CA2377143A1 - Substituted ureas - Google Patents

Abstract

The invention relates to substituted ureas of general formula (Ia) and (Ib), wherein variables X, Z, m, R and RA have the meaning cited in claim 1 and Q represents one of radicals Q1 to Q6: (Q-1), (Q-2), (Q-3), (Q-4), (Q-5), (Q-6 ), wherein R3, R4, R5, R6, R7, R8, R9, Y, Y', T and U have the meaning cited in claim 1. The invention also relates to the utilization of the inventive compounds as herbicides, to agents containing said inventive compounds and t o methods for controlling harmful plants.

Description

Substituted ureas The present invention relates to substituted ureas having a semicarbazide structure in which the hydrazino group is incorporated into a 6-membered saturated heterocycle which has a further heteroatom selected from the group consisting of oxygen and sulfur in a position which is not adjacent to the nitrogen atoms.
Moreover, the invention relates to the use of such substituted ureas as herbicidal compositions comprising these compounds as active substances, and to methods for controlling undesirable vegetation using compounds of this type.
JP 9082-372 describes herbicidally active tetrahydropyridazinecarboxylic acid derivatives and processes for their preparation.
WO 94/10173 and the German Patent Application P 198.29.745.9 describe herbicidally active bicyclic triazolinediones and processes for their preparation.
Surprisingly, it has now been found that substituted ureas of the formula Ia and Ib, as defined below, have particularly good herbicidal action. Furthermore, we have found herbicidal compositions comprising the compounds Ia and Ib and having very good herbicidal action. Moreover, we have found processes for preparing these compositions and methods for controlling undesirable vegetation using the compounds I.
Accordingly, the present invention relates to substituted ureas of the formula Ia and Ib X
~RA~m ~-NH_Q Z~N~~-NH- D
N' ~N ~Nw U ~R ~RA~m R
la Ib in which the variables X, Z, m, R and RA are as defined below:
X is S or O;

Z is O, S, S=O or 502;
m has the value 0, 1, 2 or 3;
R is hydrogen, C(0)ORlp, C(O)SRlo, C(S)ORlo, G(S)SR1~, C02H, CHO, cyano, C(0)NR11R12, C(S)NR11R12, G(O)NHC(O)C1, C(O)NHS(0)2C1, C(O)NHC(0)OR12', C(O)NHS(O)2R12~, C(O)NHS(0)20R12', C(O)R2, P(O}R1(ORl), P(O)(OR1)2, S(O)nR2 where n = 0, 1 or 2, or S02NHR1;
RA is hydroxyl, C02R1, halogen, cyano, C(O)N(R1)2, where the radicals R1 are, if appropriate, different from one another, is OR2, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, COR1, S(O)nRl where n = 0, 1 or 2, or is C(O}SR1;
Q is one of the radicals Q1 to Q6:

~ ~ R4 ~ ~ Ra ~ ~ Ra RS YY N N \ 'Y
URB ~IU'Re Y' in Which Y and Y' independently of one another are 0 or S;
T is a chemical bond or O;
U is a chemical bond, C1-C4-alkylene, O, S, SO or S02;

and the radicals R1 to R3~ are as defined below:
R1 is hydrogen, C1-C6-alkyl, C1-Cs-haloalkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
R2 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, hydroxycarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C3-C6-cycloalkoxy-C1-C6-alkyl, C3-C6-alkenyloxy-Cl-C6-alkyl, C3-C6-alkynyloxy-C1-C6-alkyl, G1-C6-haloalkoxy-C1-C6-alkyl, C3-C6-haloalkenyloxy-C1-C6-alkyl, C3-C6-haloalkynyloxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-thioalkyl, C3-C6-alkenylthio-C1-C6-alkyl, C3-C6-alkynylthio-C1-C6-alkyl, cyano-C1-C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, halo-CZ-C6-alkenyl, C1-C6-alkoxy-C3-C6-alkenyl, C1-C6-haloalkoxy-C3-C6-alkenyl, C1-C6-alkylthio-C3-C6-alkenyl, C3-C6-haloalkynyl, C1-C6-alkoxy-C3-C6-alkynyl, C1-C6-haloalkoxy-C3-C6-alkynyl, C1-C6-alkylthio-C3-C6-alkynyl, C1-C6-alkylcarbonyl, CHR1COR7, CHR1P(O)(OR7)Z, P(O)(OR7)2, CHR1P(S)(OR~)2, CHR1C(O)NR11R12, CHR1C(O)NH2, phenoxy-C1-C6-alkyl or benzyloxy-C1-C6-alkyl, where the benzene rings of the two last-mentioned groups may for their part be substituted by halogen, C1-C4-alkyl or C1-C4-haloalkyl; is benzyl which may be substituted by halogen, C1-C4-alkyl or C1-C4-haloalkyl or is phenyl or pyridyl, each of which may be substituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxy;
R3 is hydrogen or halogen;
R4 is C1-G6-alkyl, C1-C6-haloalkyl, OCH3, SCH3, OCHF2, halogen, cyano or NOZ;

0050/500$0 R5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, Ci-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, Ci-C6-haloalkoxy, C1-C6-haloalkylthio, Ci-C6-alkoxy-(C1-C6-alkyl)carbonyl, Ci-C6-alkylthio-(Ci-C6-alkyl)carbonyl, (C1-C6-alkyl)iminooxycarbonyl, Ci-C6-alkoxy-C1-C6-alkyl, Ci-C6-alkoxyamino-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkylamino-Ci-C6-alkyl, is C1-C6-alkoxy, Ci-C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C2-C6-alkenylthio, C2-C6-alkynyloxy, C2-C6-alkynylthio, (Ci-C6-alkyl)carbonyloxy, (Ci-C6-alkyl)carbonylthio, (Ci-C6-alkoxy)carbonyloxy, (C2-C6-alkenyl)carbonyloxy, (C2-C6-alkenyl)carbonylthio, (C2-C6-alkynyl)carbonyloxy, (C2-C6-alkynyl)carbonylthio, Ci-C6-alkylsulfonyloxy or Ci-C6-alkylsulfonyl, where each of the 17 last-mentioned radicals may, if desired, carry one, two or three substituents selected from the group consisting of:
- halogen, nitro, cyano, hydroxyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-alkylideneaminooxy, oxo, =N-ORi 3 ;
- phenyl, phenoxy or phenylsulfonyl, where the three last-mentioned groups may carry one, two or three substituents selected from the group consisting of halogen, nitro, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and (Ci-C6-alkoxy)carbonyl;
- _C0_Rl4r _C0_OR14, -CO-SR14, -CO-N(R14)-Rl5r _OCO-R14, -OCO-OR14 ~ , -OCO-SR14 ~ , -OCO-N ( R14 ) -R15 r _N ( R14 ) _R15 r and -C(R16)=N-OR13~
C(Zi)-R17, -C(=NRi$)R17, C(R17)(Z2R19)(Z3R20)r C(R17)=C(R21)_CN, C(R17)=C(R21)_C0_R22r -CH(R17)-CH(R21)-COR22, -C(Ri7)=C(R21)_CHZ_CO_R22r -C(R17)=C(R21)_C(R23)=C(R24)_C0_R22r -C(R17)=C(R21)_CHZ_CH(R25)_C0_R22r _C0_OR26, -CO-SR26, -CON(R26)-OR13, -CSC-CO-NHOR13, -CSC-CO-N(R26)-ORl3r -CSC-CS-NH-OR13, -CiC-CS-N(R26)-ORl3r _C(R17)=C(R21)_C0_NHOR13, -C(R17)=C(R21)_C0_N(R26)_0R13r -C ( R17 ) =C ( R21 ) _CS_NHOR13 , -C ( R17 ) =C ( R21 ) _CS_N ( R26 ) _0813 r -C ( R17 ) =C ( R21 ) _C ( R16 ) =N_OR13 r C ( R16 ) =N_OR13 r -CSC-C(Ris)=NOR13, C(Z2R19)(Z3R2o)_OR26~
-C(Z2R19) (Z2R2o)SR26, C(Z2R19) (Z3R20)_N(R27)R28~ _N(R27)-R2B~
-CO-N(RZ7)_RZe or _C(R17)=C(R21)CO-N(R2~)R28; where Zi, Z2, Z3 independently of one another are oxygen or sulfur;

R6 is hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C3-alkoxy-Ci-C3-alkyl, C3-C6-alkenyl, Ci-C3-alkoxy-C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, Ci-C3-alkoxy-C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C~-cycloalkyl, 3- to 7-membered saturated heterocyclyl, where each cycloalkyl and each heterocyclyl ring may contain a carbonyl or thiocarbonyl ring member where each cycloalkyl and heterocyclyl ring may be unsubstituted or may carry one, two, three or four substitutents, selected from the group consisting of cyano, nitro, amino, hydroxyl, halogen, Ci-C4-alkyl, Ci-C4-haloalkyl, Ci-C4-cyanoalkyl, Ci-C4-hydroxyalkyl, Ci-C4-aminoalkyl, Ci-C4-alkoxy, Ci-C4-haloalkoxy, Ci-C4-alkylthio, Ci-C4-haloalkylthio, Ci-C4-alkylsulfinyl, Ci-C4-alkylsulfonyl, Ci-C4-haloalkylsulfonyl, (Ci-C4-alkoxy)carbonyl, (Ci-C4-alkyl)carbonyl, (Ci-C4-haloalkyl)carbonyl, (Ci-C4-alkyl)carbonyloxy, (Ci-C4-haloalkyl)carbonyloxy, di(Ci-C4-alkyl)amino, C3-C6-alkenyl, C3-C6-alkynyl, C3-C4-alkenyloxg, C3-C4-alkenylthio, C3-C4-alkynyloxy and C3-C4-alkynylthio;
R7 is hydrogen, Ci-C6-alkyl, Ci-C6-haloalkyl, C1-C3-alkoxy-Ci-C3-alkyl, C2-C6-cyanoalkyl, C3-C6-alkenyl, C3-C6-alkynyl;
R8 is hydrogen, Ci-C3-alkyl, Ci-C3-haloalkyl or halogen;
R9 is hydrogen, Ci-C3-alkyl, Ci-C3-haloalkyl; or R8 and R9 together are C=O;
R10 is Ci-C15-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C3-Cio-alkynyl, Ci-C6-haloalkyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkylthio-Ci-C6-alkyl, Ci-C6-alkylsulfinyl-Ci-C6-alkyl, Ci-C6-alkylsulfonyl-Ci-C6-alkyl, Ci-C3-alkoxy-Ci-C3-alkoxy-Ci-C3-alkyl, C3-C6-cycloalkyl-C1-C6-alkyl, carboxyl-Ci-C6-alkyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-alkoxycarbonyl-C2-C6-alkenyl, C3-C6-alkenyloxycarbonyl-Ci-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyl, C3-C6-alkynyloxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C3-C6-haloalkenyloxy-C1-C6-alkyl, C3-C6-haloalkynyloxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-thioalkyl, C3-C6-alkenylthio-C1-C6-alkyl, C3-C6-alkynylthio-C1-C6-alkyl, cyano-C1-C6-alkyl, C3-C6-halocyclo-C1-C6-alkyl, halo-C3-C6-alkenyl, C1-C6-alkoxy-C3-C6-alkenyl, C1-C6-haloalkoxy-C3-C6-alkenyl, C1-C6-alkylthio-C3-C6-alkenyl, C3-C6-haloalkynyl, C1-C6-alkoxy-C3-C6-alkynyl, Cl-C6-haloalkoxy-C3-C6-alkynyl, C1-C6-alkylthio-C3-C6-alkynyl, CHR1COR7, CHR1P(0)(OR~)2, P(O)(OR7)2, CHR1P(S)(OR~)y, CHR1C(O)NR11R12, CHR1C(O)NH2, C1-C6-alkyl, which is substituted by phenoxy or benzyloxy, where the benzene rings of the two last-mentioned groups may for their part be substituted by halogen, C1-C4-alkyl or C1-CQ-haloalkyl;
is phenyl, pyridyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzthiazolyl, benzyl, which may carry a divalent substituent, such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, in adjacent positions or which may in each case be mono- to pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, amino, C1-C4-monoalkylarnino, C1-C4-dialkylamino, C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, hydroxyl, nitro or cyano;
R11 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy;
R12 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C2-C6-alkenyl, where the alkenyl chain may additionally carry one to three halogen and/or cyano radicals, are phenyl or benzyl which may carry a divalent substituent, such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, in adjacent positions or which may be mono- to pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, amino, C1-C4-monoalkylamino, C1-C4-dialkylamino, C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, hydroxyl, nitro or cyano or R11 and R1z together with the common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle which, in addition to carbon ring members, may, if desired, contain one of the following members: -0-, -S-, -N=, -NH- or N-(C1-C6-alkyl)-;
R12' is as defined for R12, but excluding hydrogen;
R13 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, in which the phenyl ring may, if desired, carry one, two or three substituents selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R14 is hydrogen, C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl, (C1-C6-alkoxy)carbonyl-CI-C6-alkyl, (C3-C6-alkenyloxy)carbonyl-C1-C6-alkyl, phenyl or phenyl-C1-C6-alkyl, where the phenyl ring of the two last-mentioned groups may be unsubstituted or may carry one, two or three radicals selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkyl)carbonyl;
R14' is as defined for R14, but excluding hydrogen;

R15 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;
R16 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, (C1-C6-alkyl)carbonyloxy, (C1-C6-haloalkyl)carbonyloxy, C1-C6-alkylsulfonyloxy or C1-C6-haloalkylsulfonyloxy, where the 12 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-alkyl)aminocarbonyl, di(C1-C6-alkyl)aminocarbonyl, (C1-C6-alkyl)carbonyloxy., C1-C6-alkoxy-(C1-C6-alkyl)aminocarbonyl;
is (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-alkenyl)carbonyloxy, CZ-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;
is 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 for their part carry one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R17 is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, CZ-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-alkoxy-C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;
R18 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-Cycl~alkenyloxy, C1-C6-haloalkoxy, w-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(Cl-C6-alkyl)amino-C1-C6-alkoxy, -N(R29)R3o, phenyl which for its part may carry one, two or three substituents, in each case selected from the group consisting of cyano, vitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, CZ-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
is phenyl-C1-C6-alkoxy, phenyl-(C1-C6-alkyl), phenyl-C3-C6-alkenyloxy or phenyl-C3-C6-alkynyloxy, where in each case one or two methylene groups of the carbon chains in the four last-mentioned groups may be replaced by -O-, -S- or -N(C1-C6-alkyl)- and where the phenyl rings in the four last-mentioned groups may be unsubstituted or may for their part carry one to three substituents, selected from the group consisting of cyano, vitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
is C3-C~-heterocyclyl, C3-C~-heterocyclyl-C1-C6-alkyl, C3-C7-heterocyclyl-C1-C6-alkoxy, C3-C7-heterocyclyl-C3-C6-alkenyloxy or C3-C7-heterocyclyl-C3-C6-alkynyloxy, where in each case one or two methylene groups of the carbon chains in the four last-mentioned groups may be replaced by -O-, -S- or -N(C1-C6-alkyl)- and where each heterocycle may be saturated, unsaturated or aromatic and is either unsubstituted or for its part carries one to three substituents, selected from the group consisting of cyano, vitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, CZ-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R19, R2o independently of one another are C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl or together are a saturated or unsaturated 2- to 4-membered carbon chain which may carry an oxo substituent, where a member of this chain which is not adjacent/ to t~~e vaiiables Z2 and Z3 may be replaced by -O-, -S-, -N=, -NH- or -N(G1-C6-alkyl)- and where the carbon chain may carry one to three substituents selected from the group consisting of cyano, nitro, amino, halogen, C1-C6-alkyl, C2-C6-alkenyl, C1-C6-alkoxy, 5 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, 10 (C1-C6-alkyl)carbonyloxy-C1-C6-alkyl and phenyl; are unsubstituted or substituted phenyl where the carbon chain may also be substituted by a fused-on or spiro-linked 3- to 7-membered ring which may contain, as ring members, one or two heteroatoms selected from the group consisting of oxygen, sulfur, nitrogen and C1-C6-alkyl-substituted nitrogen and which may for its part, if desired, carry one or two of the following substituents: cyano, C1-C6-alkyl, CZ-C6-alkenyl, C1-C6-alkoxy, cyano-C1-C6-alkyl, C1-C6-haloalkyl and (C1-C6-alkoxy)carbonyl;
Rzl is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, (C1-C6-alkyl)carbonyl or (C1-C6-alkoxy)carbonyl;
R22 is hydrogen, O-R31, S-R31, C1-C6-alkyl which may carry one or two C1-C6-alkoxy substituents, is CZ-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkyliminooxy, -N(R2~)R28 or phenyl which may be unsubstituted or may carry one to three substituents, in each case 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;
R23 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(R27)R2e or phenyl which for its part may carry one to three substituents selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-Cb-haloalkyl, C3-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R24 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, (C1-C6-alkyl)carbonyl or (C1-C6-alkoxy)carbonyl;

R25 is hydrogen, cyano, C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;
R2s~ R31 independently of one another are hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl or CZ-C6-alkynyl, where the 4 last-mentioned groups may in each case 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;
are (C1-C6-haloalkyl)carbonyl, (C1-C6-alkoxy)carbonyl, C1-C6-alkylaminocarbonyl, di(C1-C6-alkyl)aminocarbonyl, C1-C6-alkyloximino-C1-C6-alkyl, C3-C6-cycloalkyl;
are phenyl or phenyl-C1-C6-alkyl, where the phenyl rings may be unsubstituted or may for their part carry one to three substituents, in each case selected from the group consisting of cyano, vitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;
R2~, R28, R29, R3~ independently of one another are hydrogen, C1-C6-alkyl, C3-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, are (C1-C6-alkoxy)carbonyl-C2-C6-alkenyl, where the alkenyl chain may additionally carry one to three halogen and/or cyano radicals, are C1-C6-alkylsulfonyl, (C1-C6-alkoxy)carbonyl-C1-C6-alkylsulfonyl, phenyl or phenylsulfonyl, where the phenyl rings of the two last-mentioned radicals may be unsubstituted or may for their part carry one to three substituents, in each case selected from the group consisting of cyano, vitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl; or R2~ and R28 and/or R29 and R3~ together with the respective common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle 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)-;

0050!50080 and the agriculturally useful salts of the compounds Ia and Ib.
Such compounds are provided by the present invention, except for those compounds of the formula Ia in which Z and X are oxygen, m has the value 0, R is hydrogen and Q is a radical of the formula Q1 where R3 = fluorine and R4 = chlorine and R5 is selected from the group comprising isopropoxy, propargyloxy, allyloxy, benzyloxy and isopropoxycarbonyl, hydroxyiminomethyl, methoxyiminomethyl, CH=NOCH2C02CH3, -CH=N-O-C(CH3)2-COzCH3, propargyloxyiminomethyl, -CH=C(C1)-COZCH3, -CH=C(C1)C02C2H5, -CH=C(C1)-COZ-CHZ-COyCH3, -CH=C(C1)-COZ-CH(CH3)COZCH3, -CH=C(C1)-C02-CH2-C02-tert-butyl, -CH=C(Cl)-C02H, -CH=C(C1)-CONHOCH3, -CH=C(C1)-CONHOCZH5 or -CH=N-O-CH(CH3)-COZCH3;
or Q is a radical of the formula Q1 where R3 = R5 = hydrogen and R5 = chlorine, or Q is a radical of the formula Q1 where R3 = R4 =
chlorine and RS = H, methoxyiminomethyl, -CH=C(Cl)COZH or -CH=C(Cl)-C02C(CH3)3; furthermore excluding compounds of the formula Ia in which Z is oxygen and X is sulfur, m has the value 0, R is hydrogen and Q is a radical of the formula Q4 where R3 =
fluorine, Y = oxygen and T-R~ = propargyl, ally! or 3-(ethoxycarbonyl)prop-2-yl or Q is a radical Q1 where R3 = R4 =
chlorine and R5 = hydrogen.
Depending on the substitution pattern, the compounds of the formulae Ia and Ib can contain one or more chiral centers, in which case they are present as enantiomer or diastereomer mixtures. In the case of compounds Ia and Ib having at least one olefinic radical, E/Z isomers are, if appropriate, also possible.
The invention provides both the pure enantiomers or diastereomers and their mixtures.
Among the agriculturally useful salts, the salts of those cations or the acid addition salts of those acids are particularly suitable whose cations and anions, respectively, do not adversely affect the herbicidal action of the compounds Ia and Ib. Thus, suitable cations are in particular the ions of the alkali metals, preferably lithium, 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 also the ammonium ion which may, if desired, carry one to four C1-C4-alkyl substituents and/or one phenyl or benzyl substituent, preferably diisopropylammonium, tetramethylammonium, tetrabutylammonium, trimethylbenzylammonium, furthermore phosphonium ions, sulfonium ions, preferably .

tri(C1-C4-alkyl)sulfonium, and sulfoxonium ions, preferably tri(C1-C4-alkyl)sulfoxonium.
Anions of useful acid addition salts are primarily chloride, bromide, fluoride, hydrogen sulfate, sulfate, dihydrogen phosphate, hydrogen phosphate, phosphate, nitrate, hydrogen carbonate, carbonate, hexafluorosilicate, hexafluorophosphate, benzoate, and the anions of C1-C4-alkanoic acids, preferably formate, acetate, propionate and butyrate. They can be formed by reacting the compounds of the formulae Ia and Ib with an acid of the corresponding anion, preferably of hydrochloric acid, hydrobromic acid, sulfuric acid, phosphoric acid or nitric acid.
The organic molecular moieties mentioned in the definitions of R1 to R2, R4 to R31 and on phenyl, cycloalkyl and heterocyclyl rings are collective terms for individual enumerations of the individual group members. All carbon chains, i.e. all (unsubstituted or substituted) alkyl, alkenyl or alkynyl moieties can be straight-chain or branched.
Halogenated substituents preferably carry one to five identical or different halogen atoms.
The term halogen denotes in each case fluorine, bromine, chlorine or iodine, in particular fluorine or chlorine.
Examples of other meanings are:
- C1-C4-alkyl: CH3, CZHS, n-propyl, CH(CH3)2, n-butyl, CH(CH3)-C2H5, 2-methylpropyl or C(CH3)3, in particular CH3, C2H5 or CH(CH3)2:
C1-C4-haloalkyl: a C1-C4-alkyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, CH2F, CHF2, CF3, CH2C1, dichloromethyl, trichloromethyl, 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, C2F5, 2-fluoropropyl, 3-fluoropropyl, 2,2-difluoropropyl, 2,3-difluoropropyl, 2-chloropropyl, 3-chloropropyl, 2,3-dichloropropyl, 2-bromopropyl, 3-bromopropyl, 3,3,3-trifluoropropyl, 3,3,3-trichloropropyl, 2,2,3,3,3-pentafluoropropyl, heptafluoropropyl, 1-(fluoromethyl)-2-fluoroethyl, 1-(chloromethyl)-2-chloro~thyl, 1-(b~~momethyl)-2-bromoethyl, 4-fluorobuLyl, 4-chlorobutyl, 4-bromobutyl or nonafluorobutyl, in particular CH2F, CHF2, CF3, CH2C1, 2-fluoroethyl, 2-chloroethyl or 2,2,2-trifluoroethyl;
- C1-C6-alkyl: Ci-C4-alkyl as mentioned above, and also, 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, 1-ethyl-1-methylpropyl or 1-ethyl-2-methylpropyl, in particular CH3, C2H5, n-propyl, CH(CH3)2, n-butyl, C(CH3)3, n-pentyl or n-hexyl;
- C1-C15-alkyl: C1-C6-alkyl as mentioned above, and also, for example, n-heptyl, 1-methylhexyl, 2-methylhexyl, 3-methylhexyl, 4-methylhexyl, 5-methylhexyl, 1-ethylpentyl, 2-ethylpentyl, 3-ethylpentyl, 4-ethylpentyl, 1,1-dimethylpentyl, 1,2-dimethylpentyl, 1,3-dimethylpentyl, 1,4-dimethylpentyl, n-octyl, 1-methylheptyl, 2-methylheptyl, 3-methylheptyl, 4-methylheptyl, 5-methylheptyl, 6-methylheptyl, 1-ethylhexyl, 2-ethylhexyl, 3-ethylhexyl, 4-ethylhexyl, 1,1-dimethylhexyl, 1,2-dimethylhexyl, 1,3-dimethylhexyl, 1,4-dimethylhexyl, 1,5-dimethylhexyl, n-nonyl, 1-methyloctyl, 2-methyloctyl, 3-methyloctyl, 4-methyloctyl, 5-methyloctyl, 6-methyloctyl, 7-methyloctyl, 1-ethylheptyl, 2-ethylheptyl, 3-ethylheptyl, 4-ethylheptyl, 5-ethylheptyl, 6-ethylheptyl, 1,1-dimethylheptyl, 1,2-dimethylheptyl, 1,3-dimethylheptyl, 1,4-dimethylheptyl, 1,5-dimethylheptyl, 1,6-dimethylheptyl, n-decyl, 1-methylnonyl, 2-methylnonyl, 3-methylnonyl, 7-methylnonyl, 8-methylnonyl, 1-ethyloctyl, 2-ethyloctyl, 3-ethyloctyl, 4-ethyloctyl, 5-ethyloctyl, 6-ethyloctyl, 7-ethyloctyl, 8-ethyloctyl, 1,1-dimethyloctyl, 1,2-dimethyloctyl, 1,3-dimethyloctyl, 1,4-dimethyloctyl, 1,5-dimethyloctyl, 1,6-dimethyloctyl, 1,7-dimethyloctyl, n-undecyl, 1-methyldecyl, 1-ethylnonyl, 1,1-dimethylnonyl, 1-propyloctyl, 1-butylheptyl, 6-undecyl, n-dodecyl, 1-methylundecyl, 1-ethyldecyl, 1,1-dimethyldecyl, 1-propylnonyl, 1-butyloctyl, 7-dodecyl, n-tridecyl, 1-methyldodecyl, 1-ethylundecyl, l,l-dimethylundecyl, n-tetradecyl, 1-methyltridecyl, 1-ethyldodecyl, 1,1-dimethyldodecyl, n-pentadecyl, 1-methyltetradecyl, 1-ethyltridecyl, 1,1-dimethyltridecyl, in particular CH3, C2Hg, n-propyi, CH(CH3)2, ~r-butyl, (CH3)3, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n-tetradecyl, n-pentadecyl;
- C1-C6-haloalkyl: C1-C6-alkyl as mentioned above which is 5 partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, one of the radicals mentioned under C1-C4-haloalkyl, or 5-fluoro-1-pentyl, 5-chloro-1-pentyl, 5-bromo-1-pentyl, 5-iodo-1-pentyl, 5,5,5-trichloro-1-pentyl, undecafluoropentyl, 10 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;
- hydroxy-C1-C6-alkyl: 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: for example cyanomethyl, 1-cyanoeth-1-yl, 2-cyanoeth-1-yl, 1-cyanoprop-1-yl, 2-cyanoprop-1-yl, 3-cyanoprop-1-yl, 1-cyanoprop-2-yl, 2-cyanoprop-2-yl, 1-cyanobut-1-yl, 2-cyanobut-1-yl, 3-cyanobut-1-yl, 4-cyanobut-1-yl, 1-cyanobut-2-yl, 2-cyanobut-2-yl, 1-cyanobut-3-yl, 2-cyanobut-3-yl, 1-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-C1-C6-alkyl: for example benzyl, 1-phenylethyl, 2-phenylethyl, 1-phenylprop-1-y1, 2-phenylprop-1-yl, 3-phenylprop-1-yl, 1-phenylbut-1-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, 1-(phenylmethyl)eth-1-yl, 1-(phenylmethyl)-1-(methyl)eth-1-yl or 1-(phenylmethyl)prop-1-yl, in particular benzyl or 2-phenylethyl;
- phenyl-(C1-C6-alkyl)carbonyloxy: for example benzylcarbonyloxy, 1-phenylethylcarbonyloxy, 2-phenylethylcarbonyloxy, 1-phenylprop-1-ylcarbonyloxy, 2-phenylprop-1-ylcarbonyloxy, 3-phenylprop-1-ylcarbonyloxy, 1-phemylbut-1-yluarbonyloxy, 2-phenylbut-1-ylcarbonyloxy; ~~

3-phenylbut-1-ylcarbonyloxy, 4-phenylbut-1-ylcarbonyloxy, 1-phenylbut-2-ylcarbonyloxy, 2-phenylbut-2-ylcarbonyloxy, 3-phenylbut-2-ylcarbonyloxy, 4-phenylbut-2-ylcarbonyloxy, 1-(phenylmethyl)eth-1-ylcarbonyloxy, 1-(phenylmethyl)-1-(methyl)eth-1-ylcarbonyloxy or 1-(phenylmethyl)-prop-1-ylcarbonyloxy, in particular benzylcarbonyloxy or 2-phenylethylcarbonyloxy;
- phenyl-C1-C6-alkylsulfonyloxy: for example benzylsulfonyloxy, 1-phenylethylsulfonyloxy, 2-phenylethylsulfonyloxy, 1-phenylprop-1-ylsulfonyloxy, 2-phenylprop-1-ylsulfonyloxy, 3-phenylprop-1-ylsulfonyloxy, 1-phenylbut-1-ylsulfonyloxy, 2-phenylbut-1-ylsulfonyloxy, 3-phenylbut-1-ylsulfonyloxy, 4-phenylbut-1-ylsulfonyloxy, 1-phenylbut-2-ylsulfonyloxy, 2-phenylbut-2-ylsulfonyloxy, 3-phenylbut-2-ylsulfonyloxy, 4-phenylbut-2-ylsulfonyloxy, 1-(phenylmethyl)eth-1-ylsulfonyloxy, 1-(phenylmethyl)-1-(methyl)eth-1-ylsulfonyloxy or 1-(phenylmethyl)prop-1-ylsulfonyloxy, in particular benzylsulfonyloxy or 2-phenylethylsulfonyloxy;
- (C1-C6-alkyl)carbonyl: CO-CH3, CO-C2H5, n-propylcarbonyl, 1-methylethylcarbonyl, n-butylcarbonyl, 1-methylpropylcarbonyl, 2-methylpropylcarbonyl, 1,1-dimethylethylcarbonyl, n-pentylcarbonyl, 1-methylbutylcarbonyl, 2-methylbutylcarbonyl, 3-methylbutylcarbonyl, 1,1-dimethylpropylcarbonyl, 1,2-dimethylpropylcarbonyl, 2,2-dimethylpropylcarbonyl, 1-ethylpropylcarbonyl, n-hexylcarbonyl, 1-rnethylpentylcarbonyl, 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 CO-CH3, CO-C2H5 or CO-CH(CH3)2:
- (C1-C6-alkyl)carbonyl-C1-C6-alkyl: C1-C6-alkyl which is substituted by (C1-C6-alkyl)carbonyl as mentioned above, i.e., for example, methylcarbonylmethyl;
- (C1-C6-haloalkyl)carbonyl: a (C1-C6-alkyl)carbonyl radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chioroacetyl, dichloroacetyl, trichloroacetyi, 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-difluoro-ethylcarbonyl, 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-pentafluoro-propylcarbonyl, heptafluoropropylcarbonyl, 1-(fluoromethyl)-2-fluoroethylcarbonyl, 1-(chloromethyl)-2-chloroethylcarbonyl, 1-(bromomethyl)-2-bromoethylcarbonyl, 4-fluorobutylcarbonyl, 4-chlorobutylcarbonyl, 4-bromobutylcarbonyl, nonafluorobutylcarbonyl, (5-fluoro-1-pentyl)carbonyl, (5-chloro-1-pentyl)carbonyl, (5-bromo-1-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: acetyloxy, ethylcarbonyloxy, n-propylcarbonyloxy, 1-methylethylcarbonyloxy, n-butylcarbonyloxy, 1-methylpropylcarbonyloxy, 2-methylpropylcarbonyloxy, 1,1-dimethylethylcarbonyloxy, n-pentylcarbonyloxy, 1-methylbutylcarbonyloxy, 2-methylbutylcarbonyloxy, 3-methylbutylcarbonyloxy, 1,1-dimethylpropylcarbonyloxy, 1,2-dimethylpropylcarbonyloxy, 2,2-dimethylpropylcarbonyloxy, 1-ethylpropylcarbonyloxy, n-hexylcarbonyloxy, 1-methylpentylcarbonyloxy, 2-methylpentylcarbonyloxy, 3-methylpentylcarbonyloxy, 4-methylpentylcarbonyloxy, 1,1-dimethylbutylcarbonyloxy, 1,2-dimethylbutylcarbonyloxy, 1,3-dimethylbutylcarbonyloxy, 2,2-dimethylbutylcarbonyloxy, 2,3-dimethylbutylcarbonyloxy, 3,3-dimethylbutylcarbonyloxy, 1-ethylbutylcarbonyloxy, 2-ethylbutylcarbonyloxy, 1,1,2-trimethylpropylcarbonyloxy, 1,2,2-trimethylpropylcarbonyloxy, 1-ethyl-1-methylpropyl-carbonyloxy or 1-ethyl-2-methylpropylcarbonyloxy, in particular acetyloxy;

- (C1-C6-haloalkyl)carbonyloxy: a (C1-C6-alkyljcarbonyloxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloroacetyloxy, dichloroacetyloxy, trichloroacetyloxy, fluoroacetyloxy, difluoroacetyloxy, trifluoroacetyloxy, chlorofluoroacetyloxy, dichlorofluoroacetyloxy,_chlorodifluoroacetyloxy, 2-fluoroethylcarbonyloxy, 2-chloroethylcarbonyloxy, 2-bromoethylcarbonyloxy, 2-iodoethylcarbonyloxy, 2,2-difluoroethylcarbonyloxy, 2,2,2-trifluoroethyl-carbonyloxy, 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-trichloropropyl-carbonyloxy, 2,2,3,3,3-pentafluoropropylcarbonyloxy, heptafluoropropylcarbonyloxy, 1-(fluoromethyl)-2-fluoro-ethylcarbonyloxy, 1-(chloromethyl)-2-chloroethylcarbonyloxy, 1-(bromomethyl)-2-bromoethylcarbonyloxy, 4-fluorobutylcarbonyloxy, 4-chlorobutylcarbonyloxy, 4-bromobutyl or nonafluorobutyl, in particular trifluoroacetoxy;
- (C1-C6-alkyl)carbonyloxy-C1-C6-alkyl: C1-C6-alkyl which is substituted by (C1-C6-alkyl)carbonyloxy as mentioned above, i.e., for example, methylcarbonyloxymethyl, ethylcarbonyloxymethyl, 1-(methylcarbonyloxy)ethyl, 2-(methylcarbonyloxy)ethyl, 2-(ethylcarbonyloxy)ethyl, 3-(methylcarbonyloxy)propyl, 4-(methoxycarbonyloxy)butyl, 5-(methoxycarbonyloxy)pentyl or 6-(methoxycarbonyloxy)hexyl;
- (C1-C6-alkyl)carbonylthio: acetylthio, ethylcarbonylthio, n-propylcarbonylthio, 1-methylethylcarbonylthio, n-butylcarbonylthio, 1-methylpropylcarbonylthio, 2-methylpropylcarbonylthio, 1,1-dimethylethylcarbonylthio, n-pentylcarbonylthio, 1-methylbutylcarbonylthio, 2-methylbutylcarbonylthio, 3-methylbutylcarbonylthio, 1,1-dimethylpropylcarbonylthio, 1,2-dimethylpropyl-carbonylthio, 2,2-dimethylpropylcarbonylthio, 1-ethylpropylcarbonylthio, n-hexylcarbonylthio, 1-methylpentylcarbonylthio, 2-methylpentylcarbonylthio, 3-methylperrtylcarbonylthio, 4-methylpentylcarbonylthio, i,l-dimethylbutylcarbonylthio, 1,2-dimethylbutylcarbonylthio,~

005o/5ooso 1,3-dimethylbutylcarbonylthio, 2,2-dimethylbutylcarbonylthio, 2,3-dimethylbutylcarbonylthio, 3,3-dimethylbutylcarbonylthio, 1-ethylbutylcarbonylthio, 2-ethylbutylcarbonylthio, 1,1,2-trimethylpropylcarbonylthio, 1,2,2 -trimethylpropyl-carbonylthio, 1-ethyl-1-methylpropylcarbonylthio or 1-ethyl-2-methylpropylcarbonylthio, in particular acetylthio;
(C1-C6-haloalkyl)carbonylthio: a (C1-C6-alkyl)carbonylthio radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloroacetylthio, dichloroacetylthio, trichloroacetylthio, fluoroacetylthio, difluoroacetylthio, trifluoroacetylthio, chlorofluoroacetylthio, dichlorofluoroacetylthio, chlorodifluoroacetylthio, 2-fluoroethylcarbonylthio, 2-chloroethylcarbonylthio, 2-bromoethylcarbonylthio, 2-iodoethylcarbonylthio, 2,2-difluoroethylcarbonylthio, 2,2,2-trifluoroethyl-carbonylthio, 2-chloro-2-fluoroethylcarbonylthio, 2-chloro-2,2-difluoroethylcarbonylthio, 2,2-dichloro-2-fluoroethylcarbonylthio, 2,2,2-trichloroethylcarbonylthio, pentafluoroethylcarbonylthio, 2-fluoropropylcarbonylthio, 3-fluoropropylcarbonylthio, 2,2-difluoropropylcarbonylthio, 2,3-difluorapropylcarbonylthio, 2-chloropropylcarbonylthio, 3-chloropropylcarbonylthio, 2,3-dichloropropylcarbonylthio, 2-bromopropylcarbonylthio, 3-bromopropylcarbonylthio, 3,3,3-trifluoropropylcarbonylthio, 3,3,3-trichloropropyl-carbonylthio, 2,2,3,3,3-pentafluoropropylcarbonylthio, heptafluoropropylcarbonylthio, 1-(fluoromethyl)-2-fluoroethylcarbonylthio, 1-(chloromethyl)-2-chloro-ethylcarbonylthio, 1-(bromomethyl)-2-bromoethylcarbonylthio, 4-fluorobutylcarbonylthio, 4-chlorobutylcarbonylthio, 4-bromobutylthio or nonafluorobutylthio, in particular trifluoroacetylthio;
- (C1-C6-alkyl)carbamoyloxy: methylcarbarnoyloxy, ethylcarbamoyloxy, n-propylcarbamoyloxy, 1-methylethylcarbamoyloxy, n-butylcarbamoyloxy, 1-methylpropylcarbamoyloxy, 2-methylpropylcarbamoyloxy, 1,1-dimethylethylcarbamoyloxy, n-pentylcarbamoyloxy, 1-methylbutylcarbamoyloxy, 2-methylbutylcarbamoyloxy, 3-methylbutylcarbamoyloxy, 1,1-dimethylpropylcarbamoyloxy, 1,2-dimethylpropylcarbamoyloxy, 2,2-dimethylpropyl-carbamoyloxy, 1-ethylpropylcarbamoyloxy, n-hexylcarbamoyloxy, 1-methylpentylcarbamoyloxy, 2-methylpentylcarbamoyloxy, 3-methylpentylcarbamoyloxy, 4-methylpentylcarbamoyloxy, 1,1-dimethylbutylcarbamoyloxy, 1,2-dimethylbutylcarbamoyloxy, i,3-dimethylbutylcarbamoyloxy, 2,2-dimethylbutylearbamoyloxy, 2,3-dimethylbutylcarbamoyloxy, 3,3-dimethylbutylcarbamoyloxy, 1-ethylbutylcarbamoyloxy, 2-ethylbutylcarbamoyloxy, 1,1,2-trimethylpropylcarbamoyloxy, 1,2,2-trimethylpropyl-carbamoyloxy, 1-ethyl-1-methylpropylcarbamoyloxy or 5 1-ethyl-2-methylpropylcarbamoyloxy, in particular methylcarbamoyloxy;
- (C1-C6-haloalkyl)carbamoyloxy: a (C1-C6-alkyl)carbamoyloxy radical as mentioned above which is partially or fully 10 substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, chloromethylcarbamoyloxy, dichloromethylcarbamoyloxy, trichloromethylcarbamoyloxy, fluoromethylcarbamoyloxy, difluoromethylcarbamoyloxy, trifluoromethylcarbamoyloxy, chlorofluoromethylcarbamoyloxy, 15 dichlorofluoromethylcarbamoyloxy, chlorodifluoromethyl-carbamoyloxy, 2-fluoroethylcarbamoyloxy, 2-chloroethylcarbamoyloxy, 2-bromoethylcarbamoyloxy, 2-iodoethylcarbamoyloxy, 2,2-difluoroethylcarbamoyloxy, 2,2,2-trifluoroethylcarbamoyloxy, 2-chloro-2-fluoroethyl-20 carbamoyloxy, 2-chloro-2,2-difluoroethylcarbamoyloxy, 2,2-dichloro-2-fluoroethylcarbamoyloxy, 2,2,2-trichloroethyl-carbamoyloxy, pentafluoroethylcarbamoyloxy, 2-fluoropropyl-carbamoyloxy, 3-fluoropropylcarbamoyloxy, 2,2-difluoro-propylcarbamoyloxy, 2,3-difluoropropylcarbamoyloxy, 2-chloropropylcarbamoyloxy, 3-chloropropylcarbamoyloxy, 2,3-dichloropropylcarbamoyloxy, 2-bromopropylcarbamoyloxy, 3-bromopropylcarbamoyloxy, 3,3,3-trifluoropropylcarbamoyloxy, 3,3,3-trichloropropylcarbamoyloxy, 2,2,3,3,3-pentafluoro-propylcarbamoyloxy, heptafluoropropylcarbamoyloxy, 1-(fluoromethyl)-2-fluoroethylcarbamoyloxy, 1-(chloromethyl)-2-chloroethylcarbamoyloxy, 1-(bromomethyl)-2-bromoethyl-carbamoyloxy, 4-fluorobutylcarbamoyloxy, 4-chlorobutyl-carbamoyloxy, 4-bromobutylcarbamoyloxy or nonafluorobutyl-carbamoyloxy, in particular trifluoromethylcarbamoyloxy;
- C1-C6-alkoxy: for example OCH3, OCZHS, OCHz-C2H5, OCH(CH3)z.
n-butoxy, OCH(CH3)-CZHS, OCHz-CH(CH3)z, OC(CH3)3, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy, 3-methylbutoxy, 1,1-dimethylpropoxy, 1,2-dimethylpropoxy, 2,2-dimethyl-propoxy, 1-ethylpropoxy, n-hexoxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,1-dimethylbutoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, 2,2-dimethylbutoxy, 2,3-dimethylbutoxy, 3,3-dimethylbutoxy, 1-ethylbutoxy, 2-ethylbutoxy, 1,1,2-trimethylpropoxy, 1,2,2-trimethylpropoxy, 1-ethyl-1-methylpropoxy and 1-ethyl-2-methylpropoxy, in particular OCH3, OC2H5 or OCH(CH3)Z;
- C1-C4-haloalkoxy: a C1-C4-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, 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, 3-bromopropoxy, 3,3,3-trifluoropropoxy, 3,3,3-trichloropropoxy, 2,2,3,3,3-pentafluoropropoxy, heptafluoropropoxy, 1-(fluoromethyl)-2-fluoroethoxy, 1-(chloromethyl)-2-chloroethoxy, 1-(bromomethyl)-2-bromoethoxy, 4-fluorobutoxy, 4-chlorobutoxy, 4-bromobutoxy or nonafluorobutoxy, in particular 2-chloroethoxy or 2,2,2-trifluoroethoxy;
- C1-C6-haloalkoxy: a C1-C6-alkoxy radical as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, one of the radicals mentioned under C1-C4-haloalkoxy, or 5-fluoro-1-pentoxy, 5-chloro-1-pentoxy, 5-bromo-1-pentoxy, 5-iodo-1-pentoxy, 5,5,5-trichloro-1-pentoxy, undecafluoropentoxy, 6-fluoro-1-hexoxy, 6-chloro-1-hexoxy, 6-bromo-1-hexoxy, 6-iodo-1-hexoxy, 6,6,6-trichloro-1-hexoxy or dodecafluorohexoxy, in particular chloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, 2-fluoroethoxy, 2-chloroethoxy or 2,2,2-trifluoroethoxy;
hydroxy-C1-C6-alkoxy: for example OCH2-OH, OCH(CH3)-OH, OCHZ-CH2-OH, OCH(CZHS)-OH, OCHZ-CH(CH3)-OH, 3-hydroxyprop-I-yloxy, 1-hydroxybut-1-yloxy, 2-hydroxybut-1-yloxy, 3-hydroxybut-1-yloxy, 4-hydroxybut-1-yloxy, 1-hydroxybut-2-yloxy, 2-hydroxybut-2-yloxy, 3-hydroxybut-2-yloxy, 4-hydroxybut-2-yloxy, 1-(CH2-OH)-eth-1-yloxy, 1-(CH2-OH)-1-(CH3)-eth-1-yloxy or 1-(CHZ-OH)-prop-Z-yloxy, in particular OCH2-OH or OCH2-CH2-OH;

- cyano-C1-C6-alkoxy: for example OCHZ-CN, OCH(CH3)-CN, OCHz-CH2-CN, OCH(CpHS)-OH, OCH2-CH(CH3)-CN, 3-cyanoprop-1-yloxy, 1-cyanobut-1-yloxy, 2-cyanobut-1-yloxy, 3-cyanobut-1-yloxy, 4-cyanobut-1-yloxy, 1-cyanobut-2-yloxy, 2-cyanobut-2-yloxy, 3-cyanobut-2-yloxy, 4-cyanobut-2-yloxy, 1-(CH2-CN)-eth-1-yloxy, 1-(CHZ-CN)-1-(CH3)-eth-1-yloxy or 1-(CH2-CN)-prop-1-yloxy, in particular OCHZ-CN or OCH2-CH2-CN;
- phenyl-C1-C6-alkoxy: for example benzyloxy, 1-phenylethoxy, 2-phenylethoxy, 1-phenylprop-1-yloxy, 2-phenylprop-1-yloxy, 3-phenylprop-1-yloxy, 1-phenylbut-1-yloxy, 2-phenylbut-1-yloxy, 3-phenylbut-1-yloxy, 4-phenylbut-1-yloxy, 1-phenylbut-2-yloxy, 2-phenylbut-2-yloxy, 3-phenylbut-2-yloxy, 4-phenylbut-2-yloxy, 1-(benzyl)eth-1-yloxy, 1-(benzyl)-1-(methyl)eth-1-yloxy or 1-(benzyl)prop-1-yloxy, in particular benzyloxy or 2-phenylethoxy;
- heterocyclyl-C1-C6-alkoxy: for example heterocyclylmethoxy, 1-(heterocyclyl)ethoxy, 2-(heterocyclyl)ethoxy, 1-(heterocyclyl)prop-1-yloxy, 2-(heterocyclyl)prop-1-yloxy, 3-(heterocyclyl)prop-1-yloxy, 1-(heterocyclyl)but-1-yloxy, 2-(heterocyclyl)but-1-yloxy, 3-(heterocyclyl)but-1-yloxy, 4-(heterocyclyl)but-1-yloxy, 1-(heterocyclyl)but-2-yloxy, 2-(heterocyclyl)but-2-yloxy, 3-(heterocyclyl)but-2-yloxy, 4-(heterocyclyl)but-2-yloxy, 1-(heterocyclylmethyl)-eth-1-yloxy, 1-(heterocyclylmethyl)-1-(methyl)-eth-1-yloxy or 1-(heterocyclylmethyl)-prop-1-yloxy, in particular heterocyclylmethoxy or 2-(heterocyclyl)ethoxy;
- phenyl-C1-C6-alkylthio: for example benzylthio, 1-phenylethylthio, 2-phenylethylthio, 1-phenylprop-1-ylthio, 2-phenylprop-1-ylthio, 3-phenylprop-1-ylthio, 1-phenylbut-1-ylthio, 2-phenylbut-1-ylthio, 3-phenylbut-1-ylthio, 4-phenylbut-1-ylthio, 1-phenylbut-2-ylthio, 2-phenylbut-2-ylthio, 3-phenylbut-2-ylthio, 4-phenylbut-2-ylthio, 1-(phenylmethyl)eth-1-ylthio, 1-(phenylmethyl)-1-(methyl)eth-1-ylthio or 1-(phenylmethyl)prop-1-ylthio, in particular benzylthio or 2-phenylethylthio;
- (C1-C6-alkoxy)carbonyl: for example -CO-OCH3, CO-OC2H5, COO-CH2-C2H5, CO-OCH(CH3)Z, n-butoxycarbonyl, CO-OCH(CH3)-C2H5, CO-OCH2-CH(CH3)2, CO-OC(CH3)3, n-pentoxycarbonyl, I-methyibutoxycarboryl, 2-~nethylbutoxycarbonyl, 3-methylbutoxycarbonyl, 2,2-dimethylpropoxycarbonyl, 1-ethylpropoxycarbonyl, n-hexoxycarbonyl, 1,1-dimethylpropoxycarbonyl, 1,2-dimethylpropoxycarbonyl, 1-methylpentoxycarbonyl, 2-methylpentoxycarbonyl, 3-methylpentoxycarbonyl, 4-methylpentoxycarbonyl, 1,1-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 CO-OCH3, CO-OC2H5, CO-OCH(CH3)z or CO-CHZ-CH(CH3)2:
- (C1-C6-alkoxy)carbonyloxy: methoxycarbonyloxy, ethoxycarbonyloxy, n-propoxycarbonyloxy, 1-methylethoxycarbonyloxy, n-butoxycarbonyloxy, 1-methylpropoxycarbonyloxy, 2-methylpropoxycarbonyloxy, 1,1-dimethylethoxycarbonyloxy, n-pentoxycarbonyloxy, 1-methylbutoxycarbonyloxy, 2-methylbutoxycarbonyloxy, 3-methylbutoxycarbonyloxy, 2,2-dimethylpropoxycarbonyloxy, 1-ethylpropoxycarbonyloxy, n-hexoxycarbonyloxy, 1,1-dimethylpropoxycarbonyloxy, 1,2-dimethylpropoxycarbonyloxy, 1-methylpentoxycarbonyloxy, 2-methylpentoxycarbonyloxy, 3-methylpentoxycarbonyloxy, 4-methylpentoxycarbonyloxy, 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;
- (C1-C6-alkoxy)carbonylthio: methoxycarbonylthio, ethoxycarbonylthio, n-propoxycarbonylthio, 1-methylethoxycarbonylthio, n-butoxycarbonylthio, 1-methylpropoxycarbonylthio, 2-methylpropoxycarbonylthio, 1,1-dimethylethoxycarbonylthio, n-pentoxycarbonylthio, 1-methylbutoxycarbonylthio, 2-methylbutoxycarbonylthio, 3-methylbutoxycarbonylthio, 2,2-dimethylpropoxycarbonylthio, 1-ethylpropoxycarbonylthio, n-hexoxycarbonylthia, 1,1-dimethylpropoxycarbonylthio, 1, 2-dimethylpropoxycarboizylthi~, 1-methylpen'coxycarbaziylvhio, 2-methylpentoxycarbonylthio, 3-methylpentoxycarbonylthio, 4-methylpentoxycarbonylthio, 1,1-dimethylbutoxycarbonylthio, 1,2-dimethylbutoxycarbonylthio, 1,3-dimethylbutoxycarbonylthio, 2,2-dimethylbutoxycarbonylthio, 2,3-dimethylbutoxycarbonylthio, 3,3-dimethylbutoxycarbonylthio, 1-ethylbutoxycarbonylthio, 2-ethylbutoxycarbonylthio, 1,1,2-trimethylpropoxycarbonylthio, 1,2,2-trimethylpropoxycarbonylthio, 1-ethyl-1-methylpropoxycarbonylthio or 1-ethyl-2-methylpropoxycarbonylthio, in particular methoxycarbonylthio, ethoxycarbonylthio or 1-methylethoxycarbonylthio;
- C1-C6-alkylthio: SCH3, SC2H5, SCH2-C2H5, SCH(CH3)2, n-butylthio, 1-methylpropylthio, 2-methylpropylthio, SC(CH3)3.
n-pentylthio, 1-methylbutylthio, 2-methylbutylthio, 3-methylbutylthio, 2,2-dimethylpropylthio, 1-ethylpropylthio, n-hexylthio, 1,1-dimethylpropylthio, 1,2-dimethylpropylthio, 1-methylpentylthio, 2-methylpentylthio, 3-methylpentylthio, 4-methylpentylthio, I,1-dimethylbutylthio, 1,2-dimethylbutylthio, 1,3-dimethylbutylthio, 2,2-dimethylbutylthio, 2,3-dimethylbutylthio, 3,3-dimethylbutylthio, 1-ethylbutylthio, 2-ethylbutylthio, 1,1,2-trimethylpropylthio, 1,2,2-trimethylpropylthio, 1-ethyl-1-methylpropylthio and 1-ethyl-2-methylpropylthio, in particular SCH3 or SC2H5;
- C1-C6-haloalkylthio: C1-C6-alkylthio as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, SCHF2, SCF3, 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, SC2F5, 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, 1-(fluoromethyl)-2-fluoroethylthio, 1-(chloromethyl)-2-chloroethylthio, 1-(bromomethyl)-2-bromoethylthio, 4-fluorobutylthio, 4-chlorobutyltl~io, 4-broiaobutylthio, nonafluorobutyl~chio, 5-fluoropentylthio, 5-chloropentylthio, 5-bromopentylthio, 5-iodopentylthio, undecafluoropentylthio, 6-fluorohexylthio or 6-chlorohexylthio, in particular SCHZF, SCHF2, SCF3, SCHZC1, 2-fluoroethylthio, 2-chloroethylthio or 5 2,2,2-trifluoroethylthio;
C1-C6-alkylsulfinyl: SO-CH3, SO-C2H5, n-propylsulfinyl, 1-methylethylsulfinyl, n-butylsulfinyl, 1-methylpropylsulfinyl, 2-methylpropylsulfinyl, 10 1,1-dimethylethylsulfinyl, n-pentylsulfinyl, 1-methylbutylsulfinyl, 2-methylbutylsulfinyl, 3-methylbutylsulfinyl, 1,1-dimethylpropylsulfinyl, 1,2-dimethylpropylsulfinyl, 2,2-dimethylpropylsulfinyl, 1-ethylpropylsulfinyl, n-hexylsulfinyl, 15 1-methylpentylsulfinyl, 2-methylpentylsulfinyl, 3-methylpentylsulfinyl, 4-methylpentylsulfinyl, 1,1-dimethylbutylsulfinyl, 1,2-dimethylbutylsulfinyl, 1,3-dimethylbutylsulfinyl, 2,2-dimethylbutylsulfinyl, 2,3-dimethylbutylsulfinyl, 3,3-dimethylbutylsulfinyl, 20 1-ethylbutylsulfinyl, 2-ethylbutylsulfinyl, 1,1,2-trimethylpropylsulfinyl, 1,2,2-trimethylpropylsulfinyl, 1-ethyl-1-methylpropylsulfinyl or 1-ethyl-2-methylpropylsulfinyl, in particular SO-CH3;
25 - C1-C6-alkylsulfonyl: SOZ-CH3, S02-CzH5, n-propylsulfonyl, S02-CH(CH3)2, n-butylsulfonyl, 1-methylpropylsulfonyl, 2-methylpropylsulfonyl, S02-C(CH3)3, n-pentylsulfonyl, 1-methylbutylsulfonyl, 2-methylbutylsulfonyl, 3-methylbutylsulfonyl, 1,1-dimethylpropylsulfonyl, 1,2-dimethylpropylsulfonyl, 2,2-dimethylpropylsulfonyl, 1-ethylpropylsulfonyl, n-hexylsulfonyl, 1-methylpentylsulfonyl, 2-methylpentylsulfonyl, 3-methylpentylsulfonyl, 4-methylpentylsulfonyl, 1,1-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, 1-ethyl-1-methylpropylsulfonyl or 1-ethyl-2-methylpropylsulfonyl, in particular S02-CH3;
- C1-C6-alkylsulfonyloxy: O-S02-CH3, O-S02-C2H5, n-propylsulfonyloxy, O-S02-CH(CH3)Z, n-butylsulfonyloxy, 1-methylpropylsulfonyloxy, 2-methylpropylsulfonyloxy, 0-SOZ-C(CH3)3, n-pentylsulfonyloxy, 1-methylbutylsulfonyloxy, 2-methylbutylsulfonyloxy, 3-methylbutylsulfonyloxy, 1,1-dimeihylpropylsulfonyloxy, 1,2-dimethylpropylsulfonyluxy, 2,2-dimethylpropylsulfonyloxy, 1-ethylpropylsulfonyloxy, n-hexylsulfonyloxy, 1-methylpentylsulfonyloxy, 2-methylpentylsulfonyloxy, 3-methylpentylsulfonyloxy, 4-methylpentylsulfonyloxy, 1,1-dimethylbutylsulfonyloxy, 1,2-dimethylbutylsulfonyloxy, 1,3-dimethylbutylsulfonyloxy, 2,2-dimethylbutylsulfonyloxy, 2,3-dimethylbutylsulfonyloxy, 3,3-dimethylbutylsulfonyloxy, 1-ethylbutylsulfonyloxy, 2-ethylbutylsulfonyloxy, 1,1,2-trimethylpropylsulfonyloxy, 1,2,2-trimethylpropylsulfonyloxy, 1-ethyl-1-methylpropylsulfonyloxy or 1-ethyl-2-methylpropylsulfonyloxy, in particular methylsulfonyloxy;
C1-C6-haloalkylsulfonyloxy: C1-C6-alkylsulfonyloxy as mentioned above which is partially or fully substituted by fluorine, chlorine, bromine and/or iodine, i.e., for example, C1CH2-S02-O-, CH(Cl)2-SOZ-O-, C(Cl)g-SOp-O-, FCHZ-S02-O-, CHF2-S02-O-, CF3-SOz-O-, chlorofluoromethyl-SOZ-O-, dichlorofluoromethyl-S02-O-, chlorodifluoromethyl-S02-O-, 1-fluoroethyl-S02-0-, 2-fluoroethyl-S02-O-, 2-chloroethyl-S02-O-, 2-bromoethyl-SOZ-0-, 2-iodoethyl-SOZ-O-, 2,2-difluoroethyl-S02-0-, 2,2,2-trifluoroethyl-SOZ-O-, 2-chloro-2-fluoroethyl-SOz-O-, 2-chloro-2,2-difluoroethyl-SOZ-O-, 2,2-dichloro-2-fluoroethyl-SOZ-O-, 2,2,2-trichloroethyl-S02-O-, C2F5-S02-0-, 2-fluoropropyl-S02-O-, 3-fluoropropyl-S02-O-, 2,2-difluoropropyl-S02-O-, 2,3-difluoropropyl-S02-O-, 2-chloropropyl-S02-0-, 3-chloropropyl-S02-O-, 2,3-dichloropropyl-S02-O-, 2-bromopropyl-S02-O-, 3-bromopropyl-S02-0-, 3,3,3-trifluoropropyl-S02-O-, 3,3,3-trichloropropyl-S02-O-, 2,2,3,3,3-pentafluoropropyl-S02-O-, CzFS-CFZ-S02-O-, 1-(fluoromethyl)-2-fluoroethyl-S02-0-, 1-(chloromethyl)-2-chloroethyl-S02-O-, 1-(bromomethyl)-2-bromoethyl-SOz-O-, 4-fluorobutyl-SOZ-O-, 4-chlorobutyl-SOZ-O-, 4-bromobutyl-S02-O-, CzFS-CF2-CF2-S02-0-, 5-fluoropentyl-SO2-O-, 5-chloropentyl-SO2-O-, 5-bromopentyl-S02-O-, 5-iodopentyl-S02-O-, 5,5,5-trichloropentyl-S02-0-, C2F5-CFZ-CF2-CF2-S02-O-, 6-fluorohexyl-SOZ-O-, 6-chlorohexyl-S02-0-, 6-bromohexyl-SOZ-O-, 6-iodohexyl-S02-O-, 6,6,6-trichlorohexyl-S02-0- or dodecafluorohexyl-S02-O-, in particular CF3-S02-O-;

- (C1-C6-alkyl)aminocarbonyl: (C1-C4-alkyl)aminocarbonyl as mentioned above and also for example, n-pentylaminocarbonyl, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylaminocarbonyl, n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, I-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethylbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl or 1-ethyl-2-methylpropylaminocarbonyl, in particular CO-NH-CH3, CO-NH-C2H5 or CO-NH-CH(CH3)2:
- di(C1-C6-alkyl)aminocarbonyl: for example N,N-dimethylaminocarbonyl, N,N-diethylaminocarbonyl, N,N-dipropylaminocarbonyl, N,N-di(1-methylethyl)aminocarbonyl, N,N-dibutylaminocarbonyl, N,N-di(1-rnethylpropyl)aminocarbonyl, N,N-di(2-methylpropyl)aminocarbonyl, N,N-di(1,1-dimethylethyl)aminocarbonyl, N-ethyl-N-methylaminocarbonyl, N-methyl-N-propylaminocarbonyl, N-methyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-methylaminocarbonyl, N-methyl-N-(1-methylpropyl)aminocarbonyl, N-methyl-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-methylaminocarbonyl, N-ethyl-N-propylaminocarbonyl, N-ethyl-N-(1-methylethyl)aminocarbonyl, N-butyl-N-ethylaminocarbonyl, N-ethyl-N-(1-methylpropyl)aminocarbonyl, N-ethyl-N-(2-methylpropyl)aminocarbonyl, N-ethyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylethyl)-N-propylaminocarbonyl, N-butyl-N-propylaminocarbonyl, N-(1-methylpropyl)-N-propylaminocarbonyl, N-(2-methylpropyl)-N-propylaminocarbonyl, N-(1,1-dimethylethyl)-N-propylaminocarbonyl, N-butyl-N-~i-methylethyl)aminocarbonyl, - w N-(1-methylethyl)-N-(1-methylpropyl)aminocarbonyl, N-(1-methylethyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylethyl)aminocarbonyl, N-butyl-N-(1-methylpropyl)aminocarbonyl, N-butyl-N-(2-methylpropyl)aminocarbonyl, N-butyl-N-(1,1-dimethylethyl)aminocarbonyl, N-(1-methylpropyl)-N-(2-methylpropyl)aminocarbonyl, N-(1,1-dimethylethyl)-N-(1-methylpropyl)aminocarbonyl or N-(1,1-dimethylethyl)-N-(2-methylpropyl)aminocarbonyl, in particular N,N-dimethylaminocarbonyl or N,N-diethylaminocarbonyl;
- (C1-C6-alkyl)iminooxycarbonyl: methyliminooxycarbonyl, ethyliminooxycarbonyl, n-propyliminooxycarbonyl, 1-methylethyliminooxycarbonyl, n-butyliminooxycarbonyl, 1-methylpropyliminooxycarbonyl, 2-methylpropyliminooxycarbonyl, 1,1-dimethylethyliminooxycarbonyl, n-pentyliminooxycarbonyl, 1-methylbutyliminooxycarbonyl, 2-methylbutyliminooxycarbonyl, 3-methylbutyliminooxycarbonyl, 1,1-dimethylpropyliminooxycarbonyl, 1,2-dimethylpropyliminooxycarbonyl, 2,2-dimethylpropyliminooxycarbonyl, 1-ethylpropyliminooxycarbonyl, n-hexyliminooxycarbonyl, 1-methylpentyliminooxycarbonyl, 2-methylpentyliminooxycarbonyl, 3-methylpentyliminooxycarbonyl, 4-methylpentyliminooxycarbonyl, 1,1-dimethylbutyliminooxycarbonyl, 1,2-dimethylbutyliminooxycarbonyl, 1,3-dimethylbutyliminooxycarbonyl, 2,2-dimethylbutyliminooxycarbonyl, 2,3-dimethylbutyliminooxycarbonyl, 3,3-dimethylbutyliminooxycarbonyl, 1-ethylbutyliminooxycarbonyl, 2-ethylbutyliminooxycarbonyl, 1,1,2-trimethylpropyliminooxycarbonyl, 1,2,2-trimethylpropyliminooxycarbonyl, 1-ethyl-1-methylpropyliminooxycarbonyl or 1-ethyl-2-methylpropyliminooxycarbonyl, in particular methyliminooxycarbonyl, ethyliminooxycarbonyl or 1-methylethyliminooxycarbonyl;
- C1-C6-alkylideneaminooxy: 1-propylideneaminooxy, 2-propylideneaminooxy, 1-butylideneaminooxy, 2-butylideneaminooxy or 2-hexylideneaminooxy, in particular acetylideneaminooxy or 2-propylideneaminooxy;

- C1-C6-alkyliminooxy: methyliminooxy, ethyliminooxy, n-propyliminooxy, 1-methylethyliminooxy, n-butyliminooxy, 1-methylpropyliminooxy, 2-methylpropyliminooxy, n-pentyliminooxy, n-hexyliminooxy, 1-methylpentyliminooxy, 2-methylpentyliminooxy, 3-methylpentyliminooxy or 4-methylpentyliminooxy, in particular methyliminooxy, ethyliminooxy or 1-methylethyliminooxy;
- C1-C6-alkoxy-(C1-C6-alkyl)aminocarbonyl:
(C1-C6-alkyl)aminocarbonyl such as CO-NH-CH3, CO-NH-C2H5.
CO-NH-CH2-C2H5, CO-NH-CH(CH3)y, CO-NH-(CH2)3-CH3, CO-NH-CH(CH3)-C2H5, CO-NH-CH2-CH(CH3)Z, CO-NH-C(CH3)3.
CO-NH-(CH2)4-CH3, 1-methylbutylaminocarbonyl, 2-methylbutylaminocarbonyl, 3-methylbutylaminocarbonyl, 2,2-dimethylpropylaminocarbonyl, 1-ethylpropylarninocarbonyl, n-hexylaminocarbonyl, 1,1-dimethylpropylaminocarbonyl, 1,2-dimethylpropylaminocarbonyl, 1-methylpentylaminocarbonyl, 2-methylpentylaminocarbonyl, 3-methylpentylaminocarbonyl, 4-methylpentylaminocarbonyl, 1,1-dimethylbutylaminocarbonyl, 1,2-dimethyTbutylaminocarbonyl, 1,3-dimethylbutylaminocarbonyl, 2,2-dimethylbutylaminocarbonyl, 2,3-dimethylbutylaminocarbonyl, 3,3-dimethylbutylaminocarbonyl, 1-ethylbutylaminocarbonyl, 2-ethylbutylaminocarbonyl, 1,1,2-trimethylpropylaminocarbonyl, 1,2,2-trimethylpropylaminocarbonyl, 1-ethyl-1-methylpropylaminocarbonyl and 1-ethyl-2-methylpropylaminocarbonyl, preferably (C1-C4-alkyl)aminocarbonyl, which is substituted by C1-C6-alkoxy as mentioned above, i.e., for example, CO-NH-CHZ-OCH3 or CO-NH-CHZ-OCZH5;
- C1-C6-alkoxyamino-C1-C6-alkyl: for example CHZ-NH-OCH3, CH2-NH-OCZHS, CHy-NH-OCH2-C2H5, CH2-NH-OCH(CH3)yr CH2-NH-OCHp-CHZ-CyHS, CH2-NH-OCH(CH3)-C2H5, CH2-NH-OCH2-CH(CHg)2, CH2-NH-OC(CH3)3, CHZ-NH-OCH2-(CHz)3-cH3, (1-methylbutoxyamino)methyl, (2-methylbutoxyamino)methyl, (3-methylbutoxyamino)methyl, (2,2-dimethylpropoxyamino)methyl, (1-ethylpropoxyamino)methyl, n-hexoxyaminomethyl, (1,1-dimethylpropoxyamino)methyl, (1,2-dimethylpropoxyamino)methyl, (1-methylpentoxyamino)methyl, (2-methylpentoxyamino)methyl, (3-methylpentoxyamino)methyl, (4-methylpentoxyamino)methyl, (1,1-dimethylbutoxyamino)methyl, (1,2-dimethylbutoxyamino)methyl, (1,3-dimethylbutoxyamino)methyl, (2,2-dimethylbutoxyamino)methyl, (2,3-dimethylbutoxyamino)methyl, (3,3-dimethylbutoxyamino)methyl, (1-ethylbutoxyamino)methyl, 5 (2-ethylbutoxyamino)methyl, (1,1,2-trimethylpropoxyamino)methyl, (1,2,2-trimethylpropoxyamino)methyl, (1-ethyl-1-methylpropoxyamino)methyl, (1-ethyl-2-methylpropoxyamino)methyl, methoxyaminoethyl, 10 ethoxyaminoethyl, n-propoxyaminoethyl, (1-methylethoxyamino)ethyl, n-butoxyaminoethyl, (1-methylpropoxyamino)ethyl, (2-methylpropoxyamino)ethyl, (l,l-dimethylethoxyamino)ethyl, n-pentoxyaminoethyl, (1-methylbutoxyamino)ethyl, (2-methylbutoxyamino)ethyl, 15 (3-methylbutoxyamino)ethyl, (2,2-dimethylpropoxyamino)ethyl, (1-ethylpropoxyamino)ethyl, n-hexoxyaminoethyl, (1,1-dimethylpropoxyamino)ethyl, (1,2-dimethylpropoxyamino)ethyl, (1-methylpentoxyamino)ethyl, (2-methylpentoxyamino)ethyl, (3-methylpentoxyamino)ethyl, 20 (4-methylpentoxyamino)ethyl, (1,1-dimethylbutoxyamino)ethyl, (1,2-dimethylbutoxyamino)ethyl, (1,3-dimethylbutoxyamino)ethyl, (2,2-dimethylbutoxyamino)ethyl, (2,3-dimethylbutoxyamino)ethyl, 25 (3,3-dimethylbutoxyamino)ethyl, (1-ethylbutoxyamino)ethyl, (2-ethylbutoxyamino)ethyl, (1,1,2-trimethylpropoxyamino)ethyl, (1,2,2-trimethylpropoxyamino)ethyl, (1-ethyl-1-methylpropoxyamino)ethyl, 30 (1-ethyl-2-methylpropoxyamino)ethyl, 2-(methoxyamino)propyl, 3-(methoxyamino)propyl or 2-(ethoxyamino)propyl, preferably C1-C6-alkoxyamino-C1-C2-alkyl;
- C1-C6-alkoxy-C1-C6-alkylamino-C1-C6-alkyl:
C1-C6-alkylamino-C1-C6-alkyl, such as CHZ-NH-CH3, CHZ-NH-C2H5, CHZ-NH-CH2-C2H5, CH2-NH-CH(CH3)Z, CH2-NH-(CHZ)3-CH3, CHZ-NH-CH(CH3)-C2H5, CH2-NH-CHZ-CH(CH3)Z, CH2-NH-C(CH3)g, CHy-NH-(CH2)4-CH3, (1-methylbutylamino)methyl, (2-methylbutylamino)methyl, (3-methylbutylamino)methyl, (2,2-dimethylpropylamino)methyl, (1-ethylpropylamino)methyl, n-hexylamino-methyl, (1,1-dimethylpropylamino)methyl, (1,2-dimethylpropylamino)methyl, (1-methylpentylamino)methyl, (2-methylpentylamino)methyl, (3-methylpentylamino)methyl, (4-methylpentylamino)methyl, (1,1-dimethylbutylamino)methyl, (1,2-dimethylbutylamino)methyl, (1,3-dimethylbutylamino)methyl, (2,2-d~methylbutylamino)methyl, (2,3-dimethylbutylamino)methyl, (3,3-dimethylbutylamino)methyl, (1-ethylbutylamino)methyl, (2-ethylbutylamino)methyl, (1,1,2-trimethylpropylamino)methyl, (1,2,2-trimethylpropylamino)methyl, (1-ethyl-1-methylpropylamino)methyl, (1-ethyl-2-methylpropylamino)methyl, methylaminoethyl, ethylaminoethyl, n-propylaminoethyl, (1-methylethylamino)ethyl, n-butylaminoethyl, (1-methylpropylamino)ethyl, (2-methylpropylamino)ethyl, (l,l-dimethylethylamino)ethyl, n-pentylaminoethyl, (1-methylbutylamino)ethyl, (2-methylbutylamino)ethyl, (3-methylbutylamino)ethyl, (2,2-dimethylpropylamino)ethyl, (1-ethylpropylamino)ethyl, n-hexylaminoethyl, (1,1-dimethylpropylamino)ethyl, (1,2-dimethylpropylamino)ethyl, (1-methylpentylamino)ethyl, (2-methylpentylamino)ethyl, (3-methylpentylamino)ethyl, (4-methylpentylamino)ethyl, (1,1-dimethylbutylamino)ethyl, (1,2-dimethylbutylamino)ethyl, (1,3-dimethylbutylamino)ethyl, (2,2-dimethylbutylamino)ethyl, (2,3-dimethylbutylamino)ethyl, (3,3-dimethylbutylamino)ethyl, (1-ethylbutylamino)ethyl, (2-ethylbutylamino)ethyl, (1,1,2-trimethylpropylarnino)ethyl, (1,2,2-trimethylpropylamino)ethyl, (1-ethyl-1-methylpropylamino)ethyl, (1-ethyl-2-methylpropylamino)ethyl, 2-(methylamino)propyl, 3-(methylamino)propyl and 2-(ethylamino)propyl, preferably C1-C6-alkylamino-C1-CZ-alkyl, which is substituted by C1-C6-alkoxy as mentioned above, i.e., for example, CH2-NH-CHZ-OCH3 or CH2-NH-CH2-OC2H5;
- C1-C6-alkyloximino-C1-C6-alkyl: C1-C6-alkyl which is substituted by C1-C6-alkyloximino, such as methoxyimino, ethoxyimino, 1-propoxyimino, 2-propoxyimino, 1-methylethoxyimino, n-butoxyimino, sec-butoxyimino, tert-butoxyimino, 1-methyl-1-propoxyimino, 2-methyl-1-propoxyimino, 1-methyl-2-propoxyimino, 2-methyl-2-propoxyimino, n-pentoxyimino, 2-pentoxyimino, 3-pentoxyimino, 4-pentoxyimino, 1-methyl-1-butoxyimino, 2-methyl-1-butoxyimino, 3-methyl-1-butoxyimino, 1-methyl-2-butoxyimino, 2-methyl-2-butoxyimino, 3-methyl-2-butoxyimino, 1-methyl-3-butoxyimino, 2-methyl-3-butoxyimino, 3-methyl-3-butoxyimino, 1,1-dimethyl-2-propoxyimino, 1,2-dimethyl-1-propoxyimino, 1,2-dimethyl-2-propoxyimino, 1-ethyl-1-propoxyimino, 1-ethyl-2-propoxyimino, n-hexoxyimino, 2-hexoxyimino, 3-hexoxyimino, 4-hexoxyimino, 5-hexoxyimino, 1-mEthyl-1-pentoxyimino, 2-methyl-1-pentoxyimino, 3-methyl-1-pentoxyimino, 4-methyl-J.-pentoxyimino, 1-methyl-2-pentoxyimino, 2-methyl-2-pentoxyimino, 3-methyl-2-pentoxyimino, 4-methyl-2-pentoxyimino, 1-methyl-3-pentoxyimino, 2-methyl-3-pentoxyimino, 3-methyl-3-pentoxyimino, 4-methyl-3-pentoxyimino, 1-methyl-4-pentoxyimino, 2-methyl-4-pentoxyimino, 3-methyl-4-pentoxyimino, 4-methyl-4-pentoxyimino, 1,1-dimethyl-2-butoxyimino, 1,1-dimethyl-3-butoxyimino, 1,2-dimethyl-1-butoxyimino, 1,2-dimethyl-2-butoxyimino, 1,2-dimethyl-3-butoxyimino, 1,3-dimethyl-1-butoxyimino, 1,3-dimethyl-2-butoxyimino, 1,3-dimethyl-3-butoxyimino, 2,2-dimethyl-3-butoxyimino, 2,3-dimethyl-1-butoxyimino, 2,3-dimethyl-2-butoxyimino, 2,3-dimethyl-3-butoxyimino, 3,3-dimethyl-1-butoxyimino, 3,3-dimethyl-2-butoxyimino, 1-ethyl-1-butoxyimino, 1-ethyl-2-butoxyimino, 1-ethyl-3-butoxyimino, 2-ethyl-1-butoxyimino, 2-ethyl-2-butoxyimino, 2-ethyl-3-butoxyimino, 1,1,2-trimethyl-2-propoxyimino, 1-ethyl-1-methyl-2-propoxyimino, 1-ethyl-2-methyl-1-propoxyimino and 1-ethyl-2-methyl-2-propoxyimino, i.e., for example, methoxyiminomethyl;
- C1-C6-alkoxy-C1-C6-alkyl: C1-C6-alkyl which is substituted by C1-C6-alkoxy as mentioned above, i.e., for example, CH2-OCH3, CH2-OC2H5, n-propoxymethyl, CHZ-OCH(CHg)2, n-butoxymethyl, (1-methylpropoxy)methyl, (2-methylpropoxy)methyl, CHZ-OC(CH3)3, 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, 3-(n-butoxy)butyl, 3-(1-methylpropoxy)butyl, 3-(2-methylpropoxy)butyl, 3-(1,1-dimethylethoxy)butyl, 4-(methoxy)butyl, 4-(e-~hoxy)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 CH2-OCH3 or 2-methoxyethyl;
- di(C1-C6-alkoxy)-C1-C6-alkyl: for example 2,2-dimethoxyethyl or 2,2-diethoxyethyl;
Ci-C6-alkoxy-C1-C6-alkoxy: C1-C6-alkoxy which is substituted by C1-C6-alkoxy as mentioned above, i.e., for example, OCH2-OCH3, OCH2-OC2H5, n-propoxymethoxy, OCH2-OCH(CH3)Z.
n-butoxymethoxy, (1-methylpropoxy)methoxy, (2-methylpropoxy)methoxy, OCH2-OC(CH3)3, 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-(I,1-dimethylethoxy)butoxy, 5-(methoxy)pentoxy, 5-(ethoxy)pentoxy, 5-(n-propoxy)pentoxy, 5-(1-methylethoxy)pentoxy, 5-(n-butoxy)pentoxy, 5-(1-methylpropoxy)pentoxy, 5-(2-methylpropoxy)pentoxy, 5-(l,l-dimethylethoxy)pentoxy, 6-(methoxy)hexoxy, 6-(ethoxy)hexoxy, 6-(n-propoxy)hexoxy, 6-(1-methylethoxy)hexoxy, 6-(n-butoxy)hexoxy, 6-(1-methylpropoxy)hexoxy, 6-(2-methylpropoxy)hexoxy or 6-(1,1-dimethylethoxy)hexoxy, in particular OCHZ-OCH3 or OCHZ-OCZH5;

- (C1-C6-alkyl)carbonyl-C1-C6-alkoxy: C1-C6-alkoxy which is substituted by (C1-C6-alkyl)carbonyl as mentioned above, i.e., for example, OCHZ-CO-CH3, OCHz-CO-C2H5, OCH2-CO-CHZ-C2H5, OCHz-CO-CH(CH3)Z, n-butylcarbonyl-methoxy, 1-(CO-CH3)ethoxy, 2-(CO-CH3)ethoxy, 2-(CO-C2H5)ethoxy, 2-(CO-CHZ-C2H5)ethoxy, 2-(n-butylcarbonyl)ethoxy, 3-(CO-CH3)propoxy, 3-(CO-C2H5)-propoxy, 3-(CO-CH2-CZH5)propoxy, 3-(n-butylcarbonyl)propoxy, 4-(CO-CH3)butoxy, 4-(CO-C2H5)butoxy, 4-(CO-CHZ-C2H5)butoxy, 4-(n-butylcarbonyl)butoxy, 5-(CO-CH3)pentoxy, 5-(CO-C2H5)pentoxy, 5-(CO-CH2-G2H5)pentoxy, 5-(n-butylcarbonyl)butoxy, 6-(CO-CH3)hexoxy, 6-(CO-C2H5)hexoxy, 6-(CO-CH2-CZH5)hexoxy or 6-(n-butylcarbonyl)hexoxy, in particular OCH2-CO-OCH3 or 1-(CO-CH3)ethoxy;
- (C1-C6-alkoxy)carbonyl-C1-C6-alkoxy: C1-C6-alkoxy which is substituted by (C1-C6-alkoxy)carbonyl as mentioned above, i.e., for example, OCH2-CO-OCH3, OCHZ-CO-OCZHS, OCH2-CO-OCHZ-C2H5, OCH2-CO-OCH(CH3)2, n-butoxycarbonylmethoxy, 1-(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)butaxy, 4-(ethoxycarbonyl)butoxy, 4-(n-propoxycarbonyl)butoxy, 4-(n-butoxycarbonyl)butoxy, 5-(methoxycarbonyl)pentoxy, 5-(ethoxycarbonyl)pentoxy, 5-(n-propoxycarbonyl)pentoxy, 5-(n-butoxycarbonyl)butoxy, 6-(methoxycarbonyl)hexoxy, 6-(ethoxycarbonyl)hexoxy, 6-(n-propoxycarbonyl)hexoxy or 6-(n-butoxycarbonyl)hexoxy, in particular OCHZ-CO-OCH3 or 1-(methoxycarbonyl)ethoxy;
- (C1-C6-alkoxy)carbonyl-C1-C6-alkyl: C1-C6-alkyl which is substituted by (C1-C6-alkoxy)carbonyl as mentioned above, i.e., for example, methoxycarbonylmethyl, ethoxycarbonylmethyl, 1-(methoxycarbonyl)ethyl, 2-(methoxycarbonyl)ethyl, 2-(ethoxycarbonyl)ethyl, 3-(methoxycarbonyl)propyl, 4-(methoxycarbonyl)butyl, 5-(methoxycarbonyl)pentyl or 6-(methoxycarbonyl)hexyl;
- (C1-C6-alkoxy)carbonyl-C1-C6-alkylsulfonyl:
C1-C6-alkylsulfonyl which is substituted by (C1-C6-alkoxy)carbonyl as mentioned above, i.e., for example, methoxycarbonylmethylsulfonyl, ethoxycarbonylmethylsulfonyl, 1-(methoxycarbonyl)ethylsulfonyl, 2-(meth~xycarbonyl)ethylsulfonyl, w 2-(ethoxycarbonyl)ethylsulfonyl, 3-(methoxycarbonyl)propylsulfonyl, 4-(methoxycarbonyl)butylsulfonyl, 5-(methoxycarbonyl)pentylsulfonyl or 5 6-(methoxycarbonyl)hexylsulfonyl;
C1-C6-alkylthio-C1-C6-alkyl: C1-C6-alkyl which is substituted by C1-C6-alkylthio as mentioned above, i.e., for example, CH2-SCH3, CHZ-SC2H5, CH2-SCHZ-CyHS, CH2-SCH(CH3)2r 10 n-butylthiomethyl, CH2-SCH(CH3)-C2H5, CH2-SCH2-CH(CH3)2, CH2-SC(CH3)3, 2-(SCH3)ethyl, 2-(SC2H5)ethyl, 2-(SCH2-C2H5)ethyl, 2-[SCH(CH3)2]ethyl, 2-(n-butylthio)ethyl, 2-[SCH(CH3)-CaH5]ethyl, 2-(2-methylpropylthio)ethyl, 2-[SC(CH3)3]ethyl, 2-(SCH3)propyl, 3-(SCH3)propyl, 15 2-(SCZH5)propyl, 3-(SCZHS)propyl, 3-(SCH2-C2H5)propyl, 3-(butylthio)propyl, 4-(SCH3)butyl, 4-(SC2H5)butyl, 4-(SCHZ-C2H5)butyl or 4-(n-butylthio)butyl, in particular 2-(SCH3)ethyl;
20 - C1-C6-alkylthio-C1-C6-alkoxy: C1-C6-alkoxy which is substituted by C1-C6-alkylthio as mentioned above, i.e., for example, OCHZ-SCH3, OCHZ-SC2H5, OCH2-SGH2-C2H5, OCHy-SCH(CH3)2.
n-butylthiomethoxy, OCH2-SCH(CH3)-CzHS, OCH2-SCH2-CH(CH3)2, OCH2-SC(CH3)3, 2-(SCH3)ethoxy, 2-(SC2Hg)ethoxy, 25 2-(SCH2-CZH5)ethoxy, 2-[SCH(CH3)2]ethoxy, 2-(n-butylthio)ethoxy, 2-[SCH(CH3)-CZHS]ethoxy, 2-(2-methylpropylthio)ethoxy, 2-[SC(CH3)3]ethoxy, 2-(SCH3)propoxy, 3-(SCH3)propoxy, 2-(SC2H5)propoxy, 3-(SC2H5)propoxy, 3-(SCH2-C2H5)propoxy, 3-(butylthio)propoxy, 30 4-(SCH3)butoxy, 4-(SC2H5)butoxy, 4-(CH2-CyHS)butoxy or 4-(n-butylthio)butoxy, in particular 2-(SCH3)ethoxy;
- C1-C6-alkylthio-(C1-C6-alkyl)carbonyl: (C1-C6-alkyl)carbonyl which is substituted by C1-C6-alkylthio as mentioned above, 35 preferably by SCH3 or SC2H5, i.e., for example, methylthiomethylcarbonyl, ethylthiomethylcarbonyl, 1-(methylthio)ethylcarbonyl, 2-(methylthio)ethylcarbonyl, 3-(methylthio)propylcarbonyl, 4-(methylthio)butylcarbonyl, 5-(methylthio)pentylcarbonyl or 6-(methylthio)hexylcarbonyl, in particular CO-CHz-SCH3 or CO-CH(CH3)-SCH3;
- di(C1-C6-alkyl)amino-C1-C6-alkoxy: C1-C6-alkoxy which is substituted by di(C1-C6-alkyl)amino, such as N(CH3)2, N(C2H5)2, N,N-dipropylamino, N,N-di(1-methylethyl)amino, N,N-dibutylamino, N,N-di(1-methylpropyl)amino, N,N-di(2-methylpropyl)amino, N[C(CH3)312.
Iv-ethyl-N-methylami~~a, N-methyl-N-propylamino, -' N-methyl-N-(1-methylethyl)amino, N-butyl-N-methylamino, N-methyl-N-(1-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-(1,1-dimethylethyl)amino, N-(1-methylethyl)-N-propylamino, N-butyl-N-propylamino, N-(1-methylpropyl)-N-propylamino, N-(2-methylpropyl)-N-propylamino, N-(1,1-dimethylethyl)-N-propylamino, N-butyl-N-(1-methylethyl)amino, N-(1-methylethyl)-N-(1-methylpropyl)amino, N-(1-methylethyl)-N-(2-methylpropyl)amino, N-(l,l-dimethylethyl)-N-(1-methylethyl)amino, N-butyl-N-(1-methylpropyl)amino, N-butyl-N-(2-methylpropyl)amino, N-butyl-N-(1,1-dimethylethyl)amino, N-(1-methylpropyl)-N-(2-methylpropyl)amino, N-(1,1-dimethylethyl)-N-(1-methylpropyl)amino or N-(1,1-dimethylethyl)-N-(2-methylpropyl)amino, preferably by N,N-dimethylamino or N,N-diethylamino, i.e., for example, OCH2-N(CH3)2, OCHZ-N(C2H5)Z, OCH(CHg)-N(CH3)2, 2-(dimethylamino)ethoxy, OCH(CH3)-N(CZHS)2.
3-(dimethylamino)propoxy, 9-(dimethylamino)butoxy, 5-(dimethylamino)pentoxy or 6-(dimethylamino)hexoxy, in particular OCH2-N(CH3)Z or OCH(CH3)-N(CH3)2:
- C3-C6-alkenyl: for example prop-2-en-1-yl, n-buten-4-yl, 1-methylprop-2-en-1-yl, 2-methylprop-2-en-1-yl, 2-buten-1-yl, n-penten-3-yl, n-penten-4-yl, 1-methylbut-2-en-1-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, 1,1-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, 1-methylpent-3-en-1-yl, 2-methylpent-3-en-1-yl, 3-methylpent-3-en-1-yl, 4-methylpent-3-en-1-yl, 1-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-1-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-1-yl;
1-ethylbut-2-en-1-yl, 1-ethylbut-3-en--1-yl, 2-ethylbut-2-en-1-yl, 2-ethylbut-3-en-1-yl, 1,1,2-trimethylprop-2-en-1-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;
- C3-C6-haloalkenyl: C3-C6-alkenyl as mentioned above which is partially or fully substituted by fluorine, chlorine and/or bromine, i.e., for example, 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-dibromallyl, 2,3,3-tribromoallyl or 2,3-dibromobut-2-enyl, in particular 2-chloroallyl or 3,3-dichloroallyl;
- C2-C6-alkenyl: ethenyl or one of the radicals mentioned under C3-C6-alkenyl, in particular ethenyl or prop-2-en-1-yl;
- C3-C6-alkenyloxy: prop-1-en-1-yloxy, prop-2-en-1-yloxy, 1-methylethenyloxy, n-buten-1-yloxy, n-buten-2-yloxy, n-buten-3-yloxy, 1-methylprop-1-en-1-yloxy, 2-methylprop-1-en-1-yloxy, 1-methylprop-2-en-1-yloxy, 2-methylprop-2-en-1-yloxy, n-penten-1-yloxy, n-penten-2-yloxy, n-penten-3-yloxy, n-penten-4-yloxy, 1-methylbut-1-en-1-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, 1-ethylprop-1-en-2-yloxy, 1-ethylprop-2-en-1-yloxy, n-hex-1-en-1-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, 1-methylpent-1-en-1-yloxy, 2-methylpent-1-en-1-yloxy, 3-methylpent-1-en-1-yloxy, 4-methylpent-1-en-1-yloxy, 1-methylpent-2-en-1-yloxy, 2-methylpent-2-en-1-yloxy, 3-methylpent-2-en-1-yloxy, 4-methylpent-2-en-1-yloxy, 1-methylpent-3-en-1-yloxy, 2-methylpent-3-en-1-yloxy, 3-methylpent-3-en-1-yloxy, 4-methylpent-3-en-1-yloxy, 1-methylpent-4-en-1-yloxy, 2-methylpent-4-en-1-yloxy, 3-methylpent-4-en-1-yloxy, 4-methylpent-4-en-1-yloxy, 1,1-dimethylbut-2-en-1-yloxy, 1,1-dimethylbut-3-en-1-yloxy, 1,2-dimethylbut-1-en-1-yloxy, 1,2-dimethylbut-2-en-1-yloxy, 1,2-dimethylbut-3-en-1-yloxy, 1,3-dimethylbut-1-en-1-yloxy, 1,3-dimethylbut-2-en-1-yloxy, 1,3-dimethylbut-3-en-1-yloxy, 2,2-dimethylbut-3-en-1-yloxy, 2,3-dimethylbut-1-en-1-yloxy, 2,3-dimethylbut-2-en-1-yloxy, 2,3-dimethylbut-3-en-1-yloxy, 3,3-dimethylbut-1-eu-1-yloxy, 3,3-dimethylbut-2-en-1-yloxy, 1-ethylbut-1-en-1-yloxy, 1-ethylbut-2-en-1-yloxy, 1-ethylbut-3-en-1-yloxy, 2-ethylbut-1-en-1-yloxy, 2-ethylbut-2-en-1-yloxy, 2-ethylbut-3-en-1-yloxy, 1,1,2-trimethylprop-2-en-1-yloxy, 1-ethyl-1-methylprop-2-en-1-yloxy, 1-ethyl-2-methylprop-1-en-1-yloxy or 1-ethyl-2-methylprop-2-en-1-yloxy, in particular prop-2-en-1-yloxy;
- C2-C6-alkenyloxy: ethenyloxy or one of the radicals mentioned under C3-C6-alkenyloxy, in particular ethenyloxy or prop-2-en-1-yloxy;
- C3-C6-haloalkenyloxy: C3-C6-alkenyloxy as mentioned above which is partially or fully substituted by fluorine, chlorine and/or bromine, i.e., for example, 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, 3,3-dibromoallyloxy, 2,3,3-tribromoallyloxy or 2,3-dibromobut-2-enyloxy, in particular 2-chloroallyloxy or 3,3-dichloroallyloxy;
- phenyl-C3-C6-alkenyloxy: 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: for example 3-heterocyclylallyloxy, 4-heterocyclylbut-2-enyloxy, 4-heterocyclylbut-3-enyloxy or 5-heterocyclylpent-4-enyloxy, preferably 3-heterocyclylallyloxy or 4-heterocyclylbut-2-enyloxy, in particular 3-heterocyclylallyloxy;
C2-C6-alkenylthio: ethenylthio, prop-1-en-1-ylthio, prop-2-en-1-ylthio, 1-methylethenylthio, n-buten-1-ylthio, n-buten-2-ylthio, n-buten-3-ylthio, 1-methylprop-1-en-1-ylthio, 2-methylprop-1-en-1-ylthio, 1-methylprop-2-en-1-ylthio, 2-methylprop-2-en-1-ylthio, n-penten-1-ylthio, n-penten-2-ylthio, n-penten-3-ylthio, n-penten-4-ylthio, 1-methylbut-1-en-1-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, 1-methylbut-3-en-1-ylthio, ~2-methylbut-3-en-1-ylthio, 3-methylbut-3-en-1-ylthio, 1,1-dime-chylprop-2-en-1-ylthio, 1,2-dimethylprop-1-en-1-ylthio, 1,2-dimethylprop-2-en-1-ylthio, 1-ethylprop-1-en-2-ylthio, 1-ethylprop-2-en-1-ylthio, n-hex-1-en-1-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, 1-methylpent-1-en-1-ylthio, 2-methylpent-1-en-1-ylthio, 3-methylpent-1-en-1-ylthio, 4-methylpent-1-en-1-ylthio, 1-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, 1-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, 1-ethylbut-1-en-1-ylthio, 1-ethylbut-2-en-1-ylthio, 1-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-methylprop-2-en-1-ylthio, 1-ethyl-2-methylprop-1-en-1-ylthio or 1-ethyl-2-methylprop-2-en-1-ylthio, in particular ethenylthio or prop-2-en-1-ylthio;
- C3-C6-alkynyl: 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-1-yn-1-yl, n-pent-I-yn-3-yl, n-pent-1-yn-4-yl, n-pent-1-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-1-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-I-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;
- CZ-C6-alkynyl: ethynyl or one of the radicals mentioned under C3-C6-alkynyl, in particular ethynyl or prop-2-yn-1-yl;

C3-C6-alkynyloxy: prop-1-yn-1-yloxy, prop-2-yn-1-yloxy, n-but-1-yn-I-yloxy, n-but-1-yn-3-yloxy, n-but-1-yn-4-yloxy, n-but-2-yn-1-yloxy, n-pent-1-yn-I-yloxy, n-pent-1-yn-3-yloxy, n-pent-1-yn-4-yloxy, n-pent-1-yn-5-yloxy, 5 n-pent-2-yn-1-yloxy, n-pent-2-yn-4-yloxy, n-pent-2-yn-5-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, 10 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 15 particular prop-2-yn-1-yloxy;
- C2-C6-alkynyloxy: ethynyloxy or one of the radicals mentioned under C3-C6-alkynyloxy, in particular ethynyloxy or prop-2-yn-1-yloxy;
- phenyl-C3-C6-alkynyloxy: for example 3-phenylprop-2-yn-1-yloxy, 4-phenylbut-2-yn-1-yloxy, 3-phenylbut-3-yn-2-yloxy, 5-phenylpent-3-yn-1-yloxy or 6-phenylhex-4-yn-1-yloxy, in particular 3-phenylprop-2-yn-1-yloxy or 3-phenylbut-3-yn-2-yloxy;
- heterocyclyl-C3-C6-alkynyloxy: for example 3-(heterocyclyl)prop-2-yn-1-yloxy, 4-(heterocyclyl)but-2-yn-I-yloxy, 3-(heterocyclyl)but-3-yn-2-yloxy, 5-(heterocyclyl)pent-3-yn-1-yloxy or 6-(heterocyclyl)hex-4-yn-1-yloxy, in particular 3-(heterocyclyl)prop-2-yn-1-yloxy or 3-(heterocyclyl)but-3-yn-2-yloxy;
- C3-C6-alkynylthio: prop-1-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-1-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-methylpent-1-yn-5-ylthio, 4-methylpent-1-yn-1-ylthio, 4-methylpent-2-yn-4-ylthio or 4-methylpent-2-yn-5-ylthio, in particular prop-2-yn-1-ylthio;
- C2-C6-alkynylthio: ethynylthio or one of the radicals mentioned under C3-C6-alkynylthio, in particular ethynylthio or prop-2-yn-1-ylthio;
- (C3-C6-alkenyloxy)carbonyl: prop-1-en-1-yloxycarbonyl, prop-2-en-1-yloxycarbonyl, 1-methylethenyloxycarbonyl, n-buten-1-yloxycarbonyl, n-buten-2-yloxycarbonyl, n-buten-3-yloxycarbonyl, 1-methylprop-1-en-1-yloxycarbonyl, 2-methylprop-1-en-1-yloxycarbonyl, 1-methylprop-2-en-1-yloxycarbonyl, 2-methylprop-2-en-1-yloxycarbonyl, n-penten-1-yloxycarbonyl, n-penten-2-yloxycarbonyl, n-penten-3-yloxycarbonyl, n-penten-4-yloxycarbonyl, 1-methylbut-1-en-1-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, 1-methylbut-3-en-1-yloxycarbonyl, 2-methylbut-3-en-1-yloxycarbonyl, 3-methylbut-3-en-1-yloxycarbonyl, l,l-dimethylprop-2-en-1-yloxycarbonyl, 1,2-dimethylprop-1-en-1-yloxycarbonyl, 1,2-dimethylprop-2-en-1-yloxycarbonyl, 1-ethylprop-1-en-2-yloxycarbonyl, 1-ethylprop-2-en-1-yloxycarbonyl, n-hex-1-en-1-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, 1-methylpent-1-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, 1-methylpent-3-en-1-yloxycarbonyl, 2-methylpent-3-en-1-yloxycarbonyl, 3-methylpent-3-en-1-yloxycarbonyl, 4-methylpent-3-en-1-yloxycarbonyl, 1-methj~lpent-4-erg-1-yloxycarbonyl, ' ' 0050~5~0$0 CA 02377143 2001-12-19 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-1-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, 1-ethylbut-1-en-1-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, 1-ethyl-1-methylprop-2-en-1-yloxycarbonyl, 1-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-C1-C6-alkyl: C1-C6-alkyl which is substituted by (C3-C6-alkenyloxy)carbonyl as mentioned above, preferably by prop-2-en-1-yl-oxycarbonyl, i.e., for example, prop-2-en-1-yl-oxycarbonylmethyl;
- (CZ-C6-alkenyl)carbonyloxy: ethenylcarbonyloxy, prop-1-en-1-ylcarbonyloxy, prop-2-en-1-ylcarbonyloxy, 1-methylethenylcarbonyloxy, n-buten-1-ylcarbonyloxy, n-buten-2-ylcarbonyloxy, n-buten-3-ylcarbonyloxy, 1-methylprop-1-en-1-ylcarbonyloxy, 2-methylprop-1-en-1-ylcarbonyloxy, 1-methylprop-2-en-1-ylcarbonyloxy, 2-methylprop-2-en-1-ylcarbonyloxy, n-penten-1-ylcarbonyloxy, n-penten-2-ylcarbonyloxy, n-penten-3-ylcarbonyloxy, n-penten-4-ylcarbonyloxy, 1-methylbut-1-en-1-ylcarbonyloxy, 2-methylbut-1-en-1-ylcarbonyloxy, 3-methylbut-1-en-1-ylcarbonyloxy, 1-methylbui:-2-en-1-ylcarbo~iyloxy, 2-methylbut-2-en-1-ylcarbonyloxy, 3-methylbut-2-en-1-ylcarbonyloxy, 1-methylbut-3-en-1-ylcarbonyloxy, 2-methylbut-3-en-1-ylcarbonyloxy, 3-methylbut-3-en-1-ylcarbonyloxy, 1,1-dimethylprop-2-en-1-ylcarbonyloxy, 1,2-dimethylprop-1-en-1-ylcarbonyloxy, 1,2-dimethylprop-2-en-1-ylcarbonyloxy, 1-ethylprop-1-en-2-ylcarbonyloxy, 1-ethylprop-2-en-1-ylcarbonyloxy, n-hex-1-en-1-ylcarbonyloxy, n-hex-2-en-1-ylcarbonyloxy, n-hex-3-en-I-ylcarbonyloxy, n-hex-4-en-1-ylcarbonyloxy, n-hex-5-en-1-ylcarbonyloxy, 1-methylpent-1-en-I-ylcarbonyloxy, 2-methylpent-1-en-1-ylcarbonyloxy, 3-methylpent-1-en-1-ylcarbonyloxy, 4-methylpent-1-en-1-ylcarbonyloxy, 1-methylpent-2-en-1-ylcarbonyloxy, 2-methylpent-2-en-1-ylcarbonyloxy, 3-methylpent-2-en-1-ylcarbonyloxy, 4-methylpent-2-en-1-ylcarbonyloxy, 1-methylpent-3-en-1-ylcarbonyloxy, 2-methylpent-3-en-1-ylcarbonyloxy, 3-methylpent-3-en-1-ylcarbonyloxy, 4-methylpent-3-en-1-ylcarbonyloxy, 1-methylpent-4-en-1-ylcarbonyloxy, 2-methylpent-4-en-1-ylcarbonyloxy, 3-methylpent-4-en-1-ylcarbonyloxy, 4-methylpent-4-en-1-ylcarbonyloxy, 1,1-dimethylbut-2-en-1-ylcarbonyloxy, 1,1-dimethylbut-3-en-1-ylcarbonyloxy, 1,2-dimethylbut-1-en-1-ylcarbonyloxy, 1,2-dimethylbut-2-en-1-ylcarbonyloxy, 1,2-dimethylbut-3-en-1-ylcarbonyloxy, 1,3-dimethylbut-1-en-1-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-1-ylcarbonyloxy, 3,3-dimethylbut-1-en-1-ylcarbonyloxy, 3,3-dimethylbut-2-en-1-ylcarbonyloxy, 1-ethylbut-1-en-1-ylcarbonyloxy, 1-ethylbut-2-en-1-ylcarbonyloxy, 1-ethylbut-3-en-1-ylcarbonyloxy, 2-ethylbut-1-en-1-ylcarbonyloxy, 2-ethylbut-2-en-1-ylcdrbon;~loxy, 2-ethylbut-3-en-1-ylcarbonyloxy, 1,1,2-trimethylprop-2-en-1-ylcarbonyloxy, 1-ethyl-1-methylprop-2-en-1-ylcarbonyloxy, 1-ethyl-2-methylprop-1-en-1-ylcarbonyloxy or 1-ethyl-2-methylprop-2-en-1-ylcarbonyloxy, in particular ethenylcarbonyloxy or prop-2-en-1-ylcarbonyloxy;
- (CZ-C6-alkenyl)carbonylthio: ethenylcarbonylthio, prop-1-en-1-ylcarbonylthio, prop-2-en-1-ylcarbonylthio, 1-methylethenylcarbonylthio, n-buten-1-ylcarbonylthio, n-buten-2-ylcarbonylthio, n-buten-3-ylcarbonylthio, 1-methylprop-1-en-1-ylcarbonylthio, 2-methylprop-1-en-1-ylcarbonylthio, 1-methylprop-2-en-1-ylcarbonylthio, 2-methylprop-2-en-1-ylcarbonylthio, n-penten-1-ylcarbonylthio, n-penten-2-ylcarbonylthio, n-penten-3-ylcarbonylthio, n-penten-4-ylcarbonylthio, 1-methylbut-1-en-1-ylcarbonylthio, 2-methylbut-1-en-1-ylcarbonylthio, 3-methylbut-1-en-1-ylcarbonylthio, 1-methylbut-2-en-1-ylcarbonylthio, 2-rnethylbut-2-en-1-ylcarbonylthio, 3-methylbut-2-en-1-ylcarbonylthio, 1-methylbut-3-en-1-ylcarbonylthio, 2-methylbut-3-en-1-ylcarbonylthio, 3-methylbut-3-en-1-ylcarbonylthio, 1,1-dimethylprop-2-en-1-ylcarbonylthio, 1,2-dimethylprop-1-en-1-ylcarbonylthio, 1,2-dimethylprop-2-en-1-ylcarbonylthio, 1-ethylprop-1-en-2-ylcarbonylthio, 1-ethylprop-2-en-1-ylcarbonylthio, n-hex-1-en-1-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, 1-methylpent-1-en-1-ylcarbonylthio, 2-methylpent-1-en-1-ylcarbonylthio, 3-methylpent-1-en-1-ylcarbonylthio, 4-methylpent-1-en-1-ylcarbonylthio, 1-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, 1-methylYent-4-en-1-ylcarbonyltiiio,- rw 2-methylpent-4-en-1-ylcarbonylthio, 3-methylpent-4-en-1-ylcarbonylthio, 4-methylpent-4-en-1-ylcarbonylthio, 1,1-dimethylbut-2-en-1-ylcarbonylthio, 5 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, 10 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, 15 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, 1-ethylbut-2-en-1-ylcarbonylthio, 1-ethylbut-3-en-1-ylcarbonylthio, 20 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, 1-ethyl-1-methylprop-2-en-1-ylcarbonylthio, 25 1-ethyl-2-methylprop-1-en-1-ylcarbonylthio or 1-ethyl-2-methylprop-2-en-1-ylcarbonylthio, in particular ethenylcarbonylthio or prop-2-en-1-ylcarbonylthio;
- (CZ-C6-alkynyl)carbonyloxy: ethynylcarbonyloxy, 30 prop-1-yn-1-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-1-yn-1-ylcarbonyloxy, n-pent-1-yn-3-ylcarbonyloxy, n-pent-1-yn-4-ylcarbonyloxy, n-pent-1-yn-5-ylcarbonyloxy, 35 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, 40 n-hex-1-yn-5-ylcarbonyloxy, n-hex-1-yn-6-ylcarbanyloxy, 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, 45 3-methylpent-1-yn-3-ylcarbonyloxy, 3-methylpent-1-yn-4-ylcarbonyloxy,.
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 ethynylcarbonyloxy or prop-2-yn-1-ylcarbonyloxy;
_ C3-C6-alkynylsulfonyloxy: prop-1-yn-1-ylsulfonyloxy, prop-2-yn-1-ylsulfonyloxy, n-but-1-yn-1-ylsulfonyloxy, n-but-1-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-1-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-y.lsulfonyloxy, 4-methylpent-2-yn-4-ylsulfonyloxy or 4-methylpent-2-yn-5-ylsulfonyloxy, in particular prop-2-yn-1-ylsulfonyloxy;
_ (Cz-C6-alkynyl)carbonylthio: ethynylcarbonylthio, 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, n-hex-3-yn-2-ylcarbonylthio, 3-methylpent-1-yn-1-ylcarbonylthio, 3-methylpent-1-yn-3-ylcarbonylthio, -.
3-methylpent-I-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;
- (C1-C6-alkoxy)carbonyl-C2-C6-alkenyl: C2-C6-alkenyl which is substituted by (C1-C6-alkoxy)carbonyl as mentioned above, i.e., for example, methoxycarbonylprop-2-en-1-y.l;

- (C1-C6-alkoxy)carbonyl-C2-C6-alkenyloxy: C2-C6-alkenyloxy which is substituted by (C1-C6-alkoxy)carbonyl as mentioned above, i.e., for example, 1-methoxycarbonylethen-1-yloxy and methoxycarbonylprop-2-en-1-yloxy;
- C1-C6-alkoxy-C3-C6-alkenyloxy: C3-C6-alkenyloxy which is substituted by C1-C6-alkoxy as mentioned above, i.e., for example, methylprop-2-en-1-yloxy;
- C3-C6-alkenyloxy-C1-C6-alkyl: C1-C6-alkyl which is substituted by C3-C6-alkenyloxy as mentioned above, preferably allyloxy, 2-methylprop-2-en-1-yloxy, but-1-en-3-yloxy, but-1-en-4-yloxy or but-2-en-1-yloxy, i.e., for example, allyloxymethyl, 2-allyloxyethyl or but-1-en-4-yloxymethyl;
C3-C6-alkynyloxy-G1-C6-alkyl: C1-C6-alkyl which is substituted by C3-C6-alkynyloxy as mentioned above, preferably propargyloxy, but-1-yn-3-yloxy, but-1-yn-4-yloxy or but-2-yn-1-yloxy, i.e., for example, propargyloxymethyl or 2-propargyloxyethyl;
- C3-C6-cycloalkyl: cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl;
- C3-C6-cycloalkyl-C1-C6-alkoxy: for example cyclopropylmethoxy, cyclobutylmethoxy, cyclopentylmethoxy, cyclohexylmethoxy, 1-(cyclopropyl)ethoxy, 1-(cyclobutyl)ethoxy, 1-(cyclopentyl)ethoxy, 1-(cyclohexyl)ethoxy, 2-(cyclopropyl)ethoxy, 2-(cyclobutyl)ethoxy, 2-(cyclopentyl)ethoxy, 2-(cyclohexyl)ethoxy, 3-(cyclopropyl)propoxy, 3-(cyclobutyl)propoxy, 3-(cyclopentyl)propoxy, 3-(cyclohexyl)propoxy, 4-(cyclopropyl)butoxy, 4-(cyclobutyl)butoxy, 4-(cyclopentyl)butoxy, 4-(cyclohexyl)butoxy, 5-(cyclopropyl)pentoxy, 5-(cyclobutyl)pentoxy, 5-(cyclopentyl)pentoxy, 5-(cyclohexyl)pentoxy, 6-(cyclopropyl)hexoAy, 6-(cyclobutyl)hexoxy, 6-(cyclopentyl)hexoxy or 6-(cyclohexyl)hexoxy, in particular cyclopentylmethoxy or cyclohexylmethoxy;
- C3-C6-cycloalkyloxy: cyclopropyloxy, cyclobutyloxy, cyclopentyloxy or cyclohexyloxy;
- C3-C6-cycloalkylthio: cyclopropylthio, cyclobutylthio, cyclopentylthio or cyclohexylthio;
- C3-C6-cycloalkylcarbonyloxy: cyclopropylcarbonyloxy, cyclobutylcarbonyloxy, cyclopentylcarbonyloxy or cyclohexylcarbonyloxy;
- C3-C6-cycloalkylsulfonyloxy: cyclopropylsulfonyloxy, cyclobutylsulfonyloxy, cyclopentylsulfonyloxy or cyclohexylsulfonyloxy;
- C5-C7-cycloalkenyloxy: cyclopent-1-enyloxy, cyclopent-2-enyloxy, cyclopent-3-enyloxy, cyclohex-1-enyloxy, cyclohex-2-enyloxy, cyclohex-3-enyloxy, cyclohept-1-enyloxy, cyclohept-2-enyloxy, cyclohept-3-enyloxy or cyclohept-4-enyloxy.
3- to 7-membered azaheterocycles which, in addition to carbon ring members, may also comprise, as a ring member, an oxygen or sulfur atom are, for example, pyrrolidin-1-yl, isoxazolidin-2-yl, isothiazolidin-2-yl, oxazolidin-3-yl, thiazolidin-3-yl, piperidin-1-yl, morpholin-1-yl, thiomorpholin-1-yl and azepin-1-yl.
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 not only saturated, partially or fully unsaturated, but also aromatic heterocycles having one to three heteroatoms selected from a group consisting of - one to three nitrogen atoms, - one or two oxygen atoms and - one or two sulfur atoms.
Examples of saturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are:
oxiranyl, thiiranyl, aziridin-1-yl, aziridin-2-yl, diaziridin-1-yl, diaziridin-3-yl, oxetan-2-yl, oxetan-3-yl, thietan-2-yl, thietan-3-yl, azetidin-1-yl, azetidin-2-yl, azetidin-3-yl, tetrahydrofuran-2-yl, tetrahydrofuran-3-yl, tetrahydrothiophen-2-yl, tetrahydrothiophen-3-yl, pyrrolidin-1-yl, pyrrolidin-2-yl, pyrrolidin-3-yl, w 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, 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-1-yl, tetrahydropyrazol-3-yl, tetrahydropyrazol-4-yl, tetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl, tetrahydrothiopyran-2-yl, tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl, piperidin-1-yl, piperidin-2-yl, piperidin-3-yl, piperidin-4-yl, 1,3-dioxan-2-yl, 1,3-dioxan-4-yl, 1,3-dioxan-5-yl, 1,4-dioxan-2-y1, 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-1-yl, hexahydropyridazin-3-yl, hexahydropyridazin-4-yl, hexahydropyrimidin-1-yl, hexahydropyrimidin-2-yl, hexahydropyrimidin-4-yl, hexahydropyrimidin-5-yl, piperazin-1-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, 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-1-yl, hexahydroazepin-2-yl, hexahydroazepin-3-yl, hexahydroazepin-4-yl, hexahydro-1,3-diazepin-1-yl, hexahydro-1,3-diazepin-2-yl, hexahydro-1,3-diazepin-4-yl, hexahydro-1,4-diazepin-1-yl and hexahydro-1,4-diazepin-2-yl.
Examples of unsaturated heterocycles which can contain a carbonyl or thiocarbonyl ring member are:
dihydrofuran-2-yl, 1,2-oxazolin-3-yl, 1,2-oxazolin-5-yl, 1,3-oxazolin-2-yl.
Preferred amongst the heteroaromatic compounds are those with 5 and 6 members, i.e., for example furyl, such as 2-furyl and 3-furyl, thienyl, such as 2-thienyl and 3-thienyl, pyrralyl, such as 2-pyrrolyl and 3-pyrrolyl, isoxazolyl, such as 3-isoxazolyl, 4-isoxazolyl and 5-isoxazolyl, isothiazolyl, such as 3-isothiazolyl, 4-isothiazolyl and 5-isothiazolyl, pyrazolyl, such as 3-pyrazolyl, 4-pyrazolyl and 5-pyrazolyl, oxazolyl, such as 2-oxazolyl, 4-oxazolyl and 5-oxazolyl, thiazolyl, such as 2-thiazolyl, 4-thiazolyl and 5-thiazolyl, imidazolyl, such as 2-imidazolyl and 4-imidazolyl, oxadiazolyi, such as 1,2,4-oxadiazol-3-yi, 1,2,4-oxadiazol-5-yl~-and 1,3,4-oxadiazol-2-yl, thiadiazolyl, such as 1,2,4-thiadiazol-3-yl, 1,2,4-thiadiazol-5-yl and 1,3,4-thiadiazol-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 5 2-pyridinyl, 3-pyridinyl and 4-pyridinyl, pyridazinyl, such as 3-pyridazinyl and 4-pyridazinyl, pyrimidinyl, such as 2-pyrimidinyl, 4-pyrimidinyl and 5-pyrimidinyl, furthermore 2-pyrazinyl, 1,3,5-triazin-2-yl and 1,2,4-triazin-3-yl, in particular pyridyl, pyrimidyl, furanyl and thienyl.
With a view to the use of the substituted ureas of the formulae Ia and Ib according to the invention as herbicides, the variables preferably have the following meanings, in each case on their own or in combination:
Z is O or S
RA is C02R1, halogen, cyano, OR2 or C1-C3-alkyl;
Q is Q1. Qz or Q4.
X, Y and Y' independently of one another are O or S;
T is a chemical bond or O;
U is a chemical bond, C1-C4-alkylene, O or S;
R is hydrogen, C(O)OR1~, C(O)SR1~, C(S)OR1~, C(S)SR1~, CHO, CN, C(O)R2, C(O)NR11R12, C(S)NR11R1z, C(0)NHC(O)OR12~, C(O)NHS(O)2R12~, C(O)NHS(O)yORl2~;
R1 is hydrogen or C1-C3-alkyl;
R2 is C1-C3-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C3-haloalkyl, C1-C3-alkoxycarbonyl-C1-C3-alkyl, cyano-C1-C3-alkyl, benzyl, which may be substituted by halogen, C1-C4-alkyl or trifluoromethyl, or is phenyl, which may be substituted by halogen, C1-C4-alkyl, trifluoromethyl or C1-C4-alkoxy;
R3 is hydrogen, fluorine or chlorine;
R4 is chlorine, trifluoromethyl or cyano;

R5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-haloalkoxy, Ci-C6-haloalkylthio, Ci-C6-alkoxy-(C1-C6-alkyl)carbonyl, Ci-C6-alkylthio-(Ci-C6-alkyl)carbonyl, (Ci-C6-alkyl)iminooxycarbonyl, Ci-C6-alkoxy-Ci-C6-alkyl, Ci-C6-alkoxyamino-Ci-C6-alkyl, Ci-C6-alkoxy-Ci-C6-alkylamino-Ci-C6-alkyl, is Ci-C6-alkoxy, Ci-C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C2-C6-alkenyloxy, C2-C6-alkenylthio, C2-C6-alkynyloxy, C2-C6-alkynylthio, (Ci-C6-alkyl)carbonyloxy, (Ci-C6-alkyl)carbonylthio, (Ci-C6-alkoxy)carbonyloxy, (C2-C6-alkenyl)carbonyloxy, (C2-C6-alkenyl)carbonylthio, (C2-C6-alkynyl)carbonyloxy, (C2-C6-alkynyl)carbonylthio, Ci-C6-alkylsulfonyloxy or Ci-C6-alkylsulfonyl, where each of these 17 radicals may, if desired, carry one, two or three substituents, selected from the group consisting of:
- halogen, nitro, cyano, hydroxyl, C3-C6-cycloalkyl, Ci-C6-alkoxy, C3-C6-cycloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, Ci-C6-alkoxy-Ci-C6-alkoxy, Ci-C6-alkylthio, Ci-C6-alkylsulfinyl, Ci-C6-alkylsulfonyl, Ci-C6-alkylideneaminooxy, oxo, =N-OR13 - phenyl, phenoxy or phenylsulfonyl, where the three last-mentioned substituents may for their part carry one, two or three substituents, in each case selected from the group consisting of halogen, nitro, cyano, Ci-C6-alkyl, Ci-C6-haloalkyl, Ci-C6-alkoxy and (Ci-C6-alkoxy)carbonyl;
_ _CO_R14~ -CO_OR14, -CO-SR14, -CO-N(R14)-R15~ _pC0-R14, -OCO-OR14' , -OCO-SR14' , -OCO-N ( R14 ) -R15 ~ _N ( R14 ) _R15 ~
and -C(Ri6)=N-OR13;
is C(Zi)-R17, -C(=NRi~)Ri7, C(R17) (Z2R19) (Z3R2o) ~
G ( R17 ) cc ( R21 ) _CN, f ( Ri 7 ) =G ( R21 ) _Gp_R22 ~
-CH(Ri7)-CH(R21)-COR22, -C(Ri7)=C(R21)_CHZ_CO_R22~
_G(R17)=G(R21)_G(R23)=G(R24)_GO_R22~
-G(Ri7)=C(R21)-CHZ_CH(R25)-CO_R22, -CO_OR26, -CO-SR26, -CON(R26)-OR13~ _C~C-CO-NHORi3, -CSC-CO-N(R26)-OR13, -G5C-CS-NH-OR13, -CSC-CS-N(R26)-OR13, -C(R17)=C(R21)_CO-NHOR13, -C(R17)=C(R21)_CO_N(R26)_pRi3, -G(R17)=G(R21)_Gg_NHOR13, -C(R17)=G(R21)_Gc~_N(R26)-pRi3, -G ( R17 ) =G ( R21 ) -G ( R16 ) =N-OR13 ~ G ( R16 ) =N-GR13 ~ ,.

-CSC-C(R16)=NOR13, C(z2R19)(Z3R2o)-pR26, -C(Z2R19)(Z2R20)SR26, C(22R19)(Z3R20)-N(R27)R28~ -N(R27)-R28~
-CO-N(R27)-R28 or -C(R17)=C(R21)CO-N(R27)R28; in which Z1.
Z2, Z3 independently of one another are oxygen or sulfur;
R6 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, or is 3- to 7-membered saturated heterocyclyl which contains one or more oxygen and/or sulfur atoms;
R7 is hydrogen or C1-C6-alkyl;
R8 is hydrogen or Ci-C3-alkyl;
R9 is hydrogen, C1-C3-alkyl Re and R9 together are C=O;
Rlo is C1-C15-alkyl, C3-C8-cycloalkyl, C2-Clo-alkenyl, Cs-Clo-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyl, C3-C6-alkynyloxy-C1-C6-alkyl, cyano-C1-C6-alkyl, is phenyl or benzyl which may in each case be mono- to pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, amino, C2-C4-monoalkylamino, C1-C4-dialkylamino, C1-C4-alkoxycarbonyl, nitro or cyano;
R11 is hydrogen, C1-C6-alkyl or Cl-C6-alkoxy;
R12 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, phenyl or benzyl which may be mono- to pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-dialkylamino, C1-C4-alkoxycarbonyl, nitro or cyano;
or R11 and R12 together with the common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle;
R12' is as defined for R12, but excluding hydrogen;
R13 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl, cyanu-C1-C6-alkyl;

(C1-C6-alkoxy)carbonyl-C1-C6-alkyl or phenylalkyl, where the phenyl ring may be mono- to trisubstituted by halogen, cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl or C1-C3-alkoxy;
R14 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-alkenyloxycarbonyl-C1-C6-alkyl, is phenyl or benzyl which may be unsubstituted on the phenyl ring or may be mono- to trisubstituted by halogen, cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl or C1-C3-alkoxy;
R14' is as defined for R14, but excluding hydrogen;
Rl5 is hydrogen, hydroxyl, C1-C6-alkyl, Cl-C6-alkoxy, (C1-C3-alkoxy)carbonyl-C1-C3-alkoxy, C3-C6-alkenyl or C3-C6-alkynyl;
R16 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C6-alkenyloxy, (C1-C6-alkoxy)carbonylalkoxy, CZ-C6-alkenyl, (C2-C6-alkenyl)carbonyloxy, C3-C6-alkynyl, (CZ-C6-alkynyl)carbonyloxy, is phenyl, phenoxy or benzyl, where the phenyl rings of the 3 last-mentioned radicals may be unsubstituted or mono- to trisubstituted by halogen, cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy or (C1-C3-alkoxy)carbonyl;
R1~ is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;
R18 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy, (C1-C6-alkoxy)carbonyl-C1-C6-alkyl, is phenyl or phenyl-(C1-C6-alkyl), where the two last-mentioned phenyl radicals may be substituted by halogen, cyano, nitro, C1-C3-alkyl, C~_-C3-haloalkyl, C1-C3-alkoxy or (C1-C3-alkoxy)carbonyl;

0~50~5~~8~ CA 02377143 2001-12-19 Rls~ Rzo independently of one another are C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl, or Rls and Rzo together are a saturated 2- to 4-membered carbon chain which may carry an oxo substituent, where a carbon atom of this chain which is not adjacent to the variables Zz and Z3 may be replaced by -O-, -S-, -N=, -NH- or -N(C1-C6-alkyl)- and where the carbon chain may be substituted once to three times by halogen or C1-C6-alkyl;
Rzl is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy;
Rzz is hydrogen, OR31, S-R31, C1-C6-alkyl, which may carry one or two C1-C6-alkoxy substituents, is Cz-C6-alkenyl, Cz-C6-alkynyl, C1-C6-haloalkyl or C3-C6-cycloalkyl;
Rz3 is hydrogen, cyano, halogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;
Rz4 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy or C1-C6-haloalkyl;
Rz5 is hydrogen, cyano or Cl-C6-alkyl;
Rz6, R31 independently of one another are hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, Cz-C6-alkenyl or Cz-C6-alkynyl, where the 4 last-mentioned groups may in each case carry one or two of the following radicals:
cyano, halogen, C1-C6-alkoxy, C1-C6-alkylcarbonyl, (C1-C6-alkoxy)carbonyl;
or are (C1-C6-alkyl)carbonyl, (Cl-C6-alkoxy)carbonyl, phenyl or phenyl-C1-C6-alkyl;
Rz~, Rzs, Rzs, R3o independently of one another are hydrogen, C1-C6-alkyl, C3-C6-alkenyl, Cz-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylcarbonyl, (C1-C6-alkoxy)carbonyl, or Rz7 and Rzs and/or Rzs and R3o together with the respective common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle which, in addition to carbon ring members, may, if desired, contain an oxygen atom or an -NH- group;
m is 0, 1, 2 or 3.

R4 is in particular halogen and specifically fluorine or chlorine.
RA is in particular hydrogen, i.e. rn is 0.
In Q1, R5 is, in particular:
C1-C6-alkoxy, C2-C6-alkenyloxy or C2-C6-alkynyloxy, where each of the 3 last-mentioned radicals may, if desired, carry one to three substituents, in each case selected from the group consisting of halogen, Ci_C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, Ci-C6-alkylsulfonyl, -CO-R14, -CO-OR14, -CO-N(R14)-R15~ -N(R14)_R15 and _C ( Ri6 ) =N_ORi3 _Cp_R17 ~ -C ( NR18 ) _R17 ~ _C ( R17 ) ( pRl9 ) ( pR20 ) .
_C ( R17 ) =C ( R21 ) _Cp_R22 ~ _Cg ( R17 ) _Cg ( R21 ) _Cp_R22 ~ _Cp_OR26 , -Cp_N ( R26 ) _pRl3 ~ _C ( R17 ) =C ( R21 ) -L~p_N ( R26 ) _pRi3 ~
-C(R16)=N_pRl3~ -C(pRi9)(pR2o)_pg26~ _N(R27)R28~ _CON(R27)R28 or -C(R17)=C(R27)CO-N(R27)R28;
in which Ri3 to R22 and R26 to R28 are as defined above, and specifically C2-C6-alkenyloxy, C2-C6-alkynyloxy, _C(R17)(pRl9)(pR20)~ _C(R17)oC(R21)_C(p)R21~
_Cg(R17)_CH(R21)_C(O)R22~ C(O)OR26, -C(O)_N(R26)-OR13, -C(R16)=N-OR13 and C(O)N(R27)R28, in which Ri3, Rls~ Ri7~ Rls~
R2o ~ R21 ~ R22 ~ R26 ~ R27 and R28 have the meanings mentioned above and in particular those mentioned below:
R13 is Ci-C6-alkyl, Ci-C6-haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, Ci-C6-cyanoalkyl or Ci-C6_alkoxycarbonyl_Ci-C6-alkyl;
R16 is hydrogen, Ci-C6-alkyl, Ci-C6-alkoxy, Ci-C6-alkoxycarbonyl-Ci-C6-alkyl, Ci-C6-alkoxycarbonyl-Ci-C6-alkoxy or phenoxycarbonyl-Ci-C6-alkoxy;
R17 is hydrogen, Ci-C6-alkyl;
Ri9 and R2o independently of one another are Ci_C6-alkyl;

R21 is hydrogen, halogen, C1-C6-alkyl;
R2z is hydroxyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkoxycarbonyl-C1-C6-alkyl;

R26 is C1-C6-alkyl, C3-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C1-C6-alkoxyalkyl;
R27 is hydrogen, C1-C6-alkyl;
R2$ is hydrogen, C1-C6-alkyl, C1-C6-alkoxy, or R2~ and R28 together are a 6-membered saturated azaheterocycle which may have one or two not adjacent oxygen atoms in the ring.
R is preferably 'not hydrogen, in particular if Q is one of the radicals Q1, Q4, Q5 or Q6, and if Z is oxygen.
R is, in particular:
C1-C6-alkoxycarbonyl, (C1-C6-alkoxy)thiocarbonyl, (C1-C6-alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NR11R12, -C(O)NHC(O)C1, -C(O)NHS(O)zCl, C(O)NHC(O)OR12', C(O)NHS(O)ZR12', C(O)R2, P(O)R1(OR1), P(0)(OR1)y; S(0)R2, S(O)2R2 or S(O)ZNHR2 in which the variables R1, R2, R11, R12 and R12' have the meanings mentioned above and specifically those listed below:
R1 is C1-C6-alkyl R2 is C1-C6-alkyl R11 is hydrogen or C1-C6-alkyl R12 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy, and R12' is C1-C6-alkyl and C1-C6-alkyloxy.
R is particularly preferably:

hydrogen, or is C1-C6-alkoxycarbonyl or (C1-C4-alkoxycarbonyl)iminocarbonyl.
A specific class relates to compounds of the formulae Ia and Ib in which Q is Q1. Here, the variables have the meanings mentioned above and particularly preferably those below:
R is C1-C6-alkoxycarbonyl, (C1-C6-alkoxy)thiocarbonyl, (C1-C6-alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NR11R12~
-C(0)NHC(O)C1, -C(O)NHS(O)2C1, C(O)NHC(O)OR12', C(O)NHS(O)2R12~~ C(O)R2r ~''(O)R1(ORI)r p(O)(OR1)2i S(O)R2i S(O)2R2 or S(O)2NHR2 in which the variables R1, R2, R11, R12 and R12' have the following meanings:
R1 is C1-C6-alkyl, R2 is C1-C6-alkyl, R11 is hydrogen or C1-C6-alkyl, R12 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy, and R12' is C1-C6-alkyl or C1-C6-alkyloxy;
Z is O or S, in particular O

X is O or S, m has the value 0, R3 is hydrogen or halogen, in particular fluorine or chlorine, R4 is hydrogen, halogen, in particular fluorine or chlorine, or cyano, and R5 is Cl-C6-alkyl, C3-C6-alkenyl, C1-C6-haloalkyl, C3-C6-haloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy, Ci-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-haloalkenyloxy, C3-C6-alkenylthio, C3-C6-haloalkenylthio, C1-C6-alkoxycarbonyl-C1-C6-alkoxy, C3-C6-alkenyloxycarbonyl-C1-C6-alkoxy, C3-C6-alkynyloxycarbonyl-C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkoxycarbonyl-C1-C6-alkoxy, C3-C6-alkenyloxycarbonyl-C1-C6-alkoxycarbonyl-C1-C4-alkoxy, C1-C6-alkoxycarbonyl-C1-C6-alkylthio, C1-C6-alkenyloxycarbonyl-C1-C6-alkylthio, C1-C6-alkynyloxycarbonyl-C1-C6-alkylthio, C1-C6-alkoxy-Cl-C6-alkoxycarbonyl-C1-C6-alkylthio, C1-C6-alkoxyimino-C1-C6-alkyl, N-C1-C6-alkoxy-N-(C1-C6-alkyl)amino-C1-C6-alkyl, C1-C6-alkylsulfonylamino, -COOR26, -CONR2~R2~, -C(=NRls)Rl~, -C(R16)=NOR13, C(Rl~)=C(R21)_CO-R22~
where the variables R13, Rls, R1~, R21, R22~ R2s to R28 have the following meanings:
R13 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C1-C6-cyanoalkyl or C1-C6-alkoxycarbonyl-C1-C6-alkyl;
R16 is hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C1-G6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkoxy or phenoxycarbonyl-C1-C6-alkoxy;
R1~ is hydrogen, C1-C6-alkyl;
R1$ is C1-C6-alkoxy;
R21 is hydrogen, halogen, C1-C6-alkyl;
R22 is hydroxyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkoxycarbonyl-C1-C6-alkyl;

R26 is C1-C6-alkyl, C3-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C1-C6-alkoxyalkyl;
R2~ is hydrogen, C1-C6-alkyl;
R2B is hydrogen, C1-C6-alkyl, C1-C6-alkoxy, or R27 and R28 together are a 6-membered saturated azaheterocycle which may have one or two not adjacent oxygen atoms in the ring.
In particular, R5 has the following meaning:

R5 is CN, COOH, C1-C4-alkoxyiminomethyl, C1-C4-alkoxy, C3-C6-cycloalkyloxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-alkenyloxyiminomethyl, (C1-C4-alkoxycarbonyl)-C2-C6-alkenyloxy, C3-C6-alkynyloxyiminomethyl, 2-[C1-C4-alkoxycarbonylj-2-chloroethyl, 2-[C1-C4-alkoxycarbonylj-2-chloroethenyl, C1-C4-alkoxycarbonyl, (C1-C6-alkoxycarbonyl)-C1-C4-alkoxy, (C1-C6-alkoxycarbonyl)-C1-C4-thioalkyl, is COOR26, where R26 = C1-C4-alkoxy-C1-C4-alkyl or C3-C6-alkenyloxycarbonyl-C1-C4-alkyl, is CONR2~R28, where R2~ = hydrogen or C1-C4-alkyl and R28 =
hydrogen, C1-C4-alkyl or C1-C4-alkoxy;
is C(=NR17)Ri8, in which Rl~ is C1-C4-alkoxy and R1$ is C1-C4-alkoxy or C1-C4-alkoxycarbonyl-C1-C4-alkoxy.
Two further classes relate to compounds of the formulae Ia and I,b in which Q is Q2 or Q3. Here, the variables, independently of one another, particularly preferably have the following meanings:
R is C1-C6-alkoxycarbonyl, (C1-C6-alkoxy)thiocarbonyl, (C1-C6-alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NR11R12, -C(O)NHG(0)C1, -C(O)NHS(O)2C1, C(O)NHC(O)OR12~, C(0)NHS(O)2R12~~ C(O)R2. p(O)R1(OR1). p(O)(OR1)2: S(O)R2.
S(O)2R2 or S(O)2NHR2 in which the variables R1, R2, R11, R12 and R12' have the following meanings:
R1 is C1-C6-alkyl, R2 is C1-C6-alkyl, R11 is hydrogen or C1-C6-alkyl, R12 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy, and R12' is C1-C6-alkyl or C1-C6-alkyloxy;
Z is O or S, in particular O, X is O or S, m has the value 0, R3 is hydrogen or halogen, R4 is hydrogen or halogen, Y is O or S, U is a single bond, oxygen or C1-C4-alkylene and R6 is hydrogen, halogen, cyano, C1-C6-alkyl, Ci-C6-haloalkyl, C3-C7-cycloalkyl, saturated C3-C~-heterocyclyl which has one or two heteroatoms selected from the group consisting of oxygen and sulfur in the ring, is Cl-C6-alkoxyalkyl, cyano-C1-C6-alkyl, C02H, C1-C6-alkoxycarbonyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl.
Two further classes relate to compounds of the formulae Ia and Ib in which Q is Q4 or Q5. Here, the variables, independently of one another, particularly preferably have the following meanings:
R is C1-C6-alkoxycarbonyl, (C1-C6-alkoxy)thiocarbonyl, (C1-C6-alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NR11R12, -C(O)NHC(O)C1, -C(O)NHS(O)2C1, C(O)NHC(O)ORIZ', C(O)NHS(O)ZRiz', C(O)R2, P(O)R1(OR1), P(O)(OR1)2: S(O)R2, S(O)2R2 or S(O)2NHR2 in which the variables R'1, R2, R11, R12 and R12' have the following meanings-.
R1 is C1-C6-alkyl, R2 is C1-C6-alkyl, R11 is hydrogen or C1-C6-alkyl, R1z is hydrogen, C1-C6-alkyl or C1-C6-alkoxy, and R12' is C1-C6-alkyl and C1-C6-alkyloxy;
Z is O or S, in particular O, X is O or S, m has the value 0, R3 is hydrogen or halogen, Y is O or S, Y' in the formula Q5 is oxygen or sulfur, T is a single bond, oxygen or C1-C4-alkylene and R7 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C~-cycloalkyl, saturated C3-C~-heterocyclyl which has one or two heteroatoms selected from the group consisting of oxygen and sulfur in the ring, C1-C6-alkoxyalkyl, cyano-C1-C6-alkyl, C02H, C1-C6-alkoxycarbonyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl.
A further class relates to compounds of the formulae Ia and Ib in which Q is Q6. Here, the variables have the meanings mentioned above and, independently of one another, the following meanings:
R is C1-C6-alkoxycarbonyl, (C1-C6-alkoxy)thiocarbonyl, (C1-C6-alkylthio)carbonyl, -CHO, -CN, COOH, -C(O)NR11R12~
-C(O)NHC(O)Cl, -C(O)NHS(O)2C1, C(O)NHC(O)OR12', C(O)NHS(O)2R12~i C(Q)R2r P(~)R1(OR1)r 1'(~)(~R1)2: S(O)R2, .
S(O)2R2 or S(O)2NHR2 in which the variablea R1, R2, R11, Ri2 and R12' have the following meanings:
R1 is C1-C6-alkyl, R2 is C1-C6-alkyl, R11 is hydrogen or C1-C6-alkyl, R12 is hydrogen, C1-C6-alkyl or,Cl-C6-alkoxy, and R12' is C1-C6-alkyl or C1-C6-alkyloxy;
Z is O or S, in particular O, X is O or S, m has the value 0, R3 is hydrogen or halogen, R4 is hydrogen or halogen, where Rs and R9 independently of one another are hydrogen, C1-C6-alkyl, halogen, cycloalkyl or C1-C6-haloalkyl, or R8 and R9 together with the carbon atom to which they are attached are a carbonyl group.
Particular preference is given to compounds of the formula Id, in which the variables have the abovementioned meanings.
Very particular preference is given to compounds of the formula Ib, in which the variables have the meanings mentioned above as being preferred.
Specifically preferred are compounds of the formulae Ia and Ib and amongst these in particular the compounds of the formula Ib, in which Q is Q1, Z is oxygen, X is oxygen or sulfur, m has the value 0, R is hydrogen, C1-C4-alkoxycarbonyl or (C1-C4-alkoxycarbonyl)iminocarbonyl, R3 is fluorine, chlorine or hydrogen, R4 is halogen, and R5 is CN, GOOH, C1-G4-alkoxyiminomethyl, C1-C4-alkoxy, C3-C6-cycloalkyloxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-alkenyloxyiminomethyl, (C1-C4-alkoxycarbonyl)-CZ-C6-alkenyloxy, C3-C6-alkynyloxyiminomethyl, 2-[C1-C4-alkoxycarbonyl]-2-chloroethyl, 2-(C1-C4-alkoxycarbonyl]-2-chloroethenyl, C1-C4-alkoxycarbonyl, (C1-C6-alkoxycarbonyl)-C1-C4-alkoxy, (C1-C6-alkoxycarbonyl)-C1-C4-thioalkyl, is COOR26, where R26 = C1-C4-alkoxy-C1-C4-alkyl or C3-C6-alkenyloxycarbonyl-C1-C4-alkyl, 0050~5~~80 CA 02377143 2001-12-19 ~3 is CONR2~R28, where R27 = hydrogen or C1-C4-alkyl and R2$ _ is hydrogen, C1-C4-alkyl or Ci-C4-alkoxy;
is C(=NR1~)R18, in which R1~ is C1-C4-alkoxy and R1s is C1-C4-alkoxy or C1-C4-alkoxycarbonyl-C1-C4-alkoxy.

Particularly preferred compounds of the formula Ia are the compounds Ial.l to Ia1.206 listed in Table 1 below.
Table 1 X
~N~NH ~ ~ R4 I a Z N
~02CH3 No . Z X R3 R4 R5 I a.1 O S H Cl OCH2C~CH

I a.2 O S H Cl OCH2CH=CH2 I a.3 O S H Cl OCH(CH3)C$CH

I a.4 O S F Cl OCH2CsCH

I a.5 O S F C1 OCH2CH=CH2 I a.6 O S F C1 OCH(CH3)C~CH

I a.7 O S H C1 COZCH3 I a.8 O S H C1 C02CHZCH=CHZ

I a.9 O S H Cl COZCH2C~CH

I a.10 O S H C1 C02CHZCHZOCH3 I a.11 O S F C1 C02CH3 I a.12 O S F C1 C02CH2CH=CHZ

I a.13 O S F C1 C02CHZC~CH

I a.14 O S F C1 C02CHZCHZOCH3 I a.15 0 S H CN OCHZC3CH

I a.16 O S F CN OCHZC~CH

I a.17 O S H C1 OCH2C02CH3 I a.18 O S H C1 OCHZCOZCHZC~CH

I a.19 O S H C1 OCHZC02CH2CHZOCH3 I a.20 O S H C1 OCH2COzC(CH3)2C02CHZCH=CHZ

I a.21 O S F Cl OCH2COZCH3 I a.22 0 S F Cl OCH2COZCHZC~CH

I a.23 O S F C1 OCH2C02CHZCHzOCH3 I a.24 0 S F C1 OCH(CH3)C02CH3 I a.25 O S F Cl OCH(CH3)COyC2H5 I I a.26 O S F I C1 OCH(CH3)C02CHzCH=CHz I ~ I I

005~~5~080 CA 02377143 2001-12-19 No . Z X R3 R4 R5 I a.27 O S F C1 OCH(CH3)C02CHZC~CH

I a.28 O S F C1 OCH(CH3)C02CHZCH20CH3 5 I a.29 0 S F C1 OCH2C02-nC5Hi1 I a.30 O S F C1 OCH(CHg)C02-nC5Hi1 I a.31 O S H C1 COZCH2C02CH3 I a.32 O S H C1 COZCHZCO~GzH5 I a.33 O S H C1 C02C(CH3)2C02CH2CH=CHZ

I a.34 O S F C1 COZCH2C02CH3 I a.35 O S F C1 C02CHZC02C2Hg I a . O S F C1 COZC ( CH3 ) 2COZCH2CH=CH2 I a.37 O S F CN C02CH3 15 I a , O S F CN C02C2H5 I a . O S F CN C02GHZCH20CH3 I a . 0 S F CN C02CHZC02CHg I a.41 O S F CN C02CHZC02CyH5 20 I a.42 O S F CN C02C(CH3)2C02CH2CH=CH2 I a . O S F CN OCHZC02CH3 I a.44 O S F CN OCH2C02C2H5 I a . O S F CN OCH2C02CHZCeCH

25 I a.46 O S F CN OCH2C02CH2CHZOCH3 I a.47 O S F CN OCH(CH3)C02CH3 I a.48 O S F CN OCH(CH3)COZG2H5 I a.49 O O F CN OCH(CH3)C02CHZCH20CH3 I a.50 O S H C1 NHS02CHg 30 I a.51 O S H C1 NHS02C2H5 I a.52 O S H Cl NHSOZ-nC3H7 I a.53 O S H Cl NHS02-iC3H7 I a.54 O S F Cl NHS02CH3 35 I a.55 O S F C1 NHS02CZH5 I a.56 O S F C1 NHSOz-nC3H7 I a.57 O S F C1 NHSOZ-iC3H7 I a.58 O S F CN NHS02CH3 40 I a.59 O S F CN NHS02C2H5 I a.60 0 S F CN NHS02-nC3H7 I a.61 O S F CN NHS02-iC3H7 I a.62 O S H Cl OCH2C(C1)=CHz I a.63 O S C1 C1 OCH~C(C1)=CHZ

I a.64 O S F Cl OCH2C(Cl)=CH2 I a.65 O S F CN OCH2C(C1)=CHZ

NO. ~ Z X R3 Ft4 RS
' I a.66 O S Cl C1 OCH2C~CH

I a.67 O S C1 C1 OCHzCH=CH2 I a.68 O S C1 Cl OCH2COZCH3 I a.69 O S C1 Cl OCH2C02nC5H11 I a.70 O S C1 C1 OCH(CH3)COZCH3 I a.71 O S C1 Cl OCH(GH3)C02CH2CH=CHZ

I a.72 O S C1 C1 OCH(CH3)COZCH2CH20CH3 1 I a.73 O S C1 C1 C02CH3 I a.74 O S C1 Cl C02C2H5 I a.75 O S C1 Cl C02CHZC02CH3 I a. 76 O 0 C1 C1 C02C ( CH3 ) 2C02CH3 15I a.77 O S H C1 SCH2C$CH

I a.78 O S H C1 SCH2CH=CH2 I a.79 O S H Cl SCHZC02CH3 I a.80 O S H C1 SCH2C02-nC5H11 20I a.81 O S H Cl SCH(CH3)C02CH3 I a.82 O S H C1 SCH(CH3)C02CH2CH20CH3 I a.83 O S H C1 SCHZC02CHZCH20CH3 I a.84 O S H Cl OCFyCHFCl 25I a.85 O S C1 Cl SCH2C~CH

I a.86 O S C1 Cl SCH2CH=CH2 I a.87 O S C1 Cl SCHZC02CH3 I a.88 O S C1 C1 SCH2G02-nC5H11 I a.89 O S C1 C1 SCH(CH3)COZCH3 30I a.90 O S Cl C1 SCH(CH3)C02CHzCH20CH3 I a.91 O S C1 C1 SCH2C02CHZCH20CH3 I a.92 O S C1 C1 OCF2CHFC1 I a.93 O S F Cl SCH2C~CH

35I a.94 O S F C1 SCH2CH=CH2 I a.95 O S F C1 SCH2COzCH3 I a.96 O S F C1 SCH2C02-nCSHli I a.97 O S F C1 SCH(CH3)C02CH3 40I av98 O S F C1 SCH(CH3)C02CHZCHZOCHg I a.99 O S F C1 SCH2C02CHZCH20CH3 I a.100 O S F C1 OCFZCHFCl I a.101 O S F CN SCH2C~CH

I a.102 O S F CN SCH2CH=CH2 I a.103 O O F CN SCH2C02CH3 I a.104 O S F CN SCH2C02-nC5H11 No . Z X R3 R4 R5 I a.105 O S F CN SCH(CH3)C02CH3 I a.106 O S F CN SCH(CH3)COzCH2CH20CH3 I a.107 O S F CN SCH2COzCH2CHZOCH3 I a.108 O S H C1 C(O)N(CH3)z I a.109 O S F C1 C(O)N(CH3)z I a.110 O S F CN C(0)N(CH3)z I a.lll O S H C1 C(O)-N(C2H4)z0 I x,112 O S H F C(O)-N(C2H4)z0 I a.113 O S H Cl CH=N-OCH3 I a.114 O S H Cl CH=N-OC2H5 I a.115 O S H C1 C(O)NHOCH3 I a.116 O S H C1 C(0)NHOC2H5 I a.117 O S H C1 C(=N-OCH3)OCH3 I a.118 0 S H C1 C(=N-OCH3)OC2H5 I a.119 0 S H C1 C(=N-OGH3)OCH2C02CH3 I a.120 O S H C1 C(=N-OCH3)OCH(CH3)C02CH3 I a.121 O S H C1 CH=CH-C02CH3 I a.122 0 S H C1 CH=CH-C02CzH5 I a.123 O S H C1 CH=C(CH3)C02CH3 I x124 O S H Cl CH=C(CH3)C02CzH5 I a.125 O S H Cl CH=C(C1)C02CH3 I a.126 O S H C1 CH=C(C1)COzC2H5 I a.127 O S H C1 CH=C(Br)CHZC2H5 I a.128 O S H Cl CH2N(CH3)OCH3 I x,129 O O H C1 C(=N-OCH3)OCH2COyPhenyl I a.130 O S H F CH=N-OC2H5 I a.131 O S H F C(O)NHOCH3 I a.132 O S H F C(0)NHOCzHS

I a.133 0 S H F C(=N-OCH3)OCH3 I a.134 0 S H F C(=N-OCH3)OCZHS

I a.135 O S H F C(=N-OCH3)OCHzC02CH3 I a.136 0 S H F C(=N-OCH3)OCH(CH3)COzCH3 I x137 O S H F CH=CH-C02CH3 I a.138 O S H F CH=CH-COZC2H5 I a.139 0 S H F CH=C(CH3)C02CH3 I a.140 O S H F CH=C(CH3)C02C2H5 I a.141 O S H F CH=C(C1)C02CH3 I a.142 O S H F CH=C(C1)C02CZH5 I a.143 O S H F CH=C(Br)C02CZH5 6 ~3 N o . z x 3 R4 ~5 R

I a.144 O S F CHZN(CH3)OCH3 H

I a.145 O S F C(=N-OCH3)OCHzC02Phenyl H

I a.146 O S F CH=N-OCH3 H

I a.147 O S CN CH=N-OCH3 F

I a.148 0 S F CN CH=N-OC2H5 I a.149 O 5 F CN C(O)NHOCH3 I a.150 O S F CN C(O)NHOC2H5 I a.151 O S F CN C(=N-OCH3)OCH3 I a.152 O S F CN C(=N-OCH3)OCZHS

I a.153 O S F CN C(=N-OCH3)OCHZC02CH3 I a.154 O S F GN C(=N-OCH3)OCH(CH3)COZCH3 I a.155 O O F CN CH=CH-C02CH3 I a.156 O S F CN CH=CH-C02CzH5 I a.157 O S F CN CH=C(CH3)COZCH3 I a.158 O S F CN CH=C(CH3)COzC2H5 I x159 O S F CN CH=C(Cl)C02CH3 I a.160 O S F CN CH=C(C1)COZC2H5 I a.161 O S F CN CH=C(Br)COZCZHS

I a.162 O S F CN CHZ-N(CH3)OCH3 I a.163 O S F CN C(N-OCH3)OCH2C02C6H5 I a.164 O S H C1 CH=N-OCH2-C=CH

I a.165 O S H G1 CH=N-OCHZ-C(C1)=CHZ

I a.166 O S F Cl CHZ-GH(C1)C02CZH5 I a.167 O S H C1 CH=N-OCHzC02CH3 I x.168 O 5 H C1 CH=N-OCHZC02CZH5 I a.169 O S H C1 CH=N-OCH2CHZC1 I a.170 O S H C1 CH=N-OCHzCN

I a.171 O S H C1 CH=N-OCH(CH3)COZCH3 I a.172 0 S H C1 CH=C(C1)COSCH3 I a.173 O S H C1 CH=C(Br)COSCH3 I a.174 O S H C1 CH=C(C1)C02CHZG02CH3 I a.175 O S H C1 CH=C(C1)C02CH(CH3)C02CH3 I a.176 O S H C1 C(CH3)=NOGH3 I a.177 O S H C1 C(CH3)=NOC2H5 I a.178 O S H C1 C(CH3)=NOCH2C02CH3 I a.179 O S F C1 CH=N-OCHZC~CH

I a.180 O S F C1 CH=N-OCH2-C(C1)=CH2 I a.181 O S F C1 CH=N-OCH2C02CH3 I a.182 O O F C1 CH=N-OCHZC02C2H5 No . Z X R3 R4 R5 .

I a.183 0 S F C1 CH=N-OCH2CH2C1 I a.184 O S F C1 CH=N-OCH2CN

I a.185 O S F Cl CH=N-OCH(CH3)C02CH3 I a.186 O S F C1 CH=C(Cl)COSCH3 I a.187 0 S F C1 CH=C(Br)COSCH3 I a.188 0 S F C1 CH=C{C1}C02CHZC02CH3 I a.189 O S F C1 CH=C(C1)COZCH(CH3)C02CH3 I a.190 O S F C1 C(CH3)=N-OCH3 I a.191 O S F C1 C(CH3)=N-OCZH5 I a.192 O S F C1 C(CH3)=N-OCH2COZCH3 I a.193 O S C1 Cl CH=N-O-OCH2C~CH

15I x,194 O S C1 C1 CH=N-OCHZ-C(C1)=CH2 I a.195 O S C1 C1 CH=N-OCH2C02CH3 I a.196 O S C1 C1 CH=N-OCH2COZC2H5 I a.197 O S C1 C1 CH=N-OCHzCHZCl 20I a.198 O S C1 C1 CH=N-OCH2CN

I a.199 O S C1 C1 CH=N-OCH(CH3)C02CH3 I a.200 O S C1 C1 CH=C(C1)COSCH3 I a.201 0 S C1 C1 CH=C(Br)COSCH3 25I a.202 O S Cl C1 CH=C(C1)COZCH2C02CH3 I a.203 O S C1 C1 CH=C(C1)C02CH(CH3)COzCH3 I a.204 O S Cl C1 C(CH3)=NOCH3 I a.205 O S C1 C1 C(CH3)=NOC2H5 I a.206 O O C1 C1 C(CH3}=NOCH2COZCH3 Furthermore, particular preference is given to the substituted ureas of the formula Ib, in particular to the compounds Ibl.l to Ib1.206 which differ from the corresponding compounds Ial.l to 35 Ia1,206 only in that the N-substituents are inverted:
H3C02 i R3 / R4 Rs Ib1 45 preference is furthermore given to the compounds Ia2.1 to Ia2.206 in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

X
I
N~~.~ ~ \ Ra laz ~N~
5 ~ C02CzH5 s 10 Preference is furthermore given to the compounds Ib2.1 to Ib2.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

Ib2 Z~/N. -\ / R

Preference is furthermore given to the compounds Ia3.1 to Ia3.206, in which the variables Z, X, R3, R4 and RS each have the meanings mentioned in rows 1 to 206:
X
~I
N~~~ / \ R4 1a3 ~I
LUN~Cp2 s Preference is furthermore given to the compounds Ib3.1 to Ib3.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
~C~
~N\C~p R Ib3 X \ ~ Ra Preference is furthermore given to the compounds Ia4.1 to Ia4.206, in which the variables Z, X, R3, R4 and RS each have the meanings mentioned in rows 1 to 206:
X Rs N~C.~ ~ ~ R4 1a4 ~N
C02 s ~~4Ha Preference is furthermore given to the compounds Ib4.1 to Ib4.206, in which the variables Z, X, R3, R4 and R5 each have the meanings I5 mentioned in rows 1 to 206:
~'4H8 N,C~ Ra Iba ~/N~C~ /
'R
Preference is furthermore given to the compounds Ia5.1 to Ia5.206, in which the variables Z, X, R3, R4 and RS each have the meanings mentioned in rows 1 to 206:

X
I I
N~C~~ Ro las FiI
~N~ s wt-CaHa Preference is furthermore given to the compounds Ib5.1 to Ib5.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

~t-CaHs N,C02 R3 ~N~ ~~ Ib' C /
a 'R
10 Preference is furthermore given to the compounds Ia6.1 to Ia6.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

X
I
~~. / ~ Ra ~N ~ _ las Z~N~C-SCH3 s Preference is furthermore given to the compounds Ibs.l to Ib5.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
O
N~-SCH3 R3 ~N
W/ ~C' /
X ~ I Ra Preference is furthermore given to the compounds Ia7.1 to Ia7.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

X
I
N'~~~ / ~ Ra lay Z~N~CHO 5 Preference is furthermore given to the compounds Ib7.1 to Ib7.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
~N~CHO Ra zr~N.C.~ / Ib~
\ ~ Ra s Preference is furthermore given to the compounds Ias.l to Ia8.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

X

N~~.~ ~ ~ Ra laa ~N\ 5 CN
Preference is furthermore given to the compounds Ibs.l to Ib8.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
N~CN Rs ~
~N~ .~ Iba C
\ R4 Preference is furthermore given to the compounds Ia9.1 to Ia9.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

~050~5~~$0 CA 02377143 2001-12-19 R
N~"~ / \ Ra ~' - l as ~N
~C-NHCH3 s Preference is furthermore given to the compounds Ib9.1 to Ibg.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
~~ ~NHCH3 NBC Rs ~N~ ~~ Iba O
a R
Rs Preference is furthermore given to the compounds Ial~.l to Ia1~.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

X
I
N.~.~ / \ Ra ~N H la,o ~C-NHOCH3 s Preference is furthermore given to the compounds Ibl~.l to Ib1~.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
~~ ~NHOCH3 I NiC Rs Z~N\C~~ / Ib,o X ~ ~ a 'R

Preference is furthermore given to the compounds Iali.l to Ia11.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

I I
N~C~ ~ ~ Ra N ~ 1a»
U ~ s IC-~I-IC-CI
O O
Preference is furthermore given to the compounds Ibll.l to Ib11.206, in which the variables Z, X, R3, R4 and RS each have the meanings mentioned in rows 1 to 206:
O
O\~ N- ~- CI
If R3 Ib~~
~N~ ~~
C
X ~ a 'R
s Preference is furthermore given to the compounds Ia12.1 to Ia12.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
Ra X
~I
N~~~ ~ ~ Ra I ~ la~z Z,~ N
s I I
O
Preference is furthermore given to the compounds Ib12.1 to Ib12.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

~ ft ~~~ NHS02CI

Ib~2 \~N..C. /
X \ Ra s Preference is furthermore given to the compounds Ia13.1 to Ia13.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

X
I
N~~~~ ~ \ Ra H 1a13 I I
O
Preference is furthermore given to the compounds Ib13.1 to Ib13~206, in which the variables Z, X, R3, R4 and RS each have the meanings mentioned in rows 1 to 206:
~~~NHC02CH3 R3 Ib~3 ~N~
C /
X \ R4 Preference is furthermore given to the compounds Ia14.1 to Ia14.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

X
I
\
~N~ \~ R4 lava zu ~ s C-NHSOzCH3 I I
O

~~r~~~r~~p8~ CA 02377143 2001-12-19 Preference is furthermore given to the compounds Ib14.1 to Ib14.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
O
~~~NHS02CH3 R3 Ib~a ~/N~C~ /
Ra Preference is furthermore given to the compounds Ia15.1 to Ia15.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
Ra X
~I
N~~~~ ~ ~ R4 ~a~s HN
a ~ 5 I I
O
Preference is furthermore given to the compounds Ibl5.I to Ib15.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
~~~ CH3 R3 ~b~s ~/N~C~ /
Ra Preference is furthermore given to the compounds Ia16.1 to Ia16.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

X
I
N'~~ ~ ~ R4 18 ~N ~ la \il 5 P(O)CH3(OCHa) Preference is furthermore given to the compounds Ib16.1 to Ia16.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
P(O)CH3(OCH3) i R3 Ibis ~N~
C /
X \ inn Preference is furthermore given to the compounds Ia17.1 to Ia1~.206, in which the variables Z, X, R3, R4 and RS each have the meanings mentioned in rows 1 to 206:
X
N'~~ ~ ~ R4 la~~
~I

P(O)(OCH3)2 Preference is furthermore given to the compounds Ibl~.l to Ib17.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
P(O)(OCH3)2 ~ IN ~ R3 Ib,~
Z\/N~C~~ /
X \ I R4 Preference is furthermore given to the compounds Iale.l to Ia18.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

I
N~~~ ~ ~ Ra ~N ~ lace S(O)CH3 Preference is furthermore given to the compounds Ib18.1 to Ib18.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:
S(O)CH3 R3 Ib~e ~I
~N~ .
C
X ~ Ra Preference is furthermore given to the compounds Ia19.1 to Ia19.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

X
I I
N~C.~ ~ ~ Ra H lace Preference is furthermore given to the compounds Ib19.1 to Ib19.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

I
~N H R3 Ib~9 5 Z\/N~C~~ /
X \ I Ra 10 Preference is furthermore given to the compounds Ia2o.1 to IaZO.206, in which the variables Z, X, R3, R4 and R5 each have the meanings mentioned in rows 1 to 206:

X
~N~ .~ ~ ~ Ra 20 t[ I la \/ ~ s Preference is furthermore given to the compounds IbZO.l to Ib2o.206, in which the variables Z, X, R3, R4 and Rs each have the meanings mentioned in rows 1 to 206:

H R3 Ib2o Z\/N~C~~ /
X \ I Ra Preference is furthermore given to the compounds Ia2i to 40,1 to Ia21 to 40.206, in which the variables X, R3, R4 and RS each have the meanings mentioned in rows 1 to 206 and the radical R has the meaning mentioned in the formulae Tal to Ia2o:

X
I
N~~.N ~ Ra laze wao ~I H

R

Preference is furthermore given tr. the compounds Ibzl to 40,1 to Ibzl to 40,206, in which the variables X, R3, R4 and RS each have the meanings mentioned in rows 1 to 206 and the radical R has the meaning mentioned in the formulae Ibl to Ibzo:
R
R3 Iba~ ~oao I H
~N~ ,N

Ra Moreover, particular preference is given to the substituted ureas of the formula Ia.bl X
I
~N' ~~ ~ la.b~
Z~NH O
'YURS
in particular to the compounds listed in Table 2:
Table 2 No . -,, X Z Y U R6 Ia.bl 1 S S O H

Ia.bl 2 S S O CH3 Ia.bl 3 S S O CzHS

Ia.bl 4 S S 0 n-C3H7 Ia.bl 5 S S 0 i-C3H~

Ia.bl 6 S S O cyclopropyl Ia.bl 7 S S O n-C4H9 __ Ia.bl 8 S S O sec-C4H9 Ia.bl 9 S S O I-C4H9 Ia.bl 10 S S O t-C4H9 Ia.bl 11 S S 0 CHZ cyclopropyl Ia.bl 12 S S O cyclopentyl Ia.bl 13 S S O cyclohexyl Ia.bl 14 5 S 0 oxiran-2-yl Ia.bl 15 5 S 0 oxetan-2-yl No . X Z Y U R6 ~

Ia.bl 16 S S 0 tetrahydrofuran-2-yl Ia.bl 17 S S O tetrahydropyran-2-yl ~

Ia.bl 18 S S O oxepan-2-yl Ia.bl 19 S S O thiiran-2-yl Ia.bl 20 S S 0 thietan-2-yl Ia.bl 21 S S O tetrahydrothiofuran-2-yl Ia.bl 22 S S O tetrahydrothiopyran-2-yl Ia.bl 23 S S O thiepan-2-yl Ia.bl 24 S S O oxetan-3-yl Ia.b1 25 S S O tetrahydrofuran-3-yl Ia.bl 26 S S O tetrahydropyran-3-yl Ia.bl 27 S S O oxepan-3-yl Ia.b1 28 S S 0 thiethan-3-yl Ia.bl 29 S S O tetrahydrothiofuran-3-yl Ia.bl 30 S S 0 tetrahydrothiopyran-3-yl Ia.bl 31 S S O thiepan-3-yl Ia.bl 32 S S O tetrahydropyran-4-yl Ia.bl 33 S S O oxepan-4-yl Ia.bl 34 S S 0 tetrahydrothiopyran-4-yl Ia'b1 35 S S O oxepan-4-yl Ia.bl 36 S S O tetrahydrothiopyran-4-yl Ia.bl 37 S S 0 O CH3 Ia.bl 38 S S O O CZHS

Ia.bl 39 S S O O n-C3H7 Ia.bl 40 S S O O i-C3H7 Ia.bl 41 S S O O cyclopropyl Ia.bl 42 S S O COZH

Ia.bl 43 S S O COZCH3 Ia.bl 44 S S O COZC2H5 Ia.bl 45 S S O CHZCOZCH3 Ia.bl 46 S S O CH(CH3)C02CH3 Ia.bl 47 S S 0 O CH2GOyCH3 Ia.bl 48 S S O O CH(CH3)C02CH3 Ia.bl 49 S S 0 C1 Ia.bl 50 S S O CN

Ia.bl 51 S S 0 CHZC~CH

Ia.bl 52 S S O O CH2C=-CH

Ia.bl 53 S S O CHZOCH3 Ia.bl 54 S S O CH2CHZOCH3 0050500$0 CA 02377143 2001-12-19 No . ' X Z Y U R6 Ia.bl 55 S S O O CHpCHyOCH3 Ia.bl 56 S S O CH2 cyclopentyl Ia.bl 57 S 0 O H

Ia. b1 58 S O O CH3 Ia.bl 59 S O 0 C2H5 Ia.bl 60 S O O n-C3H7 Ia.bl 61 S O 0 I-C3H7 Ia.bl 62 S O 0 cyclopropyl Ia.bl 63 S O O n-C4H9 Ia.bl 64 S O O sec-C4Hg Ia.bl 65 S O 0 i-C4H9 15Ia.bl 66 S O O t-C4H9 Ia.bl 67 S O O CH2 cyclopropyl Ia.bl 68 S O O cyclopentyl Ia.bl 69 S O O cyclohexyl 20Ia.bl 70 S O O oxiran-2-yl Ia.bl 71 S O O oxetan-2-yl Ia.bl 72 S O O tetrahydrofuran-2-yl Ia.bl 73 S O O tetrahydropyran-2-yl 25Ia.bl 74 S O O oxepan-2-yl Ia.bl 75 S O O thiiran-2-yl Ia.bl 76 S O O thietan-2-yl Ia.bl 77 S O O tetrahydrothiofuran-2-yl Ia.bl 78 S O O tetrahydrothiopyran-2-yl 30Ia.bl 79 S O O thiepan-2-yl Ia.bl 80 S O O oxetan-3-yl Ia.bl 81 S O O tetrahydrofuran-3-yl Ia.bl 82 S O O tetrahydropyran-3-yl 35Ia.bl 83 S O O oxepan-3-yl Ia.bl 84 S O O thiethan-3-yl Ia.bl 85 S O 0 tetrahydrothiofuran-3-yl Ia.bl 86 S O 0 tetrahydrothiopyran-3-yl 40Ia.bl 87 S O O thiepan-3-yl Ia.bl 88 S O O tetrahydropyran-4-yl Ia.bl 89 S O O oxepan-4-yl Ia.bl 90 S O O tetrahydrothiopyran-4-yl Ia.bl 91 S O O oxepan-4-yl Ia.bl 92 S O O tetrahydrothiopyran-4-yl Ia.bl 93 S O O O CH3 ~~5~~5~~$~ CA 02377143 2001-12-19 No . X Z Y U R6 Ia.bl 94 S O O O C2H5 Ia.bl 95 S 0 O O n-C3H~

Ia.bl 96 S 0 O O i-C3H~

Ia.bl 97 S O O O cyclopropyl Ia.bl 98 S 0 O COZH

Ia.bl 99 S 0 O C02CH3 Ia.bl 100 S O O C02C2H5 Ia.bl 101 S O O CH2C02CH3 Ia.bl 102 S O O CH(CH3)C02CH3 Ia.bl 103 S O O O CHZC02CH3 Ia.bl 104 S O O O CH(CH3)COzCH3 Ia.bl 105 S O O C1 Ia.bl 106 S O O CN

Ia.bl 107 S O O CH2CcCH

Ia.bl 108 S O O O CHZC~CH

Ia.bl 109 S O O CH20CH3 Ia.bl 110 S O O CHZCHZOCH3 Ia.bl 111 S O O O CH2CHzOCH3 Ia.bl 112 S 0 O CHZ cyclopentyl Ia.bl 113 O S O H

Ia.bl 114 O S O CH3 Ia.bl 115 O S O C2H5 Ia.bl 116 O S O n-C3H~

Ia.bl 117 O S O I-C3H~

Ia.bl 118 O S O cyclopropyl Ia.bl 119 0 S O n-C4H9 Ia.bl 120 O S O sec-C4H9 Ia.bl 121 O S O i-CqH9 Ia.bl 122 0 S O t-C4H9 Ia.bl 123 O S 0 CH2 cyclopropyl Ia.bl 124 O S O cyclopentyl Ia.bl 125 0 S 0 cyclohexyl Ia.bl 126 O S O oxiran-2-yl Ia.bl 127 0 S 0 oxetan-2-yl Ia.bl 128 O S 0 tetrahydrofuran-2-yl Ia.bl 129 O S 0 tetrahydropyran-2-yl Ia.bl 130 O S 0 - oxepan-2-yl ~

Ia.bl 131 O S O thiiran-2-yl Ia.bl 132 O S O thietan-2-yl No . ~ ~~ X Z Y U R6 Ia.bl 133 O S 0 tetrahydrothiofuran-2-yl Ia.bl 134 O S O tetrahydrothiopyran-2-yl 5 Ia.bi 135 O S O thiepan-2-yl Ia.bl 136 O S O oxetan-3-yl Ia.bl 137 O S O tetrahydrofuran-3-yl Ia.bl 138 O S O tetrahydropyran-3-yl Ia.bl 139 O S O oxepan-3-yl Ia.bl 140 O S O thiethan-3-yl Ia.bl 141 O S 0 tetrahydrothiofuran-3-yl Ia.bl 142 O S O tetrahydrothiopyran-3-yl Ia.bl 143 O S O thiepan-3-yl 15Ia.bl 144 O S O tetrahydropyran-4-yl Ia.bl 145 O S O oxepan-4-yl Ia.bl 146 O S O tetrahydrothiopyran-4-yl Ia.bl 147 O S O oxepan-4-yl 20Ia.bl 148 O S O tetrahydrothiopyran-4-yl Ia.bl 149 O S O O CH3 Ia.bl 150 O S 0 O C2H5 Ia.bl 151 O S 0 O n-C3H~

25Ia.bl 152 O S O O i-C3H7 Ia.bl 153 O S O O cyclopropyl Ia.bl 154 O S O COzH

Ia.bl 155 O S O C02CH3 Ia.bl 156 O S O C02C2H5 -_ 30Ia.bl 157 O S O CHzCO2CH3 Ia.bl 158 O S O CH(CH3)C02CH3 Ia.bl 159 O S O O CH2C02CH3 Ia.bl 160 O S O O CH(CH3)C02CH3 35Ia.bl 161 O S 0 Cl Ia.bl 162 O S O CN

Ia.bl 163 0 S O CH2C=CH

Ia.bl 164 O S O 0 CH2C~CH

40Ia.bl 165 O S O CHyOCH3 Ia.bl 166 O S O CHZCHzOCH3 Ia.bl 167 O S O O CHZCH20CH3 Ia.bl 168 O S O CHZ cyclopentyl Ia.bl 169 O O O H

Ia.bl 170 O O O CH3 Ia.bl 171 O 0 0 n-C3H~

No . X Z Y U R6 Ia.bl 172 O O 0 i-C3H~
Ia.bl 173 O O O cyclopropyl Ia.bl 174 O 0 0 n-C4H9 Ia.bl 175 O O O sec-C4Hg Ia.bl 176 O 0 O 1-C4H9 Ia.bl 177 O O O t-C4H9 Ia.bl 178 O O O CH2 cyclopropyl c clo entyl Ia.bl 179 O O O Y p Ia.bl 180 O O O cyclohexyl Ia.bl 181 O O O oxiran-2-yl Ia.bl 182 O O 0 oxetan-2-yl Ia.bl 183 O O O tetrahydrofuran-2-yl Ia.bl 184 O 0 O tetrahydropyran-2-yl Ia.bl 185 O O O oxepan-2-yl Ia.bl 186 O O O thiiran-2-yl Ia.bl 187 O O O thietan-2-yl Ia.bl 188 O O O tetrahydrothiofuran-2-yl Ia.bl 189 O O O tetrahydrothiopyran-2-yl Ia.bl 190 O O O thiepan-2-yl Ia.bl 191 O O O oxetan-3-yl Ia.bl 192 O O O tetrahydrofuran-3-yl Ia.bl 193 O O O tetrahydropyran-3-yl Ia.bl 194 O O O oxepan-3-yl Ia.bl 195 O O 0 thiethan-3-yl Ia.bl 196 O O O tetrahydrothiofuran-3-yl Ia.bl 197 O O O tetrahydrothiopyran-3-yl Ia.bl 198 O 0 0 thiepan-3-yl Ia.bl 199 O O O tetrahydropyran-4-yl Ia.bl 200 O O 0 oxepan-4-yl Ia.bl 201 0 O 0 tetrahydrothiopyran-4-yl Ia.bl 202 O O 0 oxepan-4-yl Ia.bl 203 O O 0 tetrahydrothiopyran-4-yl Ia.bl 204 O O 0 O CH3 Ia.bl 205 O 0 0 0 CZHS
Ia.bl 206 O O 0 O n-C3H~
Ia.bl 207 O O O 0 i-C3H~
Ia.bl 208 O 0 O O cyclopropyl Ia.bl 209 O O 0 C02H
Ia.bl 210 O 0 O COzCH3 No . X Z Y U R6 -""

Ia.bl 211 0 O 0 C02C2H5 Ia. b1 212 0 O 0 CH2C02CH3 Ia.bl 213 0 0 O CH(CH3)C02CH3 Ia.bl 214 O O O O CHZCOZCH3 Ia.bl 215 O 0 O O CH(CH3)C02CH3 Ia.bl 216 O O O C1 Ia.bl 217 O O 0 CN

CH C~CH
Ia.bl 218 O o O 2 Ia.bl 219 O O 0 O CH2C=CH

Ia.bl 220 O O O CHaOCH3 Ia.bl 221 O O O C2H5 Ia.bl 222 O O O CH2CH20CH3 Ia.bl 223 O O O O CHZCH20CH3 Ia.bl 224 O O O CHZ cyclopentyl Preference is furthermore given to the compounds Ib.bll to Ib.b1224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
,H
~N
Z~N~C' ~ ~ I Ib.b~
U
YIURB

Preference is furthermore given to the compounds Ia.b21 to Ia.b2224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
X
CI
la. b2 a C02CH3 URs Preference is furthermore given to the compounds Ib.b21 to Ib.b2224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:

02CHa N
~N~ ~~ ~ ~ Ib.b2 a C CI
X
VY
URB
Preference is furthermore given to the compounds Ia.b31 to Ia.b3224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
X
I ~ ~ CI
N~~. _ ~N ~ ~ ~ la.b3 a i C02C2H5 ~ a Preference is furthermore given to the compounds Ib.b31 to Ib.b3224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
N
~N~ ~~ ~ ~ I Ib.b3 C C
\/ N
CURB
Preference is furthermore given to the compounds Ia.b41 to Ia.b4224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
CI
XI~
CI
N' ~ la.b4 ~N O
a C02Chi3 ~ s Preference is furthermore given to the compounds Ib.b41 to Ib.b4224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
C~2CH3 I
Ib.b4 Preference is furthermore given to the compounds Ia.b51 to Ia.b5224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
CI
X
CI
labs ZEN
[
COaC2H5 YRe Preference is furthermore given to the compounds Ib.b51 to Ib.b5224, in which the variables X, Z, U and R6 each have the meanings mentioned.in rows 1 to 224 of Table 2:
OaCxHs N CI
~N\ ~~ / ~ Ib.bS
C CI
/N
Y'UR~
Preference is furthermore given to the compounds Ia.b61 to Ia.b6224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:

CI
I / ~ c1 ~N~ '~ labs N ~N
5 a CN URs 10 Preference is furthermore given to the compounds Ib.bsl to Ib.b6224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
CN
N
15 ~ ~ Ib.bg Preference is furthermore given to the compounds Ia.b71 to Ia.b7224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
la.b~
Preference is furthermore given to the compounds Ib.b71 to Ib.b~224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
O~C~NHC02CH3 CI
N Ib.b~
f ~N~ ~~ / ~ CI
C
I I
X
/N
YI~He Preference is furthermore given to the compounds Ia.b81 to Ia.bB224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
CI
X
I ~ ~ CI
la.bB
a URB
p' ~NHSOZCH3 Preference is furthermore given to the compounds Ib.bel to.
Ib.b8224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
O~ C~NHS02CH3 CI
Ib.be uN~C~ ~ ~ CI
IXI
O' /'N
UY'RB
Preference is furthermore given to the compounds Ia.b91 to Ia.b9224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
F
X / \
CI
~~~ _ la.b9 ~N
~~02CH3 ~RB
Preference is furthermore given to the compounds Ib.b91 to Ib.b9224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:

O2rrf'13 N F
~N~ .~ ~ ~ Ib.bg C CI
X
OY
URB
Preference is furthermore given to the compounds Ia.bl°1 to Ia.bl°224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
F
X
~C\ ~ ~ CI
la.b~o N N
~ ~~2C2H5 ~ 8 Preference is furthermore given to the compounds Ib.bl~l to Ib.bl°224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
~ 02CZH5 .
N F
~N~ Ib.b~o Preference is furthermore given to the compounds Ia.blll to Ia.b11224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
F
X
CI
~N p ~ la.b~~
' /N
YIN
URg Preference is furthermore given to the compounds Ib.blll to Ib.b11224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
CN
~ F
N
~N~ Ib.bl1 a Preference is furthermore given to the compounds Ia.b121 to Ia.b1z224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
F
X
I / ~ CI
la.bl2 Z'w/NI O / N
CHO
UR°
Preference is furthermore given to the compounds Ib.b121 to Ib.b12224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
CHO
F
Z~N\C~a ~ ~ CI Ib.b~2 O' /' ~IU'RB
Preference is furthermore given to the compounds Ia.b131 to Ia.b13224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:

F
la.b~3 O~~~NHCOzCH3 Preference is furthermore given to the compounds Ib.b131 to Ib.b13224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
O~NHC02CH3 F
Ib.b~3 ~/N~C~ ~ ~ CI
I I
X
Preference is furthermore given to the compounds Ia.b141 to Ia.b14224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:
F
X
N~CL' ~ ~ CI
~ I ~ ~ la.b~4 W/N \ /N
CURB
O~~ ~NHSOaCH3 Preference is furthermore given to the compounds Ib.b141 to Ib.b14224, in which the variables X, Z, U and R6 each have the meanings mentioned in rows 1 to 224 of Table 2:

O~~C~NHS02CH3 N F
~N Ib.bya Furthermore, preference is given to the compounds Ia.bls to Zal to Ia.bls to za224 which differ from the compounds Ia.bl to 141 to Ia.bl to 14224 only in that Y is S:

l \ Ra ~N ~ la.b~s«xa ~Re and the compounds Ib.bls to 2a1 to Ib.bls to 2a224 which differ from the compounds Ia.bls to 2a1 to Ia.bls to 2e224 only in that the N
substituents are inverted:
R
Ra ~N~ .~ / \ a Ib.b~s~o2s a C R
S~N
~~U('Rs Moreover, particular preference is given to the substituted ureas of the formula Ia.cl X
~~. / \ a ~N p R la.c~
w/ ~R N~~' URB

in particular tv the compounds listed in Table 3 below:
Table 3 No R Y
.
~Z
X

I a.cl 1 S H H C 1 H
O O

I a.cl 2 S H H C l C H3 O O

I a.cl 3 S H Cl O C 2H5 O H

I a'cl 4 O S H C l O n-C3H~
H

Ia.cl O S H H Cl O i-C3H7 Ia.cl O S H H Cl O cyclopropyl Ia.cl O S H H Cl O n-C4Hg Ia.cl O S H H C1 O sec-C4Hg Ia.cl O S H H Cl O i-C4Hg Ia.cl O S H H Cl O t-C4Hg Ia.cl O S H H Cl O CH2 cyclopropyl Ia.cl O S H H C1 0 cyclopentyl Ia,cl O S H H C1 0 cyclohexyl Ia.cl O S H H C1 O oxiran-2-yl Ia.cl O S H H Cl O oxetan-2-yl Ia.cl O S H H Cl O tetrahydrofuran-2-yl Ia.cl O S H H C1 O tetrahydropyran-2-yl Ia.cl O S H H C1 0 oxepan-2-yl Ia.cl O S H H C1 O thiiran-2-yl Ia.cl O S H H C1 O thietan-2-yl Ia.cl O S H H C1 O tetrahydrothiofuran-2-yl tetrah drothio ran-2 1 Ia.cl O S H H C1 O Y pY -y Ia.cl O S H H C1 O thiepan-2-yl Ia.cl O S H H C1 O oxetan-3-yl Ia.cl O S H H C1 O tetrahydrofuran-3-yl Ia.ci O S H H G1 O tetrahydropyran-3-yl Ia.cl O. S H H C1 0 oxepan-3-yl Ia.cl O S H H C1 O thiethan-3-yl Ia.cl O S H H C1 O tetrahydrothiofuran-3-yl Ia.cl O S H H C1 0 tetrahydrothiopyran-3-yl Ia.cl O S H H C1 O thiepan-3-yl Ia.cl O S H H Cl O tetrahydropyran-4-yl Ia.cl O S H H C1 O oxepan-4-yl Ia.cl 0 S H H C1 O tetrahydrothiopyran-4-yl Ia.cl O S H H C1 O oxepan-4-yl Ia.cl O S H H C1 O tetrahydrothiopyran-4-yl No Z X R R3 R4 Y U R6 .

Ia.cl O S H H C1 O 0 CH3 Ia.cl O S H H C1 O O C2H5 Ia.cl O S H H C1 0 0 n-C3Hy Ia.cl O S H H C1 O O i-C3H~

Ia.cl O S H H Cl 0 O cyclopropyl Ia.cl O S H H C1 O COZH

Ia.cl O S H H C1 0 C02CH3 Ia.cl O S H H Cl O C02C2H5 Ia.cl O S H H C1 O CHZC02CH3 Ia.cl O S H H C1 O CH(CH3)C02CH3 Ia.cl O S H H C1 0 O CH2C02CH3 5 Ia.cl O S H H C1 O O CH(CH3)COyCH3 Ia.cl 0 S H H Cl O C1 Ia.cl O S H H C1 O CN

Ia.cl O S H H C1 O CH2CCH

Ia.cl O S H H C1 O 0 CH2C~CH

Ia.cl O S H H Cl O CH20CH3 Ia.cl O S H H C1 O CH2CH20CH3 Ia.cl O S H H C1 O 0 CHZCH20CH3 Ia'cl O S H H C1 O CH2 cyclopentyl 0050'SOO8o CA 02377143 2001-12-19 Moreover, preference is given to the compounds Ib.cll to Ib.c156 which differ from the compounds Ia.cll to Ia.c156 only in that the N substituents are inverted:

R
Ib.c~
U R°
Moreover, preference is given to the compounds Ia.c21 to Ia.cz56 which differ from the compounds Ia.cll to Ia.c156 only in that R
is COZCH3:
X
~C~ ~ ~ CI
la.c2 I~/I N ~
C02CH3 ~ a Moreover, preference is given to the compounds Ib.c21 to Ib.cz56 which differ from the compounds Ia.cll to Ia.cl56 only in that the N substituents are inverted and R is C02CH3:
2 5 ~ 02CH3 N
~N~ ~~
C CI
X
30, N'\ 'O
'U~Re Moreover, preference is given to the compounds Ia.c31 to Ia.c356 which differ from the compounds Ia.cll to Ia.c156 only in that R
35 is C02CH3 and R3 is Cl:
CI
X
CI
~N ~ la.c3 40 ~I N ~ O
C02CH3 uRe Moreover, preference is given to the compounds Ib.c31 to Ib.c356 which differ from the compounds Ia.cll to Ia.c156 only in that the 45 N substituents are inverted and R is COZCH3 and R3 is C1:

~~50~,c~~80 CA 02377143 2001-12-19 CI
I
~N~ ~~
CI Ib.c3 Nw a Moreover, preference is given to the compounds Ia.c41 to Ia.c456 which differ from the compounds Ia.cll to Ia.c156 only in that R
is COZC2H5 and R3 is C1:
CI
X
I
CI
~N ~ la.c4 UN N ~ O

Moreover, preference is given to the compounds Ib.c41 to Ib.c456 which differ from the compounds Ia.cll to Ia.c156 only in that the N substituents are inverted and R is COZC2H5 and R3 is C1:
~2''2H5 N CI
~N~ .~
2 5 ~ CI Ib.c4 N\'O
~U R°
Moreover, preference is given to the compounds Ia.c51 to Ia.c556 which differ from the compounds Ia.cll to Ia.c156 only in that R
is C(O)NHCOzCH3 and R3 is C1:
C!
X
~~~ ~ ~ CI
N
~N ~ N O la.c5 ~RB
O~' ~NHC02CH3 Moreover, preference is given to the compounds Ib.csl to Ib.c556 which differ from the compounds Ia.cll to Ia.c156 only in that the N substituents are inverted and R is C(O)NHC02CH3 and R3 is C1:

CI
~N~ ~~
C CI Ib,cs URe Moreover, preference is given to the compounds Ia.csl to Ia.c656 which differ from the compounds Ia.cll to Ia.c156 only in that R
is C(O)NHS02CH3 and R3 is C1:
CI
X
I ~ ~ CI
lace ~N N_' Y'URB
O' ~NHS02CH3 Moreover, preference is given to the compounds Ib.c61 to Ib.c656 which differ from the compounds Ia.cll to Ia.c156 only in that the N substituents .are inverted and R is C(O)NHSOZCH3 and R3 is C1:
O~~C~NHSOZCH3 CI Ib,cs Moreover, preference is given to the compounds Ia.c71 to Ia.c756 which differ from the compounds Ia.cll to Ia.c156 only in that R
is C02CH3 and R3 is F:
F
X
~N~CL\~ ~ ~ CI
hiI
ZEN N \ O la.c~
C02CH3 ~ a Moreover, preference is given to the compounds Ib.c71 to Ib.c756 which differ from the compounds Ia.cll to Ia.c156 only in that the N substituents are inverted and R is C02CH3 and R3 is F:

OaCHs N F
I
~N~
C ~ ~ CI Ib.d X
N \ 'O
IYU Rs Moreover, preference is given to the compounds Ia.c81 to Ia.c856 which differ from the compounds Ia.cll to Ia.c156 only in that R
is C02CZH5 and R3 is F:
F
X
~C~ ~ ~ CI
~N ~ N O lace Moreover, preference is given to the compounds Ib.c81 to Ib.c856 which differ from the compounds Ia.cll to Ia.c156 only in that the N substituents are inverted and R is C02C2H5 and R3 is F:
OzCzHs ~N F
I
Z~N~C'~ ~ ~ CI Ib.cB
X
N \ 'O
~'U'Rs Moreover, preference is given to the compounds Ia.c91 to Ia.c956 which differ from the compounds Ia.cll to Ia.c156 only in that R
is C(O)NHC02CH3 and R3 is F:
F
X
~C~ ~ ~ CI
N
~N ~ N O la.c9 O~' ~NHCOZCH3 Moreover, ~~ef=rence is given to the compounds Ib.c91 to Lb.cg56 which d.it_~swum the compounds Ia.cl1 to Ia.c156 only ~u r_hat the N subst:i t!_i:~:1'~.~ a re inverted and R is C ( O ) NHCOZCH3 and E? ' ., F

O\~C~NHC02CH3 F
I H
Z~N~C~b / ~ CI Ib.c9 X
N~O
~U'Rs Moreover, preference is given to the compounds Ia.cl°1 to Ia.cl°56 which differ from the compounds Ia.cll to Ia.c156 only in that R
is C(O)NHSO2CH3 and R3 is F:
F
CI
1 !, ~ I 1 la.c~o U RB

Moreover, preference is given to the compounds Ib.clll to Ib.c1156 which differ from the compounds Ia.cll to Ia.c156 only in that the N substituents are inverted and R is C(O)NHS02CH3 and R3 is F:
O\~C~NHS02CH3 ~N F
I H
Z~N~C'~ ~ ~ CI Ib.co i1 X
N\'O
3 0 C'U'RB
Moreover, preference is given to the compounds Ia.clz to zzl to Ia.clz to zz56 which differ from the compounds Ia.cl to ill to Ia.cl to 1156 only in that Y is S:
R
X
Il ~ \ Ra ~'~N'C~N
I H la.c~2 co 22 ZuN~R N w S
Moreover, preference is given to the compounds Ib.clz ~° -''~ to Ib.clz to zz56 c.rhich differ from the compounds Ia.cl t° '-- l to Ia.c to m56 only in that the t7 substituents are inverted anc: Y L~ 5:

a Ib.c~ztozz Moreover, preference is given to the compounds Ia.c23 to 331 to Ia.c23 to x356 which differ from the compounds Ia.cl to 111 to Ia.cl to 1156 only in that X is 0:

O
N~C' ~ ~ Ra la.czs to 33 ~N
w/ ~R N~S
U RB
Moreover, preference is given to the compounds Ib.c23 to 331 to Ib.c23 to 3356 which differ from the compounds Ia.cl to 111 to Ia.cl to 1156 only in that the N substituents are inverted and X is O:
~N~R Rs a z~N~C~ ~ ~ R4 Ib.C23to33 O
2 5 N \ 'S
IYURe Moreover, preference is given to the compounds Ia.c34 to 441 to Ia.c34 to 4456 which differ from the compounds Ia.cl to 111 to Ia.cl to 1156 only in that Z is S

O
~N~C\N ~ ~ R4 S~~\N~ H N S la.c3atoa4 R Y
UR
Moreover, preference is given to the compounds Ib.c34 to 441 to Ib.c34 to 4456 which differ from the compounds Ia.cl to 111 to Ia.c1 to 1156 only in that the r1 substituents are inverted and Z is S:

~NiR Ra I
S~N~Cr~~ / ~ R4 Ib.Ca4to44 I I
O
N'\'S
~5 Moreover, particular preference is given to the substituted ureas of the formula Ia.dl Ra X
~N~ ~~ la.d~
I
Z~N~R
~~ O
in particular to the compounds listed in Table 4 below:
Table 4 No Z X R R3 Y T R7 . O S H H O CH3 dl 1 Ia . O S H H O C2H5 dl 2 Ia . O S H H O n-C3H7 Ia dl 3 . O S H H O cyclopropyl dl 4 Ia . O S H H O n-C4H9 dl 5 Ia . O S H H O sec-C4H9 dl 6 Ia . O S H H O t C4H9 dl 7 0 Ia . O S H H O CH2-CH=CHz dl 8 Ia . O S H H O CHz-C=CH
d1 9 Ia . O S H H O CH2CH2C1 dl 10 Ia . O S H H O CHZCH20CH3 dl 11 Ia ~ O S H H O CH2CHZCN

dl 12 Ia . O S H H O H
dl 13 Ia . O S H H O O H
dl 14 Ia . O S H H 0 0 CH3 dl 15 _ Ia . O 0 CzHs O S H H
d1 16 Ia . O S H H O O n-C3H7 _ dl 17 Ia . O S H H - 0 cyclopropyl dl 18 0 _j Ia . O S H H 0 C) n-C4H9 .~_.
dl 19 Ia . O S H H 0 0 sec-C4H9 _~._ ~S Ia d'- 20 . O S H H - 0 ~ t C4H9 ~~-_ Ia.dl 21 -- O

No . Z X R Rs Y T R7 Ia.dl 22 O S H H O O CH2-CH=CH2 Ia.dl 23 O S H H O O CH2-C=CH

Ia. dl O S H H O O CH2CH2C1 Ia.dl 25 O S H H O O CHZCHZOCH3 Ia.dl 26 0 S H H 0 0 CHZCHZCN

Ia.dl 27 O S H H O O i-C3H7 Ia.dl 28 O S H H O 0 i-C4Hg Ia.dl 29 O S H H 0 i-C3H7 Ia.dl 30 O S H H O i-C4Hg Ia.dl 31 O S H H O O CH2COZCH3 Ia.dl 32 O S H H O O CH(CH3)C02CH3 Ia.dl 0 S H H 0 O CH(CH3)C02C2H5 Ia.dl 34 O S H H 0 CHZCOZCH3 Ia.dl 35 O S H H O CHzC02-n-C3H7 Moreover, preference is given to the compounds Ib.dll to Ib.d135 which differ from the compounds Ia.dll to Ia.d135 only in that the N substituents are inverted:
N~R Rs ~N~ .~
C Y Ib.d~
1'R' O
30-Moreover, preference is given to the compounds Ia.dzl to Ia.d235 which differ from the compounds Ia.dll to Ia.d135 only in that R
is COZCH3:

X
II ~ \
~N~C~~ Y la.dz HI
Z~N~C02CH3 N
TR' 4~ Moreover, preference is given to the compo~_mds Ib.d21 to Ib.dz35 vahich differ from the compounds Ia.dl1 to :~a.d'-35 only in that the r1 substituents are inverted and R is CO~C~I-j v OxCHa Ir _ I H
zuN~C.~ / ~ Y
I I Ib.d2 X

Moreover, preference is given to the compounds Ia.d31 to Ia.d335 which differ from the compounds Ia.dll to Ia.d135 only in that R
is C02CH3 and R3 is C1:
CI
X
~N~~\~ / ~ Y la.d3 Zu'N~C0h2iCH3 ~V
O
Moreover, preference is given to the compounds Ib.d31 to Ib.d335 which differ from the compounds Ia.dll to Ia.d135 only in that the N substituents are inverted and R is C02CH3 and R3 is C1:

~N CI
I H
zuN~C~~ / ~ Y
X Ib.d3 O
Moreover, preference is given to the compounds Ia.d41 to Ia.d435 which differ from the compounds Ia.dll to Ia.d135 only in that R
is COZC2H5 and R3 is C1:
CI
X
~N~C\~ / ~ Y la.d4 3 5 Z~N~COZCzHS ~J
O
t~toreover, preference is given to the compounds Zb.d41 to Ib.d435 ~~h.ich differ from the compounds Ia.dll to Ia_d135 only in that the c1 subst.:ituents are inverted and R is CU~C ~H~ ~~nd Rj is C1 ~5 0050~5008~ CA 02377143 2001-12-19 1~7 Z~
Ib,d4 Moreover, preference is given to the compounds Ia.d51 to Ia.d535 which differ from the compounds Ia.dll to Ia.d135 only in that R
is C(O)NHC02CH3 and R3 is Cl:
CI
X
N'~~~ / \ Y la.d5 ~N
a O
.. .

Moreover, preference is given to the compounds Ib.d51 to Ib.d535 which differ from the compounds Ia.dll to Ia.d135 only in that the N substituents are inverted and R is C(O)NHC02CH3 and R3 is C1:
O\~C~NHC02CH3 CI
~I
~N.C~ / \ ~, Ib.ds I I
X
O
Moreover, preference is given to the compounds Ia.dsl to Ia.d635 which differ from the compounds Ia.dll to Ia.d135 only in that R
is C(0)NHS02CH3 and R3 is C1:
CI
X
~~' / \
~N ~ la.dd . ZEN

O' ~NHSOZCH3 ivloreo~rer, preference is given to the compounds Ib.d«L to Ib.dti35 ;,rhich differ from the compounds Ia.dl1 to Ia.a:-5 only in that the ~1 substituents are inverted and R is C(O)NHSO::~:E~3 .~{ad R3 is C1:

0050~5~080 CA 02377143 2001-12-19 l~$
O\ C~NWS02CH3 CI
~N~ .N ~ ~ Ib.de v C Y
O
Moreover, preference is given to the compounds Ia.d71 to Ia.d~35 which differ from the compounds Ia.dll to Ia.d135 only in that R
is COzCH3 and R3 is F:
F
X
N~C~~ / \ Y la.d~
~N~C02CH3 O
Moreover, preference is given to the compounds Ib.d71 to Ib.d735 which differ from the compounds Ia.dll to Ia.d135 only in that the N substituents are inverted and R is C02CH3 and R3 is F:
02CHs ~N F
I H
zuN~C~~ I ~ Y
II Ib.d~
X
O
Moreover, preference is given to the compounds Ia.dgl to Ia.d835 which differ from the compounds Ia.dll to Ia.dl 35 only in that R
is COZCZH5 and R3 is F:
F
X
~N~C~~ ~ ~ Y lade Z~N~C0h2iCzH5 ~J
TR' O
Moreover, preference is given to the compounds Ib.dgl to Ib.d835 which differ from the compounds Ia.dll to Ia.d1 35 only in that the N substituents are inverted and R is CO?C-~H; and R' is F:

Ib.de O
Moreover, preference is given to the compounds Ia.d91 to Ia.d935 Which differ from the compounds Ia.dll to Ia.d135 only in that R
is C(O)NHCHZCH3 and R3 is F:
F
X
la. d9 ~N
ZuN
O' ~NHC02CH3 Moreover, preference is given to the compounds Ib.d91 to Ib.d935 Which differ from the compounds Ia.dll to Ia.d135 only in that the N substituents are inverted and R is C(O)NHCOZCH3 and R3 is F:
O\~C~NHC02CH3 Ib.d9 Moreover, preference is given to the compounds Ia.dl°1 to Ia.dl°35 which differ from the compounds Ia.dll to Ia.dl 35 only in that R
is C(O)NHSOZCH3 and R3 is F:
F
X
I I
N~C~N _ Y la.d~o ~N H
TRH O
O' C~NHSOZCH3 Moreover, preference is given to the compounds Ib,d'-'1 to Ib.d935 which differ :from the compounds Ia.dll to Ia.d'-?5 onl~~ in that the N substituents are in=ferted and R is C(O)NHSOZCH_~ and R3 is F:

fb,d~~
Moreover, preference is given to the compounds Ia.dlll to Ia.d1135 Which differ from the compounds Ia.dll to Ia.dl 35 only in that R
is COZCH3, R3 is F and Y is S:
F
X
' /_\ S la.d~, Z~ 'CO~H3 ~ ~ O
Moreover, preference is given to the compounds Ib.dlll to Ib.d1135 Which differ from the compounds Ia.dll to Ia.d135 only in that the N substituents are inverted and R is COzCH3, R3 is F and Y is S:
~CO~H3 ~N F
I
Z~-N~~'b i v ~~ Ib.d~~
X
N
O
Moreover, preference is given to the compounds Ia.dlz to z21 to Ia.dlz to z235 which differ from the compounds Ia.dl to 111 to Ia.dl to 1135 only in that X is O:

O
N'C'N / \ Y la.d~zcozz W H
Z~N'R
TR' O
Moreover, preference is given to the compounds Ib.dlz to z21 t o 4p Ib.dlz to 2z35 which differ from the compounds Ia.d1 to '11 to Ia.dl to 1135 only in that the N substituents are inverted and X is 0:
~1~
n muen ~u N~H R3 ~N~
C Y
I I
O

Ib.d~2 to ii Moreover, preference is given to the compounds Ia.d23 to 331 to Ia.d23 to 3335 which differ from the compounds Ia.dl to 111 to Ia.dl to 1135 only in that Z is S:

X
I
~ Y
_N ~ la.d23to33 \R ~~ O
Moreover, preference is given to the compounds Ib.d23 to 331 to Ib.dz3 to 3335 which differ from the compounds Ia.dl to 111 to Ia.dl to 1135 only in that the N substituents are inverted and Z is S:
-N' N
a I b.d23 to 33 Moreover, particular preference is given to the substituted ureas of the formula Ia.el X
I I
~N~C~~ Y la.e~
Hl ZuN~R N~O
TR' in particular to the compounds listed in Table 5 below:
Table 5 No . Z X R R3 Y T R7 ~

Ia.el 0 S H H 0 CH3 Ia.el 0 S H H O C~H

Ia.el O S H H O w -C3H~
3 ~

Ia.e1 O S H H 0 cyclopropyl Ia.el 0 S H H 0 n-C4H9 Ia.el O S H H O sec-C~H9 No Z X R R3 Y T R7 Ia.el O S H H O t-C4H9 Ia.el O S H H O CH2-CH=CH2 8 .

Ia.el O g H H ~ CHZ_~~CH -.

Ia.el O S H H O CH2CHZC1 Ia.el O S H H O CHZCH20CH3 Ia.el O S H H O CHZCH2CN

Ia.el O S H H O H

Ia.el O S H H O O H

Ia. e1 O S H H O O CH3 Ia.el O S H H O 0 CZH5 Ia.el O S H H O O n-C3H7 15 Ia.e1 O S H H O O cyclopropyl Ia.el O S H H O O n-C4H9 Ia.el O S H H O O sec-C4H9 Ia.el O S H H O O t-C4H9 20 Ia.el O S H H O O CHZ-CH=CH2 Ia.el O S H H O O CH2-C=-CH

Ia.el O S H H O O CH2CH2C1 Ia.el 0 S H H O O CHZCH20CH3 25 Ia.el O S H H O O CH2CHZCN

Ia.el O S H H O O i-C3H7 Ia.el O S H H O O i-C4H9 Ia.el O S H H O i-C3H7 Ia.el O S H H O i-C4H9 30 Ia.el O S H H O O CHZC02CH3 Ia.el O S H H O O CH(CH3)COZCH3 Ia.el O S H H O O CH(CH3)C02CZH5 Ia.el 0 S H H O CHZCOZCH3 Ia.el O S H H O CHzC02-n-C3H7 Moreover., preference is given to the compounds Ib.ell to Ib.e135 which differ from the compounds Ia.el1 to Ia.e135 only in that the N substituents are inverted:
~N~R R\,, z N~ _ i J, , Ib.e~
,N ' 0 TR' Moreover, preference is given to the compounds Ia.e21 to Ia.e235 which differ from the compounds Ia.ell to Ia.e135 only in that R
is C02CH3:

~N' '~ Y la.ez ZZ - 'O
~N'C02CH3 TR' Moreover, preference is given to the compounds Ib.e21 to Ib.e235 which differ from the compounds Ia.ell to Ia.e135 only in that the N substituents are inverted and R is COZCH3:
OzCHs ~N' C ~ Ib.ez N O
TRH
Moreover, preference is given to the compounds Ia.e31 to Ia.e335 which differ from the compounds Ia.ell to Ia.e135 only in that R
is C02CH3 and R3 is C1:
CI
X
~N' '~ Y la.e3 Z~N'COZCH3 N 7 ~O
TR
Moreover, preference is given to the compounds Ib.e31 to Ib.e335 which differ from the compounds Ia.el 1 to Ia.el 35 only in that the N substituents are inverted and R is C02CH3 and R3 is C1:

CI
H
ZuN'C'N
Ib.e3 N- \O
T R' Moreover, preference is given to the compounds Ia.e=~1 to Ia.e435 ~rhich differ from the compounds Ia.el1 to Ia.e135 only in that R
is CO~C~E!5 and R3 is Cl:

CI
X
I ~ \
' _ Y la.e~
~N' ~ ~N~O
~ C02C2H5 TR' Moreover, preference is given to the compounds Ib.e41 to Ib.e435 which differ from the compounds Ia.ell to Ia.e135 only in that the N substituents are inverted and R is C02C2H5 and R3 is C1:
~ OzCzHs ~N CI
I H
zuN~C~~
Y lb.e4 1.5 TRH O
Moreover, preference is given to the compounds Ia.e51 to Ia.e535 which differ from the compounds Ia.ell to Ia.e135 only in that R
is C(O)NHCOzCH3 and R3 is C1:
CI
X
I I
~N~C'~ Y la.es ~Z~N Fi N' \ O
TR' Moreover, preference is given to the compounds Ib.esl to Ib.e535 which differ from the compounds Ia.ell to Ia.e135 only in that the N substituents are inverted and R is C(O)NHCOzCH3 and R3 is Cl:
O\~C~NHCOZCH3 CI
~I H
z~N~C~~ ~ \ Ib.es X Y
N~O
TR' Moreover, preference is given to the compounds Ia.e61 to Ia.e535 which differ from the compounds Ia.e'-1 to Ia.e135 only in that R
is C ( O ) NHSC~~CH3 and R3 is C1:

m c1 x c ~N~ '~ Y la.ee LAN N!- 'O
TR' O' 'NHS02CH3 Moreover, preference is given to the compounds Ib.e61 to Ib.e635 which differ from the compounds Ia.ell to Ia.e135 only in that the N substituents are inverted and R is C(O)NHS02CH3 and R3 is C1:
O~ C~NHS02CH3 CI
~N' ,N ~ ~ Ib.ee C y X ~
N' 'O
TR' Moreover, preference is given to the compounds Ia.e71 to Ia.e735 which differ from the compounds Ia.ell to Ia.e135 only in that R
is COzCH3 and R3 is F:
F
X
C
N. '~ Y la.e~
~N' N~O
C02CH3 TR' Moreover, preference is given to the compounds Ib.e71 to Ib.e735 which differ from the compounds Ia.ell to Ia.e135 only in that the N substituents are inverted and R is COZCH3 and R3 is F:

~N F
I ~
ZuN'C
X Y Ib.e~
N- '' O
TR' Moreover, preference is given to the compounds Ia.esl to Ia.e~35 which differ from the compounds Ia.ell to Ia.eL3~ only in than is COzCzHS and R3 is F:

F
X
NBC' ~ ~ ~' la.ee ~N~ ~ ~N~O
CO2C2H5 TR' Moreover, preference is given to the compounds Ib.eel to Ib.e835 which differ from the compounds Ia.ell to Ia.e135 only in that the N substituents are inverted and R is COZCZHS and R3 is F:
~ 02CZH5 N F
~N~
a C ~ Ib.ee NI O
TR' Moreover, preference is given to the compounds Ia.e91 to Ia.e935 which differ from the compounds Ia.ell to Ia.e135 only in that R
1s C(O)NHC02CH3 and R3 is F:
F
X
I I
Y la. e9 ~N ~ N' \O

Moreover, preference is given to the compounds Ib.e91 to Ib.e935 which differ from the compounds Ia.ell to Ia.e135 only in that the N substituents are inverted and R is C(O)NHCOZCH3 and R3 is F:
O\~C~NHC02CH3 F
~N~ ~~ / ~ ib.e9 ~Y
N O
T~R' Moreover, preference is given to the compounds Ia.el°1 to Ia.e1°35 which differ from the compounds Ia.ell to Ia.e135 only in that R
is C(O)DIHSOzCH3 and R' is F:

0050~50~8~ CA 02377143 2001-12-19 F
X
NBC' ~ ~ Y la.e~o ~N N' \O
TR' O' NHS02CH3 Moreover, preference is given to the compounds Ib.el~l to Ib.e1~35 which differ from the compounds Ia.ell to Ia.e135 only in that the N substituents are inverted and R is C(0)NHS02CH3 and R3 is F:
O\~C~NHS02CH3 F
~N~ ~~ ~ ~ Ib.e~o I
TR' Moreover, preference is given to the compounds Ia.elll to Ia.e1135 which differ from the compounds Ia.ell to Ia.e135 only in that R
is C02CH3, R3 is F and Y is S:
F
X
N~C~ / \ S la.e~~
~ I
Z~N~COzCH3 TR' O
Moreover, preference is given to the compounds Ib.elll to Ib.e1135 which differ from the compounds Ia.ell to Ia.e135 only in that the N substituents are inverted and R is C02CH3, R3 is F and Y is S:
OzCHa ~N F
I
Z~N'C/ / \ S Ib.e"
X ~
N' \ O
TR' NSoreover, preference _Ls given to the compounds Ia.el2 to 221 to Ia.el2 to 2235 which dif.~er from the compounds Ia.el to 111 to Ia.e to 1135 only in that x ; ~ O:

if O
,I~ ~ \
N~~~~ Y la.e~zcc2x ~N~ H N' \O
a R ~R~
Moreover, preference is given to the compounds Ia.elz to zzl to Ia.elz to z235 which differ from the compounds Ia.el to 111 to Ia.el to 1135 only in that the N substituents are inverted and X is O:
~N~R
I
~N~~~ Ib.e~2~o2z X
Moreover, preference is given to the compounds Ia.ez3 to 331 to Ia.ez3 to 3335 which differ from the compounds Ia.el to 111 to Ia.el to 1135 only in that Z is S:
Rs X
,I~
N~~~~ / \ Y la.e2s~aas ~N~ H N' \O
R TR' Moreover, preference is given to the compounds Ia.ez3 to 331 to Ia.ez3 to ss35 which differ from the compounds Ia.el to 111 to Ia.el to 1135 only in that the N substituents are inverted and Z is S:
~R Rs N
I
~N, ~b I \
Ib.e23 to 3a N' \ O
T R' Moreover, particular preference is given to the substituted ureas oz the formula Ia.fl ~~ / \ R' ~..ns! ~H
la.f~
Z~.. ~I .. ~ O
O~' Rs~~Ra in particular to the compof.incls listed in Table 5 below:

Table 6 N Z X
R R3 R4. R8 R9 o. 0 S H H G1 H H
fl l Ia. 0 S H H C1 H CH3 f12 Ia. O S H H C1 H G2H5 f13 I

a. O S H H C1 H n-G3H7 f14 Ia. 0 S H H C1 H i G3H7 f15 I

a. O S H H C1 H n-C4H9 f16 I

a. O S H H C1 cyclopropyl H

f17 I

a. O S H H C1 CH3 H
flB
I

a. O S H H C1 CH3 CH3 f19 I

a. O S H H C1 CZHS H
f110 I

a. O S H H C1 C2H5 GH3 flll I

a. O S H H C1 n-C3H7 C2H5 f112 I

a. O S H H C1 n_C3H7 n_C3H7 f113 Ia. O S H H C1 C1 H
f114 I

a. O S H H C1 H C1 Ia.f115 O S H H Cl C1 CH3 f116 I

a. O S H H C1 _____ Cep) _____ f117 Ia. O S H H C1 CH3 CHZCHZC1 f118 I

a. 0 S H H C1 C2H5 G2H5 f119 I

a. O S H H C1 i-C3H7 1-C3H7 f120 I

a. O S H H C1 i C3H7 H
f121 Ia.

Moreover, preference is given to the compounds Ib.fll to Ib.f121 which differ from the compounds Ia.fll to Ia.f121 only in that the N substituents are inverted:
NCR
~I H
Ib.f~
O
O
Rs ~~d Moreover, preference is given to the compounds Ia.f21 to Ia.f221 T:rhich differ from the compounds Ia.fll to Ia.f121 only in that R
is COZCH3:

X
R4 la.i~
~N
~ ~C02CH3 O
O
Rs" RB
Moreover, preference is given to the compounds Ib.f21 to Ib.f221 which differ from the compounds Ia.fll to Ia.f121 only in that the N substituents are inverted and R is C02CH3:
02CHa Ra C R Ib.f~
O
O
Rs~Re Moreover, preference is given to the compounds Ia.f31 to Ia.f321 which differ from the compounds Ia.fll to Ia.f121 only in that R
is C02CH3 and R3 is Cl:
CI
X
II / \ Ra 2 5 . C. I a.f3 ~N
Z~N~C02CH3 O
O
Rs~Re Moreover, preference is given to the compounds Ib.f31 to Ib.f321 which differ from the compounds Ia.fll to Ia.f121 only in that the N substituents are inverted and R is COZCH3 and R3 is Cl:

3 5 ~ CI
\
C R
Ib.fa X
O
O\~
Rs~Rs P-Ioreover, preference is given to the compounds Ia.f'~l to Ia.f421 which ~~tiffer from the compounds Ia.fLl to Ia.f121 only in that R
is CO-~C:ZH~ and R3 is C1:

CI
x N~C~~ R la.f4 N. 0 a COzCxHs ~
Rs~Re Moreover, preference is given to the compounds Ib.f41 to Ib.f421 which differ from the compounds Ia.fll to Ia.f121 only in that the N substituents are inverted and R is C02CzH5 and R3 is Cl:
IC02C2Hs N CI
~N. .~ ~ ~ Ra C . I b.f4 X
O
O
Rs~Rs Moreover, preference is given to the compounds Ia.f51 to Ia.f521 which differ from the compounds Ia.fll to Ia.f121 only in that R
is C(O)NHC02CH3 and R3 is Cl:
CI
X
I / \ R4 la.fs N' O
O
Rs~Ra O' ~NHC02CH3 Moreover, preference is given to the compounds Ib.f51 to Ib.f521 which differ from the compounds Ia.fll to Ia.f121 only in that the N substituents are inverted and R is C(O)NHCOZCH3 and R3 is Cl:
3 5 O ~C~NHCOZCH3 CI
~N. ~~ ~ ~ R,, Ib.fs C
I I
X
O
O
Rs~Re Mo.reove ~_~ . creference is given to the compounds Ia. f° 1 to -.C-__m. f621 which differ L-rom the compounds Ia.fll to Ia.f121 only ~..n that R
is C ( O ) C1H~'yCu; and R3 is C1:

CI
X
Irl ~ \ Ra Ia.fe O
O~~
Rs~Ra Moreover, preference is given to the compounds Ib.fsl to Ib.f621 which differ from the compounds Ia.fll to Ia.f121 only in that the N substituents are inverted and R is C(O)NHS02CH3 and R3 is Cl:
O\ C~NHS02CH3 CI
Z~N~C~~ ~ \ Ra Ib.fs O
O~~
Ra/''Ra Moreover, preference is given to the compounds Ia.f71 to Ia.f721 which differ from the compounds Ia.fll to Ia.f121 only in that R
is COZCH3 and R3 is F:
F
X
\ Ra la.f~
~N
~C02CH3 O
O
R9"Ra Moreover, preference is given to the compounds Ib.f~l to Ib.f721 which differ from the compounds Ia.fll to Ia.f121 only in that the N substituents are inverted and R is COZCH3 and R3 is F:
~ 02CH3 ~N HF
I
Z~N~C~~ ~ \ Ra II Ib.f~
X
O
O
Rs~Ra Moreover, prezerence is given to the compounds Ia.f~l to Ia.~=~'<1 which differ srom the compounds Ia.fll to Ia.f121 on:Ly in .-.nat R
is C02CZH5 r:lnd R-'' is F

F
X
ICI ~ \ Ra la.fe ~N
uN~C02C2H5 O O
Rs~Re Moreover, preference is given to the compounds Ib.fel to Ib.f821 which differ from the compounds Ia.fll to Ia.f121 only in that the N substituents are inverted and R is C02C2H5 and R3 is F:

N F
I
N~ ~~ ~ \ a C R Ib.fe X
O
O
Rs~Ra Moreover, preference is given to the compounds Ia.f91 to Ia.f921 which differ from the compounds Ia.fll to Ia.f121 only in that R
is C(O)NHC02CH3 and R3 is F:
F
X
ICI / \ Ra N~ ~N la.fs N H
O
OJ
Rs~Rs O C~NHC02CH3 Moreover, preference is given to the compounds Ib.f91 to Ib.f921 which differ from the compounds Ia.fll to Ia.f121 only in that the N substituents are inverted and R is C(0)NHCOZCH3 and R3 is F:
3 5 ~ C~NHCO2CH3 F
~I
zVN~C~~ ~ \ R.v Ib.fs X
O
O
R9" Rg Moreover, prefereclce i.s given to the compounds Ia. fl°1 to Ia.
f'-°~ 'L
cahieh differ from. W?_~ compounds Ia.fll to Ia.f121 only in that is C ( O ) NHSOzCH; anti R.= is F

F
X
ICI / \ Ra ~N~ ~~ la.f~o ZEN p O
Re~Ra O' ~NHS02CH3 Moreover, preference is given to the compounds Ib.flol to Ib.flo21 which differ from the compounds Ia.fll to Ia.f121 only in that the N substituents are inverted and R is C(O)NHS02CH3 and R3 is F:
O~ ~NHS02CH3 ~C
F
~N\ ~a ~ \ a Ib.flo a C R
I I
X
O
O~
Rs~Re Moreover, preference is given to the compounds Ia.fll to 201 to Ia. fli to 2021 which differ from the compounds Ia. fl to 101 to Ia. fl to 1021 only in that X is O:
2 5 Ra O
II ~ \ Ra ~N~C~~ la.fic co zo Z~N~R Fi O
O\~
3 0 Rs~Ra Moreover, preference is given to the compounds Ib.fl1 to 201 to Ib.fli to 2o21 which differ from the compounds Ia.fl to lol to Ia.fl to 1021 only in that the N substituents are inverted and X is O:
~R Rs N
I
N
Z~ \C~ / \ Ra Ib.f» ca zo O
O
O\~
Rs~Ra a.to.reover, preference is given to the compounds Ia.fzi to 301 to _L3. f2i to 3021 which differ from the compounds Ia.fl to iol to Ia.f'-1'~21 anly in that Z is S:

;a X
II ~ \ Ra la.f~~ ec ao HI
S~N~ O
R O' R9x RB
M°reover, preference is given to the compounds Ib.fZl to aol to Ib. f21 to 3021 which differ from the compounds Ia. fl to lol to Ia.fl to 1021 only in that the N substituents are inverted and Z is S:
NCR F
~N~ ~~ ~ \ a Ib.f2~toso C R
O
O
Ra~Ra 12 fi To prepare the compounds of the formula Ia according to the invention where Z = O, it is possible, for example, to react the N-(2-hydroxyethyl)-N-amino-N'-acylureas known from WO 94/10173 and the later German Patent Application 198 29 745.9 according to scheme 1 with formaldehyde, for example an aqueous formaldehyde solution, to give the N-methylimino-N-(2-hydroxyethyl)-N'-acylureas, which are then cyclized in the presence of catalytic amounts of acid or a surface-active metal oxide to give the compound Ia according to the invention. For further details about the cyclization, reference is made to WO 94/10173 and the later patent application. Here and below, the variables used in the formulae are as defined above unless specifically stated otherwise.
Scheme 1 a HcHO _ ~~, , a ~N~ ~N~ ~N NH

~ A
H+ N' -NH (Ia,R=H) ~N
e.g. Si02) ~ ~H
Compounds of the formula Ia where R = hydrogen can be prepared by reacting 1H,2H-perhydrodiazines of the formula IIa (R = H) with an isocyanate (X = O) or an isothiocyanate (X = S) of the formula III. In the same manner, it is also possible to obtain compounds Ia where R ~ H if the corresponding nitrogen-substituted compounds IIa (R ~ H) are used as starting materials.
Scheme 2 X
i1 ~N'C~NHGl + X=C=N-D Z N
Z~NR ~ ~ R
II a Ill I a Analogously, i~ is also possible to react N-substituted perhydrodiazines :CIb with an isocyanate or isothiocyanate II~~ Y~>
give the end _~,-oclucts :CIb according to the following scheme:

Scheme 2a X
,H Z~N'C~H'C
Z N .1. X=C=N-D "' N
N\ (RA~
~R
(RA)m R
II b III 1 b According to a further process, shown in scheme 3, substituted triazolinediones (X = O) or -thiones (X = S) of the formula IV
can be ring-opened with an alkoxide or thiolate to give the substituted ureas Ibll) (R = C(X)YR1~ where X = O or S and Y = O
or S).
Scheme 3 X
~.J Z~N'C~NH O
Z N~ + -YR~o --~- N
N N-D (RA)~ ~C(X)YR,a (RA)m IV V I b In a corresponding manner, it is possible to prepare the substituted ureas Ibl2> (R = C(O)NR11R12) according to the invention by the process shown in scheme 3a, starting from substituted triazolinediones (X = O) or -thiones (X = S) of the formula IV by reaction with a basic amine VI.
X
Scheme 3a Z~N~ + HNR~~R~2 --= Z~N'C~NHGl N~'~N-D
(RA~N~C(O)NR~~ R,z (RA)m IV VI I b According to the process shown in scheme 4, substituted ureas of the formula Ia' where R = H can be reacted with a chlorocarbonyl isocyanate VIIa or chlorosulfonyl isocyanate VIIb or with a substituted carbonyl isocyanate VIIIa or sulfonyl isocyanate VII Ib to give the subst ituted ureas Ian 3 ~ (where R = C ( O ) NHVC1 ) or Ia141 (where R = C(O)NH~~~rRl2~).
NII~O 1 ~~) ~~50~5~~$0 CA 02377143 2001-12-19 1~$
Scheme 4 X

X=C=NVCI (RA)m II
C

~NH
~N~

+ Vlla V=CO -- ~ I
Z~N~
~NHVCI

C

X VII b V = SOz O

(RA) m I I G~
.C. 1 a(a) H

N
~N

ZvN~

H
X

X=C=NWR~2' (RA)m ICI /O
' I a ~N~ ~NH

(R = H) + VIII a W = COZ ~ Z N NHWR~2' ~
' C

VIII b W = S02 Q

VIII c W = S03 1 a(4) In a corresponding manner, it is possible to prepare the substituted ureas Ia (R ~ H) according to the process shown in scheme 5, starting with ureas of the formula Ia' (R = H), by reaction with an acid derivative IX in which A is a leaving group.
Scheme 5 A II
(R )m ~C. -D (RA)m N~C~NH O
N N H -E- R-A -~N
Z~N~H R
la'(R= H) IX la Furthermore, according to scheme 6, it is possible to hydrolyze the ureas of the formula Ib which are substituted at the second ring nitrogen and in which R is a radical which can easily be removed, such as C(X)YR1~, CO2H or CHO, to give the ureas Ib' where R = H. From these, it is then possible to prepare the substituted ureas where R = C(X)YR1~, CHO, CN, C(X)NRllRlz, C(O)Rz, P(O)(OR1)R1, P(O)(OR1)z, S(O)RB, S(O)ZR1 or S(O)zNHR1 by reaction with an acid derivative R-A in which R is as defined above and A
is a nucleophilically displaceable leaving group.

Scheme 6 X X
Z~N'C~NHGl H2O Z~N'C~NHGI
~, ~ -ROH ~N~H
(RA~N~R (RA)m Ib Ib' (R=H) X
X

Z~N'~~NHQ -I- R-A -----~- Z~N'~~NHCl N
~~ ~ ~R
~N~H (Rn~
(R ) I b' (R = H) iX I b The schemes 4 to 6 above also apply in an analogous manner to the corresponding isomer in which Z is in the respective other position, i.e. according to scheme 4, it is possible to prepare the compounds Ib~3~ and Ib~4~ from Ib' (R = H), and according to scheme 5, it is possible to prepare the compounds Ib from Ib'.
Correspondingly, according to scheme 6, the radical R in the compounds Ia can be converted via hydrolysis to give the compounds Ib' (R = H) followed by reaction with R-A. Hereinbelow, the reaction conditions and the way in which the processes are carried out are described for the preparation of the ureas Ia and Ib substituted at the second ring nitrogen; however, the instructions can be applied to the preparation of all compounds of the formulae Ia and Ib in which R is hydrogen.
The solvents which are selected for these reactions are -depending on the temperature range - hydrocarbons, such as pentane, hexane, heptane, cyclohexane, aromatic compounds, for example benzene, toluene, xylene, heteroaromatic compounds, for exarnle pyridine, a,(3,y-picoline and quinoline, chlorinated hydrocarbons, for example methylene chloride, 1,1-dichloroethane, 1,2-dichloroe-thane, 1,1,2,2-tetrachloroethane, 1,1-dichloroethylene, chlorobenzene, 1,2-, 1,3-, 1,4-dichlorobenzene, 1-chloronaphthalene and 1,2,x-trichlurobenzene, ethers, such as 1,4-ctioxane, anisole, glycol ethers, such as dimethyl glycol ether, diethyl glycol ether, diethylene glycol dimethyl ether, esters, such as ethyl acetate, pr~:~c~y? acetate, methyl isobutvrate, isobutyl acetate, cnrboxamide~~, such as DMF, N-methylpyrrolidone, ni_r_rated hydrocarbons, s~_lch as nitromethane, nitroetWne, nitropropaae and ~pr~~~ ,r~0~8~ CA 02377143 2001-12-19 nitrobenzene, ureas, such as tetraethylurea, tetrabutylurea, dimethylethyleneurea, dimethylpropyleneurea, sulfoxides, such as dimethyl sulfoxide, sulfones, such as dimethyl sulfone, diethyl sulfone, tetramethylene sulfone, nitrites, such as acetonitrile, propionitrile, butyronitrile or isobutyronitrile; water or else mixtures of individual solvents.
The molar ratios at which the starting materials of the individual reaction schemes are reacted with one another are generally 0.9 to 1.4, preferably 0.95 to 1.2, particularly preferably 0.98 to 1.15 for the ratio of aldehyde to N-amino-N'-phenylurea; or for the ratio of perhydrodiazine IIa or N-substituted perhydrodiazine IIb to isocyanate or isothiocyanate III, of triazolinedione IV to the nucleophiles V and VI, of substituted urea Ia' (where R = H) to the isocyanates VIIa or b or VIIIa, VIIIb or VIIIc or the acid radical IX. The reaction of the substituted urea Ib (where R x H) and water and of urea Ib' (R
- H) and the acid radical IX can likewise be carried out under the molar ratios mentioned.
The hydrolysis of the substituted urea Ib in scheme 6 is advantageously also carried out in an excess of water, for example in aqueous solution.
The concentrations of the starting materials in the solvent are generally from 0.1 to 5 mol/1, preferably from 0.2 to 2 mol/1.
The reaction sequence illustrated in scheme 1 is described in more detail below.
The reaction of the N-amino-N'-arylureas according to scheme d with formaldehyde or paraformaldehyde is advantageously carried out in the presence of a solvent at 0 to 150°C, preferably 10 to 100°C, particularly preferably 20 to 60°C. Aqueous formaldehyde, preferably as an about 37~ strength solution, is advantageously added at 10 to 25°C and over 2 to 20 min to a mixture of the N-amino-N'-arylurea in one of the abovementioned solvents, and the mixture is then stirred for another 0.5 to 12 hours, preferably 1 to 3 hours, at 20 to 60°C for the reaction to go to completion. However, it is also possible to add the N-amino-N'-arylurea to a mixture of formaldehyde in one of the abovementioned solvents and then to complete the reaction as above. Instead of aqueous formaldehyde, it is also possible to use paraformaldehyde. It is generally not necessary to remove the water of reaction; hovaever, the water of reaction can also be removed during the reaction via a water separator. The reaction with formaldehyde according to step 1 in scheme 1 is preferably carried out on exclusion of acidic catalysts, i.e. in neutral to slightly alkaline medium. If appropriate, acidic impurities are neutralized by addition of basic compounds, for example alkali metal or alkaline earth.metal hydroxides or bicarbonates or carbonates. If appropriate, it is also possible to add organic bases or to carry out the reaction using a basic solvent component, such as pyridine. The reaction can be carried out under atmospheric pressure or superatmospheric pressure, continuously or batchwise.
The cyclization of the N-methyleneimino-N'-arylureas to give the 4-(arylcarbamoyl)tetrahydro-4H-1,3,4-oxa(or thia)diazines is carried out with addition of, in general, 1 to 100 by weight of an acid, based on the urea, advantageously in the presence of one of the abovementioned solvents, at from 0 to 150°C, preferably 10 to 120°C, particularly preferably 20 to 80°C.
The acid used can be an aromatic sulfonic acid, for example benzenesulfonic acid, p-chlorobenzene- or p-toluenesulfonic acid, an aliphatic sulfonic acid, such as methanesulfonic acid, trifluoromethanesulfonic acid, ethanesulfonic acid and n-propylsulfonic acid, a sulfaminic acid, such as methylsulfaminic acid, ethylsulfaminic acid or isopropylsulfaminic acid, an aliphatic carboxylic acid, such as acetic acid, trifluoroacetic acid, propionic acid, butyric acid or isobutyric acid, and inorganic acid, such as hydrochloric acid, sulfuric acid, nitric acid or boric acid.
The N-methyleneimino-N'-arylurea is advantageously added at 10 to 25°C and over 2 to 20 min to the organic acid, preferably acetic acid, as reaction medium, and stirring is continued at 20 to 80°C
for 0.5 to 12 hours, preferably 1 to 3 hours. However, the acid can also be added directly to the reaction solution of the N-methyleneimino-N'-arylurea intermediate formed from N-amino-N'-arylurea and formaldehyde, and the intermediate can be cyclized without isolation, if appropriate after some of the solvent has been distilled off, to give the 4-(arylcarbamoyl)tetrahydro-4H-1,3,4-oxa(or thia)diazine.
The concentration of the starting materials in the solL~ent is generally from 0.1 to 5 mo1/1, preferably from 0.2 to 2 mol/1.
Instead of an acid, it i~ also possible to use, as cat alys-t, a neutral or acidic surface-active metal oxide, for example aluminum oxide, iron o:ti.is, boron oxide, silicon dioxide;

titanium dioxide, arsenic oxide, antimony oxide, chromium oxide or manganese oxide.
The reaction can be carried out under atmospheric pressure or superatmospheric pressure, continuously or batchwise.
If R represents hydrogen, the compounds of the formulae Ia and Ib can be cyclized analogously to known processes to give bicyclic triazolinediones (scheme la).
Scheme la X O
"~~. w ~N NH ~N N - Q
w/N~H
I a' (R = H) IV
The cyclization of the 4-(arylcarbamoyl)tetrahydro-4H-1,3,4-oxa(or thia)diazines according to scheme la is carrried out using phosgene, thiophosgene or a phosgene substitute, for example diphosgene (C1C(=O)OCC13), advantageously in the presence of one of the abovementioned anhydrous solvents, at from -10 to 120~C, preferably from 0 to 80~C, particularly preferably from 10 to 60~C.
The phosgene is advantageously introduced at 10 to 60~C and with stirring into a mixture of a 4-(phenylcarbamoyl)tetrahydro-4H-1,3,4-oxa(or thia)diazine and an amount of from 0.5 to 5% by weight, based on the starting material, of activated carbon as catalyst in one of the abovementioned anhydrous solvents, over a period of 0.5 to 20 hours, preferably 1 to 12 hours.
The reaction can additionally be promoted by a basic amide catalyst, for example DMF, which is usually employed in an amount of from 0.3 to loo by weight, based on the starting material. The basic catalyst used can also be an organic base, such as triethylamine, tri-n-propylamine, N,.N -dimethyl.anil.ine or N,N-dimethylcyclohexylamine. Also preferred is the use of pyridine, if appropriate directly as solvent.
In place of phosgene, it is also possible to use diphosgene. The diphosgene is advantageously added vap.th stirring, at from 0 to -5~r and over a period of ? to 20 min, to the mixture of the starting material and one of t he abovementioned solvents, if 13~
appropriate with addition of activated carbon, DMF or the organic base, and the mixture is allowed to warm to 10°C over a period of 1 hour and then stirred at 10 to 60°C for another 1 to 12 hours.
The molar amount of phosgene or diphosgene is 0.98 to 5, preferably 1 to 3, particularly preferably 1 to 1.3, per mol of starting material.
The concentration of the starting materials in the solvent is generally from 0.1 to 5 mol/1, preferably from 0.2 to 2 mol/1.
The reaction can be carried out under atmospheric pressure or superatmospheric pressure, continuously or batchwise.
The multistep reaction according to schemes 1 and la can also be carried out advantageously as a one-pot process, where, in the first synthesis step, the water of reaction is removed during the reaction of the N-amino-N'-phenylureas with formaldehyde, the N-methyleneimino-N'-phenylureas formed are cyclized with addition of a neutral or acidic catalyst to give the 4-(phenylcarbamoyl)tetrahydro-4H-1,3,4-oxa(or thia)diazines, and these are then, if appropriate,. cyclized using phosgene or diphosgene, if appropriate with addition of activated carbon or an amide catalyst or in the presence of a base, to give the end products Ia'. If appropriate, any acidic catalysts present are removed prior to the phosgene cyclization by phase separation or distillation, followed by ring closure to give the triazolinediones IV.
For work-up, the intermediates are taken up in a water-immiscible solvent, acidic impurities are extracted using dilute alkali or water, the mixture is dried and the solvent is removed under reduced pressure.
The reactions according to schemes 2 and 2a are illustrated in more detail below.
In the reactions according to the invention, an isocyanate or isothiocyanate III is advantageously added at 10 to 25°C and over a period of 5 to 30 min to a mixture of the perhydrodiazine IIa or IIb in one of the abovementioned solvents, and the mixture is then stirred at 20 to 80°C for another 0.5 to 24 hours, preferably 1 to 10 hours, for the reaction to go to completion. However, in the case of the reaction of the DI-su.bst.ituted perhydrodiazines R # H), it. is also possible to initially charge the isocyanate or isothiocyanate III in one of the abovementioned solvents, to add the N-substituted perhydrodiazine and then to complete the.
reaction as above.
In the ring opening of the triazolinedione IV with the nucleophiles V and VI according to schemes 3 and 3a, the nucleophile is advantageously added at 10 to 30°C and over a period of 5 to 30 min to a mixture of the triazolinedione IV in one of the abovementioned solvents, and the mixture is then stirred at 20 to 60°C for 0.5 to 24 hours, preferably for 1 to 10 hours, for the reaction to go to completion. However, it is also possible to add the triazolinedione IV to a mixture of the nucleophile in one of the abovementioned solvents and then to complete the reaction as above.
The alcohols or thiols of the formula V are advantageously employed in the form of their alkali metal or alkaline metal salts, i.e. their lithium, sodium, potassium, magnesium or calcium salts. However, the reaction can also be carried out in the presence of an organic base, for example triethylamine, tri-n-propylamine, N-ethyldiisopropylamine, pyridine, a-, (3-, ~y-picoline, 2,4-, 2,6-lutidine, N-methylpyrrolidine, triethylenediamine, dimethylaniline, N,N-dimethylcyclohexylamine, quinoline or acridine. Salt formation can furthermore be carried out using an alkali metal or alkaline earth metal hydride or hydroxide. Using one of the abovementioned bases, the alcohols or thiols are advantageously converted in an inert solvent into their corresponding salts, followed by the reaction with the triazolinedione. Depending on the reactivity of the alcohols or thiols used, the water formed during the salt formation can remain in the reaction medium or be removed azeotropically with a solvent. It is also possible to carry out the salt formation from the outset in aqueous phase and then to remove the water.
Furthermore, the salt formation can also be carried out using an alkali metal or alkaline earth metal alkoxide, preferably sodium methoxide or ethoxide, and to remove excess alcohol prior to the reaction with the triazolinedione, or to carry out the reaction directly using the same alcohol as solvent.
During the addition of the isocyanates VIIa or VIIb or VIIIa, VIIIb or VIIIc according to scheme 4 or the acid derivative IX
according to scheme 5 to the substituted urea Ia' where R = H, the isocyanates VIIa or VIIb or VIIIa, VIIIb or VIIIc or the acid derivative IX - in 'the latter case preferably in the presence of a base - are advantageously added to a mixture of the substituted urea Ia' or Lb' where R = H in one of t'ne abovementioned solvents, at 10 to 30°C, and the mixture is then stirred For IF

another 0.5 to 24 hours, preferably 1 to 10 hours, at 20 to 120~C
for the reaction to go to completion.
However, it is also possible to add the substituted urea Ia or Ib where R = H to a mixture of the isocyanates VIIa or VIIb or VIIIa, VIIIb or VIIIc or the acid derivative IX - in the latter case preferably in the presence of a base - and then to complete the reaction as above. When using the acid derivatives IX
according to scheme 5 or 6, the substituted urea Ia' is preferably initially charged together with a base and the acid derivative IX is then added as described above, or the substituted urea Ia' or Ib' where R = H is added together with a base to the acid derivative IX.
Suitable for use as base are the bases mentioned in the illustrations to schemes 3 and 3a, preferably organic bases, such as triethylamine or pyridine. However, it is also possible to convert the urea Ia' or Ib' where R = H beforehand at the NH
group into its salt, using an alkali metal hydride or alkaline earth metal hydride, preferably sodium hydride or potassium hydride. If the reaction is carried out in a two-phase system, aqueous solutions of alkali metal or alkaline earth metal bicarbonates, carbonates or hydroxides, preferably sodium hydroxide, are employed.
The base is advantageously employed in a molar ratio of from 0.9 to 1.4, preferably from 0.95 to 1.2, particularly preferably from p,g8 to 1.15, for the ratio of substituted urea Ia' (where R = H) to base.
The reaction of Ia' or Ib' with the acid derivatives IX according to scheme 5 or 6 can also be carried out in a two-phase system in the presence of a phase-transfer catalyst. Suitable phase-transfer catalysts are quaternary ammonium or phosphonium salts. Suitable compounds which may be mentioned are:
tetraalkyl-(C1-C1$)-ammonium chlorides, bromides or fluorides, N-benzyltrialkyl-( C1-C1a)-ammonium chlorides, bromides or fluorides, tetraalkyl-(C1-C18)-phosphonium chlorides or bromides, tetraphenylphosphonium chloride or bromide, (phenyl)o(a1kt11-(CL-Cls))P-phosphonium chlorides or bromides, where o = 1 to 3, p = 3 to 1 and o + p = 4. Particular preference is given to tetraethylammonium chloride and N-benzyltriethylammonium chloride. The amount of phase-transcer catalyst is generally up to 20°s by weight, preferably between 1 and 15o by weight and particularly preferably between 2 and 8~ ~%y weight, based on the acid derivative IX.

In the acid derivate IX, A is a leaving group, such as halogen, for example fluorine, chlorine or bromine, preferably chlorine, in the case of C(0)R2, it is an oxy-C1-C6-alkanoyl, oxy-C3-C6-alkenoyl or oxy-C3-C6-alkynoyl radical, and in the case of formyl, it is an oxy-C1-C6-alkanoyl radical.
If the starting material available is a substituted urea Ia or Ib in which R is a radical that can easily be cleaved off, such as C(O)OR1~, C(S)OR1~, C(S)SR1~, C(O)SR1~, COZH or CHO (urea Ib -scheme 6), this radical R can be cleaved off according to scheme 6 by hydrolysis with water, advantageously in the presence of a base, at from 10 to 100°C, advantageously from 20 to 80°C. Thus, the substituted urea Ib(1) is initially charged in one of the abovementioned solvents, for example water, the base is then added and the reaction is completed, giving the urea Ib where R =
H.
Here, the base is advantageously employed in a molar ratio of from 0.9 to 1.4, preferably from 0.95 to 1.2, particularly preferably from 0.98 to 1.15, for the ratio of substituted urea Ib to base. The bases used can be those mentioned above, preferably alkali metal or alkaline earth metal hydroxide, particularly preferably sodium hydroxide.
Finally, according to scheme 6, the resulting substituted urea Ib (or Ia') where R = H can be substituted at the free amino group by acid derivatives IX to give the novel substituted ureas Ib' where R ~ H. To this end, the acid derivative IX is advantageously added to a mixture of the substituted urea Ib where R = H in one of the abovementioned solvents, at from 10 to 30°C, advantageously in the presence of a base, and the mixture is then stirred at 20 to 120°C for another 0.5 to 24 hours, preferably 1 to 10 hours, for the reaction to go to completion.
The reaction conditions that apply to this reaction step are the same as those described for the reaction of the acid derivatives IX with the inversely substituted ureas Ia' (according to scheme 5).
In principle, the substituted ureas -Ia and Ib can be prepared according to the synthesis process according to the invention mentioned above. However, for economical or technical .reasons, it may be more advantageous to prepare some compounds :Ca and Ib from similar substituted u.reas Ia and Ib which differ in the meaning of one radical.

Work-up of the reaction mixtures is generally carried out by methods known per se, for example by diluting the reaction solution with water, followed by isolation of the product by filtration, crystallization or solvent extraction, or by removing the solvent, partitioning the residue in a mixture of water and a suitable organic solvent and work-up of the organic phase to afford the product.
The oxazine derivatives of the formula IIa used as starting materials according to scheme 2 are novel and form part of the subject matter of a parallel application. They are prepared, for example, by initially reacting a substituted hydrazine of the formula X
~RA)m _ I H (x) in which Z is O or S and RA and m are as defined above in a first step with an acid derivative R-A (formula IX), in which R is as defined above and A is a nucleophilically displaceable leaving group, or an isocyanate of the formula VIIa,b or VIIIa-c, and cyclizing the resulting hydrazide in a second step with formaldehyde in the presence of an acid to give the substituted perhydrodiazines of the formula Ia where Z = O or S, which are, if appropriate, in the case that z = S, oxidized in a further reaction step to give the sulfoxides Z = SO or sulfones Z = 502, or the radicals R are derivatized.
Examples of suitable nucleophilically displaceable leaving groups are halogen, preferably chlorine or bromine, C1-C6-alkoxy, such as methoxy, ethoxy, n-propoxy, n-butoxy, C1-C4-haloalkoxy, such as trichloromethoxy, trifluoromethoxy, pentafluoroethoxy, N-bonded heterocyclyl, such as imidazolyl, C1-C6-alkylcarbonyloxy (or C1-C6-alkanoate), such as acetate, propionate, n-butyrate, isobutyrate, pivalate and caproate, C1-C6-haloalkylcarbonyloxy, such as mono-, di- and trichloroacetate, C1-C6-alkylsulfonyloxy, such as methylsulfonyloxy, C1-C5-haloalkylsulfonyloxy, such as trifluoromethylsulfonyloxy, phenylsulfonyloxy, where the phenyl radical may, if appropriate, be mono- or disubstituted by halogen or C1-C6-alkyl, such as phenylsulfonyloxy, p-toluenesulfonyloxy and p-C1-phenylsulfony.Loxy, N-bonded nitrogen-C5-C6-heterocyclyl, such as N-imidazolyl.

Preferred leaving groups are halogen, in particular chlorine or bromine, and furthermore acetate or trifluoroacetate.
The cyclization of the 2nd preparation step can be carried out using both formaldehyde or a compound which releases formaldehyde under acidic conditions, such as paraformaldehyde or 1,3,5-trioxane, in the presence of an acid.
However, it is also possible to react the hydrazides obtained in the 1St reaction step with formaldehyde to give the Schiff base which is then cyclized by addition of an acid.
The reaction described in the scheme below is an example of the preparation of the compounds IIa where, starting from 2-hydrazinoethanol and methyl chloroformate as acid derivative, firstly the N-amino-N-methoxycarbonyl-2-hydrazinoethanol is prepared, which is cyclized in a subsequent reaction with formaldehyde to give tetrahydro-4-methoxycarbonyl-4H-1-oxa-3,4-diazine.
,COZCH3 /'~ C02CHy N
N I ~ - HCI ' [ N/ + HCHO H--'-~ I
O~NH + CI~COCH3 IOH NH O.~N~
Z H
Preferred embodiments of the process are mentioned below:
The first reaction step is explained in more detail below: The reaction of the hydrazinoethanols/-thiols X with the acid derivatives R-A is advantageously carried out in the presence of a solvent at from -30 to 100°C, preferably from -10 to 80°C, particularly preferably from 0 to 60°C.
The solvents used for these reactions are - depending on the temperature range - hydrocarbons, such as pentane, hexane, cyclopentane, cyclohexane, toluene, xylene, chlorinated hydrocarbons, such as methylene chloride, chloroform, 1,2-dichloroethane, 1,1,2,2-t etrachloroethane, chlorobenzene, 1,2-, 1,3- or 1,4-dichlorobenzene, ethers, such as 1,4-dioxane, anisole, glycol ethers, such as dimethyl glycol ether, diethyl g!vcol ether, diethylene glycol dimethyl ether, esters, such as ethyl acetate, propyl acetate, methyl isobutyrate, isobutyl acetate, carboxamides, such as DMF, N-methylpyrrolidone, nitrated hydrocarbons, such as nitrobenzene, ureas, such as tetraethylurea, tetrabutylurea, dimethylethyleneurea, dimethylpropyleneurea, sulfoxides, such as dimethyl sulfoxide, sulfones, such as dimethyl sulfone, diethyl sulfone, tetramethylene sulfone, nitriles, such as acetonitrile, propionitrile, butyronitrile or isobutyronitrile; water or else mixtures of individual solvents.
The molar ratios in which the starting materials X and IX are reacted with one another are generally from 0.9 to 1.2, preferably 0.95 to 1.1, particularly preferably 0.98 to 1.04, for the ratio of acid derivative of the formula IX to hydrazinoethanol/-thiol X.
The first reaction step is advantageously carried out under neutral conditions. If an acidic reaction product is formed in the reaction, for example hydrogen halide if A in the formula IX
is halogen, this is removed by addition of basic compounds, for example alkali metal or alkaline earth metal hydroxides or bicarbonates or carbonates. However, the reaction can also be carried out in the presence of an organic base, for example triethylamine, tri-n-propylamine, N-ethyldiisopropylamine, pyridine, a-, [3-, y-picoline, 2,4-, 2,6-lutidine, N-methylpyrrolidine, dimethylaniline, N,N-dimethylcyclohexylamine, quinoline or acridine.
Finally, the reaction can also be carried out in an aqueous two-phase system, preferably in the presence of phase-transfer catalysts, such as quaternary ammonium or phosphonium salts. The reaction conditions mentioned above and in EP-A 556737, as well as the abovementioned phase-transfer catalysts, are suitable for the two-phase reaction.
Advantageously, the acid derivative IX is added, at 0 to 60~C and over a period of 0.25 to 2 hours, to a mixture of the hydrazinoethanol/-thiol X and the base in one of the abovementioned solvents, and stirring at 0 to 60~C is continued for 0.5 to 16 hours, preferably 2 to 8 hours, for the reaction to go to completion.
If an aqueous two-phase system is used, the starting materials X
and IX can be added with stirring, in any order, to a mixture of the phase-transfer catalyst in the tG~lo phases, and the .reaction can then be completed in the temperature range mentioned by adding base.
The reaction can be carried out under atmospheric pressure or under superatmospheric pressure, continuously or batchwise.
For work-up, any precipitated salts are separated off, or their removal is completed by addition of nonpolar solvents, and the hydrazides are thus accomulated in the filtrate.
The second reaction step is explained below: the hydrazides are subsequently reacted, advantageously under acidic conditions, with a formaldehyde solution or paraformaldehyde in one of the abovementioned solvents.
For the subsequent step, advantageously 0.9 to 1.2, preferably 0.95 to 1.1, particularly preferably 0.98 to 1.04, molar equivalents of formaldehyde or paraformaldehyde are employed per mole of hydrazide derivative. The concentration of the starting materials in the solvent is 0.1 to 5 mol/1, preferably 0.2 to 2 mol/1.
The acid used can be an aromatic sulfonic acid, for example benzenesulfonic acid, p-chlorobenzene- or p-toluenesulfonic acid, an aliphatic sulfonic acid, such as methanesulfonic acid, trifluoromethanesulfonic acid, ethanesulfonic acid and n-propylsulfonic acid, a sulfaminic acid, such as methylsulfaminic acid, ethylsulfaminic acid or isopropylsulfaminic acid, an aliphatic carboxylic acid, such as acetic acid, trifluoroacetic acid, propionic acid, butyric acid or isobutyric acid, or an inorganic acid, such as hydrochloric acid, sulfuric acid, nitric acid or boric acid. Advantageously, it is also possible to use an acid such as acetic acid or propionic acid directly as reaction medium. The acidic catalyst is advantageously employed in an amount of from 1 to 20 mol%, preferably 3 to 15 mol%, particularly preferably 5 to 10 mol%, of acid per mole of hydrazide.
Preferably, a formaldehyde solution or paraformaldehyde is added over a period of 2 to 60 min to a mixture of hydrazide and the acidic catalyst in one of the abovementioned solvents at 0 to 100°C, advantageously 10 to 80°C, particularly preferably 2U to 50°C, and stirring is continued at 40 to 50°C: for 10 to 50 hours, preferably 15 to 30 hours, to bring the reaction to completion.

~~5~~~~~$~ CA 02377143 2001-12-19 1~~
If an aqueous formaldehyde solution is used, the water is advantageously removed, for example using a water separator.
However, it is also possible to add the acidic catalyst to a mixture of hydrazide and paraformaldehyde in one of the abovementioned solvents and then to complete the reaction as described.
The reaction can be carried out under atmospheric pressure or under superatmospheric pressure, continuously or batchwise.
The oxidation of the perhydrodiazines IIa where Z = S to the sulfoxides (Z = S02), which follows, if appropriate, is preferably carried out using hydrogen peroxide, the sulfoxides being obtained with approximately equivalent amounts of oxidizing agent, and the sulfones being obtained with about double the molar quantities.
The oxidation with hydrogen peroxide can be catalyzed by suitable metal compounds, for example transition metal oxides, such as vanadium pentoxide, sodium tungstate, potassium dichromate, iron oxide tungstate, sodium tungstate/molybdic acid, osmic acid, titanium trichloride, selenium dioxide, phenylselenic acid, oxovanadinyl-2,4-pentanedionate. The catalysts are generally employed in an amount of from 0.5 to 10~, but it is also possible to employ stoichiometric amounts because the inorganic catalysts can easily be filtered off and recovered.
Solvents which are suitable for the oxidation with hydrogen peroxide are, for example water, acetonitrile, alcohols, such as methanol, ethanol, isopropanol, tert-butanol, chlorinated hydrocarbons, such as methylene chloride, 1,1,2,2-tetrachloroethane, or ketones such as acetone or methyl ethyl ketone.
In addition to hydrogen peroxide, it is also possible to use, as oxidizing agents, peracids, such as perbenzoic acid, monoperphthalic acid or 3-chloroperbenzoic acid. The reaction with peracids is expediently carried out in chlorinated hydrocarbons, such as methylene chloride or 1,2-dichloroethane.
Also very suitable for oxidizing the thiols to sulfo:Yi.des or sulfones are chlorine and bromine. This oxidation is t~xpediewt:~y carried out in polar solvents, such as water, acetoc:itrile, dioxane, or in. two-phase systems, such as aqueous potassium bicarbonate solution/dichloromethane, and also acetic acid. ~t Ls furthermore ~ossihle to employ as sources of activ? halogen tk ~05~I~50~$~ CA 02377143 2001-12-19 tert-butyl hypochlorite, hypochlorous and hypobromous acid, their salts, and also N-halo compounds, such as N-bromo- and N-chlorosuccinimide, or else sulfuryl chloride.
Also suitable for the oxidation is photosensitized oxygen transfer, in which case the photosensitizers used are usually organic dyes, for example porphyrines, such as tetraphenylporphyrine, chlorophyll, protoporphyrine, xanthene dyes, such as Rose Bengal or phenothiazine dyes, such as Methylene Blue.
Suitable inert solvents are hydrocarbons, such as pentane, hexane, heptane, cyclohexane, chlorinated hydrocarbons, such as methylene chloride, 1,2-dichloroethane, 1,1,2,2-tetrachloroethane, alcohols, such as methanol, ethanol, n-propanol or isopropanol, ketones, such as acetone, methyl ethyl ketone, polar aprotic solvents, such as acetonitrile, propionitrile or aromatic hydrocarbons, such as benzene, toluene, chlorobenzene or xylene. In place of oxygen, it is also possible to use ozone in the abovementioned solvents, plus ether, 1,4-dioxane or THF.
Besides photosensitization, catalysts are also suitable for the oxidation with oxygen, for example oxides and sulfides of nickel, copper, aluminum, tungsten, chromium, vanadium, ruthenium, titanium, manganese, molybdenum, magnesium and iron.
Either the sulfoxides (IIa where Z = SO) or their sulfones (IIa where Z = S02) are obtained, depending on the stoichiometry of the oxidizing agents used. The molar ratios in which the starting materials are reacted with one another are generally 0.9 to 1.8, preferably 1.05 to 1.3, for the ratio of tetrahydrothiadiazine to oxidizing agent in the case of the oxidation to the sulfoxide and generally 1.9 to 3.5, preferably 2.05 to 2.9, in the case of oxidation to the sulfone.
The concentration of the starting materials in the solvent is generally 0.1 to 5 mol/1, preferably 0.2 to 2 moll.
It is advantageous to initially charge the 1-thiadiazine of the formula IIa where Z = S or the sulfoxide, if appropriate together with one of the abo~,rementioned catalysts, in one of the abovementioned soi~rents, and then to add the oxidizing agent over a period of 0.25 to 20 hours with stirring. The addition and t he reaction temperature depends on the optimum efficiency of the oxidizing agent .in question and on avoiding side reactions. If photosensitized oxygen is used, the reaction is generally carried out at from -20 to 80°C; however, if metal catalysis is employed, the reaction is generally carried out at from 50 to 140°C, and if ozone is used, the reaction is generally carried out at from -78 to 60°C. Owing to the limited solubility of the oxygen derivatives, they are preferably introduced continuously into the reaction mixture over a relatively long period of time (up to 20 h) until the oxidation has been completed at the sulfoxide or sulfone stage. Liquid or easily soluble oxidizing agents, such as hydrogen peroxide, hypochlorous or hypobromous acid, tert-butyl hypochlorite, chlorine or bromine, furthermore N-chloro- or N-bromosuccinimide, can be added to the reaction mixture of the thiadiazine or thiadiazine sulfoxide over shorter periods of time, such as 0.25 to 6 h, depending on the exothermic character of the reaction, and the reaction is ended after a further 1 to 60 h. Preference is furthermore given to adding the liquid or dissolved oxidizing agent gradually. In the case of hydrogen peroxide, the reaction is generally carried out at from O to 90°C, with tert-butyl hypochlorite, the reaction is generally carried out at from -78 to 30°C, and with N-halo compounds generally at from 0 to 30°C. In the case of chlorine or bromine, a reaction temperature of from 0 to 40°C is recommended.
The oxidations can be carried out under atmospheric pressure or under superatmospheric pressure, continuously or batchwise.
The multistep reaction can advantageously also be carried out as a one-pot process, where the thiadiazines IIa (Z = S) are converted directly, without isolation and purification, into the sulfoxides IIa (Z = So) or the sulfones IIa (Z = S02).
Accordingly, the reaction product Ia is, if appropriate, allowed to cool to from 90 to 20°C, a solvent, for example methylene chloride and/or water, is added, if appropriate, and the oxidizing agent is then added at the rate of its consumption.
Particularly preferred oxidizing agents are hydrogen peroxide and sodium hypochlorite.
For work-up of the oxidation mixture, the end products IIa are generally taken up in a cater-immiscible solvent, acidic impurities and/or oxidizing agents are extracted using dilute alkali or water, the mixture is dried and the solvent is removed under reduced pressure.

~~5~~5~~$~ CA 02377143 2001-12-19 I. Preparation of the starting compounds Methyl tetrahydro-N-(2,4-dichloro-5-methoxyimino-methylphenyl)-4H-1,3,4-oxadiazine-3-thiocarboxamide-4-carboxylate a) Methyl N-amino-N-2-hydroxyethylcarbamate At from 0 to 5~C, 248.4 g (2.628 mol) of methyl chloroformate were added with stirring, in the course of 30 min, to a mixture of 200 g (2.628 mol) of 2-hydrazinoethanol and 266 g (2.628 mol) of triethylamine in 1600 ml of methylene chloride. The mixture was stirred at from 3 to 22~C for 3 h, and the precipitated hydrochloride was then filtered off with suction and washed with THF, and the filtrate was concentrated under reduced pressure.
The residue was again stirred with 800 ml of THF, filtered off with suction and washed with 1 1 of THF, and the filtrate was concentrated under reduced pressure. This gave 366 g of the title compound as a colorless oil of an HPLC purity of 95.3, corresponding to a yield of 98.9 of theory. According to GC, the purity was 85.2.
1H-NMR (400 MHZ, d6-DMSO) 8(ppm): 4.4 - 4.8 (broad/3H) NHZ/OH; 3.6 (s/3H) CH30; 3.52 (t/2H) and. 3.35 (t/2H) CHz-CH2 b) Methyl tetrahydro-4H-1,3,4-oxadiazine-4-carboxylate Over the course of 2 min, 22.4 g (0.746 mol) of paraformaldehyde were added with stirring to a mixture of 100 g (0.746 mol) of methyl N-amino-N-2-hydroxyethylcarbamate in 1500 ml of methylene chloride. 8.5 g (0.045 mol) of p-toluenesulfonic acid were added, and the mixture was then stirred at 42~C for 21 h, until the precipitate had dissolved. The mixture was cooled to 20~C, magnesium sulfate was added, the mixture was filtered and the filtrate was concentrated under reduced pressure. This gave 111.8 g of the title compound as a colorless resin of a GC purity of 850, corresponding to a yield of 85.80 of theory.
1H-NMR (500 MHZ, CF3COZD) 8(ppm): 5.09 (s/2H) CHZ; 4.02 (s/3H) CH30; 3.8 - 4.25 (m/4H) CHZCHz IR a (cm-i): C=O 1703 The precursors of the formulae IIb and X listed in Tables a) and b) below were prepared in a similar manner.

0050~50~80 CA 02377143 2001-12-19 Table a) HO(CH2)2~N,R
(X) 0 Compound R nD23 v [ cm-1 ] Yield X
No.

1 C02CH3 _ _ 98. 9 2 COzC2H5 C=O 1695 cm-1, 88 NH2 3336 cm-1 3 C(O)SCH3 1.5458 85 4 C(O)SCZHS 1.5345 86 5 COZ-i-C3H7 C=O 1694 cm-1, 69 NHZ 3338 cm-1 6 C02-t-C4H9 7 C02-phenyl g COZ-p-C1-phenyl 9 COZ-benzyl 1.5442 C=O 1706 cm-1, 62 NH2 3336 cm-1 10 C(S)OCH3 11 C02-n-CgHl7 12 C02CH2CHZC1 1.4988 C=O 1706 cm-1 65 13 COZ-cyclopentyl 1.4981 C=O 1695 cm-1 50 14 C02-n-C14H19 C=O 1700 cm-1 88 15 COCH3 1.4938 22 nDZ3 = refractive index at 23~C
~' [ cm-1 l IR bands Table b) N , R
i o~N~
H

~~r~0~~r~~8~ CA 02377143 2001-12-19 Compound R nn23 v [cm-1] 1H-NMR Yield IIb No. b.p. [b(PPm)) [$J

[~C/mbar]

m.p. [QC]

1 C02CH3 - - s.o. 85.5 2 COzC2H5 100-105/0.5 C=0: 1701 4.05 78 (q/2H), 0-CH2-C;

1.18 (t/3H) 3 C(O)SCH3 103-111/0.4 C=O: 1659 75 1.5542 4 C(O)SCzHS 1.5428 C=O: 1657 74 5 C02-i-C3H7 C=O: 1702 61 6 COy-t-C4Hg 7 C02-phenyl 8 C02-p-C1-phenyl 9 C02-benzyl 7.4-7.24 43 (m, 5H) 5.1 (s,2H) 10 C(S)OCH3 11 COZ-n-C$H17 12 C02CHZCHZC1 1.5130 C=O 1709 53 13 C02-cylcopentyl145-150/0.5 C=0 1700 51 14 C02-n-C14H2g 77-81 59 15 COCH3 C=O 1683 34 nD23 = refractive index at 23~C
m.p. - melting point b.p. - boiling point at the stated pressure II. Preparation of the compounds Ia and Ib Example 1 (Compound Ib, No. 1, Table 7) Methyl ter_rahydro-N-(2,4-dichloro-5-methoxyiminomethyl-phenyl)-4H-L,3,4-oxadiazine-3-thiocarboxamide-4-carboxylar.e Over the course of 5 min, 9.11 g (0.035 mol) of 2,4-dichlnro-5-methoxyiminomethylphenyl isothincyanate w~:cP added with sti:rc.inc~ to 10.22 g (0.07 mol) of the compound from f~: in 1~0 ml of ter.rahydrofuran, and the mixture teas stirred a:. 2;e=o' For ~~.rJ~~5~08~ CA 02377143 2001-12-19 h and then at 40 to 50°C for 2 h. The reaction mixture was concentrated under reduced pressure. The residue was taken up in methylene chloride and fractionated over silica gel. This gave 11.9 g (78~ of theory) of the title compound of m.p. 80-83°C.

IR v (cm-1): C=O/C=S 1733, 1705 Example 2 (Compound Ib.2, Table 7) Tetrahydro-N-(4-chloro-5-methoxyiminomethylphenyl)-4H-1,3,4-oxadiazine-3-carboxamide 6.3 g (17.66 mmol) of methyl tetrahydro-N-(4-chloro-5-methoxy-iminomethylphenyl)-4H-1,3,4-oxadiazine-3-carboxamide-4-carboxy-late were initially charged in 150 ml of ethanol, and over the course of 20 min, a solution of 0.8 g (19.42 mmol) of sodium hydroxide in 50 ml of water was then added with stirring at 60 to 70°C. After a further 10 min of stirring, the clear solution was cooled and substantially concentrated under reduced pressure. The residue was admixed with 50 ml of water and, with stirring, acidified with 1N hydrochloric acid, which resulted in evolution of gas with formation of foam and precipitation. The resulting mixture was extracted three times with rnethylene chloride. The combined organic extracts were dried over magnesium sulfate and concentrated under reduced pressure. This gave 4.9 g (83.60 of theory) of the title compound as a colorless resin.
1H-NMR (400 MHZ d6-DMSO)8 (ppm): 8.4 (s/1H) CH=N; 8.2 (s/1H), 7.7 (m/1H), 7.36 (m/1H) phenyl; 4.0 (s/3H) N=OCH3 IR v (cm-1): C=O 1681 Example 3 (Compound Ib.3, Table 7) Methyl tetrahydro-N-(2,4-dichloro-5-methoxyphenyl)-4H-1,3,4-oxadiazine-3-carboxamide-4-carboxylate With stirring, 0.3 g (1.666 mmol) of 30o strength sodium methoxide was added to a solution of 0.5 g (1.505 mmo1) of 8-(2',4'-dichloro-5'-methyloxyphenyl)-4-oxa-7,9-dioxo-1,2,8--triazabicyclo[~.3.0)nonane in 50 ml of methanol. The mixture was stirred at 22°C for another 6 h. The reaction mixture was concentrated under reduced pressure and partitioned between methylene chloride and 1N hydrochloric acid. The organic ph~s~
was dried over magnesium sulfate and concentrated under r edu~:_ed ~1 pressure, giving 0.5 g (88.5 of theory) of the title compound as colorless crystals of m.p. 160-163°C.
IR v (cm-1): C=0 1730, 1693 Example 4 (Compound Ib.S, Table 7) Ethyl tetrahydro-N-(4-chloro-2-fluoro-5-propargyloxyphenyl)-4H-1,3,4-oxadiazine-3-thiocarboxamide-4-carboxylate With stirring, 0.17 g (2.473 mmol) of sodium ethoxide was added to a solution of 0.8 g (2.249 mmol) of 8-(4'-chloro-2'-fluoro-5'-propargyloxyphenyl)-4-oxa-7-oxo-9-thioxo-1,2,8-triazabicyclo[4.3.0]nonane in a mixture of 30 ml of ethanol and 30 ml of methylene chloride, and the mixture was stirred at 22°C for 1 h. 100 ml of methylene chloride were then added, and the mixture was extracted 2 x with 1N hydrochloric acid. The organic phase was dried and concentrated, and 0.9 g (99.4 of theory) of the title compound were isolated as a crude resin. Filtration over silica gel using methylene chloride gave 0.7 g of m.p. 143-145°C.
Example 5 (Compound Ib.95, Table 7) Tetrahydro-N-(4'-chloro-2'-fluoro-5'-propargyloxyphenyl)-4H-I,3,4 -oxadiazine-3-thiocarboxamide-4-(N'-methoxycarbonyl)carboxamide At 22°C, 0.22 g of methoxycarbonyl isocyanate (90~) is added to a solution of 0.6 g of tetrahydro-N-(4'-chloro-2'-fluoro-5'-propargyloxyphenyl)-4H-1,3,4 -oxadiazine-3-thiocarboxamite (Compound Ib, No. 5 from Table 7, prepared by hydrolysis of Compound No. Ib.4 (Table 7, Example 4) by the method described in Example 2, and the mixture was stirred for 22 h. Concentration of the mixture under reduced pressure, digestion with ether and isolation of the residue by filtration with suction gave 0.6 g of the title compound of melting point 195°C.
In addition to the compounds described above, further substituted ureas of the formulae Ia and Ib which were prepared in an analogous manner are listed in Tables 7 and 8 below, Table 7 (Compounds Ib No.l to No. 101 where Q = Q-1 and Z = O) ~N~R
O( ~N. .N ~ ~ R4 I b X
to No. R X R3 R4 R5 m.p.. [C] or IR: v [cm-1) 1 C02CH3 S C1 C1 CH=NOCH3 80 - 83C

2 H O H C1 CH=NOCH3 1681 3 C02CH3 O Cl C1 OCH3 160 - 163C

No. R X R3 R4 R5 m.p.. [C] or IR: v [cm-1) 4 COzCH3 S F C1 OCHzC=CH 156 - 160C

5 H S F Cl OCH2C=-CH 124 - 128C

6 C02CH3 S F Cl O-C(=CHZ)C02CH3 68 - 71C

7 C02CH3 S F C1 CH=NOCH3 150 - 153C

8 COZCH3 O F Cl CO-O-C(CH3)3 60 - 65C

9 COyCH3 O H CI CH=NOCH3 153 - 155C

10 C02CH3 O F C1 OCHZC~CH 130C

12 COZC2H5 O F C1 OCHzC~CH

13 C02-iC3H7 S F C1 OCH2C---CH 118 - 123C

14 C02-iC3H7 O F C1 OCHZC=CH

15 C02-nC3H7 O F C1 OCH2C---CH

16 C02-nC3H7 S F C1 OCHZC---CH

19 C02CH j S H C1 OCHZC---CH

20 COZCH3 O H C1 OCHZC=CH

21 COZCH3 S H Cl OCHZCOZCH3 22 COzCH3 0 H C1 OCHzCO2CH3 0 - -_~._ 24 COzCH3 O CI ~ OCHzCO2CH3 -- ~ ~
--25 COZCH3 S F C OCHzCO2CH3 142C

26 COZCH3 0 ~ LOCHZCOzCH3 C
L

4 27 COZCH3 S F~ C::L~ OCHZCOo-nC5H11 28 C02CH3~~ O F ~ OCH2COz-nCSHli ~~c~~~c~~0$~ CA 02377143 2001-12-19 No. R X R3 R4 R5 m.p.: [C] or IR: v [cm-1]

30 COzCH3 0 C1 C1 SCH2C02CH3 31 C02CH3 S F C1 SCHzCOzCH3 129-132C

32 C02CH3 0 F C1 SCHzCO2CH3 1737, 1701 cm-1 33 COyCH3 S H C1 OCH(CH3)COzCH3 34 COzCH3 O H Cl OCH(CH3)C02CH3 35 C02CH3 S Cl Cl OCH(CH3)COZCH3 36 C02CH3 O C1 C1 OCH(CH3)C02CH3 37 COZCH3 S F C1 OCH(CH3)C02CH3 73 - 76C

15~38 C02CH3 0 F C1 OCH(CH3)C02CH3 39 C02CH3 S F C1 SCH(CH3)COzCH3 1735 cm-1 40 C02CH3 0 F C1 SCH(CH3)C02CH3 41 COyCH3 S H Cl C02CH3 43 C02CH3 S C1 Cl C02CH3 45 COZCH3 S F Cl C02CH3 185-187C

46 C02CH3 0 F C1 COzCH3 4 COZCH3 S H C1 C02C ( CH3 ) 2C02CH2CH=CH2 4 COZCH3 0 H C1 C02C ( CH3 ) yC02CHZCH=CH2 49 C02CH3 S C1 C1 C02C(CH3)2COzCH2CH=CH2 50 C02CH3 O C1 C1 COzC ( CH3 ) 2COZCHZCH=CH2 51 C02CH3 S F C1 C02C(CH3)2C02CHZCH=CHz 52 COZCH3 O F Cl C02C ( CH3 ) 2COZCHzCH=CHz 55 COZCH3 S F C1 C(=NOCH3)OCH3 56 C02CH3 O F C1 C(=NOCH3)OCH3 57 C02CH3 S F C1 C(=NOCH3)OCH2COzCH3 58 COzCH3 0 F C1 C(=NOCH3)OCH2COzCH3 59 COZCH3 S F C1 C(O)N(CH3)OCH3 60 C02CH3 O F Cl C(O)N(CHg)OCH3 51 COZCH3 S C1 C1 CH=NOCH3 62 COzCH3 0 F C1 CH=NOCH3 03 C02CH3 S F C1 CEI=NOCH3 150 - 153C

0l COzCH3 O F C1 CH=DIOCZH3 65 ICOzCH3 ~S IF IC1ICH=NOC2H5 0050~5008~ CA 02377143 2001-12-19 No R X R3 R4 R5 m . p . : [
. oC ] or- , IR: v [cm-1]

66 C02CH3 O F Cl CH=NOCHzC02CH3 67 C02CH3 S F C1 CH=NOCHZC02CH3 68 C02CH3 O F C1 CH=NOCH(CH3)C02CH3 69 COZCH3 S F C1 CH=NOCH(CH3)C02CH3 70 C02CH3 0 F C CH=C(C1)C02C2H5 71 COZCH3 S F C1 CH=C(C1)C02C2H5 72 C02CH3 O F C1 CHz-CH(C1)C02CyH5 73 COZCH3 S F C CHZ-CH(Cl)COzC2H5 74 C02CH3 O F C1 CH=NOCH2C~CH

75 C02CH3 S F C1 CH=NOCH2C~CH

76 C(O)NHC02Et S F C1 O-cyclopentyl 195C decomp.

77 C02Et S F C1 OCHZCH=CHZ 118 - 122C

78 C02CH3 S F C1 OCH2CH=CH2 158 - 159C

79 COZ-iC3H7 S F C OCH2CH=CHp 139 - 140C

80 H S F C1 O-cyclopentyl 115 - 118C

81 C02CH3 S F C1 O-cyclopentyl 177 - 179C

82 H S Cl C1 COzH 168-170C
decomp.

83 COZEt O F C1 OCH3 56 - 58C

84 C(O)NHC02Et 0 H C1 CH=NOCH3 214-215C
decomp.

85 C02-iC3H7 S C1 Cl CN 140 - 143C

86 COZCzHS S F Cl COZCH3 160 - 163C

87 C(O)NHC02CH3 S F C1 O-cyclopentyl 190C decomp.

88 C(O)NHCOzCZHSS F C1 OCHzC=CH 172 - 174C

89 COZ-benzyl S F C1 OCHZC---CH 49 - 51C

90 C02-cyclo- S F Cl OCH2C=CH 114 - 116 C
pentyl 91 COZ-CH2CHZC1 S F C1 OCH2C---CH 1730 cm-1 92 C02-n-C14Hz9 S F C1 OCHZC=CH 35 - 36C

93 H S F C1 COzH 160C decomp.

94 C(O)NHCOZCH3 S F C1 OCHzC=CH 195C decomp.

95 COZCH3 S F C1 COz-i-C3H7 149 - 151C

g6 C02CH3 O F F H 92 - 93C

97 C02CH3 O F F NOZ 1734,1700 cm-1 gg H S F C1 OH 153 - 156C

gg H S F C1 OCHZCOzCH3 188C

100 COZCH3 S C1 Cl OCH3 1730,1704 cm-1 101 COZCH3 S F CN F 175 - 176C ii ~pr~0~5~p8~ CA 02377143 2001-12-19 Table 8:(Compounds Ia No. 1 to No. 94 wherk~ Q = Q-1 and Z = O) X
I) _ ~N ~ N \ / R l a H
R RS
No. R X R3 R4 R5 m.p.. [C] or IR: v [cm-i]

1 COZCH3 S C1 C1 CH=NOCH3 2 H O H C1 CH=NOCH3 58 - 60C

3 C02CH3 O C1 C1 OCH3 1746 cm-1 5 H S F C1 OCH2C=-CH 157 - 158C

6 COZCH3 S F Cl O-C(=CH2)COyCH3 7 C02CH3 S F Cl CH=NOCH3 8 COZCH3 O F C1 CO-O-C(CH3)3 9 COZCH3 O H C1 CH=NOCH3 13 C02-iC3H7 S F C1 OCH2C=CH

14 C02-iC3H7 O F C1 OCH2C---CH

15 CO2-nC3H7 O F C1 OCHZC~CH

16 C02-nC3H7 S F C1 OCH2C-=CH

17 COZCH3 S C1 Cl OCH2C---CH

18 C02CH3 O Cl Cl OCH2C---CH

23 COzCH3 S Cl C1 OCH2COZCH3 25 COZCH3 S F Cl OCHZC02CH3 26 COzCH3 O F C1 OCHZCOzCH3 27 COZCH3 S F C1 OCHZCOZ-nCSHii 28 COZCH3 O F C1 OCHZCOZ-nC5Hii 29 COZCH3 S C1 C1 SCHZCOzCH3 ._ 30 CC~ZCH3 O C1 C1 SCHZCOZCH3 31 COZCH3 S F Cl SCHzCOZCH3 ~~5~~500$0 CA 02377143 2001-12-19 No. R g R3 R4 R5 _. m,p. : [C]
or IR: v [cm-1]

33 C02CH3 S H C OCH(CH3)COZCH3 34 COzCH3 O H C1 OCH(CH3)C02CH3 35 COzCH3 S C1 C1 OCH(CH3)COzCH3 36 COzCH3 O C1 C1 OCH(CH3)C02CH3 37 C02CH3 S F C1 OCH(CH3)C02CH3 38 C02CH3 0 F Cl OCH(CH3)COyCH3 39 C02CH3 S F C1 SCH(CH3)C02CH3 40 COZCH3 O F C1 SCH(CH3)C02CH3 41 COzCH3 S H C1 C02CH3 42 COzCH3 O H C1 COZCH3 44 COzCH3 O C1 C1 C02CHg 45 COzCH3 S F C1 C02CH3 4 C02CH3 S H C C02C ( CH3 ) 2COzCH2CH=CH2 4 C02CH3 O H C1 C02C ( CH3 ) 2COZCH2CH=CHZ

49 COZCH3 S C1 C1 C02C(CH3)2COzCH2CH=CHZ

50 C02CH3 O C1 C1 C02C(CH3)ZC02CHZCH=CH2 51 C02CH3 S F C1 C02C ( CH3 ) 2CO2CHZCH=CH2 52 COZCH3 O F C1 C02C ( CH3 ) 2C02CH2CH=CH2 53 COzCH3 S F C COZCH2CHZOCH3 54 C02CH3 O F C1 COyCH2CHzOCH3 55 COzCH3 S F C1 C(=NOCH3)OCH3 56 COZCH3 O F C1 C ( =NOCH3 ) OCH3 57 COZCH3 S F C1 C(=NOCH3)OCHZCOzCH3 58 COZCH3 O F C1 C(=NOCH3)OCHyC02CH3 59 COZCH3 S F C1 C(O)N(CH3)OCH3 60 COpCH3 O F C1 C(O)N(CH3)OCH3 61 C02CH3 S C1 C1 CH=NOCH3 62 COZCH3 O F Cl CH=NOCH3 63 COpCH3 S F C1 CH=NOCH3 64 C02CH3 O F C1 CH=NOCZHS

65 COZCH3 S F C1 CH=NOCZHS

66 COZCH3 O F Cl CH=NOCHzCOZCH3 67 COZCH3 S F C1 CH=NOCHZCOZCH3 68 C02CH3 O F C CH=NOCH(CH3)C02CH3 69 C02CH3 S F C1 CH=NOCH(CH3)COZCH3 No. R X R3 R4 R5 m.p.: [C] or IR: v [cm-1]

70 C02CH3 O F C1 CH=C(C1)COZC2H5 71 COzCH3 S F C1 CH=C(Cl)COZCZHS

72 C02CH3 O F C1 CHZ-CH(C1)C02C2H5 73 C02CH3 S F C1 CHZ-CH(C1)C02CZH5 74 COyCH3 O F Cl CH=NOCH2C~CH

75 C02CH3 S F C1 CH=NOCH2C~CH

76 C(O)NHCOZEt S F C1 OCH2C = CH 175C decomp.

77 C(O)NHCOZEt O F C1 OCH3 189 - 190C

7g H O C1 C1 OCH3 128 - 130C

7g H O F Cl OCH3 147 - 150C

80 H O C1 Cl CH=N-OCH3 210 - 213C

81 H O F C1 CH=N-OCH3 170 - 172C

82 C(O)NHCOZEt O C1 C1 CH=N-OCH3 189C

83 C(O)NHCOZEt O F C1 CH=N-OCH3 179 - 180C

84 H S F Cl CH=N-OCH3 175 - 176C

85 C(O)NHC02Et S F C1 CH=N-OCH3 181C decomp.

86 H S F C1 OCH(CH3)C02CH3(R) 1753 cm-1 87 C(O)NHCOZCZHgS F C1 OCH(CH3)C02CH3(R) 158 - 163C

88 C(O)NHC02CH3S F C1 OCH(CH3)C02CH3(R) 174 - 178C

8g H S F Cl C02CH3 175 - 178C

90 C(O)NHC02CH3S F C1 OCHZC---CH 184C decomp.

91 C(O)NHCOzCH3S F C1 COZCH3 160C decomp.

92 C(O)NHCOzCZHSS F C1 COZCH3 159C decomp.

93 C(O)NHC02CH30 F C1 CH=N-OCH3 180-183C
decomp.

Example 6 Moreover, the compound of the formula Ib where Z = O, X = S, m =
0, R = C02CH3, where Q is a radical of the formula Q4 where R3 =
F, y = O and TR7 = propargyl, was prepared by reacting 7-fluoro-6-isothiocyanato-4-(2-propargyl)-2H-1,4-benzoxazin-3(4H)one with methyl tetrahydro-4H-1,3,4-oxadiazine-4-carboxylate. Melting point 190-193°C.
Example 7 N-[4'-Chloro-2'-fluoro-5'-methoxyiminomethylphenyl)-4H-1,3,4-thiadiazine-4-carboxamide 0050~500$~ CA 02377143 2001-12-19 At 22~C, 0.7 g (5.7 mmol) of thionyl chloride was added to a mixture of 1.2 g of N-methyleneimino-N-2-hydroxyethyl-N'-[4'-chloro-2'-fluoro-5'-(methoxyiminomethyl)phenyl]urea -prepared according to Example la of DE 198.29.745.9 in 100 ml of 1,2-dichloroethane, and the mixture was stirred at 83~C for 2 h.
After cooling, the mixture was worked up by aqueous extraction, giving, after removal of the solvent, 1.3 g of N-methyleneimino-N-2-chloroethyl-N'-[4'-chloro-2'-fluoro-5'-(methoxyimino-methyl)phenyl]urea of melting point 120-122~C.
1.2 g of the resulting chloroethyl compound and 0.7 g of thiourea in 50 ml of DMSO were reacted at 22~C for 12 h and at 50~C for 1 h. The reaction mixture was then, at room temperature, stirred into 65 ml of lOg by weight strength aqueous sodium hydroxide solution, and the mixture was stirred at 20-30~C for another hour.
At the same temperature, 75 ml of 10~ by weight strength aqueous hydrochloric acid were added, and the mixture was extracted three times with dichloromethane. The organic phase was isolated, dried and filtered through a bed of silica gel. Goncentration of the solution gave 0.2 g of the title compound. Melting point 155-162~C.
The compounds Ia and Ib and their agriculturally useful salts are suitable, both in the form of isomer mixtures and in the form of the pure isomers, as herbicides. The herbicidal compositions comprising Ia or Ib control vegetation on non-crop areas very efficiently, especially at high rates of application. They act against broad-leaved weeds and harmful grasses in crops such as wheat, rice, maize, soya and cotton without causing any significant damage to the crop plants. This effect is mainly observed at low rates of application.
Depending on the application method used, the compounds Ia and Ib, or the compositions comprising them, can additionally be employed in a further number of crop plants for eliminating undesirable plants. Examples of suitable craps are the following:
Allium cepa, Ananas comosus, Arachis hypogaea, Asparagus officinalis, Beta vulgaris spec. altissima, Beta vulgaris spec.
rapa, Brassica napus oar. napus, Brassica napus oar.
napobrassica, Brassica rapa oar. silvestris, Camellia sinensis, 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 viti.folium), Heliar~~chus annuus, Hevea brasiliensis, Ho~deum vulgare, Humulus ~~50~5~~$~ CA 02377143 2001-12-19 lupulus, Ipomoea batatas, Juglans regia, Lens culinaris, Linum usitatissimum, Lycopersicon lycopersicum, Malus spec., Manihot esculenta, Medicago sativa, Musa spec., Nicotiana tabacum (N. rustica), Olea europaea, Oryza sativa, Phaseolus lunatus, 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 faba, Vitis vinifera and zea mays.
In addition, the compounds Ia and Ib may also be used in crops which tolerate the action of herbicides owing to breeding, including genetic engineering methods.
The herbicidal compositions or the active compounds can be applied pre- or post-emergence. If the active compaunds are less well tolerated by certain crop plants, application techniques may be used in which the herbicidal compositions are sprayed, with the aid of the spraying equipment, in such a way that they come into contact as little as possible, if at all, with the leaves of the sensitive crop plants, while the active compounds reach the leaves of undesirable plants growing underneath, or. the bare soil surface (post-directed, lay-by).
The compounds Ia and Ib, or the herbicidal compositions comprising them, can be used, for example, in the form of ready-to-spray aqueous solutions, powders, suspensions, also highly concentrated aqueous, oily or other suspensions or dispersions, emulsions, oil dispersions, pastes, dusts, materials for broadcasting or granules, by means of spraying, atomizing, dusting, broadcasting or watering. The use forms depend on the intended aims; in any case, they should ensure a very fine distribution of the active compounds according to the invention.
Essentially, suitable inert auxiliaries include:
mineral oil fractions of medium to high boiling point, such as kerosene and diesel oil, furthermore coal tar oils and oils of vegetable or animal origin, aliphatic, cyclic and aromatic hydrocarbons, e.g. paraffin, tetrahydronaphthalene, alkylated naphthalenes and their derivatives, alkylated benzenes and their derivatives, alcohols such as methanol, ethanol, propanol, butanol and cyclohexanol, ketones such as cyclohexanone, or strongly polar solvents, e.g. amines such as N-methylpyrrolidone, and water.

~~5~~5~08~ CA 02377143 2001-12-19 Aqueous use forms can be prepared from emulsion concentrates, suspensions, pastes, wettable powders or water-dispersible granules by adding water. To prepare emulsions, pastes or oil dispersions, the substituted ureas, either as such or dissolved in an oil or solvent, can be homogenized in water by means of a wetting agent, tackifier, dispersant or emulsifier.
Alternatively, it is possible to prepare concentrates comprising active substance, wetting agent, tackifier, dispersant or emulsifier and, if desired, solvent or oil, which are suitable for dilution with water.
Suitable surfactants are the alkali metal salts, alkaline earth metal salts and ammonium salts of aromatic sulfonic acids, e.g.
ligno-, phenol-, naphthalene- and dibutylnaphthalenesulfonic acid, and of fatty acids, alkyl- and alkylarylsulfonates, alkyl sulfates, lauryl ether sulfates and fatty alcohol sulfates, and salts of sulfated hexa-, hepta- and octadecanols, and also of fatty alcohol glycol ethers, condensates of sulfonated naphthalene and its derivatives with formaldehyde, condensates of naphthalene, or of the naphthalenesulfonic acids with phenol and formaldehyde, polyoxyethylene octylphenol ether, ethoxylated isooctyl-, octyl- or nonylphenol, alkylphenyl or tributylphenyl 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, lignosulfite waste liquors or methylcellulose. Powders, materials for broadcasting and dusts can be prepared by mixing or grinding the active substances together with a solid carrier.
Granules, e.g. coated granules, impregnated granules and homogeneous granules, can be prepared by binding the active compounds to solid carriers. Solid carriers are mineral earths, such as silicas, silica gels, silicates, talc, kaolin, limestone, lime, chalk, bole, loess, clay, dolomite, diatomaceous earth, calcium sulfate, magnesium sulfate, magnesium oxide, ground synthetic materials, fertilizers such as ammonium sulfate, ammonium phosphate and ammonium nitrate, ureas, and products of vegetable origin, such as cereal meal, tree bark meal, wood meal and nutshell meal, cellulose powders, or other solid carriers.
The concentrations o.f the active compounds Ia or Ib in the ready-to-use preparations can be varied within wide ranges. In general, the formulations comprise from 0.001 to 98o by weight, preferably 0.01 to 95o by weight, of at least one active compound. The active compounds are employed in a purity of from 90% to 100%, preferably 95% to 100% (according to the NMR
spectrum).
The compounds Ia and Ib according to the invention can be formulated, for example, as follows:
I 20 parts by weight of the compound Ib.6 are dissolved in a mixture composed of 80 parts by weight of alkylated benzene, 10 parts by weight of the adduct of 8 to 10 mol of ethylene oxide to 1 mol of oleic acid N-monoethanolamide, 5 parts by weight of the calcium salt of dodecylbenzenesulfonic acid and 5 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
II 20 parts by weight of the compound Ib.7 are dissolved in a mixture composed 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 to 1 mol of isooctylphenol and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
III 20 parts by weight of the compound Ib.6 are dissolved in a mixture composed of 25 parts by weight of cyclohexanone, 65 parts by weight of a mineral oil fraction of boiling point 210 to 280°C and 10 parts by weight of the adduct of 40 mol of ethylene oxide to 1 mol of castor oil. Pouring the solution into 100,000 parts by weight of water and finely distributing it therein gives an aqueous dispersion which comprises 0.02% by weight of the active compound.
IV 20 parts by weight of the compound Ib.6 are mixed thoroughly with 3 parts by weight of the sodium salt of diisobutylnaphthalenesulfonic acid, 17 parts by weight o.f the sodium salt of a lignosulfonic acid from a sulfite waste liquor and 60 parts by weight of pul.verulent silica gel, and 'the mixture is ground in a hammer mill. Finely distributing the mixture in 20,000 parts by weight of water gives a spray mixture which comprises 0.1~ by weight of the active compound.
V 3 parts by weight of the compound Ib.6 are mixed with 97 parts by weight of finely divided kaolin. This gives a dust which comprises 3~ by weight of the active compound.
VI 20 parts by weight of the compound Ib.7 axe mixed intimately with 2 parts by weight of the calcium salt of dodecylbenzenesulfonic acid, 8 parts by weight of fatty alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenol/urea/formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil. This gives a stable oily dispersion.
VII 1 part by weight of the compound Ib.6 is dissolved in a mixture composed of 70 parts by weight of cyclohexanone, parts by weight of ethoxylated isooctylphenol and 10 parts by weight of ethoxylated castor oil. This gives a 20 stable emulsion concentrate.
VIII 1 part by weight of the compound Ib.7 is dissolved in a mixture composed of 80 parts by weight of cyclohexanone and 20 parts by weight of Wettol~ EM 31 (nonionic emulsifier based on ethoxylated castor oil). This gives a stable emulsion concentrate.
To widen the activity spectrum and to achieve synergistic effects, the substituted ureas Ia or Ib may be mixed with a large number of representatives of other herbicidal or growth-regulating active-compound groups and then applied concomitantly. Suitable components for mixtures are, for example, 1,2,4-thiadiazoles, 1,3,4-thiadiazoles, amides, aminophosphoric acid and its derivatives, aminotriazoles, anilides, (het)aryloxyalkanoic acid and its derivatives, benzoic acid and its derivatives, benzothiadiazinones, 2-aroyl-1,3-cyclohexanediones, hetaryl aryl ketones, benzylisoxazolidinones, meta-CF3-phenyl derivatives, carbamates, quinolinecarboxylic acid and its derivatives, chloroacetanilides, cyclohexane-1,3-dione derivatives, diazines, dichloropropionic acid and its derivatives, dihydrobenzofurans, dihydrofuran-3-ones, dinitroanilines, dinitrophenols, diphenyl ethers, dipyridyls, halocarboxylic acids and their derivatives, ureas, 3-phenyluracils, imidazoles, imidazolinones, N-phenyl-3,4,5,6-tetrahydrophthalimides, oxadiazoles, oxiranes, phenols, aryloxy- or heteroaryloxyphenoxypropionic esters, phenylacetic acid and its derivatives, phenylpropionic acid and its derivatives, pyrazoles, phenylgyrazoles, pyridazines, pyridinecarboxylic acid and its derivatives, pyrimidyl ethers, sulfonamides, sulfonylureas, triazines, triazinones, triazolinones, triazolecarboxamides and uracils.
It may furthermore be advantageous to apply the compounds Ia or Ib, alone or else concomitantly in combination with other herbicides, in the form of a mixture with other crop protection agents, for example together with agents for controlling pests or phytopathogenic fungi or bacteria. Also of interest is the miscibility with mineral salt solutions, which are employed for treating nutritional and trace element deficiencies.
Non-phytotoxic oils and oil concentrates may also be added.
The application rates of active compound are from 0.01 to 3, preferably 0.1 to 1.0, kg/ha of active substance (a.s.), depending on the control target, the season, the target plants and the growth stage.
Part B
Use Examples The herbicidal action of the substituted ureas of the formulae Ia and Ib was demonstrated by greenhouse experiments:
The culture containers used were plastic pots containing loamy sand with approximately 3.0~ of humus as the substrate. The seeds of the test plants were sawn separately for each species.
For the pre-emergence treatment, the active compounds, which had been suspended or emulsified in water, were applied directly after sowing by means of finely distributing nozzles. The containers were irrigated gently to promote germination and growth and subsequently covered with transparent plastic hoods until the plants had rooted. This cover caused uniform germination of the test plants, unless this was adversely affected by the active compound.
For the post-emergence treatment, the test plants were first grown to a height of 3 to 15 cm, depending on the plant habit, and then treated with the active compounds which had been suspended or emulsified in water. To this end, the test plants were either sown directly and grown in the same containers, or they were first grown separately as seedlings and transplanted into the test containers a few days prior to treatment. The ~~50/50080 CA 02377143 2001-12-19 application rate for the post-emergence treatment was 62.5, 31.3 or 16.6 and 7.81 g of a.s./ha.
Depending on the species, the plants were kept at 10 to 25~C or 20 to 35~C. The test period extended over 2 to 4 weeks. During this time, the plants were tended, and their response to the individual treatments was evaluated.
The evaluation was carried out using a scale from 0 to 100. 100 means no 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 were of the following species:
Bayer code Common name ABUTH velvet leaf common amaranth CHEAL lambsquarters (goosefoot) COMBS commelinal bengal GALAP harrit cleavers IPOSS morning glory POLPE redshank PHBPU common morning glory SOLNI black nightshade vERSS speedwell TRZAW winter wheat At an application rate of 62.5, 31.3 or 16.6 and 7.81 g of a.s./ha, the compounds are highly effective in controlling undesired broad-leaved plants by the post-emergence method.
The numbers given below for the compounds Ia and Ib relate to the numbers of Tables 7 and 8.
The herbicidal activities given below were determined on postemergence application of the compounds in the greenhouse.

005~~5~0$0 CA 02377143 2001-12-19 Example compound Ib No.6 Application rate 62.5 31.3 (g of a.s./ha) Test plants Example compound Ib No.7 i ~N O
.~N N
CI
3 0 p-Application rate 15.6 7.8 (g of a.s./ha) Test plants Example compound Ib No. 17 ~h2C=CH
Application rate 62.5 31.3 (g of a.s./ha) Test plants Example compound Ib No. 37 N~O~
~N N
CI
~O/

Application rate 62.5 31.3(g of a.s./ha) Test plants ~05~~5~0$~ CA 02377143 2001-12-19 Example compound Ib No. 81 O
N"O ~
~N N
S
Application rate 62.5 31.3 (g of a.s./ha) Test plants Example compound Ib No. 78 I
CI
U
~H2CH=CH2 Application rate 62.5 31.3 (g of a.s./ha) Test plants CHEAI, 100 100 Example compound Ia No. 76 Application 15.6 7.8 (g of a.s./haj rate 0~50~5~080 CA 02377143 2001-12-19 Test plants ABUTH loo loo loo loo Example compoundIa No. 4 10Application rate 15.6 7.8 (g of a.s./ha) Test plants ~gE 100 100 Example compoundIa,No. 92 20Application rate 7.8 3.9 (g of a.s./ha) Test plants ~p,RE 10 0 10 0 Example compoundIb No. 94 30Application rate 15.6 7.8 (g of a.s./ha) Test plants p~p,~ ' 100 100 Example compoundIb No. 32 Application rate 31.3 15.6 (g of a.s./ha) Test plants Compound from Example 6 I
S
CH2C~CH
Application rate 15.6 7.8 (g of a.s./ha Test plants AMARE __. 100 100

Claims (18)

we claim:-

1. A substituted urea of the formula Ia or Ib in which the variables X, Z, m, R and R A are as defined below:

X is S or O;
Z is O, S, S=O or SO2;
m has the value 0, 1, 2 or 3;

R is C(O)OR10, C(O)SR10, C(S)OR10, C(S)SR10, CO2H, CHO, cyano, C(O)NR11R12, C(S)NR11R12, C(O)NHC(O)C1, C(O)NHS(O)2C1, C(O)NHC(O)OR12', C(O)NHS(O)2R12', C(O)NHS(O)2OR12', C(O)R2, P(O)R1(OR1), P(O)(OR1)2, S(O)n R2 where n = 0, 1 or 2, or SO2NHR1;

R A is hydroxyl, CO2R1, halogen, cyano, C(O)N(R1)2, where the radicals R1 are, if appropriate, different from one another, is OR2, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, COR1, S(O)n R1 where n = 0, 1 or 2, or is C(O)SR1;
and in which Q is one of the radicals Q1 to Q6:

in which Y and Y' independently of one another are O or S;
T is a chemical bond or O;
U is a chemical bond, C1-C4-alkylene, O, S, SO or SO2;
and the radicals R1 to R30 are as defined below:

R1 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C6-alkenyl or C3-C6=alkynyl;

R2 is C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, hydroxycarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C3-C6-cycloalkyl, C3-C6-cycloalkyl-C1-C6-alkyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C3-C6-cycloalkoxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyl, C3-C6-alkynyloxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C3-C6-haloalkenyloxy-C1-C6-alkyl, C3-C6-haloalkynyloxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-thioalkyl, C3-C6-alkenylthio-C1-C6-alkyl, C3-C6-alkynylthio-C1-C6-alkyl, cyano-C1-C6-alkyl, C3-C6-halocycloalkyl-C1-C6-alkyl, halo-C2-C6-alkenyl, C1-C6-alkoxy-C3-C6-alkenyl, C1-C6-haloalkoxy-C3-C6-alkenyl, C1-C6-alkylthio-C3-C6-alkenyl, C3-C6-haloalkynyl, C1-C6-alkoxy-C3-C6-alkynyl, C1-C6-haloalkoxy-C3-C6-alkynyl, C1-C6-alkylthio-C3-C6-alkynyl, C1-C6-alkylcarbonyl, CHR1COR7, CHR1P(O)(OR7)2, P(O)(OR7)2, CHR1P(S)(OR7)2, CHR1C(O)NR11R12, CHR1C(O)NH2, phenoxy-C1-C6-alkyl or benzyloxy-C1-C6-alkyl, where the benzene rings of the two last-mentioned groups may for their part be substituted by halogen, C1-C4-alkyl or C1-C4-haloalkyl; is benzyl which may be substituted by halogen, C1-C4-alkyl or C1-C4-haloalkyl or is phenyl or pyridyl, each of which may be substituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl or C1-C4-alkoxy;

R3 is hydrogen or halogen;

R4 is C1-C6-alkyl, C1-C6-haloalkyl, OCH3, SCH3, OCHF2, halogen, cyano or NO2;

R5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, C1-C6-alkoxy-(C1-C6-alkyl)carbonyl, C1-C6-alkylthio-(C1-C6-alkyl)carbonyl, (C1-C6-alkyl)iminooxycarbonyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxyamino-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkylamino-C1-C6-alkyl, is C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C2-C6-alkenyloxy, 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-alkylsulfonyloxy or C1-C6-alkylsulfonyl, where each of the 17 last-mentioned radicals may, if desired, carry one, two or three substituents 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-alkylsulfinyl, C1-C6-alkylsulfonyl, C1-C6-alkylideneaminooxy, oxo, =N-OR13;

- phenyl, phenoxy or phenylsulfonyl, where the three last-mentioned groups may carry one, two or three substituents selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;

- -CO-R14. -CO-OR14, -CO-SR14, -CO-N(R14)-R15, -OCO-R14, -OCO-OR14', -OCO-SR14', -OCO-N(R14)-R15, -N(R14)-R15, and -C(R16)=N-OR13;

is C(Z1)-R17, -C(=NR18)R17, C(R17)(Z2R19)(Z3R20), C(R17)=C(R21)-CN, C(R17)=C(R21)-CO-R22, -CH(R17)-CH(R21)-COR22, -C(R17)=C(R21)-CH2-CO-R22, -C(R17)=C(R21)-C(R23)=C(R24)-CO-R22, -C(R17)=C(R21)-CH2-CH(R25)-CO-R22, -CO-OR26, -CO-SR26, -CON(R26)-OR13, -CSC-CO-NHOR13, -CSC-CO-N(R26)-OR13, -C=C-CS-NH-OR13, -C=C-CS-N(R26)-OR13, -C(R17)=C(R21)-CO-NHOR13, -C(R17)=C(R21)-CO-N(R26)-OR13, -C(R17)=C(R21)-CS-NHOR13, -C(R17)=C(R21)-CS-N(R26)-OR13, -C(R17)=C(R21)-C(R16)=N-OR13, C(R16)=N-OR13, -CwC-C(R16)=NOR13, C(Z2R19)(Z3R20)-OR26, -C(Z2R19)(Z2R20)SR26, C(Z2R19)(Z3R20)-N(R27)R28, -N(R27)-R28, -CO-N(R27)-R28 or -C(R17)=C(R21)CO-N(R27)R28; where Z1, Z2, Z3 independently of one another are oxygen or sulfur;

R6 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C3-alkoxy-C1-C3-alkyl, C3-C6-alkenyl, C1-C3-alkoxy-C3-C6-alkenyl, C3-C6-haloalkenyl, C3-C6-alkynyl, C1-C3-alkoxy-C3-C6-alkynyl, C3-C6-haloalkynyl, C3-C7-cycloalkyl, 3- to 7-membered saturated heterocyclyl, where each cycloalkyl and each heterocyclyl ring may contain a carbonyl or thiocarbonyl ring member where each cycloalkyl and heterocyclyl ring may be unsubstituted or may carry one, two, three or four substitutents, selected from the group consisting of cyano, nitro, amino, hydroxyl, halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-cyanoalkyl, C1-C4-hydroxyalkyl, C1-C4-aminoalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, C1-C4-alkylsulfinyl, C1-C4-alkylsulfonyl, C1-C4-haloalkylsulfonyl, (C1-C4-alkoxy)carbonyl, (C1-C4-alkyl)carbonyl, (C1-C4-haloalkyl)carbonyl, (C1-C4-alkyl)carbonyloxy, (C1-C4-haloalkyl)carbonyloxy, di(C1-C4-alkyl)amino, C3-C6-alkenyl, C3-C6-alkynyl, C3-C4-alkenyloxy, C3-C4-alkenylthio, C3-C4-alkynyloxy and C3-C4-alkynylthio;

R7 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C3-alkoxy-C1-C3-alkyl, C2-C6-cyanoalkyl, C3-C6-alkenyl, C3-C6-alkynyl;

R8 is hydrogen, C1-C3-alkyl, C1-C3-haloalkyl or halogen;
R9 is hydrogen, C1-C3-alkyl, C1-C3-haloalkyl; or R8 and R9 together are C=O;
R10 is C1-C15-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C3-C10-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkylsulfinyl-C1-C6-alkyl, C1-C6-alkylsulfonyl-C1-C6-alkyl, C1-C3-alkoxy-C1-C3-alkoxy-C1-C3-alkyl, C3-C6-cycloalkyl-C1-C6-alkyl, carboxyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C2-C6-alkenyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C3-C8-cycloalkoxy-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyl, C3-C6-alkynyloxy-C1-C6-alkyl, C1-C6-haloalkoxy-C1-C6-alkyl, C3-C6-haloalkenyloxy-C1-C6-alkyl, C3-C6-haloalkynyloxy-C1-C6-alkyl, C3-C6-cycloalkyl-C1-C6-thioalkyl, C3-C6-alkenylthio-C1-C6-alkyl, C3-C6-alkynylthio-C1-C6-alkyl, cyano-C1-C6-alkyl, C3-C6-halocyclo-C1-C6-alkyl, halo-C3-C6-alkenyl, C1-C6-alkoxy-C3-C6-alkenyl, C1-C6-haloalkoxy-C3-C6-alkenyl, C1-C6-alkylthio-C3-C6-alkenyl, C3-C6-haloalkynyl, C1-C6-alkoxy-C3-C6-alkynyl, C1-C6-haloalkoxy-C3-C6-alkynyl, C1-C6-alkylthio-C3-C6-alkynyl, CHR1COR7, CHR1P(O)(OR7)2, P(O)(OR7)2, CHR1P(S)(OR7)2, CHR1C(O)NR11R12, CHR1C(O)NH2, C1-C6-alkyl, which is substituted by phenoxy or benzyloxy, where the benzene rings of the two last-mentioned groups may for their part be substituted by halogen, C1-C4-alkyl or C1-C4-haloalkyl;

is phenyl, pyridyl, naphthyl, quinolyl, quinazolyl, quinoxalyl, 1-methylindolyl, 1-methylbenzimidazolyl, 2-methylindazolyl, benzofuranyl, benzothienyl, benzoxazolyl, benzthiazolyl, benzyl, which may carry a divalent substituent, such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, in adjacent positions or which may in each case be mono- to pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, amino, C1-C4-monoalkylamino, C1-C4-dialkylamino, C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, hydroxyl, nitro or cyano;

R11 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy;

R12 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C2-C6-alkenyl, where the alkenyl chain may additionally carry one to three halogen and/or cyano radicals, are phenyl or benzyl which may carry a divalent substituent, such as methylenedioxy, difluoromethylenedioxy, chlorofluoromethylenedioxy, dichloromethylenedioxy, in adjacent positions or which may be mono- to pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio, C1-C4-haloalkylthio, amino, C1-C4-monoalkylamino, C1-C4-dialkylamino, C3-C6-cycloalkyl, C1-C4-alkoxycarbonyl, C1-C4-alkoxycarbonyl-C1-C4-alkyl, hydroxyl, nitro or cyano or R11 and R12 together with the common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle 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)-;

R12' is as defined for R12, but excluding hydrogen;

R13 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, in which the phenyl ring may, if desired, carry one, two or three substituents selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;

R14 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 ring of the two last-mentioned groups may be unsubstituted or may carry one, two or three radicals selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkyl)carbonyl;

R14' is as defined for R14, but excluding hydrogen;

R15 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;

R16 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-alkylthio, C1-C6-haloalkylthio, (C1-C6-alkyl)carbonyloxy, (C1-C6-haloalkyl)carbonyloxy, C1-C6-alkylsulfonyloxy or C1-C6-haloalkylsulfonyloxy, where the 12 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-alkyl)aminocarbonyl, di(C1-C6-alkyl)aminocarbonyl, (C1-C6-alkyl)carbonyloxy, C1-C6-alkoxy-(C1-C6-alkyl)aminocarbonyl;

is (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-alkenyl)carbonyloxy, 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;

is 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 for their part carry one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;

R17 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;

R18 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, -N(R29)R30, phenyl which for its part may carry one, two or three substituents, in each case 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;

is phenyl-C1-C6-alkoxy, phenyl-(C1-C6-alkyl), phenyl-C3-C6-alkenyloxy or phenyl-C3-C6-alkynyloxy, where in each case one or two methylene groups of the carbon chains in the four last-mentioned groups may be replaced by -O-, -S- or -N(C1-C6-alkyl)- and where the phenyl rings in the four last-mentioned groups may be unsubstituted or may for their part carry one to three substituents, 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;

is C3-C7-heterocyclyl, C3-C7-heterocyclyl-C1-C6-alkyl, C3-C7-heterocyclyl-C1-C6-alkoxy, C3-C7-heterocyclyl-C3-C6-alkenyloxy or C3-C7-heterocyclyl-C3-C6-alkynyloxy, where in each case one or two methylene groups of the carbon chains in the four last-mentioned groups may be replaced by -O-, -S- or -N(C1-C6-alkyl)- and where each heterocycle may be saturated, unsaturated or aromatic and is either unsubstituted or for its part carries one to three substituents, 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;

R19, R20 independently of one another are C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl or together are a saturated or unsaturated 2- to 4-membered carbon chain which may carry an oxo substituent, where a member of this chain which is not adjacent to the variables Z2 and Z3 may be replaced by -O-, -S-, -N=, -NH- or -N(C1-C6-alkyl)- and where the carbon chain may carry one to three substituents 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;

are unsubstituted or substituted phenyl where the carbon chain may also be substituted by a fused-on or spiro-linked 3- to 7-membered ring which may contain, as ring members, one or two heteroatoms selected from the group consisting of oxygen, sulfur, nitrogen and C1-C6-alkyl-substituted nitrogen and which may for its part, if desired, 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;

R21 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, (C1-C6-alkyl)carbonyl or (C1-C6-alkoxy)carbonyl;

R22 is hydrogen, O-R31, S-R31, C1-C6-alkyl which may carry one or two C1-C6-alkoxy substituents, is C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C1-C6-alkylthio-C1-C6-alkyl, C1-C6-alkyliminooxy, -N(R27)R28 or phenyl which may be unsubstituted or may carry one to three substituents, in each case 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;

R23 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(R27)R28 or phenyl which for its part may carry one to three substituents 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;

R24 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-haloalkyl, (C1-C6-alkyl)carbonyl or (C1-C6-alkoxy)carbonyl;

R25 is hydrogen, cyano, C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;
R26, R31 independently of one another are hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl or C2-C6-alkynyl, where the 4 last-mentioned groups may in each case 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;

are (C1-C6-haloalkyl)carbonyl, (C1-C6-alkoxy)carbonyl, C1-C6-alkylaminocarbonyl, di(C1-C6-alkyl)aminocarbonyl, C1-C6-alkyloximino-C1-C6-alkyl, C3-C6-cycloalkyl;

are phenyl or phenyl-C1-C6-alkyl, where the phenyl rings may be unsubstituted or may for their part carry one to three substituents, in each case selected from the group consisting of cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;

R27, R28, R29, R30 independently of one another are hydrogen, C1-C6-alkyl, C3-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, are (C1-C6-alkoxy)carbonyl-C2-C6-alkenyl, where the alkenyl chain may additionally carry one to three halogen and/or cyano radicals, are C1-C6-alkylsulfonyl, (C1-C6-alkoxy)carbonyl-C1-C6-alkylsulfonyl, phenyl or phenylsulfonyl, where the phenyl rings of the two last-mentioned radicals may be unsubstituted or may for their part carry one to three substituents, in each case 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 R27 and R28 and/or R29 and R30 together with the respective common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle 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)-;

and the agriculturally useful salts of the compounds of the formulae Ia and Ib.

2. A compound of the formula Ia or Ib as claimed in claim 1 where the variables are as defined below:

Z is O or S
R A is CO2R1, halogen, cyano, OR2 or C1-C3-alkyl;
m is 0, 1, 2 or 3;
Q is Q1, Q2 or Q4;
x, Y and Y' independently of one another are O or S;
T is a chemical bond or O;
U is a chemical bond, C1-C4-alkylene, O or S;
R is C(O)OR10, C(O)SR10, C(S)OR10, C(S)SR10, CHO, CN, C(O)R2, C(O)NR11R12, C(S)NR11R12, C(O)NHC(O)OR12', C(O)NHS(O)2R12', C(O)NHS(O)2OR12';
R1 is hydrogen or C1-C3-alkyl;
R2 is C1-C3-alkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C3-haloalkyl, C1-C3-alkoxycarbonyl-C1-C3-alkyl, cyano-C1-C3-alkyl, benzyl, which may be substituted by halogen, C1-C4-alkyl or trifluoromethyl, or is phenyl, which may be substituted by halogen, C1-C4-alkyl, trifluoromethyl or C1-C4-alkoxy;
R3 is hydrogen, fluorine or chlorine;
R4 is chlorine, trifluoromethyl or cyano;
R5 is hydrogen, hydroxyl, mercapto, cyano, nitro, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-haloalkoxy, C1-C6-haloalkylthio, C1-C6-alkoxy-(C1-C6-alkyl)carbonyl, C1-C6-alkylthio-(C1-C6-alkyl)carbonyl, (C1-C6-alkyl)iminooxycarbonyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxyamino-C1-C6-alkyl, C1-C6-alkoxy-C1-C6-alkylamino-C1-C6-alkyl, is C1-C6-alkoxy, C1-C6-alkylthio, C3-C6-cycloalkoxy, C3-C6-cycloalkylthio, C2-C6-alkenyloxy, 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-alkylsulfonyloxy or C1-C6-alkylsulfonyl, where each of these 17 radicals may, if desired, carry one, two or three substituents, 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-alkylsulfinyl, C1-C6-alkylsuifonyl, C1-C6-alkylideneaminooxy, oxo, =N-OR13 - phenyl, phenoxy or phenylsulfonyl, where the three last-mentioned substituents may for their part carry one, two or three substituents, in each case selected from the group consisting of halogen, nitro, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy and (C1-C6-alkoxy)carbonyl;

- -CO-R14, -CO-OR14, -CO-SR14, -CO-N(R14)-R15, -OCO-R14, -OCO-OR14', -OCO-SR14', -OCO-N(R14)-R15, -N(R14)-R15, and -C(R16)=N-OR13;

is C(Z1)-R17, -C(=NR18)R17, C(R17)(Z2R19)(Z3R20), C(R17)=C(R21)-CN, C(R17)=C(R21)-CO-R22, -CH(R17)-CH(R21)-COR22, -C(R17)=C(R21)-CH2-CO-R22, -C(R17)=C(R21)-C(R23)=C(R24)-CO-R22, -C(R17)=C(R21)-CH2-CH(R25)-CO-R22, -CO-OR26, -CO-SR26, -CON(R26)-OR13, -C=C-CO-NHOR13, -C=C-CO-N(R26)-OR13, -C=C-CS-NH-OR13, -C=C-CS-N(R26)-OR13, -C(R17)=C(R21)-CO-NHOR13, -C(R17)=C(R21)-CO-N(R26)-OR13, -C(R17)=C(R21)-CS-NHOR13, -C(R17)=C(R21)-CS-N(R26)-OR13, -C(R17)=C(R21)-C(R16)=N-OR13, C(R16)=N-OR13, -C=C-C(R16)=NOR13, C(Z2R19)(Z3R20)-OR26, -C(Z2R19)(Z2R20)SR26, C(Z2R19)(Z3R20)-N(R27)R28, -N(R27)-R28, -CO-N(R27)-R28 or -C(R17)=C(R21)CO-N(R27)R28; in which Z1, Z2, Z3 independently of one another are oxygen or sulfur;

R6 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C7-cycloalkyl, or is 3- to 7-membered saturated heterocyclyl which contains one or more oxygen and/or sulfur atoms;

R7 is hydrogen or C1-C6-alkyl;
R8 is hydrogen or C1-C3-alkyl;
R9 is hydrogen, C1-C3-alkyl R8 and R9 together are C=O;
R10 is C1-C15-alkyl, C3-C8-cycloalkyl, C2-C10-alkenyl, C3-C10-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyloxy-C1-C6-alkyl, C3-C6-alkynyloxy-C1-C6-alkyl, cyano-C1-C6-alkyl, is phenyl or benzyl which may in each case be mono- to pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloalkoxy, amino, C2-C4-monoalkylamino, C1-C4-dialkylamino, C1-C4-alkoxycarbonyl, nitro or cyano;

R11 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy;

R12 is hydrogen, C1-C6-alkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, phenyl or benzyl which may be mono- to pentasubstituted by halogen, C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-dialkylamino, C1-C4-alkoxycarbonyl, nitro or cyano;
or R12 is as defined for R12, but excluding hydrogen;

R11 and R12 together with the common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle;

R13 is hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-cycloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl, cyano-C1-C6-alkyl, (C1-C6-alkoxy)carbonyl-C1-C6-alkyl or phenylalkyl, where the phenyl ring may be mono- to trisubstituted by halogen, cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl or C1-C3-alkoxy;

R14 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-alkenyloxycarbonyl-C1-C6-alkyl, is phenyl or benzyl which may be unsubstituted on the phenyl ring or may be mono- to trisubstituted by halogen, cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl or C1-C3-alkoxy;

R14' is as defined for R14, but excluding hydrogen;

R15 is hydrogen, hydroxyl, C1-C6-alkyl, C1-C6-alkoxy, (C1-C3-alkoxy)carbonyl-C1-C3-alkoxy, C3-C6-alkenyl or C3-C6-alkynyl;

R16 is hydrogen, halogen, C1-C6-alkyl, C1-C6-haloalkyl, C1-C6-alkoxy, C3-C6-alkenyloxy, (C1-C6-alkoxy)carbonylalkoxy, C2-C6-alkenyl, (C2-C6-alkenyl)carbonyloxy, C3-C6-alkynyl, (C2-C6-alkynyl)carbonyloxy, is phenyl, phenoxy or benzyl, where the phenyl rings of the 3 last-mentioned radicals may be unsubstituted or mono- to trisubstituted by halogen, cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy or (C1-C3-alkoxy)carbonyl;

R17 is hydrogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl or (C1-C6-alkoxy)carbonyl;

R18 is hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C3-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkoxy, (C1-C6-alkoxy)carbonyl-C1-C6-alkyl, is phenyl or phenyl-(C1-C6-alkyl), where the two last-mentioned phenyl radicals may be substituted by halogen, cyano, nitro, C1-C3-alkyl, C1-C3-haloalkyl, C1-C3-alkoxy or (C1-C3-alkoxy)carbonyl;

R19, R20 independently of one another are C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxy-C1-C6-alkyl, or R19 and R20 together are a saturated 2- to 4-membered carbon chain which may carry an oxo substituent, where a carbon atom of this chain which is not adjacent to the variables Z2 and Z3 may be replaced by -O-, -S-, -N=, -NH- or -N(C1-C6-alkyl)- and where the carbon chain may be substituted once to three times by halogen or C1-C6-alkyl;

R21 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-haloalkyl or C1-C6-alkoxy;

R22 is hydrogen, OR31, S-R31, C1-C6-alkyl, which may carry one or two C1-C6-alkoxy substituents, is C2-C6-alkenyl, C2-C6-alkynyl, C1-C6-haloalkyl or C3-C6-cycloalkyl;

R23 is hydrogen, cyano, halogen, C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl;

R24 is hydrogen, cyano, halogen, C1-C6-alkyl, C1-C6-alkoxy or C1-C6-haloalkyl;

R25 is hydrogen, cyano or C2-C6-alkyl;

R26, R31 independently of one another axe hydrogen, C1-C6-alkyl, C1-C6-haloalkyl, C2-C6-alkenyl or C2-C6-alkynyl, where the 4 last-mentioned groups may in each case carry one or two of the following radicals:
cyano, halogen, C1-C6-alkoxy, C1-C6-alkylcarbonyl, (C1-C6-alkoxy)carbonyl;

or are (C1-C6-alkyl)carbonyl, (C1-C6-alkoxy)carbonyl, phenyl or phenyl-C1-C6-alkyl;

R27, R28, R29, R30 independently of one another are hydrogen, C1-C6-alkyl, C3-C6-alkenyl, C2-C6-alkynyl, C3-C6-cycloalkyl, C1-C6-haloalkyl, C1-C6-alkoxy-C1-C6-alkyl, C1-C6-alkylcarbonyl, (Cl-C6-alkoxy)carbonyl, or R27 and R28 and/or R29 and R30 together with the respective common nitrogen atom are a saturated or unsaturated 4- to 7-membered azaheterocycle which, in addition to carbon ring members, may, if desired, contain an oxygen atom or an -NH- group.

3. A compound of the formula Ia or Ib as claimed in claim 1 or 2 in which Q is Q1 and R5 is C1-C6-alkoxy, C2-C6-alkenyloxy or C2-C6-alkynyloxy, where each of the 3 last-mentioned radicals may, if desired, carry one to three substituents, in each case selected from the group consisting of halogen, C1-C6-alkoxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C1-C6-alkylsulfonyl, -CO-R14, -CO-OR14, -CO-N(R14)-R15, -N(R14)-R15 and -C(R16)=N-OR13;

is -CO-R17, -C(NR18)-R17, -C(R17)(OR19)(OR20), -C(R17)=C(R21)-CO-R22, -CH(R17)-CH(R21)-CO-R22, -CO-OR26, -CO-N(R26)-OR13, -C(R17)=C(R21)-CO-N(R26)-OR13, -C(R16)=N-OR13, -C(OR19)(OR20)-OR26, -N(R27)R28, -CON(R27)R28 or -C(R17)=C(R27)CO-N(R27)R28;

in which R13 to R22 and R26 to R28 are as defined above.

4. A compound of the formula Ia or Ib as claimed in any of the preceding claims in which R is C1-C6-alkyloxycarbonyl, (C1-C6-alkoxy)thiocarbonyl, (C1-C6-alkylthio)carbonyl, -CHO, -CN, -C(O)NR11R12, -C(O)NHC(O)Cl, -C(O)NHS(O)2Cl, C(O)NHC(O)OR12', C(O)NHS(O)2R12', C(O)R2, P(O)R1(OR1), P(O)(OR1)2; S(O)R2, S(O)2R2 or S(O)2NHR2 in which the variables R1, R2, R11, R12 and R12' are as defined below:

R1 is C1-C6-alkyl R2 is C1-C6-alkyl R11 is hydrogen or C1-C6-alkyl R12 is hydrogen, C1-C6-alkyl or C1-C6-alkoxy, and R12' is C1-C6-alkyl or C1-C6-alkyloxy;
Z is O or S, X is O or S, and m has the value 0.

5. A compound as claimed in claim 4 in which Q is Q1, R3 is hydrogen or halogen R4 is hydrogen, halogen or cyano, and R5 is C1-C6-alkyl, C3-C6-alkenyl, C1-C6-haloalkyl, C3-C6-haloalkenyl, C1-C6-alkoxy, C1-C6-haloalkoxy, C1-C6-alkylthio, C1-C6-haloalkylthio, C3-C6-alkenyloxy, C3-C6-alkynyloxy, haloalkenyloxy, alkenylthio, haloalkenylthio, C1-C6-alkoxycarbonyl-C1-C6-alkoxy, C3-C6-alkenyloxycarbonyl-C1-C6-alkoxy, C3-C6-alkynyloxycarbonyl-C1-C6-alkoxy, C1-C6-alkoxy-C1-C6-alkoxycarbonyl-C1-C6-alkoxy, (C3-C6-alkenyloxy)carbonyl-C1-C6-alkoxycarbonyl-C1-C4-alkoxy, C1-C6-alkoxycarbonyl-C1-C6-alkylthio, C1-C6-alkenyloxycarbonyl-C1-C6-alkylthio, C1-C6-alkynyloxycarbonyl-C1-C6-alkylthio, C1-C6-alkoxy-C1-C6-alkoxycarbonyl-C1-C6-alkylthio, C1-C6-alkoxyamino-C1-C6-alkyl, N-C1-C6-alkoxy-N-(C1-C6-alkyl)amino-C1-C6-alkyl, C1-C6-alkylsulfonylamino, -COOR26, -CONR27R28, -C(=NR18)R17, -C(R16)=NOR13, C(R17)=C(R21)-CO-R22, where the variables R13, R16, R17, R21, R22, R26 to R28 are as defined below:

R13 is C1-C6-alkyl, C1-C6-haloalkyl, C3-C6-alkenyl, C3-C6-haloalkeryl, C3-C6-alkynyl, C1-C6-cyanoalkyl or C1-C6-alkoxycarbonyl-C1-C6-alkyl;
R16 is hydrogen, C1-C6-alkyl, C1-C6-alkoxy, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C1-C6-alkoxycarbonyl-C1-C6-alkoxy or phenoxycarbonyl-C1-C6-alkoxy;
R17 is hydrogen, C1-C6-alkyl;
R21 is hydrogen, halogen, C1-C6-alkyl;
R22 is hydroxyl, C1-C6-alkoxy, C1-C6-alkylthio, C1-C6-alkoxycarbonyl-C1-C6-alkyl;
R26 is C1-C6-alkyl, C3-C6-haloalkyl, C3-C6-alkenyl, C3-C6-alkynyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyloxycarbonyl-C1-C6-alkyl, C3-C6-alkynyloxycarbonyl-C1-C6-alkyl, C1-C6-alkoxyalkyl;
R27 is hydrogen, C1-C6-alkyl;
R28 is hydrogen, C1-C6-alkyl, C1-C6-alkoxy, or R27 and R28 together are a 6-membered saturated azaheterocycle which may have one or two not adjacent oxygen atoms in the ring.

6. A compound of the formula Ia or Ib as claimed in claim 4 in which Q is Q2 or Q3, where R3 is hydrogen or halogen, R4 is hydrogen or halogen, Y is O or S, U is a single bond, oxygen or C1-C4-alkylene, and R6 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C7-cycloalkyl, saturated C3-C7-heterocyclyl which has one or two heteroatoms selected from the group consisting of oxygen and sulfur in the ring, is C1-C6-alkoxyalkyl, cyano-C1-C6-alkyl, CO2H, C1-C6-alkoxycarbonyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl.

7. A compound of the formula Ia or Ib as claimed in claim 4 in which Q is Q4 or Q5, in which R3 is hydrogen or halogen Y is O or S
Y' in the formula Q5 is oxygen or sulfur T is a single bond, oxygen or C1-C4-alkylene and R7 is hydrogen, halogen, cyano, C1-C6-alkyl, C1-C6-haloalkyl, C3-C7-cycloalkyl, saturated C3-C7-heterocyclyl which has one or two heteroatoms selected from the group consisting of oxygen and sulfur in the ring, is C1-C6-alkoxyalkyl, cyano-C1-C6-alkyl, CO2H, C1-C6-alkoxycarbonyl, C1-C6-alkoxycarbonyl-C1-C6-alkyl, C3-C6-alkenyl or C3-C6-alkynyl.

8. A compound of the formula Ia or Ib as claimed in claim 4 in which Q is Q6 R3 is hydrogen or halogen R4 is hydrogen or halogen R8 and R9 independently of one another are hydrogen, C1-C6-alkyl, halogen, cycloalkyl or C1-C6-haloalkyl, or R8 and R9 together with the carbon atom to which they are attached are a carbonyl group.

9. A compound of the formula Ia or Ib as claimed in any of the preceding claims in which Q is Q1, Z is oxygen, X is oxygen or sulfur, m has the value 0, R is C1-C4-alkoxycarbonyl or (C1-C4-alkoxycarbonyl)iminocarbonyl, R3 is fluorine, chlorine or hydrogen, R4 is halogen, and R5 is CN, COOH, C1-C4-alkoxyiminomethyl, C1-C4-alkoxy, C3-C6-cycloalkyloxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-alkenyloxyiminomethyl, (C1-C4-alkoxycarbonyl)-C2-C6-alkenyloxy, C3-C6-alkynyloxyiminomethyl, 2-[C1-C4-alkoxycarbonyl]-2-chloroethyl, 2-[C1-C4-alkoxycarbonyl]-2-chloroethenyl, C1-C4-alkoxycarbonyl, (C1-C6-alkoxycarbonyl)-C1-C4-alkoxy, (C1-C6-alkoxycarbonyl)-C1-C4-thioalkyl, is COOR26 where R26 = C1-C4-alkoxy-C1-C4-alkyl or C3-C6-alkenyloxycarbonyl-C1-C4-alkyl, is CONR27R28 where R27 = hydrogen or C1-C4-alkyl and R28 =
hydrogen, C1-C4-alkyl or C1-C4-alkoxy, is C(=NR17)R18 in which R17 is C1-C4-alkoxy and R18 is C1-C4-alkoxy or C1-C4-alkoxycarbonyl-C1-C4-alkoxy.

10. A composition comprising at least one substituted urea of the formula Ia or Ib in which the variables are as defined in any of claims 1 to 9 or an agriculturally useful salt of Ia or Ib and customary auxiliaries.

11. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one substituted urea of the formula Ia or Ib in which the variables are as defined in any of claims 1 to 9 or an agriculturally useful salt of Ia or Ib to act on plants, their habitat and/or on seed.

12. The use of substituted ureas of the formula Ia or Ib in which the variables are as defined in any of claims 1 to 9 or their agriculturally useful salts as herbicides.

13. A compound of the general formula Ia or Ib as claimed in claim 1, in which Q is Q1, R is C1-C4-alkoxycarbonyl or (C1-C4-alkoxycarbonyl)imino-carbonyl, Z is O and X is O or S, m has the value 0, R3 is fluorine or chlorine, R4 is halogen, and R5 is C1-C4-alkoxyiminomethyl, C1-C4-alkoxy, C3-C6-cyclo-alkyloxy, C3-C6-alkenyloxy, C3-C6-alkynyloxy, C3-C6-alkenyloxyiminomethyl, (C1-C4-alkoxycarbonyl)-C2-C6-alkenyloxy, C3-C6-alkynyloxyiminomethyl, 2-[C1-C4-alkoxy-carbonyl]-2-chloroethyl, 2-[C1-C4-alkoxycarbonyl]-2-chloroethenyl, (C1-C6-alkoxycarbonyl)-C1-C4-alkoxy, (C1-C6-alkoxycarbonyl)-C1-C4-thioalkyl.

14. A compound of the formula Ia or Ib as claimed in claim 1, in which R is C1-C4-alkoxycarbonyl or (C1-C4-alkoxycarbonyl)imino-carbonyl, Z is O and X is O or S, m has the value 0 and Q is Q4, in which R3 is halogen and Y is O, T is a single bond and R7 is C3-C6-alkynyl.

15. A method for controlling undesirable vegetation, which comprises allowing a herbicidally effective amount of at least one substituted urea of the general formula Ia or Ib, in which the variables are as defined in any of claims 13 or 14, or an agriculturally useful salt of Ia or Ib, to act on plants, their habitat and/or seeds.

16. The use of substituted ureas of the formula Ia or Ib in which the variables are as defined in any of claims 13 or 14 or agriculturally useful salts thereof as herbicides.

17. A composition, comprising at least one substituted urea of the formula Ia or Ib in which the variables are as defined in any of claims 13 or 14 or an agriculturally useful salt of Ia or Ib and customary auxiliaries.

18. A substituted urea of the formula Ia or Ib in which the variables X, Z, m, R, R A and Q are as defined in any of claims 1 to 10, 14 or 15 and R is hydrogen, except for those compounds of the formula Ia in which Z and X
are oxygen, m has the value 0, R is hydrogen and Q is a radical of the formula Q1 in which R3 = fluorine and R4 =
chlorine and R5 is selected from the group consisting of isopropoxy, propargyloxy, allyloxy, benzyloxy, isopropoxycarbonyl, hydroxyiminomethyl, methoxyiminomethyl, CH=NOCH2CO2CH3, -CH=N-O-C(CH3)2-CO2CH3, propargyloxyimino-methyl, -CH=C(C1)-CO2CH3, -CH=C(C1)CO2C2H5, -CH=C(C1)-CO2-CH2-CO2CH3, -CH=C(C1)-CO2-CH(CH3)CO2CH3, -CH=C(C1)-CO2-CH2-CO2-tert-butyl, -CH=C(C1)-CO2H, -CH=C(C1)-CONHOCH3, -CH=C(C1)-CONHOC2H5 or -CH=N-O-CH(CH3)-CO2CH3;
or Q is a radical of the formula Q1 where R3 = R5 = hydrogen and R5 = chlorine, or Q is a radical of the formula Q1 where R3 = R4 = chlorine and R5 = H, methoxyiminomethyl, -CH=C(C1)CO2H or -CH=C(C1)-CO2C(CH3)3;

furthermore excluding compounds of the formula Ia in which Z
is oxygen and X is sulfur, m has the value 0, R is hydrogen and Q is a radical of the formula Q4, where R3 = fluorine, Y
= oxygen and T-R7 = propargyl, allyl or 3-(ethoxycarbonyl)-prop-2-yl or Q is a radical of the formula Q1 where R3 = R4 =
chlorine and R5 = hydrogen;
furthermore excluding N-(2,4-dichlorophenyl)tetrahydro-4H-1,3,4-oxadiazine-4-carbothiamide;
furthermore excluding 2,2-dimethyl-4-(p-tolylcarbamoyl)-tetrahydro-4H-1,3,4-oxadiazine.