 16 (1968), 1 et seq.

Other suitable methods for the synthesis of cG...~ounds of the formula I where R6 is -C(R11)=C(R14)-Co-R15, _CH(Rll)_CH(R14)_Co--R15, --c(Rll)=c(Rl4) - cH2 - co - Rl5~
_C(Rll)=c(Rl4)-c(Rl6)=c(Rl7)-~--R15 or--C(Rl1)=C(R14)-CH2-CH(R13)-Co-R15 and Rl4 is hydrogen, cyano, alkoxycarbonyl or alkylcarbonyl are both the Knoevenagel condensation and the Perkin condensation. Suitable conditions are described, for example, in Org. React. 15 1967, 204 et seq. (Knoevenagel)- and Johnson, Org. React. 1 (1942), 210 et seq. (Perkin).

Compounds in which Rl5 is -SR22 or -N(R23)R24 can be prepared, for example in a manner known per se, by converting corre-sponding compounds in which Rl5 is hydroxyl into their acyl halides (halogen instead of R15) and then reacting the prod-ucts with an amine H-N(R23)R24, a thiol H-SR22 or a reactive derivative of these compounds.

Process P) Reaction of compounds I or V {R6 = -CO-Rl1} with amines, hydroxylA~; nes or hydrazines:
I {R6 = CO - R11} H2N - R27~ I {R6 = - C(NR27) - Rl1}

V {R6 = CO-- Rll} H2N-- R27~ V {R6 = C(NR27) Rll}
The reaction is usually carried out in an inert organic solvent or diluent, for example in an aromatic, such as toluene or xylene, in a chlorinated hydrocarbon, such as dichloromethane, chloroform or chlorobenzene, in an ether, such as diethyl ether, 1,2-dimethoxyethane or tetrahydrofuran, in an alcohol, such as methanol or ethanol, or in a mixture of the stated solvents.

If the amines H2N-R27 are present as salts, for example as hydrochlorides or oxalates, it is advisable to add a base, preferably sodium carbonate, potassium carbonate, sodium .. ~ . _ . . . ... , . . . ~ . , .

0050/46725 CA 022~0044 1998-09-24 bicarbonate, triethylamine or pyridine, in order to liberate them.

The resulting water of reaction can, if required, be removed from the reaction mixture by distillation or with the aid of a water separator.

Usually, the reaction temperature is from -30 to 150~C, preferably from 0 to 130~C.
Process Q) Cleavage of compounds I or V where R6 is -C~NR2')-Rl' :
I {R6 = C(NR27) Rll} ~ I {R6 = C0 - Rll}

V {R6 =--C~NR27) Rll} ~ V {R6 = CO Rll}

The cleavage is carried out in the absence of a solvent or in an inert solvent or diluent, with water or with a reactive derivative of water.

The reaction can be carried out hydrolytically or under oxidative conditions, a reaction temperature of from -78 to 180~C, preferably from 0~C to the boiling point of the diluent, being advisable.
Examples of suitable solvents or diluents are aromatics, such as benzene, toluene and o-, m- and p-xylene, chlorinated hydrocarbons, such as dichloromethane, chloroform and chlorobenzene, ethers, such as dialkyl ether, 1,2-dimethoxyethane, tetrahydrofuran and dioxane, alcohols, such as methanol and ethanol, ketones, such as acetone, esters of organic acids, such as ethyl acetate, and water and mixtures of the stated solvents.
Advantageously, the reaction is carried out in the presence of a mineral acid, such as hydrochloric acid, hydrobromic acid or sulfuric acid, of a carboxylic acid, such as acetic acid or trifluoroacetic acid, or of a sulfonic acid, such as p-toluenesulfonic acid.

In order to trap the H2N-R27 ob~; ne~ in the hydrolysis or to remove it from the equilibrium, it may be advantageous to carry out the reaction in the presence of another carbonyl compound, eg. acetone, formaldehyde, glyoxalic acid or phenylglyoxylic acid, preferably formaldehyde, which forms a more stable compound with H2N-R27 than I/V (R6 = CHO).

In the procedure under oxidative conditions, oxidizing agents S such as lead tetraacetate, sodium hypochlorite and hydrogen peroxide are particularly suitable.

If desired, the reaction may additionally be carried out in the presence of a catalyst, such as copper(II) sulfate, titanium tetrachloride and boron trifluoretherate.

The amount of acid, oxidizing agent and catalyst may be varied within wide ranges. Usually, both the amount of acid and the amount of catalyst is from 5 to 200 mol%, and the amount of oxidizing agent is from 25 to 400 mol%, based on the amount of compound to be oxidized; however, they may also be used in a considerably larger excess.

Process R) 20 Reduction of a 3-(cyanobenzyl)uracil:

H3C o N ~ ~ Rs;CN
25 Rl ~ \ N- CH2 y ~ ~ 1. Reduction~ I {R6 = CHO;
~ A 2. Hydrolysis R5 7~ CN}

1. Reduction ~ I {R5 = CHO}
I {R5 = CN} 2. Hydrolysis The reaction is advantageously carried out in an inert organic solvent, for example an aromatic, such as toluene or o-, m- or p-xylene, an aliphatic or cyclic ether, such as diethyl ether, tert-butyl methyl ether, tetrahydrofuran or dioxane, a chlorinated hydrocarbon, such as methylene chloride, chloroform or chlorobenzene, or an organic ' carboxylic acid, such as formic acid.
Examples of suitable reducing agents are hydrogen and metal salts, such as tin(II) chloride, metal hydrides, such as diisobutylaluminum hydride, diisopropylaluminum hydride, lithium trisethoxyaluminum hydride or lithium bisethoxyaluminum hydride or triethylsilane. The use of , ~

0050/46725 CA 022~0044 1998-09-24 diisobutylaluminum hydride, formic acid or hydrogen is preferred.

If desired, the reduction may be carried out in the presence of a catalyst, eg. triethyloxonium tetrafluoroborate or Raney nickel.

If the reaction is carried out in the absence of a diluent in formic acid as the reducing agent, the formic acid may also be present in a relatively large excess.

- The advantageous reaction temperature is dependent on the respective reducing agent but is in general from -78 to 150~C.
Process S) Meerwein alkylation of a diazinium salt XIVb:
H3C o 20 R1 N- CH2 ~ Rs;Re R~ ~ + CH(R11)=C(R14)-Co-Rl ~ Halide XIVa {Re = NH }
XIVb {Re = N2~} I {R6 = -CH(Rll)-CH(Rl4)-Co-Rls;
R14 = Halogen}

The reaction conditions of the Meerwein reaction are known per se to a person skilled in the art (cf. for example ~.P.
Doyle et al., J. Org. Chem. 42 (1977), 2431; G. Theo~oridis et al., J. Heterocyclic Chem. 28 (1991), ô49; C.S.
Rondestvedt Jr., Org. React. 24 (1976), 225 and literature cited there); the reaction of XIVb with XVa is advantageously carried out in a similar manner.

Process T) Metal-catalyst olefin coupling with a phenyl h~ of the formula XV:

O050/46725 CA 022~0044 1998-09-24 H3C o ~ R5; Rf R2 X R3 R4 ~ CH(Rll)=C(R14)-Co-Rls (XVa) CH(R11)=C(Rl4)-CN (XVb) XVI {Rf = Bromine, Iodine, oSo2cF3 }
I {R6 = _c(Rll)=c(Rl4)-co-Rl5 -C(Rll)=C(R14)_CN}

The conditions-of this Heck reaction or reactions similar to a Heck reaction are known per se to a person skilled in the art (cf. for example, Comprehensive Organic Chemistry) and can be applied similarly to the above reaction.

The enaminoesters of the formula III are novel. Their preparation and that of the enaminoesters VI can be carried out by methods known per se, for example by one of the following processes:

Process U) Reaction of a 3-amino-prop-2-enoate X with a benzyl isocyanate XI
in the presence of a base:

25 R;
NH III (where f~~~,R5;R6 Ra = CH3) R1 ~ OLl ~ OCN CH2 y _ ) Base ~
/ ~ R3 R4 VI Ra = H) X XI
Ra is hydrogen or methyl.

The ethyl ester has proven particularly useful to date as the 3-amino-prop-2-enoate IX, but any other esters, preferably the alkyl esters, may also be used.

The reaction is advantageously carried out in the presence of an essentially anhydrous aprotic organic solvent or diluent, for example an aliphatic or cyclic ether, such as diethyl ether, 1,2-dimethoxyethane, tetrahydrofuran or dioxane, an aliphatic or aromatic hydrocarbon, such as n-hexane, benzene, toluene or the xylenes, a halogenated, aliphatic hydrocarbon, such as methylene chloride, chloroform, carbon tetrachloride, 1,2-dichlorethane or chlorobenzene, an aprotic, polar solvent, such as dimethylformamide, hP~Amethylphosphoro-triamide or dimethyl sulfoxide, or a mixture of the stated solvents.

If desired, the reaction may also be carried out in the presence of a metal hydride base, such as sodium or potassium hydride, an alkali metal or Alk~line earth metal alcoholate, such as sodium methylate, sodium ethylate or potassium tert-butylate, or an organic tertiary base, such as triethylamine or pyridine, and the organic base may simultaneously serve as the solvent.
The starting compounds a e advantageously used in stoichiometric amounts, or a small excess of up to about 10 mol% of one or other component is employed. When the reaction is carried out in the absence of a solvent and in the presence of an organic base, it is advisable to use the latter in a larger excess.

Usually, reaction temperature of from -80 to 50~C, particularly from -60 to 30~C, is sufficient.
In a particularly preferred embodiment, the enamino ester obt~;ne~ is converted with excess base directly (ie. in situ) into the corresponding desired product I or V, the purification of which can then be carried out by means of convention separation methods, such as crystallization and chromatography.
Process W) 30 Reaction of a B-ketoester XII with a benzylurea XIII:

O Ra O
Rl ~ OLl + N ~ R5;R6 III (where / ~ H N- CH2 ~ ~~~~' R2 O H / \ VI (where R3 R4Ra = H) XII XIII

The reaction is preferably carried out under essentially anhydrous conditions in an inert solvent or diluent, particularly preferably in the presence of an acidic or basic catalyst.
Particularly suitable solvents or diluents are organic solvents which are miscible with water to form an azeotropic mixture, for example aromatics, such as benzene, toluene and , CA 022~0044 1998-09-24 the xylenes, halogenated hydrocarbons, such as methylene chloride, chloroform, carbon tetrachloride and chlorobenzene, aliphatic and cyclic ethers, such as 1,2-dimethoxyethane, tetrahydrofuran and dioxane, cyclohexAne and alcohols, such as methanol and ethanol.

Preferred acidic catalysts are strong mineral acids, such as sulfuric acid and hydrochloric acid, phosphorus-contA; n; ng acids, such as orthophosphoric acid and polyphosphoric acid, organic acids, such as p-toluenesulfonic acid, and acidic cationic exchangers, such as Amberlyst 15 (Fluka).

Examples of suitable basic catalysts are metal hydrides, such as sodium hydride, and particularly preferably metal alcoholates, such as sodium methylate and ethylate.

Advantageously, the ~-ketoester XII and the benzylurea XIII
are reacted in roughly stoichiometric amounts or the reaction is carried out with a small excess of up to about 10 mol% of one or other component.
Usually, it is suf~icient to use from half to twice the molar amount, based on the amount of one of the starting compounds, of catalyst.
In general, the reaction is carried out at from 60 to 120~C, but preferably at the boiling point of the reaction mixture for rapid removal of water formed.

Process oL2 Ra O
Rl ~ OL + /N ~ ~ R ;RRa = CH3) R H VI (where R3 R4Ra = H) XIV XIII

L2 is Cl-C6-alkyl or phenyl.
This reaction may be carried out in an inert, water-miscible, organic solvent, for example an aliphatic or cyclic ether, such as 1,2-dimethoxyethane, tetrahydrofuran or dioxane, or a lower alcohol, in particular ethanol, the reaction temperature usually being from 50 to 100~C, preferably the boiling point of the reaction mixture.

.. ..

0050/46725 CA 022~0044 1998-09-24 However, the reaction may also be carried out in an aromatic diluent, such as benzene, toluene or the xylenes, in which case it is advisable to add either an acidic catalyst, such as hydrochloric acid or p-toluenesulfonic acid, or a base, for example an alkali metal alcoholate, such as sodium methylate or sodium ethylate. In this process variant too, the reaction temperature is usually from 50 to 100~C, but preferably from 60 to 80~C.
Regarding the ratios, the statements made for method W) are applicable.

The enaminocarboxylates of the formula IV are likewise novel;
they too - and the enaminocarboxylates VII - can be prepared in a 15 manner known per se, for example from a benzylamine of the formula XIV according to the following general equation ~):

O O
20 Rl ~ ~
O O ~ o H
~ R5;R6 \ ~5 ~ ~ R5;R6 XV + H2N--CH2 ~ / ~ ~ R N-- CH2 ~

2 Rl ~ OLl R3 R4 R2 o /3 \R4 XIV / XVII
XVI+ H3C - NH COOLl / ¦ + H2N COOL
~ ~
IV VII
The reaction of XV with XIV is preferably carried out in an anhydrous inert aprotic solvent, for example in a halogenated hydrocarbon, such as methylene chloride, chloroform, carbon tetrachloride or chlorobenzene, an aromatic hydrocarbon, such as benzene, toluene or the xylenes, or an aliphatic or cyclic ether, such as diethyl ether, dibutyl ether, 1,2-dimethoxyethane, tetrahydrofuran or dioxane.

In this reaction (of XV with XIV), the reaction temperature is in general from about 70 to 140~C, in particular from 100 to 120~C.
The reaction of XVI with XIV is an aminolysis, which, as a rule, is carried out either in the absence of a solvent [cf.
for example J. Soc. Dyes Col. 42 (1926), ôl, Ber. 64 (1931), 0050/46725 CA 022~0044 1998-09-24 970; Org. Synth., Coll. Vol. IV, (1963), 80, and J. Am. Chem.
Soc. 70 (1948), 2402] or in an inert anhydrous solvent/diluent, in particular in an aprotic solvent, for example in an aromatic, such as toluene or the xylenes, or a halogenated aromatic, such as chlorobenzene.

Here, it is advisable to carry out the reaction in the presence of a basic catalyst, for example a relatively high-boiling amine [cf. for example Helv. Chim. Acta 11 (1928), 779, and U.S. patent 2,416,738], or of pyridine.

The reaction temperature is preferably from about 20 to 160~C, in particular from 80~C to the boiling point of the reaction mixture or of the basic catalyst.
Advantageously, the starting compounds are reacted in each case in roughly stoichiometric amounts or a small excess of up to about 10 mol% of one or other component is employed.
This reaction is carried out in the presence of a basic catalyst, this is usually used in from half to twice the molar amount, based on the amount of one of the starting materials.

The subsequent reaction of the resulting compounds of the formula XVII with an amine H2N-COOLl or H3C-NH-COOLl is advantageously carried out in a substantially anhydrous solvent/diluent at atmospheric pressure, particularly preferably in the presence of an acidic catalyst.

Particularly suitable solvents/diluents are organic liquids which are miscible with water to form an azeotropic mixture, for example aromatics, such as benzene, toluene and the xylenes, or halogenated hydrocarbons, such as carbon tetrachloride and chlorobenzene.
Particularly suitable catalysts are strong mineral acids, such as sulfuric acid, organic acids, such as p-toluenesulfonic acid, phosphorus-cont~;ning acids, such as orthophosphoric acid and polyphosphoric acid, and acidic cationic exchangers, such as Amberlyst 15 (Fluka).

In general, the reaction temperature is from about 70 to 150~C; for the rapid removal of the resulting water of reaction, however, the reaction is advantageously carried out at the boiling point of the respective reaction mixture.

0050/46725 CA 022~0044 1998-09-24 Unless otherwise stated, all processes described above are advantageously carried out at atmospheric pressure or under the autogenous pressure of the respective reaction mixture.

5 The reaction mixtures are worked up as a rule by methods known per se, for example by dilution of the reaction solution with water and subsequent isolation of the product by means of filtration, crystallization or solvent extraction, or by L~ -val of the solvent, partition of the residue in a mixture of water 10 and a suitable organic solvent and working up of the organic phase to obtain the product.
. .
In the preparation, the substituted 1-methyl-3-benzyluracils I
may be obtA;ne~ as isomer mixtures, which, if desired, can be 15 separated into the pure isomers by the conventional methods, such as crystallization or chromatography, including chromatography over an optically active adsorbate. Pure optically active isomers can advantageously be prepared from corresponding optically active starting materials.
Agriculturally useful salts of the compounds I can be formed by reaction with a base of the corresponding cation, preferably an alkali metal hydroxide or hydride, or by reaction with an acid of the corresponding anion, preferably hydrochloric acid, 25 hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
Salts of I whose metal ion is not an alkali metal ion can also be prepared by double decomposition of the corresponding Alk~Al;
metal salt in a conventional manner, as can ammonium, 30 phosphonium, sulfonium and sulfoxonium salts by means of ammonia or phosphonium, sulfonium or sulfoxonium hydroxides.
The compounds I and their agriculturally useful salts are suitable - both as isomer mixtures and in the form of the pure 35 isomers - as herbicides. Herbicides contA;ning I permit very good control of plant growth on uncultivated areas, particularly at high application rates. In crops such as wheat, rice, corn, soybean and cotton, they act against weeds and grass weeds without significantly damaging the crops. This effect occurs in 40 particular at low application rates.

Depending on the particular application method, the compounds I
or the herbicides contAining them may be used in a further number of crops for eliminating undesirable plants. For example, the 45 following crops are suitable:

0050/46725 CA 022~0044 1998-09-24 Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec. rapa, Brassica napus var. napus, Brassica napus var.
napobrassica, Brassica rapa var. silvestris, Camellia sinensis, 5 Carthamus tinctorius, Carya illinoinensis, Citrus limon, Citrus sinensis, Coffea arabica (Coffea canephora, Coffea liberica), Cucumis sativus, Cynodon dactylon, Daucus carota, Elaeis guineensis, Fragaria vesca, Glycine max, Gossypium hirsutum, (Gossypium arboreum, Gossypium herbaceum, Gossypium vitifolium), 10 Helianthus annuus, Hevea brasiliensis, Hordeum vulgare, Humulus lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, _ycopersicon lycopers,cum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N.rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, 15 Phaseolus vulgaris, Picea abies, Pinus spec., Pisum sativum, Prunus avium, Prunus persica, Pyrus communis, Ribes sylvestre, Ricinus communis, Saccharum officinarum, Secale cereale, Solanum tuberosum, Sorghum bicolor (s. vulgare), Theobroma cacao, Trifolium pratense, Triticum aestivum, Triticum durum, Vicia 20 faba, Vitis vinifera and Zea mays.

The compounds I may also be used in crops which are tolerant to the action of herbicides as a result of breeding, including the use of genetic engineering methods.
Furthermore, the substituted l-methyl-3-benzyluracils I are suitable for the desiccation and/or defoliation of plants.

As desiccants, they are particularly suitable for drying out the 30 above-ground parts of crops, such as potatoes, rape, sunflower and soybean. This permits completely mechanical harvesting of these important crops.

Also of commercial interest is the facilitating of harvesting, 35 which is permitted by concentrated dropping or reduction of the adhesion to the tree in the case of citrus fruits, olives or other species and varieties of pornes, drupes and hard-shelled fruit. The same mechAni~, ie. the promotion of the formation of abscission tissue between fruit or leaf part and shoot part of 40 the plants, is also essential for readily controllable defoliation of crops, in particular cotton.

Furthermore, the shortening of the period in which the individual cotton plants ripen leads to higher fiber quality after 45 harvesting.

0050/46725 CA 022~0044 1998-09-24 The compounds I or the agents contA;ning them can be used, for example, in the form of directly sprayable aqueous solutions, powders, suspensions, including highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, 5 pastes, dusting agents, broadcasting agents or granules, by spraying, nebulizing, dusting, broadcasting or pouring. The application forms depend on the inte~de~ uses; they should in any case ensure very fine distribution of the novel active ingredients.
Suitable inert assistants are essentially mineral oil fractions having a medium to high boiling point, such as kerosine and diesel oil, and coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, for example 15 paraffins, tetrahydronaphthaline, alkylated naphth~1; neS and derivatives thereof, alkylated benzenes and derivatives thereof, alcohols, such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones, such as cyclohex~none, and strongly polar solvents, for example amines, such as N-methylpyrrolidone, and 20 water.

Aqueous application forms can be prepared from emulsion concentrates from suspensions, pastes, wettable powders or water-dispersible granules by adding water. For the preparation 25 of emulsions, pastes or oil dispersions, the substituted l-methyl-3-benzyluracils, as such or dissolved in an oil or solvent, can be homoogenized in water by means of wetting agents, adherents, dispersants or emulsifiers. However, it is also possible to prepare concentrates which consist of active 30 ingredients, wetting agents, adherents, dispersants or emulsifiers and possibly solvent or oil, which are suitable for dilution with water.

Suitable surfactants are the alkali metal, ~lk~s-1ine earth metal 35 and ammonium salts of aromatic sulfonic acids, eg. lignin-, phenol-, naphthaline- and dibutylnaphthalinesulfonic acid, and of fatty acids, alkylsulfonates and alkylarylsulfonates, alkylsulfates, laurylethersulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols and of fatty 40 alcohol glycol ether, condensates of sulfonated naphthaline and its derivatives with for~s1~ehyde, condensates of naphth~s1;ne or of naphthalinesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl-or nonylphenol, alkylphenyl polyglycol ether, tributylphenyl 45 polyglycol ether, alkylaryl polyether alcohols, isotridecyl alcohol, fatty alcohol/ethylene oxide condensates, ethoxylated castor oil, polyoxyethylene alkyl ethers or polyoxypropylene .

alkyl ethers, lauryl alcohol polyglycol ether acetate, sorbitol esters, ligninsulfite waste liquors and methylcellulose.

Powders, broadcasting agents and dusting agents can be prepared 5 by mixing or milling the active ingredients together with a solid carrier.

Granules, for example coated, impregnated and homogeneous granules, can be prepared by binding the active ingredients to lO solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, kieselguhr, calcium sulfate, magnesium sulfate, magnesium oxide, milled plastics, fertilizers, such as ammonium sulfate, ammonium phosphate, ammonium nitrate 15 and ureas, and vegetable products, such as grain flour, bark meal, wood meal and nutshell meal, cellulosic powders and other solid carriers.

The concentrations of the active ingredients I in the 20 ready-to-use formulations may be varied within wide ranges. In general, the formulations contain from about 0,001 to 98, preferably from 0.01 to 95, % by weight of at least one active ingredient. The active ingredients are used in a purity of from 90 to 100 %, preferably from 95 to 100 % (according to the NMR
25 spectrum).
The following formulation examples illustrate the preparation of such formulations:

30 I. 20 parts by weight of compound No. Ia.l are dissolved in a mixture which consists of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of from 8 to 10 mol of ethylene oxide with 1 mol of N-monoethanololeamide, 5 parts by weight of the calcium salt of dodecylhen2enesulfonic acid and 5 parts by weight of the adduct of 40 mol ethylene oxide with 1 mol of castor oil.
By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous ' dispersion which contains 0.02 % by weight of the active ingredient is obtained.

II. 20 parts by weight of compound No. Ia.5 are dissolved in a mixture which consists of 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 7 mol of ethylene oxide with 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol ethylene oxide with 1 mol of castor oil. By 9~
pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion which contains 0.02 % by weight of the active ingredient is obtA i ne~ .

III. 20 parts by weight of active ingredient No. Ia.39 are dissolved in a mixture which consists of 25 parts by weight of cyclohexAnone, 65 parts by weight of a mineral oil fraction boiling within the range from 210 to 280~C and 10 parts by weight of the adduct of 40 mol of ethylene oxide with 1 mol of castor oil. By pouring the solution into 100,000 parts by weight of water and finely distributing it therein, an aqueous dispersion which contains 0.02 % by weight of the active ingredient is obtained.

IV. 20 parts by weight of active ingredient No. Ia.126 are thoroughly mixed with 3 parts by weight of the sodium salt of diisobutylnaphthaline-a-sulfonic acid, 17 parts by weight of the sodium salt of a ligninsulfonic acid obtAine~
from a sulfite waste liquor and 60 parts by weight of silica gel powder, and the mixture is milled in a hammer mill. By finely distributing the mixture in 20,000 parts by weight of water, a spray liquor which contains 0.1 % by weight of the active ingredient is obtAine~.

V. 3 parts by weight of active ingredient No. Ia.131 are mixed with 97 parts by weight of finely divided kaolin. A dusting agent which contains 3 % by weight of the active ingredient is obtained in this manner.

VI. 20 parts by weight of active ingredient No. Ia.144 are thoroughly mixed with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of a fatty alcohol polyglycol ether, 2 parts by weight of sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. A stable oily dispersion is obtained.

40 VII. 1 part by weight of compound No. Ia.146 is dissolved in a mixture which consists of 70 parts by weight of cyclohe~Anone, 20 parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. A stable emulsion concentrate is obtAine~.

-0050/46725 CA 022~0044 1998-09-24 . --VIII. 1 part by weight of compound No. Ia.262 is dissolved in a mixture which consists of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol~ EM 31 (=
nonionic emulsifier based on ethoxylated castor oil; BASF
AG). A stable emulsion concentrate is obtained.

The active ingredients I or the herbicides can be applied by the preemerqence or postemergence method. If the active ingredients are less well tolerated by certain crops, it is possible to use 10 application methods in which the herbicides are sprayed with the aid of the sprayers in such a way that the leaves of the sensitive~r~ps are as far as possible not affected, while the active ingredients reach the leaves of undesirable plants growing underneath or the uncovered soil surface (post-directed, lay-by).
The application rates of active ingredient I are from 0.001 to 3.0, preferably from 0.01 to 1.0 kg/ha of active ingredient (a.i.), depe~ing on the aim of control, the season, the target plants and the state of growth.
In order to broaden the action spectrum and to achieve synergistic effects, the substituted l-methyl-3-benzyluracils I may be mixed with many members of other groups of herbicidal or growth-regulating active ingredients and applied 25 together with them. Examples of suitable components of the mixture are 1,2,4-th; A~; A zoles, 1,3,4-th; A~ iazoles, amides, aminophosphoric acid and derivatives thereof, aminotriazoles, anilides, aryloxy-/hetaryloxyalkanoic acids and derivatives thereof, beonzoic acid and derivatives thereof, 30 benzothiA~;A7inones, 2-(hetaroyl/aroyl)-1,3-cycloheYAnediones, hetaryl-aryl-ketones, benzylisoxazolidinones, meta-CF3-phenyl derivates, carbamates, quinolinecarboxylate acid and derivatives thereof, chloroacetanilides, cyclohex~ne-1,3-dionderivates, diazines, dichloropropionic acid and derivatives thereof, 35 dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and derivatives thereof, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- and 40 hetaryloxypheno~y~-o~ionic esters, phenylacetic acid and derivatives thereof, 2-phenylpropionic acid and derivatives thereof, pyrazoles, phenylpyrazoles, pyridazines, pyridinecarboxylic acid and derivatives thereof, pyrimidyl ethers, sulfonamides, sulfonylueeas, triazines, triazinones, 45 triazolinones, triazolcarboxamides and uracils.

0050/46725 CA 022~0044 1998-09-24 .

It may also be useful to apply the compounds I, alone or in combination with other herbicides, also as a mixture with further crop protection agents, for example with pesticides or agents for controlling phytopathogenic fungi or bacteria. The miscibility 5 with mineral salt solutions which are used for eliminating nutrient and trace element deficiencies is also of interest.
Nonphytotoxic oils and oil concentrates can also be added.

Preparation Examples Example 1 3-(2,3-Dichloro-4-isopropoxybenzyl)-2,4-dioxo-1-methyl-6-tri-fluoromethyl-1,2,3,4-tetrahydropyrimidine (compound No. Ia.5) IS 0.7 g of potassium carbonate and 0.7 g of methyl io~;de were added to a solution of 1.8 g of 3-(2,3-dichloro-4-isopropoxybenzyl)-2,4-dioxo-lH-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine in 50 ml of dimethylformamide at about 20~C, after which stirring was 20 carried out for 18 hours. For working up, 150 ml of ice water were added to the reaction mixture. The desired solid product was then isolated. Yield: 1.4 g; mp.: 167-168~C.
Intermediate 1:
25 2-(2,3-Dichlorophe~oxy)propane 62.9 ml of 2-bromopropane were added dropwise to a mixture of 100 g of 2,3-dichlorophenyl, 92.4 g of potassium carbonate and 400 ml of dimethylformamide. Thereafter, stirring was carried out 30 for 16 hours at about 20OC and then for a further 8 hours at 60~C.
The reaction mixture was filtered and the filtrate was then evaporated down. The residue was taken up in methylene chloride.
The organic phase was washed with water, then dried over sodium sulphate and finally evaporated down. Yield: 102 g (oil;
35 analytically pure).

Intermediate 2:
2-(2,3-Dichloro-4-chloromethylpheno~y)propane 40 Hydrogen chloride gas was passed for 13 hours into a mixture of 228 g of 2-(2,3-dichlorophenoxy)propane, 600 ml of glacial acetic acid and 220 ml of 30 % strength by weight of aqueous formaldehyde solution. Stirring was then carried out for a further 12 hours at about 20~C, after which the solvent was 45 removed. The residue was dissolved in diethyl ether. The ether , CA 022~0044 1998-09-24 phase was washed with water, then dried over sodium sulfate and finally evaporated down. Yield: 254 g (oil; analytically pure).

Intermediate 3:
5 N-(2,3-Dichloro-4-isopropoxybenzyl)-3,4,5,6-tetrahydrophthalimide 12.5 g of 2-(2,3-Dichloro-4-chloromethylphenoxy)propane were added to a solution of 9.26 g of phthalimide potassium in 250 ml of dimethylformamide at 50~C. Heating was then carried out for 3 lO hours at 120~C, after which the mixture was evaporated down. The residue was poured onto water. The product was then extracted from the aqueous phase with methylene chloride. Finally, the organic phase was dried over sodium sulfate and then evaporated down. Yield: 17 g (oil; colorless crystals having a melting point 15 of 103-105~C are obtained on crystallization from petroleum ether).
Intermediate 4:
2-(2,3-Dichloro-4-aminomethylphenoxy)propane 1.75 g of hydrazine hydrate are added to a solution of 6.5 g of N-(2,3-dichloro-4-isopropoxybenzyl)-3,4,5,6-tetrahydrophthalimide in 150 ml of ethanol, after which heating was carried out for 2 hours at 90~C. The reaction mixture was then filtered. Evaporating 25 down the filtrate gave an oil, which was taken up in ethyl acetate. The product was extracted from the resulting solution with dilute hydrochloric acid. Sodium hydroxide solution was then added to the acid solution until the pH reached 10, after which the product was again extracted with ethyl acetate. Finally, the 30 ester phase was dried over sodium sulfate and evaporated down.
Yield: 1.5 g.

Intermediate 5:
2-(2,3-Dichloro-4-isocyanatomethylphenoYy)propane 59 g of diphosgene were added to a solution of 65 g of 2-(2,3-dichloro-4-aminomethylphenoxy)propane in 400 ml of toluene. The mixture was then slowly heated to 110~C. After being stirred for 15 hours at this temperature, the reaction mixture 40 was cooled and evaporated down. Yield: 70 g (oil).

.

0050/46725 CA 022~0044 1998-09-24 Intermediate 6:
3-(2,3-Dichloro-4-isopLo~oxybenzyl)-2,4-dioxo-lH-6-trifluoro-methyl-1,2,3,4-tetrahydlopyLimidine H

F3C <\ , OC2Hs + OCN - CH2 ~ OcH(cH3)2 C-C /~
H O Cl Cl H ~ o F3C ~ N CH2 ~ OcH(cH3) 2 ~ Cl Cl A solution of 15 g of F3C-C(NH2)=CH-CO-OC2H5 in 25 ml of dimethyl-formamide was added dropwise to 3 g of sodium hydride (85%
strength by weight in mineral oil) in 200 ml of tetrahydrofuran at 0~C. After stirring had been carried out for 30 minutes at 0~C, 25 the mixture was cooled to -30~C and a solution of 359 g of 2-(2~3-dichloro-4-isocyanatomethylphenoxy)propane in 25 ml of tetrahydrofuran was slowly added dropwise at this temperature.
The reaction mixture was then warmed up to about 20~C, after which stirring was carried out for a further 2 hours. The solvent was 30 then distilled off. The residue was taken up in 200 ml of ethyl acetate. The ester solution was washed with dilute hydrochloric acid, then dried over sodium sulfate and finally evaporated down.
The oil obt~; ne~ was purified by means of chromatography over silica gel (eluent: methylene chloride). Yield: 13 g.
Example 2 3-(2,3-Dichloro-4-hydroxybenzyl)-2,4-dioxo-1-methyl-6-trifluoro-methyl-1,2,3,4-tetrahydropyrimidine (compound No. Ia.1) 40 0.28 g of boron tribromide was added dropwise to a solution of 0.6 g of 3-(2,3-dichloro-4-isopropoxybenzyl)- 2,4-dioxo-1-methyl -6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine (cf. Example 1) in 15 ml of methylene chloride at about 20~C. After stirring had been carried out for 2 hours, 100 ml of ice water were added to 45 the reaction mixture. Stirring was first carried out for a _ 0050/46725 CA 022~0044 1998-09-24 further 30 minutes before the resulting solid desired product was isolated and dried. Yield: 0.3 g (analytically pure).

Example 3 3-(2,3-Dichloro-4-[1-(methoxycarbonyl)ethoxy]benzyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3-4-tetrahydropyrimidine (compound No. Ia.51) lO 1.3 ml of methyl 2-bromopropionate were added to a solution of 3.6 g of 3-(2,3-dichloro-4-hydroxybenzyl)-2,4-dioxo-1-methyl-- ~6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine in 50 ml of dimethylformamide at about 20~C, after which stirring was carried out for 18 hours. The solvent was then distilled off. The residue 15 was taken up in 50 ml of methylene chloride. The organic phase obtained was first washed twice with water, then dried over sodium sulfate and finally evaporated down. The purification of the crude product obtained was carried out by means of chromato-graphy over silica gel (mobile phase: methylene chloride). Yield:
20 0.7 g of oil.

Example 4 3-[2,3-Dichloro-4-(hydroxycarbonylmethoxy)benzyl]-2,4-dioxo-l-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine 25 (Compound No. Ia.44) 30 ml of trifluoroacetic acid were added to a solution of 3-[2,3-dichloro-4-(tert-butoxycarbonylmethoxy)benzyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine in 30 ml 30 of methylene chloride at about 20~C. Stirring was carried out for 2 hours, after which the solvent was distilled off. 100 ml of water were added to the residue. The desired product was then extracted with three times 50 ml of methylene chloride. The combined organic phases were then furthermore dried over sodium 35 sulfate and finally evaporated down. The purification of the crude product was carried out by dissolution in a small amount of diethyl ether and precipitation by means of petroleum ether.
Yield: 2.5 g; mp.: 140~C (decomposition).

40 Example 5 3-(2,3-Dichloro-4-[1-(methoxycarbonyl)ethoxycarbonylmethoxy]-benzyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydro-pyrimidine (Compound No. Ia.131) 45 A solution of 1 g of 3-[2,3-dichloro-4-(chloroformylmethoxy)-benzyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydro-pyri~i~;ne in 5 ml of toluene was added dropwise to a mixture of OOSO/46725 CA 022~0044 1998-09-24 0.23 g of methyl lactate, 0.25 g of triethylamine and 30 ml of toluene. Stirring was then carried out for 4 hours at about 20~C, after which the reaction mixture was washed with three times 30 ml of water and then dried over sodium sulfate. Finally, it 5 was evaporated down. The residue was dissolved in 10 ml of diethyl ether. The desired product was precipitated from the solution by slowly adding petroleum ether. Yield: 0.4 g;
mp.: 151-153~C.
10 Preintermediate 3-[2,3-Dichloro-4-(chloroformylmethoxy)benzyl]-2,4-dioxo-1-methyl-6-trifLuoromethyi-1,2,3,4-tetrahydropyrimidine 2 drops of dimethylformamide were added to a solution of 15 3-[2,3-dichloro-4-(hydroxycarbonylmethoxy)benzyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine in 50 ml of toluene, after which 0.9 g of thionyl chloride was added drop-wise. Heating was then carried out at the reflux temperature for 4 hours. The reaction mixture was then evaporated down. 22 g of 20 an oil was obtA;ne~ and was further reacted without purification.

Example 6 3-[2,3-Dichloro-4-(1-[N-(methoxycarbonyl)methyl-N-methylamino-carbonyl]ethoxy)benzyl]-2,4-dioxo-1-methyl-6-trifluoromethyl-25 1,2,3,4-tetrahydropyrimidine (Compound No. Ia.133) First 0.69 g of potassium carbonate and then a solution of 1 g of 3-[2,3-dichloro-4-(1-chloroformylethoxy)benzyl]-2,4-dioxo-l-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine (prepared 30 similarly to the intermediate for Example 5) in 5 ml of tetrahy-drofuran were added to a solution of 0.35 g of sarcosine methyl ester hydrochloride in 40 ml of tetrahydrofuran. Stirring was then carried out for 52 hours at about 20~C, after which the solvent was distilled off. The residue was dissolved in 50 ml of 35 methylene chloride. The organic phase obtA;ne~ was first washed with water, then dried over sodium sulfate and finally evaporated down. The purification of the crude product obtA;ne~ was carried out by means of chromatography over silica gel (mobile phase: me-thylene chloride). Yield: 0.27 g of oil.

0050/46725 CA 022~0044 1998-09-24 Example 7 3-(2,3-Dichloro-4-[1-(methoxyaminocarbonyl)ethoxy]benzyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine (Compound No. Ia.141) 2.2 ml of triethylA~;ne were added dropwise to 2.67 g of a 25%
strength by weight solution of methoxyamine hydrochloride in 100 ml of toluene at about 20~C. A solution of 3.4 g of 3-[2,3-dichloro-4-(1-chloroformylethoxy)benzyl]-2,4-dioxo-lO l-methyl-6-trifluoromethyl-1,2,3,4-tetrahydLopylimidine (prepared similarly to the inteL e~;Ate for Example 5) in 10 ml of toluene was then added dropwise to the mixture obta~ned. After stirring had been carried out for 5 hours, the organic phase was separated off, washed with water, then dried over sodium sulfate and 15 finally evaporated down. The purification of the oil obtA;ne~ was carried out by means of chromatography over silica gel (mobile phase: methylene chloride). Yield: 1.1 g; mp. 80~C
(decomposition).

20 Example 8 3-(2~3-Dichloro-4-[l-(methoxycarbonylmethoxy)-l-(methoy;~;no) prop-2-yloxy]benzyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine (Compound No. Ia.154) 25 0.27 g of potassium carbonate was added to a solution of 0.8 g of 3-(2~3-dichloro-4-[l-(methoxyaminocarbonyl)ethoxy]benzyl)-2,4-dioxo-1-methyl-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine in 40 ml of acetone. A solution of 0.20 g of methyl bromoacetate in 5 ml of acetone was then added dropwise to the mixture 30 obtained. Stirring was then carried out for 52 hours at about 20~C, after which the solvent was distilled off. The residue was taken up in 50 ml of methylene chloride. The organic phase obtained was first washed with twice 50 ml of water, was then dried over sodium sulfate and finally evaporated down. The puri-35 fication of the crude product obtained was carried out by meansof chromatography over silica gel (mobile phase: methylene chloride). Yield: 0.2 g of oil.

The physical data of the active ingredients I described above and 40 the further novel compounds prepared in a similar ~nner are shown in Table 3 below:

0050/46725 CA 022~0044 1998-09-24 Table 3 F3C ~ N- CH2 ~ R5;R6 Ia oCl Cl No. mp. [~C]
Ia.l 241-242 Ia.51 oil Ia.57 oil Ia.50 oil Ia.31 oil Ia.33 102-105 Ia.35 oil Ia.44 140 (decomp.) Ia.45 115 (decomp.) Ia.131 151-153 Ia.130 150 Ia.127 oil Ia.133 oil Ia.132 oil Ia.141 80 (decomp.) Ia.134 oil Ia.123 161 Ia.124 190-191 Ia.37 137-140 Ia.142 104-105 Ia.171 oil Ia.14 110-112 Ia.59 160-163 Ia.36 oil Ia.260 135-140 Ia.125 153-154 Ia.146 68-70 Ia.148 130-131 Ia.147 88-90 Ia.261 60-62 Ia.262 83-84 Ia.126 138-140 Ia.39 156-158 0050/46725 CA 022~0044 1998-09-24 No. mp. [~C]
Ia.433 206-207 Ia.173 172-174 Ia.452 107-109 Ia.263 185-187 Ia.41 109-110 Ia.58 oil Ia.43 120-123 Ia.38 138-141 Ia.40 124-125 Ia.60 oil Ia.144 oil Ia.145 oil Ia.116 oil Ia.172 oil Ia.117 150-151 Ia.501 oil Ia.502 108-110 Ia.503 oil Ia.504 93-95 Ia.52 oil Ia.143 135-136 Ia.265 180-182 Ia.507 128-130 Ig.31 105-106 3 Ig.142 oil Ia.506 174-176 Ia.505 215-217 Ig.l 120-121 Ia.2 159-161 Ia.149 oil Ia.247 105-107 Ia.264 131-132 Use examples (herbicidal activity) The herbicidal action of the substituted l-methyl-3-benzyluracils I was demonstrated by the following greenhouse experiments:

0050/46725 CA 022~0044 1998-09-24 The culture vessels used were plastic flowerpots contA;ning loamy sand with about 3.0 % of humus as a substrate. Seeds of the test plants were sown separately according to species.

5 In the preemergence treatment, the active ingredients suspended or emulsified in water were applied directly after sowing, by means of finely distributing nozzles. The vessels were lightly sprinkler-irrigated in order to promote gerr;nAtion and growth and were then covered with transparent plastic covers until the 10 plants had begun to grow. This covering ensures uniform germination of the test plants, unless this has been adversely affected by the active ingredients.

For the postemergence treatment, the test plants were first grown 15 to a height of growth of from 3 to 15 cm, depen~;ng on the form of growth, and were then treated with the active ingredients suspe~ or emulsified in water. For this purpose, the test plants were either directly sown and cultivated in the same vessels or they were first grown separately as seedlings and 20 transplanted into the test vessels a few days before the treatment. The application rate for the postemergence treatment was 7.8 or 3.9 g/ha of a.i. (active ingredient).
The plants were kept at 10 - 25~C or 20 - 35~C, depen~;ng on the 25 species. The test periods ranged from 2 to 4 weeks. During this time, the plants were tended and their reaction to the individual treatments was evaluated.
The evaluation was based on a scale from 0 to 100. 100 means no 30 emergence of the plants or complete destruction of at least the above-ground parts and 0 means no damage or normal course of growth.

The plants used in the greenhouse experiments consist of the 35 following species:
p~ot~ni~l Name Common Name Triticum aestivum winter wheat Abutilon tl,cop~ ~li velvetleaf All~al ' retroflexus redroot pigweed Solanum nigrum black nig~tc~ p 0050/46725 CA 022~0044 1998-09-24 At application rates of 7.8 and 3.9 g/ha of a.i., compound No.
Ia.5 showed a very good and selective herbicidal action against Abutilon theophrasti, Amaranthus retroflexus and Solanum nigrum in wheat in the postemergence method.

Use examples (desiccant/defoliant activity) The test plants used were young 4-leaved cotton plants (without cotyledons) which were grown under greenhouse conditions 10 (relative humidity from 50 to 70 %; day/night temperature 27/20~C).

The leaves of the young cotton plants were sprayed to run off with aqueous formulations of the active ingredients (with the 15 addition of 0.15 % by weight, based on the spray liquor, of the fatty alcohol alkoxylate Plurafac~ LF 7001)). The amount of water applied was equivalent to 1000 l/ha. After 13 days, the number of dropped leaves and the degree of defoliation in % were determined.

No dropping of leaves occurred in the case of the untreated control plants.

45 1) a low-foam, nonionic surfactant from BASF AG

Claims

We claim:-

1. A substituted 1-methyl-3-benzyluracil of the formula I

where:

X is oxygen or sulfur;

R1 is C1-C4-haloalkyl;

R2 is hydrogen or halogen;

R3 is cyano, thiocyanato, halogen, C1-C4-haloalkyl, C1-C4-haloalkoxy or C1-C4-haloalkylthio;

R4 is hydrogen, cyano, thiocyanato, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-haloalkylthio or (C1-C6-alkylamino)carbonyl;

R5 in position .alpha. or .beta. is hydrogen, cyano, nitro, hydroxyl, amino, halogen, C1-C4-alkylamino, which may be substituted by C1-C4-alkyl, (C1-C4-alkyl)carboxyl or (C1-C4-alkoxy)carbonyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C3-C6-alkenyloxy, C3-C6-alkenylthio, C3-C6-alkynyloxy, C3-C6-alkynylthio, (C1-C6-alkyl)carbonyloxy, (C1-C6-alkyl)carbonylthio, (C3-C6-alkenyl)carbonyloxy, (C3-C6-alkenyl)carbonylthio, (C3-C6-alkynyl)carbonyloxy, (C3-C6-alkynyl)carbonylthio, C1-C6-alkylsulfonyloxy or C1-C6-alkylsulfonyl, where each of the last-mentioned 16 radicals may, if desired, carry from one to three substituents, each selected from the group consisting of - halogen, nitro, cyano, hydroxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfynyl, C1-C6-alkylsulfonyl, C1-C6-alkylideneaminoxy, - the phenyl, phenoxy or phenylsulfonyl group which may be unsubstituted or may carry from one to three substituents each selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-alkoxy and C1-C6-haloalkyl, - a 3- to 7-membered heterocyclyl or heterocyclyloxy group which may carry from one to three substitutents each selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and (C1-C6-alkyl)carbonyl, - -CO-R7, -CO-OR7, -CO-SR7, -CO-N(R7)R8, -OCO-R7, -OCO-OR7, -OCO-SR7, -OCO-N(R7)R8 or -N(R7)R8, where R7 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl, (C1-C6-alkoxy)-carbonyl-C1-C6-alkyl, (C3-C6-alkenyloxy)carbonyl-C1-C6-alkyl, phenyl or phenyl-C1-C6-alkyl, where the phenyl group and the phenyl ring of the phenylakyl group may be unsubstituted or may carry from one to three radicals each selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkyl)carbonyl and R8 is hydrogen, hydroxyl, C1-C6-alkyl, C3-C6-cycloalkyl, C1-C6-alkoxy, (C1-C6-alkoxy)carbonyl-C1-C6-alkoxy, C3-C6-alkenyl or C3-C6-alkenyloxy;

or R7 and R3 together with the common nitrogen atom form a 3- to 7-membered heterocyclyl group which may in turn carry from one to three substituents each selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkyl)carbonyl;

R6 in position .alpha., R5 then being in position .beta., is 1) hydroxyl, mercapto, C1-C6-haloalkoxy, C1-C6-haloalkylthio, 2) C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C5-C7-cycloalkenyloxy, C2-C6-alkenylthio, C2-C6-alkynyloxy, C2-C6-alkynylthio, (C1-C6-alkyl)carbonyloxy, (C1-C6-alkyl)carbonylthio, (C1-C6-alkoxy)- carbonyloxy, (C2-C6-alkenyl)carbonyloxy, (C2-C6-alkenyl)carbonylthio, (C2-C6-alkynyl)-carbonyloxy, (C2-C6-alkynyl)carbonylthio, C1-C6-alkylsulfonyl or C1-C6-alkylsulfonyloxy, where each of the last-mentioned 18 radicals may, if desired, carry from one to four substituents each selected from the group consisting of - halogen, nitro, cyano, hydroxyl, C3-C6-cycloalkyl, C1-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkylsulfynyl, C1-C6-alkylsulfonyl, C1-C6-alkylideneaminoxy, - the phenyl, phenoxy or phenylsulfonyl group which may be unsubstituted or may carry from one to three substituents each selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl, - a 3- to 7-membered heterocyclyl or heterocyclyloxy group which may carry from one to three substituents each selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl and (C1-C6-alkyl)carbonyl, - an oxygen atom bonded via a double bond, - a -CO-R9, -CO-OR9, -CO-SR9, -CO-N(R9)R10, -OCO-R9, -OCO-OR9, -OCO-SR9, -OCO-N(R9)R10 or -N(R9)R10, where R9 has one of the meanings of R7 and R10 has one of the meanings of R8, - =N-OR20, -C(R21)=N-OR20 or Si(R30,R31,R32), where R30, R31 and R32, independently of one another, are each C1-C6-alkyl or C2-C6-alkenyl;

3) -CY-R11, -C(R11)(Z1R12)(Z2R13), where Z1 and Z2 are in each case oxygen or sulfur, -C(R11)=C(R14)-CN, -C(R11)=C(R14)-CO-R15, -CH(R11)-CH(R14)-CO-R15, -C(R11)=C(R14)-CH2-CO-R15, -C(R11)=C(R14)-C(R16)=C(R17)-CO-R15, -C(R11)=C(R14)-CH2-CH(R18)-CO-R15, -CO-OR19, -C~C-CO-NH-OR20, -C~C-CO-N(R19)-OR20, -C~C-CS-NH-OR20, -C~C-CS-N(R19)-OR20, -C~C-C(R21)=N-OR20, -C(R11)=C(R14)-CO-NH-OR20, -C(R11)=C(R14)-CO-N(R19)-OR20, -C(R11)=C(R14)-CS-NH-OR20, -C(R11)=C(R14)-CS-N(R19)-OR20, -C(R11)=C(R14)-C(R21)=N-OR20, -N(R23)R24, or where Alk is C1-C3-alkylene which may carry a C1-C6-alkyl substituent;

R11 is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;

R12 and R13, independently of one another, are each C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl or C1-C6-alkoxy-C1-C6-alkyl or R12 and R13 together form a saturated or unsaturated, two- to four-membered carbon chain which may carry an oxosubstituent, where a member of this chain may be replaced by an oxygen, sulfut or nitrogen atom, which is not adjacent to Z1 and Z2 and where the carbon chain may furthermore carry from one to three radicals each selected from the group consisting of cyano, nitro, amino, halogen, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-alkoxy, C2-C6-alkenyloxy, C2-C6-alkynyloxy, C1-C6-haloalkyl, cyano-C1-C6-alkyl, hydroxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyl, C3-C6-alkynyloxy-C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkoxy, carboxyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)carbonyloxy-C1-C6-alkyl and phenyl which in turn may be unsubstituted or may carry from one to three substituents each selected from the group consisting of cyano, nitro, amino, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl, and where one or two members of the carbon chain may-also be part of a three- to seven-membered ring which may contain one or two heteroatoms as ring members, selected from oxygen, sulfur, nitrogen and C1-C6-alkyl-substituted nitrogen, and which, if desired, may in turn carry one or two of the following substituents: cyano, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-alkoxy, cyano-C1-C6-alkyl, C1-C6-haloalkyl and (C1-C6-alkoxy)carbonyl;

R14 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, (C1-C6-alkyl)carbonyl or (C1-C6-alkoxy)-carbonyl;

R15 is hydrogen, O-R22, S-R22, C1-C6-alkyl which may furthermore carry one or two C1-C6-alkoxy substituents, or C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkyliminoxy, -N(R23)R24 or phenyl which may be unsubstituted or may carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl, where R22 has one of the meanings of R19 and R23, R24, independently of one another, are each hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkoxy)carbonyl-C1-C6-alkyl, (C1-C6-alkoxy)-carbonyl-C2-C6-alkenyl, where the alkenyl chain may additionally carry from one to three halogen or cyano radicals, or are each C1-C6-alkylsulfonyl, (C1-C6-alkoxy)carbonyl-C1-C6-alkylsulfonyl, phenyl or phenylsulfonyl, where the two phenyl rings may be unsubstituted or may in turn carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl, or where R23 and R24, together with the common nitrogen atom, form a saturated or unsaturated 4- to 7-membered azaheterocyclic structure which, in addition to carbon ring members, may, if desired, contain one of the following members: -O-, -S-, -N=, -NH- or -N(C1-C6-alkyl)-;

R16 is hydrogen, cyano, halogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, -N(R25)R26, where R25 and R26 have one of the meanings of R23 and R24, or phenyl, which in turn may furthermore carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R17 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, (C1-C6-alkyl)carbonyl or (C1-C6-alkoxy)carbonyl;
R18 is hydrogen, cyano, C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;

R19 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl or C2-C6-alkynyl, where the 4 last-mentioned groups may each carry one or two of the following radicals: cyano, halogen, hydroxyl, hydroxycarbonyl, C1-C6-alkoxy, C1-C6-alkylthio, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkyl)carbonyloxy, (C3-C6-alkenyloxy)carbonyl or a 3- to 7-membered azaheterocyclic structure which is bonded to the nitrogen atom by a carbonyl bridge and, in addition to carbon ring members, may furthermore contain an oxygen or sulfur atom as a ring member;

or (C1-C6-alkyl)carbonyl, (C1-C6-haloalkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkylamino)carbonyl, di(C1-C6-alkyl)aminocarbonyl, C1-C6-alkoximino-C1-C6-alkyl, C3-C6-cycloalkyl, phenyl or phenyl-C1-C6-alkyl, where the phenyl rings may be unsubstituted or may in turn carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;

R20 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, hydroxy-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, cyano-C1-C6-alkyl, (C1-C6-alkyl)carbonyl-C1-C6-alkyl, (C1-C6-alkoxy)carbonyl-C1-C6-alkyl, (C1-C6-alkoxy)carbonyl-C2-C6-alkenyl, (C1-C6-alkyl)carbonyloxy-C1-C6-alkyl or phenyl-C1-C6-alkyl, where the phenyl ring may, if desired, carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;

R21 - is hydrogen, halogen, - C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, (C1-C6-alkyl)carbonyloxy, (C1-C6-haloalkyl)carbonyloxy, C1-C6-alkylsulfonyloxy or C1-C6-haloalkylsulfonyloxy, where the 11 last-mentioned radicals may carry one of the following substituents: hydroxyl, cyano, hydroxycarbonyl, C1-C6-alkoxy, C1-C6-alkylthio, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkylamino)carbonyl, di(C1-C6-alkyl)aminocarbonyl, (C1-C6-alkyl)carbonyloxy, - a 3- to 7-membered azaheterocyclic structure which is bonded to the nitrogen atom by a carbonyl bridge and, in addition to carbon ring members, may also contain an oxygen or sulfur atom as ring member, - (C1-C6-alkyl)carbonyl, (C1-C6-haloalkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkoxy)carbonyloxy, (C1-C6-alkyl)carbonylthio, (C1-C6-haloalkyl)carbonylthio, (C1-C6-alkoxy)carbonylthio, C2-C6-alkenyl, C2-C6-alkenylthio, C3-C6-alkynyl, C3-C6-alkynyloxy, C3-C6-alkynylthio, (C2-C6-alkynyl)carbonyloxy, C3-C6-alkynylsulfonyloxy, C3-C6-cycloalkyl, C3-C6-cycloalkyloxy, C3-C6-cycloalkylthio, (C3-C6-cycloalkyl)carbonyloxy, C3-C6-cycloalkylsulfonyloxy, - phenyl, phenoxy, phenylthio, benzoyloxy, phenylsulfonyloxy, phenyl-C1-C6-alkyl, phenyl-C1-C6-alkoxy, phenyl-C1-C6-alkylthio, phenyl-(C1-C6-alkyl)carbonyloxy or phenyl-(C1-C6-alkyl)sulfonyloxy, where the phenyl rings of the 10 last-mentioned radicals may be unsubstituted or may in turn carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;

Y is oxygen, sulfur or -N(R27)-, where R27 is hydrogen, hydroxyl, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-cycloalkoxy, C5-C7-cycloalkenyloxy, C1-C6-haloalkoxy, C3-C6-haloalkenyloxy, hydroxy-C1-C6-alkoxy, cyano-C1-C6-alkoxy, C3-C6-cycloalkyl-C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkoxy, C1-C6-alkoxy-C3-C6-alkenyloxy, (C1-C6-alkyl)carbonyloxy, (C1-C6-haloalkyl)carbonyloxy, (C1-C6-alkyl)carbamoyloxy, (C1-C6-haloalkyl)carbamoyloxy, (C1-C6-alkyl)carbonyl-C1-C6-alkyl, (C1-C6-alkyl)carbonyl-C1-C6-alkoxy, (C1-C6-alkoxy)carbonyl-C1-C6-alkyl, (C1-C6-alkoxy)carbonyl-C1-C6-alkoxy, C1-C6-alkylthio-C1-C6-alkoxy, di(C1-C6-alkyl)amino-C1-C6-alkoxy, phenyl which in turn may furthermore carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl, phenyl-C1-C6-alkoxy, phenyl-C3-C6-alkenyloxy or phenyl-C3-C6-alkynyloxy, where in each case one or two methylene groups of the carbon chain may be replaced by -O- , -S- or -N(C1-C6-alkyl)- and where each phenyl ring may be unsubstituted or may in turn carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl, heterocyclyl, heterocyclyl-C1-C6-alkoxy, heterocyclyl-C3-C6-alkenyloxy or heterocyclyl-C3-C6-alkynyloxy, where in each case one or two methylene groups of the carbon chains may be replaced by -O- , -S- or -N(C1-C6-alkyl)- and where each heterocyclic structure is three- to 7-membered and may in turn carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl, or -N(R28)R29, where R28 and R29 are each hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, (C1-C6-alkoxy)carbonyl-C1-C6-alkyl, (C1-C6-alkoxy)carbonyl-C2-C6-alkenyl, where the alkenyl chain may additionally carry from one to three halogen or cyano radicals, or is phenyl which may be unsubstituted or may in turn furthermore carry from one to three substituents each selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl, or R28 and R29, together with the common nitrogen atom, form a saturated or unsaturated 4- to 7-membered heterocyclic structure which, in addition to carbon ring members, may if desired furthermore contain one of the following members: -O-, -S-, -N=, -NH- or -N(C1-C6-alkyl)-;

or R6 in position .beta., R5 then being in position .alpha., has one of the meanings stated above for R6 and additionally 4) -CO-N(R19)-OR20, -C(R21)=N-OR20, -C(Z1R12)(Z2R13)OR22, -C(Z1R12)(Z2R13)SR22, -C(Z1R12)(Z2R13)NR23R24, -COO-R22, -COS-R22, -CON(R23)R24, C1-C6-alkylthio-(C1-C6-alkyl)carbonyl or (C1-C6-alkyl)iminoxycarbonyl;

and the agriculturally useful salts and enol ethers of the compounds I.

2. Use of a substituted 1-methyl-3-benzyluracil of the formula I
or of agriculturally usefyl of salts or enol ethers thereof, as claimed in claim 1, as herbicides or for desiccating/defoliating plants.

3. Herbicide containing a herbicidal amount of at least one substituted 1-methyl-3-benzyluracil of the formula I or of an agriculturally useful salt or enol ether of I, as claimed in claim 1, and at least one inert liquid or solid carrier and, if desired, at least one surfactant.

4. A plant desiccant or defoliant, containing an amount, having a desiccant or defoliant action, of at least one substituted 1-methyl-3-benzyluracil of the formula I or of an agriculturally useful salt or enol ether of I, as claimed in claim 1, and at least one inert liquid or solid carrier and, if desired, at least one surfactant.

5. A process for the preparation of a herbicide, wherein a herbicidal amount of at least one substituted 1-methyl-3-benzyluracil of the formula I or of an agriculturally useful salt or enol ether of I, as claimed in claim 1, and at least one inert liquid or solid carrier and, if desired, at least one surfactant are mixed.

6. A process for the preparation of a desiccant or defoliant, wherein an amount, having a desiccant or defoliant action, of at least one substituted 1-methyl-3-benzyluracil of the formula I or of an agriculturally useful salt or enol ether of I, as claimed in claim 1, and at least one inert liquid or solid carrier and, if desired, at least one surfactant are mixed.

7. A method for controlling undesirable plant growth, wherein a herbicidal amount of at least one substituted 1-methyl-3-benzyluracil of the formula I or of an agriculturally useful salt or enol ether of I as claimed in claim 1, is allowed to act on plants or their habitat or on seed.

8. A method for desiccating or defoliating plants, wherein an amount, having a desiccant or defoliant action, of at least one substituted 1-methyl-3-benzyluracil of the formula I or of an agriculturally useful salt of I, as claimed in claim 1, is allowed to act on plants.

9. A method as claimed in claim 8, wherein cotton is treated.

10. A process for the preparation of a substituted 1-methyl-3-benzyluracil of the formula I as claimed in claim 1, where X
is oxygen, wherein an enaminoester of the formula III

or an enaminocarboxylate of the formula IV

where L1 in each case is low molecular weight alkyl or phenyl and R1 to R6 each have the meanings stated in claim 1, is cyclized in the presence of a base.

11. A process for the preparation of a substituted l-methyl-3-benzyluracil of the formula I as claimed in claim 1, wherein a 1-H-3-benzyluracil of the formula V

where R1 to R6 have the meanings stated in claim 1, is methylated.

12. A process for the preparation of a substituted 1-methyl-3-benzyluracil of the formula I as claimed in claim 1, wherein a 1-methyl-6-haloalkyluracil of the formula VIII

in the presence of a base, or an alkali metal salt of VIII, is reacted with a benzyl halide of the formula IX

where Hal is halogen and R3 to R7 each have the meanings stated in claim 1.

13. An enaminoester of the formula III

where L1 is C1-C6-alkyl or phenyl and R1 to R6 each have the meaning stated in claim 1.

14. An enaminocarboxylate of the formula IV

where L1 is C1-C6-alkyl or phenyl and R1 to R6 each have the meanings stated in claim 1.

15. A 1-methyl-6-haloalkyluracil of the formula VIII

where X is oxygen or sulfur, R1 is C1-C4-haloalkyl and R2 is hydrogen or halogen.

16. A compound of the formula VIII as claimed in claim 15, where X is oxygen, R1 is trifluoromethyl and R2 is hydrogen.